MiMeDB: Showing metabocard for 19-hydroxypenitrem A (MMDBc0013945)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 05:07:16 UTC

Update Date

2022-08-31 06:36:56 UTC

Metabolite ID

MMDBc0013945

Metabolite Identification

Common Name

19-hydroxypenitrem A

Description

19-Hydroxypenitrem A 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. 19-Hydroxypenitrem A is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152107072D          

 53 62  0  0  1  0            999 V2000
    4.2155   -1.7697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8867   -0.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3573   -0.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7689    1.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7660    1.8756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7956   -1.4211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1245   -1.4508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1899   -1.8007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9928   -1.6109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7039    0.7597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9011    0.5699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1768   -1.3053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7530    1.1090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5829   -2.3070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4525   -0.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5346   -0.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5147   -1.2236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0697    0.1196    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.3615   -2.0343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9574   -1.7690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9743    0.8364    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6241   -1.2003    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.1106   -0.9584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3672   -0.6006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8892   -0.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4925    0.0005    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2554   -0.7897    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7973   -1.1970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0945    0.1780    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2953    0.1903    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.2309    1.1941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2298   -0.8207    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.0327   -0.6309    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2698    0.1593    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6640   -0.2203    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.2470    0.0577    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8611   -0.4101    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.9870   -2.5723    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.1884   -1.9234    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9267    0.6009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5881    0.9204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5592    0.5980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4233    0.1038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8212   -1.3901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4523    0.9214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0982    0.3801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8110    0.4816    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0204    1.6601    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0583   -0.5999    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7295    0.7907    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6896   -0.1893    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9183    0.1320    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5324    0.9805    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0  0  0  0
 11 10  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 12  1  0  0  0  0
 18 13  1  0  0  0  0
 18 16  1  0  0  0  0
 19 14  2  0  0  0  0
 19 17  1  0  0  0  0
 20 14  1  0  0  0  0
 21 13  1  0  0  0  0
 22  8  1  0  0  0  0
 23 20  2  0  0  0  0
 24 23  1  0  0  0  0
 25 17  2  0  0  0  0
 25 23  1  0  0  0  0
 27 15  1  6  0  0  0
 27 26  1  0  0  0  0
 28 24  2  0  0  0  0
 29 24  1  0  0  0  0
 30 26  1  0  0  0  0
 31  4  1  0  0  0  0
 31  5  1  0  0  0  0
 31 21  1  0  0  0  0
 32  6  1  6  0  0  0
 32  9  1  0  0  0  0
 33  7  1  1  0  0  0
 33 28  1  0  0  0  0
 33 32  1  0  0  0  0
 34 10  1  0  0  0  0
 34 29  1  0  0  0  0
 34 33  1  0  0  0  0
 35 11  1  0  0  0  0
 35 32  1  0  0  0  0
 36 18  1  0  0  0  0
 36 21  1  0  0  0  0
 36 25  1  0  0  0  0
 37 22  1  0  0  0  0
 37 30  1  0  0  0  0
 37 35  1  0  0  0  0
 38 19  1  0  0  0  0
 39 20  1  0  0  0  0
 39 28  1  0  0  0  0
 26 40  1  6  0  0  0
 34 41  1  6  0  0  0
 35 42  1  1  0  0  0
 36 43  1  1  0  0  0
 44 22  1  0  0  0  0
 44 27  1  0  0  0  0
 45 29  1  0  0  0  0
 45 31  1  0  0  0  0
 46 30  1  0  0  0  0
 37 46  1  1  0  0  0
 18 47  1  1  0  0  0
 21 48  1  6  0  0  0
 22 49  1  1  0  0  0
 26 50  1  1  0  0  0
 27 51  1  1  0  0  0
 29 52  1  1  0  0  0
 30 53  1  6  0  0  0
M  END


  Mrv1652305152107072D          

 53 62  0  0  1  0            999 V2000
    4.2155   -1.7697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8867   -0.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3573   -0.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7689    1.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7660    1.8756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7956   -1.4211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1245   -1.4508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1899   -1.8007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9928   -1.6109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7039    0.7597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9011    0.5699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1768   -1.3053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7530    1.1090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5829   -2.3070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4525   -0.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5346   -0.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5147   -1.2236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0697    0.1196    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.3615   -2.0343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9574   -1.7690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9743    0.8364    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6241   -1.2003    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.1106   -0.9584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3672   -0.6006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8892   -0.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4925    0.0005    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2554   -0.7897    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7973   -1.1970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0945    0.1780    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2953    0.1903    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.2309    1.1941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2298   -0.8207    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.0327   -0.6309    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2698    0.1593    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6640   -0.2203    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.2470    0.0577    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8611   -0.4101    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.9870   -2.5723    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.1884   -1.9234    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9267    0.6009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5881    0.9204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5592    0.5980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4233    0.1038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8212   -1.3901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4523    0.9214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0982    0.3801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8110    0.4816    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0204    1.6601    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0583   -0.5999    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7295    0.7907    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6896   -0.1893    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9183    0.1320    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5324    0.9805    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0  0  0  0
 11 10  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 12  1  0  0  0  0
 18 13  1  0  0  0  0
 18 16  1  0  0  0  0
 19 14  2  0  0  0  0
 19 17  1  0  0  0  0
 20 14  1  0  0  0  0
 21 13  1  0  0  0  0
 22  8  1  0  0  0  0
 23 20  2  0  0  0  0
 24 23  1  0  0  0  0
 25 17  2  0  0  0  0
 25 23  1  0  0  0  0
 27 15  1  6  0  0  0
 27 26  1  0  0  0  0
 28 24  2  0  0  0  0
 29 24  1  0  0  0  0
 30 26  1  0  0  0  0
 31  4  1  0  0  0  0
 31  5  1  0  0  0  0
 31 21  1  0  0  0  0
 32  6  1  6  0  0  0
 32  9  1  0  0  0  0
 33  7  1  1  0  0  0
 33 28  1  0  0  0  0
 33 32  1  0  0  0  0
 34 10  1  0  0  0  0
 34 29  1  0  0  0  0
 34 33  1  0  0  0  0
 35 11  1  0  0  0  0
 35 32  1  0  0  0  0
 36 18  1  0  0  0  0
 36 21  1  0  0  0  0
 36 25  1  0  0  0  0
 37 22  1  0  0  0  0
 37 30  1  0  0  0  0
 37 35  1  0  0  0  0
 38 19  1  0  0  0  0
 39 20  1  0  0  0  0
 39 28  1  0  0  0  0
 26 40  1  6  0  0  0
 34 41  1  6  0  0  0
 35 42  1  1  0  0  0
 36 43  1  1  0  0  0
 44 22  1  0  0  0  0
 44 27  1  0  0  0  0
 45 29  1  0  0  0  0
 45 31  1  0  0  0  0
 46 30  1  0  0  0  0
 37 46  1  1  0  0  0
 18 47  1  1  0  0  0
 21 48  1  6  0  0  0
 22 49  1  1  0  0  0
 26 50  1  1  0  0  0
 27 51  1  1  0  0  0
 29 52  1  1  0  0  0
 30 53  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0013945

> <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(O)[C@]([H])(C[C@]7([H])C(C)(C)O[C@@]6([H])[C@]4(O)CC[C@@]13O)C(=C)C5)O[C@]([H])(C(C)=C)[C@]2([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C37H44ClNO7/c1-15(2)27-26(40)30-37(46-30)22(44-27)8-9-32(6)33(7)28-24-23-20(39-28)14-19(38)17-12-16(3)18-13-21(36(18,43)25(17)23)31(4,5)45-29(24)34(33,41)10-11-35(32,37)42/h14,18,21-22,26-27,29-30,39-43H,1,3,8-13H2,2,4-7H3/t18-,21-,22+,26+,27-,29-,30-,32-,33-,34-,35+,36-,37+/m1/s1

> <INCHI_KEY>
UHWWOHUHKKMDGI-VQJUMKOMSA-N

> <FORMULA>
C37H44ClNO7

> <MOLECULAR_WEIGHT>
650.21

> <EXACT_MASS>
649.2806305

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
90

> <JCHEM_AVERAGE_POLARIZABILITY>
72.04173430128031

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,5S,6S,8R,9S,10R,12S,15R,16S,25R,27S,28R)-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-2,5,9,28-tetrol

> <ALOGPS_LOGP>
3.65

> <JCHEM_LOGP>
3.395411814666667

> <ALOGPS_LOGS>
-4.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
10

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.04244850281636

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.59470948647126

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4301154563221665

> <JCHEM_POLAR_SURFACE_AREA>
127.70000000000002

> <JCHEM_REFRACTIVITY>
170.2433

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.81e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5S,6S,8R,9S,10R,12S,15R,16S,25R,27S,28R)-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-2,5,9,28-tetrol

> <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       7.869  -3.303   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.255  -0.708   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.800  -0.933   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.969   3.397   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.097   3.501   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.418  -2.653   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.032  -2.708   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.421  -3.361   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.920  -3.007   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.247   1.418   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.749   1.064   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.597  -2.437   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.806   2.070   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      21.621  -4.306   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.311  -1.828   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      25.265  -1.049   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      23.361  -2.284   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      24.397   0.223   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      23.075  -3.797   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      20.454  -3.302   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      22.352   1.561   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.365  -2.241   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      20.740  -1.789   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      19.352  -1.121   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      22.193  -1.280   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.253   0.001   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.810  -1.474   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      18.288  -2.234   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      18.843   0.332   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.751   0.355   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      20.964   2.229   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      15.362  -1.532   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      16.861  -1.178   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      17.304   0.297   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      14.306  -0.411   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      22.861   0.108   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      12.807  -0.765   0.000  0.00  0.00           C+0
HETATM   38 Cl   UNK     0      24.242  -4.802   0.000  0.00  0.00          Cl+0
HETATM   39  N   UNK     0      19.018  -3.590   0.000  0.00  0.00           N+0
HETATM   40  O   UNK     0       9.196   1.122   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      17.898   1.718   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      14.110   1.116   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      21.323   0.194   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      10.866  -2.595   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      19.511   1.720   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      13.250   0.710   0.000  0.00  0.00           O+0
HETATM   47  H   UNK     0      25.781   0.899   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0      22.438   3.099   0.000  0.00  0.00           H+0
HETATM   49  H   UNK     0      11.309  -1.120   0.000  0.00  0.00           H+0
HETATM   50  H   UNK     0      10.695   1.476   0.000  0.00  0.00           H+0
HETATM   51  H   UNK     0       8.754  -0.353   0.000  0.00  0.00           H+0
HETATM   52  H   UNK     0      20.381   0.246   0.000  0.00  0.00           H+0
HETATM   53  H   UNK     0      12.194   1.830   0.000  0.00  0.00           H+0
CONECT    1   15                                                            
CONECT    2   15                                                            
CONECT    3   16                                                            
CONECT    4   31                                                            
CONECT    5   31                                                            
CONECT    6   32                                                            
CONECT    7   33                                                            
CONECT    8    9   22                                                       
CONECT    9    8   32                                                       
CONECT   10   11   34                                                       
CONECT   11   10   35                                                       
CONECT   12   16   17                                                       
CONECT   13   18   21                                                       
CONECT   14   19   20                                                       
CONECT   15    1    2   27                                                  
CONECT   16    3   12   18                                                  
CONECT   17   12   19   25                                                  
CONECT   18   13   16   36   47                                             
CONECT   19   14   17   38                                                  
CONECT   20   14   23   39                                                  
CONECT   21   13   31   36   48                                             
CONECT   22    8   37   44   49                                             
CONECT   23   20   24   25                                                  
CONECT   24   23   28   29                                                  
CONECT   25   17   23   36                                                  
CONECT   26   27   30   40   50                                             
CONECT   27   15   26   44   51                                             
CONECT   28   24   33   39                                                  
CONECT   29   24   34   45   52                                             
CONECT   30   26   37   46   53                                             
CONECT   31    4    5   21   45                                             
CONECT   32    6    9   33   35                                             
CONECT   33    7   28   32   34                                             
CONECT   34   10   29   33   41                                             
CONECT   35   11   32   37   42                                             
CONECT   36   18   21   25   43                                             
CONECT   37   22   30   35   46                                             
CONECT   38   19                                                            
CONECT   39   20   28                                                       
CONECT   40   26                                                            
CONECT   41   34                                                            
CONECT   42   35                                                            
CONECT   43   36                                                            
CONECT   44   22   27                                                       
CONECT   45   29   31                                                       
CONECT   46   30   37                                                       
CONECT   47   18                                                            
CONECT   48   21                                                            
CONECT   49   22                                                            
CONECT   50   26                                                            
CONECT   51   27                                                            
CONECT   52   29                                                            
CONECT   53   30                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  124    0
END

Synonyms

Not Available

Molecular Formula

C₃₇H₄₄ClNO₇

Average Mass

650.21

Monoisotopic Mass

649.2806305

IUPAC Name

(1R,2S,5S,6S,8R,9S,10R,12S,15R,16S,25R,27S,28R)-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-2,5,9,28-tetrol

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(O)[C@]([H])(C[C@]7([H])C(C)(C)O[C@@]6([H])[C@]4(O)CC[C@@]13O)C(=C)C5)O[C@]([H])(C(C)=C)[C@]2([H])O

InChI Identifier

InChI=1S/C37H44ClNO7/c1-15(2)27-26(40)30-37(46-30)22(44-27)8-9-32(6)33(7)28-24-23-20(39-28)14-19(38)17-12-16(3)18-13-21(36(18,43)25(17)23)31(4,5)45-29(24)34(33,41)10-11-35(32,37)42/h14,18,21-22,26-27,29-30,39-43H,1,3,8-13H2,2,4-7H3/t18-,21-,22+,26+,27-,29-,30-,32-,33-,34-,35+,36-,37+/m1/s1

InChI Key

UHWWOHUHKKMDGI-VQJUMKOMSA-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
3-alkylindole
Tetralin
Naphthalene
Indole or derivatives
Indole
Dioxepane
1,4-dioxepane
Benzenoid
Pyran
Oxane
Monosaccharide
Aryl halide
Aryl chloride
Heteroaromatic compound
Tertiary alcohol
Pyrrole
Cyclic alcohol
Secondary alcohol
Cyclobutanol
Oxacycle
Azacycle
Polyol
Ether
Oxirane
Dialkyl ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Alcohol
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	0.0088 g/L	ALOGPS
logP	3.65	ALOGPS
logP	3.4	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	12.59	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	127.7 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	170.24 m³·mol⁻¹	ChemAxon
Polarizability	72.04 Å³	ChemAxon
Number of Rings	10	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum

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	1	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

40256802

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122206368

PDB ID

Not Available

ChEBI ID

Not Available

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 19-hydroxypenitrem A (MMDBc0013945)

MOL for #<Metabolite:0x00007fecd9d23f70>

3D MOL for #<Metabolite:0x00007fecd9d23f70>

3D SDF for #<Metabolite:0x00007fecd9d23f70>

3D-SDF for #<Metabolite:0x00007fecd9d23f70>

PDB for #<Metabolite:0x00007fecd9d23f70>

3D PDB for #<Metabolite:0x00007fecd9d23f70>

SMILES for #<Metabolite:0x00007fecd9d23f70>

INCHI for #<Metabolite:0x00007fecd9d23f70>

Structure for #<Metabolite:0x00007fecd9d23f70>

3D Structure for #<Metabolite:0x00007fecd9d23f70>