Ingenol 3-palmitate

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	095fc1f6-08fa-46cc-9582-ac09ea9dfb19
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] hexadecanoate
SMILES (Canonical)	CCCCCCCCCCCCCCCC(=O)OC1C(=CC23C1(C(C(=CC(C2=O)C4C(C4(C)C)CC3C)CO)O)O)C
SMILES (Isomeric)	CCCCCCCCCCCCCCCC(=O)O[C@H]1C(=C[C@@]23[C@@]1([C@@H](C(=C[C@H](C2=O)[C@H]4[C@H](C4(C)C)C[C@H]3C)CO)O)O)C
InChI	InChI=1S/C36H58O6/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-29(38)42-33-24(2)22-35-25(3)20-28-30(34(28,4)5)27(32(35)40)21-26(23-37)31(39)36(33,35)41/h21-22,25,27-28,30-31,33,37,39,41H,6-20,23H2,1-5H3/t25-,27+,28-,30+,31-,33+,35+,36+/m1/s1
InChI Key	DOSPRDHNGNPKKJ-BYPUAWAASA-N
Popularity	2 references in papers

Physical and Chemical Properties

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Molecular Formula	C₃₆H₅₈O₆
Molecular Weight	586.80 g/mol
Exact Mass	586.42333957 g/mol
Topological Polar Surface Area (TPSA)	104.00 Å²
XlogP	8.10
Atomic LogP (AlogP)	6.85
H-Bond Acceptor	6
H-Bond Donor	3
Rotatable Bonds	16

Synonyms

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Ingenol 3-hexadecanoate

52557-26-3

CHEMBL2430127

[(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] hexadecanoate

BDBM50493440

Hexadecanoic acid, 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, (1aR-(1aalpha,2alpha,5beta,5abeta,6beta,8aalpha,9alpha,10aalpha))-

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9510	95.10%
Caco-2	-	0.7892	78.92%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7981	79.81%
OATP2B1 inhibitior	-	0.5724	57.24%
OATP1B1 inhibitior	+	0.8251	82.51%
OATP1B3 inhibitior	+	0.8985	89.85%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6526	65.26%
BSEP inhibitior	+	0.8795	87.95%
P-glycoprotein inhibitior	+	0.7115	71.15%
P-glycoprotein substrate	+	0.8717	87.17%
CYP3A4 substrate	+	0.6841	68.41%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8641	86.41%
CYP3A4 inhibition	-	0.6957	69.57%
CYP2C9 inhibition	+	0.8075	80.75%
CYP2C19 inhibition	-	0.8017	80.17%
CYP2D6 inhibition	-	0.9166	91.66%
CYP1A2 inhibition	-	0.7418	74.18%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.8678	86.78%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6955	69.55%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9129	91.29%
Skin irritation	-	0.6056	60.56%
Skin corrosion	-	0.9498	94.98%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.5406	54.06%
skin sensitisation	-	0.8610	86.10%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.6966	69.66%
Acute Oral Toxicity (c)	III	0.4755	47.55%
Estrogen receptor binding	+	0.6995	69.95%
Androgen receptor binding	+	0.7292	72.92%
Thyroid receptor binding	-	0.6440	64.40%
Glucocorticoid receptor binding	+	0.6249	62.49%
Aromatase binding	+	0.6123	61.23%
PPAR gamma	-	0.4836	48.36%
Honey bee toxicity	-	0.7543	75.43%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.7394	73.94%
Fish aquatic toxicity	+	0.9898	98.98%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2996	Q05655	Protein kinase C delta	5.3 nM 4.7 nM 4.7 nM	EC50 EC50 EC50	via Super-PRED via Super-PRED PMID: 23993332

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.83%	96.09%
CHEMBL230	P35354	Cyclooxygenase-2	98.15%	89.63%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.56%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.49%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	93.81%	90.17%
CHEMBL299	P17252	Protein kinase C alpha	92.91%	98.03%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.27%	97.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	91.19%	82.69%
CHEMBL5255	O00206	Toll-like receptor 4	91.09%	92.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.56%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.24%	99.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.27%	96.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.20%	95.56%
CHEMBL3045	P05771	Protein kinase C beta	87.47%	97.63%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	86.21%	92.86%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	86.16%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.86%	97.25%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	84.11%	85.94%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.10%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.99%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.97%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.94%	99.23%
CHEMBL1871	P10275	Androgen Receptor	82.42%	96.43%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.93%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.33%	89.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.65%	91.24%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.32%	93.03%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Phegopteris subaurita

Symphytum tuberosum

Thymus quinquecostatus var. przewalskii

Thymus transcaucasicus