(5R,9S,13R)-14-hydroxy-2,2,5,9,13-pentamethyl-16-oxapentacyclo[11.2.1.01,3.07,11.07,15]hexadec-11-ene-6,10-dione

Details

• Internal ID: c935d159-6613-42f5-bed4-3e0a09824ae5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Aromadendrane sesquiterpenoids
• IUPAC Name: (5R,9S,13R)-14-hydroxy-2,2,5,9,13-pentamethyl-16-oxapentacyclo[11.2.1.01,3.07,11.07,15]hexadec-11-ene-6,10-dione
• SMILES (Canonical): CC1CC2C(C23C4C(C(O3)(C=C5C4(C1=O)CC(C5=O)C)C)O)(C)C
• SMILES (Isomeric): C[C@@H]1CC2C(C23C4C([C@](O3)(C=C5C4(C1=O)C[C@@H](C5=O)C)C)O)(C)C
• InChI: InChI=1S/C20H26O4/c1-9-6-12-17(3,4)20(12)14-16(23)18(5,24-20)8-11-13(21)10(2)7-19(11,14)15(9)22/h8-10,12,14,16,23H,6-7H2,1-5H3/t9-,10+,12?,14?,16?,18-,19?,20?/m1/s1
• InChI Key: XKHKWWYWWNXZDZ-NDGXPALVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₄
• Molecular Weight: 330.40 g/mol
• Exact Mass: 330.18310931 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 2.29
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9909	99.09%
Caco-2	+	0.5927	59.27%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.6477	64.77%
OATP2B1 inhibitior	-	0.8558	85.58%
OATP1B1 inhibitior	+	0.8522	85.22%
OATP1B3 inhibitior	+	0.9518	95.18%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.9383	93.83%
P-glycoprotein inhibitior	-	0.8118	81.18%
P-glycoprotein substrate	-	0.6686	66.86%
CYP3A4 substrate	+	0.5911	59.11%
CYP2C9 substrate	-	0.7760	77.60%
CYP2D6 substrate	-	0.8457	84.57%
CYP3A4 inhibition	-	0.8474	84.74%
CYP2C9 inhibition	-	0.7459	74.59%
CYP2C19 inhibition	-	0.7769	77.69%
CYP2D6 inhibition	-	0.9268	92.68%
CYP1A2 inhibition	-	0.5420	54.20%
CYP2C8 inhibition	-	0.8344	83.44%
CYP inhibitory promiscuity	-	0.7508	75.08%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5016	50.16%
Eye corrosion	-	0.9819	98.19%
Eye irritation	-	0.8722	87.22%
Skin irritation	-	0.5235	52.35%
Skin corrosion	-	0.8924	89.24%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6277	62.77%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.5283	52.83%
skin sensitisation	-	0.6663	66.63%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.6569	65.69%
Acute Oral Toxicity (c)	III	0.3560	35.60%
Estrogen receptor binding	+	0.7695	76.95%
Androgen receptor binding	+	0.7389	73.89%
Thyroid receptor binding	+	0.7775	77.75%
Glucocorticoid receptor binding	+	0.6886	68.86%
Aromatase binding	-	0.5569	55.69%
PPAR gamma	-	0.5212	52.12%
Honey bee toxicity	-	0.8733	87.33%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9888	98.88%

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	94.49%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.83%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.70%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.59%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.20%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.28%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.07%	99.23%
CHEMBL2581	P07339	Cathepsin D	85.20%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.77%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.22%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.90%	86.33%

Plants that contains it

• Croton steenkampianus

Cross-Links

• PubChem: 162939304
• LOTUS: LTS0041780
• wikiData: Q105329476