NP-MRD: Showing NP-Card for (2"R)-2"-Hydroxyoleuropein (NP0044173)

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Record Information

Version

2.0

Created at

2021-11-12 23:54:14 UTC

Updated at

2021-11-26 17:46:14 UTC

NP-MRD ID

NP0044173

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2"R)-2"-Hydroxyoleuropein

Description

(2''R)-2''-Hydroxyoleuropein belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. (2"R)-2"-Hydroxyoleuropein is found in Fraxinus americana. (2"R)-2"-Hydroxyoleuropein was first documented in 2000 (Takenaka, et al.). Based on a literature review very few articles have been published on (2''R)-2''-Hydroxyoleuropein.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652311132100542D          

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M  END

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 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 14 16  1  1  0  0  0
 16 17  1  0  0  0  0
 13 18  1  6  0  0  0
 12 19  1  1  0  0  0
 11 20  1  6  0  0  0
  5 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
  4 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 31 36  1  0  0  0  0
 34 37  1  0  0  0  0
 33 38  1  0  0  0  0
 30 39  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0044173

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)\C(=C\C)[C@@H]1CC(=O)OC[C@H](O)C1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H32O14/c1-3-12-13(7-19(30)36-10-17(29)11-4-5-15(27)16(28)6-11)14(23(34)35-2)9-37-24(12)39-25-22(33)21(32)20(31)18(8-26)38-25/h3-6,9,13,17-18,20-22,24-29,31-33H,7-8,10H2,1-2H3/b12-3+/t13-,17-,18+,20+,21-,22+,24-,25-/m0/s1

> <INCHI_KEY>
WRDXQRMHELNFOK-PPKUYGORSA-N

> <FORMULA>
C25H32O14

> <MOLECULAR_WEIGHT>
556.517

> <EXACT_MASS>
556.17920571

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
54.70037189991311

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2S,3E,4S)-4-{2-[(2R)-2-(3,4-dihydroxyphenyl)-2-hydroxyethoxy]-2-oxoethyl}-3-ethylidene-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

> <ALOGPS_LOGP>
0.09

> <JCHEM_LOGP>
-0.8077203913333331

> <ALOGPS_LOGS>
-2.68

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.068085631175045

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.209492267575534

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810849052288235

> <JCHEM_POLAR_SURFACE_AREA>
221.89999999999995

> <JCHEM_REFRACTIVITY>
129.4257

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.18e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (4S,5E,6S)-4-{2-[(2R)-2-(3,4-dihydroxyphenyl)-2-hydroxyethoxy]-2-oxoethyl}-5-ethylidene-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-21         0                                  
HETATM    1  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.240  -8.946   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      14.670 -10.010   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      14.670  -6.930   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   25                                                  
CONECT    5    4    6   21                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12   20                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   10                                                       
CONECT   16   14   17                                                       
CONECT   17   16                                                            
CONECT   18   13                                                            
CONECT   19   12                                                            
CONECT   20   11                                                            
CONECT   21    5   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23                                                            
CONECT   25    4   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   39                                                  
CONECT   31   30   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   38                                                  
CONECT   34   33   35   37                                                  
CONECT   35   34   36                                                       
CONECT   36   35   31                                                       
CONECT   37   34                                                            
CONECT   38   33                                                            
CONECT   39   30                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₂O₁₄

Average Mass

556.5170 Da

Monoisotopic Mass

556.17921 Da

IUPAC Name

methyl (2S,3E,4S)-4-{2-[(2R)-2-(3,4-dihydroxyphenyl)-2-hydroxyethoxy]-2-oxoethyl}-3-ethylidene-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

Traditional Name

methyl (4S,5E,6S)-4-{2-[(2R)-2-(3,4-dihydroxyphenyl)-2-hydroxyethoxy]-2-oxoethyl}-5-ethylidene-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)\C(=C\C)[C@@H]1CC(=O)OC[C@H](O)C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C25H32O14/c1-3-12-13(7-19(30)36-10-17(29)11-4-5-15(27)16(28)6-11)14(23(34)35-2)9-37-24(12)39-25-22(33)21(32)20(31)18(8-26)38-25/h3-6,9,13,17-18,20-22,24-29,31-33H,7-8,10H2,1-2H3/b12-3+/t13-,17-,18+,20+,21-,22+,24-,25-/m0/s1

InChI Key

WRDXQRMHELNFOK-PPKUYGORSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Fraxinus americana	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Glycosyl compound
Secoiridoid-skeleton
O-glycosyl compound
Aromatic monoterpenoid
Monocyclic monoterpenoid
Monoterpenoid
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Sugar acid
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Monosaccharide
Benzenoid
Oxane
Alpha,beta-unsaturated carboxylic ester
Methyl ester
Enoate ester
Vinylogous ester
Secondary alcohol
Carboxylic acid ester
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Aromatic alcohol
Organic oxide
Alcohol
Hydrocarbon derivative
Carbonyl group
Primary alcohol
Organic oxygen compound
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	0.09	ALOGPS
logP	-0.81	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	221.9 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	129.43 m³·mol⁻¹	ChemAxon
Polarizability	54.7 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00036342

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

102461562

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yukiko Takenaka, Takao Tanahashi, Masashi Shintaku, Takeshi Sakai, Naotaka Nagakura, Parida (2000). Secoiridoid glucosides from Fraxinus americana. Phytochemistry 2000, 55 (3) , 275-284. https://doi.org/10.1016/S0031-9422(00)00319-8. Phytochemistry.

Showing NP-Card for (2"R)-2"-Hydroxyoleuropein (NP0044173)

MOL for NP0044173 ((2"R)-2"-Hydroxyoleuropein)

3D MOL for NP0044173 ((2"R)-2"-Hydroxyoleuropein)

3D SDF for NP0044173 ((2"R)-2"-Hydroxyoleuropein)

3D-SDF for NP0044173 ((2"R)-2"-Hydroxyoleuropein)

PDB for NP0044173 ((2"R)-2"-Hydroxyoleuropein)

3D PDB for NP0044173 ((2"R)-2"-Hydroxyoleuropein)

SMILES for NP0044173 ((2"R)-2"-Hydroxyoleuropein)

INCHI for NP0044173 ((2"R)-2"-Hydroxyoleuropein)

Structure for NP0044173 ((2"R)-2"-Hydroxyoleuropein)

3D Structure for NP0044173 ((2"R)-2"-Hydroxyoleuropein)