Phorbol

Details

• Internal ID: 2e53bc66-ad3f-48a4-92c6-159088980747
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Tigliane and ingenane diterpenoids
• IUPAC Name: (1S,2S,6R,10S,11R,13S,14R,15R)-1,6,13,14-tetrahydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyltetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dien-5-one
• SMILES (Canonical): CC1C(C2(C(C2(C)C)C3C1(C4C=C(C(=O)C4(CC(=C3)CO)O)C)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@H]([C@@]2([C@@H](C2(C)C)[C@H]3[C@]1([C@@H]4C=C(C(=O)[C@]4(CC(=C3)CO)O)C)O)O)O
• InChI: InChI=1S/C20H28O6/c1-9-5-13-18(24,15(9)22)7-11(8-21)6-12-14-17(3,4)20(14,26)16(23)10(2)19(12,13)25/h5-6,10,12-14,16,21,23-26H,7-8H2,1-4H3/t10-,12+,13-,14-,16-,18-,19-,20-/m1/s1
• InChI Key: QGVLYPPODPLXMB-UBTYZVCOSA-N
• Popularity: 7,132 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₆
• Molecular Weight: 364.40 g/mol
• Exact Mass: 364.18858861 g/mol
• Topological Polar Surface Area (TPSA): 118.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -0.07
• H-Bond Acceptor: 6
• H-Bond Donor: 5
• Rotatable Bonds: 1

Synonyms

• 17673-25-5
• UNII-XUZ76S9127
• CHEBI:8116
• 4alpha-Phorbol
• 4beta-Phorbol
• 4-beta-Phorbol
• XUZ76S9127
• 4,9,12beta,13,20-pentahydroxy-1,6-tigliadien-3-on
• (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-5H-cyclopropa[3,4]benzo[1,2-e]azulen-5-one
• 4,9,12-beta,13,20-Pentahydroxy-1,6-tigliadien-3-on
• 4,9,12beta,13,20-pentahydroxytiglia-1,6-dien-3-one
• 5H-Cyclopropa[3,4]benz[1,2-e]azulen-5-one,1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-,(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-
• CCRIS 694
• HSDB 4328
• 4-Phorbol
• 4-.beta.-Phorbol
• NSC 154778
• (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-4a,7b,9,9a-Tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-1b,4,4a,7a,7b,8,9,9a-octahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-5(1aH)-one
• 5H-Cyclopropa(3,4)benz(1,2-e)azulen-5-one, 1,1a-beta,1b-alpha,4,4a,7a-beta,7b,8,9,9a-decahydro-4a-alpha,7b-alpha,9-beta,9a-alpha-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-alpha-tetramethyl-
• 4b-phorbol
• NSC-154778
• 1,1a,1b,4,4a,7a,7b,8,9,9a-Decahydro-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5H-cyclopropa(3,4)benz(1,2-e)azulen-5-one (1aR-(1aalpha,1bbeta,4abeta,7aalpha,7balpha,8alpha,9beta,9aalpha))-
• 5H-Cyclopropa(3,4)benz(1,2-e)azulen-5-one, 1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-, (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-
• 5H-Cyclopropa(3,4)benz(1,2-e)azulen-5-one, 1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,6,8-tetramethyl-, (1aR-(1aalpha,1beta,4abeta,7aalpha,7balpha,8alpha,9beta,9aalpha))-
• 5H-Cyclopropa(3,4)benz(1,2-e)azulen-5-one, 1,1aalpha,1bbeta,4,4a,7aalpha,7b,8,9,9a-decahydro-4abeta,7balpha,9beta,9a alpha-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8alpha-tetramethyl-, (+)-
• 5H-Cyclopropa[3,4]benz[1,2-e]azulen-5-one, 1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-, (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-
• (+)-phorbol
• 4.b.-Phorbol
• tetrahydroxy-(hydroxymethyl)-tetramethyl-[?]one
• PHORBOL [HSDB]
• PHORBOL [MI]
• SCHEMBL14937
• CHEMBL124518
• DTXSID2021155
• QGVLYPPODPLXMB-UBTYZVCOSA-N
• 26241-63-4
• 5H-Cyclopropa[3,4]benz[1,2-e]azulen-5-one, 1,1a.alpha.,1b.beta.,4,4a,7a.alpha.,7b,8,9,9a-decahydro-4a.beta.,7b.alpha.,9.beta.,9a.alpha.-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8.alpha.-tetramethyl-, ()-
• 5H-Cyclopropa[3,4]benz[1,2-e]azulen-5-one, 1,1a.beta.,1b.alpha.,4,4a,7a.beta.,7b,8,9,9a-decahydro-4a.alpha.,7b.alpha.,9.beta.,9a.alpha.-tetrahydroxy-3-(hydroxymethyl)-1,1,ster
• EX-A3092
• HY-N2147
• MFCD00065450
• AKOS024418764
• CCG-268216
• CS-6052
• LMPR0104330001
• SMP2_000151
• AC-33956
• BS-16283
• P2732
• S9389
• C09155
• A881502
• SR-05000002211
• J-011221
• Q2705359
• SR-05000002211-2
• 4beta,9alpha,12beta,13alpha,20-Pentahydroxytiglia-1,6-dien-3-one
• 5-[2-(DIETHYLAMINO)ETHYL]-3-PHENYL-1,2,4-OXADIAZOLECITRATESALT
• (1AR,1BS,4AR,7AS,7BS,8R,9R,9AS)-1,1A,1B,4,4A,7A,7B,8,9,9A-DECAHYDRO-4A,7B,9,9A-TETRAHYDROXY-3-(HYDROXYMETHYL)-1,1,6,8-TETRAMETHYL-5H-CYCLOPROPA(3,4)BENZ(1,2-E)AZULEN-5-ONE
• (1S,2S,6R,10S,11R,13S,14R,15R)-1,6,13,14-tetrahydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyltetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dien-5-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9571	95.71%
Caco-2	-	0.7727	77.27%
Blood Brain Barrier	+	0.5606	56.06%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6412	64.12%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8787	87.87%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7538	75.38%
P-glycoprotein inhibitior	-	0.9218	92.18%
P-glycoprotein substrate	-	0.6615	66.15%
CYP3A4 substrate	+	0.6163	61.63%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8729	87.29%
CYP3A4 inhibition	-	0.8797	87.97%
CYP2C9 inhibition	-	0.7410	74.10%
CYP2C19 inhibition	-	0.8453	84.53%
CYP2D6 inhibition	-	0.9154	91.54%
CYP1A2 inhibition	-	0.7719	77.19%
CYP2C8 inhibition	-	0.8661	86.61%
CYP inhibitory promiscuity	-	0.8421	84.21%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6557	65.57%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9267	92.67%
Skin irritation	-	0.6824	68.24%
Skin corrosion	-	0.9306	93.06%
Ames mutagenesis	+	0.5326	53.26%
Human Ether-a-go-go-Related Gene inhibition	-	0.5319	53.19%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.6393	63.93%
skin sensitisation	-	0.7267	72.67%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.5533	55.33%
Estrogen receptor binding	+	0.6073	60.73%
Androgen receptor binding	+	0.6636	66.36%
Thyroid receptor binding	+	0.7029	70.29%
Glucocorticoid receptor binding	+	0.6201	62.01%
Aromatase binding	+	0.7267	72.67%
PPAR gamma	-	0.6155	61.55%
Honey bee toxicity	-	0.8807	88.07%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.6943	69.43%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.76%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.28%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.75%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.86%	95.56%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	86.65%	86.00%
CHEMBL2996	Q05655	Protein kinase C delta	84.81%	97.79%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.56%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	84.45%	94.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.83%	97.09%
CHEMBL4794	Q8NER1	Vanilloid receptor	82.89%	98.97%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.85%	91.11%
CHEMBL4208	P20618	Proteasome component C5	81.26%	90.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.42%	85.14%
CHEMBL3045	P05771	Protein kinase C beta	80.21%	97.63%
CHEMBL299	P17252	Protein kinase C alpha	80.17%	98.03%

Plants that contains it

• Croton tiglium
• Euphorbia tirucalli
• Gnidia chrysantha
• Rehmannia glutinosa
• Trigonostemon howii

Cross-Links

• PubChem: 442070
• NPASS: NPC163004
• LOTUS: LTS0183626
• wikiData: Q2705359