4-(2-Aminopropyl)phenol

Details

• Internal ID: 1233bd24-bc9a-422f-8b1a-b0da15e1b5de
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Phenethylamines > Amphetamines and derivatives
• IUPAC Name: 4-(2-aminopropyl)phenol
• SMILES (Canonical): CC(CC1=CC=C(C=C1)O)N
• SMILES (Isomeric): CC(CC1=CC=C(C=C1)O)N
• InChI: InChI=1S/C9H13NO/c1-7(10)6-8-2-4-9(11)5-3-8/h2-5,7,11H,6,10H2,1H3
• InChI Key: GIKNHHRFLCDOEU-UHFFFAOYSA-N
• Popularity: 508 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₃NO
• Molecular Weight: 151.21 g/mol
• Exact Mass: 151.099714038 g/mol
• Topological Polar Surface Area (TPSA): 46.20 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.28
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• hydroxyamphetamine
• Paredrine
• 103-86-6
• Hydroxyamfetamine
• Norveritol
• Pulsoton
• p-HYDROXYAMPHETAMINE
• 4-Hydroxyamphetamine
• Norpholedrine
• Oxamphetamine
• Oksamfetamin
• Oxamfetamin
• Oxamphetaminium
• Paredrinex
• Nov-Pholedrin
• Phenol, 4-(2-aminopropyl)-
• Paradrine
• Pedrolon
• Phenol,4-(2-aminopropyl)-
• Phenol, p-(2-aminopropyl)-
• p-(2-Aminopropyl)phenol
• DL-p-Hydroxyamphetamine
• 1-p-Hydroxyphenyl-2-propylamine
• 2-Amino-1-(p-hydroxyphenyl)propane
• .alpha.-Methyltyramine
• dl-4-hydroxyamphetamine
• alpha-Methyltyramine
• NSC 170995
• 1518-86-1
• 4-Hydroxy-.alpha.-methylphenethylamine
• NSC-170995
• Racemic p-hydroxyamphetamine
• FQR280JW2N
• DL-p-(2-Aminopropyl)phenol
• p-Hydroxy-.alpha.-methylphenethylamine
• p-Hydroxy-alpha-methylphenethylamine
• 4-Hydroxy-alpha-methylphenethylamine
• Hydroxyamphetamide
• Hydroxyamfetamine [INN]
• EINECS 203-152-8
• UNII-FQR280JW2N
• BRN 2413849
• Hydroxyamfetamine [INN:BAN]
• Predrolon (Salt/Mix)
• Spectrum_001243
• OH-A
• Spectrum3_001037
• Spectrum4_001174
• Spectrum5_001674
• (RS)-4-hydroxyamphetamine
• Hydroxyamphetamine,(+/-)
• WLN: Z3R DQ
• CHEMBL1546
• 4-(2-amino-propyl)-phenol
• BSPBio_002853
• KBioGR_001807
• KBioSS_001723
• 3-13-00-01709 (Beilstein Handbook Reference)
• (+/-)-4-Hydroxyamphetamine
• SCHEMBL125440
• HYDROXYAMPHETAMINE [MI]
• DTXSID3023134
• BDBM81459
• KBio2_001723
• KBio2_004291
• KBio2_006859
• KBio3_002073
• HYDROXYAMPHETAMINE [VANDF]
• CHEBI:103855
• HYDROXYAMFETAMINE [WHO-DD]
• HY-B1098
• NSC_3651
• 1-(4-Hydroxyphenyl)propane-2-amine
• NSC170995
• PDSP1_001107
• PDSP2_001091
• AKOS000155358
• AKOS017269170
• CS-4687
• DB09352
• NCGC00178433-01
• NCGC00178433-02
• (+/-)-P-(2-AMINOPROPYL)PHENOL
• BS-13447
• CAS_103-86-6
• Phenol, p-(2-aminopropyl)-, (.+/-.)-
• EN300-53926
• Phenol, 4-(2-aminopropyl)-, (.+/-.)-
• AB01563354_01
• Q5955531
• BRD-A80871782-004-01-0
• Z57102382

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.9499	94.99%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Lysosomes	0.4894	48.94%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9440	94.40%
OATP1B3 inhibitior	+	0.9575	95.75%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.9569	95.69%
P-glycoprotein inhibitior	-	0.9903	99.03%
P-glycoprotein substrate	-	0.8011	80.11%
CYP3A4 substrate	-	0.7593	75.93%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.5870	58.70%
CYP3A4 inhibition	-	0.8767	87.67%
CYP2C9 inhibition	-	0.9104	91.04%
CYP2C19 inhibition	-	0.7723	77.23%
CYP2D6 inhibition	-	0.7163	71.63%
CYP1A2 inhibition	-	0.8164	81.64%
CYP2C8 inhibition	-	0.9329	93.29%
CYP inhibitory promiscuity	-	0.8507	85.07%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.5353	53.53%
Carcinogenicity (trinary)	Non-required	0.6827	68.27%
Eye corrosion	-	0.9425	94.25%
Eye irritation	-	0.9424	94.24%
Skin irritation	-	0.5164	51.64%
Skin corrosion	+	0.8396	83.96%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7025	70.25%
Micronuclear	+	0.6985	69.85%
Hepatotoxicity	+	0.5188	51.88%
skin sensitisation	+	0.6468	64.68%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	-	0.5608	56.08%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.7656	76.56%
Acute Oral Toxicity (c)	II	0.5359	53.59%
Estrogen receptor binding	-	0.9200	92.00%
Androgen receptor binding	-	0.6029	60.29%
Thyroid receptor binding	-	0.8308	83.08%
Glucocorticoid receptor binding	-	0.8814	88.14%
Aromatase binding	-	0.8120	81.20%
PPAR gamma	-	0.7991	79.91%
Honey bee toxicity	-	0.9700	97.00%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	-	0.6875	68.75%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.96%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.93%	96.09%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	92.53%	97.23%
CHEMBL3492	P49721	Proteasome Macropain subunit	92.53%	90.24%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.46%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	87.29%	91.49%
CHEMBL242	Q92731	Estrogen receptor beta	84.33%	98.35%
CHEMBL3401	O75469	Pregnane X receptor	83.05%	94.73%
CHEMBL301	P24941	Cyclin-dependent kinase 2	83.00%	91.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.85%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.21%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.72%	99.17%
CHEMBL1255126	O15151	Protein Mdm4	81.30%	90.20%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.19%	91.71%

Plants that contains it

• Senegalia berlandieri
• Vachellia rigidula

Cross-Links

• PubChem: 3651
• LOTUS: LTS0248387
• wikiData: Q105189157