NP-MRD: Showing NP-Card for (2s)-2-[(3r,6s)-6-{2-[(1s,2r,4ar,8ar)-2,4a-dimethyl-5-methylidene-octahydronaphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoic acid (NP0159351)

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Record Information

Version

2.0

Created at

2022-09-02 17:05:28 UTC

Updated at

2022-09-02 17:05:28 UTC

NP-MRD ID

NP0159351

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-[(3r,6s)-6-{2-[(1s,2r,4ar,8ar)-2,4a-dimethyl-5-methylidene-octahydronaphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoic acid

Description

Sigmosceptrellin B belongs to the class of organic compounds known as 1,2-dioxanes. These are organic compounds containing 1,2-dioxane, an aliphatic six-member ring with two oxygen atoms in ring positions 1 and 2. (2s)-2-[(3r,6s)-6-{2-[(1s,2r,4ar,8ar)-2,4a-dimethyl-5-methylidene-octahydronaphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoic acid is found in Diacarnus bismarckensis. (2s)-2-[(3r,6s)-6-{2-[(1s,2r,4ar,8ar)-2,4a-dimethyl-5-methylidene-octahydronaphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoic acid was first documented in 2004 (PMID: 14738401). Based on a literature review a small amount of articles have been published on Sigmosceptrellin B (PMID: 22428230) (PMID: 19159277) (PMID: 20411107).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022219052D          

 27 29  0  0  1  0            999 V2000
    1.4289   -2.4750    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   -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
    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  2  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    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
    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  1  0  0  0  0  0  0  0  0  0
    4.3848    1.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7599    1.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2296    2.5512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5118    3.3265    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9815    3.9585    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1690    3.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2636    4.7337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7333    5.3657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0761    4.8770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3242    3.4697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8545    2.8377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    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
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 10 21  1  0  0  0  0
  7 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  2 26  1  0  0  0  0
  6 26  1  0  0  0  0
 26 27  1  6  0  0  0
M  END

     RDKit          3D

 65 67  0  0  0  0  0  0  0  0999 V2000
   -5.8757   -1.1617   -0.6792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5830   -1.2379   -0.5264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8261   -2.4055   -1.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8936   -2.9343    0.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0816   -1.8681    0.6881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3713   -0.5259    0.0083 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3902    0.5319    0.3897 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1631    0.4156   -0.4996 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0173    1.1749    0.0325 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2376    1.0724   -0.8267 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0295    1.4911   -2.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3382    1.8805   -0.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5982    1.0694    0.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2743   -0.3006    0.5972 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1089   -1.3670   -0.0879 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7296   -2.6987    0.5222 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5534   -1.1507    0.0650 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3041   -2.0072    0.6397 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1611   -0.0147   -0.4047 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9403   -0.6402    0.3823 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6527   -0.2653   -0.8456 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8767    1.9104    0.5718 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5630    2.4670    1.9738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2859    2.2151    0.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0004    1.1542   -0.5660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8240   -0.1541    0.1438 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3004   -0.1111    1.5693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4217   -0.3068   -0.3206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4114   -1.9573   -1.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2936   -2.2276   -1.9695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5328   -3.2603   -1.2351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5150   -3.4292    0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2313   -3.7253   -0.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1965   -1.7953    1.7841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0051   -2.0666    0.5102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2299   -0.7432   -1.0736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9967    0.1947    1.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3848    0.6150   -1.5483 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1240   -0.6753   -0.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2981    0.8200    1.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7372    2.2411    0.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1700    0.6414   -2.9771 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8267    2.2197   -2.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0693    2.0135   -2.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5832    2.7885   -0.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0348    2.2426    0.8485 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2361    1.5904    0.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1285    1.0353   -0.9224 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4671   -0.3470    1.6709 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8801   -1.4036   -1.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8380   -3.1397    0.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6275   -2.5290    1.6199 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5990   -3.3705    0.3860 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7358   -0.0546   -1.2362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2420    2.5770   -0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3834    3.1815    2.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6100    1.5938    2.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5733    2.9174    2.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3854    3.1664   -0.4202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8345    2.4744    1.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5416    1.0575   -1.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0589    1.4561   -0.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9168    0.7153    2.1609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4091   -0.0031    1.5353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0917   -1.0466    2.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 10  1  0
 10 11  1  6
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  1
 26  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
 10 21  1  0
 21 20  1  0
 15 17  1  0
 17 19  1  0
 17 18  2  0
 20 14  1  0
  6  7  1  0
  2 26  1  0
 16 51  1  0
 16 52  1  0
 16 53  1  0
 15 50  1  6
 14 49  1  1
 13 47  1  0
 13 48  1  0
 12 45  1  0
 12 46  1  0
 11 42  1  0
 11 43  1  0
 11 44  1  0
  9 40  1  0
  9 41  1  0
  8 38  1  0
  8 39  1  0
  7 37  1  1
 22 55  1  6
 23 56  1  0
 23 57  1  0
 23 58  1  0
 24 59  1  0
 24 60  1  0
 25 61  1  0
 25 62  1  0
 27 63  1  0
 27 64  1  0
 27 65  1  0
  6 36  1  6
  5 34  1  0
  5 35  1  0
  4 32  1  0
  4 33  1  0
  3 30  1  0
  3 31  1  0
  1 28  1  0
  1 29  1  0
 19 54  1  0
M  END


  Mrv1652309022219052D          

 27 29  0  0  1  0            999 V2000
    1.4289   -2.4750    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   -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
    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  2  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    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
    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  1  0  0  0  0  0  0  0  0  0
    4.3848    1.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7599    1.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2296    2.5512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5118    3.3265    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9815    3.9585    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1690    3.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2636    4.7337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7333    5.3657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0761    4.8770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3242    3.4697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8545    2.8377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    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
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 10 21  1  0  0  0  0
  7 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  2 26  1  0  0  0  0
  6 26  1  0  0  0  0
 26 27  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0159351

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]([C@H]1CC[C@](C)(CC[C@H]2[C@H](C)CC[C@]3(C)[C@@H]2CCCC3=C)OO1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H38O4/c1-15-9-14-23(5)16(2)7-6-8-19(23)18(15)10-12-22(4)13-11-20(26-27-22)17(3)21(24)25/h15,17-20H,2,6-14H2,1,3-5H3,(H,24,25)/t15-,17+,18+,19-,20-,22+,23+/m1/s1

> <INCHI_KEY>
VRMMLZKUQZCNHU-UQILNWLDSA-N

> <FORMULA>
C23H38O4

> <MOLECULAR_WEIGHT>
378.553

> <EXACT_MASS>
378.277009704

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
44.57838141185158

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(3R,6S)-6-{2-[(1S,2R,4aR,8aR)-2,4a-dimethyl-5-methylidene-decahydronaphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoic acid

> <ALOGPS_LOGP>
5.18

> <JCHEM_LOGP>
5.823965619333336

> <ALOGPS_LOGS>
-5.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.2706227348826635

> <JCHEM_PKA_STRONGEST_BASIC>
-4.838719049896132

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
105.8427

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.18e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(3R,6S)-6-{2-[(1S,2R,4aR,8aR)-2,4a-dimethyl-5-methylidene-octahydronaphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.185   3.583   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.152   3.583   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.162   4.762   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.689   6.209   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.699   7.389   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.182   7.122   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.225   8.836   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.236  10.016   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.742   9.104   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.205   6.477   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       7.195   5.297   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   26                                                  
CONECT    7    6    8   22                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   21                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   14   21                                                       
CONECT   21   20   10                                                       
CONECT   22    7   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25    2    6   27                                             
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₈O₄

Average Mass

378.5530 Da

Monoisotopic Mass

378.27701 Da

IUPAC Name

(2S)-2-[(3R,6S)-6-{2-[(1S,2R,4aR,8aR)-2,4a-dimethyl-5-methylidene-decahydronaphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoic acid

Traditional Name

(2S)-2-[(3R,6S)-6-{2-[(1S,2R,4aR,8aR)-2,4a-dimethyl-5-methylidene-octahydronaphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]([C@H]1CC[C@](C)(CC[C@H]2[C@H](C)CC[C@]3(C)[C@@H]2CCCC3=C)OO1)C(O)=O

InChI Identifier

InChI=1S/C23H38O4/c1-15-9-14-23(5)16(2)7-6-8-19(23)18(15)10-12-22(4)13-11-20(26-27-22)17(3)21(24)25/h15,17-20H,2,6-14H2,1,3-5H3,(H,24,25)/t15-,17+,18+,19-,20-,22+,23+/m1/s1

InChI Key

VRMMLZKUQZCNHU-UQILNWLDSA-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
Diacarnus bismarckensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,2-dioxanes. These are organic compounds containing 1,2-dioxane, an aliphatic six-member ring with two oxygen atoms in ring positions 1 and 2.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dioxanes

Sub Class

1,2-dioxanes

Direct Parent

1,2-dioxanes

Alternative Parents

Substituents

Ortho-dioxane
Dialkyl peroxide
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	5.18	ALOGPS
logP	5.82	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	4.27	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	105.84 m³·mol⁻¹	ChemAxon
Polarizability	44.58 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00043922

Chemspider ID

24697896

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44584775

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ibrahim SR: Diacarperoxide S, new norterpene cyclic peroxide from the sponge Diacarnus megaspinorhabdosa. Nat Prod Commun. 2012 Jan;7(1):9-12. [PubMed:22428230 ]
Youssef DT: Tasnemoxides A-C, new cytotoxic cyclic norsesterterpene peroxides from the Red Sea sponge Diacarnus erythraenus. J Nat Prod. 2004 Jan;67(1):112-4. doi: 10.1021/np0340192. [PubMed:14738401 ]
Rubio BK, Tenney K, Ang KH, Abdulla M, Arkin M, McKerrow JH, Crews P: The marine sponge Diacarnus bismarckensis as a source of peroxiterpene inhibitors of Trypanosoma brucei, the causative agent of sleeping sickness. J Nat Prod. 2009 Feb 27;72(2):218-22. doi: 10.1021/np800711a. [PubMed:19159277 ]
Cheenpracha S, Park EJ, Rostama B, Pezzuto JM, Chang LC: Inhibition of nitric oxide (NO) production in lipopolysaccharide (LPS)-activated murine macrophage RAW 264.7 cells by the norsesterterpene peroxide, epimuqubilin A. Mar Drugs. 2010 Mar 1;8(3):429-37. doi: 10.3390/md8030429. [PubMed:20411107 ]
LOTUS database [Link]

Showing NP-Card for (2s)-2-[(3r,6s)-6-{2-[(1s,2r,4ar,8ar)-2,4a-dimethyl-5-methylidene-octahydronaphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoic acid (NP0159351)

MOL for NP0159351 ((2s)-2-[(3r,6s)-6-{2-[(1s,2r,4ar,8ar)-2,4a-dimethyl-5-methylidene-octahydronaphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoic acid)

3D MOL for NP0159351 ((2s)-2-[(3r,6s)-6-{2-[(1s,2r,4ar,8ar)-2,4a-dimethyl-5-methylidene-octahydronaphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoic acid)

3D SDF for NP0159351 ((2s)-2-[(3r,6s)-6-{2-[(1s,2r,4ar,8ar)-2,4a-dimethyl-5-methylidene-octahydronaphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoic acid)

3D-SDF for NP0159351 ((2s)-2-[(3r,6s)-6-{2-[(1s,2r,4ar,8ar)-2,4a-dimethyl-5-methylidene-octahydronaphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoic acid)

PDB for NP0159351 ((2s)-2-[(3r,6s)-6-{2-[(1s,2r,4ar,8ar)-2,4a-dimethyl-5-methylidene-octahydronaphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoic acid)

3D PDB for NP0159351 ((2s)-2-[(3r,6s)-6-{2-[(1s,2r,4ar,8ar)-2,4a-dimethyl-5-methylidene-octahydronaphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoic acid)

SMILES for NP0159351 ((2s)-2-[(3r,6s)-6-{2-[(1s,2r,4ar,8ar)-2,4a-dimethyl-5-methylidene-octahydronaphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoic acid)

INCHI for NP0159351 ((2s)-2-[(3r,6s)-6-{2-[(1s,2r,4ar,8ar)-2,4a-dimethyl-5-methylidene-octahydronaphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoic acid)

Structure for NP0159351 ((2s)-2-[(3r,6s)-6-{2-[(1s,2r,4ar,8ar)-2,4a-dimethyl-5-methylidene-octahydronaphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoic acid)

3D Structure for NP0159351 ((2s)-2-[(3r,6s)-6-{2-[(1s,2r,4ar,8ar)-2,4a-dimethyl-5-methylidene-octahydronaphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoic acid)