Hoffmanniolide

Details

• Internal ID: ca99554e-366d-4e1e-a2a8-6ba65d299c12
• Taxonomy: Phenylpropanoids and polyketides > Macrolides and analogues
• IUPAC Name: [(2S,3R,4R,5S,6R)-2-(2,4-dihydroxybutyl)-4,5-dihydroxy-6-[(E)-2,3,9-trihydroxy-7,11-dimethyl-5-methylidene-12-[(5Z,11E,17E)-10,15,16-trihydroxy-19-oxo-1-oxacyclononadeca-5,11,17-trien-2-yl]dodec-7-enyl]oxan-3-yl] hydrogen sulfate
• InChI: InChI=1S/C42H70O17S/c1-26(19-27(2)23-35(49)36(50)25-37-40(52)41(53)42(59-60(54,55)56)38(58-37)24-30(45)17-18-43)20-31(46)21-28(3)22-32-13-8-6-4-5-7-11-29(44)12-9-10-14-33(47)34(48)15-16-39(51)57-32/h4,6,9,12,15-16,20,28-38,40-50,52-53H,2,5,7-8,10-11,13-14,17-19,21-25H2,1,3H3,(H,54,55,56)/b6-4-,12-9+,16-15+,26-20+/t28?,29?,30?,31?,32?,33?,34?,35?,36?,37-,38+,40-,41-,42+/m1/s1
• InChI Key: ZLGBCMITYMUWJS-LCSHLLEJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₇₀O₁₇S
• Molecular Weight: 879.10 g/mol
• Exact Mass: 878.43337193 g/mol
• Topological Polar Surface Area (TPSA): 310.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.38
• H-Bond Acceptor: 16
• H-Bond Donor: 11
• Rotatable Bonds: 18

Synonyms

• CHEBI:144398
• C20008
• [(2S,3R,4R,5S,6R)-2-(2,4-dihydroxybutyl)-4,5-dihydroxy-6-[(E)-2,3,9-trihydroxy-7,11-dimethyl-5-methylidene-12-[(5Z,11E,17E)-10,15,16-trihydroxy-19-oxo-1-oxacyclononadeca-5,11,17-trien-2-yl]dodec-7-enyl]oxan-3-yl] hydrogen sulate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5985	59.85%
Caco-2	-	0.8666	86.66%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6412	64.12%
OATP2B1 inhibitior	-	0.8661	86.61%
OATP1B1 inhibitior	+	0.8198	81.98%
OATP1B3 inhibitior	+	0.9325	93.25%
MATE1 inhibitior	-	0.9012	90.12%
OCT2 inhibitior	-	0.7346	73.46%
BSEP inhibitior	+	0.9669	96.69%
P-glycoprotein inhibitior	+	0.7227	72.27%
P-glycoprotein substrate	+	0.7728	77.28%
CYP3A4 substrate	+	0.7184	71.84%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8847	88.47%
CYP3A4 inhibition	-	0.8797	87.97%
CYP2C9 inhibition	-	0.7582	75.82%
CYP2C19 inhibition	-	0.7146	71.46%
CYP2D6 inhibition	-	0.8671	86.71%
CYP1A2 inhibition	-	0.7454	74.54%
CYP2C8 inhibition	+	0.5970	59.70%
CYP inhibitory promiscuity	-	0.9669	96.69%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.6200	62.00%
Carcinogenicity (trinary)	Non-required	0.6266	62.66%
Eye corrosion	-	0.9677	96.77%
Eye irritation	-	0.9063	90.63%
Skin irritation	-	0.7630	76.30%
Skin corrosion	-	0.8971	89.71%
Ames mutagenesis	-	0.6553	65.53%
Human Ether-a-go-go-Related Gene inhibition	+	0.8561	85.61%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.7991	79.91%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.8432	84.32%
Acute Oral Toxicity (c)	III	0.6021	60.21%
Estrogen receptor binding	+	0.7978	79.78%
Androgen receptor binding	+	0.6051	60.51%
Thyroid receptor binding	+	0.5484	54.84%
Glucocorticoid receptor binding	+	0.6892	68.92%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7574	75.74%
Honey bee toxicity	-	0.6575	65.75%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.9723	97.23%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.20%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.26%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	96.58%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	95.76%	94.73%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.78%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.26%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.62%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.00%	100.00%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	89.41%	89.67%
CHEMBL2094135	Q96BI3	Gamma-secretase	89.29%	98.05%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.17%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.67%	95.89%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.00%	93.56%
CHEMBL5255	O00206	Toll-like receptor 4	87.91%	92.50%
CHEMBL4588	P22894	Matrix metalloproteinase 8	87.76%	94.66%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	87.25%	95.83%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.07%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.57%	97.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.42%	96.00%
CHEMBL340	P08684	Cytochrome P450 3A4	85.78%	91.19%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.04%	100.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.70%	94.33%
CHEMBL5103	Q969S8	Histone deacetylase 10	84.15%	90.08%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	83.88%	96.47%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	83.49%	93.10%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.94%	97.14%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.73%	91.07%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.95%	82.69%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.86%	93.03%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.33%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.21%	94.45%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	80.77%	96.38%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.51%	97.33%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.49%	96.90%
CHEMBL4040	P28482	MAP kinase ERK2	80.25%	83.82%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.19%	99.17%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 56928152
• LOTUS: LTS0088485
• wikiData: Q105378879