NP-MRD: Showing NP-Card for (+)-Butalactin (NP0061604)

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Record Information

Version

2.0

Created at

2022-04-28 06:21:54 UTC

Updated at

2022-04-28 06:21:54 UTC

NP-MRD ID

NP0061604

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Butalactin

Description

Butalactin belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. (+)-Butalactin is found in Streptomyces sp. HIL Y-8636923. (+)-Butalactin was first documented in 2004 (PMID: 15455149). Based on a literature review very few articles have been published on Butalactin.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 32  0  0  0  0  0  0  0  0999 V2000
    4.2772   -0.8697   -0.1132 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1720    0.6162   -0.2072 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8501    1.0018   -1.6077 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0222    1.3753   -0.5428 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6183    0.8236   -0.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2721    0.0921    0.5061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0209   -0.5031    0.6824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2282   -1.2214    1.7483 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1509   -0.3922   -0.2156 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0444    0.3827   -1.3288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5067   -1.8247   -0.5951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3382   -2.3024   -1.7183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0142   -2.3356    0.5901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7295   -1.3265    1.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4525   -0.0437    0.5365 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5465    0.1223   -0.4960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7443    0.4391    0.1693 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6166   -1.4054   -0.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1158   -1.2693    0.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3217   -1.1926   -0.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0991    1.1528    0.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0318    2.4691   -0.3634 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9611    1.0497   -1.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0635   -0.0696    1.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3795    1.2962   -1.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4409   -1.1992    2.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8409   -1.5362    1.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3186    0.8263    1.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7134   -0.8843   -0.9423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3398    0.8838   -1.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6118    0.4734    1.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  6
  9 15  1  0
 15 16  1  0
 16 17  1  0
 15 14  1  0
 14 13  1  0
 13 11  1  0
 11 12  2  0
  4  2  1  0
 11  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  1
  4 22  1  1
  5 23  1  0
  6 24  1  0
 10 25  1  0
 15 28  1  1
 16 29  1  0
 16 30  1  0
 17 31  1  0
 14 26  1  0
 14 27  1  0
M  END


  Mrv1652304282208212D          

 17 18  0  0  1  0            999 V2000
   -4.8137    5.1412    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3358    4.4687    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8277    3.8064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5809    3.0191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6096    4.0695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6009    4.8945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6128    4.8662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6213    4.0562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9068    4.4687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6213    3.2312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9068    2.8187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9068    1.9937    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4943    1.2792    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3193    1.2792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7799    0.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5505    5.9231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0961    6.5419    0.0000 O   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  2  7  1  6  0  0  0
  2  8  1  1  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  1  0  0  0
  1 16  1  6  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0061604

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1O[C@H]1\C=C\C(=O)[C@]1(O)[C@@H](CO)COC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H14O6/c1-6-8(17-6)2-3-9(13)11(15)7(4-12)5-16-10(11)14/h2-3,6-8,12,15H,4-5H2,1H3/b3-2+/t6-,7+,8+,11-/m1/s1

> <INCHI_KEY>
NDWZCKPIOWDQOR-WTCWJIQASA-N

> <FORMULA>
C11H14O6

> <MOLECULAR_WEIGHT>
242.227

> <EXACT_MASS>
242.079038171

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
22.783068260696616

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,4S)-3-hydroxy-4-(hydroxymethyl)-3-[(2E)-3-[(2S,3R)-3-methyloxiran-2-yl]prop-2-enoyl]oxolan-2-one

> <ALOGPS_LOGP>
-0.61

> <JCHEM_LOGP>
-0.4925388296666664

> <ALOGPS_LOGS>
-0.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.366852707026776

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.38685719526577

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6821604187640524

> <JCHEM_POLAR_SURFACE_AREA>
96.36

> <JCHEM_REFRACTIVITY>
56.4587

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.34e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4S)-3-hydroxy-4-(hydroxymethyl)-3-[(2E)-3-[(2S,3R)-3-methyloxiran-2-yl]prop-2-enoyl]oxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -8.986   9.597   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.093   8.342   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.012   7.105   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -8.551   5.636   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0     -10.471   7.596   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0     -10.455   9.136   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -6.744   9.083   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -6.760   7.572   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -5.426   8.342   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -6.760   6.032   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.426   5.262   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.426   3.722   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.656   2.388   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -6.196   2.388   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -3.322   1.618   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.494  11.056   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -9.513  12.212   0.000  0.00  0.00           O+0
CONECT    1    2    6   16                                                  
CONECT    2    1    3    7    8                                             
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    1                                                       
CONECT    7    2                                                            
CONECT    8    2    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13   12                                                       
CONECT   15   13                                                            
CONECT   16    1   17                                                       
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
2-(4',5'-Epoxy-hex-2'(e)-en)oyl-2-hydroxy-3-hydroxymethyl-2,3-(Z)-butanolide	MeSH

Chemical Formula

C₁₁H₁₄O₆

Average Mass

242.2270 Da

Monoisotopic Mass

242.07904 Da

IUPAC Name

(3R,4S)-3-hydroxy-4-(hydroxymethyl)-3-[(2E)-3-[(2S,3R)-3-methyloxiran-2-yl]prop-2-enoyl]oxolan-2-one

Traditional Name

(3R,4S)-3-hydroxy-4-(hydroxymethyl)-3-[(2E)-3-[(2S,3R)-3-methyloxiran-2-yl]prop-2-enoyl]oxolan-2-one

CAS Registry Number

Not Available

SMILES

C[C@H]1O[C@H]1\C=C\C(=O)[C@]1(O)[C@@H](CO)COC1=O

InChI Identifier

InChI=1S/C11H14O6/c1-6-8(17-6)2-3-9(13)11(15)7(4-12)5-16-10(11)14/h2-3,6-8,12,15H,4-5H2,1H3/b3-2+/t6-,7+,8+,11-/m1/s1

InChI Key

NDWZCKPIOWDQOR-WTCWJIQASA-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
Streptomyces sp. HIL Y-8636923	Bacteria	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Acryloyl-group
Alpha-hydroxy ketone
Enone
Oxolane
Tertiary alcohol
Alpha,beta-unsaturated ketone
Ketone
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Organic oxide
Aldehyde
Organic oxygen compound
Organooxygen compound
Primary alcohol
Alcohol
Carbonyl group
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	-0.61	ALOGPS
logP	-0.49	ChemAxon
logS	-0.66	ALOGPS
pKa (Strongest Acidic)	10.39	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	96.36 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	56.46 m³·mol⁻¹	ChemAxon
Polarizability	22.78 Å³	ChemAxon
Number of Rings	2	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

C00017073

Chemspider ID

9497397

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11322443

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ueki T, Kinoshita T: Stereoselective synthesis and structure of butalactin and lactone II isolated from Streptomyces species. Org Biomol Chem. 2004 Oct 7;2(19):2777-85. doi: 10.1039/B407820A. Epub 2004 Aug 23. [PubMed:15455149 ]

Showing NP-Card for (+)-Butalactin (NP0061604)

MOL for NP0061604 ((+)-Butalactin)

3D MOL for NP0061604 ((+)-Butalactin)

3D SDF for NP0061604 ((+)-Butalactin)

3D-SDF for NP0061604 ((+)-Butalactin)

PDB for NP0061604 ((+)-Butalactin)

3D PDB for NP0061604 ((+)-Butalactin)

SMILES for NP0061604 ((+)-Butalactin)

INCHI for NP0061604 ((+)-Butalactin)

Structure for NP0061604 ((+)-Butalactin)

3D Structure for NP0061604 ((+)-Butalactin)