NP-MRD: Showing NP-Card for Aerugine (NP0004569)

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Record Information

Version

2.0

Created at

2020-12-09 02:01:41 UTC

Updated at

2021-07-15 16:49:32 UTC

NP-MRD ID

NP0004569

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aerugine

Provided By

NPAtlas

Description

Aerugine is found in Pseudomonas and Pseudomonas fluorescens. Aerugine was first documented in 2003 (PMID: 12676678). Based on a literature review very few articles have been published on 2-[(4R)-4-(hydroxymethyl)-4,5-dihydro-1,3-thiazol-2-yl]phenol (PMID: 28553520) (PMID: 30793902) (PMID: 33577297).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118073D          

 25 26  0  0  0  0            999 V2000
    2.9817   -1.6081    1.0362 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3394   -0.8421   -0.0454 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4164    0.3463   -0.2404 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4946    1.2819    0.9510 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8373    2.0571    0.6976 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1193    0.5678   -0.0621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3073    0.3155   -0.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2065    1.2510    0.3572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5730    1.0761    0.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0986   -0.0559   -0.2756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2287   -0.9844   -0.7844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8307   -0.8122   -0.7317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0099   -1.7814   -1.2605 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1142   -0.1105   -0.4434 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6055   -2.4729    0.7343 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3995   -0.4920    0.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2708   -1.4501   -0.9808 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7350    0.9437   -1.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4835    0.7535    1.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2935    2.0327    0.8375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7859    2.1522    0.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2335    1.8266    0.7123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1750   -0.2330   -0.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5946   -1.9052   -1.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0470   -1.8565   -1.3255 H   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
  3  4  1  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  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  6 14  2  0  0  0  0
 14  3  1  0  0  0  0
 12  7  1  0  0  0  0
  1 15  1  0  0  0  0
  2 16  1  0  0  0  0
  2 17  1  0  0  0  0
  3 18  1  6  0  0  0
  4 19  1  0  0  0  0
  4 20  1  0  0  0  0
  8 21  1  0  0  0  0
  9 22  1  0  0  0  0
 10 23  1  0  0  0  0
 11 24  1  0  0  0  0
 13 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004569

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C([H])C([H])=C1C1=N[C@]([H])(C([H])([H])O[H])C([H])([H])S1

> <INCHI_IDENTIFIER>
InChI=1S/C10H11NO2S/c12-5-7-6-14-10(11-7)8-3-1-2-4-9(8)13/h1-4,7,12-13H,5-6H2/t7-/m1/s1

> <INCHI_KEY>
CQCVSXXDUMTFCR-SSDOTTSWSA-N

> <FORMULA>
C10H11NO2S

> <MOLECULAR_WEIGHT>
209.26

> <EXACT_MASS>
209.051049772

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
21.527677611084478

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(4R)-4-(hydroxymethyl)-4,5-dihydro-1,3-thiazol-2-yl]phenol

> <ALOGPS_LOGP>
1.24

> <JCHEM_LOGP>
2.052579234666667

> <ALOGPS_LOGS>
-2.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.801257476698694

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.618432660559673

> <JCHEM_PKA_STRONGEST_BASIC>
3.3029980852922023

> <JCHEM_POLAR_SURFACE_AREA>
52.82000000000001

> <JCHEM_REFRACTIVITY>
57.510400000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.48e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(4R)-4-(hydroxymethyl)-4,5-dihydro-1,3-thiazol-2-yl]phenol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0       2.982  -1.608   1.036  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.339  -0.842  -0.045  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.416   0.346  -0.240  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.495   1.282   0.951  0.00  0.00           C+0
HETATM    5  S   UNK     0       0.837   2.057   0.698  0.00  0.00           S+0
HETATM    6  C   UNK     0       0.119   0.568  -0.062  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.307   0.316  -0.156  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.207   1.251   0.357  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.573   1.076   0.302  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.099  -0.056  -0.276  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.229  -0.984  -0.784  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.831  -0.812  -0.732  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.010  -1.781  -1.260  0.00  0.00           O+0
HETATM   14  N   UNK     0       1.114  -0.111  -0.443  0.00  0.00           N+0
HETATM   15  H   UNK     0       2.606  -2.473   0.734  0.00  0.00           H+0
HETATM   16  H   UNK     0       4.399  -0.492   0.005  0.00  0.00           H+0
HETATM   17  H   UNK     0       3.271  -1.450  -0.981  0.00  0.00           H+0
HETATM   18  H   UNK     0       2.735   0.944  -1.128  0.00  0.00           H+0
HETATM   19  H   UNK     0       2.483   0.754   1.903  0.00  0.00           H+0
HETATM   20  H   UNK     0       3.293   2.033   0.838  0.00  0.00           H+0
HETATM   21  H   UNK     0      -1.786   2.152   0.817  0.00  0.00           H+0
HETATM   22  H   UNK     0      -4.234   1.827   0.712  0.00  0.00           H+0
HETATM   23  H   UNK     0      -5.175  -0.233  -0.340  0.00  0.00           H+0
HETATM   24  H   UNK     0      -3.595  -1.905  -1.256  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.047  -1.857  -1.325  0.00  0.00           H+0
CONECT    1    2   15                                                       
CONECT    2    1    3   16   17                                             
CONECT    3    2    4   14   18                                             
CONECT    4    3    5   19   20                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9   21                                                  
CONECT    9    8   10   22                                                  
CONECT   10    9   11   23                                                  
CONECT   11   10   12   24                                                  
CONECT   12   11   13    7                                                  
CONECT   13   12   25                                                       
CONECT   14    6    3                                                       
CONECT   15    1                                                            
CONECT   16    2                                                            
CONECT   17    2                                                            
CONECT   18    3                                                            
CONECT   19    4                                                            
CONECT   20    4                                                            
CONECT   21    8                                                            
CONECT   22    9                                                            
CONECT   23   10                                                            
CONECT   24   11                                                            
CONECT   25   13                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₀H₁₁NO₂S

Average Mass

209.2600 Da

Monoisotopic Mass

209.05105 Da

IUPAC Name

2-[(4R)-4-(hydroxymethyl)-4,5-dihydro-1,3-thiazol-2-yl]phenol

Traditional Name

2-[(4R)-4-(hydroxymethyl)-4,5-dihydro-1,3-thiazol-2-yl]phenol

CAS Registry Number

Not Available

SMILES

OC[C@@H]1CSC(=N1)C1=CC=CC=C1O

InChI Identifier

InChI=1S/C10H11NO2S/c12-5-7-6-14-10(11-7)8-3-1-2-4-9(8)13/h1-4,7,12-13H,5-6H2/t7-/m1/s1

InChI Key

CQCVSXXDUMTFCR-SSDOTTSWSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Clerodendrum inerme	KNApSAcK Database	22123792
Linaria aeruginea	KNApSAcK Database	22123792
Pseudomonas	NPAtlas	12676678
Pseudomonas fluorescens	LOTUS Database	35616633
Stachys annua	KNApSAcK Database	22123792
Tripora divaricata	KNApSAcK Database	22123792

Chemical Taxonomy

Classification

Not classified

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	1.24	ALOGPS
logP	2.05	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	10.62	ChemAxon
pKa (Strongest Basic)	3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	52.82 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	57.51 m³·mol⁻¹	ChemAxon
Polarizability	21.53 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA018498

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

26391268

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lee JY, Moon SS, Hwang BK: Isolation and antifungal and antioomycete activities of aerugine produced by Pseudomonas fluorescens strain MM-B16. Appl Environ Microbiol. 2003 Apr;69(4):2023-31. doi: 10.1128/aem.69.4.2023-2031.2003. [PubMed:12676678 ]
Inahashi Y, Zhou S, Bibb MJ, Song L, Al-Bassam MM, Bibb MJ, Challis GL: Watasemycin biosynthesis in Streptomyces venezuelae: thiazoline C-methylation by a type B radical-SAM methylase homologue. Chem Sci. 2017 Apr 1;8(4):2823-2831. doi: 10.1039/c6sc03533g. Epub 2017 Jan 19. [PubMed:28553520 ]
Lacerna NM 2nd, Miller BW, Lim AL, Tun JO, Robes JMD, Cleofas MJB, Lin Z, Salvador-Reyes LA, Haygood MG, Schmidt EW, Concepcion GP: Mindapyrroles A-C, Pyoluteorin Analogues from a Shipworm-Associated Bacterium. J Nat Prod. 2019 Apr 26;82(4):1024-1028. doi: 10.1021/acs.jnatprod.8b00979. Epub 2019 Feb 22. [PubMed:30793902 ]
Kaplan AR, Musaev DG, Wuest WM: Pyochelin Biosynthetic Metabolites Bind Iron and Promote Growth in Pseudomonads Demonstrating Siderophore-like Activity. ACS Infect Dis. 2021 Mar 12;7(3):544-551. doi: 10.1021/acsinfecdis.0c00897. Epub 2021 Feb 12. [PubMed:33577297 ]

Showing NP-Card for Aerugine (NP0004569)

MOL for NP0004569 (Aerugine)

3D MOL for NP0004569 (Aerugine)

3D SDF for NP0004569 (Aerugine)

3D-SDF for NP0004569 (Aerugine)

PDB for NP0004569 (Aerugine)

3D PDB for NP0004569 (Aerugine)

SMILES for NP0004569 (Aerugine)

INCHI for NP0004569 (Aerugine)

Structure for NP0004569 (Aerugine)

3D Structure for NP0004569 (Aerugine)