Kalopanaxsaponin B

Details

• Internal ID: e7654d72-52e8-49d8-9647-8090ab96e2bf
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: [(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(OC(C(C2O)O)OCC3C(C(C(C(O3)OC(=O)C45CCC(CC4C6=CCC7C8(CCC(C(C8CCC7(C6(CC5)C)C)(C)CO)OC9C(C(C(CO9)O)O)OC1C(C(C(C(O1)C)O)O)O)C)(C)C)O)O)O)CO)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2O)O)OC[C@@H]3[C@H]([C@@H]([C@H]([C@@H](O3)OC(=O)[C@@]45CC[C@@]6(C(=CC[C@H]7[C@]6(CC[C@@H]8[C@@]7(CC[C@@H]([C@@]8(C)CO)O[C@H]9[C@@H]([C@H]([C@H](CO9)O)O)O[C@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)C)O)O)O)C)C)[C@@H]4CC(CC5)(C)C)C)O)O)O)CO)O)O)O
• InChI: InChI=1S/C59H96O26/c1-24-34(63)38(67)42(71)49(78-24)83-46-29(20-60)80-48(45(74)41(46)70)77-22-30-37(66)40(69)44(73)51(81-30)85-53(75)59-17-15-54(3,4)19-27(59)26-9-10-32-55(5)13-12-33(56(6,23-61)31(55)11-14-58(32,8)57(26,7)16-18-59)82-52-47(36(65)28(62)21-76-52)84-50-43(72)39(68)35(64)25(2)79-50/h9,24-25,27-52,60-74H,10-23H2,1-8H3/t24-,25-,27-,28-,29+,30+,31+,32+,33-,34-,35-,36-,37+,38+,39+,40-,41+,42+,43+,44+,45+,46+,47+,48+,49-,50-,51-,52-,55-,56-,57+,58+,59-/m0/s1
• InChI Key: RYHDIBJJJRNDSX-MCGLQMIESA-N
• Popularity: 16 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₉H₉₆O₂₆
• Molecular Weight: 1221.40 g/mol
• Exact Mass: 1220.61898316 g/mol
• Topological Polar Surface Area (TPSA): 413.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -2.54
• H-Bond Acceptor: 26
• H-Bond Donor: 15
• Rotatable Bonds: 13

Synonyms

• Kalopanaxsaponin B
• 14216-03-6
• Akeboside Sth
• Hederoside H1
• Tauroside H2
• Glycoside L-H2
• Pericarsaponin Pk
• Tauroside St-H2
• Akebia saponin PK
• Pulsatilla saponin F
• UNII-2608B2L1BQ
• CHEBI:69371
• Kizuta saponin K(12)
• EINECS 238-072-2
• 2608B2L1BQ
• Kizuta Saponin K12
• Olean-12-en-28-oic acid, 3- ((2-O-(6-deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl)oxy)-23-hydroxy-, O-6-deoxy-alpha-L-mannopyranosyl-(1-4)-O-beta-D-glucopyranosyl-(1-6)-beta-D-glucopyranosyl ester, (3beta,4alpha)-
• C59H96O26
• hederagenin 3-O-alpha-L-rhamnopyranosyl-(1->2)-O-alpha-L-arabinopyranoside 28-O-alpha-L-rhamnopyranosyl-(1->4)-O-beta-D-glucopyranosyl-(1->6)-O-beta-D-glucopyranosyl ester
• Olean-12-en-28-oic acid, 3-((2-O-(6-deoxy-alpha-l-mannopyranosyl)-alpha-l-arabinopyranosyl)oxy)-23-hydroxy-, O-6-deoxy-alpha-l-mannopyranosyl-(1.4)-O-beta-d-glucopyranosyl-(1.6)-beta-d-glucopyranosyl ester, (3beta,4alpha)-
• Hederacol
• Akebiasaponin PK
• Hederacaucaside D
• Astrantiasaponin H
• C59-H96-O26
• Pulsatillasaponin F
• 6-deoxy-alpha-L-mannopyranosyl-(1->4)-beta-D-glucopyranosyl-(1->6)-1-O-((3beta)-3-((2-O-(6-deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl)oxy)-23-hydroxy-28-oxoolean-12-en-28-yl)-beta-D-glucopyranose
• 6-deoxy-alpha-L-mannopyranosyl-(1->4)-beta-D-glucopyranosyl-(1->6)-1-O-[(3beta)-3-{[2-O-(6-deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl]oxy}-23-hydroxy-28-oxoolean-12-en-28-yl]-beta-D-glucopyranose
• Kalopanax saponin B
• Pericarpsasaponin Pk
• Pulsatillasaponin II
• HEDERACOSIDE C with HPLC
• SCHEMBL2997243
• CHEMBL1910840
• Hederasaponin C (Hederacoside C)
• DTXSID701317445
• HY-N0253
• Olean-12-en-28-oic acid, 3-[[2-O-(6-deoxy-alpha-l-mannopyranosyl)-alpha-l-arabinopyranosyl]oxy]-23-hydroxy-, O-6-deoxy-alpha-l-mannopyranosyl-(14)-O-beta-d-glucopyranosyl-(16)-beta-d-glucopyranosyl ester, (3beta,4alpha)-
• MFCD00198062
• AKOS037514687
• CCG-270660
• CS-5691
• AC-34096
• S3919
• Q27137710
• OLEAN-12-EN-28-OIC ACID, 3- ((2-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)- .ALPHA.-L-ARABINOPYRANOSYL)OXY)-23-HYDROXY-, O-6-DEOXY-.ALPHA.-L- MANNOPYRANOSYL-(1-4)-O-.BETA.-D-GLUCOPYRANOSYL-(1-6)-.BETA.-D- GLUCOPYRANOSYL ESTER, (3.BETA.,4.ALPHA.)-
• Olean-12-en-28-oic acid, 3-((2-O-(6-deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl)oxy)-23-hydroxy-, O-6-deoxy-alpha-L-mannopyranosyl-(1-4)-O-beta-D-glucopyranosyl-(1-6)-beta-D-glucopyranosyl ester, (3beta,4alpha)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7891	78.91%
Caco-2	-	0.8784	87.84%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.8567	85.67%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	-	0.5700	57.00%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	+	0.8990	89.90%
P-glycoprotein inhibitior	+	0.7444	74.44%
P-glycoprotein substrate	-	0.5139	51.39%
CYP3A4 substrate	+	0.7396	73.96%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8587	85.87%
CYP3A4 inhibition	-	0.9300	93.00%
CYP2C9 inhibition	-	0.8838	88.38%
CYP2C19 inhibition	-	0.9101	91.01%
CYP2D6 inhibition	-	0.9422	94.22%
CYP1A2 inhibition	-	0.8933	89.33%
CYP2C8 inhibition	+	0.7420	74.20%
CYP inhibitory promiscuity	-	0.9668	96.68%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6254	62.54%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.8995	89.95%
Skin irritation	-	0.6103	61.03%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7678	76.78%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.8917	89.17%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.8958	89.58%
Acute Oral Toxicity (c)	III	0.7945	79.45%
Estrogen receptor binding	+	0.7806	78.06%
Androgen receptor binding	+	0.7426	74.26%
Thyroid receptor binding	+	0.6065	60.65%
Glucocorticoid receptor binding	+	0.7801	78.01%
Aromatase binding	+	0.6790	67.90%
PPAR gamma	+	0.8355	83.55%
Honey bee toxicity	-	0.6525	65.25%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5550	55.50%
Fish aquatic toxicity	+	0.9411	94.11%

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	98.36%	91.11%
CHEMBL3714130	P46095	G-protein coupled receptor 6	96.41%	97.36%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.07%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.63%	96.09%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	93.80%	95.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.33%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.78%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.38%	86.33%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	87.39%	95.50%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.69%	86.92%
CHEMBL226	P30542	Adenosine A1 receptor	86.10%	95.93%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.89%	97.25%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.84%	96.77%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.31%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.81%	95.56%
CHEMBL2581	P07339	Cathepsin D	83.82%	98.95%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.23%	96.90%
CHEMBL5028	O14672	ADAM10	81.89%	97.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.49%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.17%	91.07%
CHEMBL5255	O00206	Toll-like receptor 4	80.70%	92.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.58%	94.00%

Plants that contains it

• Akebia quinata
• Akebia trifoliata
• Anemone coronaria
• Centaurea hermannii
• Clematis chinensis
• Clematis orientalis
• Clematis stans
• Clematis tibetana
• Eleutherococcus sieboldianus
• Hedera canariensis
• Hedera caucasigena
• Hedera colchica
• Hedera helix
• Hedera nepalensis
• Hedera pastuchovii
• Kalopanax septemlobus
• Oreopanax guatemalensis
• Patrinia scabiosifolia
• Pulsatilla cernua
• Pulsatilla dahurica
• Stauntonia chinensis

Cross-Links

• PubChem: 11491905
• NPASS: NPC76972
• ChEMBL: CHEMBL1910840
• LOTUS: LTS0046976
• wikiData: Q27137710