2-(2-Hydroxypropan-2-yl)-2,3-dihydrofuro[3,2-g]chromen-7-one

Details

• Internal ID: a59ec98d-c807-4fe8-b278-eb46abe9b8a0
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Furanocoumarins > Psoralens
• IUPAC Name: 2-(2-hydroxypropan-2-yl)-2,3-dihydrofuro[3,2-g]chromen-7-one
• SMILES (Canonical): CC(C)(C1CC2=C(O1)C=C3C(=C2)C=CC(=O)O3)O
• SMILES (Isomeric): CC(C)(C1CC2=C(O1)C=C3C(=C2)C=CC(=O)O3)O
• InChI: InChI=1S/C14H14O4/c1-14(2,16)12-6-9-5-8-3-4-13(15)18-10(8)7-11(9)17-12/h3-5,7,12,16H,6H2,1-2H3
• InChI Key: FWYSBEAFFPBAQU-UHFFFAOYSA-N
• Popularity: 23 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: 1

Synonyms

• (+/-)-Marmesin
• ( inverted exclamation markA)-Marmesin
• 2-(2-hydroxypropan-2-yl)-2,3-dihydrofuro[3,2-g]chromen-7-one
• 2-(1-Hydroxy-1-methylethyl)-2,3-dihydro-7H-furo[3,2-g]chromen-7-one
• 7H-Furo[3,2-g][1]benzopyran-7-one,2,3-dihydro-2-(1-hydroxy-1-methylethyl)-
• (+)-Marmesin;(S)-Marmesin
• Oprea1_172287
• Oprea1_468691
• SCHEMBL546574
• 2-(1-Hydroxy-1-methylethyl)-2,3-dihydro-7H-furo[3,2-g]chromen-7-one #
• CHEMBL4128429
• CHEBI:49080
• HY-N2176A
• FWYSBEAFFPBAQU-UHFFFAOYSA-N
• HMS1672K17
• STK396315
• AKOS000546749
• CS-0068783
• FT-0775401
• FT-0775691
• 2'-(1''-Hydroxy-1''-methylethyl)-psoralen
• Q-100147
• Q27121470
• 2-(1-hydroxy-1-methyl-ethyl)-2,3-dihydrofuro[3,2-g]chromen-7-one
• 2-(1-Hydroxy-1-methylethyl)-2,3-dihydrofuro[3,2-g]chromen-7-one
• 2-(2-hydroxypropan-2-yl)-2,3-dihydro-7H-furo[3,2-g]chromen-7-one
• 2,3-dihydro-2-(1-hydroxy-1-methylethyl)-7h-furo[3,2-g][1]benzopyran-7-one
• InChI=1/C14H14O4/c1-14(2,16)12-6-9-5-8-3-4-13(15)18-10(8)7-11(9)17-12/h3-5,7,12,16H,6H2,1-2H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9909	99.09%
Caco-2	+	0.6201	62.01%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7949	79.49%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.8861	88.61%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8951	89.51%
P-glycoprotein inhibitior	-	0.8674	86.74%
P-glycoprotein substrate	-	0.8530	85.30%
CYP3A4 substrate	-	0.5667	56.67%
CYP2C9 substrate	-	0.6506	65.06%
CYP2D6 substrate	-	0.8062	80.62%
CYP3A4 inhibition	-	0.8285	82.85%
CYP2C9 inhibition	-	0.7486	74.86%
CYP2C19 inhibition	-	0.7313	73.13%
CYP2D6 inhibition	-	0.8270	82.70%
CYP1A2 inhibition	-	0.6717	67.17%
CYP2C8 inhibition	-	0.8626	86.26%
CYP inhibitory promiscuity	-	0.9103	91.03%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5086	50.86%
Eye corrosion	-	0.9883	98.83%
Eye irritation	+	0.6051	60.51%
Skin irritation	-	0.6980	69.80%
Skin corrosion	-	0.9226	92.26%
Ames mutagenesis	+	0.9200	92.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4145	41.45%
Micronuclear	+	0.5259	52.59%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.7374	73.74%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.7512	75.12%
Acute Oral Toxicity (c)	III	0.5836	58.36%
Estrogen receptor binding	+	0.6480	64.80%
Androgen receptor binding	-	0.5390	53.90%
Thyroid receptor binding	-	0.5728	57.28%
Glucocorticoid receptor binding	-	0.7145	71.45%
Aromatase binding	+	0.6136	61.36%
PPAR gamma	+	0.7604	76.04%
Honey bee toxicity	-	0.9422	94.22%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9463	94.63%

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	96.22%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.10%	97.25%
CHEMBL2581	P07339	Cathepsin D	93.33%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	91.92%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.69%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.09%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.81%	94.45%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	84.52%	85.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.33%	86.33%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.92%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.53%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.77%	85.14%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.48%	90.71%

Plants that contains it

• Aegle marmelos
• Afraegle paniculata
• Ammi majus
• Amyris elemifera
• Angelica dahurica
• Angelica decursiva
• Angelica gigas
• Angelica keiskei
• Angelica pachycarpa
• Angelica pubescens
• Broussonetia papyrifera
• Chorilaena quercifolia
• Citrus lucida
• Citrus trifoliata
• Conchocarpus inopinatus
• Fatoua villosa
• Ficus nervosa
• Glehnia littoralis
• Hansenia forbesii
• Hansenia weberbaueriana
• Kitagawia praeruptora
• Melicope barbigera
• Oreoseris gossypina
• Rhadinothamnus anceps
• Rhadinothamnus rudis
• Tephrosia sinapou
• Thamnosma rhodesica
• Zanthoxylum ailanthoides
• Zanthoxylum beecheyanum
• Zanthoxylum syncarpum
• Zanthoxylum wutaiense

Cross-Links

• PubChem: 604512
• NPASS: NPC215179
• LOTUS: LTS0029816
• wikiData: Q27121470