Ptaquiloside

Details

• Internal ID: 15bc6a42-f3b5-4817-a318-0cda15c0ba28
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (2R,3aR,7S,7aR)-7-hydroxy-2,5,7-trimethyl-3a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[3,7a-dihydro-2H-indene-6,1'-cyclopropane]-1-one
• SMILES (Canonical): CC1CC2(C=C(C3(CC3)C(C2C1=O)(C)O)C)OC4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): C[C@@H]1C[C@]2(C=C(C3(CC3)[C@@]([C@H]2C1=O)(C)O)C)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
• InChI: InChI=1S/C20H30O8/c1-9-6-20(28-17-15(25)14(24)13(23)11(8-21)27-17)7-10(2)19(4-5-19)18(3,26)16(20)12(9)22/h7,9,11,13-17,21,23-26H,4-6,8H2,1-3H3/t9-,11-,13-,14+,15-,16-,17+,18+,20-/m1/s1
• InChI Key: GPHSJPVUEZFIDE-YVPLJZHISA-N
• Popularity: 183 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₈
• Molecular Weight: 398.40 g/mol
• Exact Mass: 398.19406791 g/mol
• Topological Polar Surface Area (TPSA): 137.00 Ų
• XlogP: -1.30
• Atomic LogP (AlogP): -0.74
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

• 87625-62-5
• Braxin C
• UNII-F0MN9S5699
• F0MN9S5699
• (2R,3aR,7S,7aR)-7-hydroxy-2,5,7-trimethyl-3a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[3,7a-dihydro-2H-indene-6,1'-cyclopropane]-1-one
• CCRIS 1591
• Ptaquiloside (Braxin C)
• PTAQUILOSIDE [MI]
• PTAQUILOSIDE [IARC]
• SCHEMBL3993356
• DTXSID20892005
• HY-N7882
• piro(cyclopropane-1,5'-(5H)indan)-3'(2'H)-one, 7'a-(beta-D-glucopyranosyloxy)-1',3'a,4',7'a-tetrahydro-4'-hydroxy-2',4',6'-trimethyl-, (2'R-(2'alpha,3'aalpha,4'beta.7'aalpha))-
• Spiro(cyclopropane-1,5'-(5H)indan)-3'(2'H)-one, 7'a-(beta-D-glucopyranosyloxy)-1',3'a,4',7'a-tetrahydro-4'-hydroxy-2',4',6'-trimethyl-, (2'R,3'aR,4'S,7'aR)-
• Spiro(cyclopropane-1,5'-(5H)inden)-3'(2'H)-one, 1',3'-alpha,4',7'-alpha-tetrahydro-7'-alpha-(beta-D-glucopyranosyloxy)-4'-hydroxy-2',4',6'-trimethyl-
• AKOS040762234
• CS-0138739
• (2R,3AR,4S,7AR)-7A-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,3A,4,7A-TETRAHYDRO-4-HYDROXY-2,4,6-TRIMETHYLSPIRO(CYCLOPROPANE-1,5-(5H)INDEN)-3(2H)-ONE
• SPIRO(CYCLOPROPANE-1,5'-(5H)INDEN)-3'(2'H)-ONE, 7'A-(.BETA.-D-GLUCOPYRANOSYLOXY)-1',3'A,4',7'A-TETRAHYDRO-4'-HYDROXY-2',4',6'-TRIMETHYL-, (2'R,3'AR,4'S,7'AR)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8041	80.41%
Caco-2	-	0.6684	66.84%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6946	69.46%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8878	88.78%
OATP1B3 inhibitior	+	0.8940	89.40%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9276	92.76%
BSEP inhibitior	-	0.7557	75.57%
P-glycoprotein inhibitior	-	0.8124	81.24%
P-glycoprotein substrate	-	0.8635	86.35%
CYP3A4 substrate	+	0.6468	64.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8625	86.25%
CYP3A4 inhibition	-	0.8962	89.62%
CYP2C9 inhibition	-	0.8203	82.03%
CYP2C19 inhibition	-	0.8782	87.82%
CYP2D6 inhibition	-	0.9275	92.75%
CYP1A2 inhibition	-	0.7297	72.97%
CYP2C8 inhibition	-	0.8013	80.13%
CYP inhibitory promiscuity	-	0.7440	74.40%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6885	68.85%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9701	97.01%
Skin irritation	-	0.6176	61.76%
Skin corrosion	-	0.9402	94.02%
Ames mutagenesis	+	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4521	45.21%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	-	0.6507	65.07%
skin sensitisation	-	0.8726	87.26%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.5828	58.28%
Acute Oral Toxicity (c)	III	0.4958	49.58%
Estrogen receptor binding	+	0.6392	63.92%
Androgen receptor binding	+	0.7065	70.65%
Thyroid receptor binding	+	0.5895	58.95%
Glucocorticoid receptor binding	+	0.5849	58.49%
Aromatase binding	+	0.6501	65.01%
PPAR gamma	-	0.5318	53.18%
Honey bee toxicity	-	0.7836	78.36%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.8760	87.60%

Targets

Proven Targets:

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	96.72%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.09%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.93%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.39%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	88.21%	94.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.66%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.36%	86.33%
CHEMBL3714130	P46095	G-protein coupled receptor 6	86.07%	97.36%
CHEMBL3401	O75469	Pregnane X receptor	84.99%	94.73%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.50%	96.61%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.11%	100.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.84%	86.92%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.64%	89.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.18%	91.24%

Plants that contains it

• Artemisia lactiflora
• Attalea phalerata
• Catalpa ovata
• Citrus medica
• Crepidiastrum sonchifolium
• Dipsacus inermis
• Duguetia calycina
• Garcinia pyrifera
• Greenwayodendron oliveri
• Jacaranda mimosifolia
• Ophryosporus floribundus
• Payena lucida
• Phalaris canariensis
• Philotheca spicata
• Plumbagella micrantha
• Pteridium aquilinum
• Pteridium esculentum
• Quassia indica
• Rivina humilis

Cross-Links

• PubChem: 13962857
• NPASS: NPC125641
• LOTUS: LTS0159246
• wikiData: Q76423471