MiMeDB: Showing metabocard for zymosterol intermediate 1b (MMDBc0033056)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:32:50 UTC

Update Date

2022-08-31 22:21:27 UTC

Metabolite ID

MMDBc0033056

Metabolite Identification

Common Name

zymosterol intermediate 1b

Description

Zymosterol is an intermediate in the biosynthesis of both ergosterol, a major constituent of the fungal plasma membrane, and cholesterol, the homologous component in mammalian membranes. Cholesterol and ergosterol share most of their biosythetic pathway, with differences only in the part of the pathway that is downstream of zymosterol. [Biocyc PWY-6074 and PWY-6075]

Structure

MOL SDF PDB SMILES InChI

Structure #1
  Mrv0541 02241222272D          

 33 36  0  0  0  0            999 V2000
   11.7846    0.7723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0620    0.3760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0620   -0.4631    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.7846   -0.8749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4839   -0.4631    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.1988   -0.8749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9292   -0.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9292    0.3760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1988    0.7723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4839    0.3760    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.1988    1.5804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9292    2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6285    1.5804    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.6285    0.7723    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.4132    0.5159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8795    1.1686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4132    1.8368    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.6285    2.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4839    1.1841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6285   -0.0591    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.1359    2.2409    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4818   -1.2418    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3292   -0.8936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8422    2.6838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5567    3.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2711    2.6838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2711    1.8588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9856    3.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1277    3.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4132    2.6838    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.6988    3.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7846   -1.6999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0702   -2.1124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0  0  0  0
 17 13  1  0  0  0  0
 12 13  1  0  0  0  0
 13 18  1  1  0  0  0
  8 14  1  0  0  0  0
 15 14  1  0  0  0  0
 14 20  1  6  0  0  0
 11  9  1  0  0  0  0
 10  9  1  0  0  0  0
  8  9  2  0  0  0  0
  7  8  1  0  0  0  0
  5 10  1  0  0  0  0
 10 19  1  1  0  0  0
  1 10  1  0  0  0  0
 16 17  1  0  0  0  0
 30 17  1  0  0  0  0
 17 21  1  6  0  0  0
 11 12  1  0  0  0  0
 16 15  1  0  0  0  0
  6  7  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  0  0  0  0
  2  1  1  0  0  0  0
  3  4  1  0  0  0  0
  3  2  1  0  0  0  0
  5 22  1  6  0  0  0
  3 23  1  1  0  0  0
 29 24  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  2  0  0  0  0
 27 26  1  0  0  0  0
 28 26  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
  4 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END

Structure #1
  Mrv0541 02241222272D          

 33 36  0  0  0  0            999 V2000
   11.7846    0.7723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0620    0.3760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0620   -0.4631    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.7846   -0.8749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4839   -0.4631    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.1988   -0.8749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9292   -0.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9292    0.3760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1988    0.7723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4839    0.3760    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.1988    1.5804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9292    2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6285    1.5804    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.6285    0.7723    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.4132    0.5159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8795    1.1686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4132    1.8368    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.6285    2.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4839    1.1841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6285   -0.0591    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.1359    2.2409    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4818   -1.2418    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3292   -0.8936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8422    2.6838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5567    3.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2711    2.6838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2711    1.8588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9856    3.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1277    3.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4132    2.6838    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.6988    3.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7846   -1.6999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0702   -2.1124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0  0  0  0
 17 13  1  0  0  0  0
 12 13  1  0  0  0  0
 13 18  1  1  0  0  0
  8 14  1  0  0  0  0
 15 14  1  0  0  0  0
 14 20  1  6  0  0  0
 11  9  1  0  0  0  0
 10  9  1  0  0  0  0
  8  9  2  0  0  0  0
  7  8  1  0  0  0  0
  5 10  1  0  0  0  0
 10 19  1  1  0  0  0
  1 10  1  0  0  0  0
 16 17  1  0  0  0  0
 30 17  1  0  0  0  0
 17 21  1  6  0  0  0
 11 12  1  0  0  0  0
 16 15  1  0  0  0  0
  6  7  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  0  0  0  0
  2  1  1  0  0  0  0
  3  4  1  0  0  0  0
  3  2  1  0  0  0  0
  5 22  1  6  0  0  0
  3 23  1  1  0  0  0
 29 24  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  2  0  0  0  0
 27 26  1  0  0  0  0
 28 26  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
  4 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033056

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C=O)[C@]1([H])CC3)[C@H](C)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C28H44O2/c1-18(2)7-6-8-19(3)22-11-12-23-20-9-10-24-21(17-29)26(30)14-16-28(24,5)25(20)13-15-27(22,23)4/h7,17,19,21-24,26,30H,6,8-16H2,1-5H3/t19-,21?,22-,23+,24+,26+,27-,28+/m1/s1

> <INCHI_KEY>
ZLQSSFNCEUGGJF-BZBPNLPVSA-N

> <FORMULA>
C28H44O2

> <MOLECULAR_WEIGHT>
412.6478

> <EXACT_MASS>
412.334130652

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
51.699362753982015

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,5S,7S,11R,14R,15R)-5-hydroxy-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-6-carbaldehyde

> <ALOGPS_LOGP>
6.11

> <JCHEM_LOGP>
5.883687445666668

> <ALOGPS_LOGS>
-5.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.612300647016372

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.099425303226251

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8968453281359725

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
126.36039999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.83e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
zymosterol intermediate 1b

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      21.998   1.442   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.649   0.702   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.649  -0.864   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.998  -1.633   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      23.303  -0.864   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      24.638  -1.633   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      26.001  -0.864   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.001   0.702   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      24.638   1.442   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.303   0.702   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.638   2.950   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      26.001   3.733   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      27.307   2.950   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      27.307   1.442   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      28.771   0.963   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.642   2.181   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.771   3.429   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      27.307   4.531   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      23.303   2.210   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0      27.307  -0.110   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0      30.120   4.183   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0      23.299  -2.318   0.000  0.00  0.00           H+0
HETATM   23  O   UNK     0      19.281  -1.668   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      31.439   5.010   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      32.773   5.780   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      34.106   5.010   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      34.106   3.470   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      35.440   5.780   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      30.105   5.780   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      28.771   5.010   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      27.438   5.780   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      21.998  -3.173   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      20.664  -3.943   0.000  0.00  0.00           O+0
CONECT    1   10    2                                                       
CONECT    2    1    3                                                       
CONECT    3    4    2   23                                                  
CONECT    4    5    3   32                                                  
CONECT    5   10    4    6   22                                             
CONECT    6    7    5                                                       
CONECT    7    8    6                                                       
CONECT    8   14    9    7                                                  
CONECT    9   11   10    8                                                  
CONECT   10    9    5   19    1                                             
CONECT   11    9   12                                                       
CONECT   12   13   11                                                       
CONECT   13   14   17   12   18                                             
CONECT   14   13    8   15   20                                             
CONECT   15   14   16                                                       
CONECT   16   17   15                                                       
CONECT   17   13   16   30   21                                             
CONECT   18   13                                                            
CONECT   19   10                                                            
CONECT   20   14                                                            
CONECT   21   17                                                            
CONECT   22    5                                                            
CONECT   23    3                                                            
CONECT   24   29   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   24   30                                                       
CONECT   30   17   29   31                                                  
CONECT   31   30                                                            
CONECT   32    4   33                                                       
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

Synonyms

Value	Source
4alpha-Formyl-5alpha-cholesta-8,24-dien-3beta-ol	ChEBI
4a-Formyl-5a-cholesta-8,24-dien-3b-ol	Generator
4Α-formyl-5α-cholesta-8,24-dien-3β-ol	Generator
Zymosterol intermediic acid 1b	Generator

Molecular Formula

C₂₈H₄₄O₂

Average Mass

412.6478

Monoisotopic Mass

412.334130652

IUPAC Name

(2S,5S,7S,11R,14R,15R)-5-hydroxy-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-6-carbaldehyde

Traditional Name

zymosterol intermediate 1b

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C=O)[C@]1([H])CC3)[C@H](C)CCC=C(C)C

InChI Identifier

InChI=1S/C28H44O2/c1-18(2)7-6-8-19(3)22-11-12-23-20-9-10-24-21(17-29)26(30)14-16-28(24,5)25(20)13-15-27(22,23)4/h7,17,19,21-24,26,30H,6,8-16H2,1-5H3/t19-,21?,22-,23+,24+,26+,27-,28+/m1/s1

InChI Key

ZLQSSFNCEUGGJF-BZBPNLPVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols and derivatives

Alternative Parents

Substituents

Cholesterol-skeleton
3-beta-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

aldehyde (CHEBI:52615 )
Cholesterol and derivatives (LMST01010171 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0018 g/L	ALOGPS
logP	6.11	ALOGPS
logP	5.88	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	14.1	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	126.36 m³·mol⁻¹	ChemAxon
Polarizability	51.7 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

42626458

PDB ID

Not Available

ChEBI ID

52615

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Herrgard MJ, Swainston N, Dobson P, Dunn WB, Arga KY, Arvas M, Bluthgen N, Borger S, Costenoble R, Heinemann M, Hucka M, Le Novere N, Li P, Liebermeister W, Mo ML, Oliveira AP, Petranovic D, Pettifer S, Simeonidis E, Smallbone K, Spasic I, Weichart D, Brent R, Broomhead DS, Westerhoff HV, Kirdar B, Penttila M, Klipp E, Palsson BO, Sauer U, Oliver SG, Mendes P, Nielsen J, Kell DB: A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology. Nat Biotechnol. 2008 Oct;26(10):1155-60. doi: 10.1038/nbt1492. [PubMed:18846089 ]

Showing metabocard for zymosterol intermediate 1b (MMDBc0033056)

MOL for #<Metabolite:0x00007f121000fc20>

3D MOL for #<Metabolite:0x00007f121000fc20>

3D SDF for #<Metabolite:0x00007f121000fc20>

3D-SDF for #<Metabolite:0x00007f121000fc20>

PDB for #<Metabolite:0x00007f121000fc20>

3D PDB for #<Metabolite:0x00007f121000fc20>

SMILES for #<Metabolite:0x00007f121000fc20>

INCHI for #<Metabolite:0x00007f121000fc20>

Structure for #<Metabolite:0x00007f121000fc20>

3D Structure for #<Metabolite:0x00007f121000fc20>