Milk Composition Database: Showing metabocard for N-Acetylserotonin (BMDB0001238)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:42:52 UTC

Update Date

2020-05-21 16:27:05 UTC

MCDB ID

BMDB0001238

Secondary Accession Numbers

BMDB01238

Metabolite Identification

Common Name

N-Acetylserotonin

Description

N-Acetylserotonin, also known as 5-hydroxymelatonin or ASE, belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group. N-Acetylserotonin is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetylserotonin exists in all living organisms, ranging from bacteria to humans. N-Acetylserotonin participates in a number of enzymatic reactions, within cattle. In particular, N-Acetylserotonin can be biosynthesized from serotonin and acetyl-CoA; which is mediated by the enzyme serotonin N-acetyltransferase. In addition, N-Acetylserotonin and S-adenosylmethionine can be converted into melatonin and S-adenosylhomocysteine; which is catalyzed by the enzyme acetylserotonin O-methyltransferase. In cattle, N-acetylserotonin is involved in the metabolic pathway called the tryptophan metabolism pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N-(2-(5-Hydroxy-1H-indol-3-yl)ethyl)acetamide	ChEBI
N-Acetyl-5-hydroxytryptamine	ChEBI
5-Hydroxy-N-acetyltryptamine	HMDB
5-Hydroxymelatonin	HMDB
ASE	HMDB
Desmethylmelatonin	HMDB
O-Demethylmelatonin	HMDB
N-Acetylhydroxytryptamine	HMDB

Chemical Formula

C₁₂H₁₄N₂O₂

Average Molecular Weight

218.2518

Monoisotopic Molecular Weight

218.105527702

IUPAC Name

N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]acetamide

Traditional Name

N-acetylserotonin

CAS Registry Number

1210-83-9

SMILES

CC(=O)NCCC1=CNC2=C1C=C(O)C=C2

InChI Identifier

InChI=1S/C12H14N2O2/c1-8(15)13-5-4-9-7-14-12-3-2-10(16)6-11(9)12/h2-3,6-7,14,16H,4-5H2,1H3,(H,13,15)

InChI Key

MVAWJSIDNICKHF-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Hydroxyindoles

Direct Parent

Hydroxyindoles

Alternative Parents

Substituents

Hydroxyindole
3-alkylindole
Indole
1-hydroxy-2-unsubstituted benzenoid
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Carboximidic acid
Carboximidic acid derivative
Azacycle
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organic oxygen compound
Organooxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

acetamides (CHEBI:17697 )
hydroxyindoles (CHEBI:17697 )
a small molecule (N-ACETYL-SEROTONIN )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.98	ALOGPS
logP	1	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	9.56	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	65.12 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	61.8 m³·mol⁻¹	ChemAxon
Polarizability	23.59 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0f6x-0692000000-96e09fa6d98b96bcf1e4	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0fsm-0950000000-1bfd0dec31c3cbabefdd	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0udl-0495000000-4408ea40213cdc89bf39	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0159-0690000000-15c09141663fccc3546f	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0f6x-1592000000-742cca756ead51503626	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0f6x-2695000000-c377bb4d833e7c3880da	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0f6x-1592000000-742cca756ead51503626	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0f6x-2695000000-c377bb4d833e7c3880da	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f6x-0692000000-60b556c70b30588d69f4	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f6x-0595000000-687eb11cf30796ac9321	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0159-0590000000-3fa8283c51c6d0bcbb54	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0097-5910000000-ceaf51e6bbefe5537258	2017-08-28	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9280000000-17099861a602d813f195	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-0920000000-9c0d187c13aabfa510d9	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-03di-0900000000-025ebd6d665bfe7141d3	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014i-1900000000-cdac2a24252af2ce8c65	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-03yi-2900000000-4fc1ad68abd1d2588527	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-0aor-3890000000-f3ae8731ba8f76a62c23	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-03yi-2900000000-4fc1ad68abd1d2588527	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-03di-0900000000-73493993faa05c0e2d48	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0900000000-84ee5e07619ce235bd1d	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0900000000-d1d9419199ca000ac22a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-df6a45ff48d98beeb1fe	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014i-1900000000-66437c0f9179582202ff	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-4692c1200a9a8c1fa389	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9300000000-67746f3e50ff13880bea	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014i-1900000000-7e71156411b390274e26	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014i-1900000000-cfd5be5385f370d516f6	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0900000000-a458938615e76563186f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-03di-0900000000-84b4aba2486e6b07fb07	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0900000000-d7a223841dec55cf4d51	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014i-1900000000-e6590ce23a6fddb5be97	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00or-0950000000-524beb3c0eb569b36af4	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0900000000-a01ac35d32e9651b0b18	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01qd-1900000000-23a4306d4e9b966e4141	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-1590000000-6be0bcac0c1150048e43	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00os-3920000000-16b240b30f4e9fb80a10	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9300000000-60ab04a4c74a12a09ddd	2017-07-26	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Not Available	2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 29565828	details

External Links

HMDB ID

HMDB0001238

DrugBank ID

DB04275

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB031021

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

17697

References

Synthesis Reference

Balemans M G; Mans D; Smith I; Van Benthem J The influence of GABA on the synthesis of N-acetylserotonin, melatonin, O-acetyl-5-hydroxytryptophol and O-acetyl-5-methoxytryptophol in the pineal gland of the male Wistar rat. Reproduction, nutrition, development (1983), 23(1), 151-60.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735. [PubMed:29565828 ]

Showing metabocard for N-Acetylserotonin (BMDB0001238)

Structure for BMDB0001238 (N-Acetylserotonin)