Natural Product: ENC001103

NPs Basic Information

Download MOL File
Name
Icosapent
Molecular Formula C20H30O2
IUPAC Name*
(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid
SMILES
CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O
InChI
InChI=1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-15-
InChIKey
JAZBEHYOTPTENJ-JLNKQSITSA-N
Synonyms
Eicosapentaenoic acid; Timnodonic acid; Icosapent; 10417-94-4; Icosapentaenoic acid; EPA; cis-5,8,11,14,17-Eicosapentaenoic acid; (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid; Icosapento; Icosapentum; 5,8,11,14,17-EICOSAPENTAENOIC ACID; eicosapentaenoate; 5Z,8Z,11Z,14Z,17Z-Eicosapentaenoic acid; (all-Z)-5,8,11,14,17-Eicosapentaenoic acid; Icosapent [INN]; (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-eicosapentaenoic acid; 5,8,11,14,17-Icosapentaenoic acid; Ropufa 70; CCRIS 3279; Incromega e 7010sr; AAN7QOV9EA; (5Z,8Z,11Z,14Z,17Z)-Icosapentaenoic acid; (5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoic acid; EPA 45G; CHEMBL460026; (5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoate; all-cis-5,8,11,14,17-icosapentaenoic acid; CHEBI:28364; all-cis-5,8,11,14,17-eicosapentaenoic acid; all-cis-icosa-5,8,11,14,17-pentaenoic acid; Icosapent (INN); cis-Delta(5,8,11,14,17)-eicosapentaenoic acid; 5,8,11,14,17-Eicosapentaenoic acid, (all-Z)-; Eicosapentaenoic acid (c20:5 n3); EPA;Timnodonic acid; Icosapentaenoate; (all-Z)-delta5,8,11,14,17-Eicosapentaenoic acid; C20:5n-3,6,9,12,15; cis-5,8,11,14,17-EPA; FA 20:5; NCGC00161344-03; C20:5 (n-3); EICOSAPENTAENOIC ACID (20:5 n-3); Eicosa-5Z,8Z,11Z,14Z,17Z-pentaenoic Acid (20:5, n-3); Miraxion; Eicosapentanoic acid; Eye Q; Eye-Q; 5,8,11,14,17-Eicosapentaenoic acid, (5Z,8Z,11Z,14Z,17Z)-; EPA [drug]; UNII-AAN7QOV9EA; 1553-41-9; Icosapentum [INN-Latin]; Icosapento [INN-Spanish]; (5Z,8Z,11Z,14Z,17Z)-icosapentaenoate; Timnodonate; 3gwx; all cis-5,8,11,14,17-Eicosapentaenoic Acid; MFCD00065716; all-cis-icosapentaenoate; all-cis-icosapentaenoic acid; DSSTox_CID_21023; DSSTox_RID_79612; DSSTox_GSID_41023; SCHEMBL20469; BSPBio_001328; BML3-B01; GTPL3362; DTXSID9041023; EICOSAPENTAENOIC ACID [MI]; HMS1361C10; HMS1791C10; HMS1989C10; HMS3402C10; HMS3649D19; HY-B0660; ZINC4474603; 5,8,11,14,17-Icosapentaenoate; EICOSAPENTAENOIC ACID [INCI]; Tox21_111991; 5,8,11,14,17-Eicosapentaenoate; BDBM50242349; EICOSAPENTAENOIC ACID [VANDF]; LMFA01030759; s6476; EICOSAPENTAENOIC ACID [MART.]; AKOS027470327; EICOSAPENTAENOIC ACID [USP-RS]; EICOSAPENTAENOIC ACID [WHO-DD]; CCG-207957; CCG-208136; DB00159; cis-5,8,11,14,17-eicosapentaenoate; IDI1_033798; NCGC00161344-01; NCGC00161344-02; NCGC00161344-04; NCGC00161344-07; 5Z,8Z,11Z,14Z,17Z-Eicosapentaenoate; AC-31072; AS-53730; CAS-10417-94-4; E0441; 5,8,11,14,17-Eicosapentaenoic acid (6CI); all cis-5,8,11,14,17-Icosapentaenoic Acid; C06428; D08061; P16966; EN300-7403855; (all-cis)-5,8,11,14,17-Eicosapentaenoic acid; EICOSAPENTAENOIC ACID (EPA) (C20:5 N3); L001256; Q409990; SR-01000946647; FA(20:5(5Z,8Z,11Z,14Z,17Z)); J-001125; SR-01000946647-1; z,z,z,z,z-eicosa-5,8,11,14,17-pentaenoic acid; (Z,Z,Z,Z,Z)-5,8,11,14,17-eicosapentaenoic acid; BRD-K47192521-001-02-1; cis-5,8,11,14,17-Eicosapentaenoic acid, >=99%; 7F8BF016-B146-4F72-A52E-B9298BA3A9AB; C20H30O2 (cis-5,8,11,14,17-eicosapentaenoic acid); Eicosapentaenoic acid, 5,8,11,14,17-(Z,Z,Z,Z,Z)-; 5,8,11,14,17-Eicosapentaenoic acid, (all-Z)- (8CI); cis-5,8,11,14,17-Eicosapentaenoic acid, >=85%, liquid; cis-5,8,11,14,17-Eicosapentaenoic acid, analytical standard; (5Z,8Z,11 Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid; (5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenoic acid; cis, cis, cis, cis, cis-eicosa-5,8,11,14,17-pentaenoic acid; 5,8,11,14,17-Eicosapentaenoic acid, (5Z,8Z,11Z,14Z,17Z)- (9CI); cis-5,8,11,14,17-Eicosapentaenoic acid, 500 mug/mL in ethanol, certified reference material
CAS 10417-94-4
PubChem CID 446284
ChEMBL ID CHEMBL460026
*Note: the IUPAC Name was collected from PubChem.
Chemical Classification:
  • Kingdom: Organic compounds
    • Superclass: Lipids and lipid-like mol
      • Class: Fatty Acyls
        • Subclass: Fatty acids and conjugate
          • Direct Parent: Long-chain fatty acids

ClassyFire Version 1.0
PMID:27867422

NPs Species Source

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NPs Physi-Chem Properties

Molecular Weight: 302.5 ALogp: 5.6
HBD: 1 HBA: 2
Rotatable Bonds: 13 Lipinski's rule of five: Rejected
Polar Surface Area: 37.3 Aromatic Rings: 0
Heavy Atoms: 22 QED Weighted: 0.332

NPs ADMET Properties*

ADMET: Absorption

Caco-2 Permeability: -5.322 MDCK Permeability: 0.00021600
Pgp-inhibitor: 0 Pgp-substrate: 0
Human Intestinal Absorption (HIA): 0.044 20% Bioavailability (F20%): 1
30% Bioavailability (F30%): 1

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB): 0.001 Plasma Protein Binding (PPB): 100.31%
Volume Distribution (VD): 0.671 Fu: 0.72%

ADMET: Metabolism

CYP1A2-inhibitor: 0.09 CYP1A2-substrate: 0.874
CYP2C19-inhibitor: 0.067 CYP2C19-substrate: 0.165
CYP2C9-inhibitor: 0.113 CYP2C9-substrate: 0.989
CYP2D6-inhibitor: 0.134 CYP2D6-substrate: 0.951
CYP3A4-inhibitor: 0.081 CYP3A4-substrate: 0.081

ADMET: Excretion

Clearance (CL): 2.471 Half-life (T1/2): 0.941

ADMET: Toxicity

hERG Blockers: 0.022 Human Hepatotoxicity (H-HT): 0.271
Drug-inuced Liver Injury (DILI): 0.004 AMES Toxicity: 0.975
Rat Oral Acute Toxicity: 0.001 Maximum Recommended Daily Dose: 0.429
Skin Sensitization: 0.958 Carcinogencity: 0.895
Eye Corrosion: 0.051 Eye Irritation: 0.312
Respiratory Toxicity: 0.875
*Note: the ADMET properties was calculated by ADMETlab 2.0. Reference: PMID: 33893803.

Similar Compounds*

Compounds similar to EMNPD with top10 similarity:

*Note: the compound similarity was calculated by RDKIT.