NP-MRD: Showing NP-Card for (1s,3r,8r,11s,12s,15r,16r)-7,7,12,16-tetramethyl-15-[(2r)-6-methyl-5-oxoheptan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-one (NP0235043)

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Record Information

Version

2.0

Created at

2022-09-06 17:26:53 UTC

Updated at

2022-09-06 17:26:53 UTC

NP-MRD ID

NP0235043

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3r,8r,11s,12s,15r,16r)-7,7,12,16-tetramethyl-15-[(2r)-6-methyl-5-oxoheptan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-one

Description

Cycloartane-3,24-dione belongs to the class of organic compounds known as cycloartanols and derivatives. These are steroids containing a cycloartanol moiety. (1s,3r,8r,11s,12s,15r,16r)-7,7,12,16-tetramethyl-15-[(2r)-6-methyl-5-oxoheptan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-one is found in Bistorta officinalis and Larix kaempferi. (1s,3r,8r,11s,12s,15r,16r)-7,7,12,16-tetramethyl-15-[(2r)-6-methyl-5-oxoheptan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-one was first documented in 2005 (PMID: 16112695). Based on a literature review a small amount of articles have been published on cycloartane-3,24-dione (PMID: 17348850) (PMID: 16643035).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062219262D          

 32 36  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309062219262D          

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  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
 10  8  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 18 26  1  0  0  0  0
 26 27  1  1  0  0  0
 28 27  1  1  0  0  0
 15 28  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 10 31  1  0  0  0  0
 13 31  1  0  0  0  0
 31 32  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0235043

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CCC(=O)C(C)C)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@@H]4[C@]5(C[C@@]35CC[C@]12C)CCC(=O)C4(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O2/c1-19(2)22(31)9-8-20(3)21-12-14-28(7)24-11-10-23-26(4,5)25(32)13-15-29(23)18-30(24,29)17-16-27(21,28)6/h19-21,23-24H,8-18H2,1-7H3/t20-,21-,23+,24+,27-,28+,29-,30+/m1/s1

> <INCHI_KEY>
UMXQMWZSVMNHGK-HDMIJCIJSA-N

> <FORMULA>
C30H48O2

> <MOLECULAR_WEIGHT>
440.712

> <EXACT_MASS>
440.365430786

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
55.049625404055746

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,8R,11S,12S,15R,16R)-7,7,12,16-tetramethyl-15-[(2R)-6-methyl-5-oxoheptan-2-yl]pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-one

> <JCHEM_LOGP>
7.593519023000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.881773636465407

> <JCHEM_PKA_STRONGEST_BASIC>
-7.133580561422233

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
131.02819999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,8R,11S,12S,15R,16R)-7,7,12,16-tetramethyl-15-[(2R)-6-methyl-5-oxoheptan-2-yl]pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-one

> <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      17.683   7.130   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.157   7.340   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.577   8.767   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.212   6.125   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      15.792   4.698   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      13.686   6.335   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.741   5.119   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.216   5.330   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.635   6.757   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.270   4.114   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.698   2.635   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.424   1.771   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.208   2.716   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.839   1.221   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.692   2.445   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.169   0.996   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.653   0.725   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.660   1.903   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.144   1.632   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.674   0.186   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.812   0.858   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.151   2.809   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.365   2.538   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.675   4.257   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.191   4.528   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.183   3.351   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.707   4.799   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.699   3.622   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.222   5.071   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.738   5.342   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.731   4.164   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.403   5.550   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                                                  
CONECT    9    8                                                            
CONECT   10    8   11   31                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   31                                             
CONECT   14   13                                                            
CONECT   15   13   16   28                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   26                                                  
CONECT   19   18   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   18   27   28                                             
CONECT   27   26   28                                                       
CONECT   28   27   15   26   29                                             
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   10   13   32                                             
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₈O₂

Average Mass

440.7120 Da

Monoisotopic Mass

440.36543 Da

IUPAC Name

(1S,3R,8R,11S,12S,15R,16R)-7,7,12,16-tetramethyl-15-[(2R)-6-methyl-5-oxoheptan-2-yl]pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-one

Traditional Name

(1S,3R,8R,11S,12S,15R,16R)-7,7,12,16-tetramethyl-15-[(2R)-6-methyl-5-oxoheptan-2-yl]pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-one

CAS Registry Number

Not Available

SMILES

C[C@H](CCC(=O)C(C)C)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@@H]4[C@]5(C[C@@]35CC[C@]12C)CCC(=O)C4(C)C

InChI Identifier

InChI=1S/C30H48O2/c1-19(2)22(31)9-8-20(3)21-12-14-28(7)24-11-10-23-26(4,5)25(32)13-15-29(23)18-30(24,29)17-16-27(21,28)6/h19-21,23-24H,8-18H2,1-7H3/t20-,21-,23+,24+,27-,28+,29-,30+/m1/s1

InChI Key

UMXQMWZSVMNHGK-HDMIJCIJSA-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
Bistorta officinalis	LOTUS Database	35616633
Larix kaempferi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cycloartanols and derivatives. These are steroids containing a cycloartanol moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cycloartanols and derivatives

Direct Parent

Cycloartanols and derivatives

Alternative Parents

Substituents

Cycloartanol-skeleton
9b,19-cyclo-lanostane-skeleton
Cycloartane-skeleton
Triterpenoid
24-oxosteroid
Bile acid, alcohol, or derivatives
3-oxosteroid
Oxosteroid
3-oxo-5-alpha-steroid
Ketone
Cyclic ketone
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organooxygen compound
Organic oxygen 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	7.59	ChemAxon
pKa (Strongest Acidic)	19.88	ChemAxon
pKa (Strongest Basic)	-7.1	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	5	ChemAxon
Refractivity	131.03 m³·mol⁻¹	ChemAxon
Polarizability	55.05 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00057234

Chemspider ID

23283648

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44423576

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Manoharan KP, Yang D, Hsu A, Huat BT: Evaluation of Polygonum bistorta for anticancer potential using selected cancer cell lines. Med Chem. 2007 Mar;3(2):121-6. doi: 10.2174/157340607780059495. [PubMed:17348850 ]
Manoharan KP, Benny TK, Yang D: Cycloartane type triterpenoids from the rhizomes of Polygonum bistorta. Phytochemistry. 2005 Oct;66(19):2304-8. doi: 10.1016/j.phytochem.2005.07.008. [PubMed:16112695 ]
Akihisa T, Watanabe K, Yoneima R, Suzuki T, Kimura Y: Biotransformation of cycloartane-type triterpenes by the fungus Glomerella fusarioides. J Nat Prod. 2006 Apr;69(4):604-7. doi: 10.1021/np058120d. [PubMed:16643035 ]
LOTUS database [Link]

Showing NP-Card for (1s,3r,8r,11s,12s,15r,16r)-7,7,12,16-tetramethyl-15-[(2r)-6-methyl-5-oxoheptan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-one (NP0235043)

MOL for NP0235043 ((1s,3r,8r,11s,12s,15r,16r)-7,7,12,16-tetramethyl-15-[(2r)-6-methyl-5-oxoheptan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-one)

3D MOL for NP0235043 ((1s,3r,8r,11s,12s,15r,16r)-7,7,12,16-tetramethyl-15-[(2r)-6-methyl-5-oxoheptan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-one)

3D SDF for NP0235043 ((1s,3r,8r,11s,12s,15r,16r)-7,7,12,16-tetramethyl-15-[(2r)-6-methyl-5-oxoheptan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-one)

3D-SDF for NP0235043 ((1s,3r,8r,11s,12s,15r,16r)-7,7,12,16-tetramethyl-15-[(2r)-6-methyl-5-oxoheptan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-one)

PDB for NP0235043 ((1s,3r,8r,11s,12s,15r,16r)-7,7,12,16-tetramethyl-15-[(2r)-6-methyl-5-oxoheptan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-one)

3D PDB for NP0235043 ((1s,3r,8r,11s,12s,15r,16r)-7,7,12,16-tetramethyl-15-[(2r)-6-methyl-5-oxoheptan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-one)

SMILES for NP0235043 ((1s,3r,8r,11s,12s,15r,16r)-7,7,12,16-tetramethyl-15-[(2r)-6-methyl-5-oxoheptan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-one)

INCHI for NP0235043 ((1s,3r,8r,11s,12s,15r,16r)-7,7,12,16-tetramethyl-15-[(2r)-6-methyl-5-oxoheptan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-one)

Structure for NP0235043 ((1s,3r,8r,11s,12s,15r,16r)-7,7,12,16-tetramethyl-15-[(2r)-6-methyl-5-oxoheptan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-one)

3D Structure for NP0235043 ((1s,3r,8r,11s,12s,15r,16r)-7,7,12,16-tetramethyl-15-[(2r)-6-methyl-5-oxoheptan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-one)