Phlomoidoside

Details

• Internal ID: f21c1524-2349-46a0-a690-48ff472b7030
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [(3R,4R,5R,6S)-6-[[(1S,4aR,5S,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-5-yl]oxy]-4,5-dihydroxyoxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): C1C(C(C(C(O1)OC2C=C(C3C2C=COC3OC4C(C(C(C(O4)CO)O)O)O)CO)O)O)OC(=O)C=CC5=CC=C(C=C5)O
• SMILES (Isomeric): C1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]2C=C([C@@H]3[C@H]2C=CO[C@H]3O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)CO)O)O)OC(=O)/C=C/C5=CC=C(C=C5)O
• InChI: InChI=1S/C29H36O15/c30-10-14-9-17(16-7-8-39-27(21(14)16)44-29-26(38)24(36)22(34)18(11-31)43-29)42-28-25(37)23(35)19(12-40-28)41-20(33)6-3-13-1-4-15(32)5-2-13/h1-9,16-19,21-32,34-38H,10-12H2/b6-3+/t16-,17+,18+,19+,21+,22+,23-,24-,25+,26+,27-,28-,29-/m0/s1
• InChI Key: QMXKOUSEDUDBEY-LNYAFLLHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₆O₁₅
• Molecular Weight: 624.60 g/mol
• Exact Mass: 624.20542044 g/mol
• Topological Polar Surface Area (TPSA): 234.00 Ų
• XlogP: -2.20
• Atomic LogP (AlogP): -2.37
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6298	62.98%
Caco-2	-	0.8996	89.96%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.6247	62.47%
OATP2B1 inhibitior	-	0.8558	85.58%
OATP1B1 inhibitior	+	0.8285	82.85%
OATP1B3 inhibitior	+	0.9624	96.24%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6227	62.27%
P-glycoprotein inhibitior	-	0.4789	47.89%
P-glycoprotein substrate	-	0.5194	51.94%
CYP3A4 substrate	+	0.6821	68.21%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8685	86.85%
CYP3A4 inhibition	-	0.9134	91.34%
CYP2C9 inhibition	-	0.8779	87.79%
CYP2C19 inhibition	-	0.7286	72.86%
CYP2D6 inhibition	-	0.8416	84.16%
CYP1A2 inhibition	-	0.8379	83.79%
CYP2C8 inhibition	+	0.7007	70.07%
CYP inhibitory promiscuity	-	0.5536	55.36%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6364	63.64%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9155	91.55%
Skin irritation	-	0.7884	78.84%
Skin corrosion	-	0.9592	95.92%
Ames mutagenesis	+	0.6109	61.09%
Human Ether-a-go-go-Related Gene inhibition	-	0.3829	38.29%
Micronuclear	-	0.5567	55.67%
Hepatotoxicity	-	0.8319	83.19%
skin sensitisation	-	0.8116	81.16%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.7747	77.47%
Acute Oral Toxicity (c)	III	0.4333	43.33%
Estrogen receptor binding	+	0.7498	74.98%
Androgen receptor binding	+	0.5813	58.13%
Thyroid receptor binding	-	0.5421	54.21%
Glucocorticoid receptor binding	+	0.5427	54.27%
Aromatase binding	+	0.5446	54.46%
PPAR gamma	+	0.6415	64.15%
Honey bee toxicity	-	0.6716	67.16%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5455	54.55%
Fish aquatic toxicity	+	0.8179	81.79%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.48%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.46%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.01%	89.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	92.54%	91.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.56%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.67%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.47%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.93%	96.09%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	87.70%	89.67%
CHEMBL3194	P02766	Transthyretin	84.47%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.93%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.98%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.68%	86.92%
CHEMBL5678	P34947	G protein-coupled receptor kinase 5	82.46%	88.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	82.44%	93.10%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.35%	97.28%
CHEMBL2581	P07339	Cathepsin D	81.00%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	80.49%	95.93%

Plants that contains it

• Dimorphotheca fruticosa
• Glinus oppositifolius
• Hypericum reflexum
• Markhamia stipulata
• Nicotiana alata
• Senecio sandersonii
• Sideritis soluta
• Sideritis trojana
• Sidneya tenuifolia
• Verbascum phlomoides
• Vinca minor

Cross-Links

• PubChem: 102445639
• NPASS: NPC97309
• LOTUS: LTS0064036
• wikiData: Q105224227