NP-MRD: Showing NP-Card for 2-{[1-(5-ethyl-6-methylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-4,5-dihydroxyoxan-3-yl tetracosanoate (NP0323098)

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Record Information

Version

2.0

Created at

2022-09-12 02:18:50 UTC

Updated at

2022-09-12 02:18:50 UTC

NP-MRD ID

NP0323098

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{[1-(5-ethyl-6-methylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-4,5-dihydroxyoxan-3-yl tetracosanoate

Description

2-{[14-(5-Ethyl-6-methylhept-3-en-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-5-yl]oxy}-4,5-dihydroxyoxan-3-yl tetracosanoate belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. 2-{[1-(5-ethyl-6-methylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-4,5-dihydroxyoxan-3-yl tetracosanoate is found in Asparagus adscendens. 2-{[14-(5-Ethyl-6-methylhept-3-en-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-5-yl]oxy}-4,5-dihydroxyoxan-3-yl tetracosanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241516232D          

 64 68  0  0  0  0            999 V2000
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M  END


  Mrv1533004241516232D          

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M  END
> <DATABASE_ID>
NP0323098

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCCCCCCCCCC(=O)OC1C(O)C(O)COC1OC1CCC2(C)C3CCC4(C)C(CCC4C3CC=C2C1)C(C)C=CC(CC)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C58H102O6/c1-8-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-29-30-53(60)64-55-54(61)52(59)42-62-56(55)63-47-37-39-57(6)46(41-47)33-34-48-50-36-35-49(58(50,7)40-38-51(48)57)44(5)31-32-45(9-2)43(3)4/h31-33,43-45,47-52,54-56,59,61H,8-30,34-42H2,1-7H3

> <INCHI_KEY>
BGRNFVBVVITQRP-UHFFFAOYSA-N

> <FORMULA>
C58H102O6

> <MOLECULAR_WEIGHT>
895.448

> <EXACT_MASS>
894.767641004

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
166

> <JCHEM_AVERAGE_POLARIZABILITY>
115.79423568932879

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[14-(5-ethyl-6-methylhept-3-en-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxy}-4,5-dihydroxyoxan-3-yl tetracosanoate

> <ALOGPS_LOGP>
10.37

> <JCHEM_LOGP>
16.819657654000007

> <ALOGPS_LOGS>
-7.74

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.32590051095217

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.812756552401204

> <JCHEM_PKA_STRONGEST_BASIC>
-3.527302841493439

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
267.73290000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
31

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.65e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[14-(5-ethyl-6-methylhept-3-en-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxy}-4,5-dihydroxyoxan-3-yl tetracosanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0     -17.329 -33.329   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -15.936 -33.987   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -14.670 -33.110   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -13.278 -33.768   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -12.012 -32.891   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.620 -33.549   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -9.354 -32.671   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -7.961 -33.329   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.695 -32.452   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.303 -33.110   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.037 -32.233   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.645 -32.891   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.379 -32.014   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.014 -32.671   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.280 -31.794   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.672 -32.452   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.938 -31.575   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.330 -32.233   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.596 -31.356   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.989 -32.014   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.255 -31.137   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.647 -31.794   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.913 -30.917   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.305 -31.575   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      14.571 -30.698   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      13.432 -33.110   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      14.824 -33.768   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.951 -35.303   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      13.685 -36.180   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      16.343 -35.960   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      16.470 -37.495   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      17.609 -35.083   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      17.483 -33.549   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      16.090 -32.891   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      15.964 -31.356   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      17.230 -30.479   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      17.103 -28.944   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      18.369 -28.067   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      19.761 -28.725   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      19.635 -27.190   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      21.027 -27.848   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      20.901 -26.313   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      22.166 -25.436   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      23.559 -26.094   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      23.593 -24.554   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      24.979 -25.499   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      25.984 -26.666   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      25.184 -27.982   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      23.685 -27.629   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      22.420 -28.506   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      22.546 -30.040   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      21.280 -30.917   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      19.888 -30.260   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      18.622 -31.137   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      25.333 -24.000   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      26.808 -23.557   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      24.212 -22.945   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      24.566 -21.446   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      23.445 -20.390   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      21.970 -20.833   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      20.849 -19.777   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      23.799 -18.891   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      25.274 -18.448   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      22.678 -17.835   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   34                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   27   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   54                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   41   53                                             
CONECT   40   39                                                            
CONECT   41   39   42   50                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45   46   49                                             
CONECT   45   44                                                            
CONECT   46   44   47   55                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   44   50                                                  
CONECT   50   49   41   51                                                  
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   39   54                                                  
CONECT   54   53   36                                                       
CONECT   55   46   56   57                                                  
CONECT   56   55                                                            
CONECT   57   55   58                                                       
CONECT   58   57   59                                                       
CONECT   59   58   60   62                                                  
CONECT   60   59   61                                                       
CONECT   61   60                                                            
CONECT   62   59   63   64                                                  
CONECT   63   62                                                            
CONECT   64   62                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  136    0
END

View in JSmol

Synonyms

Value	Source
2-{[14-(5-ethyl-6-methylhept-3-en-2-yl)-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadec-7-en-5-yl]oxy}-4,5-dihydroxyoxan-3-yl tetracosanoic acid	Generator
2-{[14-(5-ethyl-6-methylhept-3-en-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxy}-4,5-dihydroxyoxan-3-yl tetracosanoic acid	Generator

Chemical Formula

C₅₈H₁₀₂O₆

Average Mass

895.4480 Da

Monoisotopic Mass

894.76764 Da

IUPAC Name

2-{[14-(5-ethyl-6-methylhept-3-en-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxy}-4,5-dihydroxyoxan-3-yl tetracosanoate

Traditional Name

2-{[14-(5-ethyl-6-methylhept-3-en-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxy}-4,5-dihydroxyoxan-3-yl tetracosanoate

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCCCCCCCCC(=O)OC1C(O)C(O)COC1OC1CCC2(C)C3CCC4(C)C(CCC4C3CC=C2C1)C(C)C=CC(CC)C(C)C

InChI Identifier

InChI=1S/C58H102O6/c1-8-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-29-30-53(60)64-55-54(61)52(59)42-62-56(55)63-47-37-39-57(6)46(41-47)33-34-48-50-36-35-49(58(50,7)40-38-51(48)57)44(5)31-32-45(9-2)43(3)4/h31-33,43-45,47-52,54-56,59,61H,8-30,34-42H2,1-7H3

InChI Key

BGRNFVBVVITQRP-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Asparagus adscendens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Stigmastanes and derivatives

Direct Parent

Stigmastanes and derivatives

Alternative Parents

Substituents

C24-propyl-sterol-skeleton
Stigmastane-skeleton
Triterpenoid
Steroidal glycoside
Delta-5-steroid
Glycosyl compound
O-glycosyl compound
Oxane
Monosaccharide
Secondary alcohol
1,2-diol
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Acetal
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
Alcohol
Organooxygen compound
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	10.37	ALOGPS
logP	16.82	ChemAxon
logS	-7.7	ALOGPS
pKa (Strongest Acidic)	12.81	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	31	ChemAxon
Refractivity	267.73 m³·mol⁻¹	ChemAxon
Polarizability	115.79 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

LOTUS database [Link]

Showing NP-Card for 2-{[1-(5-ethyl-6-methylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-4,5-dihydroxyoxan-3-yl tetracosanoate (NP0323098)

MOL for NP0323098 (2-{[1-(5-ethyl-6-methylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-4,5-dihydroxyoxan-3-yl tetracosanoate)

3D MOL for NP0323098 (2-{[1-(5-ethyl-6-methylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-4,5-dihydroxyoxan-3-yl tetracosanoate)

3D SDF for NP0323098 (2-{[1-(5-ethyl-6-methylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-4,5-dihydroxyoxan-3-yl tetracosanoate)

3D-SDF for NP0323098 (2-{[1-(5-ethyl-6-methylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-4,5-dihydroxyoxan-3-yl tetracosanoate)

PDB for NP0323098 (2-{[1-(5-ethyl-6-methylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-4,5-dihydroxyoxan-3-yl tetracosanoate)

3D PDB for NP0323098 (2-{[1-(5-ethyl-6-methylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-4,5-dihydroxyoxan-3-yl tetracosanoate)

SMILES for NP0323098 (2-{[1-(5-ethyl-6-methylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-4,5-dihydroxyoxan-3-yl tetracosanoate)

INCHI for NP0323098 (2-{[1-(5-ethyl-6-methylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-4,5-dihydroxyoxan-3-yl tetracosanoate)

Structure for NP0323098 (2-{[1-(5-ethyl-6-methylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-4,5-dihydroxyoxan-3-yl tetracosanoate)

3D Structure for NP0323098 (2-{[1-(5-ethyl-6-methylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-4,5-dihydroxyoxan-3-yl tetracosanoate)