MiMeDB: Showing metabocard for (1S,4R)-isodihydrocarvone (MMDBc0054780)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:34:33 UTC

Update Date

2022-08-12 20:09:04 UTC

Metabolite ID

MMDBc0054780

Metabolite Identification

Common Name

(1S,4R)-isodihydrocarvone

Description

2-caffeoylisocitric acid, also known as (e)-caffeoylisocitrate, belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. Based on a literature review very few articles have been published on 2-caffeoylisocitric acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221342D          

 27 27  0  0  0  0            999 V2000
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    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
   -0.7145   -1.2375    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
   -4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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
   -2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    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
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  7  1  1  0  0  0  0
  7  2  1  0  0  0  0
  7  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  3  1  0  0  0  0
 10  5  1  0  0  0  0
 10  9  2  0  0  0  0
 11  6  1  0  0  0  0
 12  4  1  0  0  0  0
 13  8  1  0  0  0  0
 14  8  1  0  0  0  0
 15 13  1  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
 18 11  2  0  0  0  0
 19 11  1  0  0  0  0
 20 12  2  0  0  0  0
 21 14  2  0  0  0  0
 22 14  1  0  0  0  0
 23 15  2  0  0  0  0
 24 15  1  0  0  0  0
 25 12  1  0  0  0  0
 25 13  1  0  0  0  0
 26  2  1  0  0  0  0
 27  4  1  0  0  0  0
M  END


  Mrv1652306172221342D          

 27 27  0  0  0  0            999 V2000
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    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
   -0.7145   -1.2375    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
   -4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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
   -2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    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
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  7  1  1  0  0  0  0
  7  2  1  0  0  0  0
  7  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  3  1  0  0  0  0
 10  5  1  0  0  0  0
 10  9  2  0  0  0  0
 11  6  1  0  0  0  0
 12  4  1  0  0  0  0
 13  8  1  0  0  0  0
 14  8  1  0  0  0  0
 15 13  1  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
 18 11  2  0  0  0  0
 19 11  1  0  0  0  0
 20 12  2  0  0  0  0
 21 14  2  0  0  0  0
 22 14  1  0  0  0  0
 23 15  2  0  0  0  0
 24 15  1  0  0  0  0
 25 12  1  0  0  0  0
 25 13  1  0  0  0  0
 26  2  1  0  0  0  0
 27  4  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054780

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(=C(/[H])C1=CC(O)=C(O)C=C1)C(=O)OC(C(CC(O)=O)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O10/c16-9-3-1-7(5-10(9)17)2-4-12(20)25-13(15(23)24)8(14(21)22)6-11(18)19/h1-5,8,13,16-17H,6H2,(H,18,19)(H,21,22)(H,23,24)/b4-2-

> <INCHI_KEY>
KYSQDMNDMYECNZ-RQOWECAXSA-N

> <FORMULA>
C15H14O10

> <MOLECULAR_WEIGHT>
354.267

> <EXACT_MASS>
354.058696651

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
31.377737952501178

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propane-1,2,3-tricarboxylic acid

> <JCHEM_LOGP>
0.9804318249999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
4.64067035189161

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0073428857351203

> <JCHEM_PKA_STRONGEST_BASIC>
-6.283762314039575

> <JCHEM_POLAR_SURFACE_AREA>
178.65999999999997

> <JCHEM_REFRACTIVITY>
79.2456

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-caffeoylisocitric acid

> <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      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -8.002   6.160   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0     -10.669   4.620   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   26  H   UNK     0      -9.336  -0.770   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0      -6.668  -2.310   0.000  0.00  0.00           H+0
CONECT    1    3    7                                                       
CONECT    2    4    7   26                                                  
CONECT    3    1    9                                                       
CONECT    4    2   12   27                                                  
CONECT    5    7   10                                                       
CONECT    6    8   11                                                       
CONECT    7    1    2    5                                                  
CONECT    8    6   13   14                                                  
CONECT    9    3   10   16                                                  
CONECT   10    5    9   17                                                  
CONECT   11    6   18   19                                                  
CONECT   12    4   20   25                                                  
CONECT   13    8   15   25                                                  
CONECT   14    8   21   22                                                  
CONECT   15   13   23   24                                                  
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   11                                                            
CONECT   19   11                                                            
CONECT   20   12                                                            
CONECT   21   14                                                            
CONECT   22   14                                                            
CONECT   23   15                                                            
CONECT   24   15                                                            
CONECT   25   12   13                                                       
CONECT   26    2                                                            
CONECT   27    4                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   54    0
END

Synonyms

Value	Source
(e)-Caffeoylisocitrate	ChEBI
2-Caffeoylisocitrate	ChEBI
(e)-Caffeoylisocitric acid	Generator

Molecular Formula

C₁₅H₁₄O₁₀

Average Mass

354.267

Monoisotopic Mass

354.058696651

IUPAC Name

1-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propane-1,2,3-tricarboxylic acid

Traditional Name

2-caffeoylisocitric acid

CAS Registry Number

Not Available

SMILES

[H]\C(=C(/[H])C1=CC(O)=C(O)C=C1)C(=O)OC(C(CC(O)=O)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C15H14O10/c16-9-3-1-7(5-10(9)17)2-4-12(20)25-13(15(23)24)8(14(21)22)6-11(18)19/h1-5,8,13,16-17H,6H2,(H,18,19)(H,21,22)(H,23,24)/b4-2-

InChI Key

KYSQDMNDMYECNZ-RQOWECAXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monosaccharide
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Carboxylic acid
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Carbonyl group
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

tricarboxylic acid (CHEBI:16166 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	0.98	ChemAxon
pKa (Strongest Acidic)	3.01	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	178.66 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	79.25 m³·mol⁻¹	ChemAxon
Polarizability	31.38 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_10) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum

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

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0016634	(1S,4R)-isodihydrocarvone	(3S,6R)-6-isopropenyl-3-methyloxepan-2-one	Monocyclic monoterpene ketone monooxygenase	Oxygenation	RHEA	34755880
MMDBr0016635	(1S,4R)-isodihydrocarvone	(3S,6R)-6-isopropenyl-3-methyloxepan-2-one	Monocyclic monoterpene ketone monooxygenase	Oxygenation	RHEA	34755880

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
Bacteria	Actinobacteria	1	Human

Exposure Sources

Source Type	Source Sub-type	Species	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

4444181

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5280552

PDB ID

Not Available

ChEBI ID

16166

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 (1S,4R)-isodihydrocarvone (MMDBc0054780)

MOL for #<Metabolite:0x00007fa4ea384b68>

3D MOL for #<Metabolite:0x00007fa4ea384b68>

3D SDF for #<Metabolite:0x00007fa4ea384b68>

3D-SDF for #<Metabolite:0x00007fa4ea384b68>

PDB for #<Metabolite:0x00007fa4ea384b68>

3D PDB for #<Metabolite:0x00007fa4ea384b68>

SMILES for #<Metabolite:0x00007fa4ea384b68>

INCHI for #<Metabolite:0x00007fa4ea384b68>

Structure for #<Metabolite:0x00007fa4ea384b68>

3D Structure for #<Metabolite:0x00007fa4ea384b68>