Piperchabaoside B

Details

• Internal ID: 1655aaf9-7b1b-417d-b26f-b402a6f6c5cb
• Taxonomy: Lipids and lipid-like molecules > Saccharolipids
• IUPAC Name: (3S)-5-[[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-[(E)-3-phenylprop-2-enoxy]-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]-3-hydroxy-3-methyl-5-oxopentanoic acid
• SMILES (Canonical): CC(CC(=O)O)(CC(=O)OCC1C(C(C(C(O1)OCC=CC2=CC=CC=C2)O)O)OC3C(C(C(C(O3)CO)O)O)O)O
• SMILES (Isomeric): C[C@](CC(=O)O)(CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC/C=C/C2=CC=CC=C2)O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
• InChI: InChI=1S/C27H38O15/c1-27(37,10-17(29)30)11-18(31)39-13-16-24(42-26-22(35)20(33)19(32)15(12-28)40-26)21(34)23(36)25(41-16)38-9-5-8-14-6-3-2-4-7-14/h2-8,15-16,19-26,28,32-37H,9-13H2,1H3,(H,29,30)/b8-5+/t15-,16-,19-,20+,21-,22-,23-,24-,25-,26+,27+/m1/s1
• InChI Key: GPOFKRODKLWYCU-GSKCIDPISA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₈O₁₅
• Molecular Weight: 602.60 g/mol
• Exact Mass: 602.22107050 g/mol
• Topological Polar Surface Area (TPSA): 242.00 Ų
• XlogP: -2.50
• Atomic LogP (AlogP): -2.49
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8016	80.16%
Caco-2	-	0.8928	89.28%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.7744	77.44%
OATP2B1 inhibitior	-	0.8603	86.03%
OATP1B1 inhibitior	+	0.8013	80.13%
OATP1B3 inhibitior	+	0.9458	94.58%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6067	60.67%
P-glycoprotein inhibitior	-	0.5461	54.61%
P-glycoprotein substrate	-	0.7967	79.67%
CYP3A4 substrate	+	0.6385	63.85%
CYP2C9 substrate	-	0.8107	81.07%
CYP2D6 substrate	-	0.8827	88.27%
CYP3A4 inhibition	-	0.8957	89.57%
CYP2C9 inhibition	-	0.9201	92.01%
CYP2C19 inhibition	-	0.9071	90.71%
CYP2D6 inhibition	-	0.9348	93.48%
CYP1A2 inhibition	-	0.9415	94.15%
CYP2C8 inhibition	+	0.5595	55.95%
CYP inhibitory promiscuity	-	0.9513	95.13%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6171	61.71%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.9360	93.60%
Skin irritation	-	0.8316	83.16%
Skin corrosion	-	0.9517	95.17%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7579	75.79%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	-	0.7682	76.82%
skin sensitisation	-	0.8712	87.12%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.8648	86.48%
Acute Oral Toxicity (c)	III	0.6714	67.14%
Estrogen receptor binding	+	0.7743	77.43%
Androgen receptor binding	-	0.5318	53.18%
Thyroid receptor binding	-	0.5094	50.94%
Glucocorticoid receptor binding	+	0.6359	63.59%
Aromatase binding	+	0.6163	61.63%
PPAR gamma	+	0.6455	64.55%
Honey bee toxicity	-	0.7578	75.78%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.8719	87.19%

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	97.28%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	95.11%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.05%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.43%	96.00%
CHEMBL2581	P07339	Cathepsin D	94.33%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.66%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.82%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.97%	99.17%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	89.33%	94.62%
CHEMBL5028	O14672	ADAM10	87.90%	97.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.68%	89.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	85.41%	96.61%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	84.40%	94.23%

Plants that contains it

• Brickellia longifolia
• Bupleurum rigidum
• Carpesium longifolium
• Cochlearia officinalis
• Coelogyne nitida
• Crocus corsicus
• Dichotomanthes tristaniicarpa
• Dracontium spruceanum
• Euphorbia micractina
• Frullania brasiliensis
• Heptapleurum venulosum
• Homalium laurifolium
• Lychnis coronata
• Matsumurella chinensis
• Palisota barteri
• Piper retrofractum
• Retrophyllum minus
• Verbesina virginica

Cross-Links

• PubChem: 44521607
• NPASS: NPC7359
• LOTUS: LTS0089677
• wikiData: Q105015028