Griseofulvin

Details

• Internal ID: 98fd0f6a-555e-419a-a500-f5175cb7e2f6
• Taxonomy: Organoheterocyclic compounds > Benzofurans
• IUPAC Name: (2S,5'R)-7-chloro-3',4,6-trimethoxy-5'-methylspiro[1-benzofuran-2,4'-cyclohex-2-ene]-1',3-dione
• SMILES (Canonical): CC1CC(=O)C=C(C12C(=O)C3=C(O2)C(=C(C=C3OC)OC)Cl)OC
• SMILES (Isomeric): C[C@@H]1CC(=O)C=C([C@]12C(=O)C3=C(O2)C(=C(C=C3OC)OC)Cl)OC
• InChI: InChI=1S/C17H17ClO6/c1-8-5-9(19)6-12(23-4)17(8)16(20)13-10(21-2)7-11(22-3)14(18)15(13)24-17/h6-8H,5H2,1-4H3/t8-,17+/m1/s1
• InChI Key: DDUHZTYCFQRHIY-RBHXEPJQSA-N
• Popularity: 7,483 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₇ClO₆
• Molecular Weight: 352.80 g/mol
• Exact Mass: 352.0713660 g/mol
• Topological Polar Surface Area (TPSA): 71.10 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.81
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• 126-07-8
• Amudane
• (+)-Griseofulvin
• Griseofulvinum
• Grisactin
• Grifulvin
• Grisefuline
• Griseofulvina
• Grisofulvin
• Grizeofulvin
• Spirofulvin
• Grisovin
• Lamoryl
• Likuden
• Fulcin
• Grysio
• Fulvicin
• Griseofulvine
• Poncyl
• Curling factor
• Delmofulvina
• Fulvinil
• Fulvistatin
• Fungivin
• Gresfeed
• Grifulin
• Griscofulvin
• Griseomix
• Guservin
• Murfulvin
• Fulcine
• Fulvina
• Greosin
• Biogrisin-FP
• Neo-Fulcin
• Fulvican grisactin
• Griseofulvin forte
• Griseofulvin-forte
• Fulvicin-P/G
• Xuanjing
• Grisactin V
• Fulvidex (Veterinary)
• Griseofulvine [INN-French]
• Griseofulvinum [INN-Latin]
• Griseofulvina [INN-Spanish]
• Gricin
• Griseo
• GRISEOFULVIN, MICROCRYSTALLINE
• Fulvidex
• USAF SC-2
• Griseofulvin microsize
• Grisetin
• Caswell No. 471B
• Fulvicin-U/F
• GRISEOFULVIN, ULTRAMICROCRYSTALLINE
• CCRIS 320
• HSDB 1722
• fulvicin UF
• EINECS 204-767-4
• UNII-32HRV3E3D5
• MFCD00082343
• NSC 34533
• EPA Pesticide Chemical Code 471400
• NSC-755822
• BRN 0095226
• 32HRV3E3D5
• DTXSID8020674
• Grisovin FP
• CHEBI:27779
• AI3-51015
• Griseofulvin permeability diameter
• Griseofulvin (Standard)
• GRISEOFULVIN, ULTRAMICROSIZE
• NSC-34533
• Spiro(benzofuran-2(3H),1'-(2)cyclohexene)-3,4'-dione, 7-chloro-2',4,6-trimethoxy-6'-methyl-, (1'S-trans)-
• 7-Chloro-4,6,2'-trimethoxy-6'-methylgris-2'-en-3,4'-dione
• Grisactin Ultra
• DTXCID20674
• Fulvicin P/G
• (2S,6'R)-7-chloro-2',4,6-trimethoxy-6'-methyl-3H-spiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione
• Griseofulvin [USP:INN:BAN:JAN]
• 5-18-05-00150 (Beilstein Handbook Reference)
• 7-Chloro-2',4,6-trimethoxy-6'beta-methylspiro(benzofuran-2(3H),1'-(2)cyclohexene)-3,4'-dione
• 7-Chloro-4,6-dimethoxycoumaran-3-one-2-spiro-1'-(2'-methoxy-6'-methylcyclohex-2'-en-4'-one)
• (1'S,6'R)-7-Chloro-2',4,6-trimethoxy-6'-methylspiro(benzofuran-2(3H),1'-(2)cyclohexene)-3,4'-dione
• (2S-trans)-7-Chloro-2',4,6-trimethoxy-6'-methylspiro(benzofuran-2(3H),1'-(2)cyclohexene)-3,4'-dione
• Spiro(benzofuran-2(3H),1'-(2)cyclohexene)-3,4'-dione, 7-chloro-2',4,6-trimethoxy-6'-methyl-, (2S-trans)-
• NCGC00091120-01
• Griseofulvin (USP:INN)
• Griseofulvin [USP:INN]
• GRISEOFULVIN (IARC)
• GRISEOFULVIN [IARC]
• Griseofulvine (INN-French)
• Griseofulvinum (INN-Latin)
• Griseofulvina (INN-Spanish)
• GRISEOFULVIN (MART.)
• GRISEOFULVIN [MART.]
• (1'S-trans)- 7-Chloro-2',4,6-trimethoxy-6'-methylspiro(benzofuran-2(3H),1'-cyclohex-2'-ene)-3,4'-dione
• (2S,5'R)-7-chloro-3',4,6-trimethoxy-5'-methylspiro[1-benzofuran-2,4'-cyclohex-2-ene]-1',3-dione
• (2S,6'R)-7-chloro-2',4,6-trimethoxy-6'-methyl-3H,4'H-spiro[1-benzofuran-2,1'-cyclohex[2]ene]-3,4'-dione
• (2S,6'R)-7-chloro-2',4,6-trimethoxy-6'-methyl-3H-spiro[benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione
• ULTRAGRIS-165
• ULTRAGRIS-330
• GRISEOFULVIN (USP-RS)
• GRISEOFULVIN [USP-RS]
• Fulvicin Bolus
• Fulvicin-U/F (Veterinary)
• Fulvicin Bolus (Veterinary)
• FULVICIN P/G 165
• FULVICIN P/G 330
• GRISEOFULVIN (EP MONOGRAPH)
• Griseofulvin (USP:INN:BAN:JAN)
• GRISEOFULVIN [EP MONOGRAPH]
• GRISEOFULVIN (USP MONOGRAPH)
• GRISEOFULVIN [USP MONOGRAPH]
• Griseofulvin, (+)-
• (1'S,6'R)-7-chloro-2',4,6-trimethoxy-6'-methyl-3H-spiro[benzofuran-2,1'-cyclohex[2]ene]-3,4'-dione
• GRE
• SMR000718755
• Spiro(benzofuran-2(3H),1'-(2)cyclohexene)-3,4'-dione, 7-chloro-2',4,6-trimethoxy-6'-methyl-, (1'S,6'R)-
• GRISEOFULVIN PERMEABILITY DIAMETER (USP-RS)
• GRISEOFULVIN PERMEABILITY DIAMETER [USP-RS]
• SR-05000001535
• GRISEOFULVIN POWDER
• Griseofulvin and Alpha-IFN
• Griseoflulvin
• GRISEOFULVIN, MICROSIZE
• Griseofulvin,(S)
• (2S,5'R)-7-chloro-3',4,6-trimethoxy-5'-methyl-spiro[benzofuran-2,4'-cyclohex-2-ene]-1',3-dione
• (2S,6'R)-7-chloro-2',4,6-trimethoxy-6'-methyl-3H,4'H-spiro(1-benzofuran-2,1'-cyclohex(2)ene)-3,4'-dione
• Prestwick_247
• Grysio (Microsize)
• Grisactin V (TN)
• Gris-peg (TN)
• IDIFULVIN
• Fulvicin U/F Powder
• Griseofulvin,microsize
• Fulvicin U/F Tablets
• Spectrum_000816
• CPD000718755
• SpecPlus_000336
• Griseofulvin (microsize)
• Griseofulviin (microsize)
• Prestwick3_000226
• Spectrum2_000213
• Spectrum3_000161
• Spectrum4_000927
• Spectrum5_000648
• GRISEOFULVIN [MI]
• Ultramicrosize Griseofulvin
• GRISEOFULVIN [INN]
• GRISEOFULVIN [JAN]
• CHEMBL562
• GRISEOFULVIN [HSDB]
• Griseofulvin Oral Suspension
• GRISEOFULVIN [VANDF]
• SCHEMBL21988
• Amudane, Fulvicin, Grisactin
• BSPBio_000271
• BSPBio_001621
• KBioGR_001454
• KBioSS_001296
• SPECTRUM200046
• MLS001304062
• MLS002152905
• MLS002154239
• BIDD:GT0024
• DivK1c_000154
• DivK1c_006432
• GRISEOFULVIN [WHO-DD]
• GRISEOFULVIN [WHO-IP]
• Fulvicin U/F Bolus Veterinary
• Griseofulvin (JAN/USP/INN)
• SPBio_000225
• BPBio1_000299
• MEGxm0_000184
• ACon0_000953
• ACon1_001843
• BDBM31775
• Fulvicin-U/F Powder and Tablets
• HMS500H16
• KBio1_000154
• KBio1_001376
• KBio2_001296
• KBio2_003864
• KBio2_006432
• KBio3_001121
• D01AA08
• D01BA01
• GRISEOFULVIN [GREEN BOOK]
• DDUHZTYCFQRHIY-RBHXEPJQSA-N
• NINDS_000154
• GRISEOFULVIN [ORANGE BOOK]
• HMS1923E09
• HMS2091A03
• HMS2095N13
• HMS2235F13
• HMS3259D05
• HMS3712N13
• Pharmakon1600-00200046
• Ultramicrosize Griseofulvin Tablets
• 7-CHLORO-2',4,6-TRIMETHOXY-6'-METHYLSPIRO(BENZOFURAN-2(3H),1'-(2)CYCLOHEXENE)-3,4'-DIONE
• 7-CHLORO-2',4,6-TRIMETHOXY-6'.BETA.-METHYLSPIRO(BENZOFURAN-2(3H),1'-(2)CYCLOHEXENE)-3,4'-DIONE
• Tox21_111087
• Tox21_202235
• Tox21_303005
• CCG-38416
• HY-17583R
• LMPK13060001
• NSC755822
• s4071
• GRISEOFULVINUM [WHO-IP LATIN]
• AKOS015896380
• Tox21_111087_1
• CS-3426
• DB00400
• NC00616
• SDCCGMLS-0066450.P001
• IDI1_000154
• NCGC00091120-02
• NCGC00091120-03
• NCGC00091120-04
• NCGC00091120-05
• NCGC00091120-06
• NCGC00091120-07
• NCGC00091120-08
• NCGC00091120-09
• NCGC00091120-13
• NCGC00256353-01
• NCGC00259784-01
• (2S,6'R)-7-chloro-2',4,6-trimethoxy-6'-methylbenzofuran-2-spiro-1'-cyclohex-2'-ene-3,4'-dione
• AS-13736
• BT164513
• HY-17583
• Griseofulvin 100 microg/mL in Acetonitrile
• CS-0695022
• G0384
• EN300-52615
• BIM-0051396.0001
• C06686
• D00209
• AB00052005_07
• Griseofulvin, VETRANAL(TM), analytical standard
• Q416096
• SR-01000837512
• Griseofulvin, Antibiotic for Culture Media Use Only
• Q-201178
• SR-01000837512-2
• SR-05000001535-1
• SR-05000001535-3
• SR-05000001535-4
• BRD-K08273968-001-05-9
• BRD-K08273968-001-09-1
• BRD-K08273968-001-19-0
• Z756424454
• Griseofulvin, British Pharmacopoeia (BP) Reference Standard
• Griseofulvin, from Penicillium griseofulvum, 97.0-102.0%
• Griseofulvin, European Pharmacopoeia (EP) Reference Standard
• (2S-TRANS)-7-CHLORO-2',4,6-TRIMETHOXY-6'-METHYLSPIRO
• Griseofulvin, United States Pharmacopeia (USP) Reference Standard
• Griseofulvin Permeability Diameter, United States Pharmacopeia (USP) Reference Standard
• Griseofulvin, Pharmaceutical Secondary Standard; Certified Reference Material
• (1'S-trans)-7-Chloro-2',4,6-trimethoxy-6'-methylspiro(benzofuran-2(3H),1'-cyclohex-2'-ene)-3,4'-dione
• (2S,6'R)-7-Chloro-2',4,6-trimethoxy-6'-methylspiro(benzo(b)furan-2(3H),1'-(cyclohex-2'-ene))-3,4'-dione
• 107912-37-8
• 7-CHLORO-2',4,6-TRIMETHOXY-6'-BETA-SPIRO(BENZOFURAN-2(3H), 1'-(2)CYCLOHEXENE-3,4'-DIONE
• 7-Chloro-2',4,6-trimethoxy-6'-methylspiro[benzofuran-2(3H),1',- [2]cyclohexene]-3,4'-dione
• 7-CHLORO-4,6-DIMETHOXYCOUMARAN-3-ONE-2-SPIRO-1'-(2'-MET HOXY-6'-METHYLCYCLOHEX-2'-EN-4'-ONE)
• 7-CHLORO-4,6-DIMETHOXYCOUMARAN-3-ONE-2-SPIRO-1'-(2'-METHOXY)-6'-METHYLCYCLO-HEX-2'-EN-4'-ONE
• SPIRO(BENZOFURAN-2(3H),1'-(2)CYCLOHEXENE)-3,4'-DIONE, 7 -CHLORO-2',4,6-TRIMETHOXY-6'-BETA-METHYL-
• SPIRO(BENZOFURAN-2(3H),1'-(2)CYCLOHEXENE)-3,4'-DIONE, 7-CHLORO-2',4,6-TRIMETHOXY-6'BETA-METHYL-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.9313	93.13%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.7286	72.86%
Subcellular localzation	Mitochondria	0.5780	57.80%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9526	95.26%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.6158	61.58%
P-glycoprotein inhibitior	-	0.6556	65.56%
P-glycoprotein substrate	-	0.8263	82.63%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7942	79.42%
CYP3A4 inhibition	+	0.7043	70.43%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	-	0.6673	66.73%
CYP inhibitory promiscuity	+	0.8235	82.35%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8311	83.11%
Carcinogenicity (trinary)	Danger	0.6231	62.31%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9541	95.41%
Skin irritation	-	0.7906	79.06%
Skin corrosion	-	0.9271	92.71%
Ames mutagenesis	-	0.8800	88.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6097	60.97%
Micronuclear	-	0.5741	57.41%
Hepatotoxicity	+	0.8677	86.77%
skin sensitisation	-	0.6986	69.86%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	+	0.7855	78.55%
Acute Oral Toxicity (c)	IV	0.6158	61.58%
Estrogen receptor binding	+	0.9107	91.07%
Androgen receptor binding	+	0.8697	86.97%
Thyroid receptor binding	+	0.6299	62.99%
Glucocorticoid receptor binding	+	0.8371	83.71%
Aromatase binding	-	0.5356	53.56%
PPAR gamma	+	0.8708	87.08%
Honey bee toxicity	-	0.7573	75.73%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.7100	71.00%
Fish aquatic toxicity	+	0.9940	99.40%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	398.1 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.08%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.87%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	93.34%	83.82%
CHEMBL2581	P07339	Cathepsin D	92.78%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.50%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.95%	94.45%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	90.83%	97.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.76%	86.33%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	88.96%	86.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.98%	94.00%
CHEMBL1871	P10275	Androgen Receptor	86.00%	96.43%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	85.54%	94.03%
CHEMBL4208	P20618	Proteasome component C5	85.38%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.00%	95.89%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.59%	96.77%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.31%	97.25%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	82.97%	94.80%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.65%	97.09%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	81.10%	96.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.80%	96.95%

Plants that contains it

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Cross-Links

• PubChem: 441140
• LOTUS: LTS0097934
• wikiData: Q416096