NP-MRD: Showing NP-Card for (1s,2s,5s,6s,7r,8s,9s,12r)-5,8-bis(acetyloxy)-2,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate (NP0209382)

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Record Information

Version

2.0

Created at

2022-09-05 06:46:14 UTC

Updated at

2022-09-05 06:46:14 UTC

NP-MRD ID

NP0209382

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,5s,6s,7r,8s,9s,12r)-5,8-bis(acetyloxy)-2,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate

Description

Reissantin E belongs to the class of organic compounds known as agarofurans. These are organic compounds containing an agarofuran moiety( a three-ring system, with core fragment oxatricyclo[7.2.1.0^{1,6}]Dodec-2-ene). (1s,2s,5s,6s,7r,8s,9s,12r)-5,8-bis(acetyloxy)-2,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate is found in Reissantia buchananii. Based on a literature review very few articles have been published on reissantin E.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052208462D          

 35 38  0  0  1  0            999 V2000
   -1.7714   -0.3502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3884   -1.0810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8298   -1.7780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5641   -1.1147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1227   -0.4177    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5293    0.3486    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1300    0.6872    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5457   -0.0254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7353    1.0853    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0278    1.6403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7226    1.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309052208462D          

 35 38  0  0  1  0            999 V2000
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 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 30 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0209382

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1CC[C@](C)(O)[C@@]23OC(C)(C)[C@@H]([C@H]2O)[C@H](OC(C)=O)[C@H](OC(=O)C2=CC=CC=C2)[C@]13C

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O9/c1-14(27)32-17-12-13-24(5,31)26-20(29)18(23(3,4)35-26)19(33-15(2)28)21(25(17,26)6)34-22(30)16-10-8-7-9-11-16/h7-11,17-21,29,31H,12-13H2,1-6H3/t17-,18+,19-,20+,21-,24-,25-,26-/m0/s1

> <INCHI_KEY>
VDMRSWTYKXKIDN-SWHFUDTGSA-N

> <FORMULA>
C26H34O9

> <MOLECULAR_WEIGHT>
490.549

> <EXACT_MASS>
490.220282675

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
49.948288009743386

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,5S,6S,7R,8S,9S,12R)-5,8-bis(acetyloxy)-2,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-7-yl benzoate

> <JCHEM_LOGP>
1.8691887006666674

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.044042800266578

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.305487771057887

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3408320558867644

> <JCHEM_POLAR_SURFACE_AREA>
128.59000000000003

> <JCHEM_REFRACTIVITY>
121.47250000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5S,6S,7R,8S,9S,12R)-5,8-bis(acetyloxy)-2,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-7-yl benzoate

> <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      -3.307  -0.654   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.592  -2.018   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.416  -3.319   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -1.053  -2.081   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.229  -0.780   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.988   0.651   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.243   1.283   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.019  -0.047   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.372   2.026   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.052   3.062   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.349   2.226   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.286   3.448   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.880   2.057   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.387   3.253   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.029   3.979   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.829   4.728   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.937   3.110   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.579   1.702   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.694   0.434   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.345  -0.961   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.879  -1.095   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.531  -2.490   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.762   0.167   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.143   0.571   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.870  -0.787   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.366  -0.853   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.121  -2.195   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.336  -3.520   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.204  -3.503   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.092  -4.862   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.632  -4.879   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.387  -6.221   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.602  -7.547   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.062  -7.530   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.307  -6.188   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   26                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   14   24                                             
CONECT   10    9   11                                                       
CONECT   11   10    6   12   13                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   19    9   25   26                                             
CONECT   25   24                                                            
CONECT   26   24    5   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   30                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₄O₉

Average Mass

490.5490 Da

Monoisotopic Mass

490.22028 Da

IUPAC Name

(1S,2S,5S,6S,7R,8S,9S,12R)-5,8-bis(acetyloxy)-2,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-7-yl benzoate

Traditional Name

(1S,2S,5S,6S,7R,8S,9S,12R)-5,8-bis(acetyloxy)-2,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-7-yl benzoate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1CC[C@](C)(O)[C@@]23OC(C)(C)[C@@H]([C@H]2O)[C@H](OC(C)=O)[C@H](OC(=O)C2=CC=CC=C2)[C@]13C

InChI Identifier

InChI=1S/C26H34O9/c1-14(27)32-17-12-13-24(5,31)26-20(29)18(23(3,4)35-26)19(33-15(2)28)21(25(17,26)6)34-22(30)16-10-8-7-9-11-16/h7-11,17-21,29,31H,12-13H2,1-6H3/t17-,18+,19-,20+,21-,24-,25-,26-/m0/s1

InChI Key

VDMRSWTYKXKIDN-SWHFUDTGSA-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
Reissantia buchananii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as agarofurans. These are organic compounds containing an agarofuran moiety( a three-ring system, with core fragment oxatricyclo[7.2.1.0^{1,6}]Dodec-2-ene).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Agarofurans

Alternative Parents

Substituents

Agarofuran
Benzoate ester
Benzoic acid or derivatives
Tricarboxylic acid or derivatives
Benzoyl
Oxepane
Benzenoid
Monocyclic benzene moiety
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Dialkyl ether
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Ether
Alcohol
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	1.87	ChemAxon
pKa (Strongest Acidic)	13.31	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	128.59 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	121.47 m³·mol⁻¹	ChemAxon
Polarizability	49.95 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00045042

Chemspider ID

8498745

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10323282

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s,5s,6s,7r,8s,9s,12r)-5,8-bis(acetyloxy)-2,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate (NP0209382)

MOL for NP0209382 ((1s,2s,5s,6s,7r,8s,9s,12r)-5,8-bis(acetyloxy)-2,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate)

3D MOL for NP0209382 ((1s,2s,5s,6s,7r,8s,9s,12r)-5,8-bis(acetyloxy)-2,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate)

3D SDF for NP0209382 ((1s,2s,5s,6s,7r,8s,9s,12r)-5,8-bis(acetyloxy)-2,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate)

3D-SDF for NP0209382 ((1s,2s,5s,6s,7r,8s,9s,12r)-5,8-bis(acetyloxy)-2,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate)

PDB for NP0209382 ((1s,2s,5s,6s,7r,8s,9s,12r)-5,8-bis(acetyloxy)-2,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate)

3D PDB for NP0209382 ((1s,2s,5s,6s,7r,8s,9s,12r)-5,8-bis(acetyloxy)-2,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate)

SMILES for NP0209382 ((1s,2s,5s,6s,7r,8s,9s,12r)-5,8-bis(acetyloxy)-2,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate)

INCHI for NP0209382 ((1s,2s,5s,6s,7r,8s,9s,12r)-5,8-bis(acetyloxy)-2,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate)

Structure for NP0209382 ((1s,2s,5s,6s,7r,8s,9s,12r)-5,8-bis(acetyloxy)-2,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate)

3D Structure for NP0209382 ((1s,2s,5s,6s,7r,8s,9s,12r)-5,8-bis(acetyloxy)-2,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate)