(1R,8S,9S,10S)-3,8-dihydroxy-4-methoxy-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: e0287440-c8fc-420b-92f7-cb11fd4a4db3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (1R,8S,9S,10S)-3,8-dihydroxy-4-methoxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[7.5.2.01,10.02,7]hexadeca-2,4,6-trien-15-one
• InChI: InChI=1S/C21H28O5/c1-10(2)11-9-12-13(15(23)16(11)25-5)21-8-6-7-20(3,4)18(21)17(14(12)22)26-19(21)24/h9-10,14,17-18,22-23H,6-8H2,1-5H3/t14-,17+,18-,21-/m0/s1
• InChI Key: KQQFZKKHMREZAF-NFQYFHPZSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₈O₅
• Molecular Weight: 360.40 g/mol
• Exact Mass: 360.19367399 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.56
• 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	+	0.9758	97.58%
Caco-2	+	0.6523	65.23%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7390	73.90%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8404	84.04%
OATP1B3 inhibitior	+	0.8941	89.41%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.8235	82.35%
P-glycoprotein inhibitior	-	0.7147	71.47%
P-glycoprotein substrate	-	0.7109	71.09%
CYP3A4 substrate	+	0.6445	64.45%
CYP2C9 substrate	-	0.5994	59.94%
CYP2D6 substrate	+	0.3466	34.66%
CYP3A4 inhibition	-	0.5260	52.60%
CYP2C9 inhibition	-	0.5610	56.10%
CYP2C19 inhibition	-	0.5000	50.00%
CYP2D6 inhibition	-	0.8362	83.62%
CYP1A2 inhibition	+	0.6971	69.71%
CYP2C8 inhibition	-	0.7178	71.78%
CYP inhibitory promiscuity	-	0.6520	65.20%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.5283	52.83%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.9087	90.87%
Skin irritation	-	0.6952	69.52%
Skin corrosion	-	0.9265	92.65%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8147	81.47%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	+	0.6338	63.38%
skin sensitisation	-	0.8744	87.44%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.8522	85.22%
Acute Oral Toxicity (c)	III	0.4797	47.97%
Estrogen receptor binding	+	0.7480	74.80%
Androgen receptor binding	+	0.6159	61.59%
Thyroid receptor binding	+	0.6609	66.09%
Glucocorticoid receptor binding	+	0.8004	80.04%
Aromatase binding	+	0.5604	56.04%
PPAR gamma	+	0.7999	79.99%
Honey bee toxicity	-	0.7932	79.32%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9926	99.26%

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	99.05%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.34%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.88%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.98%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.96%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.85%	99.15%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	90.60%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.07%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.58%	86.33%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.30%	93.56%
CHEMBL2581	P07339	Cathepsin D	88.24%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.05%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.00%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.99%	97.09%
CHEMBL1937	Q92769	Histone deacetylase 2	87.59%	94.75%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.88%	96.77%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.74%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	85.85%	91.19%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.74%	92.62%
CHEMBL213	P08588	Beta-1 adrenergic receptor	85.18%	95.56%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.13%	91.07%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.50%	94.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.88%	93.99%
CHEMBL3286	P00749	Urokinase-type plasminogen activator	80.46%	97.88%

Plants that contains it

• Lepechinia meyenii

Cross-Links

• PubChem: 102110181
• LOTUS: LTS0005978
• wikiData: Q104398649