MiMeDB: Showing metabocard for Penitrem F (MMDBc0006575)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-14 23:43:11 UTC

Update Date

2022-08-31 06:25:41 UTC

Metabolite ID

MMDBc0006575

Metabolite Identification

Common Name

Penitrem F

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. Based on a literature review a significant number of articles have been published on PENITREM F.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152101432D          

 53 62  0  0  1  0            999 V2000
    2.0169    5.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6881    4.4872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1587    4.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5703    2.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5674    2.2325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5970    5.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9389    5.5573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5053    3.3484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9913    5.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7941    5.7190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7025    3.5382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9782    5.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5544    2.9991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3843    6.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    5.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3360    4.6701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8711    3.9886    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.3161    5.3318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0711    3.9488    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7757    3.2718    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1629    6.1424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7588    5.8772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4255    5.3084    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0484    4.0504    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.6906    4.7938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9120    5.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1686    4.7087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2939    4.1076    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0568    4.8978    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8959    3.9301    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5124    5.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0967    3.9178    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0323    2.9140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0312    4.9288    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8341    4.7390    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4654    4.3284    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6625    4.5182    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.7884    6.6804    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.9898    6.0316    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7281    3.5072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3606    3.5101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6226    5.4982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2537    3.1867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8996    3.7280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6124    3.6266    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3895    3.1877    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1607    3.8217    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597    4.7080    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5133    4.7320    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5309    3.3174    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4910    4.2974    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7196    3.9761    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3338    3.1276    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0  0  0  0
 11  8  1  0  0  0  0
 15  1  2  0  0  0  0
 15  2  1  0  0  0  0
 16  3  2  0  0  0  0
 16 12  1  0  0  0  0
 17 13  1  0  0  0  0
 17 16  1  0  0  0  0
 18 12  1  0  0  0  0
 19  8  1  0  0  0  0
 20 13  1  0  0  0  0
 21 14  2  0  0  0  0
 21 18  1  0  0  0  0
 22 14  1  0  0  0  0
 23  9  1  0  0  0  0
 24 17  1  0  0  0  0
 24 20  1  0  0  0  0
 25 18  2  0  0  0  0
 25 24  1  0  0  0  0
 26 22  2  0  0  0  0
 26 25  1  0  0  0  0
 27 26  1  0  0  0  0
 29 15  1  1  0  0  0
 29 28  1  0  0  0  0
 30 19  1  0  0  0  0
 30 27  1  0  0  0  0
 31 27  2  0  0  0  0
 32 28  1  0  0  0  0
 33  4  1  0  0  0  0
 33  5  1  0  0  0  0
 33 20  1  0  0  0  0
 34  6  1  1  0  0  0
 34 10  1  0  0  0  0
 35  7  1  6  0  0  0
 35 19  1  0  0  0  0
 35 31  1  0  0  0  0
 35 34  1  0  0  0  0
 36 11  1  0  0  0  0
 36 34  1  0  0  0  0
 37 23  1  0  0  0  0
 37 32  1  0  0  0  0
 37 36  1  0  0  0  0
 38 21  1  0  0  0  0
 39 22  1  0  0  0  0
 39 31  1  0  0  0  0
 28 40  1  1  0  0  0
 36 41  1  6  0  0  0
 42 23  1  0  0  0  0
 42 29  1  0  0  0  0
 43 30  1  0  0  0  0
 43 33  1  0  0  0  0
 44 32  1  0  0  0  0
 37 44  1  6  0  0  0
 17 45  1  6  0  0  0
 19 46  1  1  0  0  0
 20 47  1  1  0  0  0
 23 48  1  6  0  0  0
 24 49  1  6  0  0  0
 28 50  1  6  0  0  0
 29 51  1  6  0  0  0
 30 52  1  6  0  0  0
 32 53  1  1  0  0  0
M  END


  Mrv1652305152101432D          

 53 62  0  0  1  0            999 V2000
    2.0169    5.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6881    4.4872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1587    4.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5703    2.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5674    2.2325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5970    5.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9389    5.5573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5053    3.3484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9913    5.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7941    5.7190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7025    3.5382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9782    5.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5544    2.9991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3843    6.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    5.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3360    4.6701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8711    3.9886    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.3161    5.3318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0711    3.9488    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7757    3.2718    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1629    6.1424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7588    5.8772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4255    5.3084    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0484    4.0504    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.6906    4.7938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9120    5.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1686    4.7087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2939    4.1076    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0568    4.8978    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8959    3.9301    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5124    5.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0967    3.9178    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0323    2.9140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0312    4.9288    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8341    4.7390    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4654    4.3284    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6625    4.5182    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.7884    6.6804    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.9898    6.0316    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7281    3.5072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3606    3.5101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6226    5.4982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2537    3.1867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8996    3.7280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6124    3.6266    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3895    3.1877    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1607    3.8217    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597    4.7080    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5133    4.7320    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5309    3.3174    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4910    4.2974    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7196    3.9761    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3338    3.1276    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0  0  0  0
 11  8  1  0  0  0  0
 15  1  2  0  0  0  0
 15  2  1  0  0  0  0
 16  3  2  0  0  0  0
 16 12  1  0  0  0  0
 17 13  1  0  0  0  0
 17 16  1  0  0  0  0
 18 12  1  0  0  0  0
 19  8  1  0  0  0  0
 20 13  1  0  0  0  0
 21 14  2  0  0  0  0
 21 18  1  0  0  0  0
 22 14  1  0  0  0  0
 23  9  1  0  0  0  0
 24 17  1  0  0  0  0
 24 20  1  0  0  0  0
 25 18  2  0  0  0  0
 25 24  1  0  0  0  0
 26 22  2  0  0  0  0
 26 25  1  0  0  0  0
 27 26  1  0  0  0  0
 29 15  1  1  0  0  0
 29 28  1  0  0  0  0
 30 19  1  0  0  0  0
 30 27  1  0  0  0  0
 31 27  2  0  0  0  0
 32 28  1  0  0  0  0
 33  4  1  0  0  0  0
 33  5  1  0  0  0  0
 33 20  1  0  0  0  0
 34  6  1  1  0  0  0
 34 10  1  0  0  0  0
 35  7  1  6  0  0  0
 35 19  1  0  0  0  0
 35 31  1  0  0  0  0
 35 34  1  0  0  0  0
 36 11  1  0  0  0  0
 36 34  1  0  0  0  0
 37 23  1  0  0  0  0
 37 32  1  0  0  0  0
 37 36  1  0  0  0  0
 38 21  1  0  0  0  0
 39 22  1  0  0  0  0
 39 31  1  0  0  0  0
 28 40  1  1  0  0  0
 36 41  1  6  0  0  0
 42 23  1  0  0  0  0
 42 29  1  0  0  0  0
 43 30  1  0  0  0  0
 43 33  1  0  0  0  0
 44 32  1  0  0  0  0
 37 44  1  6  0  0  0
 17 45  1  6  0  0  0
 19 46  1  1  0  0  0
 20 47  1  1  0  0  0
 23 48  1  6  0  0  0
 24 49  1  6  0  0  0
 28 50  1  6  0  0  0
 29 51  1  6  0  0  0
 30 52  1  6  0  0  0
 32 53  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0006575

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@]12O[C@@]11[C@]([H])(CC[C@]3(C)[C@@]4(C)C5=C6C7=C(N5)C=C(Cl)C5=C7[C@@]7([H])[C@]([H])(C[C@]7([H])C(C)(C)O[C@@]6([H])[C@]4([H])CC[C@@]13O)C(=C)C5)O[C@]([H])(C(C)=C)[C@]2([H])O

> <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

> <ALOGPS_LOGP>
5.57

> <JCHEM_LOGP>
5.360639697666668

> <ALOGPS_LOGS>
-6.41

> <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

> <ALOGPS_SOLUBILITY>
2.43e-04 g/l

> <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                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0       3.765  10.972   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.151   8.376   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.696   8.602   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.865   4.272   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.993   4.167   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.314  10.321   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.953  10.374   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.143   6.250   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.317  11.030   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.816  10.676   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.645   6.605   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.493  10.105   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.701   5.598   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.517  11.975   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.207   9.497   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.161   8.717   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.293   7.445   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      19.257   9.953   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.199   7.371   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      18.248   6.107   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.971  11.466   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.350  10.971   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.261   9.909   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.757   7.561   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      18.089   8.948   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      16.636   9.457   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.248   8.790   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.149   7.668   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.706   9.143   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.739   7.336   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.023   9.723   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.647   7.313   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      16.860   5.440   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.258   9.200   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      12.757   8.846   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.202   8.080   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.703   8.434   0.000  0.00  0.00           C+0
HETATM   38 Cl   UNK     0      20.138  12.470   0.000  0.00  0.00          Cl+0
HETATM   39  N   UNK     0      14.914  11.259   0.000  0.00  0.00           N+0
HETATM   40  O   UNK     0       5.092   6.547   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      10.006   6.552   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       6.762  10.263   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      15.407   5.949   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       9.146   6.959   0.000  0.00  0.00           O+0
HETATM   45  H   UNK     0      21.677   6.770   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0      13.794   5.950   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0      17.100   7.134   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0       7.205   8.788   0.000  0.00  0.00           H+0
HETATM   49  H   UNK     0      19.625   8.833   0.000  0.00  0.00           H+0
HETATM   50  H   UNK     0       6.591   6.193   0.000  0.00  0.00           H+0
HETATM   51  H   UNK     0       4.650   8.022   0.000  0.00  0.00           H+0
HETATM   52  H   UNK     0      16.277   7.422   0.000  0.00  0.00           H+0
HETATM   53  H   UNK     0       8.090   5.838   0.000  0.00  0.00           H+0
CONECT    1   15                                                            
CONECT    2   15                                                            
CONECT    3   16                                                            
CONECT    4   33                                                            
CONECT    5   33                                                            
CONECT    6   34                                                            
CONECT    7   35                                                            
CONECT    8   11   19                                                       
CONECT    9   10   23                                                       
CONECT   10    9   34                                                       
CONECT   11    8   36                                                       
CONECT   12   16   18                                                       
CONECT   13   17   20                                                       
CONECT   14   21   22                                                       
CONECT   15    1    2   29                                                  
CONECT   16    3   12   17                                                  
CONECT   17   13   16   24   45                                             
CONECT   18   12   21   25                                                  
CONECT   19    8   30   35   46                                             
CONECT   20   13   24   33   47                                             
CONECT   21   14   18   38                                                  
CONECT   22   14   26   39                                                  
CONECT   23    9   37   42   48                                             
CONECT   24   17   20   25   49                                             
CONECT   25   18   24   26                                                  
CONECT   26   22   25   27                                                  
CONECT   27   26   30   31                                                  
CONECT   28   29   32   40   50                                             
CONECT   29   15   28   42   51                                             
CONECT   30   19   27   43   52                                             
CONECT   31   27   35   39                                                  
CONECT   32   28   37   44   53                                             
CONECT   33    4    5   20   43                                             
CONECT   34    6   10   35   36                                             
CONECT   35    7   19   31   34                                             
CONECT   36   11   34   37   41                                             
CONECT   37   23   32   36   44                                             
CONECT   38   21                                                            
CONECT   39   22   31                                                       
CONECT   40   28                                                            
CONECT   41   36                                                            
CONECT   42   23   29                                                       
CONECT   43   30   33                                                       
CONECT   44   32   37                                                       
CONECT   45   17                                                            
CONECT   46   19                                                            
CONECT   47   20                                                            
CONECT   48   23                                                            
CONECT   49   24                                                            
CONECT   50   28                                                            
CONECT   51   29                                                            
CONECT   52   30                                                            
CONECT   53   32                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  124    0
END

Synonyms

Not Available

Molecular Formula

C₃₇H₄₄ClNO₅

Average Mass

618.21

Monoisotopic Mass

617.2908012

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

[H][C@]12O[C@@]11[C@]([H])(CC[C@]3(C)[C@@]4(C)C5=C6C7=C(N5)C=C(Cl)C5=C7[C@@]7([H])[C@]([H])(C[C@]7([H])C(C)(C)O[C@@]6([H])[C@]4([H])CC[C@@]13O)C(=C)C5)O[C@]([H])(C(C)=C)[C@]2([H])O

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

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

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.00024 g/L	ALOGPS
logP	5.57	ALOGPS
logP	5.36	ChemAxon
logS	-6.4	ALOGPS
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

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	2	Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

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

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for Penitrem F (MMDBc0006575)

MOL for #<Metabolite:0x00007fece8ec1aa8>

3D MOL for #<Metabolite:0x00007fece8ec1aa8>

3D SDF for #<Metabolite:0x00007fece8ec1aa8>

3D-SDF for #<Metabolite:0x00007fece8ec1aa8>

PDB for #<Metabolite:0x00007fece8ec1aa8>

3D PDB for #<Metabolite:0x00007fece8ec1aa8>

SMILES for #<Metabolite:0x00007fece8ec1aa8>

INCHI for #<Metabolite:0x00007fece8ec1aa8>

Structure for #<Metabolite:0x00007fece8ec1aa8>

3D Structure for #<Metabolite:0x00007fece8ec1aa8>