NP-MRD: Showing NP-Card for 4-[(1r,3as,5ar,7r,9r,9as,11ar)-3a,7,9-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one (NP0330607)

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Record Information

Version

2.0

Created at

2022-09-12 16:07:07 UTC

Updated at

2022-09-12 16:07:07 UTC

NP-MRD ID

NP0330607

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[(1r,3as,5ar,7r,9r,9as,11ar)-3a,7,9-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one

Description

Acovenosigenin belongs to the class of organic compounds known as cardenolides and derivatives. These are steroid lactones containing a furan-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative. 4-[(1r,3as,5ar,7r,9r,9as,11ar)-3a,7,9-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one is found in Streptocaulon juventas. 4-[(1r,3as,5ar,7r,9r,9as,11ar)-3a,7,9-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one was first documented in 2003 (PMID: 14640513). Based on a literature review a small amount of articles have been published on Acovenosigenin (PMID: 31250411) (PMID: 23286880) (PMID: 17510995).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122218072D          

 28 32  0  0  1  0            999 V2000
    1.8069   -1.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266   -1.9173    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3387   -1.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -0.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -1.4816    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3228   -0.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -1.5084    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2939   -0.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0646   -0.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7474    0.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7742    1.2229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3987   -0.1080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1184   -0.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168   -2.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -2.7639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826   -2.2576    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4850   -3.0585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705   -2.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902   -3.1787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -3.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -2.6932    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4342   -2.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976   -2.2077    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9098   -2.3529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -1.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -1.2866    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2751   -0.5107    0.0000 O   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  1  0  0  0
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  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  6 17  1  0  0  0  0
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 17 19  1  0  0  0  0
  3 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  6  0  0  0
  2 22  1  0  0  0  0
 22 23  1  0  0  0  0
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 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
  2 27  1  0  0  0  0
 27 28  1  1  0  0  0
M  END

     RDKit          3D

 62 66  0  0  0  0  0  0  0  0999 V2000
   -2.7617   -1.2527   -1.6966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2502   -0.5344   -0.4803 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7500   -0.5495   -0.5256 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2625    0.2532   -1.7164 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2133    0.0589   -1.9526 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0303    0.3678   -0.6873 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3428    1.8612   -0.8163 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2150   -0.5250   -0.7176 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3697   -0.1590    0.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8347   -0.9476    1.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9794   -0.3261    1.7376 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1689    0.8699    1.1428 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2173    1.0431    0.1421 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6432   -1.8414   -0.2684 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7326   -1.4253    0.8591 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9115    0.7742    1.6102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1220    0.1293    0.6650 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6731    1.4803    0.9192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0829    1.7128    0.5845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6905    0.9097   -0.4948 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2028    0.9401   -0.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7498    0.1729    0.7412 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1322    0.1123    0.6078 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2314   -1.2180    0.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7171   -1.1370    0.8094 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1176   -2.3594    1.0853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0535   -2.0753   -1.9487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7746   -1.6343   -1.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7715   -0.5106   -2.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4456   -1.6118   -0.5938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7882   -0.0395   -2.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3898    1.3262   -1.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4572    0.7878   -2.7781 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5183    2.3797   -1.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3410    2.3881    0.1326 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2250    1.9837   -1.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5168   -0.6013   -1.8062 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6504    1.9772    0.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3740   -2.6179   -0.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0533   -2.3444   -1.0822 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2538   -1.5468    1.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8277   -2.0700    0.9173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4661    1.6113    1.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4176   -0.5080    1.5553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0265    2.2409    0.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5509    1.6909    2.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2055    2.8030    0.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7399    1.6077    1.4985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4538    1.2941   -1.5268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5598    1.9848   -0.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6310    0.5027   -1.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5650    0.6956    1.7243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5409    0.9943    0.4493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6610   -1.9513    0.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4644   -1.5544    1.9274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4531   -0.4079    1.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8988   -2.7917    0.2258 H   0  0  0  0  0  0  0  0  0  0  0  0
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 27  2  1  0
  2  1  1  6
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 14  9  1  0
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  1 29  1  0
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 18 48  1  0
 16 46  1  0
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 15 44  1  0
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  8 40  1  6
 10 41  1  0
 14 42  1  0
 14 43  1  0
M  END


  Mrv1652309122218072D          

 28 32  0  0  1  0            999 V2000
    1.8069   -1.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266   -1.9173    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3387   -1.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -0.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -1.4816    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3228   -0.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -1.5084    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2939   -0.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0646   -0.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7474    0.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7742    1.2229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3987   -0.1080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1184   -0.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168   -2.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -2.7639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826   -2.2576    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4850   -3.0585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705   -2.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902   -3.1787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -3.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4342   -2.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976   -2.2077    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9098   -2.3529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -1.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2751   -0.5107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  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  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  2  0  0  0  0
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 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
  3 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  6  0  0  0
  2 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
  2 27  1  0  0  0  0
 27 28  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0330607

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12CCC3C(CC[C@@H]4C[C@@H](O)C[C@@H](O)[C@]34C)[C@@]1(O)CC[C@@H]2C1=CC(=O)OC1

> <INCHI_IDENTIFIER>
InChI=1S/C23H34O5/c1-21-7-5-17-18(4-3-14-10-15(24)11-19(25)22(14,17)2)23(21,27)8-6-16(21)13-9-20(26)28-12-13/h9,14-19,24-25,27H,3-8,10-12H2,1-2H3/t14-,15-,16-,17?,18?,19-,21-,22+,23+/m1/s1

> <INCHI_KEY>
CSKIDXJFNAYMTR-YTAKEYINSA-N

> <FORMULA>
C23H34O5

> <MOLECULAR_WEIGHT>
390.52

> <EXACT_MASS>
390.240624195

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
42.99690456876364

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(2S,3R,5R,7R,11S,14R,15R)-3,5,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
1.7637495140000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.504113414953647

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.182636201315128

> <JCHEM_PKA_STRONGEST_BASIC>
0.24218183448938857

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
105.1125

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-[(2S,3R,5R,7R,11S,14R,15R)-3,5,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-5H-furan-2-one

> <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       3.373  -2.131   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.850  -3.579   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.366  -3.308   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.889  -1.859   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.405  -1.588   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.398  -2.766   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.069  -1.380   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.937  -2.816   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.882  -1.600   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.454  -0.121   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.728   0.744   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.779   2.283   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      11.944  -0.202   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      11.421  -1.650   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.365  -4.295   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.090  -5.159   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.874  -4.214   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.505  -5.709   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.358  -4.485   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.835  -5.934   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.319  -6.205   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.326  -5.027   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.810  -5.298   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.182  -4.121   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.698  -4.392   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.341  -2.673   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.857  -2.402   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.380  -0.953   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   22   27                                             
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   17                                             
CONECT    7    6                                                            
CONECT    8    6    9   15                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    9                                                       
CONECT   15    8   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    6   18   19                                             
CONECT   18   17                                                            
CONECT   19   17    3   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    2   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26    2   28                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₄O₅

Average Mass

390.5200 Da

Monoisotopic Mass

390.24062 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@]12CCC3C(CC[C@@H]4C[C@@H](O)C[C@@H](O)[C@]34C)[C@@]1(O)CC[C@@H]2C1=CC(=O)OC1

InChI Identifier

InChI=1S/C23H34O5/c1-21-7-5-17-18(4-3-14-10-15(24)11-19(25)22(14,17)2)23(21,27)8-6-16(21)13-9-20(26)28-12-13/h9,14-19,24-25,27H,3-8,10-12H2,1-2H3/t14-,15-,16-,17?,18?,19-,21-,22+,23+/m1/s1

InChI Key

CSKIDXJFNAYMTR-YTAKEYINSA-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
Streptocaulon juventas	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cardenolides and derivatives. These are steroid lactones containing a furan-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

Cardenolides and derivatives

Alternative Parents

Substituents

Cardanolide-skeleton
3-hydroxysteroid
1-hydroxysteroid
3-beta-hydroxysteroid
14-hydroxysteroid
Hydroxysteroid
2-furanone
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Lactone
Polyol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
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

12022

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12539

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Pecio L, Hassan EM, Omer EA, Gajek G, Kontek R, Sobieraj A, Stochmal A, Oleszek W: Cytotoxic Cardenolides from the Leaves of Acokanthera oblongifolia. Planta Med. 2019 Aug;85(11-12):965-972. doi: 10.1055/a-0958-2566. Epub 2019 Jun 27. [PubMed:31250411 ]
Xue R, Han N, Ye C, Wang HB, Yin J: Cardenolide glycosides from root of Streptocaulon juventas. Phytochemistry. 2013 Apr;88:105-11. doi: 10.1016/j.phytochem.2012.12.004. Epub 2012 Dec 31. [PubMed:23286880 ]
Zhang XH, Zhu HL, Yu Q, Xuan LJ: Cytotoxic cardenolides from Streptocaulon griffithii. Chem Biodivers. 2007 May;4(5):998-1002. doi: 10.1002/cbdv.200790091. [PubMed:17510995 ]
Ueda JY, Tezuka Y, Banskota AH, Tran QL, Tran QK, Saiki I, Kadota S: Constituents of the Vietnamese medicinal plant Streptocaulon juventas and their antiproliferative activity against the human HT-1080 fibrosarcoma cell line. J Nat Prod. 2003 Nov;66(11):1427-33. doi: 10.1021/np030177h. [PubMed:14640513 ]
LOTUS database [Link]

Showing NP-Card for 4-[(1r,3as,5ar,7r,9r,9as,11ar)-3a,7,9-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one (NP0330607)

MOL for NP0330607 (4-[(1r,3as,5ar,7r,9r,9as,11ar)-3a,7,9-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

3D MOL for NP0330607 (4-[(1r,3as,5ar,7r,9r,9as,11ar)-3a,7,9-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

3D SDF for NP0330607 (4-[(1r,3as,5ar,7r,9r,9as,11ar)-3a,7,9-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

3D-SDF for NP0330607 (4-[(1r,3as,5ar,7r,9r,9as,11ar)-3a,7,9-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

PDB for NP0330607 (4-[(1r,3as,5ar,7r,9r,9as,11ar)-3a,7,9-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

3D PDB for NP0330607 (4-[(1r,3as,5ar,7r,9r,9as,11ar)-3a,7,9-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

SMILES for NP0330607 (4-[(1r,3as,5ar,7r,9r,9as,11ar)-3a,7,9-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

INCHI for NP0330607 (4-[(1r,3as,5ar,7r,9r,9as,11ar)-3a,7,9-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

Structure for NP0330607 (4-[(1r,3as,5ar,7r,9r,9as,11ar)-3a,7,9-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

3D Structure for NP0330607 (4-[(1r,3as,5ar,7r,9r,9as,11ar)-3a,7,9-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)