Molecule

Apratoxin A

AlkaPlorer ID: AK002185

Synonym: None

IUPAC Name: (2S,3S,5S,7S,10S,16S,19S,22S,25E,27S)-16-[(2S)-butan-2-yl]-7-tert-butyl-3-hydroxy-22-[(4-methoxyphenyl)methyl]-2,5,17,19,20,25-hexamethyl-8-oxa-29-thia-14,17,20,23,30-pentazatricyclo[25.2.1.010,14]triaconta-1(30),25-diene-9,15,18,21,24-pentone

Structure

SMILES: CC[C@H](C)[C@H]1C(=O)N2CCC[C@H]2C(=O)O[C@H](C(C)(C)C)C[C@@H](C)C[C@H](O)[C@H](C)C2=N[C@@H](/C=C(\C)C(O)=N[C@@H](CC3=CC=C(OC)C=C3)C(=O)N(C)[C@@H](C)C(=O)N1C)CS2

InChI: InChI=1S/C45H69N5O8S/c1-13-27(3)38-43(55)50-20-14-15-35(50)44(56)58-37(45(7,8)9)22-26(2)21-36(51)29(5)40-46-32(25-59-40)23-28(4)39(52)47-34(24-31-16-18-33(57-12)19-17-31)42(54)48(10)30(6)41(53)49(38)11/h16-19,23,26-27,29-30,32,34-38,51H,13-15,20-22,24-25H2,1-12H3,(H,47,52)/b28-23+/t26-,27-,29-,30-,32-,34-,35-,36-,37-,38-/m0/s1

InChIKey: KXUJXPZXILTXDA-CKIYSKEDSA-N

Reference

Ulongamides A−F, New β-Amino Acid-Containing Cyclodepsipeptides from Palauan Collections of the Marine Cyanobacterium <i>Lyngbya</i> sp.

PubChem CID: 6326668

CAS: 350791-64-9

LOTUS: LTS0109278

SuperNatural Ⅲ: SN0198308-08

NPASS: NPC184933

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Lyngbya majuscula	Lyngbya	Oscillatoriaceae	Oscillatoriales	Cyanophyceae	Cyanobacteriota	None	Bacteria

Properties Information

Molecule Weight: 840.1409999999998

TPSA？: 161.64

MolLogP？: 6.118800000000007

Number of H-Donors: 2

Number of H-Acceptors: 10

RingCount: 4

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Homo sapiens	786-0	GI50	4.52	nM	10.1038/nchembio769
Homo sapiens	786-0	GI50	41.0	nM	10.1021/acs.jmedchem.7b00833
Homo sapiens	A549	GI50	5.38	nM	10.1038/nchembio769
Homo sapiens	A549	GI50	6.4	nM	10.1021/acs.jmedchem.7b00833
Homo sapiens	ACHN	GI50	2.69	nM	10.1038/nchembio769
Homo sapiens	BXPC-3	GI50	4.9	nM	10.1021/acs.jmedchem.7b00833
Homo sapiens	CAKI-1	GI50	4.05	nM	10.1038/nchembio769
Homo sapiens	COLO 205	GI50	2.71	nM	10.1038/nchembio769
Homo sapiens	DU-145	GI50	10.3	nM	10.1038/nchembio769
Homo sapiens	EKVX	GI50	7.56	nM	10.1038/nchembio769
Homo sapiens	Fibroblast growth factor receptor	Inhibition	nan	%	10.1038/nchembio769
Homo sapiens	HCC 2998	GI50	3.65	nM	10.1038/nchembio769
Homo sapiens	HCT-116	GI50	0.916	nM	10.1038/nchembio769
Homo sapiens	HCT-116	GI50	11.0	nM	10.1021/acs.jmedchem.7b00833
Homo sapiens	HCT-116	IC50	1.49	nM	10.1021/ml200176m
Homo sapiens	HCT-116	IC50	2.8	nM	10.1021/acs.jmedchem.7b00833
Homo sapiens	HCT-116	IC50	5.97	nM	10.1021/ml200176m
Homo sapiens	HCT-116	Inhibition	nan	%	10.1021/acs.jnatprod.9b00826
Homo sapiens	HCT-15	GI50	4.29	nM	10.1038/nchembio769
Homo sapiens	HeLa	IC50	10.0	nM	10.1021/np700717s
Homo sapiens	HL-60(TB)	GI50	0.851	nM	10.1038/nchembio769
Homo sapiens	HOP-62	GI50	7.68	nM	10.1038/nchembio769
Homo sapiens	HOP-92	GI50	3.09	nM	10.1038/nchembio769
Homo sapiens	HT-29	FC	-3.68	None	10.1038/nchembio769
Homo sapiens	HT-29	FC	-2.79	None	10.1038/nchembio769
Homo sapiens	HT-29	FC	-2.52	None	10.1038/nchembio769
Homo sapiens	HT-29	FC	-2.35	None	10.1038/nchembio769
Homo sapiens	HT-29	FC	-2.2	None	10.1038/nchembio769
Homo sapiens	HT-29	FC	-2.17	None	10.1038/nchembio769
Homo sapiens	HT-29	FC	2.0	None	10.1038/nchembio769
Homo sapiens	HT-29	FC	2.21	None	10.1038/nchembio769
Homo sapiens	HT-29	FC	2.49	None	10.1038/nchembio769
Homo sapiens	HT-29	FC	2.56	None	10.1038/nchembio769
Homo sapiens	HT-29	FC	2.68	None	10.1038/nchembio769
Homo sapiens	HT-29	FC	3.78	None	10.1038/nchembio769
Homo sapiens	HT-29	FC	4.09	None	10.1038/nchembio769
Homo sapiens	HT-29	FC	5.19	None	10.1038/nchembio769
Homo sapiens	HT-29	FC	6.35	None	10.1038/nchembio769
Homo sapiens	HT-29	FC	6.82	None	10.1038/nchembio769
Homo sapiens	HT-29	FC	7.38	None	10.1038/nchembio769
Homo sapiens	HT-29	FC	7.57	None	10.1038/nchembio769
Homo sapiens	HT-29	FC	10.01	None	10.1038/nchembio769
Homo sapiens	HT-29	FC	10.37	None	10.1038/nchembio769
Homo sapiens	HT-29	FC	10.46	None	10.1038/nchembio769
Homo sapiens	HT-29	FC	12.09	None	10.1038/nchembio769
Homo sapiens	HT-29	FC	12.65	None	10.1038/nchembio769
Homo sapiens	HT-29	FC	16.18	None	10.1038/nchembio769
Homo sapiens	HT-29	GI50	1.04	nM	10.1038/nchembio769
Homo sapiens	HT-29	IC50	1.4	nM	10.1021/np700717s
Homo sapiens	HT-29	LC50	75.2	nM	10.1038/nchembio769
Homo sapiens	Huh-7	GI50	7.2	nM	10.1021/acs.jmedchem.7b00833
Homo sapiens	HUVEC	Activity	nan	None	10.1038/nchembio769
Homo sapiens	IGROV-1	GI50	0.742	nM	10.1038/nchembio769
Homo sapiens	K562	GI50	14.8	nM	10.1038/nchembio769
Homo sapiens	KM12	GI50	3.52	nM	10.1038/nchembio769
Homo sapiens	Liver	Drug metabolism	86.0	%	10.1021/acs.jmedchem.7b00833
Homo sapiens	LOX IMVI	GI50	2.3	nM	10.1038/nchembio769
Homo sapiens	LOX IMVI	LC50	23.2	nM	10.1038/nchembio769
Homo sapiens	M14	GI50	2.09	nM	10.1038/nchembio769
Homo sapiens	Malme-3M	GI50	4.77	nM	10.1038/nchembio769
Homo sapiens	MCF7	GI50	6.57	nM	10.1038/nchembio769
Homo sapiens	MCF7	GI50	1000.0	nM	10.1021/acs.jmedchem.7b00833
Homo sapiens	MDA-MB-231	GI50	1.46	nM	10.1038/nchembio769
Homo sapiens	MDA-MB-435	GI50	3.35	nM	10.1038/nchembio769
Homo sapiens	MKN-74	GI50	9.7	nM	10.1021/acs.jmedchem.7b00833
Homo sapiens	MOLT-4	GI50	48.0	nM	10.1038/nchembio769
Homo sapiens	NCI/ADR-RES	GI50	15.3	nM	10.1038/nchembio769
Homo sapiens	NCI-H226	GI50	1.31	nM	10.1038/nchembio769
Homo sapiens	NCI-H23	GI50	8.23	nM	10.1038/nchembio769
Homo sapiens	NCI-H322M	GI50	3.99	nM	10.1038/nchembio769
Homo sapiens	NCI-H460	GI50	2.77	nM	10.1038/nchembio769
Homo sapiens	NCI-H460	IC50	2.5	nM	10.1021/np4004992
Homo sapiens	NCI-H522	GI50	6.03	nM	10.1038/nchembio769
Homo sapiens	OVCAR-3	GI50	16.9	nM	10.1038/nchembio769
Homo sapiens	OVCAR-4	GI50	100.0	nM	10.1038/nchembio769
Homo sapiens	OVCAR-5	GI50	100.0	nM	10.1038/nchembio769
Homo sapiens	OVCAR-8	GI50	7.26	nM	10.1038/nchembio769
Homo sapiens	PC-3	GI50	4.96	nM	10.1038/nchembio769
Homo sapiens	RXF 393	GI50	7.12	nM	10.1038/nchembio769
Homo sapiens	SF-268	GI50	50.8	nM	10.1038/nchembio769
Homo sapiens	SF-295	GI50	1.26	nM	10.1038/nchembio769
Homo sapiens	SF-295	LC50	70.3	nM	10.1038/nchembio769
Homo sapiens	SF-539	GI50	0.503	nM	10.1038/nchembio769
Homo sapiens	SF-539	LC50	69.4	nM	10.1038/nchembio769
Homo sapiens	SK-MEL-2	GI50	100.0	nM	10.1038/nchembio769
Homo sapiens	SK-MEL-28	GI50	5.49	nM	10.1038/nchembio769
Homo sapiens	SK-MEL-5	GI50	2.31	nM	10.1038/nchembio769
Homo sapiens	SK-OV-3	GI50	5.27	nM	10.1038/nchembio769
Homo sapiens	SK-OV-3	GI50	31.0	nM	10.1021/acs.jmedchem.7b00833
Homo sapiens	SN12C	GI50	3.94	nM	10.1038/nchembio769
Homo sapiens	SNB-19	GI50	7.0	nM	10.1038/nchembio769
Homo sapiens	SNB-75	GI50	1.96	nM	10.1038/nchembio769
Homo sapiens	SR	GI50	1.5	nM	10.1038/nchembio769
Homo sapiens	SR	LC50	27.4	nM	10.1038/nchembio769
Homo sapiens	SW-620	GI50	3.16	nM	10.1038/nchembio769
Homo sapiens	T47D	GI50	3.63	nM	10.1038/nchembio769
Homo sapiens	TK-10	GI50	2.63	nM	10.1038/nchembio769
Homo sapiens	U-251	GI50	1.56	nM	10.1038/nchembio769
Homo sapiens	U2OS	Activity	nan	None	10.1038/nchembio769
Homo sapiens	U2OS	FC	20.0	None	10.1038/nchembio769
Homo sapiens	U2OS	IC50	10.0	nM	10.1021/np700717s
Homo sapiens	U2OS	IC50	50.0	nM	10.1038/nchembio769
Homo sapiens	U2OS	Inhibition	0.8	%	10.1038/nchembio769
Homo sapiens	U2OS	Inhibition	5.5	%	10.1038/nchembio769
Homo sapiens	U2OS	Inhibition	22.6	%	10.1038/nchembio769
Homo sapiens	U2OS	Inhibition	28.0	%	10.1038/nchembio769
Homo sapiens	U2OS	Inhibition	28.2	%	10.1038/nchembio769
Homo sapiens	U2OS	Inhibition	42.7	%	10.1038/nchembio769
Homo sapiens	U2OS	Inhibition	50.2	%	10.1038/nchembio769
Homo sapiens	U2OS	Inhibition	58.0	%	10.1038/nchembio769
Homo sapiens	U2OS	Inhibition	61.6	%	10.1038/nchembio769
Homo sapiens	U2OS	Inhibition	68.3	%	10.1038/nchembio769
Homo sapiens	U2OS	Inhibition	82.1	%	10.1038/nchembio769
Homo sapiens	U2OS	Inhibition	nan	%	10.1038/nchembio769
Homo sapiens	U-87 MG	GI50	18.0	nM	10.1021/acs.jmedchem.7b00833
Homo sapiens	UACC-257	GI50	7.15	nM	10.1038/nchembio769
Homo sapiens	UACC-62	GI50	3.28	nM	10.1038/nchembio769
Homo sapiens	UO-31	GI50	2.95	nM	10.1038/nchembio769
Mus musculus	Liver	Drug metabolism	81.0	%	10.1021/acs.jmedchem.7b00833
Mus musculus	Mus musculus	Activity	nan	None	10.1021/ml200176m
None	ADMET	FC	30.0	None	10.1038/nchembio769
None	ADMET	IC50	60.0	nM	10.1038/nchembio769
None	ADMET	IC50	1800.0	nM	10.1038/nchembio769
None	NON-PROTEIN TARGET	GI50	1.28	nM	10.1038/nchembio769
None	NON-PROTEIN TARGET	LC50	69.0	nM	10.1038/nchembio769
None	Unchecked	GI50	39.0	nM	10.1021/acs.jmedchem.7b00833
None	Unchecked	Inhibition	25.0	%	10.1038/nchembio769
None	Unchecked	Inhibition	40.0	%	10.1038/nchembio769
None	Unchecked	Inhibition	87.5	%	10.1038/nchembio769
None	Unchecked	Inhibition	100.0	%	10.1038/nchembio769
None	Unchecked	Inhibition	nan	%	10.1038/nchembio769

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT000413	*C(=O)[C@@H]1CCCN1C(=O)[C@H]([C@@H](C)CC)N(C)C(=O)[C@H](C)N(C)C(=O)[C@H](Cc1ccc(OC)cc1)NC(=O)/C(C)=C/C1CSC([C@@H](C)[C@@H](O)C[C@H](C)C[C@H](O)C(C)(C)C)=N1>>CC[C@H](C)[C@H]1C(=O)N2CCC[C@H]2C(=O)O[C@H](C(C)(C)C)C[C@@H](C)C[C@H](O)[C@H](C)C2=N[C@@H](/C=C(\C)C(=O)N[C@@H](Cc3ccc(OC)cc3)C(=O)N(C)[C@@H](C)C(=O)N1C)CS2	RXN-23097