NP-MRD: Showing NP-Card for (+)-Sinocrassoside B1 (NP0072316)

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Record Information

Version

2.0

Created at

2022-04-28 17:40:36 UTC

Updated at

2022-04-28 17:40:36 UTC

NP-MRD ID

NP0072316

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Sinocrassoside B1

Description

(2S,3R,4R,5S,6S)-2-{[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxo-4H-chromen-7-yl]oxy}-3,5-dihydroxy-6-methyloxan-4-yl 2-methylpropanoate belongs to the class of organic compounds known as flavonoid-7-o-glycosides. (+)-Sinocrassoside B1 is found in Sinocrassula indica . These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position (2S,3R,4R,5S,6S)-2-{[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxo-4H-chromen-7-yl]oxy}-3,5-dihydroxy-6-methyloxan-4-yl 2-methylpropanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309272006422D          

 37 40  0  0  0  0            999 V2000
10014.293310010.2655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  6  7  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309272006422D          

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M  END
> <DATABASE_ID>
NP0072316

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)O[C@@H]1[C@@H](O)[C@H](C)O[C@@H](OC2=CC(O)=C3C(OC(C4=CC(O)=C(O)C=C4)=C(O)C3=O)=C2)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H26O12/c1-9(2)24(33)37-23-18(29)10(3)34-25(21(23)32)35-12-7-15(28)17-16(8-12)36-22(20(31)19(17)30)11-4-5-13(26)14(27)6-11/h4-10,18,21,23,25-29,31-32H,1-3H3/t10-,18-,21+,23+,25-/m0/s1

> <INCHI_KEY>
XIMBHDHJSKJECM-BRBYZNOMSA-N

> <FORMULA>
C25H26O12

> <MOLECULAR_WEIGHT>
518.471

> <EXACT_MASS>
518.142426277

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
51.31305727288502

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4R,5S,6S)-2-{[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxo-4H-chromen-7-yl]oxy}-3,5-dihydroxy-6-methyloxan-4-yl 2-methylpropanoate

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
2.6197888729999996

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.455852756991433

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.077916661978591

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6269985317871463

> <JCHEM_POLAR_SURFACE_AREA>
192.43999999999997

> <JCHEM_REFRACTIVITY>
125.81579999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.52e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R,5S,6S)-2-{[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxochromen-7-yl]oxy}-3,5-dihydroxy-6-methyloxan-4-yl 2-methylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8693.3488685.829   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8700.0118692.774   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8690.6838685.829   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8688.0208690.468   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8685.3578692.008   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8682.6868690.468   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8681.3528689.695   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8680.0198690.468   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8678.6858689.695   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8680.0198692.008   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8681.3528688.155   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8685.3578685.848   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    8682.6868687.388   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0    8698.6808692.008   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8697.3478692.778   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8696.0138692.008   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8696.0138690.468   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8697.3468689.698   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8698.6808690.468   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8690.6838690.460   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8689.3498689.690   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8689.3498688.150   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8690.6838687.379   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0    8693.3468690.460   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0    8692.0128689.690   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8692.0128688.149   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8694.6808689.690   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8693.3468687.380   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8694.6808688.149   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0    8696.0108687.373   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0    8685.3548690.466   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8684.0218689.696   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0    8684.0218688.156   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0    8685.3548687.386   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0    8686.6888688.156   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0    8686.6888689.696   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0    8697.3468694.320   0.000  0.00  0.00           O+0
CONECT    1   28                                                            
CONECT    2   14                                                            
CONECT    3   23                                                            
CONECT    4   21   36                                                       
CONECT    5   31                                                            
CONECT    6    7   32                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7                                                            
CONECT   12   34                                                            
CONECT   13   33                                                            
CONECT   14   15   19    2                                                  
CONECT   15   14   16   37                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   27                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20   21   25                                                       
CONECT   21   20   22    4                                                  
CONECT   22   21   23                                                       
CONECT   23   22   26    3                                                  
CONECT   24   25   27                                                       
CONECT   25   26   24   20                                                  
CONECT   26   25   23   28                                                  
CONECT   27   24   17   29                                                  
CONECT   28   29   26    1                                                  
CONECT   29   28   30   27                                                  
CONECT   30   29                                                            
CONECT   31   32   36    5                                                  
CONECT   32   31   33    6                                                  
CONECT   33   32   34   13                                                  
CONECT   34   33   35   12                                                  
CONECT   35   34   36                                                       
CONECT   36   31   35    4                                                  
CONECT   37   15                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R,4R,5S,6S)-2-{[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxo-4H-chromen-7-yl]oxy}-3,5-dihydroxy-6-methyloxan-4-yl 2-methylpropanoic acid	Generator

Chemical Formula

C₂₅H₂₆O₁₂

Average Mass

518.4710 Da

Monoisotopic Mass

518.14243 Da

IUPAC Name

(2S,3R,4R,5S,6S)-2-{[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxo-4H-chromen-7-yl]oxy}-3,5-dihydroxy-6-methyloxan-4-yl 2-methylpropanoate

Traditional Name

(2S,3R,4R,5S,6S)-2-{[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxochromen-7-yl]oxy}-3,5-dihydroxy-6-methyloxan-4-yl 2-methylpropanoate

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)O[C@@H]1[C@@H](O)[C@H](C)O[C@@H](OC2=CC(O)=C3C(OC(C4=CC(O)=C(O)C=C4)=C(O)C3=O)=C2)[C@@H]1O

InChI Identifier

InChI=1S/C25H26O12/c1-9(2)24(33)37-23-18(29)10(3)34-25(21(23)32)35-12-7-15(28)17-16(8-12)36-22(20(31)19(17)30)11-4-5-13(26)14(27)6-11/h4-10,18,21,23,25-29,31-32H,1-3H3/t10-,18-,21+,23+,25-/m0/s1

InChI Key

XIMBHDHJSKJECM-BRBYZNOMSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Sinocrassula indica	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
3-hydroxyflavone
Hydroxyflavonoid
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Phenolic glycoside
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Chromone
Benzopyran
1-benzopyran
Catechol
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Pyran
Oxane
Monosaccharide
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Acetal
Organic oxide
Carbonyl group
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen 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	2.71	ALOGPS
logP	2.62	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.08	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	192.44 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	125.82 m³·mol⁻¹	ChemAxon
Polarizability	51.31 Å³	ChemAxon
Number of Rings	4	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

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

23651305

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Sinocrassoside B1 (NP0072316)

MOL for NP0072316 ((+)-Sinocrassoside B1)

3D MOL for NP0072316 ((+)-Sinocrassoside B1)

3D SDF for NP0072316 ((+)-Sinocrassoside B1)

3D-SDF for NP0072316 ((+)-Sinocrassoside B1)

PDB for NP0072316 ((+)-Sinocrassoside B1)

3D PDB for NP0072316 ((+)-Sinocrassoside B1)

SMILES for NP0072316 ((+)-Sinocrassoside B1)

INCHI for NP0072316 ((+)-Sinocrassoside B1)

Structure for NP0072316 ((+)-Sinocrassoside B1)

3D Structure for NP0072316 ((+)-Sinocrassoside B1)