Showing Compound Isocitric acid (FDB003281)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:44 UTC

Update date

2019-11-26 02:58:48 UTC

Primary ID

FDB003281

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Isocitric acid

Description

Isocitric acid, also known as isocitrate or i-cit, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Isocitric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Isocitric acid exists in all living species, ranging from bacteria to humans. Isocitric acid is found, on average, in the highest concentration within milk (cow). Isocitric acid has also been detected, but not quantified in, several different foods, such as apples, wild celeries, gooseberries, carrots, and soursops. This could make isocitric acid a potential biomarker for the consumption of these foods.

CAS Number

320-77-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1-Hydroxypropane-1,2,3-tricarboxylic acid	ChEBI
1-Hydroxytricarballylic acid	ChEBI
1-Hydroxypropane-1,2,3-tricarboxylate	Generator
1-Hydroxytricarballylate	Generator
Isocitrate	Generator
1-Hydroxy-1,2,3-propanetricarboxylate	HMDB
1-Hydroxy-1,2,3-propanetricarboxylic acid	HMDB
3-Carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylate	HMDB
3-Carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylic acid	HMDB
3-Carboxy-2,3-dideoxy-pentarate	HMDB
3-Carboxy-2,3-dideoxy-pentaric acid	HMDB
D-Isocitrate	HMDB
I-cit	HMDB
Threo-D(S)-iso-citrate	HMDB
Threo-DS-isocitrate	HMDB
Isocitric acid, sodium salt	HMDB
Isocitric acid, trisodium salt	HMDB
Isocitric acid, disodium salt	HMDB
Isocitric acid, (11)C-labeled	HMDB
Isocitric acid, calcium salt	HMDB
Isocitric acid, potassium salt	HMDB
3-Carboxy-3,4-dideoxypentaric acid, 9CI	db_source
threo-D(S)-Iso-citrate	HMDB
threo-Ds-isocitrate	HMDB

Predicted Properties

Property	Value	Source
Water Solubility	52.5 g/L	ALOGPS
logP	-0.35	ALOGPS
logP	-1.4	ChemAxon
logS	-0.56	ALOGPS
pKa (Strongest Acidic)	3.07	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	132.13 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	35.72 m³·mol⁻¹	ChemAxon
Polarizability	15.55 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C6H8O7

IUPAC name

1-hydroxypropane-1,2,3-tricarboxylic acid

InChI Identifier

InChI=1S/C6H8O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2,4,9H,1H2,(H,7,8)(H,10,11)(H,12,13)

InChI Key

ODBLHEXUDAPZAU-UHFFFAOYSA-N

Isomeric SMILES

OC(C(CC(O)=O)C(O)=O)C(O)=O

Average Molecular Weight

192.1235

Monoisotopic Molecular Weight

192.02700261

Classification

Description

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

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Beta-hydroxy acid
Monosaccharide
Hydroxy acid
Alpha-hydroxy acid
Secondary alcohol
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

tricarboxylic acid (CHEBI:30887 )

Ontology

Physiological effect

Health effect:

Health condition:

Anoxia

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Biological location:

Organ and components:

Endocrine gland:

Adrenal gland

Subcellular:

Biofluid and excreta:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 37.51%; H 4.20%; O 58.29%	DFC
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Isocitric acid, 4 TMS, GC-MS Spectrum	splash10-0002-1952000000-7c34751686a6bdb54cab	Spectrum
GC-MS	Isocitric acid, 4 TMS, GC-MS Spectrum	splash10-0002-0963000000-459b45ff9246b5f55914	Spectrum
GC-MS	Isocitric acid, non-derivatized, GC-MS Spectrum	splash10-0002-0942000000-61204d02a28e43d21607	Spectrum
GC-MS	Isocitric acid, 4 TMS, GC-MS Spectrum	splash10-00di-9420000000-4e1a59fe735855d52ce2	Spectrum
GC-MS	Isocitric acid, 4 TMS, GC-MS Spectrum	splash10-00ea-3793000000-84858fa896697420275f	Spectrum
GC-MS	Isocitric acid, non-derivatized, GC-MS Spectrum	splash10-0002-1952000000-7c34751686a6bdb54cab	Spectrum
GC-MS	Isocitric acid, non-derivatized, GC-MS Spectrum	splash10-0002-0963000000-459b45ff9246b5f55914	Spectrum
GC-MS	Isocitric acid, non-derivatized, GC-MS Spectrum	splash10-00di-9420000000-4e1a59fe735855d52ce2	Spectrum
GC-MS	Isocitric acid, non-derivatized, GC-MS Spectrum	splash10-00ea-3793000000-84858fa896697420275f	Spectrum
Predicted GC-MS	Isocitric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00ba-7900000000-96194d87d52b155cf1b9	Spectrum
Predicted GC-MS	Isocitric acid, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-02vi-7029500000-2bb65fc897e48cc21750	Spectrum
Predicted GC-MS	Isocitric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isocitric acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isocitric acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isocitric acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isocitric acid, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isocitric acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isocitric acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isocitric acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isocitric acid, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isocitric acid, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isocitric acid, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isocitric acid, TMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isocitric acid, TMS_3_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isocitric acid, TMS_3_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0udi-1900000000-8e1185b0504ea1547715	Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-05fr-7900000000-0855c1ceb168d556b7f2	Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0bu1-9500000000-140b46d0f1dc8fcd9e49	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00fu-0940000000-033739944b190c47c6a7	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-053r-1900000000-89ff897aa220452bfa16	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0900000000-36aeb28d857c9039938b	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-03di-1900000000-53373dc0755caa954310	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0006-0901310000-883764bf7b686ca7fd17	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03di-0900000000-66d03405eeb126c6ad9d	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-00di-0900000000-cdad17a11f419421c787	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udi-0009000000-d3440c84a488b3e22212	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0006-0900000000-3aa263561a7a49df7d3d	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0006-1900000000-3636f87026e4206a1638	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-01w3-9600000000-ab1a2b9a29528a623d0b	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0079-9000000000-3c33cefeb87f85efd5de	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-059m-9000000000-34775db8bbc008018633	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-0900000000-3aa263561a7a49df7d3d	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-1900000000-3636f87026e4206a1638	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-01w3-9600000000-ab1a2b9a29528a623d0b	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004j-0900000000-a75a4b486df1552d6d93	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0gla-4900000000-d04fec4218cafd6195df	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fk9-8900000000-4e5fbbb415df9fbc8f31	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00ke-1900000000-c364bae4640e201c366d	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0v4j-4900000000-d00f263a75673b7981c7	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pk9-9200000000-156693398229f972d717	Spectrum

NMR

Type	Description	View
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Spectrum