Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR2290)
Drug Name
Lauric acid
Synonyms
Aliphat No. 4; Coconut oil fatty acids; DODECANOIC ACID; Dodecoic acid; Dodecylcarboxylate; Dodecylic acid; Duodecyclic acid; Duodecylic acid; Hydrofol acid 1255; Hydrofol acid 1295; Hystrene 9512; Lauric acid (natural); Lauric acid, pure; Laurinsaeure; Laurostearic acid; Neo-fat 12; Neo-fat 12-43; Ninol AA62 Extra; Undecane-1-carboxylic acid; Univol U-314; Vulvic acid; Wecoline 1295; lauric acid; n-Dodecanoate; n-Dodecanoic acid; 1-Undecanecarboxylic acid; 143-07-7; ABL; C-1297; C12 fatty acid; CCRIS 669; NSC-5026; UNII-1160N9NU9U
Indication Alzheimer disease [ICD11: 8A20] Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 200.32 Topological Polar Surface Area 37.3
Heavy Atom Count 14 Rotatable Bond Count 10
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
3893
PubChem SID
5649 ; 71199 ; 587917 ; 819797 ; 819951 ; 821886 ; 822246 ; 826382 ; 830803 ; 830815 ; 832379 ; 833825 ; 838007 ; 838335 ; 3133731 ; 3718095 ; 5673162 ; 7849666 ; 7886898 ; 7888608 ; 7888612 ; 8014369 ; 8026553 ; 8026610 ; 8026623 ; 8026781 ; 8027199 ; 8027947 ; 8027951 ; 8027953 ; 8137853 ; 8145220 ; 8152452 ; 10507982 ; 11456907 ; 15195524 ; 17388953 ; 17389665 ; 24770717 ; 24874804 ; 24896365 ; 24896407 ; 24901204 ; 24901205 ; 26703021 ; 26703023 ; 26703378 ; 26703414 ; 26710306 ; 26710331
ChEBI ID
CHEBI:30805
CAS Number
143-07-7
TTD Drug ID
D0N0UC
Formula
C12H24O2
Canonical SMILES
CCCCCCCCCCCC(=O)O
InChI
1S/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14)
InChIKey
POULHZVOKOAJMA-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
11-hydroxylauric acid DM004955
169433
Oxidation - Hydrolyzationn 1 [4]
12-Hydroxydodecanoic Acid DM004952
79034
Oxidation - Aliphatic hydroxylation 1 [5] , [4]
2-hydroxylauric acid DM004956
97783
Oxidation - Hydrolyzationn 1 [4]
12,12-Dihydroxydodecanoic Acid DM004953
54548147
Oxidation - Oxidationn 2 [5] , [4]
Dodecanedioic Acid DM004954
12736
Oxidation - Oxidationn 3 [5] , [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005368 Lauric acid 12-Hydroxydodecanoic Acid Oxidation - Aliphatic hydroxylation CYP2C8 ... [5], [4]
MR005371 Lauric acid 11-hydroxylauric acid Oxidation - Hydrolyzationn CYP2B6 ... [4]
MR005372 Lauric acid 2-hydroxylauric acid Oxidation - Hydrolyzationn CYP2B6 [4]
MR005369 12-Hydroxydodecanoic Acid 12,12-Dihydroxydodecanoic Acid Oxidation - Oxidationn Cyp4a1 [5], [4]
MR005370 12,12-Dihydroxydodecanoic Acid Dodecanedioic Acid Oxidation - Oxidationn Cyp4a1 [5], [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 107L2 (cyp107) DME2063 Streptomyces avermitilis
PIKC_STRVZ
1.14.15.11
[2] , [3]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[4]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[5] , [4]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[5] , [4]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[4]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[5] , [4]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Cytochrome P450 4A10 (Cyp4a1) DMEN251 Rattus norvegicus
CP4AA_RAT
1.14.14.80
[5] , [4]
Lauric acid omega-hydroxylase (CYP4A11) DME0029 Homo sapiens
CP4AB_HUMAN
1.14.15.3
[4]
⏷ Show the Full List of 9  DME(s)
References
1 Lauric acid alleviates neuroinflammatory responses by activated microglia: involvement of the GPR40-dependent pathway. Neurochem Res. 2018 Sep;43(9):1723-1735.
2 The metagenome of Caracolus marginella gut microbiome using culture independent approaches and shotgun sequencing. Data Brief. 2017 Nov 22;16:501-505.
3 Structural insights into the binding of lauric acid to CYP107L2 from Streptomyces avermitilis. Biochem Biophys Res Commun. 2017 Jan 22;482(4):902-908.
4 Cytochrome P450 4A11 inhibition assays based on characterization of lauric acid metabolites
5 The omega-hydroxlyation of lauric acid: oxidation of 12-hydroxlauric acid to dodecanedioic acid by a purified recombinant fusion protein containing P450 4A1 and NADPH-P450 reductase

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