NP-MRD: Showing NP-Card for (+)-13,28-Epoxy-11-oleanene-3-one (NP0082246)

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Record Information

Version

2.0

Created at

2022-04-29 03:17:24 UTC

Updated at

2022-04-29 03:17:24 UTC

NP-MRD ID

NP0082246

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-13,28-Epoxy-11-oleanene-3-one

Description

(1S,4S,5R,8S,13S,14R,17R,18R)-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]Tetracos-15-en-10-one belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (+)-13,28-Epoxy-11-oleanene-3-one is found in Viburnum awabuki. Based on a literature review very few articles have been published on (1S,4S,5R,8S,13S,14R,17R,18R)-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]Tetracos-15-en-10-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304292205172D          

 32 37  0  0  1  0            999 V2000
    1.2711   -1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1795   -0.5154    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4765   -0.0836    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2489   -0.4764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2714   -1.3011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4315   -1.7330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0245   -2.4506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7989   -2.4717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0124    0.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8674    0.5776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2226   -0.2150    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7519   -0.9613    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2429   -1.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0773   -1.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4777   -0.9192    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0587   -0.2085    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4648    0.5097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2897    0.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7087   -0.1935    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3026   -0.9117    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7216   -1.6224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5466   -1.6149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9526   -0.8968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7775   -0.8893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5336   -0.1861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2293    0.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5550    0.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8966   -1.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6402    0.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0032   -1.4601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2908   -0.9541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1752    0.6086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 20 28  1  1  0  0  0
 16 29  1  1  0  0  0
 12 30  1  6  0  0  0
 30 31  1  0  0  0  0
  3 31  1  1  0  0  0
 11 32  1  6  0  0  0
M  END


  Mrv1652304292205172D          

 32 37  0  0  1  0            999 V2000
    1.2711   -1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1795   -0.5154    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4765   -0.0836    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2489   -0.4764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2714   -1.3011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4315   -1.7330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0245   -2.4506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7989   -2.4717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0124    0.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8674    0.5776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2226   -0.2150    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7519   -0.9613    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2429   -1.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0773   -1.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4777   -0.9192    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0587   -0.2085    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4648    0.5097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2897    0.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7087   -0.1935    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3026   -0.9117    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7216   -1.6224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5466   -1.6149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9526   -0.8968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7775   -0.8893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5336   -0.1861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2293    0.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5550    0.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8966   -1.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6402    0.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0032   -1.4601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2908   -0.9541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1752    0.6086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 20 28  1  1  0  0  0
 16 29  1  1  0  0  0
 12 30  1  6  0  0  0
 30 31  1  0  0  0  0
  3 31  1  1  0  0  0
 11 32  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0082246

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CC[C@]23CO[C@]4(C=C[C@@H]5[C@@]6(C)CCC(=O)C(C)(C)[C@H]6CC[C@@]5(C)[C@]4(C)CC2)[C@@H]3C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O2/c1-24(2)14-16-29-17-15-28(7)27(6)12-8-20-25(3,4)23(31)10-11-26(20,5)21(27)9-13-30(28,32-19-29)22(29)18-24/h9,13,20-22H,8,10-12,14-19H2,1-7H3/t20-,21-,22-,26+,27-,28+,29-,30-/m1/s1

> <INCHI_KEY>
BFSRJRKZZSIEFP-MOHLSBLISA-N

> <FORMULA>
C30H46O2

> <MOLECULAR_WEIGHT>
438.696

> <EXACT_MASS>
438.349780721

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
25.047810348041313

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4S,5R,8S,13S,14R,17R,18R)-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracos-15-en-10-one

> <ALOGPS_LOGP>
5.92

> <JCHEM_LOGP>
6.965820205333333

> <ALOGPS_LOGS>
-7.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.91588272225339

> <JCHEM_PKA_STRONGEST_BASIC>
-4.203569442362231

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
130.9133

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.24e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,5R,8S,13S,14R,17R,18R)-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracos-15-en-10-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       2.373  -2.456   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.202  -0.962   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.889  -0.156   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.465  -0.889   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.507  -2.429   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.806  -3.235   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.046  -4.574   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.491  -4.614   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.890   1.129   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.486   1.078   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.149  -0.401   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.270  -1.794   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.187  -3.095   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.744  -3.071   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.492  -1.716   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.710  -0.389   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.468   0.951   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.007   0.965   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.790  -0.361   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.032  -1.702   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.814  -3.028   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.354  -3.015   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.111  -1.674   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      12.651  -1.660   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.329  -0.347   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.628   0.481   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.369   1.192   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.274  -3.042   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.928   0.938   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.873  -2.726   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.543  -1.781   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.060   1.136   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   12                                                  
CONECT    3    2    4    9   31                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7    8                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    3   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16   32                                             
CONECT   12   11    2   13   30                                             
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   11   17   29                                             
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19   15   21   28                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   19   26   27                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   20                                                            
CONECT   29   16                                                            
CONECT   30   12   31                                                       
CONECT   31   30    3                                                       
CONECT   32   11                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₆O₂

Average Mass

438.6960 Da

Monoisotopic Mass

438.34978 Da

IUPAC Name

(1S,4S,5R,8S,13S,14R,17R,18R)-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracos-15-en-10-one

Traditional Name

(1S,4S,5R,8S,13S,14R,17R,18R)-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracos-15-en-10-one

CAS Registry Number

Not Available

SMILES

CC1(C)CC[C@]23CO[C@]4(C=C[C@@H]5[C@@]6(C)CCC(=O)C(C)(C)[C@H]6CC[C@@]5(C)[C@]4(C)CC2)[C@@H]3C1

InChI Identifier

InChI=1S/C30H46O2/c1-24(2)14-16-29-17-15-28(7)27(6)12-8-20-25(3,4)23(31)10-11-26(20,5)21(27)9-13-30(28,32-19-29)22(29)18-24/h9,13,20-22H,8,10-12,14-19H2,1-7H3/t20-,21-,22-,26+,27-,28+,29-,30-/m1/s1

InChI Key

BFSRJRKZZSIEFP-MOHLSBLISA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Viburnum awabuki	Plant	KNApSAcK

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
Oxepane
Tetrahydrofuran
Cyclic ketone
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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	5.92	ALOGPS
logP	6.97	ChemAxon
logS	-7.3	ALOGPS
pKa (Strongest Acidic)	19.92	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	130.91 m³·mol⁻¹	ChemAxon
Polarizability	25.05 Å³	ChemAxon
Number of Rings	6	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

162975862

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-13,28-Epoxy-11-oleanene-3-one (NP0082246)

MOL for NP0082246 ((+)-13,28-Epoxy-11-oleanene-3-one)

3D MOL for NP0082246 ((+)-13,28-Epoxy-11-oleanene-3-one)

3D SDF for NP0082246 ((+)-13,28-Epoxy-11-oleanene-3-one)

3D-SDF for NP0082246 ((+)-13,28-Epoxy-11-oleanene-3-one)

PDB for NP0082246 ((+)-13,28-Epoxy-11-oleanene-3-one)

3D PDB for NP0082246 ((+)-13,28-Epoxy-11-oleanene-3-one)

SMILES for NP0082246 ((+)-13,28-Epoxy-11-oleanene-3-one)

INCHI for NP0082246 ((+)-13,28-Epoxy-11-oleanene-3-one)

Structure for NP0082246 ((+)-13,28-Epoxy-11-oleanene-3-one)

3D Structure for NP0082246 ((+)-13,28-Epoxy-11-oleanene-3-one)