(+)-Norepinephrine

Details

• Internal ID: e5b7f6ce-f6ee-4f13-8b96-65b9acda2ebf
• Taxonomy: Benzenoids > Phenols > Benzenediols > Catechols
• IUPAC Name: 4-[(1S)-2-amino-1-hydroxyethyl]benzene-1,2-diol
• 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-/m1/s1
• InChI Key: SFLSHLFXELFNJZ-MRVPVSSYSA-N
• Popularity: 653 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

• d-Norepinephrine
• (s)-norepinephrine
• (+)-Norepinephrine
• Norepinephrine, (+)-
• 887AEE91JI
• DTXSID901316081
• RefChem:905477
• DTXCID001745954
• (S)-noradrenaline
• 4-[(1S)-2-amino-1-hydroxyethyl]benzene-1,2-diol
• D-noradrenaline
• (S)-4-(2-Amino-1-hydroxyethyl)pyrocatechol
• d-Arterenol
• CHEBI:33571
• 1,2-Benzenediol, 4-[(1S)-2-amino-1-hydroxyethyl]-
• (+)-Noradrenaline
• 4-((1S)-2-amino-1-hydroxyethyl)benzene-1,2-diol
• UNII-887AEE91JI
• 1,2-BENZENEDIOL, 4-((1S)-2-AMINO-1-HYDROXYETHYL)-
• EINECS 205-750-4
• CHEMBL18824
• S-(+)-NOREPINEPHRINE
• (-)arte-renol bitartrate salt
• SCHEMBL3489077
• SCHEMBL29460319
• BDBM162127
• BENZYL ALCOHOL, alpha-(AMINOMETHYL)-3,4-DIHYDROXY-, (+)-
• PDSP1_001513
• PDSP2_001497
• SBB064179
• AKOS025117033
• NCGC00094737-01
• NCGC00094737-02
• NCGC00094737-03
• NCGC00094737-04
• AC-10037
• NS00079475
• EN300-1837474
• BRD-K39981244-001-01-5
• Q26841322

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+]	35481.3 nM	Potency	via CMAUP
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; 14125.4 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL246	P13945	Beta-3 adrenergic receptor	5.5 nM	EC50	via Super-PRED
CHEMBL1293237	P54132	Bloom syndrome protein	12589.3 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	31622.8 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	794.3 nM; 3981.1 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	3548.1 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	39810.7 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	35481.3 nM; 22387.2 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	11.2 nM	Potency	via Super-PRED
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	501.2 nM; 44668.4 nM; 17782.8 nM; 398.1 nM	Potency; Potency; Potency; Potency	via Super-PRED; via CMAUP; via CMAUP; via CMAUP

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: 5814
• NPASS: NPC118522
• ChEMBL: CHEMBL18824