NP-MRD: Showing NP-Card for Ferulic acid 4-sulfate (NP0339416)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2024-09-11 21:43:45 UTC

Updated at

2024-09-11 21:43:45 UTC

NP-MRD ID

NP0339416

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ferulic acid 4-sulfate

Description

Ferulic acid 4-O-sulfate, also known as ferulic acid sulfuric acid or ferulate sulfate, 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. Ferulic acid 4-O-sulfate is an extremely weak basic (essentially neutral) compound (based on its pKa). Ferulic acid 4-O-sulfate (CAS: 86321-29-1) Is a phenolic acid metabolite. It is also a coffee metabolite found in blood or urine. Ferulic acid 4-O-sulfate was found to be elevated in rat urine after whole rye consumption which makes this compound a potential urinary biomarker of whole grain intake (PMID: 26862900 ).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303102016542D          

 18 18  0  0  0  0            999 V2000
    1.7860    0.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5007    0.0015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7860    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718    0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    0.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718   -1.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0715    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3569    0.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5007    0.4126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5008    1.2377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9314   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2172   -0.8247    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8042   -0.1081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6300   -0.1081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5007   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9  4  1  0  0  0  0
  1 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11  4  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  2  0  0  0  0
 15 18  1  0  0  0  0
  7 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339416

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OS(O)(=O)=O)C=CC(\C=C\C(O)=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O7S/c1-16-9-6-7(3-5-10(11)12)2-4-8(9)17-18(13,14)15/h2-6H,1H3,(H,11,12)(H,13,14,15)/b5-3+

> <INCHI_KEY>
PZPATWACAAOHTJ-HWKANZROSA-N

> <FORMULA>
C10H10O7S

> <MOLECULAR_WEIGHT>
274.247

> <EXACT_MASS>
274.014723364

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
24.70287240233766

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
-0.32

> <JCHEM_LOGP>
1.1995363263333336

> <ALOGPS_LOGS>
-2.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.2287615296312224

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.2470360660650037

> <JCHEM_PKA_STRONGEST_BASIC>
-4.9204853045642185

> <JCHEM_POLAR_SURFACE_AREA>
110.13000000000001

> <JCHEM_REFRACTIVITY>
61.49580000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.25e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-[3-methoxy-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       3.334   0.772   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.668   0.003   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.334   2.310   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.001   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.334   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.334  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.667  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.000   0.001   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.666   0.771   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.668   0.770   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.668   2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -7.339  -2.310   0.000  0.00  0.00           O+0
HETATM   15  S   UNK     0      -6.005  -1.539   0.000  0.00  0.00           S+0
HETATM   16  O   UNK     0      -5.235  -0.202   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -6.776  -0.202   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -4.668  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2    3   10                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    5    9   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    1   11                                                       
CONECT   11   10    4                                                       
CONECT   12    6   13                                                       
CONECT   13   12                                                            
CONECT   14   15                                                            
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15    7                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Value	Source
Ferulic acid sulfate	ChEBI
Ferulate sulfate	Generator
Ferulate sulphate	Generator
Ferulic acid sulfuric acid	Generator
Ferulic acid sulphuric acid	Generator
Ferulate 4-O-sulfate	Generator
Ferulate 4-O-sulphate	Generator
Ferulic acid 4-O-sulfuric acid	Generator
Ferulic acid 4-O-sulphuric acid	Generator
Ferulate 4-sulfate	HMDB
Ferulate 4-sulphate	HMDB
Ferulic acid 4-sulfuric acid	HMDB
Ferulic acid 4-sulphuric acid	HMDB
(2E)-3-[3-Methoxy-4-(sulfooxy)phenyl]-2-propenoic acid	HMDB
Ferulic acid-4'-sulfate	HMDB
(e)-Ferulic acid 4-O-sulfate	HMDB
(e)-Ferulic acid-4'-sulfate	HMDB
trans-Ferulic acid 4-O-sulfate	HMDB
trans-Ferulic acid-4'-sulfate	HMDB
Ferulic acid 4-sulfate	HMDB
(e)-Ferulic acid 4-O-sulphate	HMDB
(e)-Ferulic acid-4'-sulphate	HMDB
(e)-Ferulic acid-4’-sulfate	HMDB
(e)-Ferulic acid-4’-sulphate	HMDB
Ferulic acid 4-O-sulphate	HMDB
Ferulic acid 4-sulphate	HMDB
Ferulic acid-4'-sulphate	HMDB
Ferulic acid-4’-sulfate	HMDB
Ferulic acid-4’-sulphate	HMDB
trans-Ferulic acid 4-O-sulphate	HMDB
trans-Ferulic acid-4'-sulphate	HMDB
trans-Ferulic acid-4’-sulfate	HMDB
trans-Ferulic acid-4’-sulphate	HMDB
Ferulic acid 4-O-sulfate	HMDB

Chemical Formula

C₁₀H₁₀O₇S

Average Mass

274.2470 Da

Monoisotopic Mass

274.01472 Da

IUPAC Name

(2E)-3-[3-methoxy-4-(sulfooxy)phenyl]prop-2-enoic acid

Traditional Name

(2E)-3-[3-methoxy-4-(sulfooxy)phenyl]prop-2-enoic acid

CAS Registry Number

Not Available

SMILES

COC1=C(OS(O)(=O)=O)C=CC(\C=C\C(O)=O)=C1

InChI Identifier

InChI=1S/C10H10O7S/c1-16-9-6-7(3-5-10(11)12)2-4-8(9)17-18(13,14)15/h2-6H,1H3,(H,11,12)(H,13,14,15)/b5-3+

InChI Key

PZPATWACAAOHTJ-HWKANZROSA-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
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Styrene
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Sulfuric acid ester
Sulfate-ester
Sulfuric acid monoester
Organic sulfuric acid or derivatives
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Carbonyl group
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	-0.32	ALOGPS
logP	1.2	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	-2.2	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	61.5 m³·mol⁻¹	ChemAxon
Polarizability	24.7 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

HMDB0029200

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029900

KNApSAcK ID

Not Available

Chemspider ID

4878542

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6305574

PDB ID

Not Available

ChEBI ID

133508

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Ferulic acid 4-sulfate (NP0339416)

MOL for NP0339416 (Ferulic acid 4-sulfate)

3D MOL for NP0339416 (Ferulic acid 4-sulfate)

3D SDF for NP0339416 (Ferulic acid 4-sulfate)

3D-SDF for NP0339416 (Ferulic acid 4-sulfate)

PDB for NP0339416 (Ferulic acid 4-sulfate)

3D PDB for NP0339416 (Ferulic acid 4-sulfate)

SMILES for NP0339416 (Ferulic acid 4-sulfate)

INCHI for NP0339416 (Ferulic acid 4-sulfate)

Structure for NP0339416 (Ferulic acid 4-sulfate)

3D Structure for NP0339416 (Ferulic acid 4-sulfate)