(1S,3S,5R,6R,7S,8R,11R,12S,13S,16S,18S,19R,21R,22S)-6,7-dihydroxy-5-(hydroxymethyl)-12-(4-hydroxyphenyl)-18-methyl-2,4,9,15,20-pentaoxahexacyclo[9.8.2.113,16.03,8.013,21.019,22]docosane-10,14-dione

Details

• Internal ID: fb1b3a26-d966-4eb9-86c4-25d64a5052c5
• Taxonomy: Lipids and lipid-like molecules > Saccharolipids
• IUPAC Name: (1S,3S,5R,6R,7S,8R,11R,12S,13S,16S,18S,19R,21R,22S)-6,7-dihydroxy-5-(hydroxymethyl)-12-(4-hydroxyphenyl)-18-methyl-2,4,9,15,20-pentaoxahexacyclo[9.8.2.113,16.03,8.013,21.019,22]docosane-10,14-dione
• SMILES (Canonical): CC1CC2C3C1C4OC5C3(C(C5C(=O)OC6C(C(C(OC6O4)CO)O)O)C7=CC=C(C=C7)O)C(=O)O2
• SMILES (Isomeric): C[C@H]1C[C@H]2[C@H]3[C@@H]1[C@H]4O[C@H]5[C@@]3([C@@H]([C@H]5C(=O)O[C@@H]6[C@H]([C@H]([C@H](O[C@H]6O4)CO)O)O)C7=CC=C(C=C7)O)C(=O)O2
• InChI: InChI=1S/C25H28O11/c1-8-6-11-16-13(8)22-35-20-14(15(25(16,20)24(31)33-11)9-2-4-10(27)5-3-9)21(30)34-19-18(29)17(28)12(7-26)32-23(19)36-22/h2-5,8,11-20,22-23,26-29H,6-7H2,1H3/t8-,11-,12+,13+,14+,15+,16-,17-,18-,19+,20+,22-,23-,25-/m0/s1
• InChI Key: NJRMZLCAZRKLEM-KHTKHXNGSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₈O₁₁
• Molecular Weight: 504.50 g/mol
• Exact Mass: 504.16316171 g/mol
• Topological Polar Surface Area (TPSA): 161.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): -0.60
• H-Bond Acceptor: 11
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6570	65.70%
Caco-2	-	0.8773	87.73%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7266	72.66%
OATP2B1 inhibitior	-	0.8595	85.95%
OATP1B1 inhibitior	+	0.7798	77.98%
OATP1B3 inhibitior	+	0.9607	96.07%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.6726	67.26%
P-glycoprotein inhibitior	-	0.6522	65.22%
P-glycoprotein substrate	+	0.5764	57.64%
CYP3A4 substrate	+	0.6767	67.67%
CYP2C9 substrate	-	0.6016	60.16%
CYP2D6 substrate	-	0.8407	84.07%
CYP3A4 inhibition	-	0.7977	79.77%
CYP2C9 inhibition	-	0.8626	86.26%
CYP2C19 inhibition	-	0.8708	87.08%
CYP2D6 inhibition	-	0.9510	95.10%
CYP1A2 inhibition	-	0.8980	89.80%
CYP2C8 inhibition	+	0.5648	56.48%
CYP inhibitory promiscuity	-	0.8904	89.04%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4753	47.53%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9418	94.18%
Skin irritation	-	0.7720	77.20%
Skin corrosion	-	0.9264	92.64%
Ames mutagenesis	-	0.5191	51.91%
Human Ether-a-go-go-Related Gene inhibition	-	0.4762	47.62%
Micronuclear	+	0.5574	55.74%
Hepatotoxicity	+	0.5927	59.27%
skin sensitisation	-	0.8740	87.40%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.8259	82.59%
Acute Oral Toxicity (c)	III	0.5276	52.76%
Estrogen receptor binding	+	0.8177	81.77%
Androgen receptor binding	+	0.6695	66.95%
Thyroid receptor binding	-	0.5277	52.77%
Glucocorticoid receptor binding	+	0.6239	62.39%
Aromatase binding	+	0.5494	54.94%
PPAR gamma	+	0.6413	64.13%
Honey bee toxicity	-	0.7137	71.37%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.8566	85.66%

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	98.05%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.92%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.38%	96.09%
CHEMBL4072	P07858	Cathepsin B	93.63%	93.67%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.17%	94.45%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	89.14%	93.10%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.08%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.42%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.05%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.94%	86.33%
CHEMBL226	P30542	Adenosine A1 receptor	84.14%	95.93%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.07%	86.92%
CHEMBL2581	P07339	Cathepsin D	83.85%	98.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.45%	95.89%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	83.33%	85.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.30%	95.89%
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	82.77%	95.48%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	81.83%	96.37%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.55%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	81.04%	94.73%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.85%	97.25%
CHEMBL5103	Q969S8	Histone deacetylase 10	80.70%	90.08%
CHEMBL2996	Q05655	Protein kinase C delta	80.32%	97.79%

Plants that contains it

• Verbena litoralis

Cross-Links

• PubChem: 15484633
• LOTUS: LTS0121599
• wikiData: Q105180285