Ingenol Mebutate

Details

• Internal ID: 60c0a087-aded-476e-8394-9b58b8242703
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Tigliane and ingenane diterpenoids
• IUPAC Name: [(1S,4S,5S,6R,9S,10R,12R,14R)-5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxo-4-tetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dienyl] (Z)-2-methylbut-2-enoate
• InChI: InChI=1S/C25H34O6/c1-7-12(2)22(29)31-21-13(3)10-24-14(4)8-17-18(23(17,5)6)16(20(24)28)9-15(11-26)19(27)25(21,24)30/h7,9-10,14,16-19,21,26-27,30H,8,11H2,1-6H3/b12-7-/t14-,16+,17-,18+,19-,21+,24+,25+/m1/s1
• InChI Key: VDJHFHXMUKFKET-WDUFCVPESA-N
• Popularity: 787 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₄O₆
• Molecular Weight: 430.50 g/mol
• Exact Mass: 430.23553880 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.33
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• Ingenol 3-angelate
• Ingenol-3-angelate
• 3-Ingenyl angelate
• 3-Angeloylingenol
• 75567-37-2
• PEP-005
• PEP005
• PEP 005
• mebutate d'ingenol
• mebutato de ingenol
• Euphorbia factor H1
• Euphorbia factor An1
• ingenoli mebutas
• 7686S50JAH
• AGN204332
• CHEBI:66913
• DTXSID301025610
• (1aR,2S,5R,5aS,6S,8aS,9R,10aR)-5,5a-dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-11-oxo-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[E][10]annulen-6-yl (2Z)-2-methylbut-2-enoate
• [(1S,4S,5S,6R,9S,10R,12R,14R)-5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxo-4-tetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dienyl] (Z)-2-methylbut-2-enoate
• 2-Butenoic acid, 2-methyl-, (1aR,2S,5R,5aS,6S,8aS,9R,10aR)-1a,2,5,5a,6,9,10,10a-octahydro-5,5a-dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-11-oxo-1H-2,8a-methanocyclopenta(a)cyclopropa(e)cyclodecen-6-yl ester, (2Z)-
• 3-ingenol angelate
• ((1S,4S,5S,6R,9S,10R,12R,14R)-5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxo-4-tetracyclo(7.5.1.01,5.010,12)pentadeca-2,7-dienyl) (Z)-2-methylbut-2-enoate
• (1aR,2S,5R,5aS,6S,8aS,9R,10aR)-5,5a-dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-11-oxo-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta(a)cyclopropa(E)(10)annulen-6-yl (2Z)-2-methylbut-2-enoate
• (1AR,2S,5R,5AS,6S,8AS,9R,10AR)-5,5A-DIHYDROXY-4-(HYDROXYMETHYL)-1,1,7,9-TETRAMETHYL-11-OXO-1A,2,5,5A,6,9,10,10A-OCTAHYDRO-1H-2,8A-METHANOCYCLOPENTA(A)CYCLOPROPA(E)CYCLODECEN-6-YL (2Z)-2-METHYLBUT-2-ENOATE
• (1aR,2S,5R,5aS,6S,8aS,9R,10aR)-5,5a-Dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-11-oxo-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[E]cyclodecen-6-yl (2Z)-2-methylbut-2-enoate
• RefChem:56864
• D06BX02
• DTXCID401509875
• (5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxo-4-tetracyclo(7.5.1.01,5.010,12)pentadeca-2,7-dienyl) 2-methylbut-2-enoate
• 688-125-2
• Picato
• Ingenol mebutate [USAN]
• AGN 204332
• Ingenol mebutate (USAN)
• MFCD22683801
• Picato (TN)
• UNII-7686S50JAH
• Ingenol mebutate [USAN:INN]
• ingenol-mebutate
• [dihydroxy-(hydroxymethyl)-tetramethyl-oxo-[?]yl] (Z)-2-methylbut-2-enoate
• Ingenol 3-angelate?
• Ingenol-3-O-Angelate
• INGENOL MEBUTATE [MI]
• INGENOL MEBUTATE [INN]
• GTPL7443
• orb1297586
• SCHEMBL2526605
• CHEMBL1863513
• INGENOL MEBUTATE [VANDF]
• HSDB 8308
• INGENOL MEBUTATE [MART.]
• CHEBI:228675
• INGENOL MEBUTATE [WHO-DD]
• GLXC-01716
• BDBM50470108
• EBC-98091
• HB0482
• LMFA07010911
• AKOS024457952
• INGENOL MEBUTATE [ORANGE BOOK]
• DB05013
• Ingenol-3-angelate, >=95% (HPLC)
• AS-79013
• NS00018295
• D09393
• Q426386
• BRD-K93779381-001-01-9
• (1aR,2S,5R,5aS,6S,8aS,9R,10aR)-5,5a-Dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-11-oxo-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a- methanocyclopenta(a)cyclopropa(e)cyclodecen-6-yl (2Z)-2-methylbut-2-enoate
• (1S,4S,5S,6R,9S,10R,12R,14R)-5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0^{1,5}.0^{10,12}]pentadeca-2,7-dien-4-yl (2Z)-2-methylbut-2-enoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9322	93.22%
Caco-2	-	0.5331	53.31%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6625	66.25%
OATP2B1 inhibitior	-	0.7190	71.90%
OATP1B1 inhibitior	+	0.8376	83.76%
OATP1B3 inhibitior	+	0.8950	89.50%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8815	88.15%
P-glycoprotein inhibitior	-	0.5155	51.55%
P-glycoprotein substrate	+	0.9344	93.44%
CYP3A4 substrate	+	0.6805	68.05%
CYP2C9 substrate	-	0.8100	81.00%
CYP2D6 substrate	-	0.9011	90.11%
CYP3A4 inhibition	-	0.8095	80.95%
CYP2C9 inhibition	-	0.5257	52.57%
CYP2C19 inhibition	-	0.8170	81.70%
CYP2D6 inhibition	-	0.9137	91.37%
CYP1A2 inhibition	-	0.6961	69.61%
CYP2C8 inhibition	-	0.6257	62.57%
CYP inhibitory promiscuity	-	0.8368	83.68%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6702	67.02%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9413	94.13%
Skin irritation	-	0.6822	68.22%
Skin corrosion	-	0.9397	93.97%
Ames mutagenesis	+	0.5746	57.46%
Human Ether-a-go-go-Related Gene inhibition	-	0.4520	45.20%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	+	0.5895	58.95%
skin sensitisation	-	0.7770	77.70%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.5704	57.04%
Acute Oral Toxicity (c)	III	0.5190	51.90%
Estrogen receptor binding	+	0.7993	79.93%
Androgen receptor binding	+	0.7074	70.74%
Thyroid receptor binding	+	0.5893	58.93%
Glucocorticoid receptor binding	+	0.7588	75.88%
Aromatase binding	+	0.6910	69.10%
PPAR gamma	+	0.5483	54.83%
Honey bee toxicity	-	0.5583	55.83%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9780	97.80%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2996	Q05655	Protein kinase C delta	4.1 nM	EC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.84%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.55%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.33%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.08%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.46%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.27%	96.95%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	89.06%	89.34%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.79%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.63%	89.00%
CHEMBL2581	P07339	Cathepsin D	88.29%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	87.34%	90.17%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.39%	82.69%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.49%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.34%	92.94%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.38%	93.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.09%	91.24%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.22%	94.62%

Plants that contains it

• Euphorbia canariensis
• Euphorbia peplus

Cross-Links

• PubChem: 6918670
• LOTUS: LTS0163943
• wikiData: Q426386