Vitalboside A

Details

• Internal ID: 57fa055e-9afd-4a08-b96b-f9a33f61f1bc
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• SMILES (Canonical): CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)OC6C(C(C(C(O6)CO)O)O)O)C)C)C2C1)C)C(=O)O)C
• SMILES (Isomeric): C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C(=O)O)C)C)(C)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
• InChI: InChI=1S/C36H58O8/c1-31(2)14-16-36(30(41)42)17-15-34(6)20(21(36)18-31)8-9-24-33(5)12-11-25(32(3,4)23(33)10-13-35(24,34)7)44-29-28(40)27(39)26(38)22(19-37)43-29/h8,21-29,37-40H,9-19H2,1-7H3,(H,41,42)/t21-,22+,23-,24+,25-,26+,27-,28+,29-,33-,34+,35+,36-/m0/s1
• InChI Key: ZNFRITHWVZXJRK-YHFBEQRYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₅₈O₈
• Molecular Weight: 618.80 g/mol
• Exact Mass: 618.41316880 g/mol
• Topological Polar Surface Area (TPSA): 137.00 Ų
• XlogP: 5.90
• Atomic LogP (AlogP): 5.06
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

• SCHEMBL3003182
• CHEMBL2047219
• CHEBI:182952
• BDBM50235147
• C22130
• (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8533	85.33%
Caco-2	-	0.8191	81.91%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8727	87.27%
OATP2B1 inhibitior	-	0.5733	57.33%
OATP1B1 inhibitior	-	0.3747	37.47%
OATP1B3 inhibitior	-	0.5192	51.92%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5776	57.76%
BSEP inhibitior	-	0.5810	58.10%
P-glycoprotein inhibitior	+	0.6795	67.95%
P-glycoprotein substrate	-	0.9302	93.02%
CYP3A4 substrate	+	0.6884	68.84%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8798	87.98%
CYP3A4 inhibition	-	0.8908	89.08%
CYP2C9 inhibition	-	0.8072	80.72%
CYP2C19 inhibition	-	0.8635	86.35%
CYP2D6 inhibition	-	0.9352	93.52%
CYP1A2 inhibition	-	0.7238	72.38%
CYP2C8 inhibition	+	0.5444	54.44%
CYP inhibitory promiscuity	-	0.8928	89.28%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7092	70.92%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.9280	92.80%
Skin irritation	-	0.6096	60.96%
Skin corrosion	-	0.9521	95.21%
Ames mutagenesis	-	0.9170	91.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.3656	36.56%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.9697	96.97%
skin sensitisation	-	0.8899	88.99%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.6625	66.25%
Nephrotoxicity	-	0.7230	72.30%
Acute Oral Toxicity (c)	III	0.8024	80.24%
Estrogen receptor binding	+	0.6376	63.76%
Androgen receptor binding	+	0.7035	70.35%
Thyroid receptor binding	-	0.5578	55.78%
Glucocorticoid receptor binding	+	0.5998	59.98%
Aromatase binding	+	0.6509	65.09%
PPAR gamma	+	0.6203	62.03%
Honey bee toxicity	-	0.7860	78.60%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6605	66.05%
Fish aquatic toxicity	+	0.9734	97.34%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4081	P13726	Coagulation factor III	0.095 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.82%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.22%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.04%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.98%	94.45%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	88.55%	95.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.26%	95.56%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.07%	96.21%
CHEMBL5255	O00206	Toll-like receptor 4	85.05%	92.50%
CHEMBL2581	P07339	Cathepsin D	84.10%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.37%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.64%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.69%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	81.68%	90.17%

Plants that contains it

• Albizia gummifera
• Aralia armata
• Aralia elata
• Atriplex nummularia
• Bassia muricata
• Chenopodium album
• Clematis grata
• Swartzia schomburgkii

Cross-Links

• PubChem: 9986341
• LOTUS: LTS0171043
• wikiData: Q105380036