NP-MRD: Showing NP-Card for (ent-2b,4S,9a)-2,4,9-Trihydroxy-10(14)-oplopen-3-one 2-(2-methylbutanoate) 9-(3-methyl-2E-pentenoate) (NP0335403)

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Record Information

Version

2.0

Created at

2024-09-11 01:26:56 UTC

Updated at

2024-09-11 01:26:57 UTC

NP-MRD ID

NP0335403

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(ent-2b,4S,9a)-2,4,9-Trihydroxy-10(14)-oplopen-3-one 2-(2-methylbutanoate) 9-(3-methyl-2E-pentenoate)

Description

(Ent-2b,4S,9a)-2,4,9-Trihydroxy-10(14)-oplopen-3-one 2-(2-methylbutanoate) 9-(3-methyl-2E-pentenoate) belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review very few articles have been published on (ent-2b,4S,9a)-2,4,9-Trihydroxy-10(14)-oplopen-3-one 2-(2-methylbutanoate) 9-(3-methyl-2E-pentenoate).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262303592D          

 32 33  0  0  0  0            999 V2000
    7.9571   -1.8101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1015    2.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0836    4.7369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1455    3.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4473   -0.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5304    1.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1304    1.4999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4177    5.6463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5092   -1.1970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8159    3.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8063    0.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0414    2.5546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3385    3.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2542   -0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5304    2.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6824    2.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9026    4.9789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7865    3.3392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4894    1.9415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5513    0.9854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4275    2.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5670    4.2252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9795    3.5107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7601    4.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6738    3.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2449    3.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7231    5.0651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1034    1.5984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1470    4.6057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2449    4.0582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7444    1.1569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9594    2.8207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  0  0  0  0
 10  2  1  0  0  0  0
 13  3  1  0  0  0  0
 13  4  1  0  0  0  0
 14  5  1  0  0  0  0
 14  9  1  0  0  0  0
 14 11  2  0  0  0  0
 15  6  1  0  0  0  0
 15 10  1  0  0  0  0
 16  7  2  0  0  0  0
 17  8  1  0  0  0  0
 18 12  1  0  0  0  0
 18 13  1  0  0  0  0
 19 12  1  0  0  0  0
 19 16  1  0  0  0  0
 20 11  1  0  0  0  0
 21 16  1  0  0  0  0
 22 17  1  0  0  0  0
 23 18  1  0  0  0  0
 23 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 22  1  0  0  0  0
 25 21  1  0  0  0  0
 25 24  1  0  0  0  0
 26 15  1  0  0  0  0
 27 17  1  0  0  0  0
 28 20  2  0  0  0  0
 29 24  2  0  0  0  0
 30 26  2  0  0  0  0
 31 19  1  0  0  0  0
 31 20  1  0  0  0  0
 32 25  1  0  0  0  0
 32 26  1  0  0  0  0
M  END


  Mrv2104 05262303592D          

 32 33  0  0  0  0            999 V2000
    7.9571   -1.8101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1015    2.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0836    4.7369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1455    3.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4473   -0.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5304    1.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1304    1.4999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4177    5.6463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5092   -1.1970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8159    3.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8063    0.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0414    2.5546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3385    3.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2542   -0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5304    2.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6824    2.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9026    4.9789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7865    3.3392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4894    1.9415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5513    0.9854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4275    2.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5670    4.2252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9795    3.5107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7601    4.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6738    3.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2449    3.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7231    5.0651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1034    1.5984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1470    4.6057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2449    4.0582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7444    1.1569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9594    2.8207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  0  0  0  0
 10  2  1  0  0  0  0
 13  3  1  0  0  0  0
 13  4  1  0  0  0  0
 14  5  1  0  0  0  0
 14  9  1  0  0  0  0
 14 11  2  0  0  0  0
 15  6  1  0  0  0  0
 15 10  1  0  0  0  0
 16  7  2  0  0  0  0
 17  8  1  0  0  0  0
 18 12  1  0  0  0  0
 18 13  1  0  0  0  0
 19 12  1  0  0  0  0
 19 16  1  0  0  0  0
 20 11  1  0  0  0  0
 21 16  1  0  0  0  0
 22 17  1  0  0  0  0
 23 18  1  0  0  0  0
 23 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 22  1  0  0  0  0
 25 21  1  0  0  0  0
 25 24  1  0  0  0  0
 26 15  1  0  0  0  0
 27 17  1  0  0  0  0
 28 20  2  0  0  0  0
 29 24  2  0  0  0  0
 30 26  2  0  0  0  0
 31 19  1  0  0  0  0
 31 20  1  0  0  0  0
 32 25  1  0  0  0  0
 32 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0335403

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C(=O)OC1C2C(C(C(C)O)C1=O)C(CC(OC(=O)\C=C(/C)CC)C2=C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1/C26H40O6/c1-9-14(5)11-20(28)31-19-12-18(13(3)4)23-21(16(19)7)25(24(29)22(23)17(8)27)32-26(30)15(6)10-2/h11,13,15,17-19,21-23,25,27H,7,9-10,12H2,1-6,8H3/b14-11+

> <INCHI_KEY>
YTOWGNDHXAGFBR-SDNWHVSQNA-N

> <FORMULA>
C26H40O6

> <MOLECULAR_WEIGHT>
448.6

> <EXACT_MASS>
448.282489008

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
50.20419817915919

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(1-hydroxyethyl)-3-[(2-methylbutanoyl)oxy]-4-methylidene-2-oxo-7-(propan-2-yl)-octahydro-1H-inden-5-yl (2E)-3-methylpent-2-enoate

> <JCHEM_LOGP>
5.290455133999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.347192674991035

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.085086015274912

> <JCHEM_PKA_STRONGEST_BASIC>
-2.761415874485886

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
123.17599999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
1-(1-hydroxyethyl)-7-isopropyl-3-[(2-methylbutanoyl)oxy]-4-methylidene-2-oxo-hexahydro-1H-inden-5-yl (2E)-3-methylpent-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      14.853  -3.379   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.923   5.265   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.089   8.842   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.072   7.057   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.902  -0.449   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.590   3.725   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.443   2.800   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.980  10.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.884  -2.234   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.256   6.035   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.438   0.375   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.011   4.769   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.565   7.378   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.408  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.590   5.265   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.474   3.944   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.885   9.294   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.535   6.233   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.980   3.624   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.962   1.839   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.998   5.409   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.258   7.887   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.028   6.553   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.752   7.567   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.591   6.035   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.924   6.035   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      14.416   9.455   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      16.993   2.984   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       9.608   8.597   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       7.924   7.575   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      14.456   2.160   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       9.258   5.265   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   13                                                            
CONECT    4   13                                                            
CONECT    5   14                                                            
CONECT    6   15                                                            
CONECT    7   16                                                            
CONECT    8   17                                                            
CONECT    9    1   14                                                       
CONECT   10    2   15                                                       
CONECT   11   14   20                                                       
CONECT   12   18   19                                                       
CONECT   13    3    4   18                                                  
CONECT   14    5    9   11                                                  
CONECT   15    6   10   26                                                  
CONECT   16    7   19   21                                                  
CONECT   17    8   22   27                                                  
CONECT   18   12   13   23                                                  
CONECT   19   12   16   31                                                  
CONECT   20   11   28   31                                                  
CONECT   21   16   23   25                                                  
CONECT   22   17   23   24                                                  
CONECT   23   18   21   22                                                  
CONECT   24   22   25   29                                                  
CONECT   25   21   24   32                                                  
CONECT   26   15   30   32                                                  
CONECT   27   17                                                            
CONECT   28   20                                                            
CONECT   29   24                                                            
CONECT   30   26                                                            
CONECT   31   19   20                                                       
CONECT   32   25   26                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   66    0
END

View in JSmol

Synonyms

Value	Source
(ent-2b,4S,9a)-2,4,9-Trihydroxy-10(14)-oplopen-3-one 2-(2-methylbutanoic acid) 9-(3-methyl-2E-pentenoic acid)	Generator

Chemical Formula

C₂₆H₄₀O₆

Average Mass

448.6000 Da

Monoisotopic Mass

448.28249 Da

IUPAC Name

1-(1-hydroxyethyl)-3-[(2-methylbutanoyl)oxy]-4-methylidene-2-oxo-7-(propan-2-yl)-octahydro-1H-inden-5-yl (2E)-3-methylpent-2-enoate

Traditional Name

1-(1-hydroxyethyl)-7-isopropyl-3-[(2-methylbutanoyl)oxy]-4-methylidene-2-oxo-hexahydro-1H-inden-5-yl (2E)-3-methylpent-2-enoate

CAS Registry Number

Not Available

SMILES

CCC(C)C(=O)OC1C2C(C(C(C)O)C1=O)C(CC(OC(=O)\C=C(/C)CC)C2=C)C(C)C

InChI Identifier

InChI=1/C26H40O6/c1-9-14(5)11-20(28)31-19-12-18(13(3)4)23-21(16(19)7)25(24(29)22(23)17(8)27)32-26(30)15(6)10-2/h11,13,15,17-19,21-23,25,27H,7,9-10,12H2,1-6,8H3/b14-11+

InChI Key

YTOWGNDHXAGFBR-SDNWHVSQNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Oplopane sesquiterpenoid
Fatty acid ester
Alpha-acyloxy ketone
Dicarboxylic acid or derivatives
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
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	5.29	ChemAxon
pKa (Strongest Acidic)	15.09	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	123.18 m³·mol⁻¹	ChemAxon
Polarizability	50.2 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (ent-2b,4S,9a)-2,4,9-Trihydroxy-10(14)-oplopen-3-one 2-(2-methylbutanoate) 9-(3-methyl-2E-pentenoate) (NP0335403)

MOL for NP0335403 ((ent-2b,4S,9a)-2,4,9-Trihydroxy-10(14)-oplopen-3-one 2-(2-methylbutanoate) 9-(3-methyl-2E-pentenoate))

3D MOL for NP0335403 ((ent-2b,4S,9a)-2,4,9-Trihydroxy-10(14)-oplopen-3-one 2-(2-methylbutanoate) 9-(3-methyl-2E-pentenoate))

3D SDF for NP0335403 ((ent-2b,4S,9a)-2,4,9-Trihydroxy-10(14)-oplopen-3-one 2-(2-methylbutanoate) 9-(3-methyl-2E-pentenoate))

3D-SDF for NP0335403 ((ent-2b,4S,9a)-2,4,9-Trihydroxy-10(14)-oplopen-3-one 2-(2-methylbutanoate) 9-(3-methyl-2E-pentenoate))

PDB for NP0335403 ((ent-2b,4S,9a)-2,4,9-Trihydroxy-10(14)-oplopen-3-one 2-(2-methylbutanoate) 9-(3-methyl-2E-pentenoate))

3D PDB for NP0335403 ((ent-2b,4S,9a)-2,4,9-Trihydroxy-10(14)-oplopen-3-one 2-(2-methylbutanoate) 9-(3-methyl-2E-pentenoate))

SMILES for NP0335403 ((ent-2b,4S,9a)-2,4,9-Trihydroxy-10(14)-oplopen-3-one 2-(2-methylbutanoate) 9-(3-methyl-2E-pentenoate))

INCHI for NP0335403 ((ent-2b,4S,9a)-2,4,9-Trihydroxy-10(14)-oplopen-3-one 2-(2-methylbutanoate) 9-(3-methyl-2E-pentenoate))

Structure for NP0335403 ((ent-2b,4S,9a)-2,4,9-Trihydroxy-10(14)-oplopen-3-one 2-(2-methylbutanoate) 9-(3-methyl-2E-pentenoate))

3D Structure for NP0335403 ((ent-2b,4S,9a)-2,4,9-Trihydroxy-10(14)-oplopen-3-one 2-(2-methylbutanoate) 9-(3-methyl-2E-pentenoate))