bastadin 13

ID: ALA445712

Chembl Id: CHEMBL445712

PubChem CID: 23426999

Max Phase: Preclinical

Molecular Formula: C34H28Br4N4O8

Molecular Weight: 940.23

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Bastadin 13 | Bastadin 13|CHEMBL445712

Canonical SMILES:  O=C1NCCc2ccc(c(Br)c2)Oc2cc(ccc2O)CCNC(=O)/C(=N/O)Cc2cc(Br)c(O)c(c2)Oc2c(Br)cc(cc2Br)C/C1=N\O

Standard InChI:  InChI=1S/C34H28Br4N4O8/c35-21-9-17-2-4-28(21)49-29-15-18(1-3-27(29)43)6-8-40-34(46)26(42-48)14-20-10-22(36)31(44)30(16-20)50-32-23(37)11-19(12-24(32)38)13-25(41-47)33(45)39-7-5-17/h1-4,9-12,15-16,43-44,47-48H,5-8,13-14H2,(H,39,45)(H,40,46)/b41-25+,42-26+

Standard InChI Key:  XNGIESBQQZJDTL-RIVOPQIESA-N

Alternative Forms

1. Parent:

   

   ALA445712

   BASTADIN 13

Molecule Features

Natural Product: No

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: 940.23

Molecular Weight (Monoisotopic): 935.8641

AlogP: 7.51

#Rotatable Bonds: ┄

Polar Surface Area: 182.30

Molecular Species: NEUTRAL

HBA: 10

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 4

CX Acidic pKa: 6.96

CX Basic pKa: ┄

CX LogP: 8.20

CX LogD: 7.47

Aromatic Rings: 4

Heavy Atoms: 50

QED Weighted: 0.08

Np Likeness Score: 1.18

References

1. Pettit GR, Butler MS, Bass CG, Doubek DL, Williams MD, Schmidt JM, Pettit RK, Hooper JN, Tackett LP, Filiatrault MJ..  (1995)  Antineoplastic agents, 326. The stereochemistry of bastadins 8, 10, and 12 from the Bismarck archipelago marine sponge Ianthella basta.,  58  (5): [PMID:7623047] [10.1021/np50119a005]

2. Gulavita NK, Wright AE, McCarthy PJ, Pomponi SA, Kelly-Borges M, Chin M, Sills MA..  (1993)  Isolation and structure elucidation of 34-sulfatobastadin 13, an inhibitor of the endothelin A receptor, from a marine sponge of the genus Ianthella.,  56  (9): [PMID:8254355] [10.1021/np50099a026]

3. Calcul L, Inman WD, Morris AA, Tenney K, Ratnam J, McKerrow JH, Valeriote FA, Crews P..  (2010)  Additional insights on the bastadins: isolation of analogues from the sponge Ianthella cf. reticulata and exploration of the oxime configurations.,  73  (3): [PMID:20102170] [10.1021/np9005986]

4. Bedos-Belval F, Rouch A, Vanucci-Bacque C, Baltas M.  (2012)  Diaryl ether derivatives as anticancer agents a review,  3  (11): [10.1039/C2MD20199B]

Source

Source(1):

• Scientific Literature