NP-MRD: Showing NP-Card for 6-{[1-(5-ethyl-6-methylheptan-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-dihydroxy-2-(hydroxymethyl)oxan-3-yl icosanoate (NP0297602)

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Record Information

Version

2.0

Created at

2022-09-10 08:05:43 UTC

Updated at

2022-09-10 08:05:44 UTC

NP-MRD ID

NP0297602

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-{[1-(5-ethyl-6-methylheptan-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-dihydroxy-2-(hydroxymethyl)oxan-3-yl icosanoate

Description

6-{[14-(5-Ethyl-6-methylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-5-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl icosanoate 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. 6-{[1-(5-ethyl-6-methylheptan-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-dihydroxy-2-(hydroxymethyl)oxan-3-yl icosanoate is found in Citrus reticulata. 6-{[14-(5-Ethyl-6-methylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-5-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl icosanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004161513562D          

 62 66  0  0  0  0            999 V2000
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M  END


  Mrv1533004161513562D          

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M  END
> <DATABASE_ID>
NP0297602

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCCCCCC(=O)OC1C(CO)OC(OC2CCC3(C)C4CCC5(C)C(CCC5C4CC=C3C2)C(C)CCC(CC)C(C)C)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C55H98O7/c1-8-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-49(57)62-52-48(38-56)61-53(51(59)50(52)58)60-43-33-35-54(6)42(37-43)29-30-44-46-32-31-45(55(46,7)36-34-47(44)54)40(5)27-28-41(9-2)39(3)4/h29,39-41,43-48,50-53,56,58-59H,8-28,30-38H2,1-7H3

> <INCHI_KEY>
CBLYMGCSIKNWSM-UHFFFAOYSA-N

> <FORMULA>
C55H98O7

> <MOLECULAR_WEIGHT>
871.382

> <EXACT_MASS>
870.731255496

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
160

> <JCHEM_AVERAGE_POLARIZABILITY>
111.95503677171816

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-{[14-(5-ethyl-6-methylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl icosanoate

> <ALOGPS_LOGP>
10.01

> <JCHEM_LOGP>
14.772969708666672

> <ALOGPS_LOGS>
-7.30

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.803023021197614

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.269093988366242

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9818002080504433

> <JCHEM_POLAR_SURFACE_AREA>
105.45000000000002

> <JCHEM_REFRACTIVITY>
254.1748000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
29

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.33e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-{[14-(5-ethyl-6-methylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl icosanoate

> <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      -9.322 -28.760   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.917 -29.391   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668 -28.490   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.264 -29.121   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.015 -28.220   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.610 -28.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.361 -27.949   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.044 -28.580   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.292 -27.679   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.697 -28.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.946 -27.409   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.351 -28.039   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.507 -29.571   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.912 -30.202   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.161 -29.301   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.566 -29.932   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.814 -29.031   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.219 -29.662   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.468 -28.760   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.873 -29.391   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      15.029 -30.923   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      16.122 -28.490   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      15.965 -26.958   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.561 -26.327   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      13.312 -27.228   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      14.404 -24.795   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      13.000 -24.164   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      15.653 -23.894   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      15.497 -22.362   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      16.746 -21.461   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.590 -19.928   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      17.839 -19.027   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      19.243 -19.658   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      19.087 -18.126   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      20.492 -18.757   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      20.336 -17.225   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      21.585 -16.324   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      22.990 -16.954   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      22.995 -15.414   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      24.399 -16.333   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      25.425 -17.480   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      24.651 -18.811   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      23.146 -18.486   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      21.897 -19.388   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      22.053 -20.920   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      20.804 -21.821   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      19.400 -21.190   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      18.151 -22.091   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      24.724 -14.827   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      26.190 -14.356   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      23.582 -13.793   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      23.907 -12.288   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      22.766 -11.254   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      23.091  -9.748   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      21.950  -8.714   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      21.300 -11.725   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      20.975 -13.230   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      20.159 -10.691   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      17.058 -24.525   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      17.214 -26.057   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      18.619 -26.688   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0      18.775 -28.220   0.000  0.00  0.00           O+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   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   60                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   59                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   48                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35   47                                             
CONECT   34   33                                                            
CONECT   35   33   36   44                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   40   43                                             
CONECT   39   38                                                            
CONECT   40   38   41   49                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   38   44                                                  
CONECT   44   43   35   45                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   33   48                                                  
CONECT   48   47   30                                                       
CONECT   49   40   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54   56                                                  
CONECT   54   53   55                                                       
CONECT   55   54                                                            
CONECT   56   53   57   58                                                  
CONECT   57   56                                                            
CONECT   58   56                                                            
CONECT   59   28   60                                                       
CONECT   60   59   23   61                                                  
CONECT   61   60   62                                                       
CONECT   62   61                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  132    0
END

View in JSmol

Synonyms

Value	Source
6-{[14-(5-ethyl-6-methylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadec-7-en-5-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl icosanoic acid	Generator
6-{[14-(5-ethyl-6-methylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl icosanoic acid	Generator

Chemical Formula

C₅₅H₉₈O₇

Average Mass

871.3820 Da

Monoisotopic Mass

870.73126 Da

IUPAC Name

6-{[14-(5-ethyl-6-methylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl icosanoate

Traditional Name

6-{[14-(5-ethyl-6-methylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl icosanoate

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCCCCC(=O)OC1C(CO)OC(OC2CCC3(C)C4CCC5(C)C(CCC5C4CC=C3C2)C(C)CCC(CC)C(C)C)C(O)C1O

InChI Identifier

InChI=1S/C55H98O7/c1-8-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-49(57)62-52-48(38-56)61-53(51(59)50(52)58)60-43-33-35-54(6)42(37-43)29-30-44-46-32-31-45(55(46,7)36-34-47(44)54)40(5)27-28-41(9-2)39(3)4/h29,39-41,43-48,50-53,56,58-59H,8-28,30-38H2,1-7H3

InChI Key

CBLYMGCSIKNWSM-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Citrus reticulata	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
Saccharolipid
Delta-5-steroid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Monosaccharide
Oxane
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Primary alcohol
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	10.01	ALOGPS
logP	14.77	ChemAxon
logS	-7.3	ALOGPS
pKa (Strongest Acidic)	12.27	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	29	ChemAxon
Refractivity	254.17 m³·mol⁻¹	ChemAxon
Polarizability	111.96 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 6-{[1-(5-ethyl-6-methylheptan-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-dihydroxy-2-(hydroxymethyl)oxan-3-yl icosanoate (NP0297602)

MOL for NP0297602 (6-{[1-(5-ethyl-6-methylheptan-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-dihydroxy-2-(hydroxymethyl)oxan-3-yl icosanoate)

3D MOL for NP0297602 (6-{[1-(5-ethyl-6-methylheptan-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-dihydroxy-2-(hydroxymethyl)oxan-3-yl icosanoate)

3D SDF for NP0297602 (6-{[1-(5-ethyl-6-methylheptan-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-dihydroxy-2-(hydroxymethyl)oxan-3-yl icosanoate)

3D-SDF for NP0297602 (6-{[1-(5-ethyl-6-methylheptan-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-dihydroxy-2-(hydroxymethyl)oxan-3-yl icosanoate)

PDB for NP0297602 (6-{[1-(5-ethyl-6-methylheptan-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-dihydroxy-2-(hydroxymethyl)oxan-3-yl icosanoate)

3D PDB for NP0297602 (6-{[1-(5-ethyl-6-methylheptan-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-dihydroxy-2-(hydroxymethyl)oxan-3-yl icosanoate)

SMILES for NP0297602 (6-{[1-(5-ethyl-6-methylheptan-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-dihydroxy-2-(hydroxymethyl)oxan-3-yl icosanoate)

INCHI for NP0297602 (6-{[1-(5-ethyl-6-methylheptan-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-dihydroxy-2-(hydroxymethyl)oxan-3-yl icosanoate)

Structure for NP0297602 (6-{[1-(5-ethyl-6-methylheptan-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-dihydroxy-2-(hydroxymethyl)oxan-3-yl icosanoate)

3D Structure for NP0297602 (6-{[1-(5-ethyl-6-methylheptan-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-dihydroxy-2-(hydroxymethyl)oxan-3-yl icosanoate)