19-oxofasciospongine A

ID: ALA556261

PubChem CID: 25227567

Max Phase: Preclinical

Molecular Formula: C30H45N3O6S

Molecular Weight: 575.77

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 19-Oxofasciospongine A | 19-oxofasciospongine A|CHEMBL556261

Canonical SMILES:  C[C@H]1CC[C@H]2C(=CCCC2(C)C)[C@@]1(C)CCC(CCCC1=CC(=O)N(CCc2c[nH]cn2)C1=O)COS(=O)(=O)O

Standard InChI:  InChI=1S/C30H45N3O6S/c1-21-10-11-25-26(9-6-14-29(25,2)3)30(21,4)15-12-22(19-39-40(36,37)38)7-5-8-23-17-27(34)33(28(23)35)16-13-24-18-31-20-32-24/h9,17-18,20-22,25H,5-8,10-16,19H2,1-4H3,(H,31,32)(H,36,37,38)/t21-,22?,25-,30-/m0/s1

Standard InChI Key:  KYSKWYJBCHWKSD-VMBXUYBNSA-N

Molfile:  

     RDKit          2D

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   16.7495   -2.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7495   -0.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4615   -0.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4580   -1.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1668   -2.1674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8836   -1.7602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8871   -0.9352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1738   -0.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4500   -2.5750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.6037   -0.5265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1762    0.3076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8918    0.7180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.3292   -2.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9583   -2.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6098    1.9535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1809    1.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4652    1.5471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7519    1.9617    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.0333    2.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1649    2.6759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3425    1.2454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3231    1.5390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0388    1.9494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7520    1.5349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8340    0.7163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6405    0.5424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.0551    1.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5047    1.8703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9739   -0.2122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4871   -0.8783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8205   -1.6329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4116   -2.3446    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9619   -2.9592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7166   -2.6258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.6326   -1.8051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8833   -0.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8758    1.3397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2188    0.1666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 19 20  1  0
  8  9  1  0
 20 21  1  0
  9 10  1  0
 21 22  1  0
  5  6  1  0
 21 23  2  0
  6 11  1  1
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 18 25  1  0
  9 12  1  1
 25 26  1  0
  1  2  1  0
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 27 28  1  0
 10 13  1  0
  1  4  1  0
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  2  3  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 27  2  0
 14 15  1  0
 29 32  1  0
  3  6  1  0
 32 33  1  0
  3 16  1  0
 33 34  1  0
 34 35  1  0
  5  4  2  0
  3 17  1  0
  5 10  1  0
 15 18  1  0
 35 36  2  0
 36 37  1  0
 37 38  1  0
 38 34  2  0
  6  7  1  0
 10 39  1  6
 15 19  1  0
 30 40  2  0
  7  8  1  0
 28 41  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA556261

   19-OXOFASCIOSPONGINE A

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: 575.77

Molecular Weight (Monoisotopic): 575.3029

AlogP: 5.43

#Rotatable Bonds: 13

Polar Surface Area: 129.66

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -1.34

CX Basic pKa: 6.55

CX LogP: 2.70

CX LogD: 2.57

Aromatic Rings: 1

Heavy Atoms: 40

QED Weighted: 0.18

Np Likeness Score: 2.11

References

1. Yao G, Kondratyuk TP, Tan GT, Pezzuto JM, Chang LC..  (2009)  Bioactive sulfated sesterterpene alkaloids and sesterterpene sulfates from the marine sponge Fasciospongia sp.,  72  (2): [PMID:19178162] [10.1021/np8005343]

Source

Source(1):

• Scientific Literature