NP-MRD: Showing NP-Card for (1s,2r,5s,6s,8r,9s,10r,12s,15r,16s,25s,27s,28s)-21-chloro-15,16,33,33-tetramethyl-24-methylidene-10-(prop-1-en-2-yl)-7,11,32-trioxa-18-azadecacyclo[25.4.2.0²,¹⁶.0⁵,¹⁵.0⁶,⁸.0⁶,¹².0¹⁷,³¹.0¹⁹,³⁰.0²²,²⁹.0²⁵,²⁸]tritriaconta-17(31),19,21,29-tetraene-5,9-diol (NP0223328)

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Record Information

Version

1.0

Created at

2022-09-06 01:23:40 UTC

Updated at

2022-09-06 01:23:40 UTC

NP-MRD ID

NP0223328

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,5s,6s,8r,9s,10r,12s,15r,16s,25s,27s,28s)-21-chloro-15,16,33,33-tetramethyl-24-methylidene-10-(prop-1-en-2-yl)-7,11,32-trioxa-18-azadecacyclo[25.4.2.0²,¹⁶.0⁵,¹⁵.0⁶,⁸.0⁶,¹².0¹⁷,³¹.0¹⁹,³⁰.0²²,²⁹.0²⁵,²⁸]tritriaconta-17(31),19,21,29-tetraene-5,9-diol

Description

PENITREM F belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. (1s,2r,5s,6s,8r,9s,10r,12s,15r,16s,25s,27s,28s)-21-chloro-15,16,33,33-tetramethyl-24-methylidene-10-(prop-1-en-2-yl)-7,11,32-trioxa-18-azadecacyclo[25.4.2.0²,¹⁶.0⁵,¹⁵.0⁶,⁸.0⁶,¹².0¹⁷,³¹.0¹⁹,³⁰.0²²,²⁹.0²⁵,²⁸]tritriaconta-17(31),19,21,29-tetraene-5,9-diol is found in Penicillium solitum. It was first documented in 2011 (PMID: 21646818). Based on a literature review a significant number of articles have been published on PENITREM F (PMID: 24273638) (PMID: 29338236) (PMID: 28671569) (PMID: 24211635).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062203232D          

 44 53  0  0  1  0            999 V2000
   10.3068   -4.7796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4844   -4.7147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1293   -3.9701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3069   -3.9052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3166   -3.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9939   -2.7670    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.5390   -2.9627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9116   -3.4984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1431   -3.3412    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7493   -4.0662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3172   -4.6647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0618   -4.3096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8395   -4.5851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1946   -5.3298    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.0170   -5.3946    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.6967   -6.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9191   -6.1074    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1744   -6.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7101   -7.0899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7071   -7.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3968   -6.1870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0417   -5.4423    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2170   -5.4206    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6490   -6.0190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8468   -5.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6126   -5.0353    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5048   -5.8532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8104   -4.8426    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0447   -5.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2425   -5.4410    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4403   -5.2483    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8723   -5.8466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2061   -4.4572    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4039   -4.2645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1641   -4.8629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1697   -3.4735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7740   -3.8589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5762   -4.0515    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1442   -3.4532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9464   -3.6459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1806   -4.4369    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7485   -3.8385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9828   -4.6296    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0775   -3.8101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  5  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
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  2  0  0  0  0
  4 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  1  0  0  0
 17 16  1  6  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 11  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 30 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 34  1  1  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 33 37  1  0  0  0  0
 38 37  1  1  0  0  0
 28 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 26 41  1  0  0  0  0
 41 42  1  1  0  0  0
 41 43  1  0  0  0  0
 10 43  1  0  0  0  0
 23 43  1  0  0  0  0
 43 44  1  6  0  0  0
M  END


  Mrv1652309062203232D          

 44 53  0  0  1  0            999 V2000
   10.3068   -4.7796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4844   -4.7147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1293   -3.9701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3069   -3.9052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3166   -3.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9939   -2.7670    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.5390   -2.9627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9116   -3.4984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1431   -3.3412    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7493   -4.0662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3172   -4.6647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0618   -4.3096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8395   -4.5851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1946   -5.3298    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.0170   -5.3946    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.6967   -6.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9191   -6.1074    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1744   -6.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7101   -7.0899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7071   -7.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3968   -6.1870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0417   -5.4423    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2170   -5.4206    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6490   -6.0190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8468   -5.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6126   -5.0353    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5048   -5.8532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8104   -4.8426    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0447   -5.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2425   -5.4410    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4403   -5.2483    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8723   -5.8466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2061   -4.4572    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4039   -4.2645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1641   -4.8629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1697   -3.4735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7740   -3.8589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5762   -4.0515    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1442   -3.4532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9464   -3.6459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1806   -4.4369    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7485   -3.8385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9828   -4.6296    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0775   -3.8101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  5  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
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  2  0  0  0  0
  4 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  1  0  0  0
 17 16  1  6  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 11  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 30 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 34  1  1  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 33 37  1  0  0  0  0
 38 37  1  1  0  0  0
 28 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 26 41  1  0  0  0  0
 41 42  1  1  0  0  0
 41 43  1  0  0  0  0
 10 43  1  0  0  0  0
 23 43  1  0  0  0  0
 43 44  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0223328

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)[C@H]1O[C@H]2CC[C@]3(C)[C@]4(C)[C@@H](CC[C@@]3(O)[C@]22O[C@@H]2[C@H]1O)[C@@H]1OC(C)(C)[C@H]2C[C@H]3[C@@H]2C2=C5C(NC4=C15)=CC(Cl)=C2CC3=C

> <INCHI_IDENTIFIER>
InChI=1S/C37H44ClNO5/c1-15(2)29-28(40)32-37(44-32)23(42-29)9-10-34(6)35(7)19(8-11-36(34,37)41)30-27-26-22(39-31(27)35)14-21(38)18-12-16(3)17-13-20(24(17)25(18)26)33(4,5)43-30/h14,17,19-20,23-24,28-30,32,39-41H,1,3,8-13H2,2,4-7H3/t17-,19+,20+,23+,24+,28+,29-,30+,32-,34-,35-,36+,37+/m1/s1

> <INCHI_KEY>
YWORPEZTBDVGCS-JCMMWUKFSA-N

> <FORMULA>
C37H44ClNO5

> <MOLECULAR_WEIGHT>
618.21

> <EXACT_MASS>
617.2908012

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
88

> <JCHEM_AVERAGE_POLARIZABILITY>
70.53443427356802

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,6S,8R,9S,10R,12S,15R,16S,25S,27S,28S)-21-chloro-15,16,33,33-tetramethyl-24-methylidene-10-(prop-1-en-2-yl)-7,11,32-trioxa-18-azadecacyclo[25.4.2.0^{2,16}.0^{5,15}.0^{6,8}.0^{6,12}.0^{17,31}.0^{19,30}.0^{22,29}.0^{25,28}]tritriaconta-17(31),19(30),20,22(29)-tetraene-5,9-diol

> <JCHEM_LOGP>
5.360639697666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
10

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.412714868698469

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.798320256725923

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6011931834560853

> <JCHEM_POLAR_SURFACE_AREA>
87.24000000000001

> <JCHEM_REFRACTIVITY>
167.59389999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,6S,8R,9S,10R,12S,15R,16S,25S,27S,28S)-21-chloro-15,16,33,33-tetramethyl-24-methylidene-10-(prop-1-en-2-yl)-7,11,32-trioxa-18-azadecacyclo[25.4.2.0^{2,16}.0^{5,15}.0^{6,8}.0^{6,12}.0^{17,31}.0^{19,30}.0^{22,29}.0^{25,28}]tritriaconta-17(31),19(30),20,22(29)-tetraene-5,9-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      19.239  -8.922   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.704  -8.801   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.041  -7.411   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.506  -7.290   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.524  -6.045   0.000  0.00  0.00           C+0
HETATM    6 Cl   UNK     0      16.789  -5.165   0.000  0.00  0.00          Cl+0
HETATM    7  C   UNK     0      14.073  -5.530   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.902  -6.530   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      11.467  -6.237   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      10.732  -7.590   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.792  -8.707   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.182  -8.045   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.634  -8.559   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.297  -9.949   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.832 -10.070   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.234 -11.915   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.782 -11.400   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.392 -12.063   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.392 -13.234   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.520 -13.332   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      11.941 -11.549   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      11.278 -10.159   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.738 -10.119   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.678 -11.235   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.181 -10.876   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.744  -9.399   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.542 -10.926   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.246  -9.040   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.683 -10.516   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.186 -10.156   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.689  -9.797   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.628 -10.914   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.251  -8.320   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.754  -7.960   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.306  -9.077   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.317  -6.484   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       3.312  -7.203   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       4.809  -7.563   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.869  -6.446   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       7.367  -6.806   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       7.804  -8.282   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       8.864  -7.165   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       9.301  -8.642   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       9.478  -7.112   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   43                                                  
CONECT   11   10   12   22                                                  
CONECT   12   11    8   13                                                  
CONECT   13   12    4   14                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14    2   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   14   18                                                  
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22                                                       
CONECT   22   21   11   23                                                  
CONECT   23   22   24   43                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28   41                                             
CONECT   27   26                                                            
CONECT   28   26   29   30   38                                             
CONECT   29   28   30                                                       
CONECT   30   29   28   31                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   37                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   33   38                                                       
CONECT   38   37   28   39                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   26   42   43                                             
CONECT   42   41                                                            
CONECT   43   41   10   23   44                                             
CONECT   44   43                                                            
MASTER        0    0    0    0    0    0    0    0   44    0  106    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₇H₄₄ClNO₅

Average Mass

618.2100 Da

Monoisotopic Mass

617.29080 Da

IUPAC Name

(1S,2R,5S,6S,8R,9S,10R,12S,15R,16S,25S,27S,28S)-21-chloro-15,16,33,33-tetramethyl-24-methylidene-10-(prop-1-en-2-yl)-7,11,32-trioxa-18-azadecacyclo[25.4.2.0^{2,16}.0^{5,15}.0^{6,8}.0^{6,12}.0^{17,31}.0^{19,30}.0^{22,29}.0^{25,28}]tritriaconta-17(31),19(30),20,22(29)-tetraene-5,9-diol

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(=C)[C@H]1O[C@H]2CC[C@]3(C)[C@]4(C)[C@@H](CC[C@@]3(O)[C@]22O[C@@H]2[C@H]1O)[C@@H]1OC(C)(C)[C@H]2C[C@H]3[C@@H]2C2=C5C(NC4=C15)=CC(Cl)=C2CC3=C

InChI Identifier

InChI=1S/C37H44ClNO5/c1-15(2)29-28(40)32-37(44-32)23(42-29)9-10-34(6)35(7)19(8-11-36(34,37)41)30-27-26-22(39-31(27)35)14-21(38)18-12-16(3)17-13-20(24(17)25(18)26)33(4,5)43-30/h14,17,19-20,23-24,28-30,32,39-41H,1,3,8-13H2,2,4-7H3/t17-,19+,20+,23+,24+,28+,29-,30+,32-,34-,35-,36+,37+/m1/s1

InChI Key

YWORPEZTBDVGCS-JCMMWUKFSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Penicillium solitum	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthalene
Tetralin
3-alkylindole
Indole or derivatives
Indole
1,4-dioxepane
Dioxepane
Pyran
Oxane
Aryl halide
Monosaccharide
Benzenoid
Aryl chloride
Heteroaromatic compound
Cyclic alcohol
Tertiary alcohol
Pyrrole
Secondary alcohol
Dialkyl ether
Oxacycle
Oxirane
Ether
Azacycle
Organic oxygen compound
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
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	5.36	ChemAxon
pKa (Strongest Acidic)	12.8	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	87.24 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	167.59 m³·mol⁻¹	ChemAxon
Polarizability	70.53 Å³	ChemAxon
Number of Rings	10	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00023574

Chemspider ID

2342793

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3086086

PDB ID

Not Available

ChEBI ID

176916

Good Scents ID

Not Available

References

General References

Sallam AA, Houssen WE, Gissendanner CR, Orabi KY, Foudah AI, El Sayed KA: Bioguided discovery and pharmacophore modeling of the mycotoxic indole diterpene alkaloids penitrems as breast cancer proliferation, migration, and invasion inhibitors. Medchemcomm. 2013 Oct;4(10). doi: 10.1039/C3MD00198A. [PubMed:24273638 ]
Kalinina SA, Jagels A, Hickert S, Mauriz Marques LM, Cramer B, Humpf HU: Detection of the Cytotoxic Penitrems A-F in Cheese from the European Single Market by HPLC-MS/MS. J Agric Food Chem. 2018 Feb 7;66(5):1264-1269. doi: 10.1021/acs.jafc.7b06001. Epub 2018 Jan 25. [PubMed:29338236 ]
Kalinina SA, Jagels A, Cramer B, Geisen R, Humpf HU: Influence of Environmental Factors on the Production of Penitrems A-F by Penicillium crustosum. Toxins (Basel). 2017 Jul 1;9(7):210. doi: 10.3390/toxins9070210. [PubMed:28671569 ]
Sallam AA, Ayoub NM, Foudah AI, Gissendanner CR, Meyer SA, El Sayed KA: Indole diterpene alkaloids as novel inhibitors of the Wnt/beta-catenin pathway in breast cancer cells. Eur J Med Chem. 2013;70:594-606. doi: 10.1016/j.ejmech.2013.09.045. Epub 2013 Oct 8. [PubMed:24211635 ]
Ahn HS, dela Pena I, Kim YC, Cheong JH: 4-Chloro-7-trifluoromethyl-10H- benzo[4,5]furo[3,2-b]indole-1-carboxylic acid (TBIC), a putative BK(Ca) channel opener with uterine relaxant activities. Pharmacology. 2011;87(5-6):331-40. doi: 10.1159/000328141. Epub 2011 Jun 1. [PubMed:21646818 ]
LOTUS database [Link]