reblastatin

ID: ALA267792

PubChem CID: 9807556

Max Phase: Preclinical

Molecular Formula: C29H44N2O8

Molecular Weight: 548.68

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Reblastatin | reblastatin|CHEMBL267792|SCHEMBL13009052|CHEBI:208919|BDBM50542414|[(4E,8S,9S,10E,12S,13R,14S,16R)-13,20-dihydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-3-oxo-2-azabicyclo[16.3.1]docosa-1(22),4,10,18,20-pentaen-9-yl] carbamate

Canonical SMILES:  COc1c(O)cc2cc1C[C@@H](C)C[C@H](OC)[C@H](O)[C@@H](C)/C=C(\C)[C@H](OC(N)=O)[C@@H](OC)CC/C=C(\C)C(=O)N2

Standard InChI:  InChI=1S/C29H44N2O8/c1-16-11-20-14-21(15-22(32)27(20)38-7)31-28(34)17(2)9-8-10-23(36-5)26(39-29(30)35)19(4)13-18(3)25(33)24(12-16)37-6/h9,13-16,18,23-26,32-33H,8,10-12H2,1-7H3,(H2,30,35)(H,31,34)/b17-9+,19-13+/t16-,18+,23+,24+,25-,26+/m1/s1

Standard InChI Key:  VFJOOSVDHSUNKR-DQJDZTSCSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA267792

   REBLASTATIN

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: 548.68

Molecular Weight (Monoisotopic): 548.3098

AlogP: 4.09

#Rotatable Bonds: 4

Polar Surface Area: 149.57

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.77

CX Basic pKa: ┄

CX LogP: 3.94

CX LogD: 3.94

Aromatic Rings: 1

Heavy Atoms: 39

QED Weighted: 0.41

Np Likeness Score: 1.95

References

1. Onodera H, Kaneko M, Takahashi Y, Uochi Y, Funahashi J, Nakashima T, Soga S, Suzuki M, Ikeda S, Yamashita Y, Rahayu ES, Kanda Y, Ichimura M..  (2008)  Conformational significance of EH21A1-A4, phenolic derivatives of geldanamycin, for Hsp90 inhibitory activity.,  18  (5): [PMID:18243703] [10.1016/j.bmcl.2008.01.072]

2. Nong XH, Tu ZC, Qi SH..  (2020)  Ansamycin derivatives from the marine-derived Streptomyces sp. SCSGAA 0027 and their cytotoxic and antiviral activities.,  30  (11): [PMID:32273216] [10.1016/j.bmcl.2020.127168]

3. Skrzypczak N,Pyta K,Ruszkowski P,Gdaniec M,Bartl F,Przybylski P.  (2020)  Synthesis, structure and anticancer activity of new geldanamycin amine analogs containing C(17)- or C(20)- flexible and rigid arms as well as closed or open ansa-bridges.,  202  [PMID:32663707] [10.1016/j.ejmech.2020.112624]

Source

Source(1):

• Scientific Literature