Yuccagenin

Details

• Internal ID: 3681116f-0ae6-49e9-a5e9-d6910b4fc3bd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,15R,16R)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-15,16-diol
• SMILES (Canonical): CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CC=C6C5(CC(C(C6)O)O)C)C)C)OC1
• SMILES (Isomeric): C[C@@H]1CC[C@@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC=C6[C@@]5(C[C@H]([C@@H](C6)O)O)C)C)C)OC1
• InChI: InChI=1S/C27H42O4/c1-15-7-10-27(30-14-15)16(2)24-23(31-27)12-20-18-6-5-17-11-21(28)22(29)13-26(17,4)19(18)8-9-25(20,24)3/h5,15-16,18-24,28-29H,6-14H2,1-4H3/t15-,16+,18-,19+,20+,21-,22-,23+,24+,25+,26+,27-/m1/s1
• InChI Key: ORXKASWXOVPKDV-UBWBUNFISA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₂O₄
• Molecular Weight: 430.60 g/mol
• Exact Mass: 430.30830982 g/mol
• Topological Polar Surface Area (TPSA): 58.90 Ų
• XlogP: 4.70
• Atomic LogP (AlogP): 4.68
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• 511-97-7
• Spirost-5-ene-2,3-diol, (2alpha,3beta,25R)-
• (25R)-spirost-5-en-2alpha,3beta-diol
• (1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,15R,16R)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-15,16-diol
• spirost-5-en-2,3-diol
• DTXSID70965379
• CHEBI:178609
• LMST01080011
• (25r)-spirost-5-ene-2alpha,3beta-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9718	97.18%
Caco-2	-	0.6026	60.26%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7971	79.71%
OATP2B1 inhibitior	-	0.5777	57.77%
OATP1B1 inhibitior	+	0.9273	92.73%
OATP1B3 inhibitior	+	0.9591	95.91%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.6631	66.31%
P-glycoprotein inhibitior	-	0.5827	58.27%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.7293	72.93%
CYP2C9 substrate	-	0.8005	80.05%
CYP2D6 substrate	-	0.7682	76.82%
CYP3A4 inhibition	-	0.8667	86.67%
CYP2C9 inhibition	-	0.9276	92.76%
CYP2C19 inhibition	-	0.9495	94.95%
CYP2D6 inhibition	-	0.9259	92.59%
CYP1A2 inhibition	-	0.8845	88.45%
CYP2C8 inhibition	+	0.6475	64.75%
CYP inhibitory promiscuity	-	0.9591	95.91%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4864	48.64%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9698	96.98%
Skin irritation	+	0.5213	52.13%
Skin corrosion	-	0.9372	93.72%
Ames mutagenesis	-	0.9400	94.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7368	73.68%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.8780	87.80%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.4596	45.96%
Acute Oral Toxicity (c)	III	0.4116	41.16%
Estrogen receptor binding	+	0.7296	72.96%
Androgen receptor binding	+	0.6909	69.09%
Thyroid receptor binding	+	0.6536	65.36%
Glucocorticoid receptor binding	+	0.7944	79.44%
Aromatase binding	+	0.7492	74.92%
PPAR gamma	+	0.5292	52.92%
Honey bee toxicity	-	0.5914	59.14%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9629	96.29%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.56%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	94.26%	100.00%
CHEMBL1914	P06276	Butyrylcholinesterase	94.06%	95.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.51%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.33%	91.11%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	90.31%	89.05%
CHEMBL226	P30542	Adenosine A1 receptor	89.86%	95.93%
CHEMBL221	P23219	Cyclooxygenase-1	89.86%	90.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.12%	97.25%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	86.53%	86.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.43%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.67%	94.45%
CHEMBL218	P21554	Cannabinoid CB1 receptor	85.22%	96.61%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.22%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.03%	95.89%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.49%	93.56%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.12%	95.50%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.07%	82.69%

Plants that contains it

• Aframomum zambesiacum
• Agave lechuguilla
• Alisma plantago-aquatica
• Allium karataviense
• Allium rotundum
• Allium stipitatum
• Allium turcomanicum
• Ambrosia cumanensis
• Angostura granulosa
• Buckiella undulata
• Chamaecrista dentata
• Clausena anisum-olens
• Clinostemon mahuba
• Cnidium monnieri
• Dioscorea cirrhosa
• Echinops bannaticus
• Euonymus lucidus
• Euphorbia lamprocarpa
• Ferula transiliensis
• Fraxinus angustifolia
• Genista hystrix
• Helichrysum anomalum
• Heptapleurum bodinieri
• Hippomane mancinella
• Isatis costata
• Kartalinia acaulis
• Machilus thunbergii
• Prunus sibirica
• Rhododendron ponticum
• Senecio roseus
• Seriphidium aucheri
• Speranskia tuberculata
• Trigonella foenum-graecum
• Veronica hederifolia
• Viguiera dentata
• Yucca flaccida
• Yucca gloriosa

Cross-Links

• PubChem: 3083608
• NPASS: NPC209912
• LOTUS: LTS0216205
• wikiData: Q76279837