3,14-Dihydroxycard-20(22)-enolide

Details

• Internal ID: f297503c-8a7f-4328-8165-fe39385c5e47
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives
• IUPAC Name: 3-(3,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl)-2H-furan-5-one
• SMILES (Canonical): CC12CCC(CC1CCC3C2CCC4(C3(CCC4C5=CC(=O)OC5)O)C)O
• SMILES (Isomeric): CC12CCC(CC1CCC3C2CCC4(C3(CCC4C5=CC(=O)OC5)O)C)O
• InChI: InChI=1S/C23H34O4/c1-21-8-5-16(24)12-15(21)3-4-19-18(21)6-9-22(2)17(7-10-23(19,22)26)14-11-20(25)27-13-14/h11,15-19,24,26H,3-10,12-13H2,1-2H3
• InChI Key: XZTUSOXSLKTKJQ-UHFFFAOYSA-N
• Popularity: 14 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₄O₄
• Molecular Weight: 374.50 g/mol
• Exact Mass: 374.24570956 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 3.60
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• NSC277290
• 5alpha-Card-20(22)-enolide,14-dihydroxy-
• 5.alpha.-Card-20(22)-enolide,14-dihydroxy-
• MLS002701726
• 3,14-Dihydroxycard-20(22)-enolide
• Card-20(22)-enolide,14-dihydroxy-, (3.beta.,5.alpha.)-
• NSC407806
• NSC-119993
• NSC-277290
• ODORIGENINB
• SCHEMBL1152954
• DTXSID60871617
• XZTUSOXSLKTKJQ-UHFFFAOYSA-N
• NSC119993
• NSC224424
• UZARIGENIN B614014K070
• AKOS032948827
• NSC-224424
• 3-(3,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl)-2H-furan-5-one
• LS-15019
• NCI60_002256
• NCI60_003892
• SMR001565322
• B0005-190236
• 3-[(3S,5S,8R,9S,10S,13R,14S,17R)-3,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
• 4-(3,14-dihydroxy-10,13-dimethyl-hexadecahydrocyclopenta[a]phenanthren-17-yl)-5h-furan-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9945	99.45%
Caco-2	+	0.5900	59.00%
Blood Brain Barrier	-	0.6645	66.45%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8605	86.05%
OATP2B1 inhibitior	-	0.7300	73.00%
OATP1B1 inhibitior	+	0.9251	92.51%
OATP1B3 inhibitior	+	0.9667	96.67%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6493	64.93%
BSEP inhibitior	+	0.8300	83.00%
P-glycoprotein inhibitior	-	0.8811	88.11%
P-glycoprotein substrate	+	0.7446	74.46%
CYP3A4 substrate	+	0.6852	68.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9060	90.60%
CYP3A4 inhibition	-	0.6717	67.17%
CYP2C9 inhibition	-	0.9355	93.55%
CYP2C19 inhibition	-	0.9237	92.37%
CYP2D6 inhibition	-	0.9253	92.53%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.8743	87.43%
CYP inhibitory promiscuity	-	0.8681	86.81%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5341	53.41%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.9561	95.61%
Skin irritation	-	0.5148	51.48%
Skin corrosion	-	0.9425	94.25%
Ames mutagenesis	-	0.6424	64.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.4684	46.84%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.5127	51.27%
skin sensitisation	-	0.8671	86.71%
Respiratory toxicity	+	0.9222	92.22%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.6990	69.90%
Acute Oral Toxicity (c)	III	0.4005	40.05%
Estrogen receptor binding	+	0.9180	91.80%
Androgen receptor binding	+	0.8593	85.93%
Thyroid receptor binding	+	0.5761	57.61%
Glucocorticoid receptor binding	+	0.8863	88.63%
Aromatase binding	+	0.7039	70.39%
PPAR gamma	-	0.5323	53.23%
Honey bee toxicity	-	0.7636	76.36%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9922	99.22%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4096	P04637	Cellular tumor antigen p53	158.5 nM	Potency	via Super-PRED
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	251.2 nM	Potency	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	17.8 nM	Potency	via Super-PRED
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	794.3 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.90%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.56%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	94.85%	82.69%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.07%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.03%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.23%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.62%	97.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.22%	96.77%
CHEMBL1871	P10275	Androgen Receptor	88.42%	96.43%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	87.15%	93.04%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.00%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.50%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.50%	99.23%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	82.81%	81.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.89%	97.25%

Plants that contains it

• Asclepias albicans
• Asclepias curassavica
• Asclepias tuberosa
• Calotropis gigantea
• Calotropis procera
• Cerbera manghas
• Coronilla scorpioides
• Coronilla valentina subsp. glauca
• Digitalis grandiflora
• Digitalis lanata
• Elaeodendron croceum
• Erysimum inconspicuum
• Erysimum leptophyllum
• Gomphocarpus fruticosus
• Gomphocarpus sinaicus
• Nerium oleander
• Plumeria obtusa

Cross-Links

• PubChem: 274159
• LOTUS: LTS0102008
• wikiData: Q105345172