NP-MRD: Showing NP-Card for (-)-cereolactam (NP0010322)

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Record Information

Version

2.0

Created at

2021-01-05 19:52:45 UTC

Updated at

2021-07-15 17:05:46 UTC

NP-MRD ID

NP0010322

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-cereolactam

Provided By

NPAtlas

Description

(-)-Cereolactam belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. (-)-cereolactam is found in Coniothyrium and Neosetophoma cerealis. (-)-cereolactam was first documented in 2011 (PMID: 21923104). Based on a literature review very few articles have been published on (-)-Cereolactam.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242107373D          

 39 42  0  0  0  0            999 V2000
    1.2585   -2.9139   -0.5996 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9756   -1.6667   -0.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3477   -1.5669   -0.2544 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9718   -0.3501    0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3407   -0.2818    0.0750 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2412    0.7952    0.2509 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8781    0.6589    0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2377    1.8465    0.4239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1438    1.8189    0.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8287    3.0010    0.6174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8181    0.6301    0.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1582   -0.5642   -0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2177   -0.5169   -0.0850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721   -1.5720   -0.3738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2690   -0.9204   -0.8440 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4748   -1.7698   -0.7029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2610    0.3126    0.0081 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7812   -0.0654    1.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0589    1.4433   -0.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2360    2.8580    0.6679 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5170    2.2061    0.5617 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6599    2.6640    0.6906 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9743   -3.7643   -0.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7473   -2.9019   -1.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5507   -3.1407    0.2373 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9771   -2.4556   -0.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8141    0.5740    0.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3867    3.8735    0.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0314   -0.6245   -1.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0843   -1.5881    0.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1386   -1.5898   -1.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1525   -2.8428   -0.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8855    0.0182    1.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4632   -1.1065    1.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3052    0.5627    2.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4689    1.8994   -1.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0063    0.9981   -0.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2394    2.1877    0.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0825    3.8540    0.8781 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 13  2  1  0  0  0  0
 21  6  1  0  0  0  0
 13  7  1  0  0  0  0
 17 11  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
  3 26  1  0  0  0  0
  5 27  1  0  0  0  0
 10 28  1  0  0  0  0
 15 29  1  6  0  0  0
 16 30  1  0  0  0  0
 16 31  1  0  0  0  0
 16 32  1  0  0  0  0
 18 33  1  0  0  0  0
 18 34  1  0  0  0  0
 18 35  1  0  0  0  0
 19 36  1  0  0  0  0
 19 37  1  0  0  0  0
 19 38  1  0  0  0  0
 20 39  1  0  0  0  0
M  END

     RDKit          3D

 39 42  0  0  0  0  0  0  0  0999 V2000
    1.2585   -2.9139   -0.5996 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9756   -1.6667   -0.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3477   -1.5669   -0.2544 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9718   -0.3501    0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3407   -0.2818    0.0750 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2412    0.7952    0.2509 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8781    0.6589    0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2377    1.8465    0.4239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1438    1.8189    0.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8287    3.0010    0.6174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8181    0.6301    0.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1582   -0.5642   -0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2177   -0.5169   -0.0850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721   -1.5720   -0.3738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2690   -0.9204   -0.8440 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4748   -1.7698   -0.7029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2610    0.3126    0.0081 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7812   -0.0654    1.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0589    1.4433   -0.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2360    2.8580    0.6679 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5170    2.2061    0.5617 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6599    2.6640    0.6906 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9743   -3.7643   -0.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7473   -2.9019   -1.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5507   -3.1407    0.2373 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9771   -2.4556   -0.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8141    0.5740    0.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3867    3.8735    0.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0314   -0.6245   -1.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0843   -1.5881    0.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1386   -1.5898   -1.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1525   -2.8428   -0.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8855    0.0182    1.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4632   -1.1065    1.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3052    0.5627    2.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4689    1.8994   -1.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0063    0.9981   -0.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2394    2.1877    0.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0825    3.8540    0.8781 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  1
 17 19  1  0
  8 20  1  0
 20 21  1  0
 21 22  2  0
 13  2  1  0
 21  6  1  0
 13  7  1  0
 17 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  5 27  1  0
 10 28  1  0
 15 29  1  6
 16 30  1  0
 16 31  1  0
 16 32  1  0
 18 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
 20 39  1  0
M  END


  Mrv1652306242107373D          

 39 42  0  0  0  0            999 V2000
    1.2585   -2.9139   -0.5996 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9756   -1.6667   -0.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3477   -1.5669   -0.2544 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9718   -0.3501    0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3407   -0.2818    0.0750 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2412    0.7952    0.2509 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8781    0.6589    0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2377    1.8465    0.4239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1438    1.8189    0.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8287    3.0010    0.6174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8181    0.6301    0.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1582   -0.5642   -0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2177   -0.5169   -0.0850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721   -1.5720   -0.3738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2690   -0.9204   -0.8440 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4748   -1.7698   -0.7029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2610    0.3126    0.0081 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7812   -0.0654    1.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0589    1.4433   -0.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2360    2.8580    0.6679 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5170    2.2061    0.5617 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6599    2.6640    0.6906 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9743   -3.7643   -0.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7473   -2.9019   -1.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5507   -3.1407    0.2373 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9771   -2.4556   -0.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8141    0.5740    0.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3867    3.8735    0.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0314   -0.6245   -1.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0843   -1.5881    0.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1386   -1.5898   -1.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1525   -2.8428   -0.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8855    0.0182    1.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4632   -1.1065    1.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3052    0.5627    2.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4689    1.8994   -1.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0063    0.9981   -0.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2394    2.1877    0.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0825    3.8540    0.8781 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 13  2  1  0  0  0  0
 21  6  1  0  0  0  0
 13  7  1  0  0  0  0
 17 11  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
  3 26  1  0  0  0  0
  5 27  1  0  0  0  0
 10 28  1  0  0  0  0
 15 29  1  6  0  0  0
 16 30  1  0  0  0  0
 16 31  1  0  0  0  0
 16 32  1  0  0  0  0
 18 33  1  0  0  0  0
 18 34  1  0  0  0  0
 18 35  1  0  0  0  0
 19 36  1  0  0  0  0
 19 37  1  0  0  0  0
 19 38  1  0  0  0  0
 20 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0010322

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(=O)N([H])C3=C2C(=C2O[C@@]([H])(C([H])([H])[H])C(C2=C3O[H])(C([H])([H])[H])C([H])([H])[H])C(=C1[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C17H17NO4/c1-6-5-8(19)10-11-9(6)15-12(17(3,4)7(2)22-15)14(20)13(11)18-16(10)21/h5,7,19-20H,1-4H3,(H,18,21)/t7-/m0/s1

> <INCHI_KEY>
ZEVXHSMDHQZKIS-ZETCQYMHSA-N

> <FORMULA>
C17H17NO4

> <MOLECULAR_WEIGHT>
299.326

> <EXACT_MASS>
299.115758031

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
31.785644204118434

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S)-7,12-dihydroxy-4,5,5,14-tetramethyl-3-oxa-9-azatetracyclo[6.6.1.0^{2,6}.0^{11,15}]pentadeca-1,6,8(15),11,13-pentaen-10-one

> <ALOGPS_LOGP>
3.14

> <JCHEM_LOGP>
3.02941825

> <ALOGPS_LOGS>
-2.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.017590849872205

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.7213633524649135

> <JCHEM_PKA_STRONGEST_BASIC>
-4.488787891667816

> <JCHEM_POLAR_SURFACE_AREA>
78.78999999999999

> <JCHEM_REFRACTIVITY>
84.04799999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.38e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S)-7,12-dihydroxy-4,5,5,14-tetramethyl-3-oxa-9-azatetracyclo[6.6.1.0^{2,6}.0^{11,15}]pentadeca-1,6,8(15),11,13-pentaen-10-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 39 42  0  0  0  0  0  0  0  0999 V2000
    1.2585   -2.9139   -0.5996 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9756   -1.6667   -0.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3477   -1.5669   -0.2544 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9718   -0.3501    0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3407   -0.2818    0.0750 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2412    0.7952    0.2509 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8781    0.6589    0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2377    1.8465    0.4239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1438    1.8189    0.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8287    3.0010    0.6174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8181    0.6301    0.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1582   -0.5642   -0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2177   -0.5169   -0.0850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721   -1.5720   -0.3738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2690   -0.9204   -0.8440 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4748   -1.7698   -0.7029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2610    0.3126    0.0081 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7812   -0.0654    1.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0589    1.4433   -0.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2360    2.8580    0.6679 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5170    2.2061    0.5617 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6599    2.6640    0.6906 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9743   -3.7643   -0.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7473   -2.9019   -1.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5507   -3.1407    0.2373 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9771   -2.4556   -0.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8141    0.5740    0.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3867    3.8735    0.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0314   -0.6245   -1.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0843   -1.5881    0.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1386   -1.5898   -1.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1525   -2.8428   -0.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8855    0.0182    1.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4632   -1.1065    1.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3052    0.5627    2.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4689    1.8994   -1.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0063    0.9981   -0.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2394    2.1877    0.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0825    3.8540    0.8781 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  1
 17 19  1  0
  8 20  1  0
 20 21  1  0
 21 22  2  0
 13  2  1  0
 21  6  1  0
 13  7  1  0
 17 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  5 27  1  0
 10 28  1  0
 15 29  1  6
 16 30  1  0
 16 31  1  0
 16 32  1  0
 18 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
 20 39  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       1.258  -2.914  -0.600  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.976  -1.667  -0.312  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.348  -1.567  -0.254  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.972  -0.350   0.024  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.341  -0.282   0.075  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.241   0.795   0.251  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.878   0.659   0.185  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.238   1.847   0.424  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.144   1.819   0.381  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.829   3.001   0.617  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.818   0.630   0.108  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.158  -0.564  -0.132  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.218  -0.517  -0.085  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.072  -1.572  -0.374  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.269  -0.920  -0.844  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.475  -1.770  -0.703  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.261   0.313   0.008  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.781  -0.065   1.378  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.059   1.443  -0.599  0.00  0.00           C+0
HETATM   20  N   UNK     0       2.236   2.858   0.668  0.00  0.00           N+0
HETATM   21  C   UNK     0       3.517   2.206   0.562  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.660   2.664   0.691  0.00  0.00           O+0
HETATM   23  H   UNK     0       1.974  -3.764  -0.618  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.747  -2.902  -1.581  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.551  -3.141   0.237  0.00  0.00           H+0
HETATM   26  H   UNK     0       3.977  -2.456  -0.429  0.00  0.00           H+0
HETATM   27  H   UNK     0       5.814   0.574   0.272  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.387   3.874   0.817  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.031  -0.625  -1.891  0.00  0.00           H+0
HETATM   30  H   UNK     0      -4.084  -1.588   0.186  0.00  0.00           H+0
HETATM   31  H   UNK     0      -4.139  -1.590  -1.587  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.152  -2.843  -0.765  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.886   0.018   1.429  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.463  -1.107   1.586  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.305   0.563   2.166  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.469   1.899  -1.398  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.006   0.998  -0.973  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.239   2.188   0.203  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.083   3.854   0.878  0.00  0.00           H+0
CONECT    1    2   23   24   25                                             
CONECT    2    1    3   13                                                  
CONECT    3    2    4   26                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4   27                                                       
CONECT    6    4    7   21                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9   20                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9   28                                                       
CONECT   11    9   12   17                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    2    7                                                  
CONECT   14   12   15                                                       
CONECT   15   14   16   17   29                                             
CONECT   16   15   30   31   32                                             
CONECT   17   15   18   19   11                                             
CONECT   18   17   33   34   35                                             
CONECT   19   17   36   37   38                                             
CONECT   20    8   21   39                                                  
CONECT   21   20   22    6                                                  
CONECT   22   21                                                            
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    3                                                            
CONECT   27    5                                                            
CONECT   28   10                                                            
CONECT   29   15                                                            
CONECT   30   16                                                            
CONECT   31   16                                                            
CONECT   32   16                                                            
CONECT   33   18                                                            
CONECT   34   18                                                            
CONECT   35   18                                                            
CONECT   36   19                                                            
CONECT   37   19                                                            
CONECT   38   19                                                            
CONECT   39   20                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

RDKit          3D

39 42  0  0  0  0  0  0  0  0999 V2000
    1.2585   -2.9139   -0.5996 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9756   -1.6667   -0.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3477   -1.5669   -0.2544 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9718   -0.3501    0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3407   -0.2818    0.0750 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2412    0.7952    0.2509 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8781    0.6589    0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2377    1.8465    0.4239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1438    1.8189    0.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8287    3.0010    0.6174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8181    0.6301    0.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1582   -0.5642   -0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2177   -0.5169   -0.0850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721   -1.5720   -0.3738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2690   -0.9204   -0.8440 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4748   -1.7698   -0.7029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2610    0.3126    0.0081 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7812   -0.0654    1.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0589    1.4433   -0.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2360    2.8580    0.6679 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5170    2.2061    0.5617 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6599    2.6640    0.6906 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9743   -3.7643   -0.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7473   -2.9019   -1.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5507   -3.1407    0.2373 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9771   -2.4556   -0.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8141    0.5740    0.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3867    3.8735    0.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0314   -0.6245   -1.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0843   -1.5881    0.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1386   -1.5898   -1.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1525   -2.8428   -0.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8855    0.0182    1.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4632   -1.1065    1.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3052    0.5627    2.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4689    1.8994   -1.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0063    0.9981   -0.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2394    2.1877    0.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0825    3.8540    0.8781 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  1
 17 19  1  0
  8 20  1  0
 20 21  1  0
 21 22  2  0
 13  2  1  0
 21  6  1  0
 13  7  1  0
 17 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  5 27  1  0
 10 28  1  0
 15 29  1  6
 16 30  1  0
 16 31  1  0
 16 32  1  0
 18 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
 20 39  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₇H₁₇NO₄

Average Mass

299.3260 Da

Monoisotopic Mass

299.11576 Da

IUPAC Name

(4S)-7,12-dihydroxy-4,5,5,14-tetramethyl-3-oxa-9-azatetracyclo[6.6.1.0^{2,6}.0^{11,15}]pentadeca-1,6,8(15),11,13-pentaen-10-one

Traditional Name

(4S)-7,12-dihydroxy-4,5,5,14-tetramethyl-3-oxa-9-azatetracyclo[6.6.1.0^{2,6}.0^{11,15}]pentadeca-1,6,8(15),11,13-pentaen-10-one

CAS Registry Number

Not Available

SMILES

C[C@@H]1OC2=C(C(O)=C3NC(=O)C4=C(O)C=C(C)C2=C34)C1(C)C

InChI Identifier

InChI=1S/C17H17NO4/c1-6-5-8(19)10-11-9(6)15-12(17(3,4)7(2)22-15)14(20)13(11)18-16(10)21/h5,7,19-20H,1-4H3,(H,18,21)/t7-/m0/s1

InChI Key

ZEVXHSMDHQZKIS-ZETCQYMHSA-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
Coniothyrium	NPAtlas	21923104
Neosetophoma cerealis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four 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

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
2-naphthol
Naphthalene
Isoindolone
Coumaran
Indole or derivatives
Isoindole or derivatives
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Vinylogous acid
Carboxamide group
Lactam
Secondary carboxylic acid amide
Azacycle
Oxacycle
Ether
Carboxylic acid derivative
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

naphthofuran (CHEBI:69034 )

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	3.14	ALOGPS
logP	3.03	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	7.72	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	78.79 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	84.05 m³·mol⁻¹	ChemAxon
Polarizability	31.79 Å³	ChemAxon
Number of Rings	4	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

NPA002628

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

26635891

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

56598201

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Elsebai MF, Natesan L, Kehraus S, Mohamed IE, Schnakenburg G, Sasse F, Shaaban S, Gutschow M, Konig GM: HLE-inhibitory alkaloids with a polyketide skeleton from the marine-derived fungus Coniothyrium cereale. J Nat Prod. 2011 Oct 28;74(10):2282-5. doi: 10.1021/np2004227. Epub 2011 Sep 16. [PubMed:21923104 ]

Showing NP-Card for (-)-cereolactam (NP0010322)

MOL for NP0010322 ((-)-cereolactam)

3D MOL for NP0010322 ((-)-cereolactam)

3D SDF for NP0010322 ((-)-cereolactam)

3D-SDF for NP0010322 ((-)-cereolactam)

PDB for NP0010322 ((-)-cereolactam)

3D PDB for NP0010322 ((-)-cereolactam)

SMILES for NP0010322 ((-)-cereolactam)

INCHI for NP0010322 ((-)-cereolactam)

Structure for NP0010322 ((-)-cereolactam)

3D Structure for NP0010322 ((-)-cereolactam)