MiMeDB: Showing metabocard for Dihydrocarolic acid (MMDBc0012802)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 04:15:27 UTC

Update Date

2025-10-07 16:06:03 UTC

Metabolite ID

MMDBc0012802

Metabolite Identification

Common Name

Dihydrocarolic acid

Description

Dihydrocarolic acid is a natural product classified as a metabolite within the chemical class of organic acids. It has been identified as an inhibitor of CD45 tyrosine phosphatase, a crucial enzyme involved in the regulation of immune responses. This compound, along with penitricin D, was isolated from the fermentation broth of the fungus Aspergillus niger, showcasing the potential of fungal metabolites in biochemistry and pharmacology. The purification process employed high-speed countercurrent chromatography (HSCCC) followed by high-performance liquid chromatography (HPLC), highlighting the advanced techniques used to isolate bioactive compounds from natural sources. The relevance of dihydrocarolic acid in the context of immune modulation suggests its potential utility in therapeutic applications, particularly in disorders where CD45 activity is implicated. Further research into its biological activity and mechanisms of action may provide insights into its role in cellular signaling pathways and its possible applications in medicine. (PMID:10805569 )

Structure

MOL SDF PDB SMILES InChI

Dihydrocarolic acid
  Mrv1652309242002302D          

 13 14  0  0  0  0            999 V2000
    1.5268    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7018    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2169    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4718    1.4521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5678    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2352    0.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0198    0.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5048    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0198    1.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2352    1.7224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5678   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2352   -0.8974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2169   -0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13  2  1  0  0  0  0
 10  6  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0012802

> <DATABASE_NAME>
MIME

> <SMILES>
C=C1OC(=O)\C(=C2/CCCO2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H8O4/c1-5-8(10)7(9(11)13-5)6-3-2-4-12-6/h1-4H2/b7-6+

> <INCHI_KEY>
NBPJTZQIOVMOFS-VOTSOKGWSA-N

> <FORMULA>
C9H8O4

> <MOLECULAR_WEIGHT>
180.159

> <EXACT_MASS>
180.042258738

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
17.14085503621519

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(E)-5'-methylidene-3,4-dihydro-2'H,4'H,5H,5'H-[2,3'-bioxolylidene]-2',4'-dione

> <ALOGPS_LOGP>
0.68

> <JCHEM_LOGP>
0.6987003799999998

> <ALOGPS_LOGS>
-1.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.847533332858435

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
45.38010000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.20e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(E)-5'-methylidene-4,5-dihydro-3H-[2,3'-bioxolylidene]-2',4'-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Dihydrocarolic acid                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-SEP-20         0                                  
HETATM    1  C   UNK     0       2.850   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.310   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.405   1.246   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.881   2.711   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.060   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.306   1.675   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.770   1.199   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.676   2.445   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.770   3.691   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.306   3.215   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.060  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.306  -1.675   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.405  -1.246   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   11                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    6                                                       
CONECT   11    5   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    2                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

Synonyms

Value	Source
Dihydrocarolate	Generator

Molecular Formula

C₉H₈O₄

Average Mass

180.159

Monoisotopic Mass

180.042258738

IUPAC Name

(E)-5'-methylidene-3,4-dihydro-2'H,4'H,5H,5'H-[2,3'-bioxolylidene]-2',4'-dione

Traditional Name

(E)-5'-methylidene-4,5-dihydro-3H-[2,3'-bioxolylidene]-2',4'-dione

CAS Registry Number

Not Available

SMILES

C=C1OC(=O)\C(=C2/CCCO2)C1=O

InChI Identifier

InChI=1S/C9H8O4/c1-5-8(10)7(9(11)13-5)6-3-2-4-12-6/h1-4H2/b7-6+

InChI Key

NBPJTZQIOVMOFS-VOTSOKGWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydrofurans

Sub Class

Furanones

Direct Parent

Furanones

Alternative Parents

Substituents

3-furanone
Enol ester
Oxolane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous ester
Cyclic ketone
Lactone
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Carbonyl group
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	12 g/L	ALOGPS
logP	0.68	ALOGPS
logP	0.7	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	45.38 m³·mol⁻¹	ChemAxon
Polarizability	17.14 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

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-09	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (void)	2025-10-23	124.2
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (void)	2025-10-23	30.2
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	370.9
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	465.8
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	416.7
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-23	361.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	1840.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	128.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	645.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	364.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	264.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	238.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	137.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	172.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	618.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	98.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	367.9
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1181.0
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	969.7

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

8617708

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10442289

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 Dihydrocarolic acid (MMDBc0012802)

MOL for #<Metabolite:0x00007f9ab8945ca0>

3D MOL for #<Metabolite:0x00007f9ab8945ca0>

3D SDF for #<Metabolite:0x00007f9ab8945ca0>

3D-SDF for #<Metabolite:0x00007f9ab8945ca0>

PDB for #<Metabolite:0x00007f9ab8945ca0>

3D PDB for #<Metabolite:0x00007f9ab8945ca0>

SMILES for #<Metabolite:0x00007f9ab8945ca0>

INCHI for #<Metabolite:0x00007f9ab8945ca0>

Structure for #<Metabolite:0x00007f9ab8945ca0>

3D Structure for #<Metabolite:0x00007f9ab8945ca0>