NP-MRD: Showing NP-Card for 12-(acetyloxy)-1,9-dihydroxy-6-isopropyl-3,9-dimethyl-13-methylidene-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl butanoate (NP0153006)

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Record Information

Version

2.0

Created at

2022-09-02 09:35:38 UTC

Updated at

2022-09-02 09:35:38 UTC

NP-MRD ID

NP0153006

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-(acetyloxy)-1,9-dihydroxy-6-isopropyl-3,9-dimethyl-13-methylidene-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl butanoate

Description

12-(Acetyloxy)-1,9-dihydroxy-3,9-dimethyl-13-methylidene-6-(propan-2-yl)-15-oxatricyclo[6.6.1.0²,⁷]Pentadecan-3-yl butanoate belongs to the class of organic compounds known as eunicellane and asbestinane diterpenoids. These are diterpenoids with a structure based on either the eunicellane (5,14-cyclocembrane) or the asbestinane skeleton. 12-(acetyloxy)-1,9-dihydroxy-6-isopropyl-3,9-dimethyl-13-methylidene-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl butanoate is found in Cladiella australis. 12-(Acetyloxy)-1,9-dihydroxy-3,9-dimethyl-13-methylidene-6-(propan-2-yl)-15-oxatricyclo[6.6.1.0²,⁷]Pentadecan-3-yl butanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161521302D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004161521302D          

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 25 26  1  0  0  0  0
 16 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 18 33  1  0  0  0  0
  7 33  1  0  0  0  0
 15 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0153006

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(=O)OC1(C)CCC(C(C)C)C2C3OC(O)(CC(=C)C(CCC3(C)O)OC(C)=O)C12

> <INCHI_IDENTIFIER>
InChI=1S/C26H42O7/c1-8-9-20(28)32-25(7)13-10-18(15(2)3)21-22(25)26(30)14-16(4)19(31-17(5)27)11-12-24(6,29)23(21)33-26/h15,18-19,21-23,29-30H,4,8-14H2,1-3,5-7H3

> <INCHI_KEY>
MOLHYXXXUDUQTC-UHFFFAOYSA-N

> <FORMULA>
C26H42O7

> <MOLECULAR_WEIGHT>
466.615

> <EXACT_MASS>
466.293053692

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
51.57709102678014

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
12-(acetyloxy)-1,9-dihydroxy-3,9-dimethyl-13-methylidene-6-(propan-2-yl)-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl butanoate

> <ALOGPS_LOGP>
3.41

> <JCHEM_LOGP>
3.5717087699999994

> <ALOGPS_LOGS>
-4.22

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.045531793255876

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.65848987953353

> <JCHEM_PKA_STRONGEST_BASIC>
-3.220632493026611

> <JCHEM_POLAR_SURFACE_AREA>
102.29000000000002

> <JCHEM_REFRACTIVITY>
122.8321

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.79e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-(acetyloxy)-1,9-dihydroxy-6-isopropyl-3,9-dimethyl-13-methylidene-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -7.497   4.402   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.164   3.632   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.830   4.402   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.496   3.632   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -3.496   2.092   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -2.163   4.402   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.829   3.632   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.302   5.079   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.819   2.452   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.292   1.005   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.224   0.738   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.751  -0.709   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.268  -0.977   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.239  -1.889   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.214   1.917   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.491   1.056   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.328   2.778   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.112   4.845   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.165   5.706   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.326   5.793   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.865   5.847   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.289   7.327   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.141   4.986   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.668   3.539   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.244   2.058   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.030   1.110   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.123   0.025   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.890  -0.424   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       6.355   5.934   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       7.783   5.357   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.996   6.305   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       7.997   3.832   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.688   3.365   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    9   33                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   11   16   33                                                  
CONECT   16   15   17   26                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20   33                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   16   27   28                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   23   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   18    7   15                                                  
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
12-(Acetyloxy)-1,9-dihydroxy-3,9-dimethyl-13-methylidene-6-(propan-2-yl)-15-oxatricyclo[6.6.1.0,]pentadecan-3-yl butanoic acid	Generator
12-(Acetyloxy)-1,9-dihydroxy-3,9-dimethyl-13-methylidene-6-(propan-2-yl)-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl butanoic acid	Generator

Chemical Formula

C₂₆H₄₂O₇

Average Mass

466.6150 Da

Monoisotopic Mass

466.29305 Da

IUPAC Name

12-(acetyloxy)-1,9-dihydroxy-3,9-dimethyl-13-methylidene-6-(propan-2-yl)-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl butanoate

Traditional Name

12-(acetyloxy)-1,9-dihydroxy-6-isopropyl-3,9-dimethyl-13-methylidene-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl butanoate

CAS Registry Number

Not Available

SMILES

CCCC(=O)OC1(C)CCC(C(C)C)C2C3OC(O)(CC(=C)C(CCC3(C)O)OC(C)=O)C12

InChI Identifier

InChI=1S/C26H42O7/c1-8-9-20(28)32-25(7)13-10-18(15(2)3)21-22(25)26(30)14-16(4)19(31-17(5)27)11-12-24(6,29)23(21)33-26/h15,18-19,21-23,29-30H,4,8-14H2,1-3,5-7H3

InChI Key

MOLHYXXXUDUQTC-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
Cladiella australis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eunicellane and asbestinane diterpenoids. These are diterpenoids with a structure based on either the eunicellane (5,14-cyclocembrane) or the asbestinane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Eunicellane and asbestinane diterpenoids

Alternative Parents

Substituents

Eunicellane-type diterpenoid
Cladiellane diterpenoid
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty acyl
Tertiary alcohol
Tetrahydrofuran
Carboxylic acid ester
Hemiacetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
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	3.41	ALOGPS
logP	3.57	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	11.66	ChemAxon
pKa (Strongest Basic)	-3.2	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	7	ChemAxon
Refractivity	122.83 m³·mol⁻¹	ChemAxon
Polarizability	51.58 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

85429635

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 12-(acetyloxy)-1,9-dihydroxy-6-isopropyl-3,9-dimethyl-13-methylidene-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl butanoate (NP0153006)

MOL for NP0153006 (12-(acetyloxy)-1,9-dihydroxy-6-isopropyl-3,9-dimethyl-13-methylidene-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl butanoate)

3D MOL for NP0153006 (12-(acetyloxy)-1,9-dihydroxy-6-isopropyl-3,9-dimethyl-13-methylidene-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl butanoate)

3D SDF for NP0153006 (12-(acetyloxy)-1,9-dihydroxy-6-isopropyl-3,9-dimethyl-13-methylidene-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl butanoate)

3D-SDF for NP0153006 (12-(acetyloxy)-1,9-dihydroxy-6-isopropyl-3,9-dimethyl-13-methylidene-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl butanoate)

PDB for NP0153006 (12-(acetyloxy)-1,9-dihydroxy-6-isopropyl-3,9-dimethyl-13-methylidene-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl butanoate)

3D PDB for NP0153006 (12-(acetyloxy)-1,9-dihydroxy-6-isopropyl-3,9-dimethyl-13-methylidene-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl butanoate)

SMILES for NP0153006 (12-(acetyloxy)-1,9-dihydroxy-6-isopropyl-3,9-dimethyl-13-methylidene-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl butanoate)

INCHI for NP0153006 (12-(acetyloxy)-1,9-dihydroxy-6-isopropyl-3,9-dimethyl-13-methylidene-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl butanoate)

Structure for NP0153006 (12-(acetyloxy)-1,9-dihydroxy-6-isopropyl-3,9-dimethyl-13-methylidene-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl butanoate)

3D Structure for NP0153006 (12-(acetyloxy)-1,9-dihydroxy-6-isopropyl-3,9-dimethyl-13-methylidene-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl butanoate)