NP-MRD: Showing NP-Card for 3'-(acetyloxy)-2'-(hydroxymethyl)-2-methyl-5'-(6-methylhepta-2,5-dien-2-yl)-5-oxo-[1,1'-bi(cyclopentane)]-3-yl acetate (NP0253129)

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Record Information

Version

2.0

Created at

2022-09-07 16:54:27 UTC

Updated at

2022-09-07 16:54:27 UTC

NP-MRD ID

NP0253129

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3'-(acetyloxy)-2'-(hydroxymethyl)-2-methyl-5'-(6-methylhepta-2,5-dien-2-yl)-5-oxo-[1,1'-bi(cyclopentane)]-3-yl acetate

Description

3'-(Acetyloxy)-2-(hydroxymethyl)-2'-methyl-5-(6-methylhepta-2,5-dien-2-yl)-5'-oxo-[1,1'-bi(cyclopentane)]-3-yl acetate belongs to the class of organic compounds known as spatane and 4,10-secospatane diterpenoids. These are diterpenoids with a structure based on the spatane or 4,10-secospatane skeleton. The spatane skeleton is formally derived from a prenylgermacrane by 1,5- and 6,10-cyclisation. 3'-(acetyloxy)-2'-(hydroxymethyl)-2-methyl-5'-(6-methylhepta-2,5-dien-2-yl)-5-oxo-[1,1'-bi(cyclopentane)]-3-yl acetate is found in Dilophus marginatus. 3'-(Acetyloxy)-2-(hydroxymethyl)-2'-methyl-5-(6-methylhepta-2,5-dien-2-yl)-5'-oxo-[1,1'-bi(cyclopentane)]-3-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004201501422D          

 30 31  0  0  0  0            999 V2000
    1.2564   -0.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2564   -1.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5890   -1.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8439   -2.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6689   -2.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1538   -2.9422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9239   -1.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7085   -1.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9634   -0.4506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4785    0.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6580    0.1306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7884   -0.4506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0434   -1.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3759   -1.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3759   -2.5451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6615   -2.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6615   -3.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9470   -4.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2325   -3.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5180   -4.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2325   -2.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0904   -2.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2733    0.2169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9378    0.9705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1173    1.0568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4227    1.6380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1956   -1.2352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8087   -1.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5934   -1.5323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6372   -2.5942    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  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  4  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 15 22  1  0  0  0  0
 12 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
  3 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
M  END


  Mrv1533004201501422D          

 30 31  0  0  0  0            999 V2000
    1.2564   -0.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2564   -1.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5890   -1.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8439   -2.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6689   -2.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1538   -2.9422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9239   -1.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7085   -1.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9634   -0.4506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4785    0.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6580    0.1306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7884   -0.4506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0434   -1.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3759   -1.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3759   -2.5451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6615   -2.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6615   -3.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9470   -4.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2325   -3.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5180   -4.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2325   -2.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0904   -2.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2733    0.2169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9378    0.9705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1173    1.0568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4227    1.6380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1956   -1.2352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8087   -1.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5934   -1.5323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6372   -2.5942    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  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  4  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 15 22  1  0  0  0  0
 12 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
  3 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0253129

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C(CC(=O)C1C1C(CO)C(CC1C(C)=CCC=C(C)C)OC(C)=O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H36O6/c1-13(2)8-7-9-14(3)18-10-22(30-17(6)27)19(12-25)24(18)23-15(4)21(11-20(23)28)29-16(5)26/h8-9,15,18-19,21-25H,7,10-12H2,1-6H3

> <INCHI_KEY>
NZWVOVFKAOWSBT-UHFFFAOYSA-N

> <FORMULA>
C24H36O6

> <MOLECULAR_WEIGHT>
420.546

> <EXACT_MASS>
420.251188879

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
46.96363296643418

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[3-(acetyloxy)-2-(hydroxymethyl)-5-(6-methylhepta-2,5-dien-2-yl)cyclopentyl]-2-methyl-4-oxocyclopentyl acetate

> <ALOGPS_LOGP>
3.21

> <JCHEM_LOGP>
2.6158977076666656

> <ALOGPS_LOGS>
-4.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.028773723868266

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.376367574635395

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6336181093364965

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
115.3822

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.01e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[3-(acetyloxy)-2-(hydroxymethyl)-5-(6-methylhepta-2,5-dien-2-yl)cyclopentyl]-2-methyl-4-oxocyclopentyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       2.345  -0.336   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.345  -1.876   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.099  -2.782   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.575  -4.246   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.115  -4.246   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.021  -5.492   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.591  -2.782   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.056  -2.306   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.532  -0.841   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.627   0.405   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.095   0.244   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.072  -0.841   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.548  -2.306   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.302  -3.211   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.302  -4.751   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.968  -5.521   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.968  -7.061   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.634  -7.831   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.301  -7.061   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.967  -7.831   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.301  -5.521   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.635  -5.521   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.977   0.405   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.351   1.812   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.819   1.973   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.256   3.058   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.365  -2.306   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.510  -3.336   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.974  -2.860   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.189  -4.843   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   27                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    2    8                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   23                                                  
CONECT   13   12   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   15                                                            
CONECT   23   12   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27    3   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

View in JSmol

Synonyms

Value	Source
3'-(Acetyloxy)-2-(hydroxymethyl)-2'-methyl-5-(6-methylhepta-2,5-dien-2-yl)-5'-oxo-[1,1'-bi(cyclopentane)]-3-yl acetic acid	Generator

Chemical Formula

C₂₄H₃₆O₆

Average Mass

420.5460 Da

Monoisotopic Mass

420.25119 Da

IUPAC Name

3-[3-(acetyloxy)-2-(hydroxymethyl)-5-(6-methylhepta-2,5-dien-2-yl)cyclopentyl]-2-methyl-4-oxocyclopentyl acetate

Traditional Name

3-[3-(acetyloxy)-2-(hydroxymethyl)-5-(6-methylhepta-2,5-dien-2-yl)cyclopentyl]-2-methyl-4-oxocyclopentyl acetate

CAS Registry Number

Not Available

SMILES

CC1C(CC(=O)C1C1C(CO)C(CC1C(C)=CCC=C(C)C)OC(C)=O)OC(C)=O

InChI Identifier

InChI=1S/C24H36O6/c1-13(2)8-7-9-14(3)18-10-22(30-17(6)27)19(12-25)24(18)23-15(4)21(11-20(23)28)29-16(5)26/h8-9,15,18-19,21-25H,7,10-12H2,1-6H3

InChI Key

NZWVOVFKAOWSBT-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Dilophus marginatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as spatane and 4,10-secospatane diterpenoids. These are diterpenoids with a structure based on the spatane or 4,10-secospatane skeleton. The spatane skeleton is formally derived from a prenylgermacrane by 1,5- and 6,10-cyclisation.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Spatane and 4,10-secospatane diterpenoids

Alternative Parents

Substituents

4,10-secospatane diterpenoid
Dicarboxylic acid or derivatives
Cyclic ketone
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	3.21	ALOGPS
logP	2.62	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	15.38	ChemAxon
pKa (Strongest Basic)	-2.6	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	9	ChemAxon
Refractivity	115.38 m³·mol⁻¹	ChemAxon
Polarizability	46.96 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

74052120

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3'-(acetyloxy)-2'-(hydroxymethyl)-2-methyl-5'-(6-methylhepta-2,5-dien-2-yl)-5-oxo-[1,1'-bi(cyclopentane)]-3-yl acetate (NP0253129)

MOL for NP0253129 (3'-(acetyloxy)-2'-(hydroxymethyl)-2-methyl-5'-(6-methylhepta-2,5-dien-2-yl)-5-oxo-[1,1'-bi(cyclopentane)]-3-yl acetate)

3D MOL for NP0253129 (3'-(acetyloxy)-2'-(hydroxymethyl)-2-methyl-5'-(6-methylhepta-2,5-dien-2-yl)-5-oxo-[1,1'-bi(cyclopentane)]-3-yl acetate)

3D SDF for NP0253129 (3'-(acetyloxy)-2'-(hydroxymethyl)-2-methyl-5'-(6-methylhepta-2,5-dien-2-yl)-5-oxo-[1,1'-bi(cyclopentane)]-3-yl acetate)

3D-SDF for NP0253129 (3'-(acetyloxy)-2'-(hydroxymethyl)-2-methyl-5'-(6-methylhepta-2,5-dien-2-yl)-5-oxo-[1,1'-bi(cyclopentane)]-3-yl acetate)

PDB for NP0253129 (3'-(acetyloxy)-2'-(hydroxymethyl)-2-methyl-5'-(6-methylhepta-2,5-dien-2-yl)-5-oxo-[1,1'-bi(cyclopentane)]-3-yl acetate)

3D PDB for NP0253129 (3'-(acetyloxy)-2'-(hydroxymethyl)-2-methyl-5'-(6-methylhepta-2,5-dien-2-yl)-5-oxo-[1,1'-bi(cyclopentane)]-3-yl acetate)

SMILES for NP0253129 (3'-(acetyloxy)-2'-(hydroxymethyl)-2-methyl-5'-(6-methylhepta-2,5-dien-2-yl)-5-oxo-[1,1'-bi(cyclopentane)]-3-yl acetate)

INCHI for NP0253129 (3'-(acetyloxy)-2'-(hydroxymethyl)-2-methyl-5'-(6-methylhepta-2,5-dien-2-yl)-5-oxo-[1,1'-bi(cyclopentane)]-3-yl acetate)

Structure for NP0253129 (3'-(acetyloxy)-2'-(hydroxymethyl)-2-methyl-5'-(6-methylhepta-2,5-dien-2-yl)-5-oxo-[1,1'-bi(cyclopentane)]-3-yl acetate)

3D Structure for NP0253129 (3'-(acetyloxy)-2'-(hydroxymethyl)-2-methyl-5'-(6-methylhepta-2,5-dien-2-yl)-5-oxo-[1,1'-bi(cyclopentane)]-3-yl acetate)