NP-MRD: Showing NP-Card for 2-(acetyloxy)-7-formyl-11-hydroxy-11-methyl-16-oxo-4-(prop-1-en-2-yl)-15,17,18-trioxatetracyclo[11.2.2.1⁶,⁹.0¹,¹⁴]octadeca-6,8-dien-10-yl acetate (NP0207479)

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Record Information

Version

2.0

Created at

2022-09-05 04:06:39 UTC

Updated at

2022-09-05 04:06:39 UTC

NP-MRD ID

NP0207479

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(acetyloxy)-7-formyl-11-hydroxy-11-methyl-16-oxo-4-(prop-1-en-2-yl)-15,17,18-trioxatetracyclo[11.2.2.1⁶,⁹.0¹,¹⁴]octadeca-6,8-dien-10-yl acetate

Description

2-(Acetyloxy)-7-formyl-11-hydroxy-11-methyl-16-oxo-4-(prop-1-en-2-yl)-15,17,18-trioxatetracyclo[11.2.2.1⁶,⁹.0¹,¹⁴]Octadeca-6,8-dien-10-yl acetate belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. 2-(acetyloxy)-7-formyl-11-hydroxy-11-methyl-16-oxo-4-(prop-1-en-2-yl)-15,17,18-trioxatetracyclo[11.2.2.1⁶,⁹.0¹,¹⁴]octadeca-6,8-dien-10-yl acetate is found in Leptogorgia violacea. Based on a literature review very few articles have been published on 2-(acetyloxy)-7-formyl-11-hydroxy-11-methyl-16-oxo-4-(prop-1-en-2-yl)-15,17,18-trioxatetracyclo[11.2.2.1⁶,⁹.0¹,¹⁴]Octadeca-6,8-dien-10-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052206062D          

 34 37  0  0  0  0            999 V2000
    4.7363    2.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0668    1.4868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8694    1.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4360    1.0779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2155    0.2024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5690   -0.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

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M  END


  Mrv1652309052206062D          

 34 37  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0207479

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CC(CC2=C(C=O)C=C(O2)C(OC(C)=O)C(C)(O)CC2OC(=O)C11OC21)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C24H28O10/c1-11(2)14-6-16-15(10-25)7-17(32-16)20(31-13(4)27)23(5,29)9-18-21-24(34-21,22(28)33-18)19(8-14)30-12(3)26/h7,10,14,18-21,29H,1,6,8-9H2,2-5H3

> <INCHI_KEY>
OUHXJMJQHKDXIW-UHFFFAOYSA-N

> <FORMULA>
C24H28O10

> <MOLECULAR_WEIGHT>
476.478

> <EXACT_MASS>
476.168247102

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
46.81547080185874

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(acetyloxy)-7-formyl-11-hydroxy-11-methyl-16-oxo-4-(prop-1-en-2-yl)-15,17,18-trioxatetracyclo[11.2.2.1^{6,9}.0^{1,14}]octadeca-6,8-dien-10-yl acetate

> <JCHEM_LOGP>
1.0059103263333329

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.651891808919586

> <JCHEM_PKA_STRONGEST_BASIC>
-2.994304671435605

> <JCHEM_POLAR_SURFACE_AREA>
141.87

> <JCHEM_REFRACTIVITY>
114.27899999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-(acetyloxy)-7-formyl-11-hydroxy-11-methyl-16-oxo-4-(prop-1-en-2-yl)-15,17,18-trioxatetracyclo[11.2.2.1^{6,9}.0^{1,14}]octadeca-6,8-dien-10-yl 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       8.841   5.370   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.899   4.251   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.397   4.607   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.458   2.775   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.956   3.131   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.014   2.012   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      11.602   0.378   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      12.262  -1.014   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.638   0.123   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.512   1.658   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.680   2.662   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      14.394   4.175   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      11.143  -2.071   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      11.340  -3.598   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      12.762  -4.191   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.959  -5.718   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      13.986  -3.256   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       9.791  -1.333   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.178  -2.824   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.968  -2.635   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.136  -1.652   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.078  -0.532   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.544  -0.408   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.187   1.090   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.737   1.608   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.462   2.063   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.021   0.587   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.519   0.943   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.902   3.539   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.845   4.658   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.285   6.134   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.228   7.253   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.783   6.490   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       8.400   3.895   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   34                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9    6   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    8   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22                                                       
CONECT   22   21   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28   29                                             
CONECT   27   26   28                                                       
CONECT   28   27   22   26                                                  
CONECT   29   26   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   29    4                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
2-(Acetyloxy)-7-formyl-11-hydroxy-11-methyl-16-oxo-4-(prop-1-en-2-yl)-15,17,18-trioxatetracyclo[11.2.2.1,.0,]octadeca-6,8-dien-10-yl acetic acid	Generator

Chemical Formula

C₂₄H₂₈O₁₀

Average Mass

476.4780 Da

Monoisotopic Mass

476.16825 Da

IUPAC Name

2-(acetyloxy)-7-formyl-11-hydroxy-11-methyl-16-oxo-4-(prop-1-en-2-yl)-15,17,18-trioxatetracyclo[11.2.2.1^{6,9}.0^{1,14}]octadeca-6,8-dien-10-yl acetate

Traditional Name

2-(acetyloxy)-7-formyl-11-hydroxy-11-methyl-16-oxo-4-(prop-1-en-2-yl)-15,17,18-trioxatetracyclo[11.2.2.1^{6,9}.0^{1,14}]octadeca-6,8-dien-10-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CC(CC2=C(C=O)C=C(O2)C(OC(C)=O)C(C)(O)CC2OC(=O)C11OC21)C(C)=C

InChI Identifier

InChI=1S/C24H28O10/c1-11(2)14-6-16-15(10-25)7-17(32-16)20(31-13(4)27)23(5,29)9-18-21-24(34-21,22(28)33-18)19(8-14)30-12(3)26/h7,10,14,18-21,29H,1,6,8-9H2,2-5H3

InChI Key

OUHXJMJQHKDXIW-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
Leptogorgia violacea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Tricarboxylic acid or derivatives
Aryl-aldehyde
Para-dioxane
Gamma butyrolactone
Furan
Heteroaromatic compound
Tertiary alcohol
Tetrahydrofuran
Carboxylic acid ester
Lactone
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aldehyde
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	1.01	ChemAxon
pKa (Strongest Acidic)	13.65	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	141.87 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	114.28 m³·mol⁻¹	ChemAxon
Polarizability	46.82 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	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

73837026

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(acetyloxy)-7-formyl-11-hydroxy-11-methyl-16-oxo-4-(prop-1-en-2-yl)-15,17,18-trioxatetracyclo[11.2.2.1⁶,⁹.0¹,¹⁴]octadeca-6,8-dien-10-yl acetate (NP0207479)

MOL for NP0207479 (2-(acetyloxy)-7-formyl-11-hydroxy-11-methyl-16-oxo-4-(prop-1-en-2-yl)-15,17,18-trioxatetracyclo[11.2.2.1⁶,⁹.0¹,¹⁴]octadeca-6,8-dien-10-yl acetate)

3D MOL for NP0207479 (2-(acetyloxy)-7-formyl-11-hydroxy-11-methyl-16-oxo-4-(prop-1-en-2-yl)-15,17,18-trioxatetracyclo[11.2.2.1⁶,⁹.0¹,¹⁴]octadeca-6,8-dien-10-yl acetate)

3D SDF for NP0207479 (2-(acetyloxy)-7-formyl-11-hydroxy-11-methyl-16-oxo-4-(prop-1-en-2-yl)-15,17,18-trioxatetracyclo[11.2.2.1⁶,⁹.0¹,¹⁴]octadeca-6,8-dien-10-yl acetate)

3D-SDF for NP0207479 (2-(acetyloxy)-7-formyl-11-hydroxy-11-methyl-16-oxo-4-(prop-1-en-2-yl)-15,17,18-trioxatetracyclo[11.2.2.1⁶,⁹.0¹,¹⁴]octadeca-6,8-dien-10-yl acetate)

PDB for NP0207479 (2-(acetyloxy)-7-formyl-11-hydroxy-11-methyl-16-oxo-4-(prop-1-en-2-yl)-15,17,18-trioxatetracyclo[11.2.2.1⁶,⁹.0¹,¹⁴]octadeca-6,8-dien-10-yl acetate)

3D PDB for NP0207479 (2-(acetyloxy)-7-formyl-11-hydroxy-11-methyl-16-oxo-4-(prop-1-en-2-yl)-15,17,18-trioxatetracyclo[11.2.2.1⁶,⁹.0¹,¹⁴]octadeca-6,8-dien-10-yl acetate)

SMILES for NP0207479 (2-(acetyloxy)-7-formyl-11-hydroxy-11-methyl-16-oxo-4-(prop-1-en-2-yl)-15,17,18-trioxatetracyclo[11.2.2.1⁶,⁹.0¹,¹⁴]octadeca-6,8-dien-10-yl acetate)

INCHI for NP0207479 (2-(acetyloxy)-7-formyl-11-hydroxy-11-methyl-16-oxo-4-(prop-1-en-2-yl)-15,17,18-trioxatetracyclo[11.2.2.1⁶,⁹.0¹,¹⁴]octadeca-6,8-dien-10-yl acetate)

Structure for NP0207479 (2-(acetyloxy)-7-formyl-11-hydroxy-11-methyl-16-oxo-4-(prop-1-en-2-yl)-15,17,18-trioxatetracyclo[11.2.2.1⁶,⁹.0¹,¹⁴]octadeca-6,8-dien-10-yl acetate)

3D Structure for NP0207479 (2-(acetyloxy)-7-formyl-11-hydroxy-11-methyl-16-oxo-4-(prop-1-en-2-yl)-15,17,18-trioxatetracyclo[11.2.2.1⁶,⁹.0¹,¹⁴]octadeca-6,8-dien-10-yl acetate)