NP-MRD: Showing NP-Card for (2s,3s)-3-(3,4-dihydroxy-5-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one (NP0174679)

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Record Information

Version

2.0

Created at

2022-09-03 11:58:00 UTC

Updated at

2022-09-03 11:58:01 UTC

NP-MRD ID

NP0174679

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3s)-3-(3,4-dihydroxy-5-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one

Description

5'-Demethylaquillochin 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. (2s,3s)-3-(3,4-dihydroxy-5-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one is found in Mallotus apelta. (2s,3s)-3-(3,4-dihydroxy-5-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one was first documented in 2008 (PMID: 18421750). Based on a literature review a small amount of articles have been published on 5'-Demethylaquillochin (PMID: 20686865) (PMID: 19439309).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032213582D          

 29 32  0  0  1  0            999 V2000
   -1.2671    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4421    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0296   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4454   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -1.5395    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0329   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0296   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4421   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4421   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2671   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 13 19  1  0  0  0  0
 19 20  2  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  6 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
  5 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
  3 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END

     RDKit          3D

 47 50  0  0  0  0  0  0  0  0999 V2000
    3.5120    2.3520    2.3049 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3961    1.3005    1.9530 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8906    0.2112    1.2565 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5678    0.0967    0.8867 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0838   -0.9890    0.1972 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6542   -1.0965   -0.1939 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2247    0.1476   -0.7306 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1418    0.4088   -0.8129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6164    1.5135   -1.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7393    2.4028   -2.0953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1710    3.5373   -2.7850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9667    1.7883   -1.5729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8925    0.9457   -0.9853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2381    1.2291   -1.0829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1180    0.3574   -0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5701   -0.7280    0.1719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4108   -1.5179    0.7211 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2789   -0.9523    0.2355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4057   -0.1590   -0.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0659   -0.4433   -0.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5618   -1.5483    0.4473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2368   -1.4283    0.9574 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1089   -2.7238    1.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0521   -3.8005    0.7492 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9413   -2.0050   -0.1419 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2702   -1.9339    0.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1657   -2.9662   -0.1325 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7217   -0.8280    0.8989 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0824   -0.7517    1.2573 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9017    2.6596    1.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8259    2.0014    3.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0652    3.2704    2.6014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8916    0.9055    1.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5000   -1.8453   -0.9905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8808    4.1327   -2.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2966    4.2022   -2.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6736    3.2907   -3.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3502    2.6527   -2.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6410    2.0872   -1.6000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2059    0.5202   -0.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2255   -0.6199    1.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0490   -2.6871    2.1967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7039   -2.9113    2.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3404   -3.4867   -0.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6154   -2.8882   -0.6868 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7928   -3.7581   -0.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4186    0.0547    1.7641 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
 26 28  2  0
 28 29  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
 28  3  1  0
 22  6  1  0
 20  8  1  0
 19 13  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
 25 45  1  0
 27 46  1  0
 29 47  1  0
  6 34  1  6
 11 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 14 39  1  0
 15 40  1  0
 22 41  1  1
 23 42  1  0
 23 43  1  0
 24 44  1  0
M  END


  Mrv1652309032213582D          

 29 32  0  0  1  0            999 V2000
   -1.2671    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4421    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0296   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4454   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -1.5395    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0329   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0296   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4421   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4421   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2671   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 13 19  1  0  0  0  0
 19 20  2  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  6 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
  5 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
  3 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0174679

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O9/c1-25-12-7-10(5-11(22)16(12)24)17-14(8-21)27-20-18-9(3-4-15(23)28-18)6-13(26-2)19(20)29-17/h3-7,14,17,21-22,24H,8H2,1-2H3/t14-,17-/m0/s1

> <INCHI_KEY>
ATBGMZCSYDMJJM-YOEHRIQHSA-N

> <FORMULA>
C20H18O9

> <MOLECULAR_WEIGHT>
402.355

> <EXACT_MASS>
402.09508216

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
39.70147227671051

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S)-3-(3,4-dihydroxy-5-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2H,3H,9H-[1,4]dioxino[2,3-h]chromen-9-one

> <ALOGPS_LOGP>
1.74

> <JCHEM_LOGP>
1.5279242113333336

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.007053938355305

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.397010558089763

> <JCHEM_PKA_STRONGEST_BASIC>
-2.990496526081322

> <JCHEM_POLAR_SURFACE_AREA>
123.91000000000003

> <JCHEM_REFRACTIVITY>
99.6395

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.94e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S)-3-(3,4-dihydroxy-5-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2H,3H-[1,4]dioxino[2,3-h]chromen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.365   1.127   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.825   1.127   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.055  -0.206   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.485  -0.206   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.255  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.795  -1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.565  -0.206   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.105  -0.206   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.875   1.127   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.105   2.461   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.875   3.795   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.415   1.127   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.185  -0.206   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.725  -0.206   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.495  -1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.725  -2.874   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      11.495  -4.207   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       9.185  -2.874   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.415  -1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.875  -1.540   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.105  -2.874   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.565  -2.874   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.795  -4.207   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.255  -4.207   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.485  -2.874   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.055  -2.874   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.825  -4.207   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -0.825  -1.540   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.365  -1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   28                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   25                                                  
CONECT    6    5    7   22                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   20                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   13   20                                                  
CONECT   20   19    8   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21    6   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25    5   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26    3   29                                                  
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₈O₉

Average Mass

402.3550 Da

Monoisotopic Mass

402.09508 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H18O9/c1-25-12-7-10(5-11(22)16(12)24)17-14(8-21)27-20-18-9(3-4-15(23)28-18)6-13(26-2)19(20)29-17/h3-7,14,17,21-22,24H,8H2,1-2H3/t14-,17-/m0/s1

InChI Key

ATBGMZCSYDMJJM-YOEHRIQHSA-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
Mallotus apelta	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
Phenylbenzodioxane
2-phenylbenzo-1,4-dioxane
P-dioxolo[2,3-h]coumarin
Coumarin
1-benzopyran
Methoxyphenol
Benzopyran
Benzodioxane
Benzo-1,4-dioxane
Phenoxy compound
Methoxybenzene
Phenol ether
Catechol
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Phenol
Alkyl aryl ether
Benzenoid
Pyran
Para-dioxin
Monocyclic benzene moiety
Heteroaromatic compound
Lactone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
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

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

113611428

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

133561782

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 ]
Xu JF, Feng ZM, Liu J, Zhang PC: New hepatoprotective coumarinolignoids from Mallotus apelta. Chem Biodivers. 2008 Apr;5(4):591-7. doi: 10.1002/cbdv.200890055. [PubMed:18421750 ]
Cheng L, Zhang X, Zhang M, Zhang P, Song Z, Ma Z, Cheng Y, Qu H: Characterization of chemopreventive agents from the dichloromethane extract of Eurycorymbus cavaleriei by liquid chromatography-ion trap mass spectrometry. J Chromatogr A. 2009 Jun 12;1216(24):4859-67. doi: 10.1016/j.chroma.2009.04.031. Epub 2009 Apr 16. [PubMed:19439309 ]
LOTUS database [Link]

Showing NP-Card for (2s,3s)-3-(3,4-dihydroxy-5-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one (NP0174679)

MOL for NP0174679 ((2s,3s)-3-(3,4-dihydroxy-5-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one)

3D MOL for NP0174679 ((2s,3s)-3-(3,4-dihydroxy-5-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one)

3D SDF for NP0174679 ((2s,3s)-3-(3,4-dihydroxy-5-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one)

3D-SDF for NP0174679 ((2s,3s)-3-(3,4-dihydroxy-5-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one)

PDB for NP0174679 ((2s,3s)-3-(3,4-dihydroxy-5-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one)

3D PDB for NP0174679 ((2s,3s)-3-(3,4-dihydroxy-5-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one)

SMILES for NP0174679 ((2s,3s)-3-(3,4-dihydroxy-5-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one)

INCHI for NP0174679 ((2s,3s)-3-(3,4-dihydroxy-5-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one)

Structure for NP0174679 ((2s,3s)-3-(3,4-dihydroxy-5-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one)

3D Structure for NP0174679 ((2s,3s)-3-(3,4-dihydroxy-5-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one)