Molecule

Kahalalide F

AlkaPlorer ID: AK023515

Synonym: None

IUPAC Name: (2R)-N-[(2S)-5-amino-1-[[(2R,3S)-1-[[(3S,6Z,9S,12R,15R,18R,19R)-9-benzyl-15-[(2S)-butan-2-yl]-6-ethylidene-19-methyl-2,5,8,11,14,17-hexaoxo-3,12-di(propan-2-yl)-1-oxa-4,7,10,13,16-pentazacyclononadec-18-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1-oxopentan-2-yl]-1-[(2R)-2-[[(2S)-2-[[(2S,3R)-3-hydroxy-2-[[(2R)-3-methyl-2-(5-methylhexanoylamino)butanoyl]amino]butanoyl]amino]-3-methylbutanoyl]amino]-3-methylbutanoyl]pyrrolidine-2-carboxamide

Structure

SMILES: C/C=C1\N=C(O)[C@H](CC2=CC=CC=C2)N=C(O)[C@@H](C(C)C)N=C(O)[C@@H]([C@@H](C)CC)N=C(O)[C@H](N=C(O)[C@H](N=C(O)[C@H](CCCN)N=C(O)[C@H]2CCCN2C(=O)[C@H](N=C(O)[C@@H](N=C(O)[C@@H](N=C(O)[C@H](N=C(O)CCCC(C)C)C(C)C)[C@@H](C)O)C(C)C)C(C)C)[C@@H](C)CC)[C@@H](C)OC(=O)[C@H](C(C)C)N=C1O

InChI: InChI=1S/C75H124N14O16/c1-20-44(16)59(71(100)88-62-47(19)105-75(104)58(43(14)15)84-63(92)49(22-3)77-65(94)51(37-48-30-24-23-25-31-48)79-67(96)55(40(8)9)81-70(99)60(45(17)21-2)86-73(62)102)85-64(93)50(32-27-35-76)78-66(95)52-33-28-36-89(52)74(103)57(42(12)13)83-69(98)56(41(10)11)82-72(101)61(46(18)90)87-68(97)54(39(6)7)80-53(91)34-26-29-38(4)5/h22-25,30-31,38-47,50-52,54-62,90H,20-21,26-29,32-37,76H2,1-19H3,(H,77,94)(H,78,95)(H,79,96)(H,80,91)(H,81,99)(H,82,101)(H,83,98)(H,84,92)(H,85,93)(H,86,102)(H,87,97)(H,88,100)/b49-22-/t44-,45-,46+,47+,50-,51-,52+,54+,55+,56-,57+,58-,59+,60+,61-,62+/m0/s1

InChIKey: RCGXNDQKCXNWLO-YUHQQKLOSA-N

Reference

A microbial factory for defensive kahalalides in a tripartite marine symbiosis

PubChem CID: 9898671

CAS: 149204-42-2

SuperNatural Ⅲ: SN0321478-12

NPASS: NPC7817

{

NPAtlas: NPA033470

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Beauveria tenella	Beauveria	Cordycipitaceae	Hypocreales	Sordariomycetes	Ascomycota	Fungi	Eukaryota
Monachosorum flagellare	Monachosorum	Dennstaedtiaceae	Polypodiales	Polypodiopsida	Streptophyta	Viridiplantae	Eukaryota
Podocarpus nivalis	Podocarpus	Podocarpaceae	Araucariales	Pinopsida	Streptophyta	Viridiplantae	Eukaryota
Vibrio cholerae	Vibrio	Vibrionaceae	Vibrionales	Gammaproteobacteria	Pseudomonadota	None	Bacteria
Drypetes laciniata	Drypetes	Putranjivaceae	Malpighiales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Clostridium pasteurianum	Clostridium	Clostridiaceae	Eubacteriales	Clostridia	Bacillota	None	Bacteria
Bidens aurea	Bidens	Asteraceae	Asterales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Synoicum adareanum	Synoicum	Polyclinidae	Aplousobranchia	Ascidiacea	Chordata	Metazoa	Eukaryota
Rheum australe	Rheum	Polygonaceae	Caryophyllales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Aparisthmium cordatum	Aparisthmium	Euphorbiaceae	Malpighiales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Melia azedarach	Melia	Meliaceae	Sapindales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota

Properties Information

Molecule Weight: 1477.8989999999978

TPSA？: 483.94000000000017

MolLogP？: 11.919999999999998

Number of H-Donors: 14

Number of H-Acceptors: 17

RingCount: 3

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Homo sapiens	786-0	GI50	1737.8	nM	None
Homo sapiens	A549	GI50	135.83	nM	None
Homo sapiens	ACHN	GI50	1671.09	nM	None
Homo sapiens	BT-549	GI50	3443.5	nM	None
Homo sapiens	CCRF-CEM	GI50	2864.18	nM	None
Homo sapiens	EKVX	GI50	264.85	nM	None
Homo sapiens	HCC 2998	GI50	290.4	nM	None
Homo sapiens	HCT-15	GI50	271.64	nM	None
Homo sapiens	HL-60	GI50	39355.01	nM	None
Homo sapiens	HOP-62	GI50	1761.98	nM	None
Homo sapiens	Hs-578T	GI50	161.44	nM	None
Homo sapiens	HT-29	GI50	160.69	nM	None
Homo sapiens	IGROV-1	GI50	1438.8	nM	None
Homo sapiens	K562	GI50	3589.22	nM	None
Homo sapiens	KM12	GI50	183.23	nM	None
Homo sapiens	LOX IMVI	GI50	3639.15	nM	None
Homo sapiens	M14	GI50	1380.38	nM	None
Homo sapiens	Malme-3M	GI50	1999.86	nM	None
Homo sapiens	MCF7	GI50	461.32	nM	None
Homo sapiens	MDA-MB-435	GI50	1137.63	nM	None
Homo sapiens	MOLT-4	GI50	12078.14	nM	None
Homo sapiens	NCI/ADR-RES	GI50	3040.89	nM	None
Homo sapiens	NCI-H226	GI50	2233.57	nM	None
Homo sapiens	NCI-H23	GI50	4197.59	nM	None
Homo sapiens	NCI-H322M	GI50	192.75	nM	None
Homo sapiens	NCI-H460	GI50	1517.05	nM	None
Homo sapiens	NCI-H522	GI50	3706.81	nM	None
Homo sapiens	OVCAR-3	GI50	1358.31	nM	None
Homo sapiens	OVCAR-4	GI50	862.98	nM	None
Homo sapiens	OVCAR-5	GI50	1625.55	nM	None
Homo sapiens	OVCAR-8	GI50	4634.47	nM	None
Homo sapiens	PC-3	GI50	167.88	nM	None
Homo sapiens	RPMI-8226	GI50	1733.8	nM	None
Homo sapiens	RXF 393	GI50	3104.56	nM	None
Homo sapiens	SF-268	GI50	1419.06	nM	None
Homo sapiens	SF-295	GI50	1690.44	nM	None
Homo sapiens	SF-539	GI50	1694.34	nM	None
Homo sapiens	SK-MEL-2	GI50	2312.06	nM	None
Homo sapiens	SK-MEL-28	GI50	1503.14	nM	None
Homo sapiens	SK-MEL-5	GI50	456.04	nM	None
Homo sapiens	SK-OV-3	GI50	189.23	nM	None
Homo sapiens	SN12C	GI50	2636.33	nM	None
Homo sapiens	SNB-19	GI50	346.74	nM	None
Homo sapiens	SNB-75	GI50	222.33	nM	None
Homo sapiens	SR	GI50	14354.89	nM	None
Homo sapiens	SW-620	GI50	343.56	nM	None
Homo sapiens	TK-10	GI50	1845.02	nM	None
Homo sapiens	U-251	GI50	343.56	nM	None
Homo sapiens	UACC-257	GI50	1020.94	nM	None
Homo sapiens	UACC-62	GI50	1415.79	nM	None
Homo sapiens	UO-31	GI50	2103.78	nM	None
Mus musculus	L5178Y	IC50	4300.0	nM	10.1021/acs.jnatprod.8b00723
Mus musculus	L5178Y	IC50	4300.0	nM	10.1021/acs.jnatprod.9b00151
Mycobacterium tuberculosis	Mycobacterium tuberculosis	Inhibition	67.0	%	10.1016/j.ejmech.2019.01.026