NP-MRD: Showing NP-Card for (2s,3s,4r,4as,10ar)-3,4-bis(acetyloxy)-7-formyl-5,10a-dihydroxy-1,1,4a,8-tetramethyl-3,4,9,10-tetrahydro-2h-phenanthren-2-yl acetate (NP0183703)

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Record Information

Version

2.0

Created at

2022-09-03 22:39:34 UTC

Updated at

2022-09-03 22:39:35 UTC

NP-MRD ID

NP0183703

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3s,4r,4as,10ar)-3,4-bis(acetyloxy)-7-formyl-5,10a-dihydroxy-1,1,4a,8-tetramethyl-3,4,9,10-tetrahydro-2h-phenanthren-2-yl acetate

Description

Norcaesalpinin MB 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. Based on a literature review very few articles have been published on Norcaesalpinin MB.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042200392D          

 34 36  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
    0.7954   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    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  1  0  0  0  0  0  0  0  0  0
    1.2079   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0296   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6701    0.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5886    0.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -0.1105    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.6039    0.0000 O   0  0  0  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  0  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9829   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3954   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -1.5395    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   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.8250    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
    4.0954   -1.5395    0.0000 C   0  0  0  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
    3.6829   -3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -2.9684    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  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 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  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 21 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  0  0  0  0
 14 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
M  END

     RDKit          3D

 66 68  0  0  0  0  0  0  0  0999 V2000
    2.9749    2.2986    2.8822 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8539    1.8836    1.4703 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6351    2.3786    0.6277 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9485    0.9843    0.9640 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8232    0.5831   -0.3708 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1922   -0.8330   -0.6049 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6775   -1.5065    0.5372 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9565   -2.0332    0.6208 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4742   -2.7434    1.8139 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7111   -1.8975   -0.3731 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0769   -1.6398   -1.2093 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2864   -3.0729   -0.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3141   -1.8029   -2.6501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2602   -1.2522   -0.7070 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1456   -1.3785    0.7119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3645   -2.1370   -1.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7509   -1.6035   -0.8633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7469   -0.4192    0.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8434   -0.2437    0.8949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9945   -1.1861    0.7686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8665    0.7932    1.7816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9550    0.9958    2.7064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9411    0.2475    2.8652 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8027    1.6624    1.8239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7028    1.5317    1.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6528    2.4302    1.0770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6687    0.4917    0.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6046    0.2338   -0.8660 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3619    0.2597   -2.2205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5506    1.0803   -1.0373 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5437    2.4421   -1.0108 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8054    3.3562   -2.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7491    4.8191   -1.7827 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1011    2.8946   -3.1314 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2505    3.1147    3.0461 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6649    1.4437    3.5199 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0200    2.5972    3.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6425    1.1852   -0.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0370   -0.8544   -1.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6558   -3.0425    2.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2274   -2.0915    2.2921 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0063   -3.6457    1.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0023   -3.0596    0.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6045   -3.7775   -1.1292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3620   -3.3184   -0.7430 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8379   -1.0952   -3.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1677   -2.8198   -3.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4240   -1.6325   -2.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7262   -2.0737    1.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2600   -3.0897   -0.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3700   -2.5352   -2.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3826   -1.4810   -1.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3069   -2.4104   -0.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0190   -1.5838   -0.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9674   -2.0098    1.4906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9621   -0.5957    0.8183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9773    1.8865    3.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7674    2.5089    2.5124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6234    3.1998    1.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3867    0.6524   -2.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8724    0.9877   -2.9306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3952   -0.6710   -2.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8470    0.9229   -2.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2849    5.1994   -1.6585 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3082    5.0815   -0.8411 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2310    5.3902   -2.5916 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  0
 11 13  1  0
 11 14  1  0
 14 15  1  1
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  2  0
 21 24  2  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 27 28  1  0
 28 29  1  6
 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
 27 18  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  5 38  1  6
  6 39  1  6
  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
 20 54  1  0
 20 55  1  0
 20 56  1  0
 22 57  1  0
 24 58  1  0
 26 59  1  0
 29 60  1  0
 29 61  1  0
 29 62  1  0
 30 63  1  6
 33 64  1  0
 33 65  1  0
 33 66  1  0
M  END


  Mrv1652309042200392D          

 34 36  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
    0.7954   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    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  1  0  0  0  0  0  0  0  0  0
    1.2079   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0296   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6701    0.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5886    0.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -0.1105    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.6039    0.0000 O   0  0  0  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  0  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9829   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3954   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -1.5395    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   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.8250    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
    4.0954   -1.5395    0.0000 C   0  0  0  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
    3.6829   -3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -2.9684    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  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 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  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 21 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  0  0  0  0
 14 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0183703

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

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

> <INCHI_KEY>
XYAKDNAIOYILCC-LJDQNPOQSA-N

> <FORMULA>
C25H32O9

> <MOLECULAR_WEIGHT>
476.522

> <EXACT_MASS>
476.20463261

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
48.69741693247188

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,4R,4aS,10aR)-3,4-bis(acetyloxy)-7-formyl-5,10a-dihydroxy-1,1,4a,8-tetramethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-2-yl acetate

> <JCHEM_LOGP>
2.3296944956666654

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.789540040590516

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.18832079814811

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3503877421529547

> <JCHEM_POLAR_SURFACE_AREA>
136.43

> <JCHEM_REFRACTIVITY>
120.05519999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4R,4aS,10aR)-3,4-bis(acetyloxy)-7-formyl-5,10a-dihydroxy-1,1,4a,8-tetramethyl-3,4,9,10-tetrahydro-2H-phenanthren-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-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  O   UNK     0       2.255  -1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.485  -0.206   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.255   1.127   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.055  -0.206   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.565  -0.206   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.118   0.320   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.832   1.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.105  -0.206   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.335   1.127   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.875   1.127   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.415   1.127   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.185  -0.206   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.725  -0.206   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.495   1.127   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.495  -1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.035  -1.540   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      13.805  -2.874   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.725  -2.874   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.185  -2.874   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.415  -4.207   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.415  -1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.875  -1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.645  -2.874   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.105  -2.874   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.875  -4.207   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.105  -5.541   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.875  -6.875   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.565  -5.541   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   30                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    6   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15   16   28                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   27                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   18   28                                                  
CONECT   28   27   14   29   30                                             
CONECT   29   28                                                            
CONECT   30   28    5   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₂O₉

Average Mass

476.5220 Da

Monoisotopic Mass

476.20463 Da

IUPAC Name

(2S,3S,4R,4aS,10aR)-3,4-bis(acetyloxy)-7-formyl-5,10a-dihydroxy-1,1,4a,8-tetramethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-2-yl acetate

Traditional Name

(2S,3S,4R,4aS,10aR)-3,4-bis(acetyloxy)-7-formyl-5,10a-dihydroxy-1,1,4a,8-tetramethyl-3,4,9,10-tetrahydro-2H-phenanthren-2-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)=CC(O)=C3[C@@]2(C)[C@H]1OC(C)=O

InChI Identifier

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

InChI Key

XYAKDNAIOYILCC-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, 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

Not Available

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
Tertiary alcohol
Cyclic alcohol
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Alcohol
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	2.33	ChemAxon
pKa (Strongest Acidic)	9.19	ChemAxon
pKa (Strongest Basic)	-3.4	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	48.7 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

C00043781

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

101366092

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3s,4r,4as,10ar)-3,4-bis(acetyloxy)-7-formyl-5,10a-dihydroxy-1,1,4a,8-tetramethyl-3,4,9,10-tetrahydro-2h-phenanthren-2-yl acetate (NP0183703)

MOL for NP0183703 ((2s,3s,4r,4as,10ar)-3,4-bis(acetyloxy)-7-formyl-5,10a-dihydroxy-1,1,4a,8-tetramethyl-3,4,9,10-tetrahydro-2h-phenanthren-2-yl acetate)

3D MOL for NP0183703 ((2s,3s,4r,4as,10ar)-3,4-bis(acetyloxy)-7-formyl-5,10a-dihydroxy-1,1,4a,8-tetramethyl-3,4,9,10-tetrahydro-2h-phenanthren-2-yl acetate)

3D SDF for NP0183703 ((2s,3s,4r,4as,10ar)-3,4-bis(acetyloxy)-7-formyl-5,10a-dihydroxy-1,1,4a,8-tetramethyl-3,4,9,10-tetrahydro-2h-phenanthren-2-yl acetate)

3D-SDF for NP0183703 ((2s,3s,4r,4as,10ar)-3,4-bis(acetyloxy)-7-formyl-5,10a-dihydroxy-1,1,4a,8-tetramethyl-3,4,9,10-tetrahydro-2h-phenanthren-2-yl acetate)

PDB for NP0183703 ((2s,3s,4r,4as,10ar)-3,4-bis(acetyloxy)-7-formyl-5,10a-dihydroxy-1,1,4a,8-tetramethyl-3,4,9,10-tetrahydro-2h-phenanthren-2-yl acetate)

3D PDB for NP0183703 ((2s,3s,4r,4as,10ar)-3,4-bis(acetyloxy)-7-formyl-5,10a-dihydroxy-1,1,4a,8-tetramethyl-3,4,9,10-tetrahydro-2h-phenanthren-2-yl acetate)

SMILES for NP0183703 ((2s,3s,4r,4as,10ar)-3,4-bis(acetyloxy)-7-formyl-5,10a-dihydroxy-1,1,4a,8-tetramethyl-3,4,9,10-tetrahydro-2h-phenanthren-2-yl acetate)

INCHI for NP0183703 ((2s,3s,4r,4as,10ar)-3,4-bis(acetyloxy)-7-formyl-5,10a-dihydroxy-1,1,4a,8-tetramethyl-3,4,9,10-tetrahydro-2h-phenanthren-2-yl acetate)

Structure for NP0183703 ((2s,3s,4r,4as,10ar)-3,4-bis(acetyloxy)-7-formyl-5,10a-dihydroxy-1,1,4a,8-tetramethyl-3,4,9,10-tetrahydro-2h-phenanthren-2-yl acetate)

3D Structure for NP0183703 ((2s,3s,4r,4as,10ar)-3,4-bis(acetyloxy)-7-formyl-5,10a-dihydroxy-1,1,4a,8-tetramethyl-3,4,9,10-tetrahydro-2h-phenanthren-2-yl acetate)