Diazepinomicin

ID: ALA550961

Chembl Id: CHEMBL550961

Cas Number: 179981-40-9

PubChem CID: 9868980

Max Phase: Phase

Molecular Formula: C28H34N2O4

Molecular Weight: 462.59

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Amo-01 | Diazepinomicin | BU-4664L | ECO-4601 | TLN-4601 | Diazepinomicin|TLN-4601|733035-26-2|BU-4664L|ECO-4601|Amo-01|UNII-YPH994Y0RF|YPH994Y0RF|ECO 4601|TLN 4601|11H-Dibenzo(b,E)(1,4)diazepin-11-one, 5,10-dihydro-4,6,8-trihydroxy-10-((2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-yl)-|TLN4601|ECO-04601|1,3,10-trihydroxy-5-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]-11H-benzo[b][1,4]benzodiazepin-6-one|4,6,8-trihydroxy-10-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)-5H-dibenzo[b,e][1,Show More⌵

Canonical SMILES:  CC(C)=CCC/C(C)=C/CC/C(C)=C/CN1C(=O)c2cccc(O)c2Nc2c(O)cc(O)cc21

Standard InChI:  InChI=1S/C28H34N2O4/c1-18(2)8-5-9-19(3)10-6-11-20(4)14-15-30-23-16-21(31)17-25(33)27(23)29-26-22(28(30)34)12-7-13-24(26)32/h7-8,10,12-14,16-17,29,31-33H,5-6,9,11,15H2,1-4H3/b19-10+,20-14+

Standard InChI Key:  SALVHVNECODMJP-GNUCVDFRSA-N

Alternative Forms

1. Parent:

   

   ALA550961

   DIAZEPINOMICIN

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 462.59

Molecular Weight (Monoisotopic): 462.2519

AlogP: 6.93

#Rotatable Bonds: 8

Polar Surface Area: 93.03

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.88

CX Basic pKa: 0.73

CX LogP: 7.47

CX LogD: 7.45

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.19

Np Likeness Score: 1.36

References

1. Ratnayake AS, Janso JE, Feng X, Schlingmann G, Goljer I, Carter GT..  (2009)  Evaluating indole-related derivatives as precursors in the directed biosynthesis of diazepinomicin analogues.,  72  (3): [PMID:19199816] [10.1021/np800664u]

2. Miyanaga S, Sakurai H, Saiki I, Onaka H, Igarashi Y..  (2010)  Anti-invasive and anti-angiogenic activities of naturally occurring dibenzodiazepine BU-4664L and its derivatives.,  20  (3): [PMID:20056543] [10.1016/j.bmcl.2009.12.055]

3. Unpublished dataset, 

4. Liu C, Xu YY, Wen ZH, Dong YH, Liu ZP..  (2022)  Synthesis and biological evaluation of BU-4664L derivatives as potential anticancer agents.,  55  [PMID:34838651] [10.1016/j.bmcl.2021.128474]

Source

Source(2):

• Scientific Literature
• Clinical Candidates