Molecule

4-hydroxyproline

AlkaPlorer ID: AK003359

Synonym: '4-Hydroxyproline', 'cis-4-Hydroxy-L-Proline', '51-35-4', 'Hydroxyproline', 'L-Hydroxyproline', '(2S)-4-hydroxypyrrolidine-2-carboxylic acid', '4-Hydroxy-L-proline', '49761-17-3', 'cis-4-Hydroxy-D-proline', '4-hydroxy-L-proline', '618-27-9', 'trans-4-Hydroxy-L-proline', '3398-22-9', 'L-threo-4-hydroxyproline', 'Hydroxy-L-proline', '(2S,4R)-4-hydroxy-2-pyrrolidinecarboxylic acid', 'L-4-Hydroxyproline', 'Hyp', 'trans-4-Hydroxyproline', '618-28-0', 'cis-4-hydroxy-D-proline', 'trans-L-Hydroxyproline', 'trans-Hydroxyproline', 'Hypro', '4Hyp', '(2S,4R)-trans-4-hydroxyproline', '2584-71-6', 'trans-4-hydroxy-L-proline', 'delta-hydroxyproline', 'hydroxy-L-proline'

IUPAC Name: (2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid

Structure

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

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

Reference

Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles

PubChem CID: 6971053

CAS: 13504-85-3

LOTUS: LTS0236149

SuperNatural Ⅲ: SN0289481-02

NPASS: NPC196359

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Ginkgo biloba	Ginkgo	Ginkgoaceae	Ginkgoales	Ginkgoopsida	Streptophyta	Viridiplantae	Eukaryota
Cistanche deserticola	Cistanche	Orobanchaceae	Lamiales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Calvatia gigantea	Calvatia	Lycoperdaceae	Agaricales	Agaricomycetes	Basidiomycota	Fungi	Eukaryota
Homo sapiens	Homo	Hominidae	Primates	Mammalia	Chordata	Metazoa	Eukaryota
Arabidopsis thaliana	Arabidopsis	Brassicaceae	Brassicales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Allium sativum	Allium	Amaryllidaceae	Asparagales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Calvatia fenzlii	Calvatia	Lycoperdaceae	Agaricales	Agaricomycetes	Basidiomycota	Fungi	Eukaryota
Calvatia lilacina	Calvatia	Lycoperdaceae	Agaricales	Agaricomycetes	Basidiomycota	Fungi	Eukaryota
Lablab purpureus	Lablab	Fabaceae	Fabales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Mus musculus	Mus	Muridae	Rodentia	Mammalia	Chordata	Metazoa	Eukaryota
Holothuria leucospilota	Holothuria	Holothuriidae	Aspidochirotida	Holothuroidea	Echinodermata	Metazoa	Eukaryota
Santalum album	Santalum	Santalaceae	Santalales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota

Properties Information

Molecule Weight: 131.131

TPSA？: 69.56

MolLogP？: -1.2062

Number of H-Donors: 3

Number of H-Acceptors: 3

RingCount: 1

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Homo sapiens	786-0	GI50	100000.0	nM	None
Homo sapiens	A498	GI50	100000.0	nM	None
Homo sapiens	A549	GI50	100000.0	nM	None
Homo sapiens	Acetylcholinesterase	AC50	30000.0	nM	10.1038/s41467-023-40064-9
Homo sapiens	ACHN	GI50	100000.0	nM	None
Homo sapiens	Adenosine A3 receptor	AC50	30000.0	nM	10.1038/s41467-023-40064-9
Homo sapiens	Alpha-1a adrenergic receptor	AC50	30000.0	nM	10.1038/s41467-023-40064-9
Homo sapiens	Alpha-2a adrenergic receptor	AC50	30000.0	nM	10.1038/s41467-023-40064-9
Homo sapiens	Androgen Receptor	AC50	30000.0	nM	10.1038/s41467-023-40064-9
Homo sapiens	BT-549	GI50	100000.0	nM	None
Homo sapiens	CAKI-1	GI50	100000.0	nM	None
Homo sapiens	CCRF-CEM	GI50	100000.0	nM	None
Homo sapiens	COLO 205	GI50	100000.0	nM	None
Homo sapiens	Cyclooxygenase-1	AC50	30000.0	nM	10.1038/s41467-023-40064-9
Homo sapiens	Dopamine D1 receptor	AC50	30000.0	nM	10.1038/s41467-023-40064-9
Homo sapiens	Dopamine transporter	AC50	30000.0	nM	10.1038/s41467-023-40064-9
Homo sapiens	DU-145	GI50	100000.0	nM	None
Homo sapiens	Egl nine homolog 1	Inhibition	nan	%	10.1016/j.bmcl.2011.05.050
Homo sapiens	EKVX	GI50	100000.0	nM	None
Homo sapiens	Estrogen receptor alpha	AC50	30000.0	nM	10.1038/s41467-023-40064-9
Homo sapiens	HCC 2998	GI50	100000.0	nM	None
Homo sapiens	HCT-116	GI50	100000.0	nM	None
Homo sapiens	HCT-15	GI50	100000.0	nM	None
Homo sapiens	HERG	AC50	30000.0	nM	10.1038/s41467-023-40064-9
Homo sapiens	Histamine H3 receptor	AC50	30000.0	nM	10.1038/s41467-023-40064-9
Homo sapiens	Histone deacetylase 6	Inhibition	-1.23	%	10.6019/CHEMBL4808148
Homo sapiens	Histone deacetylase 6	Inhibition	16.12	%	10.6019/CHEMBL4808148
Homo sapiens	HL-60	GI50	100000.0	nM	None
Homo sapiens	HOP-62	GI50	100000.0	nM	None
Homo sapiens	HOP-92	GI50	100000.0	nM	None
Homo sapiens	Hs-578T	GI50	100000.0	nM	None
Homo sapiens	HT-29	GI50	100000.0	nM	None
Homo sapiens	IGROV-1	GI50	100000.0	nM	None
Homo sapiens	K562	GI50	100000.0	nM	None
Homo sapiens	KM12	GI50	100000.0	nM	None
Homo sapiens	LOX IMVI	GI50	100000.0	nM	None
Homo sapiens	M14	GI50	100000.0	nM	None
Homo sapiens	Malme-3M	GI50	100000.0	nM	None
Homo sapiens	MCF7	GI50	100000.0	nM	None
Homo sapiens	MDA-MB-231	GI50	100000.0	nM	None
Homo sapiens	MDA-MB-435	GI50	100000.0	nM	None
Homo sapiens	MDA-N	GI50	100000.0	nM	None
Homo sapiens	MOLT-4	GI50	100000.0	nM	None
Homo sapiens	Monoamine oxidase A	AC50	30000.0	nM	10.1038/s41467-023-40064-9
Homo sapiens	Mu opioid receptor	AC50	10000.0	nM	10.1038/s41467-023-40064-9
Homo sapiens	Muscarinic acetylcholine receptor M1	AC50	30000.0	nM	10.1038/s41467-023-40064-9
Homo sapiens	Muscarinic acetylcholine receptor M2	AC50	30000.0	nM	10.1038/s41467-023-40064-9
Homo sapiens	NCI/ADR-RES	GI50	100000.0	nM	None
Homo sapiens	NCI-H226	GI50	100000.0	nM	None
Homo sapiens	NCI-H23	GI50	100000.0	nM	None
Homo sapiens	NCI-H322M	GI50	100000.0	nM	None
Homo sapiens	NCI-H460	GI50	100000.0	nM	None
Homo sapiens	Neutral amino acid transporter A	IC50	188000.0	nM	None
Homo sapiens	Neutral amino acid transporter A	IC50	2000000.0	nM	None
Homo sapiens	Neutral amino acid transporter B(0)	IC50	2000000.0	nM	None
Homo sapiens	Neutral amino acid transporter B(0)	IC50	3475000.0	nM	None
Homo sapiens	Norepinephrine transporter	AC50	30000.0	nM	10.1038/s41467-023-40064-9
Homo sapiens	OVCAR-3	GI50	100000.0	nM	None
Homo sapiens	OVCAR-4	GI50	100000.0	nM	None
Homo sapiens	OVCAR-5	GI50	100000.0	nM	None
Homo sapiens	OVCAR-8	GI50	100000.0	nM	None
Homo sapiens	PC-3	GI50	100000.0	nM	None
Homo sapiens	Phosphodiesterase 3A	AC50	30000.0	nM	10.1038/s41467-023-40064-9
Homo sapiens	Phosphodiesterase 4A	AC50	30000.0	nM	10.1038/s41467-023-40064-9
Homo sapiens	Progesterone receptor	AC50	30000.0	nM	10.1038/s41467-023-40064-9
Homo sapiens	Proton-coupled amino acid transporter 1	Ki	9000000.0	nM	10.1016/j.bmc.2011.08.058
Homo sapiens	Proton-coupled amino acid transporter 1	pKi	-0.95	mM	10.1016/j.bmc.2011.08.058
Homo sapiens	RPMI-8226	GI50	100000.0	nM	None
Homo sapiens	RXF 393	GI50	100000.0	nM	None
Homo sapiens	Serotonin 1a (5-HT1a) receptor	AC50	30000.0	nM	10.1038/s41467-023-40064-9
Homo sapiens	Serotonin 2b (5-HT2b) receptor	AC50	30000.0	nM	10.1038/s41467-023-40064-9
Homo sapiens	Serotonin transporter	AC50	30000.0	nM	10.1038/s41467-023-40064-9
Homo sapiens	SF-268	GI50	100000.0	nM	None
Homo sapiens	SF-295	GI50	100000.0	nM	None
Homo sapiens	SF-539	GI50	100000.0	nM	None
Homo sapiens	SK-MEL-2	GI50	100000.0	nM	None
Homo sapiens	SK-MEL-28	GI50	100000.0	nM	None
Homo sapiens	SK-MEL-5	GI50	100000.0	nM	None
Homo sapiens	SK-OV-3	GI50	100000.0	nM	None
Homo sapiens	SN12C	GI50	100000.0	nM	None
Homo sapiens	SNB-19	GI50	100000.0	nM	None
Homo sapiens	SNB-75	GI50	100000.0	nM	None
Homo sapiens	SR	GI50	100000.0	nM	None
Homo sapiens	SW-620	GI50	100000.0	nM	None
Homo sapiens	T47D	GI50	100000.0	nM	None
Homo sapiens	Thrombin	AC50	30000.0	nM	10.1038/s41467-023-40064-9
Homo sapiens	Thromboxane A2 receptor	AC50	30000.0	nM	10.1038/s41467-023-40064-9
Homo sapiens	TK-10	GI50	100000.0	nM	None
Homo sapiens	U-251	GI50	100000.0	nM	None
Homo sapiens	UACC-257	GI50	100000.0	nM	None
Homo sapiens	UACC-62	GI50	100000.0	nM	None
Homo sapiens	UO-31	GI50	100000.0	nM	None
Homo sapiens	Vascular endothelial growth factor receptor 2	AC50	30000.0	nM	10.1038/s41467-023-40064-9
Homo sapiens	Von Hippel-Lindau disease tumor suppressor	Activity	nan	None	10.1021/ml400296c
Rattus norvegicus	Amino acid transporter	IC50	16000.0	nM	None
Rattus norvegicus	Amino acid transporter	IC50	17200.0	nM	None
Rattus norvegicus	Amino acid transporter	IC50	38900.0	nM	None
Rattus norvegicus	Amino acid transporter	IC50	2989000.0	nM	None
Rattus norvegicus	Amino acid transporter	IC50	3047000.0	nM	None
Rattus norvegicus	Amino acid transporter	Inhibition	25.0	%	None
Rattus norvegicus	Amino acid transporter	Inhibition	nan	%	None
Rattus norvegicus	Asc-type amino acid transporter 1	IC50	10000000.0	nM	None
Rattus norvegicus	Carnitine/acylcarnitine translocase	Experimental DPM	5346.0	None	10.1021/jm00155a045
Rattus norvegicus	GABA receptor alpha-1 subunit	AC50	30000.0	nM	10.1038/s41467-023-40064-9
Rattus norvegicus	Glutamate NMDA receptor	Activity	nan	None	None
Severe acute respiratory syndrome coronavirus 2	Replicase polyprotein 1ab	Inhibition	3.712	%	10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	Inhibition	-0.11	%	10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	Inhibition	33.43	%	10.21203/rs.3.rs-23951/v1
None	Unchecked	Activity	3.0	uM	None

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT000411	C(=O)[C@@H](NC(=O)[C@H](CCCN)NC(=O)CCCCCCC/C=C\C/C=C\CCCCC)[C@@H](C)O.O=C(O)[C@@H]1C[C@@H](O)CN1>>C(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@@H](NC(=O)C(CCCN)NC(=O)CCCCCCC/C=C\C/C=C\CCCCC)[C@@H](C)O	RXN-16502
AKRT004455	CC(=O)[32S].O=C(O)[C@@H]1C[C@@H](O)CN1>>CC(=O)N1C[C@H](O)C[C@H]1C(=O)O	None
AKRT004754	CC(=O)[CoA].O=C(O)[C@@H]1C[C@@H](O)CN1>>CC(=O)N1C[C@H](O)C[C@H]1C(=O)O	enzymemap_30376
AKRT012931	C[C@@H](O)[C@H](N)C(=O)O.Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O.O=C(O)[C@@H]1C[C@@H](O)CN1>>C[C@@H](O)[C@H](NC(=O)[C@@H]1C[C@@H](O)CN1)C(=O)O.Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O	None
AKRT012942	C[C@@H](O)[C@H](N)C(=O)O.O=C(O)[C@@H]1C[C@@H](O)CN1>>C[C@@H](O)[C@H](NC(=O)[C@@H]1C[C@@H](O)CN1)C(=O)O	enzymemap_90859
AKRT015424	Cc1ncc(C[n+]2csc(CCO)c2C)c(N)n1.O=C(O)[C@@H]1C[C@@H](O)CN1>>Cc1ncc(CN2C[C@H](O)CC2C(=O)O)c(N)n1	enzymemap_40245
AKRT017532	NCC(=O)N1C[C@H](O)C[C@H]1C(=O)O>>O=C(O)[C@@H]1C[C@@H](O)CN1	enzymemap_66558
AKRT022541	O=C(Nc1ccc2ccccc2c1)[C@@H]1C[C@@H](O)CN1>>Nc1ccc2ccccc2c1.O=C(O)[C@@H]1C[C@@H](O)CN1	None
AKRT022542	O=C(Nc1ccc2ccccc2c1)[C@@H]1C[C@@H](O)CN1>>O=C(O)[C@@H]1C[C@@H](O)CN1	enzymemap_65916
AKRT022655	O=C(O)C1=NC[C@H](O)C1>>O=C(O)[C@@H]1C[C@@H](O)CN1	enzymemap_22833
AKRT022667	O=C(O)C1CC(O)C=N1>>O=C(O)[C@@H]1C[C@@H](O)CN1	enzymemap_22910
AKRT022874	O=C(O)CNC(=O)[C@@H]1C[C@@H](O)CN1>>O=C(O)[C@@H]1C[C@@H](O)CN1	enzymemap_65988
AKRT023029	O=C(O)[C@@H]1CCCN1>>O=C(O)[C@@H]1C[C@@H](O)CN1	R01252
AKRT023046	O=C(O)[C@@H]1C[C@@H](O)CN1>>O=C(O)C1=NC[C@H](O)C1	enzymemap_22833
AKRT023047	O=C(O)[C@@H]1C[C@@H](O)CN1>>O=C(O)[C@@H]1CCC=N1	R11819
AKRT023048	O=C(O)[C@@H]1C[C@@H](O)CN1>>O=C(O)[C@@H]1C[C@@H](O)C=N1	RXN66-545
AKRT023049	O=C(O)[C@@H]1C[C@@H](O)CN1>>O=C(O)[C@H]1C[C@@H](O)CN1	4-HYDROXYPROLINE-EPIMERASE-RXN
AKRT023051	O=C(O)[C@@H]1C[C@@H](O)CN1C(=O)[C@@H]1CCCN1>>O=C(O)[C@@H]1C[C@@H](O)CN1	enzymemap_66557
AKRT023052	O=C(O)[C@@H]1C[C@@H](O)CN1[C@H]1O[C@@H](CO)[C@H](O)[C@H]1O>>O=C(O)[C@@H]1C[C@@H](O)CN1	enzymemap_60300
AKRT023053	O=C(O)[C@@H]1C[C@@H](O)CN1[C@H]1O[C@@H](CO)[C@H](O)[C@H]1O>>O=C(O)[C@@H]1C[C@@H](O)CN1.OC[C@@H]1O[C@H](O)[C@H](O)[C@H]1O	None
AKRT023057	O=C(O)[C@@H]1C[C@H](O[C@H]2O[C@@H](CO)[C@H](O)[C@H]2O)CN1>>O=C(O)[C@@H]1C[C@@H](O)CN1	enzymemap_60300
AKRT023058	O=C(O)[C@@H]1C[C@H](O[C@H]2O[C@@H](CO)[C@H](O)[C@H]2O)CN1>>O=C(O)[C@@H]1C[C@@H](O)CN1.OC[C@@H]1O[C@H](O)[C@H](O)[C@H]1O	None
AKRT023111	O=C(O)[C@H]1C[C@@H](O)CN1>>O=C(O)[C@@H]1C[C@@H](O)CN1	R03296
AKRT023572	O=C1CN[C@H](C(=O)O)C1>>O=C(O)[C@@H]1C[C@@H](O)CN1	enzymemap_707