Monotropein

Details

• Internal ID: 5d41add9-c09d-49aa-b498-41af935ce1b1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (1S,4aS,7R,7aS)-7-hydroxy-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,7a-dihydro-1H-cyclopenta[c]pyran-4-carboxylic acid
• SMILES (Canonical): C1=CC(C2C1C(=COC2OC3C(C(C(C(O3)CO)O)O)O)C(=O)O)(CO)O
• SMILES (Isomeric): C1=C[C@@]([C@@H]2[C@H]1C(=CO[C@H]2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C(=O)O)(CO)O
• InChI: InChI=1S/C16H22O11/c17-3-8-10(19)11(20)12(21)15(26-8)27-14-9-6(1-2-16(9,24)5-18)7(4-25-14)13(22)23/h1-2,4,6,8-12,14-15,17-21,24H,3,5H2,(H,22,23)/t6-,8-,9-,10-,11+,12-,14+,15+,16+/m1/s1
• InChI Key: HPWWQPXTUDMRBI-NJPMDSMTSA-N
• Popularity: 90 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₂O₁₁
• Molecular Weight: 390.34 g/mol
• Exact Mass: 390.11621151 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: -3.10
• Atomic LogP (AlogP): -3.35
• H-Bond Acceptor: 10
• H-Bond Donor: 7
• Rotatable Bonds: 5

Synonyms

• 5945-50-6
• Monotropeine
• UNII-0Y61M84O2T
• 0Y61M84O2T
• NSC 88926
• NSC 291303
• CHEBI:6988
• NSC-88926
• NSC-291303
• (1S,4aS,7R,7aS)-7-Hydroxy-7-(hydroxymethyl)-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,7,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid
• Cyclopenta(c)pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,7,7a-tetrahydro-7-hydroxy-7-(hydroxymethyl)-, (1S-(1alpha,4aalpha,7beta,7aalpha))-
• (1S,2S,6S,9R)-9-HYDROXY-9-(HYDROXYMETHYL)-2-[(2S,3R,4S,5R,6R)-3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)OXAN-2-YL]OXY-3-OXABICYCLO[4.3.0]NONA-4,7-DIENE-5-CARBOXYLIC ACID
• (1S,4aS,7R,7aS)-1-(beta-D-glucopyranosyloxy)-7-hydroxy-7-(hydroxymethyl)-1,4a,7,7a-tetrahydrocyclopenta(c)pyran-4-carboxylic acid
• (1S,4aS,7R,7aS)-1-(beta-D-glucopyranosyloxy)-7-hydroxy-7-(hydroxymethyl)-1,4a,7,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid
• CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A,7,7A-TETRAHYDRO-7-HYDROXY-7-(HYDROXYMETHYL)-, (1S-(1.ALPHA.,4A.ALPHA.,7.BETA.,7A.ALPHA.))-
• Cyclopenta[c]pyran-4-carboxylic acid, 1-(.beta.-D-glucopyranosyloxy)-1,4a,7,7a-tetrahydro-7-hydroxy-7-(hydroxymethyl)-, [1S-(1.alpha.,4a.alpha.,7.beta.,7a.alpha.)]-
• MONOTROPEIN [MI]
• SCHEMBL422339
• Monotropein, >=98% (HPLC)
• HY-N0648
• s5471
• AKOS015897158
• CCG-268524
• LMPR0102070012
• AC-34713
• BS-49948
• CS-0009674
• C09788
• Q-100689
• Q27107380
• CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A,7,7A-TETRAHYDRO-7-HYDROXY-7-(HYDROXYMETHYL)-, (1S,4AS,7R,7AS)-
• CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-(beta-D-GLUCOPYRANOSYLOXY)-1,4A,7,7A-TETRAHYDRO-7-HYDROXY-7-(HYDROXYMETHYL)-, (1S,4AS,7R,7AS)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5000	50.00%
Caco-2	-	0.8761	87.61%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6372	63.72%
OATP2B1 inhibitior	-	0.8547	85.47%
OATP1B1 inhibitior	+	0.7837	78.37%
OATP1B3 inhibitior	+	0.9491	94.91%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9635	96.35%
P-glycoprotein inhibitior	-	0.8933	89.33%
P-glycoprotein substrate	-	0.9075	90.75%
CYP3A4 substrate	+	0.5640	56.40%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8771	87.71%
CYP3A4 inhibition	-	0.9545	95.45%
CYP2C9 inhibition	-	0.9185	91.85%
CYP2C19 inhibition	-	0.8350	83.50%
CYP2D6 inhibition	-	0.8851	88.51%
CYP1A2 inhibition	-	0.8970	89.70%
CYP2C8 inhibition	-	0.7422	74.22%
CYP inhibitory promiscuity	-	0.8723	87.23%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6552	65.52%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9420	94.20%
Skin irritation	-	0.7687	76.87%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.5493	54.93%
Human Ether-a-go-go-Related Gene inhibition	-	0.7356	73.56%
Micronuclear	-	0.7141	71.41%
Hepatotoxicity	-	0.7964	79.64%
skin sensitisation	-	0.8533	85.33%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.4619	46.19%
Acute Oral Toxicity (c)	III	0.3695	36.95%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	-	0.5193	51.93%
Thyroid receptor binding	-	0.4939	49.39%
Glucocorticoid receptor binding	-	0.4934	49.34%
Aromatase binding	+	0.6398	63.98%
PPAR gamma	+	0.5576	55.76%
Honey bee toxicity	-	0.8281	82.81%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7350	73.50%
Fish aquatic toxicity	-	0.5706	57.06%

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	96.49%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.48%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.77%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.64%	86.33%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.67%	94.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.62%	95.56%
CHEMBL4208	P20618	Proteasome component C5	82.15%	90.00%
CHEMBL2581	P07339	Cathepsin D	81.92%	98.95%

Plants that contains it

• Alangium platanifolium
• Arbutus unedo
• Cornus officinalis
• Croton penduliflorus
• Elliottia paniculata
• Galium album
• Galium humifusum
• Galium mirum
• Galium mollugo
• Galium rivale
• Gynochthodes officinalis
• Lychnophora salicifolia
• Monotropa uniflora
• Morinda citrifolia
• Neolitsea konishii
• Populus tomentosa
• Pyrola elliptica
• Pyrola japonica
• Pyrola renifolia
• Rhododendron luteum
• Saprosma scortechinii
• Stigmaphyllon palmatum
• Vaccinium dunalianum
• Vaccinium macrocarpon
• Vaccinium myrtillus
• Vepris louisii

Cross-Links

• PubChem: 73466
• NPASS: NPC221546
• LOTUS: LTS0064429
• wikiData: Q27107380