desacetylbufotalin-3-O-sulfite

ID: ALA1094625

PubChem CID: 46210591

Max Phase: Preclinical

Molecular Formula: C24H34O8S

Molecular Weight: 482.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12CC[C@H](OS(=O)(=O)O)C[C@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](c3ccc(=O)oc3)[C@@H](O)C[C@]12O

Standard InChI:  InChI=1S/C24H34O8S/c1-22-9-7-16(32-33(28,29)30)11-15(22)4-5-18-17(22)8-10-23(2)21(19(25)12-24(18,23)27)14-3-6-20(26)31-13-14/h3,6,13,15-19,21,25,27H,4-5,7-12H2,1-2H3,(H,28,29,30)/t15-,16+,17+,18-,19+,21+,22+,23-,24+/m1/s1

Standard InChI Key:  AKBDSCBYBRPAMM-QDLCSJEJSA-N

Molfile:  

     RDKit          2D

 36 40  0  0  0  0  0  0  0  0999 V2000
    9.8313   -7.9897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8313   -8.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5459   -9.2285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5459   -7.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2603   -7.9897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2614   -8.8170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9750   -9.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6879   -8.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9729   -7.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6825   -7.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6903   -6.3405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9737   -6.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4041   -6.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4006   -7.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1815   -7.8382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6694   -7.1785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1873   -6.5106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5952   -5.7942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4233   -5.7880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8278   -5.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4127   -4.3558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5844   -4.3621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1714   -5.0836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8197   -3.6363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3981   -5.9320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3939   -8.4055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2530   -7.1626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2571   -9.6443    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1149   -9.2337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6747   -7.1666    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9680   -8.3972    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4026   -8.8214    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.6893   -9.2322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8087   -8.1062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9856   -8.1062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4925   -7.1833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
 17 13  1  0
 18 19  1  0
  7  8  1  0
  8 10  1  0
  9 10  1  0
  3  6  1  0
  5  4  1  0
  5  6  1  0
 18 23  2  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 17 18  1  1
 21 24  2  0
  9 12  1  0
 13 25  1  1
 10 14  1  0
 14 26  1  1
 13 11  1  0
  5 27  1  1
 11 12  1  0
  6 28  1  1
 13 14  1  0
  2 29  1  1
  1  2  1  0
 10 30  1  1
  1  4  1  0
  9 31  1  6
  2  3  1  0
 29 32  1  0
  5  9  1  0
 32 33  1  0
  6  7  1  0
 32 34  2  0
 14 15  1  0
 32 35  2  0
 15 16  1  0
 16 36  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1094625

   [(3S,5R,8R,9S,10S,13R,14S,16S,17R)-14,16-dihydroxy-10,13-dimethyl-17-(6-oxopyran-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfate

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: 482.60

Molecular Weight (Monoisotopic): 482.1974

AlogP: 3.04

#Rotatable Bonds: 3

Polar Surface Area: 134.27

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -1.45

CX Basic pKa: ┄

CX LogP: 0.53

CX LogD: -0.43

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.56

Np Likeness Score: 2.74

References

1. Gao H, Zehl M, Kaehlig H, Schneider P, Stuppner H, Moreno Y Banuls L, Kiss R, Kopp B..  (2010)  Rapid structural identification of cytotoxic bufadienolide sulfates in toad venom from Bufo melanosticus by LC-DAD-MS(n) and LC-SPE-NMR.,  73  (4): [PMID:20361780] [10.1021/np900746k]

Source

Source(1):

• Scientific Literature