Carenolide N-3

Details

• Internal ID: 78aca295-1884-477b-80ce-ba1b36b1de1c
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: 3-[(1S,3R,5R,7S,8R,11R,12S,15S,17R)-15-[(2R,4R,5S,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-8,12-dimethyl-2,6-dioxahexacyclo[9.8.0.01,3.03,8.05,7.012,17]nonadecan-7-yl]-2H-furan-5-one
• SMILES (Canonical): CC1C(C(CC(O1)OC2CCC3(C(C2)CCC45C3CCC6(C4(O5)CC7C6(O7)C8=CC(=O)OC8)C)C)OC)O
• SMILES (Isomeric): C[C@@H]1[C@@H]([C@@H](C[C@@H](O1)O[C@H]2CC[C@]3([C@@H](C2)CC[C@]45[C@@H]3CC[C@]6([C@]4(O5)C[C@@H]7[C@]6(O7)C8=CC(=O)OC8)C)C)OC)O
• InChI: InChI=1S/C30H42O8/c1-16-25(32)20(33-4)13-24(35-16)36-19-6-8-26(2)17(11-19)5-10-28-21(26)7-9-27(3)29(28,38-28)14-22-30(27,37-22)18-12-23(31)34-15-18/h12,16-17,19-22,24-25,32H,5-11,13-15H2,1-4H3/t16-,17-,19+,20-,21-,22-,24+,25+,26+,27+,28+,29-,30-/m1/s1
• InChI Key: SEHQMXOXGIZASS-KMNGBJDXSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₂O₈
• Molecular Weight: 530.60 g/mol
• Exact Mass: 530.28796829 g/mol
• Topological Polar Surface Area (TPSA): 99.30 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 3.43
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• CHEMBL229203

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9851	98.51%
Caco-2	-	0.7600	76.00%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7962	79.62%
OATP2B1 inhibitior	-	0.7155	71.55%
OATP1B1 inhibitior	+	0.8858	88.58%
OATP1B3 inhibitior	+	0.9496	94.96%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.8937	89.37%
P-glycoprotein inhibitior	+	0.6975	69.75%
P-glycoprotein substrate	+	0.6904	69.04%
CYP3A4 substrate	+	0.7342	73.42%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8898	88.98%
CYP3A4 inhibition	-	0.7777	77.77%
CYP2C9 inhibition	-	0.8098	80.98%
CYP2C19 inhibition	-	0.8716	87.16%
CYP2D6 inhibition	-	0.9424	94.24%
CYP1A2 inhibition	-	0.8128	81.28%
CYP2C8 inhibition	-	0.5720	57.20%
CYP inhibitory promiscuity	-	0.9017	90.17%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6112	61.12%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.9295	92.95%
Skin irritation	-	0.6647	66.47%
Skin corrosion	-	0.9387	93.87%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3861	38.61%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	-	0.6519	65.19%
skin sensitisation	-	0.8666	86.66%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	I	0.4639	46.39%
Estrogen receptor binding	+	0.6908	69.08%
Androgen receptor binding	+	0.7800	78.00%
Thyroid receptor binding	-	0.5226	52.26%
Glucocorticoid receptor binding	+	0.7995	79.95%
Aromatase binding	+	0.7178	71.78%
PPAR gamma	+	0.6361	63.61%
Honey bee toxicity	-	0.6438	64.38%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.6600	66.00%
Fish aquatic toxicity	+	0.9701	97.01%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL226	P30542	Adenosine A1 receptor	96.74%	95.93%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.96%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.79%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	93.42%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.80%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.99%	89.00%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	91.15%	94.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.36%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.91%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.52%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.40%	95.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.82%	97.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.95%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.81%	99.23%
CHEMBL1871	P10275	Androgen Receptor	85.79%	96.43%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.14%	94.45%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	82.10%	97.33%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.32%	95.71%
CHEMBL1859	O95180	Voltage-gated T-type calcium channel alpha-1H subunit	80.98%	98.57%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.91%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.73%	82.69%
CHEMBL1937	Q92769	Histone deacetylase 2	80.12%	94.75%
CHEMBL344	Q99705	Melanin-concentrating hormone receptor 1	80.00%	92.50%

Plants that contains it

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

Cross-Links

• PubChem: 16756312
• NPASS: NPC115349
• ChEMBL: CHEMBL229203
• LOTUS: LTS0071726
• wikiData: Q105251174