NP-MRD: Showing NP-Card for 3,4-dihydroxy-5-[(8e,10e,14e,16e)-1,2,3,4,5-pentahydroxy-6,20-dimethylhenicosa-8,10,14,16-tetraen-1-yl]oxolan-2-one (NP0306734)

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Record Information

Version

2.0

Created at

2022-09-10 23:24:26 UTC

Updated at

2022-09-10 23:24:26 UTC

NP-MRD ID

NP0306734

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4-dihydroxy-5-[(8e,10e,14e,16e)-1,2,3,4,5-pentahydroxy-6,20-dimethylhenicosa-8,10,14,16-tetraen-1-yl]oxolan-2-one

Description

Butyrolactol B belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. 3,4-dihydroxy-5-[(8e,10e,14e,16e)-1,2,3,4,5-pentahydroxy-6,20-dimethylhenicosa-8,10,14,16-tetraen-1-yl]oxolan-2-one is found in Streptomyces rochei. Based on a literature review very few articles have been published on Butyrolactol B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112201242D          

 36 36  0  0  0  0            999 V2000
   -5.7773   -3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0628   -4.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0628   -5.1455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3484   -3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6339   -4.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9194   -3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2049   -4.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4905   -3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7760   -4.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 80 80  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652309112201242D          

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   10.1198   -5.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4554   -6.0662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3128   -5.1410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6997   -5.6930    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 29 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0306734

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC\C=C\C=C\CC\C=C\C=C\CC(C)C(O)C(O)C(O)C(O)C(O)C1OC(=O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O9/c1-17(2)15-13-11-9-7-5-4-6-8-10-12-14-16-18(3)19(28)20(29)21(30)22(31)23(32)26-24(33)25(34)27(35)36-26/h5,7-12,14,17-26,28-34H,4,6,13,15-16H2,1-3H3/b7-5+,10-8+,11-9+,14-12+

> <INCHI_KEY>
QOXADYBJIYSAHC-MSPXPRSUSA-N

> <FORMULA>
C27H44O9

> <MOLECULAR_WEIGHT>
512.64

> <EXACT_MASS>
512.298532997

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
57.233231418387255

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4-dihydroxy-5-[(8E,10E,14E,16E)-1,2,3,4,5-pentahydroxy-6,20-dimethylhenicosa-8,10,14,16-tetraen-1-yl]oxolan-2-one

> <JCHEM_LOGP>
1.731086013666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.482649249691313

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.571777111931302

> <JCHEM_PKA_STRONGEST_BASIC>
-3.290313090687828

> <JCHEM_POLAR_SURFACE_AREA>
167.91

> <JCHEM_REFRACTIVITY>
139.50970000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3,4-dihydroxy-5-[(8E,10E,14E,16E)-1,2,3,4,5-pentahydroxy-6,20-dimethylhenicosa-8,10,14,16-tetraen-1-yl]oxolan-2-one

> <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     -10.784  -7.295   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.451  -8.065   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.451  -9.605   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.117  -7.295   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.783  -8.065   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.450  -7.295   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.116  -8.065   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.782  -7.295   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.449  -8.065   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.115  -7.295   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.219  -8.065   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.552  -7.295   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.886  -8.065   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.220  -7.295   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.554  -8.065   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.887  -7.295   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.221  -8.065   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.221  -9.605   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.555  -7.295   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.555  -5.755   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      11.888  -8.065   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      11.888  -9.605   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      13.222  -7.295   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      13.222  -5.755   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      14.556  -8.065   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      14.556  -9.605   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      15.889  -7.295   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      15.889  -5.755   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      17.223  -8.065   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      18.630  -7.439   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      19.660  -8.583   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      21.192  -8.422   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      18.890  -9.917   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      19.517 -11.324   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      17.384  -9.597   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      16.239 -10.627   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    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                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   35                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   29   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   72    0
END

View in JSmol

Synonyms

Value	Source
Butyrolactol-b	MeSH

Chemical Formula

C₂₇H₄₄O₉

Average Mass

512.6400 Da

Monoisotopic Mass

512.29853 Da

IUPAC Name

3,4-dihydroxy-5-[(8E,10E,14E,16E)-1,2,3,4,5-pentahydroxy-6,20-dimethylhenicosa-8,10,14,16-tetraen-1-yl]oxolan-2-one

Traditional Name

3,4-dihydroxy-5-[(8E,10E,14E,16E)-1,2,3,4,5-pentahydroxy-6,20-dimethylhenicosa-8,10,14,16-tetraen-1-yl]oxolan-2-one

CAS Registry Number

Not Available

SMILES

CC(C)CC\C=C\C=C\CC\C=C\C=C\CC(C)C(O)C(O)C(O)C(O)C(O)C1OC(=O)C(O)C1O

InChI Identifier

InChI=1S/C27H44O9/c1-17(2)15-13-11-9-7-5-4-6-8-10-12-14-16-18(3)19(28)20(29)21(30)22(31)23(32)26-24(33)25(34)27(35)36-26/h5,7-12,14,17-26,28-34H,4,6,13,15-16H2,1-3H3/b7-5+,10-8+,11-9+,14-12+

InChI Key

QOXADYBJIYSAHC-MSPXPRSUSA-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
Streptomyces rochei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Fatty alcohols

Alternative Parents

Substituents

Fatty alcohol
Gamma butyrolactone
Oxolane
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organooxygen compound
Alcohol
Organic oxygen compound
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	1.73	ChemAxon
pKa (Strongest Acidic)	11.57	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	167.91 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	139.51 m³·mol⁻¹	ChemAxon
Polarizability	57.23 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	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

C00016754

Chemspider ID

4943881

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6439478

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,4-dihydroxy-5-[(8e,10e,14e,16e)-1,2,3,4,5-pentahydroxy-6,20-dimethylhenicosa-8,10,14,16-tetraen-1-yl]oxolan-2-one (NP0306734)

MOL for NP0306734 (3,4-dihydroxy-5-[(8e,10e,14e,16e)-1,2,3,4,5-pentahydroxy-6,20-dimethylhenicosa-8,10,14,16-tetraen-1-yl]oxolan-2-one)

3D MOL for NP0306734 (3,4-dihydroxy-5-[(8e,10e,14e,16e)-1,2,3,4,5-pentahydroxy-6,20-dimethylhenicosa-8,10,14,16-tetraen-1-yl]oxolan-2-one)

3D SDF for NP0306734 (3,4-dihydroxy-5-[(8e,10e,14e,16e)-1,2,3,4,5-pentahydroxy-6,20-dimethylhenicosa-8,10,14,16-tetraen-1-yl]oxolan-2-one)

3D-SDF for NP0306734 (3,4-dihydroxy-5-[(8e,10e,14e,16e)-1,2,3,4,5-pentahydroxy-6,20-dimethylhenicosa-8,10,14,16-tetraen-1-yl]oxolan-2-one)

PDB for NP0306734 (3,4-dihydroxy-5-[(8e,10e,14e,16e)-1,2,3,4,5-pentahydroxy-6,20-dimethylhenicosa-8,10,14,16-tetraen-1-yl]oxolan-2-one)

3D PDB for NP0306734 (3,4-dihydroxy-5-[(8e,10e,14e,16e)-1,2,3,4,5-pentahydroxy-6,20-dimethylhenicosa-8,10,14,16-tetraen-1-yl]oxolan-2-one)

SMILES for NP0306734 (3,4-dihydroxy-5-[(8e,10e,14e,16e)-1,2,3,4,5-pentahydroxy-6,20-dimethylhenicosa-8,10,14,16-tetraen-1-yl]oxolan-2-one)

INCHI for NP0306734 (3,4-dihydroxy-5-[(8e,10e,14e,16e)-1,2,3,4,5-pentahydroxy-6,20-dimethylhenicosa-8,10,14,16-tetraen-1-yl]oxolan-2-one)

Structure for NP0306734 (3,4-dihydroxy-5-[(8e,10e,14e,16e)-1,2,3,4,5-pentahydroxy-6,20-dimethylhenicosa-8,10,14,16-tetraen-1-yl]oxolan-2-one)

3D Structure for NP0306734 (3,4-dihydroxy-5-[(8e,10e,14e,16e)-1,2,3,4,5-pentahydroxy-6,20-dimethylhenicosa-8,10,14,16-tetraen-1-yl]oxolan-2-one)