Phorbol 12,13-dibutyrate

Details

• Internal ID: a3d782d8-b109-486d-8a2e-920c3c6ec4ea
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Tigliane and ingenane diterpenoids > Phorbol esters
• IUPAC Name: [(1S,2S,6R,10S,11R,13S,14R,15R)-13-butanoyloxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-14-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] butanoate
• SMILES (Canonical): CCCC(=O)OC1C(C2(C(C=C(CC3(C2C=C(C3=O)C)O)CO)C4C1(C4(C)C)OC(=O)CCC)O)C
• SMILES (Isomeric): CCCC(=O)O[C@@H]1[C@H]([C@]2([C@@H](C=C(C[C@]3([C@H]2C=C(C3=O)C)O)CO)[C@H]4[C@@]1(C4(C)C)OC(=O)CCC)O)C
• InChI: InChI=1S/C28H40O8/c1-7-9-20(30)35-24-16(4)27(34)18(22-25(5,6)28(22,24)36-21(31)10-8-2)12-17(14-29)13-26(33)19(27)11-15(3)23(26)32/h11-12,16,18-19,22,24,29,33-34H,7-10,13-14H2,1-6H3/t16-,18+,19-,22-,24-,26-,27-,28-/m1/s1
• InChI Key: BQJRUJTZSGYBEZ-YVQNUNKESA-N
• Popularity: 2,933 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₀O₈
• Molecular Weight: 504.60 g/mol
• Exact Mass: 504.27231823 g/mol
• Topological Polar Surface Area (TPSA): 130.00 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.63
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 7

Synonyms

• 37558-16-0
• PDBU
• Phorbol 12,13-dibutanoate
• Phorbol-12,13-dibutyrate
• CHEBI:17598
• DTXSID50958628
• 67MX82CL58
• (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-9aH-cyclopropa[3,4]benzo[1,2-e]azulene-9,9a-diyl dibutanoate
• NSC-622507
• Butanoic acid, 1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-9aH-cyclopropa(3,4)benz(1,2-e)azulene-9,9a-diyl ester, (1aR-(1aalpha,1bbeta,4abeta,7aalpha,7balpha,8alpha,9beta,9aalpha))-
• Phorbol 12,13 Dibutyrate
• 12,13-Dibutyrate, Phorbol
• (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-9aH-cyclopropa(3,4)benzo(1,2-e)azulene-9,9a-diyl dibutanoate
• RefChem:861880
• DTXCID501386529
• 636-433-2
• Phorbol dibutyrate
• PHORBOL12,13-DIBUTYRATE
• MFCD00036783
• 61557-88-8
• [(1S,2S,6R,10S,11R,13S,14R,15R)-13-butanoyloxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-14-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] butanoate
• Butanoic acid, (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-9aH-cyclopropa[3,4]benz[1,2-e]azulene-9,9a-diyl ester
• Phorbol dibutyrate;PDBu
• SR-05000002331
• CHEMBL27768
• NSC 622507
• 4Alpha-Phorbol 12,13-Dibutyrate
• C28H40O8
• UNII-67MX82CL58
• NSC622507
• [butanoyloxy-dihydroxy-(hydroxymethyl)-tetramethyl-oxo-[?]yl] butanoate
• PKC Activator II
• Butanoic acid, (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-9aH-cyclopropa(3,4)benz(1,2-e)azulene-9,9a-diyl ester
• Phorbol-12
• orb1706793
• SCHEMBL29366787
• [3H]-Phorbol 12,13-Dibutyrate
• MBA55816
• Phorbol 12,13-Dibutyrate >99%
• EX-A14596
• HSCI1_000181
• 4-.beta.-Phorbol 12,13-dibutyrate
• AKOS024458006
• CCG-208247
• NCGC00163607-01
• Butanoic acid, 1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-9ah-cyclopropa(3,4)benz(1,2-e)azulene-9,9a-diyl ester, (1aR-(1a-alpha,1b-beta,4a-beta,7a-alpha,7b-alpha,8-alpha,9-beta,9a-alpha))-
• Butanoic acid, diester with 1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-4a,7b,9,9a-tetrahydro-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5H-cyclopropya(3,4)benz(1,2-e)azulen-5-one, (1aR-(1aalpha,1bbeta,4abeta,7aalpha,7balpha,8alpha,9beta,9aalpha))-
• DA-76825
• HY-18985
• MS-29372
• CS-0014826
• C03634
• G12092
• Phorbol 12,13-dibutyrate, >=98% (TLC), powder
• Q7187368
• SR-05000002331-2
• SR-05000002331-3
• BRD-K81365681-001-01-8
• Butanoic acid, (1aR,1bS,4aR,7bS,8R,9R,9aS)-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-9aH-cyclopropa(3,4)benz(1,2-e)azulene-9,9a-diyl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9670	96.70%
Caco-2	-	0.7184	71.84%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7048	70.48%
OATP2B1 inhibitior	-	0.8581	85.81%
OATP1B1 inhibitior	+	0.8334	83.34%
OATP1B3 inhibitior	+	0.9233	92.33%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.7526	75.26%
BSEP inhibitior	+	0.8832	88.32%
P-glycoprotein inhibitior	+	0.8906	89.06%
P-glycoprotein substrate	+	0.5921	59.21%
CYP3A4 substrate	+	0.6520	65.20%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9180	91.80%
CYP3A4 inhibition	-	0.7730	77.30%
CYP2C9 inhibition	+	0.7518	75.18%
CYP2C19 inhibition	-	0.8842	88.42%
CYP2D6 inhibition	-	0.9142	91.42%
CYP1A2 inhibition	-	0.8742	87.42%
CYP2C8 inhibition	+	0.5220	52.20%
CYP inhibitory promiscuity	-	0.7494	74.94%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6494	64.94%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9263	92.63%
Skin irritation	-	0.6062	60.62%
Skin corrosion	-	0.9358	93.58%
Ames mutagenesis	-	0.6837	68.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5062	50.62%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.5809	58.09%
skin sensitisation	-	0.8177	81.77%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.7906	79.06%
Acute Oral Toxicity (c)	III	0.5825	58.25%
Estrogen receptor binding	+	0.7280	72.80%
Androgen receptor binding	+	0.6925	69.25%
Thyroid receptor binding	+	0.5743	57.43%
Glucocorticoid receptor binding	+	0.7526	75.26%
Aromatase binding	+	0.7743	77.43%
PPAR gamma	+	0.5459	54.59%
Honey bee toxicity	-	0.8347	83.47%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5432	54.32%
Fish aquatic toxicity	+	0.9137	91.37%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL299	P17252	Protein kinase C alpha	0.2 nM; 1.55 nM; 0.78 nM; 0.28 nM	Ki; Ki; Ki; Kd	PMID: 10715158; PMID: 11266177; PMID: 8176711; via Super-PRED
CHEMBL3045	P05771	Protein kinase C beta	1.8 nM; 1.97 nM	Ki; Ki	PMID: 11266177; PMID: 11266177
CHEMBL2996	Q05655	Protein kinase C delta	0.8 nM; 0.193 nM; 1.03 nM; 21.6 nM; 12 nM	Ki; Kd; Ki; Ki; Ki	PMID: 9135029; via Super-PRED; PMID: 11266177; PMID: 9135029; PMID: 9135029
CHEMBL3582	Q02156	Protein kinase C epsilon	0.22 nM; 1.35 nM; 14.9 nM	Kd; Ki; Ki	via Super-PRED; PMID: 11266177; PMID: 11266177
CHEMBL3616	P24723	Protein kinase C eta	0.95 nM; 10.2 nM	Ki; Ki	PMID: 11266177; PMID: 11266177
CHEMBL2938	P05129	Protein kinase C gamma	1.58 nM; 2.91 nM	Ki; Ki	PMID: 11266177; PMID: 11266177
CHEMBL3920	Q04759	Protein kinase C theta	1.54 nM	Ki	PMID: 11266177

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.94%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.40%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.39%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.96%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.26%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.17%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.38%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.04%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.89%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.29%	96.61%
CHEMBL1871	P10275	Androgen Receptor	80.98%	96.43%
CHEMBL5255	O00206	Toll-like receptor 4	80.08%	92.50%

Plants that contains it

• Croton tiglium

Cross-Links

• PubChem: 37783
• NPASS: NPC171905
• ChEMBL: CHEMBL27768