NP-MRD: Showing NP-Card for (3z,5e,8s,9e,11z,14s,16r,17e,19e,24s)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl (2e)-but-2-enoate (NP0186661)

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Record Information

Version

2.0

Created at

2022-09-04 02:35:54 UTC

Updated at

2022-09-04 02:35:54 UTC

NP-MRD ID

NP0186661

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3z,5e,8s,9e,11z,14s,16r,17e,19e,24s)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl (2e)-but-2-enoate

Description

7-O-2'E-butenoyl macrolactin A 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. (3z,5e,8s,9e,11z,14s,16r,17e,19e,24s)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl (2e)-but-2-enoate was first documented in 2016 (PMID: 27071303). Based on a literature review very few articles have been published on 7-O-2'E-butenoyl macrolactin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042204352D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309042204352D          

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M  END
> <DATABASE_ID>
NP0186661

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C\C(=O)O[C@H]1C\C=C\C=C/C(=O)O[C@@H](C)CCC\C=C\C=C\[C@H](O)C[C@@H](O)C\C=C/C=C/1

> <INCHI_IDENTIFIER>
InChI=1S/C28H38O6/c1-3-15-27(31)34-26-19-12-7-11-18-25(30)22-24(29)17-10-6-4-5-9-16-23(2)33-28(32)21-14-8-13-20-26/h3-4,6-8,10-15,17,19,21,23-26,29-30H,5,9,16,18,20,22H2,1-2H3/b6-4+,11-7-,13-8+,15-3+,17-10+,19-12+,21-14-/t23-,24-,25-,26+/m0/s1

> <INCHI_KEY>
GPAVSOORVSIRRW-DEHRZPGBSA-N

> <FORMULA>
C28H38O6

> <MOLECULAR_WEIGHT>
470.606

> <EXACT_MASS>
470.266838944

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
53.21755961887072

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3Z,5E,8S,9E,11Z,14S,16R,17E,19E,24S)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl (2E)-but-2-enoate

> <JCHEM_LOGP>
5.330731583333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.386664363301392

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.629219062819345

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7499811754467682

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
142.95180000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3Z,5E,8S,9E,11Z,14S,16R,17E,19E,24S)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl (2E)-but-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       6.647  12.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.448  11.243   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.026  10.651   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.828   9.124   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.406   8.533   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       6.051   8.188   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.852   6.661   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.276   6.074   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.803   5.875   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.026   4.939   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.965   3.719   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.557   2.297   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.760   0.771   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      13.300   0.773   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      11.561  -0.756   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.974  -2.180   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.197  -3.116   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       9.754  -3.119   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.818  -4.343   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.291  -4.546   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.869  -5.137   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.342  -4.938   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.919  -4.351   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.695  -3.415   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.756  -2.195   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.576  -2.967   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.165  -0.773   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -0.038   0.753   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.578   0.751   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.160   2.280   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.748   3.704   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.968   4.643   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.904   5.867   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.326   6.458   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   34                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33    7                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₈O₆

Average Mass

470.6060 Da

Monoisotopic Mass

470.26684 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C\C=C\C(=O)O[C@H]1C\C=C\C=C/C(=O)O[C@@H](C)CCC\C=C\C=C\[C@H](O)C[C@@H](O)C\C=C/C=C/1

InChI Identifier

InChI=1S/C28H38O6/c1-3-15-27(31)34-26-19-12-7-11-18-25(30)22-24(29)17-10-6-4-5-9-16-23(2)33-28(32)21-14-8-13-20-26/h3-4,6-8,10-15,17,19,21,23-26,29-30H,5,9,16,18,20,22H2,1-2H3/b6-4+,11-7-,13-8+,15-3+,17-10+,19-12+,21-14-/t23-,24-,25-,26+/m0/s1

InChI Key

GPAVSOORVSIRRW-DEHRZPGBSA-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

Not Available

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
Fatty acid ester
Fatty acyl
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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

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

58197347

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139591585

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li W, Tang XX, Yan X, Wu Z, Yi ZW, Fang MJ, Su X, Qiu YK: A new macrolactin antibiotic from deep sea-derived bacteria Bacillus subtilis B5. Nat Prod Res. 2016 Dec;30(24):2777-2782. doi: 10.1080/14786419.2016.1155576. Epub 2016 Apr 13. [PubMed:27071303 ]
LOTUS database [Link]

Showing NP-Card for (3z,5e,8s,9e,11z,14s,16r,17e,19e,24s)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl (2e)-but-2-enoate (NP0186661)

MOL for NP0186661 ((3z,5e,8s,9e,11z,14s,16r,17e,19e,24s)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl (2e)-but-2-enoate)

3D MOL for NP0186661 ((3z,5e,8s,9e,11z,14s,16r,17e,19e,24s)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl (2e)-but-2-enoate)

3D SDF for NP0186661 ((3z,5e,8s,9e,11z,14s,16r,17e,19e,24s)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl (2e)-but-2-enoate)

3D-SDF for NP0186661 ((3z,5e,8s,9e,11z,14s,16r,17e,19e,24s)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl (2e)-but-2-enoate)

PDB for NP0186661 ((3z,5e,8s,9e,11z,14s,16r,17e,19e,24s)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl (2e)-but-2-enoate)

3D PDB for NP0186661 ((3z,5e,8s,9e,11z,14s,16r,17e,19e,24s)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl (2e)-but-2-enoate)

SMILES for NP0186661 ((3z,5e,8s,9e,11z,14s,16r,17e,19e,24s)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl (2e)-but-2-enoate)

INCHI for NP0186661 ((3z,5e,8s,9e,11z,14s,16r,17e,19e,24s)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl (2e)-but-2-enoate)

Structure for NP0186661 ((3z,5e,8s,9e,11z,14s,16r,17e,19e,24s)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl (2e)-but-2-enoate)

3D Structure for NP0186661 ((3z,5e,8s,9e,11z,14s,16r,17e,19e,24s)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl (2e)-but-2-enoate)