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Showing NP-Card for Sinapic acid sulfate (NP0341761)

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Record Information
Version2.0
Created at2024-09-12 10:44:38 UTC
Updated at2024-09-12 10:44:38 UTC
NP-MRD IDNP0341761
Secondary Accession NumbersNone
Natural Product Identification
Common NameSinapic acid sulfate
DescriptionSinapic acid 4-O-sulfate, also known as sinapate 4-O-sulfate or (e)-sinapic acid sulphate, belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. It was first documented in 2012 (PMID: 22827565). Sinapic acid 4-O-sulfate is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 26862900).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0341761 (Sinapic acid sulfate)


  Mrv1652303102016582D          

 22 22  0  0  0  0            999 V2000
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -0.9355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -2.3645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  7  3  1  0  0  0  0
  7  5  2  0  0  0  0
  7  6  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  4  1  0  0  0  0
 11  8  2  0  0  0  0
 11  9  1  0  0  0  0
 12 10  2  0  0  0  0
 13 10  1  0  0  0  0
 17  1  1  0  0  0  0
 17  8  1  0  0  0  0
 18  2  1  0  0  0  0
 18  9  1  0  0  0  0
 19 11  1  0  0  0  0
 20 14  1  0  0  0  0
 20 15  2  0  0  0  0
 20 16  2  0  0  0  0
 20 19  1  0  0  0  0
 21  3  1  0  0  0  0
 22  4  1  0  0  0  0
M  END
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3D MOL for NP0341761 (Sinapic acid sulfate)

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3D SDF for NP0341761 (Sinapic acid sulfate)

  Mrv1652303102016582D          

 22 22  0  0  0  0            999 V2000
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -0.9355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -2.3645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  7  3  1  0  0  0  0
  7  5  2  0  0  0  0
  7  6  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  4  1  0  0  0  0
 11  8  2  0  0  0  0
 11  9  1  0  0  0  0
 12 10  2  0  0  0  0
 13 10  1  0  0  0  0
 17  1  1  0  0  0  0
 17  8  1  0  0  0  0
 18  2  1  0  0  0  0
 18  9  1  0  0  0  0
 19 11  1  0  0  0  0
 20 14  1  0  0  0  0
 20 15  2  0  0  0  0
 20 16  2  0  0  0  0
 20 19  1  0  0  0  0
 21  3  1  0  0  0  0
 22  4  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0341761

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O8S/c1-17-8-5-7(3-4-10(12)13)6-9(18-2)11(8)19-20(14,15)16/h3-6H,1-2H3,(H,12,13)(H,14,15,16)/b4-3+

> <INCHI_KEY>
KJWQVTFGBFEXMV-ONEGZZNKSA-N

> <FORMULA>
C11H12O8S

> <MOLECULAR_WEIGHT>
304.27

> <EXACT_MASS>
304.02528852

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
27.437801114910474

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-[3,5-dimethoxy-4-(sulfooxy)phenyl]prop-2-enoic acid

> <ALOGPS_LOGP>
-0.13

> <JCHEM_LOGP>
1.0418650606666664

> <ALOGPS_LOGS>
-2.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.1720630393332843

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.275646768008195

> <JCHEM_PKA_STRONGEST_BASIC>
-4.630949903285977

> <JCHEM_POLAR_SURFACE_AREA>
119.36

> <JCHEM_REFRACTIVITY>
67.95900000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.32e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-[3,5-dimethoxy-4-(sulfooxy)phenyl]prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0341761 (Sinapic acid sulfate)
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PDB for NP0341761 (Sinapic acid sulfate)
HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       3.437  -1.746   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       4.001  -3.850   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.897  -4.414   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   20  S   UNK     0       2.667  -3.080   0.000  0.00  0.00           S+0
HETATM   21  H   UNK     0       2.667   4.620   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0      -1.334   3.850   0.000  0.00  0.00           H+0
CONECT    1   17                                                            
CONECT    2   18                                                            
CONECT    3    4    7   21                                                  
CONECT    4    3   10   22                                                  
CONECT    5    7    8                                                       
CONECT    6    7    9                                                       
CONECT    7    3    5    6                                                  
CONECT    8    5   11   17                                                  
CONECT    9    6   11   18                                                  
CONECT   10    4   12   13                                                  
CONECT   11    8    9   19                                                  
CONECT   12   10                                                            
CONECT   13   10                                                            
CONECT   14   20                                                            
CONECT   15   20                                                            
CONECT   16   20                                                            
CONECT   17    1    8                                                       
CONECT   18    2    9                                                       
CONECT   19   11   20                                                       
CONECT   20   14   15   16   19                                             
CONECT   21    3                                                            
CONECT   22    4                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

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3D PDB for NP0341761 (Sinapic acid sulfate)
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SMILES for NP0341761 (Sinapic acid sulfate)
[H]\C(=C(\[H])C1=CC(OC)=C(OS(O)(=O)=O)C(OC)=C1)C(O)=O
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INCHI for NP0341761 (Sinapic acid sulfate)
InChI=1S/C11H12O8S/c1-17-8-5-7(3-4-10(12)13)6-9(18-2)11(8)19-20(14,15)16/h3-6H,1-2H3,(H,12,13)(H,14,15,16)/b4-3+
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Synonyms
ValueSource
Sinapate 4-O-sulfateGenerator
Sinapate 4-O-sulphateGenerator
Sinapic acid 4-O-sulfuric acidGenerator
Sinapic acid 4-O-sulphuric acidGenerator
(2E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acid sulfateHMDB
(2E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acid sulphateHMDB
(e)-3,5-Dimethoxy-4-hydroxycinnamic acid sulfateHMDB
(e)-3,5-Dimethoxy-4-hydroxycinnamic acid sulphateHMDB
(e)-3-(4-Hydroxy-3,5-dimethoxyphenyl)acrylic acid sulfateHMDB
(e)-3-(4-Hydroxy-3,5-dimethoxyphenyl)acrylic acid sulphateHMDB
(e)-Sinapic acid sulfateHMDB
(e)-Sinapic acid sulphateHMDB
3,5-Dimethoxy-4-hydroxy-trans-cinnamic acid sulfateHMDB
3,5-Dimethoxy-4-hydroxy-trans-cinnamic acid sulphateHMDB
3,5-Dimethoxy-4-hydroxycinnamic acid sulfateHMDB
3,5-Dimethoxy-4-hydroxycinnamic acid sulphateHMDB
3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acid sulfateHMDB
3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acid sulphateHMDB
4-Hydroxy-3,5-dimethoxycinnamic acid sulfateHMDB
4-Hydroxy-3,5-dimethoxycinnamic acid sulphateHMDB
e-Sinapinic acid sulfateHMDB
e-Sinapinic acid sulphateHMDB
Sinapic acid sulfateHMDB
Sinapic acid sulphateHMDB
Sinapic acid-4'-O-sulfateHMDB
Sinapic acid-4'-O-sulphateHMDB
Sinapic acid-4-O-sulfateHMDB
Sinapic acid-4-O-sulphateHMDB
Sinapic acid-4’-O-sulfateHMDB
Sinapic acid-4’-O-sulphateHMDB
Sinapinic acid sulfateHMDB
Sinapinic acid sulphateHMDB
Synapitic acid sulfateHMDB
Synapitic acid sulphateHMDB
trans-4-Hydroxy-3,5-dimethoxycinnamic acid sulfateHMDB
trans-4-Hydroxy-3,5-dimethoxycinnamic acid sulphateHMDB
trans-Sinapic acid sulfateHMDB
trans-Sinapic acid sulphateHMDB
trans-Sinapinic acid sulfateHMDB
trans-Sinapinic acid sulphateHMDB
Chemical FormulaC11H12O8S
Average Mass304.2700 Da
Monoisotopic Mass304.02529 Da
IUPAC Name(2E)-3-[3,5-dimethoxy-4-(sulfooxy)phenyl]prop-2-enoic acid
Traditional Name(2E)-3-[3,5-dimethoxy-4-(sulfooxy)phenyl]prop-2-enoic acid
CAS Registry NumberNot Available
SMILES
[H]\C(=C(\[H])C1=CC(OC)=C(OS(O)(=O)=O)C(OC)=C1)C(O)=O
InChI Identifier
InChI=1S/C11H12O8S/c1-17-8-5-7(3-4-10(12)13)6-9(18-2)11(8)19-20(14,15)16/h3-6H,1-2H3,(H,12,13)(H,14,15,16)/b4-3+
InChI KeyKJWQVTFGBFEXMV-ONEGZZNKSA-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 coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassCinnamic acids and derivatives  
Sub ClassHydroxycinnamic acids and derivatives  
Direct ParentCoumaric acids and derivatives  
Alternative Parents
Substituents
  • Cinnamic acid
    • 

  • Coumaric acid or derivatives
    • 

  • Phenylsulfate
    • 

  • Arylsulfate
    • 

  • M-dimethoxybenzene
    • 

  • Dimethoxybenzene
    • 

  • Anisole
    • 

  • Methoxybenzene
    • 

  • Styrene
    • 

  • Phenol ether
    • 

  • Phenoxy compound
    • 

  • Alkyl aryl ether
    • 

  • Benzenoid
    • 

  • Sulfuric acid ester
    • 

  • Sulfate-ester
    • 

  • Sulfuric acid monoester
    • 

  • Monocyclic benzene moiety
    • 

  • Organic sulfuric acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Ether
    • 

  • Organic oxide
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • 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-0.13ALOGPS
logP1.04ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)-2.3ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area119.36 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity67.96 m³·mol⁻¹ChemAxon
Polarizability27.44 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0060020  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB093756  
KNApSAcK IDNot Available
Chemspider ID28554517  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound102354829  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. van der Hooft JJ, de Vos RC, Mihaleva V, Bino RJ, Ridder L, de Roo N, Jacobs DM, van Duynhoven JP, Vervoort J: Structural elucidation and quantification of phenolic conjugates present in human urine after tea intake. Anal Chem. 2012 Aug 21;84(16):7263-71. doi: 10.1021/ac3017339. Epub 2012 Aug 2. [PubMed:22827565  ] 
  2. Ounnas F, Prive F, Salen P, Gaci N, Tottey W, Calani L, Bresciani L, Lopez-Gutierrez N, Hazane-Puch F, Laporte F, Brugere JF, Del Rio D, Demeilliers C, de Lorgeril M: Whole Rye Consumption Improves Blood and Liver n-3 Fatty Acid Profile and Gut Microbiota Composition in Rats. PLoS One. 2016 Feb 10;11(2):e0148118. doi: 10.1371/journal.pone.0148118.  eCollection 2016. [PubMed:26862900  ]