Molecule

Alvespimycin

AlkaPlorer ID: AK017754

Synonym: None

IUPAC Name: [(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-19-[2-(dimethylamino)ethylamino]-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl] carbamate

Structure

SMILES: CO[C@H]1/C=C\C=C(/C)C(O)=NC2=CC(=O)C(NCCN(C)C)=C(C[C@@H](C)C[C@H](OC)[C@H](O)[C@@H](C)/C=C(\C)[C@@H]1OC(=N)O)C2=O

InChI: InChI=1S/C32H48N4O8/c1-18-14-22-27(34-12-13-36(5)6)24(37)17-23(29(22)39)35-31(40)19(2)10-9-11-25(42-7)30(44-32(33)41)21(4)16-20(3)28(38)26(15-18)43-8/h9-11,16-18,20,25-26,28,30,34,38H,12-15H2,1-8H3,(H2,33,41)(H,35,40)/b11-9-,19-10+,21-16+/t18-,20+,25+,26+,28-,30+/m1/s1

InChIKey: KUFRQPKVAWMTJO-LMZWQJSESA-N

Reference

Hypoxia-inducible factor-1 and nuclear factor-κB inhibitory meroterpene analogues of bakuchiol, a constituent of the seeds of Psoralea corylifolia

PubChem CID: 5288674

CAS: 150270-08-9

LOTUS: LTS0204526

NPASS: NPC473249

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Trichosanthes kirilowii	Trichosanthes	Cucurbitaceae	Cucurbitales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota

Properties Information

Molecule Weight: 616.7560000000004

TPSA？: 174.0

MolLogP？: 3.167570000000002

Number of H-Donors: 5

Number of H-Acceptors: 10

RingCount: 2

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Canis lupus familiaris	Canis familiaris	MTD	8.0	mg/m2	10.1021/jm9004708
Canis lupus familiaris	Heat shock protein 90 beta	EC50	65.0	nM	10.1021/jm0603116
Hepacivirus hominis	Hepatitis C virus	EC50	1.2	nM	10.1128/aac.01081-08
Hepacivirus hominis	Hepatitis C virus	EC50	3.1	nM	10.1128/aac.01081-08
Hepacivirus hominis	Hepatitis C virus	Ratio IC50	3.0	None	10.1128/aac.01081-08
Homo sapiens	A2058	IC50	2.1	nM	10.1016/j.bmcl.2008.09.081
Homo sapiens	A2058	TGI	34.0	%	10.1021/jm200128m
Homo sapiens	A549	IC50	68.0	nM	10.1021/jm900098v
Homo sapiens	AGS	IC50	16000.0	nM	10.1016/j.bmcl.2008.03.028
Homo sapiens	AGS	IC50	16000.0	nM	10.1021/np060482d
Homo sapiens	BT-549	IC50	17100.0	nM	10.1021/acs.jmedchem.0c01180
Homo sapiens	CCRF-CEM	IC50	540.0	nM	10.1021/jm900098v
Homo sapiens	CCRF-CEM	IC50	2500.0	nM	10.1021/jm900098v
Homo sapiens	Cytochrome P450 2B6	Drug metabolism	nan	None	10.1124/dmd.110.036418
Homo sapiens	Cytochrome P450 2C9	Drug metabolism	nan	None	10.1124/dmd.110.036418
Homo sapiens	Cytochrome P450 2E1	Drug metabolism	nan	None	10.1124/dmd.110.036418
Homo sapiens	Cytochrome P450 3A5	Drug metabolism	nan	None	10.1124/dmd.110.036418
Homo sapiens	HCT-116	IC50	50.0	nM	10.1021/jm100060b
Homo sapiens	HCT-116	IC50	57.0	nM	10.1021/jm900012a
Homo sapiens	HCT-116	IC50	780.0	nM	10.1016/j.bmcl.2014.01.070
Homo sapiens	HCT-116	IC50	1210.0	nM	10.1016/j.ejmech.2014.03.061
Homo sapiens	Heat shock protein HSP90	EC50	4.0	nM	10.1021/jm0603116
Homo sapiens	Heat shock protein HSP90	EC50	7.9	nM	10.1016/j.bmcl.2008.09.081
Homo sapiens	Heat shock protein HSP90	EC50	8.0	nM	10.1021/jm0603116
Homo sapiens	Heat shock protein HSP90	EC50	14.0	nM	10.1021/jm0603116
Homo sapiens	Heat shock protein HSP90	EC50	46.0	nM	10.1021/jm0603116
Homo sapiens	Heat shock protein HSP90	EC50	62.0	nM	10.1021/jm0603116
Homo sapiens	Heat shock protein HSP90	IC50	4.5	nM	10.1016/j.bmcl.2008.09.081
Homo sapiens	Heat shock protein HSP90	IC50	17.6	nM	10.1016/j.bmcl.2008.09.081
Homo sapiens	Heat shock protein HSP90	IC50	24.0	nM	10.1021/acs.jmedchem.5b01106
Homo sapiens	Heat shock protein HSP90	IC50	24.3	nM	10.1016/j.bmcl.2008.09.081
Homo sapiens	Heat shock protein HSP90	IC50	100.0	nM	10.1021/jm200128m
Homo sapiens	Heat shock protein HSP90	IC50	100.0	nM	10.1021/jm901209q
Homo sapiens	Heat shock protein HSP90	Inhibition	nan	%	10.1021/acs.jmedchem.7b00978
Homo sapiens	Heat shock protein HSP 90-alpha	IC50	919.0	nM	10.1016/j.bmc.2016.07.067
Homo sapiens	Heat shock protein HSP 90-alpha	Kd	87.0	nM	10.1021/jm900012a
Homo sapiens	Heat shock protein HSP 90-alpha	Kd	500.0	nM	10.1016/j.bmcl.2005.08.013
Homo sapiens	Heat shock protein HSP 90-alpha	Kd	500.0	nM	10.1021/jm900012a
Homo sapiens	Heat shock protein HSP 90-alpha	Ki	680.0	nM	10.1021/jm200128m
Homo sapiens	Heat shock protein HSP 90-beta	Activity	nan	None	10.1038/nchembio.2007.10
Homo sapiens	Heat shock protein HSP 90-beta	IC50	24.0	nM	10.1016/j.bmc.2008.10.087
Homo sapiens	Heat shock protein HSP 90-beta	IC50	90.0	nM	10.1016/j.ejmech.2014.03.061
Homo sapiens	Heat shock protein HSP 90-beta	IC50	930.0	nM	10.1016/j.bmcl.2014.01.070
Homo sapiens	Heat shock protein HSP 90-beta	IC50	1410.0	nM	10.1016/j.ejmech.2014.03.061
Homo sapiens	Heat shock protein HSP 90-beta	Inhibition	88.31	%	10.1016/j.ejmech.2014.03.061
Homo sapiens	Heat shock protein HSP 90-beta	Inhibition	nan	%	10.1038/nchembio.2007.10
Homo sapiens	Heat shock protein HSP 90-beta	Kd	500.0	nM	10.1021/jm900098v
Homo sapiens	HeLa	IC50	2060.0	nM	10.1016/j.bmcl.2008.03.028
Homo sapiens	Hep 3B2	IC50	79.0	nM	10.1021/np900820p
Homo sapiens	Hep 3B2	IC50	79.5	nM	10.1021/np800491u
Homo sapiens	Histone deacetylase 6	Inhibition	6.6	%	10.6019/CHEMBL4808148
Homo sapiens	Histone deacetylase 6	Inhibition	7.69	%	10.6019/CHEMBL4808148
Homo sapiens	Homo sapiens	CL	7.4	L/hr	10.1124/dmd.110.036418
Homo sapiens	Homo sapiens	T1/2	16.0	hr	10.1124/dmd.110.036418
Homo sapiens	Hs-578T	IC50	8.4	nM	10.1021/acs.jmedchem.0c01180
Homo sapiens	Hypoxia-inducible factor 1 alpha	IC50	57.0	nM	10.1021/np900820p
Homo sapiens	Hypoxia-inducible factor 1 alpha	IC50	57.2	nM	10.1021/np800491u
Homo sapiens	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	IC50	3.6	nM	10.1016/j.bmcl.2008.03.028
Homo sapiens	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	IC50	36.0	nM	10.1021/np060482d
Homo sapiens	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	IC50	61.0	nM	10.1021/np060482d
Homo sapiens	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	IC50	30000.0	nM	10.1021/np800491u
Homo sapiens	Liver microsome	Drug metabolism	nan	None	10.1124/dmd.110.036418
Homo sapiens	Liver microsome	Inhibition	75.0	%	10.1124/dmd.110.036418
Homo sapiens	Liver microsome	Inhibition	77.0	%	10.1124/dmd.110.036418
Homo sapiens	Liver microsome	Inhibition	79.0	%	10.1124/dmd.110.036418
Homo sapiens	Liver microsome	Inhibition	81.0	%	10.1124/dmd.110.036418
Homo sapiens	Liver microsome	Inhibition	83.0	%	10.1124/dmd.110.036418
Homo sapiens	Liver microsome	Km	6610.0	nM	10.1124/dmd.110.036418
Homo sapiens	Liver microsome	Km	7830.0	nM	10.1124/dmd.110.036418
Homo sapiens	Liver microsome	Stability	24.0	%	10.1124/dmd.110.036418
Homo sapiens	Liver microsome	Stability	nan	%	10.1124/dmd.110.036418
Homo sapiens	Liver microsomes	CL	12.3	mL.min-1.g-1	10.1021/jm200128m
Homo sapiens	Liver microsomes	CLH	3.0	uL/min	10.1021/jm901209q
Homo sapiens	LN-229	Inhibition	nan	%	10.1021/jm300752n
Homo sapiens	Lysine-specific demethylase 4B	IC50	700.0	nM	10.1021/acs.jmedchem.2c00680
Homo sapiens	Lysine-specific demethylase 4C	IC50	700.0	nM	10.1021/acs.jmedchem.2c00680
Homo sapiens	Lysine-specific demethylase 5A	IC50	130.0	nM	10.1021/acs.jmedchem.2c00680
Homo sapiens	Lysine-specific demethylase 6B	IC50	400.0	nM	10.1021/acs.jmedchem.2c00680
Homo sapiens	MCF7	IC50	71.0	nM	10.1021/jm900012a
Homo sapiens	MCF7	IC50	230.0	nM	10.1021/jm900098v
Homo sapiens	MCF7	IC50	390.0	nM	10.1016/j.bmcl.2014.01.070
Homo sapiens	MCF7	IC50	800.0	nM	10.1016/j.ejmech.2014.03.061
Homo sapiens	MCF7	IC50	862.0	nM	10.1021/jm900012a
Homo sapiens	MDA-MB-231	IC50	5.8	nM	10.1016/j.bmcl.2008.09.081
Homo sapiens	MDA-MB-231	IC50	45700.0	nM	10.1021/acs.jmedchem.0c01180
Homo sapiens	NCI-H1299	Inhibition	nan	%	10.1021/jm5010144
Homo sapiens	NCI-H596	IC50	1100.0	nM	10.1021/jm900012a
Homo sapiens	PC-9	IC50	10.0	nM	10.1021/acs.jmedchem.5b01106
Homo sapiens	SK-BR-3	GI50	29.0	nM	10.1021/jm0603116
Homo sapiens	SK-BR-3	IC50	24.0	nM	10.1016/j.bmcl.2005.08.013
Homo sapiens	SK-BR-3	IC50	24.0	nM	10.1021/jm900098v
Homo sapiens	SK-BR-3	IC50	58.0	nM	10.1021/jm900012a
Homo sapiens	SK-BR-3	IC50	230.0	nM	10.1021/jm900012a
Homo sapiens	SK-OV-3	GI50	32.0	nM	10.1021/jm0603116
Homo sapiens	SK-OV-3	IC50	122.0	nM	10.1021/jm900012a
Homo sapiens	SK-OV-3	IC50	220.0	nM	10.1021/jm900098v
Mus musculus	Hepatocyte	Activity	nan	None	10.1021/acs.jmedchem.7b00978
Mus musculus	Mus musculus	Inhibition	84.0	%	10.1016/j.bmcl.2012.07.052
Mus musculus	Mus musculus	Inhibition	nan	%	10.1016/j.bmcl.2012.07.052
Mus musculus	Mus musculus	MTD	10.0	mg kg-1	10.1021/jm200128m
Rattus norvegicus	Rattus norvegicus	MTD	12.0	mg/m2	10.1021/jm9004708
Severe acute respiratory syndrome coronavirus 2	Replicase polyprotein 1ab	Inhibition	10.6	%	10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2	Replicase polyprotein 1ab	Inhibition	12.91	%	10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	Inhibition	-0.7	%	10.21203/rs.3.rs-23951/v1
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	Inhibition	-0.33	%	10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	Inhibition	-0.32	%	10.6019/CHEMBL4495565
None	NON-PROTEIN TARGET	IC50	170.0	nM	10.1016/j.ejmech.2014.03.061
None	NON-PROTEIN TARGET	IC50	1340.0	nM	10.1016/j.bmcl.2014.01.070
None	NON-PROTEIN TARGET	IC50	1600.0	nM	10.1021/jm900012a
None	NON-PROTEIN TARGET	IC50	3110.0	nM	10.1016/j.ejmech.2014.03.061
None	NON-PROTEIN TARGET	IC50	50000.0	nM	10.1021/np060482d
None	No relevant target	T1/2	0.4333	hr	10.1021/jm9004708
None	Unchecked	Activity	nan	None	10.1021/acs.jmedchem.7b00978
None	Unchecked	IC50	10.0	nM	10.1021/acs.jmedchem.5b01106
None	Unchecked	IC50	150.0	nM	10.1016/j.bmcl.2008.03.028
None	Unchecked	Kd	210.0	nM	10.1021/jm100060b
None	Unchecked	Ki	250.0	nM	10.1021/jm901209q