(1R,8S)-3,4-dimethoxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-15-one

Details

• Internal ID: 9ad8d9ae-d381-4e44-8fd5-010146a40cc2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (1R,8S)-3,4-dimethoxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-15-one
• SMILES (Canonical): CC(C)C1=C(C(=C2C(=C1)C3CC4C2(CCCC4(C)C)C(=O)O3)OC)OC
• SMILES (Isomeric): CC(C)C1=C(C(=C2C(=C1)[C@@H]3CC4[C@@]2(CCCC4(C)C)C(=O)O3)OC)OC
• InChI: InChI=1S/C22H30O4/c1-12(2)13-10-14-15-11-16-21(3,4)8-7-9-22(16,20(23)26-15)17(14)19(25-6)18(13)24-5/h10,12,15-16H,7-9,11H2,1-6H3/t15-,16?,22+/m0/s1
• InChI Key: BMUVJFGCCPHXOJ-RYVCVBLFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₀O₄
• Molecular Weight: 358.50 g/mol
• Exact Mass: 358.21440943 g/mol
• Topological Polar Surface Area (TPSA): 44.80 Ų
• XlogP: 5.00
• Atomic LogP (AlogP): 4.89
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9849	98.49%
Caco-2	+	0.8773	87.73%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7762	77.62%
OATP2B1 inhibitior	-	0.8591	85.91%
OATP1B1 inhibitior	+	0.9165	91.65%
OATP1B3 inhibitior	+	0.9768	97.68%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.4559	45.59%
P-glycoprotein inhibitior	-	0.5527	55.27%
P-glycoprotein substrate	-	0.7937	79.37%
CYP3A4 substrate	+	0.6507	65.07%
CYP2C9 substrate	-	0.5788	57.88%
CYP2D6 substrate	-	0.6906	69.06%
CYP3A4 inhibition	-	0.6634	66.34%
CYP2C9 inhibition	-	0.8923	89.23%
CYP2C19 inhibition	-	0.6893	68.93%
CYP2D6 inhibition	-	0.9085	90.85%
CYP1A2 inhibition	+	0.5828	58.28%
CYP2C8 inhibition	-	0.6877	68.77%
CYP inhibitory promiscuity	-	0.9113	91.13%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6999	69.99%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.8320	83.20%
Skin irritation	-	0.7316	73.16%
Skin corrosion	-	0.9565	95.65%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3738	37.38%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.5559	55.59%
skin sensitisation	-	0.8886	88.86%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.7233	72.33%
Acute Oral Toxicity (c)	IV	0.5822	58.22%
Estrogen receptor binding	+	0.8417	84.17%
Androgen receptor binding	+	0.6344	63.44%
Thyroid receptor binding	+	0.8194	81.94%
Glucocorticoid receptor binding	+	0.8077	80.77%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.8565	85.65%
Honey bee toxicity	-	0.7196	71.96%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9859	98.59%

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	96.99%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.37%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.87%	97.25%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	93.49%	96.77%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.04%	96.09%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	89.90%	96.38%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.74%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.66%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.60%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.41%	85.14%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.34%	93.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.72%	97.14%
CHEMBL1937	Q92769	Histone deacetylase 2	86.05%	94.75%
CHEMBL3192	Q9BY41	Histone deacetylase 8	85.87%	93.99%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.27%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.16%	95.89%
CHEMBL2581	P07339	Cathepsin D	85.03%	98.95%
CHEMBL2535	P11166	Glucose transporter	84.98%	98.75%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.96%	91.07%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.33%	90.71%
CHEMBL5203	P33316	dUTP pyrophosphatase	83.55%	99.18%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	82.59%	95.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.91%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	80.87%	91.19%

Plants that contains it

• Rosmarinus officinalis

Cross-Links

• PubChem: 14379075
• LOTUS: LTS0259263
• wikiData: Q104938584