2H,8H-Benzo[1,2-b:3,4-b']dipyran-2-one, 9,10-dihydro-9-hydroxy-8,8-dimethyl-, (R)-

Details

• Internal ID: 549d6c08-8511-4a62-9fc3-7ecac7a471ca
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Pyranocoumarins > Angular pyranocoumarins
• IUPAC Name: (9R)-9-hydroxy-8,8-dimethyl-9,10-dihydropyrano[2,3-h]chromen-2-one
• SMILES (Canonical): CC1(C(CC2=C(O1)C=CC3=C2OC(=O)C=C3)O)C
• SMILES (Isomeric): CC1([C@@H](CC2=C(O1)C=CC3=C2OC(=O)C=C3)O)C
• InChI: InChI=1S/C14H14O4/c1-14(2)11(15)7-9-10(18-14)5-3-8-4-6-12(16)17-13(8)9/h3-6,11,15H,7H2,1-2H3/t11-/m1/s1
• InChI Key: UJSHBYQGQRPVNO-LLVKDONJSA-N
• Popularity: 10 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₄O₄
• Molecular Weight: 246.26 g/mol
• Exact Mass: 246.08920892 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.87
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 19380-05-3
• 2H,8H-Benzo[1,2-b:3,4-b']dipyran-2-one, 9,10-dihydro-9-hydroxy-8,8-dimethyl-, (R)-
• (9R)-9-hydroxy-8,8-dimethyl-9,10-dihydropyrano[2,3-h]chromen-2-one
• Jatamansinol
• SMR000445662
• CHEMBL503137
• (+)-Lomatin
• MLS000728549
• MLS001163815
• UJSHBYQGQRPVNO-LLVKDONJSA-N
• HMS2203I19
• AKOS030501953
• 9-Hydroxy-8,8-dimethyl-9,10-dihydro-2H,8H-pyrano[2,3-f]chromen-2-one #
• 2H,8H-Benzo[1,2-b:3,4-b']dipyran-2-one, 9,10-dihydro-9-hydroxy-8,8-dimethyl-, (R)-()-
• 2H,8H-Benzo[1,2-b:3,4-b']dipyran-2-one, 9,10-dihydro-9-hydroxy-8,8-dimethyl-, (R)-(+)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9869	98.69%
Caco-2	+	0.5398	53.98%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6546	65.46%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9440	94.40%
OATP1B3 inhibitior	+	0.9539	95.39%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8413	84.13%
P-glycoprotein inhibitior	-	0.9219	92.19%
P-glycoprotein substrate	-	0.9214	92.14%
CYP3A4 substrate	-	0.5343	53.43%
CYP2C9 substrate	-	0.6562	65.62%
CYP2D6 substrate	-	0.7813	78.13%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9341	93.41%
CYP2C19 inhibition	-	0.9345	93.45%
CYP2D6 inhibition	-	0.8673	86.73%
CYP1A2 inhibition	-	0.7655	76.55%
CYP2C8 inhibition	-	0.8089	80.89%
CYP inhibitory promiscuity	-	0.9657	96.57%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6022	60.22%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.8045	80.45%
Skin irritation	-	0.6201	62.01%
Skin corrosion	-	0.9253	92.53%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4563	45.63%
Micronuclear	+	0.5118	51.18%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.7729	77.29%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.6099	60.99%
Acute Oral Toxicity (c)	III	0.7058	70.58%
Estrogen receptor binding	+	0.7340	73.40%
Androgen receptor binding	+	0.5942	59.42%
Thyroid receptor binding	-	0.5294	52.94%
Glucocorticoid receptor binding	+	0.6572	65.72%
Aromatase binding	-	0.5487	54.87%
PPAR gamma	+	0.7256	72.56%
Honey bee toxicity	-	0.9188	91.88%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9331	93.31%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	28183.8 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.29%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.27%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.96%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.79%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.55%	95.56%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	89.04%	85.30%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.63%	100.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.19%	94.00%

Plants that contains it

• Ammi majus
• Angelica acutiloba
• Angelica gigas
• Angelica sinensis
• Humulus scandens
• Kopsia flavida
• Lomatium nuttallii
• Ribes sanguineum
• Stachys chinensis
• Zanthoxylum spinosum

Cross-Links

• PubChem: 759302
• NPASS: NPC224543
• ChEMBL: CHEMBL503137
• LOTUS: LTS0121135
• wikiData: Q105274165