NP-MRD: Showing NP-Card for methyl 2-[(1s,2s,3r,7s,12r,14s,15s,16r,17r)-16,17-bis(acetyloxy)-14-(furan-3-yl)-12-hydroxy-2,4,4,15-tetramethyl-5-oxo-8-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-10-en-3-yl]acetate (NP0187055)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 03:05:58 UTC

Updated at

2022-09-04 03:05:59 UTC

NP-MRD ID

NP0187055

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-[(1s,2s,3r,7s,12r,14s,15s,16r,17r)-16,17-bis(acetyloxy)-14-(furan-3-yl)-12-hydroxy-2,4,4,15-tetramethyl-5-oxo-8-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-10-en-3-yl]acetate

Description

Turrapubesin C belongs to the class of organic compounds known as 17-furanylsteroids and derivatives. These are steroidal compounds having a furanyl group linked to the steroid backbone at the C17 position. methyl 2-[(1s,2s,3r,7s,12r,14s,15s,16r,17r)-16,17-bis(acetyloxy)-14-(furan-3-yl)-12-hydroxy-2,4,4,15-tetramethyl-5-oxo-8-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-10-en-3-yl]acetate is found in Turraea pubescens. Based on a literature review very few articles have been published on Turrapubesin C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042205062D          

 41 45  0  0  1  0            999 V2000
    1.5427   -3.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0745   -2.8623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8867   -3.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1670   -3.7835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4185   -2.3768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1382   -1.6009    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3261   -1.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3241   -2.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5133   -1.5970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0458   -0.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2336   -0.5346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5776   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3897   -0.1943    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9215    0.4364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7336    0.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0139   -0.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8261   -0.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4774   -0.1236    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4506    0.7010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1602   -0.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9309   -1.3791    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4373   -2.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2080   -2.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8908   -3.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5421   -2.7795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2618   -2.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1064   -1.4059    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4662   -2.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5745   -2.0366    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8548   -2.8125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1743   -3.7601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6033   -4.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1940   -3.1493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7624   -1.8914    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2306   -2.5221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5109   -3.2980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3230   -3.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9791   -3.9287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4821   -1.1154    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6700   -0.9702    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9503   -1.7461    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
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 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  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 22 26  2  0  0  0  0
 21 27  1  0  0  0  0
 17 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 29 34  1  0  0  0  0
 34 35  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 34 39  1  0  0  0  0
 39 16  1  6  0  0  0
 39 40  1  0  0  0  0
 13 40  1  0  0  0  0
  6 40  1  0  0  0  0
 40 41  1  1  0  0  0
M  END

     RDKit          3D

 81 85  0  0  0  0  0  0  0  0999 V2000
    4.1969    3.6772    2.7726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3709    3.1635    1.7809 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5638    1.8873    1.2081 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5309    1.2813    1.6730 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6746    1.4069    0.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7164    0.0353   -0.3338 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0020   -0.4480   -0.9021 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0106   -1.0816   -0.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6366    0.7428   -1.6192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7147   -1.4289   -2.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5951   -1.6682   -2.8208 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3987   -2.0462   -2.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9881   -2.2764   -0.5833 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9906   -3.1809   -0.5945 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1869   -3.1572    0.5332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4906   -1.8401    0.4932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8138   -1.6947    0.7402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8279   -2.6877    1.0822 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6672   -3.9479    0.5094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1051   -2.1116    0.5407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9141   -0.6321    0.5762 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6881   -0.1249    1.7436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7509    0.7562    1.6779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1648    0.9469    2.9681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4124    0.2387    3.7459 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5234   -0.4132    3.0682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4505   -0.3515    0.6307 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1280    0.6369    1.6621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9453    0.0546   -0.7831 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5013    1.2778   -1.0810 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3529    1.5771   -2.1055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8438    2.9682   -2.2550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6826    0.6465   -2.8810 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4114    0.2348   -0.7268 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0342    0.4467   -2.0385 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1909    1.6589   -2.6534 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5960    1.7861   -4.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0233    2.6501   -1.9023 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3001   -0.5945    0.2036 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7293   -0.9725    0.1584 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1423   -1.2945    1.6116 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2090    3.9483    2.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2491    2.9555    3.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7032    4.5852    3.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6456    2.2095   -0.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6203    1.5426    0.6150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2371    0.2101   -1.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4993   -1.9915   -0.5285 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8810   -0.3953    0.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7409   -1.3297    0.9880 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8741    1.3916   -2.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3424    1.2807   -0.9532 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2756    0.3900   -2.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5436   -3.1040   -2.4310 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6429   -1.5737   -2.6514 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8990   -2.7919   -0.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6679   -3.4220    1.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5133   -4.0209    0.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9492   -2.8147    2.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9711   -4.6159    1.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9689   -2.4643    1.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2491   -2.5127   -0.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3809   -0.2456   -0.3761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2073    1.2300    0.8286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9939    1.5900    3.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7959   -1.0637    3.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4834    1.4935    1.3767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7287    0.1814    2.5674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1016    1.1657    1.9355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2164   -0.7780   -1.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0212    3.6017   -2.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2077    3.4021   -1.3091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6712    3.0335   -2.9839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4213    1.3122   -0.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7165    1.7827   -4.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3199    2.8426   -4.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1404    1.0351   -4.7269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2038   -0.0896    1.2386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6618   -2.2341    1.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7343   -0.5141    2.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2225   -1.3431    2.2783 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  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 26  2  0
 26 25  1  0
 25 24  1  0
 24 23  2  0
 21 27  1  0
 27 28  1  1
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  2  0
 29 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 36 38  2  0
 34 39  1  0
 39 40  1  0
 40 41  1  1
 40  6  1  0
 40 13  1  0
 39 16  1  0
 27 17  1  0
 23 22  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
  5 45  1  0
  5 46  1  0
  6 47  1  6
  8 48  1  0
  8 49  1  0
  8 50  1  0
  9 51  1  0
  9 52  1  0
  9 53  1  0
 12 54  1  0
 12 55  1  0
 13 56  1  1
 15 57  1  0
 15 58  1  0
 18 59  1  1
 19 60  1  0
 20 61  1  0
 20 62  1  0
 21 63  1  6
 26 66  1  0
 24 65  1  0
 23 64  1  0
 28 67  1  0
 28 68  1  0
 28 69  1  0
 29 70  1  6
 32 71  1  0
 32 72  1  0
 32 73  1  0
 34 74  1  1
 37 75  1  0
 37 76  1  0
 37 77  1  0
 39 78  1  1
 41 79  1  0
 41 80  1  0
 41 81  1  0
M  END


  Mrv1652309042205062D          

 41 45  0  0  1  0            999 V2000
    1.5427   -3.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0745   -2.8623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8867   -3.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1670   -3.7835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4185   -2.3768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1382   -1.6009    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3261   -1.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3241   -2.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5133   -1.5970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0458   -0.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2336   -0.5346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5776   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3897   -0.1943    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9215    0.4364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7336    0.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0139   -0.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8261   -0.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4774   -0.1236    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4506    0.7010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1602   -0.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9309   -1.3791    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4373   -2.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2080   -2.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8908   -3.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5421   -2.7795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2618   -2.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1064   -1.4059    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4662   -2.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5745   -2.0366    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8548   -2.8125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1743   -3.7601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6033   -4.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1940   -3.1493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7624   -1.8914    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2306   -2.5221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5109   -3.2980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3230   -3.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9791   -3.9287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4821   -1.1154    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6700   -0.9702    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9503   -1.7461    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
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 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  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 22 26  2  0  0  0  0
 21 27  1  0  0  0  0
 17 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 29 34  1  0  0  0  0
 34 35  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 34 39  1  0  0  0  0
 39 16  1  6  0  0  0
 39 40  1  0  0  0  0
 13 40  1  0  0  0  0
  6 40  1  0  0  0  0
 40 41  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0187055

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@H]1C(C)(C)C(=O)C[C@@H]2OCC3=C4[C@H](O)C[C@@H](C5=COC=C5)[C@]4(C)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H]3[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C31H40O10/c1-15(32)40-27-26-18(14-39-23-12-22(35)29(3,4)21(31(23,26)6)11-24(36)37-7)25-20(34)10-19(17-8-9-38-13-17)30(25,5)28(27)41-16(2)33/h8-9,13,19-21,23,26-28,34H,10-12,14H2,1-7H3/t19-,20+,21-,23-,26+,27+,28-,30-,31+/m0/s1

> <INCHI_KEY>
GOHBWTWCFSTOJD-AQMYFVRYSA-N

> <FORMULA>
C31H40O10

> <MOLECULAR_WEIGHT>
572.651

> <EXACT_MASS>
572.262147488

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
58.968586041500785

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-[(1S,2S,3R,7S,12R,14R,15S,16R,17R)-16,17-bis(acetyloxy)-14-(furan-3-yl)-12-hydroxy-2,4,4,15-tetramethyl-5-oxo-8-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-10-en-3-yl]acetate

> <JCHEM_LOGP>
1.8165550403333335

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.049407815693677

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.550395537470113

> <JCHEM_PKA_STRONGEST_BASIC>
-2.856400021265655

> <JCHEM_POLAR_SURFACE_AREA>
138.57000000000002

> <JCHEM_REFRACTIVITY>
143.98580000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl [(1S,2S,3R,7S,12R,14R,15S,16R,17R)-16,17-bis(acetyloxy)-14-(furan-3-yl)-12-hydroxy-2,4,4,15-tetramethyl-5-oxo-8-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-10-en-3-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       2.880  -6.520   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.872  -5.343   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.388  -5.614   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.912  -7.062   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.381  -4.437   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.858  -2.988   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.342  -2.717   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.338  -4.257   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.825  -2.981   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.819  -1.269   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.303  -0.998   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.811  -0.092   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.327  -0.363   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.320   0.815   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.836   0.544   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.359  -0.905   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.875  -1.176   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.091  -0.231   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      12.041   1.308   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      13.366  -1.095   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.938  -2.574   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.883  -3.790   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.455  -5.269   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.730  -6.134   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      15.945  -5.188   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      15.422  -3.740   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.399  -2.624   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.070  -4.010   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.406  -3.802   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      10.929  -5.250   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       9.659  -7.019   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.460  -7.876   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.829  -5.879   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       8.890  -3.531   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       7.897  -4.708   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       8.420  -6.156   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.936  -6.427   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       7.428  -7.334   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       8.367  -2.082   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.851  -1.811   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       7.374  -3.259   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                                                       
CONECT    6    5    7   40                                                  
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   40                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   39                                                  
CONECT   17   16   18   27                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   27                                                  
CONECT   22   21   23   26                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   22                                                       
CONECT   27   21   17   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   29   35   39                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   34   16   40                                                  
CONECT   40   39   13    6   41                                             
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₄₀O₁₀

Average Mass

572.6510 Da

Monoisotopic Mass

572.26215 Da

IUPAC Name

methyl 2-[(1S,2S,3R,7S,12R,14R,15S,16R,17R)-16,17-bis(acetyloxy)-14-(furan-3-yl)-12-hydroxy-2,4,4,15-tetramethyl-5-oxo-8-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-10-en-3-yl]acetate

Traditional Name

methyl [(1S,2S,3R,7S,12R,14R,15S,16R,17R)-16,17-bis(acetyloxy)-14-(furan-3-yl)-12-hydroxy-2,4,4,15-tetramethyl-5-oxo-8-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-10-en-3-yl]acetate

CAS Registry Number

Not Available

SMILES

COC(=O)C[C@H]1C(C)(C)C(=O)C[C@@H]2OCC3=C4[C@H](O)C[C@@H](C5=COC=C5)[C@]4(C)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H]3[C@]12C

InChI Identifier

InChI=1S/C31H40O10/c1-15(32)40-27-26-18(14-39-23-12-22(35)29(3,4)21(31(23,26)6)11-24(36)37-7)25-20(34)10-19(17-8-9-38-13-17)30(25,5)28(27)41-16(2)33/h8-9,13,19-21,23,26-28,34H,10-12,14H2,1-7H3/t19-,20+,21-,23-,26+,27+,28-,30-,31+/m0/s1

InChI Key

GOHBWTWCFSTOJD-AQMYFVRYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Turraea pubescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 17-furanylsteroids and derivatives. These are steroidal compounds having a furanyl group linked to the steroid backbone at the C17 position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

17-furanylsteroids and derivatives

Direct Parent

17-furanylsteroids and derivatives

Alternative Parents

Substituents

17-furanylsteroid skeleton
3-oxosteroid
15-hydroxysteroid
Hydroxysteroid
Oxosteroid
3-oxo-5-alpha-steroid
6-oxasteroid
Tricarboxylic acid or derivatives
Oxane
Cyclic alcohol
Furan
Heteroaromatic compound
Methyl ester
Ketone
Carboxylic acid ester
Cyclic ketone
Secondary alcohol
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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	1.82	ChemAxon
pKa (Strongest Acidic)	14.55	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	138.57 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	143.99 m³·mol⁻¹	ChemAxon
Polarizability	58.97 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24763697

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 2-[(1s,2s,3r,7s,12r,14s,15s,16r,17r)-16,17-bis(acetyloxy)-14-(furan-3-yl)-12-hydroxy-2,4,4,15-tetramethyl-5-oxo-8-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-10-en-3-yl]acetate (NP0187055)

MOL for NP0187055 (methyl 2-[(1s,2s,3r,7s,12r,14s,15s,16r,17r)-16,17-bis(acetyloxy)-14-(furan-3-yl)-12-hydroxy-2,4,4,15-tetramethyl-5-oxo-8-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-10-en-3-yl]acetate)

3D MOL for NP0187055 (methyl 2-[(1s,2s,3r,7s,12r,14s,15s,16r,17r)-16,17-bis(acetyloxy)-14-(furan-3-yl)-12-hydroxy-2,4,4,15-tetramethyl-5-oxo-8-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-10-en-3-yl]acetate)

3D SDF for NP0187055 (methyl 2-[(1s,2s,3r,7s,12r,14s,15s,16r,17r)-16,17-bis(acetyloxy)-14-(furan-3-yl)-12-hydroxy-2,4,4,15-tetramethyl-5-oxo-8-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-10-en-3-yl]acetate)

3D-SDF for NP0187055 (methyl 2-[(1s,2s,3r,7s,12r,14s,15s,16r,17r)-16,17-bis(acetyloxy)-14-(furan-3-yl)-12-hydroxy-2,4,4,15-tetramethyl-5-oxo-8-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-10-en-3-yl]acetate)

PDB for NP0187055 (methyl 2-[(1s,2s,3r,7s,12r,14s,15s,16r,17r)-16,17-bis(acetyloxy)-14-(furan-3-yl)-12-hydroxy-2,4,4,15-tetramethyl-5-oxo-8-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-10-en-3-yl]acetate)

3D PDB for NP0187055 (methyl 2-[(1s,2s,3r,7s,12r,14s,15s,16r,17r)-16,17-bis(acetyloxy)-14-(furan-3-yl)-12-hydroxy-2,4,4,15-tetramethyl-5-oxo-8-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-10-en-3-yl]acetate)

SMILES for NP0187055 (methyl 2-[(1s,2s,3r,7s,12r,14s,15s,16r,17r)-16,17-bis(acetyloxy)-14-(furan-3-yl)-12-hydroxy-2,4,4,15-tetramethyl-5-oxo-8-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-10-en-3-yl]acetate)

INCHI for NP0187055 (methyl 2-[(1s,2s,3r,7s,12r,14s,15s,16r,17r)-16,17-bis(acetyloxy)-14-(furan-3-yl)-12-hydroxy-2,4,4,15-tetramethyl-5-oxo-8-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-10-en-3-yl]acetate)

Structure for NP0187055 (methyl 2-[(1s,2s,3r,7s,12r,14s,15s,16r,17r)-16,17-bis(acetyloxy)-14-(furan-3-yl)-12-hydroxy-2,4,4,15-tetramethyl-5-oxo-8-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-10-en-3-yl]acetate)

3D Structure for NP0187055 (methyl 2-[(1s,2s,3r,7s,12r,14s,15s,16r,17r)-16,17-bis(acetyloxy)-14-(furan-3-yl)-12-hydroxy-2,4,4,15-tetramethyl-5-oxo-8-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-10-en-3-yl]acetate)