Plumieride

Details

• Internal ID: 208193b9-c7fb-4c81-8f85-84414213a97e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl (1S,4aS,7R,7aS)-4'-[(1S)-1-hydroxyethyl]-5'-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[4a,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-furan]-4-carboxylate
• SMILES (Canonical): CC(C1=CC2(C=CC3C2C(OC=C3C(=O)OC)OC4C(C(C(C(O4)CO)O)O)O)OC1=O)O
• SMILES (Isomeric): C[C@@H](C1=C[C@@]2(C=C[C@H]3[C@@H]2[C@@H](OC=C3C(=O)OC)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OC1=O)O
• InChI: InChI=1S/C21H26O12/c1-8(23)10-5-21(33-18(10)28)4-3-9-11(17(27)29-2)7-30-19(13(9)21)32-20-16(26)15(25)14(24)12(6-22)31-20/h3-5,7-9,12-16,19-20,22-26H,6H2,1-2H3/t8-,9+,12+,13+,14+,15-,16+,19-,20-,21+/m0/s1
• InChI Key: AOPMSFXOYJXDNJ-IRFSQMTFSA-N
• Popularity: 16 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₆O₁₂
• Molecular Weight: 470.40 g/mol
• Exact Mass: 470.14242626 g/mol
• Topological Polar Surface Area (TPSA): 181.00 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): -2.38
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

• agoniadin
• 511-89-7
• CHEBI:8275
• UNII-71A048XW8V
• methyl (1S,4aS,7R,7aS)-4'-[(1S)-1-hydroxyethyl]-5'-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[4a,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-furan]-4-carboxylate
• 71A048XW8V
• methyl (1S,4aS,7R,7aS)-4'-[(1S)-1-hydroxyethyl]-5'-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-spiro[4a,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-furan]-4-carboxylate
• AC1L2HUJ
• AC1Q6BJ5
• NSC-609065
• PLUMIERIDE [MI]
• SureCN419720
• SCHEMBL419720
• CHEMBL464470
• DTXSID40199109
• BDBM50480285
• C21H26O12
• AKOS032948813
• NSC 609065
• Plumieride, >=95% (LC/MS-ELSD)
• C21-H26-O12
• NCGC00347624-02
• C09797
• Q27108027
• (1S,2R,4AS,7AS)-1-(.BETA.-D-GLUCOPYRANOSYLOXY)-4A,7A-DIHYDRO-4-((1S)-1-HYDROXYETHYL)-5-OXOSPIRO(CYCLOPENTA(C)PYRAN-7(1H),2(5H)-FURAN)-4-CARBOXYLIC ACID METHYL ESTER
• SPIRO(CYCLOPENTA(C)PYRAN-7(1H),2'(5'H)-FURAN)-4-CARBOXYLIC ACID, 1-(.BETA.-D-GLUCOPYRANOSYLOXY)-4A,7A-DIHYDRO-4'-((1S)-1-HYDROXYETHYL)-5'-OXO-, METHYL ESTER, (1S,2'R,4AS,7AS)-
• Spiro(cyclopenta(c)pyran-7(1H),2'(5'H)-furan)-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-4a,7a-dihydro-4-(1-hydroxyethyl)-5'-oxo-, methyl ester, (1S-(1alpha,4aalpha,7alpha(R*),7aalpha))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6235	62.35%
Caco-2	-	0.8416	84.16%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7548	75.48%
OATP2B1 inhibitior	-	0.8534	85.34%
OATP1B1 inhibitior	+	0.7843	78.43%
OATP1B3 inhibitior	+	0.9525	95.25%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.6477	64.77%
P-glycoprotein inhibitior	-	0.6793	67.93%
P-glycoprotein substrate	-	0.6040	60.40%
CYP3A4 substrate	+	0.6600	66.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8753	87.53%
CYP3A4 inhibition	-	0.8894	88.94%
CYP2C9 inhibition	-	0.8913	89.13%
CYP2C19 inhibition	-	0.8928	89.28%
CYP2D6 inhibition	-	0.9269	92.69%
CYP1A2 inhibition	-	0.9270	92.70%
CYP2C8 inhibition	+	0.4599	45.99%
CYP inhibitory promiscuity	-	0.7613	76.13%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5914	59.14%
Eye corrosion	-	0.9866	98.66%
Eye irritation	-	0.9233	92.33%
Skin irritation	-	0.7439	74.39%
Skin corrosion	-	0.9390	93.90%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5408	54.08%
Micronuclear	-	0.5741	57.41%
Hepatotoxicity	-	0.6808	68.08%
skin sensitisation	-	0.8492	84.92%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.5956	59.56%
Acute Oral Toxicity (c)	III	0.4914	49.14%
Estrogen receptor binding	+	0.6454	64.54%
Androgen receptor binding	+	0.5589	55.89%
Thyroid receptor binding	+	0.5167	51.67%
Glucocorticoid receptor binding	+	0.5790	57.90%
Aromatase binding	+	0.5620	56.20%
PPAR gamma	+	0.5350	53.50%
Honey bee toxicity	-	0.7843	78.43%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	-	0.3850	38.50%

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	97.91%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.48%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.26%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.91%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	91.34%	94.73%
CHEMBL4208	P20618	Proteasome component C5	90.18%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.73%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.39%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.59%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.55%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.77%	86.33%
CHEMBL5028	O14672	ADAM10	81.28%	97.50%

Plants that contains it

• Acacia salicina
• Achillea santolinoides subsp. wilhelmsii
• Ajania nubigena
• Allamanda blanchetii
• Allamanda cathartica
• Allamanda schottii
• Backhousia angustifolia
• Blighia welwitschii
• Cunninghamia konishii
• Dioscorea villosa
• Eria lindleyi
• Himatanthus fallax
• Juniperus ashei
• Kalanchoe blossfeldiana
• Plumeria alba
• Plumeria obtusa
• Plumeria rubra
• Sassafras albidum

Cross-Links

• PubChem: 72319
• NPASS: NPC254538
• LOTUS: LTS0113544
• wikiData: Q27108027