NP-MRD: Showing NP-Card for 15-[4-(3,3-dimethyloxiran-2-yl)-4-oxobutan-2-yl]-6,18-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-10-en-14-one (NP0182382)

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Record Information

Version

1.0

Created at

2022-09-03 21:03:15 UTC

Updated at

2022-09-03 21:03:15 UTC

NP-MRD ID

NP0182382

Secondary Accession Numbers

None

Natural Product Identification

Common Name

15-[4-(3,3-dimethyloxiran-2-yl)-4-oxobutan-2-yl]-6,18-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-10-en-14-one

Description

15-[4-(3,3-Dimethyloxiran-2-yl)-4-oxobutan-2-yl]-6,18-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]Octadec-10-en-14-one belongs to the class of organic compounds known as cycloartanols and derivatives. These are steroids containing a cycloartanol moiety. 15-[4-(3,3-dimethyloxiran-2-yl)-4-oxobutan-2-yl]-6,18-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-10-en-14-one is found in Actaea cimicifuga. 15-[4-(3,3-Dimethyloxiran-2-yl)-4-oxobutan-2-yl]-6,18-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]Octadec-10-en-14-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161507092D          

 35 40  0  0  0  0            999 V2000
    5.6974    3.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0083    2.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8256    2.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3319    3.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0210    4.1580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1492    3.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9134    3.5919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8005    2.7747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004161507092D          

 35 40  0  0  0  0            999 V2000
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    3.0532    1.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3335    2.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8017    3.3471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1456    2.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6774    2.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0373    2.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  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
 20 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 17 30  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 11 34  1  0  0  0  0
 15 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0182382

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CC(=O)C1OC1(C)C)C1C(=O)CC2(C)C3=CCC4C5(CC35C(O)CC12C)CCC(O)C4(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O5/c1-16(12-17(31)24-26(4,5)35-24)23-18(32)13-27(6)20-9-8-19-25(2,3)21(33)10-11-29(19)15-30(20,29)22(34)14-28(23,27)7/h9,16,19,21-24,33-34H,8,10-15H2,1-7H3

> <INCHI_KEY>
IGPRVRMPUFGMJK-UHFFFAOYSA-N

> <FORMULA>
C30H44O5

> <MOLECULAR_WEIGHT>
484.677

> <EXACT_MASS>
484.318874517

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
55.15904888544342

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
15-[4-(3,3-dimethyloxiran-2-yl)-4-oxobutan-2-yl]-6,18-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-10-en-14-one

> <ALOGPS_LOGP>
4.28

> <JCHEM_LOGP>
3.345720930333335

> <ALOGPS_LOGS>
-4.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.554153298064794

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.51865396582177

> <JCHEM_PKA_STRONGEST_BASIC>
-0.1956001824980128

> <JCHEM_POLAR_SURFACE_AREA>
87.13000000000001

> <JCHEM_REFRACTIVITY>
134.36759999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.40e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-[4-(3,3-dimethyloxiran-2-yl)-4-oxobutan-2-yl]-6,18-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-10-en-14-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      10.635   6.757   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.216   5.330   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.741   5.119   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.686   6.335   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      13.106   7.762   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      15.212   6.125   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      16.638   6.705   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      16.428   5.179   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.721   4.344   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.085   3.678   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.270   4.114   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.698   2.635   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      12.147   2.112   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.424   1.771   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.208   2.716   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.839   1.221   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.692   2.445   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.169   0.996   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.653   0.725   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.660   1.903   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.144   1.632   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.674   0.186   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.812   0.858   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.151   2.809   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.365   2.538   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.675   4.257   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.191   4.528   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.183   3.351   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.707   4.799   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.699   3.622   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.222   5.071   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.230   6.248   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       7.738   5.342   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.731   4.164   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.403   5.550   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6    8                                                       
CONECT    8    7    6    9   10                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    2   12   34                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17   34                                             
CONECT   16   15                                                            
CONECT   17   15   18   30                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   28                                                  
CONECT   21   20   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   20   29   30                                             
CONECT   29   28   30                                                       
CONECT   30   29   17   28   31                                             
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   11   15   35                                             
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₄O₅

Average Mass

484.6770 Da

Monoisotopic Mass

484.31887 Da

IUPAC Name

15-[4-(3,3-dimethyloxiran-2-yl)-4-oxobutan-2-yl]-6,18-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-10-en-14-one

Traditional Name

15-[4-(3,3-dimethyloxiran-2-yl)-4-oxobutan-2-yl]-6,18-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-10-en-14-one

CAS Registry Number

Not Available

SMILES

CC(CC(=O)C1OC1(C)C)C1C(=O)CC2(C)C3=CCC4C5(CC35C(O)CC12C)CCC(O)C4(C)C

InChI Identifier

InChI=1S/C30H44O5/c1-16(12-17(31)24-26(4,5)35-24)23-18(32)13-27(6)20-9-8-19-25(2,3)21(33)10-11-29(19)15-30(20,29)22(34)14-28(23,27)7/h9,16,19,21-24,33-34H,8,10-15H2,1-7H3

InChI Key

IGPRVRMPUFGMJK-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
Actaea cimicifuga	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
23-oxosteroid
3-hydroxysteroid
Hydroxysteroid
16-oxosteroid
Oxosteroid
11-hydroxysteroid
Cyclic alcohol
Ketone
Secondary alcohol
Cyclic ketone
Oxacycle
Ether
Oxirane
Dialkyl ether
Organoheterocyclic compound
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	4.28	ALOGPS
logP	3.35	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	18.52	ChemAxon
pKa (Strongest Basic)	-0.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	87.13 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	134.37 m³·mol⁻¹	ChemAxon
Polarizability	55.16 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	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

85136004

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 15-[4-(3,3-dimethyloxiran-2-yl)-4-oxobutan-2-yl]-6,18-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-10-en-14-one (NP0182382)

MOL for NP0182382 (15-[4-(3,3-dimethyloxiran-2-yl)-4-oxobutan-2-yl]-6,18-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-10-en-14-one)

3D MOL for NP0182382 (15-[4-(3,3-dimethyloxiran-2-yl)-4-oxobutan-2-yl]-6,18-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-10-en-14-one)

3D SDF for NP0182382 (15-[4-(3,3-dimethyloxiran-2-yl)-4-oxobutan-2-yl]-6,18-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-10-en-14-one)

3D-SDF for NP0182382 (15-[4-(3,3-dimethyloxiran-2-yl)-4-oxobutan-2-yl]-6,18-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-10-en-14-one)

PDB for NP0182382 (15-[4-(3,3-dimethyloxiran-2-yl)-4-oxobutan-2-yl]-6,18-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-10-en-14-one)

3D PDB for NP0182382 (15-[4-(3,3-dimethyloxiran-2-yl)-4-oxobutan-2-yl]-6,18-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-10-en-14-one)

SMILES for NP0182382 (15-[4-(3,3-dimethyloxiran-2-yl)-4-oxobutan-2-yl]-6,18-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-10-en-14-one)

INCHI for NP0182382 (15-[4-(3,3-dimethyloxiran-2-yl)-4-oxobutan-2-yl]-6,18-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-10-en-14-one)

Structure for NP0182382 (15-[4-(3,3-dimethyloxiran-2-yl)-4-oxobutan-2-yl]-6,18-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-10-en-14-one)

3D Structure for NP0182382 (15-[4-(3,3-dimethyloxiran-2-yl)-4-oxobutan-2-yl]-6,18-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-10-en-14-one)