(3S,8S,9S,10R,13S,14S,16S,17R)-17-((2S,3S,6R)-3,7-dihydroxy-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,16-diol

ID: ALA2088136

PubChem CID: 70695378

Max Phase: Preclinical

Molecular Formula: C27H46O4

Molecular Weight: 434.66

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](CO)CC[C@H](O)[C@@H](C)[C@H]1[C@@H](O)C[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

Standard InChI:  InChI=1S/C27H46O4/c1-16(15-28)5-8-23(30)17(2)25-24(31)14-22-20-7-6-18-13-19(29)9-11-26(18,3)21(20)10-12-27(22,25)4/h6,16-17,19-25,28-31H,5,7-15H2,1-4H3/t16-,17-,19+,20-,21+,22+,23+,24+,25+,26+,27+/m1/s1

Standard InChI Key:  HJMSZKKOQIZOLJ-XPMUQOCRSA-N

Molfile:  

     RDKit          2D

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   10.2125  -18.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9245  -18.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9245  -17.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6365  -17.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6330  -18.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3418  -18.9424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0586  -18.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3488  -17.2924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0622  -17.7151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0792  -16.0598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3542  -16.4656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7960  -16.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7790  -17.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.4986  -18.9427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5744  -15.4206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2822  -14.9969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8535  -15.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0032  -15.3980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7110  -14.9742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4319  -15.3753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1398  -14.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2958  -15.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.7708  -18.1375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3417  -18.1167    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.0542  -16.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.2692  -14.1720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4450  -16.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8607  -15.3527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
  7  8  1  0
 13 18  1  1
  8 10  1  0
 16 19  1  1
  9 10  1  0
  5 20  1  1
  3  6  1  0
  2 21  1  1
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  5  6  1  0
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 22 24  1  6
  9 12  1  0
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 10 14  1  0
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 13 11  1  0
 26 27  1  0
 11 12  1  0
 27 28  1  0
 13 14  1  0
 17 29  1  6
  1  2  1  0
 14 30  1  6
  1  4  1  0
  9 31  1  6
  2  3  1  0
 10 32  1  1
  5  9  1  0
 23 33  1  1
  6  7  2  0
 27 34  1  6
 14 15  1  0
 28 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2088136

   (22s,25r)-Cholest-5-ene-3beta,16beta,22,26-tetrol

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 434.66

Molecular Weight (Monoisotopic): 434.3396

AlogP: 4.30

#Rotatable Bonds: 6

Polar Surface Area: 80.92

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.14

CX LogD: 3.14

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.47

Np Likeness Score: 3.10

References

1. Challinor VL, Stuthe JM, Parsons PG, Lambert LK, Lehmann RP, Kitching W, De Voss JJ..  (2012)  Structure and bioactivity of steroidal saponins isolated from the roots of Chamaelirium luteum (false unicorn).,  75  (8): [PMID:22880631] [10.1021/np300393y]

Source

Source(1):

• Scientific Literature