NP-MRD: Showing NP-Card for 8-hydroxy-1,12-dimethyl-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-2-ene-4,11-dione (NP0329999)

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Record Information

Version

2.0

Created at

2022-09-12 14:56:37 UTC

Updated at

2022-09-12 14:56:37 UTC

NP-MRD ID

NP0329999

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-hydroxy-1,12-dimethyl-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-2-ene-4,11-dione

Description

8-Hydroxy-1,12-dimethyl-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]Hexadec-2-ene-4,11-dione belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Based on a literature review very few articles have been published on 8-hydroxy-1,12-dimethyl-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]Hexadec-2-ene-4,11-dione.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122216562D          

 21 24  0  0  0  0            999 V2000
   -0.4561   -0.4265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794   -1.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925   -1.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5771   -1.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7486   -0.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4329   -1.0129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9590    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355   -0.0000    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  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  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  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  2  0  0  0  0
 17 21  1  0  0  0  0
  2 21  1  0  0  0  0
  6 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0329999

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CCCC3(C)C1C(OC2=O)C(O)C1COC(=O)C=C31

> <INCHI_IDENTIFIER>
InChI=1S/C16H20O5/c1-15-4-3-5-16(2)13(15)12(21-14(16)19)11(18)8-7-20-10(17)6-9(8)15/h6,8,11-13,18H,3-5,7H2,1-2H3

> <INCHI_KEY>
AHMYWLVSCSDIAQ-UHFFFAOYSA-N

> <FORMULA>
C16H20O5

> <MOLECULAR_WEIGHT>
292.331

> <EXACT_MASS>
292.131073744

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
29.267058651715203

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-hydroxy-1,12-dimethyl-5,10-dioxatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadec-2-ene-4,11-dione

> <JCHEM_LOGP>
1.2596373219999997

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.201233006159725

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.545814328541084

> <JCHEM_PKA_STRONGEST_BASIC>
-3.333901845353326

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
73.2318

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
8-hydroxy-1,12-dimethyl-5,10-dioxatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadec-2-ene-4,11-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.851  -0.796   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.655  -0.476   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.335  -1.982   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.479  -3.013   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.944  -2.537   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.264  -1.030   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.541  -1.891   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.787  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.788  -0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       7.454   1.540   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.453   2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.453   3.850   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.120   1.540   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.655   2.016   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.250   0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.790   0.770   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.120  -0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   19   21                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   21                                             
CONECT    7    6                                                            
CONECT    8    6    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18    2   20                                                  
CONECT   20   19                                                            
CONECT   21   17    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₀O₅

Average Mass

292.3310 Da

Monoisotopic Mass

292.13107 Da

IUPAC Name

8-hydroxy-1,12-dimethyl-5,10-dioxatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadec-2-ene-4,11-dione

Traditional Name

8-hydroxy-1,12-dimethyl-5,10-dioxatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadec-2-ene-4,11-dione

CAS Registry Number

Not Available

SMILES

CC12CCCC3(C)C1C(OC2=O)C(O)C1COC(=O)C=C31

InChI Identifier

InChI=1S/C16H20O5/c1-15-4-3-5-16(2)13(15)12(21-14(16)19)11(18)8-7-20-10(17)6-9(8)15/h6,8,11-13,18H,3-5,7H2,1-2H3

InChI Key

AHMYWLVSCSDIAQ-UHFFFAOYSA-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 naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthalene
Dihydropyranone
Pyran
Gamma butyrolactone
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	1.26	ChemAxon
pKa (Strongest Acidic)	13.55	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	73.23 m³·mol⁻¹	ChemAxon
Polarizability	29.27 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

163064122

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8-hydroxy-1,12-dimethyl-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-2-ene-4,11-dione (NP0329999)

MOL for NP0329999 (8-hydroxy-1,12-dimethyl-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-2-ene-4,11-dione)

3D MOL for NP0329999 (8-hydroxy-1,12-dimethyl-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-2-ene-4,11-dione)

3D SDF for NP0329999 (8-hydroxy-1,12-dimethyl-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-2-ene-4,11-dione)

3D-SDF for NP0329999 (8-hydroxy-1,12-dimethyl-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-2-ene-4,11-dione)

PDB for NP0329999 (8-hydroxy-1,12-dimethyl-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-2-ene-4,11-dione)

3D PDB for NP0329999 (8-hydroxy-1,12-dimethyl-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-2-ene-4,11-dione)

SMILES for NP0329999 (8-hydroxy-1,12-dimethyl-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-2-ene-4,11-dione)

INCHI for NP0329999 (8-hydroxy-1,12-dimethyl-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-2-ene-4,11-dione)

Structure for NP0329999 (8-hydroxy-1,12-dimethyl-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-2-ene-4,11-dione)

3D Structure for NP0329999 (8-hydroxy-1,12-dimethyl-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-2-ene-4,11-dione)