NP-MRD: Showing NP-Card for 10-methoxy-2,2,4a,6b,9,9,12a,14a-octamethyl-1,3,4,5,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydropicene (NP0255632)

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Record Information

Version

2.0

Created at

2022-09-07 20:11:18 UTC

Updated at

2022-09-07 20:11:19 UTC

NP-MRD ID

NP0255632

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10-methoxy-2,2,4a,6b,9,9,12a,14a-octamethyl-1,3,4,5,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydropicene

Description

Sawamilletin, also known as crusgallin, belongs to the class of organic compounds known as scalarane sesterterpenoids. These are sesterterpenoids with a structure based on the scalarane backbone. Scalarane is a tetracyclic compound, which is similar the homoandrostane with five methyl groups at the 4-, 4-, 8-, 17-, 17a-positions. 10-methoxy-2,2,4a,6b,9,9,12a,14a-octamethyl-1,3,4,5,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydropicene is found in Acradenia frankliniae, Manilkara kauki and Saccharum spontaneum. Sawamilletin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241210092D          

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M  END

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M  END


  Mrv0541 02241210092D          

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    1.2979   -1.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  1  0  0  0  0
  1 26  1  0  0  0  0
  2  3  1  0  0  0  0
  3 16  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 11  1  0  0  0  0
  5 15  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 16  1  0  0  0  0
  9 10  1  0  0  0  0
  9 21  1  0  0  0  0
 11 12  1  0  0  0  0
 11 19  1  0  0  0  0
 12 29  1  0  0  0  0
 13 14  1  0  0  0  0
 13 19  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 32  1  0  0  0  0
 17 18  1  0  0  0  0
 17 29  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 26  1  0  0  0  0
 24 31  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0255632

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1CCC2(C)C(CCC3(C)C2CCC2(C)C4CC(C)(C)CCC4(C)CC=C32)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C31H52O/c1-26(2)18-19-28(5)14-10-22-30(7)15-11-21-27(3,4)25(32-9)13-17-29(21,6)23(30)12-16-31(22,8)24(28)20-26/h10,21,23-25H,11-20H2,1-9H3

> <INCHI_KEY>
MJIBQQFDNJYZGY-UHFFFAOYSA-N

> <FORMULA>
C31H52O

> <MOLECULAR_WEIGHT>
440.744

> <EXACT_MASS>
440.401816286

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
56.65136398406787

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-methoxy-4,4,6a,8a,11,11,12b,14b-octamethyl-1,2,3,4,4a,5,6,6a,8,8a,9,10,11,12,12a,12b,13,14,14a,14b-icosahydropicene

> <ALOGPS_LOGP>
7.83

> <JCHEM_LOGP>
8.046267338

> <ALOGPS_LOGS>
-7.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.126412936768981

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
136.6585

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.41e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-methoxy-2,2,4a,6b,9,9,12a,14a-octamethyl-1,3,4,5,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydropicene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.332  -3.079   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -3.848   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.335  -3.079   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   2.311   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.335   1.541   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.771   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -0.769   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.332  -1.539   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.332   0.001   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   1.541   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   3.081   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.336  -0.769   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -1.539   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -0.769   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.335  -1.539   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668   3.081   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668   1.541   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.336   0.771   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668   0.001   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.667  -0.769   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.001  -1.539   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.001  -3.079   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -5.333  -3.848   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -3.657  -5.029   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.667  -3.848   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.676  -5.029   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.345   5.029   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.336   3.851   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.324   5.029   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -6.668  -3.079   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.423  -2.627   0.000  0.00  0.00           C+0
CONECT    1    2    9   26                                                  
CONECT    2    1    3                                                       
CONECT    3    2   16                                                       
CONECT    4    5                                                            
CONECT    5    4    6   11   15                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    1    8   10   21                                             
CONECT   10    9                                                            
CONECT   11    5   12   19                                                  
CONECT   12   11   29                                                       
CONECT   13   14   19                                                       
CONECT   14   13   15                                                       
CONECT   15    5   14   16                                                  
CONECT   16    3    8   15   32                                             
CONECT   17   18   29                                                       
CONECT   18   17   19                                                       
CONECT   19   11   13   18   20                                             
CONECT   20   19                                                            
CONECT   21    9   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   31                                                       
CONECT   25   26                                                            
CONECT   26    1   23   25   27                                             
CONECT   27   26                                                            
CONECT   28   29                                                            
CONECT   29   12   17   28   30                                             
CONECT   30   29                                                            
CONECT   31   24                                                            
CONECT   32   16                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Value	Source
3-Methoxy-14-taraxerene	HMDB
Crusgallin	HMDB

Chemical Formula

C₃₁H₅₂O

Average Mass

440.7440 Da

Monoisotopic Mass

440.40182 Da

IUPAC Name

3-methoxy-4,4,6a,8a,11,11,12b,14b-octamethyl-1,2,3,4,4a,5,6,6a,8,8a,9,10,11,12,12a,12b,13,14,14a,14b-icosahydropicene

Traditional Name

10-methoxy-2,2,4a,6b,9,9,12a,14a-octamethyl-1,3,4,5,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydropicene

CAS Registry Number

Not Available

SMILES

COC1CCC2(C)C(CCC3(C)C2CCC2(C)C4CC(C)(C)CCC4(C)CC=C32)C1(C)C

InChI Identifier

InChI=1S/C31H52O/c1-26(2)18-19-28(5)14-10-22-30(7)15-11-21-27(3,4)25(32-9)13-17-29(21,6)23(30)12-16-31(22,8)24(28)20-26/h10,21,23-25H,11-20H2,1-9H3

InChI Key

MJIBQQFDNJYZGY-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
Acradenia frankliniae	LOTUS Database	35616633
Manilkara kauki	LOTUS Database	35616633
Saccharum spontaneum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as scalarane sesterterpenoids. These are sesterterpenoids with a structure based on the scalarane backbone. Scalarane is a tetracyclic compound, which is similar the homoandrostane with five methyl groups at the 4-, 4-, 8-, 17-, 17a-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Scalarane sesterterpenoids

Alternative Parents

Substituents

Scalarane sesterterpenoid
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	7.83	ALOGPS
logP	8.05	ChemAxon
logS	-7.3	ALOGPS
pKa (Strongest Basic)	-4.1	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	1	ChemAxon
Refractivity	136.66 m³·mol⁻¹	ChemAxon
Polarizability	56.65 Å³	ChemAxon
Number of Rings	5	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

HMDB0034918

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013503

KNApSAcK ID

Not Available

Chemspider ID

529785

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

609451

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 10-methoxy-2,2,4a,6b,9,9,12a,14a-octamethyl-1,3,4,5,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydropicene (NP0255632)

MOL for NP0255632 (10-methoxy-2,2,4a,6b,9,9,12a,14a-octamethyl-1,3,4,5,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydropicene)

3D MOL for NP0255632 (10-methoxy-2,2,4a,6b,9,9,12a,14a-octamethyl-1,3,4,5,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydropicene)

3D SDF for NP0255632 (10-methoxy-2,2,4a,6b,9,9,12a,14a-octamethyl-1,3,4,5,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydropicene)

3D-SDF for NP0255632 (10-methoxy-2,2,4a,6b,9,9,12a,14a-octamethyl-1,3,4,5,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydropicene)

PDB for NP0255632 (10-methoxy-2,2,4a,6b,9,9,12a,14a-octamethyl-1,3,4,5,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydropicene)

3D PDB for NP0255632 (10-methoxy-2,2,4a,6b,9,9,12a,14a-octamethyl-1,3,4,5,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydropicene)

SMILES for NP0255632 (10-methoxy-2,2,4a,6b,9,9,12a,14a-octamethyl-1,3,4,5,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydropicene)

INCHI for NP0255632 (10-methoxy-2,2,4a,6b,9,9,12a,14a-octamethyl-1,3,4,5,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydropicene)

Structure for NP0255632 (10-methoxy-2,2,4a,6b,9,9,12a,14a-octamethyl-1,3,4,5,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydropicene)

3D Structure for NP0255632 (10-methoxy-2,2,4a,6b,9,9,12a,14a-octamethyl-1,3,4,5,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydropicene)