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Showing NP-Card for Caffeic acid 4-O-sulphate (NP0339415)

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Record Information
Version2.0
Created at2024-09-11 21:43:25 UTC
Updated at2024-09-11 21:43:26 UTC
NP-MRD IDNP0339415
Secondary Accession NumbersNone
Natural Product Identification
Common NameCaffeic acid 4-O-sulphate
DescriptionCaffeic acid 4-O-sulfate, also known as caffeate 4-O-sulfate or caffeic acid 4-sulfuric acid, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. Caffeic acid 4-O-sulfate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0339415 (Caffeic acid 4-O-sulphate)


  Mrv1652310011916302D          

 17 17  0  0  0  0            999 V2000
    1.3701   -0.9117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0276   -1.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9832   -0.3597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8123   -0.9539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4139    0.1502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5854   -0.6568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8116    0.4473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0270    0.7022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4247    0.9993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8555    1.5092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4254   -1.5059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2538   -2.3128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2100   -1.2509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2532    1.8063    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.9407    1.8077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2168    2.5303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4462    1.9778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  8  5  1  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
  4 11  1  0  0  0  0
 11 13  1  0  0  0  0
 11 12  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 14 17  2  0  0  0  0
M  END
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3D MOL for NP0339415 (Caffeic acid 4-O-sulphate)

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3D SDF for NP0339415 (Caffeic acid 4-O-sulphate)

  Mrv1652310011916302D          

 17 17  0  0  0  0            999 V2000
    1.3701   -0.9117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0276   -1.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9832   -0.3597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8123   -0.9539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4139    0.1502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5854   -0.6568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8116    0.4473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0270    0.7022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4247    0.9993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8555    1.5092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4254   -1.5059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2538   -2.3128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2100   -1.2509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2532    1.8063    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.9407    1.8077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2168    2.5303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4462    1.9778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  8  5  1  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
  4 11  1  0  0  0  0
 11 13  1  0  0  0  0
 11 12  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 14 17  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0339415

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)\C=C\C1=CC(O)=C(OS(O)(=O)=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H8O7S/c10-7-5-6(2-4-9(11)12)1-3-8(7)16-17(13,14)15/h1-5,10H,(H,11,12)(H,13,14,15)/b4-2+

> <INCHI_KEY>
SNVAIAITQIIEMQ-DUXPYHPUSA-N

> <FORMULA>
C9H8O7S

> <MOLECULAR_WEIGHT>
260.221

> <EXACT_MASS>
259.9990733

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
22.620002939997836

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-[3-hydroxy-4-(sulfooxy)phenyl]prop-2-enoic acid

> <ALOGPS_LOGP>
-0.36

> <JCHEM_LOGP>
1.7036422703333334

> <ALOGPS_LOGS>
-2.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.1132383948463476

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.352428832120177

> <JCHEM_PKA_STRONGEST_BASIC>
-4.428269762923368

> <JCHEM_POLAR_SURFACE_AREA>
121.13000000000001

> <JCHEM_REFRACTIVITY>
57.01350000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.28e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-[3-hydroxy-4-(sulfooxy)phenyl]prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0339415 (Caffeic acid 4-O-sulphate)
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PDB for NP0339415 (Caffeic acid 4-O-sulphate)
HEADER    PROTEIN                                 01-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-OCT-19         0                                  
HETATM    1  C   UNK     0       2.558  -1.702   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.052  -2.256   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.702  -0.671   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.516  -1.781   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.773   0.280   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.093  -1.226   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.382   0.835   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.917   1.311   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.526   1.865   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.597   2.817   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.661  -2.811   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.340  -4.317   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -4.125  -2.335   0.000  0.00  0.00           O+0
HETATM   14  S   UNK     0       4.206   3.372   0.000  0.00  0.00           S+0
HETATM   15  O   UNK     0       5.489   3.374   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.138   4.723   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.700   3.692   0.000  0.00  0.00           O+0
CONECT    1    3    6                                                       
CONECT    2    4    6                                                       
CONECT    3    1    7                                                       
CONECT    4    2   11                                                       
CONECT    5    6    8                                                       
CONECT    6    1    2    5                                                  
CONECT    7    3    8    9                                                  
CONECT    8    5    7   10                                                  
CONECT    9    7   14                                                       
CONECT   10    8                                                            
CONECT   11    4   13   12                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

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3D PDB for NP0339415 (Caffeic acid 4-O-sulphate)
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SMILES for NP0339415 (Caffeic acid 4-O-sulphate)
OC(=O)\C=C\C1=CC(O)=C(OS(O)(=O)=O)C=C1
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INCHI for NP0339415 (Caffeic acid 4-O-sulphate)
InChI=1S/C9H8O7S/c10-7-5-6(2-4-9(11)12)1-3-8(7)16-17(13,14)15/h1-5,10H,(H,11,12)(H,13,14,15)/b4-2+
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View in JSmol
Synonyms
ValueSource
Caffeate 4-O-sulfateGenerator
Caffeate 4-O-sulphateGenerator
Caffeic acid 4-O-sulfuric acidGenerator
Caffeic acid 4-O-sulphuric acidGenerator
Caffeate 4-sulfateHMDB
Caffeate 4-sulphateHMDB
Caffeic acid 4-sulfuric acidHMDB
Caffeic acid 4-sulphuric acidHMDB
(2E)-3-[3-Hydroxy-4-(sulfooxy)phenyl]prop-2-enoateHMDB
(2E)-3-[3-Hydroxy-4-(sulphooxy)phenyl]prop-2-enoateHMDB
(2E)-3-[3-Hydroxy-4-(sulphooxy)phenyl]prop-2-enoic acidHMDB
(2E)-3-[3-Hydroxy-4-(sulfooxy)phenyl]-2-propenoic acidHMDB
(e)-Caffeic acid 4-O-sulfateHMDB
(e)-Caffeic acid 4-O-sulphateHMDB
(e)-Caffeic acid 4-sulfateHMDB
(e)-Caffeic acid 4-sulphateHMDB
(e)-Caffeic acid sulfateHMDB
(e)-Caffeic acid sulphateHMDB
3-[3-Hydroxy-4-(sulfooxy)phenyl]-2-propenoic acidHMDB
Caffeic acid 4-O-sulphateHMDB
Caffeic acid 4-sulfateHMDB
Caffeic acid 4-sulphateHMDB
Caffeic acid sulfateHMDB
Caffeic acid sulphateHMDB
Caffeic acid-4'-sulfateHMDB
Caffeic acid-4'-sulphateHMDB
Caffeic acid-4’-sulfateHMDB
Caffeic acid-4’-sulphateHMDB
trans-Caffeic acid 4-O-sulfateHMDB
trans-Caffeic acid 4-O-sulphateHMDB
trans-Caffeic acid 4-sulfateHMDB
trans-Caffeic acid 4-sulphateHMDB
trans-Caffeic acid sulfateHMDB
trans-Caffeic acid sulphateHMDB
Caffeic acid 4-O-sulfateHMDB
Chemical FormulaC9H8O7S
Average Mass260.2210 Da
Monoisotopic Mass259.99907 Da
IUPAC Name(2E)-3-[3-hydroxy-4-(sulfooxy)phenyl]prop-2-enoic acid
Traditional Name(2E)-3-[3-hydroxy-4-(sulfooxy)phenyl]prop-2-enoic acid
CAS Registry NumberNot Available
SMILES
OC(=O)\C=C\C1=CC(O)=C(OS(O)(=O)=O)C=C1
InChI Identifier
InChI=1S/C9H8O7S/c10-7-5-6(2-4-9(11)12)1-3-8(7)16-17(13,14)15/h1-5,10H,(H,11,12)(H,13,14,15)/b4-2+
InChI KeySNVAIAITQIIEMQ-DUXPYHPUSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassCinnamic acids and derivatives  
Sub ClassHydroxycinnamic acids and derivatives  
Direct ParentHydroxycinnamic acids  
Alternative Parents
Substituents
  • Cinnamic acid
    • 

  • Coumaric acid or derivatives
    • 

  • Hydroxycinnamic acid
    • 

  • Phenylsulfate
    • 

  • Arylsulfate
    • 

  • Phenoxy compound
    • 

  • Styrene
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Monocyclic benzene moiety
    • 

  • Benzenoid
    • 

  • Sulfuric acid ester
    • 

  • Sulfate-ester
    • 

  • Sulfuric acid monoester
    • 

  • Organic sulfuric acid or derivatives
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.36ALOGPS
logP1.7ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)-2.4ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area121.13 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity57.01 m³·mol⁻¹ChemAxon
Polarizability22.62 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0041708  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031320  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21668705  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References