Phosphoramidon

Details

• Internal ID: c86259f0-09cd-469b-b914-af2f6bb511f8
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides > Dipeptides
• IUPAC Name: (2S)-2-[[(2S)-2-[[hydroxy-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyphosphoryl]amino]-4-methylpentanoyl]amino]-3-(1H-indol-3-yl)propanoic acid
• InChI: InChI=1S/C23H34N3O10P/c1-11(2)8-16(26-37(33,34)36-23-20(29)19(28)18(27)12(3)35-23)21(30)25-17(22(31)32)9-13-10-24-15-7-5-4-6-14(13)15/h4-7,10-12,16-20,23-24,27-29H,8-9H2,1-3H3,(H,25,30)(H,31,32)(H2,26,33,34)/t12-,16-,17-,18-,19+,20+,23-/m0/s1
• InChI Key: ZPHBZEQOLSRPAK-XLCYBJAPSA-N
• Popularity: 936 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₄N₃O₁₀P
• Molecular Weight: 543.50 g/mol
• Exact Mass: 543.19818129 g/mol
• Topological Polar Surface Area (TPSA): 211.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): 0.23
• H-Bond Acceptor: 8
• H-Bond Donor: 8
• Rotatable Bonds: 11

Synonyms

• 36357-77-4
• Phosphramidon
• Phosporamidon
• N-ALPHA-L-RHAMNOPYRANOSYLOXY(HYDROXYPHOSPHINYL)-L-LEUCYL-L-TRYPTOPHAN
• CHEMBL479579
• T3G94E2LB1
• CHEBI:45353
• Phosphoramidon disodium salt
• N-(N-(((6-Deoxy-alpha-L-mannopyranosyl)oxy)hydroxyphosphinyl)-L-leucyl)-L-tryptophan
• 119942-99-3
• L-TRYPTOPHAN,N-[[(6-DEOXY-A-L-MANNOPYRANOSYL)OXY]HYDROXYPHOSPHINYL]-L-LEUCYL-
• (hydroxy(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)phosphoryl)-L-leucyl-L-tryptophan
• RDF
• UNII-T3G94E2LB1
• 1tlp
• EINECS 252-996-3
• SCHEMBL40933
• GTPL11653
• ZPHBZEQOLSRPAK-XLCYBJAPSA-N
• DTXSID601317292
• (phosphoramidon) 2-{2-[Hydroxy-(3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-phosphorylamino]-4-methyl-pentanoylamino}-3-(1H-indol-3-yl)-propionic acid
• (S)-2-{(R)-2-[Hydroxy-((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-phosphorylamino]-4-methyl-pentanoylamino}-3-(1H-indol-3-yl)-propionic acid
• 2-{2-[Hydroxy-(3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-phosphorylamino]-4-methyl-pentanoylamino}-3-(1H-indol-3-yl)-propionic acid
• HY-N2021
• L-TRYPTOPHAN, N-(((6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)OXY)HYDROXYPHOSPHINYL)-L-LEUCYL-
• BDBM50251742
• AKOS040744615
• DB02557
• (2S)-2-[[(2S)-2-[[hydroxy-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyphosphoryl]amino]-4-methylpentanoyl]amino]-3-(1H-indol-3-yl)propanoic acid
• CS-0018379
• C00563
• Q7187544
• N-(alpha-l-rhamnopyranosyloxyhydroxyphosphinyl)-l-leucyl-l-tryptophan
• L-Tryptophan, N-(N-(((6-deoxy-alpha-L-mannopyranosyl)oxy)hydroxyphosphinyl)-L-leucyl)-
• (2S)-2-((2S)-2-((Hydroxy(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)phosphoryl)amino)-4-methylpentanamido)-3-(1H-indol-3-yl)propanoic acid
• (2S)-2-((2S)-2-((Hydroxy(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)phosphoryl)amino)-4-methylpentanamido)-3-(1H-indol-3-yl)propanoicacid
• (2S)-2-[[(2S)-2-[[hydroxy-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-phosphoryl]amino]-4-methyl-pentanoyl]amino]-3-(1H-indol-3-yl)propanoic acid
• (2S)-2-{[(2S)-2-{[(S)-hydroxy{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}phosphoryl]amino}-4-methylpentanoyl]amino}-3-(1H-indol-3-yl)propanoic acid
• (2S)-2-{[(2S)-2-{[(S)-hydroxy{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}phosphoryl]amino}-4-methylpentanoyl]amino}-3-(1H-indol-3-yl)propanoic acid (non-preferred name)
• (3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-2H-pyran-2-yl hydrogen (S)-1-((S)-1-(1H-indol-3-yl)-3-oxobutan-2-ylamino)-4-methyl-1-oxopentan-2-ylphosphoramidate
• (S)-2-{(S)-2-[Hydroxy-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-phosphorylamino]-4-methyl-pentanoylamino}-3-(1H-indol-3-yl)-propionic acid
• (S)-2-{(S)-2-[Hydroxy-((3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-phosphorylamino]-4-methyl-pentanoylamino}-3-(1H-indol-3-yl)-propionic acid
• (S)-2-{(S)-2-[Hydroxy-(3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-phosphorylamino]-4-methyl-1-oxo-pentylamino}-3-(1H-indol-3-yl)-propionic acid
• (S)-2-{(S)-2-[Hydroxy-(3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-phosphorylamino]-4-methyl-pentanoylamino}-3-(1H-indol-3-yl)-propionic acid
• (S)-3-(1-Hydroxy-1H-indol-3-yl)-2-{(S)-2-[hydroxy-(3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-phosphorylamino]-4-methyl-pentanoylamino}-propionic acid
• 2-{2-[Hydroxy-(3,4,6-trihydroxy-5-methyl-tetrahydro-pyran-2-yloxy)-phosphorylamino]-4-methyl-pentanoylamino}-3-(1H-indol-3-yl)-propionic acid( Phosphoramidon)
• L-TRYPTOPHAN, N-(N-(((6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)OXY)HYDROXYPHOSPHINYL)-L-LEUCYL)-
• N-(hydroxy{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}phosphoryl)-L-leucyl-L-tryptophan

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5887	58.87%
Caco-2	-	0.8926	89.26%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.4132	41.32%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8807	88.07%
OATP1B3 inhibitior	+	0.9342	93.42%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8567	85.67%
BSEP inhibitior	+	0.8474	84.74%
P-glycoprotein inhibitior	-	0.6011	60.11%
P-glycoprotein substrate	+	0.6248	62.48%
CYP3A4 substrate	+	0.6808	68.08%
CYP2C9 substrate	-	0.6138	61.38%
CYP2D6 substrate	-	0.8528	85.28%
CYP3A4 inhibition	-	0.7460	74.60%
CYP2C9 inhibition	-	0.8278	82.78%
CYP2C19 inhibition	-	0.7963	79.63%
CYP2D6 inhibition	-	0.8910	89.10%
CYP1A2 inhibition	-	0.8286	82.86%
CYP2C8 inhibition	+	0.4633	46.33%
CYP inhibitory promiscuity	-	0.7590	75.90%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5290	52.90%
Eye corrosion	-	0.9821	98.21%
Eye irritation	-	0.9662	96.62%
Skin irritation	-	0.7808	78.08%
Skin corrosion	-	0.9286	92.86%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6425	64.25%
Micronuclear	+	0.8000	80.00%
Hepatotoxicity	-	0.6195	61.95%
skin sensitisation	-	0.8561	85.61%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.8404	84.04%
Acute Oral Toxicity (c)	III	0.5312	53.12%
Estrogen receptor binding	+	0.6463	64.63%
Androgen receptor binding	+	0.5914	59.14%
Thyroid receptor binding	+	0.5133	51.33%
Glucocorticoid receptor binding	+	0.5987	59.87%
Aromatase binding	+	0.6005	60.05%
PPAR gamma	+	0.6702	67.02%
Honey bee toxicity	-	0.7212	72.12%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6349	63.49%
Fish aquatic toxicity	+	0.8957	89.57%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4791	P42892	Endothelin-converting enzyme 1	17 nM	IC50	via Super-PRED
CHEMBL1944	P08473	Neprilysin	2 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.78%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.73%	98.95%
CHEMBL3837	P07711	Cathepsin L	97.24%	96.61%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.43%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.80%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	92.96%	90.17%
CHEMBL3359	P21462	Formyl peptide receptor 1	92.06%	93.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.99%	99.17%
CHEMBL1951	P21397	Monoamine oxidase A	89.02%	91.49%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	88.40%	89.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.38%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.33%	96.00%
CHEMBL1255126	O15151	Protein Mdm4	87.44%	90.20%
CHEMBL3401	O75469	Pregnane X receptor	87.38%	94.73%
CHEMBL5028	O14672	ADAM10	86.45%	97.50%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	85.65%	85.83%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	85.45%	98.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.34%	99.23%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.55%	100.00%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	81.23%	97.64%
CHEMBL255	P29275	Adenosine A2b receptor	80.68%	98.59%
CHEMBL3310	Q96DB2	Histone deacetylase 11	80.55%	88.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.28%	97.14%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	80.09%	83.10%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 445114
• LOTUS: LTS0250969
• wikiData: Q7187544