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

Details

• Internal ID: 14c085c5-573a-4c9b-9eb7-edf39e900661
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans
• IUPAC Name: methyl (3S,4S)-3,4,6-trihydroxy-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)O)C
• SMILES (Isomeric): CC1([C@H]([C@H](C2=C(O1)C3=CC=CC=C3C(=C2C(=O)OC)O)O)O)C
• InChI: InChI=1S/C17H18O6/c1-17(2)15(20)13(19)10-11(16(21)22-3)12(18)8-6-4-5-7-9(8)14(10)23-17/h4-7,13,15,18-20H,1-3H3/t13-,15-/m0/s1
• InChI Key: ZNHMFNWRNCFYHA-ZFWWWQNUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₈O₆
• Molecular Weight: 318.32 g/mol
• Exact Mass: 318.11033829 g/mol
• Topological Polar Surface Area (TPSA): 96.20 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 1.90
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9158	91.58%
Caco-2	-	0.6825	68.25%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7301	73.01%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7851	78.51%
OATP1B3 inhibitior	+	0.9527	95.27%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7350	73.50%
P-glycoprotein inhibitior	-	0.7584	75.84%
P-glycoprotein substrate	-	0.7479	74.79%
CYP3A4 substrate	+	0.6504	65.04%
CYP2C9 substrate	-	0.8038	80.38%
CYP2D6 substrate	-	0.8316	83.16%
CYP3A4 inhibition	-	0.8474	84.74%
CYP2C9 inhibition	-	0.9635	96.35%
CYP2C19 inhibition	-	0.8171	81.71%
CYP2D6 inhibition	-	0.8988	89.88%
CYP1A2 inhibition	+	0.5729	57.29%
CYP2C8 inhibition	+	0.5781	57.81%
CYP inhibitory promiscuity	-	0.8393	83.93%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5655	56.55%
Eye corrosion	-	0.9863	98.63%
Eye irritation	-	0.8015	80.15%
Skin irritation	-	0.7687	76.87%
Skin corrosion	-	0.9572	95.72%
Ames mutagenesis	+	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7000	70.00%
Micronuclear	+	0.7000	70.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.9129	91.29%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.5718	57.18%
Acute Oral Toxicity (c)	III	0.6384	63.84%
Estrogen receptor binding	+	0.6965	69.65%
Androgen receptor binding	-	0.4850	48.50%
Thyroid receptor binding	+	0.5776	57.76%
Glucocorticoid receptor binding	+	0.8843	88.43%
Aromatase binding	+	0.6801	68.01%
PPAR gamma	+	0.8295	82.95%
Honey bee toxicity	-	0.8646	86.46%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9572	95.72%

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	99.29%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.21%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.45%	95.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.65%	95.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.62%	99.23%
CHEMBL1951	P21397	Monoamine oxidase A	84.51%	91.49%
CHEMBL221	P23219	Cyclooxygenase-1	84.16%	90.17%
CHEMBL2581	P07339	Cathepsin D	83.56%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.18%	89.00%
CHEMBL5028	O14672	ADAM10	82.13%	97.50%
CHEMBL340	P08684	Cytochrome P450 3A4	80.98%	91.19%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.57%	94.45%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.47%	92.62%

Plants that contains it

• Dolichopentas longiflora

Cross-Links

• PubChem: 25145889
• LOTUS: LTS0141817
• wikiData: Q105380070