Details of the Drug

General Information of Drug (ID: DMQTUH8)

Drug Name
CALANOLIDE A
Synonyms NSC-675451; NSC-664737 (racemate); (+)-(10R,11S,12S)-12-Hydroxy-6,6,10,11-tetramethyl-4-propyl-6,10,11,12-tetrahydro-2H-benzo[1,2-b:3,4-b':5,6-b'']tripyran-2-one; (+)-Calanolide A
Indication
Disease Entry ICD 11 Status REF
Mycobacterium infection 1B10-1B21 Phase 1 [1]
Affected Organisms
Human Immunodeficiency Virus
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 370.4
Logarithm of the Partition Coefficient (xlogp) 3.8
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 5
ADMET Property
Half-life
The concentration or amount of drug in body reduced by one-half in 20 hours [2]
Metabolism
The drug is metabolized via the hepatic []
Chemical Identifiers
Formula
C22H26O5
IUPAC Name
(16R,17S,18S)-18-hydroxy-10,10,16,17-tetramethyl-6-propyl-3,9,15-trioxatetracyclo[12.4.0.02,7.08,13]octadeca-1(14),2(7),5,8(13),11-pentaen-4-one
Canonical SMILES
CCCC1=CC(=O)OC2=C1C3=C(C=CC(O3)(C)C)C4=C2[C@H]([C@@H]([C@H](O4)C)C)O
InChI
InChI=1S/C22H26O5/c1-6-7-13-10-15(23)26-21-16(13)20-14(8-9-22(4,5)27-20)19-17(21)18(24)11(2)12(3)25-19/h8-12,18,24H,6-7H2,1-5H3/t11-,12-,18+/m1/s1
InChIKey
NIDRYBLTWYFCFV-FMTVUPSXSA-N
Cross-matching ID
PubChem CID
64972
ChEBI ID
CHEMBL267447
CAS Number
142632-32-4
UNII
S5A9TQN46W
DrugBank ID
DB04886
TTD ID
D0S6KA
INTEDE ID
DR0258
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Human immunodeficiency virus Reverse transcriptase (HIV RT) TT84ETX POL_HV1B1 Inhibitor [3]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 ClinicalTrials.gov (NCT00005120) The Safety and Effectiveness of (+)-Calanolide A in HIV-Infected Patients Who Have Never Taken Anti-HIV Drugs. U.S. National Institutes of Health.
2 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
3 Calanolide A: a natural non-nucleoside reverse transcriptase inhibitor. BETA. 1999 Apr;12(2):8-9.
4 Metabolism of F18, a derivative of calanolide A, in human liver microsomes and cytosol. Front Pharmacol. 2017 Jul 19;8:479.