NP-MRD: Showing NP-Card for (1s,3s,4ar,7s,8s,8ar)-8-{2-[(2r,4r)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl (2s)-2-methylbutanoate (NP0217911)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 18:24:17 UTC

Updated at

2022-09-05 18:24:17 UTC

NP-MRD ID

NP0217911

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3s,4ar,7s,8s,8ar)-8-{2-[(2r,4r)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl (2s)-2-methylbutanoate

Description

Dihydromevinolin belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety. (1s,3s,4ar,7s,8s,8ar)-8-{2-[(2r,4r)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl (2s)-2-methylbutanoate was first documented in 1987 (PMID: 3656359). Based on a literature review very few articles have been published on Dihydromevinolin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052220242D          

 29 31  0  0  1  0            999 V2000
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  2  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
    5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -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  1  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 O   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 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 13 12  1  6  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  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 21 28  1  0  0  0  0
 29 18  1  6  0  0  0
  8 29  1  0  0  0  0
 13 29  1  0  0  0  0
M  END

     RDKit          3D

 67 69  0  0  0  0  0  0  0  0999 V2000
   -4.8213   -3.6952   -0.7993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5121   -3.3746    0.6243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2011   -1.9427    0.8936 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3146   -1.0037    0.5403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9669   -1.4794    0.2086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3001   -2.2959   -0.5147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4876   -0.2114    0.3027 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2779    0.2554   -0.3643 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7705    1.2454   -1.3622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4123    2.6588   -1.2224 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5529    3.4919   -1.8602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2600    3.0883    0.1828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9736    2.0536    1.1976 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1710    2.6098    2.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1383    2.5522    2.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8558    1.9597    1.0108 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1821    3.0014   -0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1048    0.7449    0.4641 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5156    0.4650   -0.9431 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8977    0.1470   -1.2838 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5640   -1.1004   -0.8335 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6954   -1.2977    0.6241 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9345   -2.1282    0.9892 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7179   -2.8636    2.1504 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3009   -3.0965   -0.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6665   -2.2081   -1.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5890   -2.5595   -2.0248 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9008   -1.0620   -1.3909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3617    0.7896    0.7047 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2663   -4.7332   -0.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9518   -3.6522   -1.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6541   -3.0333   -1.1207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3957   -3.6387    1.2507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6733   -3.9839    1.0352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0625   -1.8543    2.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6882   -1.0976   -0.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9120    0.0437    0.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1328   -1.0429    1.3138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9476   -0.6387   -0.8842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4291    0.9323   -2.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8992    1.1839   -1.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5488    2.9078   -1.8781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4417    3.3441   -1.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7835    3.1293   -2.8702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3150    4.5573   -1.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5368    3.9593    0.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2289    3.5975    0.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9648    1.7567    1.6945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6430    3.0592    3.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6941    2.9831    3.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8380    1.6820    1.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2696    3.1658   -0.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8464    3.9995    0.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6394    2.9279   -0.9625 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5546   -0.0860    1.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9577   -0.5253   -1.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0210    1.1585   -1.6768 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6292    0.9748   -1.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9444    0.1479   -2.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786   -2.0109   -1.3215 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8604   -0.3359    1.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8595   -1.9046    1.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8091   -1.4680    1.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7402   -2.9224    2.2757 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1594   -3.6950    0.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4340   -3.6963   -0.4534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5405    0.0645    1.5754 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 18 29  1  0
 29  8  1  0
 29 13  1  0
 28 21  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  1
  4 36  1  0
  4 37  1  0
  4 38  1  0
  8 39  1  6
  9 40  1  0
  9 41  1  0
 10 42  1  6
 11 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  1
 14 49  1  0
 15 50  1  0
 16 51  1  1
 17 52  1  0
 17 53  1  0
 17 54  1  0
 18 55  1  1
 19 56  1  0
 19 57  1  0
 20 58  1  0
 20 59  1  0
 21 60  1  6
 22 61  1  0
 22 62  1  0
 23 63  1  1
 24 64  1  0
 25 65  1  0
 25 66  1  0
 29 67  1  1
M  END


  Mrv1652309052220242D          

 29 31  0  0  1  0            999 V2000
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  2  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
    5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -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  1  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 O   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 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 13 12  1  6  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  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 21 28  1  0  0  0  0
 29 18  1  6  0  0  0
  8 29  1  0  0  0  0
 13 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0217911

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)C(=O)O[C@H]1C[C@@H](C)C[C@@H]2C=C[C@H](C)[C@H](CC[C@@H]3C[C@@H](O)CC(=O)O3)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C24H38O5/c1-5-15(3)24(27)29-21-11-14(2)10-17-7-6-16(4)20(23(17)21)9-8-19-12-18(25)13-22(26)28-19/h6-7,14-21,23,25H,5,8-13H2,1-4H3/t14-,15-,16-,17-,18+,19+,20-,21-,23+/m0/s1

> <INCHI_KEY>
IFIFFBWHLKGTMO-LDIGTXGYSA-N

> <FORMULA>
C24H38O5

> <MOLECULAR_WEIGHT>
406.563

> <EXACT_MASS>
406.271924324

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
46.30143852314967

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3S,4aR,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl (2S)-2-methylbutanoate

> <JCHEM_LOGP>
4.307766395666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.914537668494884

> <JCHEM_PKA_STRONGEST_BASIC>
-2.836181223800337

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
112.33239999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,4aR,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl (2S)-2-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      10.669   0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      12.003   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.337   3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.670   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.670   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.004   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.004  -1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.670  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.670  -3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.337  -1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.003  -3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.336  -3.850   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.668  -3.850   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.336  -8.470   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      10.669  -6.160   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   29                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   29                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   29                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   28                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   21                                                       
CONECT   29   18    8   13                                                  
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

View in JSmol

Synonyms

Value	Source
4a,5-Dihydromevinolin	MeSH

Chemical Formula

C₂₄H₃₈O₅

Average Mass

406.5630 Da

Monoisotopic Mass

406.27192 Da

IUPAC Name

(1S,3S,4aR,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl (2S)-2-methylbutanoate

Traditional Name

(1S,3S,4aR,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl (2S)-2-methylbutanoate

CAS Registry Number

Not Available

SMILES

CC[C@H](C)C(=O)O[C@H]1C[C@@H](C)C[C@@H]2C=C[C@H](C)[C@H](CC[C@@H]3C[C@@H](O)CC(=O)O3)[C@H]12

InChI Identifier

InChI=1S/C24H38O5/c1-5-15(3)24(27)29-21-11-14(2)10-17-7-6-16(4)20(23(17)21)9-8-19-12-18(25)13-22(26)28-19/h6-7,14-21,23,25H,5,8-13H2,1-4H3/t14-,15-,16-,17-,18+,19+,20-,21-,23+/m0/s1

InChI Key

IFIFFBWHLKGTMO-LDIGTXGYSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Delta valerolactones

Direct Parent

Delta valerolactones

Alternative Parents

Substituents

Delta_valerolactone
Fatty acid ester
Delta valerolactone
Fatty acyl
Oxane
Dicarboxylic acid or derivatives
Secondary alcohol
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	4.31	ChemAxon
pKa (Strongest Acidic)	14.91	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	112.33 m³·mol⁻¹	ChemAxon
Polarizability	46.3 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00018332

Chemspider ID

170261

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

196514

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Heathcock CH, Hadley CR, Rosen T, Theisen PD, Hecker SJ: Total synthesis and biological evaluation of structural analogues of compactin and dihydromevinolin. J Med Chem. 1987 Oct;30(10):1858-73. doi: 10.1021/jm00393a030. [PubMed:3656359 ]
LOTUS database [Link]

Showing NP-Card for (1s,3s,4ar,7s,8s,8ar)-8-{2-[(2r,4r)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl (2s)-2-methylbutanoate (NP0217911)

MOL for NP0217911 ((1s,3s,4ar,7s,8s,8ar)-8-{2-[(2r,4r)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl (2s)-2-methylbutanoate)

3D MOL for NP0217911 ((1s,3s,4ar,7s,8s,8ar)-8-{2-[(2r,4r)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl (2s)-2-methylbutanoate)

3D SDF for NP0217911 ((1s,3s,4ar,7s,8s,8ar)-8-{2-[(2r,4r)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl (2s)-2-methylbutanoate)

3D-SDF for NP0217911 ((1s,3s,4ar,7s,8s,8ar)-8-{2-[(2r,4r)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl (2s)-2-methylbutanoate)

PDB for NP0217911 ((1s,3s,4ar,7s,8s,8ar)-8-{2-[(2r,4r)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl (2s)-2-methylbutanoate)

3D PDB for NP0217911 ((1s,3s,4ar,7s,8s,8ar)-8-{2-[(2r,4r)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl (2s)-2-methylbutanoate)

SMILES for NP0217911 ((1s,3s,4ar,7s,8s,8ar)-8-{2-[(2r,4r)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl (2s)-2-methylbutanoate)

INCHI for NP0217911 ((1s,3s,4ar,7s,8s,8ar)-8-{2-[(2r,4r)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl (2s)-2-methylbutanoate)

Structure for NP0217911 ((1s,3s,4ar,7s,8s,8ar)-8-{2-[(2r,4r)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl (2s)-2-methylbutanoate)

3D Structure for NP0217911 ((1s,3s,4ar,7s,8s,8ar)-8-{2-[(2r,4r)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl (2s)-2-methylbutanoate)