MiMeDB: Showing metabocard for Aromatic amino acid (MMDBc0031941)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:55:53 UTC

Update Date

2022-08-31 18:26:38 UTC

Metabolite ID

MMDBc0031941

Metabolite Identification

Common Name

Aromatic amino acid

Description

Amino acids that include an aromatic ring

Structure

MOL SDF PDB SMILES InChI


  Mrv1652302271819192D          

 16 17  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4991   -0.6674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9840    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4991    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8347    1.4211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8045    0.0862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1401    0.8399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6551    1.5074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9907    2.2610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  8  1  0  0  0  0
  3  1  1  0  0  0  0
  3 13  1  0  0  0  0
  2  4  1  0  0  0  0
  4  3  1  0  0  0  0
  2  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 15  2  0  0  0  0
 10 11  2  0  0  0  0
 11 15  1  0  0  0  0
 13 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031941

> <DATABASE_NAME>
MIME

> <SMILES>
NC(CC1=CNC2=C1C=C(O)C=C2)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H12N2O3/c12-9(11(15)16)3-6-5-13-10-2-1-7(14)4-8(6)10/h1-2,4-5,9,13-14H,3,12H2,(H,15,16)

> <INCHI_KEY>
LDCYZAJDBXYCGN-UHFFFAOYSA-N

> <FORMULA>
C11H12N2O3

> <MOLECULAR_WEIGHT>
220.2246

> <EXACT_MASS>
220.08479226

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
22.028091206517423

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid

> <ALOGPS_LOGP>
-1.56

> <JCHEM_LOGP>
-1.3896984621581003

> <ALOGPS_LOGS>
-1.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.79536661937528

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.152663935897665

> <JCHEM_PKA_STRONGEST_BASIC>
9.18065085700301

> <JCHEM_POLAR_SURFACE_AREA>
99.33999999999999

> <JCHEM_REFRACTIVITY>
58.18370000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.63e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
DL-5-hydroxytryptophan

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-FEB-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-18         0                                  
HETATM    1  N   UNK     0       1.334  -0.770   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -2.798  -1.246   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -3.703   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.798   1.246   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.425   2.653   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.235   0.161   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.862   1.568   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667   3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.001   0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.956   2.814   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -5.583   4.221   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    8    4    5                                                  
CONECT    3    1   13    4                                                  
CONECT    4    2    3                                                       
CONECT    5    2    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    2    7    9                                                  
CONECT    9    8   15                                                       
CONECT   10    7   11                                                       
CONECT   11   10   15                                                       
CONECT   12   13                                                            
CONECT   13    3   12   14                                                  
CONECT   14   13                                                            
CONECT   15    9   11   16                                                  
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

Synonyms

Value	Source
(+-)-5-Hydroxytryptophan	ChEBI
5-HTP	ChEBI
5-Hydroxy-DL-tryptophan	ChEBI
5-Hydroxytryptophan DL-form	ChEBI
DL-5-HTP	ChEBI
DL-5-Hydroxytryptophan	ChEBI
(S)-5-Hydroxytryptophan	HMDB
5-Hydroxy-tryptophan	HMDB
5-Hydroxyl-L-tryptophan	HMDB
5-Hydroxytryptophan	HMDB, MeSH
5-Hydroxytryptophan L form	HMDB
5-Hydroxytryptophan L-form	HMDB
Cincofarm	HMDB
Hydroxytryptophan	HMDB, MeSH
L-5-Hydroxytryptophan	HMDB
Levothym	HMDB
Levotinine	HMDB
Oxitriptan	HMDB, MeSH
Oxyfan	HMDB
Oxytryptophan	HMDB, MeSH
Pretonine	HMDB
Quietim	HMDB
Serotonyl	HMDB
Telesol	HMDB
Triptene	HMDB
5 Hydroxytryptophan	MeSH
5-Hydroxy- tryptophan	MeSH
Tryptophan, 5 hydroxy	MeSH

Molecular Formula

C₁₁H₁₂N₂O₃

Average Mass

220.2246

Monoisotopic Mass

220.08479226

IUPAC Name

2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid

Traditional Name

DL-5-hydroxytryptophan

CAS Registry Number

Not Available

SMILES

NC(CC1=CNC2=C1C=C(O)C=C2)C(O)=O

InChI Identifier

InChI=1S/C11H12N2O3/c12-9(11(15)16)3-6-5-13-10-2-1-7(14)4-8(6)10/h1-2,4-5,9,13-14H,3,12H2,(H,15,16)

InChI Key

LDCYZAJDBXYCGN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as serotonins. Serotonins are compounds containing a serotonin moiety, which consists of an indole that bears an aminoethyl a position 2 and a hydroxyl group at position 5.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Tryptamines and derivatives

Direct Parent

Serotonins

Alternative Parents

Substituents

Serotonin
Indolyl carboxylic acid derivative
Alpha-amino acid
Alpha-amino acid or derivatives
Hydroxyindole
3-alkylindole
Indole
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Amino acid
Amino acid or derivatives
Azacycle
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organonitrogen compound
Primary aliphatic amine
Organic oxide
Organopnictogen compound
Organooxygen compound
Primary amine
Carbonyl group
Organic nitrogen compound
Amine
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxytryptophan (CHEBI:28171 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	3.63 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-1.4	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	2.15	ChemAxon
pKa (Strongest Basic)	9.18	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.34 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	58.18 m³·mol⁻¹	ChemAxon
Polarizability	22.03 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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 (Non-derivatized)	splash10-0006-0390000000-3c19ae217ad78448c30f	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0097-5920000000-eb294b94875b74adc6f8	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00dl-9067000000-2ab7fbf926f4f1b43002	2017-10-06	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-0090000000-823f10e31a9f15588233	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-053r-0900000000-d763102ca4968c158d29	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-053r-0900000000-500716cec2e9f8383df7	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-00rx-2930000000-9e9f041cf524d559b331	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0090000000-44c37ec15a5546b1c353	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03di-0910000000-5e6f9e21dd30ec8c20f3	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-001i-0900000000-b656dc85b8aff47fea96	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-001i-3900000000-94c7412dbb7cb04c9f32	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0w29-0790000000-233a5164a2a4514e5bb9	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fi0-0980000000-52f402588d34f0e4bf81	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0910000000-f2841345d00a265d4104	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014j-0900000000-df31c7e703c994b797fe	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-2090000000-28b52756bfbd372bccf4	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9460000000-093dd610b11a147c2056	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00e9-9500000000-d567d2ab0b6a5e8a8a22	2017-09-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00001371

Chemspider ID

Not Available

KEGG Compound ID

C01017

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

5-Hydroxytryptophan

METLIN ID

Not Available

PubChem Compound

144

PDB ID

Not Available

ChEBI ID

28171

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Sajed T, Marcu A, Ramirez M, Pon A, Guo AC, Knox C, Wilson M, Grant JR, Djoumbou Y, Wishart DS: ECMDB 2.0: A richer resource for understanding the biochemistry of E. coli. Nucleic Acids Res. 2016 Jan 4;44(D1):D495-501. doi: 10.1093/nar/gkv1060. Epub 2015 Oct 19. [PubMed:26481353 ]

Showing metabocard for Aromatic amino acid (MMDBc0031941)

MOL for #<Metabolite:0x00007fecf424f480>

3D MOL for #<Metabolite:0x00007fecf424f480>

3D SDF for #<Metabolite:0x00007fecf424f480>

3D-SDF for #<Metabolite:0x00007fecf424f480>

PDB for #<Metabolite:0x00007fecf424f480>

3D PDB for #<Metabolite:0x00007fecf424f480>

SMILES for #<Metabolite:0x00007fecf424f480>

INCHI for #<Metabolite:0x00007fecf424f480>

Structure for #<Metabolite:0x00007fecf424f480>

3D Structure for #<Metabolite:0x00007fecf424f480>