(1R,8S,9S,10S)-8-hydroxy-3,4-dimethoxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[7.5.2.01,10.02,7]hexadeca-2,4,6-trien-15-one

Details

• Internal ID: 7cb0668d-1684-4e7b-af72-158bc4251903
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (1R,8S,9S,10S)-8-hydroxy-3,4-dimethoxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[7.5.2.01,10.02,7]hexadeca-2,4,6-trien-15-one
• SMILES (Canonical): CC(C)C1=C(C(=C2C(=C1)C(C3C4C2(CCCC4(C)C)C(=O)O3)O)OC)OC
• SMILES (Isomeric): CC(C)C1=C(C(=C2C(=C1)[C@@H]([C@@H]3[C@@H]4[C@@]2(CCCC4(C)C)C(=O)O3)O)OC)OC
• InChI: InChI=1S/C22H30O5/c1-11(2)12-10-13-14(17(26-6)16(12)25-5)22-9-7-8-21(3,4)19(22)18(15(13)23)27-20(22)24/h10-11,15,18-19,23H,7-9H2,1-6H3/t15-,18+,19-,22-/m0/s1
• InChI Key: WLRZIPVGEMNPES-AKYGZRSFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₀O₅
• Molecular Weight: 374.50 g/mol
• Exact Mass: 374.20932405 g/mol
• Topological Polar Surface Area (TPSA): 65.00 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 3.86
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9891	98.91%
Caco-2	+	0.7821	78.21%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7116	71.16%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8997	89.97%
OATP1B3 inhibitior	+	0.9114	91.14%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.6331	63.31%
P-glycoprotein inhibitior	-	0.5418	54.18%
P-glycoprotein substrate	-	0.7317	73.17%
CYP3A4 substrate	+	0.6282	62.82%
CYP2C9 substrate	-	0.6141	61.41%
CYP2D6 substrate	-	0.6567	65.67%
CYP3A4 inhibition	+	0.5431	54.31%
CYP2C9 inhibition	-	0.5851	58.51%
CYP2C19 inhibition	-	0.5507	55.07%
CYP2D6 inhibition	-	0.8681	86.81%
CYP1A2 inhibition	+	0.5416	54.16%
CYP2C8 inhibition	-	0.7453	74.53%
CYP inhibitory promiscuity	-	0.8467	84.67%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.5354	53.54%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.8826	88.26%
Skin irritation	-	0.7105	71.05%
Skin corrosion	-	0.9311	93.11%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7279	72.79%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	+	0.6463	64.63%
skin sensitisation	-	0.8658	86.58%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.7170	71.70%
Acute Oral Toxicity (c)	III	0.5020	50.20%
Estrogen receptor binding	+	0.7886	78.86%
Androgen receptor binding	+	0.6500	65.00%
Thyroid receptor binding	+	0.7476	74.76%
Glucocorticoid receptor binding	+	0.8200	82.00%
Aromatase binding	-	0.5236	52.36%
PPAR gamma	+	0.7910	79.10%
Honey bee toxicity	-	0.7746	77.46%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9915	99.15%

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	97.61%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.46%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.49%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.29%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	92.62%	96.77%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.57%	85.14%
CHEMBL2581	P07339	Cathepsin D	89.57%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.51%	95.56%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.99%	93.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.96%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.16%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.28%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.09%	92.62%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.09%	90.71%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.92%	91.07%
CHEMBL340	P08684	Cytochrome P450 3A4	85.79%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.30%	89.00%
CHEMBL2535	P11166	Glucose transporter	83.83%	98.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.56%	99.23%
CHEMBL1937	Q92769	Histone deacetylase 2	82.52%	94.75%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.34%	97.14%
CHEMBL213	P08588	Beta-1 adrenergic receptor	82.05%	95.56%
CHEMBL1871	P10275	Androgen Receptor	80.66%	96.43%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.61%	99.15%

Plants that contains it

• Salvia columbariae

Cross-Links

• PubChem: 163015381
• LOTUS: LTS0211701
• wikiData: Q105308185