herbimycin C

ID: ALA486827

Cas Number: 91700-92-4

PubChem CID: 23958192

Max Phase: Preclinical

Molecular Formula: C29H40N2O9

Molecular Weight: 560.64

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Herbimycin C | Herbimycin C|91700-92-4|CHEMBL486827|ACon1_002423|BDBM50533274|[(4E,6Z,8S,9S,10E,12S,13R,14S,16S,17R)-13-hydroxy-8,14,17-trimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl] carbamate

Canonical SMILES:  CO[C@H]1/C=C\C=C(/C)C(=O)NC2=CC(=O)C=C(C2=O)[C@H](OC)[C@@H](C)C[C@H](OC)[C@H](O)[C@@H](C)/C=C(\C)[C@@H]1OC(N)=O

Standard InChI:  InChI=1S/C29H40N2O9/c1-15-9-8-10-22(37-5)27(40-29(30)36)17(3)11-16(2)24(33)23(38-6)12-18(4)26(39-7)20-13-19(32)14-21(25(20)34)31-28(15)35/h8-11,13-14,16,18,22-24,26-27,33H,12H2,1-7H3,(H2,30,36)(H,31,35)/b10-8-,15-9+,17-11+/t16-,18-,22-,23-,24+,26+,27-/m0/s1

Standard InChI Key:  DWFFHRSGCPBMKD-OOJAHTAHSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA486827

   HERBIMYCIN C

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: 560.64

Molecular Weight (Monoisotopic): 560.2734

AlogP: 2.06

#Rotatable Bonds: 4

Polar Surface Area: 163.48

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.78

CX Basic pKa: ┄

CX LogP: 2.05

CX LogD: 2.05

Aromatic Rings: ┄

Heavy Atoms: 40

QED Weighted: 0.34

Np Likeness Score: 2.70

References

1. Lin LZ, Blaskó G, Cordell GA..  (1988)  1H-nmr analysis of herbimycins and dihydro-herbimycins.,  51  (6): [PMID:3236008] [10.1021/np50060a018]

2. Zhang Z, Xue N, Bian C, Yan R, Jin L, Chen X, Yu X..  (2016)  C15-methoxyphenylated 18-deoxy-herbimycin A analogues, their in vitro anticancer activity and heat shock protein 90 binding affinity.,  26  (17): [PMID:27476419] [10.1016/j.bmcl.2016.07.040]

3. 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]

Source

Source(1):

• Scientific Literature