(5R,6S)-5,6-dihydroxy-2-methoxy-5-[(1R)-1-phenylprop-2-enyl]cyclohex-2-ene-1,4-dione

Details

• Internal ID: ee010958-692e-4f15-9caa-02ffeab05944
• Taxonomy: Phenylpropanoids and polyketides > Neoflavonoids > Dalbergiones
• IUPAC Name: (5R,6S)-5,6-dihydroxy-2-methoxy-5-[(1R)-1-phenylprop-2-enyl]cyclohex-2-ene-1,4-dione
• SMILES (Canonical): COC1=CC(=O)C(C(C1=O)O)(C(C=C)C2=CC=CC=C2)O
• SMILES (Isomeric): COC1=CC(=O)[C@]([C@@H](C1=O)O)([C@H](C=C)C2=CC=CC=C2)O
• InChI: InChI=1S/C16H16O5/c1-3-11(10-7-5-4-6-8-10)16(20)13(17)9-12(21-2)14(18)15(16)19/h3-9,11,15,19-20H,1H2,2H3/t11-,15-,16+/m1/s1
• InChI Key: WQCNPLOKEWOMRG-LYRGGWFBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₆O₅
• Molecular Weight: 288.29 g/mol
• Exact Mass: 288.09977361 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 0.73
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9593	95.93%
Caco-2	-	0.6231	62.31%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8483	84.83%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9452	94.52%
OATP1B3 inhibitior	+	0.9684	96.84%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.5910	59.10%
P-glycoprotein inhibitior	-	0.7103	71.03%
P-glycoprotein substrate	-	0.8933	89.33%
CYP3A4 substrate	+	0.5616	56.16%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8263	82.63%
CYP3A4 inhibition	-	0.8101	81.01%
CYP2C9 inhibition	-	0.6941	69.41%
CYP2C19 inhibition	-	0.7050	70.50%
CYP2D6 inhibition	-	0.9157	91.57%
CYP1A2 inhibition	-	0.6438	64.38%
CYP2C8 inhibition	-	0.8714	87.14%
CYP inhibitory promiscuity	-	0.7994	79.94%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7072	70.72%
Carcinogenicity (trinary)	Non-required	0.5766	57.66%
Eye corrosion	-	0.9666	96.66%
Eye irritation	-	0.6863	68.63%
Skin irritation	-	0.6594	65.94%
Skin corrosion	-	0.8829	88.29%
Ames mutagenesis	-	0.5854	58.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.7309	73.09%
Micronuclear	+	0.5800	58.00%
Hepatotoxicity	+	0.6552	65.52%
skin sensitisation	-	0.5911	59.11%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.7000	70.00%
Nephrotoxicity	+	0.6156	61.56%
Acute Oral Toxicity (c)	III	0.6015	60.15%
Estrogen receptor binding	+	0.5472	54.72%
Androgen receptor binding	+	0.6454	64.54%
Thyroid receptor binding	-	0.5242	52.42%
Glucocorticoid receptor binding	+	0.6177	61.77%
Aromatase binding	+	0.6571	65.71%
PPAR gamma	+	0.5452	54.52%
Honey bee toxicity	-	0.4687	46.87%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6600	66.00%
Fish aquatic toxicity	+	0.9791	97.91%

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	97.54%	91.11%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	95.66%	94.08%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	95.35%	94.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.68%	95.56%
CHEMBL2581	P07339	Cathepsin D	92.72%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.17%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.96%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	85.83%	91.19%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	85.67%	94.23%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	83.96%	94.97%
CHEMBL1951	P21397	Monoamine oxidase A	83.26%	91.49%

Plants that contains it

• Dalbergia sissoo

Cross-Links

• PubChem: 163055796
• LOTUS: LTS0194950
• wikiData: Q105310346