NP-MRD: Showing NP-Card for fatuamide A (NP0333788)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2024-09-08 21:45:14 UTC

Updated at

2025-12-21 01:41:04 UTC

NP-MRD ID

NP0333788

Natural Product DOI

https://doi.org/10.57994/3266

Secondary Accession Numbers

None

Natural Product Identification

Common Name

fatuamide A

Description

Fatuamide A belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. Based on a literature review very few articles have been published on fatuamide A.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05242300172D          

 59 62  0  0  1  0            999 V2000
   -4.4190   -7.7999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7545   -7.0462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5750   -6.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9106   -6.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4256   -5.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6052   -5.6251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2696   -6.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4491   -6.4650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8971   -5.8519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2296   -7.0080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0366   -7.1795    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4515   -6.6368    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -5.7750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -5.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2881   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -5.7750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0026   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -6.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10  9  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 12  1  0  0  0  0
 10 13  1  1  0  0  0
 10 14  1  6  0  0  0
 15 14  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 24  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 29 28  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 31 36  1  0  0  0  0
 29 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  2  0  0  0  0
 40 46  2  0  0  0  0
 27 47  2  0  0  0  0
 25 48  1  1  0  0  0
 23 49  1  1  0  0  0
 22 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  2  0  0  0  0
 52 53  1  0  0  0  0
 53 54  2  0  0  0  0
 54 55  1  0  0  0  0
 55 56  2  0  0  0  0
 51 56  1  0  0  0  0
 20 57  2  0  0  0  0
 17 58  1  6  0  0  0
 15 59  1  1  0  0  0
M  END


  Mrv2104 05242300172D          

 59 62  0  0  1  0            999 V2000
   -4.4190   -7.7999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7545   -7.0462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5750   -6.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9106   -6.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4256   -5.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6052   -5.6251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2696   -6.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4491   -6.4650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8971   -5.8519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2296   -7.0080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0366   -7.1795    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4515   -6.6368    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -5.7750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -5.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2881   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -5.7750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0026   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -6.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10  9  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 12  1  0  0  0  0
 10 13  1  1  0  0  0
 10 14  1  6  0  0  0
 15 14  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 24  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 29 28  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 31 36  1  0  0  0  0
 29 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  2  0  0  0  0
 40 46  2  0  0  0  0
 27 47  2  0  0  0  0
 25 48  1  1  0  0  0
 23 49  1  1  0  0  0
 22 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  2  0  0  0  0
 52 53  1  0  0  0  0
 53 54  2  0  0  0  0
 54 55  1  0  0  0  0
 55 56  2  0  0  0  0
 51 56  1  0  0  0  0
 20 57  2  0  0  0  0
 17 58  1  6  0  0  0
 15 59  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0333788

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(C[C@H](C)C[C@@H](C)CCC(=O)N[C@@H](CC2=CC=CC=C2)[C@H](O)C[C@H](O)CC(=O)N[C@@H](CC2=CC=CC=C2)[C@H](O)CC(=O)NCC(O)=O)CSC(=N1)C1=CC=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C44H58N4O9S/c1-28(19-29(2)20-32-27-58-44(46-32)34-15-9-10-16-37(34)50)17-18-40(53)47-35(21-30-11-5-3-6-12-30)38(51)23-33(49)24-42(55)48-36(22-31-13-7-4-8-14-31)39(52)25-41(54)45-26-43(56)57/h3-16,28-29,32-33,35-36,38-39,49-52H,17-27H2,1-2H3,(H,45,54)(H,47,53)(H,48,55)(H,56,57)/t28-,29+,32+,33-,35-,36-,38+,39+/m0/s1

> <INCHI_KEY>
JAQGSGYEGBOSBI-WKZOPCGPSA-N

> <FORMULA>
C44H58N4O9S

> <MOLECULAR_WEIGHT>
819.03

> <EXACT_MASS>
818.392450638

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
116

> <JCHEM_AVERAGE_POLARIZABILITY>
89.3799466871099

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(3R,4S)-4-[(3S,5R,6S)-3,5-dihydroxy-6-[(4S,6R)-7-[(4R)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-4,6-dimethylheptanamido]-7-phenylheptanamido]-3-hydroxy-5-phenylpentanamido]acetic acid

> <JCHEM_LOGP>
3.393856012436592

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.620304918012605

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.485766682765665

> <JCHEM_PKA_STRONGEST_BASIC>
4.5131937322581175

> <JCHEM_POLAR_SURFACE_AREA>
217.87999999999997

> <JCHEM_REFRACTIVITY>
222.89610000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
24

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(3R,4S)-4-[(3S,5R,6S)-3,5-dihydroxy-6-[(4S,6R)-7-[(4R)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-4,6-dimethylheptanamido]-7-phenylheptanamido]-3-hydroxy-5-phenylpentanamido]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-MAY-23         0                                  
HETATM    1  O   UNK     0      -8.249 -14.560   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -8.875 -13.153   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.407 -12.992   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -11.033 -11.585   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -10.128 -10.339   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.596 -10.500   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -7.970 -11.907   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.438 -12.068   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -5.408 -10.924   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.162 -13.082   0.000  0.00  0.00           C+0
HETATM   12  S   UNK     0      -5.668 -13.402   0.000  0.00  0.00           S+0
HETATM   13  H   UNK     0      -2.709 -12.389   0.000  0.00  0.00           H+0
HETATM   14  C   UNK     0      -2.667 -10.780   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000 -10.780   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667 -10.780   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335 -10.780   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       6.668 -11.550   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       8.002 -10.780   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.669 -10.780   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.337 -10.780   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      16.004 -10.780   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      17.338 -11.550   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      17.338 -13.090   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      18.672 -13.860   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      20.005 -13.090   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      21.339 -13.860   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      21.339 -15.400   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      20.005 -16.170   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      18.672 -15.400   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      18.672 -10.780   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      18.672  -9.240   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      20.005 -11.550   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      21.339 -10.780   0.000  0.00  0.00           C+0
HETATM   41  N   UNK     0      22.673 -11.550   0.000  0.00  0.00           N+0
HETATM   42  C   UNK     0      24.006 -10.780   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      25.340 -11.550   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      26.674 -10.780   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      25.340 -13.090   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      21.339  -9.240   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      14.670 -13.090   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      12.003 -13.090   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0       9.336 -13.090   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       9.336  -8.470   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      10.669  -6.160   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      12.003  -8.470   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0       1.334 -13.090   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      -1.334 -13.090   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   13   14                                             
CONECT   11   10   12                                                       
CONECT   12   11    8                                                       
CONECT   13   10                                                            
CONECT   14   10   15                                                       
CONECT   15   14   16   59                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   58                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   57                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   50                                                  
CONECT   23   22   24   49                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   48                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   47                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   37                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   31                                                       
CONECT   37   29   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39   41   46                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43                                                            
CONECT   46   40                                                            
CONECT   47   27                                                            
CONECT   48   25                                                            
CONECT   49   23                                                            
CONECT   50   22   51                                                       
CONECT   51   50   52   56                                                  
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   51                                                       
CONECT   57   20                                                            
CONECT   58   17                                                            
CONECT   59   15                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  124    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₄H₅₈N₄O₉S

Average Mass

819.0300 Da

Monoisotopic Mass

818.39245 Da

IUPAC Name

2-[(3R,4S)-4-[(3S,5R,6S)-3,5-dihydroxy-6-[(4S,6R)-7-[(4R)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-4,6-dimethylheptanamido]-7-phenylheptanamido]-3-hydroxy-5-phenylpentanamido]acetic acid

Traditional Name

[(3R,4S)-4-[(3S,5R,6S)-3,5-dihydroxy-6-[(4S,6R)-7-[(4R)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-4,6-dimethylheptanamido]-7-phenylheptanamido]-3-hydroxy-5-phenylpentanamido]acetic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]1(C[C@H](C)C[C@@H](C)CCC(=O)N[C@@H](CC2=CC=CC=C2)[C@H](O)C[C@H](O)CC(=O)N[C@@H](CC2=CC=CC=C2)[C@H](O)CC(=O)NCC(O)=O)CSC(=N1)C1=CC=CC=C1O

InChI Identifier

InChI=1S/C44H58N4O9S/c1-28(19-29(2)20-32-27-58-44(46-32)34-15-9-10-16-37(34)50)17-18-40(53)47-35(21-30-11-5-3-6-12-30)38(51)23-33(49)24-42(55)48-36(22-31-13-7-4-8-14-31)39(52)25-41(54)45-26-43(56)57/h3-16,28-29,32-33,35-36,38-39,49-52H,17-27H2,1-2H3,(H,45,54)(H,47,53)(H,48,55)(H,56,57)/t28-,29+,32+,33-,35-,36-,38+,39+/m0/s1

InChI Key

JAQGSGYEGBOSBI-WKZOPCGPSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	kelseya@uic.edu	Not Available	Not Available	2024-09-08	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	kelseya@uic.edu	Not Available	Not Available	2024-09-08	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD3OD, experimental)	kelseya@uic.edu	Not Available	Not Available	2024-09-08	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	kelseya@uic.edu	Not Available	Not Available	2024-09-08	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500.15991521, CD₃OD, simulated)	kelseya@uic.edu	Not Available	Not Available	2024-09-08	View Spectrum

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
Amphetamine or derivatives
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acyl
Imidothiolactone
Benzenoid
N-acyl-amine
Fatty amide
Monocyclic benzene moiety
Meta-thiazoline
Secondary alcohol
Imidothioester
Carboxamide group
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Sulfenyl compound
Monocarboxylic acid or derivatives
Imidothioic acid or derivatives
Carboxylic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.39	ChemAxon
pKa (Strongest Acidic)	3.49	ChemAxon
pKa (Strongest Basic)	4.51	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	217.88 Å²	ChemAxon
Rotatable Bond Count	24	ChemAxon
Refractivity	222.9 m³·mol⁻¹	ChemAxon
Polarizability	89.38 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

DOI: 10.1021/acs.jnatprod.4c01051

Showing NP-Card for fatuamide A (NP0333788)

MOL for NP0333788 (fatuamide A)

3D MOL for NP0333788 (fatuamide A)

3D SDF for NP0333788 (fatuamide A)

3D-SDF for NP0333788 (fatuamide A)

PDB for NP0333788 (fatuamide A)

3D PDB for NP0333788 (fatuamide A)

SMILES for NP0333788 (fatuamide A)

INCHI for NP0333788 (fatuamide A)

Structure for NP0333788 (fatuamide A)

3D Structure for NP0333788 (fatuamide A)