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]
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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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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: CHEBI:65552
CAS Number: 142632-32-4
UNII: S5A9TQN46W
DrugBank ID: DB04886
TTD ID: D0S6KA
INTEDE ID: DR0258

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]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)_{Main DME}	DE4LYSA	CP3A4_HUMAN	Substrate	[4]

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Molecular Interaction Atlas (MIA)

MIA Detail

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.