NP-MRD: Showing NP-Card for 2-[4-hydroxy-2-(3-hydroxypropyl)-3,4-dimethyl-3-(4,9,12-trimethyltrideca-3,7,11-trien-1-yl)cyclohexylidene]propanal (NP0188511)

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Record Information

Version

2.0

Created at

2022-09-04 04:51:26 UTC

Updated at

2022-09-04 04:51:26 UTC

NP-MRD ID

NP0188511

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[4-hydroxy-2-(3-hydroxypropyl)-3,4-dimethyl-3-(4,9,12-trimethyltrideca-3,7,11-trien-1-yl)cyclohexylidene]propanal

Description

2-[4-Hydroxy-2-(3-hydroxypropyl)-3,4-dimethyl-3-(4,9,12-trimethyltrideca-3,7,11-trien-1-yl)cyclohexylidene]propanal belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. 2-[4-hydroxy-2-(3-hydroxypropyl)-3,4-dimethyl-3-(4,9,12-trimethyltrideca-3,7,11-trien-1-yl)cyclohexylidene]propanal is found in Iris germanica. 2-[4-Hydroxy-2-(3-hydroxypropyl)-3,4-dimethyl-3-(4,9,12-trimethyltrideca-3,7,11-trien-1-yl)cyclohexylidene]propanal is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251512162D          

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M  END

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M  END


  Mrv1533004251512162D          

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    0.3983    4.1952    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  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  8  2  1  4  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  4  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  4  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 16 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 12 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0188511

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CC=C(C)C)C=CCCC(C)=CCCC1(C)C(CCCO)C(CCC1(C)O)=C(C)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O3/c1-23(2)16-17-25(4)13-9-8-12-24(3)14-10-19-29(6)28(15-11-21-31)27(26(5)22-32)18-20-30(29,7)33/h9,13-14,16,22,25,28,31,33H,8,10-12,15,17-21H2,1-7H3

> <INCHI_KEY>
VWZKPZARAHDCMM-UHFFFAOYSA-N

> <FORMULA>
C30H50O3

> <MOLECULAR_WEIGHT>
458.727

> <EXACT_MASS>
458.37599547

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
57.108963363287685

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[4-hydroxy-2-(3-hydroxypropyl)-3,4-dimethyl-3-(4,9,12-trimethyltrideca-3,7,11-trien-1-yl)cyclohexylidene]propanal

> <ALOGPS_LOGP>
6.56

> <JCHEM_LOGP>
6.668968165333336

> <ALOGPS_LOGS>
-5.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.855571330629395

> <JCHEM_PKA_STRONGEST_BASIC>
-0.2754808903277247

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
145.21050000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.44e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[4-hydroxy-2-(3-hydroxypropyl)-3,4-dimethyl-3-(4,9,12-trimethyltrideca-3,7,11-trien-1-yl)cyclohexylidene]propanal

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       7.736  12.015   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.263  10.568   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.780  10.301   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.769  11.480   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.286  11.213   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.276  12.393   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.813   9.766   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.273   9.388   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.756   9.656   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.767   8.476   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.250   8.743   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.260   7.564   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.787   6.117   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.797   4.937   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.539   1.594   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.816   2.846   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.743   7.831   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    2    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   33                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   30                                             
CONECT   17   16                                                            
CONECT   18   16   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   18   24   28                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26                                                            
CONECT   28   23   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   16   31   32                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   12                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₅₀O₃

Average Mass

458.7270 Da

Monoisotopic Mass

458.37600 Da

IUPAC Name

2-[4-hydroxy-2-(3-hydroxypropyl)-3,4-dimethyl-3-(4,9,12-trimethyltrideca-3,7,11-trien-1-yl)cyclohexylidene]propanal

Traditional Name

2-[4-hydroxy-2-(3-hydroxypropyl)-3,4-dimethyl-3-(4,9,12-trimethyltrideca-3,7,11-trien-1-yl)cyclohexylidene]propanal

CAS Registry Number

Not Available

SMILES

CC(CC=C(C)C)C=CCCC(C)=CCCC1(C)C(CCCO)C(CCC1(C)O)=C(C)C=O

InChI Identifier

InChI=1S/C30H50O3/c1-23(2)16-17-25(4)13-9-8-12-24(3)14-10-19-29(6)28(15-11-21-31)27(26(5)22-32)18-20-30(29,7)33/h9,13-14,16,22,25,28,31,33H,8,10-12,15,17-21H2,1-7H3

InChI Key

VWZKPZARAHDCMM-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
Iris germanica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

P-menthane monoterpenoid
Monocyclic monoterpenoid
Tertiary alcohol
Enal
Cyclic alcohol
Alpha,beta-unsaturated aldehyde
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Aldehyde
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	6.56	ALOGPS
logP	6.67	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	16.86	ChemAxon
pKa (Strongest Basic)	-0.28	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	145.21 m³·mol⁻¹	ChemAxon
Polarizability	57.11 Å³	ChemAxon
Number of Rings	1	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 2-[4-hydroxy-2-(3-hydroxypropyl)-3,4-dimethyl-3-(4,9,12-trimethyltrideca-3,7,11-trien-1-yl)cyclohexylidene]propanal (NP0188511)

MOL for NP0188511 (2-[4-hydroxy-2-(3-hydroxypropyl)-3,4-dimethyl-3-(4,9,12-trimethyltrideca-3,7,11-trien-1-yl)cyclohexylidene]propanal)

3D MOL for NP0188511 (2-[4-hydroxy-2-(3-hydroxypropyl)-3,4-dimethyl-3-(4,9,12-trimethyltrideca-3,7,11-trien-1-yl)cyclohexylidene]propanal)

3D SDF for NP0188511 (2-[4-hydroxy-2-(3-hydroxypropyl)-3,4-dimethyl-3-(4,9,12-trimethyltrideca-3,7,11-trien-1-yl)cyclohexylidene]propanal)

3D-SDF for NP0188511 (2-[4-hydroxy-2-(3-hydroxypropyl)-3,4-dimethyl-3-(4,9,12-trimethyltrideca-3,7,11-trien-1-yl)cyclohexylidene]propanal)

PDB for NP0188511 (2-[4-hydroxy-2-(3-hydroxypropyl)-3,4-dimethyl-3-(4,9,12-trimethyltrideca-3,7,11-trien-1-yl)cyclohexylidene]propanal)

3D PDB for NP0188511 (2-[4-hydroxy-2-(3-hydroxypropyl)-3,4-dimethyl-3-(4,9,12-trimethyltrideca-3,7,11-trien-1-yl)cyclohexylidene]propanal)

SMILES for NP0188511 (2-[4-hydroxy-2-(3-hydroxypropyl)-3,4-dimethyl-3-(4,9,12-trimethyltrideca-3,7,11-trien-1-yl)cyclohexylidene]propanal)

INCHI for NP0188511 (2-[4-hydroxy-2-(3-hydroxypropyl)-3,4-dimethyl-3-(4,9,12-trimethyltrideca-3,7,11-trien-1-yl)cyclohexylidene]propanal)

Structure for NP0188511 (2-[4-hydroxy-2-(3-hydroxypropyl)-3,4-dimethyl-3-(4,9,12-trimethyltrideca-3,7,11-trien-1-yl)cyclohexylidene]propanal)

3D Structure for NP0188511 (2-[4-hydroxy-2-(3-hydroxypropyl)-3,4-dimethyl-3-(4,9,12-trimethyltrideca-3,7,11-trien-1-yl)cyclohexylidene]propanal)