Isopropyl (2S)-2-[[[(8R,9S,13S,14S,17S)-17-Hydroxyl-13-methyl-6,7,8,9,11,12, 14,15,16,17-decahydrocyclopenta[a]-phenanthrene-3-yl]oxy(methoxymethyl)phosphoryl]amino]-propanoate

ID: ALA4079329

PubChem CID: 137651535

Max Phase: Preclinical

Molecular Formula: C26H40NO6P

Molecular Weight: 493.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCP(=O)(N[C@@H](C)C(=O)OC(C)C)Oc1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12

Standard InChI:  InChI=1S/C26H40NO6P/c1-16(2)32-25(29)17(3)27-34(30,15-31-5)33-19-7-9-20-18(14-19)6-8-22-21(20)12-13-26(4)23(22)10-11-24(26)28/h7,9,14,16-17,21-24,28H,6,8,10-13,15H2,1-5H3,(H,27,30)/t17-,21+,22+,23-,24-,26-,34?/m0/s1

Standard InChI Key:  CAJLYEOLCGJIKH-GGCXRRCPSA-N

Molfile:  

     RDKit          2D

 37 40  0  0  0  0  0  0  0  0999 V2000
   17.0110  -11.2343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0099  -12.0538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7179  -12.4628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7161  -10.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4248  -11.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4236  -12.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1337  -12.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8495  -12.0579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1360  -10.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8506  -11.2363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   19.1381   -9.9905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5755  -10.0016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5668  -10.8281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3502  -11.0918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8432  -10.4282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   21.6250   -8.9800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   16.3018  -12.4619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1297  -11.6305    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.5619  -11.6429    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.5945  -12.0527    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.8864  -12.4607    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5951  -11.2355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8053  -12.8422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2270  -13.4196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4379  -14.2091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1790  -12.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4710  -12.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1797  -11.2344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7636  -12.0505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4704  -13.2768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0556  -12.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3482  -12.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0549  -13.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5  9  1  0
  6  7  1  0
  7  8  1  0
  8 10  1  0
  9 10  1  0
  9 12  1  0
 10 14  1  0
 13 11  1  0
 11 12  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
 13 18  1  1
 17 19  1  1
 10 20  1  1
  2 21  1  0
  9 22  1  6
 14 23  1  6
 21 24  1  0
 24 25  1  0
 24 26  2  0
 24 27  1  0
 27 28  1  0
 28 29  1  0
 25 30  1  0
 30 31  1  0
 30 32  1  6
 31 33  1  0
 31 34  2  0
 33 35  1  0
 35 36  1  0
 35 37  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4079329

   ---

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: 493.58

Molecular Weight (Monoisotopic): 493.2593

AlogP: 5.01

#Rotatable Bonds: 8

Polar Surface Area: 94.09

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.36

CX Basic pKa: ┄

CX LogP: 4.04

CX LogD: 4.04

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.39

Np Likeness Score: 1.03

References

1. Wei Y, Qiu G, Lei B, Qin L, Chu H, Lu Y, Zhu G, Gao Q, Huang Q, Qian G, Liao P, Luo X, Zhang X, Zhang C, Li Y, Zheng S, Yu Y, Tang P, Ni J, Yan P, Zhou Y, Li P, Huang X, Gong A, Liu J..  (2017)  Oral Delivery of Propofol with Methoxymethylphosphonic Acid as the Delivery Vehicle.,  60  (20): [PMID:28968087] [10.1021/acs.jmedchem.7b01133]

Source

Source(1):

• Scientific Literature