NP-MRD: Showing NP-Card for (2s)-5,7-dihydroxy-6-(2-hydroxy-4,5,6,7-tetrahydro-3h-1,3-diazepin-4-yl)-2-phenyl-2,3-dihydro-1-benzopyran-4-one (NP0329490)

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Record Information

Version

2.0

Created at

2022-09-12 13:55:27 UTC

Updated at

2022-09-12 13:55:27 UTC

NP-MRD ID

NP0329490

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-5,7-dihydroxy-6-(2-hydroxy-4,5,6,7-tetrahydro-3h-1,3-diazepin-4-yl)-2-phenyl-2,3-dihydro-1-benzopyran-4-one

Description

Aquiledine belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. (2s)-5,7-dihydroxy-6-(2-hydroxy-4,5,6,7-tetrahydro-3h-1,3-diazepin-4-yl)-2-phenyl-2,3-dihydro-1-benzopyran-4-one is found in Aquilegia ecalcarata. (2s)-5,7-dihydroxy-6-(2-hydroxy-4,5,6,7-tetrahydro-3h-1,3-diazepin-4-yl)-2-phenyl-2,3-dihydro-1-benzopyran-4-one was first documented in 2020 (PMID: 33081470). Based on a literature review very few articles have been published on Aquiledine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122215552D          

 27 30  0  0  1  0            999 V2000
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9685   -1.1853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7568   -1.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0582   -2.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6457   -2.9109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8299   -3.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5868   -3.8222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2252   -2.4727    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    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  1  1  0  0  0
  5  6  2  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  2  0  0  0  0
  5 10  1  0  0  0  0
  4 11  1  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  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 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
 22 24  1  0  0  0  0
 17 24  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 12 27  1  0  0  0  0
  2 27  1  0  0  0  0
M  END

     RDKit          3D

 47 50  0  0  0  0  0  0  0  0999 V2000
    1.6157    1.9231    1.2642 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6590    1.1987    0.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7505    1.2412   -0.7625 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2684   -0.1469   -0.8997 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5532   -0.2981   -0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2813   -1.5246   -0.5015 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4626   -1.7145    0.1006 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1558   -0.9238    0.9522 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4184    0.3335    1.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2385    0.5083    0.5995 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3458   -1.1843   -0.5884 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9925   -1.0013   -0.3887 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0216   -1.9544   -0.6137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2983   -1.6442   -0.3742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2222   -2.6591   -0.6141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7446   -0.4206    0.0840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1262   -0.0713    0.4284 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4862    1.2105   -0.2935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3879    2.1824    0.3059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6608    1.6699    0.9252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1544    0.4342    0.3962 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5566   -0.6705    0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3832   -1.6759   -0.3773 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1541   -1.0127    0.3065 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7476    0.5225    0.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9330    1.7914    0.8077 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5937    0.2297    0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2915    1.5564   -1.7796 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4752    2.0085   -0.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4553   -0.3364   -2.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7971   -2.2009   -1.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0160   -2.6940   -0.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0791   -1.0358    1.4401 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9324    0.9862    1.8774 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6750    1.4675    0.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3478   -2.9470   -0.9507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8904   -3.5527   -0.9456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0666    0.2714    1.5257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9841    0.8473   -1.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5866    1.6810   -0.7334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6353    2.9238   -0.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8894    2.8352    1.0506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5115    1.6429    2.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4169    2.4930    0.7673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8964   -2.5077   -0.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0190   -2.0490    0.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6750    2.2671    1.1446 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 16 25  1  0
 25 26  1  0
 25 27  2  0
 27  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  4 11  1  0
 11 12  1  0
 12 13  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 13 14  1  0
 10  5  1  0
 24 17  1  0
 12 27  1  0
 15 37  1  0
 17 38  1  1
 18 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
 23 45  1  0
 24 46  1  0
 26 47  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  6
 13 36  1  0
  6 31  1  0
  7 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
M  END


  Mrv1652309122215552D          

 27 30  0  0  1  0            999 V2000
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9685   -1.1853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7568   -1.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0582   -2.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6457   -2.9109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8299   -3.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5868   -3.8222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2252   -2.4727    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    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  1  1  0  0  0
  5  6  2  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  2  0  0  0  0
  5 10  1  0  0  0  0
  4 11  1  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  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 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
 22 24  1  0  0  0  0
 17 24  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 12 27  1  0  0  0  0
  2 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0329490

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=C(C2CCCN=C(O)N2)C(O)=C2C(=O)C[C@H](OC2=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H20N2O5/c23-13-10-16-18(14(24)9-15(27-16)11-5-2-1-3-6-11)19(25)17(13)12-7-4-8-21-20(26)22-12/h1-3,5-6,10,12,15,23,25H,4,7-9H2,(H2,21,22,26)/t12?,15-/m0/s1

> <INCHI_KEY>
NBILMSHCIXKQRW-CVRLYYSRSA-N

> <FORMULA>
C20H20N2O5

> <MOLECULAR_WEIGHT>
368.389

> <EXACT_MASS>
368.137221752

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
38.427299554284204

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-5,7-dihydroxy-6-(2-hydroxy-4,5,6,7-tetrahydro-1H-1,3-diazepin-7-yl)-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one

> <JCHEM_LOGP>
1.724753909336563

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.062166475511786

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.005961088288336

> <JCHEM_PKA_STRONGEST_BASIC>
14.835442076633798

> <JCHEM_POLAR_SURFACE_AREA>
111.38000000000001

> <JCHEM_REFRACTIVITY>
98.5324

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-5,7-dihydroxy-6-(2-hydroxy-4,5,6,7-tetrahydro-3H-1,3-diazepin-4-yl)-2-phenyl-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.274  -2.212   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.746  -2.666   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.309  -4.100   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      10.539  -5.434   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       9.016  -5.663   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.562  -7.135   0.000  0.00  0.00           O+0
HETATM   24  N   UNK     0       7.887  -4.616   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   27                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11    4   12                                                       
CONECT   12   11   13   27                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   25                                                  
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   17                                                       
CONECT   25   16   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   12    2                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₀N₂O₅

Average Mass

368.3890 Da

Monoisotopic Mass

368.13722 Da

IUPAC Name

(2S)-5,7-dihydroxy-6-(2-hydroxy-4,5,6,7-tetrahydro-1H-1,3-diazepin-7-yl)-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(2S)-5,7-dihydroxy-6-(2-hydroxy-4,5,6,7-tetrahydro-3H-1,3-diazepin-4-yl)-2-phenyl-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

OC1=C(C2CCCN=C(O)N2)C(O)=C2C(=O)C[C@H](OC2=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C20H20N2O5/c23-13-10-16-18(14(24)9-15(27-16)11-5-2-1-3-6-11)19(25)17(13)12-7-4-8-21-20(26)22-12/h1-3,5-6,10,12,15,23,25H,4,7-9H2,(H2,21,22,26)/t12?,15-/m0/s1

InChI Key

NBILMSHCIXKQRW-CVRLYYSRSA-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
Aquilegia ecalcarata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavanones

Alternative Parents

Substituents

Hydroxyflavonoid
Flavanone
5-hydroxyflavonoid
7-hydroxyflavonoid
Chromone
Chromane
1-benzopyran
Benzopyran
Aryl ketone
Aryl alkyl ketone
1,3-diazepane
1-hydroxy-4-unsubstituted benzenoid
Phenol
Diazepane
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Urea
Ketone
Ether
Organoheterocyclic compound
Oxacycle
Azacycle
Organic nitrogen compound
Carbonyl group
Organonitrogen compound
Organooxygen 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	1.72	ChemAxon
pKa (Strongest Acidic)	-3	ChemAxon
pKa (Strongest Basic)	14.84	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	111.38 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	98.53 m³·mol⁻¹	ChemAxon
Polarizability	38.43 Å³	ChemAxon
Number of Rings	4	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

C00045650

Chemspider ID

8722370

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10546979

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kawazoe R, Matsuo Y, Saito Y, Tanaka T: Computationally Assisted Structural Revision of Flavoalkaloids with a Seven-Membered Ring: Aquiledine, Isoaquiledine, and Cheliensisine. J Nat Prod. 2020 Nov 25;83(11):3347-3353. doi: 10.1021/acs.jnatprod.0c00691. Epub 2020 Oct 21. [PubMed:33081470 ]
LOTUS database [Link]

Showing NP-Card for (2s)-5,7-dihydroxy-6-(2-hydroxy-4,5,6,7-tetrahydro-3h-1,3-diazepin-4-yl)-2-phenyl-2,3-dihydro-1-benzopyran-4-one (NP0329490)

MOL for NP0329490 ((2s)-5,7-dihydroxy-6-(2-hydroxy-4,5,6,7-tetrahydro-3h-1,3-diazepin-4-yl)-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

3D MOL for NP0329490 ((2s)-5,7-dihydroxy-6-(2-hydroxy-4,5,6,7-tetrahydro-3h-1,3-diazepin-4-yl)-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

3D SDF for NP0329490 ((2s)-5,7-dihydroxy-6-(2-hydroxy-4,5,6,7-tetrahydro-3h-1,3-diazepin-4-yl)-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

3D-SDF for NP0329490 ((2s)-5,7-dihydroxy-6-(2-hydroxy-4,5,6,7-tetrahydro-3h-1,3-diazepin-4-yl)-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

PDB for NP0329490 ((2s)-5,7-dihydroxy-6-(2-hydroxy-4,5,6,7-tetrahydro-3h-1,3-diazepin-4-yl)-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

3D PDB for NP0329490 ((2s)-5,7-dihydroxy-6-(2-hydroxy-4,5,6,7-tetrahydro-3h-1,3-diazepin-4-yl)-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

SMILES for NP0329490 ((2s)-5,7-dihydroxy-6-(2-hydroxy-4,5,6,7-tetrahydro-3h-1,3-diazepin-4-yl)-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

INCHI for NP0329490 ((2s)-5,7-dihydroxy-6-(2-hydroxy-4,5,6,7-tetrahydro-3h-1,3-diazepin-4-yl)-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

Structure for NP0329490 ((2s)-5,7-dihydroxy-6-(2-hydroxy-4,5,6,7-tetrahydro-3h-1,3-diazepin-4-yl)-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

3D Structure for NP0329490 ((2s)-5,7-dihydroxy-6-(2-hydroxy-4,5,6,7-tetrahydro-3h-1,3-diazepin-4-yl)-2-phenyl-2,3-dihydro-1-benzopyran-4-one)