Rapamycin analogue

ID: ALA216404

Chembl Id: CHEMBL216404

PubChem CID: 44280039

Max Phase: Preclinical

Molecular Formula: C52H80N2O14

Molecular Weight: 957.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)N[C@@H]1C[C@@H]2CC[C@@H](C)[C@@](O)(O2)C(=O)C(=O)N2CCCC[C@H]2C(=O)O[C@H]([C@H](C)C[C@@H]2CC[C@@H](O)[C@H](OC)C2)CC(=O)[C@H](C)/C=C(\C)[C@@H](O)[C@@H](OC)C(=O)[C@H](C)C[C@H](C)/C=C/C=C/C=C/1C

Standard InChI:  InChI=1S/C52H80N2O14/c1-30-16-12-11-13-17-31(2)39(53-51(62)66-10)28-38-21-19-36(7)52(63,68-38)48(59)49(60)54-23-15-14-18-40(54)50(61)67-43(33(4)26-37-20-22-41(55)44(27-37)64-8)29-42(56)32(3)25-35(6)46(58)47(65-9)45(57)34(5)24-30/h11-13,16-17,25,30,32-34,36-41,43-44,46-47,55,58,63H,14-15,18-24,26-29H2,1-10H3,(H,53,62)/b13-11+,16-12+,31-17+,35-25+/t30-,32-,33-,34-,36-,37+,38+,39-,40+,41-,43+,44-,46-,47+,52-/m1/s1

Standard InChI Key:  DZCMVIOVXITEOT-OXKLTXKKSA-N

Alternative Forms

1. Parent:

   

   ALA216404

   methyl N-[(1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30R,32S,35R)-1,18-dihydroxy-12-[(2R)-1-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl]-19-methoxy-15,17,21,23,29,35-hexamethyl-2,3,10,14,20-pentaoxo-11,36-dioxa-4-azatricyclo[30.3.1.04,9]hexa

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: 957.21

Molecular Weight (Monoisotopic): 956.5610

AlogP: 5.89

#Rotatable Bonds: 6

Polar Surface Area: 224.53

Molecular Species: NEUTRAL

HBA: 14

HBD: 4

#RO5 Violations: 3

HBA (Lipinski): 16

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 9.96

CX Basic pKa: ┄

CX LogP: 7.14

CX LogD: 7.14

Aromatic Rings: ┄

Heavy Atoms: 68

QED Weighted: 0.14

Np Likeness Score: 1.68

References

1. Dickman DA, Ding H, Li Q, Nilius AM, Balli DJ, Ballaron SJ, Trevillyan JM, Smith ML, Seif LS, Kim K, Sarthy A, Goldman RC, Plattner JJ, Bennani YL..  (2000)  Antifungal rapamycin analogues with reduced immunosuppressive activity.,  10  (13): [PMID:10888319] [10.1016/s0960-894x(00)00184-0]

2. Guduru SKR, Arya P..  (2018)  Synthesis and biological evaluation of rapamycin-derived, next generation small molecules.,  9  (1): [PMID:30108899] [10.1039/C7MD00474E]

Source

Source(1):

• Scientific Literature