NP-MRD: Showing NP-Card for (2s)-2-({1-[(2r)-10-acetyl-11,13-dihydroxy-2,12-dimethyl-3,5-dioxo-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),6,10,12-tetraen-4-ylidene]ethyl}amino)pentanedioic acid (NP0214657)

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Record Information

Version

2.0

Created at

2022-09-05 14:01:31 UTC

Updated at

2022-09-05 14:01:31 UTC

NP-MRD ID

NP0214657

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-({1-[(2r)-10-acetyl-11,13-dihydroxy-2,12-dimethyl-3,5-dioxo-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),6,10,12-tetraen-4-ylidene]ethyl}amino)pentanedioic acid

Description

Usimine B belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. (2s)-2-({1-[(2r)-10-acetyl-11,13-dihydroxy-2,12-dimethyl-3,5-dioxo-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),6,10,12-tetraen-4-ylidene]ethyl}amino)pentanedioic acid is found in Stereocaulon alpinum. (2s)-2-({1-[(2r)-10-acetyl-11,13-dihydroxy-2,12-dimethyl-3,5-dioxo-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),6,10,12-tetraen-4-ylidene]ethyl}amino)pentanedioic acid was first documented in 2010 (PMID: 20355318). Based on a literature review very few articles have been published on Usimine B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052216012D          

 34 36  0  0  1  0            999 V2000
    7.4779   11.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5641   11.0973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3178   10.7617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8966   10.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1430   10.9479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0567   11.7684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4755   10.4630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7219   10.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5618    9.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8943    9.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3154    9.3070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9829    9.7919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6503    9.3070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3954    8.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    7.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3954    7.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    6.3789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    7.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579    6.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    6.3789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204    5.6645    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0954    5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454    4.2355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454    5.6645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204    4.2355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579    7.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    7.8079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    8.5224    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7499    8.6086    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  0  0  0  0
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 14 15  2  0  0  0  0
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 18 19  2  0  0  0  0
 19 20  1  4  0  0  0
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 18 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 14 33  1  0  0  0  0
 11 33  1  0  0  0  0
 33 34  1  1  0  0  0
M  END

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
   -7.0248    0.7533    1.6343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6754    0.1685    1.6412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5454   -0.8213    2.4491 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5383    0.5813    0.8630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5636    1.6324   -0.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6376    2.4263   -0.2998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3952    1.9628   -0.7673 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1477    1.5720   -1.3057 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3667   -0.1723    1.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0767   -1.2534    1.9350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7039   -1.5815    1.7592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8724   -2.3186    2.4552 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5304   -2.4759    2.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2299   -3.2451    2.8148 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0382   -1.7502    0.9557 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2869   -1.8758    0.5731 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1841   -2.7777    1.3295 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8543   -1.1940   -0.5422 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1017   -0.4338   -0.4055 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3915    0.1782   -1.7499 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6328    0.9969   -1.8216 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8222    1.5298   -3.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1038    2.4786   -3.5703 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7612    0.9679   -4.0224 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9542    0.5230    0.6952 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8890    0.6280    1.3491 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9918    1.3527    1.0588 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0853   -0.8656    0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6440   -0.0913   -0.6015 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2952   -0.9353    0.5190 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8746   -2.0277   -0.5703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1142    1.7657    2.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5748    0.6534    0.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7001    0.1511    2.3621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5213    2.4869   -0.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4934    3.3489   -1.9525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8922    3.9893   -1.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9748    2.7995   -2.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1311    2.3219   -1.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3020   -2.8128    3.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3387   -2.4655    2.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1733   -2.7993    0.7903 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8641   -3.8355    1.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3994   -1.2368   -1.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9274   -1.1620   -0.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5246    0.7968   -2.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3989   -0.6797   -2.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5299    1.8427   -1.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5585    0.4606   -1.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2665    0.1146   -3.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8306    2.3577    1.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9221   -2.0665   -0.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7054   -1.4897   -1.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3188   -2.9388   -0.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
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  7  8  1  0
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 31 32  2  0
 31 33  1  0
 33 34  1  6
 12  4  1  0
 33 14  1  0
 33 11  1  0
  1 35  1  0
  1 36  1  0
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  8 39  1  0
  8 40  1  0
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 10 42  1  0
 15 43  1  0
 20 44  1  0
 20 45  1  0
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 21 47  1  0
 22 48  1  1
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 23 50  1  0
 24 51  1  0
 24 52  1  0
 27 53  1  0
 30 54  1  0
 34 55  1  0
 34 56  1  0
 34 57  1  0
M  END


  Mrv1652309052216012D          

 34 36  0  0  1  0            999 V2000
    7.4779   11.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5641   11.0973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3178   10.7617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8966   10.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1430   10.9479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0567   11.7684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4755   10.4630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7219   10.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5618    9.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8943    9.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3154    9.3070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9829    9.7919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6503    9.3070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3954    8.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    7.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3954    7.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    6.3789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    7.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579    6.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    6.3789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204    5.6645    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0954    5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454    4.2355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454    5.6645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204    4.2355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579    7.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    7.8079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    8.5224    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7499    8.6086    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
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 18 19  2  0  0  0  0
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M  END
> <DATABASE_ID>
NP0214657

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)C1=C(O)C(C)=C(O)C2=C1OC1=CC(=O)C(=C(C)N[C@@H](CCC(O)=O)C(O)=O)C(=O)[C@]21C

> <INCHI_IDENTIFIER>
InChI=1S/C23H23NO10/c1-8-18(29)16(10(3)25)20-17(19(8)30)23(4)13(34-20)7-12(26)15(21(23)31)9(2)24-11(22(32)33)5-6-14(27)28/h7,11,24,29-30H,5-6H2,1-4H3,(H,27,28)(H,32,33)/t11-,23-/m0/s1

> <INCHI_KEY>
YAJFSGDAEAKHBU-RULNZOCKSA-N

> <FORMULA>
C23H23NO10

> <MOLECULAR_WEIGHT>
473.434

> <EXACT_MASS>
473.132195945

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
46.49059120582086

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-({1-[(2R)-10-acetyl-11,13-dihydroxy-2,12-dimethyl-3,5-dioxo-8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(9),6,10,12-tetraen-4-ylidene]ethyl}amino)pentanedioic acid

> <JCHEM_LOGP>
1.747467883666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.0147944449828135

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.179955420680343

> <JCHEM_PKA_STRONGEST_BASIC>
-5.379828797101173

> <JCHEM_POLAR_SURFACE_AREA>
187.52999999999997

> <JCHEM_REFRACTIVITY>
118.68009999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-({1-[(2R)-10-acetyl-11,13-dihydroxy-2,12-dimethyl-3,5-dioxo-8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(9),6,10,12-tetraen-4-ylidene]ethyl}amino)pentanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      13.959  22.247   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.120  20.715   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      15.526  20.089   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      12.874  19.810   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.467  20.436   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      11.306  21.968   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.221  19.531   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.814  20.157   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.382  17.999   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.136  17.094   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      11.789  17.373   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.035  18.278   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      14.281  17.373   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      13.805  15.908   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.575  14.575   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.805  13.241   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      14.575  11.907   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      12.265  13.241   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.495  11.907   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.265  10.574   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       9.955  11.907   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       9.185  10.574   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.645  10.574   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.875   9.240   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.565   7.906   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       4.565  10.574   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       9.955   9.240   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      11.495   9.240   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       9.185   7.906   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      11.495  14.575   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.955  14.575   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      12.265  15.908   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.733  16.069   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   12                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   33                                                  
CONECT   12   11    4   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   33                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   31                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   22   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   18   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   14   11   34                                             
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₃NO₁₀

Average Mass

473.4340 Da

Monoisotopic Mass

473.13220 Da

IUPAC Name

(2S)-2-({1-[(2R)-10-acetyl-11,13-dihydroxy-2,12-dimethyl-3,5-dioxo-8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(9),6,10,12-tetraen-4-ylidene]ethyl}amino)pentanedioic acid

Traditional Name

(2S)-2-({1-[(2R)-10-acetyl-11,13-dihydroxy-2,12-dimethyl-3,5-dioxo-8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(9),6,10,12-tetraen-4-ylidene]ethyl}amino)pentanedioic acid

CAS Registry Number

Not Available

SMILES

CC(=O)C1=C(O)C(C)=C(O)C2=C1OC1=CC(=O)C(=C(C)N[C@@H](CCC(O)=O)C(O)=O)C(=O)[C@]21C

InChI Identifier

InChI=1S/C23H23NO10/c1-8-18(29)16(10(3)25)20-17(19(8)30)23(4)13(34-20)7-12(26)15(21(23)31)9(2)24-11(22(32)33)5-6-14(27)28/h7,11,24,29-30H,5-6H2,1-4H3,(H,27,28)(H,32,33)/t11-,23-/m0/s1

InChI Key

YAJFSGDAEAKHBU-RULNZOCKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Stereocaulon alpinum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamic acid and derivatives

Alternative Parents

Substituents

Glutamic acid or derivatives
Alpha-amino acid
L-alpha-amino acid
Acetophenone
Coumaran
Quinomethane
O-quinomethane
Aryl ketone
Aryl alkyl ketone
Hydroxy fatty acid
Phenol
Amino fatty acid
Cyclohexenone
Fatty acyl
Benzenoid
Dicarboxylic acid or derivatives
Vinylogous ester
Vinylogous amide
Vinylogous acid
Ketone
Cyclic ketone
Amino acid
Carboxylic acid
Secondary aliphatic amine
Enamine
Oxacycle
Organoheterocyclic compound
Secondary amine
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Amine
Organic oxide
Carbonyl group
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	1.75	ChemAxon
pKa (Strongest Acidic)	3.18	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	187.53 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	118.68 m³·mol⁻¹	ChemAxon
Polarizability	46.49 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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

C00047302

Chemspider ID

34890615

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101865653

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Paudel B, Bhattarai HD, Lee HK, Oh H, Shin HW, Yim JH: Antibacterial activities of Ramalin, usnic acid and its three derivatives isolated from the Antarctic lichen Ramalina terebrata. Z Naturforsch C J Biosci. 2010 Jan-Feb;65(1-2):34-8. doi: 10.1515/znc-2010-1-206. [PubMed:20355318 ]
LOTUS database [Link]

Showing NP-Card for (2s)-2-({1-[(2r)-10-acetyl-11,13-dihydroxy-2,12-dimethyl-3,5-dioxo-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),6,10,12-tetraen-4-ylidene]ethyl}amino)pentanedioic acid (NP0214657)

MOL for NP0214657 ((2s)-2-({1-[(2r)-10-acetyl-11,13-dihydroxy-2,12-dimethyl-3,5-dioxo-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),6,10,12-tetraen-4-ylidene]ethyl}amino)pentanedioic acid)

3D MOL for NP0214657 ((2s)-2-({1-[(2r)-10-acetyl-11,13-dihydroxy-2,12-dimethyl-3,5-dioxo-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),6,10,12-tetraen-4-ylidene]ethyl}amino)pentanedioic acid)

3D SDF for NP0214657 ((2s)-2-({1-[(2r)-10-acetyl-11,13-dihydroxy-2,12-dimethyl-3,5-dioxo-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),6,10,12-tetraen-4-ylidene]ethyl}amino)pentanedioic acid)

3D-SDF for NP0214657 ((2s)-2-({1-[(2r)-10-acetyl-11,13-dihydroxy-2,12-dimethyl-3,5-dioxo-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),6,10,12-tetraen-4-ylidene]ethyl}amino)pentanedioic acid)

PDB for NP0214657 ((2s)-2-({1-[(2r)-10-acetyl-11,13-dihydroxy-2,12-dimethyl-3,5-dioxo-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),6,10,12-tetraen-4-ylidene]ethyl}amino)pentanedioic acid)

3D PDB for NP0214657 ((2s)-2-({1-[(2r)-10-acetyl-11,13-dihydroxy-2,12-dimethyl-3,5-dioxo-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),6,10,12-tetraen-4-ylidene]ethyl}amino)pentanedioic acid)

SMILES for NP0214657 ((2s)-2-({1-[(2r)-10-acetyl-11,13-dihydroxy-2,12-dimethyl-3,5-dioxo-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),6,10,12-tetraen-4-ylidene]ethyl}amino)pentanedioic acid)

INCHI for NP0214657 ((2s)-2-({1-[(2r)-10-acetyl-11,13-dihydroxy-2,12-dimethyl-3,5-dioxo-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),6,10,12-tetraen-4-ylidene]ethyl}amino)pentanedioic acid)

Structure for NP0214657 ((2s)-2-({1-[(2r)-10-acetyl-11,13-dihydroxy-2,12-dimethyl-3,5-dioxo-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),6,10,12-tetraen-4-ylidene]ethyl}amino)pentanedioic acid)

3D Structure for NP0214657 ((2s)-2-({1-[(2r)-10-acetyl-11,13-dihydroxy-2,12-dimethyl-3,5-dioxo-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),6,10,12-tetraen-4-ylidene]ethyl}amino)pentanedioic acid)