NP-MRD: Showing NP-Card for 5',5',9'-trimethylspiro[oxirane-2,14'-tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan]-6'-yl acetate (NP0320480)

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Record Information

Version

2.0

Created at

2022-09-11 22:09:09 UTC

Updated at

2022-09-11 22:09:09 UTC

NP-MRD ID

NP0320480

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5',5',9'-trimethylspiro[oxirane-2,14'-tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan]-6'-yl acetate

Description

5',5',9'-Trimethylspiro[oxirane-2,14'-tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecane]-6'-yl acetate belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. 5',5',9'-trimethylspiro[oxirane-2,14'-tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan]-6'-yl acetate is found in Achillea clypeolata. 5',5',9'-Trimethylspiro[oxirane-2,14'-tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecane]-6'-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 04121521082D          

 25 29  0  0  0  0            999 V2000
    8.7862    3.2074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9795    3.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4264    3.6465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7261    2.2493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9194    2.0763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6659    1.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8593    1.1182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3061    1.7302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0520    0.9454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4903    1.5567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3158    0.7052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4874    0.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8741    1.1060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4052    1.6229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8672    2.1809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1941    2.9687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0107    3.1391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5596    2.5153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3662    2.6883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2215    3.5005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9586    3.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0282    2.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4420    1.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6901    1.5164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7720    2.3374    0.0000 O   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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 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
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  1  0  0  0  0
  5 19  1  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
 22 23  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 25  1  0  0  0  0
M  END


  Mrv0541 04121521082D          

 25 29  0  0  0  0            999 V2000
    8.7862    3.2074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9795    3.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4264    3.6465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7261    2.2493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9194    2.0763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6659    1.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8593    1.1182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3061    1.7302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0520    0.9454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4903    1.5567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3158    0.7052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4874    0.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8741    1.1060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4052    1.6229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8672    2.1809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1941    2.9687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0107    3.1391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5596    2.5153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3662    2.6883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2215    3.5005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9586    3.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0282    2.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4420    1.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6901    1.5164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7720    2.3374    0.0000 O   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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 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
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  1  0  0  0  0
  5 19  1  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
 22 23  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0320480

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CCC2(C)C3CCC4CC3(CC43CO3)CCC2C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C22H34O3/c1-14(23)25-18-8-9-20(4)16(19(18,2)3)7-10-21-11-15(5-6-17(20)21)22(12-21)13-24-22/h15-18H,5-13H2,1-4H3

> <INCHI_KEY>
HQJKVPHKXMCWCU-UHFFFAOYSA-N

> <FORMULA>
C22H34O3

> <MOLECULAR_WEIGHT>
346.511

> <EXACT_MASS>
346.250794955

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
40.424674321824995

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5',5',9'-trimethylspiro[oxirane-2,14'-tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane]-6'-yl acetate

> <ALOGPS_LOGP>
3.95

> <JCHEM_LOGP>
3.9736847003333335

> <ALOGPS_LOGS>
-6.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.203998161451852

> <JCHEM_POLAR_SURFACE_AREA>
38.83

> <JCHEM_REFRACTIVITY>
96.25159999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.72e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5',5',9'-trimethylspiro[oxirane-2,14'-tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane]-6'-yl acetate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  C   UNK     0      16.401   5.987   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.895   5.664   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      13.863   6.807   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      14.422   4.199   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      12.916   3.876   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.443   2.410   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.937   2.087   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.905   3.230   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.430   1.765   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.382   2.906   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.056   1.316   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.510   0.919   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.365   2.064   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.356   3.029   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.219   4.071   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.829   5.542   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.353   5.860   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.378   4.695   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.884   5.018   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.613   6.534   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.989   6.090   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.653   4.675   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.558   3.464   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.155   2.831   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.308   4.363   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   19                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   18                                             
CONECT    9    8                                                            
CONECT   10    8   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   23                                                  
CONECT   14   13   15                                                       
CONECT   15   14   10   16   22                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    8   19                                                  
CONECT   19   18    5   20   21                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   15   23                                                       
CONECT   23   22   13   24   25                                             
CONECT   24   23   25                                                       
CONECT   25   24   23                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Value	Source
5',5',9'-Trimethylspiro[oxirane-2,14'-tetracyclo[11.2.1.0,.0,]hexadecane]-6'-yl acetic acid	Generator
5',5',9'-Trimethylspiro[oxirane-2,14'-tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane]-6'-yl acetic acid	Generator

Chemical Formula

C₂₂H₃₄O₃

Average Mass

346.5110 Da

Monoisotopic Mass

346.25079 Da

IUPAC Name

5',5',9'-trimethylspiro[oxirane-2,14'-tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane]-6'-yl acetate

Traditional Name

5',5',9'-trimethylspiro[oxirane-2,14'-tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane]-6'-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CCC2(C)C3CCC4CC3(CC43CO3)CCC2C1(C)C

InChI Identifier

InChI=1S/C22H34O3/c1-14(23)25-18-8-9-20(4)16(19(18,2)3)7-10-21-11-15(5-6-17(20)21)22(12-21)13-24-22/h15-18H,5-13H2,1-4H3

InChI Key

HQJKVPHKXMCWCU-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Achillea clypeolata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Substituents

Kaurane diterpenoid
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Oxirane
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	3.95	ALOGPS
logP	3.97	ChemAxon
logS	-6.8	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	96.25 m³·mol⁻¹	ChemAxon
Polarizability	40.42 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

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 5',5',9'-trimethylspiro[oxirane-2,14'-tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan]-6'-yl acetate (NP0320480)

MOL for NP0320480 (5',5',9'-trimethylspiro[oxirane-2,14'-tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan]-6'-yl acetate)

3D MOL for NP0320480 (5',5',9'-trimethylspiro[oxirane-2,14'-tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan]-6'-yl acetate)

3D SDF for NP0320480 (5',5',9'-trimethylspiro[oxirane-2,14'-tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan]-6'-yl acetate)

3D-SDF for NP0320480 (5',5',9'-trimethylspiro[oxirane-2,14'-tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan]-6'-yl acetate)

PDB for NP0320480 (5',5',9'-trimethylspiro[oxirane-2,14'-tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan]-6'-yl acetate)

3D PDB for NP0320480 (5',5',9'-trimethylspiro[oxirane-2,14'-tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan]-6'-yl acetate)

SMILES for NP0320480 (5',5',9'-trimethylspiro[oxirane-2,14'-tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan]-6'-yl acetate)

INCHI for NP0320480 (5',5',9'-trimethylspiro[oxirane-2,14'-tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan]-6'-yl acetate)

Structure for NP0320480 (5',5',9'-trimethylspiro[oxirane-2,14'-tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan]-6'-yl acetate)

3D Structure for NP0320480 (5',5',9'-trimethylspiro[oxirane-2,14'-tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan]-6'-yl acetate)