NP-MRD: Showing NP-Card for 12,15-dihydroxy-13-methoxy-5,9-dimethyl-4-oxatricyclo[9.4.0.0³,⁵]pentadeca-1(15),8,11,13-tetraen-2-one (NP0330973)

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Record Information

Version

1.0

Created at

2022-09-12 16:50:40 UTC

Updated at

2022-09-12 16:50:40 UTC

NP-MRD ID

NP0330973

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12,15-dihydroxy-13-methoxy-5,9-dimethyl-4-oxatricyclo[9.4.0.0³,⁵]pentadeca-1(15),8,11,13-tetraen-2-one

Description

12,15-dihydroxy-13-methoxy-5,9-dimethyl-4-oxatricyclo[9.4.0.0³,⁵]pentadeca-1(15),8,11,13-tetraen-2-one is found in Tricholoma terreum. Based on a literature review very few articles have been published on 12,15-dihydroxy-13-methoxy-5,9-dimethyl-4-oxatricyclo[9.4.0.0³,⁵]Pentadeca-1(11),8,12,14-tetraen-2-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122218502D          

 22 24  0  0  0  0            999 V2000
    6.9399    0.9952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8116    0.1802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0417   -0.1162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4001    0.4025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6301    0.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9885    0.6247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5018   -0.7088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1434   -1.2275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9133   -0.9311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5550   -1.4497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0151   -2.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2451   -2.3388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1168   -3.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6035   -1.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8336   -2.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1920   -1.5979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3203   -0.7829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5053   -0.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4486    0.0320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0902   -0.4866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7319   -1.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1490   -1.5891    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  4  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
  7 21  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0330973

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(CC(C)=CCCC3(C)OC3C2=O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C17H20O5/c1-9-5-4-6-17(2)16(22-17)15(20)13-10(7-9)14(19)12(21-3)8-11(13)18/h5,8,16,18-19H,4,6-7H2,1-3H3

> <INCHI_KEY>
GZXQQAXUUCDUEA-UHFFFAOYSA-N

> <FORMULA>
C17H20O5

> <MOLECULAR_WEIGHT>
304.342

> <EXACT_MASS>
304.131073744

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
31.643599606292998

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
12,15-dihydroxy-13-methoxy-5,9-dimethyl-4-oxatricyclo[9.4.0.0^{3,5}]pentadeca-1(15),8,11,13-tetraen-2-one

> <JCHEM_LOGP>
3.3223477473333327

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.02840710891546

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.097746321951668

> <JCHEM_PKA_STRONGEST_BASIC>
-4.192956281673887

> <JCHEM_POLAR_SURFACE_AREA>
79.28999999999999

> <JCHEM_REFRACTIVITY>
82.53609999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
12,15-dihydroxy-13-methoxy-5,9-dimethyl-4-oxatricyclo[9.4.0.0^{3,5}]pentadeca-1(15),8,11,13-tetraen-2-one

> <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      12.955   1.858   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.715   0.336   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.278  -0.217   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.080   0.751   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.643   0.198   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.445   1.166   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.403  -1.323   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.601  -2.291   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.038  -1.738   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      12.236  -2.706   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.361  -3.813   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.924  -4.366   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.685  -5.887   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.727  -3.398   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.289  -3.951   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.092  -2.983   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.331  -1.461   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.810  -1.222   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.571   0.060   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.768  -0.908   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.966  -1.876   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.878  -2.966   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   21                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8    3   10                                                  
CONECT   10    9                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   17   21                                                  
CONECT   21   20    7   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₀O₅

Average Mass

304.3420 Da

Monoisotopic Mass

304.13107 Da

IUPAC Name

12,15-dihydroxy-13-methoxy-5,9-dimethyl-4-oxatricyclo[9.4.0.0^{3,5}]pentadeca-1(15),8,11,13-tetraen-2-one

Traditional Name

12,15-dihydroxy-13-methoxy-5,9-dimethyl-4-oxatricyclo[9.4.0.0^{3,5}]pentadeca-1(15),8,11,13-tetraen-2-one

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(CC(C)=CCCC3(C)OC3C2=O)=C1O

InChI Identifier

InChI=1S/C17H20O5/c1-9-5-4-6-17(2)16(22-17)15(20)13-10(7-9)14(19)12(21-3)8-11(13)18/h5,8,16,18-19H,4,6-7H2,1-3H3

InChI Key

GZXQQAXUUCDUEA-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Tricholoma terreum	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	3.32	ChemAxon
pKa (Strongest Acidic)	9.1	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.29 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	82.54 m³·mol⁻¹	ChemAxon
Polarizability	31.64 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

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

78167893

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 12,15-dihydroxy-13-methoxy-5,9-dimethyl-4-oxatricyclo[9.4.0.0³,⁵]pentadeca-1(15),8,11,13-tetraen-2-one (NP0330973)

MOL for NP0330973 (12,15-dihydroxy-13-methoxy-5,9-dimethyl-4-oxatricyclo[9.4.0.0³,⁵]pentadeca-1(15),8,11,13-tetraen-2-one)

3D MOL for NP0330973 (12,15-dihydroxy-13-methoxy-5,9-dimethyl-4-oxatricyclo[9.4.0.0³,⁵]pentadeca-1(15),8,11,13-tetraen-2-one)

3D SDF for NP0330973 (12,15-dihydroxy-13-methoxy-5,9-dimethyl-4-oxatricyclo[9.4.0.0³,⁵]pentadeca-1(15),8,11,13-tetraen-2-one)

3D-SDF for NP0330973 (12,15-dihydroxy-13-methoxy-5,9-dimethyl-4-oxatricyclo[9.4.0.0³,⁵]pentadeca-1(15),8,11,13-tetraen-2-one)

PDB for NP0330973 (12,15-dihydroxy-13-methoxy-5,9-dimethyl-4-oxatricyclo[9.4.0.0³,⁵]pentadeca-1(15),8,11,13-tetraen-2-one)

3D PDB for NP0330973 (12,15-dihydroxy-13-methoxy-5,9-dimethyl-4-oxatricyclo[9.4.0.0³,⁵]pentadeca-1(15),8,11,13-tetraen-2-one)

SMILES for NP0330973 (12,15-dihydroxy-13-methoxy-5,9-dimethyl-4-oxatricyclo[9.4.0.0³,⁵]pentadeca-1(15),8,11,13-tetraen-2-one)

INCHI for NP0330973 (12,15-dihydroxy-13-methoxy-5,9-dimethyl-4-oxatricyclo[9.4.0.0³,⁵]pentadeca-1(15),8,11,13-tetraen-2-one)

Structure for NP0330973 (12,15-dihydroxy-13-methoxy-5,9-dimethyl-4-oxatricyclo[9.4.0.0³,⁵]pentadeca-1(15),8,11,13-tetraen-2-one)

3D Structure for NP0330973 (12,15-dihydroxy-13-methoxy-5,9-dimethyl-4-oxatricyclo[9.4.0.0³,⁵]pentadeca-1(15),8,11,13-tetraen-2-one)