CALANOLIDE A

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H26O5
Molecular Weight	370.4388
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCC1=CC(=O)OC2=C1C3=C(C=CC(C)(C)O3)C4=C2[C@@H](O)[C@H](C)[C@@H](C)O4

InChI

InChIKey=NIDRYBLTWYFCFV-FMTVUPSXSA-N

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

HIDE SMILES / InChI

Molecular Formula	C22H26O5
Molecular Weight	370.4388
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28769808 | https://www.ncbi.nlm.nih.gov/pubmed/15193138 | https://www.ncbi.nlm.nih.gov/pubmed/14980631

Calanolide A is a new non-nucleoside reverse transcriptase inhibitor (NNRTI) originally extracted from a tropical tree (Calophyllum lanigerum) in the Malaysian rain forest. Viral life-cycle studies indicate that calanolide A acts early in the infection process, similar to the known HIV reverse transcriptase (RT) inhibitor 2', 3'-dideoxycytidine. In enzyme inhibition assays, calanolide A potently and selectively inhibits recombinant HIV type 1 RT but not cellular DNA polymerases or HIV type 2 RT within the concentration range tested. Phase I studies have found that calanolide A is well tolerated. Consequently, it has potential clinical applications in combination with other antiviral drugs to suppress HIV-1 mutants. Nevertheless, the development of calanolide A has been delayed due to its low therapeutic index (range: 16–279), non-ideal antiviral activity, and the complexity of its extraction from plants

Approval Year

PubMed

Title	Date	PubMed
Characteristics of a group of nonnucleoside reverse transcriptase inhibitors with structural diversity and potent anti-human immunodeficiency virus activity.	1995 Oct	7475321
Structure-activity modifications of the HIV-1 inhibitors (+)-calanolide A and (-)-calanolide B.	1996 Oct 25	8893846
Sensitivity and resistance to (+)-calanolide A of wild-type and mutated forms of HIV-1 reverse transcriptase.	1999	10723499
Inhibition of HIV-1 reverse transcriptase and HIV-1 replication by Calophyllum coumarins and xanthones.	2002 Jan	11842340
Safety and pharmacokinetic profile of multiple escalating doses of (+)-calanolide A, a naturally occurring nonnucleoside reverse transcriptase inhibitor, in healthy HIV-negative volunteers.	2002 Nov-Dec	12501127

Patents

Substance Class	Chemical Created by `admin` on `Sat Dec 16 04:58:02 GMT 2023` Edited by `admin` on `Sat Dec 16 04:58:02 GMT 2023`
Record UNII	S5A9TQN46W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CALANOLIDE A

Common Name

English

(+)-(10R,11S,12S)-10,11-TRANS-DIHYDRO-12-HYDROXY-6,6,10,11-TETRAMETHYL-4-PROPYL-2H,6H-BENZO(1,2-B:3,4-B':5,6-B'')TRIPYRAN-2-ONE

Common Name

English

NSC-650886

Code

English

Code System Code Type Description

EPA CompTox

DTXSID601316787