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56-45-1 molecular structure
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(2S)-2-amino-3-hydroxypropanoic acid

ChemBase ID: 19
Molecular Formular: C3H7NO3
Molecular Mass: 105.09258
Monoisotopic Mass: 105.04259309
SMILES and InChIs

SMILES:
OC[C@H](N)C(=O)O
Canonical SMILES:
OC[C@@H](C(=O)O)N
InChI:
InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m0/s1
InChIKey:
MTCFGRXMJLQNBG-REOHCLBHSA-N

Cite this record

CBID:19 http://www.chembase.cn/molecule-19.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2S)-2-amino-3-hydroxypropanoic acid
IUPAC Traditional name
L-serine
Synonyms
(-)-Serine
Serine
L-Ser
L-3-Hydroxy-2-aminopropionic acid
L-(-)-Serine
b-Hydroxy-L-alanine
3-Hydroxyalanine
2-Amino-3-hydroxypropionic acid
(S)-Serine
(S)-a-Amino-b-hydroxypropionic acid
(S)-2-Amino-3-hydroxypropanoic acid
L-Serine
(S)-2-Amino-3-hydroxypropanoic acid
beta-HYDROXYALANINE
L-SERINE, USP GRADE
2-Amino-3-hydroxypropanoic acid
L-2-Amino-3-hydroxypropionic acid
(S)-2-Amino-3-hydroxypropionic acid
Serinum
Hydroxyalanine
L-Serine
H-Ser-OH
Serine
(S)-2-氨基-3-羟基丙酸
L-丝氨酸
丝氨酸
CAS Number
56-45-1
EC Number
206-130-6
200-274-3
MDL Number
MFCD00064224
Beilstein Number
1721404
Merck Index
148460
PubChem SID
24888286
24899473
24899605
160963482
24887156
24899599
46506450
PubChem CID
617
5951
CHEBI ID
17115
CHEMBL
11298
Chemspider ID
5736
DrugBank ID
DB00133
IUPHAR ligand ID
726
Unique Ingredient Identifier
452VLY9402
Wikipedia Title
Serine

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 2.03399  H Acceptors
H Donor LogD (pH = 5.5) -3.8875728 
LogD (pH = 7.4) -3.8992038  Log P -3.8877351 
Molar Refractivity 22.041 cm3 Polarizability 9.0643015 Å3
Polar Surface Area 83.55 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -3.42  LOG S 0.66 
Solubility (Water) 4.80e+02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
1 M HCl: soluble0.5 M at 20 °C, clear, colorless expand Show data source
425 g/L expand Show data source
H2O: soluble50 mg/mL expand Show data source
soluble in water expand Show data source
Apperance
powder expand Show data source
white crystals or powder expand Show data source
Melting Point
> 228°C expand Show data source
214-224°C dec. expand Show data source
222 °C (dec.)(lit.) expand Show data source
246 °C decomp. expand Show data source
Density
1.603 g/cm3 (22 °C) expand Show data source
Optical Rotation
[α]20/D +13±0.5°, c = 5% in 5 M HCl expand Show data source
[α]20/D +13±1°, c = 5% in 5 M HCl expand Show data source
+15 (c=9 in 1N HCl) expand Show data source
Absorption Wavelength
λ: 260 nm Amax: 0.05 expand Show data source
λ: 280 nm Amax: 0.05 expand Show data source
Hydrophobicity(logP)
-4 expand Show data source
pKa
2.21 (carboxyl), 9.15 (amino) expand Show data source
Storage Condition
Room Temperature (15-30°C) expand Show data source
Storage Warning
IRRITANT expand Show data source
RTECS
VT8100000 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
1 expand Show data source
TSCA Listed
false expand Show data source
expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Purity
≥99% expand Show data source
≥98.5% expand Show data source
≥99% (TLC) expand Show data source
≥99.0% (NT) expand Show data source
≥99.5% (NT) expand Show data source
95+% expand Show data source
97% expand Show data source
98% expand Show data source
98.5-101.0% expand Show data source
99% expand Show data source
Grade
certified reference material expand Show data source
EP expand Show data source
Ph Eur expand Show data source
PharmaGrade expand Show data source
ReagentPlus® expand Show data source
TraceCERT® expand Show data source
USP expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Suitability
meets EP, USP testing specifications expand Show data source
suitable for cell culture expand Show data source
suitable for manufacturing use expand Show data source
Ignition Residue
≤0.1% (as SO4) expand Show data source
Impurities
≤0.3% foreign amino acids expand Show data source
≤0.5% foreign amino acids expand Show data source
endotoxin, tested expand Show data source
insoluble matter, passes filter test expand Show data source
Cation Traces
Al: ≤5 mg/kg expand Show data source
As: ≤0.1 mg/kg expand Show data source
Ba: ≤5 mg/kg expand Show data source
Bi: ≤5 mg/kg expand Show data source
Ca: ≤50 mg/kg expand Show data source
Cd: ≤5 mg/kg expand Show data source
Co: ≤5 mg/kg expand Show data source
Cr: ≤5 mg/kg expand Show data source
Cu: ≤5 mg/kg expand Show data source
Fe: ≤5 mg/kg expand Show data source
K: ≤50 mg/kg expand Show data source
Li: ≤5 mg/kg expand Show data source
Mg: ≤5 mg/kg expand Show data source
Mn: ≤5 mg/kg expand Show data source
Mo: ≤5 mg/kg expand Show data source
Na: ≤50 mg/kg expand Show data source
NH4+: ≤100 mg/kg expand Show data source
Ni: ≤5 mg/kg expand Show data source
Pb: ≤5 mg/kg expand Show data source
Sr: ≤5 mg/kg expand Show data source
Zn: ≤5 mg/kg expand Show data source
Antion Traces
chloride (Cl-): ≤50 mg/kg expand Show data source
sulfate (SO42-): ≤100 mg/kg expand Show data source
sulfate (SO42-): ≤50 mg/kg expand Show data source
Biological Source
from non-animal source expand Show data source
Shelf Life
(limited shelf life, expiry date on the label) expand Show data source
Loss on Drying
≤0.1% loss on drying, 20 °C (HV) expand Show data source
≤0.2% loss on drying, 110 °C expand Show data source
Quality Level
GMP-COMPENDIA expand Show data source
λ
0.5 M in 1 M HCl expand Show data source
Pharmacopeia
testing & handling conforms to Pharmacopeia expand Show data source
Product Line
BioUltra expand Show data source
Linear Formula
HOCH2CH(NH2)CO2H expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich MP Biomedicals MP Biomedicals Wikipedia Wikipedia
DrugBank - DB00133 external link
Item Information
Drug Groups approved; nutraceutical
Description A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from glycine or threonine. It is involved in the biosynthesis of purines; pyrimidines; and other amino acids. [PubChem]
Indication Used as a natural moisturizing agent in some cosmetics and skin care products.
Pharmacology Serine is classified as a nutritionally non-essential amino acid. Serine is critical for the production of the body's proteins, enzymes and muscle tissue. Serine is needed for the proper metabolism of fats and fatty acids. It also helps in the production of antibodies. Serine is used as a natural moisturizing agent in some cosmetics and skin care products. The main source of essential amino acids is from the diet, non-essential amino acids are normally synthesize by humans and other mammals from common intermediates.
Affected Organisms
Humans and other mammals
External Links
Wikipedia
DrugBank - DB03375 external link
Drug information: experimental
Sigma Aldrich - S4311 external link
Biochem/physiol Actions
通过丝氨酸羟甲基转移酶获得甘氨酸时的前体。
Sigma Aldrich - 84959 external link
Biochem/physiol Actions
Precursor of glycine by serine hydroxymethyltransferase.
Other Notes
Synthesis of labels for protonation studies by Fourier Transform infrared methods1; Stabilizes mung bean nuclease at pH values below seven2; Amino acid spacing in isotachophoresis on polyacrylamide gel - a critical evaluation3; Growth requirement of various microorganisms4
Sigma Aldrich - S4500 external link
Biochem/physiol Actions
通过丝氨酸羟甲基转移酶获得甘氨酸时的前体。
包装
1 kg in poly bottle
1, 100 g in poly bottle
法律信息
ReagentPlus 注册商标 Sigma-Aldrich Co. LLC
Sigma Aldrich - 78682 external link
Biochem/physiol Actions
Precursor of glycine by serine hydroxymethyltransferase.
Sigma Aldrich - S1315 external link
Biochem/physiol Actions
Precursor of glycine by serine hydroxymethyltransferase.
Packaging
Manufactured and Packaged under cGMP
Sigma Aldrich - 84960 external link
Biochem/physiol Actions
Precursor of glycine by serine hydroxymethyltransferase.
Sigma Aldrich - 54763 external link
Analysis Note
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34. This CRM is traceable to NIST SRM.
Biochem/physiol Actions
Precursor of glycine by serine hydroxymethyltransferase.
General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
Legal Information
TraceCERT is a registered trademark of Sigma-Aldrich Co. LLC
MP Biomedicals - 02194737 external link
Cell Culture Reagent
Purity: 99+%
Crystalline
MP Biomedicals - 02199560 external link
White powder
MP Biomedicals - 02102873 external link
Purity: 99+%
Crystalline

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Has been used in a synthesis of D-amino acids. The configuration is inverted by conversion of the carboxyl group to the new alkyl chain by reaction with an organolithium reagent to give the ketone, which is deoxygenated by Raney nickel desulfurization of the thioketal, the hydroxymethyl group becoming the new carboxyl group by oxidation with oxygen over a Pt catalyst: J. Am. Chem. Soc., 106, 1095 (1984):
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PATENTS

PATENTS

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INTERNET

INTERNET

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