(3R)-3abeta,4,5,5a,6,7,8,9,9abeta,9balpha-Decahydro-3alpha,5aalpha,9-trimethyl-6alpha,9beta-dihydroxynaphtho[1,2-b]furan-2(3H)-one

Details

• Internal ID: ed35daea-5158-4f0b-b675-6a974231a043
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3R,3aS,5aR,6R,9R,9aS,9bS)-6,9-dihydroxy-3,5a,9-trimethyl-3a,4,5,6,7,8,9a,9b-octahydro-3H-benzo[g][1]benzofuran-2-one
• SMILES (Canonical): CC1C2CCC3(C(CCC(C3C2OC1=O)(C)O)O)C
• SMILES (Isomeric): C[C@@H]1[C@@H]2CC[C@]3([C@@H](CC[C@@]([C@@H]3[C@H]2OC1=O)(C)O)O)C
• InChI: InChI=1S/C15H24O4/c1-8-9-4-6-14(2)10(16)5-7-15(3,18)12(14)11(9)19-13(8)17/h8-12,16,18H,4-7H2,1-3H3/t8-,9+,10-,11+,12-,14+,15-/m1/s1
• InChI Key: JZWIOLGEFWVOLI-XUUGXOGISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄O₄
• Molecular Weight: 268.35 g/mol
• Exact Mass: 268.16745924 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.49
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9834	98.34%
Caco-2	-	0.5128	51.28%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6749	67.49%
OATP2B1 inhibitior	-	0.8549	85.49%
OATP1B1 inhibitior	+	0.9346	93.46%
OATP1B3 inhibitior	+	0.9058	90.58%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7071	70.71%
BSEP inhibitior	-	0.9063	90.63%
P-glycoprotein inhibitior	-	0.9147	91.47%
P-glycoprotein substrate	-	0.8093	80.93%
CYP3A4 substrate	+	0.6326	63.26%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8405	84.05%
CYP3A4 inhibition	-	0.6898	68.98%
CYP2C9 inhibition	-	0.8951	89.51%
CYP2C19 inhibition	-	0.9037	90.37%
CYP2D6 inhibition	-	0.9742	97.42%
CYP1A2 inhibition	-	0.6949	69.49%
CYP2C8 inhibition	-	0.9599	95.99%
CYP inhibitory promiscuity	-	0.9718	97.18%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5839	58.39%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.9626	96.26%
Skin irritation	+	0.6497	64.97%
Skin corrosion	-	0.8594	85.94%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7065	70.65%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	+	0.7033	70.33%
skin sensitisation	-	0.8733	87.33%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.5792	57.92%
Acute Oral Toxicity (c)	I	0.3904	39.04%
Estrogen receptor binding	+	0.7623	76.23%
Androgen receptor binding	+	0.5485	54.85%
Thyroid receptor binding	+	0.6868	68.68%
Glucocorticoid receptor binding	+	0.6858	68.58%
Aromatase binding	-	0.6218	62.18%
PPAR gamma	-	0.7340	73.40%
Honey bee toxicity	-	0.8775	87.75%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9673	96.73%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.60%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.48%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.77%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.48%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.61%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.08%	89.00%
CHEMBL1871	P10275	Androgen Receptor	85.00%	96.43%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	83.06%	89.05%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.42%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.90%	96.09%
CHEMBL2581	P07339	Cathepsin D	81.80%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.74%	94.45%

Plants that contains it

• Achillea collina
• Annona rensoniana
• Archidendron clypearia
• Aristolochia maxima
• Artemisia valentina
• Bergenia purpurascens
• Betula pendula subsp. mandshurica
• Bischofia javanica
• Caragana tibetica
• Crataegus sinaica
• Discaria chacaye
• Euphorbia ferganensis
• Gardenia jasminoides
• Isodon rubescens
• Jasminum officinale
• Lasiocephalus ovatus
• Ligularia platyglossa
• Macrotyloma axillare
• Magnolia kachirachirai
• Malus asiatica
• Mikania obtusata
• Montrouziera sphaeroidea
• Pimpinella saxifraga
• Polygala myrtifolia
• Polystichum deltodon
• Rhodiola stephani
• Sarcomelicope argyrophylla
• Scrophularia wattii
• Seriphidium vachanicum
• Solanum bahamense
• Tinospora smilacina
• Trigonostemon reidioides
• Tropaeolum speciosum
• Vatica diospyroides

Cross-Links

• PubChem: 14110909
• NPASS: NPC299089
• LOTUS: LTS0032126
• wikiData: Q105137672