NP-MRD: Showing NP-Card for 12-(but-2-en-2-yl)-8-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3,9-dimethyl-2,6-dioxo-1-oxacyclododeca-4,9-dien-7-yl 3-methylbutanoate (NP0153038)

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Record Information

Version

2.0

Created at

2022-09-02 09:37:34 UTC

Updated at

2022-09-02 09:37:34 UTC

NP-MRD ID

NP0153038

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-(but-2-en-2-yl)-8-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3,9-dimethyl-2,6-dioxo-1-oxacyclododeca-4,9-dien-7-yl 3-methylbutanoate

Description

12-(But-2-en-2-yl)-8-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3,9-dimethyl-2,6-dioxo-1-oxacyclododeca-4,9-dien-7-yl 3-methylbutanoate belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. 12-(but-2-en-2-yl)-8-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3,9-dimethyl-2,6-dioxo-1-oxacyclododeca-4,9-dien-7-yl 3-methylbutanoate is found in Pyxidicoccus fallax. Based on a literature review very few articles have been published on 12-(but-2-en-2-yl)-8-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3,9-dimethyl-2,6-dioxo-1-oxacyclododeca-4,9-dien-7-yl 3-methylbutanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022211372D          

 37 38  0  0  0  0            999 V2000
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  5 37  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309022211372D          

 37 38  0  0  0  0            999 V2000
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    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  4  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  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  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 10 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 21 29  1  0  0  0  0
 29 30  2  0  0  0  0
 31 29  1  4  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
  5 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0153038

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=C(C)C1CC=C(C)C(OC2OC(CO)C(O)C2O)C(OC(=O)CC(C)C)C(=O)C=CC(C)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O10/c1-7-15(4)19-11-9-16(5)24(37-27-23(32)22(31)20(13-28)35-27)25(36-21(30)12-14(2)3)18(29)10-8-17(6)26(33)34-19/h7-10,14,17,19-20,22-25,27-28,31-32H,11-13H2,1-6H3

> <INCHI_KEY>
CYOPPYPXPLWQGX-UHFFFAOYSA-N

> <FORMULA>
C27H40O10

> <MOLECULAR_WEIGHT>
524.607

> <EXACT_MASS>
524.262147488

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
54.88689032744958

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
12-(but-2-en-2-yl)-8-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3,9-dimethyl-2,6-dioxo-1-oxacyclododeca-4,9-dien-7-yl 3-methylbutanoate

> <ALOGPS_LOGP>
1.86

> <JCHEM_LOGP>
2.8682630253333317

> <ALOGPS_LOGS>
-3.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.825396060798635

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.276092133602425

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9811436141574488

> <JCHEM_POLAR_SURFACE_AREA>
148.82

> <JCHEM_REFRACTIVITY>
135.0898

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.52e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-(but-2-en-2-yl)-8-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3,9-dimethyl-2,6-dioxo-1-oxacyclododeca-4,9-dien-7-yl 3-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.428   3.556   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667   3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.073   3.224   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.104   4.368   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.635   4.207   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.262   2.800   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.334   5.702   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.960   7.109   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.173   5.382   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.317   6.412   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   37                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   21                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   12   20                                                  
CONECT   20   19                                                            
CONECT   21   10   22   29                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   21   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35    5                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   76    0
END

View in JSmol

Synonyms

Value	Source
12-(But-2-en-2-yl)-8-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3,9-dimethyl-2,6-dioxo-1-oxacyclododeca-4,9-dien-7-yl 3-methylbutanoic acid	Generator

Chemical Formula

C₂₇H₄₀O₁₀

Average Mass

524.6070 Da

Monoisotopic Mass

524.26215 Da

IUPAC Name

12-(but-2-en-2-yl)-8-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3,9-dimethyl-2,6-dioxo-1-oxacyclododeca-4,9-dien-7-yl 3-methylbutanoate

Traditional Name

12-(but-2-en-2-yl)-8-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3,9-dimethyl-2,6-dioxo-1-oxacyclododeca-4,9-dien-7-yl 3-methylbutanoate

CAS Registry Number

Not Available

SMILES

CC=C(C)C1CC=C(C)C(OC2OC(CO)C(O)C2O)C(OC(=O)CC(C)C)C(=O)C=CC(C)C(=O)O1

InChI Identifier

InChI=1S/C27H40O10/c1-7-15(4)19-11-9-16(5)24(37-27-23(32)22(31)20(13-28)35-27)25(36-21(30)12-14(2)3)18(29)10-8-17(6)26(33)34-19/h7-10,14,17,19-20,22-25,27-28,31-32H,11-13H2,1-6H3

InChI Key

CYOPPYPXPLWQGX-UHFFFAOYSA-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
Pyxidicoccus fallax	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
O-glycosyl compound
Glycosyl compound
Pentose monosaccharide
Alpha-acyloxy ketone
Fatty acid ester
Fatty acyl
Monosaccharide
Dicarboxylic acid or derivatives
Tetrahydrofuran
Cyclic ketone
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	1.86	ALOGPS
logP	2.87	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	12.28	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	148.82 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	135.09 m³·mol⁻¹	ChemAxon
Polarizability	54.89 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162952770

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 12-(but-2-en-2-yl)-8-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3,9-dimethyl-2,6-dioxo-1-oxacyclododeca-4,9-dien-7-yl 3-methylbutanoate (NP0153038)

MOL for NP0153038 (12-(but-2-en-2-yl)-8-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3,9-dimethyl-2,6-dioxo-1-oxacyclododeca-4,9-dien-7-yl 3-methylbutanoate)

3D MOL for NP0153038 (12-(but-2-en-2-yl)-8-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3,9-dimethyl-2,6-dioxo-1-oxacyclododeca-4,9-dien-7-yl 3-methylbutanoate)

3D SDF for NP0153038 (12-(but-2-en-2-yl)-8-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3,9-dimethyl-2,6-dioxo-1-oxacyclododeca-4,9-dien-7-yl 3-methylbutanoate)

3D-SDF for NP0153038 (12-(but-2-en-2-yl)-8-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3,9-dimethyl-2,6-dioxo-1-oxacyclododeca-4,9-dien-7-yl 3-methylbutanoate)

PDB for NP0153038 (12-(but-2-en-2-yl)-8-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3,9-dimethyl-2,6-dioxo-1-oxacyclododeca-4,9-dien-7-yl 3-methylbutanoate)

3D PDB for NP0153038 (12-(but-2-en-2-yl)-8-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3,9-dimethyl-2,6-dioxo-1-oxacyclododeca-4,9-dien-7-yl 3-methylbutanoate)

SMILES for NP0153038 (12-(but-2-en-2-yl)-8-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3,9-dimethyl-2,6-dioxo-1-oxacyclododeca-4,9-dien-7-yl 3-methylbutanoate)

INCHI for NP0153038 (12-(but-2-en-2-yl)-8-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3,9-dimethyl-2,6-dioxo-1-oxacyclododeca-4,9-dien-7-yl 3-methylbutanoate)

Structure for NP0153038 (12-(but-2-en-2-yl)-8-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3,9-dimethyl-2,6-dioxo-1-oxacyclododeca-4,9-dien-7-yl 3-methylbutanoate)

3D Structure for NP0153038 (12-(but-2-en-2-yl)-8-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3,9-dimethyl-2,6-dioxo-1-oxacyclododeca-4,9-dien-7-yl 3-methylbutanoate)