(3S,4S)-4-(3,4-dihydroxyphenyl)-6,7-dihydroxy-3-methoxycarbonyl-3,4-dihydronaphthalene-2-carboxylic acid

Details

• Internal ID: b8246c64-1c45-48ff-8e56-a8f515de40c8
• Taxonomy: Lignans, neolignans and related compounds > Aryltetralin lignans
• IUPAC Name: (3S,4S)-4-(3,4-dihydroxyphenyl)-6,7-dihydroxy-3-methoxycarbonyl-3,4-dihydronaphthalene-2-carboxylic acid
• SMILES (Canonical): COC(=O)C1C(C2=CC(=C(C=C2C=C1C(=O)O)O)O)C3=CC(=C(C=C3)O)O
• SMILES (Isomeric): COC(=O)[C@H]1[C@H](C2=CC(=C(C=C2C=C1C(=O)O)O)O)C3=CC(=C(C=C3)O)O
• InChI: InChI=1S/C19H16O8/c1-27-19(26)17-11(18(24)25)4-9-6-14(22)15(23)7-10(9)16(17)8-2-3-12(20)13(21)5-8/h2-7,16-17,20-23H,1H3,(H,24,25)/t16-,17+/m0/s1
• InChI Key: AVJRJNWOJPUZBH-DLBZAZTESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₆O₈
• Molecular Weight: 372.30 g/mol
• Exact Mass: 372.08451746 g/mol
• Topological Polar Surface Area (TPSA): 145.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.91
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9885	98.85%
Caco-2	-	0.7158	71.58%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8291	82.91%
OATP2B1 inhibitior	-	0.5693	56.93%
OATP1B1 inhibitior	+	0.9377	93.77%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.7971	79.71%
P-glycoprotein substrate	-	0.8226	82.26%
CYP3A4 substrate	+	0.5172	51.72%
CYP2C9 substrate	-	0.5928	59.28%
CYP2D6 substrate	-	0.8737	87.37%
CYP3A4 inhibition	-	0.8760	87.60%
CYP2C9 inhibition	+	0.8830	88.30%
CYP2C19 inhibition	-	0.5137	51.37%
CYP2D6 inhibition	-	0.8603	86.03%
CYP1A2 inhibition	+	0.6861	68.61%
CYP2C8 inhibition	+	0.5586	55.86%
CYP inhibitory promiscuity	-	0.5437	54.37%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8427	84.27%
Carcinogenicity (trinary)	Non-required	0.4429	44.29%
Eye corrosion	-	0.9929	99.29%
Eye irritation	+	0.6925	69.25%
Skin irritation	-	0.6560	65.60%
Skin corrosion	-	0.9474	94.74%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7166	71.66%
Micronuclear	+	0.8700	87.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.8074	80.74%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.5943	59.43%
Acute Oral Toxicity (c)	IV	0.4018	40.18%
Estrogen receptor binding	+	0.7494	74.94%
Androgen receptor binding	+	0.7115	71.15%
Thyroid receptor binding	+	0.5258	52.58%
Glucocorticoid receptor binding	+	0.8415	84.15%
Aromatase binding	-	0.6692	66.92%
PPAR gamma	+	0.5440	54.40%
Honey bee toxicity	-	0.8226	82.26%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.9974	99.74%

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	99.27%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.48%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.24%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.11%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.49%	85.14%
CHEMBL1951	P21397	Monoamine oxidase A	88.18%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.39%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	84.33%	91.19%
CHEMBL2581	P07339	Cathepsin D	82.72%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.37%	99.17%

Plants that contains it

• Pellia epiphylla

Cross-Links

• PubChem: 162857754
• LOTUS: LTS0019814
• wikiData: Q104919587