Octopamine

Details

• Internal ID: 2a94d64c-8fe9-4cbf-83d2-adef881d1bc8
• Taxonomy: Benzenoids > Phenols > 1-hydroxy-2-unsubstituted benzenoids
• IUPAC Name: 4-(2-amino-1-hydroxyethyl)phenol
• SMILES (Canonical): C1=CC(=CC=C1C(CN)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C(CN)O)O
• InChI: InChI=1S/C8H11NO2/c9-5-8(11)6-1-3-7(10)4-2-6/h1-4,8,10-11H,5,9H2
• InChI Key: QHGUCRYDKWKLMG-UHFFFAOYSA-N
• Popularity: 4,354 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₁₁NO₂
• Molecular Weight: 153.18 g/mol
• Exact Mass: 153.078978594 g/mol
• Topological Polar Surface Area (TPSA): 66.50 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): 0.38
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• 104-14-3
• Norsynephrine
• 4-(2-Amino-1-hydroxyethyl)phenol
• Norsympatol
• Octopamina
• octopaminum
• ND 50
• 1-(p-Hydroxyphenyl)-2-aminoethanol
• alpha-(Aminoethyl)-4-hydroxybenzenemethanol
• alpha-(Aminomethyl)-p-hydroxybenzyl alcohol
• 4-Octopamine
• DTXSID7043873
• Benzenemethanol, alpha-(aminomethyl)-4-hydroxy-
• 14O50WS8JD
• CHEBI:17134
• ND-50
• NSC-757399
• DTXCID5023873
• para-Octopamine
• 1-(4-Hydroxyphenyl)-2-aminoethanol
• Octopamine 1531
• RefChem:56540
• C01CA18
• 203-179-5
• Norsympathol
• Norphen
• Analet
• Norden
• Octopamine [INN]
• Paraoxyphenyl aminoethanol
• WIN 5512
• alpha-(aminomethyl)-4-hydroxybenzenemethanol
• Octapamine
• p-Norsynephrin
• 1,3-Benzenediol,4-(2-aminoethyl)-
• NCGC00015760-06
• Octopaminum [Latin]
• Octopamina [Spanish]
• .alpha.-(Aminomethyl)-p-hydroxybenzyl alcohol
• Octopaminum [INN-Latin]
• Octopamina [INN-Spanish]
• Octopamin
• 2-amino-1-(4-hydroxyphenyl)ethan-1-ol
• beta-hydroxytyramine
• CAS-104-14-3
• alpha-Aminoethyl-4-hydroxybenzylalkohol
• alpha-(Aminoethyl)-p-hydroxybenzyl alcohol
• benzene, 1-(2-amino-1-hydroxy)ethyl-4-hydroxy-
• EINECS 203-179-5
• BRN 1211019
• UNII-14O50WS8JD
• 4-(2-amino-1-hydroxyethyl)phenol;hydrochloride
• 2-Amino-1-(4-hydroxyphenyl)ethanol
• 4-(2-Amino-1-hydroxy-ethyl)phenol
• Spectrum_000201
• OCTOPAMINE [MI]
• Prestwick0_000949
• Prestwick1_000949
• Prestwick2_000949
• Prestwick3_000949
• Spectrum2_000222
• Spectrum3_000275
• Spectrum4_000402
• Spectrum5_001543
• (.+/-.)-Octopamine
• Benzyl alcohol, alpha-(aminomethyl)-p-hydroxy-
• OCTOPAMINE [MART.]
• OCTOPAMINE [WHO-DD]
• Lopac0_000932
• SCHEMBL22605
• BSPBio_000918
• BSPBio_001750
• KBioGR_000664
• KBioSS_000681
• 4-13-00-02656 (Beilstein Handbook Reference)
• CHEMBL53929
• DivK1c_000245
• SPBio_000263
• SPBio_003077
• BPBio1_001010
• cid_102484
• GTPL2149
• SCHEMBL6455311
• BDBM32764
• CTK4E4110
• KBio1_000245
• KBio2_000681
• KBio2_003249
• KBio2_005817
• KBio3_001250
• (A+/-)-Octopamine hydrochloride
• NINDS_000245
• ALBB-025791
• HY-B0528
• Tox21_110215
• BBL009983
• MFCD00044589
• PDSP1_001544
• PDSP2_001528
• SBB072689
• STK801377
• 4-(2-Amino-1-hydroxyethyl)phenol #
• AKOS000123349
• Tox21_110215_1
• CCG-205013
• DB13251
• NSC 757399
• SDCCGMLS-0066599.P001
• SDCCGSBI-0050906.P004
• IDI1_000245
• SMP1_000221
• 4-[(rs)-2-amino-1-hydroxyethyl]phenol
• NCGC00015760-03
• NCGC00015760-05
• NCGC00015760-07
• NCGC00015760-08
• NCGC00015760-09
• NCGC00015760-10
• NCGC00015760-12
• NCGC00015760-14
• NCGC00015760-23
• NCGC00015760-24
• NCGC00091918-03
• NCGC00091918-04
• 4-[(1rs)-2-amino-1-hydroxyethyl]phenol
• 4-[(IRS)-2-amino-1-hydroxyethyl]phenol
• SBI-0050906.P003
• DB-040514
• AB00053571
• ST45028935
• 4-(2-amino-1-hydroxy-ethyl)phenol;hydrochloride
• AB00053571-13
• AB00053571_14
• AB00053571_15
• EN300-1264124
• 104O143
• 4-(2-azanyl-1-oxidanyl-ethyl)phenol;hydrochloride
• Benzenemethanol, .alpha.-(aminomethyl)-4-hydroxy-
• Benzyl alcohol, .alpha.-(aminomethyl)-p-hydroxy-
• Q424979
• 3,5-DIBROMOTYROSINETRIFLUOROACETAMIDEMETHYLESTER
• BRD-A14240607-003-24-6
• BRD-A14240607-003-25-3
• BRD-A14240607-003-26-1
• BRD-A14240607-003-27-9
• (.+/-.)-.alpha.-(Aminomethyl)-p-hydroxybenzyl alcohol
• 64C59BC0-9C98-49EF-A853-8849F02ABAAC
• F2173-0210
• RACTOPAMINE HYDROCHLORIDE SUSPENSION IMPURITY, OCTOPAMINE- [USP IMPURITY]

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9949	99.49%
Caco-2	+	0.7081	70.81%
Blood Brain Barrier	-	0.9250	92.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Lysosomes	0.5754	57.54%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9336	93.36%
OATP1B3 inhibitior	+	0.9573	95.73%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9780	97.80%
P-glycoprotein inhibitior	-	0.9899	98.99%
P-glycoprotein substrate	-	0.8886	88.86%
CYP3A4 substrate	-	0.7905	79.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.5117	51.17%
CYP3A4 inhibition	-	0.8626	86.26%
CYP2C9 inhibition	-	0.9746	97.46%
CYP2C19 inhibition	-	0.9142	91.42%
CYP2D6 inhibition	-	0.9636	96.36%
CYP1A2 inhibition	-	0.9294	92.94%
CYP2C8 inhibition	-	0.7591	75.91%
CYP inhibitory promiscuity	-	0.8952	89.52%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.6018	60.18%
Carcinogenicity (trinary)	Non-required	0.6160	61.60%
Eye corrosion	+	0.7277	72.77%
Eye irritation	+	0.8021	80.21%
Skin irritation	-	0.5421	54.21%
Skin corrosion	-	0.7084	70.84%
Ames mutagenesis	-	0.8624	86.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.8415	84.15%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.7003	70.03%
skin sensitisation	+	0.6646	66.46%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.7517	75.17%
Acute Oral Toxicity (c)	II	0.7545	75.45%
Estrogen receptor binding	-	0.7903	79.03%
Androgen receptor binding	-	0.6941	69.41%
Thyroid receptor binding	-	0.7713	77.13%
Glucocorticoid receptor binding	-	0.7884	78.84%
Aromatase binding	-	0.8852	88.52%
PPAR gamma	-	0.7096	70.96%
Honey bee toxicity	-	0.8740	87.40%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	-	0.9582	95.82%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1899	P46098	Serotonin 3a (5-HT3a) receptor	24 nM	EC50	PMID: 18033297

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.25%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.55%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.48%	94.45%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	85.73%	97.23%
CHEMBL3902	P09211	Glutathione S-transferase Pi	84.26%	93.81%
CHEMBL242	Q92731	Estrogen receptor beta	84.05%	98.35%
CHEMBL2581	P07339	Cathepsin D	83.50%	98.95%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	83.29%	93.10%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.25%	89.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.05%	99.17%

Plants that contains it

• Citrus × aurantium
• Citrus × aurantium nothof. deliciosa
• Lyallia kerguelensis

Cross-Links

• PubChem: 4581
• NPASS: NPC145638
• ChEMBL: CHEMBL53929
• LOTUS: LTS0111281
• wikiData: Q424979