NP-MRD: Showing NP-Card for Jatrophenediol (NP0331622)

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Record Information

Version

2.0

Created at

2023-05-09 20:01:55 UTC

Updated at

2024-09-03 04:16:18 UTC

NP-MRD ID

NP0331622

Natural Product DOI

https://doi.org/10.57994/0609

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Jatrophenediol

Description

Jatrophenediol belongs to the class of organic compounds known as pseudoguaianes. These are sesquiterpenoids with a structure based on the pseudoguaiane skeleton, which arises by the migration of the a methyl group of the bicyclic guaiane skeleton from the C4 to the C5 position. Based on a literature review very few articles have been published on Jatrophenediol.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305092322012D          

 18 19  0  0  1  0            999 V2000
    1.2796   -0.7556    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5363   -1.1136    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2483   -1.3685    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5033   -2.1531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7333   -0.7011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2483   -0.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5363   -0.2886    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3890    0.5232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1813    0.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9856    0.0422    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5000    0.6872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1986    1.4552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3158    0.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3436   -0.7011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9856   -1.4444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1813   -1.6280    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3829   -2.4280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6526   -2.2613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0331622

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12[C@@H](O)CC[C@@]1(C)C[C@@H](CC[C@@]2(C)O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H26O2/c1-10(2)11-5-8-15(4,17)13-12(16)6-7-14(13,3)9-11/h11-13,16-17H,1,5-9H2,2-4H3/t11-,12+,13+,14+,15-/m1/s1

> <INCHI_KEY>
SXIYOGCJAFXRHB-CAEXGNQWSA-N

> <FORMULA>
C15H26O2

> <MOLECULAR_WEIGHT>
238.371

> <EXACT_MASS>
238.193280077

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
28.11203460715189

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3aS,5R,8R,8aR)-3a,8-dimethyl-5-(prop-1-en-2-yl)-decahydroazulene-1,8-diol

> <JCHEM_LOGP>
2.264519848

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.172762647243392

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.459705913741118

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8673630985493386

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
69.8552

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3aS,5R,8R,8aR)-3a,8-dimethyl-5-(prop-1-en-2-yl)-octahydroazulene-1,8-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-MAY-23         0                                  
HETATM    1  H   UNK     0       2.389  -1.411   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       1.001  -2.079   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.464  -2.555   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.939  -4.019   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.369  -1.309   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.464  -0.063   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.001  -0.539   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.726   0.977   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.205   0.421   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.706   0.079   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.667   1.283   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.104   2.716   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.189   1.053   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.375  -1.309   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.706  -2.696   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.205  -3.039   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.581  -4.532   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.218  -4.221   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7   16                                             
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2    8    9                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    2   17   18                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₆O₂

Average Mass

238.3710 Da

Monoisotopic Mass

238.19328 Da

IUPAC Name

(1S,3aS,5R,8R,8aR)-3a,8-dimethyl-5-(prop-1-en-2-yl)-decahydroazulene-1,8-diol

Traditional Name

(1S,3aS,5R,8R,8aR)-3a,8-dimethyl-5-(prop-1-en-2-yl)-octahydroazulene-1,8-diol

CAS Registry Number

Not Available

SMILES

[H][C@]12[C@@H](O)CC[C@@]1(C)C[C@@H](CC[C@@]2(C)O)C(C)=C

InChI Identifier

InChI=1S/C15H26O2/c1-10(2)11-5-8-15(4,17)13-12(16)6-7-14(13,3)9-11/h11-13,16-17H,1,5-9H2,2-4H3/t11-,12+,13+,14+,15-/m1/s1

InChI Key

SXIYOGCJAFXRHB-CAEXGNQWSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 700 MHz, CDCl3, experimental)	francisco.bautista@ipicyt.edu.mx	Not Available	Not Available	2023-05-09	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, CDCl3, experimental)	francisco.bautista@ipicyt.edu.mx	Not Available	Not Available	2023-05-09	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 700 MHz, CDCl3, experimental)	francisco.bautista@ipicyt.edu.mx	Not Available	Not Available	2023-05-09	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 700 MHz, CDCl3, experimental)	francisco.bautista@ipicyt.edu.mx	Not Available	Not Available	2023-05-09	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 700 MHz, CDCl3, experimental)	francisco.bautista@ipicyt.edu.mx	Not Available	Not Available	2023-05-09	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl3, experimental)	francisco.bautista@ipicyt.edu.mx	Not Available	Not Available	2023-05-09	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as pseudoguaianes. These are sesquiterpenoids with a structure based on the pseudoguaiane skeleton, which arises by the migration of the a methyl group of the bicyclic guaiane skeleton from the C4 to the C5 position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Pseudoguaianes

Alternative Parents

Substituents

Pseudoguaiane sesquiterpenoid
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
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	2.26	ChemAxon
pKa (Strongest Acidic)	14.46	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	69.86 m³·mol⁻¹	ChemAxon
Polarizability	28.11 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

DOI: 10.1016/j.tetlet.2022.154040

Showing NP-Card for Jatrophenediol (NP0331622)

MOL for NP0331622 (Jatrophenediol)

3D MOL for NP0331622 (Jatrophenediol)

3D SDF for NP0331622 (Jatrophenediol)

3D-SDF for NP0331622 (Jatrophenediol)

PDB for NP0331622 (Jatrophenediol)

3D PDB for NP0331622 (Jatrophenediol)

SMILES for NP0331622 (Jatrophenediol)

INCHI for NP0331622 (Jatrophenediol)

Structure for NP0331622 (Jatrophenediol)

3D Structure for NP0331622 (Jatrophenediol)