5-Hydroxytryptophan

Details

• Internal ID: e4f879f7-4b12-4f59-b92c-b7da8367abfb
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Tryptamines and derivatives > Serotonins
• IUPAC Name: 2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid
• SMILES (Canonical): C1=CC2=C(C=C1O)C(=CN2)CC(C(=O)O)N
• SMILES (Isomeric): C1=CC2=C(C=C1O)C(=CN2)CC(C(=O)O)N
• InChI: InChI=1S/C11H12N2O3/c12-9(11(15)16)3-6-5-13-10-2-1-7(14)4-8(6)10/h1-2,4-5,9,13-14H,3,12H2,(H,15,16)
• InChI Key: LDCYZAJDBXYCGN-UHFFFAOYSA-N
• Popularity: 8,728 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₂N₂O₃
• Molecular Weight: 220.22 g/mol
• Exact Mass: 220.08479225 g/mol
• Topological Polar Surface Area (TPSA): 99.30 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): 0.83
• H-Bond Acceptor: 3
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

• 56-69-9
• 5-Hydroxy-DL-tryptophan
• DL-5-Hydroxytryptophan
• 2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid
• 114-03-4
• 5-HTP
• (+-)-5-Hydroxytryptophan
• DL-Hydroxytryptophan
• DL-5-HTP
• 5-Hydroxytryptophan DL-form
• D,L-5-hydroxytryptophan
• Tryptophan, 5-hydroxy-
• 5-hydroxy l-tryptophan
• NSC-92523
• (+/-)-5-Hydroxytryptophan
• 5-hydroxytryptophan (5-HTP)
• CHEBI:28171
• 9181P3OI6N
• MFCD00005651
• 72572-98-6
• DL-Pretonine
• Dl-oxitriptan
• H-DL-Trp(5-OH)-OH
• 5-hydroxy tryptophan
• USAF CB-96
• 5-hydroxytryptophan, dl-
• 5-Hydroxytryptophan L form
• HSDB 4295
• dl-5-Hydroxytryptophane
• NCI-C56644
• Tryptophan, 5-hydroxy-, dl
• 5-22-14-00278 (Beilstein Handbook Reference)
• EINECS 200-284-8
• Tryptophan, 5-hydroxy-, L-
• NSC 92523
• BRN 0088199
• DL-Tryptophan, 5-hydroxy-
• UNII-9181P3OI6N
• MFCD00064341
• 5-Hydroxytryptophan #
• H-L-Trp(5-OH)-OH
• 5-hydroxytryptophan(5-HTP)
• SCHEMBL43242
• MLS006011926
• 2-Amino-3-(5-hydroxy-1H-indol-3-yl)propanoicacid
• (.+-.)-5-Hydroxytryptophan
• CHEMBL162789
• 5-Hydroxytryptophan, AldrichCPR
• SCHEMBL19871232
• 5-HYDROXYTRYPTOPHAN [MI]
• DTXSID50859863
• HMS3372G05
• HMS3656M11
• HMS3884H15
• WLN: T56 BMJ D1YZVQ GQ
• 5-HYDROXYTRYPTOPHAN [HSDB]
• HY-N0122
• NSC92523
• s2374
• AKOS003382640
• AKOS016050369
• CCG-235444
• NCGC00015526-02
• NCGC00015526-04
• AC-13632
• AC-23979
• SMR000326745
• SY030569
• SY048412
• VS-03256
• A2320
• CS-0007832
• FT-0620484
• FT-0620490
• FT-0620491
• FT-0620498
• FT-0627633
• SW219417-1
• C01017
• DL-2-Amino-3-(5-hydroxyindolyl)propionic acid
• EN300-244707
• H-8280
• N88462
• SR-01000003309
• Q-102914
• SR-01000003309-1
• Q27103541
• (S)-2-Amino-3-(5-hydroxy-1H-indol-3-yl)-propionic acid;C5-Hydroxy-L-tryptophan;5-HTP;Oxitriptan

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9959	99.59%
Caco-2	-	0.8085	80.85%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	+	0.7857	78.57%
Subcellular localzation	Mitochondria	0.4856	48.56%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9253	92.53%
OATP1B3 inhibitior	+	0.9483	94.83%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7123	71.23%
P-glycoprotein inhibitior	-	0.9897	98.97%
P-glycoprotein substrate	-	0.7721	77.21%
CYP3A4 substrate	-	0.6378	63.78%
CYP2C9 substrate	-	0.8108	81.08%
CYP2D6 substrate	-	0.7013	70.13%
CYP3A4 inhibition	-	0.9642	96.42%
CYP2C9 inhibition	-	0.9072	90.72%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.6357	63.57%
CYP inhibitory promiscuity	-	0.8947	89.47%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8223	82.23%
Carcinogenicity (trinary)	Non-required	0.6474	64.74%
Eye corrosion	-	0.9954	99.54%
Eye irritation	-	0.7964	79.64%
Skin irritation	-	0.8365	83.65%
Skin corrosion	-	0.9618	96.18%
Ames mutagenesis	-	0.9200	92.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6841	68.41%
Micronuclear	+	0.8674	86.74%
Hepatotoxicity	-	0.6761	67.61%
skin sensitisation	-	0.7983	79.83%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.9223	92.23%
Acute Oral Toxicity (c)	II	0.7340	73.40%
Estrogen receptor binding	-	0.7754	77.54%
Androgen receptor binding	-	0.6879	68.79%
Thyroid receptor binding	-	0.6929	69.29%
Glucocorticoid receptor binding	-	0.4862	48.62%
Aromatase binding	-	0.8514	85.14%
PPAR gamma	+	0.6089	60.89%
Honey bee toxicity	-	0.9465	94.65%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.8149	81.49%
Fish aquatic toxicity	-	0.6627	66.27%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293235	P02545	Prelamin-A/C	39.8 nM	Potency	via Super-PRED
CHEMBL214	P08908	Serotonin 1a (5-HT1a) receptor	0.91 nM	Ki	via Super-PRED
CHEMBL224	P28223	Serotonin 2a (5-HT2a) receptor	1.349 nM	EC50	via Super-PRED
CHEMBL1833	P41595	Serotonin 2b (5-HT2b) receptor	1 nM	EC50	via Super-PRED
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	0.18 nM	EC50	via Super-PRED
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	2.12 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.61%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.06%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.59%	96.09%
CHEMBL1255126	O15151	Protein Mdm4	95.13%	90.20%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.19%	94.45%
CHEMBL2581	P07339	Cathepsin D	91.45%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.81%	95.56%
CHEMBL213	P08588	Beta-1 adrenergic receptor	88.12%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.23%	99.17%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	86.93%	83.10%
CHEMBL2535	P11166	Glucose transporter	86.87%	98.75%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	86.70%	91.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.86%	99.15%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	84.69%	94.62%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.00%	96.95%
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	80.96%	95.48%
CHEMBL4101	P17612	cAMP-dependent protein kinase alpha-catalytic subunit	80.93%	82.86%

Plants that contains it

• Atalantia buxifolia
• Thapsia gymnesica

Cross-Links

• PubChem: 144
• LOTUS: LTS0175675
• wikiData: Q105144066