NP-MRD: Showing NP-Card for (2s,3r,6s,8s,9r,10r,12s,13s,16s,22r,26r)-9,13-dihydroxy-2,3,23,23,25,25-hexamethyl-8-{2-[(3-methylbut-2-en-1-yl)oxy]propan-2-yl}-7,11,24-trioxa-32-azanonacyclo[16.14.0.0²,¹⁶.0³,¹³.0⁶,¹².0¹⁰,¹².0¹⁹,³¹.0²⁰,²⁸.0²²,²⁶]dotriaconta-1(18),19,28,30-tetraen-27-one (NP0291351)

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Record Information

Version

1.0

Created at

2022-09-09 22:24:29 UTC

Updated at

2022-09-09 22:24:29 UTC

NP-MRD ID

NP0291351

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,6s,8s,9r,10r,12s,13s,16s,22r,26r)-9,13-dihydroxy-2,3,23,23,25,25-hexamethyl-8-{2-[(3-methylbut-2-en-1-yl)oxy]propan-2-yl}-7,11,24-trioxa-32-azanonacyclo[16.14.0.0²,¹⁶.0³,¹³.0⁶,¹².0¹⁰,¹².0¹⁹,³¹.0²⁰,²⁸.0²²,²⁶]dotriaconta-1(18),19,28,30-tetraen-27-one

Description

Lolitrem E 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. Lolitrem E is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. (2s,3r,6s,8s,9r,10r,12s,13s,16s,22r,26r)-9,13-dihydroxy-2,3,23,23,25,25-hexamethyl-8-{2-[(3-methylbut-2-en-1-yl)oxy]propan-2-yl}-7,11,24-trioxa-32-azanonacyclo[16.14.0.0²,¹⁶.0³,¹³.0⁶,¹².0¹⁰,¹².0¹⁹,³¹.0²⁰,²⁸.0²²,²⁶]dotriaconta-1(18),19,28,30-tetraen-27-one is found in Epichloe festucae and Lolium perenne. It was first documented in 2019 (PMID: 31766147). Based on a literature review a significant number of articles have been published on Lolitrem E (PMID: 34834850) (PMID: 36013386) (PMID: 32125583) (PMID: 31137882).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102200242D          

 50 58  0  0  1  0            999 V2000
   -4.1952    1.0431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 48 50  1  0  0  0  0
M  END

     RDKit          3D

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   10.3029   -0.1518   -1.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7014    0.2890    0.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5922    0.4428    3.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0747    0.1346    2.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5443   -0.6038    1.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2739    2.0863    2.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7017    3.4555    1.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8510    2.8891    3.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  1
 17 29  1  0
 29 28  1  0
 28 27  1  0
 27 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 42  1  0
 42 43  2  0
 42 41  1  0
 41 40  1  0
 40 39  1  0
 39 25  1  0
 25 26  2  0
 40 48  1  0
 48 49  1  0
 48 50  1  0
 48 47  1  0
 47 44  1  0
 44 45  1  0
 44 46  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  1
 32 34  1  0
 34 35  1  1
 35 36  1  0
 36 37  1  0
 37 38  1  0
 37 10  1  0
 34 12  1  0
 36 34  1  0
 32 15  1  0
 19 17  1  0
 26 21  1  0
 26 27  1  0
 25 24  1  0
 44 41  1  0
  1 51  1  0
  1 52  1  0
  1 53  1  0
  3 54  1  0
  3 55  1  0
  3 56  1  0
  4 57  1  0
  5 58  1  0
  5 59  1  0
  8 60  1  0
  8 61  1  0
  8 62  1  0
  9 63  1  0
  9 64  1  0
  9 65  1  0
 10 66  1  1
 12 67  1  1
 13 68  1  0
 13 69  1  0
 14 70  1  0
 14 71  1  0
 16 72  1  0
 16 73  1  0
 16 74  1  0
 18 75  1  0
 18 76  1  0
 18 77  1  0
 29 83  1  6
 28 81  1  0
 28 82  1  0
 20 78  1  0
 22 79  1  0
 23 80  1  0
 41 95  1  1
 40 94  1  6
 39 92  1  0
 39 93  1  0
 49102  1  0
 49103  1  0
 49104  1  0
 50105  1  0
 50106  1  0
 50107  1  0
 45 96  1  0
 45 97  1  0
 45 98  1  0
 46 99  1  0
 46100  1  0
 46101  1  0
 30 84  1  0
 30 85  1  0
 31 86  1  0
 31 87  1  0
 33 88  1  0
 36 89  1  1
 37 90  1  6
 38 91  1  0
M  END


  Mrv1652309102200242D          

 50 58  0  0  1  0            999 V2000
   -4.1952    1.0431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3769    0.9380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8768    1.5941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0588    0.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2405    0.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7404    0.7278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9221    0.6227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0272   -0.1956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8170    1.4410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1038    0.5176    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3963    1.1737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2146    1.0686    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7148    1.7247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5331    1.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8512    0.8584    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3513    1.5145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6695    0.7533    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6884    1.5781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2951    1.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4852    2.0939    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3074    2.1612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8076    2.8173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6258    2.7122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9440    1.9510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4438    1.2949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6255    1.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9999    0.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8098    0.0595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9876   -0.0079    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4874   -0.6640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6692   -0.5589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3510    0.2023    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3320   -0.6225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5327    0.3074    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8509   -0.4538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0326   -0.3487    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2143   -0.2436    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2858   -0.8997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7619    0.5337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5802    0.4287    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.0804    1.0848    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7622    1.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2624    2.5021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8589    0.8118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0490    1.6146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6772    0.7067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8399   -0.0130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0496   -0.2498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1941   -1.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4297   -0.7941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
 10  7  1  1  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
 19 27  2  0  0  0  0
 27 28  1  0  0  0  0
 29 28  1  6  0  0  0
 17 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 15 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
 12 34  1  0  0  0  0
 34 35  1  6  0  0  0
 36 35  1  6  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 10 37  1  0  0  0  0
 37 38  1  6  0  0  0
 25 39  1  0  0  0  0
 40 39  1  6  0  0  0
 40 41  1  0  0  0  0
 41 42  1  1  0  0  0
 24 42  1  0  0  0  0
 42 43  2  0  0  0  0
 41 44  1  0  0  0  0
 44 45  1  0  0  0  0
 44 46  1  0  0  0  0
 44 47  1  0  0  0  0
 47 48  1  0  0  0  0
 40 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0291351

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCOC(C)(C)[C@H]1O[C@H]2CC[C@]3(C)[C@]4(C)[C@H](CC5=C4NC4=CC=C6C(=O)[C@@H]7[C@@H](CC6=C54)C(C)(C)OC7(C)C)CC[C@@]3(O)[C@]22O[C@@H]2[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C42H57NO7/c1-21(2)15-18-47-38(7,8)34-32(45)35-42(49-35)28(48-34)14-16-39(9)40(10)22(13-17-41(39,42)46)19-25-29-24-20-26-30(37(5,6)50-36(26,3)4)31(44)23(24)11-12-27(29)43-33(25)40/h11-12,15,22,26,28,30,32,34-35,43,45-46H,13-14,16-20H2,1-10H3/t22-,26+,28-,30-,32+,34-,35+,39+,40+,41-,42-/m0/s1

> <INCHI_KEY>
XERCMAQJPCQQAO-OKQVYEMSSA-N

> <FORMULA>
C42H57NO7

> <MOLECULAR_WEIGHT>
687.918

> <EXACT_MASS>
687.413503179

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
107

> <JCHEM_AVERAGE_POLARIZABILITY>
80.763445693264

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,6S,8S,9R,10R,12S,13S,16S,22R,26R)-9,13-dihydroxy-2,3,23,23,25,25-hexamethyl-8-{2-[(3-methylbut-2-en-1-yl)oxy]propan-2-yl}-7,11,24-trioxa-32-azanonacyclo[16.14.0.0^{2,16}.0^{3,13}.0^{6,12}.0^{10,12}.0^{19,31}.0^{20,28}.0^{22,26}]dotriaconta-1(18),19(31),20(28),29-tetraen-27-one

> <JCHEM_LOGP>
5.711569423333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.381382789075175

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.778644562155936

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6010598370056073

> <JCHEM_POLAR_SURFACE_AREA>
113.54000000000002

> <JCHEM_REFRACTIVITY>
191.69619999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,6S,8S,9R,10R,12S,13S,16S,22R,26R)-9,13-dihydroxy-2,3,23,23,25,25-hexamethyl-8-{2-[(3-methylbut-2-en-1-yl)oxy]propan-2-yl}-7,11,24-trioxa-32-azanonacyclo[16.14.0.0^{2,16}.0^{3,13}.0^{6,12}.0^{10,12}.0^{19,31}.0^{20,28}.0^{22,26}]dotriaconta-1(18),19(31),20(28),29-tetraen-27-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -7.831   1.947   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.304   1.751   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.370   2.976   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.710   0.330   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.182   0.134   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -3.249   1.359   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.721   1.162   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.917  -0.365   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.525   2.690   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.194   0.966   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.740   2.191   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.267   1.995   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.201   3.219   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.728   3.023   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.322   1.602   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.256   2.827   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.850   1.406   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.885   2.946   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.018   2.410   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       8.372   3.909   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       9.907   4.034   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.841   5.259   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.368   5.063   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.962   3.642   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.028   2.417   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.501   2.613   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.333   1.610   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.978   0.111   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.443  -0.015   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.510  -1.239   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.982  -1.043   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.389   0.378   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.353  -1.162   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.861   0.574   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       3.455  -0.847   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       1.928  -0.651   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.400  -0.455   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -0.534  -1.679   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      12.622   0.996   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      14.150   0.800   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      15.083   2.025   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      14.490   3.446   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      15.423   4.670   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      16.537   1.515   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      16.891   3.014   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      18.064   1.319   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      16.501  -0.024   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      15.026  -0.466   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      15.296  -1.982   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      13.869  -1.482   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11   37                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   34                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   32                                             
CONECT   16   15                                                            
CONECT   17   15   18   19   29                                             
CONECT   18   17                                                            
CONECT   19   17   20   27                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   42                                                  
CONECT   25   24   26   39                                                  
CONECT   26   25   21   27                                                  
CONECT   27   26   19   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   17   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   15   33   34                                             
CONECT   33   32                                                            
CONECT   34   32   12   35   36                                             
CONECT   35   34   36                                                       
CONECT   36   35   34   37                                                  
CONECT   37   36   10   38                                                  
CONECT   38   37                                                            
CONECT   39   25   40                                                       
CONECT   40   39   41   48                                                  
CONECT   41   40   42   44                                                  
CONECT   42   41   24   43                                                  
CONECT   43   42                                                            
CONECT   44   41   45   46   47                                             
CONECT   45   44                                                            
CONECT   46   44                                                            
CONECT   47   44   48                                                       
CONECT   48   47   40   49   50                                             
CONECT   49   48                                                            
CONECT   50   48                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  116    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₂H₅₇NO₇

Average Mass

687.9180 Da

Monoisotopic Mass

687.41350 Da

IUPAC Name

(2S,3R,6S,8S,9R,10R,12S,13S,16S,22R,26R)-9,13-dihydroxy-2,3,23,23,25,25-hexamethyl-8-{2-[(3-methylbut-2-en-1-yl)oxy]propan-2-yl}-7,11,24-trioxa-32-azanonacyclo[16.14.0.0^{2,16}.0^{3,13}.0^{6,12}.0^{10,12}.0^{19,31}.0^{20,28}.0^{22,26}]dotriaconta-1(18),19(31),20(28),29-tetraen-27-one

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(C)=CCOC(C)(C)[C@H]1O[C@H]2CC[C@]3(C)[C@]4(C)[C@H](CC5=C4NC4=CC=C6C(=O)[C@@H]7[C@@H](CC6=C54)C(C)(C)OC7(C)C)CC[C@@]3(O)[C@]22O[C@@H]2[C@@H]1O

InChI Identifier

InChI=1S/C42H57NO7/c1-21(2)15-18-47-38(7,8)34-32(45)35-42(49-35)28(48-34)14-16-39(9)40(10)22(13-17-41(39,42)46)19-25-29-24-20-26-30(37(5,6)50-36(26,3)4)31(44)23(24)11-12-27(29)43-33(25)40/h11-12,15,22,26,28,30,32,34-35,43,45-46H,13-14,16-20H2,1-10H3/t22-,26+,28-,30-,32+,34-,35+,39+,40+,41-,42-/m0/s1

InChI Key

XERCMAQJPCQQAO-OKQVYEMSSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Epichloe festucae	LOTUS Database	35616633
Lolium perenne	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
Naphthofuran
Naphthalene
Tetralin
3-alkylindole
Indole
Indole or derivatives
Aryl ketone
Aryl alkyl ketone
1,4-dioxepane
Dioxepane
Benzenoid
Pyran
Oxane
Monosaccharide
Cyclic alcohol
Heteroaromatic compound
Tetrahydrofuran
Tertiary alcohol
Pyrrole
Secondary alcohol
Ketone
Azacycle
Oxacycle
Dialkyl ether
Oxirane
Ether
Organic nitrogen compound
Alcohol
Organooxygen compound
Organic oxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxide
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	5.71	ChemAxon
pKa (Strongest Acidic)	12.78	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.54 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	191.7 m³·mol⁻¹	ChemAxon
Polarizability	80.76 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00023577

Chemspider ID

30790758

KEGG Compound ID

C20550

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72734305

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fernando K, Reddy P, Vassiliadis S, Spangenberg GC, Rochfort SJ, Guthridge KM: The Known Antimammalian and Insecticidal Alkaloids Are Not Responsible for the Antifungal Activity of Epichloe Endophytes. Plants (Basel). 2021 Nov 17;10(11). pii: plants10112486. doi: 10.3390/plants10112486. [PubMed:34834850 ]
Ludlow EJ, Vassiliadis S, Ekanayake PN, Hettiarachchige IK, Reddy P, Sawbridge TI, Rochfort SJ, Spangenberg GC, Guthridge KM: Analysis of the Indole Diterpene Gene Cluster for Biosynthesis of the Epoxy-Janthitrems in Epichloe Endophytes. Microorganisms. 2019 Nov 13;7(11). pii: microorganisms7110560. doi: 10.3390/microorganisms7110560. [PubMed:31766147 ]
Lin W, Gao C, Wang J, Xu W, Wang M, Li M, Ma B, Tian P: Effects of Drought Stress on Peramine and Lolitrem B in Epichloe-Endophyte-Infected Perennial Ryegrass. Life (Basel). 2022 Aug 8;12(8):1207. doi: 10.3390/life12081207. [PubMed:36013386 ]
Hewitt KG, Mace WJ, McKenzie CM, Matthew C, Popay AJ: Fungal Alkaloid Occurrence in Endophyte-Infected Perennial Ryegrass during Seedling Establishment. J Chem Ecol. 2020 Apr;46(4):410-421. doi: 10.1007/s10886-020-01162-w. Epub 2020 Mar 3. [PubMed:32125583 ]
Reddy P, Guthridge K, Vassiliadis S, Hemsworth J, Hettiarachchige I, Spangenberg G, Rochfort S: Tremorgenic Mycotoxins: Structure Diversity and Biological Activity. Toxins (Basel). 2019 May 27;11(5):302. doi: 10.3390/toxins11050302. [PubMed:31137882 ]
LOTUS database [Link]