Vaccaroside H

Details

• Internal ID: 465700db-4cdc-4ff3-863d-97fc99a65c16
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3S,4S,5R,6R)-6-[[(3S,4R,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-[(2S,3R,4S,5S,6R)-5-acetyloxy-4-[(2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-[(2S,3R,4S,5R,6S)-3,4-dihydroxy-6-methyl-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxycarbonyl-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4-dihydroxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC(=O)C34CCC(CC3C5=CCC6C7(CCC(C(C7CCC6(C5(CC4)C)C)(C)CO)OC8C(C(C(C(O8)C(=O)O)O)O)OC9C(C(C(C(O9)CO)O)O)O)C)(C)C)C)OC(=O)C)OC1C(C(C(O1)CO)O)O)O)O)OC1C(C(C(CO1)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@H]([C@H](O[C@H]2OC(=O)[C@@]34CC[C@@]5(C(=CC[C@H]6[C@]5(CC[C@@H]7[C@@]6(CC[C@@H]([C@@]7(C)CO)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)C(=O)O)O)O)O[C@H]9[C@@H]([C@H]([C@H]([C@H](O9)CO)O)O)O)C)C)[C@@H]3CC(CC4)(C)C)C)C)OC(=O)C)O[C@H]1[C@H]([C@@H]([C@H](O1)CO)O)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O
• InChI: InChI=1S/C66H104O32/c1-25-47(93-54-43(79)36(72)30(71)23-86-54)42(78)46(82)55(87-25)97-52-51(96-56-44(80)38(74)32(22-68)91-56)48(89-27(3)70)26(2)88-59(52)98-60(85)66-18-16-61(4,5)20-29(66)28-10-11-34-62(6)14-13-35(63(7,24-69)33(62)12-15-65(34,9)64(28,8)17-19-66)92-58-50(41(77)40(76)49(94-58)53(83)84)95-57-45(81)39(75)37(73)31(21-67)90-57/h10,25-26,29-52,54-59,67-69,71-82H,11-24H2,1-9H3,(H,83,84)/t25-,26+,29-,30+,31+,32+,33+,34+,35-,36-,37-,38+,39-,40-,41-,42-,43+,44-,45+,46+,47-,48-,49-,50+,51-,52+,54-,55-,56-,57-,58+,59-,62-,63-,64+,65+,66-/m0/s1
• InChI Key: ALJRUXNCESPXRE-NRWSPOIMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆₆H₁₀₄O₃₂
• Molecular Weight: 1409.50 g/mol
• Exact Mass: 1408.6510711 g/mol
• Topological Polar Surface Area (TPSA): 495.00 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): -3.42
• H-Bond Acceptor: 31
• H-Bond Donor: 16
• Rotatable Bonds: 17

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8427	84.27%
Caco-2	-	0.8652	86.52%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.8733	87.33%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7836	78.36%
OATP1B3 inhibitior	+	0.8381	83.81%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.9757	97.57%
P-glycoprotein inhibitior	+	0.7442	74.42%
P-glycoprotein substrate	+	0.5175	51.75%
CYP3A4 substrate	+	0.7433	74.33%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8804	88.04%
CYP3A4 inhibition	-	0.8187	81.87%
CYP2C9 inhibition	-	0.8372	83.72%
CYP2C19 inhibition	-	0.9259	92.59%
CYP2D6 inhibition	-	0.9408	94.08%
CYP1A2 inhibition	-	0.9133	91.33%
CYP2C8 inhibition	+	0.7857	78.57%
CYP inhibitory promiscuity	-	0.9476	94.76%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4689	46.89%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.8971	89.71%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9368	93.68%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7647	76.47%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	-	0.9098	90.98%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.8078	80.78%
Acute Oral Toxicity (c)	III	0.6742	67.42%
Estrogen receptor binding	+	0.6800	68.00%
Androgen receptor binding	+	0.7523	75.23%
Thyroid receptor binding	+	0.6809	68.09%
Glucocorticoid receptor binding	+	0.8060	80.60%
Aromatase binding	+	0.6876	68.76%
PPAR gamma	+	0.8379	83.79%
Honey bee toxicity	-	0.6473	64.73%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9692	96.92%

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	98.21%	91.11%
CHEMBL3714130	P46095	G-protein coupled receptor 6	95.97%	97.36%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.46%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.45%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.82%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.68%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.13%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.10%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.51%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.57%	100.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.24%	93.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.01%	86.92%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.89%	95.50%
CHEMBL5028	O14672	ADAM10	84.51%	97.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.73%	99.17%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.24%	96.77%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.98%	95.89%

Plants that contains it

• Vaccaria hispanica

Cross-Links

• PubChem: 102316526
• NPASS: NPC308083