ID: ALA295292

Max Phase: Preclinical

Molecular Formula: C46H48N2O8

Molecular Weight: 756.90

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1cc(C)cc2c(-c3c(O)cc(O)c4c3C[C@@H](C)N[C@@H]4C)cc(-c3cc(-c4c(O)cc(O)c5c4C[C@@H](C)N[C@@H]5C)c4cc(C)cc(OC)c4c3O)c(O)c12

Standard InChI:  InChI=1S/C46H48N2O8/c1-19-9-25-27(41-31-13-21(3)47-23(5)39(31)33(49)17-35(41)51)15-29(45(53)43(25)37(11-19)55-7)30-16-28(26-10-20(2)12-38(56-8)44(26)46(30)54)42-32-14-22(4)48-24(6)40(32)34(50)18-36(42)52/h9-12,15-18,21-24,47-54H,13-14H2,1-8H3/t21-,22-,23-,24-/m1/s1

Standard InChI Key:  GMLBVLXDRNJFGR-MOUTVQLLSA-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: 756.90

Molecular Weight (Monoisotopic): 756.3411

AlogP: 9.05

#Rotatable Bonds: 5

Polar Surface Area: 163.90

Molecular Species: BASE

HBA: 10

HBD: 8

#RO5 Violations: 3

HBA (Lipinski): 10

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 7.72

CX Basic pKa: 10.88

CX LogP: 6.15

CX LogD: 5.24

Aromatic Rings: 6

Heavy Atoms: 56

QED Weighted: 0.09

Np Likeness Score: 1.02

References

1. Boyd MR, Hallock YF, Cardellina JH, Manfredi KP, Blunt JW, McMahon JB, Buckheit RW, Bringmann G, Schäffer M, Cragg GM..  (1994)  Anti-HIV michellamines from Ancistrocladus korupensis.,  37  (12): [PMID:8021914] [10.1021/jm00038a003]

2. Boyd MR, Hallock YF, Cardellina JH, Manfredi KP, Blunt JW, McMahon JB, Buckheit RW, Bringmann G, Schäffer M, Cragg GM..  (1994)  Anti-HIV michellamines from Ancistrocladus korupensis.,  37  (12): [PMID:8021914] [10.1021/jm00038a003]

3. Boyd MR, Hallock YF, Cardellina JH, Manfredi KP, Blunt JW, McMahon JB, Buckheit RW, Bringmann G, Schäffer M, Cragg GM..  (1994)  Anti-HIV michellamines from Ancistrocladus korupensis.,  37  (12): [PMID:8021914] [10.1021/jm00038a003]

4. Hallock YF, Manfredi KP, Dai JR, Cardellina JH, Gulakowski RJ, McMahon JB, Schäffer M, Stahl M, Gulden KP, Bringmann G, François G, Boyd MR..  (1997)  Michellamines D-F, new HIV-inhibitory dimeric naphthylisoquinoline alkaloids, and korupensamine E, a new antimalarial monomer, from Ancistrocladus korupensis.,  60  (7): [PMID:9249970] [10.1021/np9700679]

5. Yang SS, Cragg GM, Newman DJ, Bader JP..  (2001)  Natural product-based anti-HIV drug discovery and development facilitated by the NCI developmental therapeutics program.,  64  (2): [PMID:11430019] [10.1021/np0003995]

6. Mihalyi A, Jamshidi S, Slikas J, Bugg TD..  (2014)  Identification of novel inhibitors of phospho-MurNAc-pentapeptide translocase MraY from library screening: Isoquinoline alkaloid michellamine B and xanthene dye phloxine B.,  22  (17): [PMID:25127465] [10.1016/j.bmc.2014.07.035]

Source

Source(1):

• Scientific Literature