UCSF

ZINC03802189

Draw Identity 99% 90% 80% 70%

Substance Information

In ZINC since Heavy atoms Benign functionality
December 7th, 2005 20 Yes

Popular Name: LINOLENIC ACID LINOLENIC ACID

Find On: PubMed — Wikipedia — Google

CAS Numbers: 463-40-1 , 68424-45-3 , [463-40-1]

Other Names:

(9,12,15)-linolenate; (9,12,15)-linolenic acid; (9Z,12Z,15Z)-Octadecatrienoate; (9Z,12Z,15Z)-Octadecatrienoic acid; (Z,Z,Z)-9,12,15-Octadecatrienoate; (Z,Z,Z)-9,12,15-Octadecatrienoic acid; 9,12,15-Octadecatrienoate; 9,12,15-Octadecatrienoic acid; 9-cis,1

(9,12,15)-linolenate; (9,12,15)-linolenic acid; 463-40-1; 9Z,12Z,15Z-octadecatrienoate; 9Z,12Z,15Z-octadecatrienoic acid; LINOLENIC_ACID; alpha-linolenate; linolenate

(9,12,15)-linolenate; (9Z,12Z,15Z)-octadecatrienoate; all-cis--9,12,15-octadecatrienoate; cis,cis,cis-9,12,15-octadecatrienoate; linolenate

(9,12,15)-linolenate;(9,12,15)-linolenic acid;(9Z,12Z,15Z)-Octadecatrienoate;(9Z,12Z,15Z)-Octadecatrienoic acid;(Z,Z,Z)-9,12,15-Octadecatrienoate;(Z,Z,Z)-9,12,15-Octadecatrienoic acid;9,12,15-Octadecatrienoate;9,12,15-Octadecatrienoic acid;9-cis,12-cis,15

(9,12,15)-linolenic acid; (Z,Z,Z)-9,12,15-octadecatrienoic acid; 9-cis,12-cis,15-cis-octadecatrienoic acid; ALA; all-cis-9,12,15-octadecatrienoic acid; alpha-linolenic acid; cis,cis,cis-9,12,15-octadecatrienoic acid; cis-Delta(9,12,15)-octadecatrienoic ac

(9Z,12Z,15Z)-Octadeca-9,12,15-trienoic acid

(9Z,12Z,15Z)-Octadecatrienoic acid

(9Z,12Z,15Z)-Octadecatrienoic acid; 463-40-1; 9,12,15-Octadecatrienoic acid; C06427; Linolenate; alpha-Linolenate; alpha-Linolenic acid

.alpha.-Linolenic Acid

673

9,12,15-Octadecatrienoic acid

9Z,12Z,15Z-octadecatrienoic acid

ALA

alpha-Linolenate

alpha-linolenic acid

BRD-K33396764-001-02-0

CHEBI:43891; CHEBI:22462; CHEBI:10298

cis-9, cis-12, cis-15-octadecatrienoic acid; C18:3n-3,6,9

DNC013630

α-linolenic acid

linolenate

Linolenic acid, 99%

Linolenic-17,17,18,18,18-D5 Acid

MFCD00065720

Download: MOL2 SDF SMILES Flexibase

Annotations

Vendors

Physical Representations

Type pH range xlogP Des A‑Pol Apolar desolvation (kcal/mol) Des Pol Polar desolvation (kcal/mol) H Don H-bond donors H Acc H-bond acceptors Chg Net charge tPSA (Ų) MWT Molecular weight (g/mol) RB Rotatable bonds DL
Ref Reference (pH 7) 5.84 13.66 -43.79 0 2 -1 40 277.428 13 ↓
Lo Low (pH 4.5-6) 5.84 11.68 -5.61 1 2 0 37 278.436 13 ↓

Vendor Notes

Note Type Comments Provided By
Mp [°C] 11 Acros Organics
Molecular_Solubility 7.11 Bitter DB
UniProt Database Links 017L_FRG3G; 019R_FRG3G; 027R_FRG3G; 032R_FRG3G; 057R_FRG3G; 2AAA_CAEEL; 2ABB_RAT; 41_DROME; 5HT2A_DROME; 7LESS_DROME; AAH_ARATH; AAH_ORYSJ; AAK1_BOVIN; AAK1_HUMAN; AAK1_MOUSE; AAK1_PIG; AAK1_RAT; AAM_RHOER; AAP3_ARATH; AB17C_HUMAN; ABCA4_HUMAN; ABCB7_MOUS ChEBI
ALOGPS_SOLUBILITY 2.66e-04 g/l DrugBank-nutriceuticals
BP [°C] 230 - 232 (p=1 torr) Acros Organics
BP 232 / 17 TCI
Purity 70% Fluorochem
UniProt Database Links ACP1_ARATH; LILIP_NOSS1; LOX1_SOYBN; LOX21_HORVU; LOX21_SOLTU; LOX22_HORVU; LOX23_HORVU; LOX2_ARATH; LOX31_SOLTU; LOX3_ARATH; LOX4_ARATH; LOX5_ORYSJ; LOX6_ARATH; LOX6_ORYSJ; LOXA_PHAVU; LOXB_PHAVU; LOXC1_ORYSJ; LOXC2_ORYSJ; LOX_PSEAI; OLHYD_MACCJ ChEBI
Patent Database Links EP1676488; EP1685834; EP1854462; EP1961311; US2004131648; US2005014826; US2006035350; US2007196445; US2007265341; US2008058418; US2008166781; US2008176956 ChEBI
H phrase H319: Causes serious eye irritation Acros Organics
P phrase P261: Avoid breathing dust/fume/gas/mist/vapors/spray Acros Organics
R phrase R36/37/38: Irritating to eyes, respiratory system and skin. Acros Organics
Reactome Database Links REACT_121179; REACT_19175; REACT_21408 ChEBI
S phrase S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Acros Organics
Target Trans-acting T-cell-specific transcription factor GATA-3(P23771)&Interleukin-2(P60568)&Interleukin-4(P05112)&Interleukin-5(P05113)&Interleukin-13(P35225)&Corticoliberin(P06850)&Pro-opiomelanocortin(P01189) Herbal Ingredients Targets
Hazard XI: Irritant Acros Organics

Activity (Go SEA)

Clustered Target Annotations
Code Description Organism Class Affinity (nM) LE (kcal/mol/atom) Type
FFAR1-1-E Free Fatty Acid Receptor 1 (cluster #1 Of 2), Eukaryotic Eukaryotes 5200 0.37 Functional ≤ 10μM
O3FA1-2-E G-protein Coupled Receptor 120 (cluster #2 Of 2), Eukaryotic Eukaryotes 2600 0.39 Functional ≤ 10μM
ChEMBL Target Annotations
Uniprot Swissprot Description Affinity (nM) LE (kcal/mol/atom) Type
FFAR1_HUMAN O14842 Free Fatty Acid Receptor 1, Human 5200 0.37 Functional ≤ 10μM
O3FA1_HUMAN Q5NUL3 G-protein Coupled Receptor 120, Human 2600 0.39 Functional ≤ 10μM

Direct Reactome Annotations (via ChEBI)

Description Species
Activation of gene expression by SREBF (SREBP)
alpha-linolenic acid (ALA) metabolism
BMAL1:CLOCK,NPAS2 activates circadian gene expression
Circadian Clock
Free fatty acid receptors
PPARA activates gene expression
Regulation of lipid metabolism by Peroxisome proliferator-activated receptor alp
REV-ERBA represses gene expression
RORA activates circadian gene expression
Synthesis, secretion, and inactivation of Glucagon-like Peptide-1 (GLP-1)
Transcriptional activation of mitochondrial biogenesis
Transcriptional regulation of white adipocyte differentiation
YAP1- and WWTR1 (TAZ)-stimulated gene expression

Reactome Annotations from Targets (via Uniprot)

Description Species
Fatty Acids bound to GPR40 (FFAR1) regulate insulin secretion
Free fatty acid receptors
G alpha (q) signalling events
Synthesis, secretion, and inactivation of Glucagon-like Peptide-1 (GLP-1)
Synthesis, secretion, and inactivation of Glucose-dependent Insulinotropic Polyp

Analogs ( Draw Identity 99% 90% 80% 70% )