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

Endophyte ID Endophyte Name Family Genus Taxonomy ID GenBank ID Closest GenBank ID Reference
Endophyte ID Endophyte Name Family Genus Taxonomy ID GenBank ID Closest GenBank ID Reference

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

Bioactivity Name Target ID Target Name Target Type Target Organism Target Organism ID Potency of Bioactivity Activity Type Value Unit Endophyte ID Endophyte Name
Bioactivity Name Target ID Target Name Target Type Target Organism Target Organism ID Potency of Bioactivity Activity Type Value Unit Endophyte ID Endophyte Name

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:

Similar NPs Similar Drugs
NPs ID NPs 2D Structure Similarity Score TTD ID Drug 2D Structure Similarity Score
ENC001471 1.000 D0KN2M 0.570
ENC001917 0.811 D0V9EN 0.457
ENC001440 0.457 D0I3RO 0.293
ENC001579 0.408 D08HVR 0.284
ENC002582 0.373 D0BA6T 0.277
ENC001101 0.346 D0P7JZ 0.267
ENC004024 0.345 D0U0OT 0.259
ENC002823 0.323 D00KRE 0.245
ENC000002 0.315 D0Y6KO 0.242
ENC004911 0.313 D0E6OC 0.241
*Note: the compound similarity was calculated by RDKIT.