(9S)-3,9-dihydroxy-16,17-dimethoxytricyclo[12.3.1.12,6]nonadeca-1(17),2,4,6(19),14(18),15-hexaen-7-one

Details

• Internal ID: 7d051398-83cf-4d70-aca2-7914e8f466e3
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Cyclic diarylheptanoids > Meta,meta-bridged biphenyls
• IUPAC Name: (9S)-3,9-dihydroxy-16,17-dimethoxytricyclo[12.3.1.12,6]nonadeca-1(17),2,4,6(19),14(18),15-hexaen-7-one
• SMILES (Canonical): COC1=CC2=CC(=C1OC)C3=C(C=CC(=C3)C(=O)CC(CCCC2)O)O
• SMILES (Isomeric): COC1=CC2=CC(=C1OC)C3=C(C=CC(=C3)C(=O)C[C@H](CCCC2)O)O
• InChI: InChI=1S/C21H24O5/c1-25-20-10-13-5-3-4-6-15(22)12-19(24)14-7-8-18(23)16(11-14)17(9-13)21(20)26-2/h7-11,15,22-23H,3-6,12H2,1-2H3/t15-/m0/s1
• InChI Key: HBPMCGRQMGSKIQ-HNNXBMFYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₄O₅
• Molecular Weight: 356.40 g/mol
• Exact Mass: 356.16237386 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.74
• 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	+	0.9886	98.86%
Caco-2	+	0.7681	76.81%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8903	89.03%
OATP2B1 inhibitior	-	0.8536	85.36%
OATP1B1 inhibitior	+	0.9136	91.36%
OATP1B3 inhibitior	+	0.9390	93.90%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9071	90.71%
BSEP inhibitior	+	0.7871	78.71%
P-glycoprotein inhibitior	-	0.6155	61.55%
P-glycoprotein substrate	-	0.6845	68.45%
CYP3A4 substrate	+	0.6116	61.16%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3490	34.90%
CYP3A4 inhibition	-	0.6963	69.63%
CYP2C9 inhibition	-	0.8409	84.09%
CYP2C19 inhibition	-	0.5106	51.06%
CYP2D6 inhibition	-	0.8475	84.75%
CYP1A2 inhibition	+	0.9422	94.22%
CYP2C8 inhibition	+	0.7074	70.74%
CYP inhibitory promiscuity	-	0.8610	86.10%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6150	61.50%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.7958	79.58%
Skin irritation	-	0.6720	67.20%
Skin corrosion	-	0.9290	92.90%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4085	40.85%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.8833	88.33%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.7951	79.51%
Acute Oral Toxicity (c)	III	0.5841	58.41%
Estrogen receptor binding	+	0.7396	73.96%
Androgen receptor binding	+	0.7130	71.30%
Thyroid receptor binding	+	0.5279	52.79%
Glucocorticoid receptor binding	+	0.7888	78.88%
Aromatase binding	+	0.5681	56.81%
PPAR gamma	+	0.5647	56.47%
Honey bee toxicity	-	0.8292	82.92%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5151	51.51%
Fish aquatic toxicity	+	0.9622	96.22%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.25%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.93%	91.11%
CHEMBL241	Q14432	Phosphodiesterase 3A	95.72%	92.94%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.11%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.49%	95.56%
CHEMBL2535	P11166	Glucose transporter	92.91%	98.75%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.76%	99.15%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.72%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.05%	86.33%
CHEMBL3438	Q05513	Protein kinase C zeta	89.77%	88.48%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.76%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.48%	89.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.15%	90.71%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	87.29%	96.00%
CHEMBL5747	Q92793	CREB-binding protein	87.11%	95.12%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.07%	92.62%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	84.02%	95.53%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.70%	93.04%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.65%	95.78%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	83.35%	96.38%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	83.34%	92.88%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.05%	97.09%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	81.48%	82.67%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.00%	99.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.81%	95.50%

Plants that contains it

• Rhoiptelea chiliantha

Cross-Links

• PubChem: 134835192
• LOTUS: LTS0275728
• wikiData: Q105025426