NP-MRD: Showing NP-Card for (3s,7r,10s,13s)-3,7,13-trimethyl-10-(prop-1-en-2-yl)cyclotetradecane-1,6-dione (NP0247180)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 08:55:30 UTC

Updated at

2022-09-07 08:55:31 UTC

NP-MRD ID

NP0247180

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,7r,10s,13s)-3,7,13-trimethyl-10-(prop-1-en-2-yl)cyclotetradecane-1,6-dione

Description

3Beta,9beta,13alpha-Trimethyl-6alpha-isopropenylcyclotetradecane-1,10-dione belongs to the class of organic compounds known as cembrane diterpenoids. These are diterpenoids with a structure based a cembrane skeleton, which is characterized by the presence of an isopropyl group at C-1 and by three symmetrically disposed methyl groups a the t C-4, -8 and -12 positions. (3s,7r,10s,13s)-3,7,13-trimethyl-10-(prop-1-en-2-yl)cyclotetradecane-1,6-dione is found in Pseudoplexaura flagellosa. Based on a literature review very few articles have been published on 3beta,9beta,13alpha-Trimethyl-6alpha-isopropenylcyclotetradecane-1,10-dione.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072210552D          

 22 22  0  0  1  0            999 V2000
    0.7060    1.8206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5161    1.6647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0562    2.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.8851    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3263    1.5088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1364    1.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4064    0.5733    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2166    0.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8664   -0.0503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1364   -0.8299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9465   -0.9858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5963   -1.4535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -1.2976    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0562   -2.0772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2461   -1.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4360   -1.7654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1659   -0.9858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6442   -0.8299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7060   -0.3622    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5161   -0.5181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4360    0.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9760    1.0410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
  4 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0247180

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC[C@@H](CC[C@@H](C)C(=O)CC[C@H](C)CC(=O)C1)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O2/c1-14(2)18-9-6-15(3)12-19(21)13-16(4)7-11-20(22)17(5)8-10-18/h15-18H,1,6-13H2,2-5H3/t15-,16-,17+,18-/m0/s1

> <INCHI_KEY>
UJGSGRUKHMYDMU-FJIDUMEYSA-N

> <FORMULA>
C20H34O2

> <MOLECULAR_WEIGHT>
306.49

> <EXACT_MASS>
306.255880335

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
37.528272432424544

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,7R,10S,13S)-3,7,13-trimethyl-10-(prop-1-en-2-yl)cyclotetradecane-1,6-dione

> <JCHEM_LOGP>
5.653511377000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.079777199523595

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
92.84419999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S,7R,10S,13S)-3,7,13-trimethyl-10-(prop-1-en-2-yl)cyclotetradecane-1,6-dione

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       1.318   3.398   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.830   3.107   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.838   4.272   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.334   1.652   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.342   2.816   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.855   2.525   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.359   1.070   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.871   0.779   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.351  -0.094   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.855  -1.549   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.367  -1.840   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.846  -2.713   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.334  -2.422   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.838  -3.877   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.326  -3.586   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.814  -3.295   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.310  -1.840   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.203  -1.549   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.318  -0.676   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.830  -0.967   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.814   0.779   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.822   1.943   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   22                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21    4                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

View in JSmol

Synonyms

Value	Source
3b,9b,13a-Trimethyl-6a-isopropenylcyclotetradecane-1,10-dione	Generator
3Β,9β,13α-trimethyl-6α-isopropenylcyclotetradecane-1,10-dione	Generator

Chemical Formula

C₂₀H₃₄O₂

Average Mass

306.4900 Da

Monoisotopic Mass

306.25588 Da

IUPAC Name

(3S,7R,10S,13S)-3,7,13-trimethyl-10-(prop-1-en-2-yl)cyclotetradecane-1,6-dione

Traditional Name

(3S,7R,10S,13S)-3,7,13-trimethyl-10-(prop-1-en-2-yl)cyclotetradecane-1,6-dione

CAS Registry Number

Not Available

SMILES

C[C@H]1CC[C@@H](CC[C@@H](C)C(=O)CC[C@H](C)CC(=O)C1)C(C)=C

InChI Identifier

InChI=1S/C20H34O2/c1-14(2)18-9-6-15(3)12-19(21)13-16(4)7-11-20(22)17(5)8-10-18/h15-18H,1,6-13H2,2-5H3/t15-,16-,17+,18-/m0/s1

InChI Key

UJGSGRUKHMYDMU-FJIDUMEYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Pseudoplexaura flagellosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cembrane diterpenoids. These are diterpenoids with a structure based a cembrane skeleton, which is characterized by the presence of an isopropyl group at C-1 and by three symmetrically disposed methyl groups a the t C-4, -8 and -12 positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Cembrane diterpenoids

Alternative Parents

Substituents

Cembrane diterpenoid
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	5.65	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	92.84 m³·mol⁻¹	ChemAxon
Polarizability	37.53 Å³	ChemAxon
Number of Rings	1	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

28185160

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

56834684

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s,7r,10s,13s)-3,7,13-trimethyl-10-(prop-1-en-2-yl)cyclotetradecane-1,6-dione (NP0247180)

MOL for NP0247180 ((3s,7r,10s,13s)-3,7,13-trimethyl-10-(prop-1-en-2-yl)cyclotetradecane-1,6-dione)

3D MOL for NP0247180 ((3s,7r,10s,13s)-3,7,13-trimethyl-10-(prop-1-en-2-yl)cyclotetradecane-1,6-dione)

3D SDF for NP0247180 ((3s,7r,10s,13s)-3,7,13-trimethyl-10-(prop-1-en-2-yl)cyclotetradecane-1,6-dione)

3D-SDF for NP0247180 ((3s,7r,10s,13s)-3,7,13-trimethyl-10-(prop-1-en-2-yl)cyclotetradecane-1,6-dione)

PDB for NP0247180 ((3s,7r,10s,13s)-3,7,13-trimethyl-10-(prop-1-en-2-yl)cyclotetradecane-1,6-dione)

3D PDB for NP0247180 ((3s,7r,10s,13s)-3,7,13-trimethyl-10-(prop-1-en-2-yl)cyclotetradecane-1,6-dione)

SMILES for NP0247180 ((3s,7r,10s,13s)-3,7,13-trimethyl-10-(prop-1-en-2-yl)cyclotetradecane-1,6-dione)

INCHI for NP0247180 ((3s,7r,10s,13s)-3,7,13-trimethyl-10-(prop-1-en-2-yl)cyclotetradecane-1,6-dione)

Structure for NP0247180 ((3s,7r,10s,13s)-3,7,13-trimethyl-10-(prop-1-en-2-yl)cyclotetradecane-1,6-dione)

3D Structure for NP0247180 ((3s,7r,10s,13s)-3,7,13-trimethyl-10-(prop-1-en-2-yl)cyclotetradecane-1,6-dione)