NP-MRD: Showing NP-Card for (1,2-dihydroxy-1-isopropyl-3a-methyl-2,3,4,7,8,8a-hexahydroazulen-6-yl)methyl octadec-9-enoate (NP0260046)

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Record Information

Version

2.0

Created at

2022-09-08 02:05:50 UTC

Updated at

2022-09-08 02:05:50 UTC

NP-MRD ID

NP0260046

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1,2-dihydroxy-1-isopropyl-3a-methyl-2,3,4,7,8,8a-hexahydroazulen-6-yl)methyl octadec-9-enoate

Description

[2,3-Dihydroxy-8a-methyl-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-6-yl]methyl octadec-9-enoate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (1,2-dihydroxy-1-isopropyl-3a-methyl-2,3,4,7,8,8a-hexahydroazulen-6-yl)methyl octadec-9-enoate is found in Trichoderma virens. [2,3-Dihydroxy-8a-methyl-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-6-yl]methyl octadec-9-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241514432D          

 37 38  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004241514432D          

 37 38  0  0  0  0            999 V2000
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    2.1462   -6.7805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8607   -7.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5751   -6.7805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2896   -7.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0041   -6.7805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7185   -7.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4330   -6.7805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4330   -5.9555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1475   -7.1930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8620   -6.7805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5764   -7.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2581   -6.7283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0464   -6.9715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3478   -7.7394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8813   -7.1101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1548   -7.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2410   -8.7314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9555   -9.1439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4874   -9.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8999   -9.7815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8199   -9.5519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0662   -9.2164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9062  -10.3724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9353   -8.4539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1195   -8.5769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5148   -8.0157    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  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  4  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 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
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  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
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 30 35  1  0  0  0  0
 25 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 22 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0260046

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCC=CCCCCCCCC(=O)OCC1=CCC2(C)CC(O)C(O)(C(C)C)C2CC1

> <INCHI_IDENTIFIER>
InChI=1S/C33H58O4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-31(35)37-26-28-21-22-29-32(4,24-23-28)25-30(34)33(29,36)27(2)3/h12-13,23,27,29-30,34,36H,5-11,14-22,24-26H2,1-4H3

> <INCHI_KEY>
IRNSDAKENNBILA-UHFFFAOYSA-N

> <FORMULA>
C33H58O4

> <MOLECULAR_WEIGHT>
518.823

> <EXACT_MASS>
518.433510348

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
95

> <JCHEM_AVERAGE_POLARIZABILITY>
65.7709131699277

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[2,3-dihydroxy-8a-methyl-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-6-yl]methyl octadec-9-enoate

> <ALOGPS_LOGP>
8.79

> <JCHEM_LOGP>
8.800250249666668

> <ALOGPS_LOGS>
-6.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.873888169308323

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.350879575705981

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2501541219245533

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
156.24920000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.42e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1,2-dihydroxy-1-isopropyl-3a-methyl-2,3,4,7,8,8a-hexahydroazulen-6-yl)methyl octadec-9-enoate

> <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      -3.996  -1.877   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.996  -3.417   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.662  -4.187   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.662  -5.727   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.329  -6.497   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.329  -8.037   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.005  -8.807   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.005 -10.347   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.339 -11.117   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.339 -12.657   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.673 -13.427   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.006 -12.657   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.340 -13.427   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.674 -12.657   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.007 -13.427   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.341 -12.657   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.675 -13.427   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.008 -12.657   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      12.008 -11.117   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      13.342 -13.427   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      14.676 -12.657   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.009 -13.427   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      17.282 -12.559   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.753 -13.013   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      19.316 -14.447   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      20.312 -13.272   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      20.822 -14.767   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      20.983 -16.299   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      22.317 -17.069   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      19.576 -16.925   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      20.346 -18.259   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      18.331 -17.830   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      16.924 -17.204   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      18.491 -19.362   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      18.546 -15.781   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      17.023 -16.010   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      15.894 -14.963   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   37                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27   35                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32   35                                             
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   30   25   36                                                  
CONECT   36   35   37                                                       
CONECT   37   36   22                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   76    0
END

View in JSmol

Synonyms

Value	Source
[2,3-Dihydroxy-8a-methyl-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-6-yl]methyl octadec-9-enoic acid	Generator

Chemical Formula

C₃₃H₅₈O₄

Average Mass

518.8230 Da

Monoisotopic Mass

518.43351 Da

IUPAC Name

[2,3-dihydroxy-8a-methyl-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-6-yl]methyl octadec-9-enoate

Traditional Name

(1,2-dihydroxy-1-isopropyl-3a-methyl-2,3,4,7,8,8a-hexahydroazulen-6-yl)methyl octadec-9-enoate

CAS Registry Number

Not Available

SMILES

CCCCCCCCC=CCCCCCCCC(=O)OCC1=CCC2(C)CC(O)C(O)(C(C)C)C2CC1

InChI Identifier

InChI=1S/C33H58O4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-31(35)37-26-28-21-22-29-32(4,24-23-28)25-30(34)33(29,36)27(2)3/h12-13,23,27,29-30,34,36H,5-11,14-22,24-26H2,1-4H3

InChI Key

IRNSDAKENNBILA-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
Trichoderma virens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Daucane sesquiterpenoid
Sesquiterpenoid
Fatty acid ester
Fatty acyl
Cyclic alcohol
Tertiary alcohol
1,2-diol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	8.79	ALOGPS
logP	8.8	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Acidic)	13.35	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	156.25 m³·mol⁻¹	ChemAxon
Polarizability	65.77 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1,2-dihydroxy-1-isopropyl-3a-methyl-2,3,4,7,8,8a-hexahydroazulen-6-yl)methyl octadec-9-enoate (NP0260046)

MOL for NP0260046 ((1,2-dihydroxy-1-isopropyl-3a-methyl-2,3,4,7,8,8a-hexahydroazulen-6-yl)methyl octadec-9-enoate)

3D MOL for NP0260046 ((1,2-dihydroxy-1-isopropyl-3a-methyl-2,3,4,7,8,8a-hexahydroazulen-6-yl)methyl octadec-9-enoate)

3D SDF for NP0260046 ((1,2-dihydroxy-1-isopropyl-3a-methyl-2,3,4,7,8,8a-hexahydroazulen-6-yl)methyl octadec-9-enoate)

3D-SDF for NP0260046 ((1,2-dihydroxy-1-isopropyl-3a-methyl-2,3,4,7,8,8a-hexahydroazulen-6-yl)methyl octadec-9-enoate)

PDB for NP0260046 ((1,2-dihydroxy-1-isopropyl-3a-methyl-2,3,4,7,8,8a-hexahydroazulen-6-yl)methyl octadec-9-enoate)

3D PDB for NP0260046 ((1,2-dihydroxy-1-isopropyl-3a-methyl-2,3,4,7,8,8a-hexahydroazulen-6-yl)methyl octadec-9-enoate)

SMILES for NP0260046 ((1,2-dihydroxy-1-isopropyl-3a-methyl-2,3,4,7,8,8a-hexahydroazulen-6-yl)methyl octadec-9-enoate)

INCHI for NP0260046 ((1,2-dihydroxy-1-isopropyl-3a-methyl-2,3,4,7,8,8a-hexahydroazulen-6-yl)methyl octadec-9-enoate)

Structure for NP0260046 ((1,2-dihydroxy-1-isopropyl-3a-methyl-2,3,4,7,8,8a-hexahydroazulen-6-yl)methyl octadec-9-enoate)

3D Structure for NP0260046 ((1,2-dihydroxy-1-isopropyl-3a-methyl-2,3,4,7,8,8a-hexahydroazulen-6-yl)methyl octadec-9-enoate)