NP-MRD: Showing NP-Card for 12-(3,4-dihydroxyphenyl)-7,8,16,17-tetrahydroxy-4-oxa-1-azapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-5,7,9,12,14,16,18,20-octaen-3-one (NP0221257)

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Record Information

Version

2.0

Created at

2022-09-05 22:46:48 UTC

Updated at

2022-09-05 22:46:48 UTC

NP-MRD ID

NP0221257

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-(3,4-dihydroxyphenyl)-7,8,16,17-tetrahydroxy-4-oxa-1-azapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-5,7,9,12,14,16,18,20-octaen-3-one

Description

Lamellarin H belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids. 12-(3,4-dihydroxyphenyl)-7,8,16,17-tetrahydroxy-4-oxa-1-azapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-5,7,9,12,14,16,18,20-octaen-3-one was first documented in 2016 (PMID: 26741300). Based on a literature review a small amount of articles have been published on Lamellarin H (PMID: 31782470) (PMID: 31433662) (PMID: 28665125) (PMID: 28421766).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062200462D          

 34 39  0  0  0  0            999 V2000
    1.3376   -6.5759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0827   -5.7913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2757   -5.6198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0208   -4.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7862   -4.6637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0412   -3.8790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8481   -3.7075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4891   -3.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7441   -2.4813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3179   -3.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5728   -4.2221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3798   -4.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0472   -3.9087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0472   -3.0837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3327   -2.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3327   -1.8462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0472   -1.4337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0472   -0.6087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7617   -1.8462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4761   -1.4337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7617   -2.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7146   -4.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5216   -4.2221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7766   -3.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5835   -3.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8385   -2.4813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1356   -3.8790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9425   -3.7075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8806   -4.6637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0736   -4.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8187   -5.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0117   -5.7913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4597   -5.1782    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6347   -5.1782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  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  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 14 21  1  0  0  0  0
 13 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 23 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
 22 33  1  0  0  0  0
 33 34  1  0  0  0  0
  2 34  1  0  0  0  0
 12 34  1  0  0  0  0
M  END

     RDKit          3D

 51 56  0  0  0  0  0  0  0  0999 V2000
    0.5700   -1.3447   -3.9126 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3571   -1.2691   -2.9169 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4632   -0.4460   -2.9128 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0658   -0.0639   -1.7274 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1857    0.7674   -1.7814 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8221    1.1695   -0.6018 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9379    2.0022   -0.7098 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3191    0.7267    0.5971 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9291    1.1082    1.7731 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1938   -0.1071    0.6277 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5634   -0.5038   -0.5250 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3715   -1.3461   -0.4686 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1168   -0.5827   -0.1676 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0657    0.5649    0.7377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1491    1.8472    0.1965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1841    2.9788    0.9592 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0011    2.8763    2.3461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0436    4.0671    3.0818 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2113    1.6411    2.8942 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3970    1.5292    4.2589 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2400    0.5052    2.0883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8795   -1.2072   -0.7399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3537   -1.0795   -0.5631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9228   -0.1286    0.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3010   -0.0933    0.3599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8970    0.8656    1.1627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1072   -0.9926   -0.2964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4864   -1.0137   -0.2166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5201   -1.9560   -1.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1415   -2.0056   -1.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5814   -3.0600   -2.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2733   -3.1657   -2.2329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3905   -2.2641   -1.5850 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0713   -2.1109   -1.6886 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6024    1.1317   -2.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3910    2.2903    0.1388 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7136    1.6790    1.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8362   -0.4508    1.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4324   -2.0995    0.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2959    1.9236   -0.8838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3478    3.9688    0.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0916    4.0238    4.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3974    2.2685    4.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4098   -0.4393    2.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3499    0.5600    0.7747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8700    0.9931    1.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9558   -0.3363    0.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1482   -2.6561   -1.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2753   -3.7398   -2.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8614   -3.9537   -2.8629 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5788   -3.0719   -1.8182 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 14  2  0
 14 21  1  0
 21 19  2  0
 19 20  1  0
 14 13  1  0
 13 22  2  0
 22 33  1  0
 33 32  1  0
 32 31  2  0
 31 30  1  0
 30 29  2  0
 29 27  1  0
 27 28  1  0
 27 25  2  0
 25 26  1  0
 25 24  1  0
 24 23  2  0
 33 34  1  0
 34 12  1  0
 12 11  1  0
 11 10  2  0
 10  8  1  0
  8  9  1  0
  8  6  2  0
  6  7  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
 19 17  1  0
 12 13  1  0
  4 11  1  0
 23 22  1  0
  2 34  1  0
 23 30  1  0
 18 42  1  0
 16 41  1  0
 15 40  1  0
 21 44  1  0
 20 43  1  0
 32 50  1  0
 31 49  1  0
 29 48  1  0
 28 47  1  0
 26 46  1  0
 24 45  1  0
 34 51  1  6
 12 39  1  1
 10 38  1  0
  9 37  1  0
  7 36  1  0
  5 35  1  0
M  END


  Mrv1652309062200462D          

 34 39  0  0  0  0            999 V2000
    1.3376   -6.5759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0827   -5.7913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2757   -5.6198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0208   -4.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7862   -4.6637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0412   -3.8790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8481   -3.7075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4891   -3.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7441   -2.4813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3179   -3.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5728   -4.2221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3798   -4.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0472   -3.9087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0472   -3.0837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3327   -2.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3327   -1.8462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0472   -1.4337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0472   -0.6087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7617   -1.8462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4761   -1.4337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7617   -2.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7146   -4.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5216   -4.2221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7766   -3.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5835   -3.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8385   -2.4813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1356   -3.8790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9425   -3.7075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8806   -4.6637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0736   -4.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8187   -5.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0117   -5.7913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4597   -5.1782    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6347   -5.1782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  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  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 14 21  1  0  0  0  0
 13 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 23 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
 22 33  1  0  0  0  0
 33 34  1  0  0  0  0
  2 34  1  0  0  0  0
 12 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0221257

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1O)C1=C2N(C=CC3=CC(O)=C(O)C=C23)C2C1C1=CC(O)=C(O)C=C1OC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H17NO8/c27-14-2-1-11(6-15(14)28)21-22-13-8-18(31)19(32)9-20(13)34-25(33)24(22)26-4-3-10-5-16(29)17(30)7-12(10)23(21)26/h1-9,22,24,27-32H

> <INCHI_KEY>
KIRMMCLRVYLQSV-UHFFFAOYSA-N

> <FORMULA>
C25H17NO8

> <MOLECULAR_WEIGHT>
459.41

> <EXACT_MASS>
459.095416511

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
44.86681893592795

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
12-(3,4-dihydroxyphenyl)-7,8,16,17-tetrahydroxy-4-oxa-1-azapentacyclo[11.8.0.0^{2,11}.0^{5,10}.0^{14,19}]henicosa-5,7,9,12,14,16,18,20-octaen-3-one

> <JCHEM_LOGP>
2.8963477993333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.06085485978002

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.56950920847283

> <JCHEM_PKA_STRONGEST_BASIC>
2.4639540663582804

> <JCHEM_POLAR_SURFACE_AREA>
150.92000000000002

> <JCHEM_REFRACTIVITY>
121.85559999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
12-(3,4-dihydroxyphenyl)-7,8,16,17-tetrahydroxy-4-oxa-1-azapentacyclo[11.8.0.0^{2,11}.0^{5,10}.0^{14,19}]henicosa-5,7,9,12,14,16,18,20-octaen-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  O   UNK     0       2.497 -12.275   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.021 -10.810   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.515 -10.490   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.039  -9.026   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.468  -8.705   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.943  -7.241   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.450  -6.921   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.913  -6.096   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.389  -4.632   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.593  -6.417   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.069  -7.881   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.576  -8.201   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.821  -7.296   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.821  -5.756   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.488  -4.986   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.488  -3.446   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.821  -2.676   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.821  -1.136   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.155  -3.446   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.489  -2.676   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.155  -4.986   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.067  -8.201   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.574  -7.881   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.050  -6.417   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.556  -6.096   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.032  -4.632   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       9.586  -7.241   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      11.093  -6.921   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       9.110  -8.705   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.604  -9.026   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.128 -10.490   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.622 -10.810   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0       4.591  -9.666   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0       3.051  -9.666   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   34                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    4   12                                                  
CONECT   12   11   13   34                                                  
CONECT   13   12   14   22                                                  
CONECT   14   13   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   14                                                       
CONECT   22   13   23   33                                                  
CONECT   23   22   24   30                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   23   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   22   34                                                  
CONECT   34   33    2   12                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₁₇NO₈

Average Mass

459.4100 Da

Monoisotopic Mass

459.09542 Da

IUPAC Name

12-(3,4-dihydroxyphenyl)-7,8,16,17-tetrahydroxy-4-oxa-1-azapentacyclo[11.8.0.0^{2,11}.0^{5,10}.0^{14,19}]henicosa-5,7,9,12,14,16,18,20-octaen-3-one

Traditional Name

12-(3,4-dihydroxyphenyl)-7,8,16,17-tetrahydroxy-4-oxa-1-azapentacyclo[11.8.0.0^{2,11}.0^{5,10}.0^{14,19}]henicosa-5,7,9,12,14,16,18,20-octaen-3-one

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1O)C1=C2N(C=CC3=CC(O)=C(O)C=C23)C2C1C1=CC(O)=C(O)C=C1OC2=O

InChI Identifier

InChI=1S/C25H17NO8/c27-14-2-1-11(6-15(14)28)21-22-13-8-18(31)19(32)9-20(13)34-25(33)24(22)26-4-3-10-5-16(29)17(30)7-12(10)23(21)26/h1-9,22,24,27-32H

InChI Key

KIRMMCLRVYLQSV-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid esters

Alternative Parents

Substituents

Alpha-amino acid ester
3,4-dihydrocoumarin
3-phenylpyrroline
Chromane
Benzopyran
1-benzopyran
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Pyrrole
Pyrroline
Carboxylic acid ester
Lactone
Tertiary aliphatic amine
Tertiary amine
Azacycle
Monocarboxylic acid or derivatives
Enamine
Oxacycle
Organoheterocyclic compound
Polyol
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
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	2.9	ChemAxon
pKa (Strongest Acidic)	8.57	ChemAxon
pKa (Strongest Basic)	2.46	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	150.92 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	121.86 m³·mol⁻¹	ChemAxon
Polarizability	44.87 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

405517

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

460908

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Watanabe T, Mutoh Y, Saito S: Synthesis of lactone-fused pyrroles by ruthenium-catalyzed 1,2-carbon migration-cycloisomerization. Org Biomol Chem. 2019 Dec 18;18(1):81-85. doi: 10.1039/c9ob02363a. [PubMed:31782470 ]
Kumar V, Awasthi A, Salam A, Khan T: Scalable Total Syntheses of Some Natural and Unnatural Lamellarins: Application of a One-Pot Domino Process for Regioselective Access to the Central 1,2,4-Trisubstituted Pyrrole Core. J Org Chem. 2019 Sep 20;84(18):11596-11603. doi: 10.1021/acs.joc.9b01521. Epub 2019 Sep 4. [PubMed:31433662 ]
B Manjappa K, Lin JM, Yang DY: Construction of Pentacyclic Lamellarin Skeleton via Grob Reaction: Application to Total Synthesis of Lamellarins H and D. J Org Chem. 2017 Jul 21;82(14):7648-7656. doi: 10.1021/acs.joc.7b01061. Epub 2017 Jun 30. [PubMed:28665125 ]
Lade DM, Pawar AB, Mainkar PS, Chandrasekhar S: Total Synthesis of Lamellarin D Trimethyl Ether, Lamellarin D, and Lamellarin H. J Org Chem. 2017 May 5;82(9):4998-5004. doi: 10.1021/acs.joc.7b00636. Epub 2017 Apr 24. [PubMed:28421766 ]
Manjappa KB, Syu JR, Yang DY: Visible-Light-Promoted and Yb(OTf)3-Catalyzed Constructions of Coumarin-Pyrrole-(Iso)quinoline-Fused Pentacycles: Synthesis of Lamellarin Core, Lamellarin D Trimethyl Ether, and Lamellarin H. Org Lett. 2016 Jan 15;18(2):332-5. doi: 10.1021/acs.orglett.5b03524. Epub 2016 Jan 7. [PubMed:26741300 ]
LOTUS database [Link]

Showing NP-Card for 12-(3,4-dihydroxyphenyl)-7,8,16,17-tetrahydroxy-4-oxa-1-azapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-5,7,9,12,14,16,18,20-octaen-3-one (NP0221257)

MOL for NP0221257 (12-(3,4-dihydroxyphenyl)-7,8,16,17-tetrahydroxy-4-oxa-1-azapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-5,7,9,12,14,16,18,20-octaen-3-one)

3D MOL for NP0221257 (12-(3,4-dihydroxyphenyl)-7,8,16,17-tetrahydroxy-4-oxa-1-azapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-5,7,9,12,14,16,18,20-octaen-3-one)

3D SDF for NP0221257 (12-(3,4-dihydroxyphenyl)-7,8,16,17-tetrahydroxy-4-oxa-1-azapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-5,7,9,12,14,16,18,20-octaen-3-one)

3D-SDF for NP0221257 (12-(3,4-dihydroxyphenyl)-7,8,16,17-tetrahydroxy-4-oxa-1-azapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-5,7,9,12,14,16,18,20-octaen-3-one)

PDB for NP0221257 (12-(3,4-dihydroxyphenyl)-7,8,16,17-tetrahydroxy-4-oxa-1-azapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-5,7,9,12,14,16,18,20-octaen-3-one)

3D PDB for NP0221257 (12-(3,4-dihydroxyphenyl)-7,8,16,17-tetrahydroxy-4-oxa-1-azapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-5,7,9,12,14,16,18,20-octaen-3-one)

SMILES for NP0221257 (12-(3,4-dihydroxyphenyl)-7,8,16,17-tetrahydroxy-4-oxa-1-azapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-5,7,9,12,14,16,18,20-octaen-3-one)

INCHI for NP0221257 (12-(3,4-dihydroxyphenyl)-7,8,16,17-tetrahydroxy-4-oxa-1-azapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-5,7,9,12,14,16,18,20-octaen-3-one)

Structure for NP0221257 (12-(3,4-dihydroxyphenyl)-7,8,16,17-tetrahydroxy-4-oxa-1-azapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-5,7,9,12,14,16,18,20-octaen-3-one)

3D Structure for NP0221257 (12-(3,4-dihydroxyphenyl)-7,8,16,17-tetrahydroxy-4-oxa-1-azapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-5,7,9,12,14,16,18,20-octaen-3-one)