(1R,2S,5S)-Pentanoic acid (3S,5R,8R,9S,10S,13R,17S)-10,13-dimethyl-17-(3-oxo-2,7-dioxa-bicyclo[4.1.0]hept4-en-6-yl)-hexadecahydro-20-oxa-cyclopropa[14,15]cyclopenta[a]phenanthren-3-yl ester

ID: ALA454990

PubChem CID: 44559579

Max Phase: Preclinical

Molecular Formula: C29H40O6

Molecular Weight: 484.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCC(=O)O[C@H]1CC[C@@]2(C)[C@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H]([C@@]45C=CC(=O)O[C@@H]4O5)C[C@H]4O[C@]342)C1

Standard InChI:  InChI=1S/C29H40O6/c1-4-5-6-23(30)32-18-9-12-26(2)17(15-18)7-8-20-19(26)10-13-27(3)21(16-22-29(20,27)34-22)28-14-11-24(31)33-25(28)35-28/h11,14,17-22,25H,4-10,12-13,15-16H2,1-3H3/t17-,18+,19+,20-,21+,22-,25-,26+,27-,28+,29-/m1/s1

Standard InChI Key:  CBERTSGIPSJWBL-GIUJEAEVSA-N

Molfile:  

     RDKit          2D

 41 47  0  0  0  0  0  0  0  0999 V2000
   10.0292   -1.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0292   -2.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7412   -2.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7412   -1.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4532   -1.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4543   -2.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1653   -2.7301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8799   -2.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1632   -1.0801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8807   -1.4947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8795    0.1598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1595   -0.2538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5970   -0.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8720   -0.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3869   -0.0015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4576    0.9463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7162    1.7259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1695    2.3442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3605    2.1774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4303    3.1268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4458   -0.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4500   -3.1417    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3153   -2.7344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8750   -0.6667    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1583   -1.9042    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.2083    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.3818   -1.3436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5960   -1.0859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7658   -1.8953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9625   -1.9250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.1792    0.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6002   -2.3229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8864   -2.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5990   -1.4979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6476    0.7744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0954    1.3838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8438    0.6009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2667    1.3917    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1713   -2.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4574   -2.7385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7423   -2.3271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
 18 19  1  0
 19 36  1  0
 15 35  1  0
  9 10  1  0
 18 20  2  0
  3  6  1  0
  5 21  1  1
  5  4  1  0
  6 22  1  1
  5  6  1  0
  2 23  1  1
 10 24  1  1
  9 12  1  0
  9 25  1  6
 10 28  1  0
 15 26  1  6
 28 27  1  0
 28 29  1  1
 27 29  1  0
 13 11  1  0
 11 12  1  0
 13 28  1  0
  1  2  1  0
 27 30  1  6
  1  4  1  0
 13 31  1  1
  2  3  1  0
 23 32  1  0
 27 14  1  0
 32 33  1  0
 14 15  1  0
 32 34  2  0
 36 35  1  0
 37 36  1  0
 35 37  1  1
 15 13  1  0
 35 16  1  0
  5  9  1  0
  6  7  1  0
 36 38  1  6
  7  8  1  0
 33 39  1  0
  8 10  1  0
 39 40  1  0
 16 17  2  0
 40 41  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA454990

   [(1R,2S,4R,6S,7R,10S,11S,14S,16R)-7,11-dimethyl-6-[(1S,6S)-3-oxo-2,7-dioxabicyclo[4.1.0]hept-4-en-6-yl]-3-oxapentacyclo[8.8.0.02,4.02,7.011,16]octadecan-14-yl] pentanoate

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: 484.63

Molecular Weight (Monoisotopic): 484.2825

AlogP: 5.09

#Rotatable Bonds: 5

Polar Surface Area: 77.66

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.55

CX LogD: 5.55

Aromatic Rings: ┄

Heavy Atoms: 35

QED Weighted: 0.40

Np Likeness Score: 3.02

References

1. Enomoto A, Rho MC, Komiyama K, Hayashi M..  (2004)  Inhibitory effects of bufadienolides on interleukin-6 in MH-60 cells.,  67  (12): [PMID:15620253] [10.1021/np049950e]

Source

Source(1):

• Scientific Literature