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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:45 UTC

HMDB ID

HMDB0014847

Secondary Accession Numbers

HMDB14847

Metabolite Identification

Common Name

Lamivudine

Description

Lamivudine is only found in individuals that have used or taken this drug. It is a reverse transcriptase inhibitor and zalcitabine analog in which a sulfur atom replaces the 3' carbon of the pentose ring. It is used to treat Human Immunodeficiency Virus Type 1 (HIV-1) and hepatitis B (HBV).Lamivudine is a synthetic nucleoside analogue and is phosphorylated intracellularly to its active 5'-triphosphate metabolite, lamivudine triphosphate (L-TP). This nucleoside analogue is incorporated into viral DNA by HIV reverse transcriptase and HBV polymerase, resulting in DNA chain termination.

Structure

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

709
  Mrv0541 02231214572D          

 15 16  0  0  1  0            999 V2000
    2.6665   -1.4952    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7465   -0.7106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6409   -2.9164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.5994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.5994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    3.0744    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.2256    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4115   -0.7106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916   -1.4952    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9764   -2.1627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.0119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.0119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  1 10  1  0  0  0  0
  2  8  1  0  0  0  0
  2 10  1  0  0  0  0
  3 11  1  0  0  0  0
  4 13  2  0  0  0  0
  8  5  1  1  0  0  0
  5 12  1  0  0  0  0
  5 13  1  0  0  0  0
  6 13  1  0  0  0  0
  6 15  2  0  0  0  0
  7 15  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  1  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014847

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=NC(=O)N(C=C1)[C@@H]1CS[C@H](CO)O1

> <INCHI_IDENTIFIER>
InChI=1S/C8H11N3O3S/c9-5-1-2-11(8(13)10-5)6-4-15-7(3-12)14-6/h1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7+/m0/s1

> <INCHI_KEY>
JTEGQNOMFQHVDC-NKWVEPMBSA-N

> <FORMULA>
C8H11N3O3S

> <MOLECULAR_WEIGHT>
229.256

> <EXACT_MASS>
229.052111923

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
21.69986366490535

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one

> <ALOGPS_LOGP>
-1.29

> <JCHEM_LOGP>
-1.0951075880000003

> <ALOGPS_LOGS>
-1.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.294605913828615

> <JCHEM_PKA_STRONGEST_BASIC>
-0.16058074296490987

> <JCHEM_POLAR_SURFACE_AREA>
88.15

> <JCHEM_REFRACTIVITY>
55.1645

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.76e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lamivudine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 709                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       4.977  -2.791   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       6.993  -1.326   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       6.796  -5.444   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.080   1.119   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       5.748   1.119   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       4.414   3.429   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       5.748   5.739   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       5.748  -0.421   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.501  -1.326   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.518  -2.791   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.423  -4.037   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.081   1.889   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414   1.889   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.081   3.429   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.748   4.199   0.000  0.00  0.00           C+0
CONECT    1    9   10                                                       
CONECT    2    8   10                                                       
CONECT    3   11                                                            
CONECT    4   13                                                            
CONECT    5    8   12   13                                                  
CONECT    6   13   15                                                       
CONECT    7   15                                                            
CONECT    8    2    5    9                                                  
CONECT    9    1    8                                                       
CONECT   10    1    2   11                                                  
CONECT   11    3   10                                                       
CONECT   12    5   14                                                       
CONECT   13    4    5    6                                                  
CONECT   14   12   15                                                       
CONECT   15    6    7   14                                                  
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(-)-1-((2R,5S)-2-(Hydroxymethyl)-1,3-oxathiolan-5-yl)cytosine	ChEBI
(-)-2'-Deoxy-3'-thiacytidine	ChEBI
2',3'-Dideoxy-3'-thiacytidine	ChEBI
3'-Thia-2',3'-dideoxycytidine	ChEBI
3TC	ChEBI
beta-L-2',3'-Dideoxy-3'-thiacytidine	ChEBI
beta-L-3'-Thia-2',3'-dideoxycytidine	ChEBI
Epivir	ChEBI
b-L-2',3'-Dideoxy-3'-thiacytidine	Generator
Β-L-2',3'-dideoxy-3'-thiacytidine	Generator
b-L-3'-Thia-2',3'-dideoxycytidine	Generator
Β-L-3'-thia-2',3'-dideoxycytidine	Generator
2',3' Dideoxy 3' thiacytidine	HMDB
BCH 189	HMDB
BCH-189	HMDB
Lamivudine, (2S-cis)-isomer	HMDB

Chemical Formula

C₈H₁₁N₃O₃S

Average Molecular Weight

229.256

Monoisotopic Molecular Weight

229.052111923

IUPAC Name

4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one

Traditional Name

lamivudine

CAS Registry Number

134678-17-4

SMILES

NC1=NC(=O)N(C=C1)[C@@H]1CS[C@H](CO)O1

InChI Identifier

InChI=1S/C8H11N3O3S/c9-5-1-2-11(8(13)10-5)6-4-15-7(3-12)14-6/h1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7+/m0/s1

InChI Key

JTEGQNOMFQHVDC-NKWVEPMBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3'-thia pyrimidine nucleosides. These are nucleoside analogues with a structure that consists of a pyrimidine base, which is N-substituted at the 1-position with a 3'-thia derivative (1,3-oxazolidine) of the ribose moiety that is characteristic of nucleosides.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Nucleoside and nucleotide analogues

Sub Class

3'-thia pyrimidine nucleosides

Direct Parent

3'-thia pyrimidine nucleosides

Alternative Parents

Substituents

3'-thia pyrimidine nucleoside
Hydroxypyrimidine
Hydropyrimidine
Pyrimidine
Monothioacetal
Oxathiolane
Heteroaromatic compound
Azacycle
Organoheterocyclic compound
Oxacycle
Organopnictogen compound
Organic oxygen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

primary alcohol (CHEBI:63577 )
oxacycle (CHEBI:63577 )
monothioacetal (CHEBI:63577 )

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

Cytoplasm (HMDB: HMDB0014847)
Membrane (HMDB: HMDB0014847)

Source

Exogenous

Exogenous (HMDB: HMDB0014847)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Lamivudine Metabolism Pathway (PathBank: SMP0000649)

Drug action pathway

Lamivudine Action Pathway (PathBank: SMP0000742)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	160 - 162 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	2.76 g/L	Not Available
LogP	-1.4	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.76 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-1.1	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	14.29	ChemAxon
pKa (Strongest Basic)	-0.16	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	88.15 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	55.16 m³·mol⁻¹	ChemAxon
Polarizability	21.7 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	149.62	31661259
DarkChem	[M-H]-	148.767	31661259
DeepCCS	[M+H]+	147.576	30932474
DeepCCS	[M-H]-	145.18	30932474
DeepCCS	[M-2H]-	178.242	30932474
DeepCCS	[M+Na]+	153.588	30932474
AllCCS	[M+H]+	149.5	32859911
AllCCS	[M+H-H2O]+	145.7	32859911
AllCCS	[M+NH4]+	153.1	32859911
AllCCS	[M+Na]+	154.1	32859911
AllCCS	[M-H]-	148.3	32859911
AllCCS	[M+Na-2H]-	148.6	32859911
AllCCS	[M+HCOO]-	149.1	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.	2.24 minutes	32390414
Predicted by Siyang on May 30, 2022	9.3791 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.54 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	34.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	594.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	259.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	83.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	161.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	59.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	280.5 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	277.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	265.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	638.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	99.5 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	753.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	188.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	180.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	426.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	285.5 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	119.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lamivudine	NC1=NC(=O)N(C=C1)[C@@H]1CS[C@H](CO)O1	3687.0	Standard polar	33892256
Lamivudine	NC1=NC(=O)N(C=C1)[C@@H]1CS[C@H](CO)O1	2263.2	Standard non polar	33892256
Lamivudine	NC1=NC(=O)N(C=C1)[C@@H]1CS[C@H](CO)O1	2592.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lamivudine,1TMS,isomer #1	C[Si](C)(C)OC[C@@H]1O[C@H](N2C=CC(N)=NC2=O)CS1	2350.4	Semi standard non polar	33892256
Lamivudine,1TMS,isomer #2	C[Si](C)(C)NC1=NC(=O)N([C@@H]2CS[C@H](CO)O2)C=C1	2393.8	Semi standard non polar	33892256
Lamivudine,2TMS,isomer #1	C[Si](C)(C)NC1=NC(=O)N([C@@H]2CS[C@H](CO[Si](C)(C)C)O2)C=C1	2422.3	Semi standard non polar	33892256
Lamivudine,2TMS,isomer #1	C[Si](C)(C)NC1=NC(=O)N([C@@H]2CS[C@H](CO[Si](C)(C)C)O2)C=C1	2424.8	Standard non polar	33892256
Lamivudine,2TMS,isomer #1	C[Si](C)(C)NC1=NC(=O)N([C@@H]2CS[C@H](CO[Si](C)(C)C)O2)C=C1	3363.0	Standard polar	33892256
Lamivudine,2TMS,isomer #2	C[Si](C)(C)N(C1=NC(=O)N([C@@H]2CS[C@H](CO)O2)C=C1)[Si](C)(C)C	2370.6	Semi standard non polar	33892256
Lamivudine,2TMS,isomer #2	C[Si](C)(C)N(C1=NC(=O)N([C@@H]2CS[C@H](CO)O2)C=C1)[Si](C)(C)C	2468.6	Standard non polar	33892256
Lamivudine,2TMS,isomer #2	C[Si](C)(C)N(C1=NC(=O)N([C@@H]2CS[C@H](CO)O2)C=C1)[Si](C)(C)C	3401.5	Standard polar	33892256
Lamivudine,3TMS,isomer #1	C[Si](C)(C)OC[C@@H]1O[C@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)CS1	2396.3	Semi standard non polar	33892256
Lamivudine,3TMS,isomer #1	C[Si](C)(C)OC[C@@H]1O[C@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)CS1	2507.1	Standard non polar	33892256
Lamivudine,3TMS,isomer #1	C[Si](C)(C)OC[C@@H]1O[C@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)CS1	2963.2	Standard polar	33892256
Lamivudine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H]1O[C@H](N2C=CC(N)=NC2=O)CS1	2594.8	Semi standard non polar	33892256
Lamivudine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2CS[C@H](CO)O2)C=C1	2650.4	Semi standard non polar	33892256
Lamivudine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2CS[C@H](CO[Si](C)(C)C(C)(C)C)O2)C=C1	2866.3	Semi standard non polar	33892256
Lamivudine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2CS[C@H](CO[Si](C)(C)C(C)(C)C)O2)C=C1	2874.3	Standard non polar	33892256
Lamivudine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2CS[C@H](CO[Si](C)(C)C(C)(C)C)O2)C=C1	3384.1	Standard polar	33892256
Lamivudine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=NC(=O)N([C@@H]2CS[C@H](CO)O2)C=C1)[Si](C)(C)C(C)(C)C	2810.3	Semi standard non polar	33892256
Lamivudine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=NC(=O)N([C@@H]2CS[C@H](CO)O2)C=C1)[Si](C)(C)C(C)(C)C	2926.2	Standard non polar	33892256
Lamivudine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=NC(=O)N([C@@H]2CS[C@H](CO)O2)C=C1)[Si](C)(C)C(C)(C)C	3355.2	Standard polar	33892256
Lamivudine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H]1O[C@H](N2C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)CS1	3010.4	Semi standard non polar	33892256
Lamivudine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H]1O[C@H](N2C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)CS1	3155.1	Standard non polar	33892256
Lamivudine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H]1O[C@H](N2C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)CS1	3149.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Lamivudine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00uv-9710000000-73bdde0fcb4c41646b42	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lamivudine GC-MS (1 TMS) - 70eV, Positive	splash10-00dr-9810000000-86fa390c1f35b5657b84	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lamivudine 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lamivudine 35V, Negative-QTOF	splash10-001i-0900000000-0426dfea67e7b18668a9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lamivudine 35V, Positive-QTOF	splash10-03di-0900000000-ee992d3b04ad0899fd5c	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lamivudine 10V, Positive-QTOF	splash10-03di-0910000000-93346cf49eef73914c7c	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lamivudine 20V, Positive-QTOF	splash10-03di-4900000000-07c6901608fdcd9b93b8	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lamivudine 40V, Positive-QTOF	splash10-03dj-9600000000-5e58e487d2a852e72115	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lamivudine 10V, Negative-QTOF	splash10-004i-4970000000-db3826710ed881faa506	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lamivudine 20V, Negative-QTOF	splash10-00n0-1900000000-f8fcf86f0a9e8e88d032	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lamivudine 40V, Negative-QTOF	splash10-00di-9100000000-7bf9d4c9292e16f5a8cf	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lamivudine 10V, Positive-QTOF	splash10-03di-0900000000-fe19e5cac381204da398	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lamivudine 20V, Positive-QTOF	splash10-03di-2900000000-ff3d600bf7691abf5f26	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lamivudine 40V, Positive-QTOF	splash10-014i-9100000000-c64b48056159e06e836a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lamivudine 10V, Negative-QTOF	splash10-004i-0490000000-d2646f253431399eff22	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lamivudine 20V, Negative-QTOF	splash10-001l-4900000000-c1bd605b7601b28c7acc	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lamivudine 40V, Negative-QTOF	splash10-0006-9400000000-1e16c0091c211dd73c16	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)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Lamivudine Metabolism Pathway		Not Available
Lamivudine Action Pathway		Not Available

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 DB00709	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00709	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00709

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

54812

KEGG Compound ID

C07065

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lamivudine

METLIN ID

Not Available

PubChem Compound

60825

PDB ID

3TC

ChEBI ID

63577

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

Fox Z, Dragsted UB, Gerstoft J, Phillips AN, Kjaer J, Mathiesen L, Youle M, Katlama C, Hill A, Bruun JN, Clumeck N, Dellamonica P, Lundgren JD: A randomized trial to evaluate continuation versus discontinuation of lamivudine in individuals failing a lamivudine-containing regimen: the COLATE trial. Antivir Ther. 2006;11(6):761-70. [PubMed:17310820 ]

Transporters

Enzyme Details

1. Multidrug resistance-associated protein 1

General function:: Involved in ATP binding
Specific function:: Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o- glucuronide, methotrexate, antiviral drugs and other xenobiotics. Confers resistance to anticancer drugs. Hydrolyzes ATP with low efficiency
Gene Name:: ABCC1
Uniprot ID:: P33527
Molecular weight:: 171589.5

References

Olson DP, Scadden DT, D'Aquila RT, De Pasquale MP: The protease inhibitor ritonavir inhibits the functional activity of the multidrug resistance related-protein 1 (MRP-1). AIDS. 2002 Sep 6;16(13):1743-7. [PubMed:12218384 ]

Enzyme Details

2. ATP-binding cassette sub-family G member 2

General function:: Involved in ATP binding
Specific function:: Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from the brain. May be involved in brain-to-blood efflux. Appears to play a major role in the multidrug resistance phenotype of several cancer cell lines. When overexpressed, the transfected cells become resistant to mitoxantrone, daunorubicin and doxorubicin, display diminished intracellular accumulation of daunorubicin, and manifest an ATP- dependent increase in the efflux of rhodamine 123
Gene Name:: ABCG2
Uniprot ID:: Q9UNQ0
Molecular weight:: 72313.5

References

Wang X, Furukawa T, Nitanda T, Okamoto M, Sugimoto Y, Akiyama S, Baba M: Breast cancer resistance protein (BCRP/ABCG2) induces cellular resistance to HIV-1 nucleoside reverse transcriptase inhibitors. Mol Pharmacol. 2003 Jan;63(1):65-72. [PubMed:12488537 ]

Enzyme Details

3. Solute carrier family 22 member 6

General function:: Involved in ion transmembrane transporter activity
Specific function:: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:: SLC22A6
Uniprot ID:: Q4U2R8
Molecular weight:: 61815.8

References

Wada S, Tsuda M, Sekine T, Cha SH, Kimura M, Kanai Y, Endou H: Rat multispecific organic anion transporter 1 (rOAT1) transports zidovudine, acyclovir, and other antiviral nucleoside analogs. J Pharmacol Exp Ther. 2000 Sep;294(3):844-9. [PubMed:10945832 ]

Showing metabocard for Lamivudine (HMDB0014847)

MOL for HMDB0014847 (Lamivudine)

3D MOL for HMDB0014847 (Lamivudine)

3D SDF for HMDB0014847 (Lamivudine)

3D-SDF for HMDB0014847 (Lamivudine)

PDB for HMDB0014847 (Lamivudine)

3D PDB for HMDB0014847 (Lamivudine)

SMILES for HMDB0014847 (Lamivudine)

INCHI for HMDB0014847 (Lamivudine)

Structure for HMDB0014847 (Lamivudine)

3D Structure for HMDB0014847 (Lamivudine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Transporters

References

References

References