NP-MRD: Showing NP-Card for (1r,2r,3r,4s,7r,8r,10z,14r)-14-(acetyloxy)-3-isopropyl-6,10,14-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadeca-5,10-dien-4-yl acetate (NP0219882)

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Record Information

Version

2.0

Created at

2022-09-05 21:01:18 UTC

Updated at

2022-09-05 21:01:18 UTC

NP-MRD ID

NP0219882

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,3r,4s,7r,8r,10z,14r)-14-(acetyloxy)-3-isopropyl-6,10,14-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadeca-5,10-dien-4-yl acetate

Description

Calicophirin B belongs to the class of organic compounds known as eunicellane and asbestinane diterpenoids. These are diterpenoids with a structure based on either the eunicellane (5,14-cyclocembrane) or the asbestinane skeleton. Based on a literature review very few articles have been published on calicophirin B.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052223012D          

 29 31  0  0  1  0            999 V2000
   -2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4849   -0.6674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2695   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5391   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5391    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5391    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    1.7474    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7545    2.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846    2.4148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1202    3.1685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9407    3.2547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6353    3.8359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4849    1.4924    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2149    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9  7  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  1  0  0  0
 10 24  1  1  0  0  0
 25 23  1  1  0  0  0
  9 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
M  END


  Mrv1652309052223012D          

 29 31  0  0  1  0            999 V2000
   -2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4849   -0.6674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2695   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5391   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5391    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5391    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    1.7474    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7545    2.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846    2.4148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1202    3.1685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9407    3.2547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6353    3.8359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4849    1.4924    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2149    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9  7  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  1  0  0  0
 10 24  1  1  0  0  0
 25 23  1  1  0  0  0
  9 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0219882

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H]1[C@H]2[C@H]3O[C@H](C\C(C)=C/CC[C@@]3(C)OC(C)=O)[C@H]2C(C)=C[C@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H36O5/c1-13(2)20-19(27-16(5)25)12-15(4)21-18-11-14(3)9-8-10-24(7,29-17(6)26)23(28-18)22(20)21/h9,12-13,18-23H,8,10-11H2,1-7H3/b14-9-/t18-,19-,20+,21-,22-,23-,24-/m1/s1

> <INCHI_KEY>
OKHREEBDBYKLKA-AHVUDZSWSA-N

> <FORMULA>
C24H36O5

> <MOLECULAR_WEIGHT>
404.547

> <EXACT_MASS>
404.256274259

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
45.66033619275667

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,3R,4S,7R,8R,10Z,14R)-14-(acetyloxy)-6,10,14-trimethyl-3-(propan-2-yl)-15-oxatricyclo[6.6.1.0^{2,7}]pentadeca-5,10-dien-4-yl acetate

> <JCHEM_LOGP>
3.705862881

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.1939384436714455

> <JCHEM_POLAR_SURFACE_AREA>
61.83

> <JCHEM_REFRACTIVITY>
112.41850000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,3R,4S,7R,8R,10Z,14R)-14-(acetyloxy)-3-isopropyl-6,10,14-trimethyl-15-oxatricyclo[6.6.1.0^{2,7}]pentadeca-5,10-dien-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -6.668   2.310   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.905  -1.246   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.370  -1.722   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.834  -1.246   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.740  -2.492   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.740   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.740   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.834   2.786   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.370   3.262   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.275   4.508   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.465   4.508   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.091   5.915   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.623   6.075   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.186   7.160   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.905   2.786   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.401   0.770   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.000   4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   26                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   25                                                  
CONECT   10    9   11   24                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   23                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   17   24   25                                                  
CONECT   24   23   10                                                       
CONECT   25   23    9   26                                                  
CONECT   26   25    5   27                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₆O₅

Average Mass

404.5470 Da

Monoisotopic Mass

404.25627 Da

IUPAC Name

(1R,2R,3R,4S,7R,8R,10Z,14R)-14-(acetyloxy)-6,10,14-trimethyl-3-(propan-2-yl)-15-oxatricyclo[6.6.1.0^{2,7}]pentadeca-5,10-dien-4-yl acetate

Traditional Name

(1R,2R,3R,4S,7R,8R,10Z,14R)-14-(acetyloxy)-3-isopropyl-6,10,14-trimethyl-15-oxatricyclo[6.6.1.0^{2,7}]pentadeca-5,10-dien-4-yl acetate

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H]1[C@H]2[C@H]3O[C@H](C\C(C)=C/CC[C@@]3(C)OC(C)=O)[C@H]2C(C)=C[C@H]1OC(C)=O

InChI Identifier

InChI=1S/C24H36O5/c1-13(2)20-19(27-16(5)25)12-15(4)21-18-11-14(3)9-8-10-24(7,29-17(6)26)23(28-18)22(20)21/h9,12-13,18-23H,8,10-11H2,1-7H3/b14-9-/t18-,19-,20+,21-,22-,23-,24-/m1/s1

InChI Key

OKHREEBDBYKLKA-AHVUDZSWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eunicellane and asbestinane diterpenoids. These are diterpenoids with a structure based on either the eunicellane (5,14-cyclocembrane) or the asbestinane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Eunicellane and asbestinane diterpenoids

Alternative Parents

Substituents

Cladiellane diterpenoid
Eunicellane-type diterpenoid
Dicarboxylic acid or derivatives
Tetrahydrofuran
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	3.71	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	112.42 m³·mol⁻¹	ChemAxon
Polarizability	45.66 Å³	ChemAxon
Number of Rings	3	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

102064353

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,3r,4s,7r,8r,10z,14r)-14-(acetyloxy)-3-isopropyl-6,10,14-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadeca-5,10-dien-4-yl acetate (NP0219882)

MOL for NP0219882 ((1r,2r,3r,4s,7r,8r,10z,14r)-14-(acetyloxy)-3-isopropyl-6,10,14-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadeca-5,10-dien-4-yl acetate)

3D MOL for NP0219882 ((1r,2r,3r,4s,7r,8r,10z,14r)-14-(acetyloxy)-3-isopropyl-6,10,14-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadeca-5,10-dien-4-yl acetate)

3D SDF for NP0219882 ((1r,2r,3r,4s,7r,8r,10z,14r)-14-(acetyloxy)-3-isopropyl-6,10,14-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadeca-5,10-dien-4-yl acetate)

3D-SDF for NP0219882 ((1r,2r,3r,4s,7r,8r,10z,14r)-14-(acetyloxy)-3-isopropyl-6,10,14-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadeca-5,10-dien-4-yl acetate)

PDB for NP0219882 ((1r,2r,3r,4s,7r,8r,10z,14r)-14-(acetyloxy)-3-isopropyl-6,10,14-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadeca-5,10-dien-4-yl acetate)

3D PDB for NP0219882 ((1r,2r,3r,4s,7r,8r,10z,14r)-14-(acetyloxy)-3-isopropyl-6,10,14-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadeca-5,10-dien-4-yl acetate)

SMILES for NP0219882 ((1r,2r,3r,4s,7r,8r,10z,14r)-14-(acetyloxy)-3-isopropyl-6,10,14-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadeca-5,10-dien-4-yl acetate)

INCHI for NP0219882 ((1r,2r,3r,4s,7r,8r,10z,14r)-14-(acetyloxy)-3-isopropyl-6,10,14-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadeca-5,10-dien-4-yl acetate)

Structure for NP0219882 ((1r,2r,3r,4s,7r,8r,10z,14r)-14-(acetyloxy)-3-isopropyl-6,10,14-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadeca-5,10-dien-4-yl acetate)

3D Structure for NP0219882 ((1r,2r,3r,4s,7r,8r,10z,14r)-14-(acetyloxy)-3-isopropyl-6,10,14-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadeca-5,10-dien-4-yl acetate)