NP-MRD: Showing NP-Card for 12-hydroxy-8,16-dimethyl-14-oxapentacyclo[11.2.2.1⁹,¹².0¹,¹¹.0⁴,¹⁰]octadeca-4,7,9-triene-6,15-dione (NP0222344)

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Record Information

Version

2.0

Created at

2022-09-06 00:09:39 UTC

Updated at

2022-09-06 00:09:40 UTC

NP-MRD ID

NP0222344

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-hydroxy-8,16-dimethyl-14-oxapentacyclo[11.2.2.1⁹,¹².0¹,¹¹.0⁴,¹⁰]octadeca-4,7,9-triene-6,15-dione

Description

12-Hydroxy-8,16-dimethyl-14-oxapentacyclo[11.2.2.1⁹,¹².0¹,¹¹.0⁴,¹⁰]Octadeca-4,7,9-triene-6,15-dione belongs to the class of organic compounds known as tropones. Tropones are compounds containing a tropone ring, which is a cycloheptatrienone ring bearing a ketone group. 12-hydroxy-8,16-dimethyl-14-oxapentacyclo[11.2.2.1⁹,¹².0¹,¹¹.0⁴,¹⁰]octadeca-4,7,9-triene-6,15-dione is found in Cephalotaxus fortunei. 12-Hydroxy-8,16-dimethyl-14-oxapentacyclo[11.2.2.1⁹,¹².0¹,¹¹.0⁴,¹⁰]Octadeca-4,7,9-triene-6,15-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004171520462D          

 23 27  0  0  0  0            999 V2000
    6.9803    1.2445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4646    0.6005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8371   -0.1799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0613   -0.5227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9753    0.3136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2086    1.2123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7049    1.8714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5339    0.8134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0406    1.5226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2472    1.7597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8252    1.0270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0862    1.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4037    0.9619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6766    1.3516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3806    0.1174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9274   -0.5275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5448   -1.2584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7818   -0.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0888    0.1991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9485    0.1570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2139   -0.6640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4972   -1.4388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4804   -1.0997    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  2  0  0  0  0
  6  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  0  0  0  0
  4 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 18 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0222344

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CC2OC(=O)C11CCC3=CC(=O)C=C(C)C4=C3C1C2(O)C4

> <INCHI_IDENTIFIER>
InChI=1S/C19H20O4/c1-9-5-12(20)7-11-3-4-18-10(2)6-14(23-17(18)21)19(22)8-13(9)15(11)16(18)19/h5,7,10,14,16,22H,3-4,6,8H2,1-2H3

> <INCHI_KEY>
PKYNSKWZQXVGLT-UHFFFAOYSA-N

> <FORMULA>
C19H20O4

> <MOLECULAR_WEIGHT>
312.365

> <EXACT_MASS>
312.136159124

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
32.92147779275605

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
12-hydroxy-8,16-dimethyl-14-oxapentacyclo[11.2.2.1⁹,¹².0¹,¹¹.0⁴,¹⁰]octadeca-4,7,9-triene-6,15-dione

> <ALOGPS_LOGP>
1.70

> <JCHEM_LOGP>
1.2424250863333337

> <ALOGPS_LOGS>
-3.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.81768833143384

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.390187443215435

> <JCHEM_PKA_STRONGEST_BASIC>
-3.502923391895097

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
85.5371

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.54e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-hydroxy-8,16-dimethyl-14-oxapentacyclo[11.2.2.1⁹,¹².0¹,¹¹.0⁴,¹⁰]octadeca-4,7,9-triene-6,15-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      13.030   2.323   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.067   1.121   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.763  -0.336   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.314  -0.976   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      11.154   0.585   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      11.589   2.263   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      12.516   3.493   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.330   1.518   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.409   2.842   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.928   3.285   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.140   1.917   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.761   2.694   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.487   1.796   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.130   2.523   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.444   0.219   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.465  -0.985   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.750  -2.349   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.059  -1.140   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.632   0.372   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.237   0.293   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.733  -1.239   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.261  -2.686   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.363  -2.053   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   21                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    2    9   20                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   23                                                  
CONECT   19   18   11   20                                                  
CONECT   20   19    8   21                                                  
CONECT   21   20    4   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   18                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₀O₄

Average Mass

312.3650 Da

Monoisotopic Mass

312.13616 Da

IUPAC Name

12-hydroxy-8,16-dimethyl-14-oxapentacyclo[11.2.2.1⁹,¹².0¹,¹¹.0⁴,¹⁰]octadeca-4,7,9-triene-6,15-dione

Traditional Name

12-hydroxy-8,16-dimethyl-14-oxapentacyclo[11.2.2.1⁹,¹².0¹,¹¹.0⁴,¹⁰]octadeca-4,7,9-triene-6,15-dione

CAS Registry Number

Not Available

SMILES

CC1CC2OC(=O)C11CCC3=CC(=O)C=C(C)C4=C3C1C2(O)C4

InChI Identifier

InChI=1S/C19H20O4/c1-9-5-12(20)7-11-3-4-18-10(2)6-14(23-17(18)21)19(22)8-13(9)15(11)16(18)19/h5,7,10,14,16,22H,3-4,6,8H2,1-2H3

InChI Key

PKYNSKWZQXVGLT-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cephalotaxus fortunei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tropones. Tropones are compounds containing a tropone ring, which is a cycloheptatrienone ring bearing a ketone group.

Kingdom

Organic compounds

Super Class

Hydrocarbon derivatives

Class

Tropones

Sub Class

Not Available

Direct Parent

Tropones

Alternative Parents

Substituents

Tropone
Delta valerolactone
Delta_valerolactone
Oxane
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Lactone
Cyclic ketone
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Carbonyl group
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	1.7	ALOGPS
logP	1.24	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	13.39	ChemAxon
pKa (Strongest Basic)	-3.5	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	0	ChemAxon
Refractivity	85.54 m³·mol⁻¹	ChemAxon
Polarizability	32.92 Å³	ChemAxon
Number of Rings	5	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

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 12-hydroxy-8,16-dimethyl-14-oxapentacyclo[11.2.2.1⁹,¹².0¹,¹¹.0⁴,¹⁰]octadeca-4,7,9-triene-6,15-dione (NP0222344)

MOL for NP0222344 (12-hydroxy-8,16-dimethyl-14-oxapentacyclo[11.2.2.1⁹,¹².0¹,¹¹.0⁴,¹⁰]octadeca-4,7,9-triene-6,15-dione)

3D MOL for NP0222344 (12-hydroxy-8,16-dimethyl-14-oxapentacyclo[11.2.2.1⁹,¹².0¹,¹¹.0⁴,¹⁰]octadeca-4,7,9-triene-6,15-dione)

3D SDF for NP0222344 (12-hydroxy-8,16-dimethyl-14-oxapentacyclo[11.2.2.1⁹,¹².0¹,¹¹.0⁴,¹⁰]octadeca-4,7,9-triene-6,15-dione)

3D-SDF for NP0222344 (12-hydroxy-8,16-dimethyl-14-oxapentacyclo[11.2.2.1⁹,¹².0¹,¹¹.0⁴,¹⁰]octadeca-4,7,9-triene-6,15-dione)

PDB for NP0222344 (12-hydroxy-8,16-dimethyl-14-oxapentacyclo[11.2.2.1⁹,¹².0¹,¹¹.0⁴,¹⁰]octadeca-4,7,9-triene-6,15-dione)

3D PDB for NP0222344 (12-hydroxy-8,16-dimethyl-14-oxapentacyclo[11.2.2.1⁹,¹².0¹,¹¹.0⁴,¹⁰]octadeca-4,7,9-triene-6,15-dione)

SMILES for NP0222344 (12-hydroxy-8,16-dimethyl-14-oxapentacyclo[11.2.2.1⁹,¹².0¹,¹¹.0⁴,¹⁰]octadeca-4,7,9-triene-6,15-dione)

INCHI for NP0222344 (12-hydroxy-8,16-dimethyl-14-oxapentacyclo[11.2.2.1⁹,¹².0¹,¹¹.0⁴,¹⁰]octadeca-4,7,9-triene-6,15-dione)

Structure for NP0222344 (12-hydroxy-8,16-dimethyl-14-oxapentacyclo[11.2.2.1⁹,¹².0¹,¹¹.0⁴,¹⁰]octadeca-4,7,9-triene-6,15-dione)

3D Structure for NP0222344 (12-hydroxy-8,16-dimethyl-14-oxapentacyclo[11.2.2.1⁹,¹².0¹,¹¹.0⁴,¹⁰]octadeca-4,7,9-triene-6,15-dione)