Periplocoside O

Details

• Internal ID: 0b4db31a-e825-433d-a898-32a88ac1dd47
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: 6-[[17-hydroxy-17-[1-[5-hydroxy-4-(methoxymethoxy)-6-methyloxan-2-yl]oxyethyl]-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl]oxy]-4-methoxy-2-methyl-2H-pyran-5-one
• SMILES (Canonical): CC1C=C(C(=O)C(O1)OC2CCC3(C4CCC5(C(C4CC=C3C2)CCC5(C(C)OC6CC(C(C(O6)C)O)OCOC)O)C)C)OC
• SMILES (Isomeric): CC1C=C(C(=O)C(O1)OC2CCC3(C4CCC5(C(C4CC=C3C2)CCC5(C(C)OC6CC(C(C(O6)C)O)OCOC)O)C)C)OC
• InChI: InChI=1S/C36H56O10/c1-20-16-28(41-7)32(38)33(43-20)46-24-10-13-34(4)23(17-24)8-9-25-26(34)11-14-35(5)27(25)12-15-36(35,39)22(3)45-30-18-29(42-19-40-6)31(37)21(2)44-30/h8,16,20-22,24-27,29-31,33,37,39H,9-15,17-19H2,1-7H3
• InChI Key: OPDVJOHDZLWTNG-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₅₆O₁₀
• Molecular Weight: 648.80 g/mol
• Exact Mass: 648.38734798 g/mol
• Topological Polar Surface Area (TPSA): 122.00 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 4.80
• H-Bond Acceptor: 10
• H-Bond Donor: 2
• Rotatable Bonds: 9

Synonyms

• 116709-67-2
• RefChem:171789
• 6-[[17-hydroxy-17-[1-[5-hydroxy-4-(methoxymethoxy)-6-methyloxan-2-yl]oxyethyl]-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl]oxy]-4-methoxy-2-methyl-2H-pyran-5-one
• DTXSID60922133
• REA70967
• 17-Hydroxy-3-[(4-methoxy-6-methyl-3-oxo-3,6-dihydro-2H-pyran-2-yl)oxy]pregn-5-en-20-yl 2,6-dideoxy-3-O-(methoxymethyl)hexopyranoside
• 2H-Pyran-3(6H)-one, 2-(((3beta,20S)-20-((2,6-dideoxy-3-O-(methoxymethyl)-beta-D-arabino-hexopyranosyl)oxy)-17-hydroxypregn-5-en-3-yl)oxy)-4-methoxy-6-methyl-
• 6-[[17-hydroxy-17-[1-[5-hydroxy-4-(methoxymethoxy)-6-methyl-tetrahydropyran-2-yl]oxyethyl]-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl]oxy]-4-methoxy-2-methyl-2H-pyran-5-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9715	97.15%
Caco-2	-	0.8299	82.99%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7882	78.82%
OATP2B1 inhibitior	-	0.8601	86.01%
OATP1B1 inhibitior	+	0.8592	85.92%
OATP1B3 inhibitior	+	0.9351	93.51%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.9063	90.63%
P-glycoprotein inhibitior	+	0.7830	78.30%
P-glycoprotein substrate	+	0.7305	73.05%
CYP3A4 substrate	+	0.7462	74.62%
CYP2C9 substrate	-	0.8021	80.21%
CYP2D6 substrate	-	0.8864	88.64%
CYP3A4 inhibition	-	0.7465	74.65%
CYP2C9 inhibition	-	0.8971	89.71%
CYP2C19 inhibition	-	0.9261	92.61%
CYP2D6 inhibition	-	0.9378	93.78%
CYP1A2 inhibition	-	0.8958	89.58%
CYP2C8 inhibition	+	0.7005	70.05%
CYP inhibitory promiscuity	-	0.9366	93.66%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5384	53.84%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9302	93.02%
Skin irritation	+	0.5167	51.67%
Skin corrosion	-	0.9439	94.39%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6549	65.49%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.8791	87.91%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.5887	58.87%
Acute Oral Toxicity (c)	I	0.4322	43.22%
Estrogen receptor binding	+	0.7422	74.22%
Androgen receptor binding	+	0.7708	77.08%
Thyroid receptor binding	-	0.5865	58.65%
Glucocorticoid receptor binding	+	0.7014	70.14%
Aromatase binding	+	0.7132	71.32%
PPAR gamma	+	0.6382	63.82%
Honey bee toxicity	-	0.6846	68.46%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9182	91.82%

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	99.23%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.56%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.30%	97.25%
CHEMBL226	P30542	Adenosine A1 receptor	93.69%	95.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	93.52%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	93.01%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.15%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.55%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.29%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.16%	85.14%
CHEMBL2581	P07339	Cathepsin D	90.60%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.25%	94.45%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.94%	97.14%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	88.82%	96.38%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.66%	96.77%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.62%	94.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.76%	91.07%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	87.73%	93.40%
CHEMBL1871	P10275	Androgen Receptor	87.67%	96.43%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	87.39%	97.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.13%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.06%	89.00%
CHEMBL1914	P06276	Butyrylcholinesterase	82.34%	95.00%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	82.00%	94.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.17%	95.56%

Plants that contains it

• Periploca sepium

Cross-Links

• PubChem: 196729
• NPASS: NPC186610
• LOTUS: LTS0030131
• wikiData: Q82895459