(+)-Acuminatin

Details

• Internal ID: 123cb5e6-c5a3-4130-800d-d64cb915b12a
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (2R,3R)-2-(3,4-dimethoxyphenyl)-7-methoxy-3-methyl-5-[(E)-prop-1-enyl]-2,3-dihydro-1-benzofuran
• InChI: InChI=1S/C21H24O4/c1-6-7-14-10-16-13(2)20(25-21(16)19(11-14)24-5)15-8-9-17(22-3)18(12-15)23-4/h6-13,20H,1-5H3/b7-6+/t13-,20-/m1/s1
• InChI Key: ITFKWUHXYCXXFF-XSOBDOKWSA-N
• Popularity: 25 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₄O₄
• Molecular Weight: 340.40 g/mol
• Exact Mass: 340.16745924 g/mol
• Topological Polar Surface Area (TPSA): 36.90 Ų
• XlogP: 4.70
• Atomic LogP (AlogP): 4.98
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

• 41744-39-2
• (+)-Acuminatin
• JA2WFP75V2
• (2R,3R)-2-(3,4-dimethoxyphenyl)-7-methoxy-3-methyl-5-[(E)-prop-1-enyl]-2,3-dihydro-1-benzofuran
• CHEBI:132649
• DTXSID201317357
• Benzofuran, 2-(3,4-dimethoxyphenyl)-2,3-dihydro-7-methoxy-3-methyl-5-(1-propenyl)-, (2R-(2alpha,3beta,5(E)))-
• (2R,3R)-2-(3,4-dimethoxyphenyl)-7-methoxy-3-methyl-5-((E)-prop-1-enyl)-2,3-dihydro-1-benzofuran
• RefChem:109602
• DTXCID001747174
• CHEMBL571195
• UNII-JA2WFP75V2
• orb1683225
• SCHEMBL29477358
• HY-N2817
• BDBM50303154
• AKOS032948844
• FS-9883
• (2R,3R)-2-(3,4-dimethoxyphenyl)-7-methoxy-3-methyl-5-[(1E)-prop-1-en-1-yl]-2,3-dihydro-1-benzofuran
• BENZOFURAN, 2-(3,4-DIMETHOXYPHENYL)-2,3-DIHYDRO-7-METHOXY-3-METHYL-5-(1E)-1-PROPEN-1-YL-, (2R,3R)-
• DA-60801
• CS-0023377
• Q27281398
• (2R,3R)-2-(3,4-DIMETHOXYPHENYL)-2,3-DIHYDRO-7-METHOXY-3-METHYL-5-(1E)-1-PROPEN-1-YLBENZOFURAN
• (2R,3R)-2-(3,4-Dimethoxyphenyl)-7-methoxy-3-methyl-5-((E)-prop-1-en-1-yl)-2,3-dihydrobenzofuran
• BENZOFURAN, 2-(3,4-DIMETHOXYPHENYL)-2,3-DIHYDRO-7-METHOXY-3-METHYL-5-(1-PROPENYL)-, (2R-(2.ALPHA.,3.BETA.,5(E)))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9970	99.70%
Caco-2	+	0.9524	95.24%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6378	63.78%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8803	88.03%
OATP1B3 inhibitior	+	0.9725	97.25%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8737	87.37%
P-glycoprotein inhibitior	+	0.8188	81.88%
P-glycoprotein substrate	-	0.7475	74.75%
CYP3A4 substrate	+	0.5343	53.43%
CYP2C9 substrate	+	0.6124	61.24%
CYP2D6 substrate	-	0.6772	67.72%
CYP3A4 inhibition	+	0.8294	82.94%
CYP2C9 inhibition	+	0.6677	66.77%
CYP2C19 inhibition	+	0.8943	89.43%
CYP2D6 inhibition	-	0.7937	79.37%
CYP1A2 inhibition	+	0.9269	92.69%
CYP2C8 inhibition	+	0.6601	66.01%
CYP inhibitory promiscuity	+	0.9738	97.38%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9218	92.18%
Carcinogenicity (trinary)	Danger	0.4835	48.35%
Eye corrosion	-	0.9866	98.66%
Eye irritation	-	0.8616	86.16%
Skin irritation	-	0.8019	80.19%
Skin corrosion	-	0.9806	98.06%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8555	85.55%
Micronuclear	+	0.6459	64.59%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.8223	82.23%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.7147	71.47%
Acute Oral Toxicity (c)	III	0.4905	49.05%
Estrogen receptor binding	+	0.8700	87.00%
Androgen receptor binding	-	0.4934	49.34%
Thyroid receptor binding	+	0.7892	78.92%
Glucocorticoid receptor binding	+	0.7208	72.08%
Aromatase binding	+	0.5707	57.07%
PPAR gamma	-	0.5146	51.46%
Honey bee toxicity	-	0.7787	77.87%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.9851	98.51%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.41%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.22%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.07%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.24%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.48%	85.14%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	87.41%	97.31%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.99%	91.11%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.50%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.04%	89.00%
CHEMBL5939	Q9NZ08	Endoplasmic reticulum aminopeptidase 1	83.19%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	82.98%	94.73%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.85%	92.94%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	82.08%	94.03%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.27%	89.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.11%	95.89%
CHEMBL2535	P11166	Glucose transporter	80.94%	98.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.93%	97.09%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.03%	97.21%

Plants that contains it

• Casuarina equisetifolia
• Epimedium brevicornu
• Epimedium grandiflorum
• Epimedium koreanum
• Epimedium pubescens
• Epimedium sagittatum
• Epimedium sempervirens
• Epimedium wushanense
• Juniperus sabina
• Machilus obovatifolia
• Machilus thunbergii
• Magnolia acuminata
• Magnolia acuminata
• Magnolia denudata
• Magnolia ovata
• Mollugo pentaphylla
• Nectandra amazonum
• Piper kadsura
• Sesamum indicum

Cross-Links

• PubChem: 6441048
• NPASS: NPC98745
• ChEMBL: CHEMBL571195
• LOTUS: LTS0198896
• wikiData: Q27281398