NP-MRD: Showing NP-Card for (5R,6R,8S,9R,10S,12S)-15,16-epoxy-2-oxo-6-O-(beta-D-glucopyranosyl)-clero+ (NP0035184)

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Record Information

Version

2.0

Created at

2021-06-20 18:42:05 UTC

Updated at

2021-06-30 00:06:01 UTC

NP-MRD ID

NP0035184

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5R,6R,8S,9R,10S,12S)-15,16-epoxy-2-oxo-6-O-(beta-D-glucopyranosyl)-clero+

Provided By

JEOL Database JEOL Logo

Description

(5R,6R,8S,9R,10S,12S)-15,16-epoxy-2-oxo-6-O-(beta-D-glucopyranosyl)-clero+ is found in Tinospora crispa. (5R,6R,8S,9R,10S,12S)-15,16-epoxy-2-oxo-6-O-(beta-D-glucopyranosyl)-clero+ was first documented in 2010 (Choudhary, M. I., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120423D          

 73 77  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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 14 52  1  1
 25 26  1  0
 19 18  1  0
 29 28  1  0
 28 27  1  0
 10 11  1  0
 15 19  2  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 38 25  1  0
 23 56  1  1
 25 24  1  0
  2  1  1  0
 29 30  1  0
 27 26  1  0
 31 64  1  0
 27 60  1  6
 32 65  1  1
 33 66  1  0
 34 67  1  6
 35 68  1  0
 36 69  1  1
 37 70  1  0
 30 62  1  0
 30 63  1  0
 29 61  1  6
  6 43  1  0
  9 44  1  0
  9 45  1  0
 25 59  1  6
 24 57  1  0
 24 58  1  0
 13 50  1  0
 13 51  1  0
 12 47  1  0
 12 48  1  0
 12 49  1  0
 39 71  1  0
 39 72  1  0
 39 73  1  0
 19 55  1  0
 17 54  1  0
 16 53  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
M  END


  Mrv1652306202120423D          

 73 77  0  0  0  0            999 V2000
   -1.5823    0.4729   -5.6872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9782   -0.5469   -4.8912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8250   -1.1500   -4.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0217   -0.9139   -3.9283 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1221   -2.1762   -3.1807 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1030   -2.5731   -3.5659 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8206   -3.6393   -2.8474 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9880   -3.8882   -3.1347 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0601   -4.4467   -1.8342 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9168   -3.5977   -1.0016 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2689   -2.8510    0.2397 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3979   -3.9156    1.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8317   -1.8572   -0.1805 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2610   -0.9638    0.9775 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3608   -0.0213    0.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3365    1.4049    0.5629 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5734    1.8181    0.1300 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3677    0.7478   -0.1185 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6335   -0.3597    0.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1376   -0.2307    1.4846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0242   -0.8388    1.7784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8035   -0.3057    2.5706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3767   -2.1591    1.0965 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7194   -2.0114    0.3504 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5322   -1.5674   -1.1028 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6935   -0.4093   -1.1341 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3872    0.8462   -1.0677 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9828    0.9650    0.2180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5889    2.2320    0.4809 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2389    2.1491    1.8675 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2540    2.0702    2.8945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5341    3.3436    0.4025 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0938    4.6400    0.6335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9190    3.3279   -0.9961 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8744    4.3123   -1.0881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3390    1.9524   -1.3120 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8735    1.9533   -2.6716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8570   -2.7185   -1.9387 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9794   -3.6679   -2.4564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7904    0.9815   -6.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0937    1.2118   -5.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2789    0.0259   -6.4029 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6311   -2.1732   -4.4248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4869   -5.2195   -2.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7768   -4.9787   -1.2039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5728   -4.3471   -0.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6448   -3.5008    2.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2743   -4.7638    1.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3300   -4.3062    0.7479 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7029   -2.4024   -0.5639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4941   -1.2215   -1.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6539   -1.5615    1.8088 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5145    2.0511    0.8394 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0231    2.7861   -0.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1445   -1.3004   -0.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5998   -2.8204    1.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2589   -2.9664    0.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3736   -1.3099    0.8779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5153   -1.3286   -1.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1576    0.8755   -1.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3886    2.4011   -0.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8771    1.2628    1.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8524    3.0340    2.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7794    1.2143    2.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309    3.1937    1.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2235    4.7115    1.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6615    3.6149   -1.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2636    5.1268   -0.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4570    1.7680   -0.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2828    2.7309   -2.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5161   -4.1462   -1.6297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5751   -4.4647   -3.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7307   -3.1366   -3.0497 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 23  1  0  0  0  0
 11 23  1  0  0  0  0
 32 33  1  0  0  0  0
 34 35  1  0  0  0  0
 36 37  1  0  0  0  0
 30 31  1  0  0  0  0
  7  6  1  0  0  0  0
 11 13  1  0  0  0  0
 23 21  1  0  0  0  0
 21 20  1  0  0  0  0
 20 14  1  0  0  0  0
 14 13  1  0  0  0  0
  5  3  1  0  0  0  0
 27 36  1  0  0  0  0
  3  2  1  0  0  0  0
 36 34  1  0  0  0  0
  3  4  2  0  0  0  0
 34 32  1  0  0  0  0
 21 22  2  0  0  0  0
  7  9  1  0  0  0  0
 14 15  1  0  0  0  0
  6  5  2  0  0  0  0
 11 12  1  1  0  0  0
  5 38  1  0  0  0  0
  7  8  2  0  0  0  0
 10  9  1  0  0  0  0
 10 46  1  1  0  0  0
 10 38  1  0  0  0  0
 38 39  1  6  0  0  0
 32 29  1  0  0  0  0
 14 52  1  1  0  0  0
 25 26  1  0  0  0  0
 19 18  1  0  0  0  0
 29 28  1  0  0  0  0
 28 27  1  0  0  0  0
 10 11  1  0  0  0  0
 15 19  2  0  0  0  0
 18 17  1  0  0  0  0
 17 16  2  0  0  0  0
 16 15  1  0  0  0  0
 38 25  1  0  0  0  0
 23 56  1  1  0  0  0
 25 24  1  0  0  0  0
  2  1  1  0  0  0  0
 29 30  1  0  0  0  0
 27 26  1  0  0  0  0
 31 64  1  0  0  0  0
 27 60  1  6  0  0  0
 32 65  1  1  0  0  0
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 34 67  1  6  0  0  0
 35 68  1  0  0  0  0
 36 69  1  1  0  0  0
 37 70  1  0  0  0  0
 30 62  1  0  0  0  0
 30 63  1  0  0  0  0
 29 61  1  6  0  0  0
  6 43  1  0  0  0  0
  9 44  1  0  0  0  0
  9 45  1  0  0  0  0
 25 59  1  6  0  0  0
 24 57  1  0  0  0  0
 24 58  1  0  0  0  0
 13 50  1  0  0  0  0
 13 51  1  0  0  0  0
 12 47  1  0  0  0  0
 12 48  1  0  0  0  0
 12 49  1  0  0  0  0
 39 71  1  0  0  0  0
 39 72  1  0  0  0  0
 39 73  1  0  0  0  0
 19 55  1  0  0  0  0
 17 54  1  0  0  0  0
 16 53  1  0  0  0  0
  1 40  1  0  0  0  0
  1 41  1  0  0  0  0
  1 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0035184

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@]1([H])O[C@]([H])(O[C@]2([H])C([H])([H])[C@]3([H])C(=O)O[C@]([H])(C4=C([H])OC([H])=C4[H])C([H])([H])[C@]3(C([H])([H])[H])[C@]3([H])C([H])([H])C(=O)C([H])=C(C(=O)OC([H])([H])[H])[C@]23C([H])([H])[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H34O12/c1-26-9-16(12-4-5-36-11-12)37-24(34)14(26)8-19(39-25-22(32)21(31)20(30)17(10-28)38-25)27(2)15(23(33)35-3)6-13(29)7-18(26)27/h4-6,11,14,16-22,25,28,30-32H,7-10H2,1-3H3/t14-,16+,17+,18+,19-,20+,21-,22+,25-,26+,27+/m1/s1

> <INCHI_KEY>
YMNCHYBBYDAUSZ-RPXCJDHLSA-N

> <FORMULA>
C27H34O12

> <MOLECULAR_WEIGHT>
550.557

> <EXACT_MASS>
550.205026535

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
53.333250448915166

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2S,4aS,6R,6aR,10aS,10bR)-2-(furan-3-yl)-6a,10b-dimethyl-4,9-dioxo-6-{[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,2H,4H,4aH,5H,6H,6aH,9H,10H,10aH,10bH-naphtho[2,1-c]pyran-7-carboxylate

> <ALOGPS_LOGP>
0.52

> <JCHEM_LOGP>
0.004806651999999176

> <ALOGPS_LOGS>
-2.84

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.20007865483381

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.210532704988514

> <JCHEM_PKA_STRONGEST_BASIC>
-2.861384891716726

> <JCHEM_POLAR_SURFACE_AREA>
182.19

> <JCHEM_REFRACTIVITY>
130.10720000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.04e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2S,4aS,6R,6aR,10aS,10bR)-2-(furan-3-yl)-6a,10b-dimethyl-4,9-dioxo-6-{[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,2H,4aH,5H,6H,10H,10aH-naphtho[2,1-c]pyran-7-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 73 77  0  0  0  0  0  0  0  0999 V2000
   -1.5823    0.4729   -5.6872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9782   -0.5469   -4.8912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8250   -1.1500   -4.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0217   -0.9139   -3.9283 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1221   -2.1762   -3.1807 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1030   -2.5731   -3.5659 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8206   -3.6393   -2.8474 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9880   -3.8882   -3.1347 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0601   -4.4467   -1.8342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9168   -3.5977   -1.0016 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2689   -2.8510    0.2397 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3979   -3.9156    1.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8317   -1.8572   -0.1805 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2610   -0.9638    0.9775 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.9794   -3.6679   -2.4564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7904    0.9815   -6.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6311   -2.1732   -4.4248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4869   -5.2195   -2.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7768   -4.9787   -1.2039 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.582   0.473  -5.687  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.978  -0.547  -4.891  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.825  -1.150  -4.020  0.00  0.00           C+0
HETATM    4  O   UNK     0      -3.022  -0.914  -3.928  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.122  -2.176  -3.181  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.103  -2.573  -3.566  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.821  -3.639  -2.847  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.988  -3.888  -3.135  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.060  -4.447  -1.834  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.917  -3.598  -1.002  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.269  -2.851   0.240  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.398  -3.916   1.168  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.832  -1.857  -0.181  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.261  -0.964   0.978  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.361  -0.021   0.576  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.337   1.405   0.563  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.573   1.818   0.130  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.368   0.748  -0.119  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.634  -0.360   0.155  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.138  -0.231   1.485  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.024  -0.839   1.778  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.804  -0.306   2.571  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.377  -2.159   1.097  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.719  -2.011   0.350  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.532  -1.567  -1.103  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.694  -0.409  -1.134  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.387   0.846  -1.068  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.983   0.965   0.218  0.00  0.00           O+0
HETATM   29  C   UNK     0      -3.589   2.232   0.481  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.239   2.149   1.867  0.00  0.00           C+0
HETATM   31  O   UNK     0      -3.254   2.070   2.894  0.00  0.00           O+0
HETATM   32  C   UNK     0      -2.534   3.344   0.403  0.00  0.00           C+0
HETATM   33  O   UNK     0      -3.094   4.640   0.634  0.00  0.00           O+0
HETATM   34  C   UNK     0      -1.919   3.328  -0.996  0.00  0.00           C+0
HETATM   35  O   UNK     0      -0.874   4.312  -1.088  0.00  0.00           O+0
HETATM   36  C   UNK     0      -1.339   1.952  -1.312  0.00  0.00           C+0
HETATM   37  O   UNK     0      -0.874   1.953  -2.672  0.00  0.00           O+0
HETATM   38  C   UNK     0      -1.857  -2.719  -1.939  0.00  0.00           C+0
HETATM   39  C   UNK     0      -2.979  -3.668  -2.456  0.00  0.00           C+0
HETATM   40  H   UNK     0      -0.790   0.982  -6.244  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.094   1.212  -5.063  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.279   0.026  -6.403  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.631  -2.173  -4.425  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.487  -5.220  -2.388  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.777  -4.979  -1.204  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.573  -4.347  -0.530  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.645  -3.501   2.152  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.274  -4.764   1.342  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.330  -4.306   0.748  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.703  -2.402  -0.564  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.494  -1.222  -1.002  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.654  -1.562   1.809  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.515   2.051   0.839  0.00  0.00           H+0
HETATM   54  H   UNK     0       4.023   2.786  -0.042  0.00  0.00           H+0
HETATM   55  H   UNK     0       4.144  -1.300  -0.001  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.600  -2.820   1.948  0.00  0.00           H+0
HETATM   57  H   UNK     0      -3.259  -2.966   0.378  0.00  0.00           H+0
HETATM   58  H   UNK     0      -3.374  -1.310   0.878  0.00  0.00           H+0
HETATM   59  H   UNK     0      -3.515  -1.329  -1.527  0.00  0.00           H+0
HETATM   60  H   UNK     0      -3.158   0.876  -1.848  0.00  0.00           H+0
HETATM   61  H   UNK     0      -4.389   2.401  -0.252  0.00  0.00           H+0
HETATM   62  H   UNK     0      -4.877   1.263   1.948  0.00  0.00           H+0
HETATM   63  H   UNK     0      -4.852   3.034   2.062  0.00  0.00           H+0
HETATM   64  H   UNK     0      -2.779   1.214   2.767  0.00  0.00           H+0
HETATM   65  H   UNK     0      -1.731   3.194   1.135  0.00  0.00           H+0
HETATM   66  H   UNK     0      -3.224   4.712   1.600  0.00  0.00           H+0
HETATM   67  H   UNK     0      -2.662   3.615  -1.751  0.00  0.00           H+0
HETATM   68  H   UNK     0      -1.264   5.127  -0.709  0.00  0.00           H+0
HETATM   69  H   UNK     0      -0.457   1.768  -0.688  0.00  0.00           H+0
HETATM   70  H   UNK     0      -0.283   2.731  -2.730  0.00  0.00           H+0
HETATM   71  H   UNK     0      -3.516  -4.146  -1.630  0.00  0.00           H+0
HETATM   72  H   UNK     0      -2.575  -4.465  -3.091  0.00  0.00           H+0
HETATM   73  H   UNK     0      -3.731  -3.137  -3.050  0.00  0.00           H+0
CONECT    1    2   40   41   42                                             
CONECT    2    3    1                                                       
CONECT    3    5    2    4                                                  
CONECT    4    3                                                            
CONECT    5    3    6   38                                                  
CONECT    6    7    5   43                                                  
CONECT    7    6    9    8                                                  
CONECT    8    7                                                            
CONECT    9    7   10   44   45                                             
CONECT   10    9   46   38   11                                             
CONECT   11   23   13   12   10                                             
CONECT   12   11   47   48   49                                             
CONECT   13   11   14   50   51                                             
CONECT   14   20   13   15   52                                             
CONECT   15   14   19   16                                                  
CONECT   16   17   15   53                                                  
CONECT   17   18   16   54                                                  
CONECT   18   19   17                                                       
CONECT   19   18   15   55                                                  
CONECT   20   21   14                                                       
CONECT   21   23   20   22                                                  
CONECT   22   21                                                            
CONECT   23   24   11   21   56                                             
CONECT   24   23   25   57   58                                             
CONECT   25   26   38   24   59                                             
CONECT   26   25   27                                                       
CONECT   27   36   28   26   60                                             
CONECT   28   29   27                                                       
CONECT   29   32   28   30   61                                             
CONECT   30   31   29   62   63                                             
CONECT   31   30   64                                                       
CONECT   32   33   34   29   65                                             
CONECT   33   32   66                                                       
CONECT   34   35   36   32   67                                             
CONECT   35   34   68                                                       
CONECT   36   37   27   34   69                                             
CONECT   37   36   70                                                       
CONECT   38    5   10   39   25                                             
CONECT   39   38   71   72   73                                             
CONECT   40    1                                                            
CONECT   41    1                                                            
CONECT   42    1                                                            
CONECT   43    6                                                            
CONECT   44    9                                                            
CONECT   45    9                                                            
CONECT   46   10                                                            
CONECT   47   12                                                            
CONECT   48   12                                                            
CONECT   49   12                                                            
CONECT   50   13                                                            
CONECT   51   13                                                            
CONECT   52   14                                                            
CONECT   53   16                                                            
CONECT   54   17                                                            
CONECT   55   19                                                            
CONECT   56   23                                                            
CONECT   57   24                                                            
CONECT   58   24                                                            
CONECT   59   25                                                            
CONECT   60   27                                                            
CONECT   61   29                                                            
CONECT   62   30                                                            
CONECT   63   30                                                            
CONECT   64   31                                                            
CONECT   65   32                                                            
CONECT   66   33                                                            
CONECT   67   34                                                            
CONECT   68   35                                                            
CONECT   69   36                                                            
CONECT   70   37                                                            
CONECT   71   39                                                            
CONECT   72   39                                                            
CONECT   73   39                                                            
MASTER        0    0    0    0    0    0    0    0   73    0  154    0
END

RDKit          3D

73 77  0  0  0  0  0  0  0  0999 V2000
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    0.4941   -1.2215   -1.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6539   -1.5615    1.8088 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5145    2.0511    0.8394 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0231    2.7861   -0.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1445   -1.3004   -0.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5998   -2.8204    1.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2589   -2.9664    0.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3736   -1.3099    0.8779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5153   -1.3286   -1.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1576    0.8755   -1.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3886    2.4011   -0.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8771    1.2628    1.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8524    3.0340    2.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7794    1.2143    2.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309    3.1937    1.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2235    4.7115    1.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6615    3.6149   -1.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2636    5.1268   -0.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4570    1.7680   -0.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2828    2.7309   -2.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5161   -4.1462   -1.6297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5751   -4.4647   -3.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7307   -3.1366   -3.0497 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 23  1  0
 11 23  1  0
 32 33  1  0
 34 35  1  0
 36 37  1  0
 30 31  1  0
  7  6  1  0
 11 13  1  0
 23 21  1  0
 21 20  1  0
 20 14  1  0
 14 13  1  0
  5  3  1  0
 27 36  1  0
  3  2  1  0
 36 34  1  0
  3  4  2  0
 34 32  1  0
 21 22  2  0
  7  9  1  0
 14 15  1  0
  6  5  2  0
 11 12  1  1
  5 38  1  0
  7  8  2  0
 10  9  1  0
 10 46  1  1
 10 38  1  0
 38 39  1  6
 32 29  1  0
 14 52  1  1
 25 26  1  0
 19 18  1  0
 29 28  1  0
 28 27  1  0
 10 11  1  0
 15 19  2  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 38 25  1  0
 23 56  1  1
 25 24  1  0
  2  1  1  0
 29 30  1  0
 27 26  1  0
 31 64  1  0
 27 60  1  6
 32 65  1  1
 33 66  1  0
 34 67  1  6
 35 68  1  0
 36 69  1  1
 37 70  1  0
 30 62  1  0
 30 63  1  0
 29 61  1  6
  6 43  1  0
  9 44  1  0
  9 45  1  0
 25 59  1  6
 24 57  1  0
 24 58  1  0
 13 50  1  0
 13 51  1  0
 12 47  1  0
 12 48  1  0
 12 49  1  0
 39 71  1  0
 39 72  1  0
 39 73  1  0
 19 55  1  0
 17 54  1  0
 16 53  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₄O₁₂

Average Mass

550.5570 Da

Monoisotopic Mass

550.20503 Da

IUPAC Name

methyl (2S,4aS,6R,6aR,10aS,10bR)-2-(furan-3-yl)-6a,10b-dimethyl-4,9-dioxo-6-{[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,2H,4H,4aH,5H,6H,6aH,9H,10H,10aH,10bH-naphtho[2,1-c]pyran-7-carboxylate

Traditional Name

methyl (2S,4aS,6R,6aR,10aS,10bR)-2-(furan-3-yl)-6a,10b-dimethyl-4,9-dioxo-6-{[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,2H,4aH,5H,6H,10H,10aH-naphtho[2,1-c]pyran-7-carboxylate

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])[C@]1([H])O[C@]([H])(O[C@]2([H])C([H])([H])[C@]3([H])C(=O)O[C@]([H])(C4=C([H])OC([H])=C4[H])C([H])([H])[C@]3(C([H])([H])[H])[C@]3([H])C([H])([H])C(=O)C([H])=C(C(=O)OC([H])([H])[H])[C@]23C([H])([H])[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]1([H])O[H]

InChI Identifier

InChI=1S/C27H34O12/c1-26-9-16(12-4-5-36-11-12)37-24(34)14(26)8-19(39-25-22(32)21(31)20(30)17(10-28)38-25)27(2)15(23(33)35-3)6-13(29)7-18(26)27/h4-6,11,14,16-22,25,28,30-32H,7-10H2,1-3H3/t14-,16+,17+,18+,19-,20+,21-,22+,25-,26+,27+/m1/s1

InChI Key

YMNCHYBBYDAUSZ-RPXCJDHLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Tinospora crispa	JEOL database	Choudhary, M. I., et al, J. Nat. Prod. 73, 541 (2010)

Chemical Taxonomy

Classification

Not classified

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	0.52	ALOGPS
logP	0.0048	ChemAxon
logS	-2.8	ALOGPS
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	182.19 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	130.11 m³·mol⁻¹	ChemAxon
Polarizability	53.33 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

Not Available

References

General References

Choudhary, M. I., et al. (2010). Choudhary, M. I., et al, J. Nat. Prod. 73, 541 (2010). J. Nat. Prod..

Showing NP-Card for (5R,6R,8S,9R,10S,12S)-15,16-epoxy-2-oxo-6-O-(beta-D-glucopyranosyl)-clero+ (NP0035184)

MOL for NP0035184 ((5R,6R,8S,9R,10S,12S)-15,16-epoxy-2-oxo-6-O-(beta-D-glucopyranosyl)-clero+)

3D MOL for NP0035184 ((5R,6R,8S,9R,10S,12S)-15,16-epoxy-2-oxo-6-O-(beta-D-glucopyranosyl)-clero+)

3D SDF for NP0035184 ((5R,6R,8S,9R,10S,12S)-15,16-epoxy-2-oxo-6-O-(beta-D-glucopyranosyl)-clero+)

3D-SDF for NP0035184 ((5R,6R,8S,9R,10S,12S)-15,16-epoxy-2-oxo-6-O-(beta-D-glucopyranosyl)-clero+)

PDB for NP0035184 ((5R,6R,8S,9R,10S,12S)-15,16-epoxy-2-oxo-6-O-(beta-D-glucopyranosyl)-clero+)

3D PDB for NP0035184 ((5R,6R,8S,9R,10S,12S)-15,16-epoxy-2-oxo-6-O-(beta-D-glucopyranosyl)-clero+)

SMILES for NP0035184 ((5R,6R,8S,9R,10S,12S)-15,16-epoxy-2-oxo-6-O-(beta-D-glucopyranosyl)-clero+)

INCHI for NP0035184 ((5R,6R,8S,9R,10S,12S)-15,16-epoxy-2-oxo-6-O-(beta-D-glucopyranosyl)-clero+)

Structure for NP0035184 ((5R,6R,8S,9R,10S,12S)-15,16-epoxy-2-oxo-6-O-(beta-D-glucopyranosyl)-clero+)

3D Structure for NP0035184 ((5R,6R,8S,9R,10S,12S)-15,16-epoxy-2-oxo-6-O-(beta-D-glucopyranosyl)-clero+)