NP-MRD: Showing NP-Card for methyl 4-[(1-{10-acetyl-11,13-dihydroxy-2,12-dimethyl-3,5-dioxo-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(13),6,9,11-tetraen-4-ylidene}ethyl)amino]butanoate (NP0153425)

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Record Information

Version

1.0

Created at

2022-09-02 10:04:44 UTC

Updated at

2022-09-02 10:04:44 UTC

NP-MRD ID

NP0153425

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Methyl 4-[(1-{10-acetyl-11,13-dihydroxy-2,12-dimethyl-3,5-dioxo-8-oxatricyclo[7.4.0.0²,⁷]Trideca-1(13),6,9,11-tetraen-4-ylidene}ethyl)amino]butanoate belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom. methyl 4-[(1-{10-acetyl-11,13-dihydroxy-2,12-dimethyl-3,5-dioxo-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(13),6,9,11-tetraen-4-ylidene}ethyl)amino]butanoate is found in Usnea longissima. Based on a literature review very few articles have been published on methyl 4-[(1-{10-acetyl-11,13-dihydroxy-2,12-dimethyl-3,5-dioxo-8-oxatricyclo[7.4.0.0²,⁷]Trideca-1(13),6,9,11-tetraen-4-ylidene}ethyl)amino]butanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022212042D          

 32 34  0  0  0  0            999 V2000
    5.3866    1.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1011    1.7990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8156    1.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8156    0.5615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5300    1.7990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2445    1.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9590    1.7990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6734    1.3865    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3879    1.7990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3879    2.6240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1024    1.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8169    1.7990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8169    2.6240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5313    1.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5313    0.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1444    0.0095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8089   -0.7442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1444   -1.4979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9649   -1.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4498   -0.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3005   -2.3378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6595   -2.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9951   -2.9190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8390   -2.0791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3541   -2.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5035   -1.3254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6830   -1.2392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9884   -0.6580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8169    0.1490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1494   -0.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1024    0.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3879    0.1490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  4  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 17 28  1  0  0  0  0
 28 29  1  0  0  0  0
 15 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 11 31  1  0  0  0  0
 31 32  2  0  0  0  0
M  END

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
    9.2547   -0.7719   -0.8644 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9152   -0.5078   -0.5065 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8935   -0.6437   -1.4133 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2046   -1.0153   -2.5818 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4682   -0.3695   -1.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4414    0.0473    0.3952 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0685    0.3601    0.9045 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1392   -0.7238    0.8299 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8229   -0.5108    1.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6198   -0.4831    2.7701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8413   -0.3461    0.4570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0751   -0.3772   -0.9752 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2475   -0.5862   -1.4012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0452   -0.1671   -1.8891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2654    0.0918   -1.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4689    0.2871   -2.0539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5112    0.1928   -1.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9039    0.2645   -1.3347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3429    0.5124   -2.6912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7416    0.6129   -3.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4650    0.6548   -3.6054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7274    0.0908   -0.2446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0644    0.1387   -0.3503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1528   -0.1457    1.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1250   -0.3320    2.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8120   -0.2035    1.2243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2885   -0.4327    2.4632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9698   -0.0250    0.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5436    0.2613   -0.0019 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5558    1.8739    0.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5494   -0.1222    0.9240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7813   -0.2868    2.1428 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4491   -1.8404   -0.6864 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4639   -0.5348   -1.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9654   -0.1858   -0.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8922   -1.3030   -1.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1282    0.4823   -1.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9970   -0.6560    1.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0230    1.0099    0.4455 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7129    1.2621    0.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1913    0.7368    1.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4383   -1.6394    0.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1816    0.5107    3.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5817   -0.5356    3.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0208   -1.3327    3.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1798   -0.2348   -2.9464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3409   -0.3133   -2.9863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3026    1.4693   -2.6769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7902    0.8008   -4.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8243    0.2451   -0.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1123   -0.5766    1.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1660    0.6124    2.7575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7857   -1.1553    2.8395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8906   -0.5625    3.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3549    2.2531   -0.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5396    2.2061    0.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7959    1.9441    1.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 18 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 29 30  1  6
 29 31  1  0
 31 32  2  0
 31 11  1  0
 29 15  1  0
 28 17  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
 10 43  1  0
 10 44  1  0
 10 45  1  0
 14 46  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
 23 50  1  0
 25 51  1  0
 25 52  1  0
 25 53  1  0
 27 54  1  0
 30 55  1  0
 30 56  1  0
 30 57  1  0
M  END


  Mrv1652309022212042D          

 32 34  0  0  0  0            999 V2000
    5.3866    1.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1011    1.7990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8156    1.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8156    0.5615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5300    1.7990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2445    1.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9590    1.7990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6734    1.3865    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3879    1.7990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3879    2.6240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1024    1.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8169    1.7990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8169    2.6240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5313    1.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5313    0.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1444    0.0095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8089   -0.7442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1444   -1.4979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9649   -1.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4498   -0.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3005   -2.3378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6595   -2.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9951   -2.9190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8390   -2.0791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3541   -2.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5035   -1.3254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6830   -1.2392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9884   -0.6580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8169    0.1490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1494   -0.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1024    0.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3879    0.1490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  4  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 17 28  1  0  0  0  0
 28 29  1  0  0  0  0
 15 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 11 31  1  0  0  0  0
 31 32  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0153425

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CCCNC(C)=C1C(=O)C=C2OC3=C(C(C)=O)C(O)=C(C)C(O)=C3C2(C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H25NO8/c1-10-19(28)17(12(3)25)21-18(20(10)29)23(4)14(32-21)9-13(26)16(22(23)30)11(2)24-8-6-7-15(27)31-5/h9,24,28-29H,6-8H2,1-5H3

> <INCHI_KEY>
CJVLALQQMVPNHI-UHFFFAOYSA-N

> <FORMULA>
C23H25NO8

> <MOLECULAR_WEIGHT>
443.452

> <EXACT_MASS>
443.158016769

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
46.36526275547253

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.50

> <JCHEM_LOGP>
2.2034223436666664

> <ALOGPS_LOGS>
-4.40

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.271734249376486

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.12563821012325

> <JCHEM_PKA_STRONGEST_BASIC>
-5.360720523169072

> <JCHEM_POLAR_SURFACE_AREA>
139.23

> <JCHEM_REFRACTIVITY>
117.61929999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.75e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      10.055   2.588   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      11.389   3.358   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      12.722   2.588   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      12.722   1.048   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      14.056   3.358   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.390   2.588   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.723   3.358   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      18.057   2.588   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      19.391   3.358   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.391   4.898   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      20.724   2.588   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.058   3.358   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      22.058   4.898   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      23.392   2.588   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      23.392   1.048   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      24.536   0.018   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      23.910  -1.389   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      24.536  -2.796   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      26.068  -2.957   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      26.973  -1.711   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      26.694  -4.364   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      23.631  -4.042   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      24.257  -5.449   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      22.099  -3.881   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      21.194  -5.127   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      21.473  -2.474   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      19.942  -2.313   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      22.378  -1.228   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      22.058   0.278   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      20.812  -0.627   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      20.724   1.048   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      19.391   0.278   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   31                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   29                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   28                                                  
CONECT   18   17   19   22                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   18   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   17   29                                                  
CONECT   29   28   15   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   11   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Value	Source
Methyl 4-[(1-{10-acetyl-11,13-dihydroxy-2,12-dimethyl-3,5-dioxo-8-oxatricyclo[7.4.0.0,]trideca-1(13),6,9,11-tetraen-4-ylidene}ethyl)amino]butanoic acid	Generator

Chemical Formula

C₂₃H₂₅NO₈

Average Mass

443.4520 Da

Monoisotopic Mass

443.15802 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC(=O)CCCNC(C)=C1C(=O)C=C2OC3=C(C(C)=O)C(O)=C(C)C(O)=C3C2(C)C1=O

InChI Identifier

InChI=1S/C23H25NO8/c1-10-19(28)17(12(3)25)21-18(20(10)29)23(4)14(32-21)9-13(26)16(22(23)30)11(2)24-8-6-7-15(27)31-5/h9,24,28-29H,6-8H2,1-5H3

InChI Key

CJVLALQQMVPNHI-UHFFFAOYSA-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
Usnea longissima	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Gamma amino acids and derivatives

Alternative Parents

Substituents

Gamma amino acid or derivatives
Coumaran
Acetophenone
Aryl alkyl ketone
Aryl ketone
Quinomethane
O-quinomethane
Cyclohexenone
Fatty acid methyl ester
Fatty acid ester
Fatty acyl
Benzenoid
Vinylogous ester
Vinylogous amide
Vinylogous acid
Methyl ester
Cyclic ketone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Secondary amine
Monocarboxylic acid or derivatives
Enamine
Secondary aliphatic amine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
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	2.5	ALOGPS
logP	2.2	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	7.13	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	139.23 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	117.62 m³·mol⁻¹	ChemAxon
Polarizability	46.37 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

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

162816087

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 4-[(1-{10-acetyl-11,13-dihydroxy-2,12-dimethyl-3,5-dioxo-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(13),6,9,11-tetraen-4-ylidene}ethyl)amino]butanoate (NP0153425)

MOL for NP0153425 (methyl 4-[(1-{10-acetyl-11,13-dihydroxy-2,12-dimethyl-3,5-dioxo-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(13),6,9,11-tetraen-4-ylidene}ethyl)amino]butanoate)

3D MOL for NP0153425 (methyl 4-[(1-{10-acetyl-11,13-dihydroxy-2,12-dimethyl-3,5-dioxo-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(13),6,9,11-tetraen-4-ylidene}ethyl)amino]butanoate)

3D SDF for NP0153425 (methyl 4-[(1-{10-acetyl-11,13-dihydroxy-2,12-dimethyl-3,5-dioxo-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(13),6,9,11-tetraen-4-ylidene}ethyl)amino]butanoate)

3D-SDF for NP0153425 (methyl 4-[(1-{10-acetyl-11,13-dihydroxy-2,12-dimethyl-3,5-dioxo-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(13),6,9,11-tetraen-4-ylidene}ethyl)amino]butanoate)

PDB for NP0153425 (methyl 4-[(1-{10-acetyl-11,13-dihydroxy-2,12-dimethyl-3,5-dioxo-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(13),6,9,11-tetraen-4-ylidene}ethyl)amino]butanoate)

3D PDB for NP0153425 (methyl 4-[(1-{10-acetyl-11,13-dihydroxy-2,12-dimethyl-3,5-dioxo-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(13),6,9,11-tetraen-4-ylidene}ethyl)amino]butanoate)

SMILES for NP0153425 (methyl 4-[(1-{10-acetyl-11,13-dihydroxy-2,12-dimethyl-3,5-dioxo-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(13),6,9,11-tetraen-4-ylidene}ethyl)amino]butanoate)

INCHI for NP0153425 (methyl 4-[(1-{10-acetyl-11,13-dihydroxy-2,12-dimethyl-3,5-dioxo-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(13),6,9,11-tetraen-4-ylidene}ethyl)amino]butanoate)

Structure for NP0153425 (methyl 4-[(1-{10-acetyl-11,13-dihydroxy-2,12-dimethyl-3,5-dioxo-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(13),6,9,11-tetraen-4-ylidene}ethyl)amino]butanoate)

3D Structure for NP0153425 (methyl 4-[(1-{10-acetyl-11,13-dihydroxy-2,12-dimethyl-3,5-dioxo-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(13),6,9,11-tetraen-4-ylidene}ethyl)amino]butanoate)