alpha,beta-Dihydroxanthohumol

Details

• Internal ID: 1c7f4da4-a9d4-4f6d-854d-12bf90b63fe8
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Chalcones and dihydrochalcones > 2-Hydroxy-dihydrochalcones
• IUPAC Name: 1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)propan-1-one
• SMILES (Canonical): CC(=CCC1=C(C(=C(C=C1O)OC)C(=O)CCC2=CC=C(C=C2)O)O)C
• SMILES (Isomeric): CC(=CCC1=C(C(=C(C=C1O)OC)C(=O)CCC2=CC=C(C=C2)O)O)C
• InChI: InChI=1S/C21H24O5/c1-13(2)4-10-16-18(24)12-19(26-3)20(21(16)25)17(23)11-7-14-5-8-15(22)9-6-14/h4-6,8-9,12,22,24-25H,7,10-11H2,1-3H3
• InChI Key: SVTCZHIDEDUTBH-UHFFFAOYSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₄O₅
• Molecular Weight: 356.40 g/mol
• Exact Mass: 356.16237386 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 4.90
• Atomic LogP (AlogP): 4.14
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 7

Synonyms

• alpha,beta-dihydroxanthohumol
• MLS000863606
• 4,2',4'-Trihydroxy-6'-methoxy-3'-prenyldihydrochalcone
• 102448-00-0
• CHEBI:66332
• 1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)propan-1-one
• SMR000440746
• 1-Propanone, 1-[2,4-dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-
• a,b-Dihydroxanthohumol
• D0L2AO
• CHEMBL510279
• MEGxp0_001797
• SCHEMBL15704299
• ACon1_000059
• BDBM76566
• cid_10450920
• HMS2267A19
• LMPK12120536
• NCGC00168833-01
• BRD-K15951006-001-01-4
• Q27134880
• 2',4,4'-Trihydroxy-6'-methoxy-3'-prenyldihydrochalcone
• 1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)-1-propanone
• 1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)propan-1-one
• 3-(4-hydroxyphenyl)-1-[6-methoxy-3-(3-methylbut-2-enyl)-2,4-bis(oxidanyl)phenyl]propan-1-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9846	98.46%
Caco-2	+	0.8026	80.26%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8474	84.74%
OATP2B1 inhibitior	-	0.5741	57.41%
OATP1B1 inhibitior	+	0.8449	84.49%
OATP1B3 inhibitior	+	0.9145	91.45%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8588	85.88%
P-glycoprotein inhibitior	+	0.6456	64.56%
P-glycoprotein substrate	-	0.5978	59.78%
CYP3A4 substrate	+	0.5504	55.04%
CYP2C9 substrate	-	0.8047	80.47%
CYP2D6 substrate	-	0.7946	79.46%
CYP3A4 inhibition	+	0.5362	53.62%
CYP2C9 inhibition	+	0.7976	79.76%
CYP2C19 inhibition	+	0.9225	92.25%
CYP2D6 inhibition	-	0.5858	58.58%
CYP1A2 inhibition	+	0.8962	89.62%
CYP2C8 inhibition	+	0.8313	83.13%
CYP inhibitory promiscuity	+	0.8762	87.62%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8405	84.05%
Carcinogenicity (trinary)	Non-required	0.7687	76.87%
Eye corrosion	-	0.9900	99.00%
Eye irritation	+	0.6173	61.73%
Skin irritation	-	0.7925	79.25%
Skin corrosion	-	0.9352	93.52%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4406	44.06%
Micronuclear	-	0.6941	69.41%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	-	0.7437	74.37%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.8515	85.15%
Acute Oral Toxicity (c)	III	0.5725	57.25%
Estrogen receptor binding	+	0.9527	95.27%
Androgen receptor binding	+	0.7559	75.59%
Thyroid receptor binding	+	0.6143	61.43%
Glucocorticoid receptor binding	+	0.8559	85.59%
Aromatase binding	+	0.6930	69.30%
PPAR gamma	+	0.8653	86.53%
Honey bee toxicity	-	0.8045	80.45%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6655	66.55%
Fish aquatic toxicity	+	0.9895	98.95%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293224	P10636	Microtubule-associated protein tau	15848.9 nM; 11220.2 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1741215	Q9GZR1	Sentrin-specific protease 6	10000 nM	IC50	via CMAUP
CHEMBL1741213	Q9BQF6	Sentrin-specific protease 7	7820 nM	IC50	via CMAUP
CHEMBL1741207	Q96LD8	Sentrin-specific protease 8	13300 nM	IC50	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.85%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.50%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.11%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.87%	99.17%
CHEMBL2581	P07339	Cathepsin D	94.32%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.95%	86.33%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	90.63%	97.21%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	90.33%	95.50%
CHEMBL1255126	O15151	Protein Mdm4	90.28%	90.20%
CHEMBL4208	P20618	Proteasome component C5	89.86%	90.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.76%	96.95%
CHEMBL3401	O75469	Pregnane X receptor	88.67%	94.73%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	87.74%	95.17%
CHEMBL2535	P11166	Glucose transporter	87.73%	98.75%
CHEMBL3194	P02766	Transthyretin	86.07%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.95%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.35%	94.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.63%	96.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.31%	85.14%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	80.09%	85.00%

Plants that contains it

• Alkanna cappadocica
• Artemisia rupestris subsp. rupestris
• Atalantia racemosa
• Buddleja cordata
• Crambe tatarica
• Diospyros eriantha
• Fritillaria monantha
• Hoffmannia strigillosa
• Humulus lupulus
• Millettia erythrocalyx
• Myrsine lancifolia
• Ononis vaginalis
• Pteris semipinnata
• Salvia hispanica
• Scorzonera pseudodivaricata
• Stenocereus griseus
• Syncarpia hillii

Cross-Links

• PubChem: 10450920
• NPASS: NPC13575
• ChEMBL: CHEMBL510279
• LOTUS: LTS0055501
• wikiData: Q27134880