(-)-Maesasaponin I

Details

• Internal ID: c9e22d33-1b77-4b53-9ab2-cd88b2fbf094
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3S,4S,5R,6R)-4-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3R,4R,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]oxyoxan-2-yl]oxy-3-hydroxy-6-[[(1R,2R,4S,5R,8R,10S,13R,14R,17S,18R,21R,22R,23S)-2,22,23-trihydroxy-4,5,9,9,13,20,20-heptamethyl-21-[(Z)-2-methylbut-2-enoyl]oxy-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracosan-10-yl]oxy]-5-[(1R,2S,3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexyl]oxyoxane-2-carboxylic acid
• SMILES (Canonical): CC=C(C)C(=O)OC1C(C23C(CC1(C)C)C4(CCC5C6(CCC(C(C6CCC5(C4(CC2O)C)C)(C)C)OC7C(C(C(C(O7)C(=O)O)O)OC8C(C(C(C(O8)CO)O)O)OC9C(C(C(C(O9)O)O)O)O)OC1CC(C(C(C1O)O)O)CO)C)OC3O)O
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H]1[C@@H]([C@]23[C@@H](C[C@]4([C@@]5(CC[C@@H]6[C@@]([C@H]5CC[C@@]4([C@@H]2CC1(C)C)O[C@@H]3O)(CC[C@@H](C6(C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)C(=O)O)O)O[C@H]8[C@@H]([C@H]([C@H]([C@H](O8)CO)O)O)O[C@H]9[C@@H]([C@@H]([C@H]([C@@H](O9)O)O)O)O)O[C@@H]1C[C@@H]([C@@H]([C@@H]([C@@H]1O)O)O)CO)C)C)C)O)O
• InChI: InChI=1S/C59H94O27/c1-10-22(2)47(75)84-45-44(72)59-28(18-53(45,3)4)58(86-52(59)77)16-12-27-55(7)14-13-30(54(5,6)26(55)11-15-56(27,8)57(58,9)19-29(59)62)80-51-43(78-24-17-23(20-60)31(63)34(66)32(24)64)40(39(71)41(82-51)46(73)74)81-50-42(36(68)33(65)25(21-61)79-50)83-49-38(70)35(67)37(69)48(76)85-49/h10,23-45,48-52,60-72,76-77H,11-21H2,1-9H3,(H,73,74)/b22-10-/t23-,24-,25-,26+,27-,28+,29-,30+,31+,32-,33+,34+,35-,36+,37-,38-,39+,40+,41+,42-,43-,44+,45+,48-,49-,50+,51-,52+,55+,56-,57+,58+,59-/m1/s1
• InChI Key: MBNRNSOZEOTBEP-QSNFQEOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₉H₉₄O₂₇
• Molecular Weight: 1235.40 g/mol
• Exact Mass: 1234.59824772 g/mol
• Topological Polar Surface Area (TPSA): 441.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -2.86
• H-Bond Acceptor: 26
• H-Bond Donor: 16
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7897	78.97%
Caco-2	-	0.8713	87.13%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.8104	81.04%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7899	78.99%
OATP1B3 inhibitior	+	0.9039	90.39%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	+	0.9393	93.93%
P-glycoprotein inhibitior	+	0.7453	74.53%
P-glycoprotein substrate	+	0.6482	64.82%
CYP3A4 substrate	+	0.7499	74.99%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8830	88.30%
CYP3A4 inhibition	-	0.8456	84.56%
CYP2C9 inhibition	-	0.7544	75.44%
CYP2C19 inhibition	-	0.8882	88.82%
CYP2D6 inhibition	-	0.9398	93.98%
CYP1A2 inhibition	-	0.8958	89.58%
CYP2C8 inhibition	+	0.7978	79.78%
CYP inhibitory promiscuity	-	0.9494	94.94%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5765	57.65%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.8988	89.88%
Skin irritation	-	0.5476	54.76%
Skin corrosion	-	0.9378	93.78%
Ames mutagenesis	-	0.6978	69.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.7595	75.95%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.8156	81.56%
skin sensitisation	-	0.8994	89.94%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.6484	64.84%
Acute Oral Toxicity (c)	III	0.4566	45.66%
Estrogen receptor binding	+	0.7825	78.25%
Androgen receptor binding	+	0.7614	76.14%
Thyroid receptor binding	+	0.6133	61.33%
Glucocorticoid receptor binding	+	0.7900	79.00%
Aromatase binding	+	0.6584	65.84%
PPAR gamma	+	0.8097	80.97%
Honey bee toxicity	-	0.5924	59.24%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5445	54.45%
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
CHEMBL221	P23219	Cyclooxygenase-1	98.15%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.62%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.13%	91.11%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	92.96%	93.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.93%	94.45%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	90.31%	91.24%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.15%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.64%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.68%	95.89%
CHEMBL2581	P07339	Cathepsin D	86.97%	98.95%
CHEMBL5255	O00206	Toll-like receptor 4	86.35%	92.50%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.22%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.49%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.63%	89.00%
CHEMBL4302	P08183	P-glycoprotein 1	84.60%	92.98%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	84.46%	94.08%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	84.20%	94.23%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.31%	97.36%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.11%	93.04%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.49%	99.17%
CHEMBL340	P08684	Cytochrome P450 3A4	82.19%	91.19%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.50%	91.07%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.38%	94.00%
CHEMBL1937	Q92769	Histone deacetylase 2	81.33%	94.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.22%	86.33%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.86%	100.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.75%	94.33%
CHEMBL5028	O14672	ADAM10	80.06%	97.50%

Plants that contains it

• Maesa lanceolata

Cross-Links

• PubChem: 163105003
• LOTUS: LTS0043147
• wikiData: Q105160862