fasciospongine C

ID: ALA552096

PubChem CID: 25242869

Max Phase: Preclinical

Molecular Formula: C30H52N4O5S

Molecular Weight: 580.84

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Fasciospongine C | fasciospongine C|CHEMBL552096

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

Standard InChI:  InChI=1S/C30H52N4O5S/c1-22-12-13-25-26(11-8-16-29(25,2)3)30(22,4)17-14-23(21-39-40(36,37)38)9-7-10-24-15-20-34(27(24)35)19-6-5-18-33-28(31)32/h11,15,22-23,25H,5-10,12-14,16-21H2,1-4H3,(H4,31,32,33)(H,36,37,38)/t22-,23?,25-,30-/m0/s1

Standard InChI Key:  QFJUUZMSENDBFD-HMDKUDOWSA-N

Molfile:  

     RDKit          2D

 41 43  0  0  0  0  0  0  0  0999 V2000
   -4.7750   -7.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7750   -8.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0630   -8.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0630   -6.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3510   -7.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3545   -8.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6457   -8.6382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9289   -8.2310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9254   -7.4061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6387   -6.9882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3625   -9.0458    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2088   -6.9973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6363   -6.1633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9207   -5.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9183   -4.9278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4833   -9.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8542   -9.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2027   -4.5173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6316   -4.5133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3473   -4.9237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0606   -4.5092    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7792   -4.0958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6476   -3.7950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4700   -5.2254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4894   -4.9319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2263   -4.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9395   -4.9360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0215   -5.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8280   -5.9284    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2426   -5.2151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6922   -4.6005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1614   -6.6830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6746   -7.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0080   -8.1037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1494   -9.4301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9041   -9.0966    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8201   -8.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9292   -6.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4063   -6.3042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4834   -8.9432    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0608  -10.2503    0.0000 N   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
 21 24  2  0
 18 25  1  0
  9 12  1  1
 25 26  1  0
  1  2  1  0
 26 27  1  0
 27 28  1  0
 10 13  1  0
  1  4  1  0
 13 14  1  0
  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
  5  4  2  0
  3 17  1  0
  5 10  1  0
 35 36  1  0
 36 37  1  0
 37 34  1  0
 15 18  1  0
 10 38  1  6
  6  7  1  0
 28 39  2  0
 15 19  1  0
 35 40  1  0
  7  8  1  0
 35 41  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA552096

   FASCIOSPONGINE C

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: 580.84

Molecular Weight (Monoisotopic): 580.3658

AlogP: 5.20

#Rotatable Bonds: 15

Polar Surface Area: 145.81

Molecular Species: ZWITTERION

HBA: 5

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -1.48

CX Basic pKa: 12.15

CX LogP: 4.27

CX LogD: 4.27

Aromatic Rings: ┄

Heavy Atoms: 40

QED Weighted: 0.07

Np Likeness Score: 2.24

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