NP-MRD: Showing NP-Card for wentilactone A (NP0036486)

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Record Information

Version

2.0

Created at

2021-06-20 19:38:50 UTC

Updated at

2021-06-30 00:08:09 UTC

NP-MRD ID

NP0036486

Secondary Accession Numbers

None

Natural Product Identification

Common Name

wentilactone A

Provided By

JEOL Database JEOL Logo

Description

Wentilactone A belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. wentilactone A is found in Aspergillus wentii and Aspergillus wentii EN-48. wentilactone A was first documented in 2013 (PMID: 24309939). Based on a literature review a small amount of articles have been published on Wentilactone A (PMID: 30405782) (PMID: 26610530).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121383D          

 38 42  0  0  0  0            999 V2000
   -1.8210    0.2149    0.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7177    1.1991   -0.0682 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1013    1.4964    1.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0244    2.6109    1.9499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8826    2.8339    3.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9140    3.9331    3.6658 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6510    1.7998    3.5384 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3176    0.4684    3.1198 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9745    0.4198    1.6611 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667   -0.5632    0.8308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0687   -0.5646   -0.6357 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2627   -1.6668   -1.0278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3971   -1.3318   -2.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9115   -2.1622   -2.9213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2777    0.1621   -2.4583 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7664    0.3410   -3.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5843    0.8763   -2.8798 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7461    0.1055   -2.6072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7112    2.2325   -2.2262 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6990    2.3225   -1.1892 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3359    2.4104   -0.7667 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3085    0.6511   -1.1183 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4350   -0.1838   -0.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4250   -0.6565    0.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5083    0.7218    1.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6317    3.4396    1.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1821   -0.1658    3.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4794    0.1149    3.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9720   -1.3872    1.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0300   -0.6565   -1.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7092   -0.1714   -3.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9900    1.4010   -3.7473 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3979   -0.0771   -4.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5949    1.0305   -3.9650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4764    0.7245   -2.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6005    3.0657   -2.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9228    3.3738   -0.5015 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0308    1.4619   -1.3086 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 17  1  0  0  0  0
 19 21  1  0  0  0  0
  3  4  2  0  0  0  0
  9  8  1  0  0  0  0
  8  7  1  0  0  0  0
  7  5  1  0  0  0  0
  5  4  1  0  0  0  0
 17 15  1  0  0  0  0
  5  6  2  0  0  0  0
  2  3  1  0  0  0  0
  2  1  1  1  0  0  0
 22 11  1  0  0  0  0
 15 13  1  0  0  0  0
 11 10  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  0  0  0  0
 10  9  2  0  0  0  0
 13 14  2  0  0  0  0
  3  9  1  0  0  0  0
 22 38  1  6  0  0  0
 15 22  1  0  0  0  0
 15 16  1  6  0  0  0
  2 21  1  0  0  0  0
 17 18  1  0  0  0  0
 19 20  1  0  0  0  0
  2 22  1  0  0  0  0
 21 20  1  0  0  0  0
 19 36  1  6  0  0  0
 17 34  1  6  0  0  0
 21 37  1  6  0  0  0
 11 30  1  6  0  0  0
 10 29  1  0  0  0  0
  8 27  1  0  0  0  0
  8 28  1  0  0  0  0
  4 26  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
 16 31  1  0  0  0  0
 16 32  1  0  0  0  0
 16 33  1  0  0  0  0
 18 35  1  0  0  0  0
M  END

     RDKit          3D

 38 42  0  0  0  0  0  0  0  0999 V2000
   -1.8210    0.2149    0.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7177    1.1991   -0.0682 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1013    1.4964    1.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0244    2.6109    1.9499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8826    2.8339    3.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9140    3.9331    3.6658 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6510    1.7998    3.5384 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3176    0.4684    3.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9745    0.4198    1.6611 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667   -0.5632    0.8308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0687   -0.5646   -0.6357 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2627   -1.6668   -1.0278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3971   -1.3318   -2.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9115   -2.1622   -2.9213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2777    0.1621   -2.4583 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7664    0.3410   -3.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5843    0.8763   -2.8798 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7461    0.1055   -2.6072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7112    2.2325   -2.2262 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6990    2.3225   -1.1892 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3359    2.4104   -0.7667 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3085    0.6511   -1.1183 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4350   -0.1838   -0.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4250   -0.6565    0.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5083    0.7218    1.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6317    3.4396    1.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1821   -0.1658    3.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4794    0.1149    3.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9720   -1.3872    1.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0300   -0.6565   -1.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7092   -0.1714   -3.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9900    1.4010   -3.7473 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3979   -0.0771   -4.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5949    1.0305   -3.9650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4764    0.7245   -2.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6005    3.0657   -2.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9228    3.3738   -0.5015 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0308    1.4619   -1.3086 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 17  1  0
 19 21  1  0
  3  4  2  0
  9  8  1  0
  8  7  1  0
  7  5  1  0
  5  4  1  0
 17 15  1  0
  5  6  2  0
  2  3  1  0
  2  1  1  1
 22 11  1  0
 15 13  1  0
 11 10  1  0
 11 12  1  0
 13 12  1  0
 10  9  2  0
 13 14  2  0
  3  9  1  0
 22 38  1  6
 15 22  1  0
 15 16  1  6
  2 21  1  0
 17 18  1  0
 19 20  1  0
  2 22  1  0
 21 20  1  0
 19 36  1  6
 17 34  1  6
 21 37  1  6
 11 30  1  6
 10 29  1  0
  8 27  1  0
  8 28  1  0
  4 26  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 16 31  1  0
 16 32  1  0
 16 33  1  0
 18 35  1  0
M  END


  Mrv1652306202121383D          

 38 42  0  0  0  0            999 V2000
   -1.8210    0.2149    0.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7177    1.1991   -0.0682 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1013    1.4964    1.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0244    2.6109    1.9499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8826    2.8339    3.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9140    3.9331    3.6658 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6510    1.7998    3.5384 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3176    0.4684    3.1198 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9745    0.4198    1.6611 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667   -0.5632    0.8308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0687   -0.5646   -0.6357 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2627   -1.6668   -1.0278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3971   -1.3318   -2.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9115   -2.1622   -2.9213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2777    0.1621   -2.4583 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7664    0.3410   -3.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5843    0.8763   -2.8798 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7461    0.1055   -2.6072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7112    2.2325   -2.2262 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6990    2.3225   -1.1892 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3359    2.4104   -0.7667 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3085    0.6511   -1.1183 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4350   -0.1838   -0.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4250   -0.6565    0.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5083    0.7218    1.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6317    3.4396    1.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1821   -0.1658    3.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4794    0.1149    3.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9720   -1.3872    1.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0300   -0.6565   -1.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7092   -0.1714   -3.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9900    1.4010   -3.7473 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3979   -0.0771   -4.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5949    1.0305   -3.9650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4764    0.7245   -2.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6005    3.0657   -2.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9228    3.3738   -0.5015 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0308    1.4619   -1.3086 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 17  1  0  0  0  0
 19 21  1  0  0  0  0
  3  4  2  0  0  0  0
  9  8  1  0  0  0  0
  8  7  1  0  0  0  0
  7  5  1  0  0  0  0
  5  4  1  0  0  0  0
 17 15  1  0  0  0  0
  5  6  2  0  0  0  0
  2  3  1  0  0  0  0
  2  1  1  1  0  0  0
 22 11  1  0  0  0  0
 15 13  1  0  0  0  0
 11 10  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  0  0  0  0
 10  9  2  0  0  0  0
 13 14  2  0  0  0  0
  3  9  1  0  0  0  0
 22 38  1  6  0  0  0
 15 22  1  0  0  0  0
 15 16  1  6  0  0  0
  2 21  1  0  0  0  0
 17 18  1  0  0  0  0
 19 20  1  0  0  0  0
  2 22  1  0  0  0  0
 21 20  1  0  0  0  0
 19 36  1  6  0  0  0
 17 34  1  6  0  0  0
 21 37  1  6  0  0  0
 11 30  1  6  0  0  0
 10 29  1  0  0  0  0
  8 27  1  0  0  0  0
  8 28  1  0  0  0  0
  4 26  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
 16 31  1  0  0  0  0
 16 32  1  0  0  0  0
 16 33  1  0  0  0  0
 18 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0036486

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])[C@@]2([H])O[C@@]2([H])[C@@]2(C3=C([H])C(=O)OC([H])([H])C3=C([H])[C@@]3([H])OC(=O)[C@]1(C([H])([H])[H])[C@@]23[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O6/c1-15-7-4-9(17)20-5-6(7)3-8-11(15)16(2,14(19)21-8)12(18)10-13(15)22-10/h3-4,8,10-13,18H,5H2,1-2H3/t8-,10-,11-,12+,13-,15-,16-/m1/s1

> <INCHI_KEY>
UBQJSYFOVWBSFP-XUBUYMCTSA-N

> <FORMULA>
C16H16O6

> <MOLECULAR_WEIGHT>
304.298

> <EXACT_MASS>
304.094688235

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
29.001229847878932

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,4R,5R,6R,9R,17R)-5-hydroxy-1,6-dimethyl-3,8,13-trioxapentacyclo[7.7.1.0^{2,4}.0^{6,17}.0^{11,16}]heptadeca-10,15-diene-7,14-dione

> <ALOGPS_LOGP>
0.56

> <JCHEM_LOGP>
0.05825866200000132

> <ALOGPS_LOGS>
-1.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.412405406670871

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4932138751221604

> <JCHEM_POLAR_SURFACE_AREA>
85.36

> <JCHEM_REFRACTIVITY>
73.16250000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.85e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4R,5R,6R,9R,17R)-5-hydroxy-1,6-dimethyl-3,8,13-trioxapentacyclo[7.7.1.0^{2,4}.0^{6,17}.0^{11,16}]heptadeca-10,15-diene-7,14-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 38 42  0  0  0  0  0  0  0  0999 V2000
   -1.8210    0.2149    0.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7177    1.1991   -0.0682 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1013    1.4964    1.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0244    2.6109    1.9499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8826    2.8339    3.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9140    3.9331    3.6658 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6510    1.7998    3.5384 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3176    0.4684    3.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9745    0.4198    1.6611 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667   -0.5632    0.8308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0687   -0.5646   -0.6357 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2627   -1.6668   -1.0278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3971   -1.3318   -2.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9115   -2.1622   -2.9213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2777    0.1621   -2.4583 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7664    0.3410   -3.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5843    0.8763   -2.8798 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7461    0.1055   -2.6072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7112    2.2325   -2.2262 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6990    2.3225   -1.1892 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3359    2.4104   -0.7667 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3085    0.6511   -1.1183 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4350   -0.1838   -0.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4250   -0.6565    0.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5083    0.7218    1.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6317    3.4396    1.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1821   -0.1658    3.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4794    0.1149    3.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9720   -1.3872    1.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0300   -0.6565   -1.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7092   -0.1714   -3.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9900    1.4010   -3.7473 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3979   -0.0771   -4.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5949    1.0305   -3.9650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4764    0.7245   -2.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6005    3.0657   -2.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9228    3.3738   -0.5015 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0308    1.4619   -1.3086 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 17  1  0
 19 21  1  0
  3  4  2  0
  9  8  1  0
  8  7  1  0
  7  5  1  0
  5  4  1  0
 17 15  1  0
  5  6  2  0
  2  3  1  0
  2  1  1  1
 22 11  1  0
 15 13  1  0
 11 10  1  0
 11 12  1  0
 13 12  1  0
 10  9  2  0
 13 14  2  0
  3  9  1  0
 22 38  1  6
 15 22  1  0
 15 16  1  6
  2 21  1  0
 17 18  1  0
 19 20  1  0
  2 22  1  0
 21 20  1  0
 19 36  1  6
 17 34  1  6
 21 37  1  6
 11 30  1  6
 10 29  1  0
  8 27  1  0
  8 28  1  0
  4 26  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 16 31  1  0
 16 32  1  0
 16 33  1  0
 18 35  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.821   0.215   0.408  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.718   1.199  -0.068  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.101   1.496   1.207  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.024   2.611   1.950  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.883   2.834   3.127  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.914   3.933   3.666  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.651   1.800   3.538  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.318   0.468   3.120  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.975   0.420   1.661  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.367  -0.563   0.831  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.069  -0.565  -0.636  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.263  -1.667  -1.028  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.397  -1.332  -2.190  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.912  -2.162  -2.921  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.278   0.162  -2.458  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.766   0.341  -3.583  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.584   0.876  -2.880  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.746   0.106  -2.607  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.711   2.232  -2.226  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.699   2.322  -1.189  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.336   2.410  -0.767  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.309   0.651  -1.118  0.00  0.00           C+0
HETATM   23  H   UNK     0      -2.435  -0.184  -0.394  0.00  0.00           H+0
HETATM   24  H   UNK     0      -1.425  -0.657   0.940  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.508   0.722   1.098  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.632   3.440   1.715  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.182  -0.166   3.344  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.479   0.115   3.732  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.972  -1.387   1.201  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.030  -0.657  -1.158  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.709  -0.171  -3.364  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.990   1.401  -3.747  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.398  -0.077  -4.527  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.595   1.030  -3.965  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.476   0.725  -2.420  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.601   3.066  -2.907  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.923   3.374  -0.501  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.031   1.462  -1.309  0.00  0.00           H+0
CONECT    1    2   23   24   25                                             
CONECT    2    3    1   21   22                                             
CONECT    3    4    2    9                                                  
CONECT    4    3    5   26                                                  
CONECT    5    7    4    6                                                  
CONECT    6    5                                                            
CONECT    7    8    5                                                       
CONECT    8    9    7   27   28                                             
CONECT    9    8   10    3                                                  
CONECT   10   11    9   29                                                  
CONECT   11   22   10   12   30                                             
CONECT   12   11   13                                                       
CONECT   13   15   12   14                                                  
CONECT   14   13                                                            
CONECT   15   17   13   22   16                                             
CONECT   16   15   31   32   33                                             
CONECT   17   19   15   18   34                                             
CONECT   18   17   35                                                       
CONECT   19   17   21   20   36                                             
CONECT   20   19   21                                                       
CONECT   21   19    2   20   37                                             
CONECT   22   11   38   15    2                                             
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    4                                                            
CONECT   27    8                                                            
CONECT   28    8                                                            
CONECT   29   10                                                            
CONECT   30   11                                                            
CONECT   31   16                                                            
CONECT   32   16                                                            
CONECT   33   16                                                            
CONECT   34   17                                                            
CONECT   35   18                                                            
CONECT   36   19                                                            
CONECT   37   21                                                            
CONECT   38   22                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

RDKit          3D

38 42  0  0  0  0  0  0  0  0999 V2000
   -1.8210    0.2149    0.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7177    1.1991   -0.0682 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1013    1.4964    1.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0244    2.6109    1.9499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8826    2.8339    3.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9140    3.9331    3.6658 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6510    1.7998    3.5384 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3176    0.4684    3.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9745    0.4198    1.6611 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667   -0.5632    0.8308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0687   -0.5646   -0.6357 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2627   -1.6668   -1.0278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3971   -1.3318   -2.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9115   -2.1622   -2.9213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2777    0.1621   -2.4583 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7664    0.3410   -3.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5843    0.8763   -2.8798 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7461    0.1055   -2.6072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7112    2.2325   -2.2262 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6990    2.3225   -1.1892 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3359    2.4104   -0.7667 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3085    0.6511   -1.1183 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4350   -0.1838   -0.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4250   -0.6565    0.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5083    0.7218    1.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6317    3.4396    1.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1821   -0.1658    3.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4794    0.1149    3.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9720   -1.3872    1.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0300   -0.6565   -1.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7092   -0.1714   -3.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9900    1.4010   -3.7473 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3979   -0.0771   -4.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5949    1.0305   -3.9650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4764    0.7245   -2.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6005    3.0657   -2.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9228    3.3738   -0.5015 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0308    1.4619   -1.3086 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 17  1  0
 19 21  1  0
  3  4  2  0
  9  8  1  0
  8  7  1  0
  7  5  1  0
  5  4  1  0
 17 15  1  0
  5  6  2  0
  2  3  1  0
  2  1  1  1
 22 11  1  0
 15 13  1  0
 11 10  1  0
 11 12  1  0
 13 12  1  0
 10  9  2  0
 13 14  2  0
  3  9  1  0
 22 38  1  6
 15 22  1  0
 15 16  1  6
  2 21  1  0
 17 18  1  0
 19 20  1  0
  2 22  1  0
 21 20  1  0
 19 36  1  6
 17 34  1  6
 21 37  1  6
 11 30  1  6
 10 29  1  0
  8 27  1  0
  8 28  1  0
  4 26  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 16 31  1  0
 16 32  1  0
 16 33  1  0
 18 35  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₆O₆

Average Mass

304.2980 Da

Monoisotopic Mass

304.09469 Da

IUPAC Name

(1S,2S,4R,5R,6R,9R,17R)-5-hydroxy-1,6-dimethyl-3,8,13-trioxapentacyclo[7.7.1.0^{2,4}.0^{6,17}.0^{11,16}]heptadeca-10,15-diene-7,14-dione

Traditional Name

(1S,2S,4R,5R,6R,9R,17R)-5-hydroxy-1,6-dimethyl-3,8,13-trioxapentacyclo[7.7.1.0^{2,4}.0^{6,17}.0^{11,16}]heptadeca-10,15-diene-7,14-dione

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])[C@@]2([H])O[C@@]2([H])[C@@]2(C3=C([H])C(=O)OC([H])([H])C3=C([H])[C@@]3([H])OC(=O)[C@]1(C([H])([H])[H])[C@@]23[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C16H16O6/c1-15-7-4-9(17)20-5-6(7)3-8-11(15)16(2,14(19)21-8)12(18)10-13(15)22-10/h3-4,8,10-13,18H,5H2,1-2H3/t8-,10-,11-,12+,13-,15-,16-/m1/s1

InChI Key

UBQJSYFOVWBSFP-XUBUYMCTSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aspergillus wentii	Fungi	KNApSAcK
Aspergillus wentii EN-48	JEOL database	Sun, H. -F., et al, J. Nat. Prod. 75, 148 (2012)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthalene
Dihydropyranone
Oxepane
Dicarboxylic acid or derivatives
Gamma butyrolactone
Pyran
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Lactone
Carboxylic acid ester
Secondary alcohol
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
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	0.56	ALOGPS
logP	0.058	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	13.41	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	85.36 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	73.16 m³·mol⁻¹	ChemAxon
Polarizability	29 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

137940

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

156679

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jiang W, Meng L, Xu G, Lv C, Wang H, Tian H, Chen R, Jiao B, Wang B, Huang C: Wentilactone A induces cell apoptosis by targeting AKR1C1 gene via the IGF-1R/IRS1/PI3K/AKT/Nrf2/FLIP/Caspase-3 signaling pathway in small cell lung cancer. Oncol Lett. 2018 Nov;16(5):6445-6457. doi: 10.3892/ol.2018.9486. Epub 2018 Sep 24. [PubMed:30405782 ]
Xu R, Xu GM, Li XM, Li CS, Wang BG: Characterization of a Newly Isolated Marine Fungus Aspergillus dimorphicus for Optimized Production of the Anti-Tumor Agent Wentilactones. Mar Drugs. 2015 Nov 19;13(11):7040-54. doi: 10.3390/md13117040. [PubMed:26610530 ]
Lv C, Hong Y, Miao L, Li C, Xu G, Wei S, Wang B, Huang C, Jiao B: Wentilactone A as a novel potential antitumor agent induces apoptosis and G2/M arrest of human lung carcinoma cells, and is mediated by HRas-GTP accumulation to excessively activate the Ras/Raf/ERK/p53-p21 pathway. Cell Death Dis. 2013 Dec 5;4:e952. doi: 10.1038/cddis.2013.484. [PubMed:24309939 ]
Sun, H. -F., et al. (2012). Sun, H. -F., et al, J. Nat. Prod. 75, 148 (2012). J. Nat. Prod..

Showing NP-Card for wentilactone A (NP0036486)

MOL for NP0036486 (wentilactone A)

3D MOL for NP0036486 (wentilactone A)

3D SDF for NP0036486 (wentilactone A)

3D-SDF for NP0036486 (wentilactone A)

PDB for NP0036486 (wentilactone A)

3D PDB for NP0036486 (wentilactone A)

SMILES for NP0036486 (wentilactone A)

INCHI for NP0036486 (wentilactone A)

Structure for NP0036486 (wentilactone A)

3D Structure for NP0036486 (wentilactone A)