Karanjin

Details

• Internal ID: ad0b6ae5-3d57-4703-a84b-e4319bb8c9f1
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones > Furanoflavones
• IUPAC Name: 3-methoxy-2-phenylfuro[2,3-h]chromen-4-one
• SMILES (Canonical): COC1=C(OC2=C(C1=O)C=CC3=C2C=CO3)C4=CC=CC=C4
• SMILES (Isomeric): COC1=C(OC2=C(C1=O)C=CC3=C2C=CO3)C4=CC=CC=C4
• InChI: InChI=1S/C18H12O4/c1-20-18-15(19)13-7-8-14-12(9-10-21-14)17(13)22-16(18)11-5-3-2-4-6-11/h2-10H,1H3
• InChI Key: LKPQNZRGGNOPPU-UHFFFAOYSA-N
• Popularity: 182 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₂O₄
• Molecular Weight: 292.30 g/mol
• Exact Mass: 292.07355886 g/mol
• Topological Polar Surface Area (TPSA): 48.70 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 4.21
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• 521-88-0
• 3-methoxy-2-phenyl-4H-furo[2,3-h]chromen-4-one
• Kranjin
• 3-methoxy-2-phenylfuro[2,3-h]chromen-4-one
• UNII-WV7IM0I02M
• WV7IM0I02M
• C18H12O4
• EINECS 208-319-9
• NSC335755
• NSC 335755
• NSC-335755
• 3-Methoxy-2-phenyl-4H-furo(2,3-h)(1)benzopyran-4-one
• 3-methoxy-2-phenyl-4H-furo(2,3-h)-1-benzopyran-4-one
• 3-Methoxy-2-phenyl-4H-furo[2,3-h]-1-benzopyran-4-one
• 4H-Furo(2,3-h)-1-benzopyran-4-one, 3-methoxy-2-phenyl-
• 4H-Furo[2,3-h]-1-benzopyran-4-one, 3-methoxy-2-phenyl-
• 3-methoxy-2-phenyl-4H-furo[2,3-h][1]benzopyran-4-one
• KARANJIN [MI]
• FLAVONE (BOHLMAN)
• 3-methoxy-2-phenyl-furo[2,3-h]chromen-4-one
• 7-Methoxy-8-phenylfurano[2,3-h]chromen-6-one
• MLS001360608
• BIDD:ER0513
• SCHEMBL247164
• CHEMBL208484
• MEGxp0_001687
• DTXSID20200106
• CHEBI:166631
• LKPQNZRGGNOPPU-UHFFFAOYSA-N
• HMS3043B17
• HY-N2534
• TNP00046
• 4H-Furo[2, 3-methoxy-2-phenyl-
• BDBM50548261
• LMPK12111542
• MFCD00017406
• AKOS016010124
• KS-1474
• Karanjin 100 microg/mL in Acetonitrile
• NCGC00017182-01
• NCGC00017182-02
• NCGC00017182-03
• NCGC00142418-01
• AC-34768
• SMR001223861
• 3-methoxy-2-phenyluro[2,3-h]chromen-4-one
• CS-0022805
• FT-0603444
• A923926
• A1-03165
• Q6368495

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9949	99.49%
Caco-2	+	0.5864	58.64%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7839	78.39%
OATP2B1 inhibitior	-	0.8700	87.00%
OATP1B1 inhibitior	+	0.9616	96.16%
OATP1B3 inhibitior	+	0.9954	99.54%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7296	72.96%
P-glycoprotein inhibitior	+	0.7285	72.85%
P-glycoprotein substrate	-	0.8410	84.10%
CYP3A4 substrate	-	0.5247	52.47%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7654	76.54%
CYP3A4 inhibition	+	0.8752	87.52%
CYP2C9 inhibition	+	0.8949	89.49%
CYP2C19 inhibition	+	0.9851	98.51%
CYP2D6 inhibition	+	0.5703	57.03%
CYP1A2 inhibition	+	0.9641	96.41%
CYP2C8 inhibition	+	0.5303	53.03%
CYP inhibitory promiscuity	+	0.9181	91.81%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Warning	0.4021	40.21%
Eye corrosion	-	0.9709	97.09%
Eye irritation	-	0.7051	70.51%
Skin irritation	-	0.6442	64.42%
Skin corrosion	-	0.9724	97.24%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3600	36.00%
Micronuclear	+	0.8300	83.00%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.8528	85.28%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.5620	56.20%
Acute Oral Toxicity (c)	III	0.7380	73.80%
Estrogen receptor binding	+	0.9285	92.85%
Androgen receptor binding	+	0.8870	88.70%
Thyroid receptor binding	+	0.5436	54.36%
Glucocorticoid receptor binding	+	0.8219	82.19%
Aromatase binding	+	0.8995	89.95%
PPAR gamma	+	0.6047	60.47%
Honey bee toxicity	-	0.8561	85.61%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.9043	90.43%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	11220.2 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	35481.3 nM	Potency	via CMAUP
CHEMBL3622	P33261	Cytochrome P450 2C19	3981.1 nM	Potency	via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	1000 nM	Potency	via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	10000 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	3162.3 nM; 3162.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	31622.8 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	35481.3 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	39810.7 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	8912.5 nM	Potency	via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	39810.7 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.48%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.90%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.70%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	93.22%	99.23%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	90.93%	94.03%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.35%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.95%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.75%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.11%	96.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.60%	95.50%
CHEMBL3959	P16083	Quinone reductase 2	82.94%	89.49%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	81.58%	93.65%

Plants that contains it

• Dahlstedtia pinnata
• Fordia cauliflora
• Lonchocarpus heptaphyllus
• Millettia pulchra
• Pongamia pinnata
• Pongamia pinnata var. pinnata
• Tephrosia purpurea

Cross-Links

• PubChem: 100633
• NPASS: NPC41719
• ChEMBL: CHEMBL208484
• LOTUS: LTS0148109
• wikiData: Q6368495