NPs Basic Information

Name
Neochlorogenic acid
Molecular Formula C16H18O9
IUPAC Name*
(1R,3R,4S,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylic acid
SMILES
C1[C@H]([C@@H]([C@@H](C[C@]1(C(=O)O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)O)O
InChI
InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14+,16-/m1/s1
InChIKey
CWVRJTMFETXNAD-NXLLHMKUSA-N
Synonyms
Neochlorogenic acid; 906-33-2; 5-O-Caffeoylquinic acid; Neochlorogenate; Nochlorogenic acid; CHEBI:16384; trans-Neochlorogenic acid; (1R,3R,4S,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylic acid; 5-O-(trans-3,4-Dihydroxycinnamoyl)-D-quinic acid; CHEMBL249450; O4601UER1Z; trans-5-O-caffeoyl-D-quinic acid; trans-5-O-Caffeoylquinic acid; 5-Caffeoylquinic acid; caffeoylquinic acid; trans-5-O-caffeoyl-D-quinate; (1R,3R,4S,5R)-3-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxycyclohexanecarboxylic acid; 1D-[1(OH),3,4/5]-3-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxycyclohexanecarboxylic acid; 5-Caffeylquinic acid; 5-O-caffeoyl quinic acid; 3-CQA; (E)-Neochlorogenic Acid; UNII-O4601UER1Z; Neochlorogenic-acid; EINECS 212-997-1; MFCD10566639; Quinic acid, 5-caffeoyl-, E-; SCHEMBL13567302; SCHEMBL18317299; ACon1_000392; DTXSID301347903; HMS3886H18; HY-N0722; ZINC4096248; 3-O-(E)-CAFFEOYLQUINIC ACID; BDBM50163308; s9136; AKOS015901853; AC-6061; CCG-268077; CS-3770; Neochlorogenic acid, analytical standard; NCGC00169121-01; NCGC00169121-02; (1R,3R,4S,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxy-cyclohexanecarboxylic acid; AS-75008; Cyclohexanecarboxylic acid, 3-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1,4,5-trihydroxy-, (1R-(1alpha,3alpha,4alpha,5beta))-; N1155; C17147; 906N332; Q-100887; Q6992128; 656B3E48-4F1F-4FC8-A3B2-B0FADAB84AF5; Neochlorogenic acid, from Lonicera japonica, >=98.0% (HPLC); NEOCHLOROGENIC ACID (CONSTITUENT OF ST. JOHN'S WORT) [DSC]; (1R,3R,4S,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid; (1R-(1.ALPHA.,3.ALPHA.,4.ALPHA.,5.BETA.))-3-((3-(3,4-DIHYDROXYPHENYL)-1-OXOALLYL)OXY)-1,4,5-TRIHYDROXYCYCLOHEXANECARBOXYLIC ACID; (1R-(1alpha,3alpha,4alpha,5beta))-3-((3-(3,4-Dihydroxyphenyl)-1-oxoallyl)oxy)-1,4,5-trihydroxycyclohexanecarboxylic acid; 1,3beta,4alpha-Trihydroxy-5alpha-(3,4-dihydroxycinnamoyloxy)cyclohexane-1beta-carboxylic acid; 342811-68-1; CYCLOHEXANECARBOXYLIC ACID, 3-(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-1,4,5-TRIHYDROXY-, (1R,3R,4S,5R)-; CYCLOHEXANECARBOXYLIC ACID, 3-((3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPENYL)OXY)-1,4,5-TRIHYDROXY-, (1R-(1.ALPHA.,3.ALPHA.(E),4.ALPHA.,5.BETA.))-; CYCLOHEXANECARBOXYLIC ACID, 3-((3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPENYL)OXY)-1,4,5-TRIHYDROXY-, (1R-(1.ALPHA.,3.ALPHA.,4.ALPHA.,5.BETA.))-; Cyclohexanecarboxylic acid,3-[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxy-,(1R,3R,4S,5R)-; NCGC00169121-02!(1R,3R,4S,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylic acid
CAS 906-33-2
PubChem CID 5280633
ChEMBL ID CHEMBL249450
*Note: the IUPAC Name was collected from PubChem.
Chemical Classification:
  • Kingdom: Organic compounds
    • Superclass: Organic oxygen compounds
      • Class: Organooxygen compounds
        • Subclass: Alcohols and polyols
          • Direct Parent: Quinic acids and derivati

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: 354.31 ALogp: -0.4
HBD: 6 HBA: 9
Rotatable Bonds: 5 Lipinski's rule of five: Rejected
Polar Surface Area: 165.0 Aromatic Rings: 2
Heavy Atoms: 25 QED Weighted: 0.244

NPs ADMET Properties*

ADMET: Absorption

Caco-2 Permeability: -6.31 MDCK Permeability: 0.00001790
Pgp-inhibitor: 0 Pgp-substrate: 0.959
Human Intestinal Absorption (HIA): 0.763 20% Bioavailability (F20%): 0.955
30% Bioavailability (F30%): 0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB): 0.231 Plasma Protein Binding (PPB): 79.94%
Volume Distribution (VD): 0.312 Fu: 19.57%

ADMET: Metabolism

CYP1A2-inhibitor: 0.143 CYP1A2-substrate: 0.021
CYP2C19-inhibitor: 0.029 CYP2C19-substrate: 0.05
CYP2C9-inhibitor: 0.041 CYP2C9-substrate: 0.418
CYP2D6-inhibitor: 0.006 CYP2D6-substrate: 0.141
CYP3A4-inhibitor: 0.051 CYP3A4-substrate: 0.027

ADMET: Excretion

Clearance (CL): 2.131 Half-life (T1/2): 0.888

ADMET: Toxicity

hERG Blockers: 0.037 Human Hepatotoxicity (H-HT): 0.139
Drug-inuced Liver Injury (DILI): 0.409 AMES Toxicity: 0.034
Rat Oral Acute Toxicity: 0.031 Maximum Recommended Daily Dose: 0.019
Skin Sensitization: 0.589 Carcinogencity: 0.164
Eye Corrosion: 0.004 Eye Irritation: 0.103
Respiratory Toxicity: 0.039
*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.