Natural Product: ENC001416

NPs Basic Information

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Name
Calebin A
Molecular Formula C21H20O7
IUPAC Name*
[(E)-4-(4-hydroxy-3-methoxyphenyl)-2-oxobut-3-enyl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
SMILES
COC1=C(C=CC(=C1)/C=C/C(=O)COC(=O)/C=C/C2=CC(=C(C=C2)O)OC)O
InChI
InChI=1S/C21H20O7/c1-26-19-11-14(4-8-17(19)23)3-7-16(22)13-28-21(25)10-6-15-5-9-18(24)20(12-15)27-2/h3-12,23-24H,13H2,1-2H3/b7-3+,10-6+
InChIKey
UYEWRTKHKAVRDI-ASVGJQBISA-N
Synonyms
Calebin A; Calebin-A; 336784-82-8; U2M09W0E67; [(E)-4-(4-hydroxy-3-methoxyphenyl)-2-oxobut-3-enyl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate; 2-propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, (3E)-4-(4-hydroxy-3-methoxyphenyl)-2-oxo-3-butenyl ester, (2E)-; (E)-(E)-4-(4-Hydroxy-3-methoxyphenyl)-2-oxobut-3-en-1-yl 3-(4-hydroxy-3-methoxyphenyl)acrylate; 2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, (3E)-4-(4-hydroxy-3-methoxyphenyl)-2-oxo-3-buten-1-yl ester, (2E)-; CHEMBL86075; UNII-U2M09W0E67; SCHEMBL1231185; CHEBI:175904; DTXSID201318662; (3E)-4-(4-hydroxy-3-methoxyphenyl)-2-oxobut-3-en-1-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)acrylate; (3E)-4-(4-hydroxy-3-methoxyphenyl)-2-oxobut-3-en-1-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate; 3-(4-Hydroxy-3-methoxy-phenyl)-acrylic acid 4-(4-hydroxy-3-methoxy-phenyl)-2-oxo-but-3-enyl ester; 4''-(3'''-Methoxy-4'''-hydroxyphenyl)-2''-oxo-3''-enebutanyl 3-(3'-methoxy-4'-hydroxyphenyl)propenoate; 4''-(3'''-Methoxy-4'''-hydroxyphenyl)-2''-oxo-3''-enebutanyl-3-(3'-methoxy-4'-hydroxyphenyl)propenoate
CAS 336784-82-8
PubChem CID 637429
ChEMBL ID CHEMBL86075
*Note: the IUPAC Name was collected from PubChem.
Chemical Classification:
  • Kingdom: Organic compounds
    • Superclass: Phenylpropanoids and poly
      • Class: Cinnamic acids and deriva
        • Subclass: Hydroxycinnamic acids and
          • Direct Parent: Coumaric acids and deriva

ClassyFire Version 1.0
PMID:27867422

NPs Species Source

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NPs Content

*Note: The vaules in Content Percentage are calculated by dividing the content value by the maximum content value in NP Content.
**Note: The units with different NP content, due to their incomparable values, are separated into different tables.

NPs Biological Activity

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NPs Physi-Chem Properties

Molecular Weight: 384.4 ALogp: 3.3
HBD: 2 HBA: 7
Rotatable Bonds: 9 Lipinski's rule of five: Accepted
Polar Surface Area: 102.0 Aromatic Rings: 2
Heavy Atoms: 28 QED Weighted: 0.528

NPs ADMET Properties*

ADMET: Absorption

Caco-2 Permeability: -4.842 MDCK Permeability: 0.00001830
Pgp-inhibitor: 0.339 Pgp-substrate: 0.005
Human Intestinal Absorption (HIA): 0.182 20% Bioavailability (F20%): 0.975
30% Bioavailability (F30%): 0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB): 0.246 Plasma Protein Binding (PPB): 99.97%
Volume Distribution (VD): 0.395 Fu: 1.62%

ADMET: Metabolism

CYP1A2-inhibitor: 0.858 CYP1A2-substrate: 0.839
CYP2C19-inhibitor: 0.603 CYP2C19-substrate: 0.107
CYP2C9-inhibitor: 0.767 CYP2C9-substrate: 0.918
CYP2D6-inhibitor: 0.156 CYP2D6-substrate: 0.903
CYP3A4-inhibitor: 0.766 CYP3A4-substrate: 0.549

ADMET: Excretion

Clearance (CL): 12.621 Half-life (T1/2): 0.957

ADMET: Toxicity

hERG Blockers: 0.12 Human Hepatotoxicity (H-HT): 0.414
Drug-inuced Liver Injury (DILI): 0.887 AMES Toxicity: 0.463
Rat Oral Acute Toxicity: 0.77 Maximum Recommended Daily Dose: 0.854
Skin Sensitization: 0.952 Carcinogencity: 0.657
Eye Corrosion: 0.004 Eye Irritation: 0.228
Respiratory Toxicity: 0.545
*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.