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-2(11),5(10),6,8,12,14(19),15,17,20-nonaen-3-one (NP0217694)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 18:07:23 UTC

Updated at

2022-09-05 18:07:23 UTC

NP-MRD ID

NP0217694

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-2(11),5(10),6,8,12,14(19),15,17,20-nonaen-3-one

Description

CHEMBL465036 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. CHEMBL465036 is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171506232D          

 34 39  0  0  0  0            999 V2000
    2.9959    3.8544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9959    3.0294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7103    2.6169    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    1.3794    0.0000 C   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
    2.2814    2.6169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5669    3.0294    0.0000 O   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
    3.6633    0.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4703    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7252    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5322    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7871    1.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0842    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8912    0.7556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8293   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0223   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7674   -1.1567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604   -1.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054   -2.1129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084   -0.7152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5834   -0.7152    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0313   -1.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2243   -1.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8995    0.7556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2046    1.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3284    0.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 10 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 26 33  1  0  0  0  0
 33 34  1  0  0  0  0
  9 34  2  0  0  0  0
 23 34  1  0  0  0  0
M  END

     RDKit          3D

 49 54  0  0  0  0  0  0  0  0999 V2000
    0.2088    0.2349   -4.8787 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8647    0.1857   -3.7915 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1716    0.2225   -3.8340 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9120    0.1751   -2.7423 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2807    0.2165   -2.8432 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0584    0.1675   -1.7180 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4653    0.2118   -1.8486 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4470    0.0778   -0.5140 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1458    0.0229    0.6722 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0588    0.0344   -0.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2515    0.0818   -1.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8821    0.0407   -1.4051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0222   -0.0465   -0.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2997   -0.1299    1.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4924   -1.3129    1.7237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7978   -1.3578    3.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9347   -0.1951    3.7774 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2472   -0.2448    5.1336 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7536    1.0059    3.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9007    2.1565    3.8956 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4476    1.0347    1.7946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2912   -0.0450   -0.9436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5642   -0.1124   -0.3852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7409   -0.1976    0.9723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0143   -0.2616    1.4990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1925   -0.3486    2.8840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1333   -0.2402    0.6570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3700   -0.3070    1.2453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9236   -0.1543   -0.6939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6622   -0.0893   -1.2432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4881   -0.0021   -2.6019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2205    0.0610   -3.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1252    0.0422   -2.3023 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1847    0.0953   -2.6003 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7325    0.2881   -3.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0827    0.1796   -1.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1459    0.0487    0.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6075   -0.0385    0.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3877   -2.2314    1.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9388   -2.2996    3.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3769   -1.1341    5.5980 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7807    3.0728    3.4767 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3048    1.9870    1.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9556   -0.2166    1.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1355   -0.3938    3.2369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1893   -0.2944    0.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7883   -0.1380   -1.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3197    0.0168   -3.2741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0256    0.1313   -4.1578 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  2  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 41  1  0
 16 40  1  0
 15 39  1  0
 21 43  1  0
 20 42  1  0
 32 49  1  0
 31 48  1  0
 29 47  1  0
 28 46  1  0
 26 45  1  0
 24 44  1  0
 10 38  1  0
  9 37  1  0
  7 36  1  0
  5 35  1  0
M  END


  Mrv1533004171506232D          

 34 39  0  0  0  0            999 V2000
    2.9959    3.8544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9959    3.0294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7103    2.6169    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    1.3794    0.0000 C   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
    2.2814    2.6169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5669    3.0294    0.0000 O   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
    3.6633    0.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4703    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7252    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5322    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7871    1.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0842    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8912    0.7556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8293   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0223   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7674   -1.1567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604   -1.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054   -2.1129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084   -0.7152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5834   -0.7152    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0313   -1.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2243   -1.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8995    0.7556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2046    1.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3284    0.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 10 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 26 33  1  0  0  0  0
 33 34  1  0  0  0  0
  9 34  2  0  0  0  0
 23 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0217694

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1O)C1=C2N(C=CC3=CC(O)=C(O)C=C23)C2=C1C1=CC(O)=C(O)C=C1OC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H15NO8/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/h1-9,27-32H

> <INCHI_KEY>
BPOUMVNAKKCMPF-UHFFFAOYSA-N

> <FORMULA>
C25H15NO8

> <MOLECULAR_WEIGHT>
457.394

> <EXACT_MASS>
457.079766447

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
45.233505762762064

> <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[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-2(11),5,7,9,12,14,16,18,20-nonaen-3-one

> <ALOGPS_LOGP>
3.85

> <JCHEM_LOGP>
3.2971527339999995

> <ALOGPS_LOGS>
-4.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.480163553519095

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.574433197153682

> <JCHEM_PKA_STRONGEST_BASIC>
-6.272390936435785

> <JCHEM_POLAR_SURFACE_AREA>
152.08999999999997

> <JCHEM_REFRACTIVITY>
122.37109999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.91e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-(3,4-dihydroxyphenyl)-7,8,16,17-tetrahydroxy-4-oxa-1-azapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-2(11),5,7,9,12,14,16,18,20-nonaen-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  O   UNK     0       5.592   7.195   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.592   5.655   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.926   4.885   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.926   3.345   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.592   2.575   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.259   3.345   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.259   4.885   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.925   5.655   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.592   1.035   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.838   0.130   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.344   0.450   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.820   1.914   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.327   2.235   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      10.803   3.699   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      11.357   1.090   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.864   1.410   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.881  -0.374   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.375  -0.695   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.899  -2.159   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.393  -2.479   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.917  -3.944   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.362  -1.335   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       4.822  -1.335   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       3.792  -2.479   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.285  -2.159   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.810  -0.695   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.303  -0.374   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.173   1.090   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.679   1.410   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.858   2.235   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.382   3.699   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.364   1.914   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.840   0.450   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.346   0.130   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7                                                            
CONECT    9    5   10   34                                                  
CONECT   10    9   11   22                                                  
CONECT   11   10   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   11   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   10   23                                                  
CONECT   23   22   24   34                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   33                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   26   34                                                  
CONECT   34   33    9   23                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₁₅NO₈

Average Mass

457.3940 Da

Monoisotopic Mass

457.07977 Da

IUPAC Name

12-(3,4-dihydroxyphenyl)-7,8,16,17-tetrahydroxy-4-oxa-1-azapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-2(11),5,7,9,12,14,16,18,20-nonaen-3-one

Traditional Name

12-(3,4-dihydroxyphenyl)-7,8,16,17-tetrahydroxy-4-oxa-1-azapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-2(11),5,7,9,12,14,16,18,20-nonaen-3-one

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1O)C1=C2N(C=CC3=CC(O)=C(O)C=C23)C2=C1C1=CC(O)=C(O)C=C1OC2=O

InChI Identifier

InChI=1S/C25H15NO8/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/h1-9,27-32H

InChI Key

BPOUMVNAKKCMPF-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
1-benzopyran
Benzopyran
Isoquinoline
Pyrrolopyridine
Indolizine
Catechol
1-hydroxy-4-unsubstituted benzenoid
Pyranone
1-hydroxy-2-unsubstituted benzenoid
Phenol
Substituted pyrrole
Pyran
Monocyclic benzene moiety
Benzenoid
Pyridine
Pyrrole
Heteroaromatic compound
Lactone
Organoheterocyclic compound
Azacycle
Oxacycle
Polyol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen 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	3.85	ALOGPS
logP	3.3	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	7.57	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	152.09 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	122.37 m³·mol⁻¹	ChemAxon
Polarizability	45.23 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

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

9846904

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)-7,8,16,17-tetrahydroxy-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 (NP0217694)

MOL for NP0217694 (12-(3,4-dihydroxyphenyl)-7,8,16,17-tetrahydroxy-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 NP0217694 (12-(3,4-dihydroxyphenyl)-7,8,16,17-tetrahydroxy-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 NP0217694 (12-(3,4-dihydroxyphenyl)-7,8,16,17-tetrahydroxy-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 NP0217694 (12-(3,4-dihydroxyphenyl)-7,8,16,17-tetrahydroxy-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 NP0217694 (12-(3,4-dihydroxyphenyl)-7,8,16,17-tetrahydroxy-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 NP0217694 (12-(3,4-dihydroxyphenyl)-7,8,16,17-tetrahydroxy-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 NP0217694 (12-(3,4-dihydroxyphenyl)-7,8,16,17-tetrahydroxy-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 NP0217694 (12-(3,4-dihydroxyphenyl)-7,8,16,17-tetrahydroxy-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 NP0217694 (12-(3,4-dihydroxyphenyl)-7,8,16,17-tetrahydroxy-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 NP0217694 (12-(3,4-dihydroxyphenyl)-7,8,16,17-tetrahydroxy-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)