NP-MRD: Showing NP-Card for 2'',5''-dimethoxy-2,5,5,8a-tetramethyl-hexahydro-2h-dispiro[naphthalene-1,2':5',3''-bis(oxolane)]-4-yl acetate (NP0223908)

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Record Information

Version

2.0

Created at

2022-09-06 02:07:59 UTC

Updated at

2022-09-06 02:07:59 UTC

NP-MRD ID

NP0223908

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2'',5''-dimethoxy-2,5,5,8a-tetramethyl-hexahydro-2h-dispiro[naphthalene-1,2':5',3''-bis(oxolane)]-4-yl acetate

Description

2'',5''-Dimethoxy-2,5,5,8a-tetramethyl-octahydro-2H-dispiro[naphthalene-1,2':5',3''-Bis(oxolane)]-4-yl acetate belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 2'',5''-dimethoxy-2,5,5,8a-tetramethyl-hexahydro-2h-dispiro[naphthalene-1,2':5',3''-bis(oxolane)]-4-yl acetate is found in Vitex trifolia. 2'',5''-Dimethoxy-2,5,5,8a-tetramethyl-octahydro-2H-dispiro[naphthalene-1,2':5',3''-Bis(oxolane)]-4-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004151518122D          

 30 33  0  0  0  0            999 V2000
    6.2800   -0.7166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6745   -1.2769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8865   -1.0327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2257   -1.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5517   -1.0510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3075   -1.8390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4826   -1.8503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2170   -1.0692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8777   -0.5752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6115   -1.6296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7940   -2.4341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8234   -1.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6409   -0.5808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1471   -0.3366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7526   -0.8970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5701   -1.7015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5406   -0.6528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2464   -0.0204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0639    0.7841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3032    0.4646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6172    1.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6694    1.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4574    1.1003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6399    0.2957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0344   -0.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8594   -0.2534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7959   -0.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3019    0.3978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6272    1.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6208   -0.2517    0.0000 O   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  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
  5  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 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
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  8 25  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 27 30  1  0  0  0  0
  3 30  1  0  0  0  0
M  END


  Mrv1533004151518122D          

 30 33  0  0  0  0            999 V2000
    6.2800   -0.7166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6745   -1.2769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8865   -1.0327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2257   -1.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5517   -1.0510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3075   -1.8390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4826   -1.8503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2170   -1.0692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8777   -0.5752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6115   -1.6296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7940   -2.4341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8234   -1.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6409   -0.5808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1471   -0.3366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7526   -0.8970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5701   -1.7015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5406   -0.6528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2464   -0.0204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0639    0.7841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3032    0.4646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6172    1.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6694    1.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4574    1.1003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6399    0.2957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0344   -0.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8594   -0.2534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7959   -0.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3019    0.3978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6272    1.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6208   -0.2517    0.0000 O   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  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
  5  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 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
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  8 25  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 27 30  1  0  0  0  0
  3 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0223908

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1CC2(CCC3(O2)C(C)CC(OC(C)=O)C2C(C)(C)CCCC32C)C(OC)O1

> <INCHI_IDENTIFIER>
InChI=1S/C24H40O6/c1-15-13-17(28-16(2)25)19-21(3,4)9-8-10-22(19,5)24(15)12-11-23(30-24)14-18(26-6)29-20(23)27-7/h15,17-20H,8-14H2,1-7H3

> <INCHI_KEY>
YCGYYZXBHVNOIX-UHFFFAOYSA-N

> <FORMULA>
C24H40O6

> <MOLECULAR_WEIGHT>
424.578

> <EXACT_MASS>
424.282489008

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
47.75554144538148

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2'',5''-dimethoxy-2,5,5,8a-tetramethyl-octahydro-2H-dispiro[naphthalene-1,2':5',3''-bis(oxolane)]-4-yl acetate

> <ALOGPS_LOGP>
3.70

> <JCHEM_LOGP>
4.386333579999999

> <ALOGPS_LOGS>
-5.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7346774446495146

> <JCHEM_POLAR_SURFACE_AREA>
63.22000000000001

> <JCHEM_REFRACTIVITY>
111.16299999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.19e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2'',5''-dimethoxy-2,5,5,8a-tetramethyl-hexahydro-2H-dispiro[naphthalene-1,2':5',3''-bis(oxolane)]-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0      11.723  -1.338   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.592  -2.384   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.121  -1.928   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.888  -2.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.630  -1.962   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.174  -3.433   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.634  -3.454   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.138  -1.996   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.372  -1.074   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.008  -3.042   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.349  -4.544   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.537  -2.586   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.196  -1.084   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.275  -0.628   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.405  -1.674   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.064  -3.176   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.876  -1.218   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.327  -0.038   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.986   1.464   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.566   0.867   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.152   2.758   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.116   2.510   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.587   2.054   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.928   0.552   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.798  -0.494   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.337  -0.473   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.086  -0.491   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.164   0.743   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.771   2.158   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.626  -0.470   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   30                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9   27                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   25                                             
CONECT    9    8    5                                                       
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13   19   25                                                  
CONECT   19   18   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24    8   18   26                                             
CONECT   26   25                                                            
CONECT   27    5   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27    3                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
2'',5''-Dimethoxy-2,5,5,8a-tetramethyl-octahydro-2H-dispiro[naphthalene-1,2':5',3''-bis(oxolane)]-4-yl acetic acid	Generator

Chemical Formula

C₂₄H₄₀O₆

Average Mass

424.5780 Da

Monoisotopic Mass

424.28249 Da

IUPAC Name

2'',5''-dimethoxy-2,5,5,8a-tetramethyl-octahydro-2H-dispiro[naphthalene-1,2':5',3''-bis(oxolane)]-4-yl acetate

Traditional Name

2'',5''-dimethoxy-2,5,5,8a-tetramethyl-hexahydro-2H-dispiro[naphthalene-1,2':5',3''-bis(oxolane)]-4-yl acetate

CAS Registry Number

Not Available

SMILES

COC1CC2(CCC3(O2)C(C)CC(OC(C)=O)C2C(C)(C)CCCC32C)C(OC)O1

InChI Identifier

InChI=1S/C24H40O6/c1-15-13-17(28-16(2)25)19-21(3,4)9-8-10-22(19,5)24(15)12-11-23(30-24)14-18(26-6)29-20(23)27-7/h15,17-20H,8-14H2,1-7H3

InChI Key

YCGYYZXBHVNOIX-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Vitex trifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Grindelane diterpenoid
Tetrahydrofuran
Carboxylic acid ester
Acetal
Carboxylic acid derivative
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Carbonyl group
Organic oxide
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	3.7	ALOGPS
logP	4.39	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	63.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	111.16 m³·mol⁻¹	ChemAxon
Polarizability	47.76 Å³	ChemAxon
Number of Rings	4	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

73105256

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2'',5''-dimethoxy-2,5,5,8a-tetramethyl-hexahydro-2h-dispiro[naphthalene-1,2':5',3''-bis(oxolane)]-4-yl acetate (NP0223908)

MOL for NP0223908 (2'',5''-dimethoxy-2,5,5,8a-tetramethyl-hexahydro-2h-dispiro[naphthalene-1,2':5',3''-bis(oxolane)]-4-yl acetate)

3D MOL for NP0223908 (2'',5''-dimethoxy-2,5,5,8a-tetramethyl-hexahydro-2h-dispiro[naphthalene-1,2':5',3''-bis(oxolane)]-4-yl acetate)

3D SDF for NP0223908 (2'',5''-dimethoxy-2,5,5,8a-tetramethyl-hexahydro-2h-dispiro[naphthalene-1,2':5',3''-bis(oxolane)]-4-yl acetate)

3D-SDF for NP0223908 (2'',5''-dimethoxy-2,5,5,8a-tetramethyl-hexahydro-2h-dispiro[naphthalene-1,2':5',3''-bis(oxolane)]-4-yl acetate)

PDB for NP0223908 (2'',5''-dimethoxy-2,5,5,8a-tetramethyl-hexahydro-2h-dispiro[naphthalene-1,2':5',3''-bis(oxolane)]-4-yl acetate)

3D PDB for NP0223908 (2'',5''-dimethoxy-2,5,5,8a-tetramethyl-hexahydro-2h-dispiro[naphthalene-1,2':5',3''-bis(oxolane)]-4-yl acetate)

SMILES for NP0223908 (2'',5''-dimethoxy-2,5,5,8a-tetramethyl-hexahydro-2h-dispiro[naphthalene-1,2':5',3''-bis(oxolane)]-4-yl acetate)

INCHI for NP0223908 (2'',5''-dimethoxy-2,5,5,8a-tetramethyl-hexahydro-2h-dispiro[naphthalene-1,2':5',3''-bis(oxolane)]-4-yl acetate)

Structure for NP0223908 (2'',5''-dimethoxy-2,5,5,8a-tetramethyl-hexahydro-2h-dispiro[naphthalene-1,2':5',3''-bis(oxolane)]-4-yl acetate)

3D Structure for NP0223908 (2'',5''-dimethoxy-2,5,5,8a-tetramethyl-hexahydro-2h-dispiro[naphthalene-1,2':5',3''-bis(oxolane)]-4-yl acetate)