Molecule

Marizomib

AlkaPlorer ID: AK028625

Synonym: None

IUPAC Name: (1R,4R,5S)-4-(2-chloroethyl)-1-[(S)-[(1S)-cyclohex-2-en-1-yl]-hydroxymethyl]-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione

Structure

SMILES: C[C@@]12OC(=O)[C@]1([C@@H](O)[C@@H]1C=CCCC1)N=C(O)[C@@H]2CCCl

InChI: InChI=1S/C15H20ClNO4/c1-14-10(7-8-16)12(19)17-15(14,13(20)21-14)11(18)9-5-3-2-4-6-9/h3,5,9-11,18H,2,4,6-8H2,1H3,(H,17,19)/t9-,10+,11+,14+,15+/m1/s1

InChIKey: NGWSFRIPKNWYAO-SHTIJGAHSA-N

Reference

Salinosporamides D−J from the Marine Actinomycete <i>Salinispora tropica</i>, Bromosalinosporamide, and Thioester Derivatives Are Potent Inhibitors of the 20S Proteasome

PubChem CID: 11347535

CAS: 437742-34-2

LOTUS: LTS0244403

SuperNatural Ⅲ: SN0245197-02

NPASS: NPC12270

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NPAtlas: NPA011013

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Salinispora tropica	Salinispora	Micromonosporaceae	Micromonosporales	Actinomycetes	Actinomycetota	None	Bacteria
Salinispora sp.	Salinispora	Micromonosporaceae	Micromonosporales	Actinomycetes	Actinomycetota	None	Bacteria
Salinispora arenicola	Salinispora	Micromonosporaceae	Micromonosporales	Actinomycetes	Actinomycetota	None	Bacteria

Properties Information

Molecule Weight: 313.78100000000006

TPSA？: 79.12

MolLogP？: 1.9731

Number of H-Donors: 2

Number of H-Acceptors: 4

RingCount: 3

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Homo sapiens	20S proteasome	IC50	1.3	nM	10.1016/j.ejmech.2022.114117
Homo sapiens	HCT-116	GI50	35.0	nM	10.1016/j.ejmech.2022.114117
Homo sapiens	HCT-116	IC50	0.002	ug.mL-1	10.1016/j.bmc.2008.10.075
Homo sapiens	HCT-116	IC50	16.0	nM	10.1021/jm901098m
Homo sapiens	HCT-116	IC50	35.0	nM	10.1016/j.bmc.2011.07.017
Homo sapiens	HEK293	IC50	11.0	nM	10.1021/jm048995+
Homo sapiens	HOP-92	GI50	11.0	nM	10.1016/j.ejmech.2022.114117
Homo sapiens	LOX IMVI	GI50	11.0	nM	10.1016/j.ejmech.2022.114117
Homo sapiens	OVCAR-3	GI50	11.0	nM	10.1016/j.ejmech.2022.114117
Homo sapiens	PC-3	GI50	11.0	nM	10.1016/j.ejmech.2022.114117
Homo sapiens	Proteasome component C5	IC50	0.604	nM	10.1016/j.ejmech.2019.111646
Homo sapiens	Proteasome component C5	IC50	430.0	nM	10.1021/jm300434z
Homo sapiens	Proteasome Macropain subunit	IC50	10.6	nM	10.1016/j.ejmech.2019.111646
Homo sapiens	Proteasome Macropain subunit	IC50	28.0	nM	10.1021/jm300434z
Homo sapiens	Proteasome Macropain subunit MB1	EC50	nan	None	10.1016/j.bmcl.2013.09.066
Homo sapiens	Proteasome Macropain subunit MB1	IC50	3.5	nM	10.1016/j.ejmech.2019.111646
Homo sapiens	Proteasome Macropain subunit MB1	IC50	3.5	nM	10.1021/jm300434z
Homo sapiens	Proteasome Macropain subunit MB1	IC50	22.0	nM	10.1016/j.bmcl.2013.09.066
Homo sapiens	Proteasome Macropain subunit MB1	Inhibition	nan	%	10.1016/j.bmcl.2013.09.066
Homo sapiens	RPMI-8226	IC50	8.2	nM	10.1021/jm048995+
Homo sapiens	RPMI-8226	IC50	11.0	nM	10.1021/np800578e
Oryctolagus cuniculus	Oryctolagus cuniculus	IC50	2.6	nM	10.1021/jm048995+
Oryctolagus cuniculus	Oryctolagus cuniculus	IC50	21.0	nM	10.1021/jm048995+
Oryctolagus cuniculus	Oryctolagus cuniculus	IC50	430.0	nM	10.1021/jm048995+
Plasmodium falciparum	Plasmodium falciparum	EC50	11.0	nM	10.1016/j.bmcl.2013.03.067
Plasmodium yoelii yoelii	Plasmodium yoelii yoelii	ED50	0.25	mg/kg/day	10.1016/j.bmcl.2013.03.067
None	NON-PROTEIN TARGET	GI50	10.0	nM	10.1016/j.bmc.2008.10.075
None	No relevant target	T1/2	0.9333	hr	10.1021/jm4002296
None	No relevant target	T1/2	1.283	hr	10.1021/jm800548b
None	Unchecked	Activity	0.003	/s	10.1021/jm800548b
None	Unchecked	Activity	0.01	/s	10.1021/jm800548b
None	Unchecked	Activity	0.02	/s	10.1021/jm800548b
None	Unchecked	Activity	nan	None	10.1021/jm800548b
None	Unchecked	IC50	1.3	nM	10.1016/j.bmc.2011.07.017
None	Unchecked	IC50	1.9	nM	10.1021/jm901098m
None	Unchecked	IC50	2.0	nM	10.1021/jm800548b
None	Unchecked	IC50	2.5	nM	10.1021/jm800548b
None	Unchecked	IC50	2.6	nM	10.1016/j.bmcl.2013.02.079
None	Unchecked	IC50	2.6	nM	10.1016/j.bmcl.2014.01.072
None	Unchecked	IC50	3.5	nM	10.1021/jm800548b
None	Unchecked	IC50	4.0	nM	10.1021/np800578e
None	Unchecked	IC50	21.0	nM	10.1016/j.bmcl.2013.02.079
None	Unchecked	IC50	21.0	nM	10.1016/j.bmcl.2014.01.072
None	Unchecked	IC50	26.0	nM	10.1021/jm800548b
None	Unchecked	IC50	28.0	nM	10.1021/jm800548b
None	Unchecked	IC50	34.0	nM	10.1021/np800578e
None	Unchecked	IC50	59.0	nM	10.1021/jm800548b
None	Unchecked	IC50	330.0	nM	10.1021/jm800548b
None	Unchecked	IC50	364.0	nM	10.1021/np800578e
None	Unchecked	IC50	430.0	nM	10.1021/jm800548b
None	Unchecked	IC50	460.0	nM	10.1016/j.bmcl.2013.02.079
None	Unchecked	IC50	460.0	nM	10.1016/j.bmcl.2014.01.072
None	Unchecked	IC50	2600.0	nM	10.1021/jm800548b
None	Unchecked	INH	1.3	nM	10.1038/nchembio841
None	Unchecked	Ki	23.0	nM	10.1021/jm800548b
None	Unchecked	Ki	97.0	nM	10.1021/jm800548b
None	Unchecked	Ki	1000.0	nM	10.1021/jm800548b

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT004701	CC(=O)[CoA].N[C@@H](C[C@H]1C=CCCC1)C(=O)O.O=C(O)C(CCCl)C(=O)[CoA]>>C[C@@]12OC(=O)[C@]1([C@@H](O)[C@@H]1C=CCCC1)NC(=O)[C@@H]2CCCl	RXN-11725