NP-MRD: Showing NP-Card for (-)-Norcaesalpinin MB (NP0079230)

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Record Information

Version

2.0

Created at

2022-04-29 00:16:14 UTC

Updated at

2022-04-29 00:16:14 UTC

NP-MRD ID

NP0079230

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Norcaesalpinin MB

Description

(2S,3S,4R,4aS,10aR)-2,4-bis(acetyloxy)-7-formyl-6,10a-dihydroxy-1,1,4a,8-tetramethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-3-yl acetate belongs to the class of organic compounds known as hydrophenanthrenes. These are a phenanthrene derivative where at least one ring CC bond is substituted by hydrogenation. (-)-Norcaesalpinin MB is found in Caesalpinia crista . Based on a literature review very few articles have been published on (2S,3S,4R,4aS,10aR)-2,4-bis(acetyloxy)-7-formyl-6,10a-dihydroxy-1,1,4a,8-tetramethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-3-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292202162D          

 34 36  0  0  1  0            999 V2000
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3977    1.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2732    1.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4 10  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 17 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 16 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 15 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 14 33  1  6  0  0  0
 13 34  1  1  0  0  0
M  END

     RDKit          3D

 66 68  0  0  0  0  0  0  0  0999 V2000
   -1.7668    2.2743   -3.1771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0253    2.0146   -1.7431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8589    2.7302   -1.1561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3898    1.0211   -1.0255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6791    0.8348    0.3080 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3175   -0.5263    0.5988 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2319   -0.7717   -0.4559 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3610   -1.6278    0.8573 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7903   -2.7652   -0.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5258   -2.2707    2.2336 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0411   -1.3264    0.4966 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0618   -1.2708   -0.9208 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0180   -2.4386    0.8213 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3184   -2.1271    0.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4655   -0.7345   -0.3367 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6352    0.3314    0.0243 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8768    1.5509   -0.5083 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9305    1.7859   -1.4089 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0253    3.0785   -1.8459 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7520    0.7500   -1.7696 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8583    0.9300   -2.7083 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1399    2.0017   -3.2385 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5026   -0.5104   -1.2188 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4550   -1.5872   -1.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5787    0.0026    0.9824 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3213   -0.1647    2.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5074    0.9706    1.2431 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1235    2.2497    1.5648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2950    2.8504    2.7876 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1367    4.2369    3.0889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8442    2.1574    3.6523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9777    1.6173   -3.5938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6921    2.0803   -3.7583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5361    3.3559   -3.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4414    1.5702    0.6340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9595   -0.4291    1.5254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3972   -1.7816   -1.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0359   -1.5213   -2.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9735   -0.1243   -1.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5852   -2.5165   -1.1407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9072   -2.8442    0.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3937   -3.7379    0.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8170   -3.1155    2.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5434   -2.7248    2.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4943   -1.5758    3.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3953   -2.0768   -1.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1219   -2.6515    1.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6049   -3.3516    0.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4028   -2.7581   -0.8164 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1545   -2.4458    0.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2240    2.3546   -0.2222 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7012    3.4059   -2.4724 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5010    0.0880   -2.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5055   -1.1877   -1.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2818   -1.8763   -2.6634 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3303   -2.4879   -0.9918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1016   -0.9086    2.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6103   -0.4271    3.1354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9762    0.5821    2.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0806    4.4013    4.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2217    4.3371    2.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4725    4.9769    2.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  6 11  1  0
 11 12  1  6
 11 13  1  0
 11 14  1  0
 14 15  1  6
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 26  2  0
 26 27  1  0
 26 23  1  0
 23 24  1  0
 24 25  2  0
 23 21  2  0
 21 22  1  0
 21 20  1  0
 20 19  2  0
 19 28  1  0
 28 29  1  1
 28 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  2  0
 30  5  1  0
 28 14  1  0
 19 18  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  5 38  1  1
  6 39  1  1
  9 40  1  0
  9 41  1  0
  9 42  1  0
 12 43  1  0
 12 44  1  0
 12 45  1  0
 13 46  1  0
 13 47  1  0
 13 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 27 57  1  0
 27 58  1  0
 27 59  1  0
 24 56  1  0
 22 55  1  0
 20 54  1  0
 29 60  1  0
 29 61  1  0
 29 62  1  0
 30 63  1  1
 33 64  1  0
 33 65  1  0
 33 66  1  0
M  END


  Mrv1652304292202162D          

 34 36  0  0  1  0            999 V2000
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3977    1.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2732    1.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4 10  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 17 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 16 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 15 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 14 33  1  6  0  0  0
 13 34  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0079230

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1[C@@H](OC(C)=O)C(C)(C)[C@]2(O)CCC3=C(C)C(C=O)=C(O)C=C3[C@@]2(C)[C@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H32O9/c1-12-16-8-9-25(31)23(5,6)21(33-14(3)28)20(32-13(2)27)22(34-15(4)29)24(25,7)18(16)10-19(30)17(12)11-26/h10-11,20-22,30-31H,8-9H2,1-7H3/t20-,21+,22-,24-,25+/m0/s1

> <INCHI_KEY>
BSSJUSJUQOTDJX-LJDQNPOQSA-N

> <FORMULA>
C25H32O9

> <MOLECULAR_WEIGHT>
476.522

> <EXACT_MASS>
476.20463261

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
48.89434680982821

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,4R,4aS,10aR)-2,3-bis(acetyloxy)-7-formyl-6,10a-dihydroxy-1,1,4a,8-tetramethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-4-yl acetate

> <ALOGPS_LOGP>
2.62

> <JCHEM_LOGP>
2.9796944956666653

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.775442566272908

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.717020981015239

> <JCHEM_PKA_STRONGEST_BASIC>
-3.340651195491856

> <JCHEM_POLAR_SURFACE_AREA>
136.43

> <JCHEM_REFRACTIVITY>
120.05519999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.16e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4R,4aS,10aR)-2,3-bis(acetyloxy)-7-formyl-6,10a-dihydroxy-1,1,4a,8-tetramethyl-3,4,9,10-tetrahydro-2H-phenanthren-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       5.184  -0.564   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  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+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       9.034   0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       9.804  -0.564   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.494   3.437   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.742   2.920   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.510   3.643   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.746   0.770   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.516   2.104   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.056   2.104   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.746   3.437   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.206  -1.897   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.746  -1.897   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.516  -3.231   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.516  -0.564   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.874  -1.897   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.104  -3.231   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.874  -4.565   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.564  -3.231   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.334   3.437   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   14                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8                                                            
CONECT   10    4                                                            
CONECT   11    3   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18   34                                             
CONECT   14   13    2   15   33                                             
CONECT   15   14   16   29                                                  
CONECT   16   15   17   25                                                  
CONECT   17   16   18   21                                                  
CONECT   18   17   13   19   20                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   17   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   16   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   15   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   14                                                            
CONECT   34   13                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Value	Source
(2S,3S,4R,4AS,10ar)-2,4-bis(acetyloxy)-7-formyl-6,10a-dihydroxy-1,1,4a,8-tetramethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-3-yl acetic acid	Generator

Chemical Formula

C₂₅H₃₂O₉

Average Mass

476.5220 Da

Monoisotopic Mass

476.20463 Da

IUPAC Name

(2S,3S,4R,4aS,10aR)-2,3-bis(acetyloxy)-7-formyl-6,10a-dihydroxy-1,1,4a,8-tetramethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-4-yl acetate

Traditional Name

(2S,3S,4R,4aS,10aR)-2,3-bis(acetyloxy)-7-formyl-6,10a-dihydroxy-1,1,4a,8-tetramethyl-3,4,9,10-tetrahydro-2H-phenanthren-4-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1[C@@H](OC(C)=O)C(C)(C)[C@]2(O)CCC3=C(C)C(C=O)=C(O)C=C3[C@@]2(C)[C@H]1OC(C)=O

InChI Identifier

InChI=1S/C25H32O9/c1-12-16-8-9-25(31)23(5,6)21(33-14(3)28)20(32-13(2)27)22(34-15(4)29)24(25,7)18(16)10-19(30)17(12)11-26/h10-11,20-22,30-31H,8-9H2,1-7H3/t20-,21+,22-,24-,25+/m0/s1

InChI Key

BSSJUSJUQOTDJX-LJDQNPOQSA-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
Guilandina crista	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrophenanthrenes. These are a phenanthrene derivative where at least one ring CC bond is substituted by hydrogenation.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Hydrophenanthrenes

Direct Parent

Hydrophenanthrenes

Alternative Parents

Substituents

Hydrophenanthrene
Tetralin
Tricarboxylic acid or derivatives
1-hydroxy-2-unsubstituted benzenoid
Aryl-aldehyde
Cyclitol or derivatives
Vinylogous acid
Tertiary alcohol
Cyclic alcohol
Carboxylic acid ester
Carboxylic acid derivative
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Aldehyde
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	2.62	ALOGPS
logP	2.98	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	8.72	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	136.43 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	120.06 m³·mol⁻¹	ChemAxon
Polarizability	48.89 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

9595038

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11420152

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (-)-Norcaesalpinin MB (NP0079230)

MOL for NP0079230 ((-)-Norcaesalpinin MB)

3D MOL for NP0079230 ((-)-Norcaesalpinin MB)

3D SDF for NP0079230 ((-)-Norcaesalpinin MB)

3D-SDF for NP0079230 ((-)-Norcaesalpinin MB)

PDB for NP0079230 ((-)-Norcaesalpinin MB)

3D PDB for NP0079230 ((-)-Norcaesalpinin MB)

SMILES for NP0079230 ((-)-Norcaesalpinin MB)

INCHI for NP0079230 ((-)-Norcaesalpinin MB)

Structure for NP0079230 ((-)-Norcaesalpinin MB)

3D Structure for NP0079230 ((-)-Norcaesalpinin MB)