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Amycolatopsin A

CAT: 0804-HY-N11048Size: 1 EachDry Ice: NoHazardous: No
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Description
Amycolatopsin A is a 20-membered macrolide, that can be isolated from a strain of the rare actinomycete Amycolatopsis sp. MST‐108494. Amycolatopsin A shows antimycobacterial activity against Mycobacterium bovis (BCG) and M. tuberculosis (H37Rv) with IC50 values of 0.4 µM and 4.4 µM, respectively[1].
CAS Number
2209112-96-7
UNSPSC
12352005
Target
Bacterial
Type
Natural Products
Related Pathways
Anti-infection
Applications
COVID-19-immunoregulation
Field of Research
Cancer; Infection
Assay Protocol
https://www.medchemexpress.com/amycolatopsin-a.html
Solubility
10 mM in DMSO
Smiles
C[C@]1([C@H](O[C@](O)([C@@H]([C@H]1O)OC)[C@@H](C2([H])CC(C(/C=C(/C=C(/C=C(C(C(/C=C(/C=C(\C=C(C(O2)=O)/C)OC)CO)C)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)C)OC)O)O)/C)C)C)O)OC)C)CCCOC)O[C@H]4C[C@@H]([C@@H]([C@H](O4)C)O[C@H]5C[C@@](O)([C@@H]([C@H](O5)C)O)C)O
Molecular Formula
C60H98O23
Molecular Weight
1187.41
References & Citations
[1]Al-Fadhli AA, et al. Macrolides from rare actinomycetes: Structures and bioactivities. Int J Antimicrob Agents. 2022 Feb;59 (2) :106523.
Shipping Conditions
Room temperature
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

(3E,5Z,7Z,11E,13E,15Z)-20-[(1S)-1-[(2S,3R,4R,5S,6R)-5-[(2S,4S,5S,6R)-5-[(2S,4R,5R,6R)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-2,4-dihydroxy-3-methoxy-6-(3-methoxypropyl)-5-methyloxan-2-yl]ethyl]-10-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxy-17-hydroxy-7-(hydroxymethyl)-5,18-dimethoxy-3,9,11,13,15-pentamethyl-1-oxacycloicosa-3,5,7,11,13,15-hexaen-2-one
CAS Number2209112-96-7
PubChem CID155859118
IUPAC Name(3E,5Z,7Z,11E,13E,15Z)-20-[(1S)-1-[(2S,3R,4R,5S,6R)-5-[(2S,4S,5S,6R)-5-[(2S,4R,5R,6R)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-2,4-dihydroxy-3-methoxy-6-(3-methoxypropyl)-5-methyloxan-2-yl]ethyl]-10-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxy-17-hydroxy-7-(hydroxymethyl)-5,18-dimethoxy-3,9,11,13,15-pentamethyl-1-oxacycloicosa-3,5,7,11,13,15-hexaen-2-one
Molecular FormulaC60H98O23
Molecular Weight1187.4
XLogP0.7
Topological Polar Surface Area319
Hydrogen Bond Donor Count9
Hydrogen Bond Acceptor Count23
Rotatable Bond Count17
Heavy Atom Count83
Formal Charge0
Complexity2290
SMILES
C[C@@H]1[C@H]([C@H](C[C@@H](O1)O[C@@]2([C@H](O[C@]([C@@H]([C@H]2O)OC)([C@@H](C)C3CC(C(/C=C(\C=C(\C=C(\C(C(/C=C(/C=C(/C=C(/C(=O)O3)\C)\OC)\CO)C)O[C@@H]4[C@@H]([C@H]([C@@H]([C@H](O4)C)OC)O)O)/C)/C)/C)O)OC)O)CCCOC)C)O)O[C@H]5C[C@@]([C@@H]([C@H](O5)C)O)(C)O
InChI
InChI=1S/C60H98O23/c1-30-20-31(2)22-41(62)44(73-14)27-43(79-56(68)34(5)24-40(72-13)25-39(29-61)23-33(4)50(32(3)21-30)81-57-49(65)48(64)52(74-15)37(8)78-57)35(6)60(70)55(75-16)54(67)59(11,45(82-60)18-17-19-71-12)83-46-26-42(63)51(36(7)76-46)80-47-28-58(10,69)53(66)38(9)77-47/h20-25,33,35-38,41-55,57,61-67,69-70H,17-19,26-29H2,1-16H3/b30-20+,31-22-,32-21+,34-24+,39-23-,40-25-/t33?,35-,36+,37+,38+,41?,42-,43?,44?,45+,46-,47-,48+,49+,50?,51+,52+,53+,54+,55+,57+,58+,59+,60-/m0/s1
InChIKey
VGMCXRHEZZYRBZ-NPMLRHTESA-N
Chemical Structure
2D Structure
2D structure of (3E,5Z,7Z,11E,13E,15Z)-20-[(1S)-1-[(2S,3R,4R,5S,6R)-5-[(2S,4S,5S,6R)-5-[(2S,4R,5R,6R)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-2,4-dihydroxy-3-methoxy-6-(3-methoxypropyl)-5-methyloxan-2-yl]ethyl]-10-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxy-17-hydroxy-7-(hydroxymethyl)-5,18-dimethoxy-3,9,11,13,15-pentamethyl-1-oxacycloicosa-3,5,7,11,13,15-hexaen-2-one
CAS: 2209112-96-7
CID: 155859118
Formula: C60H98O23
MW: 1187.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight1187.4
XLogP30.7
Hydrogen Bond Donor Count9
Hydrogen Bond Acceptor Count23
Rotatable Bond Count17
Exact Mass1186.64988937
Monoisotopic Mass1186.64988937
Topological Polar Surface Area319 Ų
Heavy Atom Count83
Formal Charge0
Complexity2290
Isotope Atom Count0
Defined Atom Stereocenter Count19
Undefined Atom Stereocenter Count5
Defined Bond Stereocenter Count6
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
MBS5785225Amycolatopsin A
A208-0.5MGAmycolatopsin B
A209-0.1MGAmycolatopsin C

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