NP-MRD: Showing NP-Card for 5-(2-hydroxypropan-2-yl)-1,12-dimethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-2,4,6,9(16)-tetraene-8,11-dione (NP0271035)

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Record Information

Version

2.0

Created at

2022-09-08 17:11:27 UTC

Updated at

2022-09-08 17:11:27 UTC

NP-MRD ID

NP0271035

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(2-hydroxypropan-2-yl)-1,12-dimethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-2,4,6,9(16)-tetraene-8,11-dione

Description

5-(2-Hydroxypropan-2-yl)-1,12-dimethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]Hexadeca-2(7),3,5,9(16)-tetraene-8,11-dione belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 5-(2-hydroxypropan-2-yl)-1,12-dimethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-2,4,6,9(16)-tetraene-8,11-dione is found in Picea morrisonicola. 5-(2-Hydroxypropan-2-yl)-1,12-dimethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]Hexadeca-2(7),3,5,9(16)-tetraene-8,11-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241501102D          

 24 27  0  0  0  0            999 V2000
    5.4223    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2954    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1204    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    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
    3.2789   -0.4125    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
    2.5645    0.8250    0.0000 C   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
    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
    1.1355    0.0000    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
   -0.4561   -0.4265    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
    1.8500   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4997   -0.9209    0.0000 C   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
    0.3509    1.0799    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
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  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
 19 20  1  0  0  0  0
  8 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 13 24  1  0  0  0  0
M  END


  Mrv1533004241501102D          

 24 27  0  0  0  0            999 V2000
    5.4223    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2954    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1204    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    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
    3.2789   -0.4125    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
    2.5645    0.8250    0.0000 C   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
    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
    1.1355    0.0000    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
   -0.4561   -0.4265    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
    1.8500   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4997   -0.9209    0.0000 C   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
    0.3509    1.0799    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
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  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
 19 20  1  0  0  0  0
  8 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 13 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0271035

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)C1=CC=C2C(=C1)C(=O)C1=C3C(C)(CCCC23C)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O4/c1-18(2,23)11-6-7-13-12(10-11)14(21)15-16-19(13,3)8-5-9-20(16,4)17(22)24-15/h6-7,10,23H,5,8-9H2,1-4H3

> <INCHI_KEY>
IQMDFQYVBMPOOW-UHFFFAOYSA-N

> <FORMULA>
C20H22O4

> <MOLECULAR_WEIGHT>
326.392

> <EXACT_MASS>
326.151809188

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
35.52911971140229

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(2-hydroxypropan-2-yl)-1,12-dimethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-2,4,6,9(16)-tetraene-8,11-dione

> <ALOGPS_LOGP>
3.90

> <JCHEM_LOGP>
2.858862143333333

> <ALOGPS_LOGS>
-4.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.456341122879142

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0365963928526636

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
91.2145

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.72e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(2-hydroxypropan-2-yl)-1,12-dimethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-2,4,6,9(16)-tetraene-8,11-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      10.122   3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.788   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.018   3.644   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.558   0.976   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.121  -0.770   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       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.453   2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.453   3.850   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.120   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.120   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.655  -0.476   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.851  -0.796   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.335  -1.982   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.479  -3.013   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.944  -2.537   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.453  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.666  -1.719   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.250   0.770   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.790   0.770   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.655   2.016   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   20                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    5                                                       
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   24                                                  
CONECT   14   13   15   20                                                  
CONECT   15   14   16   17   22                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    8   14   21                                             
CONECT   21   20                                                            
CONECT   22   15   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   13                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₂O₄

Average Mass

326.3920 Da

Monoisotopic Mass

326.15181 Da

IUPAC Name

5-(2-hydroxypropan-2-yl)-1,12-dimethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-2,4,6,9(16)-tetraene-8,11-dione

Traditional Name

5-(2-hydroxypropan-2-yl)-1,12-dimethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-2,4,6,9(16)-tetraene-8,11-dione

CAS Registry Number

Not Available

SMILES

CC(C)(O)C1=CC=C2C(=C1)C(=O)C1=C3C(C)(CCCC23C)C(=O)O1

InChI Identifier

InChI=1S/C20H22O4/c1-18(2,23)11-6-7-13-12(10-11)14(21)15-16-19(13,3)8-5-9-20(16,4)17(22)24-15/h6-7,10,23H,5,8-9H2,1-4H3

InChI Key

IQMDFQYVBMPOOW-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Picea morrisonicola	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Phenanthrene
Naphthofuran
Naphthalene
Aryl ketone
Benzenoid
Dihydrofuran
Tertiary alcohol
Enol ester
Carboxylic acid ester
Ketone
Lactone
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Aromatic alcohol
Alcohol
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	3.9	ALOGPS
logP	2.86	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	14.46	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	91.21 m³·mol⁻¹	ChemAxon
Polarizability	35.53 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

72806463

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-(2-hydroxypropan-2-yl)-1,12-dimethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-2,4,6,9(16)-tetraene-8,11-dione (NP0271035)

MOL for NP0271035 (5-(2-hydroxypropan-2-yl)-1,12-dimethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-2,4,6,9(16)-tetraene-8,11-dione)

3D MOL for NP0271035 (5-(2-hydroxypropan-2-yl)-1,12-dimethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-2,4,6,9(16)-tetraene-8,11-dione)

3D SDF for NP0271035 (5-(2-hydroxypropan-2-yl)-1,12-dimethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-2,4,6,9(16)-tetraene-8,11-dione)

3D-SDF for NP0271035 (5-(2-hydroxypropan-2-yl)-1,12-dimethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-2,4,6,9(16)-tetraene-8,11-dione)

PDB for NP0271035 (5-(2-hydroxypropan-2-yl)-1,12-dimethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-2,4,6,9(16)-tetraene-8,11-dione)

3D PDB for NP0271035 (5-(2-hydroxypropan-2-yl)-1,12-dimethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-2,4,6,9(16)-tetraene-8,11-dione)

SMILES for NP0271035 (5-(2-hydroxypropan-2-yl)-1,12-dimethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-2,4,6,9(16)-tetraene-8,11-dione)

INCHI for NP0271035 (5-(2-hydroxypropan-2-yl)-1,12-dimethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-2,4,6,9(16)-tetraene-8,11-dione)

Structure for NP0271035 (5-(2-hydroxypropan-2-yl)-1,12-dimethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-2,4,6,9(16)-tetraene-8,11-dione)

3D Structure for NP0271035 (5-(2-hydroxypropan-2-yl)-1,12-dimethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-2,4,6,9(16)-tetraene-8,11-dione)