NP-MRD: Showing NP-Card for ajulemic acid (NP0249072)

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Record Information

Version

2.0

Created at

2022-09-07 11:32:00 UTC

Updated at

2022-09-07 11:32:00 UTC

NP-MRD ID

NP0249072

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ajulemic acid

Description

Ajulemic acid, also known as ajulemate, belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. Ajulemic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). ajulemic acid is found in Cannabis sativa. Ajulemic acid has been used in trials studying the treatment of Cystic Fibrosis, Dermatomyositis, and Diffuse Cutaneous Systemic Sclerosis.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05031423532D          

 31 33  0  0  1  0            999 V2000
   -5.3625    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4252    3.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5067    3.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9500    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1250    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7125    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4750    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0625    2.3645    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4125    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    0.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.2211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250    0.2211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -0.4934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    3.0789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.9355    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    3.0789    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 11 10  1  0  0  0  0
 12  9  1  0  0  0  0
 16 10  2  0  0  0  0
 16 13  1  0  0  0  0
 17 14  2  0  0  0  0
 17 15  1  0  0  0  0
 18 13  1  0  0  0  0
 19 11  1  0  0  0  0
 19 18  1  0  0  0  0
 20 14  1  0  0  0  0
 21 15  2  0  0  0  0
 22 18  1  0  0  0  0
 22 20  2  0  0  0  0
 22 21  1  0  0  0  0
 23 16  1  0  0  0  0
 24  2  1  0  0  0  0
 24  3  1  0  0  0  0
 24 12  1  0  0  0  0
 24 17  1  0  0  0  0
 25  4  1  0  0  0  0
 25  5  1  0  0  0  0
 25 19  1  0  0  0  0
 26 20  1  0  0  0  0
 27 23  2  0  0  0  0
 28 23  1  0  0  0  0
 29 21  1  0  0  0  0
 29 25  1  0  0  0  0
 18 30  1  6  0  0  0
 19 31  1  1  0  0  0
M  END

     RDKit          3D

 65 67  0  0  0  0  0  0  0  0999 V2000
    7.4433   -0.2789   -1.0288 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9357   -0.0304   -0.8091 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6644    1.4179   -0.6274 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2782    1.8466   -0.4046 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5589    1.4248    0.8148 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2375    0.0602    1.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3725   -0.8165    0.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3751   -2.1384    1.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8988   -1.2998   -0.9714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9504   -0.4227    0.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5285    0.7557   -0.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8200    1.0595   -0.5075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2099    2.2612   -1.0775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8034    0.1760   -0.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4143   -1.0023    0.4579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0753   -1.2791    0.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3860   -1.9349    0.8834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5879   -1.9424    0.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4795   -3.0073    0.6553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2262   -2.2923   -1.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1437   -0.5725    0.2257 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5067   -0.4106   -0.4053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8699    1.0156   -0.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0804    2.0039    0.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5782    3.3629    0.0242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7419    3.6084   -0.3338 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7527    4.3955    0.4186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6651    1.7605    0.4682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2390    0.4966   -0.2753 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8745   -0.3640   -0.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9059    0.5546   -1.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5208   -1.2625   -1.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6582   -0.7016    0.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4549   -0.3810   -1.7704 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3307    1.8405    0.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0676    1.9110   -1.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3117    3.0012   -0.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6625    1.7279   -1.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2669    1.7811    1.6731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7026    2.1596    1.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6400    0.1655    2.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1071   -0.5107    1.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4441   -2.3245    1.4660 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8574   -1.9742    2.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0005   -2.9790    0.5894 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9929   -0.5111   -1.7141 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7640   -1.9388   -0.7979 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0945   -1.9781   -1.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2224    1.5092   -0.7057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5715    2.9622   -1.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2011   -2.2292    1.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1065   -2.6209    1.4589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0842   -3.4984   -0.1534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8542   -3.8471    1.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9733   -1.3959   -1.9362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9740   -2.9265   -1.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2819   -2.9100   -1.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3094   -0.4014    1.3271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2541   -1.0079    0.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5600   -0.8031   -1.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8902    1.2852   -0.6571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6539    4.6650    1.4045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0191    2.6181    0.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7485    1.4458    1.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4628    0.7217   -1.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 28  1  0
 28 24  1  0
 24 23  2  0
 23 22  1  0
 22 21  1  0
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 17 15  1  0
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 10  7  1  0
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  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
 24 25  1  0
 25 27  1  0
 25 26  2  0
 21 29  1  0
 14 15  1  0
 14 29  1  0
 29 65  1  6
 28 63  1  0
 28 64  1  0
 23 61  1  0
 22 59  1  0
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 19 54  1  0
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 20 56  1  0
 20 57  1  0
 16 51  1  0
 11 49  1  0
 13 50  1  0
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
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  9 48  1  0
  6 41  1  0
  6 42  1  0
  5 39  1  0
  5 40  1  0
  4 37  1  0
  4 38  1  0
  3 35  1  0
  3 36  1  0
  2 33  1  0
  2 34  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 27 62  1  0
M  END


  Mrv0541 05031423532D          

 31 33  0  0  1  0            999 V2000
   -5.3625    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4252    3.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5067    3.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9500    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1250    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7125    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4750    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0625    2.3645    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4125    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    0.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.2211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250    0.2211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -0.4934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    3.0789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.9355    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    3.0789    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 11 10  1  0  0  0  0
 12  9  1  0  0  0  0
 16 10  2  0  0  0  0
 16 13  1  0  0  0  0
 17 14  2  0  0  0  0
 17 15  1  0  0  0  0
 18 13  1  0  0  0  0
 19 11  1  0  0  0  0
 19 18  1  0  0  0  0
 20 14  1  0  0  0  0
 21 15  2  0  0  0  0
 22 18  1  0  0  0  0
 22 20  2  0  0  0  0
 22 21  1  0  0  0  0
 23 16  1  0  0  0  0
 24  2  1  0  0  0  0
 24  3  1  0  0  0  0
 24 12  1  0  0  0  0
 24 17  1  0  0  0  0
 25  4  1  0  0  0  0
 25  5  1  0  0  0  0
 25 19  1  0  0  0  0
 26 20  1  0  0  0  0
 27 23  2  0  0  0  0
 28 23  1  0  0  0  0
 29 21  1  0  0  0  0
 29 25  1  0  0  0  0
 18 30  1  6  0  0  0
 19 31  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0249072

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC(=CC[C@@]1([H])C(C)(C)OC1=CC(=CC(O)=C21)C(C)(C)CCCCCC)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H36O4/c1-6-7-8-9-12-24(2,3)17-14-20(26)22-18-13-16(23(27)28)10-11-19(18)25(4,5)29-21(22)15-17/h10,14-15,18-19,26H,6-9,11-13H2,1-5H3,(H,27,28)/t18-,19-/m1/s1

> <INCHI_KEY>
YCHYFHOSGQABSW-RTBURBONSA-N

> <FORMULA>
C25H36O4

> <MOLECULAR_WEIGHT>
400.5509

> <EXACT_MASS>
400.26135964

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
47.46315470640921

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6aR,10aR)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-6H,6aH,7H,10H,10aH-benzo[c]isochromene-9-carboxylic acid

> <ALOGPS_LOGP>
6.21

> <JCHEM_LOGP>
6.6120532526666675

> <ALOGPS_LOGS>
-5.51

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.98579796532085

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.070611880964228

> <JCHEM_PKA_STRONGEST_BASIC>
-4.883207233550262

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
116.67639999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.25e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ajulemic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   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   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   30  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    6                                                            
CONECT    2   24                                                            
CONECT    3   24                                                            
CONECT    4   25                                                            
CONECT    5   25                                                            
CONECT    6    1    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   12                                                       
CONECT   10   11   16                                                       
CONECT   11   10   19                                                       
CONECT   12    9   24                                                       
CONECT   13   16   18                                                       
CONECT   14   17   20                                                       
CONECT   15   17   21                                                       
CONECT   16   10   13   23                                                  
CONECT   17   14   15   24                                                  
CONECT   18   13   19   22   30                                             
CONECT   19   11   18   25   31                                             
CONECT   20   14   22   26                                                  
CONECT   21   15   22   29                                                  
CONECT   22   18   20   21                                                  
CONECT   23   16   27   28                                                  
CONECT   24    2    3   12   17                                             
CONECT   25    4    5   19   29                                             
CONECT   26   20                                                            
CONECT   27   23                                                            
CONECT   28   23                                                            
CONECT   29   21   25                                                       
CONECT   30   18                                                            
CONECT   31   19                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Value	Source
Ajulemate	Generator
(6AR,10ar)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-6H,6ah,7H,10H,10ah-benzo[c]isochromene-9-carboxylate	Generator

Chemical Formula

C₂₅H₃₆O₄

Average Mass

400.5509 Da

Monoisotopic Mass

400.26136 Da

IUPAC Name

(6aR,10aR)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-6H,6aH,7H,10H,10aH-benzo[c]isochromene-9-carboxylic acid

Traditional Name

ajulemic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC(=CC[C@@]1([H])C(C)(C)OC1=CC(=CC(O)=C21)C(C)(C)CCCCCC)C(O)=O

InChI Identifier

InChI=1S/C25H36O4/c1-6-7-8-9-12-24(2,3)17-14-20(26)22-18-13-16(23(27)28)10-11-19(18)25(4,5)29-21(22)15-17/h10,14-15,18-19,26H,6-9,11-13H2,1-5H3,(H,27,28)/t18-,19-/m1/s1

InChI Key

YCHYFHOSGQABSW-RTBURBONSA-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
Cannabis sativa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

2,2-dimethyl-1-benzopyrans

Alternative Parents

Substituents

2,2-dimethyl-1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Oxacycle
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	6.21	ALOGPS
logP	6.61	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	4.07	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	116.68 m³·mol⁻¹	ChemAxon
Polarizability	47.46 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

DB12193

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

Ajulemic acid

METLIN ID

Not Available

PubChem Compound

3083542

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for ajulemic acid (NP0249072)

MOL for NP0249072 (ajulemic acid)

3D MOL for NP0249072 (ajulemic acid)

3D SDF for NP0249072 (ajulemic acid)

3D-SDF for NP0249072 (ajulemic acid)

PDB for NP0249072 (ajulemic acid)

3D PDB for NP0249072 (ajulemic acid)

SMILES for NP0249072 (ajulemic acid)

INCHI for NP0249072 (ajulemic acid)

Structure for NP0249072 (ajulemic acid)

3D Structure for NP0249072 (ajulemic acid)