NP-MRD: Showing NP-Card for Sinapic acid sulfate (NP0341761)

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Record Information

Version

2.0

Created at

2024-09-12 10:44:38 UTC

Updated at

2024-09-12 10:44:38 UTC

NP-MRD ID

NP0341761

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sinapic acid sulfate

Description

Sinapic 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. Sinapic acid 4-O-sulfate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  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

$$$$

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

View in JSmol

Synonyms

Value	Source
Sinapate 4-O-sulfate	Generator
Sinapate 4-O-sulphate	Generator
Sinapic acid 4-O-sulfuric acid	Generator
Sinapic acid 4-O-sulphuric acid	Generator
(2E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acid sulfate	HMDB
(2E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acid sulphate	HMDB
(e)-3,5-Dimethoxy-4-hydroxycinnamic acid sulfate	HMDB
(e)-3,5-Dimethoxy-4-hydroxycinnamic acid sulphate	HMDB
(e)-3-(4-Hydroxy-3,5-dimethoxyphenyl)acrylic acid sulfate	HMDB
(e)-3-(4-Hydroxy-3,5-dimethoxyphenyl)acrylic acid sulphate	HMDB
(e)-Sinapic acid sulfate	HMDB
(e)-Sinapic acid sulphate	HMDB
3,5-Dimethoxy-4-hydroxy-trans-cinnamic acid sulfate	HMDB
3,5-Dimethoxy-4-hydroxy-trans-cinnamic acid sulphate	HMDB
3,5-Dimethoxy-4-hydroxycinnamic acid sulfate	HMDB
3,5-Dimethoxy-4-hydroxycinnamic acid sulphate	HMDB
3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acid sulfate	HMDB
3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acid sulphate	HMDB
4-Hydroxy-3,5-dimethoxycinnamic acid sulfate	HMDB
4-Hydroxy-3,5-dimethoxycinnamic acid sulphate	HMDB
e-Sinapinic acid sulfate	HMDB
e-Sinapinic acid sulphate	HMDB
Sinapic acid sulfate	HMDB
Sinapic acid sulphate	HMDB
Sinapic acid-4'-O-sulfate	HMDB
Sinapic acid-4'-O-sulphate	HMDB
Sinapic acid-4-O-sulfate	HMDB
Sinapic acid-4-O-sulphate	HMDB
Sinapic acid-4’-O-sulfate	HMDB
Sinapic acid-4’-O-sulphate	HMDB
Sinapinic acid sulfate	HMDB
Sinapinic acid sulphate	HMDB
Synapitic acid sulfate	HMDB
Synapitic acid sulphate	HMDB
trans-4-Hydroxy-3,5-dimethoxycinnamic acid sulfate	HMDB
trans-4-Hydroxy-3,5-dimethoxycinnamic acid sulphate	HMDB
trans-Sinapic acid sulfate	HMDB
trans-Sinapic acid sulphate	HMDB
trans-Sinapinic acid sulfate	HMDB
trans-Sinapinic acid sulphate	HMDB

Chemical Formula

C₁₁H₁₂O₈S

Average Mass

304.2700 Da

Monoisotopic Mass

304.02529 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 Number

Not 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 Key

KJWQVTFGBFEXMV-ONEGZZNKSA-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 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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

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	-0.13	ALOGPS
logP	1.04	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	-2.3	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	67.96 m³·mol⁻¹	ChemAxon
Polarizability	27.44 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0060020

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB093756

KNApSAcK ID

Not Available

Chemspider ID

28554517

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102354829

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Sinapic acid sulfate (NP0341761)

MOL for NP0341761 (Sinapic acid sulfate)

3D MOL for NP0341761 (Sinapic acid sulfate)

3D SDF for NP0341761 (Sinapic acid sulfate)

3D-SDF for NP0341761 (Sinapic acid sulfate)

PDB for NP0341761 (Sinapic acid sulfate)

3D PDB for NP0341761 (Sinapic acid sulfate)

SMILES for NP0341761 (Sinapic acid sulfate)

INCHI for NP0341761 (Sinapic acid sulfate)

Structure for NP0341761 (Sinapic acid sulfate)

3D Structure for NP0341761 (Sinapic acid sulfate)