(3aR,4S,6E,10E,11aR)-4-hydroxy-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one

Details

• Internal ID: be09047e-b107-46fb-bdc5-ab6119c7e376
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (3aR,4S,6E,10E,11aR)-4-hydroxy-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one
• SMILES (Canonical): CC1=CC2C(C(CC(=CCC1)C)O)C(=C)C(=O)O2
• SMILES (Isomeric): C/C/1=C\[C@@H]2[C@@H]([C@H](C/C(=C/CC1)/C)O)C(=C)C(=O)O2
• InChI: InChI=1S/C15H20O3/c1-9-5-4-6-10(2)8-13-14(12(16)7-9)11(3)15(17)18-13/h5,8,12-14,16H,3-4,6-7H2,1-2H3/b9-5+,10-8+/t12-,13+,14+/m0/s1
• InChI Key: PDEJECFRCJOMEN-WQURXQIUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.32 g/mol
• Exact Mass: 248.14124450 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 2.52
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 886990-00-7
• AKOS040734145

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9953	99.53%
Caco-2	+	0.8447	84.47%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.4679	46.79%
OATP2B1 inhibitior	-	0.8582	85.82%
OATP1B1 inhibitior	+	0.9425	94.25%
OATP1B3 inhibitior	+	0.9248	92.48%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	-	0.9383	93.83%
P-glycoprotein inhibitior	-	0.8746	87.46%
P-glycoprotein substrate	-	0.9298	92.98%
CYP3A4 substrate	+	0.5000	50.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8285	82.85%
CYP3A4 inhibition	-	0.6535	65.35%
CYP2C9 inhibition	-	0.9474	94.74%
CYP2C19 inhibition	-	0.8674	86.74%
CYP2D6 inhibition	-	0.9505	95.05%
CYP1A2 inhibition	+	0.6553	65.53%
CYP2C8 inhibition	-	0.9015	90.15%
CYP inhibitory promiscuity	-	0.9573	95.73%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5945	59.45%
Eye corrosion	-	0.9472	94.72%
Eye irritation	-	0.7216	72.16%
Skin irritation	+	0.5586	55.86%
Skin corrosion	-	0.9115	91.15%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7209	72.09%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	+	0.6926	69.26%
skin sensitisation	-	0.6458	64.58%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.6604	66.04%
Acute Oral Toxicity (c)	III	0.3890	38.90%
Estrogen receptor binding	-	0.7881	78.81%
Androgen receptor binding	-	0.5914	59.14%
Thyroid receptor binding	-	0.6995	69.95%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.7944	79.44%
PPAR gamma	-	0.4887	48.87%
Honey bee toxicity	-	0.8371	83.71%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9755	97.55%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.56%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.06%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.11%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	84.88%	94.73%
CHEMBL2581	P07339	Cathepsin D	84.11%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	83.88%	83.82%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.82%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.41%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.45%	86.33%

Plants that contains it

• Agathosma betulina
• Aglaia lawii
• Amaioua guianensis
• Argyranthemum adauctum
• Arnica sachalinensis
• Baccharis santelicis
• Berchemia floribunda
• Betula maximowicziana
• Brachylaena discolor var. rotundata
• Calanthe arisanensis
• Choisya arizonica
• Chrysosplenium oppositifolium
• Epimedium sagittatum
• Eriogonum nudum
• Erythrina sandwicensis
• Euphorbia balsamifera
• Hemionitis cairon
• Hyacinthoides hispanica
• Hygrophila polysperma
• Incarvillea emodi
• Inula japonica
• Klasea erucifolia
• Mucuna sloanei
• Nervilia fordii
• Packera coahuilensis
• Picea sitchensis
• Pittosporum viridiflorum
• Pseudocedrela kotschyi
• Pseudotaxus chienii
• Roldana barba-johannis
• Rothmannia urcelliformis
• Santolina canescens
• Santolina rosmarinifolia
• Schistostephium heptalobum
• Senecio ruwenzoriensis
• Swertia decora
• Tritomaria quinquedentata
• Ursinia sericea
• Veratrum viride var. eschscholtzianum

Cross-Links

• PubChem: 12299961
• NPASS: NPC248947
• LOTUS: LTS0227634
• wikiData: Q105206397