NP-MRD: Showing NP-Card for 2,9-bis(acetyloxy)-4,5-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadeca-6,12-dien-11-yl butanoate (NP0199359)

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Record Information

Version

2.0

Created at

2022-09-04 17:59:28 UTC

Updated at

2022-09-04 17:59:29 UTC

NP-MRD ID

NP0199359

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,9-bis(acetyloxy)-4,5-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadeca-6,12-dien-11-yl butanoate

Description

2,9-Bis(acetyloxy)-4,5-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]Octadeca-6,12-dien-11-yl butanoate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 2,9-bis(acetyloxy)-4,5-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadeca-6,12-dien-11-yl butanoate is found in Briareum excavatum. Based on a literature review very few articles have been published on 2,9-bis(acetyloxy)-4,5-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]Octadeca-6,12-dien-11-yl butanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042219592D          

 39 42  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309042219592D          

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    3.9802   -0.0176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7834   -0.8188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1879   -0.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5578   -0.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7242    0.4345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8996    0.4604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2298    1.0864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0061    0.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7331    1.1969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4343    0.7622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4084   -0.0624    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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  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
 11 13  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 29 36  1  0  0  0  0
 37 36  1  4  0  0  0
 37 38  2  0  0  0  0
  7 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0199359

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(=O)OC1CC(OC(C)=O)C2(C)C=CC(O)C(C)(O)C2C(OC(C)=O)C23OC2(C)C(=O)OC3C=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C28H38O11/c1-8-9-21(32)37-17-13-19(35-15(3)29)25(5)11-10-18(31)26(6,34)22(25)23(36-16(4)30)28-20(12-14(17)2)38-24(33)27(28,7)39-28/h10-12,17-20,22-23,31,34H,8-9,13H2,1-7H3

> <INCHI_KEY>
HAQVZQHBSNIEQX-UHFFFAOYSA-N

> <FORMULA>
C28H38O11

> <MOLECULAR_WEIGHT>
550.601

> <EXACT_MASS>
550.241412044

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
55.49597346718174

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,9-bis(acetyloxy)-4,5-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0^{1,17}.0^{3,8}]octadeca-6,12-dien-11-yl butanoate

> <JCHEM_LOGP>
1.0950670023333338

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.740602467493652

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.338284405476664

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3865352383166147

> <JCHEM_POLAR_SURFACE_AREA>
158.19

> <JCHEM_REFRACTIVITY>
134.46779999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2,9-bis(acetyloxy)-4,5-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0^{1,17}.0^{3,8}]octadeca-6,12-dien-11-yl butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      16.882   3.522   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.573   4.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.216   3.606   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.907   4.418   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      12.835   5.956   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      11.073   3.242   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      11.025   1.703   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.363   1.815   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.314   0.276   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      14.071  -1.012   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      14.022  -2.551   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.331  -3.362   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      12.665  -3.279   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      11.405  -0.928   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.047  -1.656   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.762  -0.200   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.810   1.339   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.501   2.150   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.550   3.690   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.697   1.899   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.663   2.886   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.620   1.203   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.648   0.360   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.739  -0.844   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.690  -2.384   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.333  -3.111   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.285  -4.651   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.024  -2.300   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       7.430  -0.033   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       7.062  -1.528   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.951  -0.463   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.775  -1.457   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.085   0.811   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.546   0.859   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       6.029   2.028   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       7.478   1.506   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.835   2.234   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      10.144   1.423   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      10.096  -0.117   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   38                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9   15   16   23                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   14   24                                                  
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   24   30   31   36                                             
CONECT   30   29   31                                                       
CONECT   31   30   29   32   33                                             
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   29   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37    7   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Value	Source
2,9-Bis(acetyloxy)-4,5-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0,.0,]octadeca-6,12-dien-11-yl butanoic acid	Generator

Chemical Formula

C₂₈H₃₈O₁₁

Average Mass

550.6010 Da

Monoisotopic Mass

550.24141 Da

IUPAC Name

2,9-bis(acetyloxy)-4,5-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0^{1,17}.0^{3,8}]octadeca-6,12-dien-11-yl butanoate

Traditional Name

2,9-bis(acetyloxy)-4,5-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0^{1,17}.0^{3,8}]octadeca-6,12-dien-11-yl butanoate

CAS Registry Number

Not Available

SMILES

CCCC(=O)OC1CC(OC(C)=O)C2(C)C=CC(O)C(C)(O)C2C(OC(C)=O)C23OC2(C)C(=O)OC3C=C1C

InChI Identifier

InChI=1S/C28H38O11/c1-8-9-21(32)37-17-13-19(35-15(3)29)25(5)11-10-18(31)26(6,34)22(25)23(36-16(4)30)28-20(12-14(17)2)38-24(33)27(28,7)39-28/h10-12,17-20,22-23,31,34H,8-9,13H2,1-7H3

InChI Key

HAQVZQHBSNIEQX-UHFFFAOYSA-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
Briareum excavatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Briarane diterpenoid
Tetracarboxylic acid or derivatives
Fatty acid ester
Para-dioxane
Fatty acyl
Gamma butyrolactone
Tertiary alcohol
Tetrahydrofuran
Secondary alcohol
1,2-diol
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Ether
Oxirane
Carboxylic acid derivative
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
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	1.1	ChemAxon
pKa (Strongest Acidic)	13.34	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	158.19 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	134.47 m³·mol⁻¹	ChemAxon
Polarizability	55.5 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

74964568

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,9-bis(acetyloxy)-4,5-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadeca-6,12-dien-11-yl butanoate (NP0199359)

MOL for NP0199359 (2,9-bis(acetyloxy)-4,5-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadeca-6,12-dien-11-yl butanoate)

3D MOL for NP0199359 (2,9-bis(acetyloxy)-4,5-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadeca-6,12-dien-11-yl butanoate)

3D SDF for NP0199359 (2,9-bis(acetyloxy)-4,5-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadeca-6,12-dien-11-yl butanoate)

3D-SDF for NP0199359 (2,9-bis(acetyloxy)-4,5-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadeca-6,12-dien-11-yl butanoate)

PDB for NP0199359 (2,9-bis(acetyloxy)-4,5-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadeca-6,12-dien-11-yl butanoate)

3D PDB for NP0199359 (2,9-bis(acetyloxy)-4,5-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadeca-6,12-dien-11-yl butanoate)

SMILES for NP0199359 (2,9-bis(acetyloxy)-4,5-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadeca-6,12-dien-11-yl butanoate)

INCHI for NP0199359 (2,9-bis(acetyloxy)-4,5-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadeca-6,12-dien-11-yl butanoate)

Structure for NP0199359 (2,9-bis(acetyloxy)-4,5-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadeca-6,12-dien-11-yl butanoate)

3D Structure for NP0199359 (2,9-bis(acetyloxy)-4,5-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadeca-6,12-dien-11-yl butanoate)