NP-MRD: Showing NP-Card for (4ar,5s,6r,8as)-5-[(3s)-5-hydroxy-3-methylpentyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carbaldehyde (NP0250054)

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Record Information

Version

2.0

Created at

2022-09-07 12:47:09 UTC

Updated at

2022-09-07 12:47:10 UTC

NP-MRD ID

NP0250054

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4ar,5s,6r,8as)-5-[(3s)-5-hydroxy-3-methylpentyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carbaldehyde

Description

(8Alpha,9S,10beta)-15-Hydroxy-cleroda-3-ene-19-al belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. (4ar,5s,6r,8as)-5-[(3s)-5-hydroxy-3-methylpentyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carbaldehyde is found in Cistus monspeliensis. Based on a literature review very few articles have been published on (8alpha,9S,10beta)-15-Hydroxy-cleroda-3-ene-19-al.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072214472D          

 22 23  0  0  1  0            999 V2000
    7.0704    1.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0704    0.4217    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3559    0.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6414    0.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9269    0.0092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7848    0.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4993    0.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2138    0.0092    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6835   -0.6228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4959    0.7844    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.9656    1.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3084    0.9277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8387    0.2957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5565   -0.4795    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.3690   -0.3363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0868   -1.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8993   -0.9683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1815   -0.1930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8047   -1.8868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9922   -2.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4619   -1.3980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7441   -0.6228    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 16 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  6  0  0  0
 14 22  1  0  0  0  0
  8 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0250054

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CCO)CC[C@@]1(C)[C@H](C)CC[C@@]2(C)[C@@H]1CCC=C2C=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O2/c1-15(10-13-21)8-11-19(3)16(2)9-12-20(4)17(14-22)6-5-7-18(19)20/h6,14-16,18,21H,5,7-13H2,1-4H3/t15-,16+,18+,19-,20+/m0/s1

> <INCHI_KEY>
AFKYIBHTOFRQCN-GRLGQGAKSA-N

> <FORMULA>
C20H34O2

> <MOLECULAR_WEIGHT>
306.49

> <EXACT_MASS>
306.255880335

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
37.20314832904131

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aR,5S,6R,8aS)-5-[(3S)-5-hydroxy-3-methylpentyl]-5,6,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carbaldehyde

> <JCHEM_LOGP>
4.384125144

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.10979809811116

> <JCHEM_PKA_STRONGEST_BASIC>
-1.8750017103608778

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
93.22209999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4aR,5S,6R,8aS)-5-[(3S)-5-hydroxy-3-methylpentyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carbaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      13.198   2.327   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.198   0.787   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.864   0.017   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.531   0.787   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       9.197   0.017   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      14.532   0.017   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.865   0.787   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.199   0.017   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.209  -1.163   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.726   1.464   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.736   2.644   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      19.242   1.732   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      20.232   0.552   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      19.706  -0.895   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.222  -0.628   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.695  -2.075   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.212  -1.807   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      22.739  -0.360   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      20.169  -3.522   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      18.652  -3.789   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.662  -2.610   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      18.189  -1.163   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    2    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   22                                             
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   22                                             
CONECT   15   14                                                            
CONECT   16   14   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   14    8                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
(8a,9S,10b)-15-Hydroxy-cleroda-3-ene-19-al	Generator
(8Α,9S,10β)-15-hydroxy-cleroda-3-ene-19-al	Generator

Chemical Formula

C₂₀H₃₄O₂

Average Mass

306.4900 Da

Monoisotopic Mass

306.25588 Da

IUPAC Name

(4aR,5S,6R,8aS)-5-[(3S)-5-hydroxy-3-methylpentyl]-5,6,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carbaldehyde

Traditional Name

(4aR,5S,6R,8aS)-5-[(3S)-5-hydroxy-3-methylpentyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carbaldehyde

CAS Registry Number

Not Available

SMILES

C[C@H](CCO)CC[C@@]1(C)[C@H](C)CC[C@@]2(C)[C@@H]1CCC=C2C=O

InChI Identifier

InChI=1S/C20H34O2/c1-15(10-13-21)8-11-19(3)16(2)9-12-20(4)17(14-22)6-5-7-18(19)20/h6,14-16,18,21H,5,7-13H2,1-4H3/t15-,16+,18+,19-,20+/m0/s1

InChI Key

AFKYIBHTOFRQCN-GRLGQGAKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cistus monspeliensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Colensane and clerodane diterpenoids

Alternative Parents

Substituents

Clerodane diterpenoid
Fatty alcohol
Fatty acyl
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Aldehyde
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	4.38	ChemAxon
pKa (Strongest Acidic)	17.11	ChemAxon
pKa (Strongest Basic)	-1.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	93.22 m³·mol⁻¹	ChemAxon
Polarizability	37.2 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

101235638

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4ar,5s,6r,8as)-5-[(3s)-5-hydroxy-3-methylpentyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carbaldehyde (NP0250054)

MOL for NP0250054 ((4ar,5s,6r,8as)-5-[(3s)-5-hydroxy-3-methylpentyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carbaldehyde)

3D MOL for NP0250054 ((4ar,5s,6r,8as)-5-[(3s)-5-hydroxy-3-methylpentyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carbaldehyde)

3D SDF for NP0250054 ((4ar,5s,6r,8as)-5-[(3s)-5-hydroxy-3-methylpentyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carbaldehyde)

3D-SDF for NP0250054 ((4ar,5s,6r,8as)-5-[(3s)-5-hydroxy-3-methylpentyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carbaldehyde)

PDB for NP0250054 ((4ar,5s,6r,8as)-5-[(3s)-5-hydroxy-3-methylpentyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carbaldehyde)

3D PDB for NP0250054 ((4ar,5s,6r,8as)-5-[(3s)-5-hydroxy-3-methylpentyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carbaldehyde)

SMILES for NP0250054 ((4ar,5s,6r,8as)-5-[(3s)-5-hydroxy-3-methylpentyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carbaldehyde)

INCHI for NP0250054 ((4ar,5s,6r,8as)-5-[(3s)-5-hydroxy-3-methylpentyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carbaldehyde)

Structure for NP0250054 ((4ar,5s,6r,8as)-5-[(3s)-5-hydroxy-3-methylpentyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carbaldehyde)

3D Structure for NP0250054 ((4ar,5s,6r,8as)-5-[(3s)-5-hydroxy-3-methylpentyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carbaldehyde)