NP-MRD: Showing NP-Card for Isopeonidin 3-arabinoside (NP0339434)

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Record Information

Version

2.0

Created at

2024-09-11 21:50:02 UTC

Updated at

2024-09-11 21:50:02 UTC

NP-MRD ID

NP0339434

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isopeonidin 3-arabinoside

Description

Isoferulic acid 3-sulfate, also known as isoferulate 3-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. Isoferulic acid 3-sulfate is a polyphenol metabolite detected in biological fluids (PMID: 20428313 ). Isoferulic acid 3-sulfate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02271201312D          

 31 34  0  0  1  0            999 V2000
    1.4289    1.9875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    2.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    3.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290    1.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290    1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2869    1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2869    1.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.4000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.4000    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
   -1.3819   -0.5599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -1.3445    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3020   -1.3445    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0471   -0.5599    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -0.0750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7375   -0.3049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1829   -2.0120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6119   -2.0120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2763   -2.7656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  2  0  0  0  0
  9 21  1  0  0  0  0
 26 11  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 22 26  1  0  0  0  0
 25 27  1  1  0  0  0
 24 28  1  6  0  0  0
 23 29  1  1  0  0  0
 29 30  1  0  0  0  0
  4 31  1  0  0  0  0
M  CHG  1  21   1
M  END


  Mrv0541 02271201312D          

 31 34  0  0  1  0            999 V2000
    1.4289    1.9875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    2.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    3.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290    1.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290    1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2869    1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2869    1.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.4000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.4000    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
   -1.3819   -0.5599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -1.3445    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3020   -1.3445    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0471   -0.5599    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -0.0750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7375   -0.3049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1829   -2.0120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6119   -2.0120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2763   -2.7656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  2  0  0  0  0
  9 21  1  0  0  0  0
 26 11  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 22 26  1  0  0  0  0
 25 27  1  1  0  0  0
 24 28  1  6  0  0  0
 23 29  1  1  0  0  0
 29 30  1  0  0  0  0
  4 31  1  0  0  0  0
M  CHG  1  21   1
M  END
> <DATABASE_ID>
NP0339434

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C(C=C1)C1=C(O[C@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)C=C2C(O)=CC(O)=CC2=[O+]1

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O10/c1-28-14-3-2-9(4-13(14)25)20-16(30-21-19(27)18(26)17(8-22)31-21)7-11-12(24)5-10(23)6-15(11)29-20/h2-7,17-19,21-22,26-27H,8H2,1H3,(H2-,23,24,25)/p+1/t17-,18-,19+,21+/m1/s1

> <INCHI_KEY>
FXNWBJIHSLHFRS-BNDYYXHWSA-O

> <FORMULA>
C21H21O10

> <MOLECULAR_WEIGHT>
433.3854

> <EXACT_MASS>
433.113471892

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
42.22053227137587

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-1λ⁴-chromen-1-ylium

> <ALOGPS_LOGP>
1.12

> <JCHEM_LOGP>
1.0912000000000002

> <ALOGPS_LOGS>
-3.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.584663722003877

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.39904008568149

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9811524252368704

> <JCHEM_POLAR_SURFACE_AREA>
162.21

> <JCHEM_REFRACTIVITY>
114.77729999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.08e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-1λ⁴-chromen-1-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  O   UNK     0       2.667   3.710   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334   4.480   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   6.020   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.667   6.790   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.000   6.790   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   6.020   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   4.480   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   3.710   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   3.710   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667   2.170   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334   1.400   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.001   1.400   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.335   2.170   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.668   1.400   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -6.668  -0.140   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -8.002   2.170   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.002   3.710   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -9.336   4.480   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -6.668   4.480   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.335   3.710   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.001   4.480   0.000  0.00  0.00           O+1
HETATM   22  O   UNK     0      -2.580  -1.045   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.104  -2.510   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.564  -2.510   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.088  -1.045   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.334  -0.140   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.377  -0.569   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       0.341  -3.756   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -3.009  -3.756   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -2.382  -5.162   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.667   8.330   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3   31                                                       
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7    2                                                       
CONECT    9    7   10   21                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10   26                                                       
CONECT   12   10   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   13   21                                                  
CONECT   21   20    9                                                       
CONECT   22   23   26                                                       
CONECT   23   22   24   29                                                  
CONECT   24   23   25   28                                                  
CONECT   25   24   26   27                                                  
CONECT   26   11   25   22                                                  
CONECT   27   25                                                            
CONECT   28   24                                                            
CONECT   29   23   30                                                       
CONECT   30   29                                                            
CONECT   31    4                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
Isoferulate 3-sulfate	Generator
Isoferulate 3-sulphate	Generator
Isoferulic acid 3-sulfuric acid	Generator
Isoferulic acid 3-sulphuric acid	Generator
Isopeonidin 3-O-arabinoside	HMDB

Chemical Formula

C₂₁H₂₁O₁₀

Average Mass

433.3854 Da

Monoisotopic Mass

433.11347 Da

IUPAC Name

3-{[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-1λ⁴-chromen-1-ylium

Traditional Name

3-{[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-1λ⁴-chromen-1-ylium

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C(C=C1)C1=C(O[C@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)C=C2C(O)=CC(O)=CC2=[O+]1

InChI Identifier

InChI=1S/C21H20O10/c1-28-14-3-2-9(4-13(14)25)20-16(30-21-19(27)18(26)17(8-22)31-21)7-11-12(24)5-10(23)6-15(11)29-20/h2-7,17-19,21-22,26-27H,8H2,1H3,(H2-,23,24,25)/p+1/t17-,18-,19+,21+/m1/s1

InChI Key

FXNWBJIHSLHFRS-BNDYYXHWSA-O

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	1.12	ALOGPS
logP	1.09	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	6.4	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	162.21 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	114.78 m³·mol⁻¹	ChemAxon
Polarizability	42.22 Å³	ChemAxon
Number of Rings	4	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

HMDB0041748

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029918

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

71749556

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Isopeonidin 3-arabinoside (NP0339434)

MOL for NP0339434 (Isopeonidin 3-arabinoside)

3D MOL for NP0339434 (Isopeonidin 3-arabinoside)

3D SDF for NP0339434 (Isopeonidin 3-arabinoside)

3D-SDF for NP0339434 (Isopeonidin 3-arabinoside)

PDB for NP0339434 (Isopeonidin 3-arabinoside)

3D PDB for NP0339434 (Isopeonidin 3-arabinoside)

SMILES for NP0339434 (Isopeonidin 3-arabinoside)

INCHI for NP0339434 (Isopeonidin 3-arabinoside)

Structure for NP0339434 (Isopeonidin 3-arabinoside)

3D Structure for NP0339434 (Isopeonidin 3-arabinoside)