Molecule

Borrelidin

AlkaPlorer ID: AK009593

Synonym: None

IUPAC Name: (1R,2R)-2-[(2S,4E,6Z,8R,9S,11R,13S,15S,16S)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid

Structure

SMILES: C[C@@H]1C[C@H](C)C[C@H](C)[C@@H](O)CC(=O)O[C@H]([C@@H]2CCC[C@H]2C(=O)O)C/C=C/C=C(/C#N)[C@H](O)[C@@H](C)C1

InChI: InChI=1S/C28H43NO6/c1-17-12-18(2)14-20(4)27(32)21(16-29)8-5-6-11-25(22-9-7-10-23(22)28(33)34)35-26(31)15-24(30)19(3)13-17/h5-6,8,17-20,22-25,27,30,32H,7,9-15H2,1-4H3,(H,33,34)/b6-5+,21-8-/t17-,18+,19-,20-,22+,23+,24-,25-,27+/m0/s1

InChIKey: OJCKRNPLOZHAOU-UGKRXNSESA-N

Reference

Streptomyces heilongjiangensis sp. nov., a novel actinomycete that produces borrelidin isolated from the root surface of soybean [Glycine max (L.) Merr]

PubChem CID: 6436801

CAS: 7184-60-3

LOTUS: LTS0260489

SuperNatural Ⅲ: SN0266814-02

{

NPAtlas: NPA011087

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Streptomyces neyagawaensis	Streptomyces	Streptomycetaceae	Kitasatosporales	Actinomycetes	Actinomycetota	None	Bacteria

Properties Information

Molecule Weight: 489.65300000000025

TPSA？: 127.85

MolLogP？: 4.6355800000000045

Number of H-Donors: 3

Number of H-Acceptors: 6

RingCount: 2

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Aspergillus fumigatus	Aspergillus fumigatus	Activity	nan	None	10.1016/j.bmc.2018.11.005
Candida albicans	Candida albicans	Activity	nan	None	10.1016/j.bmc.2018.11.005
Candida parapsilosis	Candida parapsilosis	MIC	50.0	ug.mL-1	10.1016/j.bmc.2018.11.005
Glycine max	Glycine max	Activity	nan	None	10.1021/jf2044982
Homo sapiens	A498	Inhibition	8.0	%	10.1016/j.bmcl.2006.08.073
Homo sapiens	A549	Inhibition	nan	%	10.1021/acsmedchemlett.5b00133
Homo sapiens	DU-145	Inhibition	5.0	%	10.1016/j.bmcl.2006.08.073
Homo sapiens	HEK-293T	IC50	13.97	ug.mL-1	10.1016/j.bmc.2018.11.005
Homo sapiens	HT-29	IC50	920.0	nM	10.1021/np500727g
Homo sapiens	HUVEC	Activity	64.0	None	10.1016/j.bmcl.2006.08.073
Homo sapiens	HUVEC	Activity	65.0	None	10.1016/j.bmcl.2006.08.073
Homo sapiens	HUVEC	Activity	230.0	None	10.1016/j.bmcl.2006.08.073
Homo sapiens	HUVEC	Activity	233.0	None	10.1016/j.bmcl.2006.08.073
Homo sapiens	HUVEC	IC50	0.5	nM	10.1016/j.bmcl.2006.08.073
Homo sapiens	LNCaP	Inhibition	7.0	%	10.1016/j.bmcl.2006.08.073
Homo sapiens	MCF7	Inhibition	13.0	%	10.1016/j.bmcl.2006.08.073
Homo sapiens	MDA-MB-361	IC50	420.0	nM	10.1021/np500727g
Homo sapiens	NCI-H460	Inhibition	4.0	%	10.1016/j.bmcl.2006.08.073
Homo sapiens	NCI-N87	IC50	50.0	nM	10.1021/np500727g
Homo sapiens	OVCAR-3	Inhibition	11.0	%	10.1016/j.bmcl.2006.08.073
Homo sapiens	SF-268	Inhibition	3.0	%	10.1016/j.bmcl.2006.08.073
Homo sapiens	Threonyl-tRNA synthetase	Activity	nan	None	10.1021/acsmedchemlett.5b00133
Homo sapiens	UMSCC1	Activity	nan	None	10.1021/acsmedchemlett.5b00133
Homo sapiens	UMSCC1	Inhibition	nan	%	10.1021/acsmedchemlett.5b00133
Homo sapiens	UMSCC14A	Inhibition	nan	%	10.1021/acsmedchemlett.5b00133
Mus musculus	MEF	Inhibition	nan	%	10.1021/acsmedchemlett.5b00133
Mus musculus	Threonine--tRNA ligase, cytoplasmic	Activity	nan	None	10.1021/acsmedchemlett.5b00133
Mus musculus	Threonine--tRNA ligase, cytoplasmic	Inhibition	nan	%	10.1021/acsmedchemlett.5b00133
Mycobacterium tuberculosis	L-cysteine:1D-myo-inositol 2-amino-2-deoxy-alpha-D-glucopyranoside ligase	IC50	2000000.0	nM	10.1016/j.bmcl.2011.02.042
Phytophthora sojae	Phytophthora sojae	Activity	0.25	cm	10.1021/jf2044982
Phytophthora sojae	Phytophthora sojae	Activity	0.73	cm	10.1021/jf2044982
Phytophthora sojae	Phytophthora sojae	Activity	1.91	cm	10.1021/jf2044982
Phytophthora sojae	Phytophthora sojae	Activity	6.24	cm	10.1021/jf2044982
Phytophthora sojae	Phytophthora sojae	Activity	6.53	cm	10.1021/jf2044982
Phytophthora sojae	Phytophthora sojae	Activity	6.81	cm	10.1021/jf2044982
Phytophthora sojae	Phytophthora sojae	EC50	0.0038	ug.mL-1	10.1021/jf2044982
Phytophthora sojae	Phytophthora sojae	EC50	0.0047	ug.mL-1	10.1021/jf2044982
Phytophthora sojae	Phytophthora sojae	EC50	0.0051	ug.mL-1	10.1021/jf2044982
Phytophthora sojae	Phytophthora sojae	EC50	0.0052	ug.mL-1	10.1021/jf2044982
Phytophthora sojae	Phytophthora sojae	EC50	0.0053	ug.mL-1	10.1021/jf2044982
Phytophthora sojae	Phytophthora sojae	EC50	0.0056	ug.mL-1	10.1021/jf2044982
Phytophthora sojae	Phytophthora sojae	EC50	0.0057	ug.mL-1	10.1021/jf2044982
Phytophthora sojae	Phytophthora sojae	EC95	0.017	mg/L	10.1021/jf2044982
Phytophthora sojae	Phytophthora sojae	EC95	0.018	mg/L	10.1021/jf2044982
Phytophthora sojae	Phytophthora sojae	EC95	0.02	mg/L	10.1021/jf2044982
Phytophthora sojae	Phytophthora sojae	EC95	0.021	mg/L	10.1021/jf2044982
Phytophthora sojae	Phytophthora sojae	EC95	0.026	mg/L	10.1021/jf2044982
Phytophthora sojae	Phytophthora sojae	Efficacy	56.25	%	10.1021/jf2044982
Phytophthora sojae	Phytophthora sojae	Efficacy	80.76	%	10.1021/jf2044982
Phytophthora sojae	Phytophthora sojae	Efficacy	94.72	%	10.1021/jf2044982
Phytophthora sojae	Phytophthora sojae	GI	nan	None	10.1021/jf302857x
Phytophthora sojae	Threonyl-tRNA synthase	Activity	21.8	%	10.1021/jf302857x
Phytophthora sojae	Threonyl-tRNA synthase	Activity	22.4	%	10.1021/jf302857x
Phytophthora sojae	Threonyl-tRNA synthase	Activity	24.4	%	10.1021/jf302857x
Phytophthora sojae	Threonyl-tRNA synthase	Activity	25.7	%	10.1021/jf302857x
Phytophthora sojae	Threonyl-tRNA synthase	Activity	nan	None	10.1021/jf302857x
Phytophthora sojae	Threonyl-tRNA synthase	IC50	8000.0	nM	10.1021/jf302857x
Phytophthora sojae	Threonyl-tRNA synthase	KA	2.552	10'5/M	10.1021/jf302857x
Phytophthora sojae	Threonyl-tRNA synthase	Ki	10000.0	nM	10.1021/jf302857x
Phytophthora sojae	Threonyl-tRNA synthase	Kq	1.233	10'12L/mol/s	10.1021/jf302857x
Phytophthora sojae	Threonyl-tRNA synthase	Kq	1.331	10'12L/mol/s	10.1021/jf302857x
Phytophthora sojae	Threonyl-tRNA synthase	Kq	1.542	10'12L/mol/s	10.1021/jf302857x
Phytophthora sojae	Threonyl-tRNA synthase	KSV	1.233	10'4/M	10.1021/jf302857x
Phytophthora sojae	Threonyl-tRNA synthase	KSV	1.331	10'4/M	10.1021/jf302857x
Phytophthora sojae	Threonyl-tRNA synthase	KSV	1.542	10'4/M	10.1021/jf302857x
Plasmodium falciparum	Plasmodium falciparum	IC50	0.00088	ug.mL-1	10.1016/j.bmcl.2013.02.075
Plasmodium falciparum	Plasmodium falciparum	IC50	0.00093	ug.mL-1	10.1016/j.bmcl.2013.02.075
Plasmodium falciparum	Plasmodium falciparum	IC50	1.9	nM	10.1039/C6MD00274A
Pythium	Pythium	EC50	0.01	ug.mL-1	10.1021/jf302857x
Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC50	23000.0	nM	10.1016/s0960-894x(03)00406-2
Saccharomyces cerevisiae	Saccharomyces cerevisiae	Inhibition	75.0	%	10.1016/s0960-894x(03)00406-2
Saccharomyces cerevisiae S288c	Cell division control protein 28	IC50	24000.0	nM	10.1016/s0960-894x(03)00406-2
None	ADMET	Activity	nan	None	10.1021/acsmedchemlett.5b00133
None	ADMET	IC50	0.201	ug.mL-1	10.1016/j.bmcl.2013.02.075
None	NON-PROTEIN TARGET	Activity	201.0	ng/ml	10.1039/C6MD00274A
None	NON-PROTEIN TARGET	IC50	20.0	nM	10.1016/j.bmcl.2006.08.073
None	NON-PROTEIN TARGET	Inhibition	2.0	%	10.1016/j.bmcl.2006.08.073
None	NON-PROTEIN TARGET	Inhibition	6.0	%	10.1016/j.bmcl.2006.08.073
None	NON-PROTEIN TARGET	Inhibition	8.0	%	10.1016/j.bmcl.2006.08.073
None	NON-PROTEIN TARGET	Inhibition	12.0	%	10.1016/j.bmcl.2006.08.073
None	NON-PROTEIN TARGET	Inhibition	nan	%	10.1021/acsmedchemlett.5b00133
None	Unchecked	Ratio IC50	216.0	None	10.1016/j.bmcl.2013.02.075
None	Unchecked	Ratio IC50	228.0	None	10.1016/j.bmcl.2013.02.075
None	Unchecked	Selectivity Index	0.14	None	10.1016/j.bmc.2018.11.005
None	Unchecked	Selectivity Index	0.28	None	10.1016/j.bmc.2018.11.005