Haploperoside

Details

• Internal ID: 0393f2ba-dff8-434d-8ff0-75f7d7a61bcf
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Coumarin glycosides
• IUPAC Name: 6-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-2-one
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(C=C4C=CC(=O)OC4=C3)OC)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=C(C=C4C=CC(=O)OC4=C3)OC)O)O)O)O)O)O
• InChI: InChI=1S/C22H28O13/c1-8-15(24)17(26)19(28)21(32-8)31-7-13-16(25)18(27)20(29)22(35-13)34-12-6-10-9(5-11(12)30-2)3-4-14(23)33-10/h3-6,8,13,15-22,24-29H,7H2,1-2H3/t8-,13+,15-,16+,17+,18-,19+,20+,21+,22+/m0/s1
• InChI Key: FCIZPHNZRNLUJD-HLUXVQISSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈O₁₃
• Molecular Weight: 500.40 g/mol
• Exact Mass: 500.15299094 g/mol
• Topological Polar Surface Area (TPSA): 194.00 Ų
• XlogP: -1.90
• Atomic LogP (AlogP): -2.17
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

• Haploperoside A
• CHEBI:69043
• CHEMBL1928410
• AKOS040734412
• Q27137384
• 6-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-2-one
• 74712-71-3

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5630	56.30%
Caco-2	-	0.8667	86.67%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6091	60.91%
OATP2B1 inhibitior	-	0.8497	84.97%
OATP1B1 inhibitior	+	0.8538	85.38%
OATP1B3 inhibitior	+	0.9535	95.35%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.4582	45.82%
P-glycoprotein inhibitior	-	0.7605	76.05%
P-glycoprotein substrate	-	0.5612	56.12%
CYP3A4 substrate	+	0.5289	52.89%
CYP2C9 substrate	-	0.8389	83.89%
CYP2D6 substrate	-	0.8552	85.52%
CYP3A4 inhibition	-	0.8518	85.18%
CYP2C9 inhibition	-	0.9255	92.55%
CYP2C19 inhibition	-	0.8961	89.61%
CYP2D6 inhibition	-	0.8787	87.87%
CYP1A2 inhibition	-	0.8442	84.42%
CYP2C8 inhibition	-	0.5982	59.82%
CYP inhibitory promiscuity	-	0.7660	76.60%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7031	70.31%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.9568	95.68%
Skin irritation	-	0.8196	81.96%
Skin corrosion	-	0.9617	96.17%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4566	45.66%
Micronuclear	+	0.6892	68.92%
Hepatotoxicity	-	0.7101	71.01%
skin sensitisation	-	0.9239	92.39%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	-	0.6375	63.75%
Nephrotoxicity	-	0.8827	88.27%
Acute Oral Toxicity (c)	III	0.7195	71.95%
Estrogen receptor binding	+	0.6508	65.08%
Androgen receptor binding	-	0.6358	63.58%
Thyroid receptor binding	-	0.5303	53.03%
Glucocorticoid receptor binding	+	0.5946	59.46%
Aromatase binding	+	0.6033	60.33%
PPAR gamma	+	0.6589	65.89%
Honey bee toxicity	-	0.8623	86.23%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6649	66.49%
Fish aquatic toxicity	+	0.8104	81.04%

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	97.40%	91.11%
CHEMBL220	P22303	Acetylcholinesterase	95.24%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.96%	94.00%
CHEMBL2581	P07339	Cathepsin D	93.60%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.23%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.18%	96.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.79%	97.36%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.19%	99.17%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	86.17%	94.03%
CHEMBL3401	O75469	Pregnane X receptor	85.81%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.69%	89.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.27%	89.62%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.91%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.32%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.77%	86.92%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	81.84%	92.38%

Plants that contains it

• Citropsis articulata
• Haplophyllum acutifolium
• Haplophyllum dauricum

Cross-Links

• PubChem: 21607625
• LOTUS: LTS0242010
• wikiData: Q27137384