Oleanderolide

Details

• Internal ID: 0fdd60a2-6261-496b-8919-999f18cfe0f1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (1S,4S,5R,8R,10S,13R,14R,16S,17S,18R)-10,16-dihydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracosan-23-one
• SMILES (Canonical): CC1(CCC23CCC4(C5(CCC6C(C(CCC6(C5CC(C4(C2C1)OC3=O)O)C)O)(C)C)C)C)C
• SMILES (Isomeric): C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2C[C@@H]([C@@]45[C@]3(CC[C@@]6([C@H]4CC(CC6)(C)C)C(=O)O5)C)O)C)(C)C)O
• InChI: InChI=1S/C30H48O4/c1-24(2)12-14-29-15-13-28(7)27(6)11-8-18-25(3,4)21(31)9-10-26(18,5)19(27)16-22(32)30(28,20(29)17-24)34-23(29)33/h18-22,31-32H,8-17H2,1-7H3/t18-,19+,20+,21-,22-,26-,27+,28-,29-,30+/m0/s1
• InChI Key: CXELEGXSGVFEND-NVTHVPAHSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₈O₄
• Molecular Weight: 472.70 g/mol
• Exact Mass: 472.35526001 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 6.40
• Atomic LogP (AlogP): 5.88
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• (1S,4S,5R,8R,10S,13R,14R,16S,17S,18R)-10,16-dihydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo(15.5.2.01,18.04,17.05,14.08,13)tetracosan-23-one
• (1S,4S,5R,8R,10S,13R,14R,16S,17S,18R)-10,16-dihydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracosan-23-one
• RefChem:168077
• 3beta,12alpha-Dihydroxyolean-28,13beta-olide
• CHEMBL498230
• SCHEMBL30192725

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9788	97.88%
Caco-2	-	0.5775	57.75%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7389	73.89%
OATP2B1 inhibitior	-	0.5770	57.70%
OATP1B1 inhibitior	+	0.8831	88.31%
OATP1B3 inhibitior	+	0.9171	91.71%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6571	65.71%
BSEP inhibitior	+	0.8051	80.51%
P-glycoprotein inhibitior	-	0.7387	73.87%
P-glycoprotein substrate	-	0.8473	84.73%
CYP3A4 substrate	+	0.6977	69.77%
CYP2C9 substrate	-	0.7853	78.53%
CYP2D6 substrate	-	0.7667	76.67%
CYP3A4 inhibition	-	0.6874	68.74%
CYP2C9 inhibition	-	0.8447	84.47%
CYP2C19 inhibition	-	0.7799	77.99%
CYP2D6 inhibition	-	0.9582	95.82%
CYP1A2 inhibition	-	0.7191	71.91%
CYP2C8 inhibition	-	0.7243	72.43%
CYP inhibitory promiscuity	-	0.9605	96.05%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6378	63.78%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.8898	88.98%
Skin irritation	+	0.5437	54.37%
Skin corrosion	-	0.8931	89.31%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5835	58.35%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.8201	82.01%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.5894	58.94%
Acute Oral Toxicity (c)	III	0.5573	55.73%
Estrogen receptor binding	+	0.7529	75.29%
Androgen receptor binding	+	0.7290	72.90%
Thyroid receptor binding	+	0.5877	58.77%
Glucocorticoid receptor binding	+	0.7799	77.99%
Aromatase binding	+	0.7303	73.03%
PPAR gamma	+	0.5949	59.49%
Honey bee toxicity	-	0.8057	80.57%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9756	97.56%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	93.03%	82.69%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.26%	97.09%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	91.89%	96.38%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.16%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.50%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.19%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.20%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.86%	99.23%
CHEMBL1871	P10275	Androgen Receptor	84.52%	96.43%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.91%	95.56%
CHEMBL2581	P07339	Cathepsin D	82.73%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.48%	95.89%
CHEMBL221	P23219	Cyclooxygenase-1	82.05%	90.17%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.31%	97.14%
CHEMBL259	P32245	Melanocortin receptor 4	81.10%	95.38%

Plants that contains it

• Aconitum brevicalcaratum
• Cirsium dipsacolepis
• Crinum kirkii
• Cyclolepis genistoides
• Cytisus scoparius
• Heliomeris longifolia var. annua
• Hypericum triquetrifolium
• Isodon japonicus
• Knightia deplanchei
• Mallotus rhamnifolius
• Malva sylvestris
• Mesembryanthemum emarcidum
• Nephroia diversifolia
• Nerium oleander
• Plantago lanceolata
• Ptilidium ciliare
• Scutellaria seleriana
• Solanum pimpinellifolium
• Sophora conollyi
• Teucrium pestalozzae
• Trichotosia subsessilis
• Trifolium apertum
• Tripodanthus acutifolius
• Veronica pectinata

Cross-Links

• PubChem: 11113483
• NPASS: NPC185529
• LOTUS: LTS0156883
• wikiData: Q104971780