NP-MRD: Showing NP-Card for Cis-5-Caffeoylquinic acid (NP0336478)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2024-09-11 06:25:59 UTC

Updated at

2024-09-11 06:26:00 UTC

NP-MRD ID

NP0336478

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cis-5-Caffeoylquinic acid

Description

Cis-5-Caffeoylquinic acid, also known as cis-5-O-caffeoylquinate or cis-chlorogenic acid, belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, And 5, as well as a carboxylic acid at position 1. Cis-5-Caffeoylquinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

Structure #1
  Mrv0541 02241212132D          

 25 26  0  0  1  0            999 V2000
   -0.7436   -5.4338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0292   -5.0213    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0292   -4.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6853   -3.7838    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3998   -4.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3998   -5.0213    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0884   -5.6081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8029   -6.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8029   -6.8456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5174   -5.6081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2319   -6.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6853   -5.4338    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6853   -6.2588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2156   -3.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9957   -2.5323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0281   -3.2951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1550   -3.1518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2319   -6.8456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5174   -7.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5174   -8.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2319   -8.4956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2319   -9.3206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9463   -8.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6608   -8.4956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9464   -7.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  2 12  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 14  1  1  0  0  0
  4 17  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6 12  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 13  1  6  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 11 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 25  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0336478

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1C[C@](O)(C[C@@H](OC(=O)\C=C/C2=CC=C(O)C(O)=C2)[C@@H]1O)C(O)=O

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
CWVRJTMFETXNAD-XYXZIBEBSA-N

> <FORMULA>
C16H18O9

> <MOLECULAR_WEIGHT>
354.3087

> <EXACT_MASS>
354.095082174

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
31.870123912767014

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3R,4R,5R)-3-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid

> <ALOGPS_LOGP>
0.17

> <JCHEM_LOGP>
-0.26852975799999984

> <ALOGPS_LOGS>
-2.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.20854914523281

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3338531471838464

> <JCHEM_PKA_STRONGEST_BASIC>
-3.231823980915407

> <JCHEM_POLAR_SURFACE_AREA>
164.75

> <JCHEM_REFRACTIVITY>
83.2347

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,4R,5R)-3-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -1.388 -10.143   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.055  -9.373   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.055  -7.833   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.279  -7.063   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.613  -7.833   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.613  -9.373   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.898 -10.468   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.232 -11.238   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.232 -12.778   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.566 -10.468   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.900 -11.238   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.279 -10.143   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.279 -11.683   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.269  -5.883   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.859  -4.727   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       3.786  -6.151   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.289  -5.883   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.900 -12.778   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.566 -13.548   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.566 -15.088   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.900 -15.858   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.900 -17.398   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.233 -15.088   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.567 -15.858   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.233 -13.548   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14   17                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   18                                                       
CONECT   12    2    6   13                                                  
CONECT   13   12                                                            
CONECT   14    4   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    4                                                            
CONECT   18   11   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   18   23                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

View in JSmol

Synonyms

Value	Source
5-O-(Z)-Caffeoylquinic acid	ChEBI
cis-5-O-Caffeoylquinic acid	ChEBI
cis-Chlorogenic acid	ChEBI
5-O-(Z)-Caffeoylquinate	Generator
cis-5-O-Caffeoylquinate	Generator
cis-Chlorogenate	Generator
cis-5-Caffeoylquinate	Generator
5-O-cis-Caffeoylquinate	Generator

Chemical Formula

C₁₆H₁₈O₉

Average Mass

354.3087 Da

Monoisotopic Mass

354.09508 Da

IUPAC Name

(1S,3R,4R,5R)-3-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid

Traditional Name

(1S,3R,4R,5R)-3-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

O[C@@H]1C[C@](O)(C[C@@H](OC(=O)\C=C/C2=CC=C(O)C(O)=C2)[C@@H]1O)C(O)=O

InChI Identifier

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

InChI Key

CWVRJTMFETXNAD-XYXZIBEBSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, And 5, as well as a carboxylic acid at position 1.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Quinic acids and derivatives

Alternative Parents

Substituents

Quinic acid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Cyclohexanol
Fatty acid ester
Phenol
Fatty acyl
Hydroxy acid
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Alpha-hydroxy acid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Polyol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

cinnamate ester (CHEBI:75489 )
cyclitol carboxylic acid (CHEBI:75489 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.17	ALOGPS
logP	-0.27	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.33	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	164.75 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	83.23 m³·mol⁻¹	ChemAxon
Polarizability	31.87 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0029278

DrugBank ID

Not Available

Phenol Explorer Compound ID

521

FoodDB ID

FDB000275

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

1794425

PDB ID

Not Available

ChEBI ID

75489

Good Scents ID

Not Available

References

General References

Showing NP-Card for Cis-5-Caffeoylquinic acid (NP0336478)

MOL for NP0336478 (Cis-5-Caffeoylquinic acid)

3D MOL for NP0336478 (Cis-5-Caffeoylquinic acid)

3D SDF for NP0336478 (Cis-5-Caffeoylquinic acid)

3D-SDF for NP0336478 (Cis-5-Caffeoylquinic acid)

PDB for NP0336478 (Cis-5-Caffeoylquinic acid)

3D PDB for NP0336478 (Cis-5-Caffeoylquinic acid)

SMILES for NP0336478 (Cis-5-Caffeoylquinic acid)

INCHI for NP0336478 (Cis-5-Caffeoylquinic acid)

Structure for NP0336478 (Cis-5-Caffeoylquinic acid)

3D Structure for NP0336478 (Cis-5-Caffeoylquinic acid)