L-Pipecolate (BioCAD00000013111)
amniotic fluid blood cerebrospinal fluid (csf) feces saliva urine intestine liver placenta prostate
Metabolite Card
Formula: C6H11NO2 (129.079)
SMILES: OC(=O)C1CCCCN1
Synonyms [en]
l-Pipecolic acid; 2-piperidinecarboxylic acid; Pipecolinic acid; pipecolic acid; L-pipecolate; (S)-Piperidine-2-carboxylic acid
Last reviewed on 2024-06-28.
Cite this Page
L-Pipecolate. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China.
https://biocad_registry.innovation.ac.cn/s/(-)-arctiin
(retrieved
2026-01-03) (CAD Registry RN: BioCAD00000013111). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
Pipecolic acid is a metabolite of lysine found in human physiological fluids such as urine, plasma and CSF. However, it is uncertain if pipecolic acid originates directly from food intake or from mammalian or intestinal bacterial enzyme metabolism. Recent studies suggest that plasma pipecolic acid, particularly the D-isomer, originates mainly from the catabolism of dietary lysine by intestinal bacteria rather than by direct food intake. In classic Zellweger syndrome (a cerebro-hepato-renal genetic disorder, OMIM 214100) pipecolic acid accumulate in the plasma of the patients. It is known that plasma pipecolic acid levels are also elevated in patients with chronic liver diseases. Pipecolic acid is moderately elevated in patients with pyridoxine-dependent seizures and might therefore be a possible biochemical marker for selecting candidates for pyridoxine therapy (Plecko et al 2000). Pipecolic acid was also elevated in CSF in these vitamin B6-responsive patients (PMID 12705501). Pipecolic acid is found to be associated with adrenoleukodystrophy, infantile Refsum disease, and peroxisomal biogenesis defect, which are also inborn errors of metabolism. Pipecolic acid is a biomarker for the consumption of dried and cooked beans.
DBLinks
- CAS Registry Number: 3105-95-1
- PubChem CID: 849
- ChEBI: 30633
- HMDB: HMDB0000070
- LipidMaps:
- KEGG: C00408
- BioCyc: L-PIPECOLATE
- NCBI MeSH: pipecolic acid
- Wikipedia: Pipecolic_acid
Other DBLinks
- CAS Registry Number: 3105-95-1
- CAS Registry Number: 4043-87-2
- CAS Registry Number: 535-75-1
- PubChem: 439227
- PubChem: 849
- ChEBI: ChEBI:17964
- ChEBI: ChEBI:270397
- ChEBI: ChEBI:30633
- ChEBI: ChEBI:30913
- HMDB: HMDB0000070
- HMDB: HMDB0000716
- HMDB: HMDB00070
- KEGG: C00408
- BioCyc: CPD-20333
- BioCyc: L-PIPECOLATE
- NCBI MeSH: pipecolic acid
- Wikipedia: Pipecolic acid
- Wikipedia: Pipecolic_acid
- RefMet: RM0135981
- MoNA: BAF_UVA_POS000264
- MoNA: BAF_UVA_POS000265
- MoNA: BAF_UVA_POS000266
- MoNA: BAF_UVA_POS001036
- MoNA: CCMSLIB00000577967
- MoNA: CCMSLIB00000578201
- MoNA: CCMSLIB00005464001
- MoNA: CCMSLIB00005464002
- MoNA: CCMSLIB00005464032
- MoNA: CCMSLIB00005464078
- MoNA: CCMSLIB00005464079
- MoNA: CCMSLIB00005720405
- MoNA: CCMSLIB00005720700
- MoNA: EMBL-MCF_spec115832
- MoNA: EMBL-MCF_spec45195
- MoNA: EMBL-MCF_spec45221
- MoNA: EMBL_MCF_2_0_HRMS_Library000059
- MoNA: EMBL_MCF_2_0_HRMS_Library000299
- MoNA: FiehnHILIC000697
- MoNA: FiehnHILIC002263
- MoNA: FiehnLib000686
- MoNA: HMDB0000070_c_ms_102574
- MoNA: HMDB0000070_c_ms_102575
- MoNA: HMDB0000070_c_ms_99532
- MoNA: HMDB0000070_ms_ms_111
- MoNA: HMDB0000070_ms_ms_112
- MoNA: HMDB0000070_ms_ms_113
- MoNA: HMDB0000716_c_ms_1066
- MoNA: HMDB0000716_c_ms_1305
- MoNA: HMDB0000716_c_ms_994
- MoNA: HMDB0000716_ms_ms_1002
- MoNA: HMDB0000716_ms_ms_1003
- MoNA: HMDB0000716_ms_ms_1004
- MoNA: KO001631
- MoNA: KO001632
- MoNA: KO001633
- MoNA: KO001634
- MoNA: KO001635
- MoNA: KO003743
- MoNA: KO003744
- MoNA: KO003745
- MoNA: KO003746
- MoNA: KO003747
- MoNA: MoNA001845
- MoNA: MoNA001846
- MoNA: MoNA001847
- MoNA: MoNA002130
- MoNA: MoNA002131
- MoNA: MoNA002132
- MoNA: MoNA010501
- MoNA: MoNA010502
- MoNA: MoNA010503
- MoNA: MoNA010504
- MoNA: MoNA010505
- MoNA: MoNA010506
- MoNA: MoNA011273
- MoNA: MoNA011274
- MoNA: MoNA011275
- MoNA: MoNA011276
- MoNA: MoNA016745
- MoNA: MoNA016782
- MoNA: MoNA016911
- MoNA: MoNA024239
- MoNA: MoNA032036
- MoNA: MoNA032038
- MoNA: MoNA032039
- MoNA: MoNA033953
- MoNA: MoNA033954
- MoNA: MoNA035980
- MoNA: MoNA035981
- MoNA: MoNA035982
- MoNA: MoNA037137
- MoNA: MoNA037846
- MoNA: MoNA038538
- MoNA: MT000096
- MoNA: OUF00200
- MoNA: PM000918
- MoNA: PR100436
- MoNA: PR100437
- MoNA: PR100888
- MoNA: PS109701
- MoNA: PS109702
- MoNA: PS109703
- MoNA: PS109704
- MoNA: PS109705
- MoNA: PS109706
- MoNA: PT110970
- MoNA: PT110973
- MoNA: PT210970
- Metlin: METLIN_50
- Metlin: METLIN_63100
- Coconut NaturalProduct: CNP0076472.2
- Coconut NaturalProduct: CNP0148927.2
- Coconut NaturalProduct: CNP0217757.0
Class / Ontology
- WishartLab ClassyFire: [Amino acids, peptides, and analogues] Amino acids, peptides, and analogues
- RefMet: [Amino acids] Amino acids
- ChEBI: [CHEBI:17964] pipecolic acid
- ChEBI: [CHEBI:30913] L-pipecolic acid
- Coconut NaturalProduct: [Aminoacids] Aminoacids
| ID | EC Number | Name |
|---|---|---|
| KEGG:R00459 | C00047<=>C00408 | |
| KEGG:R02201 | 1.5.1.1 | L-pipecolate:NAD+ 2-oxidoreductase |
| KEGG:R02203 | 1.5.1.1 | L-pipecolate:NADP+ 2-oxidoreductase |
| KEGG:R02204 | 1.5.3.7 | L-pipecolate:oxygen 1,6-oxidoreductase |
| KEGG:R02205 | 1.5.99.3 | L-pipecolate:(acceptor) 1,6-oxidoreductase |
| KEGG:R02206 | 1.5.99.3 | L-pipecolate:(acceptor) 1,6-oxidoreductase |
| KEGG:R08414 | C00450<=>C00408 | |
| KEGG:R08415 | C00408<=>C16697 | |
| KEGG:R09680 | 3.5.1.101 | (S)-piperidine-2-carboxamide amidohydrolase |
| KEGG:R10277 | 4.3.1.28 | L-lysine ammonia-lyase (cyclizing; ammonia-forming) |
| BioCyc:RXN-19250 | 1.5.1.21 | DELTA1-PIPERIDEINE-2-CARBOXYLATE + NADPH + 2 PROTON --> L-PIPECOLATE + NADP |
| BioCyc:RXN-16682 | 6.3.2.- | L-PIPECOLATE + ACP + ATP --> CPD-17983 + AMP + PPI |
| BioCyc:RXN-8166 | 1.5.1.1 | DELTA1-PIPERIDEINE-2-CARBOXYLATE + NADH-P-OR-NOP + 2 PROTON --> L-PIPECOLATE + NAD-P-OR-NOP |
| BioCyc:L-PIPECOLATE-DEHYDROGENASE-RXN | 1.5.99.3 | L-PIPECOLATE + Acceptor<=>CPD-7682 + Donor-H2 + PROTON |
| BioCyc:RXN-13654 | 4.3.1.28 | LYS --> L-PIPECOLATE + AMMONIUM |
| BioCyc:RXN-21030 | 1.14.13.- | L-PIPECOLATE + OXYGEN-MOLECULE + NADH --> CPD-22664 + WATER + NAD |
| BioCyc:RXN-16267 | 1.5.1.- | CPD-7682 + NADPH + 2 PROTON --> L-PIPECOLATE + NADP |
| BioCyc:L-PIPECOLATE-OXIDASE-RXN | 1.5.3.7 | L-PIPECOLATE + OXYGEN-MOLECULE --> PROTON + CPD-7682 + HYDROGEN-PEROXIDE |
| BioCyc:RXN-10757 | 3.5.1.101 | CPD-11620 + WATER --> L-PIPECOLATE + AMMONIUM |
| BioCyc:RXN-14210 | 1.5.1.- | L-PIPECOLATE + NAD<=>DELTA1-PIPERIDEINE-2-CARBOXYLATE + NADH + 2 PROTON |
Taxonomy Source
- Foeniculum vulgare [ncbi taxid: ]
- Alkanna cappadocica [ncbi taxid: 2650392]
- Alternaria oxytropis Raft River [ncbi taxid: ]
- Angelica acutiloba [ncbi taxid: 55605]
- Angelica gigas [ncbi taxid: 85712]
- Angelica sinensis [ncbi taxid: 165353]
- Artemisia dentata [ncbi taxid: ]
- Arthroderma otae CBS113480 [ncbi taxid: ]
- Astragalux oxyphysus [ncbi taxid: ]
- Atalantia racemosa [ncbi taxid: 159026]
- Buddleja cordata [ncbi taxid: 168492]
- Buphane fischeri [ncbi taxid: ]
- Castanosperma australe [ncbi taxid: ]
- Citrullus lanatus [ncbi taxid: 3654]
- Crambe tatarica [ncbi taxid: 71346]
- Diospyros eriantha [ncbi taxid: 1009467]
- Fritillaria ningguoensis [ncbi taxid: ]
- Hoffmannia strigillosa [ncbi taxid: ]
- Homo sapiens [ncbi taxid: 9606]
- Humulus lupulus [ncbi taxid: 3486]
- Juniperus rigida var. conferta [ncbi taxid: 13102]
- Lemaireocereus griseus [ncbi taxid: ]
- Lemna gibba [ncbi taxid: 4470]
- Lemna paucicostata [ncbi taxid: ]
- Millettia erythrocalyx [ncbi taxid: 1679271]
- Mycobacterium leprae [ncbi taxid: 1769]
- Negombata magnifica [ncbi taxid: 344322]
- Ononis vaginalis [ncbi taxid: 798051]
- Phaseolus vulgaris [ncbi taxid: 3885]
- Phaseolus vulgaris L. [ncbi taxid: ]
- Pogostemon cablin [ncbi taxid: 28511]
- Prorocentrum micans [ncbi taxid: 2945]
- Pseudogymnoascus sp. VKM F-4515 [ncbi taxid: ]
- Pteris semipinnata [ncbi taxid: 265705]
- Rapanea lancifolia [ncbi taxid: ]
- Rhizoma zingiberis praeparata [ncbi taxid: ]
- Rhizoma zingiberis recens preparata [ncbi taxid: ]
- Salvia hispanica [ncbi taxid: 49212]
- Scorzonera pseudodivaricata [ncbi taxid: ]
- Syncarpia hillii [ncbi taxid: 271921]
- Trichophyton equinum CBS127.97 [ncbi taxid: ]
- Undifilum oxytropis [ncbi taxid: ]
- Xenoacremonium recifei [ncbi taxid: 1036759]
Pathway Synthetic
| pathway id | name |
|---|