MiMeDB: Showing metabocard for Versicolactone B (MMDBc0001835)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-14 20:17:37 UTC

Update Date

2022-08-31 06:18:40 UTC

Metabolite ID

MMDBc0001835

Metabolite Identification

Common Name

Versicolactone B

Description

CHEMBL4277114 belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Based on a literature review very few articles have been published on CHEMBL4277114.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305142122172D          

 30 32  0  0  1  0            999 V2000
    1.6664    4.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7283    3.5818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4949    2.8702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6671    1.1392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4956    0.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0540    1.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7110    0.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2694    1.4363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3693    3.1402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0319    0.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242    2.3556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7751    0.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2652    1.9140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0938    1.4724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9213    3.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2868    1.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0979    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0722    1.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3271    0.9579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3132    0.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0583   -0.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2333   -0.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1978    1.4724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6458    0.8593    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1341    0.7863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5432   -1.0776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7484   -1.0776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0048    1.3009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9429    2.2571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9784    0.3744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
 11  9  1  0  0  0  0
 12 10  2  0  0  0  0
 15  1  1  0  0  0  0
 15  2  1  0  0  0  0
 15  9  2  0  0  0  0
 16 10  1  0  0  0  0
 16 13  2  0  0  0  0
 16 14  1  0  0  0  0
 17  7  2  0  0  0  0
 17  8  1  0  0  0  0
 18 11  1  0  0  0  0
 18 13  1  0  0  0  0
 19 12  1  0  0  0  0
 19 18  2  0  0  0  0
 20 17  1  0  0  0  0
 21 20  2  0  0  0  0
 22 21  1  0  0  0  0
 24 14  1  1  0  0  0
 24 20  1  0  0  0  0
 24 23  1  6  0  0  0
 25 19  1  0  0  0  0
 26 21  1  0  0  0  0
 27 22  2  0  0  0  0
 28 23  2  0  0  0  0
 29  3  1  0  0  0  0
 29 23  1  0  0  0  0
 30 22  1  0  0  0  0
 30 24  1  0  0  0  0
M  END


  Mrv1652305142122172D          

 30 32  0  0  1  0            999 V2000
    1.6664    4.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7283    3.5818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4949    2.8702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6671    1.1392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4956    0.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0540    1.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7110    0.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2694    1.4363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3693    3.1402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0319    0.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242    2.3556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7751    0.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2652    1.9140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0938    1.4724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9213    3.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2868    1.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0979    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0722    1.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3271    0.9579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3132    0.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0583   -0.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2333   -0.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1978    1.4724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6458    0.8593    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1341    0.7863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5432   -1.0776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7484   -1.0776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0048    1.3009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9429    2.2571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9784    0.3744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
 11  9  1  0  0  0  0
 12 10  2  0  0  0  0
 15  1  1  0  0  0  0
 15  2  1  0  0  0  0
 15  9  2  0  0  0  0
 16 10  1  0  0  0  0
 16 13  2  0  0  0  0
 16 14  1  0  0  0  0
 17  7  2  0  0  0  0
 17  8  1  0  0  0  0
 18 11  1  0  0  0  0
 18 13  1  0  0  0  0
 19 12  1  0  0  0  0
 19 18  2  0  0  0  0
 20 17  1  0  0  0  0
 21 20  2  0  0  0  0
 22 21  1  0  0  0  0
 24 14  1  1  0  0  0
 24 20  1  0  0  0  0
 24 23  1  6  0  0  0
 25 19  1  0  0  0  0
 26 21  1  0  0  0  0
 27 22  2  0  0  0  0
 28 23  2  0  0  0  0
 29  3  1  0  0  0  0
 29 23  1  0  0  0  0
 30 22  1  0  0  0  0
 30 24  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0001835

> <DATABASE_NAME>
MIME

> <SMILES>
COC(=O)[C@]1(CC2=CC(CC=C(C)C)=C(O)C=C2)OC(=O)C(O)=C1C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H24O6/c1-15(2)9-11-18-13-16(10-12-19(18)25)14-24(23(28)29-3)20(21(26)22(27)30-24)17-7-5-4-6-8-17/h4-10,12-13,25-26H,11,14H2,1-3H3/t24-/m1/s1

> <INCHI_KEY>
RJSPVDFWIJXQRW-XMMPIXPASA-N

> <FORMULA>
C24H24O6

> <MOLECULAR_WEIGHT>
408.45

> <EXACT_MASS>
408.157288493

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
42.35254216910656

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2R)-4-hydroxy-2-{[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]methyl}-5-oxo-3-phenyl-2,5-dihydrofuran-2-carboxylate

> <ALOGPS_LOGP>
4.12

> <JCHEM_LOGP>
4.883784068333332

> <ALOGPS_LOGS>
-4.74

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.423009947556762

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.689383510212195

> <JCHEM_PKA_STRONGEST_BASIC>
-3.255214677609378

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
113.74679999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.47e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2R)-4-hydroxy-2-{[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]methyl}-5-oxo-3-phenylfuran-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 14-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-MAY-21         0                                  
HETATM    1  C   UNK     0       3.111   8.471   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.093   6.686   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.657   5.358   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.712   2.127   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.392   0.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.567   3.157   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.927   0.144   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.103   2.681   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.556   5.862   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.059   0.964   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.032   4.397   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.447   0.644   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.495   3.573   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.042   2.749   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.586   7.006   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.535   2.428   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.783   1.175   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.001   3.253   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.477   1.788   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.318   0.699   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.842  -0.766   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.302  -0.766   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.103   2.749   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.072   1.604   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.984   1.468   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -4.747  -2.012   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -1.397  -2.012   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -5.609   2.428   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -3.627   4.213   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -1.826   0.699   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   15                                                            
CONECT    3   29                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5   17                                                       
CONECT    8    6   17                                                       
CONECT    9   11   15                                                       
CONECT   10   12   16                                                       
CONECT   11    9   18                                                       
CONECT   12   10   19                                                       
CONECT   13   16   18                                                       
CONECT   14   16   24                                                       
CONECT   15    1    2    9                                                  
CONECT   16   10   13   14                                                  
CONECT   17    7    8   20                                                  
CONECT   18   11   13   19                                                  
CONECT   19   12   18   25                                                  
CONECT   20   17   21   24                                                  
CONECT   21   20   22   26                                                  
CONECT   22   21   27   30                                                  
CONECT   23   24   28   29                                                  
CONECT   24   14   20   23   30                                             
CONECT   25   19                                                            
CONECT   26   21                                                            
CONECT   27   22                                                            
CONECT   28   23                                                            
CONECT   29    3   23                                                       
CONECT   30   22   24                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

Synonyms

Not Available

Molecular Formula

C₂₄H₂₄O₆

Average Mass

408.45

Monoisotopic Mass

408.157288493

IUPAC Name

methyl (2R)-4-hydroxy-2-{[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]methyl}-5-oxo-3-phenyl-2,5-dihydrofuran-2-carboxylate

Traditional Name

methyl (2R)-4-hydroxy-2-{[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]methyl}-5-oxo-3-phenylfuran-2-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@]1(CC2=CC(CC=C(C)C)=C(O)C=C2)OC(=O)C(O)=C1C1=CC=CC=C1

InChI Identifier

InChI=1S/C24H24O6/c1-15(2)9-11-18-13-16(10-12-19(18)25)14-24(23(28)29-3)20(21(26)22(27)30-24)17-7-5-4-6-8-17/h4-10,12-13,25-26H,11,14H2,1-3H3/t24-/m1/s1

InChI Key

RJSPVDFWIJXQRW-XMMPIXPASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acid ester
Benzenoid
Dicarboxylic acid or derivatives
2-furanone
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Dihydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Enol
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0075 g/L	ALOGPS
logP	4.12	ALOGPS
logP	4.88	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	8.69	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	113.75 m³·mol⁻¹	ChemAxon
Polarizability	42.35 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

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

78440730

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139583377

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

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 Versicolactone B (MMDBc0001835)

MOL for #<Metabolite:0x00007f91f2e7aeb0>

3D MOL for #<Metabolite:0x00007f91f2e7aeb0>

3D SDF for #<Metabolite:0x00007f91f2e7aeb0>

3D-SDF for #<Metabolite:0x00007f91f2e7aeb0>

PDB for #<Metabolite:0x00007f91f2e7aeb0>

3D PDB for #<Metabolite:0x00007f91f2e7aeb0>

SMILES for #<Metabolite:0x00007f91f2e7aeb0>

INCHI for #<Metabolite:0x00007f91f2e7aeb0>

Structure for #<Metabolite:0x00007f91f2e7aeb0>

3D Structure for #<Metabolite:0x00007f91f2e7aeb0>