MiMeDB: Showing metabocard for monacolin J carboxylic acid (MMDBc0056088)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 20:16:19 UTC

Update Date

2022-08-12 20:09:34 UTC

MiMeDB ID

MMDBc0056088

Metabolite Identification

Common Name

monacolin J carboxylic acid

Description

monacolin J carboxylate, also known as monacolin J acid(1-), belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain. Based on a literature review very few articles have been published on monacolin J carboxylate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172222162D          

 31 32  0  0  1  0            999 V2000
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    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
    2.1434    2.8875    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
   -1.4289    2.4750    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
    3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  1  0  0  0  0
 11  1  1  1  0  0  0
 11  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  2  1  6  0  0  0
 12  3  1  0  0  0  0
 13  4  1  0  0  0  0
 13  7  2  0  0  0  0
 14  5  1  0  0  0  0
 14  9  1  0  0  0  0
 15  9  1  0  0  0  0
 15 10  1  0  0  0  0
 16  6  1  6  0  0  0
 16 12  1  0  0  0  0
 17  8  1  0  0  0  0
 18 10  1  0  0  0  0
 19 13  1  0  0  0  0
 19 16  1  0  0  0  0
 19 17  1  0  0  0  0
 14 20  1  1  0  0  0
 15 21  1  1  0  0  0
 17 22  1  1  0  0  0
 23 18  2  0  0  0  0
 24 18  1  0  0  0  0
 11 25  1  6  0  0  0
 12 26  1  1  0  0  0
 14 27  1  1  0  0  0
 15 28  1  1  0  0  0
 16 29  1  1  0  0  0
 17 30  1  6  0  0  0
 19 31  1  6  0  0  0
M  CHG  1  24  -1
M  END


  Mrv1652306172222162D          

 31 32  0  0  1  0            999 V2000
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    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
    2.1434    2.8875    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
   -1.4289    2.4750    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
    3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  1  0  0  0  0
 11  1  1  1  0  0  0
 11  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  2  1  6  0  0  0
 12  3  1  0  0  0  0
 13  4  1  0  0  0  0
 13  7  2  0  0  0  0
 14  5  1  0  0  0  0
 14  9  1  0  0  0  0
 15  9  1  0  0  0  0
 15 10  1  0  0  0  0
 16  6  1  6  0  0  0
 16 12  1  0  0  0  0
 17  8  1  0  0  0  0
 18 10  1  0  0  0  0
 19 13  1  0  0  0  0
 19 16  1  0  0  0  0
 19 17  1  0  0  0  0
 14 20  1  1  0  0  0
 15 21  1  1  0  0  0
 17 22  1  1  0  0  0
 23 18  2  0  0  0  0
 24 18  1  0  0  0  0
 11 25  1  6  0  0  0
 12 26  1  1  0  0  0
 14 27  1  1  0  0  0
 15 28  1  1  0  0  0
 16 29  1  1  0  0  0
 17 30  1  6  0  0  0
 19 31  1  6  0  0  0
M  CHG  1  24  -1
M  END
> <DATABASE_ID>
MMDBc0056088

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](O)(CC[C@@]1([H])[C@@]([H])(C)C=CC2=C[C@]([H])(C)C[C@]([H])(O)[C@]12[H])C[C@@]([H])(O)CC([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H30O5/c1-11-7-13-4-3-12(2)16(19(13)17(22)8-11)6-5-14(20)9-15(21)10-18(23)24/h3-4,7,11-12,14-17,19-22H,5-6,8-10H2,1-2H3,(H,23,24)/p-1/t11-,12-,14+,15+,16-,17-,19-/m0/s1

> <INCHI_KEY>
FJQFRDAWQRBFCG-IRUSZSJRSA-M

> <FORMULA>
C19H29O5

> <MOLECULAR_WEIGHT>
337.437

> <EXACT_MASS>
337.202047614

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
38.02058865496477

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,5R)-7-[(1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate

> <JCHEM_LOGP>
1.1084995889999996

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.890242523740099

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.212304105816785

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7010882021079595

> <JCHEM_POLAR_SURFACE_AREA>
100.82000000000001

> <JCHEM_REFRACTIVITY>
104.55779999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3R,5R)-7-[(1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336   5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.335   3.080   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       8.002   3.080   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      12.003   5.390   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      10.669   3.080   0.000  0.00  0.00           O-1
HETATM   25  H   UNK     0      -2.667   1.540   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.667   6.160   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       5.335   6.160   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       8.002   6.160   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.334   3.850   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.000   1.540   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.334   3.850   0.000  0.00  0.00           H+0
CONECT    1   11                                                            
CONECT    2   12                                                            
CONECT    3    4   12                                                       
CONECT    4    3   13                                                       
CONECT    5    6   14                                                       
CONECT    6    5   16                                                       
CONECT    7   11   13                                                       
CONECT    8   11   17                                                       
CONECT    9   14   15                                                       
CONECT   10   15   18                                                       
CONECT   11    1    7    8   25                                             
CONECT   12    2    3   16   26                                             
CONECT   13    4    7   19                                                  
CONECT   14    5    9   20   27                                             
CONECT   15    9   10   21   28                                             
CONECT   16    6   12   19   29                                             
CONECT   17    8   19   22   30                                             
CONECT   18   10   23   24                                                  
CONECT   19   13   16   17   31                                             
CONECT   20   14                                                            
CONECT   21   15                                                            
CONECT   22   17                                                            
CONECT   23   18                                                            
CONECT   24   18                                                            
CONECT   25   11                                                            
CONECT   26   12                                                            
CONECT   27   14                                                            
CONECT   28   15                                                            
CONECT   29   16                                                            
CONECT   30   17                                                            
CONECT   31   19                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

Synonyms

Value	Source
Monacolin J acid(1-)	ChEBI
Monacolin J carboxylic acid	Generator

Chemical Formula

C₁₉H₂₉O₅

Average Molecular Weight

337.437

Monoisotopic Molecular Weight

337.202047614

IUPAC Name

(3R,5R)-7-[(1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate

Traditional Name

(3R,5R)-7-[(1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate

CAS Registry Number

Not Available

SMILES

[H][C@@](O)(CC[C@@]1([H])[C@@]([H])(C)C=CC2=C[C@]([H])(C)C[C@]([H])(O)[C@]12[H])C[C@@]([H])(O)CC([O-])=O

InChI Identifier

InChI=1S/C19H30O5/c1-11-7-13-4-3-12(2)16(19(13)17(22)8-11)6-5-14(20)9-15(21)10-18(23)24/h3-4,7,11-12,14-17,19-22H,5-6,8-10H2,1-2H3,(H,23,24)/p-1/t11-,12-,14+,15+,16-,17-,19-/m0/s1

InChI Key

FJQFRDAWQRBFCG-IRUSZSJRSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Medium-chain hydroxy acids and derivatives

Direct Parent

Medium-chain hydroxy acids and derivatives

Alternative Parents

Substituents

Fatty alcohol
Medium-chain hydroxy acid
Medium-chain fatty acid
Beta-hydroxy acid
Hydroxy fatty acid
Fatty acyl
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organic anion
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

hydroxy monocarboxylic acid anion (CHEBI:79035 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	1.11	ChemAxon
pKa (Strongest Acidic)	4.21	ChemAxon
pKa (Strongest Basic)	-0.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	100.82 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	104.56 m³·mol⁻¹	ChemAxon
Polarizability	38.02 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

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

Proteins

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Fungi	Ascomycota	3	Human Feces

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

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

34448529

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

29918871

PDB ID

Not Available

ChEBI ID

79035

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for monacolin J carboxylic acid (MMDBc0056088)

MOL for #<Metabolite:0x000055b76dfa6e58>

3D MOL for #<Metabolite:0x000055b76dfa6e58>

3D SDF for #<Metabolite:0x000055b76dfa6e58>

3D-SDF for #<Metabolite:0x000055b76dfa6e58>

PDB for #<Metabolite:0x000055b76dfa6e58>

3D PDB for #<Metabolite:0x000055b76dfa6e58>

SMILES for #<Metabolite:0x000055b76dfa6e58>

INCHI for #<Metabolite:0x000055b76dfa6e58>

Structure for #<Metabolite:0x000055b76dfa6e58>

3D Structure for #<Metabolite:0x000055b76dfa6e58>