NP-MRD: Showing NP-Card for (1s,3r,6s,8r,9s,11s,12s,14s,15r,16r)-15-[(2r,5s)-5-hydroxy-2,6,6-trimethyloxan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-6,9,14-triol (NP0288065)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 17:36:44 UTC

Updated at

2022-09-09 17:36:45 UTC

NP-MRD ID

NP0288065

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3r,6s,8r,9s,11s,12s,14s,15r,16r)-15-[(2r,5s)-5-hydroxy-2,6,6-trimethyloxan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-6,9,14-triol

Description

(20R,24S)-20,25-Epoxycycloartane-3beta,6alpha,16beta,24-tetrol belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. (1s,3r,6s,8r,9s,11s,12s,14s,15r,16r)-15-[(2r,5s)-5-hydroxy-2,6,6-trimethyloxan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-6,9,14-triol is found in Astragalus pycnocephalus. Based on a literature review very few articles have been published on (20R,24S)-20,25-Epoxycycloartane-3beta,6alpha,16beta,24-tetrol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092219362D          

 35 40  0  0  1  0            999 V2000
    6.7571    4.5783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0679    3.8141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7665    4.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2614    3.6406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0083    2.8554    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2790    3.2409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5020    2.2041    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7313    1.4116    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5072    1.1313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0484    0.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3971    1.4549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1995    0.6540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5850    1.3097    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3047    0.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926    0.3886    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2123   -0.3873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9608    1.0193    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1486    0.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4327    0.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4352    0.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6168    1.5048    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1953    1.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8971    2.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7092    2.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2411    1.7952    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5214    2.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0532    1.9404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3335    2.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1456    2.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6774    2.2309    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0373    2.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5618    2.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3684    2.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6214    3.2023    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4280    3.3758    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  6  0  0  0
  7  8  1  1  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 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  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 17 25  1  1  0  0  0
 25 26  1  1  0  0  0
 27 26  1  1  0  0  0
 13 27  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
  7 30  1  0  0  0  0
 11 30  1  0  0  0  0
 30 31  1  1  0  0  0
  5 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
  2 34  1  0  0  0  0
 34 35  1  1  0  0  0
M  END

     RDKit          3D

 85 90  0  0  0  0  0  0  0  0999 V2000
    6.4676   -0.6867    0.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3039    0.1256    0.5987 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5923    0.3444    2.0941 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0980   -0.4977    0.5250 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5364   -0.6602   -0.7001 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0854   -2.0026   -1.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0608   -0.9177   -0.5960 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8940   -2.0871    0.3664 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9043   -2.1176    1.3282 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6085   -1.8425    1.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0312   -0.7497    0.3616 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6820   -1.3879   -0.8735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0305    0.0619    1.1045 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9246   -0.7963    1.8866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3647   -0.4188    1.9494 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0222   -1.5294    2.5380 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8475   -0.1922    0.5444 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3351    0.0451    0.4648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7916    1.3421    1.0289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0859   -1.0601    1.2196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7340   -0.1173   -0.9920 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.7413    0.7933   -1.3255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5390    0.0154   -1.9039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7296    1.2069   -1.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0850    0.8987   -0.0944 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6894    2.0402    0.7498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6653    1.0207    0.1449 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6802    1.7051   -0.7049 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5550    1.0361   -1.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1678    0.1116   -0.0836 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6122    0.9111    1.0769 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9230    0.3481   -1.7357 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4393    1.6418   -1.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3461    1.4814   -0.0402 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6934    1.7469   -0.3734 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3646   -1.7653    0.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7182   -0.4236   -0.9858 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3918   -0.3819    0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4894   -0.6439    2.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8332    1.0196    2.5352 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6169    0.6927    2.2535 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9860   -1.8141   -1.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2786   -2.7224   -0.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3423   -2.4685   -1.9348 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7481   -1.1902   -1.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8571   -3.0006   -0.2464 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6236   -1.7615    2.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7496   -1.6701    2.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0178   -2.8014    1.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5035   -2.0356   -0.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1751   -0.6593   -1.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0266   -2.1090   -1.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4749    0.7158    1.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8875   -1.8712    1.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5803   -0.8859    2.9622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5886    0.4254    2.6350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7331   -1.4994    3.5037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6714   -1.1428   -0.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2773    1.9248    0.1919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6119    1.2262    1.7975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0347    1.9665    1.4943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6940   -2.0553    0.9975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2296   -0.8203    2.2744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1214   -1.0396    0.7645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1641   -1.1260   -1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4354    0.3797   -1.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9546   -0.8985   -2.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8852    0.2898   -2.9409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0353    1.4557   -2.2254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4505    2.0644   -1.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7699    3.0305    0.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6634    2.0503    1.8313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1944    2.0774   -1.6403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3950    2.6718   -0.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4184    0.4767   -2.0840 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3259    1.8029   -1.3418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5179    0.4027    2.0666 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6629    1.2631    1.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0169    1.8724    1.1067 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7091   -0.0294   -2.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0313    0.5003   -2.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0300    2.1516   -2.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6202    2.3750   -0.9762 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0951    2.2746    0.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8040    1.8936   -1.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  6
 11 10  1  0
 10  8  1  0
  8  9  1  0
  8  7  1  0
  7 30  1  0
 30 31  1  1
 30 29  1  0
 29 28  1  0
 27 28  1  6
 27 26  1  0
 25 26  1  1
 25 24  1  0
 24 23  1  0
 23 21  1  0
 21 22  1  0
 21 18  1  0
 18 19  1  0
 18 20  1  0
 18 17  1  0
 17 15  1  0
 15 16  1  0
 15 14  1  0
 14 13  1  0
  7  5  1  0
  5  6  1  6
  5 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 34  2  1  0
  2  1  1  0
  2  3  1  0
  2  4  1  0
 30 11  1  0
 25 27  1  0
 17 25  1  0
  4  5  1  0
 13 11  1  0
 13 27  1  0
 12 50  1  0
 12 51  1  0
 12 52  1  0
 10 48  1  0
 10 49  1  0
  8 46  1  6
  9 47  1  0
  7 45  1  6
 31 77  1  0
 31 78  1  0
 31 79  1  0
 29 75  1  0
 29 76  1  0
 28 73  1  0
 28 74  1  0
 26 71  1  0
 26 72  1  0
 24 69  1  0
 24 70  1  0
 23 67  1  0
 23 68  1  0
 21 65  1  1
 22 66  1  0
 19 59  1  0
 19 60  1  0
 19 61  1  0
 20 62  1  0
 20 63  1  0
 20 64  1  0
 17 58  1  6
 15 56  1  1
 16 57  1  0
 14 54  1  0
 14 55  1  0
 13 53  1  1
  6 42  1  0
  6 43  1  0
  6 44  1  0
 32 80  1  0
 32 81  1  0
 33 82  1  0
 33 83  1  0
 34 84  1  1
 35 85  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  3 39  1  0
  3 40  1  0
  3 41  1  0
M  END


  Mrv1652309092219362D          

 35 40  0  0  1  0            999 V2000
    6.7571    4.5783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0679    3.8141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7665    4.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2614    3.6406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0083    2.8554    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2790    3.2409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5020    2.2041    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7313    1.4116    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5072    1.1313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0484    0.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3971    1.4549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1995    0.6540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5850    1.3097    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3047    0.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926    0.3886    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2123   -0.3873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9608    1.0193    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1486    0.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4327    0.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4352    0.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6168    1.5048    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1953    1.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8971    2.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7092    2.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2411    1.7952    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5214    2.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0532    1.9404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3335    2.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1456    2.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6774    2.2309    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0373    2.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5618    2.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3684    2.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6214    3.2023    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4280    3.3758    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  6  0  0  0
  7  8  1  1  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 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  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 17 25  1  1  0  0  0
 25 26  1  1  0  0  0
 27 26  1  1  0  0  0
 13 27  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
  7 30  1  0  0  0  0
 11 30  1  0  0  0  0
 30 31  1  1  0  0  0
  5 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
  2 34  1  0  0  0  0
 34 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0288065

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]12C[C@H](O)[C@@H]([C@@]1(C)CC[C@@]13C[C@@]11CC[C@H](O)C(C)(C)[C@@H]1[C@@H](O)C[C@@H]23)[C@@]1(C)CC[C@H](O)C(C)(C)O1

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O5/c1-24(2)20(33)9-11-30-16-29(30)13-12-26(5)23(28(7)10-8-21(34)25(3,4)35-28)18(32)15-27(26,6)19(29)14-17(31)22(24)30/h17-23,31-34H,8-16H2,1-7H3/t17-,18-,19-,20-,21-,22-,23-,26+,27-,28+,29-,30+/m0/s1

> <INCHI_KEY>
VIOYSPVPEAYUTR-UOUCMYEWSA-N

> <FORMULA>
C30H50O5

> <MOLECULAR_WEIGHT>
490.725

> <EXACT_MASS>
490.36582471

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
57.6802340620672

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-15-[(2R,5S)-5-hydroxy-2,6,6-trimethyloxan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecane-6,9,14-triol

> <JCHEM_LOGP>
2.5997933190000007

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.43227128717913

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.835653290631466

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8423453849030924

> <JCHEM_POLAR_SURFACE_AREA>
90.15

> <JCHEM_REFRACTIVITY>
135.71599999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-15-[(2R,5S)-5-hydroxy-2,6,6-trimethyloxan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecane-6,9,14-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      12.613   8.546   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.193   7.120   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.498   7.939   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      11.688   6.796   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      11.216   5.330   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.854   6.050   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.270   4.114   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.698   2.635   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.147   2.112   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.424   1.771   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.208   2.716   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.839   1.221   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.692   2.445   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.169   0.996   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.653   0.725   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.130  -0.723   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.660   1.903   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.144   1.632   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.674   0.186   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.812   0.858   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.151   2.809   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.365   2.538   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.675   4.257   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.191   4.528   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.183   3.351   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.707   4.799   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.699   3.622   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.222   5.071   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.738   5.342   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.731   4.164   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.403   5.550   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.249   4.188   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.754   4.512   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      14.227   5.978   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      15.732   6.301   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   34                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7   32                                             
CONECT    6    5                                                            
CONECT    7    5    8   30                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13   30                                             
CONECT   12   11                                                            
CONECT   13   11   14   27                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   25                                                  
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   17   26   27                                             
CONECT   26   25   27                                                       
CONECT   27   26   13   25   28                                             
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29    7   11   31                                             
CONECT   31   30                                                            
CONECT   32    5   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33    2   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Value	Source
(20R,24S)-20,25-Epoxycycloartane-3b,6a,16b,24-tetrol	Generator
(20R,24S)-20,25-Epoxycycloartane-3β,6α,16β,24-tetrol	Generator

Chemical Formula

C₃₀H₅₀O₅

Average Mass

490.7250 Da

Monoisotopic Mass

490.36582 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@]12C[C@H](O)[C@@H]([C@@]1(C)CC[C@@]13C[C@@]11CC[C@H](O)C(C)(C)[C@@H]1[C@@H](O)C[C@@H]23)[C@@]1(C)CC[C@H](O)C(C)(C)O1

InChI Identifier

InChI=1S/C30H50O5/c1-24(2)20(33)9-11-30-16-29(30)13-12-26(5)23(28(7)10-8-21(34)25(3,4)35-28)18(32)15-27(26,6)19(29)14-17(31)22(24)30/h17-23,31-34H,8-16H2,1-7H3/t17-,18-,19-,20-,21-,22-,23-,26+,27-,28+,29-,30+/m0/s1

InChI Key

VIOYSPVPEAYUTR-UOUCMYEWSA-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
Astragalus pycnocephalus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Triterpene saponins

Alternative Parents

Substituents

Triterpene saponin
Cycloartanol-skeleton
9b,19-cyclo-lanostane-skeleton
Cycloartane-skeleton
Triterpenoid
24-hydroxysteroid
3-hydroxysteroid
6-hydroxysteroid
Hydroxysteroid
3-beta-hydroxysteroid
16-hydroxysteroid
16-beta-hydroxysteroid
Steroid
Oxane
Cyclic alcohol
Secondary alcohol
Organoheterocyclic compound
Ether
Dialkyl ether
Oxacycle
Polyol
Organooxygen compound
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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

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

10214395

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21592457

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3r,6s,8r,9s,11s,12s,14s,15r,16r)-15-[(2r,5s)-5-hydroxy-2,6,6-trimethyloxan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-6,9,14-triol (NP0288065)

MOL for NP0288065 ((1s,3r,6s,8r,9s,11s,12s,14s,15r,16r)-15-[(2r,5s)-5-hydroxy-2,6,6-trimethyloxan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-6,9,14-triol)

3D MOL for NP0288065 ((1s,3r,6s,8r,9s,11s,12s,14s,15r,16r)-15-[(2r,5s)-5-hydroxy-2,6,6-trimethyloxan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-6,9,14-triol)

3D SDF for NP0288065 ((1s,3r,6s,8r,9s,11s,12s,14s,15r,16r)-15-[(2r,5s)-5-hydroxy-2,6,6-trimethyloxan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-6,9,14-triol)

3D-SDF for NP0288065 ((1s,3r,6s,8r,9s,11s,12s,14s,15r,16r)-15-[(2r,5s)-5-hydroxy-2,6,6-trimethyloxan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-6,9,14-triol)

PDB for NP0288065 ((1s,3r,6s,8r,9s,11s,12s,14s,15r,16r)-15-[(2r,5s)-5-hydroxy-2,6,6-trimethyloxan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-6,9,14-triol)

3D PDB for NP0288065 ((1s,3r,6s,8r,9s,11s,12s,14s,15r,16r)-15-[(2r,5s)-5-hydroxy-2,6,6-trimethyloxan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-6,9,14-triol)

SMILES for NP0288065 ((1s,3r,6s,8r,9s,11s,12s,14s,15r,16r)-15-[(2r,5s)-5-hydroxy-2,6,6-trimethyloxan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-6,9,14-triol)

INCHI for NP0288065 ((1s,3r,6s,8r,9s,11s,12s,14s,15r,16r)-15-[(2r,5s)-5-hydroxy-2,6,6-trimethyloxan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-6,9,14-triol)

Structure for NP0288065 ((1s,3r,6s,8r,9s,11s,12s,14s,15r,16r)-15-[(2r,5s)-5-hydroxy-2,6,6-trimethyloxan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-6,9,14-triol)

3D Structure for NP0288065 ((1s,3r,6s,8r,9s,11s,12s,14s,15r,16r)-15-[(2r,5s)-5-hydroxy-2,6,6-trimethyloxan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-6,9,14-triol)