MiMeDB: Showing metabocard for Penitrem D (MMDBc0018546)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 08:43:59 UTC

Update Date

2022-08-31 06:44:00 UTC

Metabolite ID

MMDBc0018546

Metabolite Identification

Common Name

Penitrem D

Description

penitrem D, also known as tremortin, 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 very few articles have been published on penitrem D.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152110442D          

 50 58  0  0  1  0            999 V2000
    9.4859   -2.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8147   -1.0908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6559   -1.2118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9325    1.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9354    1.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9058   -2.1328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5639   -2.1609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3398   -2.7460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1185   -3.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9974    0.0480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5115   -2.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7086   -2.3226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8003   -0.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5245   -2.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9484    0.3973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4060   -0.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2489   -1.6912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1668   -1.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1867   -1.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6317   -0.5921    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4316   -0.5524    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8402   -1.1218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7271    0.1247    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7439   -2.4807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2089   -0.7112    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0773   -1.9120    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8121   -1.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4544   -0.6540    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5908   -1.6700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3342   -1.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4460   -1.5014    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6068   -0.5336    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9904   -1.8122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4704    0.4824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4716   -1.5324    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6687   -1.3426    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0374   -0.9320    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5130   -2.6351    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7747   -0.1108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6032   -0.3316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8802   -2.1018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2491    0.2097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1096   -0.2301    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1133    0.2087    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3421   -0.4252    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0118   -0.9010    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6431   -1.3116    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9895   -1.3355    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6830   -2.2916    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7831   -0.5797    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  2  0  0  0  0
 12 11  1  0  0  0  0
 13 10  1  0  0  0  0
 17  1  2  0  0  0  0
 17  2  1  0  0  0  0
 18  3  2  0  0  0  0
 18 14  1  0  0  0  0
 19  8  1  0  0  0  0
 19 14  1  0  0  0  0
 20 15  1  0  0  0  0
 20 18  1  0  0  0  0
 21 10  1  0  0  0  0
 22 16  2  0  0  0  0
 23 15  1  0  0  0  0
 24  9  1  0  0  0  0
 25 16  1  0  0  0  0
 26 11  1  0  0  0  0
 26 22  1  0  0  0  0
 27 19  2  0  0  0  0
 28 20  1  0  0  0  0
 28 23  1  0  0  0  0
 28 27  1  0  0  0  0
 29 24  2  0  0  0  0
 29 27  1  0  0  0  0
 30 29  1  0  0  0  0
 31 17  1  1  0  0  0
 31 25  1  0  0  0  0
 32 21  1  0  0  0  0
 32 30  1  0  0  0  0
 33 30  2  0  0  0  0
 34  4  1  0  0  0  0
 34  5  1  0  0  0  0
 34 23  1  0  0  0  0
 35  6  1  1  0  0  0
 35 12  1  0  0  0  0
 36  7  1  6  0  0  0
 36 21  1  0  0  0  0
 36 33  1  0  0  0  0
 36 35  1  0  0  0  0
 37 13  1  0  0  0  0
 37 22  1  0  0  0  0
 37 35  1  0  0  0  0
 38 24  1  0  0  0  0
 38 33  1  0  0  0  0
 25 39  1  1  0  0  0
 37 40  1  6  0  0  0
 41 26  1  0  0  0  0
 41 31  1  0  0  0  0
 42 32  1  0  0  0  0
 42 34  1  0  0  0  0
 20 43  1  6  0  0  0
 21 44  1  1  0  0  0
 23 45  1  1  0  0  0
 25 46  1  6  0  0  0
 26 47  1  6  0  0  0
 28 48  1  6  0  0  0
 31 49  1  6  0  0  0
 32 50  1  6  0  0  0
M  END


  Mrv1652305152110442D          

 50 58  0  0  1  0            999 V2000
    9.4859   -2.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8147   -1.0908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6559   -1.2118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9325    1.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9354    1.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9058   -2.1328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5639   -2.1609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3398   -2.7460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1185   -3.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9974    0.0480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5115   -2.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7086   -2.3226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8003   -0.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5245   -2.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9484    0.3973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4060   -0.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2489   -1.6912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1668   -1.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1867   -1.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6317   -0.5921    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4316   -0.5524    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8402   -1.1218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7271    0.1247    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7439   -2.4807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2089   -0.7112    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0773   -1.9120    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8121   -1.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4544   -0.6540    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5908   -1.6700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3342   -1.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4460   -1.5014    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6068   -0.5336    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9904   -1.8122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4704    0.4824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4716   -1.5324    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6687   -1.3426    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0374   -0.9320    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5130   -2.6351    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7747   -0.1108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6032   -0.3316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8802   -2.1018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2491    0.2097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1096   -0.2301    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1133    0.2087    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3421   -0.4252    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0118   -0.9010    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6431   -1.3116    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9895   -1.3355    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6830   -2.2916    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7831   -0.5797    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  2  0  0  0  0
 12 11  1  0  0  0  0
 13 10  1  0  0  0  0
 17  1  2  0  0  0  0
 17  2  1  0  0  0  0
 18  3  2  0  0  0  0
 18 14  1  0  0  0  0
 19  8  1  0  0  0  0
 19 14  1  0  0  0  0
 20 15  1  0  0  0  0
 20 18  1  0  0  0  0
 21 10  1  0  0  0  0
 22 16  2  0  0  0  0
 23 15  1  0  0  0  0
 24  9  1  0  0  0  0
 25 16  1  0  0  0  0
 26 11  1  0  0  0  0
 26 22  1  0  0  0  0
 27 19  2  0  0  0  0
 28 20  1  0  0  0  0
 28 23  1  0  0  0  0
 28 27  1  0  0  0  0
 29 24  2  0  0  0  0
 29 27  1  0  0  0  0
 30 29  1  0  0  0  0
 31 17  1  1  0  0  0
 31 25  1  0  0  0  0
 32 21  1  0  0  0  0
 32 30  1  0  0  0  0
 33 30  2  0  0  0  0
 34  4  1  0  0  0  0
 34  5  1  0  0  0  0
 34 23  1  0  0  0  0
 35  6  1  1  0  0  0
 35 12  1  0  0  0  0
 36  7  1  6  0  0  0
 36 21  1  0  0  0  0
 36 33  1  0  0  0  0
 36 35  1  0  0  0  0
 37 13  1  0  0  0  0
 37 22  1  0  0  0  0
 37 35  1  0  0  0  0
 38 24  1  0  0  0  0
 38 33  1  0  0  0  0
 25 39  1  1  0  0  0
 37 40  1  6  0  0  0
 41 26  1  0  0  0  0
 41 31  1  0  0  0  0
 42 32  1  0  0  0  0
 42 34  1  0  0  0  0
 20 43  1  6  0  0  0
 21 44  1  1  0  0  0
 23 45  1  1  0  0  0
 25 46  1  6  0  0  0
 26 47  1  6  0  0  0
 28 48  1  6  0  0  0
 31 49  1  6  0  0  0
 32 50  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0018546

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@]12C[C@@]3([H])[C@@]1([H])C1=C(CC2=C)C=CC2=C1C1=C(N2)[C@@]2(C)[C@@]([H])(CC[C@@]4(O)C5=C[C@@]([H])(O)[C@]([H])(O[C@@]5([H])CC[C@]24C)C(C)=C)[C@]1([H])OC3(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C37H45NO4/c1-17(2)31-25(39)16-22-26(41-31)11-12-35(6)36(7)21(10-13-37(22,35)40)32-30-29-24(38-33(30)36)9-8-19-14-18(3)20-15-23(28(20)27(19)29)34(4,5)42-32/h8-9,16,20-21,23,25-26,28,31-32,38-40H,1,3,10-15H2,2,4-7H3/t20-,21+,23+,25-,26+,28+,31-,32+,35-,36-,37-/m1/s1

> <INCHI_KEY>
XOASTWITKYDKAJ-PPQPEBMASA-N

> <FORMULA>
C37H45NO4

> <MOLECULAR_WEIGHT>
567.77

> <EXACT_MASS>
567.334858933

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
66.5139288207263

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,8R,9R,11S,14R,15S,24S,26S,27S)-14,15,32,32-tetramethyl-23-methylidene-9-(prop-1-en-2-yl)-10,31-dioxa-17-azanonacyclo[24.4.2.0^{2,15}.0^{5,14}.0^{6,11}.0^{16,30}.0^{18,29}.0^{21,28}.0^{24,27}]dotriaconta-6,16(30),18(29),19,21(28)-pentaene-5,8-diol

> <ALOGPS_LOGP>
5.17

> <JCHEM_LOGP>
5.111700419666668

> <ALOGPS_LOGS>
-6.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.036356181799423

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.423976272998328

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3536229414809915

> <JCHEM_POLAR_SURFACE_AREA>
74.71000000000001

> <JCHEM_REFRACTIVITY>
164.5676

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.17e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,8R,9R,11S,14R,15S,24S,26S,27S)-14,15,32,32-tetramethyl-23-methylidene-9-(prop-1-en-2-yl)-10,31-dioxa-17-azanonacyclo[24.4.2.0^{2,15}.0^{5,14}.0^{6,11}.0^{16,30}.0^{18,29}.0^{21,28}.0^{24,27}]dotriaconta-6,16(30),18(29),19,21(28)-pentaene-5,8-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      17.707  -4.632   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.321  -2.036   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.224  -2.262   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.607   2.068   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.479   2.173   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.157  -3.981   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.519  -4.034   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.501  -5.126   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.954  -5.635   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.329   0.090   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.155  -4.690   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.656  -4.335   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.827  -0.265   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.979  -3.765   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.770   0.742   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.825  -0.973   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.265  -3.157   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.311  -2.377   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.215  -3.613   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.179  -1.105   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.272  -1.031   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.768  -2.094   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.224   0.233   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.122  -4.631   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.323  -1.328   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.211  -3.569   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.383  -2.608   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.715  -1.221   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.836  -3.117   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.224  -2.450   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      15.766  -2.803   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.733  -0.996   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.449  -3.383   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.612   0.901   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.214  -2.860   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.715  -2.506   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      11.270  -1.740   0.000  0.00  0.00           C+0
HETATM   38  N   UNK     0       6.558  -4.919   0.000  0.00  0.00           N+0
HETATM   39  O   UNK     0      16.379  -0.207   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      12.326  -0.619   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      14.710  -3.923   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       6.065   0.392   0.000  0.00  0.00           O+0
HETATM   43  H   UNK     0      -0.205  -0.430   0.000  0.00  0.00           H+0
HETATM   44  H   UNK     0       7.678   0.390   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0       4.372  -0.794   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0      16.822  -1.682   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0      14.267  -2.448   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.847  -2.493   0.000  0.00  0.00           H+0
HETATM   49  H   UNK     0      16.208  -4.278   0.000  0.00  0.00           H+0
HETATM   50  H   UNK     0       5.195  -1.082   0.000  0.00  0.00           H+0
CONECT    1   17                                                            
CONECT    2   17                                                            
CONECT    3   18                                                            
CONECT    4   34                                                            
CONECT    5   34                                                            
CONECT    6   35                                                            
CONECT    7   36                                                            
CONECT    8    9   19                                                       
CONECT    9    8   24                                                       
CONECT   10   13   21                                                       
CONECT   11   12   26                                                       
CONECT   12   11   35                                                       
CONECT   13   10   37                                                       
CONECT   14   18   19                                                       
CONECT   15   20   23                                                       
CONECT   16   22   25                                                       
CONECT   17    1    2   31                                                  
CONECT   18    3   14   20                                                  
CONECT   19    8   14   27                                                  
CONECT   20   15   18   28   43                                             
CONECT   21   10   32   36   44                                             
CONECT   22   16   26   37                                                  
CONECT   23   15   28   34   45                                             
CONECT   24    9   29   38                                                  
CONECT   25   16   31   39   46                                             
CONECT   26   11   22   41   47                                             
CONECT   27   19   28   29                                                  
CONECT   28   20   23   27   48                                             
CONECT   29   24   27   30                                                  
CONECT   30   29   32   33                                                  
CONECT   31   17   25   41   49                                             
CONECT   32   21   30   42   50                                             
CONECT   33   30   36   38                                                  
CONECT   34    4    5   23   42                                             
CONECT   35    6   12   36   37                                             
CONECT   36    7   21   33   35                                             
CONECT   37   13   22   35   40                                             
CONECT   38   24   33                                                       
CONECT   39   25                                                            
CONECT   40   37                                                            
CONECT   41   26   31                                                       
CONECT   42   32   34                                                       
CONECT   43   20                                                            
CONECT   44   21                                                            
CONECT   45   23                                                            
CONECT   46   25                                                            
CONECT   47   26                                                            
CONECT   48   28                                                            
CONECT   49   31                                                            
CONECT   50   32                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  116    0
END

Synonyms

Value	Source
Penitrem e	MeSH
Penitrems	MeSH
Penitrem b	MeSH
Tremortin	MeSH
Penitrem a	MeSH
Tremortin a	MeSH
Tremortin b	MeSH

Molecular Formula

C₃₇H₄₅NO₄

Average Mass

567.77

Monoisotopic Mass

567.334858933

IUPAC Name

(1S,2R,5S,8R,9R,11S,14R,15S,24S,26S,27S)-14,15,32,32-tetramethyl-23-methylidene-9-(prop-1-en-2-yl)-10,31-dioxa-17-azanonacyclo[24.4.2.0^{2,15}.0^{5,14}.0^{6,11}.0^{16,30}.0^{18,29}.0^{21,28}.0^{24,27}]dotriaconta-6,16(30),18(29),19,21(28)-pentaene-5,8-diol

Traditional Name

CAS Registry Number

Not Available

SMILES

[H][C@]12C[C@@]3([H])[C@@]1([H])C1=C(CC2=C)C=CC2=C1C1=C(N2)[C@@]2(C)[C@@]([H])(CC[C@@]4(O)C5=C[C@@]([H])(O)[C@]([H])(O[C@@]5([H])CC[C@]24C)C(C)=C)[C@]1([H])OC3(C)C

InChI Identifier

InChI=1S/C37H45NO4/c1-17(2)31-25(39)16-22-26(41-31)11-12-35(6)36(7)21(10-13-37(22,35)40)32-30-29-24(38-33(30)36)9-8-19-14-18(3)20-15-23(28(20)27(19)29)34(4,5)42-32/h8-9,16,20-21,23,25-26,28,31-32,38-40H,1,3,10-15H2,2,4-7H3/t20-,21+,23+,25-,26+,28+,31-,32+,35-,36-,37-/m1/s1

InChI Key

XOASTWITKYDKAJ-PPQPEBMASA-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
Indole or derivatives
Pyran
Benzenoid
Cyclic alcohol
Heteroaromatic compound
Pyrrole
Tertiary alcohol
Secondary alcohol
Ether
Dialkyl ether
Oxacycle
Azacycle
Alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen 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	0.00032 g/L	ALOGPS
logP	5.17	ALOGPS
logP	5.11	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	13.42	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	74.71 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	164.57 m³·mol⁻¹	ChemAxon
Polarizability	66.51 Å³	ChemAxon
Number of Rings	9	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

C00023572

Chemspider ID

2299505

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3035208

PDB ID

Not Available

ChEBI ID

138854

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 D (MMDBc0018546)

MOL for #<Metabolite:0x00007fecf4ef60d0>

3D MOL for #<Metabolite:0x00007fecf4ef60d0>

3D SDF for #<Metabolite:0x00007fecf4ef60d0>

3D-SDF for #<Metabolite:0x00007fecf4ef60d0>

PDB for #<Metabolite:0x00007fecf4ef60d0>

3D PDB for #<Metabolite:0x00007fecf4ef60d0>

SMILES for #<Metabolite:0x00007fecf4ef60d0>

INCHI for #<Metabolite:0x00007fecf4ef60d0>

Structure for #<Metabolite:0x00007fecf4ef60d0>

3D Structure for #<Metabolite:0x00007fecf4ef60d0>