NP-MRD: Showing NP-Card for (1s,3r)-2,2-dimethyl-4-methylidene-3-[(3e,7e,11e)-3,8,12,16-tetramethylheptadeca-3,7,11,15-tetraen-1-yl]cyclohexan-1-ol (NP0258252)

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Record Information

Version

2.0

Created at

2022-09-07 23:37:12 UTC

Updated at

2022-09-07 23:37:12 UTC

NP-MRD ID

NP0258252

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3r)-2,2-dimethyl-4-methylidene-3-[(3e,7e,11e)-3,8,12,16-tetramethylheptadeca-3,7,11,15-tetraen-1-yl]cyclohexan-1-ol

Description

Achilleol A belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (1s,3r)-2,2-dimethyl-4-methylidene-3-[(3e,7e,11e)-3,8,12,16-tetramethylheptadeca-3,7,11,15-tetraen-1-yl]cyclohexan-1-ol is found in Achillea nobilis, Bupleurum fruticescens, Camellia oleifera, Camellia sasanqua and Santolina elegans. (1s,3r)-2,2-dimethyl-4-methylidene-3-[(3e,7e,11e)-3,8,12,16-tetramethylheptadeca-3,7,11,15-tetraen-1-yl]cyclohexan-1-ol was first documented in 1999 (PMID: 10606037). Based on a literature review a small amount of articles have been published on achilleol A (PMID: 10075756) (PMID: 10814317) (PMID: 10930258) (PMID: 12081472).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082201372D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309082201372D          

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 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0258252

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC[C@@H]1C(=C)CC[C@H](O)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O/c1-23(2)13-11-16-25(4)18-12-17-24(3)14-9-10-15-26(5)19-21-28-27(6)20-22-29(31)30(28,7)8/h13-15,18,28-29,31H,6,9-12,16-17,19-22H2,1-5,7-8H3/b24-14+,25-18+,26-15+/t28-,29+/m1/s1

> <INCHI_KEY>
ANKPMKKGZZQDIC-HJSIMFEZSA-N

> <FORMULA>
C30H50O

> <MOLECULAR_WEIGHT>
426.729

> <EXACT_MASS>
426.38616623

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
56.25026371899696

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R)-2,2-dimethyl-4-methylidene-3-[(3E,7E,11E)-3,8,12,16-tetramethylheptadeca-3,7,11,15-tetraen-1-yl]cyclohexan-1-ol

> <JCHEM_LOGP>
8.888916621

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.5757002546092

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7973887086339352

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
142.23030000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R)-2,2-dimethyl-4-methylidene-3-[(3E,7E,11E)-3,8,12,16-tetramethylheptadeca-3,7,11,15-tetraen-1-yl]cyclohexan-1-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.670   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.004   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      17.338   2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.672   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      18.672   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      20.005   2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      21.339   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      22.673   2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      24.006   1.540   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      25.340   2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      24.006   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7    2   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   62    0
END

View in JSmol

Synonyms

Value	Source
(-)-Achilleol a	ChEBI

Chemical Formula

C₃₀H₅₀O

Average Mass

426.7290 Da

Monoisotopic Mass

426.38617 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC[C@@H]1C(=C)CC[C@H](O)C1(C)C

InChI Identifier

InChI=1S/C30H50O/c1-23(2)13-11-16-25(4)18-12-17-24(3)14-9-10-15-26(5)19-21-28-27(6)20-22-29(31)30(28,7)8/h13-15,18,28-29,31H,6,9-12,16-17,19-22H2,1-5,7-8H3/b24-14+,25-18+,26-15+/t28-,29+/m1/s1

InChI Key

ANKPMKKGZZQDIC-HJSIMFEZSA-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
Achillea nobilis	LOTUS Database	35616633
Bupleurum fruticescens	LOTUS Database	35616633
Camellia oleifera	LOTUS Database	35616633
Camellia sasanqua	LOTUS Database	35616633
Santolina elegans	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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

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

4581493

KEGG Compound ID

Not Available

BioCyc ID

CPD-13286

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5471312

PDB ID

Not Available

ChEBI ID

189410

Good Scents ID

Not Available

References

General References

Akihisa T, Koike K, Kimura Y, Sashida N, Matsumoto T, Ukiya M, Nikaido T: Acyclic and incompletely cyclized triterpene alcohols in the seed oils of theaceae and gramineae. Lipids. 1999 Nov;34(11):1151-7. doi: 10.1007/s11745-999-0466-5. [PubMed:10606037 ]
Akihisa T, Arai K, Kimura Y, Koike K, Kokke WCMC, Shibata T, Nikaido T: Camelliols A-C, three novel incompletely cyclized triterpene alcohols from sasanqua oil (Camellia sasanqua). J Nat Prod. 1999 Feb;62(2):265-8. doi: 10.1021/np980336a. [PubMed:10075756 ]
Joubert BM, Hua L, Matsuda SP: Steric bulk at position 454 in Saccharomyces cerevisiae lanosterol synthase influences B-ring formation but not deprotonation. Org Lett. 2000 Feb 10;2(3):339-41. doi: 10.1021/ol9912940. [PubMed:10814317 ]
Matsuda SP, Darr LB, Hart EA, Herrera JB, McCann KE, Meyer MM, Pang J, Schepmann HG: Steric bulk at cycloartenol synthase position 481 influences cyclization and deprotonation. Org Lett. 2000 Jul 27;2(15):2261-3. doi: 10.1021/ol006018w. [PubMed:10930258 ]
Wu TK, Griffin JH: Conversion of a plant oxidosqualene-cycloartenol synthase to an oxidosqualene-lanosterol cyclase by random mutagenesis. Biochemistry. 2002 Jul 2;41(26):8238-44. doi: 10.1021/bi0200920. [PubMed:12081472 ]
LOTUS database [Link]

Showing NP-Card for (1s,3r)-2,2-dimethyl-4-methylidene-3-[(3e,7e,11e)-3,8,12,16-tetramethylheptadeca-3,7,11,15-tetraen-1-yl]cyclohexan-1-ol (NP0258252)

MOL for NP0258252 ((1s,3r)-2,2-dimethyl-4-methylidene-3-[(3e,7e,11e)-3,8,12,16-tetramethylheptadeca-3,7,11,15-tetraen-1-yl]cyclohexan-1-ol)

3D MOL for NP0258252 ((1s,3r)-2,2-dimethyl-4-methylidene-3-[(3e,7e,11e)-3,8,12,16-tetramethylheptadeca-3,7,11,15-tetraen-1-yl]cyclohexan-1-ol)

3D SDF for NP0258252 ((1s,3r)-2,2-dimethyl-4-methylidene-3-[(3e,7e,11e)-3,8,12,16-tetramethylheptadeca-3,7,11,15-tetraen-1-yl]cyclohexan-1-ol)

3D-SDF for NP0258252 ((1s,3r)-2,2-dimethyl-4-methylidene-3-[(3e,7e,11e)-3,8,12,16-tetramethylheptadeca-3,7,11,15-tetraen-1-yl]cyclohexan-1-ol)

PDB for NP0258252 ((1s,3r)-2,2-dimethyl-4-methylidene-3-[(3e,7e,11e)-3,8,12,16-tetramethylheptadeca-3,7,11,15-tetraen-1-yl]cyclohexan-1-ol)

3D PDB for NP0258252 ((1s,3r)-2,2-dimethyl-4-methylidene-3-[(3e,7e,11e)-3,8,12,16-tetramethylheptadeca-3,7,11,15-tetraen-1-yl]cyclohexan-1-ol)

SMILES for NP0258252 ((1s,3r)-2,2-dimethyl-4-methylidene-3-[(3e,7e,11e)-3,8,12,16-tetramethylheptadeca-3,7,11,15-tetraen-1-yl]cyclohexan-1-ol)

INCHI for NP0258252 ((1s,3r)-2,2-dimethyl-4-methylidene-3-[(3e,7e,11e)-3,8,12,16-tetramethylheptadeca-3,7,11,15-tetraen-1-yl]cyclohexan-1-ol)

Structure for NP0258252 ((1s,3r)-2,2-dimethyl-4-methylidene-3-[(3e,7e,11e)-3,8,12,16-tetramethylheptadeca-3,7,11,15-tetraen-1-yl]cyclohexan-1-ol)

3D Structure for NP0258252 ((1s,3r)-2,2-dimethyl-4-methylidene-3-[(3e,7e,11e)-3,8,12,16-tetramethylheptadeca-3,7,11,15-tetraen-1-yl]cyclohexan-1-ol)