NP-MRD: Showing NP-Card for 4-(acetyloxy)-8-hydroxy-12-(3-hydroxy-3-methylpent-4-en-1-yl)-5,5,9-trimethyl-10-oxatricyclo[7.2.1.0¹,⁶]dodecan-3-yl 2-methylbut-2-enoate (NP0249142)

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Record Information

Version

2.0

Created at

2022-09-07 11:37:01 UTC

Updated at

2022-09-07 11:37:01 UTC

NP-MRD ID

NP0249142

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-(acetyloxy)-8-hydroxy-12-(3-hydroxy-3-methylpent-4-en-1-yl)-5,5,9-trimethyl-10-oxatricyclo[7.2.1.0¹,⁶]dodecan-3-yl 2-methylbut-2-enoate

Description

4-(Acetyloxy)-8-hydroxy-12-(3-hydroxy-3-methylpent-4-en-1-yl)-5,5,9-trimethyl-10-oxatricyclo[7.2.1.0¹,⁶]Dodecan-3-yl 2-methylbut-2-enoate 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. 4-(acetyloxy)-8-hydroxy-12-(3-hydroxy-3-methylpent-4-en-1-yl)-5,5,9-trimethyl-10-oxatricyclo[7.2.1.0¹,⁶]dodecan-3-yl 2-methylbut-2-enoate is found in Waitzia acuminata. Based on a literature review very few articles have been published on 4-(acetyloxy)-8-hydroxy-12-(3-hydroxy-3-methylpent-4-en-1-yl)-5,5,9-trimethyl-10-oxatricyclo[7.2.1.0¹,⁶]Dodecan-3-yl 2-methylbut-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072213372D          

 34 36  0  0  0  0            999 V2000
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M  END

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M  END


  Mrv1652309072213372D          

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  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
  9 17  1  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
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 32 33  1  4  0  0  0
 26 34  1  0  0  0  0
  9 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0249142

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=C(C)C(=O)OC1CC23COC(C)(C2CCC(C)(O)C=C)C(O)CC3C(C)(C)C1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H42O7/c1-9-16(3)23(30)34-18-14-27-15-32-26(8,19(27)11-12-25(7,31)10-2)21(29)13-20(27)24(5,6)22(18)33-17(4)28/h9-10,18-22,29,31H,2,11-15H2,1,3-8H3

> <INCHI_KEY>
GCLQXUMZGLUCEL-UHFFFAOYSA-N

> <FORMULA>
C27H42O7

> <MOLECULAR_WEIGHT>
478.626

> <EXACT_MASS>
478.293053692

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
52.73004372225658

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-(acetyloxy)-8-hydroxy-12-(3-hydroxy-3-methylpent-4-en-1-yl)-5,5,9-trimethyl-10-oxatricyclo[7.2.1.0^{1,6}]dodecan-3-yl 2-methylbut-2-enoate

> <JCHEM_LOGP>
3.4912349686666655

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.254469111128635

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.982464367740846

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3746256591044315

> <JCHEM_POLAR_SURFACE_AREA>
102.29000000000002

> <JCHEM_REFRACTIVITY>
128.46729999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-(acetyloxy)-8-hydroxy-12-(3-hydroxy-3-methylpent-4-en-1-yl)-5,5,9-trimethyl-10-oxatricyclo[7.2.1.0^{1,6}]dodecan-3-yl 2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       3.145  -8.656   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.558  -7.172   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.480  -6.072   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.580  -4.994   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.381  -7.151   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.402  -4.973   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.883  -3.247   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.500  -1.722   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.617  -0.994   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.344   0.091   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.074  -0.698   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.234  -2.280   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.336  -2.670   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.922  -3.740   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.315  -4.769   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.523  -3.867   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.377  -2.465   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.948  -2.512   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.313  -3.446   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.596  -4.035   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.787  -1.206   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.422  -1.270   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.570  -0.201   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.226   1.300   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      10.043  -0.653   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.090   0.180   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.990   1.592   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.395   3.100   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.352   4.306   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.871   3.326   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.914   2.120   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.306   4.758   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.782   4.984   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.551   0.274   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10   17   34                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    8   13   14                                             
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16    9   18                                                  
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   21   27   34                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32                                                            
CONECT   34   26    9                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Value	Source
4-(Acetyloxy)-8-hydroxy-12-(3-hydroxy-3-methylpent-4-en-1-yl)-5,5,9-trimethyl-10-oxatricyclo[7.2.1.0,]dodecan-3-yl 2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₇H₄₂O₇

Average Mass

478.6260 Da

Monoisotopic Mass

478.29305 Da

IUPAC Name

4-(acetyloxy)-8-hydroxy-12-(3-hydroxy-3-methylpent-4-en-1-yl)-5,5,9-trimethyl-10-oxatricyclo[7.2.1.0^{1,6}]dodecan-3-yl 2-methylbut-2-enoate

Traditional Name

4-(acetyloxy)-8-hydroxy-12-(3-hydroxy-3-methylpent-4-en-1-yl)-5,5,9-trimethyl-10-oxatricyclo[7.2.1.0^{1,6}]dodecan-3-yl 2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

CC=C(C)C(=O)OC1CC23COC(C)(C2CCC(C)(O)C=C)C(O)CC3C(C)(C)C1OC(C)=O

InChI Identifier

InChI=1S/C27H42O7/c1-9-16(3)23(30)34-18-14-27-15-32-26(8,19(27)11-12-25(7,31)10-2)21(29)13-20(27)24(5,6)22(18)33-17(4)28/h9-10,18-22,29,31H,2,11-15H2,1,3-8H3

InChI Key

GCLQXUMZGLUCEL-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
Waitzia acuminata	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

Fatty acid ester
Oxepane
Dicarboxylic acid or derivatives
Fatty acyl
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Ether
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
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
logP	3.49	ChemAxon
pKa (Strongest Acidic)	13.98	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	102.29 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	128.47 m³·mol⁻¹	ChemAxon
Polarizability	52.73 Å³	ChemAxon
Number of Rings	3	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

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

163034485

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-(acetyloxy)-8-hydroxy-12-(3-hydroxy-3-methylpent-4-en-1-yl)-5,5,9-trimethyl-10-oxatricyclo[7.2.1.0¹,⁶]dodecan-3-yl 2-methylbut-2-enoate (NP0249142)

MOL for NP0249142 (4-(acetyloxy)-8-hydroxy-12-(3-hydroxy-3-methylpent-4-en-1-yl)-5,5,9-trimethyl-10-oxatricyclo[7.2.1.0¹,⁶]dodecan-3-yl 2-methylbut-2-enoate)

3D MOL for NP0249142 (4-(acetyloxy)-8-hydroxy-12-(3-hydroxy-3-methylpent-4-en-1-yl)-5,5,9-trimethyl-10-oxatricyclo[7.2.1.0¹,⁶]dodecan-3-yl 2-methylbut-2-enoate)

3D SDF for NP0249142 (4-(acetyloxy)-8-hydroxy-12-(3-hydroxy-3-methylpent-4-en-1-yl)-5,5,9-trimethyl-10-oxatricyclo[7.2.1.0¹,⁶]dodecan-3-yl 2-methylbut-2-enoate)

3D-SDF for NP0249142 (4-(acetyloxy)-8-hydroxy-12-(3-hydroxy-3-methylpent-4-en-1-yl)-5,5,9-trimethyl-10-oxatricyclo[7.2.1.0¹,⁶]dodecan-3-yl 2-methylbut-2-enoate)

PDB for NP0249142 (4-(acetyloxy)-8-hydroxy-12-(3-hydroxy-3-methylpent-4-en-1-yl)-5,5,9-trimethyl-10-oxatricyclo[7.2.1.0¹,⁶]dodecan-3-yl 2-methylbut-2-enoate)

3D PDB for NP0249142 (4-(acetyloxy)-8-hydroxy-12-(3-hydroxy-3-methylpent-4-en-1-yl)-5,5,9-trimethyl-10-oxatricyclo[7.2.1.0¹,⁶]dodecan-3-yl 2-methylbut-2-enoate)

SMILES for NP0249142 (4-(acetyloxy)-8-hydroxy-12-(3-hydroxy-3-methylpent-4-en-1-yl)-5,5,9-trimethyl-10-oxatricyclo[7.2.1.0¹,⁶]dodecan-3-yl 2-methylbut-2-enoate)

INCHI for NP0249142 (4-(acetyloxy)-8-hydroxy-12-(3-hydroxy-3-methylpent-4-en-1-yl)-5,5,9-trimethyl-10-oxatricyclo[7.2.1.0¹,⁶]dodecan-3-yl 2-methylbut-2-enoate)

Structure for NP0249142 (4-(acetyloxy)-8-hydroxy-12-(3-hydroxy-3-methylpent-4-en-1-yl)-5,5,9-trimethyl-10-oxatricyclo[7.2.1.0¹,⁶]dodecan-3-yl 2-methylbut-2-enoate)

3D Structure for NP0249142 (4-(acetyloxy)-8-hydroxy-12-(3-hydroxy-3-methylpent-4-en-1-yl)-5,5,9-trimethyl-10-oxatricyclo[7.2.1.0¹,⁶]dodecan-3-yl 2-methylbut-2-enoate)