Rokitamycin

ID: ALA1908350

Cas Number: 74014-51-0

PubChem CID: 5282211

Max Phase: Phase

Molecular Formula: C42H69NO15

Molecular Weight: 828.01

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 3''-propionylleucomycin a5 | Ricamycin | TMS 19Q | TMS-19Q | rokitamycin|Ricamycin|74014-51-0|TMS 19Q|Propionylleucomycin|TMS-19Q|ZPT03UEM0E|3''-propionylleucomycin a5|Leucomycin V, 4B-butanoate 3B-propanoate|[(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-6-[[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-4,10-dihydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy-2,4-dimethyl-4-propanoyloxyoxan-3-yl] butanoate|Rokitamicina|RokitamyShow More⌵

Canonical SMILES:  CCCC(=O)O[C@H]1[C@H](C)O[C@@H](O[C@H]2[C@H](N(C)C)[C@@H](O)[C@H](O[C@H]3[C@@H](CC=O)C[C@@H](C)[C@@H](O)/C=C/C=C/C[C@@H](C)OC(=O)C[C@@H](O)[C@@H]3OC)O[C@@H]2C)C[C@@]1(C)OC(=O)CC

Standard InChI:  InChI=1S/C42H69NO15/c1-11-16-32(48)55-40-27(6)53-34(23-42(40,7)58-31(47)12-2)56-37-26(5)54-41(36(50)35(37)43(8)9)57-38-28(19-20-44)21-24(3)29(45)18-15-13-14-17-25(4)52-33(49)22-30(46)39(38)51-10/h13-15,18,20,24-30,34-41,45-46,50H,11-12,16-17,19,21-23H2,1-10H3/b14-13+,18-15+/t24-,25-,26-,27+,28+,29+,30-,34+,35-,36-,37-,38+,39+,40+,41+,42-/m1/s1

Standard InChI Key:  VYWWNRMSAPEJLS-MDWYKHENSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA1908350

   ROKITAMYCIN

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: 828.01

Molecular Weight (Monoisotopic): 827.4667

AlogP: 3.16

#Rotatable Bonds: 13

Polar Surface Area: 206.05

Molecular Species: NEUTRAL

HBA: 16

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.71

CX Basic pKa: 7.90

CX LogP: 3.63

CX LogD: 3.01

Aromatic Rings: ┄

Heavy Atoms: 58

QED Weighted: 0.14

Np Likeness Score: 2.07

References

1. Morozumi M, Iwata S, Hasegawa K, Chiba N, Takayanagi R, Matsubara K, Nakayama E, Sunakawa K, Ubukata K, Acute Respiratory Diseases Study Group..  (2008)  Increased macrolide resistance of Mycoplasma pneumoniae in pediatric patients with community-acquired pneumonia.,  52  (1): [PMID:17954691] [10.1128/aac.00779-07]

2. Miura T, Natsume S, Kanemoto K, Shitara E, Fushimi H, Yoshida T, Ajito K..  (2010)  Novel azalides derived from 16-membered macrolides. III. Azalides modified at the C-15 and 4'' positions: Improved antibacterial activities.,  18  (7): [PMID:20236827] [10.1016/j.bmc.2010.02.017]

3. 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]

4. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

5. Biour M, Ben Salem C, Chazouillères O, Grangé JD, Serfaty L, Poupon R..  (2004)  [Drug-induced liver injury; fourteenth updated edition of the bibliographic database of liver injuries and related drugs].,  28  (8-9): [PMID:15646539] [10.1016/s0399-8320(04)95062-2]

6. WHO Anatomical Therapeutic Chemical Classification, 

7. Sutherland JJ, Yonchev D, Fekete A, Urban L..  (2023)  A preclinical secondary pharmacology resource illuminates target-adverse drug reaction associations of marketed drugs.,  14  (1): [PMID:37468498] [10.1038/s41467-023-40064-9]

Source

Source(3):

• Scientific Literature
• USP Dictionary of USAN and International Drug Names
• WHO Anatomical Therapeutic Chemical Classification