(1R,8R,10S)-3,4-dihydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-triene-9,15-dione

Details

• Internal ID: 630f3066-8ac4-447a-9983-68035ec7eefa
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (1R,8R,10S)-3,4-dihydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-triene-9,15-dione
• SMILES (Canonical): CC(C)C1=C(C(=C2C(=C1)C3C(=O)C4C2(CCCC4(C)C)C(=O)O3)O)O
• SMILES (Isomeric): CC(C)C1=C(C(=C2C(=C1)[C@@H]3C(=O)[C@@H]4[C@@]2(CCCC4(C)C)C(=O)O3)O)O
• InChI: InChI=1S/C20H24O5/c1-9(2)10-8-11-12(14(22)13(10)21)20-7-5-6-19(3,4)17(20)15(23)16(11)25-18(20)24/h8-9,16-17,21-22H,5-7H2,1-4H3/t16-,17+,20+/m1/s1
• InChI Key: LGMZDFRDZKIULZ-UWVAXJGDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₅
• Molecular Weight: 344.40 g/mol
• Exact Mass: 344.16237386 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.47
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8681	86.81%
Caco-2	+	0.6090	60.90%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8086	80.86%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8208	82.08%
OATP1B3 inhibitior	+	0.9493	94.93%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.8917	89.17%
P-glycoprotein inhibitior	-	0.7997	79.97%
P-glycoprotein substrate	-	0.8084	80.84%
CYP3A4 substrate	+	0.6235	62.35%
CYP2C9 substrate	-	0.5725	57.25%
CYP2D6 substrate	-	0.7958	79.58%
CYP3A4 inhibition	-	0.8999	89.99%
CYP2C9 inhibition	-	0.8324	83.24%
CYP2C19 inhibition	-	0.8613	86.13%
CYP2D6 inhibition	-	0.9278	92.78%
CYP1A2 inhibition	+	0.7082	70.82%
CYP2C8 inhibition	-	0.7500	75.00%
CYP inhibitory promiscuity	-	0.9569	95.69%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.7069	70.69%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.8087	80.87%
Skin irritation	-	0.6369	63.69%
Skin corrosion	-	0.8732	87.32%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8711	87.11%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	+	0.6178	61.78%
skin sensitisation	-	0.8346	83.46%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.7747	77.47%
Acute Oral Toxicity (c)	III	0.6623	66.23%
Estrogen receptor binding	+	0.7074	70.74%
Androgen receptor binding	+	0.6648	66.48%
Thyroid receptor binding	+	0.6447	64.47%
Glucocorticoid receptor binding	+	0.8550	85.50%
Aromatase binding	+	0.5900	59.00%
PPAR gamma	+	0.7526	75.26%
Honey bee toxicity	-	0.8386	83.86%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9929	99.29%

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	98.61%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.96%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.57%	94.45%
CHEMBL2581	P07339	Cathepsin D	93.58%	98.95%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	93.00%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.55%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.53%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.08%	85.14%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	88.33%	96.38%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.20%	95.89%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.03%	96.77%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.02%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	86.57%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.38%	86.33%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.81%	93.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.74%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.52%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.64%	99.23%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.35%	96.21%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.39%	91.07%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.09%	93.04%
CHEMBL1951	P21397	Monoamine oxidase A	81.95%	91.49%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.73%	93.40%

Plants that contains it

• Salvia mellifera

Cross-Links

• PubChem: 162977601
• LOTUS: LTS0093121
• wikiData: Q105151465