Cannabis Compound Database: Showing Compound Card for Indolelactic acid (CDB005146)

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Record Information

Version

1.0

Created at

2020-04-17 19:13:58 UTC

Updated at

2020-11-18 16:39:26 UTC

CannabisDB ID

CDB005146

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Indolelactic acid

Description

Indolelactic acid, also known as indolelactate, belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring. Indolelactic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Tryptophan is metabolized by two major pathways in humans, either through kynurenine or via a series of indoles, and some of its metabolites are known to be biologically active. Indolelactic acid (CAS: 1821-52-9) is a tryptophan metabolite found in human plasma, serum, and urine. Indolelactic acid is also a microbial metabolite; urinary indole-3-lactate is produced by Clostridium sporogenes (PMID: 29168502 ). Indolelactic acid is present in various amounts, significantly higher in umbilical fetal plasma than in maternal plasma in the protein-bound form (PMID 2361979 , 1400722 , 3597614 , 11060358 , 1400722 ). Indolelactic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Indolelactate	Generator
3-(indol-3-yl) LACTic acid	HMDB
(2S)-2-Hydroxy-3-(1H-indol-3-yl)propanoic acid	HMDB
(2S)-2-Hydroxy-3-(1H-indol-3-yl)propionic acid	HMDB
(2S)-2-Hydroxy-3-indoylpropanoic acid	HMDB
(2S)-2-Hydroxy-3-indoylpropionic acid	HMDB
(S)-2-Hydroxy-3-(1H-indol-3-yl)propanoic acid	HMDB
(S)-2-Hydroxy-3-(1H-indol-3-yl)propionic acid	HMDB
(S)-Indole-3-lactic acid	HMDB
(AlphaS)-alpha-hydroxy-1H-indole-3-propanoic acid	HMDB
(AlphaS)-alpha-hydroxy-1H-indole-3-propionic acid	HMDB
(ΑS)-α-hydroxy-1H-indole-3-propanoic acid	HMDB
(ΑS)-α-hydroxy-1H-indole-3-propionic acid	HMDB
2-(1H-indol-3-yl)Acetaldehyde	HMDB
2-Hydroxy-3-(1H-indol-3-yl)propanoic acid	HMDB
2-Hydroxy-3-(1H-indol-3-yl)propionic acid	HMDB
2-Hydroxy-3-(3-indolyl)propanoic acid	HMDB
2-Hydroxy-3-(3-indolyl)propionic acid	HMDB
3-(3-Indolyl)-2-hydroxypropanoic acid	HMDB
3-(3-Indolyl)-2-hydroxypropionic acid	HMDB
3-(3-Indolyl)-DL-lactic acid	HMDB
3-Indolyllactic acid	HMDB
Indole-3-L-lactic acid	HMDB
Indole-3-lactic acid	HMDB
L-3-(3-Indolyl)lactic acid	HMDB
L-Indole-3-lactic acid	HMDB
alpha-Hydroxy-1H-indole-3-propanoic acid	HMDB
alpha-Hydroxy-1H-indole-3-propionic acid	HMDB
beta-(3-Indolyl)lactic acid	HMDB
beta-Indolyllactic acid	HMDB
Α-hydroxy-1H-indole-3-propanoic acid	HMDB
Α-hydroxy-1H-indole-3-propionic acid	HMDB
Β-(3-indolyl)lactic acid	HMDB
Β-indolyllactic acid	HMDB
Indolelactic acid	HMDB

Chemical Formula

C₁₁H₁₁NO₃

Average Molecular Weight

205.21

Monoisotopic Molecular Weight

205.0739

IUPAC Name

(2S)-2-hydroxy-3-(1H-indol-3-yl)propanoic acid

Traditional Name

3-(indol-3-yl) lactate

CAS Registry Number

7417-65-4

SMILES

O[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O

InChI Identifier

InChI=1S/C11H11NO3/c13-10(11(14)15)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,10,12-13H,5H2,(H,14,15)/t10-/m0/s1

InChI Key

XGILAAMKEQUXLS-JTQLQIEISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indolyl carboxylic acids and derivatives

Alternative Parents

Substituents

Indolyl carboxylic acid derivative
3-alkylindole
Indole
Alpha-hydroxy acid
Hydroxy acid
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Azacycle
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Source:

Endogenous

Biological:

Microbe:

Clostridium:

Clostridium sporogenes

Biological location:

Tissue and substructures:

Placenta

Biofluid and excreta:

Organ and components:

Prostate

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	17 mg/mL	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.33	ALOGPS
logP	1.28	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	4.14	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	73.32 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	54.55 m³·mol⁻¹	ChemAxon
Polarizability	20.7 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

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Indolelactic acid, 2 TMS, GC-MS Spectrum	splash10-001i-0900000000-a73dacebbb4e696069e3	Spectrum
GC-MS	Indolelactic acid, 3 TMS, GC-MS Spectrum	splash10-0udi-0290000000-fabadc12766d82241f9d	Spectrum
GC-MS	Indolelactic acid, non-derivatized, GC-MS Spectrum	splash10-001i-0900000000-a73dacebbb4e696069e3	Spectrum
GC-MS	Indolelactic acid, non-derivatized, GC-MS Spectrum	splash10-0udi-0290000000-fabadc12766d82241f9d	Spectrum
GC-MS	Indolelactic acid, non-derivatized, GC-MS Spectrum	splash10-001i-0900000000-026f2953e75b09c74d71	Spectrum
GC-MS	Indolelactic acid, non-derivatized, GC-MS Spectrum	splash10-0udi-0390000000-f0750c125bcd98a91da9	Spectrum
Predicted GC-MS	Indolelactic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-053f-3900000000-518956592de7aaad712f	Spectrum
Predicted GC-MS	Indolelactic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Indolelactic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Indolelactic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Indolelactic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Indolelactic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Indolelactic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Indolelactic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Indolelactic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Indolelactic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Indolelactic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Indolelactic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Indolelactic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Indolelactic acid, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Indolelactic acid, TBDMS_2_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)	splash10-0bti-0950000000-59498880ad7081aa3753	2020-02-10	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0159-0900000000-6a8d0e31efc5b93545e6	2020-02-10	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-015c-2900000000-90fc3496f234f903c6de	2020-02-10	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-00lr-0900000000-887bb7e62bbec731a8f7	2020-02-10	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-01p9-0900000000-a21984d35288538673d9	2020-02-10	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-00lr-0900000000-887bb7e62bbec731a8f7	2020-02-10	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0bu9-0930000000-eb637fab2d892b6f884b	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01q9-0900000000-71208d388abba707ce94	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900000000-11da08a6a64282a294a3	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-3590000000-4f5f452c037ff1151799	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0m8c-2910000000-63debafc3bcaff103bdd	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-4900000000-ab106b4b81c99f1d7ebd	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0g4r-5950000000-3f3287f11e17b591ca4c	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-9800000000-e6a4bb98ed20d6fc95e1	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-1900000000-302e068c5b69a4503cc6	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0buc-0920000000-3019b4b814cdf115acfb	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02al-0900000000-484d4e288555da486bce	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001l-2900000000-4f3f55f2b6430ce9ce50	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000671

DrugBank ID

DB07060

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

676157

PDB ID

Not Available

ChEBI ID

Not Available

References

General References

Dodd D, Spitzer MH, Van Treuren W, Merrill BD, Hryckowian AJ, Higginbottom SK, Le A, Cowan TM, Nolan GP, Fischbach MA, Sonnenburg JL: A gut bacterial pathway metabolizes aromatic amino acids into nine circulating metabolites. Nature. 2017 Nov 30;551(7682):648-652. doi: 10.1038/nature24661. Epub 2017 Nov 22. [PubMed:29168502 ]
Morita I, Kawamoto M, Hattori M, Eguchi K, Sekiba K, Yoshida H: Determination of tryptophan and its metabolites in human plasma and serum by high-performance liquid chromatography with automated sample clean-up system. J Chromatogr. 1990 Apr 6;526(2):367-74. doi: 10.1016/s0378-4347(00)82520-7. [PubMed:2361979 ]
Morita I, Kawamoto M, Yoshida H: Difference in the concentration of tryptophan metabolites between maternal and umbilical foetal blood. J Chromatogr. 1992 May 8;576(2):334-9. doi: 10.1016/0378-4347(92)80208-8. [PubMed:1400722 ]
Artigas F, Gelpi E: Evaluation of the potential of thermospray liquid chromatography-mass spectrometry in neurochemistry. J Chromatogr. 1987 May 8;394(1):123-34. doi: 10.1016/s0021-9673(01)94166-4. [PubMed:3597614 ]
Salen G, Xu G, Tint GS, Batta AK, Shefer S: Hyperabsorption and retention of campestanol in a sitosterolemic homozygote: comparison with her mother and three control subjects. J Lipid Res. 2000 Nov;41(11):1883-9. [PubMed:11060358 ]

Showing Compound Card for Indolelactic acid (CDB005146)

Structure for CDB005146 (Indolelactic acid)