NP-MRD: Showing NP-Card for 4-Hydroxy-5-methyl-3-[8'-oxo-9'-hydroxyfarnesyl]-coumarin (NP0063157)

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Record Information

Version

2.0

Created at

2022-04-28 07:37:46 UTC

Updated at

2022-04-28 07:37:47 UTC

NP-MRD ID

NP0063157

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-Hydroxy-5-methyl-3-[8'-oxo-9'-hydroxyfarnesyl]-coumarin

Description

4-Hydroxy-3-[(2E,6E,9R)-9-hydroxy-3,7,11-trimethyl-8-oxododeca-2,6,10-trien-1-yl]-5-methyl-2H-chromen-2-one belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. 4-Hydroxy-5-methyl-3-[8'-oxo-9'-hydroxyfarnesyl]-coumarin is found in Aphyllocladus denticulatus and Gypothamnium pinifolium. Based on a literature review very few articles have been published on 4-hydroxy-3-[(2E,6E,9R)-9-hydroxy-3,7,11-trimethyl-8-oxododeca-2,6,10-trien-1-yl]-5-methyl-2H-chromen-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282209372D          

 30 31  0  0  1  0            999 V2000
   -0.7145   -0.4125    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    2.1434   -0.4125    0.0000 C   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   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   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
    2.8579    0.8250    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
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   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
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  4 12  1  0  0  0  0
  9 13  1  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  1  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
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 22 27  1  1  0  0  0
 19 28  1  0  0  0  0
 15 29  1  0  0  0  0
  8 30  1  0  0  0  0
M  END

     RDKit          3D

 60 61  0  0  0  0  0  0  0  0999 V2000
    6.2227   -0.9119    2.8859 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8039   -0.8879    1.5122 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2735   -1.1895    1.3809 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0838   -0.6178    0.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6329   -0.3264    0.6288 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5438    0.8978    1.2387 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9042   -0.3624   -0.6407 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0134   -1.3954   -1.4070 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0536    0.7202   -1.0875 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8282    1.9052   -0.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4314    0.6449   -2.2642 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5409    1.6420   -2.8710 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1743    1.0571   -3.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4401    0.6399   -1.8332 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0693   -0.4175   -0.9460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5946    1.2993   -1.5262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3064    0.9808   -0.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6678    0.4653   -0.5303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4191    0.1778    0.6099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9053    0.3715    1.8736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6946   -0.3071    0.4789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4630   -0.6011    1.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9425   -0.4054    2.9507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7513   -1.0908    1.3572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2335   -1.2723    0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4674   -0.9793   -1.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1982   -0.4968   -0.8137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4548   -0.2125   -1.8561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2460    0.2470   -1.7403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6024    0.4930   -2.7684 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9980   -1.1193    3.6318 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3924   -1.6548    2.9148 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8002    0.0953    3.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8523   -0.2739    1.5322 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4801   -1.5722    0.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5206   -1.9306    2.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5055   -0.6042   -0.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1622   -1.0963    1.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4118    1.4094    1.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9835    2.5556   -0.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7725    2.4756   -0.1852 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5439    1.6400    0.8146 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6465   -0.2975   -2.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4798    2.5941   -2.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9673    1.8667   -3.9299 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3122    0.1644   -3.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4218    1.8437   -3.6370 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8188   -1.0152   -1.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5029    0.0145   -0.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7884   -1.1060   -0.7073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9994    2.0619   -2.1814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3659    1.9317    0.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7593    0.2820    0.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9699    0.7269    2.0363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7608   -0.7334    3.6635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0996   -1.0926    3.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7611    0.6490    3.2318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3526   -1.3208    2.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2493   -1.6585   -0.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8114   -1.1086   -2.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
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 17 18  1  0
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 19 20  1  0
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 29 18  1  0
 27 21  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
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  5 38  1  1
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 10 40  1  0
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 15 48  1  0
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 17 53  1  0
 20 54  1  0
 23 55  1  0
 23 56  1  0
 23 57  1  0
 24 58  1  0
 25 59  1  0
 26 60  1  0
M  END


  Mrv1652304282209372D          

 30 31  0  0  1  0            999 V2000
   -0.7145   -0.4125    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    2.1434   -0.4125    0.0000 C   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   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   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
    2.8579    0.8250    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
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   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
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  4 12  1  0  0  0  0
  9 13  1  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  1  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
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 22 27  1  1  0  0  0
 19 28  1  0  0  0  0
 15 29  1  0  0  0  0
  8 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0063157

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=C[C@@H](O)C(=O)C(\C)=C\CC\C(C)=C\CC1=C(O)C2=C(C)C=CC=C2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H30O5/c1-15(2)14-20(26)23(27)18(5)10-6-8-16(3)12-13-19-24(28)22-17(4)9-7-11-21(22)30-25(19)29/h7,9-12,14,20,26,28H,6,8,13H2,1-5H3/b16-12+,18-10+/t20-/m1/s1

> <INCHI_KEY>
WIZFKDIIVAZHGC-MCNHRCEFSA-N

> <FORMULA>
C25H30O5

> <MOLECULAR_WEIGHT>
410.51

> <EXACT_MASS>
410.209324066

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
45.09100870010028

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-3-[(2E,6E,9R)-9-hydroxy-3,7,11-trimethyl-8-oxododeca-2,6,10-trien-1-yl]-5-methyl-2H-chromen-2-one

> <ALOGPS_LOGP>
3.92

> <JCHEM_LOGP>
5.090916933000001

> <ALOGPS_LOGS>
-5.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.008131205478055

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.771317931830765

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6587835670256297

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
121.67739999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.76e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-3-[(2E,6E,9R)-9-hydroxy-3,7,11-trimethyl-8-oxododeca-2,6,10-trien-1-yl]-5-methylchromen-2-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      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.002   9.240   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      10.669   9.240   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.669  10.780   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.003  11.550   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.003  13.090   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.337  10.780   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      12.003   8.470   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9   30                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    4                                                       
CONECT   13    9   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   29                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   28                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   22                                                            
CONECT   28   19                                                            
CONECT   29   15                                                            
CONECT   30    8                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₀O₅

Average Mass

410.5100 Da

Monoisotopic Mass

410.20932 Da

IUPAC Name

4-hydroxy-3-[(2E,6E,9R)-9-hydroxy-3,7,11-trimethyl-8-oxododeca-2,6,10-trien-1-yl]-5-methyl-2H-chromen-2-one

Traditional Name

4-hydroxy-3-[(2E,6E,9R)-9-hydroxy-3,7,11-trimethyl-8-oxododeca-2,6,10-trien-1-yl]-5-methylchromen-2-one

CAS Registry Number

Not Available

SMILES

CC(C)=C[C@@H](O)C(=O)C(\C)=C\CC\C(C)=C\CC1=C(O)C2=C(C)C=CC=C2OC1=O

InChI Identifier

InChI=1S/C25H30O5/c1-15(2)14-20(26)23(27)18(5)10-6-8-16(3)12-13-19-24(28)22-17(4)9-7-11-21(22)30-25(19)29/h7,9-12,14,20,26,28H,6,8,13H2,1-5H3/b16-12+,18-10+/t20-/m1/s1

InChI Key

WIZFKDIIVAZHGC-MCNHRCEFSA-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
Aphyllocladus denticulatus	Plant	KNApSAcK
Gypothamnium pinifolium	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Farsesane sesquiterpenoid
Sesquiterpenoid
Hydroxycoumarin
4-hydroxycoumarin
Coumarin
1-benzopyran
Benzopyran
Fatty alcohol
Pyranone
Fatty acyl
Alpha-branched alpha,beta-unsaturated-ketone
Benzenoid
Pyran
Acyloin
Heteroaromatic compound
Vinylogous acid
Alpha,beta-unsaturated ketone
Enone
Alpha-hydroxy ketone
Acryloyl-group
Secondary alcohol
Lactone
Ketone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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
logP	3.92	ALOGPS
logP	5.09	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	5.77	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	121.68 m³·mol⁻¹	ChemAxon
Polarizability	45.09 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

162892895

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4-Hydroxy-5-methyl-3-[8'-oxo-9'-hydroxyfarnesyl]-coumarin (NP0063157)

MOL for NP0063157 (4-Hydroxy-5-methyl-3-[8'-oxo-9'-hydroxyfarnesyl]-coumarin)

3D MOL for NP0063157 (4-Hydroxy-5-methyl-3-[8'-oxo-9'-hydroxyfarnesyl]-coumarin)

3D SDF for NP0063157 (4-Hydroxy-5-methyl-3-[8'-oxo-9'-hydroxyfarnesyl]-coumarin)

3D-SDF for NP0063157 (4-Hydroxy-5-methyl-3-[8'-oxo-9'-hydroxyfarnesyl]-coumarin)

PDB for NP0063157 (4-Hydroxy-5-methyl-3-[8'-oxo-9'-hydroxyfarnesyl]-coumarin)

3D PDB for NP0063157 (4-Hydroxy-5-methyl-3-[8'-oxo-9'-hydroxyfarnesyl]-coumarin)

SMILES for NP0063157 (4-Hydroxy-5-methyl-3-[8'-oxo-9'-hydroxyfarnesyl]-coumarin)

INCHI for NP0063157 (4-Hydroxy-5-methyl-3-[8'-oxo-9'-hydroxyfarnesyl]-coumarin)

Structure for NP0063157 (4-Hydroxy-5-methyl-3-[8'-oxo-9'-hydroxyfarnesyl]-coumarin)

3D Structure for NP0063157 (4-Hydroxy-5-methyl-3-[8'-oxo-9'-hydroxyfarnesyl]-coumarin)