Pumiloside

Details

• Internal ID: 530920f9-4843-4437-8ffe-e63731014a3d
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (1S,18S,19R,20S)-19-ethenyl-18-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-2(11),4,6,8,15-pentaene-10,14-dione
• SMILES (Canonical): C=CC1C2CC3C4=C(CN3C(=O)C2=COC1OC5C(C(C(C(O5)CO)O)O)O)C(=O)C6=CC=CC=C6N4
• SMILES (Isomeric): C=C[C@@H]1[C@@H]2C[C@H]3C4=C(CN3C(=O)C2=CO[C@H]1O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C(=O)C6=CC=CC=C6N4
• InChI: InChI=1S/C26H28N2O9/c1-2-11-13-7-17-19-14(20(30)12-5-3-4-6-16(12)27-19)8-28(17)24(34)15(13)10-35-25(11)37-26-23(33)22(32)21(31)18(9-29)36-26/h2-6,10-11,13,17-18,21-23,25-26,29,31-33H,1,7-9H2,(H,27,30)/t11-,13+,17+,18-,21-,22+,23-,25+,26+/m1/s1
• InChI Key: ODQBQUXGRYBRTP-FWMZWJSFSA-N
• Popularity: 11 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₈N₂O₉
• Molecular Weight: 512.50 g/mol
• Exact Mass: 512.17948047 g/mol
• Topological Polar Surface Area (TPSA): 158.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -0.21
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

• 126722-26-7
• (1S,18S,19R,20S)-19-ethenyl-18-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-2(11),4,6,8,15-pentaene-10,14-dione
• MEGxp0_001994
• ACon1_001104
• CHEBI:80683
• DTXSID401318337
• AKOS040763317
• NCGC00169672-02
• BRD-K15525563-001-01-1
• Q27149724
• (3S)-4alpha-Ethenyl-3beta-(beta-D-glucopyranosyloxy)-4,4abeta,5,5aalpha,6,12-hexahydro-3H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-11,14-dione
• NCGC00169672-02_C26H28N2O9_14H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-11,14(3H)-dione, 4-ethenyl-3-(beta-D-glucopyranosyloxy)-4,4a,5,5a,6,12-hexahydro-, (3S,4R,4aS,5aS)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8158	81.58%
Caco-2	-	0.8396	83.96%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.9000	90.00%
Subcellular localzation	Mitochondria	0.4195	41.95%
OATP2B1 inhibitior	-	0.8521	85.21%
OATP1B1 inhibitior	+	0.8266	82.66%
OATP1B3 inhibitior	+	0.9294	92.94%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8474	84.74%
P-glycoprotein inhibitior	-	0.4520	45.20%
P-glycoprotein substrate	-	0.5695	56.95%
CYP3A4 substrate	+	0.6965	69.65%
CYP2C9 substrate	-	0.6041	60.41%
CYP2D6 substrate	-	0.8571	85.71%
CYP3A4 inhibition	-	0.6673	66.73%
CYP2C9 inhibition	-	0.7900	79.00%
CYP2C19 inhibition	-	0.8419	84.19%
CYP2D6 inhibition	-	0.8787	87.87%
CYP1A2 inhibition	-	0.6557	65.57%
CYP2C8 inhibition	+	0.6420	64.20%
CYP inhibitory promiscuity	-	0.6478	64.78%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5302	53.02%
Eye corrosion	-	0.9857	98.57%
Eye irritation	-	0.9583	95.83%
Skin irritation	-	0.7690	76.90%
Skin corrosion	-	0.9337	93.37%
Ames mutagenesis	+	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6542	65.42%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	-	0.5442	54.42%
skin sensitisation	-	0.8652	86.52%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.4807	48.07%
Acute Oral Toxicity (c)	III	0.5610	56.10%
Estrogen receptor binding	+	0.8136	81.36%
Androgen receptor binding	+	0.6998	69.98%
Thyroid receptor binding	+	0.5836	58.36%
Glucocorticoid receptor binding	+	0.5457	54.57%
Aromatase binding	+	0.5208	52.08%
PPAR gamma	+	0.6633	66.33%
Honey bee toxicity	-	0.7250	72.50%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9598	95.98%

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	98.64%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.73%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.06%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	95.27%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.07%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.88%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.87%	97.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	94.67%	86.92%
CHEMBL2581	P07339	Cathepsin D	94.26%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.70%	85.14%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	88.40%	95.83%
CHEMBL4302	P08183	P-glycoprotein 1	86.57%	92.98%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.78%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.12%	99.23%
CHEMBL3310	Q96DB2	Histone deacetylase 11	83.35%	88.56%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	83.34%	85.00%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	82.31%	94.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.84%	86.33%

Plants that contains it

• Camptotheca acuminata
• Cinnamodendron axillare
• Nauclea orientalis
• Ophiorrhiza kuroiwai
• Ophiorrhiza pumila

Cross-Links

• PubChem: 10346314
• NPASS: NPC280417
• LOTUS: LTS0065306
• wikiData: Q27149724