Tegaserod

Details

• Internal ID: 2fb96aa8-7e03-4753-8b4d-e4080308e8f9
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Indoles
• IUPAC Name: 1-[(E)-(5-methoxy-1H-indol-3-yl)methylideneamino]-2-pentylguanidine
• InChI: InChI=1S/C16H23N5O/c1-3-4-5-8-18-16(17)21-20-11-12-10-19-15-7-6-13(22-2)9-14(12)15/h6-7,9-11,19H,3-5,8H2,1-2H3,(H3,17,18,21)/b20-11+
• InChI Key: IKBKZGMPCYNSLU-RGVLZGJSSA-N
• Popularity: 357 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₃N₅O
• Molecular Weight: 301.39 g/mol
• Exact Mass: 301.19026037 g/mol
• Topological Polar Surface Area (TPSA): 87.80 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.60
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 7

Synonyms

• 145158-71-0
• tegaserodum
• SDZ-HTF-919
• HTF919
• DTXSID6045955
• 1-(((5-Methoxyindol-3-yl)methylene)amino)-3-pentylguanidine
• CHEBI:51043
• 458VC51857
• 1-[(E)-(5-methoxy-1H-indol-3-yl)methylideneamino]-2-pentylguanidine
• Hydrazinecarboximidamide, 2-[(5-methoxy-1H-indol-3-yl)methylene]-N-pentyl-
• Hydrazinecarboximidamide, 2-((5-methoxy-1H-indol-3-yl)methylene)-N-pentyl-
• 2-[(5-methoxy-2,3-dihydro-1H-indol-3-yl)methylene]-N-pentylhydrazinecarboximidamide
• 1-[[(5-Methoxyindol-3-yl)methylene]amino]-3-pentylguanidine
• 1-((E)-(5-methoxy-1H-indol-3-yl)methylideneamino)-2-pentylguanidine
• 2-((5-methoxy-2,3-dihydro-1H-indol-3-yl)methylene)-N-pentylhydrazinecarboximidamide
• RefChem:57725
• SDZ HTF-919
• A06AX06
• DTXCID20810446
• 5-methoxyindol-3-carboxaldehyde amino(pentylamino)methylenehydrazone hydrogen maleate
• Zelnorm
• Zelmac
• HTF 919
• CHEMBL76370
• NCGC00095192-01
• 2-((5-Methoxy-1H-indol-3-yl)methylene)-N-pentylhydrazinecarboximidamide
• SDZ HTF 919
• DTXCID4025955
• MLS001401406
• 1044642-88-7
• CAS-145158-71-0
• Tegaserod (USAN/INN)
• SMR000471618
• Tegaserod (maleate)?
• TEGASEROD [INN]
• TEGASEROD [MI]
• TEGASEROD [USAN]
• Spectrum5_001691
• TEGASEROD [VANDF]
• TEGASEROD [WHO-DD]
• SCHEMBL16464
• BSPBio_002344
• BSPBio_003270
• GTPL226
• TEGASEROD [EMA EPAR]
• SPECTRUM1505823
• SCHEMBL7335966
• SCHEMBL8229619
• N'-[(E)-[(5-methoxy-1H-indol-3-yl)methylidene]amino]-N-pentylguanidine
• SCHEMBL25238967
• BDBM79022
• CHEBI:94540
• cid_6918369
• (E)-2-((5-methoxy-1H-indol-3-yl)methylene)-N-pentylhydrazine-1-carboximidamide
• HMS1922J08
• Tox21_111481
• BDBM50240618
• BDBM50248157
• EBC-04413
• N'-{[(5-methoxy-1H-indol-3-yl)methylidene]amino}-N-pentylguanidine
• AKOS015913793
• Tox21_111481_1
• AC-4564
• DB01079
• FT39316
• NCGC00095192-02
• NCGC00095192-03
• NCGC00095192-04
• NCGC00095192-05
• NCGC00095192-08
• NCGC00095192-11
• HY-14153
• LS-14526
• CS-0003233
• NS00009294
• 58T710
• D06056
• EN300-117255
• Q44944
• AB01209613-01
• AB01209613-03
• AB01563050_01
• BRD-K88743730-001-01-0
• BRD-K88743730-050-03-3
• BRD-K88743730-050-04-1
• Z1501480423
• 1-[(5-methoxy-3-indolylidene)methylamino]2-pentylguanidine
• 1-[(E)-(5-methoxy-1H-indol-3-yl)methyleneamino]-2-pentyl-guanidine
• (2E)-2-[(5-methoxy-1H-indol-3-yl)methylene]-N-pentylhydrazinecarboximidamide
• (Z)-2-butenedioic acid;1-[[(Z)-(5-methoxy-3-indolylidene)methyl]amino]-2-pentylguanidine
• (Z)-but-2-enedioic acid;1-[[(Z)-(5-methoxyindol-3-ylidene)methyl]amino]-2-pentylguanidine
• 2-amyl-1-[[(Z)-(5-methoxyindol-3-ylidene)methyl]amino]guanidine;maleic acid
• HYDRAZINECARBOXIMIDAMIDE, 2-((5-METHOXY-1H-INDOL-3-YL)METHYLENE)-N-PENTYL-, (2E)-
• (Z)-but-2-enedioic acid;1-[[(Z)-(5-methoxyindol-3-ylidene)methyl]amino]-2-pentyl-guanidine

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9943	99.43%
Caco-2	-	0.5710	57.10%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.5365	53.65%
OATP2B1 inhibitior	-	0.8588	85.88%
OATP1B1 inhibitior	+	0.8995	89.95%
OATP1B3 inhibitior	+	0.9409	94.09%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.8086	80.86%
P-glycoprotein inhibitior	-	0.8278	82.78%
P-glycoprotein substrate	+	0.8059	80.59%
CYP3A4 substrate	-	0.5310	53.10%
CYP2C9 substrate	-	0.8225	82.25%
CYP2D6 substrate	-	0.7365	73.65%
CYP3A4 inhibition	-	0.7900	79.00%
CYP2C9 inhibition	-	0.6998	69.98%
CYP2C19 inhibition	-	0.6082	60.82%
CYP2D6 inhibition	-	0.5940	59.40%
CYP1A2 inhibition	+	0.6144	61.44%
CYP2C8 inhibition	+	0.6306	63.06%
CYP inhibitory promiscuity	-	0.6269	62.69%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8000	80.00%
Carcinogenicity (trinary)	Non-required	0.6014	60.14%
Eye corrosion	-	0.9865	98.65%
Eye irritation	-	0.9781	97.81%
Skin irritation	-	0.7509	75.09%
Skin corrosion	-	0.8976	89.76%
Ames mutagenesis	+	0.5146	51.46%
Human Ether-a-go-go-Related Gene inhibition	+	0.7609	76.09%
Micronuclear	+	0.6100	61.00%
Hepatotoxicity	-	0.6676	66.76%
skin sensitisation	-	0.8352	83.52%
Respiratory toxicity	+	0.9222	92.22%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.8544	85.44%
Acute Oral Toxicity (c)	III	0.6119	61.19%
Estrogen receptor binding	+	0.8352	83.52%
Androgen receptor binding	+	0.5784	57.84%
Thyroid receptor binding	+	0.8747	87.47%
Glucocorticoid receptor binding	+	0.6342	63.42%
Aromatase binding	+	0.8146	81.46%
PPAR gamma	+	0.6567	65.67%
Honey bee toxicity	-	0.9232	92.32%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5402	54.02%
Fish aquatic toxicity	+	0.8437	84.37%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.82%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.60%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.96%	96.09%
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	94.05%	93.24%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.66%	99.17%
CHEMBL230	P35354	Cyclooxygenase-2	93.24%	89.63%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.53%	95.56%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	91.35%	92.08%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.97%	96.00%
CHEMBL2535	P11166	Glucose transporter	90.14%	98.75%
CHEMBL255	P29275	Adenosine A2b receptor	89.71%	98.59%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	88.95%	89.62%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	88.29%	91.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.02%	95.89%
CHEMBL2581	P07339	Cathepsin D	87.41%	98.95%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	87.32%	92.88%
CHEMBL4581	P52732	Kinesin-like protein 1	87.19%	93.18%
CHEMBL4208	P20618	Proteasome component C5	86.59%	90.00%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	84.76%	91.81%
CHEMBL1951	P21397	Monoamine oxidase A	84.20%	91.49%
CHEMBL5443	O00311	Cell division cycle 7-related protein kinase	83.39%	96.11%
CHEMBL1781	P11387	DNA topoisomerase I	81.41%	97.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.09%	97.09%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 135409453
• LOTUS: LTS0142806
• wikiData: Q44944