Hydroxyproline

Details

• Internal ID: 1a7251e7-3d52-4a87-9116-d937fb2af662
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Proline and derivatives
• IUPAC Name: (2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid
• SMILES (Canonical): C1C(CNC1C(=O)O)O
• SMILES (Isomeric): C1[C@H](CN[C@@H]1C(=O)O)O
• 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
• InChI Key: PMMYEEVYMWASQN-DMTCNVIQSA-N
• Popularity: 1,047 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅H₉NO₃
• Molecular Weight: 131.13 g/mol
• Exact Mass: 131.058243149 g/mol
• Topological Polar Surface Area (TPSA): 69.60 Ų
• XlogP: -3.30
• Atomic LogP (AlogP): -1.21
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• hydroxyproline
• 51-35-4
• L-Hydroxyproline
• (2S,4R)-4-Hydroxypyrrolidine-2-carboxylic acid
• trans-4-Hydroxyproline
• L-4-hydroxyproline
• Hypro
• H-Hyp-OH
• hydroxy-L-proline
• 4-Hydroxy-L-proline
• 4-hydroxyproline
• trans-L-Hydroxyproline
• L-Proline, 4-hydroxy-, (4R)-
• trans-Hydroxyproline
• (4R)-4-hydroxy-L-proline
• 4-Hydroxy-2-pyrrolidinecarboxylic acid
• delta-Hydroxyproline
• L-Proline, 4-hydroxy-, trans-
• Proline, 4-hydroxy-, L-
• Hydroxyproline (VAN)
• L-Proline, 4-hydroxy-
• Ls-Hydroxyproline
• UNII-RMB44WO89X
• RMB44WO89X
• (2S,4R)-4-hydroxyproline
• 4-L-Hydroxyproline
• Proline, 4-hydroxy- (VAN)
• LUMISTOR
• CHEBI:18095
• (2S,4R)-trans-4-hydroxyproline
• trans-4-hydroxy-proline
• L-threo-4-hydroxyproline
• EINECS 200-091-9
• NSC 46704
• NSC-46704
• Proline, 4-hydroxy-
• CHEMBL352418
• Hyp
• trans-L-4-hydroxyproline
• DTXSID10883225
• (2S,4R)-4-hydroxy-2-pyrrolidinecarboxylic acid
• NSC46704
• trans-oxyproline
• 618-28-0
• trans-hydroxy-L-proline
• (2S,4R)-rel-4-Hydroxypyrrolidine-2-carboxylic acid
• L-Hydroxyprolin
• trans-L-4-hydroxy-proline
• MFCD00064320
• L-Proline, 4-hydroxy-, trans- (9CI)
• SMR000857104
• 6912-67-0
• CHEBI:18240
• hydroxiproline
• oxyproline
• hydroxy-proline
• L-Hydroxyproline;
• H-trans-Hyp-OH
• Hydroxyproline,(l)
• L-Proline, trans-
• NMH-Pro
• (4r)-hydroxyproline
• 4(R)-hydroxyproline
• (2S,4R)-(-)-4-Hydroxy-2-Pyrrolidinecarboxylic Acid
• .delta.-Hydroxyproline
• L-Hydroxyproline,(S)
• L- 4- hydroxyproline
• L-4-transhydroxyproline
• 4 HYDROXYPROLINE
• trans-4-hydroxyL-proline
• trans-4-D-Hydroxyproline
• Trans4-hydroxy-L-proline
• bmse000123
• bmse000966
• D02YMI
• L-trans-4-hydroxy-proline
• trans-4-hydroxy(L)proline
• HYDROXYPROLINE [MI]
• trans-4-hydroxyl-l-proline
• SCHEMBL21185
• HYDROXYPROLINE [INCI]
• MLS001332463
• MLS001332464
• trans-4-hydroxy-(L)-proline
• (2S, 4R)-4-hydroxyproline
• GTPL4704
• (2s,4r)-4-hydroxy-l-proline
• HYDROXYPROLINE [WHO-DD]
• (2S, 4R)-4-hydroxy-proline
• CHEBI:24741
• PMMYEEVYMWASQN-DMTCNVIQSA-N
• DTXCID001022774
• L-prolina, 4-hidroxi-, (4R)-
• BDBM50357233
• s5820
• trans-4-Hydroxy-L-proline, >=99%
• AKOS007930607
• AC-2249
• AM81829
• CS-W008928
• DB08847
• PS-5807
• (2S,4R)-2-carboxy-4-hydroxypyrrolidine
• BP-10638
• HY-40135
• NCI60_004102
• L-Hydroxyproline;trans-4-Hydroxy-L-Proline
• 4(R)-hydroxy-2(S)-pyrrolidinecarboxylic acid
• EN300-53732
• C01157
• H-7290
• M03214
• P16433
• trans-4-Hydroxy-L-proline, analytical standard
• (2S, 4R)-4-hydroxy-2-pyrrolidinecarboxylic acid
• (2S,4R)-4-hydroxy-pyrrolidine-2-carboxylic acid
• 4-(R)-hydroxy-pyrrolidine-2-(S)-carboxylic acid
• A905519
• (2S, 4R)-4-hydroxy-2-pyrrolidine-carboxylic acid
• J-525022
• Q27089020
• trans-4-Hydroxy-L-proline, BioXtra, >=99.0% (NT)
• F8889-8652
• Z802856442
• F05487BD-FA1D-4C80-83AD-3A91E2078031
• trans-4-Hydroxy-L-proline, microbial, cell culture tested
• trans-4-Hydroxy-L-proline, Vetec(TM) reagent grade, 99%
• trans-4-Hydroxy-L-proline, BioReagent, suitable for cell culture, >=98.5%
• Hydroxyproline, Pharmaceutical Secondary Standard; Certified Reference Material

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9439	94.39%
Caco-2	-	0.8873	88.73%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5864	58.64%
OATP2B1 inhibitior	-	0.8372	83.72%
OATP1B1 inhibitior	+	0.9680	96.80%
OATP1B3 inhibitior	+	0.9447	94.47%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9768	97.68%
P-glycoprotein inhibitior	-	0.9917	99.17%
P-glycoprotein substrate	-	0.9622	96.22%
CYP3A4 substrate	-	0.6657	66.57%
CYP2C9 substrate	-	0.8075	80.75%
CYP2D6 substrate	-	0.6868	68.68%
CYP3A4 inhibition	-	1.0000	100.00%
CYP2C9 inhibition	-	0.9619	96.19%
CYP2C19 inhibition	-	0.9623	96.23%
CYP2D6 inhibition	-	0.9367	93.67%
CYP1A2 inhibition	-	0.9332	93.32%
CYP2C8 inhibition	-	0.9834	98.34%
CYP inhibitory promiscuity	-	0.9913	99.13%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7268	72.68%
Eye corrosion	-	0.9702	97.02%
Eye irritation	+	0.7898	78.98%
Skin irritation	-	0.7804	78.04%
Skin corrosion	-	0.7918	79.18%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8414	84.14%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	+	0.6033	60.33%
skin sensitisation	-	0.8915	89.15%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.4549	45.49%
Acute Oral Toxicity (c)	III	0.5577	55.77%
Estrogen receptor binding	-	0.9115	91.15%
Androgen receptor binding	-	0.8918	89.18%
Thyroid receptor binding	-	0.8852	88.52%
Glucocorticoid receptor binding	-	0.8167	81.67%
Aromatase binding	-	0.8784	87.84%
PPAR gamma	-	0.8425	84.25%
Honey bee toxicity	-	0.8629	86.29%
Biodegradation	+	0.7250	72.50%
Crustacea aquatic toxicity	-	0.8400	84.00%
Fish aquatic toxicity	-	0.9709	97.09%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	91.18%	96.95%
CHEMBL4040	P28482	MAP kinase ERK2	89.75%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.49%	96.09%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	88.97%	97.21%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.34%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.33%	94.45%

Plants that contains it

• Afzelia bella
• Arabidopsis thaliana
• Prunus domestica

Cross-Links

• PubChem: 5810
• NPASS: NPC196359
• LOTUS: LTS0236149
• wikiData: Q12460151