NP-MRD: Showing NP-Card for Aquillochin (NP0071969)

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Record Information

Version

2.0

Created at

2022-04-28 17:21:35 UTC

Updated at

2022-04-28 17:21:35 UTC

NP-MRD ID

NP0071969

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aquillochin

Description

Cleomiscosin C belongs to the class of organic compounds known as coumarinolignans. These are lignans with a structure characterized by the presence of a 1,4-dioxane bridge substituted by a phenyl group, and fused to a coumarin. Aquillochin is found in Acer nikoense , Aceraceae nikoense, Artemisia minor, Coptis japonica, Hibiscus syriacus , Hibiscus taiwanensis, Pileostegia viburnoides var. glabrescens, Rhododendron collettianum and Xanthium strumarium. Aquillochin was first documented in 2007 (PMID: 17424931). Based on a literature review a small amount of articles have been published on Cleomiscosin C (PMID: 20686865) (PMID: 31816856) (PMID: 21854171) (PMID: 20120038).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282219212D          

 30 33  0  0  1  0            999 V2000
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  5 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  8 17  1  0  0  0  0
 16 18  1  1  0  0  0
 18 19  1  0  0  0  0
 15 20  1  6  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 23 28  1  0  0  0  0
 22 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END

     RDKit          3D

 50 53  0  0  0  0  0  0  0  0999 V2000
    3.4385    3.7873    0.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2692    2.6740    0.2838 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7569    1.3893    0.3010 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4241    1.1980    0.0992 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8920   -0.0736    0.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4691   -0.3282   -0.0996 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3692    0.5563    0.6347 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7370    0.3712    0.4262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6807    0.8409    1.3211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2428    1.5113    2.4505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1272    2.0240    3.4153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0328    0.6588    1.1164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4443   -0.0182   -0.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8008   -0.2255   -0.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1783   -0.9003   -1.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2067   -1.3532   -2.2849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6000   -1.9733   -3.3306 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9323   -1.1545   -2.0449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5453   -0.5069   -0.9509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1980   -0.2935   -0.6914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2695   -0.7796   -1.6136 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0357   -0.2307   -1.5416 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9918   -0.9167   -2.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0991   -2.2632   -2.1889 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7396   -1.1400    0.3334 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1002   -0.9822    0.5424 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9504   -2.0610    0.7651 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3653   -3.3692    0.7722 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5850    0.2986    0.5210 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9410    0.5481    0.7220 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0040    4.7086   -0.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8154    3.5479   -0.8447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7142    3.8250    0.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7172    2.0088   -0.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2058   -1.3500    0.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5300    2.3421    4.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7112    2.8899    3.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8411    1.2417    3.7690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7958    1.0131    1.7958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4966    0.1584    0.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2382   -1.0604   -1.6075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0405    0.8372   -1.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9466   -0.3826   -2.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5675   -0.8101   -3.5041 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3898   -2.7361   -2.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3643   -2.1584    0.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1440   -4.1384    0.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6613   -3.4589    1.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8573   -3.5415   -0.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5732   -0.2243    0.8853 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 26 29  2  0
 29 30  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 29  3  1  0
 22  6  1  0
 20  8  1  0
 19 13  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
 25 46  1  0
 28 47  1  0
 28 48  1  0
 28 49  1  0
 30 50  1  0
  6 35  1  1
 11 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 14 40  1  0
 15 41  1  0
 22 42  1  6
 23 43  1  0
 23 44  1  0
 24 45  1  0
M  END


  Mrv1652304282219212D          

 30 33  0  0  1  0            999 V2000
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  5 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  8 17  1  0  0  0  0
 16 18  1  1  0  0  0
 18 19  1  0  0  0  0
 15 20  1  6  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 23 28  1  0  0  0  0
 22 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0071969

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(OC)=C1O)[C@H]1OC2=C(OC)C=C3C=CC(=O)OC3=C2O[C@@H]1CO

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O9/c1-25-12-7-11(8-13(26-2)17(12)24)18-15(9-22)28-21-19-10(4-5-16(23)29-19)6-14(27-3)20(21)30-18/h4-8,15,18,22,24H,9H2,1-3H3/t15-,18-/m1/s1

> <INCHI_KEY>
GZXPCBAETDEQAX-CRAIPNDOSA-N

> <FORMULA>
C21H20O9

> <MOLECULAR_WEIGHT>
416.382

> <EXACT_MASS>
416.110732224

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
41.572901024906585

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R)-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2H,3H,9H-[1,4]dioxino[2,3-h]chromen-9-one

> <ALOGPS_LOGP>
2.26

> <JCHEM_LOGP>
1.673818267333334

> <ALOGPS_LOGS>
-3.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.561738754067257

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.300181615123964

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9904965266241605

> <JCHEM_POLAR_SURFACE_AREA>
112.91000000000003

> <JCHEM_REFRACTIVITY>
104.12180000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.66e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R)-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2H,3H-[1,4]dioxino[2,3-h]chromen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.494   3.437   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.184   2.104   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.104  -3.231   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.874  -4.565   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.564  -0.564   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.104   2.104   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.206   3.437   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.564   4.771   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.746   0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.516  -0.564   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.056  -0.564   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.826   0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.056   2.104   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.516   2.104   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -4.826   3.437   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -6.366   3.437   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -6.366   0.770   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -4.826  -1.897   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -6.366  -1.897   0.000  0.00  0.00           C+0
CONECT    1    2    3    7                                                  
CONECT    2    1                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    1                                                       
CONECT    8    6    9   17                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10    5                                                       
CONECT   12   10   13                                                       
CONECT   13   12                                                            
CONECT   14    9   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16    8                                                       
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20   15   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   29                                                  
CONECT   23   22   24   28                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24   20                                                       
CONECT   26   24   27                                                       
CONECT   27   26                                                            
CONECT   28   23                                                            
CONECT   29   22   30                                                       
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₀O₉

Average Mass

416.3820 Da

Monoisotopic Mass

416.11073 Da

IUPAC Name

(2R,3R)-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2H,3H,9H-[1,4]dioxino[2,3-h]chromen-9-one

Traditional Name

(2R,3R)-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2H,3H-[1,4]dioxino[2,3-h]chromen-9-one

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1O)[C@H]1OC2=C(OC)C=C3C=CC(=O)OC3=C2O[C@@H]1CO

InChI Identifier

InChI=1S/C21H20O9/c1-25-12-7-11(8-13(26-2)17(12)24)18-15(9-22)28-21-19-10(4-5-16(23)29-19)6-14(27-3)20(21)30-18/h4-8,15,18,22,24H,9H2,1-3H3/t15-,18-/m1/s1

InChI Key

GZXPCBAETDEQAX-CRAIPNDOSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Acer nikoense	Plant	KNApSAcK
Aceraceae nikoense	-	KNApSAcK
Artemisia minor	Plant	KNApSAcK
Coptis japonica	LOTUS Database	35616633
Hibiscus syriacus	Plant	KNApSAcK
Hibiscus taiwanensis	Plant	KNApSAcK
Pileostegia viburnoides var. glabrescens	Plant	KNApSAcK
Rhododendron collettianum	Plant	KNApSAcK
Xanthium strumarium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarinolignans. These are lignans with a structure characterized by the presence of a 1,4-dioxane bridge substituted by a phenyl group, and fused to a coumarin.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Coumarinolignans

Sub Class

Not Available

Direct Parent

Coumarinolignans

Alternative Parents

Substituents

Angular-fused coumarolignan skeleton
2-phenylbenzo-1,4-dioxane
Phenylbenzodioxane
P-dioxolo[2,3-h]coumarin
Coumarin
Benzo-1,4-dioxane
Benzodioxane
M-dimethoxybenzene
Dimethoxybenzene
Benzopyran
1-benzopyran
Methoxyphenol
Anisole
Methoxybenzene
Phenoxy compound
Phenol ether
Pyranone
Phenol
Alkyl aryl ether
Para-dioxin
Pyran
Benzenoid
Monocyclic benzene moiety
Heteroaromatic compound
Lactone
Ether
Organoheterocyclic compound
Oxacycle
Primary alcohol
Organooxygen compound
Organic oxygen compound
Organic oxide
Alcohol
Hydrocarbon derivative
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	2.26	ALOGPS
logP	1.67	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	9.3	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	112.91 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	104.12 m³·mol⁻¹	ChemAxon
Polarizability	41.57 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

C00031605

Chemspider ID

9639016

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11464176

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yoshikawa K, Kawahara Y, Arihara S, Hashimoto T: Aromatic compounds and their antioxidant activity of Acer saccharum. J Nat Med. 2011 Jan;65(1):191-3. doi: 10.1007/s11418-010-0450-5. Epub 2010 Aug 5. [PubMed:20686865 ]
Makong YS, Mouthe Happi G, Djouaka Bavoua JL, Wansi JD, Nahar L, Kamdem Waffo AF, Martin C, Sewald N, Sarker SD: Cytotoxic Stilbenes and Canthinone Alkaloids from Brucea antidysenterica (Simaroubaceae). Molecules. 2019 Dec 3;24(23). pii: molecules24234412. doi: 10.3390/molecules24234412. [PubMed:31816856 ]
Kan S, Chen G, Han C, Chen Z, Song X, Ren M, Jiang H: Chemical constituents from the roots of Xanthium sibiricum. Nat Prod Res. 2011 Aug;25(13):1243-9. doi: 10.1080/14786419.2010.539182. [PubMed:21854171 ]
Kaur R, Kumar S, Chatterjee A, Chattopadhyay SK: High-performance liquid chromatographic method for identification and quantification of three potent liver protective coumarinolignoids-cleomiscosin A, cleomiscosin B and cleomiscosin C-in extracts of Cleome viscosa. Biomed Chromatogr. 2010 Sep;24(9):1000-5. doi: 10.1002/bmc.1399. [PubMed:20120038 ]
Jin W, Thuong PT, Su ND, Min BS, Son KH, Chang HW, Kim HP, Kang SS, Sok DE, Bae K: Antioxidant activity of cleomiscosins A and C isolated from Acer okamotoanum. Arch Pharm Res. 2007 Mar;30(3):275-81. doi: 10.1007/BF02977606. [PubMed:17424931 ]

Showing NP-Card for Aquillochin (NP0071969)

MOL for NP0071969 (Aquillochin)

3D MOL for NP0071969 (Aquillochin)

3D SDF for NP0071969 (Aquillochin)

3D-SDF for NP0071969 (Aquillochin)

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3D PDB for NP0071969 (Aquillochin)

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INCHI for NP0071969 (Aquillochin)

Structure for NP0071969 (Aquillochin)

3D Structure for NP0071969 (Aquillochin)