NP-MRD: Showing NP-Card for [(1r,6r,7s,8r,10r,11r)-8-hydroxy-3,6,7-trimethyl-4-oxo-12,13-dioxatetracyclo[8.2.1.0¹,⁶.0⁷,¹¹]tridec-2-en-11-yl]methyl acetate (NP0220618)

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Record Information

Version

2.0

Created at

2022-09-05 21:59:14 UTC

Updated at

2022-09-05 21:59:14 UTC

NP-MRD ID

NP0220618

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1r,6r,7s,8r,10r,11r)-8-hydroxy-3,6,7-trimethyl-4-oxo-12,13-dioxatetracyclo[8.2.1.0¹,⁶.0⁷,¹¹]tridec-2-en-11-yl]methyl acetate

Description

13-Acetoxyloukacinol A 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. [(1r,6r,7s,8r,10r,11r)-8-hydroxy-3,6,7-trimethyl-4-oxo-12,13-dioxatetracyclo[8.2.1.0¹,⁶.0⁷,¹¹]tridec-2-en-11-yl]methyl acetate is found in Holarrhena floribunda. Based on a literature review very few articles have been published on 13-Acetoxyloukacinol A.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052223592D          

 23 26  0  0  1  0            999 V2000
   -1.3581    0.0258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4733    0.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0548   -0.5410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1333    1.0752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9697    1.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6645    1.1537    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0469    0.3983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7116    0.9130    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0936    0.6820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7361    1.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6050    1.2904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6069    2.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2931    2.5821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1549    2.3477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7752    1.8009    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7274    2.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5859    1.9418    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8778    2.8154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4034    2.1847    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1275    2.6612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8297    1.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2705    0.7558    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5642    0.2052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
  6 22  1  0  0  0  0
 22 23  1  1  0  0  0
  8 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0220618

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@@]12O[C@@]34O[C@@H]1C[C@@H](O)[C@]2(C)[C@@]3(C)CC(=O)C(C)=C4

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O6/c1-9-6-17-14(3,7-11(9)19)15(4)12(20)5-13(22-17)16(15,23-17)8-21-10(2)18/h6,12-13,20H,5,7-8H2,1-4H3/t12-,13-,14-,15-,16-,17-/m1/s1

> <INCHI_KEY>
RKLCSLYSBLMPLN-HDKMNVHJSA-N

> <FORMULA>
C17H22O6

> <MOLECULAR_WEIGHT>
322.357

> <EXACT_MASS>
322.141638428

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
33.16314980142404

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1R,6R,7S,8R,10R,11R)-8-hydroxy-3,6,7-trimethyl-4-oxo-12,13-dioxatetracyclo[8.2.1.0^{1,6}.0^{7,11}]tridec-2-en-11-yl]methyl acetate

> <JCHEM_LOGP>
1.0499726296666658

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.397337844266747

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.484817494583694

> <JCHEM_PKA_STRONGEST_BASIC>
-3.018491443257658

> <JCHEM_POLAR_SURFACE_AREA>
82.06

> <JCHEM_REFRACTIVITY>
79.23689999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,6R,7S,8R,10R,11R)-8-hydroxy-3,6,7-trimethyl-4-oxo-12,13-dioxatetracyclo[8.2.1.0^{1,6}.0^{7,11}]tridec-2-en-11-yl]methyl acetate

> <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      -2.535   0.048   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.884   0.616   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.102  -1.010   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.249   2.007   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.810   2.565   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.107   2.154   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.954   0.743   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.328   1.704   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.175   1.273   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.374   2.256   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.996   2.409   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.133   3.795   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.414   4.820   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.289   4.382   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.447   3.362   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.358   5.211   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.960   3.625   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.505   5.255   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.486   4.078   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.838   4.968   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.282   2.710   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.238   1.411   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.920   0.383   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   17   22                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   15   23                                             
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    8   16   17                                             
CONECT   16   15                                                            
CONECT   17   15    6   18   19                                             
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21    6   23                                                  
CONECT   23   22    8                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₂O₆

Average Mass

322.3570 Da

Monoisotopic Mass

322.14164 Da

IUPAC Name

[(1R,6R,7S,8R,10R,11R)-8-hydroxy-3,6,7-trimethyl-4-oxo-12,13-dioxatetracyclo[8.2.1.0^{1,6}.0^{7,11}]tridec-2-en-11-yl]methyl acetate

Traditional Name

[(1R,6R,7S,8R,10R,11R)-8-hydroxy-3,6,7-trimethyl-4-oxo-12,13-dioxatetracyclo[8.2.1.0^{1,6}.0^{7,11}]tridec-2-en-11-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@@]12O[C@@]34O[C@@H]1C[C@@H](O)[C@]2(C)[C@@]3(C)CC(=O)C(C)=C4

InChI Identifier

InChI=1S/C17H22O6/c1-9-6-17-14(3,7-11(9)19)15(4)12(20)5-13(22-17)16(15,23-17)8-21-10(2)18/h6,12-13,20H,5,7-8H2,1-4H3/t12-,13-,14-,15-,16-,17-/m1/s1

InChI Key

RKLCSLYSBLMPLN-HDKMNVHJSA-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
Holarrhena floribunda	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

Ketal
Cyclohexenone
Oxepane
Oxane
Meta-dioxolane
Cyclic alcohol
Tetrahydrofuran
Carboxylic acid ester
Ketone
Cyclic ketone
Secondary alcohol
Acetal
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organooxygen compound
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
logP	1.05	ChemAxon
pKa (Strongest Acidic)	14.48	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	79.24 m³·mol⁻¹	ChemAxon
Polarizability	33.16 Å³	ChemAxon
Number of Rings	4	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10269560

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10567834

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(1r,6r,7s,8r,10r,11r)-8-hydroxy-3,6,7-trimethyl-4-oxo-12,13-dioxatetracyclo[8.2.1.0¹,⁶.0⁷,¹¹]tridec-2-en-11-yl]methyl acetate (NP0220618)

MOL for NP0220618 ([(1r,6r,7s,8r,10r,11r)-8-hydroxy-3,6,7-trimethyl-4-oxo-12,13-dioxatetracyclo[8.2.1.0¹,⁶.0⁷,¹¹]tridec-2-en-11-yl]methyl acetate)

3D MOL for NP0220618 ([(1r,6r,7s,8r,10r,11r)-8-hydroxy-3,6,7-trimethyl-4-oxo-12,13-dioxatetracyclo[8.2.1.0¹,⁶.0⁷,¹¹]tridec-2-en-11-yl]methyl acetate)

3D SDF for NP0220618 ([(1r,6r,7s,8r,10r,11r)-8-hydroxy-3,6,7-trimethyl-4-oxo-12,13-dioxatetracyclo[8.2.1.0¹,⁶.0⁷,¹¹]tridec-2-en-11-yl]methyl acetate)

3D-SDF for NP0220618 ([(1r,6r,7s,8r,10r,11r)-8-hydroxy-3,6,7-trimethyl-4-oxo-12,13-dioxatetracyclo[8.2.1.0¹,⁶.0⁷,¹¹]tridec-2-en-11-yl]methyl acetate)

PDB for NP0220618 ([(1r,6r,7s,8r,10r,11r)-8-hydroxy-3,6,7-trimethyl-4-oxo-12,13-dioxatetracyclo[8.2.1.0¹,⁶.0⁷,¹¹]tridec-2-en-11-yl]methyl acetate)

3D PDB for NP0220618 ([(1r,6r,7s,8r,10r,11r)-8-hydroxy-3,6,7-trimethyl-4-oxo-12,13-dioxatetracyclo[8.2.1.0¹,⁶.0⁷,¹¹]tridec-2-en-11-yl]methyl acetate)

SMILES for NP0220618 ([(1r,6r,7s,8r,10r,11r)-8-hydroxy-3,6,7-trimethyl-4-oxo-12,13-dioxatetracyclo[8.2.1.0¹,⁶.0⁷,¹¹]tridec-2-en-11-yl]methyl acetate)

INCHI for NP0220618 ([(1r,6r,7s,8r,10r,11r)-8-hydroxy-3,6,7-trimethyl-4-oxo-12,13-dioxatetracyclo[8.2.1.0¹,⁶.0⁷,¹¹]tridec-2-en-11-yl]methyl acetate)

Structure for NP0220618 ([(1r,6r,7s,8r,10r,11r)-8-hydroxy-3,6,7-trimethyl-4-oxo-12,13-dioxatetracyclo[8.2.1.0¹,⁶.0⁷,¹¹]tridec-2-en-11-yl]methyl acetate)

3D Structure for NP0220618 ([(1r,6r,7s,8r,10r,11r)-8-hydroxy-3,6,7-trimethyl-4-oxo-12,13-dioxatetracyclo[8.2.1.0¹,⁶.0⁷,¹¹]tridec-2-en-11-yl]methyl acetate)