NP-MRD: Showing NP-Card for Vibralactone B (NP0007965)

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Record Information

Version

2.0

Created at

2020-12-09 05:34:52 UTC

Updated at

2021-07-15 16:59:03 UTC

NP-MRD ID

NP0007965

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Vibralactone B

Provided By

NPAtlas

Description

Vibralactone B belongs to the class of organic compounds known as lactones. These are cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. Vibralactone B is found in Boreostereum vibrans. Vibralactone B was first documented in 2008 (PMID: 18758102). Based on a literature review very few articles have been published on Vibralactone B (PMID: 26020559) (PMID: 29209983) (PMID: 28528973).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106053D          

 32 34  0  0  0  0            999 V2000
   -4.1297   -1.3978   -0.5764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7206   -1.0800   -0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5075   -0.9522    1.3113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8150   -0.9313   -1.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4250   -0.6447   -1.1258 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5610   -0.4397   -0.1282 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9216   -1.4629    0.8792 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6933   -2.6508    1.1454 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6970   -0.4288    1.4517 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5941    0.4179    1.0286 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0527    1.7644    0.5115 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1910    1.3570   -0.3789 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6031    1.6394    0.0364 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1241    2.6973   -0.7060 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9025    0.9997   -1.6807 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9237   -0.0619   -0.8144 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8689   -1.0848    0.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2245   -2.4498   -0.8739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2951   -0.7635   -1.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7525   -1.6176    1.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3965    0.1233    1.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4860   -1.2381    1.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2763   -1.0740   -2.0800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0018   -1.4466   -1.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3593    0.2608   -1.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0906    0.4273    1.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3578    2.4416    1.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2071    2.1896   -0.0646 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2568    0.7682   -0.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6489    1.8880    1.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9222    3.5746   -0.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6888   -0.8247   -0.8492 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  3  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  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 10  6  1  0  0  0  0
 16 12  1  0  0  0  0
 16  6  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  3 20  1  0  0  0  0
  3 21  1  0  0  0  0
  3 22  1  0  0  0  0
  4 23  1  0  0  0  0
  5 24  1  0  0  0  0
  5 25  1  0  0  0  0
 10 26  1  1  0  0  0
 11 27  1  0  0  0  0
 11 28  1  0  0  0  0
 13 29  1  0  0  0  0
 13 30  1  0  0  0  0
 14 31  1  0  0  0  0
 16 32  1  6  0  0  0
M  END

     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
   -4.1297   -1.3978   -0.5764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7206   -1.0800   -0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5075   -0.9522    1.3113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8150   -0.9313   -1.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4250   -0.6447   -1.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5610   -0.4397   -0.1282 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9216   -1.4629    0.8792 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6933   -2.6508    1.1454 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6970   -0.4288    1.4517 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5941    0.4179    1.0286 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0527    1.7644    0.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1910    1.3570   -0.3789 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6031    1.6394    0.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1241    2.6973   -0.7060 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9025    0.9997   -1.6807 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9237   -0.0619   -0.8144 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8689   -1.0848    0.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2245   -2.4498   -0.8739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2951   -0.7635   -1.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7525   -1.6176    1.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3965    0.1233    1.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4860   -1.2381    1.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2763   -1.0740   -2.0800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0018   -1.4466   -1.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3593    0.2608   -1.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0906    0.4273    1.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3578    2.4416    1.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2071    2.1896   -0.0646 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2568    0.7682   -0.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6489    1.8880    1.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9222    3.5746   -0.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6888   -0.8247   -0.8492 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  6  5  1  6
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  6
 13 14  1  0
 12 15  1  0
 15 16  1  0
 10  6  1  0
 16 12  1  0
 16  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
 10 26  1  1
 11 27  1  0
 11 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  6
M  END


  Mrv1652306242106053D          

 32 34  0  0  0  0            999 V2000
   -4.1297   -1.3978   -0.5764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7206   -1.0800   -0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5075   -0.9522    1.3113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8150   -0.9313   -1.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4250   -0.6447   -1.1258 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5610   -0.4397   -0.1282 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9216   -1.4629    0.8792 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6933   -2.6508    1.1454 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6970   -0.4288    1.4517 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5941    0.4179    1.0286 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0527    1.7644    0.5115 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1910    1.3570   -0.3789 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6031    1.6394    0.0364 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1241    2.6973   -0.7060 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9025    0.9997   -1.6807 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9237   -0.0619   -0.8144 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8689   -1.0848    0.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2245   -2.4498   -0.8739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2951   -0.7635   -1.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7525   -1.6176    1.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3965    0.1233    1.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4860   -1.2381    1.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2763   -1.0740   -2.0800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0018   -1.4466   -1.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3593    0.2608   -1.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0906    0.4273    1.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3578    2.4416    1.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2071    2.1896   -0.0646 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2568    0.7682   -0.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6489    1.8880    1.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9222    3.5746   -0.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6888   -0.8247   -0.8492 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  3  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  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 10  6  1  0  0  0  0
 16 12  1  0  0  0  0
 16  6  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  3 20  1  0  0  0  0
  3 21  1  0  0  0  0
  3 22  1  0  0  0  0
  4 23  1  0  0  0  0
  5 24  1  0  0  0  0
  5 25  1  0  0  0  0
 10 26  1  1  0  0  0
 11 27  1  0  0  0  0
 11 28  1  0  0  0  0
 13 29  1  0  0  0  0
 13 30  1  0  0  0  0
 14 31  1  0  0  0  0
 16 32  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0007965

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]12O[C@]1([H])[C@]1(C(=O)O[C@@]1([H])C2([H])[H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C12H16O4/c1-7(2)3-4-12-8(15-10(12)14)5-11(6-13)9(12)16-11/h3,8-9,13H,4-6H2,1-2H3/t8-,9-,11+,12-/m0/s1

> <INCHI_KEY>
NOIVROLINHAPPT-XPXLGCRWSA-N

> <FORMULA>
C12H16O4

> <MOLECULAR_WEIGHT>
224.256

> <EXACT_MASS>
224.104858995

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
23.211898059835846

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,4R,6S)-4-(hydroxymethyl)-1-(3-methylbut-2-en-1-yl)-3,7-dioxatricyclo[4.2.0.0^{2,4}]octan-8-one

> <ALOGPS_LOGP>
0.73

> <JCHEM_LOGP>
0.6672694019999994

> <ALOGPS_LOGS>
-1.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.278628348313223

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1143279604477963

> <JCHEM_POLAR_SURFACE_AREA>
59.06

> <JCHEM_REFRACTIVITY>
56.476

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.15e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4R,6S)-4-(hydroxymethyl)-1-(3-methylbut-2-en-1-yl)-3,7-dioxatricyclo[4.2.0.0^{2,4}]octan-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
   -4.1297   -1.3978   -0.5764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7206   -1.0800   -0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5075   -0.9522    1.3113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8150   -0.9313   -1.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4250   -0.6447   -1.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5610   -0.4397   -0.1282 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9216   -1.4629    0.8792 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6933   -2.6508    1.1454 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6970   -0.4288    1.4517 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5941    0.4179    1.0286 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0527    1.7644    0.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1910    1.3570   -0.3789 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6031    1.6394    0.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1241    2.6973   -0.7060 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9025    0.9997   -1.6807 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9237   -0.0619   -0.8144 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8689   -1.0848    0.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2245   -2.4498   -0.8739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2951   -0.7635   -1.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7525   -1.6176    1.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3965    0.1233    1.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4860   -1.2381    1.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2763   -1.0740   -2.0800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0018   -1.4466   -1.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3593    0.2608   -1.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0906    0.4273    1.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3578    2.4416    1.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2071    2.1896   -0.0646 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2568    0.7682   -0.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6489    1.8880    1.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9222    3.5746   -0.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6888   -0.8247   -0.8492 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  6  5  1  6
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  6
 13 14  1  0
 12 15  1  0
 15 16  1  0
 10  6  1  0
 16 12  1  0
 16  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
 10 26  1  1
 11 27  1  0
 11 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  6
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.130  -1.398  -0.576  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.721  -1.080  -0.127  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.507  -0.952   1.311  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.815  -0.931  -1.018  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.425  -0.645  -1.126  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.561  -0.440  -0.128  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.922  -1.463   0.879  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.693  -2.651   1.145  0.00  0.00           O+0
HETATM    9  O   UNK     0       1.697  -0.429   1.452  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.594   0.418   1.029  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.053   1.764   0.511  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.191   1.357  -0.379  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.603   1.639   0.036  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.124   2.697  -0.706  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.903   1.000  -1.681  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.924  -0.062  -0.814  0.00  0.00           C+0
HETATM   17  H   UNK     0      -4.869  -1.085   0.183  0.00  0.00           H+0
HETATM   18  H   UNK     0      -4.224  -2.450  -0.874  0.00  0.00           H+0
HETATM   19  H   UNK     0      -4.295  -0.764  -1.473  0.00  0.00           H+0
HETATM   20  H   UNK     0      -1.753  -1.618   1.757  0.00  0.00           H+0
HETATM   21  H   UNK     0      -2.397   0.123   1.634  0.00  0.00           H+0
HETATM   22  H   UNK     0      -3.486  -1.238   1.829  0.00  0.00           H+0
HETATM   23  H   UNK     0      -2.276  -1.074  -2.080  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.002  -1.447  -1.851  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.359   0.261  -1.848  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.091   0.427   1.853  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.358   2.442   1.327  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.207   2.190  -0.065  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.257   0.768  -0.155  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.649   1.888   1.099  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.922   3.575  -0.296  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.689  -0.825  -0.849  0.00  0.00           H+0
CONECT    1    2   17   18   19                                             
CONECT    2    1    3    4                                                  
CONECT    3    2   20   21   22                                             
CONECT    4    2    5   23                                                  
CONECT    5    4    6   24   25                                             
CONECT    6    5    7   10   16                                             
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11    6   26                                             
CONECT   11   10   12   27   28                                             
CONECT   12   11   13   15   16                                             
CONECT   13   12   14   29   30                                             
CONECT   14   13   31                                                       
CONECT   15   12   16                                                       
CONECT   16   15   12    6   32                                             
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    1                                                            
CONECT   20    3                                                            
CONECT   21    3                                                            
CONECT   22    3                                                            
CONECT   23    4                                                            
CONECT   24    5                                                            
CONECT   25    5                                                            
CONECT   26   10                                                            
CONECT   27   11                                                            
CONECT   28   11                                                            
CONECT   29   13                                                            
CONECT   30   13                                                            
CONECT   31   14                                                            
CONECT   32   16                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

RDKit          3D

32 34  0  0  0  0  0  0  0  0999 V2000
   -4.1297   -1.3978   -0.5764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7206   -1.0800   -0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5075   -0.9522    1.3113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8150   -0.9313   -1.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4250   -0.6447   -1.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5610   -0.4397   -0.1282 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9216   -1.4629    0.8792 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6933   -2.6508    1.1454 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6970   -0.4288    1.4517 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5941    0.4179    1.0286 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0527    1.7644    0.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1910    1.3570   -0.3789 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6031    1.6394    0.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1241    2.6973   -0.7060 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9025    0.9997   -1.6807 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9237   -0.0619   -0.8144 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8689   -1.0848    0.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2245   -2.4498   -0.8739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2951   -0.7635   -1.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7525   -1.6176    1.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3965    0.1233    1.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4860   -1.2381    1.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2763   -1.0740   -2.0800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0018   -1.4466   -1.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3593    0.2608   -1.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0906    0.4273    1.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3578    2.4416    1.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2071    2.1896   -0.0646 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2568    0.7682   -0.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6489    1.8880    1.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9222    3.5746   -0.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6888   -0.8247   -0.8492 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  6  5  1  6
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  6
 13 14  1  0
 12 15  1  0
 15 16  1  0
 10  6  1  0
 16 12  1  0
 16  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
 10 26  1  1
 11 27  1  0
 11 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  6
M  END

View in JSmol View NMR Assignments View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₁₂H₁₆O₄

Average Mass

224.2560 Da

Monoisotopic Mass

224.10486 Da

IUPAC Name

(1S,2R,4R,6S)-4-(hydroxymethyl)-1-(3-methylbut-2-en-1-yl)-3,7-dioxatricyclo[4.2.0.0^{2,4}]octan-8-one

Traditional Name

(1S,2R,4R,6S)-4-(hydroxymethyl)-1-(3-methylbut-2-en-1-yl)-3,7-dioxatricyclo[4.2.0.0^{2,4}]octan-8-one

CAS Registry Number

Not Available

SMILES

CC(C)=CC[C@@]12[C@H]3O[C@@]3(CO)C[C@@H]1OC2=O

InChI Identifier

InChI=1S/C12H16O4/c1-7(2)3-4-12-8(15-10(12)14)5-11(6-13)9(12)16-11/h3,8-9,13H,4-6H2,1-2H3/t8-,9-,11+,12-/m0/s1

InChI Key

NOIVROLINHAPPT-XPXLGCRWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Boreostereum vibrans	NPAtlas	18758102

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lactones. These are cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Not Available

Direct Parent

Lactones

Alternative Parents

Substituents

Caprolactone
Oxepane
Oxane
Beta_propiolactone
Carboxylic acid ester
Lactone
Oxetane
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Alcohol
Carbonyl group
Organic oxide
Organic oxygen compound
Primary 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	0.73	ALOGPS
logP	0.67	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	14.28	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	56.48 m³·mol⁻¹	ChemAxon
Polarizability	23.21 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	No	ChemAxon

External Links

NPAtlas ID

NPA008010

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00032486

Chemspider ID

28285602

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102473701

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jiang MY, Wang F, Yang XL, Fang LZ, Dong ZJ, Zhu HJ, Liu JK: Derivatives of vibralactone from cultures of the basidiomycete Boreostereum vibrans. Chem Pharm Bull (Tokyo). 2008 Sep;56(9):1286-8. doi: 10.1248/cpb.56.1286. [PubMed:18758102 ]
Aqueveque P, Cespedes CL, Becerra J, Davila M, Sterner O: Bioactive compounds isolated from submerged fermentations of the Chilean fungus Stereum rameale. Z Naturforsch C J Biosci. 2015;70(3-4):97-102. doi: 10.1515/znc-2015-5005. [PubMed:26020559 ]
Chen HP, Jiang MY, Zhao ZZ, Feng T, Li ZH, Liu JK: Vibralactone Biogenesis-Associated Analogues from Submerged Cultures of the Fungus Boreostereum vibrans. Nat Prod Bioprospect. 2018 Feb;8(1):37-45. doi: 10.1007/s13659-017-0147-5. Epub 2017 Dec 5. [PubMed:29209983 ]
Aqueveque P, Cespedes CL, Becerra J, Aranda M, Sterner O: Antifungal activities of secondary metabolites isolated from liquid fermentations of Stereum hirsutum (Sh134-11) against Botrytis cinerea (grey mould agent). Food Chem Toxicol. 2017 Nov;109(Pt 2):1048-1054. doi: 10.1016/j.fct.2017.05.036. Epub 2017 May 18. [PubMed:28528973 ]

Showing NP-Card for Vibralactone B (NP0007965)

MOL for NP0007965 (Vibralactone B)

3D MOL for NP0007965 (Vibralactone B)

3D SDF for NP0007965 (Vibralactone B)

3D-SDF for NP0007965 (Vibralactone B)

PDB for NP0007965 (Vibralactone B)

3D PDB for NP0007965 (Vibralactone B)

SMILES for NP0007965 (Vibralactone B)

INCHI for NP0007965 (Vibralactone B)

Structure for NP0007965 (Vibralactone B)

3D Structure for NP0007965 (Vibralactone B)