Cyclocumarol

Details

• Internal ID: 3a570ad9-3db2-4948-9774-508d04627bc8
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Pyranocoumarins > Angular pyranocoumarins
• IUPAC Name: 2-methoxy-2-methyl-4-phenyl-3,4-dihydropyrano[3,2-c]chromen-5-one
• SMILES (Canonical): CC1(CC(C2=C(O1)C3=CC=CC=C3OC2=O)C4=CC=CC=C4)OC
• SMILES (Isomeric): CC1(CC(C2=C(O1)C3=CC=CC=C3OC2=O)C4=CC=CC=C4)OC
• InChI: InChI=1S/C20H18O4/c1-20(22-2)12-15(13-8-4-3-5-9-13)17-18(24-20)14-10-6-7-11-16(14)23-19(17)21/h3-11,15H,12H2,1-2H3
• InChI Key: ZGFASEKBKWVCGP-UHFFFAOYSA-N
• Popularity: 313 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₈O₄
• Molecular Weight: 322.40 g/mol
• Exact Mass: 322.12050905 g/mol
• Topological Polar Surface Area (TPSA): 44.80 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 4.07
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• CYCLOCUMAROL
• Cyclocoumarol
• 518-20-7
• Cumopyran
• Pyranocumarin
• Cumopyrin
• Methanopyranorin
• Anticoagulans 63
• Compound 63 link
• Pyranocumarin [German]
• BL 5
• Cyclocoumarol [BAN]
• 2-methoxy-2-methyl-4-phenyl-3,4-dihydropyrano[3,2-c]chromen-5-one
• EINECS 208-248-3
• methopyranorin
• UNII-725P8AW50M
• 725P8AW50M
• C20H18O4
• 3,4-Dihydro-2-methoxy-2-methyl-4-phenyl-2H,5H-pyrano(3,2-c)(1)benzopyran-5-one
• 2-Methyl-2-methoxy-4-phenyl-3,4-dihydro-pyrano-(3,2-c)-cumarin [German]
• 2-Methyl-2-methoxy-4-phenyl-3,4-dihydro-pyrano-(3,2-c)-cumarin
• 3,4-Dihydro-2-methoxy-2-methyl-4-phenylpyrano(3,2-c)chromen-5-one
• 2H,5H-Pyrano(3,2-c)(1)benzopyran-5-one, 3,4-dihydro-2-methoxy-2-methyl-4-phenyl-
• 2H,5H-Pyrano[3,2-c][1]benzopyran-5-one, 3,4-dihydro-2-methoxy-2-methyl-4-phenyl-
• 2H-Pyran-5-carboxylic acid, 3,4-dihydro-6-(o-hydroxyphenyl)-2-methoxy-2-methyl-4-phenyl-, delta-lactone
• 3,4-dihydro-2-methoxy-2-methyl-4-phenylpyrano[3,2-c]chromen-5-one
• 3,4-Dihydro-2-methoxy-2-methyl-4-phenyl-2H,5H-pyrano[3,2-c][1]benzopyran-5-one
• anticoagulant No. 63
• starbld0009647
• CYCLOCUMAROL [MI]
• Cyclocoumarol [INN:BAN]
• SCHEMBL38087
• BL-5
• CHEMBL2104144
• DTXSID60862101
• CHEBI:135368
• ZGFASEKBKWVCGP-UHFFFAOYSA-N
• NCGC00166195-01
• LS-127334
• FT-0708808
• Pyranocoumarin, PESTANAL(R), analytical standard
• SR-01000883723
• SR-01000883723-1
• Q27266024
• 3,4-(2'-Methyl-2'-methoxy-4'-phenyl)dihydropyranocoumarin
• 2-methyl-2-methoxy-4-phenyl-5-oxodihydropyrano[3,2-c][1]benzopyran
• 2-methoxy-2-methyl-4-phenyl-3,4-dihydropyrano[3,2-c]chromen-5(2H)-one
• 2-Methoxy-2-methyl-4-phenyl-3,4-dihydro-2H,5H-pyrano[3,2-c]chromen-5-one #
• 2H-Pyran-5-carboxylic acid, 3,4-dihydro-6-(o-hydroxyphenyl)-2-methoxy-2-methyl-4-phenyl-, .delta.-lactone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9864	98.64%
Caco-2	+	0.8602	86.02%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6716	67.16%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8908	89.08%
OATP1B3 inhibitior	+	0.9591	95.91%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8000	80.00%
P-glycoprotein inhibitior	-	0.4773	47.73%
P-glycoprotein substrate	-	0.7461	74.61%
CYP3A4 substrate	+	0.6357	63.57%
CYP2C9 substrate	-	0.5788	57.88%
CYP2D6 substrate	-	0.8536	85.36%
CYP3A4 inhibition	-	0.5324	53.24%
CYP2C9 inhibition	-	0.6471	64.71%
CYP2C19 inhibition	-	0.5427	54.27%
CYP2D6 inhibition	-	0.8311	83.11%
CYP1A2 inhibition	-	0.5372	53.72%
CYP2C8 inhibition	-	0.6026	60.26%
CYP inhibitory promiscuity	-	0.6413	64.13%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9513	95.13%
Carcinogenicity (trinary)	Non-required	0.5775	57.75%
Eye corrosion	-	0.9717	97.17%
Eye irritation	-	0.9704	97.04%
Skin irritation	-	0.7515	75.15%
Skin corrosion	-	0.9712	97.12%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6958	69.58%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	+	0.6551	65.51%
skin sensitisation	-	0.8991	89.91%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.5808	58.08%
Acute Oral Toxicity (c)	III	0.7742	77.42%
Estrogen receptor binding	+	0.9124	91.24%
Androgen receptor binding	+	0.8345	83.45%
Thyroid receptor binding	-	0.4940	49.40%
Glucocorticoid receptor binding	+	0.6400	64.00%
Aromatase binding	+	0.8186	81.86%
PPAR gamma	+	0.7990	79.90%
Honey bee toxicity	-	0.7800	78.00%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9599	95.99%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.87%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.15%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.88%	97.09%
CHEMBL2581	P07339	Cathepsin D	92.93%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.92%	99.23%
CHEMBL2039	P27338	Monoamine oxidase B	90.37%	92.51%
CHEMBL4040	P28482	MAP kinase ERK2	88.07%	83.82%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.70%	89.00%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	85.82%	96.39%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.26%	97.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.19%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.48%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.13%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	81.89%	91.49%
CHEMBL1907	P15144	Aminopeptidase N	80.89%	93.31%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.55%	96.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.39%	92.62%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	80.22%	96.67%

Plants that contains it

• Angelica decursiva
• Cullen corylifolium
• Glycyrrhiza uralensis
• Kitagawia praeruptora

Cross-Links

• PubChem: 10606
• NPASS: NPC24355
• LOTUS: LTS0160896
• wikiData: Q27266024