MiMeDB: Showing metabocard for (-)-9-hydroxyhexylitaconic acid (MMDBc0009990)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 02:19:43 UTC

Update Date

2025-10-07 16:05:41 UTC

Metabolite ID

MMDBc0009990

Metabolite Identification

Common Name

(-)-9-hydroxyhexylitaconic acid

Description

(-)-9-hydroxyhexylitaconic acid is a metabolite belonging to the class of organic acids. It has been identified in the context of natural product chemistry, particularly in studies involving marine-derived fungi. This compound was isolated alongside other metabolites from the fungus Aspergillus aculeatus, highlighting its potential significance in the study of fungal secondary metabolites and their biological activities. The isolation of (-)-9-hydroxyhexylitaconic acid, along with pre-aurantiamine and other known compounds, suggests that it may play a role in the ecological interactions of the producing organism or possess bioactive properties that warrant further investigation. The presence of such metabolites in fungi indicates a rich source of chemical diversity that could lead to the discovery of novel compounds with pharmaceutical potential. Understanding the biosynthesis and function of (-)-9-hydroxyhexylitaconic acid may provide insights into its role in the organism and its potential applications in drug development or biochemistry. (PMID:21397285 )

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241502502D          

 16 15  0  0  0  0            999 V2000
    2.2836    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    0.9059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    0.9059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  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  2  0  0  0  0
  9 11  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0009990

> <DATABASE_NAME>
MIME

> <SMILES>
CC(O)CCCCC(C(O)=O)C(=C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H18O5/c1-7(12)5-3-4-6-9(11(15)16)8(2)10(13)14/h7,9,12H,2-6H2,1H3,(H,13,14)(H,15,16)

> <INCHI_KEY>
SPTZQYLKDFWPGO-UHFFFAOYSA-N

> <FORMULA>
C11H18O5

> <MOLECULAR_WEIGHT>
230.26

> <EXACT_MASS>
230.11542368

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
23.80919059257805

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(5-hydroxyhexyl)-3-methylidenebutanedioic acid

> <ALOGPS_LOGP>
1.00

> <JCHEM_LOGP>
1.3539820283333333

> <ALOGPS_LOGS>
-1.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.873464757354492

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.1141196202207935

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6252300250872564

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
57.24090000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.40e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(5-hydroxyhexyl)-3-methylidenebutanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       4.263   4.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.596   6.311   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.265   2.461   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      13.598   1.691   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      10.931   1.691   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.598   6.311   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      16.266   4.771   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      14.932   2.461   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

Synonyms

Value	Source
2-(5-Hydroxyhexyl)-3-methylidenebutanedioate	Generator

Molecular Formula

C₁₁H₁₈O₅

Average Mass

230.26

Monoisotopic Mass

230.11542368

IUPAC Name

2-(5-hydroxyhexyl)-3-methylidenebutanedioic acid

Traditional Name

2-(5-hydroxyhexyl)-3-methylidenebutanedioic acid

CAS Registry Number

Not Available

SMILES

CC(O)CCCCC(C(O)=O)C(=C)C(O)=O

InChI Identifier

InChI=1S/C11H18O5/c1-7(12)5-3-4-6-9(11(15)16)8(2)10(13)14/h7,9,12H,2-6H2,1H3,(H,13,14)(H,15,16)

InChI Key

SPTZQYLKDFWPGO-UHFFFAOYSA-N

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

Medium-chain hydroxy acid
Medium-chain fatty acid
Branched fatty acid
Hydroxy fatty acid
Methyl-branched fatty acid
Dicarboxylic acid or derivatives
Fatty acyl
Fatty acid
Unsaturated fatty acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	4.4 g/L	ALOGPS
logP	1	ALOGPS
logP	1.35	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	4.11	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	57.24 m³·mol⁻¹	ChemAxon
Polarizability	23.81 Å³	ChemAxon
Number of Rings	0	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_2_3) - 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
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	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 (eluted)	2025-10-23	179.9
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	121.0
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	354.8
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	413.9
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	324.6
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	234.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-23	1562.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	132.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	377.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	271.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	185.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	160.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	112.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	192.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	403.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	97.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	297.5
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1090.6
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	756.1

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	(-)-9-hydroxyhexylitaconic acid_TMS_1	C=C(C(=O)O)C(CCCCC(C)O[Si](C)(C)C)C(=O)O	standard non polar	2025-10-23	2194.98
Gas Chromatography	(-)-9-hydroxyhexylitaconic acid_TMS_2	C=C(C(=O)O)C(CCCCC(C)O)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	2149.3
Gas Chromatography	(-)-9-hydroxyhexylitaconic acid_TMS_3	C=C(C(=O)O[Si](C)(C)C)C(CCCCC(C)O)C(=O)O	standard non polar	2025-10-23	1650.44
Gas Chromatography	(-)-9-hydroxyhexylitaconic acid_TMS_4	C=C(C(=O)O[Si](C)(C)C)C(CCCCC(C)O[Si](C)(C)C)C(=O)O	standard non polar	2025-10-23	1730.98
Gas Chromatography	(-)-9-hydroxyhexylitaconic acid_TMS_5	C=C(C(=O)O)C(CCCCC(C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	2242.55
Gas Chromatography	(-)-9-hydroxyhexylitaconic acid_TMS_6	C=C(C(=O)O[Si](C)(C)C)C(CCCCC(C)O)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	1420.29
Gas Chromatography	(-)-9-hydroxyhexylitaconic acid_TMS_7	C=C(C(=O)O[Si](C)(C)C)C(CCCCC(C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	1313.69
Gas Chromatography	(-)-9-hydroxyhexylitaconic acid_TMS_1	C=C(C(=O)O)C(CCCCC(C)O[Si](C)(C)C)C(=O)O	standard polar	2025-10-23	2114.58
Gas Chromatography	(-)-9-hydroxyhexylitaconic acid_TMS_2	C=C(C(=O)O)C(CCCCC(C)O)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	1994.87
Gas Chromatography	(-)-9-hydroxyhexylitaconic acid_TMS_3	C=C(C(=O)O[Si](C)(C)C)C(CCCCC(C)O)C(=O)O	standard polar	2025-10-23	2087.62
Gas Chromatography	(-)-9-hydroxyhexylitaconic acid_TMS_4	C=C(C(=O)O[Si](C)(C)C)C(CCCCC(C)O[Si](C)(C)C)C(=O)O	standard polar	2025-10-23	1679.06
Gas Chromatography	(-)-9-hydroxyhexylitaconic acid_TMS_5	C=C(C(=O)O)C(CCCCC(C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	1842.44
Gas Chromatography	(-)-9-hydroxyhexylitaconic acid_TMS_6	C=C(C(=O)O[Si](C)(C)C)C(CCCCC(C)O)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	2407.48
Gas Chromatography	(-)-9-hydroxyhexylitaconic acid_TMS_7	C=C(C(=O)O[Si](C)(C)C)C(CCCCC(C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	1830.64

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	2	Human feces; Human sputum; Human	Metabolic reconstruction
Fungi	Ascomycota	1

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11253216

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 (-)-9-hydroxyhexylitaconic acid (MMDBc0009990)

MOL for #<Metabolite:0x00007f2e50a85270>

3D MOL for #<Metabolite:0x00007f2e50a85270>

3D SDF for #<Metabolite:0x00007f2e50a85270>

3D-SDF for #<Metabolite:0x00007f2e50a85270>

PDB for #<Metabolite:0x00007f2e50a85270>

3D PDB for #<Metabolite:0x00007f2e50a85270>

SMILES for #<Metabolite:0x00007f2e50a85270>

INCHI for #<Metabolite:0x00007f2e50a85270>

Structure for #<Metabolite:0x00007f2e50a85270>

3D Structure for #<Metabolite:0x00007f2e50a85270>