Primulasaponin

Details

• Internal ID: 63b5c3c7-cd08-4027-813a-6ce4f4c0256d
• 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-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3-hydroxy-6-[[(1S,2R,4S,5R,8R,10S,13R,14R,17S,18R)-2-hydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracosan-10-yl]oxy]-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3C(C(OC(C3OC4C(C(C(C(O4)CO)O)O)O)OC5CCC6(C(C5(C)C)CCC7(C6CCC89C7(CC(C1(C8CC(CC1)(C)C)CO9)O)C)C)C)C(=O)O)O)CO)O)O)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]2O[C@H]3[C@@H]([C@H](O[C@H]([C@@H]3O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O[C@H]5CC[C@@]6([C@H]7CC[C@@]89[C@@H]1CC(CC[C@]1(CO8)[C@@H](C[C@]9([C@@]7(CC[C@H]6C5(C)C)C)C)O)(C)C)C)C(=O)O)O)CO)O)O)O)O)O
• InChI: InChI=1S/C54H88O23/c1-22-30(58)33(61)36(64)44(70-22)76-41-35(63)32(60)24(20-56)72-46(41)74-39-38(66)40(43(67)68)75-47(42(39)77-45-37(65)34(62)31(59)23(19-55)71-45)73-29-11-12-50(6)25(49(29,4)5)9-13-51(7)26(50)10-14-54-27-17-48(2,3)15-16-53(27,21-69-54)28(57)18-52(51,54)8/h22-42,44-47,55-66H,9-21H2,1-8H3,(H,67,68)/t22-,23+,24+,25-,26+,27+,28+,29-,30-,31+,32-,33+,34-,35-,36+,37+,38-,39-,40-,41+,42+,44-,45-,46-,47+,50-,51+,52-,53+,54-/m0/s1
• InChI Key: DQUUSJCGJNQFPG-CBMAJASRSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₈₈O₂₃
• Molecular Weight: 1105.30 g/mol
• Exact Mass: 1104.57163905 g/mol
• Topological Polar Surface Area (TPSA): 363.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): -1.23
• H-Bond Acceptor: 22
• H-Bond Donor: 13
• Rotatable Bonds: 11

Synonyms

• 65312-86-9
• Primulic acid I
• PRIMULIC ACID 1
• C08970
• CHEBI:8414
• DTXSID40678545
• HY-N10414
• CS-0527798
• Q27108071
• (3beta,13alpha,16alpha,17alpha)-16-Hydroxy-13,28-epoxyoleanan-3-yl 6-deoxy-alpha-L-mannopyranosyl-(1->2)-beta-D-galactopyranosyl-(1->3)-[beta-D-glucopyranosyl-(1->2)]-beta-D-glucopyranosiduronic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6397	63.97%
Caco-2	-	0.8880	88.80%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7227	72.27%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7879	78.79%
OATP1B3 inhibitior	+	0.9276	92.76%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.8368	83.68%
P-glycoprotein inhibitior	+	0.7486	74.86%
P-glycoprotein substrate	-	0.5791	57.91%
CYP3A4 substrate	+	0.7311	73.11%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8745	87.45%
CYP3A4 inhibition	-	0.9228	92.28%
CYP2C9 inhibition	-	0.8526	85.26%
CYP2C19 inhibition	-	0.8627	86.27%
CYP2D6 inhibition	-	0.9523	95.23%
CYP1A2 inhibition	-	0.9157	91.57%
CYP2C8 inhibition	+	0.6922	69.22%
CYP inhibitory promiscuity	-	0.9693	96.93%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6545	65.45%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9023	90.23%
Skin irritation	-	0.6766	67.66%
Skin corrosion	-	0.9455	94.55%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7975	79.75%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.8295	82.95%
skin sensitisation	-	0.9229	92.29%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.8779	87.79%
Acute Oral Toxicity (c)	I	0.6300	63.00%
Estrogen receptor binding	+	0.7989	79.89%
Androgen receptor binding	+	0.7524	75.24%
Thyroid receptor binding	-	0.5144	51.44%
Glucocorticoid receptor binding	+	0.7222	72.22%
Aromatase binding	+	0.6515	65.15%
PPAR gamma	+	0.8040	80.40%
Honey bee toxicity	-	0.6162	61.62%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5455	54.55%
Fish aquatic toxicity	+	0.8764	87.64%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.83%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.66%	91.11%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.95%	97.36%
CHEMBL2581	P07339	Cathepsin D	88.44%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.21%	86.33%
CHEMBL233	P35372	Mu opioid receptor	88.06%	97.93%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	86.46%	96.38%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.32%	95.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.21%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.07%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.47%	89.00%
CHEMBL203	P00533	Epidermal growth factor receptor erbB1	85.37%	97.34%
CHEMBL226	P30542	Adenosine A1 receptor	85.14%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.77%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	84.65%	92.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.83%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.80%	99.17%
CHEMBL237	P41145	Kappa opioid receptor	83.56%	98.10%
CHEMBL2243	O00519	Anandamide amidohydrolase	83.24%	97.53%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.52%	95.89%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.18%	100.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.99%	94.33%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	80.72%	97.86%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.68%	91.24%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.32%	93.00%

Plants that contains it

• Lysimachia clethroides
• Myrsine africana
• Primula elatior

Cross-Links

• PubChem: 49787015
• NPASS: NPC53810
• LOTUS: LTS0268310
• wikiData: Q27108071