(2R,3R)-8-hydroxy-3-(hydroxymethyl)-2,3,9-trimethyl-2H-furo[3,2-c]chromen-4-one

Details

• Internal ID: bbcc55e2-e57c-4bef-9ce9-d9717a6a88b3
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Furanocoumarins > Angular furanocoumarins
• IUPAC Name: (2R,3R)-8-hydroxy-3-(hydroxymethyl)-2,3,9-trimethyl-2H-furo[3,2-c]chromen-4-one
• SMILES (Canonical): CC1C(C2=C(O1)C3=C(C=CC(=C3C)O)OC2=O)(C)CO
• SMILES (Isomeric): C[C@@H]1[C@@](C2=C(O1)C3=C(C=CC(=C3C)O)OC2=O)(C)CO
• InChI: InChI=1S/C15H16O5/c1-7-9(17)4-5-10-11(7)13-12(14(18)20-10)15(3,6-16)8(2)19-13/h4-5,8,16-17H,6H2,1-3H3/t8-,15-/m1/s1
• InChI Key: AMXIALDGAYCNAK-ANRSDYALSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₅
• Molecular Weight: 276.28 g/mol
• Exact Mass: 276.09977361 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.84
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9735	97.35%
Caco-2	+	0.7658	76.58%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7150	71.50%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8743	87.43%
OATP1B3 inhibitior	+	0.8890	88.90%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.5572	55.72%
P-glycoprotein inhibitior	-	0.9083	90.83%
P-glycoprotein substrate	-	0.7349	73.49%
CYP3A4 substrate	+	0.5418	54.18%
CYP2C9 substrate	-	0.6233	62.33%
CYP2D6 substrate	-	0.8440	84.40%
CYP3A4 inhibition	-	0.8508	85.08%
CYP2C9 inhibition	-	0.6030	60.30%
CYP2C19 inhibition	-	0.7193	71.93%
CYP2D6 inhibition	-	0.9255	92.55%
CYP1A2 inhibition	+	0.5565	55.65%
CYP2C8 inhibition	-	0.8095	80.95%
CYP inhibitory promiscuity	-	0.6560	65.60%
UGT catelyzed	+	0.5362	53.62%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5818	58.18%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.6497	64.97%
Skin irritation	-	0.7493	74.93%
Skin corrosion	-	0.9513	95.13%
Ames mutagenesis	+	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8110	81.10%
Micronuclear	-	0.5226	52.26%
Hepatotoxicity	+	0.6375	63.75%
skin sensitisation	-	0.8328	83.28%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.8007	80.07%
Acute Oral Toxicity (c)	III	0.5869	58.69%
Estrogen receptor binding	+	0.8199	81.99%
Androgen receptor binding	+	0.6059	60.59%
Thyroid receptor binding	-	0.5840	58.40%
Glucocorticoid receptor binding	+	0.6084	60.84%
Aromatase binding	+	0.6464	64.64%
PPAR gamma	+	0.7999	79.99%
Honey bee toxicity	-	0.9047	90.47%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.9811	98.11%

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	97.09%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.81%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.43%	99.23%
CHEMBL4040	P28482	MAP kinase ERK2	90.56%	83.82%
CHEMBL2581	P07339	Cathepsin D	89.49%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.81%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.09%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.97%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	84.50%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.61%	97.09%

Plants that contains it

• Glaucidium palmatum

Cross-Links

• PubChem: 44347289
• LOTUS: LTS0030541
• wikiData: Q104914993