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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2023-02-21 17:18:26 UTC

HMDB ID

HMDB0015188

Secondary Accession Numbers

HMDB15188

Metabolite Identification

Common Name

Mimosine

Description

Mimosine is only found in individuals that have used or taken this drug. It is an antineoplastic alanine-substituted pyridine derivative isolated from Leucena glauca. [PubChem]Mimosine causes inhibition of DNA replication, changes in the progression of the cells in the cell cycle, and apoptosis. Mimosine appears to introduce breaks into DNA. Mimosine is an iron/zinc chelator. Iron depletion induces DNA double-strand breaks in treated cells, and activates a DNA damage response that results in focal phosphorylation of histones. This leads to inhibition of DNA replication and/or DNA elongation. Some studies indicate that mimosine prevents the initiation of DNA replication, whereas other studies indicate that mimosine disrupts elongation of the replication fork by impairing deoxyribonucleotide synthesis by inhibiting the activity of the iron-dependent enzyme ribonucleotide reductase and the transcription of the cytoplasmic serine hydroxymethyltransferase gene (SHMT). Inhibition of serine hydroxymethyltransferase is moderated by a zinc responsive unit located in front of the SHMT gene.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

1055
  Mrv0541 02231215122D          

 14 14  0  0  1  0            999 V2000
    2.0930    2.2193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -1.9058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    2.2193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -2.7308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.2558    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    0.5693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    0.9818    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2365   -0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    1.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -1.4933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.4933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.9058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  2 12  1  0  0  0  0
  3 11  2  0  0  0  0
  4 14  2  0  0  0  0
  5  7  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  8  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  2  0  0  0  0
 10 13  2  0  0  0  0
 12 14  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015188

> <DATABASE_NAME>
hmdb

> <SMILES>
N[C@@H](CN1C=CC(=O)C(O)=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H10N2O4/c9-5(8(13)14)3-10-2-1-6(11)7(12)4-10/h1-2,4-5,12H,3,9H2,(H,13,14)/t5-/m0/s1

> <INCHI_KEY>
WZNJWVWKTVETCG-YFKPBYRVSA-N

> <FORMULA>
C8H10N2O4

> <MOLECULAR_WEIGHT>
198.176

> <EXACT_MASS>
198.064056818

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
18.20032148272685

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-(3-hydroxy-4-oxo-1,4-dihydropyridin-1-yl)propanoic acid

> <ALOGPS_LOGP>
-2.43

> <JCHEM_LOGP>
-2.9592000692311604

> <ALOGPS_LOGS>
-1.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.58274729332331

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.935149912523551

> <JCHEM_PKA_STRONGEST_BASIC>
8.884676445822928

> <JCHEM_POLAR_SURFACE_AREA>
103.85999999999999

> <JCHEM_REFRACTIVITY>
48.6582

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.31e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mimosine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1055                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       3.907   4.143   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       9.242  -3.557   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       6.574   4.143   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.574  -5.097   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       6.574  -0.477   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       3.907   1.063   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       6.574   1.063   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.241   1.833   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.908  -1.247   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.241  -1.247   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.241   3.373   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.908  -2.787   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.241  -2.787   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.574  -3.557   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2   12                                                            
CONECT    3   11                                                            
CONECT    4   14                                                            
CONECT    5    7    9   10                                                  
CONECT    6    8                                                            
CONECT    7    5    8                                                       
CONECT    8    6    7   11                                                  
CONECT    9    5   12                                                       
CONECT   10    5   13                                                       
CONECT   11    1    3    8                                                  
CONECT   12    2    9   14                                                  
CONECT   13   10   14                                                       
CONECT   14    4   12   13                                                  
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(S)-2-Amino-3-(3-hydroxy-4-oxo-4H-pyridin-1-yl)propanoate	ChEBI
Leucenol	Kegg
(S)-2-Amino-3-(3-hydroxy-4-oxo-4H-pyridin-1-yl)propanoic acid	Generator
L-Mimosine	HMDB
Leucaenine	HMDB
Leucaenol	HMDB
Leucenine	HMDB
Mimosin	HMDB
Mimosine	MeSH

Chemical Formula

C₈H₁₀N₂O₄

Average Molecular Weight

198.176

Monoisotopic Molecular Weight

198.064056818

IUPAC Name

(2S)-2-amino-3-(3-hydroxy-4-oxo-1,4-dihydropyridin-1-yl)propanoic acid

Traditional Name

mimosine

CAS Registry Number

500-44-7

SMILES

N[C@@H](CN1C=CC(=O)C(O)=C1)C(O)=O

InChI Identifier

InChI=1S/C8H10N2O4/c9-5(8(13)14)3-10-2-1-6(11)7(12)4-10/h1-2,4-5,12H,3,9H2,(H,13,14)/t5-/m0/s1

InChI Key

WZNJWVWKTVETCG-YFKPBYRVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Dihydropyridine
Hydroxypyridine
Hydropyridine
Pyridine
Heteroaromatic compound
Vinylogous amide
Amino acid
Cyclic ketone
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Amine
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxide
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:29063 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0015188)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	228 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	13.1 g/L	Not Available
LogP	-2.5	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	143.467	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001951

Predicted Molecular Properties

Property	Value	Source
Water Solubility	13.1 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-3	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	1.94	ChemAxon
pKa (Strongest Basic)	8.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	103.86 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	48.66 m³·mol⁻¹	ChemAxon
Polarizability	18.2 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	145.845	31661259
DarkChem	[M-H]-	141.169	31661259
DeepCCS	[M+H]+	141.173	30932474
DeepCCS	[M-H]-	138.777	30932474
DeepCCS	[M-2H]-	172.833	30932474
DeepCCS	[M+Na]+	147.368	30932474
AllCCS	[M+H]+	142.9	32859911
AllCCS	[M+H-H2O]+	138.9	32859911
AllCCS	[M+NH4]+	146.6	32859911
AllCCS	[M+Na]+	147.7	32859911
AllCCS	[M-H]-	140.8	32859911
AllCCS	[M+Na-2H]-	141.4	32859911
AllCCS	[M+HCOO]-	142.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.43 minutes	32390414
Predicted by Siyang on May 30, 2022	9.6728 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	8.52 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	390.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	459.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	302.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	39.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	178.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	73.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	306.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	220.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	942.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	591.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	49.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	670.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	188.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	266.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	686.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	648.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	358.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Mimosine	N[C@@H](CN1C=CC(=O)C(O)=C1)C(O)=O	2387.0	Standard polar	33892256
Mimosine	N[C@@H](CN1C=CC(=O)C(O)=C1)C(O)=O	1555.9	Standard non polar	33892256
Mimosine	N[C@@H](CN1C=CC(=O)C(O)=C1)C(O)=O	2132.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Mimosine,1TMS,isomer #1	C[Si](C)(C)OC1=CN(C[C@H](N)C(=O)O)C=CC1=O	2049.7	Semi standard non polar	33892256
Mimosine,1TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](N)CN1C=CC(=O)C(O)=C1	2028.2	Semi standard non polar	33892256
Mimosine,1TMS,isomer #3	C[Si](C)(C)N[C@@H](CN1C=CC(=O)C(O)=C1)C(=O)O	2114.3	Semi standard non polar	33892256
Mimosine,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)CN1C=CC(=O)C(O[Si](C)(C)C)=C1	2030.5	Semi standard non polar	33892256
Mimosine,2TMS,isomer #2	C[Si](C)(C)N[C@@H](CN1C=CC(=O)C(O[Si](C)(C)C)=C1)C(=O)O	2084.4	Semi standard non polar	33892256
Mimosine,2TMS,isomer #3	C[Si](C)(C)N[C@@H](CN1C=CC(=O)C(O)=C1)C(=O)O[Si](C)(C)C	2082.5	Semi standard non polar	33892256
Mimosine,2TMS,isomer #4	C[Si](C)(C)N([C@@H](CN1C=CC(=O)C(O)=C1)C(=O)O)[Si](C)(C)C	2198.2	Semi standard non polar	33892256
Mimosine,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CN1C=CC(=O)C(O[Si](C)(C)C)=C1)C(=O)O[Si](C)(C)C	2063.0	Semi standard non polar	33892256
Mimosine,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CN1C=CC(=O)C(O[Si](C)(C)C)=C1)C(=O)O[Si](C)(C)C	2161.5	Standard non polar	33892256
Mimosine,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CN1C=CC(=O)C(O[Si](C)(C)C)=C1)C(=O)O[Si](C)(C)C	2381.1	Standard polar	33892256
Mimosine,3TMS,isomer #2	C[Si](C)(C)OC1=CN(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=CC1=O	2217.4	Semi standard non polar	33892256
Mimosine,3TMS,isomer #2	C[Si](C)(C)OC1=CN(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=CC1=O	2271.9	Standard non polar	33892256
Mimosine,3TMS,isomer #2	C[Si](C)(C)OC1=CN(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=CC1=O	2508.6	Standard polar	33892256
Mimosine,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CN1C=CC(=O)C(O)=C1)N([Si](C)(C)C)[Si](C)(C)C	2198.5	Semi standard non polar	33892256
Mimosine,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CN1C=CC(=O)C(O)=C1)N([Si](C)(C)C)[Si](C)(C)C	2204.8	Standard non polar	33892256
Mimosine,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CN1C=CC(=O)C(O)=C1)N([Si](C)(C)C)[Si](C)(C)C	2497.8	Standard polar	33892256
Mimosine,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CN1C=CC(=O)C(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C	2250.0	Semi standard non polar	33892256
Mimosine,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CN1C=CC(=O)C(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C	2290.1	Standard non polar	33892256
Mimosine,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CN1C=CC(=O)C(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C	2288.0	Standard polar	33892256
Mimosine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CN(C[C@H](N)C(=O)O)C=CC1=O	2308.4	Semi standard non polar	33892256
Mimosine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CN1C=CC(=O)C(O)=C1	2313.9	Semi standard non polar	33892256
Mimosine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CN1C=CC(=O)C(O)=C1)C(=O)O	2390.5	Semi standard non polar	33892256
Mimosine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CN1C=CC(=O)C(O[Si](C)(C)C(C)(C)C)=C1	2538.4	Semi standard non polar	33892256
Mimosine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CN1C=CC(=O)C(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O	2612.1	Semi standard non polar	33892256
Mimosine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CN1C=CC(=O)C(O)=C1)C(=O)O[Si](C)(C)C(C)(C)C	2588.7	Semi standard non polar	33892256
Mimosine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@@H](CN1C=CC(=O)C(O)=C1)C(=O)O)[Si](C)(C)C(C)(C)C	2708.8	Semi standard non polar	33892256
Mimosine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CN1C=CC(=O)C(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O[Si](C)(C)C(C)(C)C	2770.0	Semi standard non polar	33892256
Mimosine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CN1C=CC(=O)C(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O[Si](C)(C)C(C)(C)C	2794.0	Standard non polar	33892256
Mimosine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CN1C=CC(=O)C(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O[Si](C)(C)C(C)(C)C	2723.8	Standard polar	33892256
Mimosine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CN(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=CC1=O	2970.3	Semi standard non polar	33892256
Mimosine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CN(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=CC1=O	2862.8	Standard non polar	33892256
Mimosine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CN(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=CC1=O	2777.9	Standard polar	33892256
Mimosine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CN1C=CC(=O)C(O)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2920.1	Semi standard non polar	33892256
Mimosine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CN1C=CC(=O)C(O)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2795.0	Standard non polar	33892256
Mimosine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CN1C=CC(=O)C(O)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2744.4	Standard polar	33892256
Mimosine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CN1C=CC(=O)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3182.5	Semi standard non polar	33892256
Mimosine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CN1C=CC(=O)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3058.5	Standard non polar	33892256
Mimosine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CN1C=CC(=O)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2701.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Mimosine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fmi-3900000000-bb110a21987d7171e5d0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mimosine GC-MS (2 TMS) - 70eV, Positive	splash10-00gi-9652000000-0c3fa7766f970282f998	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mimosine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mimosine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mimosine 10V, Positive-QTOF	splash10-0f6t-1900000000-d4b420c6ab7e4090ba98	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mimosine 20V, Positive-QTOF	splash10-0udl-5900000000-8d371af9d194b02ebfac	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mimosine 40V, Positive-QTOF	splash10-0006-9300000000-551ced305fa27ac63ef1	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mimosine 10V, Negative-QTOF	splash10-0002-0900000000-df7fdf320b76d3658905	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mimosine 20V, Negative-QTOF	splash10-01ot-1900000000-e74701d243ce8e114551	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mimosine 40V, Negative-QTOF	splash10-0zfr-9000000000-f4afc202a2e71b5e27f2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mimosine 10V, Positive-QTOF	splash10-0f6t-0900000000-45380b42191a8225bb28	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mimosine 20V, Positive-QTOF	splash10-0irs-0900000000-99914b272ce6f0d1b66b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mimosine 40V, Positive-QTOF	splash10-0kgo-9400000000-54f0e3570578d6cb4055	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mimosine 10V, Negative-QTOF	splash10-01ot-0900000000-77fcfdd520ba3d482d31	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mimosine 20V, Negative-QTOF	splash10-0229-4900000000-44ec3271bb93c6855581	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mimosine 40V, Negative-QTOF	splash10-0wmi-9300000000-edd7c9b7a184acdd01f4	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01055	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01055	21059682	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01055

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00001383

Chemspider ID

389405

KEGG Compound ID

C04771

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Mimosine

METLIN ID

Not Available

PubChem Compound

440473

PDB ID

Not Available

ChEBI ID

29063

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Tyrosinase

General function:: Involved in oxidoreductase activity
Specific function:: This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA to DOPA-quinone and possibly 5,6-dihydroxyindole to indole-5,6 quinone.
Gene Name:: TYR
Uniprot ID:: P14679
Molecular weight:: 60392.69

References

Ahmad VU, Ullah F, Hussain J, Farooq U, Zubair M, Khan MT, Choudhary MI: Tyrosinase inhibitors from Rhododendron collettianum and their structure-activity relationship (SAR) studies. Chem Pharm Bull (Tokyo). 2004 Dec;52(12):1458-61. [PubMed:15577244 ]
Khan KM, Mughal UR, Khan MT, Zia-Ullah, Perveen S, Choudhary MI: Oxazolones: new tyrosinase inhibitors; synthesis and their structure-activity relationships. Bioorg Med Chem. 2006 Sep 1;14(17):6027-33. Epub 2006 Jun 5. [PubMed:16750372 ]
Sugumaran M: Tyrosinase catalyzes an unusual oxidative decarboxylation of 3,4-dihydroxymandelate. Biochemistry. 1986 Aug 12;25(16):4489-92. [PubMed:3094574 ]
Woolery GL, Powers L, Winkler M, Solomon EI, Lerch K, Spiro TG: Extended X-ray absorption fine structure study of the coupled binuclear copper active site of tyrosinase from Neurospora crassa. Biochim Biophys Acta. 1984 Jul 31;788(2):155-61. [PubMed:6234942 ]

Enzyme Details

2. Serine hydroxymethyltransferase, cytosolic

General function:: Involved in catalytic activity
Specific function:: Interconversion of serine and glycine.
Gene Name:: SHMT1
Uniprot ID:: P34896
Molecular weight:: 53082.18

References

Oppenheim EW, Nasrallah IM, Mastri MG, Stover PJ: Mimosine is a cell-specific antagonist of folate metabolism. J Biol Chem. 2000 Jun 23;275(25):19268-74. [PubMed:10766749 ]
Conti P, Frydas S, Reale M, Barbacane RC, Di Gioacchino M, Felaco M, Trakatellis A: Inhibition of MCP-1 and MIP-2 transcription and translation by mimosine in muscle tissue infected with the parasite Trichinella spiralis. Mol Cell Biochem. 2002 Jan;229(1-2):129-37. [PubMed:11936838 ]
Perry C, Sastry R, Nasrallah IM, Stover PJ: Mimosine attenuates serine hydroxymethyltransferase transcription by chelating zinc. Implications for inhibition of DNA replication. J Biol Chem. 2005 Jan 7;280(1):396-400. Epub 2004 Nov 4. [PubMed:15531579 ]
Lin HB, Falchetto R, Mosca PJ, Shabanowitz J, Hunt DF, Hamlin JL: Mimosine targets serine hydroxymethyltransferase. J Biol Chem. 1996 Feb 2;271(5):2548-56. [PubMed:8576220 ]

Enzyme Details

3. C-C motif chemokine 2

General function:: Involved in chemokine activity
Specific function:: Chemotactic factor that attracts monocytes and basophils but not neutrophils or eosinophils. Augments monocyte anti-tumor activity. Has been implicated in the pathogenesis of diseases characterized by monocytic infiltrates, like psoriasis, rheumatoid arthritis or atherosclerosis. May be involved in the recruitment of monocytes into the arterial wall during the disease process of atherosclerosis
Gene Name:: CCL2
Uniprot ID:: P13500
Molecular weight:: 11024.9

References

Conti P, Frydas S, Reale M, Barbacane RC, Di Gioacchino M, Felaco M, Trakatellis A: Inhibition of MCP-1 and MIP-2 transcription and translation by mimosine in muscle tissue infected with the parasite Trichinella spiralis. Mol Cell Biochem. 2002 Jan;229(1-2):129-37. [PubMed:11936838 ]
Frydas S, Papaioannou N, Papazahariadou M, Hatzistilianou M, Karagouni E, Trakatelli M, Brellou G, Petrarca C, Castellani ML, Conti P, Riccioni G, Patruno A, Grilli A: Inhibition of MCP-1 and MIP-2 chemokines in murine trichinellosis: effect of the anti-inflammatory compound L-mimosine. Int J Immunopathol Pharmacol. 2005 Jan-Mar;18(1):85-94. [PubMed:15698514 ]

Showing metabocard for Mimosine (HMDB0015188)

MOL for HMDB0015188 (Mimosine)

3D MOL for HMDB0015188 (Mimosine)

3D SDF for HMDB0015188 (Mimosine)

3D-SDF for HMDB0015188 (Mimosine)

PDB for HMDB0015188 (Mimosine)

3D PDB for HMDB0015188 (Mimosine)

SMILES for HMDB0015188 (Mimosine)

INCHI for HMDB0015188 (Mimosine)

Structure for HMDB0015188 (Mimosine)

3D Structure for HMDB0015188 (Mimosine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

References

References

References