Molecule

Dexfosfoserine

AlkaPlorer ID: AK002961

Synonym: None

IUPAC Name: (2S)-2-amino-3-phosphonooxypropanoic acid

Structure

SMILES: N[C@@H](COP(=O)(O)O)C(=O)O

InChI: InChI=1S/C3H8NO6P/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)/t2-/m0/s1

InChIKey: BZQFBWGGLXLEPQ-REOHCLBHSA-N

Reference

QUANTITATIVE ANALYSE DER FREIEN AMINOSÄUREN AUS SAPROPHYTISCHEN KULTUREN VON<i>CLAVICEPS PURPUREA</i>

PubChem CID: 57689797

CAS: 1446756-47-3

LOTUS: LTS0108147

SuperNatural Ⅲ: SN0039789-01

NPASS: NPC316779

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Homo sapiens	Homo	Hominidae	Primates	Mammalia	Chordata	Metazoa	Eukaryota
Saccharomyces cerevisiae	Saccharomyces	Saccharomycetaceae	Saccharomycetales	Saccharomycetes	Ascomycota	Fungi	Eukaryota
Mus musculus	Mus	Muridae	Rodentia	Mammalia	Chordata	Metazoa	Eukaryota
Escherichia coli	Escherichia	Enterobacteriaceae	Enterobacterales	Gammaproteobacteria	Pseudomonadota	None	Bacteria

Properties Information

Molecule Weight: 185.072

TPSA？: 130.07999999999998

MolLogP？: -1.4924000000000002

Number of H-Donors: 4

Number of H-Acceptors: 4

RingCount: 0

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Bacillus anthracis	Anthrax lethal factor	FC	2.8	None	10.1128/aac.01184-06
Bacillus subtilis	4'-phosphopantetheinyl transferase ffp	Potency	39810.7	nM	None
Escherichia coli K-12	Endonuclease 4	Potency	10000.0	nM	None
Giardia intestinalis	Putative fructose-1,6-bisphosphate aldolase	Potency	39716.4	nM	None
Homo sapiens	Aldehyde dehydrogenase 1A1	Potency	3548.1	nM	None
Homo sapiens	Bloom syndrome protein	Potency	2.8	nM	None
Homo sapiens	Carbonic anhydrase I	KA	0.1	mM	10.1016/j.bmcl.2005.01.049
Homo sapiens	Carbonic anhydrase II	Ki	420000.0	nM	10.1016/j.bmcl.2005.01.049
Homo sapiens	Carbonic anhydrase IV	Ki	4260000.0	nM	10.1016/j.bmcl.2005.01.049
Homo sapiens	Carbonic anhydrase IX	Ki	920000.0	nM	10.1016/j.bmcl.2005.01.049
Homo sapiens	Carbonic anhydrase VA	Ki	360000.0	nM	10.1016/j.bmcl.2005.01.049
Homo sapiens	Cytochrome P450 1A2	AC50	25118.86	nM	None
Homo sapiens	Cytochrome P450 2C19	AC50	nan	None	None
Homo sapiens	Cytochrome P450 2C19	Potency	31622.8	nM	None
Homo sapiens	Cytochrome P450 2C9	AC50	nan	None	None
Homo sapiens	Cytochrome P450 2D6	AC50	nan	None	None
Homo sapiens	Cytochrome P450 3A4	AC50	794.33	nM	None
Homo sapiens	Cytochrome P450 3A4	Potency	794.3	nM	None
Homo sapiens	Glutamate carboxypeptidase II	IC50	523000.0	nM	10.1021/jm070133w
Homo sapiens	Histone acetyltransferase GCN5	Potency	22387.2	nM	None
Homo sapiens	Histone deacetylase 6	Inhibition	-10.66	%	10.6019/CHEMBL4808148
Homo sapiens	Histone deacetylase 6	Inhibition	15.01	%	10.6019/CHEMBL4808148
Homo sapiens	Huh-7	CC50	10000.0	nM	10.1073/pnas.0802982105
Homo sapiens	Lysine-specific demethylase 4D-like	Potency	39810.7	nM	None
Homo sapiens	Metabotropic glutamate receptor 2	Activity	nan	None	10.1016/j.bmc.2018.08.012
Homo sapiens	Metabotropic glutamate receptor 4	Activity	nan	None	10.1016/j.bmc.2018.08.012
Homo sapiens	Metabotropic glutamate receptor 4	EC50	1000.0	nM	10.1016/s0960-894x(00)00247-x
Homo sapiens	Metabotropic glutamate receptor 4	EC50	1300.0	nM	10.1021/jm00009a001
Homo sapiens	Metabotropic glutamate receptor 7	EC50	200000.0	nM	10.1021/jm00009a001
Homo sapiens	Thyroid hormone receptor beta-1	Potency	44668.4	nM	None
Homo sapiens	Tyrosyl-DNA phosphodiesterase 1	Potency	16788.9	nM	None
Homo sapiens	Tyrosyl-DNA phosphodiesterase 1	Potency	21136.0	nM	None
Homo sapiens	Tyrosyl-DNA phosphodiesterase 1	Potency	70794.6	nM	None
Plasmodium falciparum	Plasmodium falciparum	EC50	1065.0	nM	10.1073/pnas.0802982105
Plasmodium falciparum	Plasmodium falciparum	EC50	1080.0	nM	10.1073/pnas.0802982105
Rattus norvegicus	Metabotropic glutamate receptor 4	EC50	4000.0	nM	10.1021/jm00009a001
Rattus norvegicus	Metabotropic glutamate receptor 4	EC50	100000.0	nM	10.1021/jm049092j
Rattus norvegicus	Metabotropic glutamate receptor 6	EC50	2700.0	nM	10.1021/jm00009a001
Rattus norvegicus	Metabotropic glutamate receptor 7	EC50	160000.0	nM	10.1021/jm00009a001
Rattus norvegicus	Thioredoxin reductase 1, cytoplasmic	Potency	398.1	nM	None
Severe acute respiratory syndrome coronavirus 2	Replicase polyprotein 1ab	Inhibition	11.56	%	10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2	Replicase polyprotein 1ab	Inhibition	14.04	%	10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	Inhibition	-0.1	%	10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	Inhibition	0.19	%	10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	Inhibition	2.74	%	10.21203/rs.3.rs-23951/v1
None	NON-PROTEIN TARGET	Potency	11220.2	nM	None
None	Unchecked	Ac50	5.623	uM	None
None	Unchecked	Ac50	19.95	uM	None
None	Unchecked	AC50	5623.4	nM	None
None	Unchecked	AC50	19952.6	nM	None
None	Unchecked	Activity	nan	None	10.1016/j.bmc.2013.12.006
None	Unchecked	IFI	0.0	%	10.1073/pnas.0802982105
None	Unchecked	Inhibition	nan	%	10.1038/nchembio873
None	Unchecked	Potency	8.9	nM	None
None	Unchecked	Potency	39810.7	nM	None

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT000292	C(=O)OCC(CO)OC()=O.N[C@@H](COP(=O)(O)O)C(=O)O>>C(=O)OCC(COP(=O)(O)OCC(N)C(=O)O)OC()=O	MNXR133423
AKRT000581	NCC(=O)NCC(=O)S.N[C@@H](COP(=O)(O)O)C(=O)O>>NCC(=O)NCC(=O)SC[C@H](N)C(=O)O	RXN-14566
AKRT000583	NCC(=O)NCC(=O)[S-].N[C@@H](COP(=O)(O)O)C(=O)O>>NCC(=O)NCC(=O)SC[C@H](N)C(=O)O	MNXR183458
AKRT000852	OP(=O)(O)OC[C@H]1O[C@@H](n2ccc(N)nc2=O)[C@H](O)[C@@H]1OP(=O)(O)OC[C@H]1O[C@@H](n2ccc(N)nc2=O)[C@H](O)[C@@H]1OP(=O)(O)OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O.N[C@@H](COP(=O)(O)O)C(=O)O>>OP(=O)(O)OC[C@H]1O[C@@H](n2ccc(N)nc2=O)[C@H](O)[C@@H]1OP(=O)(O)OC[C@H]1O[C@@H](n2ccc(N)nc2=O)[C@H](O)[C@@H]1OP(=O)(O)OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](OC(=O)[C@@H](N)COP(=O)(O)O)[C@@H]1O	RXN-10718
AKRT007923	CCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@H](N)C(=O)O)OC(=O)CCCCC>>N[C@@H](COP(=O)(O)O)C(=O)O	enzymemap_57446
AKRT008302	CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@H](N)C(=O)O)OC(=O)CCCCCCC/C=C\CCCCCCCC>>N[C@@H](COP(=O)(O)O)C(=O)O	enzymemap_57431
AKRT013659	C[C@H](N)C(=O)O>>N[C@@H](COP(=O)(O)O)C(=O)O	enzymemap_42474
AKRT019100	N[C@@H](CCC(=O)O)C(=O)O.N[C@@H](COP(=O)(O)O)C(=O)O>>N[C@@H](CN[C@@H](CCC(=O)O)C(=O)O)C(=O)O	RXN-18395
AKRT019143	N[C@@H](CCC(=O)O)C(=O)O.O=C(O)C(=O)COP(=O)(O)O>>N[C@@H](COP(=O)(O)O)C(=O)O	PSERTRANSAM-RXN
AKRT019516	N[C@@H](CO)C(=O)O>>N[C@@H](COP(=O)(O)O)C(=O)O	RXN-19824
AKRT019526	N[C@@H](COP(=O)(O)O)C(=O)O.N[C@@H](CCC(=O)O)C(=O)O>>N[C@@H](CN[C@@H](CCC(=O)O)C(=O)O)C(=O)O	enzymemap_40034
AKRT019527	N[C@@H](COP(=O)(O)O)C(=O)O.O=C(O)CCC(=O)C(=O)O>>N[C@@H](CCC(=O)O)C(=O)O	R04173
AKRT019528	N[C@@H](COP(=O)(O)O)C(=O)O.O=C(O)CCC(=O)C(=O)O>>N[C@@H](CCC(=O)O)C(=O)O.O=C(O)C(=O)COP(=O)(O)O	None
AKRT019529	N[C@@H](COP(=O)(O)O)C(=O)O.O=C(O)CCC(=O)C(=O)O>>O=C(O)C(=O)COP(=O)(O)O	R04173
AKRT019530	N[C@@H](COP(=O)(O)O)C(=O)O.c1ccc2[nH]ccc2c1>>N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O	MNXR172579
AKRT019531	N[C@@H](COP(=O)(O)O)C(=O)O>>C[C@H](N)C(=O)O	enzymemap_42474
AKRT019532	N[C@@H](COP(=O)(O)O)C(=O)O>>NCCOP(=O)(O)O	69548
AKRT019533	N[C@@H](COP(=O)(O)O)C(=O)O>>N[C@@H](CO)C(=O)O	RXN0-5114
AKRT019534	N[C@@H](COP(=O)(O)O)C(=O)O>>N[C@@H](CS(=O)(=O)O)C(=O)O	RXN-11108
AKRT019535	N[C@@H](COP(=O)(O)O)C(=O)O>>N[C@@H](CS)C(=O)O	2.5.1.65-RXN
AKRT019536	N[C@@H](COP(=O)(O)O)C(=O)O>>N[C@@H](CSS(=O)(=O)O)C(=O)O	R12092
AKRT019537	N[C@@H](COP(=O)(O)O)C(=O)O>>O=C(O)C(=O)COP(=O)(O)O	MNXR162779
AKRT019538	N[C@@H](COP(=O)(O)O)C(=O)O>>O=C=O	69548
AKRT022579	O=C(O)C(=O)COP(=O)(O)O>>N[C@@H](COP(=O)(O)O)C(=O)O	enzymemap_42462