(10Z)-4,17-dihydroxy-3,11-dimethoxytricyclo[12.3.1.12,6]nonadeca-1(17),2,4,6(19),10,14(18),15-heptaen-9-one

Details

• Internal ID: 38a0dfdb-6540-4c91-a69d-4454ff81fc6f
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Cyclic diarylheptanoids > Meta,meta-bridged biphenyls
• IUPAC Name: (10Z)-4,17-dihydroxy-3,11-dimethoxytricyclo[12.3.1.12,6]nonadeca-1(17),2,4,6(19),10,14(18),15-heptaen-9-one
• SMILES (Canonical): COC1=CC(=O)CCC2=CC(=C(C(=C2)O)OC)C3=C(C=CC(=C3)CC1)O
• SMILES (Isomeric): CO/C/1=C\C(=O)CCC2=CC(=C(C(=C2)O)OC)C3=C(C=CC(=C3)CC1)O
• InChI: InChI=1S/C21H22O5/c1-25-16-7-4-13-5-8-19(23)17(9-13)18-10-14(3-6-15(22)12-16)11-20(24)21(18)26-2/h5,8-12,23-24H,3-4,6-7H2,1-2H3/b16-12-
• InChI Key: ZRXSYFITKRMPDZ-VBKFSLOCSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₅
• Molecular Weight: 354.40 g/mol
• Exact Mass: 354.14672380 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.75
• H-Bond Acceptor: 5
• 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	+	0.9913	99.13%
Caco-2	+	0.8815	88.15%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8253	82.53%
OATP2B1 inhibitior	-	0.8549	85.49%
OATP1B1 inhibitior	+	0.9238	92.38%
OATP1B3 inhibitior	+	0.9667	96.67%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8287	82.87%
BSEP inhibitior	+	0.8976	89.76%
P-glycoprotein inhibitior	-	0.5313	53.13%
P-glycoprotein substrate	-	0.8560	85.60%
CYP3A4 substrate	+	0.5206	52.06%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7801	78.01%
CYP3A4 inhibition	-	0.7442	74.42%
CYP2C9 inhibition	-	0.7036	70.36%
CYP2C19 inhibition	+	0.6649	66.49%
CYP2D6 inhibition	-	0.7898	78.98%
CYP1A2 inhibition	+	0.9453	94.53%
CYP2C8 inhibition	-	0.7942	79.42%
CYP inhibitory promiscuity	+	0.5541	55.41%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.8863	88.63%
Carcinogenicity (trinary)	Non-required	0.6316	63.16%
Eye corrosion	-	0.9909	99.09%
Eye irritation	+	0.5966	59.66%
Skin irritation	-	0.6402	64.02%
Skin corrosion	-	0.9393	93.93%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	-	0.5035	50.35%
skin sensitisation	-	0.8024	80.24%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.6412	64.12%
Acute Oral Toxicity (c)	III	0.4472	44.72%
Estrogen receptor binding	+	0.9009	90.09%
Androgen receptor binding	+	0.6780	67.80%
Thyroid receptor binding	+	0.6485	64.85%
Glucocorticoid receptor binding	+	0.8462	84.62%
Aromatase binding	+	0.6259	62.59%
PPAR gamma	+	0.7689	76.89%
Honey bee toxicity	-	0.9206	92.06%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9901	99.01%

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	98.13%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.12%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.49%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.33%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	91.23%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.60%	95.56%
CHEMBL4208	P20618	Proteasome component C5	89.91%	90.00%
CHEMBL2535	P11166	Glucose transporter	89.65%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.40%	94.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.96%	93.99%

Plants that contains it

• Garuga pinnata

Cross-Links

• PubChem: 101426347
• LOTUS: LTS0221972
• wikiData: Q105382328