methyl (3S,4S)-4,6-dihydroxy-3-methoxy-2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5-carboxylate

Details

• Internal ID: 6bf56c37-d924-4054-9c01-e7a8473f53db
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans
• IUPAC Name: methyl (3S,4S)-4,6-dihydroxy-3-methoxy-2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5-carboxylate
• SMILES (Canonical): CC1(C(C(C2=C(O1)C3=CC=CC=C3C(=C2C(=O)OC)O)O)OC)C
• SMILES (Isomeric): CC1([C@H]([C@H](C2=C(O1)C3=CC=CC=C3C(=C2C(=O)OC)O)O)OC)C
• InChI: InChI=1S/C18H20O6/c1-18(2)16(22-3)14(20)11-12(17(21)23-4)13(19)9-7-5-6-8-10(9)15(11)24-18/h5-8,14,16,19-20H,1-4H3/t14-,16-/m0/s1
• InChI Key: OXENTHYAVBFFDI-HOCLYGCPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₀O₆
• Molecular Weight: 332.30 g/mol
• Exact Mass: 332.12598835 g/mol
• Topological Polar Surface Area (TPSA): 85.20 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.55
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9513	95.13%
Caco-2	-	0.5443	54.43%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7391	73.91%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7831	78.31%
OATP1B3 inhibitior	+	0.9344	93.44%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6635	66.35%
P-glycoprotein inhibitior	-	0.5437	54.37%
P-glycoprotein substrate	-	0.7524	75.24%
CYP3A4 substrate	+	0.6726	67.26%
CYP2C9 substrate	-	0.8019	80.19%
CYP2D6 substrate	-	0.8280	82.80%
CYP3A4 inhibition	-	0.8327	83.27%
CYP2C9 inhibition	-	0.8988	89.88%
CYP2C19 inhibition	-	0.7367	73.67%
CYP2D6 inhibition	-	0.8417	84.17%
CYP1A2 inhibition	+	0.6075	60.75%
CYP2C8 inhibition	+	0.6674	66.74%
CYP inhibitory promiscuity	-	0.7236	72.36%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5374	53.74%
Eye corrosion	-	0.9857	98.57%
Eye irritation	-	0.7624	76.24%
Skin irritation	-	0.7762	77.62%
Skin corrosion	-	0.9718	97.18%
Ames mutagenesis	+	0.6446	64.46%
Human Ether-a-go-go-Related Gene inhibition	-	0.6606	66.06%
Micronuclear	+	0.7000	70.00%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.9242	92.42%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.6844	68.44%
Acute Oral Toxicity (c)	III	0.6592	65.92%
Estrogen receptor binding	+	0.7985	79.85%
Androgen receptor binding	+	0.5993	59.93%
Thyroid receptor binding	+	0.6178	61.78%
Glucocorticoid receptor binding	+	0.8263	82.63%
Aromatase binding	+	0.6461	64.61%
PPAR gamma	+	0.8370	83.70%
Honey bee toxicity	-	0.8476	84.76%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9498	94.98%

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	99.40%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	95.71%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.98%	96.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	91.11%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.57%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.05%	99.23%
CHEMBL2581	P07339	Cathepsin D	88.13%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	87.57%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.67%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.95%	89.00%
CHEMBL5028	O14672	ADAM10	82.59%	97.50%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.18%	85.14%

Plants that contains it

• Rubia cordifolia

Cross-Links

• PubChem: 162884073
• LOTUS: LTS0153001
• wikiData: Q105202548