NP-MRD: Showing NP-Card for Cleomiscosin A (NP0051716)

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Record Information

Version

2.0

Created at

2022-04-27 22:58:40 UTC

Updated at

2022-04-27 22:58:40 UTC

NP-MRD ID

NP0051716

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cleomiscosin A

Description

Cleomiscosin A 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. Cleomiscosin A is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Cleomiscosin A is found in Acer nikoense, Amaroria soulameoides, Artemisia minor, Brucea javanica, Christiana africana, Cleome icosandra , Coptis japonica, Dodonaea viscosa, Duranta erecta, Erycibe obtusifolia, Euphorbia lagascae, Hibiscus syriacus , Hibiscus taiwanensis, Hyoscyamus niger L. , Jatropha gossypiifolia, Jatropha multifida , Mallotus apelta, Matayba arborescens , Protium heptaphyllum, Quassia undulata, Rhododendron collettianum, Simaba multiflora , Simaba orinocensis, Soulamea soulameoides and Xanthium sibiricum. Cleomiscosin A was first documented in 2012 (PMID: 23302528). Based on a literature review a significant number of articles have been published on cleomiscosin A (PMID: 30205569) (PMID: 32356087) (PMID: 31816856) (PMID: 31153100) (PMID: 30717533) (PMID: 24199564).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200582D          

 28 31  0  0  1  0            999 V2000
    2.3645   -1.0164    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
    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
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 O   0  0  0  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
    2.7770    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.4454    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  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
  9 11  1  0  0  0  0
  4 11  1  0  0  0  0
  3 12  1  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
  2 15  1  0  0  0  0
 14 16  1  1  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 19 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 13 25  1  6  0  0  0
 25 26  1  0  0  0  0
  1 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END

     RDKit          3D

 46 49  0  0  0  0  0  0  0  0999 V2000
    5.4196   -0.9649    1.8794 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4870    0.0576    0.9229 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3982    0.5370    0.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1161    0.0578    0.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0463    0.5463   -0.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7192   -0.0326   -0.1270 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2895    0.9833   -0.0143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5937    0.5121    0.1319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5499    1.3418    0.6846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1801    2.6200    1.0770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1885    3.4392    1.6387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8402    0.8640    0.8249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1752   -0.4164    0.4230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4639   -0.8815    0.5677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7131   -2.1695    0.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6791   -2.9076   -0.3957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9815   -4.0912   -0.7690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4577   -2.4459   -0.5250 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1941   -1.2235   -0.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8899   -0.7771   -0.2829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9009   -1.5832   -0.8348 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2569   -0.9099   -1.2973 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3462   -1.8797   -1.6958 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8264   -2.6753   -2.7154 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3012    1.5517   -1.2569 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5887    2.0511   -1.4253 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6384    1.5522   -0.7008 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9197    2.0551   -0.8740 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6727   -1.7472    1.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4157   -1.4944    1.8431 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3230   -0.5770    2.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9844   -0.7476    1.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7184   -0.6879    0.7590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7497    2.9311    2.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9701    3.6833    0.8608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7941    4.4185    1.9713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6192    1.4884    1.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2608   -0.2856    0.9921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7222   -2.5988    0.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0036   -0.2673   -2.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6901   -2.4639   -0.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1566   -1.2703   -2.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2730   -2.0665   -3.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4805    1.9509   -1.8321 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7483    2.8413   -2.1389 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6904    1.6823   -0.3358 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 27  2  0
 27 28  1  0
 27 26  1  0
 26 25  2  0
 25  5  1  0
  5  4  2  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
  4  3  1  0
 22  6  1  0
 20  8  1  0
 19 13  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 28 46  1  0
 26 45  1  0
 25 44  1  0
  4 32  1  0
  6 33  1  1
 11 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 14 38  1  0
 15 39  1  0
 22 40  1  6
 23 41  1  0
 23 42  1  0
 24 43  1  0
M  END


  Mrv1652304282200582D          

 28 31  0  0  1  0            999 V2000
    2.3645   -1.0164    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
    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
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 O   0  0  0  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
    2.7770    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.4454    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  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
  9 11  1  0  0  0  0
  4 11  1  0  0  0  0
  3 12  1  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
  2 15  1  0  0  0  0
 14 16  1  1  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 19 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 13 25  1  6  0  0  0
 25 26  1  0  0  0  0
  1 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051716

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(=C1)[C@H]1OC2=C(OC)C=C3C=CC(=O)OC3=C2O[C@@H]1CO

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O8/c1-24-13-7-10(3-5-12(13)22)17-15(9-21)26-20-18-11(4-6-16(23)27-18)8-14(25-2)19(20)28-17/h3-8,15,17,21-22H,9H2,1-2H3/t15-,17-/m1/s1

> <INCHI_KEY>
OCBGWPJNUZMLCA-NVXWUHKLSA-N

> <FORMULA>
C20H18O8

> <MOLECULAR_WEIGHT>
386.356

> <EXACT_MASS>
386.10016754

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
38.47413645927763

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.28

> <JCHEM_LOGP>
1.8314895329999998

> <ALOGPS_LOGS>
-3.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.56174793514992

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.908128879776871

> <JCHEM_PKA_STRONGEST_BASIC>
-2.990495687673924

> <JCHEM_POLAR_SURFACE_AREA>
103.68000000000002

> <JCHEM_REFRACTIVITY>
97.6586

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.60e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cleomiscosin A

> <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       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.104   2.104   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       5.184   2.104   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.724  -0.564   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.344   2.104   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.114   0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.344  -0.564   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.804  -0.564   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      13.654   0.770   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      12.114   3.437   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      13.654   3.437   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.494   3.437   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.034   3.437   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       5.184  -3.231   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.414  -4.565   0.000  0.00  0.00           C+0
CONECT    1    2    6   27                                                  
CONECT    2    1    3   15                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    4                                                       
CONECT   12    3   13                                                       
CONECT   13   12   14   25                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14    2                                                       
CONECT   16   14   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   19                                                            
CONECT   23   18   24                                                       
CONECT   24   23                                                            
CONECT   25   13   26                                                       
CONECT   26   25                                                            
CONECT   27    1   28                                                       
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₈O₈

Average Mass

386.3560 Da

Monoisotopic Mass

386.10017 Da

IUPAC Name

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

Traditional Name

cleomiscosin A

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(=C1)[C@H]1OC2=C(OC)C=C3C=CC(=O)OC3=C2O[C@@H]1CO

InChI Identifier

InChI=1S/C20H18O8/c1-24-13-7-10(3-5-12(13)22)17-15(9-21)26-20-18-11(4-6-16(23)27-18)8-14(25-2)19(20)28-17/h3-8,15,17,21-22H,9H2,1-2H3/t15-,17-/m1/s1

InChI Key

OCBGWPJNUZMLCA-NVXWUHKLSA-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	LOTUS Database	35616633
Amaroria soulameoides	LOTUS Database	35616633
Artemisia minor	LOTUS Database	35616633
Brucea javanica	LOTUS Database	35616633
Christiana africana	LOTUS Database	35616633
Cleome icosandra	Plant	KNApSAcK
Coptis japonica	LOTUS Database	35616633
Dodonaea viscosa	LOTUS Database	35616633
Duranta erecta	LOTUS Database	35616633
Erycibe obtusifolia	Plant	KNApSAcK
Euphorbia lagascae	LOTUS Database	35616633
Hibiscus syriacus	Plant	KNApSAcK
Hibiscus taiwanensis	Plant	KNApSAcK
Hyoscyamus niger	Plant	KNApSAcK
Jatropha gossypifolia	LOTUS Database	35616633
Jatropha multifida	Plant	KNApSAcK
Mallotus apelta	LOTUS Database	35616633
Matayba arborescens	Plant	KNApSAcK
Protium heptaphyllum	LOTUS Database	35616633
Quassia undulata	LOTUS Database	35616633
Rhododendron collettianum	Plant	KNApSAcK
Simaba multiflora	Plant	KNApSAcK
Simaba orinocensis	LOTUS Database	35616633
Soulamea soulameoides	Plant	KNApSAcK
Xanthium sibiricum	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
Benzopyran
Methoxyphenol
1-benzopyran
Anisole
Methoxybenzene
Phenol ether
Phenoxy compound
Pyranone
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Pyran
Para-dioxin
Benzenoid
Heteroaromatic compound
Lactone
Oxacycle
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Alcohol
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:3740 )
organic heterotricyclic compound (CHEBI:3740 )
phenols (CHEBI:3740 )
primary alcohol (CHEBI:3740 )
delta-lactone (CHEBI:3740 )

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	2.28	ALOGPS
logP	1.83	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	9.91	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	103.68 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	97.66 m³·mol⁻¹	ChemAxon
Polarizability	38.47 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

C00002984

Chemspider ID

390936

KEGG Compound ID

C09922

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442510

PDB ID

Not Available

ChEBI ID

3740

Good Scents ID

rw1486771

References

General References

Chang FP, Chao W, Wang SY, Huang HC, Sung PJ, Chen JJ, Cheng MJ, Huang GJ, Kuo YH: Three New Iridoid Derivatives Have Been Isolated from the Stems of Neonauclea reticulata (Havil.) Merr. with Cytotoxic Activity on Hepatocellular Carcinoma Cells. Molecules. 2018 Sep 8;23(9). pii: molecules23092297. doi: 10.3390/molecules23092297. [PubMed:30205569 ]
Kumar SS, Hira K, Begum Ahil S, Kulkarni OP, Araya H, Fujimoto Y: New synthetic coumarinolignans as attenuators of pro-inflammatory cytokines in LPS-induced sepsis and carrageenan-induced paw oedema models. Inflammopharmacology. 2020 Oct;28(5):1365-1373. doi: 10.1007/s10787-020-00710-w. Epub 2020 Apr 30. [PubMed:32356087 ]
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 ]
Santhosh Kumar S, Sajeli Begum A, Hira K, Niazi S, Prashantha Kumar BR, Araya H, Fujimoto Y: Structure-based design and synthesis of new 4-methylcoumarin-based lignans as pro-inflammatory cytokines (TNF-alpha, IL-6 and IL-1beta) inhibitors. Bioorg Chem. 2019 Aug;89:102991. doi: 10.1016/j.bioorg.2019.102991. Epub 2019 May 20. [PubMed:31153100 ]
Guo XX, Zhao LN, Wang J, Liu S, Bi QR, Wang Z, Tan NH: [Chemical constituents from root barks of Dictamnus dasycarpus and their cytotoxic activities]. Zhongguo Zhong Yao Za Zhi. 2018 Dec;43(24):4869-4877. doi: 10.19540/j.cnki.cjcmm.20180926.002. [PubMed:30717533 ]
Chen H, Bai J, Fang ZF, Ma SG, Yu SS, Chen XG: [Chemical constituents from stems of Brucea mollis and their cytotoxic activity]. Zhongguo Zhong Yao Za Zhi. 2013 Jul;38(14):2321-4. [PubMed:24199564 ]
Chen DL, Li G, Liu YY, Ma GX, Zheng W, Sun XB, Xu XD: A new cadinane sesquiterpenoid glucoside with cytotoxicity from Abelmoschus sagittifolius. Nat Prod Res. 2019 Jun;33(12):1699-1704. doi: 10.1080/14786419.2018.1431635. Epub 2018 Feb 6. [PubMed:29409349 ]
Zhou D, Zhang Y, Jiang Z, Hou Y, Jiao K, Yan C, Li N: Biotransformation of isofraxetin-6-O-beta-d-glucopyranoside by Angelica sinensis (Oliv.) Diels callus. Bioorg Med Chem Lett. 2017 Jan 15;27(2):248-253. doi: 10.1016/j.bmcl.2016.11.069. Epub 2016 Nov 24. [PubMed:27919656 ]
Dzoyem JP, Donfack AR, Tane P, McGaw LJ, Eloff JN: Inhibition of Nitric Oxide Production in LPS-Stimulated RAW 264.7 Macrophages and 15-LOX Activity by Anthraquinones from Pentas schimperi. Planta Med. 2016 Sep;82(14):1246-51. doi: 10.1055/s-0042-104417. Epub 2016 Apr 19. [PubMed:27093247 ]
Zhang XY, Cai XH, Luo XD: Chemical constituents of Allophylus longipes. Chin J Nat Med. 2012 Jan;10(1):36-9. doi: 10.1016/S1875-5364(12)60008-9. [PubMed:23302528 ]

Showing NP-Card for Cleomiscosin A (NP0051716)

MOL for NP0051716 (Cleomiscosin A)

3D MOL for NP0051716 (Cleomiscosin A)

3D SDF for NP0051716 (Cleomiscosin A)

3D-SDF for NP0051716 (Cleomiscosin A)

PDB for NP0051716 (Cleomiscosin A)

3D PDB for NP0051716 (Cleomiscosin A)

SMILES for NP0051716 (Cleomiscosin A)

INCHI for NP0051716 (Cleomiscosin A)

Structure for NP0051716 (Cleomiscosin A)

3D Structure for NP0051716 (Cleomiscosin A)