Molecule

Sangivamycin

AlkaPlorer ID: AK006859

Synonym: None

IUPAC Name: 4-amino-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrrolo[2,3-d]pyrimidine-5-carboxamide

Structure

SMILES: NC(=O)C1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C2=NC=NC(N)=C12

InChI: InChI=1S/C12H15N5O5/c13-9-6-4(10(14)21)1-17(11(6)16-3-15-9)12-8(20)7(19)5(2-18)22-12/h1,3,5,7-8,12,18-20H,2H2,(H2,14,21)(H2,13,15,16)/t5-,7-,8-,12-/m1/s1

InChIKey: OBZJZDHRXBKKTJ-JTFADIMSSA-N

Reference

Direct broth assay for sparsomycin and related nucleoside antitumor antibiotics using reversed-phase high-performance liquid chromatography

PubChem CID: 14978

CAS: 18417-89-5

LOTUS: LTS0006799

SuperNatural Ⅲ: SN0261278-03

NPASS: NPC222174

{

NPAtlas: NPA005297

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Streptomyces sp.	Streptomyces	Streptomycetaceae	Kitasatosporales	Actinomycetes	Actinomycetota	None	Bacteria
Jaspis splendens	Jaspis	Ancorinidae	Tetractinellida	Demospongiae	Porifera	Metazoa	Eukaryota

Properties Information

Molecule Weight: 309.28200000000004

TPSA？: 169.74000000000004

MolLogP？: -2.2761

Number of H-Donors: 5

Number of H-Acceptors: 9

RingCount: 3

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Chlorocebus sabaeus	Vero	MCC	0.4	ug.mL-1	10.1021/jm00369a010
Chlorocebus sabaeus	Vero	MTC	0.4	ug ml-1	10.1021/jm00386a007
Coxsackievirus B4	Coxsackievirus B4	MIC	0.02	ug.mL-1	10.1021/jm00369a010
Coxsackievirus B4	Coxsackievirus B4	MIC	0.04	ug.mL-1	10.1021/jm00369a010
Coxsackievirus B4	Coxsackievirus B4	MIC50	0.02	ug.mL-1	10.1021/jm00386a007
Coxsackievirus B4	Coxsackievirus B4	MIC50	0.4	ug.mL-1	10.1021/jm00386a007
Homo sapiens	Adenosine kinase	IC50	470.0	nM	10.1016/s0960-894x(02)00042-2
Homo sapiens	Adenosine kinase	IC50	470.0	nM	10.1021/jm000024g
Homo sapiens	Adenosine kinase	IC50	2127649080.27	nM	10.1016/s0960-894x(02)00042-2
Homo sapiens	Adenosine kinase	IC50	2137962089.5	nM	10.1016/j.bmcl.2004.04.040
Homo sapiens	Adenosine kinase	log(10'3/IC50)	3.33	None	10.1016/j.bmc.2008.03.027
Homo sapiens	Adenosine kinase	logIC50	-0.3279	None	10.1007/s00044-004-0048-0
Homo sapiens	Apoptosis regulator Bcl-X	Activity	nan	None	10.1074/jbc.m701362200
Homo sapiens	c-Jun N-terminal kinase, JNK	Activity	nan	None	10.1074/jbc.m701362200
Homo sapiens	G-protein coupled receptor kinase 2	Ki	67000.0	nM	10.1074/jbc.m701362200
Homo sapiens	Heat shock cognate 71 kDa protein	Kd	3235.94	nM	10.1021/acs.jmedchem.5b02001
Homo sapiens	Heat shock cognate 71 kDa protein	Kd	3300.0	nM	10.1021/acs.jmedchem.5b02001
Homo sapiens	HeLa	MCC	0.4	ug.mL-1	10.1021/jm00369a010
Homo sapiens	HeLa	MTC	0.4	ug ml-1	10.1021/jm00386a007
Homo sapiens	HFF	IC50	10.0	nM	10.1021/jm950444j
Homo sapiens	HFF	IC50	8000.0	nM	10.1021/jm00174a011
Homo sapiens	Histone-lysine N-methyltransferase, H3 lysine-79 specific	IC50	26000.0	nM	10.1016/j.bmcl.2016.07.041
Homo sapiens	KB	IC50	80.0	nM	10.1021/jm950444j
Homo sapiens	MCF-10A	Activity	nan	None	10.1074/jbc.m701362200
Homo sapiens	MDA-MB-231	Activity	nan	None	10.1074/jbc.m701362200
Homo sapiens	MDA-MB-468	Activity	nan	None	10.1074/jbc.m701362200
Homo sapiens	Proto-oncogene c-JUN	Activity	nan	None	10.1074/jbc.m701362200
Homo sapiens	Rhodopsin kinase	Ki	180.0	nM	10.1074/jbc.m701362200
Human alphaherpesvirus 1	Human alphaherpesvirus 1	IC50	13000.0	nM	10.1021/jm00174a011
Human alphaherpesvirus 1	Human alphaherpesvirus 1	IC90	900.0	nM	10.1021/jm00174a011
Human alphaherpesvirus 1	Human alphaherpesvirus 1	MIC	0.07	ug.mL-1	10.1021/jm00369a010
Human alphaherpesvirus 1	Human alphaherpesvirus 1	MIC50	0.07	ug.mL-1	10.1021/jm00386a007
Human alphaherpesvirus 2	Human alphaherpesvirus 2	MIC	0.07	ug.mL-1	10.1021/jm00369a010
Human alphaherpesvirus 2	Human alphaherpesvirus 2	MIC50	0.07	ug.mL-1	10.1021/jm00386a007
Human betaherpesvirus 5	Human betaherpesvirus 5	IC50	30.0	nM	10.1021/jm00122a019
Human betaherpesvirus 5	Human betaherpesvirus 5	IC50	30.0	nM	10.1021/jm950444j
Human betaherpesvirus 5	Human betaherpesvirus 5	IC50	600.0	nM	10.1021/jm00174a011
Human betaherpesvirus 5	Human betaherpesvirus 5	IC90	1000.0	nM	10.1021/jm00174a011
Human respirovirus 3	Human respirovirus 3	MIC	0.02	ug.mL-1	10.1021/jm00369a010
Human respirovirus 3	Human respirovirus 3	MIC50	0.02	ug.mL-1	10.1021/jm00386a007
Mammalian orthoreovirus 1	Mammalian orthoreovirus 1	MIC	0.1	ug.mL-1	10.1021/jm00369a010
Mammalian orthoreovirus 1	Mammalian orthoreovirus 1	MIC50	0.4	ug.mL-1	10.1021/jm00386a007
Mus musculus	L1210	Control	0.0	%	10.1021/jm00174a011
Mus musculus	L1210	IC50	3.0	nM	10.1021/jm00122a019
Mus musculus	L1210	ID50	0.019	ug ml-1	10.1021/jm00369a010
Mus musculus	L1210	ID50	3.4	M	10.1021/jm00355a006
Mus musculus	L1210	ILS	37.0	%	10.1021/jm00355a006
Mus musculus	L1210	MIC50	0.014	ug.mL-1	10.1021/jm00386a007
Mus musculus	L1210	MIC50	0.019	ug.mL-1	10.1021/jm00386a007
Mus musculus	L1210	MIC50	100.0	ug.mL-1	10.1021/jm00386a007
Mus musculus	L1210	Toxicity	nan	None	10.1021/jm00355a006
Mus musculus	Monoamine oxidase A	Activity	nan	None	10.1021/jm800656v
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)	Adenosine kinase	IC50	16500.0	nM	10.1021/acs.jmedchem.9b00020
Oryctolagus cuniculus	Oryctolagus cuniculus	MCC	10.0	ug.mL-1	10.1021/jm00369a010
Oryctolagus cuniculus	Oryctolagus cuniculus	MTC	1.0	ug ml-1	10.1021/jm00386a007
Plasmodium falciparum	Plasmodium falciparum	IC37	0.3	uM	10.1021/acs.jmedchem.9b00182
Plasmodium falciparum	Plasmodium falciparum	ID50	25.0	uM	10.1021/acs.jmedchem.9b00182
Poliovirus 1	Poliovirus 1	MIC	0.07	ug.mL-1	10.1021/jm00369a010
Poliovirus 1	Poliovirus 1	MIC50	0.07	ug.mL-1	10.1021/jm00386a007
Sindbis virus	Sindbis virus	MIC	0.2	ug.mL-1	10.1021/jm00369a010
Sindbis virus	Sindbis virus	MIC50	0.4	ug.mL-1	10.1021/jm00386a007
Vaccinia virus	Vaccinia virus	MIC	0.02	ug.mL-1	10.1021/jm00369a010
Vaccinia virus	Vaccinia virus	MIC50	0.02	ug.mL-1	10.1021/jm00386a007
Vesicular stomatitis virus	Vesicular stomatitis virus	MIC	0.02	ug.mL-1	10.1021/jm00369a010
Vesicular stomatitis virus	Vesicular stomatitis virus	MIC	0.04	ug.mL-1	10.1021/jm00369a010
Vesicular stomatitis virus	Vesicular stomatitis virus	MIC50	0.02	ug.mL-1	10.1021/jm00386a007
Vesicular stomatitis virus	Vesicular stomatitis virus	MIC50	0.04	ug.mL-1	10.1021/jm00386a007
None	ADMET	IC50	80.0	nM	10.1021/jm00122a019
None	ADMET	IC50	200.0	nM	10.1021/jm00122a019
None	ADMET	IC50	30000.0	nM	10.1021/jm00174a011
None	ADMET	IC50	100000.0	nM	10.1021/jm00174a011
None	Molecular identity unknown	Activity	1.0	%	10.1074/jbc.m701362200
None	Molecular identity unknown	Activity	3.0	%	10.1074/jbc.m701362200
None	Molecular identity unknown	Activity	4.0	%	10.1074/jbc.m701362200
None	Molecular identity unknown	Activity	8.0	%	10.1074/jbc.m701362200
None	Molecular identity unknown	Activity	9.0	%	10.1074/jbc.m701362200
None	Molecular identity unknown	Activity	11.0	%	10.1074/jbc.m701362200
None	Molecular identity unknown	Activity	17.0	%	10.1074/jbc.m701362200
None	Molecular identity unknown	Activity	20.0	%	10.1074/jbc.m701362200
None	Molecular identity unknown	Activity	23.0	%	10.1074/jbc.m701362200
None	Molecular identity unknown	Activity	25.0	%	10.1074/jbc.m701362200
None	Molecular identity unknown	Activity	27.0	%	10.1074/jbc.m701362200
None	Molecular identity unknown	Activity	28.0	%	10.1074/jbc.m701362200
None	Molecular identity unknown	Activity	33.0	%	10.1074/jbc.m701362200
None	Molecular identity unknown	Activity	40.0	%	10.1074/jbc.m701362200
None	Molecular identity unknown	Activity	48.0	%	10.1074/jbc.m701362200
None	Molecular identity unknown	Activity	50.0	%	10.1074/jbc.m701362200
None	Molecular identity unknown	Activity	57.0	%	10.1074/jbc.m701362200
None	Molecular identity unknown	Activity	61.0	%	10.1074/jbc.m701362200
None	Molecular identity unknown	Activity	nan	None	10.1074/jbc.m701362200
None	NON-PROTEIN TARGET	Activity	nan	None	10.1074/jbc.m701362200
None	No relevant target	LogD7.4	-0.87	None	10.6019/CHEMBL3301361
None	Unchecked	Activity	95.0	%	10.1074/jbc.m701362200
None	Unchecked	Activity	nan	None	10.1021/acs.jnatprod.5b00987
None	Unchecked	Activity	nan	None	10.1074/jbc.m701362200
None	Unchecked	IC50	50000.0	nM	10.1074/jbc.m701362200
None	Unchecked	Ki	10000.0	nM	10.1074/jbc.m701362200
None	Unchecked	Ki	100000.0	nM	10.1074/jbc.m701362200
None	Unchecked	Ki	200000.0	nM	10.1074/jbc.m701362200

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT015806	N#Cc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c2ncnc(N)c12>>NC(=O)c1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c2ncnc(N)c12	enzymemap_84428
AKRT015807	N#Cc1cn([C@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c2ncnc(N)c12>>NC(=O)c1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c2ncnc(N)c12	RXN-12159
AKRT017299	NC(=O)c1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c2ncnc(N)c12>>N#Cc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c2ncnc(N)c12	MNXR176290