NP-MRD: Showing NP-Card for Brefeldin D (NP0016794)

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Record Information

Version

2.0

Created at

2021-01-06 01:41:21 UTC

Updated at

2021-07-15 17:23:42 UTC

NP-MRD ID

NP0016794

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Brefeldin D

Provided By

NPAtlas

Description

Brefeldin D is found in Penicillium. Brefeldin D was first documented in 2018 (PMID: 28722499).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242104173D          

 40 41  0  0  0  0            999 V2000
    3.6147    0.9096   -0.6261 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5875    0.0823    0.1500 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7628    0.9578    1.0123 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4081    2.2917    0.5641 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7959    2.5660   -0.5692 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708    1.6306   -1.5529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6817    0.8439   -1.4676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6457    0.6892   -0.4629 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8861    1.5672    0.6732 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1336    0.8830    1.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9778    1.3796    1.9161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1640   -0.5476    0.7465 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7549   -0.6670    0.2400 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3318   -1.8250   -0.5100 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4857   -2.5478   -0.9071 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4906   -2.8131    0.2428 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8229   -2.8976    0.0990 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6596   -2.0937   -0.7648 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2273   -2.7320   -1.7519 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9560   -0.7741   -0.7160 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2266    1.3753   -1.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4143    0.1760   -0.9419 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1316    1.5998    0.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2706   -0.5225    0.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3220    1.0417    2.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8768    0.4169    1.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6852    3.1300    1.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6536    3.6424   -0.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9150    1.5271   -2.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8326    0.1752   -2.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6671    0.7073   -1.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1660    2.5863    0.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2043    1.5502    1.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3305   -1.2002    1.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8975   -0.7129   -0.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1237   -0.5820    1.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8179   -1.6104   -1.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3301   -3.0446   -1.7423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0527   -3.4585    0.9272 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2729   -3.6999    0.7254 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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20  2  1  0  0  0  0
 13  8  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  2 24  1  1  0  0  0
  3 25  1  0  0  0  0
  3 26  1  0  0  0  0
  4 27  1  0  0  0  0
  5 28  1  0  0  0  0
  6 29  1  0  0  0  0
  7 30  1  0  0  0  0
  8 31  1  6  0  0  0
  9 32  1  0  0  0  0
  9 33  1  0  0  0  0
 12 34  1  0  0  0  0
 12 35  1  0  0  0  0
 13 36  1  1  0  0  0
 14 37  1  6  0  0  0
 15 38  1  0  0  0  0
 16 39  1  0  0  0  0
 17 40  1  0  0  0  0
M  END

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
    3.6147    0.9096   -0.6261 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5875    0.0823    0.1500 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7628    0.9578    1.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4081    2.2917    0.5641 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7959    2.5660   -0.5692 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708    1.6306   -1.5529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6817    0.8439   -1.4676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6457    0.6892   -0.4629 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8861    1.5672    0.6732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1336    0.8830    1.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9778    1.3796    1.9161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1640   -0.5476    0.7465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7549   -0.6670    0.2400 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3318   -1.8250   -0.5100 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4857   -2.5478   -0.9071 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4906   -2.8131    0.2428 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8229   -2.8976    0.0990 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6596   -2.0937   -0.7648 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2273   -2.7320   -1.7519 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9560   -0.7741   -0.7160 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2266    1.3753   -1.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4143    0.1760   -0.9419 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1316    1.5998    0.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2706   -0.5225    0.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3220    1.0417    2.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8768    0.4169    1.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6852    3.1300    1.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6536    3.6424   -0.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9150    1.5271   -2.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8326    0.1752   -2.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6671    0.7073   -1.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1660    2.5863    0.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2043    1.5502    1.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3305   -1.2002    1.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8975   -0.7129   -0.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1237   -0.5820    1.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8179   -1.6104   -1.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3301   -3.0446   -1.7423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0527   -3.4585    0.9272 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2729   -3.6999    0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20  2  1  0
 13  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  1
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  6
  9 32  1  0
  9 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  1
 14 37  1  6
 15 38  1  0
 16 39  1  0
 17 40  1  0
M  END


  Mrv1652306242104173D          

 40 41  0  0  0  0            999 V2000
    3.6147    0.9096   -0.6261 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5875    0.0823    0.1500 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7628    0.9578    1.0123 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4081    2.2917    0.5641 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7959    2.5660   -0.5692 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708    1.6306   -1.5529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6817    0.8439   -1.4676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6457    0.6892   -0.4629 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8861    1.5672    0.6732 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1336    0.8830    1.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9778    1.3796    1.9161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1640   -0.5476    0.7465 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7549   -0.6670    0.2400 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3318   -1.8250   -0.5100 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4857   -2.5478   -0.9071 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4906   -2.8131    0.2428 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8229   -2.8976    0.0990 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6596   -2.0937   -0.7648 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2273   -2.7320   -1.7519 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9560   -0.7741   -0.7160 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2266    1.3753   -1.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4143    0.1760   -0.9419 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1316    1.5998    0.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2706   -0.5225    0.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3220    1.0417    2.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8768    0.4169    1.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6852    3.1300    1.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6536    3.6424   -0.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9150    1.5271   -2.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8326    0.1752   -2.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6671    0.7073   -1.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1660    2.5863    0.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2043    1.5502    1.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3305   -1.2002    1.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8975   -0.7129   -0.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1237   -0.5820    1.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8179   -1.6104   -1.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3301   -3.0446   -1.7423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0527   -3.4585    0.9272 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2729   -3.6999    0.7254 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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20  2  1  0  0  0  0
 13  8  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  2 24  1  1  0  0  0
  3 25  1  0  0  0  0
  3 26  1  0  0  0  0
  4 27  1  0  0  0  0
  5 28  1  0  0  0  0
  6 29  1  0  0  0  0
  7 30  1  0  0  0  0
  8 31  1  6  0  0  0
  9 32  1  0  0  0  0
  9 33  1  0  0  0  0
 12 34  1  0  0  0  0
 12 35  1  0  0  0  0
 13 36  1  1  0  0  0
 14 37  1  6  0  0  0
 15 38  1  0  0  0  0
 16 39  1  0  0  0  0
 17 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0016794

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])\C([H])=C([H])/C(=O)O[C@@]([H])(C([H])([H])[H])C([H])([H])\C([H])=C(\[H])/C(/[H])=C([H])\[C@]2([H])C([H])([H])C(=O)C([H])([H])[C@@]12[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H20O4/c1-11-5-3-2-4-6-12-9-13(17)10-14(12)15(18)7-8-16(19)20-11/h2-4,6-8,11-12,14-15,18H,5,9-10H2,1H3/b3-2-,6-4-,8-7-/t11-,12+,14+,15+/m0/s1

> <INCHI_KEY>
FYDHFALTOZKRET-QNGDLURSSA-N

> <FORMULA>
C16H20O4

> <MOLECULAR_WEIGHT>
276.332

> <EXACT_MASS>
276.136159124

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
29.02719287626679

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,6S,11aS,14aR)-1-hydroxy-6-methyl-1H,4H,6H,7H,11aH,12H,13H,14H,14aH-cyclopenta[f]oxacyclotridecane-4,13-dione

> <ALOGPS_LOGP>
1.76

> <JCHEM_LOGP>
1.8527950526666666

> <ALOGPS_LOGS>
-2.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.21803181782225

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.48004103260088

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0260402476240067

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
78.83729999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.80e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,6S,11aS,14aR)-1-hydroxy-6-methyl-1H,6H,7H,11aH,12H,14H,14aH-cyclopenta[f]oxacyclotridecane-4,13-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
    3.6147    0.9096   -0.6261 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5875    0.0823    0.1500 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7628    0.9578    1.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4081    2.2917    0.5641 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7959    2.5660   -0.5692 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708    1.6306   -1.5529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6817    0.8439   -1.4676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6457    0.6892   -0.4629 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8861    1.5672    0.6732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1336    0.8830    1.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9778    1.3796    1.9161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1640   -0.5476    0.7465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7549   -0.6670    0.2400 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3318   -1.8250   -0.5100 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4857   -2.5478   -0.9071 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4906   -2.8131    0.2428 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8229   -2.8976    0.0990 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6596   -2.0937   -0.7648 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2273   -2.7320   -1.7519 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9560   -0.7741   -0.7160 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2266    1.3753   -1.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4143    0.1760   -0.9419 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1316    1.5998    0.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2706   -0.5225    0.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3220    1.0417    2.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8768    0.4169    1.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6852    3.1300    1.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6536    3.6424   -0.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9150    1.5271   -2.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8326    0.1752   -2.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6671    0.7073   -1.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1660    2.5863    0.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2043    1.5502    1.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3305   -1.2002    1.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8975   -0.7129   -0.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1237   -0.5820    1.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8179   -1.6104   -1.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3301   -3.0446   -1.7423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0527   -3.4585    0.9272 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2729   -3.6999    0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20  2  1  0
 13  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  1
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  6
  9 32  1  0
  9 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  1
 14 37  1  6
 15 38  1  0
 16 39  1  0
 17 40  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       3.615   0.910  -0.626  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.587   0.082   0.150  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.763   0.958   1.012  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.408   2.292   0.564  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.796   2.566  -0.569  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.371   1.631  -1.553  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.682   0.844  -1.468  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.646   0.689  -0.463  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.886   1.567   0.673  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.134   0.883   1.218  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.978   1.380   1.916  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.164  -0.548   0.747  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.755  -0.667   0.240  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.332  -1.825  -0.510  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.486  -2.548  -0.907  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.491  -2.813   0.243  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.823  -2.898   0.099  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.660  -2.094  -0.765  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.227  -2.732  -1.752  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.956  -0.774  -0.716  0.00  0.00           O+0
HETATM   21  H   UNK     0       3.227   1.375  -1.525  0.00  0.00           H+0
HETATM   22  H   UNK     0       4.414   0.176  -0.942  0.00  0.00           H+0
HETATM   23  H   UNK     0       4.132   1.600   0.075  0.00  0.00           H+0
HETATM   24  H   UNK     0       3.271  -0.523   0.839  0.00  0.00           H+0
HETATM   25  H   UNK     0       2.322   1.042   2.003  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.877   0.417   1.299  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.685   3.130   1.252  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.654   3.642  -0.731  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.915   1.527  -2.530  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.833   0.175  -2.362  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.667   0.707  -1.024  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.166   2.586   0.333  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.204   1.550   1.525  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.330  -1.200   1.637  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.898  -0.713  -0.042  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.124  -0.582   1.162  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.818  -1.610  -1.476  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.330  -3.045  -1.742  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.053  -3.458   0.927  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.273  -3.700   0.725  0.00  0.00           H+0
CONECT    1    2   21   22   23                                             
CONECT    2    1    3   20   24                                             
CONECT    3    2    4   25   26                                             
CONECT    4    3    5   27                                                  
CONECT    5    4    6   28                                                  
CONECT    6    5    7   29                                                  
CONECT    7    6    8   30                                                  
CONECT    8    7    9   13   31                                             
CONECT    9    8   10   32   33                                             
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   34   35                                             
CONECT   13   12   14    8   36                                             
CONECT   14   13   15   16   37                                             
CONECT   15   14   38                                                       
CONECT   16   14   17   39                                                  
CONECT   17   16   18   40                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    2                                                       
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    2                                                            
CONECT   25    3                                                            
CONECT   26    3                                                            
CONECT   27    4                                                            
CONECT   28    5                                                            
CONECT   29    6                                                            
CONECT   30    7                                                            
CONECT   31    8                                                            
CONECT   32    9                                                            
CONECT   33    9                                                            
CONECT   34   12                                                            
CONECT   35   12                                                            
CONECT   36   13                                                            
CONECT   37   14                                                            
CONECT   38   15                                                            
CONECT   39   16                                                            
CONECT   40   17                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   82    0
END

RDKit          3D

40 41  0  0  0  0  0  0  0  0999 V2000
    3.6147    0.9096   -0.6261 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5875    0.0823    0.1500 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7628    0.9578    1.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4081    2.2917    0.5641 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7959    2.5660   -0.5692 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708    1.6306   -1.5529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6817    0.8439   -1.4676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6457    0.6892   -0.4629 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8861    1.5672    0.6732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1336    0.8830    1.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9778    1.3796    1.9161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1640   -0.5476    0.7465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7549   -0.6670    0.2400 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3318   -1.8250   -0.5100 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4857   -2.5478   -0.9071 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4906   -2.8131    0.2428 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8229   -2.8976    0.0990 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6596   -2.0937   -0.7648 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2273   -2.7320   -1.7519 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9560   -0.7741   -0.7160 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2266    1.3753   -1.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4143    0.1760   -0.9419 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1316    1.5998    0.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2706   -0.5225    0.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3220    1.0417    2.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8768    0.4169    1.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6852    3.1300    1.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6536    3.6424   -0.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9150    1.5271   -2.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8326    0.1752   -2.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6671    0.7073   -1.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1660    2.5863    0.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2043    1.5502    1.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3305   -1.2002    1.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8975   -0.7129   -0.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1237   -0.5820    1.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8179   -1.6104   -1.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3301   -3.0446   -1.7423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0527   -3.4585    0.9272 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2729   -3.6999    0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20  2  1  0
 13  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  1
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  6
  9 32  1  0
  9 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  1
 14 37  1  6
 15 38  1  0
 16 39  1  0
 17 40  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₆H₂₀O₄

Average Mass

276.3320 Da

Monoisotopic Mass

276.13616 Da

IUPAC Name

(1R,6S,11aS,14aR)-1-hydroxy-6-methyl-1H,4H,6H,7H,11aH,12H,13H,14H,14aH-cyclopenta[f]oxacyclotridecane-4,13-dione

Traditional Name

(1R,6S,11aS,14aR)-1-hydroxy-6-methyl-1H,6H,7H,11aH,12H,14H,14aH-cyclopenta[f]oxacyclotridecane-4,13-dione

CAS Registry Number

Not Available

SMILES

C[C@H]1C\C=C/C=C\[C@@H]2CC(=O)C[C@H]2[C@H](O)\C=C/C(=O)O1

InChI Identifier

InChI=1S/C16H20O4/c1-11-5-3-2-4-6-12-9-13(17)10-14(12)15(18)7-8-16(19)20-11/h2-4,6-8,11-12,14-15,18H,5,9-10H2,1H3/b3-2-,6-4-,8-7-/t11-,12+,14+,15+/m0/s1

InChI Key

FYDHFALTOZKRET-QNGDLURSSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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
Penicillium	NPAtlas	28722499

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	1.76	ALOGPS
logP	1.85	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	14.48	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	78.84 m³·mol⁻¹	ChemAxon
Polarizability	29.03 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

Not Available

References

General References

Cheng X, Yu L, Wang Q, Ding W, Chen Z, Ma Z: New brefeldins and penialidins from marine fungus Penicillium janthinellum DT-F29. Nat Prod Res. 2018 Feb;32(3):282-286. doi: 10.1080/14786419.2017.1354188. Epub 2017 Jul 19. [PubMed:28722499 ]

Showing NP-Card for Brefeldin D (NP0016794)

MOL for NP0016794 (Brefeldin D)

3D MOL for NP0016794 (Brefeldin D)

3D SDF for NP0016794 (Brefeldin D)

3D-SDF for NP0016794 (Brefeldin D)

PDB for NP0016794 (Brefeldin D)

3D PDB for NP0016794 (Brefeldin D)

SMILES for NP0016794 (Brefeldin D)

INCHI for NP0016794 (Brefeldin D)

Structure for NP0016794 (Brefeldin D)

3D Structure for NP0016794 (Brefeldin D)