Makaluvamine F

ID: ALA509890

Chembl Id: CHEMBL509890

PubChem CID: 135407624

Max Phase: Preclinical

Molecular Formula: C18H14BrN3O2S

Molecular Weight: 416.30

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (-)-Makaluvamine F | Makaluvamine F

Canonical SMILES:  O=C1C(NC2Cc3cc(Br)c(O)cc3S2)=CC2=NCCc3c[nH]c1c32

Standard InChI:  InChI=1S/C18H14BrN3O2S/c19-10-3-9-4-15(25-14(9)6-13(10)23)22-12-5-11-16-8(1-2-20-11)7-21-17(16)18(12)24/h3,5-7,15,21-23H,1-2,4H2

Standard InChI Key:  ZEIRCDSUNJVVPP-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA509890

   MAKALUVAMINE F

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: 416.30

Molecular Weight (Monoisotopic): 414.9990

AlogP: 3.17

#Rotatable Bonds: 2

Polar Surface Area: 77.48

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.48

CX Basic pKa: 7.65

CX LogP: 2.36

CX LogD: 2.15

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.70

Np Likeness Score: 1.82

References

1. Schmidt EW, Harper MK, Faulkner DJ..  (1995)  Makaluvamines H-M and damirone C from the pohnpeian sponge Zyzzya fuliginosa.,  58  (12): [PMID:8691207] [10.1021/np50126a008]

2. Jeon JE, Na Z, Jung M, Lee HS, Sim CJ, Nahm K, Oh KB, Shin J..  (2010)  Discorhabdins from the Korean marine sponge Sceptrella sp.,  73  (2): [PMID:20055495] [10.1021/np9005629]

3. Davis RA, Buchanan MS, Duffy S, Avery VM, Charman SA, Charman WN, White KL, Shackleford DM, Edstein MD, Andrews KT, Camp D, Quinn RJ..  (2012)  Antimalarial activity of pyrroloiminoquinones from the Australian marine sponge Zyzzya sp.,  55  (12): [PMID:22686608] [10.1021/jm3002795]

4. Goey AK, Chau CH, Sissung TM, Cook KM, Venzon DJ, Castro A, Ransom TR, Henrich CJ, McKee TC, McMahon JB, Grkovic T, Cadelis MM, Copp BR, Gustafson KR, Figg WD..  (2016)  Screening and Biological Effects of Marine Pyrroloiminoquinone Alkaloids: Potential Inhibitors of the HIF-1α/p300 Interaction.,  79  (5): [PMID:27140429] [10.1021/acs.jnatprod.5b00846]

Source

Source(1):

• Scientific Literature