MiMeDB: Showing metabocard for 6,8a-Seco-6,8a-deoxy-2,5-didehydroaverme (MMDBc0004479)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-14 22:26:35 UTC

Update Date

2022-08-31 06:22:30 UTC

Metabolite ID

MMDBc0004479

Metabolite Identification

Common Name

6,8a-Seco-6,8a-deoxy-2,5-didehydroaverme

Description

6,8a-Seco-6,8a-deoxy-2,5-didehydroaverme belongs to the class of organic compounds known as milbemycins. These are a group of macrolides with a structure containing a 16-membered lactone ring fused to a 1,7-dioxaspiroundecane ring system and to either a benzofuran (or hydrogenated derivative thereof). In some cases (e.g. Milbemycin E), the tetrahydrofuranyl ring is missing. Milbemycins can be o-glycosylated at C13 to form Avermectins. Milbemycins are produced by Streptomyces species. Based on a literature review very few articles have been published on 6,8a-Seco-6,8a-deoxy-2,5-didehydroaverme.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152100262D          

 65 70  0  0  0  0            999 V2000
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M  END


  Mrv1652305152100262D          

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M  END
> <DATABASE_ID>
MMDBc0004479

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C1=C(C)\C(OC2CC(OC)C(OC3CC(OC)C(O)C(C)O3)C(C)O2)C(C)\C([H])=C(\[H])/C(/[H])=C(C)\C2=C(C=C(C)C(O)=C2)C(=O)OC2CC(C1)OC1(CC(O)C(C)C(O1)C(C)CC)C2

> <INCHI_IDENTIFIER>
InChI=1S/C48H72O13/c1-12-25(2)45-30(7)38(50)24-48(61-45)23-34-19-33(60-48)17-16-28(5)44(27(4)15-13-14-26(3)35-20-37(49)29(6)18-36(35)47(52)57-34)58-42-22-40(54-11)46(32(9)56-42)59-41-21-39(53-10)43(51)31(8)55-41/h13-16,18,20,25,27,30-34,38-46,49-51H,12,17,19,21-24H2,1-11H3/b15-13-,26-14-,28-16-

> <INCHI_KEY>
ZRYHPEOHTDJRCY-VZUATFRUSA-N

> <FORMULA>
C48H72O13

> <MOLECULAR_WEIGHT>
857.091

> <EXACT_MASS>
856.497292378

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
133

> <JCHEM_AVERAGE_POLARIZABILITY>
97.41223349448731

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(10'Z,12'Z,16'Z)-6-(butan-2-yl)-4,7'-dihydroxy-15'-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-5,6',10',14',16'-pentamethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0^{4,9}]tricosane]-4',6',8',10',12',16'-hexaen-3'-one

> <ALOGPS_LOGP>
4.94

> <JCHEM_LOGP>
8.397418640666668

> <ALOGPS_LOGS>
-5.40

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.201244909948958

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.773370174969699

> <JCHEM_PKA_STRONGEST_BASIC>
-2.928949393066614

> <JCHEM_POLAR_SURFACE_AREA>
160.83

> <JCHEM_REFRACTIVITY>
230.70740000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.39e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(10'Z,12'Z,16'Z)-4,7'-dihydroxy-15'-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-5,6',10',14',16'-pentamethyl-6-(sec-butyl)-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0^{4,9}]tricosane]-4',6',8',10',12',16'-hexaen-3'-one

> <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       5.808   1.036   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.425  -0.588   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.994  -0.145   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.903  -6.739   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.759  -6.059   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.903   5.406   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.572   4.030   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.909  -6.587   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.028  -7.675   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      28.234 -11.034   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.839 -12.778   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.166   1.763   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.006  -3.477   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      21.547  -2.036   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      19.954  -4.602   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.446  -3.699   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.809  -2.296   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.081   3.457   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.115  -0.030   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      22.331   1.354   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      24.161 -11.146   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.706  -9.306   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.855   2.321   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.546   3.133   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.474   0.951   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      21.495  -0.496   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      18.552  -5.239   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.571  -4.750   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      21.554   3.906   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.880   3.218   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      24.660  -8.107   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      20.587  -8.219   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.757  -0.757   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      15.164   1.509   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      20.858   0.906   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      19.733   1.957   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      22.679   2.854   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      11.238   3.945   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      25.602 -10.602   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      18.897 -10.282   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      22.970 -10.170   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      17.955  -7.787   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      25.851  -9.082   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      17.013  -5.291   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       9.832   1.679   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      20.338  -9.738   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      18.291   2.498   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      12.498   1.594   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      24.153   3.303   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      11.287   5.484   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      27.292  -8.539   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      18.541   4.018   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      26.793 -11.578   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      18.648 -11.802   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      23.219  -8.651   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      19.396  -7.243   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      16.752   2.446   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      16.764  -6.811   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      21.529 -10.714   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      12.449   0.055   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0      11.140   0.867   0.000  0.00  0.00           O+0
HETATM   62  H   UNK     0      22.314  -4.289   0.000  0.00  0.00           H+0
HETATM   63  H   UNK     0      23.067  -2.285   0.000  0.00  0.00           H+0
HETATM   64  H   UNK     0      20.852  -5.853   0.000  0.00  0.00           H+0
HETATM   65  H   UNK     0      13.195  -4.597   0.000  0.00  0.00           H+0
CONECT    1   12                                                            
CONECT    2   25                                                            
CONECT    3   26                                                            
CONECT    4   27                                                            
CONECT    5   28                                                            
CONECT    6   29                                                            
CONECT    7   30                                                            
CONECT    8   31                                                            
CONECT    9   32                                                            
CONECT   10   53                                                            
CONECT   11   54                                                            
CONECT   12    1   25                                                       
CONECT   13   14   15   62                                                  
CONECT   14   13   26   63                                                  
CONECT   15   13   27   64                                                  
CONECT   16   17   28   65                                                  
CONECT   17   16   33                                                       
CONECT   18   29   36                                                       
CONECT   19   33   34                                                       
CONECT   20   35   37                                                       
CONECT   21   39   41                                                       
CONECT   22   40   42                                                       
CONECT   23   34   48                                                       
CONECT   24   38   48                                                       
CONECT   25    2   12   45                                                  
CONECT   26    3   14   35                                                  
CONECT   27    4   15   44                                                  
CONECT   28    5   16   44                                                  
CONECT   29    6   18   37                                                  
CONECT   30    7   38   45                                                  
CONECT   31    8   43   55                                                  
CONECT   32    9   46   56                                                  
CONECT   33   17   19   60                                                  
CONECT   34   19   23   57                                                  
CONECT   35   20   26   36                                                  
CONECT   36   18   35   47                                                  
CONECT   37   20   29   49                                                  
CONECT   38   24   30   50                                                  
CONECT   39   21   43   53                                                  
CONECT   40   22   46   54                                                  
CONECT   41   21   55   59                                                  
CONECT   42   22   56   58                                                  
CONECT   43   31   39   51                                                  
CONECT   44   27   28   58                                                  
CONECT   45   25   30   61                                                  
CONECT   46   32   40   59                                                  
CONECT   47   36   52   57                                                  
CONECT   48   23   24   60   61                                             
CONECT   49   37                                                            
CONECT   50   38                                                            
CONECT   51   43                                                            
CONECT   52   47                                                            
CONECT   53   10   39                                                       
CONECT   54   11   40                                                       
CONECT   55   31   41                                                       
CONECT   56   32   42                                                       
CONECT   57   34   47                                                       
CONECT   58   42   44                                                       
CONECT   59   41   46                                                       
CONECT   60   33   48                                                       
CONECT   61   45   48                                                       
CONECT   62   13                                                            
CONECT   63   14                                                            
CONECT   64   15                                                            
CONECT   65   16                                                            
MASTER        0    0    0    0    0    0    0    0   65    0  140    0
END

Synonyms

Not Available

Molecular Formula

C₄₈H₇₂O₁₃

Average Mass

857.091

Monoisotopic Mass

856.497292378

IUPAC Name

(10'Z,12'Z,16'Z)-6-(butan-2-yl)-4,7'-dihydroxy-15'-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-5,6',10',14',16'-pentamethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0^{4,9}]tricosane]-4',6',8',10',12',16'-hexaen-3'-one

Traditional Name

(10'Z,12'Z,16'Z)-4,7'-dihydroxy-15'-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-5,6',10',14',16'-pentamethyl-6-(sec-butyl)-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0^{4,9}]tricosane]-4',6',8',10',12',16'-hexaen-3'-one

CAS Registry Number

Not Available

SMILES

[H]\C1=C(C)\C(OC2CC(OC)C(OC3CC(OC)C(O)C(C)O3)C(C)O2)C(C)\C([H])=C(\[H])/C(/[H])=C(C)\C2=C(C=C(C)C(O)=C2)C(=O)OC2CC(C1)OC1(CC(O)C(C)C(O1)C(C)CC)C2

InChI Identifier

InChI=1S/C48H72O13/c1-12-25(2)45-30(7)38(50)24-48(61-45)23-34-19-33(60-48)17-16-28(5)44(27(4)15-13-14-26(3)35-20-37(49)29(6)18-36(35)47(52)57-34)58-42-22-40(54-11)46(32(9)56-42)59-41-21-39(53-10)43(51)31(8)55-41/h13-16,18,20,25,27,30-34,38-46,49-51H,12,17,19,21-24H2,1-11H3/b15-13-,26-14-,28-16-

InChI Key

ZRYHPEOHTDJRCY-VZUATFRUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as milbemycins. These are a group of macrolides with a structure containing a 16-membered lactone ring fused to a 1,7-dioxaspiroundecane ring system and to either a benzofuran (or hydrogenated derivative thereof). In some cases (e.G. Milbemycin E), the tetrahydrofuranyl ring is missing. Milbemycins can be o-glycosylated at C13 to form Avermectins. Milbemycins are produced by Streptomyces species.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Milbemycins

Direct Parent

Milbemycins

Alternative Parents

Substituents

Milbemycin
O-glycosyl compound
Glycosyl compound
Disaccharide
1-hydroxy-2-unsubstituted benzenoid
Ketal
Benzenoid
Oxane
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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	0.0034 g/L	ALOGPS
logP	4.94	ALOGPS
logP	8.4	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	8.77	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	160.83 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	230.71 m³·mol⁻¹	ChemAxon
Polarizability	97.41 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
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)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	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
Bacteria	Actinobacteria	1		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

78443961

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139584134

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 6,8a-Seco-6,8a-deoxy-2,5-didehydroaverme (MMDBc0004479)

MOL for #<Metabolite:0x00007f4697289d00>

3D MOL for #<Metabolite:0x00007f4697289d00>

3D SDF for #<Metabolite:0x00007f4697289d00>

3D-SDF for #<Metabolite:0x00007f4697289d00>

PDB for #<Metabolite:0x00007f4697289d00>

3D PDB for #<Metabolite:0x00007f4697289d00>

SMILES for #<Metabolite:0x00007f4697289d00>

INCHI for #<Metabolite:0x00007f4697289d00>

Structure for #<Metabolite:0x00007f4697289d00>

3D Structure for #<Metabolite:0x00007f4697289d00>