NP-MRD: Showing NP-Card for 2-(furan-3-yl)-4a,9,10-trihydroxy-10b-methyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydronaphtho[2,1-c]pyran-4-one (NP0320640)

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Record Information

Version

2.0

Created at

2022-09-11 22:24:18 UTC

Updated at

2022-09-11 22:24:19 UTC

NP-MRD ID

NP0320640

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(furan-3-yl)-4a,9,10-trihydroxy-10b-methyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydronaphtho[2,1-c]pyran-4-one

Description

2-(Furan-3-yl)-4a,9,10-trihydroxy-10b-methyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1H-naphtho[2,1-c]pyran-4-one belongs to the class of organic compounds known as naphthopyranone glycosides. Naphthopyranone glycosides are compounds containing a carbohydrate moiety glycosidically linked to a naphthopyranone moiety. 2-(furan-3-yl)-4a,9,10-trihydroxy-10b-methyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydronaphtho[2,1-c]pyran-4-one is found in Tinospora sinensis. 2-(Furan-3-yl)-4a,9,10-trihydroxy-10b-methyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1H-naphtho[2,1-c]pyran-4-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241516452D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004241516452D          

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 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
  2 19  1  0  0  0  0
 12 19  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  1  0  0  0  0
  4 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 32 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0320640

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CC(OC(=O)C1(O)CCC1C(CC(O)C(O)C21)OC1OC(CO)C(O)C(O)C1O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H34O12/c1-23-7-14(10-3-5-33-9-10)36-22(31)24(23,32)4-2-11-13(6-12(26)17(27)16(11)23)34-21-20(30)19(29)18(28)15(8-25)35-21/h3,5,9,11-21,25-30,32H,2,4,6-8H2,1H3

> <INCHI_KEY>
CFUUZLCSNHHURL-UHFFFAOYSA-N

> <FORMULA>
C24H34O12

> <MOLECULAR_WEIGHT>
514.524

> <EXACT_MASS>
514.205026535

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
51.264051918365396

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(furan-3-yl)-4a,9,10-trihydroxy-10b-methyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1H-naphtho[2,1-c]pyran-4-one

> <ALOGPS_LOGP>
-1.63

> <JCHEM_LOGP>
-2.2099687553333336

> <ALOGPS_LOGS>
-1.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.3805042093961

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.792703524831866

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8886357326212644

> <JCHEM_POLAR_SURFACE_AREA>
199.51

> <JCHEM_REFRACTIVITY>
117.51650000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.14e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(furan-3-yl)-4a,9,10-trihydroxy-10b-methyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydronaphtho[2,1-c]pyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       7.494   0.770   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.494  -1.897   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.954  -1.897   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.874   3.437   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.206  -1.897   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.746  -1.897   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.516  -3.231   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -4.056  -3.231   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.826  -4.565   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -6.366  -4.565   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -4.826  -1.897   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -6.366  -1.897   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -4.056  -0.564   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.826   0.770   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.516  -0.564   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.746   0.770   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       7.494   3.437   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.867   4.844   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       8.012   5.875   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       9.345   5.105   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.025   3.598   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8   19                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   32                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    2    9   10                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    2   12                                                  
CONECT   20   13   21                                                       
CONECT   21   20   22   30                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   21   31                                                  
CONECT   31   30                                                            
CONECT   32    4   33   36                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   32                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₄O₁₂

Average Mass

514.5240 Da

Monoisotopic Mass

514.20503 Da

IUPAC Name

2-(furan-3-yl)-4a,9,10-trihydroxy-10b-methyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1H-naphtho[2,1-c]pyran-4-one

Traditional Name

2-(furan-3-yl)-4a,9,10-trihydroxy-10b-methyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydronaphtho[2,1-c]pyran-4-one

CAS Registry Number

Not Available

SMILES

CC12CC(OC(=O)C1(O)CCC1C(CC(O)C(O)C21)OC1OC(CO)C(O)C(O)C1O)C1=COC=C1

InChI Identifier

InChI=1S/C24H34O12/c1-23-7-14(10-3-5-33-9-10)36-22(31)24(23,32)4-2-11-13(6-12(26)17(27)16(11)23)34-21-20(30)19(29)18(28)15(8-25)35-21/h3,5,9,11-21,25-30,32H,2,4,6-8H2,1H3

InChI Key

CFUUZLCSNHHURL-UHFFFAOYSA-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
Tinospora sinensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyranone glycosides. Naphthopyranone glycosides are compounds containing a carbohydrate moiety glycosidically linked to a naphthopyranone moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Naphthopyranones

Direct Parent

Naphthopyranone glycosides

Alternative Parents

Substituents

Naphthopyranone glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Naphthalene
Delta valerolactone
Delta_valerolactone
Cyclitol or derivatives
Monosaccharide
Pyran
Oxane
Cyclic alcohol
Furan
Heteroaromatic compound
Tertiary alcohol
Lactone
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Oxacycle
Acetal
Carboxylic acid derivative
Polyol
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Organic oxide
Carbonyl group
Primary alcohol
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	-1.6	ALOGPS
logP	-2.2	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	11.79	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	199.51 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	117.52 m³·mol⁻¹	ChemAxon
Polarizability	51.26 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(furan-3-yl)-4a,9,10-trihydroxy-10b-methyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydronaphtho[2,1-c]pyran-4-one (NP0320640)

MOL for NP0320640 (2-(furan-3-yl)-4a,9,10-trihydroxy-10b-methyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydronaphtho[2,1-c]pyran-4-one)

3D MOL for NP0320640 (2-(furan-3-yl)-4a,9,10-trihydroxy-10b-methyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydronaphtho[2,1-c]pyran-4-one)

3D SDF for NP0320640 (2-(furan-3-yl)-4a,9,10-trihydroxy-10b-methyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydronaphtho[2,1-c]pyran-4-one)

3D-SDF for NP0320640 (2-(furan-3-yl)-4a,9,10-trihydroxy-10b-methyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydronaphtho[2,1-c]pyran-4-one)

PDB for NP0320640 (2-(furan-3-yl)-4a,9,10-trihydroxy-10b-methyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydronaphtho[2,1-c]pyran-4-one)

3D PDB for NP0320640 (2-(furan-3-yl)-4a,9,10-trihydroxy-10b-methyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydronaphtho[2,1-c]pyran-4-one)

SMILES for NP0320640 (2-(furan-3-yl)-4a,9,10-trihydroxy-10b-methyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydronaphtho[2,1-c]pyran-4-one)

INCHI for NP0320640 (2-(furan-3-yl)-4a,9,10-trihydroxy-10b-methyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydronaphtho[2,1-c]pyran-4-one)

Structure for NP0320640 (2-(furan-3-yl)-4a,9,10-trihydroxy-10b-methyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydronaphtho[2,1-c]pyran-4-one)

3D Structure for NP0320640 (2-(furan-3-yl)-4a,9,10-trihydroxy-10b-methyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydronaphtho[2,1-c]pyran-4-one)