NP-MRD: Showing NP-Card for 12-(3,4-dihydroxyphenyl)-7,8,17-trihydroxy-16-methoxy-4-oxa-1-azapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-2(11),5(10),6,8,12,14(19),15,17,20-nonaen-3-one (NP0247411)

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Record Information

Version

2.0

Created at

2022-09-07 09:15:36 UTC

Updated at

2022-09-07 09:15:36 UTC

NP-MRD ID

NP0247411

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-(3,4-dihydroxyphenyl)-7,8,17-trihydroxy-16-methoxy-4-oxa-1-azapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-2(11),5(10),6,8,12,14(19),15,17,20-nonaen-3-one

Description

Lamellarin S belongs to the class of organic compounds known as 6,7-dihydroxycoumarins. These are coumarins bearing two hydroxyl groups at positions 6 and 7 of the coumarin skeleton, respectively. Based on a literature review very few articles have been published on Lamellarin S.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072211152D          

 35 40  0  0  0  0            999 V2000
    6.5941   -1.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7871   -1.1567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5322   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7252   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4703    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0223    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7674    1.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    2.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084    1.5402    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6633    0.7556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9959    0.2706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9959   -0.5544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7103   -0.9669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7103   -1.7919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9959   -2.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9959   -3.0294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2814   -1.7919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5669   -2.2044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2814   -0.9669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3284    0.7556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2046   -1.1567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8995    0.0694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2243    1.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0313    2.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2863    2.9379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5834    1.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8293    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0842    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8912    0.0694    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  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
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  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
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 12 19  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 20 32  2  0  0  0  0
  9 32  1  0  0  0  0
  6 33  2  0  0  0  0
 33 34  1  0  0  0  0
  3 34  2  0  0  0  0
 34 35  1  0  0  0  0
M  END

     RDKit          3D

 52 57  0  0  0  0  0  0  0  0999 V2000
    3.7794    2.6185    0.7936 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5710    1.7383    0.0027 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9820    0.6057   -0.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6419    0.3242   -0.4248 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1243   -0.8010   -1.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9322   -1.6318   -1.7943 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4185   -2.7610   -2.4029 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0910   -3.0310   -2.2296 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2807   -2.2446   -1.4968 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7930   -1.1502   -0.9110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2866   -0.5601   -0.2364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2171    0.6651    0.5606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0532    0.5817    1.9038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1087    1.7369    2.6465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1068    2.9564    2.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0502    4.1403    2.7949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3771    3.0302    0.6884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5902    4.2619    0.0932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4322    1.8765   -0.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4297   -1.3126   -0.4298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7633   -1.2080   -0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1619   -0.1604    0.7866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5097   -0.1277    1.1644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8925    0.9414    1.9695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4091   -1.0962    0.7645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7386   -1.0071    1.1745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9538   -2.1243   -0.0328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6322   -2.1961   -0.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2322   -3.1975   -1.1949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9928   -3.2837   -1.5796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6434   -4.2596   -2.3151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0355   -2.3614   -1.2252 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2704   -1.3196   -1.9399 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7992   -0.2055   -1.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1478    0.1028   -1.4935 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1326    3.2688    0.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1787    2.0152    1.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4443    3.2471    1.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0734    0.9903    0.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0912   -3.3750   -2.9858 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6534   -3.9191   -2.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2287   -0.3986    2.4059 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3164    1.7298    3.7011 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1475    4.0828    3.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7901    4.3614   -0.8852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6520    1.9363   -1.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5007    0.5971    1.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2578    1.6405    2.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3620   -1.7268    0.8654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6413   -2.9135   -0.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8752   -1.9959   -2.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5242    0.9190   -1.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 34  2  0
 34 35  1  0
 34 33  1  0
 33  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 32  1  0
 32 20  2  0
 20 11  1  0
 11 10  2  0
 10  5  1  0
  5  4  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
  4  3  1  0
 19 12  1  0
 28 21  1  0
  5  6  1  0
 10  9  1  0
 30 32  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
 35 52  1  0
 33 51  1  0
  7 40  1  0
  8 41  1  0
  4 39  1  0
 13 42  1  0
 14 43  1  0
 16 44  1  0
 18 45  1  0
 19 46  1  0
 22 47  1  0
 24 48  1  0
 26 49  1  0
 27 50  1  0
M  END


  Mrv1652309072211152D          

 35 40  0  0  0  0            999 V2000
    6.5941   -1.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7871   -1.1567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5322   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7252   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4703    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0223    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7674    1.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    2.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084    1.5402    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6633    0.7556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9959    0.2706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9959   -0.5544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7103   -0.9669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7103   -1.7919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9959   -2.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9959   -3.0294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2814   -1.7919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5669   -2.2044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2814   -0.9669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3284    0.7556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2046   -1.1567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8995    0.0694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2243    1.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0313    2.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2863    2.9379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5834    1.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8293    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0842    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8912    0.0694    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  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
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  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
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 12 19  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 20 32  2  0  0  0  0
  9 32  1  0  0  0  0
  6 33  2  0  0  0  0
 33 34  1  0  0  0  0
  3 34  2  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0247411

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C2C=CN3C4=C(C(=C3C2=C1)C1=CC=C(O)C(O)=C1)C1=CC(O)=C(O)C=C1OC4=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H17NO8/c1-34-21-9-13-11(6-19(21)32)4-5-27-24(13)22(12-2-3-15(28)16(29)7-12)23-14-8-17(30)18(31)10-20(14)35-26(33)25(23)27/h2-10,28-32H,1H3

> <INCHI_KEY>
OAFHLIVUBAZODD-UHFFFAOYSA-N

> <FORMULA>
C26H17NO8

> <MOLECULAR_WEIGHT>
471.421

> <EXACT_MASS>
471.095416511

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
47.163699196669455

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
3.4430467899999995

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.798236955236685

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.608644831743816

> <JCHEM_PKA_STRONGEST_BASIC>
-4.900794448387824

> <JCHEM_POLAR_SURFACE_AREA>
141.09

> <JCHEM_REFRACTIVITY>
126.85339999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      12.309  -2.479   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.803  -2.159   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      10.327  -0.695   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.820  -0.374   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.344   1.090   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.375   2.235   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.899   3.699   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.393   4.019   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       6.362   2.875   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       6.838   1.410   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.592   0.505   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.592  -1.035   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.926  -1.805   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.926  -3.345   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.592  -4.115   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.592  -5.655   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.259  -3.345   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.925  -4.115   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.259  -1.805   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.346   1.410   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.840   1.090   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.364  -0.374   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.858  -0.695   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.382  -2.159   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.173   0.450   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.679   0.130   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.303   1.914   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.810   2.235   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.285   3.699   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.792   4.019   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.268   5.484   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.822   2.875   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.881   1.914   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.357   0.450   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      12.864   0.130   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7   33                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   32                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10   12   20                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   12                                                       
CONECT   20   11   21   32                                                  
CONECT   21   20   22   28                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   21   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   20    9                                                  
CONECT   33    6   34                                                       
CONECT   34   33    3   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₁₇NO₈

Average Mass

471.4210 Da

Monoisotopic Mass

471.09542 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C2C=CN3C4=C(C(=C3C2=C1)C1=CC=C(O)C(O)=C1)C1=CC(O)=C(O)C=C1OC4=O

InChI Identifier

InChI=1S/C26H17NO8/c1-34-21-9-13-11(6-19(21)32)4-5-27-24(13)22(12-2-3-15(28)16(29)7-12)23-14-8-17(30)18(31)10-20(14)35-26(33)25(23)27/h2-10,28-32H,1H3

InChI Key

OAFHLIVUBAZODD-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 6,7-dihydroxycoumarins. These are coumarins bearing two hydroxyl groups at positions 6 and 7 of the coumarin skeleton, respectively.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Hydroxycoumarins

Direct Parent

6,7-dihydroxycoumarins

Alternative Parents

Substituents

6,7-dihydroxycoumarin
3-phenylpyrrole
Benzopyran
Isoquinoline
1-benzopyran
Indolizine
Pyrrolopyridine
Anisole
Catechol
Phenol ether
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Pyridine
Pyran
Monocyclic benzene moiety
Benzenoid
Substituted pyrrole
Pyrrole
Heteroaromatic compound
Lactone
Polyol
Organoheterocyclic compound
Oxacycle
Azacycle
Ether
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen 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	3.44	ChemAxon
pKa (Strongest Acidic)	7.61	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	141.09 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	126.85 m³·mol⁻¹	ChemAxon
Polarizability	47.16 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

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

102293212

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 12-(3,4-dihydroxyphenyl)-7,8,17-trihydroxy-16-methoxy-4-oxa-1-azapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-2(11),5(10),6,8,12,14(19),15,17,20-nonaen-3-one (NP0247411)

MOL for NP0247411 (12-(3,4-dihydroxyphenyl)-7,8,17-trihydroxy-16-methoxy-4-oxa-1-azapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-2(11),5(10),6,8,12,14(19),15,17,20-nonaen-3-one)

3D MOL for NP0247411 (12-(3,4-dihydroxyphenyl)-7,8,17-trihydroxy-16-methoxy-4-oxa-1-azapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-2(11),5(10),6,8,12,14(19),15,17,20-nonaen-3-one)

3D SDF for NP0247411 (12-(3,4-dihydroxyphenyl)-7,8,17-trihydroxy-16-methoxy-4-oxa-1-azapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-2(11),5(10),6,8,12,14(19),15,17,20-nonaen-3-one)

3D-SDF for NP0247411 (12-(3,4-dihydroxyphenyl)-7,8,17-trihydroxy-16-methoxy-4-oxa-1-azapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-2(11),5(10),6,8,12,14(19),15,17,20-nonaen-3-one)

PDB for NP0247411 (12-(3,4-dihydroxyphenyl)-7,8,17-trihydroxy-16-methoxy-4-oxa-1-azapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-2(11),5(10),6,8,12,14(19),15,17,20-nonaen-3-one)

3D PDB for NP0247411 (12-(3,4-dihydroxyphenyl)-7,8,17-trihydroxy-16-methoxy-4-oxa-1-azapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-2(11),5(10),6,8,12,14(19),15,17,20-nonaen-3-one)

SMILES for NP0247411 (12-(3,4-dihydroxyphenyl)-7,8,17-trihydroxy-16-methoxy-4-oxa-1-azapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-2(11),5(10),6,8,12,14(19),15,17,20-nonaen-3-one)

INCHI for NP0247411 (12-(3,4-dihydroxyphenyl)-7,8,17-trihydroxy-16-methoxy-4-oxa-1-azapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-2(11),5(10),6,8,12,14(19),15,17,20-nonaen-3-one)

Structure for NP0247411 (12-(3,4-dihydroxyphenyl)-7,8,17-trihydroxy-16-methoxy-4-oxa-1-azapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-2(11),5(10),6,8,12,14(19),15,17,20-nonaen-3-one)

3D Structure for NP0247411 (12-(3,4-dihydroxyphenyl)-7,8,17-trihydroxy-16-methoxy-4-oxa-1-azapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-2(11),5(10),6,8,12,14(19),15,17,20-nonaen-3-one)