ID: ALA403143

Max Phase: Preclinical

Molecular Formula: C54H76N2O12

Molecular Weight: 945.20

Molecule Type: Small molecule

Representations

Synonyms (1): Cephalostatin 12
Synonyms from Alternative Forms(1):

Canonical SMILES:  C[C@@H]1[C@]2(O[C@H]3C=C4[C@@H]5CC[C@H]6Cc7nc8c(nc7C[C@]6(C)[C@H]5C[C@@H](O)[C@]4(C)[C@]31O)C[C@@H]1CC[C@H]3C4=C[C@@H]5O[C@]6(O[C@](C)(CO)C[C@H]6O)[C@@H](C)[C@]5(O)[C@@]4(C)[C@H](O)C[C@@H]3[C@@]1(C)C8)O[C@](C)(CO)C[C@H]2O

Standard InChI:  InChI=1S/C54H76N2O12/c1-25-51(63)43(65-53(25)41(61)21-45(3,23-57)67-53)17-33-29-11-9-27-13-35-37(19-47(27,5)31(29)15-39(59)49(33,51)7)55-36-14-28-10-12-30-32(48(28,6)20-38(36)56-35)16-40(60)50(8)34(30)18-44-52(50,64)26(2)54(66-44)42(62)22-46(4,24-58)68-54/h17-18,25-32,39-44,57-64H,9-16,19-24H2,1-8H3/t25-,26-,27-,28-,29+,30+,31-,32-,39+,40+,41+,42+,43-,44-,45-,46-,47-,48-,49+,50+,51+,52+,53-,54-/m0/s1

Standard InChI Key:  NVRMDLWDRHEFNO-LGANMPMMSA-N

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

Properties

Molecular Weight: 945.20

Molecular Weight (Monoisotopic): 944.5398

AlogP: 3.38

#Rotatable Bonds: 2

Polar Surface Area: 224.54

Molecular Species: NEUTRAL

HBA: 14

HBD: 8

#RO5 Violations: 3

HBA (Lipinski): 14

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.40

CX Basic pKa: 1.52

CX LogP: 1.60

CX LogD: 1.60

Aromatic Rings: 1

Heavy Atoms: 68

QED Weighted: 0.20

Np Likeness Score: 1.20

References

1. Pettit GR, Ichihara Y, Xu J, Boyd MR, Williams MD.  (1994)  Isolation and structure of the symmetrical disteroidal alkaloids cephalostatin 12 and cephalostatin 13,  4  (12): [10.1016/S0960-894X(01)80522-9]

2. Moser BR..  (2008)  Review of cytotoxic cephalostatins and ritterazines: isolation and synthesis.,  71  (3): [PMID:18197599] [10.1021/np070536z]

3. Pettit GR, Moser BR, Mendonça RF, Knight JC, Hogan F..  (2012)  The cephalostatins. 22. synthesis of bis-steroidal pyrazine pyrones (1).,  75  (6): [PMID:22607450] [10.1021/np300069z]

4. Pettit GR, Xu JP, Chapuis JC, Melody N..  (2015)  The Cephalostatins. 24. Isolation, Structure, and Cancer Cell Growth Inhibition of Cephalostatin 20.,  78  (6): [PMID:26042639] [10.1021/acs.jnatprod.5b00129]

Source

Source(1):

• Scientific Literature