Hirsutenone

Details

• Internal ID: 35c13787-25f2-4522-b7f3-a09d456aa8ee
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids
• IUPAC Name: (E)-1,7-bis(3,4-dihydroxyphenyl)hept-4-en-3-one
• SMILES (Canonical): C1=CC(=C(C=C1CCC=CC(=O)CCC2=CC(=C(C=C2)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1CC/C=C/C(=O)CCC2=CC(=C(C=C2)O)O)O)O
• InChI: InChI=1S/C19H20O5/c20-15(8-5-14-7-10-17(22)19(24)12-14)4-2-1-3-13-6-9-16(21)18(23)11-13/h2,4,6-7,9-12,21-24H,1,3,5,8H2/b4-2+
• InChI Key: VWHYFMQKJYFLCC-DUXPYHPUSA-N
• Popularity: 28 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₀O₅
• Molecular Weight: 328.40 g/mol
• Exact Mass: 328.13107373 g/mol
• Topological Polar Surface Area (TPSA): 98.00 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.20
• H-Bond Acceptor: 5
• H-Bond Donor: 4
• Rotatable Bonds: 7

Synonyms

• Hirsutanone
• 41137-87-5
• Dehydrohirsutanonol
• 1,7-Bis-(3,4-dihydroxyphenyl)-4-hepten-3-one
• VQ04K2MMM5
• (E)-1,7-bis(3,4-dihydroxyphenyl)hept-4-en-3-one
• (4E)-1,7-Bis(3,4-dihydroxyphenyl)-4-hepten-3-one
• 4-hepten-3-one, 1,7-bis(3,4-dihydroxyphenyl)-, (4E)-
• (4E)-1,7-bis(3,4-dihydroxyphenyl)hept-4-en-3-one
• UNII-VQ04K2MMM5
• CHEMBL464274
• SCHEMBL1225021
• DTXSID00873736
• CHEBI:183478
• (4E)-1,7-Bis(3,4-dihydroxyphenyl)-4-hepten-3-one; 1,7-Bis-(3,4-dihydroxyphenyl)-4-hepten-3-one; Hirsutanone
• HY-N4042
• BDBM50478445
• AKOS040761834
• Hirsutenone, >=95% (LC/MS-ELSD)
• CS-0024513
• 1,7-Bis-(3,4-dihydroxy-phenyl)-hept-4-en-3-one
• 1,7-Di-(3',4'-dihydroxyphenyl)-4-hepten-3-one
• (4E)-1,7-Bis(3,4-dihydroxyphenyl)-4-heptene-3-one
• InChI=1/C19H20O5/c20-15(8-5-14-7-10-17(22)19(24)12-14)4-2-1-3-13-6-9-16(21)18(23)11-13/h2,4,6-7,9-12,21-24H,1,3,5,8H2/b4-2

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9419	94.19%
Caco-2	-	0.8688	86.88%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8797	87.97%
OATP2B1 inhibitior	-	0.5728	57.28%
OATP1B1 inhibitior	+	0.9445	94.45%
OATP1B3 inhibitior	+	0.9700	97.00%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8367	83.67%
P-glycoprotein inhibitior	-	0.6522	65.22%
P-glycoprotein substrate	-	0.9586	95.86%
CYP3A4 substrate	-	0.6118	61.18%
CYP2C9 substrate	-	0.7936	79.36%
CYP2D6 substrate	-	0.8180	81.80%
CYP3A4 inhibition	-	0.5495	54.95%
CYP2C9 inhibition	+	0.5078	50.78%
CYP2C19 inhibition	-	0.5000	50.00%
CYP2D6 inhibition	-	0.8766	87.66%
CYP1A2 inhibition	+	0.7903	79.03%
CYP2C8 inhibition	-	0.6318	63.18%
CYP inhibitory promiscuity	-	0.6016	60.16%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.7823	78.23%
Carcinogenicity (trinary)	Non-required	0.6287	62.87%
Eye corrosion	-	0.9808	98.08%
Eye irritation	+	0.7228	72.28%
Skin irritation	-	0.6303	63.03%
Skin corrosion	-	0.9270	92.70%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4763	47.63%
Micronuclear	-	0.5741	57.41%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	+	0.6272	62.72%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.6375	63.75%
Nephrotoxicity	-	0.7597	75.97%
Acute Oral Toxicity (c)	III	0.7662	76.62%
Estrogen receptor binding	+	0.8824	88.24%
Androgen receptor binding	+	0.8086	80.86%
Thyroid receptor binding	+	0.7025	70.25%
Glucocorticoid receptor binding	+	0.7785	77.85%
Aromatase binding	+	0.7670	76.70%
PPAR gamma	+	0.8438	84.38%
Honey bee toxicity	-	0.9076	90.76%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9843	98.43%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.07%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.55%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.74%	94.45%
CHEMBL3194	P02766	Transthyretin	85.22%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.57%	86.33%
CHEMBL4208	P20618	Proteasome component C5	83.20%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.80%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.40%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.37%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	82.04%	94.73%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.28%	90.71%

Plants that contains it

• Alnus firma
• Alnus hirsuta
• Alnus japonica
• Pinus flexilis
• Viscum cruciatum

Cross-Links

• PubChem: 637394
• NPASS: NPC61062
• ChEMBL: CHEMBL464274
• LOTUS: LTS0266832
• wikiData: Q72482499