NP-MRD: Showing NP-Card for 3-{[(3z,5e,8s,9e,11z,14s,16r,17e,19e,24r)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl]oxy}-3-oxopropanoic acid (NP0309380)

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Record Information

Version

2.0

Created at

2022-09-11 03:56:48 UTC

Updated at

2022-09-11 03:56:48 UTC

NP-MRD ID

NP0309380

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-{[(3z,5e,8s,9e,11z,14s,16r,17e,19e,24r)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl]oxy}-3-oxopropanoic acid

Description

7-O-MALONYL 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. 3-{[(3z,5e,8s,9e,11z,14s,16r,17e,19e,24r)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl]oxy}-3-oxopropanoic acid is found in Bacillus velezensis. 3-{[(3z,5e,8s,9e,11z,14s,16r,17e,19e,24r)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl]oxy}-3-oxopropanoic acid was first documented in 2012 (PMID: 22385216). Based on a literature review a small amount of articles have been published on 7-O-MALONYL MACROLACTIN A (PMID: 27071303) (PMID: 29856856) (PMID: 25322261).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112205562D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309112205562D          

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 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 20 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
  2 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0309380

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CCC\C=C\C=C\[C@H](O)C[C@@H](O)C\C=C/C=C/[C@H](C\C=C\C=C/C(=O)O1)OC(=O)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H36O8/c1-21-13-7-3-2-4-8-14-22(28)19-23(29)15-9-5-10-16-24(35-27(33)20-25(30)31)17-11-6-12-18-26(32)34-21/h2,4-6,8-12,14,16,18,21-24,28-29H,3,7,13,15,17,19-20H2,1H3,(H,30,31)/b4-2+,9-5-,11-6+,14-8+,16-10+,18-12-/t21-,22+,23+,24-/m1/s1

> <INCHI_KEY>
ZJSLOGHFCRASLO-BFRQYJOGSA-N

> <FORMULA>
C27H36O8

> <MOLECULAR_WEIGHT>
488.577

> <EXACT_MASS>
488.241018119

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
51.736828736171844

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[(3Z,5E,8S,9E,11Z,14S,16R,17E,19E,24R)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl]oxy}-3-oxopropanoic acid

> <JCHEM_LOGP>
3.846698694333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.62921906283227

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.1862848992251935

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7499811754467647

> <JCHEM_POLAR_SURFACE_AREA>
130.36

> <JCHEM_REFRACTIVITY>
138.9747

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(3Z,5E,8S,9E,11Z,14S,16R,17E,19E,24R)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl]oxy}-3-oxopropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       3.773 -15.674   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.773 -14.134   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.247 -13.933   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.824 -13.344   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.398 -12.406   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.987 -10.984   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.925  -9.762   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.724  -8.235   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.925  -6.708   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.335  -5.286   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.669  -4.516   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.398  -4.064   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.824  -3.126   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.054  -1.793   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.247  -2.537   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.773  -2.336   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.300  -2.537   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.522  -3.474   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.945  -4.064   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.882  -5.286   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.216  -4.516   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      11.550  -5.286   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      11.550  -6.826   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      12.883  -4.516   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.217  -5.286   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      15.551  -4.516   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      14.217  -6.826   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       9.472  -6.708   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.271  -8.235   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.472  -9.762   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.882 -11.185   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.945 -12.406   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.723 -13.344   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       7.493 -14.678   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       5.300 -13.933   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   20   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    2                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₆O₈

Average Mass

488.5770 Da

Monoisotopic Mass

488.24102 Da

IUPAC Name

3-{[(3Z,5E,8S,9E,11Z,14S,16R,17E,19E,24R)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl]oxy}-3-oxopropanoic acid

Traditional Name

3-{[(3Z,5E,8S,9E,11Z,14S,16R,17E,19E,24R)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl]oxy}-3-oxopropanoic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]1CCC\C=C\C=C\[C@H](O)C[C@@H](O)C\C=C/C=C/[C@H](C\C=C\C=C/C(=O)O1)OC(=O)CC(O)=O

InChI Identifier

InChI=1S/C27H36O8/c1-21-13-7-3-2-4-8-14-22(28)19-23(29)15-9-5-10-16-24(35-27(33)20-25(30)31)17-11-6-12-18-26(32)34-21/h2,4-6,8-12,14,16,18,21-24,28-29H,3,7,13,15,17,19-20H2,1H3,(H,30,31)/b4-2+,9-5-,11-6+,14-8+,16-10+,18-12-/t21-,22+,23+,24-/m1/s1

InChI Key

ZJSLOGHFCRASLO-BFRQYJOGSA-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
Bacillus velezensis	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
Tricarboxylic acid or derivatives
1,3-dicarbonyl compound
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organic oxide
Carbonyl group
Organooxygen compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
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	3.85	ChemAxon
pKa (Strongest Acidic)	4.19	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	130.36 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	138.97 m³·mol⁻¹	ChemAxon
Polarizability	51.74 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

31111754

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71479384

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 ]
Chen L, Heng J, Qin S, Bian K: A comprehensive understanding of the biocontrol potential of Bacillus velezensis LM2303 against Fusarium head blight. PLoS One. 2018 Jun 1;13(6):e0198560. doi: 10.1371/journal.pone.0198560. eCollection 2018. [PubMed:29856856 ]
Huang J, Wei Z, Tan S, Mei X, Shen Q, Xu Y: Suppression of bacterial wilt of tomato by bioorganic fertilizer made from the antibacterial compound producing strain Bacillus amyloliquefaciens HR62. J Agric Food Chem. 2014 Nov 5;62(44):10708-16. doi: 10.1021/jf503136a. Epub 2014 Oct 21. [PubMed:25322261 ]
Yuan J, Li B, Zhang N, Waseem R, Shen Q, Huang Q: Production of bacillomycin- and macrolactin-type antibiotics by Bacillus amyloliquefaciens NJN-6 for suppressing soilborne plant pathogens. J Agric Food Chem. 2012 Mar 28;60(12):2976-81. doi: 10.1021/jf204868z. Epub 2012 Mar 13. [PubMed:22385216 ]
LOTUS database [Link]

Showing NP-Card for 3-{[(3z,5e,8s,9e,11z,14s,16r,17e,19e,24r)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl]oxy}-3-oxopropanoic acid (NP0309380)

MOL for NP0309380 (3-{[(3z,5e,8s,9e,11z,14s,16r,17e,19e,24r)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl]oxy}-3-oxopropanoic acid)

3D MOL for NP0309380 (3-{[(3z,5e,8s,9e,11z,14s,16r,17e,19e,24r)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl]oxy}-3-oxopropanoic acid)

3D SDF for NP0309380 (3-{[(3z,5e,8s,9e,11z,14s,16r,17e,19e,24r)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl]oxy}-3-oxopropanoic acid)

3D-SDF for NP0309380 (3-{[(3z,5e,8s,9e,11z,14s,16r,17e,19e,24r)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl]oxy}-3-oxopropanoic acid)

PDB for NP0309380 (3-{[(3z,5e,8s,9e,11z,14s,16r,17e,19e,24r)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl]oxy}-3-oxopropanoic acid)

3D PDB for NP0309380 (3-{[(3z,5e,8s,9e,11z,14s,16r,17e,19e,24r)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl]oxy}-3-oxopropanoic acid)

SMILES for NP0309380 (3-{[(3z,5e,8s,9e,11z,14s,16r,17e,19e,24r)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl]oxy}-3-oxopropanoic acid)

INCHI for NP0309380 (3-{[(3z,5e,8s,9e,11z,14s,16r,17e,19e,24r)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl]oxy}-3-oxopropanoic acid)

Structure for NP0309380 (3-{[(3z,5e,8s,9e,11z,14s,16r,17e,19e,24r)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl]oxy}-3-oxopropanoic acid)

3D Structure for NP0309380 (3-{[(3z,5e,8s,9e,11z,14s,16r,17e,19e,24r)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl]oxy}-3-oxopropanoic acid)