NP-MRD: Showing NP-Card for (1r,3as,5as,7s,9as,11ar)-3a,5a,7-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde (NP0200669)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 19:33:29 UTC

Updated at

2022-09-04 19:33:29 UTC

NP-MRD ID

NP0200669

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3as,5as,7s,9as,11ar)-3a,5a,7-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde

Description

(2S,5S,7S,11S,14S,15R)-5,7,11-trihydroxy-15-methyl-14-(2-oxo-2H-pyran-5-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecane-2-carbaldehyde belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative. (1r,3as,5as,7s,9as,11ar)-3a,5a,7-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde is found in Duttaphrynus melanostictus, Helleborus viridis and Kalanchoe laciniata. Based on a literature review very few articles have been published on (2S,5S,7S,11S,14S,15R)-5,7,11-trihydroxy-15-methyl-14-(2-oxo-2H-pyran-5-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecane-2-carbaldehyde.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042221332D          

 30 34  0  0  1  0            999 V2000
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8898   -0.5288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5807   -3.4873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3708   -0.9394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8728   -3.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3665   -4.5563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5492   -4.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0429   -5.0948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2383   -3.6793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7447   -3.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  5 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  2  0  0  0  0
  6 19  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  2 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 24 30  2  0  0  0  0
M  END

     RDKit          3D

 62 66  0  0  0  0  0  0  0  0999 V2000
   -2.3430   -0.3070    1.7698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8376   -0.5382    0.3999 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8523   -1.6943    0.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2392   -1.4554    1.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9922   -0.1655    1.1733 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2098    0.9386    0.6159 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9440    1.9522   -0.2079 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2176    1.4922   -0.8238 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0254    0.8371    0.2678 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9229    1.6810    1.3951 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4625    0.7371   -0.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5596   -0.2577   -1.2480 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9171   -0.5106   -1.4405 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9037   -1.5468   -0.9080 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4287   -1.3964   -0.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3611   -0.4475    0.6142 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2262   -1.0826    1.6875 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7072   -0.3152    2.5009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0873    0.6360   -0.0913 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9440    1.7543    0.1514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0156    0.4766   -1.5437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1049   -0.5331   -1.9169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8535   -0.8230   -0.6499 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1328   -0.1334   -0.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1345   -0.6623    0.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3322   -0.0029    0.3094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4970    1.1628   -0.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6075    1.7678   -0.3345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5184    1.6173   -1.1578 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3494    1.0278   -1.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5701   -1.2398    2.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5182    0.1793    2.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1748    0.4214    1.8061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4219   -2.5838    0.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5038   -1.9082   -0.6206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2473   -1.5076    2.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9197   -2.3314    1.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2735    0.1272    2.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1693    1.5522    1.5044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3085    2.3572   -1.0401 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2018    2.8903    0.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8045    2.4133   -1.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1417    0.9032   -1.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3228    2.5391    1.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7867    1.7117   -0.5108 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1101    0.4870    0.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1661    0.1914   -2.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4067   -0.4769   -0.5717 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4036   -1.9842   -0.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0180   -2.2294   -1.7759 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1415   -2.4505   -0.2332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8095   -1.1721   -1.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4118   -2.1314    1.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7488    2.4808   -0.4849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2092    1.4598   -2.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0935    0.1035   -1.9825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6711   -0.0971   -2.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6465   -1.4684   -2.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0951   -1.9316   -0.5414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9554   -1.5990    0.7893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1134   -0.4146    0.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5952    1.4998   -1.9322 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  1
  9 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
 17 18  2  0
  6 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 30  2  0
 30 29  1  0
 29 27  1  0
 27 28  2  0
 27 26  1  0
 26 25  2  0
 19  2  1  0
 25 24  1  0
 23  2  1  0
 16  5  1  0
 16  9  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  1
  6 39  1  1
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
 10 44  1  0
 11 45  1  0
 11 46  1  0
 12 47  1  6
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 15 52  1  0
 17 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 22 57  1  0
 22 58  1  0
 23 59  1  6
 30 62  1  0
 26 61  1  0
 25 60  1  0
M  END


  Mrv1652309042221332D          

 30 34  0  0  1  0            999 V2000
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8898   -0.5288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5807   -3.4873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3708   -0.9394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8728   -3.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3665   -4.5563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5492   -4.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0429   -5.0948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2383   -3.6793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7447   -3.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  5 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  2  0  0  0  0
  6 19  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  2 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 24 30  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0200669

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12CCC3C(CC[C@]4(O)C[C@@H](O)CC[C@]34C=O)[C@@]1(O)CC[C@@H]2C1=COC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O6/c1-21-8-5-18-19(6-10-23(28)12-16(26)4-9-22(18,23)14-25)24(21,29)11-7-17(21)15-2-3-20(27)30-13-15/h2-3,13-14,16-19,26,28-29H,4-12H2,1H3/t16-,17+,18?,19?,21+,22-,23-,24-/m0/s1

> <INCHI_KEY>
TVKPTWJPKVSGJB-RTTJAOCVSA-N

> <FORMULA>
C24H32O6

> <MOLECULAR_WEIGHT>
416.514

> <EXACT_MASS>
416.21988875

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
44.22081353642253

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,5S,7S,11S,14S,15R)-5,7,11-trihydroxy-15-methyl-14-(2-oxo-2H-pyran-5-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-2-carbaldehyde

> <JCHEM_LOGP>
1.0777440793333322

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.302563573407674

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.064862183805445

> <JCHEM_PKA_STRONGEST_BASIC>
0.2958659271409845

> <JCHEM_POLAR_SURFACE_AREA>
104.06000000000002

> <JCHEM_REFRACTIVITY>
110.76499999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,5S,7S,11S,14S,15R)-5,7,11-trihydroxy-15-methyl-14-(6-oxopyran-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-2-carbaldehyde

> <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       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      12.861  -0.987   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.284  -6.510   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.159  -1.754   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.417  -8.505   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.892  -8.295   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.947  -9.510   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       2.312  -6.868   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   19   23                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   16                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    5    9   17                                             
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19    6    2   20   21                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22    2   24                                                  
CONECT   24   23   25   30                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   24                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₂O₆

Average Mass

416.5140 Da

Monoisotopic Mass

416.21989 Da

IUPAC Name

(2S,5S,7S,11S,14S,15R)-5,7,11-trihydroxy-15-methyl-14-(2-oxo-2H-pyran-5-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-2-carbaldehyde

Traditional Name

(2S,5S,7S,11S,14S,15R)-5,7,11-trihydroxy-15-methyl-14-(6-oxopyran-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-2-carbaldehyde

CAS Registry Number

Not Available

SMILES

C[C@]12CCC3C(CC[C@]4(O)C[C@@H](O)CC[C@]34C=O)[C@@]1(O)CC[C@@H]2C1=COC(=O)C=C1

InChI Identifier

InChI=1S/C24H32O6/c1-21-8-5-18-19(6-10-23(28)12-16(26)4-9-22(18,23)14-25)24(21,29)11-7-17(21)15-2-3-20(27)30-13-15/h2-3,13-14,16-19,26,28-29H,4-12H2,1H3/t16-,17+,18?,19?,21+,22-,23-,24-/m0/s1

InChI Key

TVKPTWJPKVSGJB-RTTJAOCVSA-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
Duttaphrynus melanostictus	LOTUS Database	35616633
Helleborus viridis	LOTUS Database	35616633
Kalanchoe laciniata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Bufanolides and derivatives

Alternative Parents

Substituents

Bufanolide-skeleton
19-oxosteroid
3-hydroxysteroid
14-hydroxysteroid
5-hydroxysteroid
Hydroxysteroid
Oxosteroid
3-beta-hydroxysteroid
Pyranone
Pyran
Cyclic alcohol
Heteroaromatic compound
Tertiary alcohol
Lactone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Polyol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Aldehyde
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	1.08	ChemAxon
pKa (Strongest Acidic)	14.06	ChemAxon
pKa (Strongest Basic)	0.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	110.76 m³·mol⁻¹	ChemAxon
Polarizability	44.22 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

9672

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10068

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3as,5as,7s,9as,11ar)-3a,5a,7-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde (NP0200669)

MOL for NP0200669 ((1r,3as,5as,7s,9as,11ar)-3a,5a,7-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

3D MOL for NP0200669 ((1r,3as,5as,7s,9as,11ar)-3a,5a,7-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

3D SDF for NP0200669 ((1r,3as,5as,7s,9as,11ar)-3a,5a,7-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

3D-SDF for NP0200669 ((1r,3as,5as,7s,9as,11ar)-3a,5a,7-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

PDB for NP0200669 ((1r,3as,5as,7s,9as,11ar)-3a,5a,7-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

3D PDB for NP0200669 ((1r,3as,5as,7s,9as,11ar)-3a,5a,7-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

SMILES for NP0200669 ((1r,3as,5as,7s,9as,11ar)-3a,5a,7-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

INCHI for NP0200669 ((1r,3as,5as,7s,9as,11ar)-3a,5a,7-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

Structure for NP0200669 ((1r,3as,5as,7s,9as,11ar)-3a,5a,7-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

3D Structure for NP0200669 ((1r,3as,5as,7s,9as,11ar)-3a,5a,7-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)