Calotropagenin

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	6caffe9e-29c7-459a-afa5-5b83610c1c64
Taxonomy	Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives
IUPAC Name	(2R,3R,5S,8R,9S,10R,13R,14S,17R)-2,3,14-trihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-10-carbaldehyde
SMILES (Canonical)	CC12CCC3C(C1(CCC2C4=CC(=O)OC4)O)CCC5C3(CC(C(C5)O)O)C=O
SMILES (Isomeric)	C[C@]12CC[C@H]3[C@H]([C@]1(CC[C@@H]2C4=CC(=O)OC4)O)CC[C@@H]5[C@@]3(C[C@H]([C@@H](C5)O)O)C=O
InChI	InChI=1S/C23H32O6/c1-21-6-4-16-17(3-2-14-9-18(25)19(26)10-22(14,16)12-24)23(21,28)7-5-15(21)13-8-20(27)29-11-13/h8,12,14-19,25-26,28H,2-7,9-11H2,1H3/t14-,15+,16-,17+,18+,19+,21+,22+,23-/m0/s1
InChI Key	VRDLGTLMAZPOMK-CSWSNCTRSA-N
Popularity	3 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₃H₃₂O₆
Molecular Weight	404.50 g/mol
Exact Mass	404.21988874 g/mol
Topological Polar Surface Area (TPSA)	104.00 Å²
XlogP	0.30
Atomic LogP (AlogP)	1.75
H-Bond Acceptor	6
H-Bond Donor	3
Rotatable Bonds	2

Synonyms

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CHEMBL495033

Card-20(22)-enolide, 2,3,14-trihydroxy-19-oxo-, (2.alpha.,3.beta.,5.alpha.)-

(2R,3R,5S,8R,9S,10R,13R,14S,17R)-2,3,14-trihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-10-carbaldehyde

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9824	98.24%
Caco-2	-	0.7059	70.59%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8851	88.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9325	93.25%
OATP1B3 inhibitior	+	0.9683	96.83%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7042	70.42%
BSEP inhibitior	+	0.5869	58.69%
P-glycoprotein inhibitior	-	0.8710	87.10%
P-glycoprotein substrate	+	0.6978	69.78%
CYP3A4 substrate	+	0.6836	68.36%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8975	89.75%
CYP3A4 inhibition	-	0.8707	87.07%
CYP2C9 inhibition	-	0.8939	89.39%
CYP2C19 inhibition	-	0.8785	87.85%
CYP2D6 inhibition	-	0.9284	92.84%
CYP1A2 inhibition	-	0.8861	88.61%
CYP2C8 inhibition	-	0.7585	75.85%
CYP inhibitory promiscuity	-	0.9602	96.02%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5112	51.12%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9768	97.68%
Skin irritation	+	0.5063	50.63%
Skin corrosion	-	0.9246	92.46%
Ames mutagenesis	-	0.6570	65.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4088	40.88%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.5746	57.46%
skin sensitisation	-	0.8902	89.02%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.5630	56.30%
Acute Oral Toxicity (c)	III	0.3956	39.56%
Estrogen receptor binding	+	0.9452	94.52%
Androgen receptor binding	+	0.8528	85.28%
Thyroid receptor binding	+	0.5439	54.39%
Glucocorticoid receptor binding	+	0.8435	84.35%
Aromatase binding	+	0.7373	73.73%
PPAR gamma	-	0.5551	55.51%
Honey bee toxicity	-	0.7316	73.16%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9922	99.22%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
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	96.29%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.94%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.98%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.86%	94.45%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	93.32%	82.69%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.19%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.01%	85.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	90.06%	96.77%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.89%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.42%	95.89%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	86.14%	93.04%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.11%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.39%	97.14%
CHEMBL4208	P20618	Proteasome component C5	82.82%	90.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.63%	99.23%
CHEMBL1871	P10275	Androgen Receptor	82.21%	96.43%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.91%	89.00%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Anemone narcissiflora

Asclepias curassavica