2-[(10R,13R,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]-malonic acid

ID: ALA440794

PubChem CID: 44279123

Max Phase: Preclinical

Molecular Formula: C30H48O4

Molecular Weight: 472.71

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)CCC[C@@H](C)[C@H]1CCC2C3CC=C4CC(C(C(=O)O)C(=O)O)CC[C@]4(C)C3CC[C@@]21C

Standard InChI:  InChI=1S/C30H48O4/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-21-17-20(26(27(31)32)28(33)34)13-15-29(21,4)25(22)14-16-30(23,24)5/h9,18-20,22-26H,6-8,10-17H2,1-5H3,(H,31,32)(H,33,34)/t19-,20?,22?,23-,24?,25?,29+,30-/m1/s1

Standard InChI Key:  JIEJBESLFFLEPM-VHWXEIKLSA-N

Molfile:  

     RDKit          2D

 35 38  0  0  1  0  0  0  0  0999 V2000
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    4.6167   -7.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3417   -7.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0542   -7.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4625   -8.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8917   -8.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0542   -5.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0542   -8.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7417  -10.1042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8167   -5.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7417   -7.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1750  -10.1042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8625   -5.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6167   -6.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8417   -4.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6167   -5.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2375   -4.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6417   -4.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8542   -3.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6542   -3.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2667   -2.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5537   -5.9518    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  1  0
  3  2  1  0
  4  1  1  0
  5 17  1  0
  6  4  1  0
  7  8  1  0
  8 20  1  0
  9  1  1  0
 10 15  1  0
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 13  3  1  0
 14  1  1  0
 15  6  1  0
 16  2  1  0
 17 14  1  0
 18  4  1  0
  9 19  1  0
 20 16  1  0
 21 11  2  0
 22 12  2  0
 23  9  1  0
 24 11  1  0
 25 12  1  0
  1 26  1  1
  2 27  1  1
 28 29  1  0
 29 23  1  0
 23 30  1  6
 31 28  1  0
 32 31  1  0
 33 32  1  0
 34 32  1  0
 19 18  1  0
  5  6  1  0
 10  3  2  0
  8 13  1  0
  9 35  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA440794

   2-[(10R,13R,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]propanedioic acid

Molecule Features

Natural Product: No

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: 472.71

Molecular Weight (Monoisotopic): 472.3553

AlogP: 7.43

#Rotatable Bonds: 8

Polar Surface Area: 74.60

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.48

CX Basic pKa: ┄

CX LogP: 7.65

CX LogD: 3.59

Aromatic Rings: ┄

Heavy Atoms: 34

QED Weighted: 0.28

Np Likeness Score: 1.95

References

1. Veeneman GH, Van Der Hulst RG, Van Boeckel CA, Philipsen RL, Ruigt G, Tonnaer JA, Van Delft TM, Konings PN.  (1995)  Synthesis of sialic acid-lipid conjugates and their neuritogenic effects on N1E.115 neuroblastoma cells,  5  (1): [10.1016/0960-894X(94)00450-T]

Source

Source(1):

• Scientific Literature