NP-MRD: Showing NP-Card for isorhamnetin 3-rutinoside-7-glucoside (NP0050048)

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Record Information

Version

2.0

Created at

2022-03-17 21:22:22 UTC

Updated at

2022-03-17 21:22:22 UTC

NP-MRD ID

NP0050048

Secondary Accession Numbers

None

Natural Product Identification

Common Name

isorhamnetin 3-rutinoside-7-glucoside

Description

(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate belongs to the class of organic compounds known as hydroxycinnamic acid glycosides. isorhamnetin 3-rutinoside-7-glucoside is found in Lathyrus aphaca , Limnanthes douglasii, Mercurialis annua and Rubus sanctus. These are glycosylated hydoxycinnamic acids derivatives (2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652308141918272D          

 22 23  0  0  1  0            999 V2000
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    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
    0.0000    4.9500    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
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  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    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    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
   -0.7145    2.0625    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
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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
  7  1  1  0  0  0  0
  7  2  1  0  0  0  0
  7  5  2  0  0  0  0
  8  3  1  0  0  0  0
  9  5  1  0  0  0  0
  9  8  2  0  0  0  0
 10  6  1  0  0  0  0
 11  4  1  0  0  0  0
 12 10  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15  8  1  0  0  0  0
 16  9  1  0  0  0  0
 10 17  1  6  0  0  0
 18 11  2  0  0  0  0
 12 19  1  1  0  0  0
 13 20  1  6  0  0  0
 21  6  1  0  0  0  0
 14 21  1  0  0  0  0
 22 11  1  0  0  0  0
 14 22  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0050048

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1CO[C@@H](OC(=O)\C=C\C2=CC(O)=C(O)C=C2)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H16O8/c15-8-3-1-7(5-9(8)16)2-4-11(18)22-14-13(20)12(19)10(17)6-21-14/h1-5,10,12-17,19-20H,6H2/b4-2+/t10-,12+,13-,14+/m1/s1

> <INCHI_KEY>
PSYRONNZYLYIOG-RBBVTJSLSA-N

> <FORMULA>
C14H16O8

> <MOLECULAR_WEIGHT>
312.274

> <EXACT_MASS>
312.084517475

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
29.687068177854883

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
-0.40

> <JCHEM_LOGP>
0.12455579866666658

> <ALOGPS_LOGS>
-1.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.079906120923509

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.208025542032937

> <JCHEM_PKA_STRONGEST_BASIC>
-3.52660100247705

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
73.49040000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.41e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 14-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-AUG-19         0                                  
HETATM    1  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  10.780   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  11.550   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  10.780   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.334  13.090   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -1.334  11.550   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    3    7                                                       
CONECT    2    4    7                                                       
CONECT    3    1    8                                                       
CONECT    4    2   11                                                       
CONECT    5    7    9                                                       
CONECT    6   10   21                                                       
CONECT    7    1    2    5                                                  
CONECT    8    3    9   15                                                  
CONECT    9    5    8   16                                                  
CONECT   10    6   12   17                                                  
CONECT   11    4   18   22                                                  
CONECT   12   10   13   19                                                  
CONECT   13   12   14   20                                                  
CONECT   14   13   21   22                                                  
CONECT   15    8                                                            
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   13                                                            
CONECT   21    6   14                                                       
CONECT   22   11   14                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R,4S,5R)-3,4,5-Trihydroxyoxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₁₄H₁₆O₈

Average Mass

312.2740 Da

Monoisotopic Mass

312.08452 Da

IUPAC Name

(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

O[C@@H]1CO[C@@H](OC(=O)\C=C\C2=CC(O)=C(O)C=C2)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C14H16O8/c15-8-3-1-7(5-9(8)16)2-4-11(18)22-14-13(20)12(19)10(17)6-21-14/h1-5,10,12-17,19-20H,6H2/b4-2+/t10-,12+,13-,14+/m1/s1

InChI Key

PSYRONNZYLYIOG-RBBVTJSLSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Lathyrus aphaca	Plant	KNApSAcK
Limnanthes douglasii	Plant	KNApSAcK
Mercurialis annua	Plant	KNApSAcK
Rubus sanctus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acid glycosides. These are glycosylated hydoxycinnamic acids derivatives.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acid glycosides

Alternative Parents

Substituents

Hydroxycinnamic acid glycoside
O-cinnamoyl glycoside
Coumaric acid or derivatives
Cinnamic acid ester
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Monosaccharide
Fatty acyl
Benzenoid
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Alcohol
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	-0.4	ALOGPS
logP	0.12	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	73.49 m³·mol⁻¹	ChemAxon
Polarizability	29.69 Å³	ChemAxon
Number of Rings	2	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9198545

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11023363

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for isorhamnetin 3-rutinoside-7-glucoside (NP0050048)

MOL for NP0050048 (isorhamnetin 3-rutinoside-7-glucoside)

3D MOL for NP0050048 (isorhamnetin 3-rutinoside-7-glucoside)

3D SDF for NP0050048 (isorhamnetin 3-rutinoside-7-glucoside)

3D-SDF for NP0050048 (isorhamnetin 3-rutinoside-7-glucoside)

PDB for NP0050048 (isorhamnetin 3-rutinoside-7-glucoside)

3D PDB for NP0050048 (isorhamnetin 3-rutinoside-7-glucoside)

SMILES for NP0050048 (isorhamnetin 3-rutinoside-7-glucoside)

INCHI for NP0050048 (isorhamnetin 3-rutinoside-7-glucoside)

Structure for NP0050048 (isorhamnetin 3-rutinoside-7-glucoside)

3D Structure for NP0050048 (isorhamnetin 3-rutinoside-7-glucoside)