NP-MRD: Showing NP-Card for Scillarenin (NP0073176)

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Record Information

Version

2.0

Created at

2022-04-28 18:26:26 UTC

Updated at

2022-04-28 18:26:26 UTC

NP-MRD ID

NP0073176

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Scillarenin

Description

Scillarenin, also known as cardiogenin, 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. Thus, scillarenin is considered to be a sterol. Scillarenin is found in Urginea maritima and Drimia hesperia. Scillarenin was first documented in 2010 (PMID: 20656985). Based on a literature review a small amount of articles have been published on scillarenin (PMID: 33909413) (PMID: 30686259).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282220262D          

 28 32  0  0  1  0            999 V2000
    4.2475    2.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278    1.3777    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9960    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838    0.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035    1.6682    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4354    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914    1.8134    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5596    1.1827    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8399    0.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520    0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475    1.3279    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4672    2.1038    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9990    2.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111    2.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574    2.0770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5867    1.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962    0.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637    2.7283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6810    2.6155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1873    3.2668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8764    4.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3828    4.6823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0592    4.1438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5528    3.4925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1073    2.8462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9451    0.5269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6232    2.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399    1.2325    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  6  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 15 18  1  6  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 18 24  1  0  0  0  0
 12 25  1  6  0  0  0
 11 26  1  6  0  0  0
  5 27  1  6  0  0  0
  2 28  1  6  0  0  0
M  END

     RDKit          3D

 60 64  0  0  0  0  0  0  0  0999 V2000
   -3.1961   -1.6281    0.3845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5244   -0.3079    0.2473 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9941    0.5702    1.4161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4555    0.8917    1.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5130    1.8870    0.0304 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7790    2.2865   -0.3154 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7425    1.3660   -1.1449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8649    0.3929   -1.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1369   -0.0762   -2.2392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2756   -1.2645   -1.9996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4796   -1.2970   -0.7530 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0366   -0.3396    0.2697 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4328   -0.8034    1.5790 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0094   -0.3993    1.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7529   -0.7490    0.2910 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7485   -1.8498    0.6864 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4799    0.5136   -0.1646 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6260    0.8938    0.6226 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5826    1.9837    1.4620 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7018    2.3433    2.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8483    1.5840    2.1221 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8784    1.8988    2.8132 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8534    0.5597    1.3178 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8046    0.1946    0.5791 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7301    0.2461   -1.6096 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3201   -0.1863   -2.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0028   -1.1597   -0.9144 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4803   -2.3974   -1.3587 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9143   -1.6521    1.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4424   -2.4261    0.6293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7729   -1.9358   -0.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4220    1.4981    1.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9121   -0.0597    2.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9043    1.2477    2.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0279   -0.0040    0.8386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9668    2.8096    0.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9493    3.2556   -0.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9624    1.8553   -2.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9134   -0.3545   -2.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5873    0.7777   -2.7065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9329   -2.1789   -2.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5927   -1.3366   -2.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6434   -2.3233   -0.2954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6606    0.6733    0.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8892   -0.2984    2.4464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4674   -1.9076    1.6571 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4796   -0.8208    2.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0139    0.7129    1.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2269   -2.3099   -0.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0719   -2.6593    1.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3832   -1.5681    1.5257 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6627    1.3041   -0.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7061    2.6039    1.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7091    3.1901    2.8964 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9580   -0.6761   -0.0411 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3690   -0.6455   -1.7822 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0665    1.1221   -2.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4176   -0.6627   -3.0122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7062    0.7176   -2.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8024   -3.1023   -1.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  1
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  2  0
  7  5  1  0
  5  6  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  1  6
 11 27  1  0
 27 28  1  6
 27 26  1  0
 26 25  1  0
 25 17  1  0
 17 18  1  0
 18 24  2  0
 24 23  1  0
 23 21  1  0
 21 22  2  0
 21 20  1  0
 20 19  2  0
 27 15  1  0
 19 18  1  0
 17 15  1  0
  2 12  1  0
  2  8  1  0
 16 49  1  0
 16 50  1  0
 16 51  1  0
 14 47  1  0
 14 48  1  0
 13 45  1  0
 13 46  1  0
 12 44  1  6
 11 43  1  1
 10 41  1  0
 10 42  1  0
  9 39  1  0
  9 40  1  0
  7 38  1  0
  5 36  1  1
  6 37  1  0
  4 34  1  0
  4 35  1  0
  3 32  1  0
  3 33  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 28 60  1  0
 26 58  1  0
 26 59  1  0
 25 56  1  0
 25 57  1  0
 17 52  1  6
 24 55  1  0
 20 54  1  0
 19 53  1  0
M  END


  Mrv1652304282220262D          

 28 32  0  0  1  0            999 V2000
    4.2475    2.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278    1.3777    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9960    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838    0.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035    1.6682    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4354    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914    1.8134    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5596    1.1827    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8399    0.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520    0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475    1.3279    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4672    2.1038    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9990    2.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111    2.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574    2.0770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5867    1.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962    0.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637    2.7283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6810    2.6155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1873    3.2668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8764    4.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3828    4.6823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0592    4.1438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5528    3.4925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1073    2.8462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9451    0.5269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6232    2.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399    1.2325    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  6  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 15 18  1  6  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 18 24  1  0  0  0  0
 12 25  1  6  0  0  0
 11 26  1  6  0  0  0
  5 27  1  6  0  0  0
  2 28  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0073176

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12CC[C@H]3[C@@H](CCC4=C[C@@H](O)CC[C@]34C)[C@@]1(O)CC[C@@H]2C1=COC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O4/c1-22-10-7-17(25)13-16(22)4-5-20-19(22)8-11-23(2)18(9-12-24(20,23)27)15-3-6-21(26)28-14-15/h3,6,13-14,17-20,25,27H,4-5,7-12H2,1-2H3/t17-,18+,19-,20+,22-,23+,24-/m0/s1

> <INCHI_KEY>
OVUOVMIMOCJILI-KFZANIOBSA-N

> <FORMULA>
C24H32O4

> <MOLECULAR_WEIGHT>
384.516

> <EXACT_MASS>
384.23005951

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
42.78512817909883

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(1S,2R,5S,10R,11S,14S,15R)-5,11-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl]-2H-pyran-2-one

> <ALOGPS_LOGP>
3.15

> <JCHEM_LOGP>
3.0270894823333325

> <ALOGPS_LOGS>
-4.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.50441592215265

> <JCHEM_PKA_STRONGEST_BASIC>
0.3001086611251217

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
109.18469999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.16e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[(1S,2R,5S,10R,11S,14S,15R)-5,11-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl]pyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       7.929   4.020   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.452   2.572   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.459   1.394   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.943   1.666   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.420   3.114   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.413   4.291   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.904   3.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.911   2.208   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.434   0.759   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.950   0.488   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.395   2.479   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.872   3.927   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.865   5.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.381   4.833   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.667   3.877   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.095   2.398   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.179   1.534   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.612   5.093   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.138   4.882   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.083   6.098   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.503   7.525   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.448   8.740   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.977   7.735   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.032   6.519   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.200   5.313   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.764   0.984   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.897   4.562   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.968   2.301   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   28                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   27                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   14                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12   17   26                                             
CONECT   12   11   13   15   25                                             
CONECT   13   12   14                                                       
CONECT   14   13    7                                                       
CONECT   15   12   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   11                                                       
CONECT   18   15   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   18                                                       
CONECT   25   12                                                            
CONECT   26   11                                                            
CONECT   27    5                                                            
CONECT   28    2                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   64    0
END

View in JSmol

Synonyms

Value	Source
beta-Scillarenin	ChEBI
Cardiogenin	ChEBI
Scillarenin a	ChEBI
b-Scillarenin	Generator
Β-scillarenin	Generator
3,14-Dihydroxybufa-4,20,22-trienolide	MeSH

Chemical Formula

C₂₄H₃₂O₄

Average Mass

384.5160 Da

Monoisotopic Mass

384.23006 Da

IUPAC Name

5-[(1S,2R,5S,10R,11S,14S,15R)-5,11-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl]-2H-pyran-2-one

Traditional Name

5-[(1S,2R,5S,10R,11S,14S,15R)-5,11-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl]pyran-2-one

CAS Registry Number

Not Available

SMILES

C[C@]12CC[C@H]3[C@@H](CCC4=C[C@@H](O)CC[C@]34C)[C@@]1(O)CC[C@@H]2C1=COC(=O)C=C1

InChI Identifier

InChI=1S/C24H32O4/c1-22-10-7-17(25)13-16(22)4-5-20-19(22)8-11-23(2)18(9-12-24(20,23)27)15-3-6-21(26)28-14-15/h3,6,13-14,17-20,25,27H,4-5,7-12H2,1-2H3/t17-,18+,19-,20+,22-,23+,24-/m0/s1

InChI Key

OVUOVMIMOCJILI-KFZANIOBSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Drimia maritima	Plant	KNApSAcK
Squilla hesperia	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
3-hydroxy-delta-4-steroid
3-hydroxysteroid
14-hydroxysteroid
Hydroxysteroid
3-beta-hydroxysteroid
Delta-4-steroid
Pyranone
Pyran
Cyclic alcohol
Heteroaromatic compound
Tertiary alcohol
Lactone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

3beta-hydroxy steroid (CHEBI:38248 )
14beta-hydroxy steroid (CHEBI:38248 )
Bufanolides and derivatives (LMST01130003 )

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	3.15	ALOGPS
logP	3.03	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	17.5	ChemAxon
pKa (Strongest Basic)	0.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	109.18 m³·mol⁻¹	ChemAxon
Polarizability	42.79 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

C00033368

Chemspider ID

16736018

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12315393

PDB ID

Not Available

ChEBI ID

38248

Good Scents ID

Not Available

References

General References

Black GP, He G, Denison MS, Young TM: Using Estrogenic Activity and Nontargeted Chemical Analysis to Identify Contaminants in Sewage Sludge. Environ Sci Technol. 2021 May 18;55(10):6729-6739. doi: 10.1021/acs.est.0c07846. Epub 2021 Apr 28. [PubMed:33909413 ]
Saket K, Afshari JT, Saburi E, Yousefi M, Salari R: Therapeutic Aspects of Squill; An Evidence-Based Review. Curr Drug Discov Technol. 2020;17(3):318-324. doi: 10.2174/1570163816666190125154745. [PubMed:30686259 ]
Mahringer A, Karamustafa S, Klotz D, Kahl S, Konkimalla VB, Wang Y, Wang J, Liu HY, Boechzelt H, Hao X, Bauer R, Fricker G, Efferth T: Inhibition of P-glycoprotein at the blood-brain barrier by phytochemicals derived from traditional Chinese medicine. Cancer Genomics Proteomics. 2010 Jul-Aug;7(4):191-205. [PubMed:20656985 ]

Showing NP-Card for Scillarenin (NP0073176)

MOL for NP0073176 (Scillarenin)

3D MOL for NP0073176 (Scillarenin)

3D SDF for NP0073176 (Scillarenin)

3D-SDF for NP0073176 (Scillarenin)

PDB for NP0073176 (Scillarenin)

3D PDB for NP0073176 (Scillarenin)

SMILES for NP0073176 (Scillarenin)

INCHI for NP0073176 (Scillarenin)

Structure for NP0073176 (Scillarenin)

3D Structure for NP0073176 (Scillarenin)