NP-MRD: Showing NP-Card for (2s,4ar,6as,7r,9s,10r,10ar,10bs)-9-(acetyloxy)-2-(furan-3-yl)-10b-methyl-4-oxo-7-{[(2r,3r,4s,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydro-1h-naphtho[2,1-c]pyran-10-yl acetate (NP0253744)

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Record Information

Version

2.0

Created at

2022-09-07 17:42:00 UTC

Updated at

2022-09-07 17:42:01 UTC

NP-MRD ID

NP0253744

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,4ar,6as,7r,9s,10r,10ar,10bs)-9-(acetyloxy)-2-(furan-3-yl)-10b-methyl-4-oxo-7-{[(2r,3r,4s,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydro-1h-naphtho[2,1-c]pyran-10-yl acetate

Description

(2S,4aR,6aS,7R,9S,10R,10aR,10bS)-10-(acetyloxy)-2-(furan-3-yl)-10b-methyl-4-oxo-7-{[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1H-naphtho[2,1-c]pyran-9-yl acetate belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. (2s,4ar,6as,7r,9s,10r,10ar,10bs)-9-(acetyloxy)-2-(furan-3-yl)-10b-methyl-4-oxo-7-{[(2r,3r,4s,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydro-1h-naphtho[2,1-c]pyran-10-yl acetate is found in Tinospora sinensis. Based on a literature review very few articles have been published on (2S,4aR,6aS,7R,9S,10R,10aR,10bS)-10-(acetyloxy)-2-(furan-3-yl)-10b-methyl-4-oxo-7-{[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1H-naphtho[2,1-c]pyran-9-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072219422D          

 41 45  0  0  1  0            999 V2000
    0.7954   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0329   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -1.5395    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0329   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -0.1105    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079    0.6039    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7954   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0296   -0.1105    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4421   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2671   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4421    0.6039    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2671    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0296    1.3184    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4421    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2704   -0.1105    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    4.5079    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1579    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1579   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  2  4  1  0  0  0  0
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 16 18  1  0  0  0  0
  9 18  1  0  0  0  0
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  7 20  1  0  0  0  0
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 34 35  1  6  0  0  0
 36 34  1  6  0  0  0
 20 36  1  0  0  0  0
 36 37  1  0  0  0  0
  5 37  1  0  0  0  0
 37 38  1  1  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
M  END

     RDKit          3D

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    2.1446    1.9383   -1.3666 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2347    2.9992   -2.3270 C   0  0  0  0  0  0  0  0  0  0  0  0
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 32 69  1  0
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M  END


  Mrv1652309072219422D          

 41 45  0  0  1  0            999 V2000
    0.7954   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0296    1.3184    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4421    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954    1.3184    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2079    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -0.1105    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6829    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.1105    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -1.5395    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1579   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8223   -3.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4354   -3.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1499   -3.1471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9784   -2.3402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0954   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2704   -1.5395    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6829   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -3.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  1  0  0  0
  7 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 23 22  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 28 32  2  0  0  0  0
 27 33  1  0  0  0  0
 33 34  1  0  0  0  0
 23 34  1  0  0  0  0
 34 35  1  6  0  0  0
 36 34  1  6  0  0  0
 20 36  1  0  0  0  0
 36 37  1  0  0  0  0
  5 37  1  0  0  0  0
 37 38  1  1  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0253744

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1C[C@@H](O[C@@H]2O[C@@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]2CC[C@H]3C(=O)O[C@@H](C[C@@]3(C)[C@@H]2[C@H]1OC(C)=O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H38O13/c1-12(30)37-18-8-17(40-27-24(34)23(33)22(32)20(10-29)41-27)15-4-5-16-26(35)39-19(14-6-7-36-11-14)9-28(16,3)21(15)25(18)38-13(2)31/h6-7,11,15-25,27,29,32-34H,4-5,8-10H2,1-3H3/t15-,16+,17-,18+,19+,20+,21+,22-,23+,24-,25+,27-,28-/m1/s1

> <INCHI_KEY>
PESHKZMKILHZFJ-DNECIHPDSA-N

> <FORMULA>
C28H38O13

> <MOLECULAR_WEIGHT>
582.599

> <EXACT_MASS>
582.231241284

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
57.580072334252236

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,4aR,6aS,7R,9S,10R,10aR,10bS)-9-(acetyloxy)-2-(furan-3-yl)-10b-methyl-4-oxo-7-{[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1H-naphtho[2,1-c]pyran-10-yl acetate

> <JCHEM_LOGP>
-0.5802928116666669

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.200089707320487

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.210560463226727

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8612364332045663

> <JCHEM_POLAR_SURFACE_AREA>
191.42

> <JCHEM_REFRACTIVITY>
134.4195

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4aR,6aS,7R,9S,10R,10aR,10bS)-9-(acetyloxy)-2-(furan-3-yl)-10b-methyl-4-oxo-7-{[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydro-1H-naphtho[2,1-c]pyran-10-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       1.485  -2.874   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.255  -4.207   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.485  -5.541   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.795  -4.207   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.565  -2.874   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.795  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.565  -0.206   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.795   1.127   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.255   1.127   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.485  -0.206   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.055  -0.206   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.825  -1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.365  -1.540   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.825   1.127   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.365   1.127   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.055   2.461   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.825   3.795   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.485   2.461   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.255   3.795   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.105  -0.206   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.875   1.127   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.415   1.127   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.185  -0.206   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.725  -0.206   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      11.495   1.127   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      11.495  -1.540   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.725  -2.874   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.495  -4.207   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.868  -5.614   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.013  -6.645   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      13.346  -5.875   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      13.026  -4.368   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.185  -2.874   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.415  -1.540   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.645  -2.874   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.875  -1.540   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.105  -2.874   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       6.875  -4.207   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       6.105  -5.541   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.565  -5.541   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       6.875  -6.875   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   37                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    9   19                                                  
CONECT   19   18                                                            
CONECT   20    7   21   36                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   34                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   33                                                  
CONECT   28   27   29   32                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   28                                                       
CONECT   33   27   34                                                       
CONECT   34   33   23   35   36                                             
CONECT   35   34                                                            
CONECT   36   34   20   37                                                  
CONECT   37   36    5   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Value	Source
(2S,4AR,6as,7R,9S,10R,10ar,10BS)-10-(acetyloxy)-2-(furan-3-yl)-10b-methyl-4-oxo-7-{[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1H-naphtho[2,1-c]pyran-9-yl acetic acid	Generator

Chemical Formula

C₂₈H₃₈O₁₃

Average Mass

582.5990 Da

Monoisotopic Mass

582.23124 Da

IUPAC Name

(2S,4aR,6aS,7R,9S,10R,10aR,10bS)-9-(acetyloxy)-2-(furan-3-yl)-10b-methyl-4-oxo-7-{[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1H-naphtho[2,1-c]pyran-10-yl acetate

Traditional Name

(2S,4aR,6aS,7R,9S,10R,10aR,10bS)-9-(acetyloxy)-2-(furan-3-yl)-10b-methyl-4-oxo-7-{[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydro-1H-naphtho[2,1-c]pyran-10-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1C[C@@H](O[C@@H]2O[C@@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]2CC[C@H]3C(=O)O[C@@H](C[C@@]3(C)[C@@H]2[C@H]1OC(C)=O)C1=COC=C1

InChI Identifier

InChI=1S/C28H38O13/c1-12(30)37-18-8-17(40-27-24(34)23(33)22(32)20(10-29)41-27)15-4-5-16-26(35)39-19(14-6-7-36-11-14)9-28(16,3)21(15)25(18)38-13(2)31/h6-7,11,15-25,27,29,32-34H,4-5,8-10H2,1-3H3/t15-,16+,17-,18+,19+,20+,21+,22-,23+,24-,25+,27-,28-/m1/s1

InChI Key

PESHKZMKILHZFJ-DNECIHPDSA-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 naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Naphthalene
Tricarboxylic acid or derivatives
Delta_valerolactone
Delta valerolactone
Pyran
Oxane
Monosaccharide
Cyclitol or derivatives
Heteroaromatic compound
Furan
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Polyol
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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	-0.58	ChemAxon
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	191.42 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	134.42 m³·mol⁻¹	ChemAxon
Polarizability	57.58 Å³	ChemAxon
Number of Rings	5	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

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

163031792

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,4ar,6as,7r,9s,10r,10ar,10bs)-9-(acetyloxy)-2-(furan-3-yl)-10b-methyl-4-oxo-7-{[(2r,3r,4s,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydro-1h-naphtho[2,1-c]pyran-10-yl acetate (NP0253744)

MOL for NP0253744 ((2s,4ar,6as,7r,9s,10r,10ar,10bs)-9-(acetyloxy)-2-(furan-3-yl)-10b-methyl-4-oxo-7-{[(2r,3r,4s,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydro-1h-naphtho[2,1-c]pyran-10-yl acetate)

3D MOL for NP0253744 ((2s,4ar,6as,7r,9s,10r,10ar,10bs)-9-(acetyloxy)-2-(furan-3-yl)-10b-methyl-4-oxo-7-{[(2r,3r,4s,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydro-1h-naphtho[2,1-c]pyran-10-yl acetate)

3D SDF for NP0253744 ((2s,4ar,6as,7r,9s,10r,10ar,10bs)-9-(acetyloxy)-2-(furan-3-yl)-10b-methyl-4-oxo-7-{[(2r,3r,4s,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydro-1h-naphtho[2,1-c]pyran-10-yl acetate)

3D-SDF for NP0253744 ((2s,4ar,6as,7r,9s,10r,10ar,10bs)-9-(acetyloxy)-2-(furan-3-yl)-10b-methyl-4-oxo-7-{[(2r,3r,4s,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydro-1h-naphtho[2,1-c]pyran-10-yl acetate)

PDB for NP0253744 ((2s,4ar,6as,7r,9s,10r,10ar,10bs)-9-(acetyloxy)-2-(furan-3-yl)-10b-methyl-4-oxo-7-{[(2r,3r,4s,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydro-1h-naphtho[2,1-c]pyran-10-yl acetate)

3D PDB for NP0253744 ((2s,4ar,6as,7r,9s,10r,10ar,10bs)-9-(acetyloxy)-2-(furan-3-yl)-10b-methyl-4-oxo-7-{[(2r,3r,4s,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydro-1h-naphtho[2,1-c]pyran-10-yl acetate)

SMILES for NP0253744 ((2s,4ar,6as,7r,9s,10r,10ar,10bs)-9-(acetyloxy)-2-(furan-3-yl)-10b-methyl-4-oxo-7-{[(2r,3r,4s,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydro-1h-naphtho[2,1-c]pyran-10-yl acetate)

INCHI for NP0253744 ((2s,4ar,6as,7r,9s,10r,10ar,10bs)-9-(acetyloxy)-2-(furan-3-yl)-10b-methyl-4-oxo-7-{[(2r,3r,4s,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydro-1h-naphtho[2,1-c]pyran-10-yl acetate)

Structure for NP0253744 ((2s,4ar,6as,7r,9s,10r,10ar,10bs)-9-(acetyloxy)-2-(furan-3-yl)-10b-methyl-4-oxo-7-{[(2r,3r,4s,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydro-1h-naphtho[2,1-c]pyran-10-yl acetate)

3D Structure for NP0253744 ((2s,4ar,6as,7r,9s,10r,10ar,10bs)-9-(acetyloxy)-2-(furan-3-yl)-10b-methyl-4-oxo-7-{[(2r,3r,4s,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydro-1h-naphtho[2,1-c]pyran-10-yl acetate)