Natural Product (NP) Details

General Information of the NP (ID: NP3710)
Name
Gamma linolenic acid
Synonyms
gamma-Linolenic acid; GAMOLENIC ACID; 506-26-3; (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid; (Z,Z,Z)-6,9,12-Octadecatrienoic acid; (6,9,12)-linolenic acid; CCRIS 7668; all-cis-6,9,12-Octadecatrienoic acid; gamoleic acid; Ligla; UNII-78YC2MAX4O; 6,9,12-Octadecatrienoic acid, (Z,Z,Z)-; GLA; (6Z,9Z,12Z)-Octadecatrienoic acid; Gamma-?Linolenic acid; .gamma.-Linolenic Acid; 6Z,9Z,12Z-octadecatrienoic acid; (6Z,9Z,12Z)-6,9,12-Octadecatrienoic acid; 78YC2MAX4O; cis-Delta(6,9,12)-octadecatrienoic acid; 6(Z),9(Z),12(Z)-Octadecatrienoic acid; 6-cis,9-cis,12-cis-Octadecatrienoic acid; cis,cis,cis-6,9,12-Octadecatrienoic acid; CHEMBL464982; CHEBI:28661; MFCD00065718; 6,9,12-Octadecatrienoic acid; 6,9,12-all-cis-Octadecatrienoic acid; NCGC00160469-01; GAMMA-LINOLENIC ACID (18:3 n-6); C18:3n-6,9,12; cis-6, cis-9, cis-12-octadecatrienoic acid; 18:3 (n-6); Efamast; Epogam; Acido gamolenico; 6Z,9Z,12Z-octadecatrienoate; Acide gamolenique; Acide gamolenique [French]; Acido gamolenico [Spanish]; Acidum gamolenicum; Acidum gamolenicum [Latin]; Gamolenic acid [INN:BAN]; (6Z,9Z,12Z)-Octadecatrienoate; SMR000058609; all-cis-6,9,12-octadecatrienoate; cis-Delta(6,9,12)-octadecatrienoate; Viacutan; Gammolenic acid; gamma-Linolensaeure; Gamma-linoleic acid; gamma-linolenic-acid; gamma-Llnolenic acid; C18:3,n-6; Gamolenic acid (INN); cis-6,cis-9,cis-12-Octadecatrienoic acid; 6,9,12-Octadecatrienoate; DSSTox_CID_26170; DSSTox_RID_81401; DSSTox_GSID_46170; SCHEMBL19418; BSPBio_001338; MLS001333661; MLS001333662; Octadeca-6,9,12-triensaeure; BML3-B06; GTPL4710; DTXSID7046170; NDI 609; HMS1361C20; HMS1791C20; HMS1989C20; HMS2230A18; HMS3402C20; HMS3649H09; 6,9,12-all-cis-Octadecatrienoate; HY-N7140; ZINC3777423; Tox21_111835; BDBM50269532; LMFA01030141; s5743; C18:3, n-6,9,12 all-cis; (Z,Z,Z)-6,9,12-Octadecatrienoate; AKOS022175367; z,z,z-6,9,12-Octadecatrienoic acid; CS-W012291; DB13854; gamma-Linolenic acid, >=99%, liquid; z,z,z-octadeca-6,9,12-trienoic acid; 6(Z),9(Z),12(Z)-Octadecatrienoate; IDI1_033808; gamma-Linolenic acid, analytical standard; NCGC00160469-02; NCGC00160469-03; NCGC00160469-04; C18:3 (n-6); CAS-506-26-3; DS-10685; M520; DB-029858; L0152; Octadecatrienoic acid, 6,9,12-(Z,Z,Z)-; C06426; D07213; 506L263; Q415885; SR-01000838334; SR-01000838334-2; 18:3(N-6); BRD-K18059238-001-02-1; D58CCA4A-7FFA-4E8B-A758-EAA7D073B343; C18H30O2 (cis,cis,cis-octadeca-6,9,12-trienoic acid); UNII-116Z6MZN1M component VZCCETWTMQHEPK-QNEBEIHSSA-N; UNII-44NH37HHP9 component VZCCETWTMQHEPK-QNEBEIHSSA-N; UNII-F85N2YHE4E component VZCCETWTMQHEPK-QNEBEIHSSA-N; cis,cis,cis,6,9,12-Octa-decatrienoic acid-18:3 n6 lithium salt
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Species Origin Gossypium hirsutum ...     Click to Show/Hide
Gossypium hirsutum
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Malvales
Family: Malvaceae
Genus: Gossypium
Species: Gossypium hirsutum
Disease Allergic/hypersensitivity disorder [ICD-11: 4A80-4A85] Approved [1]
Structure
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2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -5.014
 
MDCK Permeability
 -4.77
 
PAMPA
 - - -
 
HIA
 - - -
 
Distribution
VDss
 -0.65
 
PPB
 98.4%
 
BBB
 - - -
 
Metabolism
CYP1A2 inhibitor
 - - -
CYP1A2 substrate
 - - -
CYP2C19 inhibitor
 - - -
CYP2C19 substrate
 - - -
CYP2C9 inhibitor
 - - -
CYP2C9 substrate
 +++
CYP2D6 inhibitor
 - - -
CYP2D6 substrate
 ++
CYP3A4 inhibitor
 - - -
CYP3A4 substrate
 - - -
CYP2B6 inhibitor
 +++
CYP2B6 substrate
 +++
CYP2C8 inhibitor
 +++
HLM Stability
 - - -
 
Excretion
CLplasma
 5.869
 
T1/2
 0.234
Toxicity
DILI
 - - -
 
Rat Oral Acute Toxicity
 - - -
 
FDAMDD
 - - -
 
Respiratory
 ++
 
Human Hepatotoxicity
 - - -
 
Ototoxicity
 - -
 
Drug-induced Nephrotoxicity
 -
 
Drug-induced Neurotoxicity
 - - -
 
Hematotoxicity
 - - -
 
Genotoxicity
 - - -
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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Formula
C18H30O2
PubChem CID
5280933
Canonical SMILES
CCCCCC=CCC=CCC=CCCCCC(=O)O
InChI
1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,12-13H,2-5,8,11,14-17H2,1H3,(H,19,20)/b7-6-,10-9-,13-12-
InChIKey
VZCCETWTMQHEPK-QNEBEIHSSA-N
CAS Number
CAS 506-26-3
ChEBI ID
CHEBI:28661
TTD Drug ID
D0UE9X
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          5-fluorouracil      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model MIA PaCa-2 CVCL_0428 Pancreatic ductal adenocarcinoma Homo sapiens
PANC-1 CVCL_0480 Pancreatic ductal adenocarcinoma Homo sapiens
                    Experimental
                    Result(s)		 GLA has a synergistic effect with gemcitabine at concentrations that correspond to in vivo therapeutic doses. GLA with 5-FU is synergistic only at a tight range of high concentrations of 5-FU. GLA lacks toxic side effects and may be useful in combination with gemcitabine.
          Vinorelbine      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model MDA-MB-231 CVCL_0062 Breast adenocarcinoma Homo sapiens
T-47D CVCL_0553 Invasive breast carcinoma Homo sapiens
SK-BR-3 CVCL_0033 Breast adenocarcinoma Homo sapiens
MCF-7 CVCL_0031 Invasive breast carcinoma Homo sapiens
                    Experimental
                    Result(s)		 Some UFAs can be used as modulators of tumor cell chemosensitivity.
References
Reference 1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
Reference 2 Synergistic activity of gamma-linolenic acid and cytotoxic drugs against pancreatic adenocarcinoma cell lines. Pancreatology. 2003;3(5):367-73; discussion 373-4.
Reference 3 Synergistic interaction between vinorelbine and gamma-linolenic acid in breast cancer cells. Breast Cancer Res Treat. 2002 Apr;72(3):203-19.
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