NPs Basic Information

Name
Cryptochlorogenic acid
Molecular Formula C16H18O9
IUPAC Name*
(3R,5R)-4-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,3,5-trihydroxycyclohexane-1-carboxylic acid
SMILES
C1[C@H](C([C@@H](CC1(C(=O)O)O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)O
InChI
InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(21)25-14-11(19)6-16(24,15(22)23)7-12(14)20/h1-5,11-12,14,17-20,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14?,16?/m1/s1
InChIKey
GYFFKZTYYAFCTR-AVXJPILUSA-N
Synonyms
Cryptochlorogenic acid; 905-99-7; 4-Caffeoylquinic acid; 4-O-Caffeoylquinic acid; 4-Cqa; 4-o-Caffeoyl quinic acid; Quinic acid 4-O-caffeate; 4-O-trans-caffeoylquinic acid; 4-O-(3,4-Dihydroxycinnamoyl)-D-quinic acid; F23DJ84IZ9; (3R,5R)-4-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,3,5-trihydroxycyclohexane-1-carboxylic acid; CHEMBL4203706; 4-(3,4-Dihydroxycinnamoyl)quinic acid; 82638-23-1; 87099-73-8; rel-(1S,3R,4S,5R)-4-(((E)-3-(3,4-Dihydroxyphenyl)acryloyl)oxy)-1,3,5-trihydroxycyclohexanecarboxylic acid; MFCD10566638; Cryptochlorogenic-acid; Quinic acid, 4-caffeoyl-; UNII-F23DJ84IZ9; 4-O-(E)-caffeoylquinic acid; CHEMBL3092676; Cinnamic acid, 3,4-dihydroxy-, 4-carboxy-2,4,6-trihydroxycyclohexyl ester; Quinic acid, 4-caffeoyl-, E-; SCHEMBL18180782; SCHEMBL20883249; ACon1_000120; CHEBI:75491; HY-N0787; BDBM50455380; s9319; ZINC31154929; 4-O-Caffeoylquinic acid, >=98.0%; AKOS037514601; ZINC100038257; ZINC103240311; CCG-268076; CS-3767; NCGC00180861-01; (1alpha,3alpha,4alpha,5beta)-4-(3-(3,4-(Dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1,3,5-trihydroxycyclohexanecarboxylic acid; (3R,5R)-4-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,3,5-trihydroxy-cyclohexanecarboxylic acid; BS-17821; Cryptochlorogenic acid, analytical standard; 4-Caffeoylquinic acid/ Cryptochlorogenic acid; 905C997; Q-100886; B0B55D52-5101-4E6D-AA67-72D1CECBAA5A; Q27145347; 49B68A4C-6EC9-4441-B7D7-E3B740A8CDEC; (1alpha,3R,4alpha,5R)-4-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-1,3,5-trihydroxycyclohexanecarboxylic acid; (1S,3R,4S,5R)-4-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,3,5-trihydroxycyclohexanecarboxylic acid; 1,3beta,5alpha-Trihydroxy-4alpha-(3,4-dihydroxycinnamoyloxy)cyclohexane-1beta-carboxylic acid; CYCLOHEXANECARBOXYLIC ACID, 4-(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-1,3,5-TRIHYDROXY-, (1.ALPHA.,3R,4.ALPHA.,5R)-; Cyclohexanecarboxylic acid, 4-(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-1,3,5-trihydroxy-, (1alpha,3R,4alpha,5R)-; Cyclohexanecarboxylic acid, 4-((3-(3,4-dihydroxyphenyl)-1-oxo-2-1R-propenyl)oxy)-1,3,5-trihydroxy-, (1R-(1alpha,3alpha,4alpha,5beta))-; CYCLOHEXANECARBOXYLIC ACID, 4-((3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-1,3,5-TRIHYDROXY-, (1.ALPHA.,3R,4.ALPHA.,5R)-; Cyclohexanecarboxylic acid, 4-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-1,3,5-trihydroxy-, (1alpha,3R,4alpha,5R)-; Cyclohexanecarboxylic acid, 4-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1,3,5-trihydroxy-, (1alpha,3R,4alpha,5R)-; NCGC00180861-02!(3R,5R)-4-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,3,5-trihydroxycyclohexane-1-carboxylic acid
CAS 905-99-7
PubChem CID 9798666
ChEMBL ID CHEMBL4203706
*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: -6.451 MDCK Permeability: 0.00010925
Pgp-inhibitor: 0 Pgp-substrate: 0.978
Human Intestinal Absorption (HIA): 0.864 20% Bioavailability (F20%): 0.981
30% Bioavailability (F30%): 0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB): 0.732 Plasma Protein Binding (PPB): 44.12%
Volume Distribution (VD): 0.48 Fu: 49.69%

ADMET: Metabolism

CYP1A2-inhibitor: 0.169 CYP1A2-substrate: 0.031
CYP2C19-inhibitor: 0.017 CYP2C19-substrate: 0.048
CYP2C9-inhibitor: 0.016 CYP2C9-substrate: 0.107
CYP2D6-inhibitor: 0.012 CYP2D6-substrate: 0.121
CYP3A4-inhibitor: 0.082 CYP3A4-substrate: 0.047

ADMET: Excretion

Clearance (CL): 1.828 Half-life (T1/2): 0.914

ADMET: Toxicity

hERG Blockers: 0.036 Human Hepatotoxicity (H-HT): 0.234
Drug-inuced Liver Injury (DILI): 0.088 AMES Toxicity: 0.031
Rat Oral Acute Toxicity: 0.081 Maximum Recommended Daily Dose: 0.46
Skin Sensitization: 0.557 Carcinogencity: 0.048
Eye Corrosion: 0.003 Eye Irritation: 0.05
Respiratory Toxicity: 0.081
*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 0.811 D0KN2M 0.487
ENC001543 0.811 D0V9EN 0.457
ENC001440 0.457 D0I3RO 0.293
ENC001579 0.408 D08HVR 0.284
ENC002582 0.361 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
ENC000035 0.303 D0E6OC 0.241
*Note: the compound similarity was calculated by RDKIT.