NP-MRD: Showing NP-Card for (1r,2s,4as,8as)-1-(3-methoxy-3-methylpent-4-en-1-yl)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalene (NP0220647)

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Record Information

Version

2.0

Created at

2022-09-05 22:01:22 UTC

Updated at

2022-09-05 22:01:22 UTC

NP-MRD ID

NP0220647

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,4as,8as)-1-(3-methoxy-3-methylpent-4-en-1-yl)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalene

Description

(+)-O-methylkolavelool 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. (1r,2s,4as,8as)-1-(3-methoxy-3-methylpent-4-en-1-yl)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalene is found in Herpetosiphon aurantiacus. (1r,2s,4as,8as)-1-(3-methoxy-3-methylpent-4-en-1-yl)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalene was first documented in 2015 (PMID: 25694050). Based on a literature review very few articles have been published on (+)-O-methylkolavelool.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062200012D          

 22 23  0  0  1  0            999 V2000
    0.4024   -5.0965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1202   -4.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6505   -3.6892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2825   -4.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1808   -3.0572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9592   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0185   -3.1589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1618   -2.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  1  0  0  0
 13 20  1  0  0  0  0
  7 20  1  0  0  0  0
  3 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0220647

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H36O/c1-8-19(4,22-7)14-15-21(6)17(3)12-13-20(5)16(2)10-9-11-18(20)21/h8,10,17-18H,1,9,11-15H2,2-7H3/t17-,18+,19?,20+,21+/m0/s1

> <INCHI_KEY>
VRVYZZJPEDVTBX-POFDQXHJSA-N

> <FORMULA>
C21H36O

> <MOLECULAR_WEIGHT>
304.518

> <EXACT_MASS>
304.276615779

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
38.00384710737749

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4R,4aS,8aS)-4-(3-methoxy-3-methylpent-4-en-1-yl)-3,4,8,8a-tetramethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalene

> <JCHEM_LOGP>
5.889612436333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.1698362432298275

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
96.90199999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4aS,8aS)-1-(3-methoxy-3-methylpent-4-en-1-yl)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       0.751  -9.513   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.224  -8.066   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.214  -6.887   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.394  -7.876   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.204  -5.707   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.677  -4.260   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.657  -4.260   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.035  -5.897   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.302  -4.380   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   21                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   20                                             
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   20                                             
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   13    7                                                  
CONECT   21    3   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
O-Methylkolavelool	MeSH

Chemical Formula

C₂₁H₃₆O

Average Mass

304.5180 Da

Monoisotopic Mass

304.27662 Da

IUPAC Name

(3S,4R,4aS,8aS)-4-(3-methoxy-3-methylpent-4-en-1-yl)-3,4,8,8a-tetramethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalene

Traditional Name

(1R,2S,4aS,8aS)-1-(3-methoxy-3-methylpent-4-en-1-yl)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalene

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C21H36O/c1-8-19(4,22-7)14-15-21(6)17(3)12-13-20(5)16(2)10-9-11-18(20)21/h8,10,17-18H,1,9,11-15H2,2-7H3/t17-,18+,19?,20+,21+/m0/s1

InChI Key

VRVYZZJPEDVTBX-POFDQXHJSA-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
Herpetosiphon aurantiacus	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
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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	5.89	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	96.9 m³·mol⁻¹	ChemAxon
Polarizability	38 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

76963095

KEGG Compound ID

Not Available

BioCyc ID

CPD-20432

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102335044

PDB ID

Not Available

ChEBI ID

139480

Good Scents ID

Not Available

References

General References

Nakano C, Oshima M, Kurashima N, Hoshino T: Identification of a new diterpene biosynthetic gene cluster that produces O-methylkolavelool in Herpetosiphon aurantiacus. Chembiochem. 2015 Mar 23;16(5):772-81. doi: 10.1002/cbic.201402652. Epub 2015 Feb 18. [PubMed:25694050 ]
LOTUS database [Link]

Showing NP-Card for (1r,2s,4as,8as)-1-(3-methoxy-3-methylpent-4-en-1-yl)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalene (NP0220647)

MOL for NP0220647 ((1r,2s,4as,8as)-1-(3-methoxy-3-methylpent-4-en-1-yl)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalene)

3D MOL for NP0220647 ((1r,2s,4as,8as)-1-(3-methoxy-3-methylpent-4-en-1-yl)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalene)

3D SDF for NP0220647 ((1r,2s,4as,8as)-1-(3-methoxy-3-methylpent-4-en-1-yl)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalene)

3D-SDF for NP0220647 ((1r,2s,4as,8as)-1-(3-methoxy-3-methylpent-4-en-1-yl)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalene)

PDB for NP0220647 ((1r,2s,4as,8as)-1-(3-methoxy-3-methylpent-4-en-1-yl)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalene)

3D PDB for NP0220647 ((1r,2s,4as,8as)-1-(3-methoxy-3-methylpent-4-en-1-yl)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalene)

SMILES for NP0220647 ((1r,2s,4as,8as)-1-(3-methoxy-3-methylpent-4-en-1-yl)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalene)

INCHI for NP0220647 ((1r,2s,4as,8as)-1-(3-methoxy-3-methylpent-4-en-1-yl)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalene)

Structure for NP0220647 ((1r,2s,4as,8as)-1-(3-methoxy-3-methylpent-4-en-1-yl)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalene)

3D Structure for NP0220647 ((1r,2s,4as,8as)-1-(3-methoxy-3-methylpent-4-en-1-yl)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalene)