NP-MRD: Showing NP-Card for 9,12-bis(acetyloxy)-5,13-dihydroxy-6-isopropyl-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl acetate (NP0205427)

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Record Information

Version

2.0

Created at

2022-09-05 01:20:17 UTC

Updated at

2022-09-05 01:20:17 UTC

NP-MRD ID

NP0205427

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9,12-bis(acetyloxy)-5,13-dihydroxy-6-isopropyl-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl acetate

Description

9,12-Bis(acetyloxy)-5,13-dihydroxy-3,9,13-trimethyl-6-(propan-2-yl)-15-oxatricyclo[6.6.1.0²,⁷]Pentadecan-3-yl acetate 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. 9,12-bis(acetyloxy)-5,13-dihydroxy-6-isopropyl-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl acetate is found in Klyxum simplex. 9,12-Bis(acetyloxy)-5,13-dihydroxy-3,9,13-trimethyl-6-(propan-2-yl)-15-oxatricyclo[6.6.1.0²,⁷]Pentadecan-3-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241503412D          

 35 37  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004241503412D          

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  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 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  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  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
 15 30  1  0  0  0  0
 29 31  1  0  0  0  0
  4 31  1  0  0  0  0
 14 31  1  0  0  0  0
 20 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0205427

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1C2C3OC(CC(C)(O)C(CCC3(C)OC(C)=O)OC(C)=O)C2C(C)(CC1O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H42O9/c1-13(2)20-17(30)11-26(8,35-16(5)29)22-18-12-24(6,31)19(32-14(3)27)9-10-25(7,34-15(4)28)23(33-18)21(20)22/h13,17-23,30-31H,9-12H2,1-8H3

> <INCHI_KEY>
CMFFEVGUTXFGMQ-UHFFFAOYSA-N

> <FORMULA>
C26H42O9

> <MOLECULAR_WEIGHT>
498.613

> <EXACT_MASS>
498.282882932

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
53.1449929353936

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9,12-bis(acetyloxy)-5,13-dihydroxy-3,9,13-trimethyl-6-(propan-2-yl)-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl acetate

> <ALOGPS_LOGP>
2.13

> <JCHEM_LOGP>
0.836982992

> <ALOGPS_LOGS>
-3.93

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.887222928640181

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.89529209108418

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8713637094345374

> <JCHEM_POLAR_SURFACE_AREA>
128.59

> <JCHEM_REFRACTIVITY>
124.71770000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.91e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9,12-bis(acetyloxy)-5,13-dihydroxy-6-isopropyl-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.324  -1.950   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.344  -1.950   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.870  -3.397   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.119  -4.577   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.387  -3.664   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.905  -1.246   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.370  -1.722   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.834  -1.246   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.834  -2.786   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.299  -1.722   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.740  -0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.740   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.834   2.786   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.370   3.262   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.275   4.508   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.465   4.508   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.091   5.915   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.186   7.160   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.623   6.075   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.905   2.786   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.401   0.770   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.204  -0.476   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       7.349   0.555   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       7.029   2.061   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       8.813   0.079   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   31                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10   14                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    8   15   31                                                  
CONECT   15   14   16   30                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17   21   32                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25   29                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   23   30   31                                                  
CONECT   30   29   15                                                       
CONECT   31   29    4   14                                                  
CONECT   32   20   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Value	Source
9,12-Bis(acetyloxy)-5,13-dihydroxy-3,9,13-trimethyl-6-(propan-2-yl)-15-oxatricyclo[6.6.1.0,]pentadecan-3-yl acetic acid	Generator
9,12-Bis(acetyloxy)-5,13-dihydroxy-3,9,13-trimethyl-6-(propan-2-yl)-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl acetic acid	Generator

Chemical Formula

C₂₆H₄₂O₉

Average Mass

498.6130 Da

Monoisotopic Mass

498.28288 Da

IUPAC Name

9,12-bis(acetyloxy)-5,13-dihydroxy-3,9,13-trimethyl-6-(propan-2-yl)-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl acetate

Traditional Name

9,12-bis(acetyloxy)-5,13-dihydroxy-6-isopropyl-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl acetate

CAS Registry Number

Not Available

SMILES

CC(C)C1C2C3OC(CC(C)(O)C(CCC3(C)OC(C)=O)OC(C)=O)C2C(C)(CC1O)OC(C)=O

InChI Identifier

InChI=1S/C26H42O9/c1-13(2)20-17(30)11-26(8,35-16(5)29)22-18-12-24(6,31)19(32-14(3)27)9-10-25(7,34-15(4)28)23(33-18)21(20)22/h13,17-23,30-31H,9-12H2,1-8H3

InChI Key

CMFFEVGUTXFGMQ-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
Klyxum simplex	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
Tricarboxylic acid or derivatives
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Carboxylic acid ester
Secondary alcohol
Ether
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
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	2.13	ALOGPS
logP	0.84	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	13.9	ChemAxon
pKa (Strongest Basic)	-2.9	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	124.72 m³·mol⁻¹	ChemAxon
Polarizability	53.14 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

56670928

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 9,12-bis(acetyloxy)-5,13-dihydroxy-6-isopropyl-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl acetate (NP0205427)

MOL for NP0205427 (9,12-bis(acetyloxy)-5,13-dihydroxy-6-isopropyl-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl acetate)

3D MOL for NP0205427 (9,12-bis(acetyloxy)-5,13-dihydroxy-6-isopropyl-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl acetate)

3D SDF for NP0205427 (9,12-bis(acetyloxy)-5,13-dihydroxy-6-isopropyl-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl acetate)

3D-SDF for NP0205427 (9,12-bis(acetyloxy)-5,13-dihydroxy-6-isopropyl-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl acetate)

PDB for NP0205427 (9,12-bis(acetyloxy)-5,13-dihydroxy-6-isopropyl-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl acetate)

3D PDB for NP0205427 (9,12-bis(acetyloxy)-5,13-dihydroxy-6-isopropyl-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl acetate)

SMILES for NP0205427 (9,12-bis(acetyloxy)-5,13-dihydroxy-6-isopropyl-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl acetate)

INCHI for NP0205427 (9,12-bis(acetyloxy)-5,13-dihydroxy-6-isopropyl-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl acetate)

Structure for NP0205427 (9,12-bis(acetyloxy)-5,13-dihydroxy-6-isopropyl-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl acetate)

3D Structure for NP0205427 (9,12-bis(acetyloxy)-5,13-dihydroxy-6-isopropyl-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl acetate)