Khellin

Details

• Internal ID: cb4876c1-d4d9-4538-a6a6-4d5af286e475
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Chromones > Furanochromones
• IUPAC Name: 4,9-dimethoxy-7-methylfuro[3,2-g]chromen-5-one
• SMILES (Canonical): CC1=CC(=O)C2=C(C3=C(C(=C2O1)OC)OC=C3)OC
• SMILES (Isomeric): CC1=CC(=O)C2=C(C3=C(C(=C2O1)OC)OC=C3)OC
• InChI: InChI=1S/C14H12O5/c1-7-6-9(15)10-11(16-2)8-4-5-18-12(8)14(17-3)13(10)19-7/h4-6H,1-3H3
• InChI Key: HSMPDPBYAYSOBC-UHFFFAOYSA-N
• Popularity: 1,334 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₂O₅
• Molecular Weight: 260.24 g/mol
• Exact Mass: 260.06847348 g/mol
• Topological Polar Surface Area (TPSA): 57.90 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.86
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• 82-02-0
• Visammin
• Methafrone
• Amicardine
• Viscardan
• Coronin
• Ammivisnagen
• Amikellin
• Ammipuran
• Benecardin
• Corafurone
• Gynokhellan
• Kelourin
• Khelloyd
• Medekellin
• Rykellin
• Ammivin
• Ammispasmin
• Interkellin
• Interkhellin
• Kelicorin
• Khelangin
• Khellamine
• Khellanals
• Khellinorm
• Visammimix
• Visnagalin
• Kalangin
• Kelamin
• Kelincor
• Norkel
• Simeskellina
• Kellosal
• Khelfren
• Khelisem
• Lynamine
• Mefurina
• Vasokellina
• Visnagen
• Amiptan
• Chellin
• Kelicor
• Kellin
• Kellina
• Keloid
• Eskel
• Cardio-khellin
• Ammi-khellin
• Bi-Kellina
• Benekardin
• Khelline I
• Chellina
• Khelline
• Khellinum
• Quelina
• 4,9-Dimethoxy-7-methyl-5H-furo[3,2-g]chromen-5-one
• Ammicardine
• 5,8-Dimethoxy-2-methyl-6,7-furanochromone
• 4,9-Dimethoxy-7-methyl-5H-furo(3,2-g)(1)benzopyran-5-one
• 4,9-Dimethoxy-7-methyl-5-oxofuro(3,2-g)-1,2-chromene
• 5,8-Dimethoxy-2-methyl-4',5'-furo-6,7-chromone
• IT-033
• CHEBI:6133
• Viscardin
• 5H-Furo[3,2-g][1]benzopyran-5-one, 4,9-dimethoxy-7-methyl-
• 5,8-Dimethoxy-2-methyl-4',5'-furano-6,7-chromone
• EINECS 201-392-8
• UNII-5G117T0TJZ
• NSC 25509
• NSC 37744
• NSC-25509
• NSC-37744
• 4,9-Dimethoxy-7-methyl-5-oxo-1,8-dioxabenz-(f)indene
• 4,9-Dimethoxy-7-methyl-5-oxofuro(3,2-g)(1)benzopyran
• BRN 0263185
• 5G117T0TJZ
• 5H-Furo(3,2-g)(1)benzopyran-5-one, 4,9-dimethoxy-7-methyl-
• DTXSID9045267
• AI3-52114
• NSC37744
• MFCD00005007
• 4,9-dimethoxy-7-methylfuro[3,2-g]chromen-5-one
• Chorafurone
• Vismagen
• Khell
• MLS000028448
• DTXCID7025267
• 4,9-Dimethoxy-7-methyl-5H-furo[3,2-g][1]benzopyran-5-one
• NSC8519
• 5-19-06-00320 (Beilstein Handbook Reference)
• 5,7-furanochromone
• CAS-82-02-0
• NCGC00016327-01
• SMR000058278
• 4,2-g][1]benzopyran
• KHELLIN (MART.)
• KHELLIN [MART.]
• 4,8-dioxabenz-[f]indene
• 4,2-g]-1,2-chromene
• 5,5'-furo-6,7-chromone
• 5,5'-furano-6,7-chromone
• Chellina [Italian]
• 4,2-g][1]benzopyran-5-one
• Khellin [INN:DCF]
• Khelline [INN-French]
• Khellinum [INN-Latin]
• Quelina [INN-Spanish]
• 5H-Furo[3, 4,9-dimethoxy-7-methyl-
• WLN: T C566 DO JV MOJ BO1 HO1 L1
• SR-01000000072
• 4,9-dimethoxy-7-methyl-5H-furo(3,2-g)chromen-5-one
• kelina
• Gynokhellin
• Intercellin
• Hkelfren
• Prestwick_287
• Spectrum_000079
• Khellin, for microscopy
• Opera_ID_372
• 4,9-Dimethoxy-7-methyl-5H-furo[3,2-g]-[1]benzopyran-5-one
• KHELLIN [INN]
• KHELLIN [MI]
• Prestwick0_000091
• Prestwick1_000091
• Prestwick2_000091
• Prestwick3_000091
• Spectrum2_000593
• Spectrum3_000654
• Spectrum4_001557
• Spectrum5_000154
• KHELLIN [WHO-DD]
• bmse000751
• SCHEMBL9655
• Khellin, analytical standard
• BSPBio_000042
• BSPBio_002287
• KBioGR_002054
• KBioSS_000479
• SPECTRUM210866
• MLS001076533
• CHEMBL44746
• DivK1c_000046
• 5,9-dimethoxy-2-methylfurano[3,2-g]chromen-4-one
• SPBio_000466
• SPBio_001981
• BPBio1_000048
• MEGxp0_000331
• ACon0_000983
• ACon1_000350
• HMS500C08
• HSMPDPBYAYSOBC-UHFFFAOYSA-
• KBio1_000046
• KBio2_000479
• KBio2_003047
• KBio2_005615
• KBio3_001507
• NINDS_000046
• HMS1568C04
• HMS1923M07
• HMS2095C04
• HMS2230B16
• HMS3371C21
• HMS3712C04
• Pharmakon1600-00210866
• HY-B1394
• NSC-8519
• NSC25509
• Tox21_110374
• BDBM50480260
• CCG-36453
• LMPK13110001
• NSC755826
• s5887
• AKOS002281934
• Tox21_110374_1
• NSC-755826
• SDCCGMLS-0003040.P003
• IDI1_000046
• NCGC00016327-02
• NCGC00016327-03
• NCGC00016327-04
• NCGC00016327-05
• NCGC00016327-06
• NCGC00016327-07
• NCGC00016327-08
• NCGC00016327-09
• NCGC00016327-11
• NCGC00023424-03
• NCGC00023424-04
• NCGC00169160-01
• NCGC00169160-02
• NCGC00169160-03
• AS-35307
• SY051635
• SBI-0051567.P002
• CS-0013121
• FT-0627578
• K0039
• C09010
• K-3400
• AB00052134_16
• 4,9-Dimethoxy-7-methyl-furo[3,2-g]chromen-5-one
• Q2079998
• SR-01000000072-3
• SR-01000000072-4
• SR-01000000072-5
• SR-01000000072-6
• BRD-K80353807-001-05-5
• BRD-K80353807-001-06-3
• BRD-K80353807-001-16-2
• 4,9-dimethoxy-7-methylpyrano[3,2-f][1]benzoxol-5-one
• 4,9-Dimethoxy-7-methyl-5H-furo[3,2-g]chromen-5-one #
• InChI=1/C14H12O5/c1-7-6-9(15)10-11(16-2)8-4-5-18-12(8)14(17-3)13(10)19-7/h4-6H,1-3H3

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9906	99.06%
Caco-2	+	0.7169	71.69%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6845	68.45%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9644	96.44%
OATP1B3 inhibitior	+	0.8547	85.47%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.7164	71.64%
P-glycoprotein inhibitior	-	0.7822	78.22%
P-glycoprotein substrate	-	0.8957	89.57%
CYP3A4 substrate	-	0.5389	53.89%
CYP2C9 substrate	-	0.8494	84.94%
CYP2D6 substrate	-	0.8309	83.09%
CYP3A4 inhibition	+	0.7959	79.59%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	+	0.8993	89.93%
CYP2D6 inhibition	+	0.8554	85.54%
CYP1A2 inhibition	+	0.9413	94.13%
CYP2C8 inhibition	-	0.7035	70.35%
CYP inhibitory promiscuity	+	0.7583	75.83%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Warning	0.3837	38.37%
Eye corrosion	-	0.9485	94.85%
Eye irritation	+	0.6794	67.94%
Skin irritation	-	0.7287	72.87%
Skin corrosion	-	0.9863	98.63%
Ames mutagenesis	+	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3646	36.46%
Micronuclear	+	0.7500	75.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.8363	83.63%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.6685	66.85%
Acute Oral Toxicity (c)	II	0.7527	75.27%
Estrogen receptor binding	+	0.7060	70.60%
Androgen receptor binding	+	0.7148	71.48%
Thyroid receptor binding	+	0.5167	51.67%
Glucocorticoid receptor binding	+	0.6543	65.43%
Aromatase binding	+	0.6284	62.84%
PPAR gamma	+	0.7272	72.72%
Honey bee toxicity	-	0.8595	85.95%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.7915	79.15%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	8.9 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.30%	94.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.42%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	92.06%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.70%	95.56%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	88.53%	94.03%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	87.76%	93.65%
CHEMBL2581	P07339	Cathepsin D	87.37%	98.95%
CHEMBL3192	Q9BY41	Histone deacetylase 8	86.38%	93.99%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.17%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.03%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.01%	99.23%
CHEMBL1951	P21397	Monoamine oxidase A	83.56%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.64%	86.33%
CHEMBL2535	P11166	Glucose transporter	81.64%	98.75%

Plants that contains it

• Allium nutans
• Annona muricata
• Dioscorea deltoidea
• Dioscorea sinoparviflora
• Visnaga daucoides

Cross-Links

• PubChem: 3828
• LOTUS: LTS0166864
• wikiData: Q2079998