NP-MRD: Showing NP-Card for (2s,3s)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-3-yl 5-(3,4-dihydroxyphenyl)-3-hydroxypentanoate (NP0257089)

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Record Information

Version

2.0

Created at

2022-09-07 22:07:07 UTC

Updated at

2022-09-07 22:07:08 UTC

NP-MRD ID

NP0257089

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3s)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-3-yl 5-(3,4-dihydroxyphenyl)-3-hydroxypentanoate

Description

NSC607319 belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-Tiol. (2s,3s)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-3-yl 5-(3,4-dihydroxyphenyl)-3-hydroxypentanoate is found in Phyllocladus alpinus and Phyllocladus trichomanoides. Based on a literature review very few articles have been published on NSC607319.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082200072D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309082200072D          

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M  END
> <DATABASE_ID>
NP0257089

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(CCC1=CC=C(O)C(O)=C1)CC(=O)O[C@H]1CC2=C(O)C=C(O)C=C2O[C@H]1C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H26O10/c27-15(4-1-13-2-5-18(29)21(32)7-13)11-25(34)35-24-12-17-20(31)9-16(28)10-23(17)36-26(24)14-3-6-19(30)22(33)8-14/h2-3,5-10,15,24,26-33H,1,4,11-12H2/t15?,24-,26-/m0/s1

> <INCHI_KEY>
FKDRTLFRRHQTGU-XEOYHGAXSA-N

> <FORMULA>
C26H26O10

> <MOLECULAR_WEIGHT>
498.484

> <EXACT_MASS>
498.152597037

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
48.58892628571701

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 5-(3,4-dihydroxyphenyl)-3-hydroxypentanoate

> <JCHEM_LOGP>
3.56633653

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.255398900825709

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.760408698146751

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8037762285219046

> <JCHEM_POLAR_SURFACE_AREA>
177.14

> <JCHEM_REFRACTIVITY>
127.1534

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 5-(3,4-dihydroxyphenyl)-3-hydroxypentanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    8                                                       
CONECT   16    2   17                                                       
CONECT   17   16   18   28                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   26                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   19   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   17   29                                                  
CONECT   29   28   30   36                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   29                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₆O₁₀

Average Mass

498.4840 Da

Monoisotopic Mass

498.15260 Da

IUPAC Name

(2S,3S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 5-(3,4-dihydroxyphenyl)-3-hydroxypentanoate

Traditional Name

(2S,3S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 5-(3,4-dihydroxyphenyl)-3-hydroxypentanoate

CAS Registry Number

Not Available

SMILES

OC(CCC1=CC=C(O)C(O)=C1)CC(=O)O[C@H]1CC2=C(O)C=C(O)C=C2O[C@H]1C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C26H26O10/c27-15(4-1-13-2-5-18(29)21(32)7-13)11-25(34)35-24-12-17-20(31)9-16(28)10-23(17)36-26(24)14-3-6-19(30)22(33)8-14/h2-3,5-10,15,24,26-33H,1,4,11-12H2/t15?,24-,26-/m0/s1

InChI Key

FKDRTLFRRHQTGU-XEOYHGAXSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Phyllocladus alpinus	LOTUS Database	35616633
Phyllocladus trichomanoides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-Tiol.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Catechins

Alternative Parents

Substituents

Catechin
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Chromane
Benzopyran
1-benzopyran
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Beta-hydroxy acid
Fatty acid ester
Phenol
Benzenoid
Hydroxy acid
Monocyclic benzene moiety
Fatty acyl
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carbonyl group
Organic oxide
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	3.57	ChemAxon
pKa (Strongest Acidic)	8.76	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	177.14 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	127.15 m³·mol⁻¹	ChemAxon
Polarizability	48.59 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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

Not Available

Chemspider ID

314922

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

354776

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3s)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-3-yl 5-(3,4-dihydroxyphenyl)-3-hydroxypentanoate (NP0257089)

MOL for NP0257089 ((2s,3s)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-3-yl 5-(3,4-dihydroxyphenyl)-3-hydroxypentanoate)

3D MOL for NP0257089 ((2s,3s)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-3-yl 5-(3,4-dihydroxyphenyl)-3-hydroxypentanoate)

3D SDF for NP0257089 ((2s,3s)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-3-yl 5-(3,4-dihydroxyphenyl)-3-hydroxypentanoate)

3D-SDF for NP0257089 ((2s,3s)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-3-yl 5-(3,4-dihydroxyphenyl)-3-hydroxypentanoate)

PDB for NP0257089 ((2s,3s)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-3-yl 5-(3,4-dihydroxyphenyl)-3-hydroxypentanoate)

3D PDB for NP0257089 ((2s,3s)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-3-yl 5-(3,4-dihydroxyphenyl)-3-hydroxypentanoate)

SMILES for NP0257089 ((2s,3s)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-3-yl 5-(3,4-dihydroxyphenyl)-3-hydroxypentanoate)

INCHI for NP0257089 ((2s,3s)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-3-yl 5-(3,4-dihydroxyphenyl)-3-hydroxypentanoate)

Structure for NP0257089 ((2s,3s)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-3-yl 5-(3,4-dihydroxyphenyl)-3-hydroxypentanoate)

3D Structure for NP0257089 ((2s,3s)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-3-yl 5-(3,4-dihydroxyphenyl)-3-hydroxypentanoate)