Embelin

Details

• Internal ID: bc21ee95-842c-4479-a340-245b2e40cb3c
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Benzoquinones > P-benzoquinones
• IUPAC Name: 2,5-dihydroxy-3-undecylcyclohexa-2,5-diene-1,4-dione
• SMILES (Canonical): CCCCCCCCCCCC1=C(C(=O)C=C(C1=O)O)O
• SMILES (Isomeric): CCCCCCCCCCCC1=C(C(=O)C=C(C1=O)O)O
• InChI: InChI=1S/C17H26O4/c1-2-3-4-5-6-7-8-9-10-11-13-16(20)14(18)12-15(19)17(13)21/h12,18,21H,2-11H2,1H3
• InChI Key: IRSFLDGTOHBADP-UHFFFAOYSA-N
• Popularity: 489 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₆O₄
• Molecular Weight: 294.40 g/mol
• Exact Mass: 294.18310931 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 5.40
• Atomic LogP (AlogP): 4.31
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 10

Synonyms

• 550-24-3
• Embelic acid
• 2,5-dihydroxy-3-undecylcyclohexa-2,5-diene-1,4-dione
• Emberine
• 2,5-Dihydroxy-3-undecyl-1,4-benzoquinone
• 2,5-Dihydroxy-3-undecyl-p-benzoquinone
• 2,5-Dihydroxy-3-undecyl-2,5-cyclohexadiene-1,4-dione
• NSC 91874
• CHEBI:4778
• NSC91874
• EINECS 208-979-8
• UNII-SHC6U8F5ER
• SHC6U8F5ER
• BRN 1885786
• p-Benzoquinone, 2,5-dihydroxy-3-undecyl-
• NSC-91874
• 2,5-Cyclohexadiene-1,4-dione, 2,5-dihydroxy-3-undecyl-
• 4-08-00-02769 (Beilstein Handbook Reference)
• SR-01000597536
• Embeliaquinone
• MFCD00016369
• Spectrum_001513
• Tocris-2156
• SpecPlus_000501
• EMBELIN [MI]
• Spectrum3_001931
• Spectrum4_001760
• Spectrum5_000620
• D05HSW
• BSPBio_003531
• KBioGR_002240
• KBioSS_001993
• MLS000563189
• BIDD:ER0529
• DivK1c_006597
• SCHEMBL148744
• SPECTRUM1504074
• CHEMBL221137
• GTPL11209
• KBio1_001541
• KBio2_001993
• KBio2_004561
• KBio2_007129
• KBio3_002783
• DTXSID80203537
• IRSFLDGTOHBADP-UHFFFAOYSA-N
• HMS1922B07
• HMS2271A03
• HMS3268N13
• HMS3413I11
• HMS3652J16
• HMS3677I11
• BCP31134
• TNP00137
• BDBM50078850
• CCG-39906
• Embelin, >=98% (HPLC), powder
• HSCI1_000123
• AKOS016010144
• CS-1879
• p-Benzoquinone,5-dihydroxy-3-undecyl-
• SDCCGMLS-0066817.P001
• 2,4-dione, 2,5-dihydroxy-3-undecyl-
• NCGC00017248-01
• NCGC00017248-02
• NCGC00017248-03
• NCGC00017248-04
• NCGC00017248-05
• NCGC00017248-06
• NCGC00017248-07
• NCGC00017248-08
• NCGC00017248-10
• NCGC00025359-01
• NCGC00025359-02
• NCGC00025359-03
• NCGC00025359-04
• NCGC00025359-05
• AC-34763
• AS-55903
• BP-25395
• HY-17473
• LS-40347
• NCI60_042031
• SMR000470851
• 2,5-Dihydroxy-3-undecyl-[1,4]benzoquinone
• FT-0712499
• S7025
• SW219508-1
• A830443
• SR-01000597536-1
• SR-01000597536-3
• Q27068169
• Embelic acid;2,5-Dihydroxy-3-undecyl-1,4-benzoquinone
• Embelic acid; Emberine; NSC 91874; NSC91874; NSC 91874
• NCGC00017248-12!2,5-dihydroxy-3-undecylcyclohexa-2,5-diene-1,4-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9732	97.32%
Caco-2	-	0.5276	52.76%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8799	87.99%
OATP2B1 inhibitior	-	0.8516	85.16%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9527	95.27%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7064	70.64%
BSEP inhibitior	-	0.8335	83.35%
P-glycoprotein inhibitior	-	0.8841	88.41%
P-glycoprotein substrate	-	0.7921	79.21%
CYP3A4 substrate	-	0.5484	54.84%
CYP2C9 substrate	-	0.8037	80.37%
CYP2D6 substrate	-	0.8667	86.67%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	+	0.7217	72.17%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	-	0.8824	88.24%
CYP inhibitory promiscuity	-	0.8416	84.16%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8923	89.23%
Carcinogenicity (trinary)	Non-required	0.6341	63.41%
Eye corrosion	-	0.9686	96.86%
Eye irritation	+	0.9349	93.49%
Skin irritation	-	0.5128	51.28%
Skin corrosion	-	0.9259	92.59%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4592	45.92%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	+	0.5507	55.07%
skin sensitisation	-	0.6237	62.37%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.6145	61.45%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	+	0.7838	78.38%
Acute Oral Toxicity (c)	III	0.6314	63.14%
Estrogen receptor binding	+	0.6827	68.27%
Androgen receptor binding	+	0.7152	71.52%
Thyroid receptor binding	+	0.7090	70.90%
Glucocorticoid receptor binding	+	0.6582	65.82%
Aromatase binding	-	0.6241	62.41%
PPAR gamma	+	0.8725	87.25%
Honey bee toxicity	-	0.9823	98.23%
Biodegradation	+	0.6250	62.50%
Crustacea aquatic toxicity	+	0.7937	79.37%
Fish aquatic toxicity	+	0.9957	99.57%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	25118.9 nM; 14125.4 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	23755.8 nM; 19952.6 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3687	P18054	Arachidonate 12-lipoxygenase	8912.5 nM	Potency	via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	5011.9 nM	Potency	via CMAUP
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	230 nM; 170 nM; 170 nM; 180 nM; 190 nM; 220 nM; 60 nM; 380 nM; 60 nM; 1700 nM; 60 nM; 800 nM	IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50	via Super-PRED; via Super-PRED; via Super-PRED; via Super-PRED; via Super-PRED; via Super-PRED; PMID: 25765759; via Super-PRED; via Super-PRED; PMID: 25765759; PMID: 25765759; PMID: 25765759
CHEMBL4096	P04637	Cellular tumor antigen p53	12589.3 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3622	P33261	Cytochrome P450 2C19	39810.7 nM	Potency	via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	25118.9 nM	Potency	via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	1995.3 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	3162.3 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3714079	Q9NQS5	G-protein coupled receptor 84	23.6 nM	Ki	via Super-PRED
CHEMBL5500	Q92831	Histone acetyltransferase PCAF	7200 nM	IC50	PMID: 26701186
CHEMBL4198	P98170	Inhibitor of apoptosis protein 3	4100 nM; 4100 nM	IC50; IC50	PMID: 15115387; PMID: 15115387
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	19952.6 nM; 4466.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3414409	Q2M385	Macrophage-expressed gene 1 protein	210 nM; 800 nM; 210 nM; 900 nM; 210 nM	IC50; IC50; IC50; IC50; IC50	via Super-PRED; via Super-PRED; PMID: 25765759; via Super-PRED; PMID: 25765759
CHEMBL4040	P28482	MAP kinase ERK2	125.9 nM; 125.9 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	39810.7 nM; 31622.8 nM; 11220.2 nM; 25118.9 nM; 39810.7 nM; 10000 nM; 19952.6 nM; 39810.7 nM; 39810.7 nM	Potency; Potency; Potency; Potency; Potency; Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP; via CMAUP; via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL5658	O14684	Prostaglandin E synthase	200 nM	IC50	via Super-PRED
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	5011.9 nM	Potency	via CMAUP
CHEMBL1293227	O75604	Ubiquitin carboxyl-terminal hydrolase 2	3162.3 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.23%	98.95%
CHEMBL230	P35354	Cyclooxygenase-2	94.24%	89.63%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	93.20%	92.08%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.16%	91.11%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	89.02%	85.94%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.39%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.64%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.38%	99.23%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.59%	100.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.34%	90.71%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.51%	97.25%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.58%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.23%	86.33%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	80.85%	92.86%

Plants that contains it

• Aegiceras corniculatum
• Ardisia crenata
• Ardisia japonica
• Ardisia oxyphylla
• Clematis chinensis
• Embelia madagascariensis
• Embelia ribes
• Embelia schimperi
• Embelia tsjeriam-cottam
• Ipomoea nil
• Lysimachia punctata
• Myrsine africana
• Myrsine laetevirens
• Myrsine melanophloeos
• Myrsine seguinii
• Myrsine umbellata
• Oxalis erythrorhiza

Cross-Links

• PubChem: 3218
• NPASS: NPC143168
• ChEMBL: CHEMBL221137
• LOTUS: LTS0136079
• wikiData: Q27068169