NP-MRD: Showing NP-Card for Sporothriolide (NP0022739)

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Record Information

Version

2.0

Created at

2021-01-06 07:55:06 UTC

Updated at

2021-07-15 17:39:51 UTC

NP-MRD ID

NP0022739

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sporothriolide

Provided By

NPAtlas

Description

Sporothriolide is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Sporothriolide is found in Sporothrix sp. Sporothriolide was first documented in 1994 (PMID: 8119853). Based on a literature review a small amount of articles have been published on Sporothriolide (PMID: 29043802) (PMID: 11483061) (PMID: 25379335) (PMID: 27017876).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105373D          

 35 36  0  0  0  0            999 V2000
   -5.2798    0.4157    0.4905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9679    0.5003    0.4688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1424    1.2450    1.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4944    1.9356    2.4009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7872    1.0926    1.0414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7921    0.6776   -0.3214 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0718   -0.1308   -0.4931 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6077   -1.4789   -0.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2308   -2.3140    0.6671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3564   -1.6150   -0.6563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7120   -0.3597   -0.5732 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2472   -0.4226    0.5920 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2902   -1.4696    0.2961 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0462   -1.1203   -0.9534 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7034    0.2193   -0.8098 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6660    0.1845    0.3515 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3434    1.5410    0.4720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8840    0.9250    1.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8584   -0.1500   -0.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7893    1.5010   -1.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4260   -0.1259   -1.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2355   -0.0530   -1.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6830    0.5637    0.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3886   -0.7727    1.4646 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9611   -1.6427    1.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7392   -2.4446    0.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8232   -1.9301   -1.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4137   -1.1072   -1.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2460    0.4988   -1.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9594    1.0351   -0.6346 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3771   -0.6415    0.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0550   -0.0125    1.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0991    1.4430    1.2665 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5508    2.2749    0.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8202    1.7378   -0.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  7  2  1  0  0  0  0
 11  6  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  6 20  1  6  0  0  0
  7 21  1  6  0  0  0
 11 22  1  6  0  0  0
 12 23  1  0  0  0  0
 12 24  1  0  0  0  0
 13 25  1  0  0  0  0
 13 26  1  0  0  0  0
 14 27  1  0  0  0  0
 14 28  1  0  0  0  0
 15 29  1  0  0  0  0
 15 30  1  0  0  0  0
 16 31  1  0  0  0  0
 16 32  1  0  0  0  0
 17 33  1  0  0  0  0
 17 34  1  0  0  0  0
 17 35  1  0  0  0  0
M  END

     RDKit          3D

 35 36  0  0  0  0  0  0  0  0999 V2000
   -5.2798    0.4157    0.4905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9679    0.5003    0.4688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1424    1.2450    1.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4944    1.9356    2.4009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7872    1.0926    1.0414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7921    0.6776   -0.3214 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0718   -0.1308   -0.4931 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6077   -1.4789   -0.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2308   -2.3140    0.6671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3564   -1.6150   -0.6563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7120   -0.3597   -0.5732 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2472   -0.4226    0.5920 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2902   -1.4696    0.2961 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0462   -1.1203   -0.9534 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7034    0.2193   -0.8098 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6660    0.1845    0.3515 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3434    1.5410    0.4720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8840    0.9250    1.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8584   -0.1500   -0.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7893    1.5010   -1.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4260   -0.1259   -1.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2355   -0.0530   -1.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6830    0.5637    0.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3886   -0.7727    1.4646 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9611   -1.6427    1.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7392   -2.4446    0.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8232   -1.9301   -1.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4137   -1.1072   -1.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2460    0.4988   -1.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9594    1.0351   -0.6346 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3771   -0.6415    0.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0550   -0.0125    1.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0991    1.4430    1.2665 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5508    2.2749    0.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8202    1.7378   -0.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  7  2  1  0
 11  6  1  0
  1 18  1  0
  1 19  1  0
  6 20  1  6
  7 21  1  6
 11 22  1  6
 12 23  1  0
 12 24  1  0
 13 25  1  0
 13 26  1  0
 14 27  1  0
 14 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
M  END


  Mrv1652306242105373D          

 35 36  0  0  0  0            999 V2000
   -5.2798    0.4157    0.4905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9679    0.5003    0.4688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1424    1.2450    1.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4944    1.9356    2.4009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7872    1.0926    1.0414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7921    0.6776   -0.3214 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0718   -0.1308   -0.4931 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6077   -1.4789   -0.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2308   -2.3140    0.6671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3564   -1.6150   -0.6563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7120   -0.3597   -0.5732 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2472   -0.4226    0.5920 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2902   -1.4696    0.2961 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0462   -1.1203   -0.9534 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7034    0.2193   -0.8098 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6660    0.1845    0.3515 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3434    1.5410    0.4720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8840    0.9250    1.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8584   -0.1500   -0.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7893    1.5010   -1.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4260   -0.1259   -1.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2355   -0.0530   -1.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6830    0.5637    0.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3886   -0.7727    1.4646 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9611   -1.6427    1.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7392   -2.4446    0.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8232   -1.9301   -1.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4137   -1.1072   -1.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2460    0.4988   -1.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9594    1.0351   -0.6346 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3771   -0.6415    0.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0550   -0.0125    1.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0991    1.4430    1.2665 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5508    2.2749    0.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8202    1.7378   -0.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  7  2  1  0  0  0  0
 11  6  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  6 20  1  6  0  0  0
  7 21  1  6  0  0  0
 11 22  1  6  0  0  0
 12 23  1  0  0  0  0
 12 24  1  0  0  0  0
 13 25  1  0  0  0  0
 13 26  1  0  0  0  0
 14 27  1  0  0  0  0
 14 28  1  0  0  0  0
 15 29  1  0  0  0  0
 15 30  1  0  0  0  0
 16 31  1  0  0  0  0
 16 32  1  0  0  0  0
 17 33  1  0  0  0  0
 17 34  1  0  0  0  0
 17 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0022739

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])=C1C(=O)O[C@@]2([H])[C@]([H])(OC(=O)[C@@]12[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C13H18O4/c1-3-4-5-6-7-9-11-10(13(15)16-9)8(2)12(14)17-11/h9-11H,2-7H2,1H3/t9-,10+,11+/m1/s1

> <INCHI_KEY>
AENZSPQGLJVLND-VWYCJHECSA-N

> <FORMULA>
C13H18O4

> <MOLECULAR_WEIGHT>
238.283

> <EXACT_MASS>
238.12050906

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
25.36511996128319

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,6R,6aR)-6-hexyl-3-methylidene-hexahydrofuro[2,3-c]furan-2,4-dione

> <ALOGPS_LOGP>
2.91

> <JCHEM_LOGP>
2.964352524

> <ALOGPS_LOGS>
-2.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.866745183149977

> <JCHEM_PKA_STRONGEST_BASIC>
-6.7114995538049005

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
60.589

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.30e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,6R,6aR)-6-hexyl-3-methylidene-dihydro-3aH-furo[2,3-c]furan-2,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 35 36  0  0  0  0  0  0  0  0999 V2000
   -5.2798    0.4157    0.4905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9679    0.5003    0.4688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1424    1.2450    1.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4944    1.9356    2.4009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7872    1.0926    1.0414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7921    0.6776   -0.3214 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0718   -0.1308   -0.4931 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6077   -1.4789   -0.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2308   -2.3140    0.6671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3564   -1.6150   -0.6563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7120   -0.3597   -0.5732 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2472   -0.4226    0.5920 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2902   -1.4696    0.2961 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0462   -1.1203   -0.9534 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7034    0.2193   -0.8098 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6660    0.1845    0.3515 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3434    1.5410    0.4720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8840    0.9250    1.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8584   -0.1500   -0.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7893    1.5010   -1.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4260   -0.1259   -1.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2355   -0.0530   -1.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6830    0.5637    0.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3886   -0.7727    1.4646 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9611   -1.6427    1.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7392   -2.4446    0.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8232   -1.9301   -1.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4137   -1.1072   -1.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2460    0.4988   -1.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9594    1.0351   -0.6346 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3771   -0.6415    0.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0550   -0.0125    1.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0991    1.4430    1.2665 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5508    2.2749    0.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8202    1.7378   -0.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  7  2  1  0
 11  6  1  0
  1 18  1  0
  1 19  1  0
  6 20  1  6
  7 21  1  6
 11 22  1  6
 12 23  1  0
 12 24  1  0
 13 25  1  0
 13 26  1  0
 14 27  1  0
 14 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
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      -5.280   0.416   0.491  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.968   0.500   0.469  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.142   1.245   1.406  0.00  0.00           C+0
HETATM    4  O   UNK     0      -3.494   1.936   2.401  0.00  0.00           O+0
HETATM    5  O   UNK     0      -1.787   1.093   1.041  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.792   0.678  -0.321  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.072  -0.131  -0.493  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.608  -1.479  -0.070  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.231  -2.314   0.667  0.00  0.00           O+0
HETATM   10  O   UNK     0      -1.356  -1.615  -0.656  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.712  -0.360  -0.573  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.247  -0.423   0.592  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.290  -1.470   0.296  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.046  -1.120  -0.953  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.703   0.219  -0.810  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.666   0.185   0.352  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.343   1.541   0.472  0.00  0.00           C+0
HETATM   18  H   UNK     0      -5.884   0.925   1.254  0.00  0.00           H+0
HETATM   19  H   UNK     0      -5.858  -0.150  -0.226  0.00  0.00           H+0
HETATM   20  H   UNK     0      -1.789   1.501  -1.029  0.00  0.00           H+0
HETATM   21  H   UNK     0      -3.426  -0.126  -1.533  0.00  0.00           H+0
HETATM   22  H   UNK     0      -0.236  -0.053  -1.528  0.00  0.00           H+0
HETATM   23  H   UNK     0       0.683   0.564   0.854  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.389  -0.773   1.465  0.00  0.00           H+0
HETATM   25  H   UNK     0       1.961  -1.643   1.159  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.739  -2.445   0.160  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.823  -1.930  -1.112  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.414  -1.107  -1.857  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.246   0.499  -1.759  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.959   1.035  -0.635  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.377  -0.642   0.174  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.055  -0.013   1.278  0.00  0.00           H+0
HETATM   33  H   UNK     0       5.099   1.443   1.266  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.551   2.275   0.706  0.00  0.00           H+0
HETATM   35  H   UNK     0       4.820   1.738  -0.503  0.00  0.00           H+0
CONECT    1    2   18   19                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   11   20                                             
CONECT    7    6    8    2   21                                             
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12    6   22                                             
CONECT   12   11   13   23   24                                             
CONECT   13   12   14   25   26                                             
CONECT   14   13   15   27   28                                             
CONECT   15   14   16   29   30                                             
CONECT   16   15   17   31   32                                             
CONECT   17   16   33   34   35                                             
CONECT   18    1                                                            
CONECT   19    1                                                            
CONECT   20    6                                                            
CONECT   21    7                                                            
CONECT   22   11                                                            
CONECT   23   12                                                            
CONECT   24   12                                                            
CONECT   25   13                                                            
CONECT   26   13                                                            
CONECT   27   14                                                            
CONECT   28   14                                                            
CONECT   29   15                                                            
CONECT   30   15                                                            
CONECT   31   16                                                            
CONECT   32   16                                                            
CONECT   33   17                                                            
CONECT   34   17                                                            
CONECT   35   17                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   72    0
END

RDKit          3D

35 36  0  0  0  0  0  0  0  0999 V2000
   -5.2798    0.4157    0.4905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9679    0.5003    0.4688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1424    1.2450    1.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4944    1.9356    2.4009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7872    1.0926    1.0414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7921    0.6776   -0.3214 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0718   -0.1308   -0.4931 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6077   -1.4789   -0.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2308   -2.3140    0.6671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3564   -1.6150   -0.6563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7120   -0.3597   -0.5732 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2472   -0.4226    0.5920 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2902   -1.4696    0.2961 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0462   -1.1203   -0.9534 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7034    0.2193   -0.8098 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6660    0.1845    0.3515 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3434    1.5410    0.4720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8840    0.9250    1.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8584   -0.1500   -0.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7893    1.5010   -1.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4260   -0.1259   -1.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2355   -0.0530   -1.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6830    0.5637    0.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3886   -0.7727    1.4646 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9611   -1.6427    1.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7392   -2.4446    0.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8232   -1.9301   -1.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4137   -1.1072   -1.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2460    0.4988   -1.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9594    1.0351   -0.6346 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3771   -0.6415    0.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0550   -0.0125    1.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0991    1.4430    1.2665 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5508    2.2749    0.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8202    1.7378   -0.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  7  2  1  0
 11  6  1  0
  1 18  1  0
  1 19  1  0
  6 20  1  6
  7 21  1  6
 11 22  1  6
 12 23  1  0
 12 24  1  0
 13 25  1  0
 13 26  1  0
 14 27  1  0
 14 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
6-N-Hexyl-3,3a,6,6a-tetrahydro-3-methylenefuro(3,4-b)furan-2,4-dione	MeSH

Chemical Formula

C₁₃H₁₈O₄

Average Mass

238.2830 Da

Monoisotopic Mass

238.12051 Da

IUPAC Name

(3aS,6R,6aR)-6-hexyl-3-methylidene-hexahydrofuro[2,3-c]furan-2,4-dione

Traditional Name

(3aS,6R,6aR)-6-hexyl-3-methylidene-dihydro-3aH-furo[2,3-c]furan-2,4-dione

CAS Registry Number

Not Available

SMILES

CCCCCC[C@H]1OC(=O)[C@@H]2[C@H]1OC(=O)C2=C

InChI Identifier

InChI=1S/C13H18O4/c1-3-4-5-6-7-9-11-10(13(15)16-9)8(2)12(14)17-11/h9-11H,2-7H2,1H3/t9-,10+,11+/m1/s1

InChI Key

AENZSPQGLJVLND-VWYCJHECSA-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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Sporothrix sp.	NPAtlas	8119853

Chemical Taxonomy

Classification

Not classified

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	2.91	ALOGPS
logP	2.96	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	18.87	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	60.59 m³·mol⁻¹	ChemAxon
Polarizability	25.37 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

NPAtlas ID

NPA017246

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00016931

Chemspider ID

9119699

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10944473

PDB ID

Not Available

ChEBI ID

141338

Good Scents ID

Not Available

References

General References

Leman-Loubiere C, Le Goff G, Retailleau P, Debitus C, Ouazzani J: Sporothriolide-Related Compounds from the Fungus Hypoxylon monticulosum CLL-205 Isolated from a Sphaerocladina Sponge from the Tahiti Coast. J Nat Prod. 2017 Oct 27;80(10):2850-2854. doi: 10.1021/acs.jnatprod.7b00714. Epub 2017 Oct 18. [PubMed:29043802 ]
Krohn K, Ludewig K, Aust HJ, Draeger S, Schulz B: Biologically active metabolites from fungi. 3. Sporothriolide, discosiolide, and 4-epi-ethisolide--new furofurandiones from Sporothrix sp., Discosia sp., and Pezicula livida. J Antibiot (Tokyo). 1994 Jan;47(1):113-8. doi: 10.7164/antibiotics.47.113. [PubMed:8119853 ]
Yu M, Lynch V, Pagenkopf BL: Intramolecular cyclopropanation of glycals: studies toward the synthesis of canadensolide, sporothriolide, and xylobovide. Org Lett. 2001 Aug 9;3(16):2563-6. doi: 10.1021/ol016239h. [PubMed:11483061 ]
Surup F, Kuhnert E, Lehmann E, Heitkamper S, Hyde KD, Fournier J, Stadler M: Sporothriolide derivatives as chemotaxonomic markers for Hypoxylon monticulosum. Mycology. 2014 Jul 3;5(3):110-119. doi: 10.1080/21501203.2014.929600. Epub 2014 Jun 26. [PubMed:25379335 ]
Cao LL, Zhang YY, Liu YJ, Yang TT, Zhang JL, Zhang ZG, Shen L, Liu JY, Ye YH: Anti-phytopathogenic activity of sporothriolide, a metabolite from endophyte Nodulisporium sp. A21 in Ginkgo biloba. Pestic Biochem Physiol. 2016 May;129:7-13. doi: 10.1016/j.pestbp.2015.10.002. Epub 2015 Oct 21. [PubMed:27017876 ]

Showing NP-Card for Sporothriolide (NP0022739)

MOL for NP0022739 (Sporothriolide)

3D MOL for NP0022739 (Sporothriolide)

3D SDF for NP0022739 (Sporothriolide)

3D-SDF for NP0022739 (Sporothriolide)

PDB for NP0022739 (Sporothriolide)

3D PDB for NP0022739 (Sporothriolide)

SMILES for NP0022739 (Sporothriolide)

INCHI for NP0022739 (Sporothriolide)

Structure for NP0022739 (Sporothriolide)

3D Structure for NP0022739 (Sporothriolide)