MiMeDB: Showing metabocard for Higginsianin B (MMDBc0021788)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 11:56:51 UTC

Update Date

2022-08-31 06:47:32 UTC

Metabolite ID

MMDBc0021788

Metabolite Identification

Common Name

Higginsianin B

Description

Higginsianin B belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Based on a literature review a small amount of articles have been published on Higginsianin B.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152113562D          

 34 36  0  0  1  0            999 V2000
    4.5989   -3.8590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2562   -3.3702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0421   -1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8205   -1.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3508   -2.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1027   -1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0686   -3.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2295    1.3951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0  0  0  0
 11 10  1  0  0  0  0
 13  8  1  0  0  0  0
 14 12  1  0  0  0  0
 16  1  1  0  0  0  0
 16  2  1  0  0  0  0
 16  9  2  0  0  0  0
 17  3  2  0  0  0  0
 17 10  1  0  0  0  0
 18  4  1  0  0  0  0
 19  5  1  0  0  0  0
 19 18  2  0  0  0  0
 20 15  1  0  0  0  0
 21 15  1  6  0  0  0
 21 17  1  0  0  0  0
 22 11  1  0  0  0  0
 23 12  1  0  0  0  0
 24 18  1  0  0  0  0
 24 20  2  0  0  0  0
 25 20  1  0  0  0  0
 26  6  1  6  0  0  0
 26 14  1  0  0  0  0
 26 21  1  0  0  0  0
 26 22  1  0  0  0  0
 27  7  1  6  0  0  0
 27 13  1  1  0  0  0
 27 22  1  0  0  0  0
 27 23  1  0  0  0  0
 23 28  1  1  0  0  0
 29 24  1  0  0  0  0
 30 25  2  0  0  0  0
 31 19  1  0  0  0  0
 31 25  1  0  0  0  0
 21 32  1  6  0  0  0
 22 33  1  1  0  0  0
 23 34  1  6  0  0  0
M  END


  Mrv1652305152113562D          

 34 36  0  0  1  0            999 V2000
    4.5989   -3.8590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2562   -3.3702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0421   -1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8205   -1.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3508   -2.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1027   -1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0686   -3.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2295    1.3951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0  0  0  0
 11 10  1  0  0  0  0
 13  8  1  0  0  0  0
 14 12  1  0  0  0  0
 16  1  1  0  0  0  0
 16  2  1  0  0  0  0
 16  9  2  0  0  0  0
 17  3  2  0  0  0  0
 17 10  1  0  0  0  0
 18  4  1  0  0  0  0
 19  5  1  0  0  0  0
 19 18  2  0  0  0  0
 20 15  1  0  0  0  0
 21 15  1  6  0  0  0
 21 17  1  0  0  0  0
 22 11  1  0  0  0  0
 23 12  1  0  0  0  0
 24 18  1  0  0  0  0
 24 20  2  0  0  0  0
 25 20  1  0  0  0  0
 26  6  1  6  0  0  0
 26 14  1  0  0  0  0
 26 21  1  0  0  0  0
 26 22  1  0  0  0  0
 27  7  1  6  0  0  0
 27 13  1  1  0  0  0
 27 22  1  0  0  0  0
 27 23  1  0  0  0  0
 23 28  1  1  0  0  0
 29 24  1  0  0  0  0
 30 25  2  0  0  0  0
 31 19  1  0  0  0  0
 31 25  1  0  0  0  0
 21 32  1  6  0  0  0
 22 33  1  1  0  0  0
 23 34  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0021788

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]1(O)CC[C@]2(C)[C@]([H])(CC3=C(O)C(C)=C(C)OC3=O)C(=C)CC[C@@]2([H])[C@]1(C)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O4/c1-16(2)9-8-13-27(7)22-11-10-17(3)21(26(22,6)14-12-23(27)28)15-20-24(29)18(4)19(5)31-25(20)30/h9,21-23,28-29H,3,8,10-15H2,1-2,4-7H3/t21-,22-,23-,26-,27+/m1/s1

> <INCHI_KEY>
DZEAYBRRTVFUAI-GYPJDVINSA-N

> <FORMULA>
C27H40O4

> <MOLECULAR_WEIGHT>
428.613

> <EXACT_MASS>
428.292659768

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
50.5533481727488

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[(1R,4aR,5S,6R,8aR)-6-hydroxy-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-decahydronaphthalen-1-yl]methyl}-4-hydroxy-5,6-dimethyl-2H-pyran-2-one

> <ALOGPS_LOGP>
5.20

> <JCHEM_LOGP>
5.488969379000003

> <ALOGPS_LOGS>
-4.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.89653378800173

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.725625933430972

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6570559648472817

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
127.83739999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.44e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(1R,4aR,5S,6R,8aR)-6-hydroxy-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-hexahydro-1H-naphthalen-1-yl]methyl}-4-hydroxy-5,6-dimethylpyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0       8.585  -7.203   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.078  -6.291   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.679  -1.950   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.132  -3.397   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.121  -4.577   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.658  -1.950   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.595  -6.024   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       0.428   2.604   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   32  H   UNK     0       4.001   0.770   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0       5.335  -1.540   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0       8.002  -1.540   0.000  0.00  0.00           H+0
CONECT    1   16                                                            
CONECT    2   16                                                            
CONECT    3   17                                                            
CONECT    4   18                                                            
CONECT    5   19                                                            
CONECT    6   26                                                            
CONECT    7   27                                                            
CONECT    8    9   13                                                       
CONECT    9    8   16                                                       
CONECT   10   11   17                                                       
CONECT   11   10   22                                                       
CONECT   12   14   23                                                       
CONECT   13    8   27                                                       
CONECT   14   12   26                                                       
CONECT   15   20   21                                                       
CONECT   16    1    2    9                                                  
CONECT   17    3   10   21                                                  
CONECT   18    4   19   24                                                  
CONECT   19    5   18   31                                                  
CONECT   20   15   24   25                                                  
CONECT   21   15   17   26   32                                             
CONECT   22   11   26   27   33                                             
CONECT   23   12   27   28   34                                             
CONECT   24   18   20   29                                                  
CONECT   25   20   30   31                                                  
CONECT   26    6   14   21   22                                             
CONECT   27    7   13   22   23                                             
CONECT   28   23                                                            
CONECT   29   24                                                            
CONECT   30   25                                                            
CONECT   31   19   25                                                       
CONECT   32   21                                                            
CONECT   33   22                                                            
CONECT   34   23                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

Synonyms

Not Available

Molecular Formula

C₂₇H₄₀O₄

Average Mass

428.613

Monoisotopic Mass

428.292659768

IUPAC Name

3-{[(1R,4aR,5S,6R,8aR)-6-hydroxy-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-decahydronaphthalen-1-yl]methyl}-4-hydroxy-5,6-dimethyl-2H-pyran-2-one

Traditional Name

3-{[(1R,4aR,5S,6R,8aR)-6-hydroxy-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-hexahydro-1H-naphthalen-1-yl]methyl}-4-hydroxy-5,6-dimethylpyran-2-one

CAS Registry Number

Not Available

SMILES

[H][C@@]1(O)CC[C@]2(C)[C@]([H])(CC3=C(O)C(C)=C(C)OC3=O)C(=C)CC[C@@]2([H])[C@]1(C)CCC=C(C)C

InChI Identifier

InChI=1S/C27H40O4/c1-16(2)9-8-13-27(7)22-11-10-17(3)21(26(22,6)14-12-23(27)28)15-20-24(29)18(4)19(5)31-25(20)30/h9,21-23,28-29H,3,8,10-15H2,1-2,4-7H3/t21-,22-,23-,26-,27+/m1/s1

InChI Key

DZEAYBRRTVFUAI-GYPJDVINSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Pyranone
Pyran
Vinylogous acid
Cyclic alcohol
Heteroaromatic compound
Secondary alcohol
Lactone
Oxacycle
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0094 g/L	ALOGPS
logP	5.2	ALOGPS
logP	5.49	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	7.73	ChemAxon
pKa (Strongest Basic)	-0.66	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	127.84 m³·mol⁻¹	ChemAxon
Polarizability	50.55 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	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	Metabolic reconstruction

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

58917300

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

127033674

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for Higginsianin B (MMDBc0021788)

MOL for #<Metabolite:0x0000560be228c5c8>

3D MOL for #<Metabolite:0x0000560be228c5c8>

3D SDF for #<Metabolite:0x0000560be228c5c8>

3D-SDF for #<Metabolite:0x0000560be228c5c8>

PDB for #<Metabolite:0x0000560be228c5c8>

3D PDB for #<Metabolite:0x0000560be228c5c8>

SMILES for #<Metabolite:0x0000560be228c5c8>

INCHI for #<Metabolite:0x0000560be228c5c8>

Structure for #<Metabolite:0x0000560be228c5c8>

3D Structure for #<Metabolite:0x0000560be228c5c8>