Plantagineoside A

Details

• Internal ID: c75c3287-8a55-486a-b9e1-780dda355648
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids
• IUPAC Name: 1,7-bis[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]heptan-3-one
• InChI: InChI=1S/C31H42O15/c32-13-22-24(37)26(39)28(41)30(45-22)43-20-9-6-15(11-18(20)35)3-1-2-4-17(34)8-5-16-7-10-21(19(36)12-16)44-31-29(42)27(40)25(38)23(14-33)46-31/h6-7,9-12,22-33,35-42H,1-5,8,13-14H2/t22-,23-,24-,25-,26+,27+,28-,29-,30-,31-/m1/s1
• InChI Key: AHSFPZHWAFXABZ-GNZBLXBPSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₂O₁₅
• Molecular Weight: 654.70 g/mol
• Exact Mass: 654.25237063 g/mol
• Topological Polar Surface Area (TPSA): 256.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -1.63
• H-Bond Acceptor: 15
• H-Bond Donor: 10
• Rotatable Bonds: 14

Synonyms

• RefChem:174733
• 1,7-bis(3-hydroxy-4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyphenyl)heptan-3-one
• CHEMBL2159605
• BDBM50394346

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8087	80.87%
Caco-2	-	0.8795	87.95%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8243	82.43%
OATP2B1 inhibitior	-	0.7115	71.15%
OATP1B1 inhibitior	+	0.9102	91.02%
OATP1B3 inhibitior	+	0.9210	92.10%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.6674	66.74%
P-glycoprotein inhibitior	+	0.6743	67.43%
P-glycoprotein substrate	-	0.8173	81.73%
CYP3A4 substrate	+	0.5720	57.20%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8222	82.22%
CYP3A4 inhibition	-	0.8927	89.27%
CYP2C9 inhibition	-	0.7470	74.70%
CYP2C19 inhibition	-	0.7847	78.47%
CYP2D6 inhibition	-	0.9008	90.08%
CYP1A2 inhibition	-	0.8597	85.97%
CYP2C8 inhibition	+	0.6097	60.97%
CYP inhibitory promiscuity	-	0.8853	88.53%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.7103	71.03%
Eye corrosion	-	0.9923	99.23%
Eye irritation	-	0.8943	89.43%
Skin irritation	-	0.8531	85.31%
Skin corrosion	-	0.9730	97.30%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6993	69.93%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.9375	93.75%
skin sensitisation	-	0.8712	87.12%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	-	0.6750	67.50%
Nephrotoxicity	-	0.7846	78.46%
Acute Oral Toxicity (c)	III	0.6175	61.75%
Estrogen receptor binding	+	0.6204	62.04%
Androgen receptor binding	-	0.4901	49.01%
Thyroid receptor binding	-	0.5191	51.91%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.5530	55.30%
PPAR gamma	+	0.5797	57.97%
Honey bee toxicity	-	0.7872	78.72%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7005	70.05%
Fish aquatic toxicity	+	0.8684	86.84%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL239	Q07869	Peroxisome proliferator-activated receptor alpha	47100 nM	EC50	PMID: 22180047
CHEMBL3979	Q03181	Peroxisome proliferator-activated receptor delta	11000 nM	EC50	PMID: 18442289

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.09%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.43%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.82%	99.17%
CHEMBL2581	P07339	Cathepsin D	93.59%	98.95%
CHEMBL3194	P02766	Transthyretin	89.80%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.88%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.72%	86.92%
CHEMBL220	P22303	Acetylcholinesterase	87.79%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.49%	96.95%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	86.98%	83.57%
CHEMBL3401	O75469	Pregnane X receptor	86.76%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.03%	94.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.20%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.66%	96.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.11%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.75%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.31%	86.33%

Plants that contains it

• Tacca plantaginea

Cross-Links

• PubChem: 71453290
• NPASS: NPC116229
• ChEMBL: CHEMBL2159605
• LOTUS: LTS0197681
• wikiData: Q104912424