NP-MRD: Showing NP-Card for Phytocassane D (NP0049779)

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Record Information

Version

2.0

Created at

2022-03-17 21:17:59 UTC

Updated at

2022-03-17 21:18:00 UTC

NP-MRD ID

NP0049779

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Phytocassane D

Description

Phytocassane D belongs to the class of organic compounds known as isocopalane and spongiane diterpenoids. These are diterpenoids with a structure based on the isocopalane (Tetradecahydro-1,1,4a,7,8,8a-hexamethylphenanthrene) or the 15,16-epoxyisocopalane skeleton. Phytocassane D is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Phytocassane D has been detected, but not quantified in, cereals and cereal products and rices. Phytocassane D is found in Oryza sativa L. . This could make phytocassane D a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061312212D          

 23 25  0  0  0  0            999 V2000
    5.2520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4452   -1.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4733   -0.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  2  0  0  0  0
  8  7  1  0  0  0  0
 11  2  1  0  0  0  0
 12  6  1  0  0  0  0
 12  9  2  0  0  0  0
 12 11  1  0  0  0  0
 13  7  1  0  0  0  0
 13 11  1  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
 16  8  1  0  0  0  0
 17 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18 15  1  0  0  0  0
 19  3  1  0  0  0  0
 19  4  1  0  0  0  0
 19 16  1  0  0  0  0
 19 18  1  0  0  0  0
 20  5  1  0  0  0  0
 20 10  1  0  0  0  0
 20 16  1  0  0  0  0
 20 17  1  0  0  0  0
 21 14  2  0  0  0  0
 22 15  2  0  0  0  0
 23 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049779

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2CCC3C(C)(C)C(O)C(=O)CC3(C)C2C(=O)C=C1C=C

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O3/c1-6-12-9-14(21)17-13(11(12)2)7-8-16-19(3,4)18(23)15(22)10-20(16,17)5/h6,9,11,13,16-18,23H,1,7-8,10H2,2-5H3

> <INCHI_KEY>
DGUIKAVSMBLZCL-UHFFFAOYSA-N

> <FORMULA>
C20H28O3

> <MOLECULAR_WEIGHT>
316.4345

> <EXACT_MASS>
316.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
36.08395534741062

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-ethenyl-2-hydroxy-1,1,4a,8-tetramethyl-1,2,3,4,4a,4b,5,8,8a,9,10,10a-dodecahydrophenanthrene-3,5-dione

> <ALOGPS_LOGP>
2.24

> <JCHEM_LOGP>
3.404582373333333

> <ALOGPS_LOGS>
-4.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.45383988251

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.974883304966774

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6845832878841875

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
91.31469999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.50e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-ethenyl-2-hydroxy-1,1,4a,8-tetramethyl-2,4,4b,8,8a,9,10,10a-octahydrophenanthrene-3,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.494  -1.897   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.831  -2.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.883  -1.090   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.414   3.437   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -1.746   0.770   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2   11                                                            
CONECT    3   19                                                            
CONECT    4   19                                                            
CONECT    5   20                                                            
CONECT    6    1   12                                                       
CONECT    7    8   13                                                       
CONECT    8    7   16                                                       
CONECT    9   12   14                                                       
CONECT   10   15   20                                                       
CONECT   11    2   12   13                                                  
CONECT   12    6    9   11                                                  
CONECT   13    7   11   17                                                  
CONECT   14    9   17   21                                                  
CONECT   15   10   18   22                                                  
CONECT   16    8   19   20                                                  
CONECT   17   13   14   20                                                  
CONECT   18   15   19   23                                                  
CONECT   19    3    4   16   18                                             
CONECT   20    5   10   16   17                                             
CONECT   21   14                                                            
CONECT   22   15                                                            
CONECT   23   18                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
(-)-Phytocassane D	HMDB

Chemical Formula

C₂₀H₂₈O₃

Average Mass

316.4345 Da

Monoisotopic Mass

316.20384 Da

IUPAC Name

7-ethenyl-2-hydroxy-1,1,4a,8-tetramethyl-1,2,3,4,4a,4b,5,8,8a,9,10,10a-dodecahydrophenanthrene-3,5-dione

Traditional Name

7-ethenyl-2-hydroxy-1,1,4a,8-tetramethyl-2,4,4b,8,8a,9,10,10a-octahydrophenanthrene-3,5-dione

CAS Registry Number

166547-24-6

SMILES

CC1C2CCC3C(C)(C)C(O)C(=O)CC3(C)C2C(=O)C=C1C=C

InChI Identifier

InChI=1S/C20H28O3/c1-6-12-9-14(21)17-13(11(12)2)7-8-16-19(3,4)18(23)15(22)10-20(16,17)5/h6,9,11,13,16-18,23H,1,7-8,10H2,2-5H3

InChI Key

DGUIKAVSMBLZCL-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Oryza sativa	FooDB	KNAPSACK
Oryza sativa L.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isocopalane and spongiane diterpenoids. These are diterpenoids with a structure based on the isocopalane (Tetradecahydro-1,1,4a,7,8,8a-hexamethylphenanthrene) or the 15,16-epoxyisocopalane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Isocopalane and spongiane diterpenoids

Alternative Parents

Substituents

Isocopalane diterpenoid
Phenanthrene
Hydrophenanthrene
Cyclohexenone
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	2.24	ALOGPS
logP	3.4	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	12.97	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	91.31 m³·mol⁻¹	ChemAxon
Polarizability	36.08 Å³	ChemAxon
Number of Rings	3	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

HMDB0041057

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020931

KNApSAcK ID

C00034143

Chemspider ID

24785124

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72781133

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Phytocassane D (NP0049779)

MOL for NP0049779 (Phytocassane D)

3D MOL for NP0049779 (Phytocassane D)

3D SDF for NP0049779 (Phytocassane D)

3D-SDF for NP0049779 (Phytocassane D)

PDB for NP0049779 (Phytocassane D)

3D PDB for NP0049779 (Phytocassane D)

SMILES for NP0049779 (Phytocassane D)

INCHI for NP0049779 (Phytocassane D)

Structure for NP0049779 (Phytocassane D)

3D Structure for NP0049779 (Phytocassane D)