trans-4-hydroxy-L-proline (CHEBI:18095)

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CHEBI:18095 - trans-4-hydroxy-L-proline

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ChEBI Name	trans-4-hydroxy-L-proline

ChEBI ID	CHEBI:18095

ChEBI ASCII Name	trans-4-hydroxy-L-proline

Definition	An optically active form of 4-hydroxyproline having L-trans-configuration.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:43318, CHEBI:43172, CHEBI:43210, CHEBI:43227, CHEBI:49360, CHEBI:10714, CHEBI:27060, CHEBI:12864

Supplier Information	ZINC000263614187

Download	Molfile XML SDF

more structures >>

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The Resolver thinks Mol

HYP - Ideal conformer

RDKit 3D

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Time for openFile( HYP - Ideal conformer

RDKit 3D

18 18 0 0 0 0 0 0 0 0999 V2000

0.1680 1.3600 -0.2820 N 0 0 0 0 0 0 0 0 0 0 0 0

-0.3840 -0.0030 -0.4930 C 0 0 2 0 0 0 0 0 0 0 0 0

-1.8110 -0.0720 -0.0130 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.2330 0.7640 0.7500 O 0 0 0 0 0 0 0 0 0 0 0 0

0.5150 -0.9240 0.3590 C 0 0 0 0 0 0 0 0 0 0 0 0

1.8470 -0.1590 0.5050 C 0 0 2 0 0 0 0 0 0 0 0 0

1.6400 1.1590 -0.2710 C 0 0 0 0 0 0 0 0 0 0 0 0

2.9170 -0.9110 -0.0710 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.6140 -1.0630 -0.4330 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.1070 1.9810 -1.0280 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.3250 -0.2780 -1.5460 H 0 0 0 0 0 0 0 0 0 0 0 0

0.0660 -1.0920 1.3370 H 0 0 0 0 0 0 0 0 0 0 0 0

0.6780 -1.8730 -0.1530 H 0 0 0 0 0 0 0 0 0 0 0 0

2.0520 0.0480 1.5550 H 0 0 0 0 0 0 0 0 0 0 0 0

2.0180 1.0650 -1.2890 H 0 0 0 0 0 0 0 0 0 0 0 0

2.1320 1.9850 0.2430 H 0 0 0 0 0 0 0 0 0 0 0 0

3.7800 -0.4790 -0.0090 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.5200 -1.0660 -0.0980 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 1 0

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2 3 1 0

2 5 1 0

2 11 1 6

3 4 2 0

3 9 1 0

5 6 1 0

5 12 1 0

5 13 1 0

6 7 1 0

6 8 1 0

6 14 1 1

7 15 1 0

7 16 1 0

8 17 1 0

9 18 1 0

M END): 19 ms

reading 18 atoms

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1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

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18 atoms created

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Molfile expand

Formula

C5H9NO3

Net Charge

Average Mass

131.131

Monoisotopic Mass

131.05824

InChI

InChI=1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4+/m1/s1

InChIKey

PMMYEEVYMWASQN-DMTCNVIQSA-N

SMILES

[C@H]1(C[C@@H](O)CN1)C(O)=O

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Arabidopsis thaliana (NCBI:txid3702)	See: DOI
Homo sapiens (NCBI:txid9606)	See: DOI

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). (via 4-hydroxyproline ) mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	trans-4-hydroxy-L-proline (CHEBI:18095) has role human metabolite (CHEBI:77746) trans-4-hydroxy-L-proline (CHEBI:18095) has role mouse metabolite (CHEBI:75771) trans-4-hydroxy-L-proline (CHEBI:18095) has role plant metabolite (CHEBI:76924) trans-4-hydroxy-L-proline (CHEBI:18095) is a 4-hydroxyproline (CHEBI:20392) trans-4-hydroxy-L-proline (CHEBI:18095) is tautomer of trans-4-hydroxy-L-proline zwitterion (CHEBI:58375)

Incoming	(R)-4-hydroxy-1-methyl-L-proline (CHEBI:134543) has functional parent trans-4-hydroxy-L-proline (CHEBI:18095) L-hydroxyproline 2-naphthylamide (CHEBI:90449) has functional parent trans-4-hydroxy-L-proline (CHEBI:18095) Gly-Hyp (CHEBI:138515) has functional parent trans-4-hydroxy-L-proline (CHEBI:18095) Pro-Hyp (CHEBI:74767) has functional parent trans-4-hydroxy-L-proline (CHEBI:18095) trans-4-hydroxy-L-proline residue (CHEBI:61965) is substituent group from trans-4-hydroxy-L-proline (CHEBI:18095) trans-4-hydroxy-L-proline zwitterion (CHEBI:58375) is tautomer of trans-4-hydroxy-L-proline (CHEBI:18095)

IUPAC Name

(4R)-4-hydroxy-L-proline

Synonyms	Sources
(2S,4R)-4-hydroxy-2-pyrrolidinecarboxylic acid	ChEBI
(2S,4R)-trans-4-hydroxyproline	ChEBI
δ-hydroxyproline	NIST Chemistry WebBook
Hydroxy-L-proline	ChemIDplus
Hydroxyproline	ChemIDplus
Hyp	ChEBI
Hypro	ChemIDplus
L-4-Hydroxyproline	ChemIDplus
L-threo-4-hydroxyproline	ChEBI
trans-4-hydroxy-L-proline	ChEBI
trans-4-Hydroxy-L-proline	KEGG COMPOUND
trans-Hydroxyproline	NIST Chemistry WebBook
trans-L-Hydroxyproline	NIST Chemistry WebBook

Manual Xrefs	Databases
4-HYDROXY-L-PROLINE	MetaCyc
4272	DrugCentral
C00001370	KNApSAcK
C01157	KEGG COMPOUND
HMDB0000725	HMDB
HYP	PDBeChem
HYP_LEO2	PDBeChem
HYP_LL	PDBeChem
HYP_LSN3	PDBeChem
View more database links

Registry Numbers	Types	Sources
51-35-4	CAS Registry Number	KEGG COMPOUND
51-35-4	CAS Registry Number	ChemIDplus
51-35-4	CAS Registry Number	NIST Chemistry WebBook
81441	Reaxys Registry Number	Reaxys

Citations

Last Modified

03 April 2025

CHEBI:18095 - trans-4-hydroxy-L-proline

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