ID: ALA413

Max Phase: Approved

First Approval: 1999

Molecular Formula: C51H79NO13

Molecular Weight: 914.19

Molecule Type: Small molecule

Representations

Synonyms (11): Fyarro | Hyftor | Npc-12g | Rapalimus | Rapamycin | Sirolimus | AY-22989 | L04AA10 | NSC-226080 | SM-88 COMPONENT SIROLIMUS | WY-090217
Synonyms from Alternative Forms(11):

Trade Names(4): Fyarro | Hyftor | Rapamune | Sirolimus

Canonical SMILES:  CO[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/C51H79NO13/c1-30-16-12-11-13-17-31(2)42(61-8)28-38-21-19-36(7)51(60,65-38)48(57)49(58)52-23-15-14-18-39(52)50(59)64-43(33(4)26-37-20-22-40(53)44(27-37)62-9)29-41(54)32(3)25-35(6)46(56)47(63-10)45(55)34(5)24-30/h11-13,16-17,25,30,32-34,36-40,42-44,46-47,53,56,60H,14-15,18-24,26-29H2,1-10H3/b13-11+,16-12+,31-17+,35-25+/t30-,32-,33-,34-,36-,37+,38+,39+,40-,42+,43+,44-,46-,47+,51-/m1/s1

Standard InChI Key:  QFJCIRLUMZQUOT-HPLJOQBZSA-N

Molecule Features

Natural Product: No

Oral: Yes

Chemical Probe: Yes

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: Yes

Chirality: Yes

Availability: Yes

Prodrug: No

Properties

Molecular Weight: 914.19

Molecular Weight (Monoisotopic): 913.5551

AlogP: 6.18

#Rotatable Bonds: 6

Polar Surface Area: 195.43

Molecular Species: NEUTRAL

HBA: 13

HBD: 3

#RO5 Violations: 3

HBA (Lipinski): 14

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 9.96

CX Basic pKa:

CX LogP: 7.45

CX LogD: 7.45

Aromatic Rings: 0

Heavy Atoms: 65

QED Weighted: 0.16

Np Likeness Score: 1.94

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Source

Source(18):

• Scientific Literature
• Sanger Institute Genomics of Drug Sensitivity in Cancer
• PubChem BioAssays
• Clinical Candidates
• FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book)
• USP Dictionary of USAN and International Drug Names
• DrugMatrix
• TP-search Transporter Database
• AstraZeneca Deposited Data
• Curated Drug Metabolism Pathways
• Patent Bioactivity Data
• CO-ADD antimicrobial screening data
• WHO Anatomical Therapeutic Chemical Classification
• British National Formulary
• Kuster lab chemical proteomics drug profiling
• SARS-CoV-2 Screening Data 2020-21
• Fraunhofer HDAC6
• European Medicines Agency