Isoeugenitol

Details

• Internal ID: 0687a58f-4d04-4f27-a941-c4ef5771efc2
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Chromones
• IUPAC Name: 5,7-dihydroxy-2,8-dimethylchromen-4-one
• SMILES (Canonical): CC1=CC(=O)C2=C(C=C(C(=C2O1)C)O)O
• SMILES (Isomeric): CC1=CC(=O)C2=C(C=C(C(=C2O1)C)O)O
• InChI: InChI=1S/C11H10O4/c1-5-3-8(13)10-9(14)4-7(12)6(2)11(10)15-5/h3-4,12,14H,1-2H3
• InChI Key: XSSGQRFNGHRFBC-UHFFFAOYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₀O₄
• Molecular Weight: 206.19 g/mol
• Exact Mass: 206.05790880 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 1.82
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• 5,7-dihydroxy-2,8-dimethylchromone
• 479-06-1
• KBio1_001073
• Spectrum_000601
• SpecPlus_000033
• Spectrum2_000569
• Spectrum3_000687
• Spectrum4_001501
• Spectrum5_000261
• BSPBio_002413
• KBioGR_002161
• KBioSS_001081
• SPECTRUM200449
• DivK1c_006129
• SPBio_000358
• CHEMBL1371435
• SCHEMBL18517012
• CHEBI:92103
• KBio2_001081
• KBio2_003649
• KBio2_006217
• KBio3_001633
• DTXSID601318026
• CCG-38735
• SDCCGMLS-0066885.P001
• NCGC00095479-01
• NCGC00095479-02
• NCGC00178664-01
• 5,7-dihydroxy-2,8-dimethyl-4H-chromen-4-one
• 5,7-dihydroxy-2,8-dimethyl-1-benzopyran-4-one
• BRD-K05737787-001-02-2
• Q27163895

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9596	95.96%
Caco-2	+	0.6388	63.88%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7045	70.45%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.6000	60.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9358	93.58%
P-glycoprotein inhibitior	-	0.8836	88.36%
P-glycoprotein substrate	-	0.9524	95.24%
CYP3A4 substrate	-	0.6134	61.34%
CYP2C9 substrate	-	0.6157	61.57%
CYP2D6 substrate	-	0.8583	85.83%
CYP3A4 inhibition	+	0.7650	76.50%
CYP2C9 inhibition	+	0.5771	57.71%
CYP2C19 inhibition	+	0.5854	58.54%
CYP2D6 inhibition	-	0.8449	84.49%
CYP1A2 inhibition	+	0.9707	97.07%
CYP2C8 inhibition	-	0.9387	93.87%
CYP inhibitory promiscuity	+	0.6875	68.75%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7155	71.55%
Eye corrosion	-	0.9821	98.21%
Eye irritation	+	0.9372	93.72%
Skin irritation	-	0.5203	52.03%
Skin corrosion	-	0.9335	93.35%
Ames mutagenesis	-	0.5564	55.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.7386	73.86%
Micronuclear	+	0.9300	93.00%
Hepatotoxicity	+	0.5033	50.33%
skin sensitisation	-	0.8216	82.16%
Respiratory toxicity	-	0.6889	68.89%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.5614	56.14%
Acute Oral Toxicity (c)	III	0.6826	68.26%
Estrogen receptor binding	+	0.5820	58.20%
Androgen receptor binding	+	0.6569	65.69%
Thyroid receptor binding	-	0.6181	61.81%
Glucocorticoid receptor binding	+	0.7207	72.07%
Aromatase binding	-	0.5658	56.58%
PPAR gamma	+	0.5325	53.25%
Honey bee toxicity	-	0.9523	95.23%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9219	92.19%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4096	P04637	Cellular tumor antigen p53	31622.8 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	25118.9 nM; 25118.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	28183.8 nM; 25118.9 nM; 35481.3 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.41%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	94.39%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.00%	95.56%
CHEMBL2581	P07339	Cathepsin D	88.77%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.93%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.29%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	87.09%	91.49%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	83.36%	93.65%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.45%	99.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.97%	90.71%

Plants that contains it

• Aconitum sajanense
• Allium sativum
• Artemisia jacutica
• Bersama abyssinica
• Damnacanthus major
• Piper attenuatum
• Rubus sanctus
• Senna santanderensis
• Stauntonia hexaphylla
• Strychnos trinervis
• Syzygium aromaticum

Cross-Links

• PubChem: 5318562
• NPASS: NPC93756
• ChEMBL: CHEMBL1371435
• LOTUS: LTS0241346
• wikiData: Q27163895