(1R,4aS,7S,7aS)-7-hydroxy-7-methyl-1-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2R,3R,4S,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]oxyoxan-2-yl]methoxy]-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carbaldehyde

Details

• Internal ID: 4eda15ea-11fd-4fb9-ba0b-6f156528cdad
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Iridoids and derivatives
• IUPAC Name: (1R,4aS,7S,7aS)-7-hydroxy-7-methyl-1-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2R,3R,4S,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]oxyoxan-2-yl]methoxy]-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carbaldehyde
• SMILES (Canonical): CC1(CCC2C1C(OC=C2C=O)OCC3C(C(C(C(O3)OC4C(C(C(OC4O)CO)O)O)O)O)O)O
• SMILES (Isomeric): C[C@@]1(CC[C@H]2[C@@H]1[C@@H](OC=C2C=O)OC[C@@H]3[C@H]([C@@H]([C@H]([C@@H](O3)O[C@@H]4[C@H]([C@@H]([C@H](O[C@H]4O)CO)O)O)O)O)O)O
• InChI: InChI=1S/C22H34O14/c1-22(31)3-2-9-8(4-23)6-32-20(12(9)22)33-7-11-14(26)15(27)17(29)21(35-11)36-18-16(28)13(25)10(5-24)34-19(18)30/h4,6,9-21,24-31H,2-3,5,7H2,1H3/t9-,10-,11-,12-,13-,14-,15+,16+,17-,18-,19-,20+,21+,22+/m1/s1
• InChI Key: WILPSDUESCCQEW-KZBZQOKASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₄O₁₄
• Molecular Weight: 522.50 g/mol
• Exact Mass: 522.19485575 g/mol
• Topological Polar Surface Area (TPSA): 225.00 Ų
• XlogP: -4.20
• Atomic LogP (AlogP): -4.16
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6693	66.93%
Caco-2	-	0.9028	90.28%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7087	70.87%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7677	76.77%
OATP1B3 inhibitior	+	0.9158	91.58%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7629	76.29%
BSEP inhibitior	-	0.9529	95.29%
P-glycoprotein inhibitior	-	0.7306	73.06%
P-glycoprotein substrate	-	0.7438	74.38%
CYP3A4 substrate	+	0.6665	66.65%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8530	85.30%
CYP3A4 inhibition	-	0.9593	95.93%
CYP2C9 inhibition	-	0.8950	89.50%
CYP2C19 inhibition	-	0.8913	89.13%
CYP2D6 inhibition	-	0.9164	91.64%
CYP1A2 inhibition	-	0.8711	87.11%
CYP2C8 inhibition	+	0.4926	49.26%
CYP inhibitory promiscuity	-	0.9060	90.60%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6226	62.26%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9535	95.35%
Skin irritation	-	0.6152	61.52%
Skin corrosion	-	0.9328	93.28%
Ames mutagenesis	-	0.7270	72.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7443	74.43%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.8025	80.25%
skin sensitisation	-	0.8928	89.28%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.5669	56.69%
Acute Oral Toxicity (c)	III	0.4470	44.70%
Estrogen receptor binding	+	0.7450	74.50%
Androgen receptor binding	-	0.4866	48.66%
Thyroid receptor binding	-	0.5284	52.84%
Glucocorticoid receptor binding	+	0.5507	55.07%
Aromatase binding	+	0.6889	68.89%
PPAR gamma	+	0.5934	59.34%
Honey bee toxicity	-	0.7779	77.79%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5655	56.55%
Fish aquatic toxicity	+	0.6853	68.53%

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	97.49%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.75%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	93.93%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.53%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.30%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.38%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.88%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.30%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.89%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.18%	86.92%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.58%	95.50%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.40%	95.83%
CHEMBL2581	P07339	Cathepsin D	83.38%	98.95%
CHEMBL5255	O00206	Toll-like receptor 4	82.83%	92.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.69%	89.00%
CHEMBL4208	P20618	Proteasome component C5	81.47%	90.00%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	80.54%	83.57%

Plants that contains it

• Pedicularis plicata

Cross-Links

• PubChem: 163038474
• LOTUS: LTS0260424
• wikiData: Q105306348