NP-MRD: Showing NP-Card for 5,5′-dimethyl-4,4′,7,7′-tetramethoxy-8,8′-bicoumarin (NP0332550)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2024-02-22 12:16:32 UTC

Updated at

2024-09-03 04:19:35 UTC

NP-MRD ID

NP0332550

Natural Product DOI

https://doi.org/10.57994/1807

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,5′-dimethyl-4,4′,7,7′-tetramethoxy-8,8′-bicoumarin

Description

(+)-Kotanin belongs to the class of organic compounds known as coumarins and derivatives. 5,5′-dimethyl-4,4′,7,7′-tetramethoxy-8,8′-bicoumarin was first documented in 1971 (PMID: 5551701). These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one) (+)-kotanin is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 17315249).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231518422D          

 32 35  0  0  0  0            999 V2000
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   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   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   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
    0.0000   -1.6500    0.0000 O   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  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
    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
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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
    2.8579    0.8250    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  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  2  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 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
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 17 30  1  0  0  0  0
 24 30  2  0  0  0  0
 25 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
    1.0137    0.2891    4.0354 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4338    0.3480    2.7487 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3210    0.2404    1.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6587    0.0886    1.8310 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4786   -0.0115    0.7117 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9428   -0.1780    0.8569 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9226    0.0448   -0.5536 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7265   -0.0534   -1.6625 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0863   -0.2081   -1.5479 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8803   -0.3055   -2.7129 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1355    0.0070   -2.9059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7616    0.1636   -2.9585 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2606    0.2141   -4.1336 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0165    0.2548   -1.9017 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5427    0.2015   -0.7128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7247    0.3014    0.4191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7228    0.4658    0.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3289    1.6954    0.1424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4819    2.8165    0.2233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0439    4.1009    0.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6766    1.8560   -0.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4699    0.7028   -0.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9308    0.8017   -0.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9103   -0.5742   -0.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6751   -1.7179   -0.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0281   -1.6124   -0.2422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9288   -2.6718   -0.3309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0294   -2.9443    0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6656   -2.9531    0.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0600   -4.0758    0.2880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9709   -1.8541    0.2554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5337   -0.6760    0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4570   -0.7335    4.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2797    0.4763    4.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8200    1.0597    4.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1017    0.0436    2.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3190   -1.1641    0.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5357    0.6877    0.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1518   -0.1970    1.9765 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9553   -0.3606   -2.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6468    0.4777   -3.4460 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6308   -1.3085   -3.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7167   -0.0647   -3.8224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9427    4.1971    0.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3485    4.3736   -0.8881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3121    4.8410    0.5254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1491    2.8091   -0.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4922    0.4525    0.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3035    0.4171   -1.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1709    1.9162   -0.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7313   -3.4762    0.4257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0468   -3.0772   -1.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9452   -2.2706   -0.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6212   -3.8554   -0.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  1  0
  8 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15  7  2  0
  7  5  1  0
  5  6  1  0
  5  4  2  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  3 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 32  2  0
 32 31  1  0
 31 29  1  0
 29 30  2  0
 29 28  1  0
 28 25  2  0
 25 26  1  0
 26 27  1  0
  7  8  1  0
 32 17  1  0
 16 15  1  0
 25 24  1  0
 10 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
  6 37  1  0
  6 38  1  0
  6 39  1  0
  4 36  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
 21 47  1  0
 23 48  1  0
 23 49  1  0
 23 50  1  0
 28 54  1  0
 27 51  1  0
 27 52  1  0
 27 53  1  0
M  END


  Mrv1533004231518422D          

 32 35  0  0  0  0            999 V2000
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   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   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   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
    0.0000   -1.6500    0.0000 O   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  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
    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
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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
    2.8579    0.8250    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  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  2  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 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
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 17 30  1  0  0  0  0
 24 30  2  0  0  0  0
 25 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332550

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)OC2=C1C(C)=CC(OC)=C2C1=C(OC)C=C(C)C2=C1OC(=O)C=C2OC

> <INCHI_IDENTIFIER>
InChI=1S/C24H22O8/c1-11-7-13(27-3)21(23-19(11)15(29-5)9-17(25)31-23)22-14(28-4)8-12(2)20-16(30-6)10-18(26)32-24(20)22/h7-10H,1-6H3

> <INCHI_KEY>
CSJOUDOXDHMIAH-UHFFFAOYSA-N

> <FORMULA>
C24H22O8

> <MOLECULAR_WEIGHT>
438.432

> <EXACT_MASS>
438.131467668

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
44.66730245719559

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-(4,7-dimethoxy-5-methyl-2-oxo-2H-chromen-8-yl)-4,7-dimethoxy-5-methyl-2H-chromen-2-one

> <ALOGPS_LOGP>
3.32

> <JCHEM_LOGP>
2.670760004666667

> <ALOGPS_LOGS>
-4.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.253657273067388

> <JCHEM_POLAR_SURFACE_AREA>
89.52000000000001

> <JCHEM_REFRACTIVITY>
118.47119999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.83e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-(4,7-dimethoxy-5-methyl-2-oxochromen-8-yl)-4,7-dimethoxy-5-methylchromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8    3   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13    8   17                                                  
CONECT   17   16   18   30                                                  
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   30                                                  
CONECT   25   24   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   17   24                                                  
CONECT   31   25   32                                                       
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
(+)-4,4',7,7'-Tetramethoxy-5,5'-dimethyl-2H,2'H-8,8'-bichromene-2,2'-dione	ChEBI
(AS)-(+)-4,4',7,7'-tetramethoxy-5,5'-dimethyl-2H,2'H-8,8'-bichromene-2,2'-dione	ChEBI
(p)-4,4',7,7'-Tetramethoxy-5,5'-dimethyl-2H,2'H-8,8'-bichromene-2,2'-dione	ChEBI
(S)-(+)-4,4',7,7'-Tetramethoxy-5,5'-dimethyl-2H,2'H-8,8'-bichromene-2,2'-dione	ChEBI
(S)-4,4',7,7'-Tetramethoxy-5,5'-dimethyl-2H,2'H-8,8'-bichromene-2,2'-dione	ChEBI
Kotanin	ChEBI

Chemical Formula

C₂₄H₂₂O₈

Average Mass

438.4320 Da

Monoisotopic Mass

438.13147 Da

IUPAC Name

8-(4,7-dimethoxy-5-methyl-2-oxo-2H-chromen-8-yl)-4,7-dimethoxy-5-methyl-2H-chromen-2-one

Traditional Name

8-(4,7-dimethoxy-5-methyl-2-oxochromen-8-yl)-4,7-dimethoxy-5-methylchromen-2-one

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)OC2=C1C(C)=CC(OC)=C2C1=C(OC)C=C(C)C2=C1OC(=O)C=C2OC

InChI Identifier

InChI=1S/C24H22O8/c1-11-7-13(27-3)21(23-19(11)15(29-5)9-17(25)31-23)22-14(28-4)8-12(2)20-16(30-6)10-18(26)32-24(20)22/h7-10H,1-6H3

InChI Key

CSJOUDOXDHMIAH-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C2D6OS, experimental)	yijing0212@163.com	南方医科大学	Jing Yi	2024-02-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	yijing0212@163.com	南方医科大学	Jing Yi	2024-02-22	View Spectrum

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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Not Available

Direct Parent

Coumarins and derivatives

Alternative Parents

Substituents

Coumarin
Benzopyran
1-benzopyran
Anisole
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous ester
Lactone
Organoheterocyclic compound
Oxacycle
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

8,8'-bicoumarins (CHEBI:64454 )

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	3.32	ALOGPS
logP	2.67	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	89.52 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	118.47 m³·mol⁻¹	ChemAxon
Polarizability	44.67 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

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

34059

PDB ID

Not Available

ChEBI ID

64454

Good Scents ID

Not Available

References

General References

Huttel W, Muller M: Regio- and stereoselective intermolecular oxidative phenol coupling in kotanin biosynthesis by Aspergillus niger. Chembiochem. 2007 Mar 26;8(5):521-9. doi: 10.1002/cbic.200600434. [PubMed:17315249 ]
Buchi G, Klaubert DH, Shank RC, Weinreb SM, Wogan GN: Structure and synthesis of kotanin and desmethylkotanin, metabolites of Aspergillus glaucus. J Org Chem. 1971 Apr 23;36(8):1143-7. doi: 10.1021/jo00807a028. [PubMed:5551701 ]

Showing NP-Card for 5,5′-dimethyl-4,4′,7,7′-tetramethoxy-8,8′-bicoumarin (NP0332550)

MOL for NP0332550 (5,5′-dimethyl-4,4′,7,7′-tetramethoxy-8,8′-bicoumarin)

3D MOL for NP0332550 (5,5′-dimethyl-4,4′,7,7′-tetramethoxy-8,8′-bicoumarin)

3D SDF for NP0332550 (5,5′-dimethyl-4,4′,7,7′-tetramethoxy-8,8′-bicoumarin)

3D-SDF for NP0332550 (5,5′-dimethyl-4,4′,7,7′-tetramethoxy-8,8′-bicoumarin)

PDB for NP0332550 (5,5′-dimethyl-4,4′,7,7′-tetramethoxy-8,8′-bicoumarin)

3D PDB for NP0332550 (5,5′-dimethyl-4,4′,7,7′-tetramethoxy-8,8′-bicoumarin)

SMILES for NP0332550 (5,5′-dimethyl-4,4′,7,7′-tetramethoxy-8,8′-bicoumarin)

INCHI for NP0332550 (5,5′-dimethyl-4,4′,7,7′-tetramethoxy-8,8′-bicoumarin)

Structure for NP0332550 (5,5′-dimethyl-4,4′,7,7′-tetramethoxy-8,8′-bicoumarin)

3D Structure for NP0332550 (5,5′-dimethyl-4,4′,7,7′-tetramethoxy-8,8′-bicoumarin)