NP-MRD: Showing NP-Card for methyl (1r,2s,4ar,6ar,7s,11as,11bs)-1,2-bis(acetyloxy)-4a-hydroxy-4,4,11b-trimethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylate (NP0322487)

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Record Information

Version

2.0

Created at

2022-09-12 01:17:04 UTC

Updated at

2022-09-12 01:17:05 UTC

NP-MRD ID

NP0322487

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,2s,4ar,6ar,7s,11as,11bs)-1,2-bis(acetyloxy)-4a-hydroxy-4,4,11b-trimethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylate

Description

Caesalpinin MF belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Based on a literature review very few articles have been published on Caesalpinin MF.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122203172D          

 33 36  0  0  1  0            999 V2000
    4.8038   -2.4961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5235   -1.7202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7114   -1.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1796   -2.2057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.7991    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9629   -0.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -0.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340    1.1139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705    0.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.1221    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6190   -0.6539    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0872   -1.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2751   -1.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -0.3634    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4630   -0.9941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6302   -0.3595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1807   -1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342    1.1884    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1539    1.9643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6582    2.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1901    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9385    2.8855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463    1.0432    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7781    1.6739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4978    2.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6857    2.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0296    3.0805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    0.2673    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0584    0.8980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 10  2  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 27 32  1  0  0  0  0
 12 32  1  0  0  0  0
 16 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END

     RDKit          3D

 67 70  0  0  0  0  0  0  0  0999 V2000
    5.6235    0.9587   -1.8928 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3335    1.0294   -1.3220 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0836    0.4840   -0.0912 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0547   -0.0782    0.4990 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7596    0.5025    0.6048 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8595   -0.1240    1.9423 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8614   -0.1923    2.8900 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3725   -0.9192    3.9522 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1534   -1.2564    3.6427 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8022   -0.8036    2.4508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4838   -0.9914    1.7632 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4538   -0.2586    0.4881 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7531   -0.3001   -0.2368 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7839    0.2371   -1.6073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5417    0.1220   -2.4424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6270    0.4195   -1.5292 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2500    1.6465   -0.9176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8981    0.6969   -2.2296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7618    1.9771   -3.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3059   -0.3804   -3.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9989    0.9516   -1.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7174    0.5380    0.1575 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1011    1.4846    0.9763 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6409    1.9887    2.1287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9849    2.9948    2.9984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7867    1.5595    2.4725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9868   -0.7853    0.1065 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0413   -1.4639    1.3153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7087   -2.6695    1.4687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7777   -3.4061    2.7460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2894   -3.1698    0.4709 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6188   -0.6475   -0.4839 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2373   -2.0200   -0.9840 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7213    0.0042   -2.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3742    0.9085   -1.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8280    1.7769   -2.6095 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4595    1.5747    0.6560 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8309    0.2591    2.7745 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9218   -1.1596    4.8782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2558   -0.5448    2.4969 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2866   -2.0544    1.7580 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2816    0.8328    0.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1478   -1.3433   -0.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5996   -0.2548   -2.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0581    1.3216   -1.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6530    0.8610   -3.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4519   -0.8475   -2.9748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7546    2.4029   -1.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2674    2.8494   -2.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3084    1.9050   -4.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7591    2.3000   -3.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6504    0.0771   -4.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4969   -1.0518   -3.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2348   -0.9217   -2.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3255    2.0298   -1.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9130    0.4142   -1.6150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7104    0.3035    0.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3976    3.9904    2.6868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8961    3.0318    2.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2973    2.8036    4.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5631   -1.4018   -0.6363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8271   -3.6345    3.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3058   -2.8818    3.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2938   -4.4020    2.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7449   -2.1199   -1.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0557   -2.4627   -1.6271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2340   -2.6906   -0.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 22 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 27 32  1  0
 32 33  1  6
 32 12  1  0
 12 11  1  0
 11 10  1  0
 10  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  6  5  1  0
 12 13  1  0
  9 10  1  0
 32 16  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  5 37  1  1
 13 43  1  6
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 17 48  1  0
 19 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 22 57  1  1
 25 58  1  0
 25 59  1  0
 25 60  1  0
 27 61  1  6
 30 62  1  0
 30 63  1  0
 30 64  1  0
 33 65  1  0
 33 66  1  0
 33 67  1  0
 12 42  1  1
 11 40  1  0
 11 41  1  0
  7 38  1  0
  8 39  1  0
M  END


  Mrv1652309122203172D          

 33 36  0  0  1  0            999 V2000
    4.8038   -2.4961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5235   -1.7202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7114   -1.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1796   -2.2057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.7991    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9629   -0.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -0.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340    1.1139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705    0.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.1221    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6190   -0.6539    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0872   -1.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2751   -1.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -0.3634    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4630   -0.9941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6302   -0.3595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1807   -1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342    1.1884    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1539    1.9643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6582    2.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1901    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9385    2.8855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463    1.0432    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7781    1.6739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4978    2.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6857    2.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0296    3.0805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    0.2673    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0584    0.8980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 10  2  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 27 32  1  0  0  0  0
 12 32  1  0  0  0  0
 16 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0322487

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@H]1[C@@H]2CC[C@@]3(O)C(C)(C)C[C@H](OC(C)=O)[C@H](OC(C)=O)[C@]3(C)[C@H]2CC2=C1C=CO2

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O8/c1-13(26)32-19-12-23(3,4)25(29)9-7-15-17(24(25,5)21(19)33-14(2)27)11-18-16(8-10-31-18)20(15)22(28)30-6/h8,10,15,17,19-21,29H,7,9,11-12H2,1-6H3/t15-,17+,19+,20+,21+,24+,25-/m1/s1

> <INCHI_KEY>
HOGJRIMKVUXURE-PFOQEMQTSA-N

> <FORMULA>
C25H34O8

> <MOLECULAR_WEIGHT>
462.539

> <EXACT_MASS>
462.225368055

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
48.97356956345974

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1S,2S,3R,4S,7R,10R,11S)-3,4-bis(acetyloxy)-7-hydroxy-2,6,6-trimethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-diene-11-carboxylate

> <JCHEM_LOGP>
2.157634193333332

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.960320948462396

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8237061960964978

> <JCHEM_POLAR_SURFACE_AREA>
112.27000000000001

> <JCHEM_REFRACTIVITY>
116.141

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,2S,3R,4S,7R,10R,11S)-3,4-bis(acetyloxy)-7-hydroxy-2,6,6-trimethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-diene-11-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       8.967  -4.659   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.444  -3.211   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.928  -2.940   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.935  -4.117   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.405  -1.492   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.398  -0.314   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.937  -0.264   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.365   1.215   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.090   2.079   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.874   1.134   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.358   1.405   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.366   0.228   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.889  -1.221   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.896  -2.398   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.380  -2.127   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.857  -0.678   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.864  -1.856   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.176  -0.671   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.337  -1.947   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.810   2.218   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.287   3.667   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.229   3.938   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.221   2.761   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.752   5.386   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.319   3.125   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.796   4.573   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.280   4.844   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.789   5.750   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.850   0.499   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.842   1.676   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   13                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    6   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   32                                                  
CONECT   13   12    5   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   32                                             
CONECT   17   16                                                            
CONECT   18   16   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   22   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   27   12   16   33                                             
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₄O₈

Average Mass

462.5390 Da

Monoisotopic Mass

462.22537 Da

IUPAC Name

methyl (1S,2S,3R,4S,7R,10R,11S)-3,4-bis(acetyloxy)-7-hydroxy-2,6,6-trimethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-diene-11-carboxylate

Traditional Name

methyl (1S,2S,3R,4S,7R,10R,11S)-3,4-bis(acetyloxy)-7-hydroxy-2,6,6-trimethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-diene-11-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@H]1[C@@H]2CC[C@@]3(O)C(C)(C)C[C@H](OC(C)=O)[C@H](OC(C)=O)[C@]3(C)[C@H]2CC2=C1C=CO2

InChI Identifier

InChI=1S/C25H34O8/c1-13(26)32-19-12-23(3,4)25(29)9-7-15-17(24(25,5)21(19)33-14(2)27)11-18-16(8-10-31-18)20(15)22(28)30-6/h8,10,15,17,19-21,29H,7,9,11-12H2,1-6H3/t15-,17+,19+,20+,21+,24+,25-/m1/s1

InChI Key

HOGJRIMKVUXURE-PFOQEMQTSA-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 diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Abscisic acid
Naphthofuran
Tricarboxylic acid or derivatives
Benzofuran
Heteroaromatic compound
Methyl ester
Tertiary alcohol
Furan
Cyclic alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	2.16	ChemAxon
pKa (Strongest Acidic)	13.96	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	112.27 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	116.14 m³·mol⁻¹	ChemAxon
Polarizability	48.97 Å³	ChemAxon
Number of Rings	4	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

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

101370653

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1r,2s,4ar,6ar,7s,11as,11bs)-1,2-bis(acetyloxy)-4a-hydroxy-4,4,11b-trimethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylate (NP0322487)

MOL for NP0322487 (methyl (1r,2s,4ar,6ar,7s,11as,11bs)-1,2-bis(acetyloxy)-4a-hydroxy-4,4,11b-trimethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylate)

3D MOL for NP0322487 (methyl (1r,2s,4ar,6ar,7s,11as,11bs)-1,2-bis(acetyloxy)-4a-hydroxy-4,4,11b-trimethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylate)

3D SDF for NP0322487 (methyl (1r,2s,4ar,6ar,7s,11as,11bs)-1,2-bis(acetyloxy)-4a-hydroxy-4,4,11b-trimethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylate)

3D-SDF for NP0322487 (methyl (1r,2s,4ar,6ar,7s,11as,11bs)-1,2-bis(acetyloxy)-4a-hydroxy-4,4,11b-trimethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylate)

PDB for NP0322487 (methyl (1r,2s,4ar,6ar,7s,11as,11bs)-1,2-bis(acetyloxy)-4a-hydroxy-4,4,11b-trimethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylate)

3D PDB for NP0322487 (methyl (1r,2s,4ar,6ar,7s,11as,11bs)-1,2-bis(acetyloxy)-4a-hydroxy-4,4,11b-trimethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylate)

SMILES for NP0322487 (methyl (1r,2s,4ar,6ar,7s,11as,11bs)-1,2-bis(acetyloxy)-4a-hydroxy-4,4,11b-trimethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylate)

INCHI for NP0322487 (methyl (1r,2s,4ar,6ar,7s,11as,11bs)-1,2-bis(acetyloxy)-4a-hydroxy-4,4,11b-trimethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylate)

Structure for NP0322487 (methyl (1r,2s,4ar,6ar,7s,11as,11bs)-1,2-bis(acetyloxy)-4a-hydroxy-4,4,11b-trimethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylate)

3D Structure for NP0322487 (methyl (1r,2s,4ar,6ar,7s,11as,11bs)-1,2-bis(acetyloxy)-4a-hydroxy-4,4,11b-trimethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylate)