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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 02:51:47 UTC

HMDB ID

HMDB0014925

Secondary Accession Numbers

HMDB14925

Metabolite Identification

Common Name

Aciclovir

Description

Aciclovir is only found in individuals that have used or taken this drug. It is a guanosine analog that acts as an antimetabolite. Viruses are especially susceptible. Used especially against herpes. [PubChem]Viral (HSV-1, HSV-2 and VZV) thymidine kinase converts aciclovir to the aciclovir monophosphate, which is then converted to the diphosphate by cellular guanylate kinase, and finally to the triphosphate by phosphoglycerate kinase, phosphoenolpyruvate carboxykinase, and pyruvate kinase. Aciclovir triphosphate competitively inhibits viral DNA polymerase and competes with the natural deoxyguanosine triphosphate, for incorporation into viral DNA. Once incorporated, aciclovir triphosphate inhibits DNA synthesis by acting as a chain terminator.

Structure

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

787
  Mrv0541 02231215002D          

 16 17  0  0  0  0            999 V2000
    6.0807    0.7122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -2.5562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4006    2.4506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0171   -0.2422    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.0811    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0171   -1.5700    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.3186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -0.0811    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.4936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2734    0.5420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -1.3186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4986   -0.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.7311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.4936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3370    1.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1443    1.6665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  1 15  1  0  0  0  0
  2 13  2  0  0  0  0
  3 16  1  0  0  0  0
  4  9  1  0  0  0  0
  4 10  1  0  0  0  0
  4 12  1  0  0  0  0
  5  9  1  0  0  0  0
  5 14  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  2  0  0  0  0
  7 13  1  0  0  0  0
  7 14  2  0  0  0  0
  8 14  1  0  0  0  0
  9 11  2  0  0  0  0
 11 13  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014925

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=NC(=O)C2=C(N1)N(COCCO)C=N2

> <INCHI_IDENTIFIER>
InChI=1S/C8H11N5O3/c9-8-11-6-5(7(15)12-8)10-3-13(6)4-16-2-1-14/h3,14H,1-2,4H2,(H3,9,11,12,15)

> <INCHI_KEY>
MKUXAQIIEYXACX-UHFFFAOYSA-N

> <FORMULA>
C8H11N5O3

> <MOLECULAR_WEIGHT>
225.2046

> <EXACT_MASS>
225.086189243

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
21.50793372513306

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-9-[(2-hydroxyethoxy)methyl]-6,9-dihydro-3H-purin-6-one

> <ALOGPS_LOGP>
-0.95

> <JCHEM_LOGP>
-1.0319567660000002

> <ALOGPS_LOGS>
-1.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.11725876431052

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.986608032207476

> <JCHEM_PKA_STRONGEST_BASIC>
2.6261777857739976

> <JCHEM_POLAR_SURFACE_AREA>
114.75999999999999

> <JCHEM_REFRACTIVITY>
54.6334

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.08e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
zovirax

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 787                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      11.351   1.329   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       6.574  -4.772   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      13.814   4.574   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       9.365  -0.452   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       6.574  -0.151   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       9.365  -2.931   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       5.241  -2.461   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       3.907  -0.151   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       7.908  -0.921   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.844   1.012   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.908  -2.461   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.264  -1.691   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.574  -3.231   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.241  -0.921   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.829   2.793   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.336   3.111   0.000  0.00  0.00           C+0
CONECT    1   10   15                                                       
CONECT    2   13                                                            
CONECT    3   16                                                            
CONECT    4    9   10   12                                                  
CONECT    5    9   14                                                       
CONECT    6   11   12                                                       
CONECT    7   13   14                                                       
CONECT    8   14                                                            
CONECT    9    4    5   11                                                  
CONECT   10    1    4                                                       
CONECT   11    6    9   13                                                  
CONECT   12    4    6                                                       
CONECT   13    2    7   11                                                  
CONECT   14    5    7    8                                                  
CONECT   15    1   16                                                       
CONECT   16    3   15                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0014925
HETATM    1  N1  UNL     1       3.865   1.238  -1.608  1.00  0.00           N  
HETATM    2  C1  UNL     1       3.160   0.358  -0.750  1.00  0.00           C  
HETATM    3  N2  UNL     1       3.752  -0.748  -0.254  1.00  0.00           N  
HETATM    4  C2  UNL     1       3.028  -1.540   0.553  1.00  0.00           C  
HETATM    5  O1  UNL     1       3.539  -2.573   1.033  1.00  0.00           O  
HETATM    6  C3  UNL     1       1.704  -1.260   0.890  1.00  0.00           C  
HETATM    7  N3  UNL     1       0.783  -1.860   1.648  1.00  0.00           N  
HETATM    8  C4  UNL     1      -0.353  -1.142   1.622  1.00  0.00           C  
HETATM    9  N4  UNL     1      -0.134  -0.076   0.833  1.00  0.00           N  
HETATM   10  C5  UNL     1      -1.025   1.019   0.477  1.00  0.00           C  
HETATM   11  O2  UNL     1      -1.691   0.726  -0.682  1.00  0.00           O  
HETATM   12  C6  UNL     1      -2.464  -0.394  -0.595  1.00  0.00           C  
HETATM   13  C7  UNL     1      -3.545  -0.216   0.437  1.00  0.00           C  
HETATM   14  O3  UNL     1      -4.311   0.890   0.010  1.00  0.00           O  
HETATM   15  C8  UNL     1       1.141  -0.121   0.361  1.00  0.00           C  
HETATM   16  N5  UNL     1       1.886   0.652  -0.442  1.00  0.00           N  
HETATM   17  H1  UNL     1       4.492   1.951  -1.185  1.00  0.00           H  
HETATM   18  H2  UNL     1       3.786   1.208  -2.641  1.00  0.00           H  
HETATM   19  H3  UNL     1      -1.288  -1.362   2.137  1.00  0.00           H  
HETATM   20  H4  UNL     1      -1.701   1.313   1.328  1.00  0.00           H  
HETATM   21  H5  UNL     1      -0.367   1.940   0.297  1.00  0.00           H  
HETATM   22  H6  UNL     1      -1.871  -1.303  -0.264  1.00  0.00           H  
HETATM   23  H7  UNL     1      -2.901  -0.594  -1.609  1.00  0.00           H  
HETATM   24  H8  UNL     1      -3.101  -0.030   1.420  1.00  0.00           H  
HETATM   25  H9  UNL     1      -4.196  -1.124   0.502  1.00  0.00           H  
HETATM   26  H10 UNL     1      -3.652   1.544  -0.343  1.00  0.00           H  
HETATM   27  H11 UNL     1       1.465   1.507  -0.840  1.00  0.00           H  
CONECT    1    2   17   18
CONECT    2    3    3   16
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   15   15
CONECT    7    8    8
CONECT    8    9   19
CONECT    9   10   15
CONECT   10   11   20   21
CONECT   11   12
CONECT   12   13   22   23
CONECT   13   14   24   25
CONECT   14   26
CONECT   15   16
CONECT   16   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Aciclovirum	ChEBI
Acycloguanosine	ChEBI
Zovir	ChEBI
Acyclovir	Kegg
Sitavig	Kegg
Zovirax	Kegg
9-Hyroxyethoxymethylguanine	HMDB
AC2	HMDB
Aciclovier	HMDB
Wellcome-248u	HMDB
9-((2-Hydroxyethoxy)methyl)guanine	HMDB
Abello brand OF aciclovir	HMDB
Aciclovir betapharm brand	HMDB
Aciclovir fabrigen brand	HMDB
Aciclovir grin brand	HMDB
Aciclovir liomont brand	HMDB
Aciclovir novartis brand	HMDB
Aciclovir zyma brand	HMDB
Aciclovir CT-arzneimittel brand	HMDB
Acyclo V	HMDB
Britisfarma brand OF aciclovir sodium salt	HMDB
Bull brand OF aciclovir	HMDB
Fustery brand OF aciclovir	HMDB
Hexal brand OF aciclovir sodium salt	HMDB
Isis brand OF aciclovir	HMDB
Novag brand OF aciclovir	HMDB
Opthavir	HMDB
Pensa brand OF aciclovir	HMDB
Rentschler brand OF aciclovir	HMDB
Sanorania brand OF aciclovir sodium salt	HMDB
Warner-lambert brand OF aciclovir	HMDB
Wellcome brand OF aciclovir	HMDB
Wellcome brand OF aciclovir sodium salt	HMDB
Zoliparin	HMDB
Zovirax for injection	HMDB
Curasan brand OF aciclovir sodium salt	HMDB
Aciclobeta	HMDB
Aciclovir amrad brand	HMDB
Aciclovir fustery brand	HMDB
Aciclovir mann brand	HMDB
Aciclovir niddapharm brand	HMDB
Aciclovir sanorania brand	HMDB
Aciclovir ursapharm brand	HMDB
Aciclovir-sanorania	HMDB
Activir	HMDB
Acyclo-V	HMDB
Alcon brand OF aciclovir	HMDB
Alonga brand OF aciclovir	HMDB
Avirax	HMDB
Azupharma brand OF aciclovir	HMDB
Cicloferon	HMDB
Clonmel brand OF aciclovir	HMDB
Cusiviral	HMDB
Dermapharm brand OF aciclovir	HMDB
Fabrigen brand OF aciclovir	HMDB
Grünenthal brand OF aciclovir sodium salt	HMDB
Herpofug	HMDB
Herpoviric	HMDB
Hexal brand OF aciclovir	HMDB
Isavir	HMDB
Milavir	HMDB
Parke davis brand OF aciclovir	HMDB
Pharma investi brand OF aciclovir	HMDB
ViraxPuren	HMDB
Virherpes	HMDB
Virolex	HMDB
Virzin	HMDB
Warner wellcome brand OF aciclovir	HMDB
Wolff brand OF aciclovir	HMDB
Zyclir	HMDB
Zyma brand OF aciclovir	HMDB
CT Arzneimittel brand OF aciclovir	HMDB
Aci sanorania	HMDB
Acic	HMDB
Aciclovir alonga	HMDB
Aciclovir britisfarma brand	HMDB
Aciclovir grünenthal brand	HMDB
Aciclovir isis brand	HMDB
Aciclovir kendrick brand	HMDB
Aciclovir lichtenstein brand	HMDB
Aciclovir menarini brand	HMDB
Aciclovir sanorania	HMDB
Aciclovir stada brand	HMDB
Aciclovir tad brand	HMDB
Aciclovir warner-lambert brand	HMDB
Aciclovir wellcome brand	HMDB
Aciclovir wolff brand	HMDB
Acifur	HMDB
Amrad brand OF aciclovir	HMDB
Antiherpes creme	HMDB
Britisfarma brand OF aciclovir	HMDB
Genvir	HMDB
Glaxo wellcome brand OF aciclovir	HMDB
Grünenthal brand OF aciclovir	HMDB
Herpetad	HMDB
Laciken	HMDB
Lichtenstein brand OF aciclovir	HMDB
Mapox	HMDB
Maynar	HMDB
Menarini brand OF aciclovir	HMDB
Pisa brand OF aciclovir	HMDB
Rentschler brand OF aciclovir sodium salt	HMDB
Stada brand OF aciclovir	HMDB
TAD brand OF aciclovir	HMDB
Ursapharm brand OF aciclovir	HMDB
Viclovir	HMDB
Virax puren	HMDB
Virax-puren	HMDB
Virmen	HMDB
Virupos	HMDB
Warner lambert brand OF aciclovir	HMDB
Wellcome 248u	HMDB
Wellcome248u	HMDB
Yamanouchi brand OF aciclovir	HMDB
Aciclovir von CT	HMDB
Aci-sanorania	HMDB
Aciclostad	HMDB
Aciclovir abello brand	HMDB
Aciclovir alcon brand	HMDB
Aciclovir alphapharm brand	HMDB
Aciclovir azupharma brand	HMDB
Aciclovir clonmel brand	HMDB
Aciclovir dermapharm brand	HMDB
Aciclovir hexal brand	HMDB
Aciclovir novag brand	HMDB
Aciclovir pensa brand	HMDB
Aciclovir pisa brand	HMDB
Aciclovir rentschler brand	HMDB
Aciclovir yamanouchi brand	HMDB
Acipen solutab	HMDB
Acivir	HMDB
Acyclovir sodium	HMDB
Alonga brand OF aciclovir sodium salt	HMDB
Alphapharm brand OF aciclovir	HMDB
Betapharm brand OF aciclovir	HMDB
Clonorax	HMDB
Glaxo wellcome brand OF aciclovir sodium salt	HMDB
Grin brand OF aciclovir	HMDB
Herpotern	HMDB
Kendrick brand OF aciclovir	HMDB
Liomont brand OF aciclovir	HMDB
Mann brand OF aciclovir	HMDB
Menarini brand OF aciclovir sodium salt	HMDB
Niddapharm brand OF aciclovir	HMDB
Novartis brand OF aciclovir	HMDB
Pensa brand OF aciclovir sodium salt	HMDB
Sanorania brand OF aciclovir	HMDB
Sodium, acyclovir	HMDB
Solutab, acipen	HMDB
Supraviran	HMDB
Vipral	HMDB
CT-Arzneimittel brand OF aciclovir	HMDB
Aciclovir granules	HMDB
Aciclovir ophthalmic oinment	HMDB
Aciclovir tablets	HMDB
Alonga, aciclovir	HMDB
Aciclovir	ChEBI

Chemical Formula

C₈H₁₁N₅O₃

Average Molecular Weight

225.2046

Monoisotopic Molecular Weight

225.086189243

IUPAC Name

2-amino-9-[(2-hydroxyethoxy)methyl]-6,9-dihydro-3H-purin-6-one

Traditional Name

zovirax

CAS Registry Number

59277-89-3

SMILES

NC1=NC(=O)C2=C(N1)N(COCCO)C=N2

InChI Identifier

InChI=1S/C8H11N5O3/c9-8-11-6-5(7(15)12-8)10-3-13(6)4-16-2-1-14/h3,14H,1-2,4H2,(H3,9,11,12,15)

InChI Key

MKUXAQIIEYXACX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hypoxanthines. Hypoxanthines are compounds containing the purine derivative 1H-purin-6(9H)-one. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

Hypoxanthines

Alternative Parents

Substituents

6-oxopurine
Hypoxanthine
Aminopyrimidine
Pyrimidone
N-substituted imidazole
Pyrimidine
Azole
Imidazole
Heteroaromatic compound
Vinylogous amide
Azacycle
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Alcohol
Primary amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

oxopurine (CHEBI:2453 )
2-aminopurines (CHEBI:2453 )

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: HMDB0014925)
Membrane (HMDB: HMDB0014925)

Source

Exogenous

Exogenous (HMDB: HMDB0014925)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	256.5 - 257 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	9.08 g/L	Not Available
LogP	-1.56	KRISTL,A ET AL. (1993)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	146.464	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001041

Predicted Molecular Properties

Property	Value	Source
Water Solubility	9.08 g/L	ALOGPS
logP	-0.95	ALOGPS
logP	-1	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	7.99	ChemAxon
pKa (Strongest Basic)	2.63	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	114.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	54.63 m³·mol⁻¹	ChemAxon
Polarizability	21.51 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]+	150.453	31661259
DarkChem	[M-H]-	148.42	31661259
DeepCCS	[M+H]+	148.619	30932474
DeepCCS	[M-H]-	146.261	30932474
DeepCCS	[M-2H]-	180.393	30932474
DeepCCS	[M+Na]+	155.206	30932474
AllCCS	[M+H]+	148.8	32859911
AllCCS	[M+H-H2O]+	144.9	32859911
AllCCS	[M+NH4]+	152.3	32859911
AllCCS	[M+Na]+	153.3	32859911
AllCCS	[M-H]-	149.1	32859911
AllCCS	[M+Na-2H]-	149.2	32859911
AllCCS	[M+HCOO]-	149.4	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.	1.62 minutes	32390414
Predicted by Siyang on May 30, 2022	10.2862 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.25 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	134.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	692.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	291.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	37.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	164.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	68.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	308.3 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	265.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	770.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	626.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	59.4 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	830.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	180.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	191.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	731.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	349.9 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	328.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Aciclovir	NC1=NC(=O)C2=C(N1)N(COCCO)C=N2	3240.7	Standard polar	33892256
Aciclovir	NC1=NC(=O)C2=C(N1)N(COCCO)C=N2	2279.9	Standard non polar	33892256
Aciclovir	NC1=NC(=O)C2=C(N1)N(COCCO)C=N2	2634.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Aciclovir,1TMS,isomer #1	C[Si](C)(C)OCCOCN1C=NC2=C1[NH]C(N)=NC2=O	2297.7	Semi standard non polar	33892256
Aciclovir,1TMS,isomer #2	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N(COCCO)C=N2	2352.5	Semi standard non polar	33892256
Aciclovir,1TMS,isomer #3	C[Si](C)(C)N1C(N)=NC(=O)C2=C1N(COCCO)C=N2	2340.6	Semi standard non polar	33892256
Aciclovir,2TMS,isomer #1	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N(COCCO[Si](C)(C)C)C=N2	2326.0	Semi standard non polar	33892256
Aciclovir,2TMS,isomer #1	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N(COCCO[Si](C)(C)C)C=N2	2586.0	Standard non polar	33892256
Aciclovir,2TMS,isomer #1	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N(COCCO[Si](C)(C)C)C=N2	3748.8	Standard polar	33892256
Aciclovir,2TMS,isomer #2	C[Si](C)(C)OCCOCN1C=NC2=C1N([Si](C)(C)C)C(N)=NC2=O	2289.8	Semi standard non polar	33892256
Aciclovir,2TMS,isomer #2	C[Si](C)(C)OCCOCN1C=NC2=C1N([Si](C)(C)C)C(N)=NC2=O	2513.0	Standard non polar	33892256
Aciclovir,2TMS,isomer #2	C[Si](C)(C)OCCOCN1C=NC2=C1N([Si](C)(C)C)C(N)=NC2=O	3714.7	Standard polar	33892256
Aciclovir,2TMS,isomer #3	C[Si](C)(C)N(C1=NC(=O)C2=C([NH]1)N(COCCO)C=N2)[Si](C)(C)C	2292.4	Semi standard non polar	33892256
Aciclovir,2TMS,isomer #3	C[Si](C)(C)N(C1=NC(=O)C2=C([NH]1)N(COCCO)C=N2)[Si](C)(C)C	2644.1	Standard non polar	33892256
Aciclovir,2TMS,isomer #3	C[Si](C)(C)N(C1=NC(=O)C2=C([NH]1)N(COCCO)C=N2)[Si](C)(C)C	3635.4	Standard polar	33892256
Aciclovir,2TMS,isomer #4	C[Si](C)(C)NC1=NC(=O)C2=C(N(COCCO)C=N2)N1[Si](C)(C)C	2347.0	Semi standard non polar	33892256
Aciclovir,2TMS,isomer #4	C[Si](C)(C)NC1=NC(=O)C2=C(N(COCCO)C=N2)N1[Si](C)(C)C	2617.5	Standard non polar	33892256
Aciclovir,2TMS,isomer #4	C[Si](C)(C)NC1=NC(=O)C2=C(N(COCCO)C=N2)N1[Si](C)(C)C	3612.1	Standard polar	33892256
Aciclovir,3TMS,isomer #1	C[Si](C)(C)OCCOCN1C=NC2=C1[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	2339.1	Semi standard non polar	33892256
Aciclovir,3TMS,isomer #1	C[Si](C)(C)OCCOCN1C=NC2=C1[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	2623.7	Standard non polar	33892256
Aciclovir,3TMS,isomer #1	C[Si](C)(C)OCCOCN1C=NC2=C1[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	3298.8	Standard polar	33892256
Aciclovir,3TMS,isomer #2	C[Si](C)(C)NC1=NC(=O)C2=C(N(COCCO[Si](C)(C)C)C=N2)N1[Si](C)(C)C	2336.0	Semi standard non polar	33892256
Aciclovir,3TMS,isomer #2	C[Si](C)(C)NC1=NC(=O)C2=C(N(COCCO[Si](C)(C)C)C=N2)N1[Si](C)(C)C	2557.2	Standard non polar	33892256
Aciclovir,3TMS,isomer #2	C[Si](C)(C)NC1=NC(=O)C2=C(N(COCCO[Si](C)(C)C)C=N2)N1[Si](C)(C)C	3316.3	Standard polar	33892256
Aciclovir,3TMS,isomer #3	C[Si](C)(C)N(C1=NC(=O)C2=C(N(COCCO)C=N2)N1[Si](C)(C)C)[Si](C)(C)C	2396.3	Semi standard non polar	33892256
Aciclovir,3TMS,isomer #3	C[Si](C)(C)N(C1=NC(=O)C2=C(N(COCCO)C=N2)N1[Si](C)(C)C)[Si](C)(C)C	2674.1	Standard non polar	33892256
Aciclovir,3TMS,isomer #3	C[Si](C)(C)N(C1=NC(=O)C2=C(N(COCCO)C=N2)N1[Si](C)(C)C)[Si](C)(C)C	3182.1	Standard polar	33892256
Aciclovir,4TMS,isomer #1	C[Si](C)(C)OCCOCN1C=NC2=C1N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	2407.2	Semi standard non polar	33892256
Aciclovir,4TMS,isomer #1	C[Si](C)(C)OCCOCN1C=NC2=C1N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	2648.4	Standard non polar	33892256
Aciclovir,4TMS,isomer #1	C[Si](C)(C)OCCOCN1C=NC2=C1N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	2929.2	Standard polar	33892256
Aciclovir,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCOCN1C=NC2=C1[NH]C(N)=NC2=O	2545.2	Semi standard non polar	33892256
Aciclovir,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N(COCCO)C=N2	2579.2	Semi standard non polar	33892256
Aciclovir,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(N)=NC(=O)C2=C1N(COCCO)C=N2	2535.5	Semi standard non polar	33892256
Aciclovir,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N(COCCO[Si](C)(C)C(C)(C)C)C=N2	2744.8	Semi standard non polar	33892256
Aciclovir,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N(COCCO[Si](C)(C)C(C)(C)C)C=N2	2965.6	Standard non polar	33892256
Aciclovir,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N(COCCO[Si](C)(C)C(C)(C)C)C=N2	3680.1	Standard polar	33892256
Aciclovir,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCCOCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N)=NC2=O	2725.2	Semi standard non polar	33892256
Aciclovir,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCCOCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N)=NC2=O	2919.7	Standard non polar	33892256
Aciclovir,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCCOCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N)=NC2=O	3646.6	Standard polar	33892256
Aciclovir,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=NC(=O)C2=C([NH]1)N(COCCO)C=N2)[Si](C)(C)C(C)(C)C	2709.4	Semi standard non polar	33892256
Aciclovir,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=NC(=O)C2=C([NH]1)N(COCCO)C=N2)[Si](C)(C)C(C)(C)C	3043.9	Standard non polar	33892256
Aciclovir,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=NC(=O)C2=C([NH]1)N(COCCO)C=N2)[Si](C)(C)C(C)(C)C	3546.1	Standard polar	33892256
Aciclovir,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C(N(COCCO)C=N2)N1[Si](C)(C)C(C)(C)C	2754.5	Semi standard non polar	33892256
Aciclovir,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C(N(COCCO)C=N2)N1[Si](C)(C)C(C)(C)C	2977.1	Standard non polar	33892256
Aciclovir,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C(N(COCCO)C=N2)N1[Si](C)(C)C(C)(C)C	3511.3	Standard polar	33892256
Aciclovir,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCOCN1C=NC2=C1[NH]C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O	2910.0	Semi standard non polar	33892256
Aciclovir,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCOCN1C=NC2=C1[NH]C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O	3236.1	Standard non polar	33892256
Aciclovir,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCOCN1C=NC2=C1[NH]C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O	3355.6	Standard polar	33892256
Aciclovir,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C(N(COCCO[Si](C)(C)C(C)(C)C)C=N2)N1[Si](C)(C)C(C)(C)C	2941.7	Semi standard non polar	33892256
Aciclovir,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C(N(COCCO[Si](C)(C)C(C)(C)C)C=N2)N1[Si](C)(C)C(C)(C)C	3158.7	Standard non polar	33892256
Aciclovir,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C(N(COCCO[Si](C)(C)C(C)(C)C)C=N2)N1[Si](C)(C)C(C)(C)C	3353.9	Standard polar	33892256
Aciclovir,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=NC(=O)C2=C(N(COCCO)C=N2)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2934.9	Semi standard non polar	33892256
Aciclovir,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=NC(=O)C2=C(N(COCCO)C=N2)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3253.6	Standard non polar	33892256
Aciclovir,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=NC(=O)C2=C(N(COCCO)C=N2)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3246.7	Standard polar	33892256
Aciclovir,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCOCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O	3133.6	Semi standard non polar	33892256
Aciclovir,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCOCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O	3420.8	Standard non polar	33892256
Aciclovir,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCOCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O	3188.4	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
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 DB00787	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00787	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00787

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

1945

KEGG Compound ID

C06810

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Acyclovir

METLIN ID

Not Available

PubChem Compound

2022

PDB ID

AC2

ChEBI ID

2453

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

O'Brien JJ, Campoli-Richards DM: Acyclovir. An updated review of its antiviral activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1989 Mar;37(3):233-309. [PubMed:2653790 ]
Gunness P, Aleksa K, Bend J, Koren G: Acyclovir-induced nephrotoxicity: the role of the acyclovir aldehyde metabolite. Transl Res. 2011 Nov;158(5):290-301. doi: 10.1016/j.trsl.2011.07.002. Epub 2011 Aug 3. [PubMed:22005269 ]

Transporters

Enzyme Details

1. Solute carrier family 22 member 1

General function:: Involved in ion transmembrane transporter activity
Specific function:: Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)- N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase
Gene Name:: SLC22A1
Uniprot ID:: O15245
Molecular weight:: 61187.4

References

Takeda M, Khamdang S, Narikawa S, Kimura H, Kobayashi Y, Yamamoto T, Cha SH, Sekine T, Endou H: Human organic anion transporters and human organic cation transporters mediate renal antiviral transport. J Pharmacol Exp Ther. 2002 Mar;300(3):918-24. [PubMed:11861798 ]

Enzyme Details

2. 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

Takeda M, Khamdang S, Narikawa S, Kimura H, Kobayashi Y, Yamamoto T, Cha SH, Sekine T, Endou H: Human organic anion transporters and human organic cation transporters mediate renal antiviral transport. J Pharmacol Exp Ther. 2002 Mar;300(3):918-24. [PubMed:11861798 ]
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 Aciclovir (HMDB0014925)

MOL for HMDB0014925 (Aciclovir)

3D MOL for HMDB0014925 (Aciclovir)

3D SDF for HMDB0014925 (Aciclovir)

3D-SDF for HMDB0014925 (Aciclovir)

PDB for HMDB0014925 (Aciclovir)

3D PDB for HMDB0014925 (Aciclovir)

SMILES for HMDB0014925 (Aciclovir)

INCHI for HMDB0014925 (Aciclovir)

Structure for HMDB0014925 (Aciclovir)

3D Structure for HMDB0014925 (Aciclovir)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Transporters

References

References