(1R,3R,9R)-3,5-dihydroxy-1,6,9-trimethyl-2,3,8,9-tetrahydro-1H-pyrano[3,2-f]chromen-10-one

Details

• Internal ID: 09c5bf7c-7e24-45fb-a054-1b91d32d8863
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Chromones
• IUPAC Name: (1R,3R,9R)-3,5-dihydroxy-1,6,9-trimethyl-2,3,8,9-tetrahydro-1H-pyrano[3,2-f]chromen-10-one
• SMILES (Canonical): CC1CC(OC2=C1C3=C(C(=C2O)C)OCC(C3=O)C)O
• SMILES (Isomeric): C[C@@H]1C[C@@H](OC2=C1C3=C(C(=C2O)C)OC[C@H](C3=O)C)O
• InChI: InChI=1S/C15H18O5/c1-6-4-9(16)20-15-10(6)11-12(17)7(2)5-19-14(11)8(3)13(15)18/h6-7,9,16,18H,4-5H2,1-3H3/t6-,7-,9-/m1/s1
• InChI Key: RLGFRXCJYZPFKF-ZXFLCMHBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₅
• Molecular Weight: 278.30 g/mol
• Exact Mass: 278.11542367 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.12
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9496	94.96%
Caco-2	+	0.4892	48.92%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6959	69.59%
OATP2B1 inhibitior	-	0.8515	85.15%
OATP1B1 inhibitior	+	0.8602	86.02%
OATP1B3 inhibitior	+	0.8480	84.80%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.7451	74.51%
P-glycoprotein inhibitior	-	0.8678	86.78%
P-glycoprotein substrate	-	0.6477	64.77%
CYP3A4 substrate	+	0.5637	56.37%
CYP2C9 substrate	+	0.5928	59.28%
CYP2D6 substrate	-	0.7984	79.84%
CYP3A4 inhibition	-	0.9377	93.77%
CYP2C9 inhibition	-	0.9023	90.23%
CYP2C19 inhibition	-	0.9314	93.14%
CYP2D6 inhibition	-	0.9327	93.27%
CYP1A2 inhibition	+	0.5885	58.85%
CYP2C8 inhibition	-	0.9025	90.25%
CYP inhibitory promiscuity	-	0.9274	92.74%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6136	61.36%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.7238	72.38%
Skin irritation	-	0.7529	75.29%
Skin corrosion	-	0.9600	96.00%
Ames mutagenesis	+	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7936	79.36%
Micronuclear	-	0.5141	51.41%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.7764	77.64%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.8627	86.27%
Acute Oral Toxicity (c)	III	0.6287	62.87%
Estrogen receptor binding	+	0.5590	55.90%
Androgen receptor binding	+	0.5688	56.88%
Thyroid receptor binding	+	0.6634	66.34%
Glucocorticoid receptor binding	+	0.6551	65.51%
Aromatase binding	-	0.6695	66.95%
PPAR gamma	-	0.5862	58.62%
Honey bee toxicity	-	0.8474	84.74%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.8209	82.09%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.62%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	91.00%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.61%	89.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.81%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.41%	99.23%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.63%	96.77%
CHEMBL2581	P07339	Cathepsin D	83.87%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.41%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.80%	100.00%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	80.38%	86.00%

Plants that contains it

• Thespesia populnea

Cross-Links

• PubChem: 162926498
• LOTUS: LTS0026628
• wikiData: Q105239982