(2R,3R)-2-hydroxy-3-methylbutanedioic acid; 4-(2-amino-1-hydroxyethyl)benzene-1,2-diol

• ChemBase ID: 132711
• Molecular Formular: C13H19NO8
• Molecular Mass: 317.29186
• Monoisotopic Mass: 317.11106657
• SMILES: C[C@H]([C@H](C(=O)O)O)C(=O)O.c1cc(c(cc1C(CN)O)O)O
• Canonical SMILES: OC(=O)[C@@H]([C@H](C(=O)O)C)O.NCC(c1ccc(c(c1)O)O)O
• InChI: InChI=1S/C8H11NO3.C5H8O5/c9-4-8(12)5-1-2-6(10)7(11)3-5;1-2(4(7)8)3(6)5(9)10/h1-3,8,10-12H,4,9H2;2-3,6H,1H3,(H,7,8)(H,9,10)/t;2-,3-/m.1/s1
• InChIKey: PDZZSMDCBWCGRN-GEHKUQKJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-2-hydroxy-3-methylbutanedioic acid; 4-(2-amino-1-hydroxyethyl)benzene-1,2-diol
• IUPAC Traditional name: noradrenaline D-threo-3-methylmalate
• Synonyms: (±)-Arterenol (+)-bitartrate salt; (±)-Noradrenalin (+)-bitartrate salt; 1-(3,4-Dihydroxyphenyl)-2-aminoethanol (+)-bitartrate salt; 3,4-Dihydroxyphenylethanolamine (+)-bitartrate salt; (±)-Norepinephrine (+)-bitartrate salt

Database IDs

• CAS Number: 3414-63-9
• EC Number: 222-307-0
• MDL Number: MFCD00132876
• PubChem SID: 162226988; 24278207
• PubChem CID: 16218840

CALCULATED PROPERTIES

• Acid pKa: 9.500885
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -3.0654356
• LogD (pH = 7.4): -1.8244592
• Log P: -0.6835134
• Molar Refractivity: 44.4557 cm^3
• Polarizability: 17.37873 Å^3
• Polar Surface Area: 86.71 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: CZ8462500
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 26/27/28
• Safety Statements: 28-36/37-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330
• GHS Precautionary statements: P260-P264-P280-P284-P302 + P350-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2

Pharmacology Properties

• Gene Information: human ... ADRA1A(148), ADRA1B(147), ADRA1D(146), ADRA2A(150), ADRA2B(151), ADRA2C(152), ADRB1(153), ADRB2(154), ADRB3(155)

DETAILS

Sigma Aldrich - A0937

Biochem/physiol Actions
Adrenergic neurotransmitter