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Details

Stereochemistry ACHIRAL
Molecular Formula C15H12O3
Molecular Weight 240.254
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHRYSAROBIN

SMILES

CC1=CC(O)=C2C(=O)C3=C(O)C=CC=C3CC2=C1

InChI

InChIKey=ZZBWSNKBZKPGAK-UHFFFAOYSA-N
InChI=1S/C15H12O3/c1-8-5-10-7-9-3-2-4-11(16)13(9)15(18)14(10)12(17)6-8/h2-6,16-17H,7H2,1H3

HIDE SMILES / InChI
Molecular Formula C15H12O3
Molecular Weight 240.254
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including http://www.drugfuture.com/chemdata/chrysarobin.html | http://www.google.com/patents/US4007271 | http://www.henriettes-herb.com/eclectic/kings/chrysarobin.html | https://www.ncbi.nlm.nih.gov/pubmed/1401327 | https://www.ncbi.nlm.nih.gov/pubmed/3135955 | https://www.ncbi.nlm.nih.gov/pubmed/3986797

Chrysarobin was originally extracted from Goa powder, a substance deposited in the wood of Andira Araroba, Aguiar (Nat. Ord.—Leguminosae). Chrysarobin (1,8-dihydroxy-3-methyl-9-anthrone) has enol tautomer of 1,8,9-trihydroxy-3-methyl-anthracene. Chrysarobin exerts antipsoriatic action. The use of chrysarobin has a number of quite serious disadvantages, not the least of which is that it can result in severe staining and irritation of the skin. Chrysarobin is an anthrone skin tumor promoter.

Originator

Approval Year

1921
1468
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
Activator
1447
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
Compound Cloud
68111
HongKong Chemhere
SCD43078
ZINC
ZINC000002040462
http://zinc15.docking.org/substances/ZINC000002040462
PubMed

PubMed

TitleDatePubMed
Toxicity of structurally related anthraquinones and anthrones to mammalian cells in vitro.
1994-06
History of the treatment of psoriasis.
1992-10
Modulation of chrysarobin skin tumor promotion.
1988-08
Mechanism of mouse skin tumor promotion by chrysarobin.
1985-06
Patents

Patents

EP0083359B1
1
US4699929
1

Sample Use Guides

In Vivo Use Guide
Chrysarobin was used in the form of 1-5% ointment
Route of Administration: Topical
In Vitro Use Guide
Curator's Comment: In V79 cells, the concentration of anthraquinones and structurally related compounds including chrysarobin causing 50% inhibition ranged from 0.21 to 21.6 mug/ml for cloning efficiency and from 0.86 to 14.6 mug/ml for MTT reduction.
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:54:34 GMT 2025
Edited
by admin
on Mon Mar 31 17:54:34 GMT 2025
Record UNII
6307EF51M1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CHRYSAROBINUM
HPUS  
Preferred Name English
CHRYSAROBIN
MI   WHO-DD  
Common Name English
CHRYSOPHANOL-9-ANTHRONE
Common Name English
Chrysarobin [WHO-DD]
Common Name English
CHRYSOPHANOL ANTHRONE
Common Name English
CHRYSAROBIN [MI]
Common Name English
1,8-DIHYDROXY-3-METHYL-9-ANTHRONE
Systematic Name English
1,8-DIHYDROXY-3-METHYL-9(10H)-ANTHRACENONE
Systematic Name English
CHRYSOPHANOLANTHRONE
Common Name English
CHRYSAROBINUM [HPUS]
Common Name English
CHRYSOPHANIC ACID 9-ANTHRONE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C761
Created by admin on Mon Mar 31 17:54:34 GMT 2025 , Edited by admin on Mon Mar 31 17:54:34 GMT 2025
NCI_THESAURUS C514
Created by admin on Mon Mar 31 17:54:34 GMT 2025 , Edited by admin on Mon Mar 31 17:54:34 GMT 2025
Code System Code Type Description
CHEBI
3686
Created by admin on Mon Mar 31 17:54:34 GMT 2025 , Edited by admin on Mon Mar 31 17:54:34 GMT 2025
PRIMARY
EPA CompTox
DTXSID20197683
Created by admin on Mon Mar 31 17:54:34 GMT 2025 , Edited by admin on Mon Mar 31 17:54:34 GMT 2025
PRIMARY
NCI_THESAURUS
C372
Created by admin on Mon Mar 31 17:54:34 GMT 2025 , Edited by admin on Mon Mar 31 17:54:34 GMT 2025
PRIMARY
MERCK INDEX
m3527
Created by admin on Mon Mar 31 17:54:34 GMT 2025 , Edited by admin on Mon Mar 31 17:54:34 GMT 2025
PRIMARY Merck Index
SMS_ID
100000080087
Created by admin on Mon Mar 31 17:54:34 GMT 2025 , Edited by admin on Mon Mar 31 17:54:34 GMT 2025
PRIMARY
DAILYMED
6307EF51M1
Created by admin on Mon Mar 31 17:54:34 GMT 2025 , Edited by admin on Mon Mar 31 17:54:34 GMT 2025
PRIMARY
CAS
491-58-7
Created by admin on Mon Mar 31 17:54:34 GMT 2025 , Edited by admin on Mon Mar 31 17:54:34 GMT 2025
PRIMARY
RXCUI
1860418
Created by admin on Mon Mar 31 17:54:34 GMT 2025 , Edited by admin on Mon Mar 31 17:54:34 GMT 2025
PRIMARY
EVMPD
SUB13367MIG
Created by admin on Mon Mar 31 17:54:34 GMT 2025 , Edited by admin on Mon Mar 31 17:54:34 GMT 2025
PRIMARY
MESH
C013883
Created by admin on Mon Mar 31 17:54:34 GMT 2025 , Edited by admin on Mon Mar 31 17:54:34 GMT 2025
PRIMARY
ECHA (EC/EINECS)
207-740-5
Created by admin on Mon Mar 31 17:54:34 GMT 2025 , Edited by admin on Mon Mar 31 17:54:34 GMT 2025
PRIMARY
FDA UNII
6307EF51M1
Created by admin on Mon Mar 31 17:54:34 GMT 2025 , Edited by admin on Mon Mar 31 17:54:34 GMT 2025
PRIMARY
PUBCHEM
68111
Created by admin on Mon Mar 31 17:54:34 GMT 2025 , Edited by admin on Mon Mar 31 17:54:34 GMT 2025
PRIMARY
Related Record Type Details
Structure of CHRYSAROBIN
ACTIVE MOIETY
NIH
NCATS
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