ID: ALA3085436

Max Phase: Approved

First Approval: 1982

Molecular Formula: C25H43N13O10

Molecular Weight: 685.70

Molecule Type: Protein

Representations

Synonyms (5): Celiomycin | Florimycin | Tuberactinomycin b | Vinacetin a | Vioactane
Synonyms from Alternative Forms(5):

Canonical SMILES:  NCCC[C@H](N)CC(=O)N[C@H]1CNC(=O)[C@H]([C@H]2C[C@H](O)NC(N)=N2)NC(=O)/C(=C/NC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC1=O

Standard InChI:  InChI=1S/C25H43N13O10/c26-3-1-2-10(27)4-16(41)32-12-6-30-23(47)18(11-5-17(42)37-24(28)36-11)38-20(44)13(7-31-25(29)48)33-21(45)14(8-39)35-22(46)15(9-40)34-19(12)43/h7,10-12,14-15,17-18,39-40,42H,1-6,8-9,26-27H2,(H,30,47)(H,32,41)(H,33,45)(H,34,43)(H,35,46)(H,38,44)(H3,28,36,37)(H3,29,31,48)/b13-7-/t10-,11+,12-,14-,15-,17-,18-/m0/s1

Standard InChI Key:  GXFAIFRPOKBQRV-GHXCTMGLSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: Yes

Molecule Type: Protein

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Properties

Molecular Weight: 685.70

Molecular Weight (Monoisotopic): 685.3256

AlogP: -8.88

#Rotatable Bonds: 10

Polar Surface Area: 392.86

Molecular Species: BASE

HBA: 15

HBD: 15

#RO5 Violations: 3

HBA (Lipinski): 23

HBD (Lipinski): 19

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 8.99

CX Basic pKa: 22.11

CX LogP: -10.98

CX LogD: -16.45

Aromatic Rings: 0

Heavy Atoms: 48

QED Weighted: 0.09

Np Likeness Score: 1.01

References

1. Carlson HA, Masukawa KM, Rubins K, Bushman FD, Jorgensen WL, Lins RD, Briggs JM, McCammon JA..  (2000)  Developing a dynamic pharmacophore model for HIV-1 integrase.,  43  (11): [PMID:10841789] [10.1021/jm990322h]

2. Bodoor K, Boyapati V, Gopu V, Boisdore M, Allam K, Miller J, Treleaven WD, Weldeghiorghis T, Aboul-ela F..  (2009)  Design and implementation of an ribonucleic acid (RNA) directed fragment library.,  52  (12): [PMID:19445516] [10.1021/jm9000659]

3. Feldman MB, Terry DS, Altman RB, Blanchard SC..  (2010)  Aminoglycoside activity observed on single pre-translocation ribosome complexes.,  6  (1): [PMID:19946275] [10.1038/nchembio.274]

4. Kruhlak NL, Choi SS, Contrera JF, Weaver JL, Willard JM, Hastings KL, Sancilio LF..  (2008)  Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models.,  18  (2): [PMID:20020916] [10.1080/15376510701857262]

5. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

6. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]

7. Mishra SK, Tripathi G, Kishore N, Singh RK, Singh A, Tiwari VK..  (2017)  Drug development against tuberculosis: Impact of alkaloids.,  137  [PMID:28628823] [10.1016/j.ejmech.2017.06.005]

Source

Source(3):

• Scientific Literature
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6