(4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bR)-10-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

Details

• Internal ID: 1ab1d746-03de-4007-9d21-9158cb17efe4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bR)-10-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• SMILES (Canonical): CC(=O)NC1C(C(C(OC1OC2CCC3(C(C2(C)C)CCC4(C3CC=C5C4(CC(C6(C5CC(CC6)(C)C)C(=O)O)O)C)C)C)CO)O)O
• SMILES (Isomeric): CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]4([C@@H]3CC=C5[C@]4(C[C@H]([C@@]6([C@@H]5CC(CC6)(C)C)C(=O)O)O)C)C)C)CO)O)O
• InChI: InChI=1S/C38H61NO9/c1-20(41)39-28-30(44)29(43)23(19-40)47-31(28)48-27-12-13-35(6)24(34(27,4)5)11-14-36(7)25(35)10-9-21-22-17-33(2,3)15-16-38(22,32(45)46)26(42)18-37(21,36)8/h9,22-31,40,42-44H,10-19H2,1-8H3,(H,39,41)(H,45,46)/t22-,23-,24+,25-,26-,27+,28-,29-,30-,31+,35+,36-,37-,38-/m1/s1
• InChI Key: ZZVZUHRMTUSANL-AQHHHNHRSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₆₁NO₉
• Molecular Weight: 675.90 g/mol
• Exact Mass: 675.43463252 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 4.17
• H-Bond Acceptor: 8
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6799	67.99%
Caco-2	-	0.8534	85.34%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7228	72.28%
OATP2B1 inhibitior	-	0.5840	58.40%
OATP1B1 inhibitior	-	0.3222	32.22%
OATP1B3 inhibitior	+	0.8841	88.41%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8026	80.26%
BSEP inhibitior	+	0.5857	58.57%
P-glycoprotein inhibitior	+	0.7699	76.99%
P-glycoprotein substrate	-	0.6607	66.07%
CYP3A4 substrate	+	0.7137	71.37%
CYP2C9 substrate	-	0.8140	81.40%
CYP2D6 substrate	-	0.8740	87.40%
CYP3A4 inhibition	-	0.8527	85.27%
CYP2C9 inhibition	-	0.8747	87.47%
CYP2C19 inhibition	-	0.8872	88.72%
CYP2D6 inhibition	-	0.9396	93.96%
CYP1A2 inhibition	-	0.8795	87.95%
CYP2C8 inhibition	+	0.6075	60.75%
CYP inhibitory promiscuity	-	0.8088	80.88%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.5895	58.95%
Eye corrosion	-	0.9875	98.75%
Eye irritation	-	0.9229	92.29%
Skin irritation	-	0.7143	71.43%
Skin corrosion	-	0.9344	93.44%
Ames mutagenesis	-	0.7124	71.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.6447	64.47%
Micronuclear	+	0.7300	73.00%
Hepatotoxicity	-	0.8267	82.67%
skin sensitisation	-	0.8599	85.99%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.6128	61.28%
Acute Oral Toxicity (c)	III	0.7019	70.19%
Estrogen receptor binding	+	0.6673	66.73%
Androgen receptor binding	+	0.7097	70.97%
Thyroid receptor binding	-	0.5752	57.52%
Glucocorticoid receptor binding	+	0.6841	68.41%
Aromatase binding	+	0.7143	71.43%
PPAR gamma	+	0.6869	68.69%
Honey bee toxicity	-	0.7532	75.32%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6550	65.50%
Fish aquatic toxicity	+	0.9424	94.24%

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	97.48%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.24%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.64%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.96%	97.09%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	89.45%	96.21%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.00%	99.17%
CHEMBL5028	O14672	ADAM10	85.90%	97.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.20%	94.33%
CHEMBL5255	O00206	Toll-like receptor 4	84.47%	92.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.00%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.43%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.44%	95.89%
CHEMBL2581	P07339	Cathepsin D	80.50%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.12%	89.00%

Plants that contains it

• Alstonia yunnanensis
• Rauvolfia sellowii
• Rauvolfia serpentina
• Rauvolfia sprucei
• Rauvolfia sumatrana
• Rauvolfia volkensii
• Tetrapleura tetraptera

Cross-Links

• PubChem: 44584413
• LOTUS: LTS0190019
• wikiData: Q105106368