4-(2-Amino-1-hydroxyethyl)benzene-1,2-diol

Details

• Internal ID: b06a3e28-5125-44b2-98b6-16be50d06b5d
• Taxonomy: Benzenoids > Phenols > Benzenediols > Catechols
• IUPAC Name: 4-(2-amino-1-hydroxyethyl)benzene-1,2-diol
• SMILES (Canonical): C1=CC(=C(C=C1C(CN)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C(CN)O)O)O
• InChI: InChI=1S/C8H11NO3/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8,10-12H,4,9H2
• InChI Key: SFLSHLFXELFNJZ-UHFFFAOYSA-N
• Popularity: 46,928 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₁₁NO₃
• Molecular Weight: 169.18 g/mol
• Exact Mass: 169.07389321 g/mol
• Topological Polar Surface Area (TPSA): 86.70 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): 0.09
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

• dl-Norepinephrine
• 4-(2-amino-1-hydroxyethyl)benzene-1,2-diol
• dl-Arterenol
• dl-Noradrenaline
• Noradrenalin, dl-
• 1,2-Benzenediol, 4-(2-amino-1-hydroxyethyl)-
• (+-)-Noradrenaline
• NSC 294898
• Norepinephrine, DL-
• (+/-)-noradrenaline
• EINECS 205-337-9
• Levarterenol;L-Noradrenaline
• UNII-K294OAI79V
• [3H]NE
• K294OAI79V
• CHEBI:33569
• NSC294898
• NSC-294898
• (1)-4-(2-Amino-1-hydroxyethyl)pyrocatechol
• d-Arterenol
• 1,2-Benzenediol, 4-(2-amino-1-hydroxyethyl)-, (+-)-
• 1,2-Benzenediol, 4-(2-amino-1-hydroxyethyl)-, (.+/-.)-
• BENZYL ALCOHOL, alpha-(AMINOMETHYL)-3,4-DIHYDROXY-, (+-)-
• Noradrop
• xi-Norepinephrine
• Noradrenaline,(+)
• (+/-)-norepinephrine
• (.+-.)-Noradrenaline
• (.+/-.)-Arterenol
• (.+-.)-Norepinephrine
• DL-[7-3H]norepinephrine
• (.+/-.)-Noradrenaline
• CHEMBL432
• D06GJW
• (.+/-.)-Norepinephrine
• WLN: Z1YQR CQ DQ
• SCHEMBL2610
• NORADRENALINE DL FORM
• Norepinephrine, (+)-Isomer
• GTPL484
• Norepinephrine, (+,-)-Isomer
• C(O)(CN)c1ccc(O)c(O)c1
• BDBM35234
• DTXSID20858964
• NORADRENALINE, (+/-)-
• BCP04227
• NOREPINEPHRINE DL-FORM [MI]
• 1, 4-(2-amino-1-hydroxyethyl)-
• 4-(1-Hydroxy-2-aminoethyl)catechol
• PDSP1_001514
• PDSP2_001498
• AKOS000123495
• AKOS022180874
• CCG-204148
• HR-0338
• SDCCGSBI-0050041.P003
• NCGC00185992-01
• NCGC00185992-02
• 1-(3,4-Dihydroxy)phenyl-2-aminoethanol
• AC-10030
• Benzyl alcohol,4-dihydroxy-, (.+-.)-
• LS-42677
• LS-42678
• FT-0603221
• FT-0658803
• FT-0679201
• (+-)-4-(2-amino-1-hydroxyethyl)pyrocatechol
• 4-(2-amino-1-hydroxy-ethyl)benzene-1,2-diol
• EN300-245335
• 1, 4-(2-amino-1-hydroxyethyl)-, (.+-.)-
• 4-(2-Amino-1-hydroxyethyl)-1,2-benzenediol #
• L000933
• SR-01000075279-3
• 4-[(1rs)-2-amino-1-hydroxyethyl]-1,2-benzenediol
• Q27087994
• 1,2-Benzenediol, 4-(2-amino-1-hydroxyethyl)-, (dl)-
• 1,2-Benzenediol, 4-(2-amino-1-hydroxyethyl)-, (RS)-
• 1,2-BENZENEDIOL, 4-(2-AMINO-1-HYDROXYETHYL)-, (+/-)-
• Benzyl alcohol, .alpha.-(aminomethyl)-3,4-dihydroxy-, (.+/-.)-
• DL-Arterenol, dl-Norepinephrine, EINECS 205-337-9, (+/-)-Noradrenaline
• 104655-07-4

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9891	98.91%
Caco-2	-	0.9041	90.41%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5805	58.05%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9725	97.25%
OATP1B3 inhibitior	+	0.9588	95.88%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9859	98.59%
P-glycoprotein inhibitior	-	0.9908	99.08%
P-glycoprotein substrate	-	0.9398	93.98%
CYP3A4 substrate	-	0.8080	80.80%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4514	45.14%
CYP3A4 inhibition	-	0.9209	92.09%
CYP2C9 inhibition	-	0.9675	96.75%
CYP2C19 inhibition	-	0.9446	94.46%
CYP2D6 inhibition	-	0.9798	97.98%
CYP1A2 inhibition	-	0.9135	91.35%
CYP2C8 inhibition	-	0.9138	91.38%
CYP inhibitory promiscuity	-	0.8839	88.39%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.7208	72.08%
Carcinogenicity (trinary)	Non-required	0.6152	61.52%
Eye corrosion	-	0.7397	73.97%
Eye irritation	-	0.5834	58.34%
Skin irritation	-	0.5405	54.05%
Skin corrosion	-	0.7476	74.76%
Ames mutagenesis	-	0.6870	68.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.7372	73.72%
Micronuclear	-	0.6168	61.68%
Hepatotoxicity	-	0.9125	91.25%
skin sensitisation	+	0.7536	75.36%
Respiratory toxicity	+	0.9333	93.33%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.8811	88.11%
Acute Oral Toxicity (c)	II	0.4487	44.87%
Estrogen receptor binding	-	0.7542	75.42%
Androgen receptor binding	-	0.6528	65.28%
Thyroid receptor binding	-	0.5833	58.33%
Glucocorticoid receptor binding	-	0.5305	53.05%
Aromatase binding	-	0.8774	87.74%
PPAR gamma	-	0.6357	63.57%
Honey bee toxicity	-	0.8617	86.17%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	-	0.8935	89.35%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL229	P35348	Alpha-1a adrenergic receptor	9.1 nM	EC50	via Super-PRED
CHEMBL1867	P08913	Alpha-2a adrenergic receptor	66 nM	Ki	via Super-PRED
CHEMBL1942	P18089	Alpha-2b adrenergic receptor	61.66 nM	EC50	via Super-PRED
CHEMBL1916	P18825	Alpha-2c adrenergic receptor	63 nM	Ki	via Super-PRED
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	707.9 nM	Potency	via Super-PRED
CHEMBL246	P13945	Beta-3 adrenergic receptor	5.5 nM	EC50	via Super-PRED
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	794.3 nM	Potency	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	11.2 nM	Potency	via Super-PRED
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	501.2 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.75%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.70%	99.15%
CHEMBL3902	P09211	Glutathione S-transferase Pi	86.74%	93.81%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.33%	94.45%
CHEMBL3492	P49721	Proteasome Macropain subunit	86.28%	90.24%
CHEMBL4208	P20618	Proteasome component C5	84.76%	90.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.94%	100.00%
CHEMBL2581	P07339	Cathepsin D	80.72%	98.95%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	80.65%	97.23%

Plants that contains it

• Portulaca oleracea

Cross-Links

• PubChem: 951
• NPASS: NPC115627
• ChEMBL: CHEMBL432
• LOTUS: LTS0150009
• wikiData: Q27087994