Naphthomycin A
AlkaPlorer ID: AK012608
Synonym: None
IUPAC Name: (7E,9S,10S,11S,12E,14S,16E,20S,21S,22E,24Z,26Z)-31-chloro-4,10,14,20-tetrahydroxy-3,7,9,11,17,21,27-heptamethyl-29-azatricyclo[28.3.1.05,33]tetratriaconta-1(33),2,4,7,12,16,22,24,26,30-decaene-6,18,28,32,34-pentone
Structure
SMILES: C/C1=C/C=C\C=C\[C@H](C)[C@@H](O)CC(=O)/C(C)=C/C[C@H](O)/C=C/[C@H](C)[C@H](O)[C@@H](C)/C=C(\C)C(=O)C2=C(O)C(C)=CC3=C2C(=O)C(Cl)=C(N=C1O)C3=O
InChI: InChI=1S/C40H46ClNO9/c1-20-11-9-8-10-12-23(4)40(51)42-34-33(41)39(50)31-28(38(34)49)18-26(7)37(48)32(31)36(47)25(6)17-24(5)35(46)22(3)14-16-27(43)15-13-21(2)30(45)19-29(20)44/h8-14,16-18,20,22,24,27,29,35,43-44,46,48H,15,19H2,1-7H3,(H,42,51)/b10-8-,11-9+,16-14+,21-13+,23-12-,25-17+/t20-,22-,24-,27-,29-,35-/m0/s1
InChIKey: AXEGRHYJHHPVDH-UMKVKWLOSA-N
Reference
Cloning and functional analysis of the naphthomycin biosynthetic gene cluster in Streptomyces sp. CS
PubChem CID: 10101379
LOTUS: LTS0246298
SuperNatural Ⅲ: SN0017761-07
NPASS: NPC12890
{NPAtlas: NPA000326
Source
| Species | Genus | Family | Order | Class | Phylum | Kingdom | Domain |
|---|---|---|---|---|---|---|---|
| Streptomyces sp. | Streptomyces | Streptomycetaceae | Kitasatosporales | Actinomycetes | Actinomycetota | None | Bacteria |
| Streptomyces sp. CS | Streptomyces | Streptomycetaceae | Kitasatosporales | Actinomycetes | Actinomycetota | None | Bacteria |
Properties Information
Molecule Weight: 720.259
TPSA？: 181.79
MolLogP？: 6.5306200000000105
Number of H-Donors: 5
Number of H-Acceptors: 9
RingCount: 4
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Fusarium oxysporum | Fusarium oxysporum | MIC | 400.0 | ug.mL-1 | 10.1021/np300109s |
| Fusarium verticillioides | Fusarium verticillioides | MIC | 100.0 | ug.mL-1 | 10.1021/np300109s |
| Homo sapiens | A549 | IC50 | 15910.0 | nM | 10.1021/np300109s |
| Homo sapiens | HeLa | IC50 | 30200.0 | nM | 10.1021/acs.jnatprod.6b01059 |
| Homo sapiens | HL-60 | IC50 | 2100.0 | nM | 10.1021/acs.jnatprod.6b01059 |
| Homo sapiens | HL-60 | IC50 | 25610.0 | nM | 10.1021/np300109s |
| Homo sapiens | Indoleamine 2,3-dioxygenase | IC50 | 440.0 | nM | 10.1021/acs.jnatprod.6b01059 |
| Homo sapiens | MCF7 | IC50 | 11670.0 | nM | 10.1021/np300109s |
| Homo sapiens | MDA-MB-231 | IC50 | 34600.0 | nM | 10.1021/acs.jnatprod.6b01059 |
| Homo sapiens | SMMC-7721 | IC50 | 16620.0 | nM | 10.1021/np300109s |
| Homo sapiens | SW480 | IC50 | 7600.0 | nM | 10.1021/acs.jnatprod.6b01059 |
| Homo sapiens | SW480 | IC50 | 11660.0 | nM | 10.1021/np300109s |
| Homo sapiens | U2OS | IC50 | 20500.0 | nM | 10.1021/acs.jnatprod.6b01059 |
| Pyricularia oryzae | Pyricularia oryzae | MIC | 400.0 | ug.mL-1 | 10.1021/np300109s |
| None | Molecular identity unknown | MIC | 400.0 | ug.mL-1 | 10.1021/np300109s |