NP-MRD: Showing NP-Card for (1s,5s,8s)-8-hydroxy-8-[(1e)-3-hydroxybut-1-en-1-yl]-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-3-one (NP0209870)

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Record Information

Version

2.0

Created at

2022-09-05 07:27:29 UTC

Updated at

2022-09-05 07:27:29 UTC

NP-MRD ID

NP0209870

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,5s,8s)-8-hydroxy-8-[(1e)-3-hydroxybut-1-en-1-yl]-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-3-one

Description

CHEMBL454176 belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms. (1s,5s,8s)-8-hydroxy-8-[(1e)-3-hydroxybut-1-en-1-yl]-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-3-one is found in Silene baccifera and Sesbania drummondii. Based on a literature review very few articles have been published on CHEMBL454176.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
    4.1787    1.1083    0.4196 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1211    0.3209    1.1463 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5957   -0.9899    1.3656 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9266    0.1761    0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7468   -0.2003    0.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4038   -0.3373   -0.2052 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0994   -0.8680   -1.4521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1789    0.9667   -0.3819 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3225    2.1735   -0.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2002    0.8854    0.7270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0243   -0.3393    1.3574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5064   -1.2055    0.3824 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9853   -2.4185    1.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5005   -1.4971   -0.6870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5931   -0.4627   -1.7309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2897   -0.6982   -2.7035 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9036    0.8474   -1.6924 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7469    1.7966   -0.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7965    1.7108    1.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8726    0.4389   -0.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8289    0.7982    2.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6126   -1.4230    0.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0327    0.3861   -0.8238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6839   -0.4031    1.7674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8379   -1.0812   -1.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1246    2.4689   -1.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4058    2.0938    0.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9948    3.0395   -0.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1620    1.7394    1.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2522    0.8672    0.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8160   -3.1772    1.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0818   -2.8434    0.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7897   -2.2033    2.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2096   -2.4524   -1.1987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5106   -1.7103   -0.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5815    1.6915   -1.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1054    0.8015   -2.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  6
  6  8  1  0
  8  9  1  6
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  1
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 12  6  1  0
 17  8  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  1
  3 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 17 36  1  0
 17 37  1  0
M  END


  Mrv1652309052209272D          

 17 18  0  0  1  0            999 V2000
    3.3553   -1.9327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5412   -2.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2501   -2.8385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0182   -1.4285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3541   -0.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3941   -0.0001    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3627    0.4836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1624    0.9268    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8891    1.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5174    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5174   -0.4126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1624   -0.9270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8116   -1.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667   -0.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3247   -0.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2125    0.1061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667    0.7432    0.0000 C   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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  8 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0209870

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)\C=C\[C@]1(O)[C@]2(C)CO[C@@]1(C)CC(=O)C2

> <INCHI_IDENTIFIER>
InChI=1S/C13H20O4/c1-9(14)4-5-13(16)11(2)6-10(15)7-12(13,3)17-8-11/h4-5,9,14,16H,6-8H2,1-3H3/b5-4+/t9?,11-,12-,13-/m0/s1

> <INCHI_KEY>
KENVUEOHDFOVNA-HQZIRTJDSA-N

> <FORMULA>
C13H20O4

> <MOLECULAR_WEIGHT>
240.299

> <EXACT_MASS>
240.136159124

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
25.50307336041539

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,5S,8S)-8-hydroxy-8-[(1E)-3-hydroxybut-1-en-1-yl]-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-3-one

> <JCHEM_LOGP>
0.264419750666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.28862863234356

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.874247669918805

> <JCHEM_PKA_STRONGEST_BASIC>
-2.668372306052113

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
63.81620000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5S,8S)-8-hydroxy-8-[(1E)-3-hydroxybut-1-en-1-yl]-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       6.263  -3.608   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.744  -3.858   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.200  -5.299   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.767  -2.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.394  -1.004   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.602  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.410   0.903   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.170   1.730   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.660   3.260   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.966   0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.966  -0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.170  -1.730   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.515  -3.258   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.671  -1.388   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.339  -0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.997   0.198   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.671   1.387   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   12                                             
CONECT    7    6                                                            
CONECT    8    6    9   10   17                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    6   13   14                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    8                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₂₀O₄

Average Mass

240.2990 Da

Monoisotopic Mass

240.13616 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(O)\C=C\[C@]1(O)[C@]2(C)CO[C@@]1(C)CC(=O)C2

InChI Identifier

InChI=1S/C13H20O4/c1-9(14)4-5-13(16)11(2)6-10(15)7-12(13,3)17-8-11/h4-5,9,14,16H,6-8H2,1-3H3/b5-4+/t9?,11-,12-,13-/m0/s1

InChI Key

KENVUEOHDFOVNA-HQZIRTJDSA-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
Cucubalus baccifer	LOTUS Database	35616633
Sesbania drummondii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxepanes

Sub Class

Not Available

Direct Parent

Oxepanes

Alternative Parents

Substituents

Oxepane
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Ketone
Secondary alcohol
Cyclic ketone
Ether
Dialkyl ether
Oxacycle
Organic oxide
Organooxygen compound
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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

23326886

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44559359

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,5s,8s)-8-hydroxy-8-[(1e)-3-hydroxybut-1-en-1-yl]-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-3-one (NP0209870)

MOL for NP0209870 ((1s,5s,8s)-8-hydroxy-8-[(1e)-3-hydroxybut-1-en-1-yl]-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-3-one)

3D MOL for NP0209870 ((1s,5s,8s)-8-hydroxy-8-[(1e)-3-hydroxybut-1-en-1-yl]-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-3-one)

3D SDF for NP0209870 ((1s,5s,8s)-8-hydroxy-8-[(1e)-3-hydroxybut-1-en-1-yl]-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-3-one)

3D-SDF for NP0209870 ((1s,5s,8s)-8-hydroxy-8-[(1e)-3-hydroxybut-1-en-1-yl]-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-3-one)

PDB for NP0209870 ((1s,5s,8s)-8-hydroxy-8-[(1e)-3-hydroxybut-1-en-1-yl]-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-3-one)

3D PDB for NP0209870 ((1s,5s,8s)-8-hydroxy-8-[(1e)-3-hydroxybut-1-en-1-yl]-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-3-one)

SMILES for NP0209870 ((1s,5s,8s)-8-hydroxy-8-[(1e)-3-hydroxybut-1-en-1-yl]-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-3-one)

INCHI for NP0209870 ((1s,5s,8s)-8-hydroxy-8-[(1e)-3-hydroxybut-1-en-1-yl]-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-3-one)

Structure for NP0209870 ((1s,5s,8s)-8-hydroxy-8-[(1e)-3-hydroxybut-1-en-1-yl]-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-3-one)

3D Structure for NP0209870 ((1s,5s,8s)-8-hydroxy-8-[(1e)-3-hydroxybut-1-en-1-yl]-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-3-one)