NP-MRD: Showing NP-Card for (1r,4as,4bs,6as,8s,10ar,10bs,12as)-1,4b,6a,8,10a,12a-hexamethyl-8-(4-methyl-3-oxopent-4-en-1-yl)-dodecahydrochrysen-2-one (NP0206145)

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Record Information

Version

2.0

Created at

2022-09-05 02:16:55 UTC

Updated at

2022-09-05 02:16:55 UTC

NP-MRD ID

NP0206145

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4as,4bs,6as,8s,10ar,10bs,12as)-1,4b,6a,8,10a,12a-hexamethyl-8-(4-methyl-3-oxopent-4-en-1-yl)-dodecahydrochrysen-2-one

Description

(1R,4aS,4bS,6aS,8S,10aR,10bS,12aS)-1,4b,6a,8,10a,12a-hexamethyl-8-(4-methyl-3-oxopent-4-en-1-yl)-octadecahydrochrysen-2-one 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,4as,4bs,6as,8s,10ar,10bs,12as)-1,4b,6a,8,10a,12a-hexamethyl-8-(4-methyl-3-oxopent-4-en-1-yl)-dodecahydrochrysen-2-one is found in Aster tataricus. Based on a literature review very few articles have been published on (1R,4aS,4bS,6aS,8S,10aR,10bS,12aS)-1,4b,6a,8,10a,12a-hexamethyl-8-(4-methyl-3-oxopent-4-en-1-yl)-octadecahydrochrysen-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052204162D          

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M  END

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M  END


  Mrv1652309052204162D          

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  4  5  2  0  0  0  0
  4  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  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  6  0  0  0
 19 26  1  0  0  0  0
 14 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 12 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
  8 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0206145

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O2/c1-20(2)22(31)11-13-26(4)15-18-30(8)25-12-14-28(6)21(3)23(32)9-10-24(28)29(25,7)17-16-27(30,5)19-26/h21,24-25H,1,9-19H2,2-8H3/t21-,24+,25-,26+,27-,28+,29-,30+/m0/s1

> <INCHI_KEY>
FQXDAAPLCNFRBB-QUIPRQILSA-N

> <FORMULA>
C30H48O2

> <MOLECULAR_WEIGHT>
440.712

> <EXACT_MASS>
440.365430786

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
54.37686000726745

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4aS,4bS,6aS,8S,10aR,10bS,12aS)-1,4b,6a,8,10a,12a-hexamethyl-8-(4-methyl-3-oxopent-4-en-1-yl)-octadecahydrochrysen-2-one

> <JCHEM_LOGP>
7.867148683333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.685413868682429

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
132.6603

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4aS,4bS,6aS,8S,10aR,10bS,12aS)-1,4b,6a,8,10a,12a-hexamethyl-8-(4-methyl-3-oxopent-4-en-1-yl)-dodecahydrochrysen-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -9.598  -8.886   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.252  -8.137   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.931  -8.928   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.228  -6.597   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -9.550  -5.806   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -6.883  -5.848   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.859  -4.308   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.513  -3.559   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.485  -2.364   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.009  -5.014   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.497  -5.305   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.489  -4.141   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.985  -5.596   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.977  -4.432   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.472  -5.887   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.040  -6.178   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.048  -5.014   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.552  -6.469   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.544  -3.559   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.552  -2.395   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.064  -2.686   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.568  -4.141   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.081  -4.432   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.560  -5.305   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.064  -6.760   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.032  -3.268   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.040  -2.104   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.472  -1.813   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.985  -1.522   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.993  -2.686   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.497  -1.231   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.505  -2.395   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   32                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   30                                             
CONECT   13   12                                                            
CONECT   14   12   15   26                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   24                                             
CONECT   18   17                                                            
CONECT   19   17   20   26                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   17   25                                                  
CONECT   25   24                                                            
CONECT   26   19   14   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   12   31   32                                             
CONECT   31   30                                                            
CONECT   32   30    8                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₈O₂

Average Mass

440.7120 Da

Monoisotopic Mass

440.36543 Da

IUPAC Name

(1R,4aS,4bS,6aS,8S,10aR,10bS,12aS)-1,4b,6a,8,10a,12a-hexamethyl-8-(4-methyl-3-oxopent-4-en-1-yl)-octadecahydrochrysen-2-one

Traditional Name

(1R,4aS,4bS,6aS,8S,10aR,10bS,12aS)-1,4b,6a,8,10a,12a-hexamethyl-8-(4-methyl-3-oxopent-4-en-1-yl)-dodecahydrochrysen-2-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C30H48O2/c1-20(2)22(31)11-13-26(4)15-18-30(8)25-12-14-28(6)21(3)23(32)9-10-24(28)29(25,7)17-16-27(30,5)19-26/h21,24-25H,1,9-19H2,2-8H3/t21-,24+,25-,26+,27-,28+,29-,30+/m0/s1

InChI Key

FQXDAAPLCNFRBB-QUIPRQILSA-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
Aster tataricus	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
Alpha-branched alpha,beta-unsaturated-ketone
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	7.87	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	132.66 m³·mol⁻¹	ChemAxon
Polarizability	54.38 Å³	ChemAxon
Number of Rings	4	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

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

50925134

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,4as,4bs,6as,8s,10ar,10bs,12as)-1,4b,6a,8,10a,12a-hexamethyl-8-(4-methyl-3-oxopent-4-en-1-yl)-dodecahydrochrysen-2-one (NP0206145)

MOL for NP0206145 ((1r,4as,4bs,6as,8s,10ar,10bs,12as)-1,4b,6a,8,10a,12a-hexamethyl-8-(4-methyl-3-oxopent-4-en-1-yl)-dodecahydrochrysen-2-one)

3D MOL for NP0206145 ((1r,4as,4bs,6as,8s,10ar,10bs,12as)-1,4b,6a,8,10a,12a-hexamethyl-8-(4-methyl-3-oxopent-4-en-1-yl)-dodecahydrochrysen-2-one)

3D SDF for NP0206145 ((1r,4as,4bs,6as,8s,10ar,10bs,12as)-1,4b,6a,8,10a,12a-hexamethyl-8-(4-methyl-3-oxopent-4-en-1-yl)-dodecahydrochrysen-2-one)

3D-SDF for NP0206145 ((1r,4as,4bs,6as,8s,10ar,10bs,12as)-1,4b,6a,8,10a,12a-hexamethyl-8-(4-methyl-3-oxopent-4-en-1-yl)-dodecahydrochrysen-2-one)

PDB for NP0206145 ((1r,4as,4bs,6as,8s,10ar,10bs,12as)-1,4b,6a,8,10a,12a-hexamethyl-8-(4-methyl-3-oxopent-4-en-1-yl)-dodecahydrochrysen-2-one)

3D PDB for NP0206145 ((1r,4as,4bs,6as,8s,10ar,10bs,12as)-1,4b,6a,8,10a,12a-hexamethyl-8-(4-methyl-3-oxopent-4-en-1-yl)-dodecahydrochrysen-2-one)

SMILES for NP0206145 ((1r,4as,4bs,6as,8s,10ar,10bs,12as)-1,4b,6a,8,10a,12a-hexamethyl-8-(4-methyl-3-oxopent-4-en-1-yl)-dodecahydrochrysen-2-one)

INCHI for NP0206145 ((1r,4as,4bs,6as,8s,10ar,10bs,12as)-1,4b,6a,8,10a,12a-hexamethyl-8-(4-methyl-3-oxopent-4-en-1-yl)-dodecahydrochrysen-2-one)

Structure for NP0206145 ((1r,4as,4bs,6as,8s,10ar,10bs,12as)-1,4b,6a,8,10a,12a-hexamethyl-8-(4-methyl-3-oxopent-4-en-1-yl)-dodecahydrochrysen-2-one)

3D Structure for NP0206145 ((1r,4as,4bs,6as,8s,10ar,10bs,12as)-1,4b,6a,8,10a,12a-hexamethyl-8-(4-methyl-3-oxopent-4-en-1-yl)-dodecahydrochrysen-2-one)