4-[(3S,5R,10S,13S,14S,17S)-3-(3,5-Dihydroxy-4-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-14-hydroxy-10,13-dimethyl-hexadecahydro-20-oxa-cyclopropa[11,12]cyclopenta[a]phenanthren-17-yl]-5H-furan-2-one

ID: ALA2069068

PubChem CID: 70686675

Max Phase: Preclinical

Molecular Formula: C30H44O9

Molecular Weight: 548.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@@H]1[C@@H](O)[C@H](C)O[C@@H](OC2CC[C@@]3(C)[C@H](CC[C@@H]4[C@@H]3C3OC3[C@]3(C)[C@H](C5=CC(=O)OC5)CC[C@]43O)C2)[C@@H]1O

Standard InChI:  InChI=1S/C30H44O9/c1-14-22(32)25(35-4)23(33)27(37-14)38-17-7-9-28(2)16(12-17)5-6-19-21(28)24-26(39-24)29(3)18(8-10-30(19,29)34)15-11-20(31)36-13-15/h11,14,16-19,21-27,32-34H,5-10,12-13H2,1-4H3/t14-,16+,17?,18-,19+,21+,22-,23+,24?,25+,26?,27-,28-,29-,30-/m0/s1

Standard InChI Key:  IMZJQCFFLONCLT-VYBORYGUSA-N

Molfile:  

     RDKit          2D

 42 48  0  0  0  0  0  0  0  0999 V2000
    7.2792   -5.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5667   -5.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2792   -6.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8542   -5.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8542   -4.6958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8542   -6.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5667   -6.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1708   -7.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1417   -6.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1708   -8.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4583   -9.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0667   -5.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4583   -7.5833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3208   -4.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7458   -8.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8333   -3.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1417   -7.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7458   -7.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0667   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3208   -3.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5667   -7.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -7.5833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5500   -5.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1042   -3.4042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4250   -6.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1042   -4.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4250   -7.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8542   -7.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2792   -7.1708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -7.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0667   -2.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -9.2292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2792   -4.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4583  -10.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0292   -9.2292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -6.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1417   -5.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0292   -7.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1708  -10.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1417   -8.4083    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5625   -5.9333    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8500   -7.1708    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0
  4  2  1  0
  5  2  1  0
  6  7  1  0
  7  3  1  0
  8 22  1  1
  9  6  1  0
 10  8  1  0
 11 10  1  0
 12  1  1  0
 13  8  1  0
 12 14  1  6
 15 11  1  0
 16 14  2  0
 17  9  1  0
 18 13  1  0
 19  3  1  0
 20 16  1  0
 21  7  1  0
 22 30  1  0
 23 12  1  0
 24 26  1  0
 25  9  1  0
 26 14  1  0
 27 17  1  0
 28 21  1  0
  3 29  1  1
 30 27  1  0
 31 20  2  0
 10 32  1  6
  1 33  1  1
 11 34  1  6
 15 35  1  1
 36 25  1  0
  9 37  1  1
 18 38  1  6
 39 34  1  0
 17 40  1  1
 23 19  1  0
  5  4  1  0
  4  6  1  0
 17 28  1  0
 20 24  1  0
 30 36  1  0
 15 18  1  0
  7 41  1  1
  2  1  1  0
  6 42  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA2069068

   3-[(1S,5S,6S,9S,10R,13R,18S)-15-[(2R,3R,4R,5S,6S)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-9-hydroxy-5,18-dimethyl-3-oxapentacyclo[8.8.0.02,4.05,9.013,18]octadecan-6-yl]-2H-furan-5-one

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: 548.67

Molecular Weight (Monoisotopic): 548.2985

AlogP: 2.10

#Rotatable Bonds: 4

Polar Surface Area: 127.21

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.15

CX Basic pKa: ┄

CX LogP: 1.92

CX LogD: 1.48

Aromatic Rings: ┄

Heavy Atoms: 39

QED Weighted: 0.27

Np Likeness Score: 3.26

References

1. Chang LC, Gills JJ, Bhat KP, Luyengi L, Farnsworth NR, Pezzuto JM, Kinghorn AD..  (2000)  Activity-guided isolation of constituents of Cerbera manghas with antiproliferative and antiestrogenic activities.,  10  (21): [PMID:11078194] [10.1016/s0960-894x(00)00477-7]

2. Chang LC, Gills JJ, Bhat KP, Luyengi L, Farnsworth NR, Pezzuto JM, Kinghorn AD..  (2000)  Activity-guided isolation of constituents of Cerbera manghas with antiproliferative and antiestrogenic activities.,  10  (21): [PMID:11078194] [10.1016/s0960-894x(00)00477-7]

Source

Source(1):

• Scientific Literature