NP-MRD: Showing NP-Card for Cyclopenin (NP0004755)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2020-12-09 02:10:38 UTC

Updated at

2024-09-03 04:16:46 UTC

NP-MRD ID

NP0004755

Natural Product DOI

https://doi.org/10.57994/0794

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cyclopenin

Provided By

NPAtlas

Description

Cyclopenin is found in Aspergillus nidulans, Aspergillus simplicissimum, Penicillium aurantiogriseum, Penicillium hirsutum, Penicillium cyclopium and Penicillium namyslowskii. Cyclopenin was first documented in 1954 (PMID: 13198807). Based on a literature review very few articles have been published on 2-hydroxy-4-methyl-3'-phenyl-4,5-dihydrospiro[1,4-benzodiazepine-3,2'-oxirane]-5-one (PMID: 37455565).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118093D          

 36 39  0  0  0  0            999 V2000
    0.4363    1.6410    1.6606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2933    0.7097    0.8308 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4123    1.2592    0.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3507    2.4894   -0.0931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5900    0.5644   -0.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3650    1.3394   -1.2505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5134    0.8548   -1.8371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9146   -0.4469   -1.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1353   -1.2252   -0.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9905   -0.7346   -0.1736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3049   -1.6628    0.6631 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0058   -1.5709    1.2326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7496   -2.3290    2.2224 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1077   -0.6586    0.7784 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4926   -1.1218   -0.5781 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3845   -1.2278    0.6305 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6606   -0.6125    0.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2186   -0.8385   -0.9513 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4309   -0.2933   -1.3355 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1308    0.5131   -0.4626 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5898    0.7499    0.7778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3689    0.1937    1.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2276    2.4452    2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7674    1.0929    2.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2544    2.1523    1.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0812    2.3583   -1.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1341    1.4573   -2.4971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8195   -0.8041   -2.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4234   -2.2488   -0.5447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8465   -2.5446    0.8915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5012   -2.3218    0.9076 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7124   -1.4672   -1.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8725   -0.4684   -2.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0885    0.9407   -0.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1261    1.3888    1.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0145    0.4264    2.1443 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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  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  2  0  0  0  0
 10 11  1  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  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 14  2  1  0  0  0  0
 22 17  1  0  0  0  0
 10  5  1  0  0  0  0
 16 14  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
  6 26  1  0  0  0  0
  7 27  1  0  0  0  0
  8 28  1  0  0  0  0
  9 29  1  0  0  0  0
 11 30  1  0  0  0  0
 16 31  1  1  0  0  0
 18 32  1  0  0  0  0
 19 33  1  0  0  0  0
 20 34  1  0  0  0  0
 21 35  1  0  0  0  0
 22 36  1  0  0  0  0
M  END

     RDKit          3D

 36 39  0  0  0  0  0  0  0  0999 V2000
    0.4363    1.6410    1.6606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2933    0.7097    0.8308 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4123    1.2592    0.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3507    2.4894   -0.0931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5900    0.5644   -0.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3650    1.3394   -1.2505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5134    0.8548   -1.8371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9146   -0.4469   -1.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1353   -1.2252   -0.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9905   -0.7346   -0.1736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3049   -1.6628    0.6631 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0058   -1.5709    1.2326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7496   -2.3290    2.2224 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1077   -0.6586    0.7784 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4926   -1.1218   -0.5781 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3845   -1.2278    0.6305 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6606   -0.6125    0.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2186   -0.8385   -0.9513 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4309   -0.2933   -1.3355 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1308    0.5131   -0.4626 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5898    0.7499    0.7778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3689    0.1937    1.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2276    2.4452    2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7674    1.0929    2.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2544    2.1523    1.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0812    2.3583   -1.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1341    1.4573   -2.4971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8195   -0.8041   -2.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4234   -2.2488   -0.5447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8465   -2.5446    0.8915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5012   -2.3218    0.9076 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7124   -1.4672   -1.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8725   -0.4684   -2.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0885    0.9407   -0.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1261    1.3888    1.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0145    0.4264    2.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  6
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 14  2  1  0
 22 17  1  0
 10  5  1  0
 16 14  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 11 30  1  0
 16 31  1  1
 18 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
 22 36  1  0
M  END


  Mrv1652306242118093D          

 36 39  0  0  0  0            999 V2000
    0.4363    1.6410    1.6606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2933    0.7097    0.8308 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4123    1.2592    0.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3507    2.4894   -0.0931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5900    0.5644   -0.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3650    1.3394   -1.2505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5134    0.8548   -1.8371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9146   -0.4469   -1.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1353   -1.2252   -0.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9905   -0.7346   -0.1736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3049   -1.6628    0.6631 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0058   -1.5709    1.2326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7496   -2.3290    2.2224 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1077   -0.6586    0.7784 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4926   -1.1218   -0.5781 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3845   -1.2278    0.6305 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6606   -0.6125    0.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2186   -0.8385   -0.9513 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4309   -0.2933   -1.3355 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1308    0.5131   -0.4626 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5898    0.7499    0.7778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3689    0.1937    1.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2276    2.4452    2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7674    1.0929    2.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2544    2.1523    1.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0812    2.3583   -1.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1341    1.4573   -2.4971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8195   -0.8041   -2.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4234   -2.2488   -0.5447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8465   -2.5446    0.8915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5012   -2.3218    0.9076 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7124   -1.4672   -1.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8725   -0.4684   -2.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0885    0.9407   -0.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1261    1.3888    1.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0145    0.4264    2.1443 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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  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  2  0  0  0  0
 10 11  1  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  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 14  2  1  0  0  0  0
 22 17  1  0  0  0  0
 10  5  1  0  0  0  0
 16 14  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
  6 26  1  0  0  0  0
  7 27  1  0  0  0  0
  8 28  1  0  0  0  0
  9 29  1  0  0  0  0
 11 30  1  0  0  0  0
 16 31  1  1  0  0  0
 18 32  1  0  0  0  0
 19 33  1  0  0  0  0
 20 34  1  0  0  0  0
 21 35  1  0  0  0  0
 22 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004755

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N1C2=C([H])C([H])=C([H])C([H])=C2C(=O)N(C([H])([H])[H])[C@]2(O[C@@]2([H])C2=C([H])C([H])=C([H])C([H])=C2[H])C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H14N2O3/c1-19-15(20)12-9-5-6-10-13(12)18-16(21)17(19)14(22-17)11-7-3-2-4-8-11/h2-10,14H,1H3,(H,18,21)/t14-,17+/m0/s1

> <INCHI_KEY>
APLKWZASYUZSBL-UHFFFAOYSA-N

> <FORMULA>
C17H14N2O3

> <MOLECULAR_WEIGHT>
294.31

> <EXACT_MASS>
294.100442319

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
30.39329208858895

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,3'S)-4-methyl-3'-phenyl-1,2,4,5-tetrahydrospiro[1,4-benzodiazepine-3,2'-oxirane]-2,5-dione

> <ALOGPS_LOGP>
2.07

> <JCHEM_LOGP>
3.290580842999999

> <ALOGPS_LOGS>
-2.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.086839223856918

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7291433598643673

> <JCHEM_POLAR_SURFACE_AREA>
61.940000000000005

> <JCHEM_REFRACTIVITY>
81.58640000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.43e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,3'S)-4-methyl-3'-phenyl-1H-spiro[1,4-benzodiazepine-3,2'-oxirane]-2,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 36 39  0  0  0  0  0  0  0  0999 V2000
    0.4363    1.6410    1.6606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2933    0.7097    0.8308 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4123    1.2592    0.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3507    2.4894   -0.0931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5900    0.5644   -0.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3650    1.3394   -1.2505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5134    0.8548   -1.8371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9146   -0.4469   -1.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1353   -1.2252   -0.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9905   -0.7346   -0.1736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3049   -1.6628    0.6631 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0058   -1.5709    1.2326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7496   -2.3290    2.2224 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1077   -0.6586    0.7784 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4926   -1.1218   -0.5781 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3845   -1.2278    0.6305 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6606   -0.6125    0.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2186   -0.8385   -0.9513 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4309   -0.2933   -1.3355 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1308    0.5131   -0.4626 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5898    0.7499    0.7778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3689    0.1937    1.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2276    2.4452    2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7674    1.0929    2.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2544    2.1523    1.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0812    2.3583   -1.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1341    1.4573   -2.4971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8195   -0.8041   -2.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4234   -2.2488   -0.5447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8465   -2.5446    0.8915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5012   -2.3218    0.9076 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7124   -1.4672   -1.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8725   -0.4684   -2.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0885    0.9407   -0.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1261    1.3888    1.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0145    0.4264    2.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  6
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 14  2  1  0
 22 17  1  0
 10  5  1  0
 16 14  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 11 30  1  0
 16 31  1  1
 18 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
 22 36  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       0.436   1.641   1.661  0.00  0.00           C+0
HETATM    2  N   UNK     0      -0.293   0.710   0.831  0.00  0.00           N+0
HETATM    3  C   UNK     0      -1.412   1.259   0.105  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.351   2.489  -0.093  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.590   0.564  -0.418  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.365   1.339  -1.250  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.513   0.855  -1.837  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.915  -0.447  -1.593  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.135  -1.225  -0.755  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.990  -0.735  -0.174  0.00  0.00           C+0
HETATM   11  N   UNK     0      -2.305  -1.663   0.663  0.00  0.00           N+0
HETATM   12  C   UNK     0      -1.006  -1.571   1.233  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.750  -2.329   2.222  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.108  -0.659   0.778  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.493  -1.122  -0.578  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.385  -1.228   0.631  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.661  -0.613   0.287  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.219  -0.839  -0.951  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.431  -0.293  -1.335  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.131   0.513  -0.463  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.590   0.750   0.778  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.369   0.194   1.149  0.00  0.00           C+0
HETATM   23  H   UNK     0      -0.228   2.445   2.059  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.767   1.093   2.577  0.00  0.00           H+0
HETATM   25  H   UNK     0       1.254   2.152   1.157  0.00  0.00           H+0
HETATM   26  H   UNK     0      -3.081   2.358  -1.461  0.00  0.00           H+0
HETATM   27  H   UNK     0      -5.134   1.457  -2.497  0.00  0.00           H+0
HETATM   28  H   UNK     0      -5.819  -0.804  -2.065  0.00  0.00           H+0
HETATM   29  H   UNK     0      -4.423  -2.249  -0.545  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.846  -2.545   0.892  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.501  -2.322   0.908  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.712  -1.467  -1.684  0.00  0.00           H+0
HETATM   33  H   UNK     0       4.872  -0.468  -2.307  0.00  0.00           H+0
HETATM   34  H   UNK     0       6.088   0.941  -0.773  0.00  0.00           H+0
HETATM   35  H   UNK     0       5.126   1.389   1.493  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.014   0.426   2.144  0.00  0.00           H+0
CONECT    1    2   23   24   25                                             
CONECT    2    1    3   14                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   10                                                  
CONECT    6    5    7   26                                                  
CONECT    7    6    8   27                                                  
CONECT    8    7    9   28                                                  
CONECT    9    8   10   29                                                  
CONECT   10    9   11    5                                                  
CONECT   11   10   12   30                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15    2   16                                             
CONECT   15   14   16                                                       
CONECT   16   15   17   14   31                                             
CONECT   17   16   18   22                                                  
CONECT   18   17   19   32                                                  
CONECT   19   18   20   33                                                  
CONECT   20   19   21   34                                                  
CONECT   21   20   22   35                                                  
CONECT   22   21   17   36                                                  
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    6                                                            
CONECT   27    7                                                            
CONECT   28    8                                                            
CONECT   29    9                                                            
CONECT   30   11                                                            
CONECT   31   16                                                            
CONECT   32   18                                                            
CONECT   33   19                                                            
CONECT   34   20                                                            
CONECT   35   21                                                            
CONECT   36   22                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

RDKit          3D

36 39  0  0  0  0  0  0  0  0999 V2000
    0.4363    1.6410    1.6606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2933    0.7097    0.8308 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4123    1.2592    0.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3507    2.4894   -0.0931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5900    0.5644   -0.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3650    1.3394   -1.2505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5134    0.8548   -1.8371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9146   -0.4469   -1.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1353   -1.2252   -0.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9905   -0.7346   -0.1736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3049   -1.6628    0.6631 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0058   -1.5709    1.2326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7496   -2.3290    2.2224 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1077   -0.6586    0.7784 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4926   -1.1218   -0.5781 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3845   -1.2278    0.6305 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6606   -0.6125    0.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2186   -0.8385   -0.9513 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4309   -0.2933   -1.3355 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1308    0.5131   -0.4626 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5898    0.7499    0.7778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3689    0.1937    1.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2276    2.4452    2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7674    1.0929    2.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2544    2.1523    1.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0812    2.3583   -1.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1341    1.4573   -2.4971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8195   -0.8041   -2.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4234   -2.2488   -0.5447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8465   -2.5446    0.8915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5012   -2.3218    0.9076 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7124   -1.4672   -1.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8725   -0.4684   -2.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0885    0.9407   -0.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1261    1.3888    1.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0145    0.4264    2.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  6
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 14  2  1  0
 22 17  1  0
 10  5  1  0
 16 14  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 11 30  1  0
 16 31  1  1
 18 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
 22 36  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Cyclopenin	MeSH

Chemical Formula

C₁₇H₁₄N₂O₃

Average Mass

294.3100 Da

Monoisotopic Mass

294.10044 Da

IUPAC Name

(3R,3'S)-4-methyl-3'-phenyl-1,2,4,5-tetrahydrospiro[1,4-benzodiazepine-3,2'-oxirane]-2,5-dione

Traditional Name

(3R,3'S)-4-methyl-3'-phenyl-1H-spiro[1,4-benzodiazepine-3,2'-oxirane]-2,5-dione

CAS Registry Number

Not Available

SMILES

CN1C(=O)C2=CC=CC=C2NC(=O)C11OC1C1=CC=CC=C1

InChI Identifier

InChI=1S/C17H14N2O3/c1-19-15(20)12-9-5-6-10-13(12)18-16(21)17(19)14(22-17)11-7-3-2-4-8-11/h2-10,14H,1H3,(H,18,21)

InChI Key

APLKWZASYUZSBL-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CD3OD, experimental)	llx7772699@163.com	Not Available	Not Available	2024-05-08	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD3OD, experimental)	llx7772699@163.com	Not Available	Not Available	2024-05-08	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

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500, CD₃OD, simulated)	Not Available	Not Available	Not Available	2024-05-08	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Aspergillus nidulans	Fungi	KNApSAcK
Aspergillus simplicissimum	Fungi	KNApSAcK
Penicillium aurantiogriseum	LOTUS Database	35616633
Penicillium corymbiferum	LOTUS Database	35616633
Penicillium cyclopium	NPAtlas	13198807
Penicillium namyslowskii	Fungi	KNApSAcK
versicolor HYQZ-215		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

1,4-benzodiazepines

Direct Parent

1,4-benzodiazepines

Alternative Parents

Substituents

1,4-benzodiazepine
Alpha-amino acid or derivatives
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Vinylogous amide
Carboxamide group
Lactam
Secondary carboxylic acid amide
Carboxylic acid derivative
Oxirane
Oxacycle
Azacycle
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	2.07	ALOGPS
logP	3.29	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	11.09	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	61.94 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	81.59 m³·mol⁻¹	ChemAxon
Polarizability	30.39 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

NPA015264

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

238443

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

271117

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

BRACKEN A, POCKER A, RAISTRICK H: Studies in the biochemistry of microorganisms. 93. Cyclopenin, a nitrogen-containing metabolic product of Penicillium cyclopium Westling. Biochem J. 1954 Aug;57(4):587-95. doi: 10.1042/bj0570587. [PubMed:13198807 ]
Liao LX, Huang JG, Liu QP, Yao M, Wang WJ, Yang XL: Two new quinazoline alkaloids produced by Aspergillus versicolor and their antimicrobial activities. J Asian Nat Prod Res. 2024 Mar;26(3):320-327. doi: 10.1080/10286020.2023.2230895. Epub 2023 Jul 17. [PubMed:37455565 ]

Showing NP-Card for Cyclopenin (NP0004755)

MOL for NP0004755 (Cyclopenin)

3D MOL for NP0004755 (Cyclopenin)

3D SDF for NP0004755 (Cyclopenin)

3D-SDF for NP0004755 (Cyclopenin)

PDB for NP0004755 (Cyclopenin)

3D PDB for NP0004755 (Cyclopenin)

SMILES for NP0004755 (Cyclopenin)

INCHI for NP0004755 (Cyclopenin)

Structure for NP0004755 (Cyclopenin)

3D Structure for NP0004755 (Cyclopenin)