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InChI=1S/CH4O/c1-2/h2H,1H3
,
caffeine
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ChEBI
> Main
CHEBI:131753 - (
S
)-iclaprim
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ChEBI Name
(
S
)-iclaprim
ChEBI ID
CHEBI:131753
ChEBI ASCII Name
(S)-iclaprim
Definition
A 5-[(2-cyclopropyl-7,8-dimethoxy-2
H
-chromen-5-yl)methyl]pyrimidine-2,4-diamine in which the chiral centre has
S
configuration.
Stars
This entity has been manually annotated by the ChEBI Team.
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Formula
C19H22N4O3
Net Charge
0
Average Mass
354.404
Monoisotopic Mass
354.16919
InChI
InChI=1S/C19H22N4O3/c1-
24-
15-
8-
11(7-
12-
9-
22-
19(21)
23-
18(12)
20)
13-
5-
6-
14(10-
3-
4-
10)
26-
16(13)
17(15)
25-
2/h5-
6,8-
10,14H,3-
4,7H2,1-
2H3,(H4,20,21,22,23)
/t14-
/m1/s1
InChIKey
HWJPWWYTGBZDEG-CQSZACIVSA-N
SMILES
C=1(C(=CN=C(N1)N)CC=2C=3C=C[C@@](OC3C(=C(C2)OC)OC)(C4CC4)[H])N
Roles Classification
Chemical Role
(s):
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Br
o
nsted acid).
(via
organic amino compound
)
Biological Role
(s):
EC 1.5.1.3 (dihydrofolate reductase) inhibitor
An EC 1.5.1.* (oxidoreductase acting on donor CH-NH group, NAD
+
or NADP
+
as acceptor) inhibitor that interferes with the action of dihydrofolate reductase (EC 1.5.1.3).
antibacterial drug
A drug used to treat or prevent bacterial infections.
Application
(s):
antibacterial drug
A drug used to treat or prevent bacterial infections.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
(
S
)-iclaprim (
CHEBI:131753
)
has role
antibacterial drug (
CHEBI:36047
)
(
S
)-iclaprim (
CHEBI:131753
)
has role
EC 1.5.1.3 (dihydrofolate reductase) inhibitor (
CHEBI:50683
)
(
S
)-iclaprim (
CHEBI:131753
)
is a
5-[(2-cyclopropyl-7,8-dimethoxy-2
H
-chromen-5-yl)methyl]pyrimidine-2,4-diamine (
CHEBI:131751
)
(
S
)-iclaprim (
CHEBI:131753
)
is enantiomer of
(
R
)-iclaprim (
CHEBI:131752
)
Incoming
iclaprim (
CHEBI:131724
)
has part
(
S
)-iclaprim (
CHEBI:131753
)
(
R
)-iclaprim (
CHEBI:131752
)
is enantiomer of
(
S
)-iclaprim (
CHEBI:131753
)
IUPAC Name
5-{[(2
S
)-2-cyclopropyl-7,8-dimethoxy-2
H
-chromen-5-yl]methyl}pyrimidine-2,4-diamine
Synonyms
Sources
AR 102
ChEBI
AR-102
ChEBI
Registry Number
Type
Source
20535807
Reaxys Registry Number
Reaxys
Citation
Type
Source
19622858
PubMed citation
Europe PMC
Last Modified
15 April 2016