Norepinephrine

Details

• Internal ID: a94546ff-b84e-4ee4-b6bb-35ee8397e6d5
• Taxonomy: Benzenoids > Phenols > Benzenediols > Catechols
• IUPAC Name: 4-[(1R)-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=C1[C@H](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/t8-/m0/s1
• InChI Key: SFLSHLFXELFNJZ-QMMMGPOBSA-N
• Popularity: 142,163 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

• noradrenaline
• L-Noradrenaline
• 51-41-2
• Levarterenol
• Arterenol
• (R)-Noradrenaline
• Levophed
• (-)-Norepinephrine
• L-Norepinephrine
• Levonor
• (-)-NORADRENALINE
• (R)-Norepinephrine
• Aktamin
• L-arterenol
• Levonoradrenaline
• (-)-Arterenol
• Levonorepinephrine
• 4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol
• Adrenor
• Sympathin E
• (R)-(-)-Norepinephrine
• Norepirenamine
• Noradrenalin
• Nor-Epirenan
• norepinephrinum
• Noradrenalinum
• Levarterenolo
• Levoarterenol
• Noradrenalina
• Noreinefrina
• (R)-4-(2-Amino-1-hydroxyethyl)-1,2-benzenediol
• Norartrinal
• Nor adrenalin
• D-(-)-Noradrenaline
• L-3,4-dihydroxyphenylethanolamine
• Noradrenalin, l-
• norepinefrina
• Levarterenolo [DCIT]
• Noradrenalina [Italian]
• l-1-(3,4-Dihydroxyphenyl)-2-aminoethanol
• l-2-Amino-1-(3,4-dihydroxyphenyl)ethanol
• (-)-(R)-Norepinephrine
• (-)-alpha-(Aminomethyl)protocatechuyl alcohol
• Noreinefrina [INN-Spanish]
• Nor adrenalin (TN)
• Norepinephrinum [INN-Latin]
• L-alpha-(aminomethyl)-3,4-dihydroxybenzyl alcohol
• 4-[(1R)-2-Amino-1-hydroxyethyl]-1,2-benzenediol
• Ecteinascidins
• 1,2-Benzenediol, 4-(2-amino-1-hydroxyethyl)-, (R)-
• Nor-adrenaline
• UNII-X4W3ENH1CV
• Norepinephrine [INN:JAN]
• EINECS 200-096-6
• 1,2-Benzenediol, 4-[(1R)-2-amino-1-hydroxyethyl]-
• NSC-757246
• BRN 4231961
• DTXSID5023378
• Norepinephrine (INN)
• HSDB 7772
• Noradrenaline (JP15)
• Norepinephrine l-Tartrate (1:1)
• (-)-Arterenol free base
• Norepinephrine Noradrenalin
• X4W3ENH1CV
• CHEMBL1437
• 51-41-2 (free base)
• DTXCID203378
• Benzyl alcohol, alpha-(aminomethyl)-3,4-dihydroxy-, (-)-
• Norepinephrine [INN:BAN:JAN]
• CHEBI:18357
• 4-[(1R)-2-amino-1-hydroxy-ethyl]benzene-1,2-diol
• 1,2-Benzenediol, 4-((R)-2-amino-1-hydroxyethyl)-
• NSC 757246
• NOREPINEPHRINE [INN]
• NORADRENALINE (MART.)
• NORADRENALINE [MART.]
• d-Arterenol
• (1R)-2-AMINO-1-(3,4-DIHYDROXYPHENYL)ETHANOL
• 1,2-Benzenediol, 4-((1R)-2-amino-1-hydroxyethyl)-
• D53D5E3A-2360-4CA9-8031-6C2CD4062FD5
• (+)-Noradrenaline
• NOREPINEPHRINE (USP IMPURITY)
• NOREPINEPHRINE [USP IMPURITY]
• 1,2-BENZENEDIOL, 4-(2-AMINO-1-HYDROXYETHYL)-, (R)-(R-(R*,R*))-2,3-DIHYDROXYBUTANEDIOATE
• ADRENALINE IMPURITY B (EP IMPURITY)
• ADRENALINE IMPURITY B [EP IMPURITY]
• ADRENALINE TARTRATE IMPURITY B (EP IMPURITY)
• ADRENALINE TARTRATE IMPURITY B [EP IMPURITY]
• noradranalinum
• noradrAnaline
• norepinephrin-
• R-norepinephrine
• 1-Noradrenaline
• DermX
• E5E
• (R)-4-(2-Amino-1-hydroxyethyl)benzene-1,2-diol
• ALBB-006229
• (?)-Norepinephrine
• Spectrum_001009
• Noradrenaline (JP17)
• Spectrum2_001064
• Spectrum3_000520
• Spectrum4_000078
• Spectrum5_001068
• bmse000404
• D07MOX
• D0R2UN
• 1,2-Benzenediol,4-(2-amino-1-hydroxyethyl)-
• NORADRENALINE [JAN]
• NOREPINEPHRINE [MI]
• SCHEMBL2609
• BSPBio_002079
• GTPL505
• KBioGR_000635
• KBioSS_001489
• NOREPINEPHRINE [HSDB]
• 4-(2-Amino-1-hydroxyethyl)-1,2-benzenediol
• MLS006010883
• DivK1c_000230
• NOREPINEPHRINE [VANDF]
• SPECTRUM1500436
• SPBio_001048
• Levarterenol;Levophed;Arterenol
• SGCUT00123
• NOREPINEPHRINE [WHO-DD]
• HMS500L12
• KBio1_000230
• KBio2_001489
• KBio2_004057
• KBio2_006625
• KBio3_001579
• C01CA03
• NINDS_000230
• 1-3,4-Dihydroxyphenylethanolamine
• HMS1920B08
• HMS2089E18
• HMS2091J08
• HMS3887I07
• Pharmakon1600-01500436
• to_000024
• Tox21_301944
• BDBM50029051
• CCG-40104
• MFCD00025592
• NSC757246
• PDSP1_001111
• PDSP2_001095
• s9507
• STK503776
• AKOS006345192
• AKOS015854572
• CS-O-30989
• DB00368
• SDCCGSBI-0050082.P004
• CAS-51-41-2
• IDI1_000230
• NCGC00159406-03
• NCGC00159406-04
• NCGC00159406-05
• NCGC00159406-06
• NCGC00159406-07
• NCGC00159406-08
• NCGC00159406-09
• NCGC00159406-10
• NCGC00159406-11
• NCGC00159406-17
• NCGC00255328-01
• AS-56654
• HY-13715
• LS-42676
• SMR000058585
• (-)-Norepinephrine, >=98%, crystalline
• (R)-4-(2-Amino-1-hydroxyethyl)catechol
• SBI-0050082.P003
• 1-1-(3,4-Dihydroxyphenyl)-2-aminoethanol
• 1-2-Amino-1-(3,4-dihydroxyphenyl)ethanol
• CS-0007744
• LT03330026
• (-)-alpha-(Aminomethyl)protocatechu-yl alcohol
• C00547
• D00076
• EN300-378087
• AB00052424-06
• AB00052424_07
• AB00052424_08
• 1-alpha-(Aminomethyl)-3,4-dihydroxybenzyl alcohol
• Q186242
• W-105896
• (-)-alpha-(Aminomethyl)-3,4-dihydroxybenzyl alcohol
• (-)-.ALPHA.-(AMINOMETHYL)-3,4-DIHYDROXYBENZYL ALCOHOL
• 1,2-Benzenediol, 4-(2-amino-1-hydroxyethyl)-, (R)-(-)-
• 1,2-Benzenediol, 4-(2-amino-1-hydroxyethyl)-, (R)-(9CI)
• Benzyl alcohol, .alpha.-(aminomethyl)-3,4-dihydroxy-, (+)-
• 65277-62-5

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
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	15848.9 nM	Potency	via CMAUP
CHEMBL229	P35348	Alpha-1a adrenergic receptor	2187.76 nM; 9.1 nM; 9.1 nM	EC50; EC50; EC50	PMID: 8831777; PMID: 26125514; via Super-PRED
CHEMBL232	P35368	Alpha-1b adrenergic receptor	20400 nM	Ki	PMID: 19857969
CHEMBL1867	P08913	Alpha-2a adrenergic receptor	371.54 nM; 66 nM; 371.54 nM; 371.54 nM; 371.54 nM	EC50; Ki; EC50; EC50; EC50	PMID: 18578476; via Super-PRED; PMID: 19886609; PMID: 17630725; PMID: 15566287
CHEMBL1942	P18089	Alpha-2b adrenergic receptor	61.66 nM; 61.66 nM; 61.66 nM; 61.66 nM	EC50; EC50; EC50; EC50	PMID: 17630725; PMID: 18578476; via Super-PRED; PMID: 15566287
CHEMBL1916	P18825	Alpha-2c adrenergic receptor	794.33 nM; 794.33 nM; 794.33 nM; 63 nM; 794.33 nM	EC50; EC50; EC50; Ki; EC50	PMID: 17630725; PMID: 18578476; PMID: 19886609; via Super-PRED; PMID: 15566287
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	707.9 nM; 707.9 nM; 3548.1 nM; 2238.7 nM	Potency; Potency; Potency; Potency	via CMAUP; via Super-PRED; via CMAUP; via CMAUP
CHEMBL210	P07550	Beta-2 adrenergic receptor	3300 nM; 96700 nM	Ki; Ki	PMID: 27132867; PMID: 19857969
CHEMBL246	P13945	Beta-3 adrenergic receptor	6.3 nM; 5.5 nM; 5.5 nM	EC50; EC50; EC50	PMID: 18083578; via Super-PRED; PMID: 18083578
CHEMBL1293237	P54132	Bloom syndrome protein	3548.1 nM	Potency	via CMAUP
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	794.3 nM; 794.3 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL217	P14416	Dopamine D2 receptor	8.00E-05 nM	IC50	PMID: 3156993
CHEMBL1293224	P10636	Microtubule-associated protein tau	5623.4 nM; 6309.6 nM; 3548.1 nM; 3162.3 nM; 3981.1 nM; 1258.9 nM; 6309.6 nM; 10000 nM; 7079.5 nM	Potency; Potency; Potency; Potency; Potency; Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP; via CMAUP; via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	11.2 nM; 11.2 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	501.2 nM; 891.3 nM; 501.2 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; 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

• Albizia julibrissin
• Crataegus monogyna
• Lathyrus oleraceus
• Mimosa pudica
• Murraya paniculata
• Musa × paradisiaca
• Phaseolus coccineus
• Portulaca grandiflora
• Portulaca oleracea
• Solanum tuberosum

Cross-Links

• PubChem: 439260
• NPASS: NPC169207
• ChEMBL: CHEMBL1437
• LOTUS: LTS0169380
• wikiData: Q186242