NP-MRD: Showing NP-Card for (3s,4r)-4-{[(1s,4ar,5r,8as)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methoxy}-5-methoxy-3-(methoxycarbonyl)-5-oxopentanoic acid (NP0257590)

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Record Information

Version

2.0

Created at

2022-09-07 22:45:30 UTC

Updated at

2022-09-07 22:45:30 UTC

NP-MRD ID

NP0257590

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,4r)-4-{[(1s,4ar,5r,8as)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methoxy}-5-methoxy-3-(methoxycarbonyl)-5-oxopentanoic acid

Description

Cryptoporic acid B, also known as cryptopate b, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. (3s,4r)-4-{[(1s,4ar,5r,8as)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methoxy}-5-methoxy-3-(methoxycarbonyl)-5-oxopentanoic acid is found in Cryptoporus volvatus. Based on a literature review very few articles have been published on Cryptoporic acid B.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309082200452D          

 31 32  0  0  1  0            999 V2000
   -4.2868   -1.6500    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
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0416   -4.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8163   -4.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6408   -4.0572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  1  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
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  1  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
   -2.8579    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    0.4125    0.0000 O   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 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  1  0  0  0
 13 14  1  0  0  0  0
  6 15  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

 67 68  0  0  0  0  0  0  0  0999 V2000
   -0.1782   -1.4198   -2.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9257   -0.5043   -1.9286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0445    0.1382   -2.7266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3477   -0.0353   -1.9775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1542    0.5441   -0.5788 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1606   -0.3521    0.1115 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3997   -1.8185   -0.1362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1059   -0.1152    1.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5064   -0.4899    2.0926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4373    0.5610    1.6112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4047    0.8399    0.1395 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6389    0.2033   -0.4682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6666    2.3564    0.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7935    2.7854   -1.2618 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8088   -0.0071   -0.5393 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3596   -0.4555    0.2391 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5592   -0.0618   -0.3637 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6376   -0.4811    0.4942 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4364   -1.4344   -0.2831 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2428   -1.5720   -1.5105 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4356   -2.2331    0.2753 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2052   -3.1635   -0.4554 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4456    0.7479    0.8542 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0148    1.4161   -0.4051 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7464    2.6531   -0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6308    2.6980    0.8507 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4545    3.8434   -0.7168 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5623    0.4329    1.7360 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5123    0.7784    2.9385 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6762   -0.2392    1.2851 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7304   -0.5255    2.1868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3582   -1.6992   -3.5116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6241   -1.9347   -1.9660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8323    1.1736   -2.9841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1467   -0.4558   -3.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5569   -1.1307   -1.9572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1436    0.5192   -2.5256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5933    1.5127   -0.7827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0437   -2.1724   -1.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8631   -2.3977    0.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4648   -2.1267   -0.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3390   -0.7437    2.0829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9866    0.9633    1.8249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7678   -1.5245    1.8787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4597   -0.4000    3.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4651    0.2870    1.9318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2117    1.4866    2.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4099   -0.6080   -1.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3026    0.9196   -0.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2949   -0.2709    0.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6069    2.5691    0.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8377    2.8648    0.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5537    3.7607   -1.2811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8060    1.1326   -0.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3759   -0.0668    1.2795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4142   -1.5770    0.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2320   -0.9790    1.3823 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2497   -3.2213   -0.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6981   -4.1565   -0.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1723   -3.0281   -1.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7670    1.5286    1.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2230    1.6403   -1.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7582    0.7535   -0.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4718    4.1095   -0.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4990   -1.4965    2.6692 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7784    0.3020    2.9355 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7035   -0.6237    1.6581 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 30  1  0
 30 28  1  0
 28 29  2  0
 28 23  1  0
 23 24  1  0
 24 25  1  0
 25 27  1  0
 25 26  2  0
 23 18  1  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5 11  1  0
 11 12  1  6
 11 13  1  0
 13 14  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  6  1  0
  6  7  1  1
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
  6 15  1  0
  6  5  1  0
 31 65  1  0
 31 66  1  0
 31 67  1  0
 23 61  1  1
 24 62  1  0
 24 63  1  0
 27 64  1  0
 18 57  1  1
 16 55  1  0
 16 56  1  0
 15 54  1  6
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  6
 12 48  1  0
 12 49  1  0
 12 50  1  0
 13 51  1  0
 13 52  1  0
 14 53  1  0
 10 46  1  0
 10 47  1  0
  9 44  1  0
  9 45  1  0
  8 42  1  0
  8 43  1  0
  7 39  1  0
  7 40  1  0
  7 41  1  0
 22 58  1  0
 22 59  1  0
 22 60  1  0
M  END

  Mrv1652309082200452D          

 31 32  0  0  1  0            999 V2000
   -4.2868   -1.6500    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
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0416   -4.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8163   -4.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6408   -4.0572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  1  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
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  1  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
   -2.8579    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    0.4125    0.0000 O   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 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
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  5 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  1  0  0  0
 13 14  1  0  0  0  0
  6 15  1  0  0  0  0
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 19 20  2  0  0  0  0
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 21 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  6  0  0  0
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 23 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0257590

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@H](CC(O)=O)[C@@H](OC[C@H]1C(=C)CC[C@H]2[C@](C)(CO)CCC[C@]12C)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C23H36O8/c1-14-7-8-17-22(2,13-24)9-6-10-23(17,3)16(14)12-31-19(21(28)30-5)15(11-18(25)26)20(27)29-4/h15-17,19,24H,1,6-13H2,2-5H3,(H,25,26)/t15-,16-,17-,19+,22-,23+/m0/s1

> <INCHI_KEY>
FCYLLGSBJNTSAP-DZYDHYRWSA-N

> <FORMULA>
C23H36O8

> <MOLECULAR_WEIGHT>
440.533

> <EXACT_MASS>
440.241018119

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
47.39608076825836

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,4R)-4-{[(1S,4aR,5R,8aS)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-decahydronaphthalen-1-yl]methoxy}-5-methoxy-3-(methyl carboxy)-5-oxopentanoic acid

> <JCHEM_LOGP>
2.1480347193333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.59233662010812

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.1399802912390715

> <JCHEM_PKA_STRONGEST_BASIC>
-1.22707646454311

> <JCHEM_POLAR_SURFACE_AREA>
119.36

> <JCHEM_REFRACTIVITY>
111.84709999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4R)-4-{[(1S,4aR,5R,8aS)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl]methoxy}-5-methoxy-3-(methyl carboxy)-5-oxopentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668  -3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335  -6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667  -6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.944  -7.520   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.390  -7.520   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.929  -7.573   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -5.335   3.080   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -6.668   0.770   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.334   5.390   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.000   3.080   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8   15                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    5   12   13                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13                                                            
CONECT   15    6    2   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21                                                            
CONECT   23   18   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   23   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

View in JSmol

Synonyms

Value	Source
Cryptopate b	Generator
Cryptopic acid b	Generator

Chemical Formula

C₂₃H₃₆O₈

Average Mass

440.5330 Da

Monoisotopic Mass

440.24102 Da

IUPAC Name

(3S,4R)-4-{[(1S,4aR,5R,8aS)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-decahydronaphthalen-1-yl]methoxy}-5-methoxy-3-(methyl carboxy)-5-oxopentanoic acid

Traditional Name

(3S,4R)-4-{[(1S,4aR,5R,8aS)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl]methoxy}-5-methoxy-3-(methyl carboxy)-5-oxopentanoic acid

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@H](CC(O)=O)[C@@H](OC[C@H]1C(=C)CC[C@H]2[C@](C)(CO)CCC[C@]12C)C(=O)OC

InChI Identifier

InChI=1S/C23H36O8/c1-14-7-8-17-22(2,13-24)9-6-10-23(17,3)16(14)12-31-19(21(28)30-5)15(11-18(25)26)20(27)29-4/h15-17,19,24H,1,6-13H2,2-5H3,(H,25,26)/t15-,16-,17-,19+,22-,23+/m0/s1

InChI Key

FCYLLGSBJNTSAP-DZYDHYRWSA-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
Cryptoporus volvatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Fatty acid ester
Monosaccharide
Fatty acyl
Methyl ester
Carboxylic acid ester
Ether
Dialkyl ether
Carboxylic acid
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	2.15	ChemAxon
pKa (Strongest Acidic)	4.14	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	111.85 m³·mol⁻¹	ChemAxon
Polarizability	47.4 Å³	ChemAxon
Number of Rings	2	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

C00031694

Chemspider ID

8065125

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9889454

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s,4r)-4-{[(1s,4ar,5r,8as)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methoxy}-5-methoxy-3-(methoxycarbonyl)-5-oxopentanoic acid (NP0257590)

MOL for NP0257590 ((3s,4r)-4-{[(1s,4ar,5r,8as)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methoxy}-5-methoxy-3-(methoxycarbonyl)-5-oxopentanoic acid)

3D MOL for NP0257590 ((3s,4r)-4-{[(1s,4ar,5r,8as)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methoxy}-5-methoxy-3-(methoxycarbonyl)-5-oxopentanoic acid)

3D SDF for NP0257590 ((3s,4r)-4-{[(1s,4ar,5r,8as)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methoxy}-5-methoxy-3-(methoxycarbonyl)-5-oxopentanoic acid)

3D-SDF for NP0257590 ((3s,4r)-4-{[(1s,4ar,5r,8as)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methoxy}-5-methoxy-3-(methoxycarbonyl)-5-oxopentanoic acid)

PDB for NP0257590 ((3s,4r)-4-{[(1s,4ar,5r,8as)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methoxy}-5-methoxy-3-(methoxycarbonyl)-5-oxopentanoic acid)

3D PDB for NP0257590 ((3s,4r)-4-{[(1s,4ar,5r,8as)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methoxy}-5-methoxy-3-(methoxycarbonyl)-5-oxopentanoic acid)

SMILES for NP0257590 ((3s,4r)-4-{[(1s,4ar,5r,8as)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methoxy}-5-methoxy-3-(methoxycarbonyl)-5-oxopentanoic acid)

INCHI for NP0257590 ((3s,4r)-4-{[(1s,4ar,5r,8as)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methoxy}-5-methoxy-3-(methoxycarbonyl)-5-oxopentanoic acid)

Structure for NP0257590 ((3s,4r)-4-{[(1s,4ar,5r,8as)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methoxy}-5-methoxy-3-(methoxycarbonyl)-5-oxopentanoic acid)

3D Structure for NP0257590 ((3s,4r)-4-{[(1s,4ar,5r,8as)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methoxy}-5-methoxy-3-(methoxycarbonyl)-5-oxopentanoic acid)