NP-MRD: Showing NP-Card for 9-(hydroxymethyl)-4,4,12b-trimethyl-1,2,3,4a,5,6-hexahydrotetraphene-8,11-dione (NP0218742)

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Record Information

Version

1.0

Created at

2022-09-05 19:30:36 UTC

Updated at

2022-09-05 19:30:36 UTC

NP-MRD ID

NP0218742

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-(hydroxymethyl)-4,4,12b-trimethyl-1,2,3,4a,5,6-hexahydrotetraphene-8,11-dione

Description

9-(Hydroxymethyl)-4,4,12b-trimethyl-1,2,3,4,4a,5,6,8,11,12b-decahydrotetraphene-8,11-dione belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 9-(hydroxymethyl)-4,4,12b-trimethyl-1,2,3,4a,5,6-hexahydrotetraphene-8,11-dione is found in Phyllosticta spinarum. 9-(Hydroxymethyl)-4,4,12b-trimethyl-1,2,3,4,4a,5,6,8,11,12b-decahydrotetraphene-8,11-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004251509252D          

 25 28  0  0  0  0            999 V2000
    2.2177   -1.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0323   -1.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0194   -0.6140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023   -2.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124   -2.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3825   -1.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9226   -2.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8424   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124   -0.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9226   -0.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4627   -0.9711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2728   -0.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129   -1.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6230   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931   -0.5034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1631   -1.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931   -2.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0829   -2.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129   -3.6216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7327   -2.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926   -1.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9732   -1.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2433   -0.9711    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 14 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
  7 23  1  0  0  0  0
 12 23  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END


  Mrv1533004251509252D          

 25 28  0  0  0  0            999 V2000
    2.2177   -1.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0323   -1.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0194   -0.6140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023   -2.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124   -2.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3825   -1.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9226   -2.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8424   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124   -0.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9226   -0.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4627   -0.9711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2728   -0.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129   -1.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6230   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931   -0.5034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1631   -1.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931   -2.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0829   -2.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129   -3.6216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7327   -2.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926   -1.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9732   -1.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2433   -0.9711    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 14 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
  7 23  1  0  0  0  0
 12 23  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0218742

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCCC2(C)C1CCC1=CC3=C(C=C21)C(=O)C=C(CO)C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H26O3/c1-21(2)7-4-8-22(3)17-11-15-16(9-13(17)5-6-19(21)22)20(25)14(12-23)10-18(15)24/h9-11,19,23H,4-8,12H2,1-3H3

> <INCHI_KEY>
FTPYFKFDSUGCPB-UHFFFAOYSA-N

> <FORMULA>
C22H26O3

> <MOLECULAR_WEIGHT>
338.447

> <EXACT_MASS>
338.188194697

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
39.01111041887322

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-(hydroxymethyl)-4,4,12b-trimethyl-1,2,3,4,4a,5,6,8,11,12b-decahydrotetraphene-8,11-dione

> <ALOGPS_LOGP>
4.19

> <JCHEM_LOGP>
3.947914445666666

> <ALOGPS_LOGS>
-5.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.623514863419803

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.397957364774896

> <JCHEM_PKA_STRONGEST_BASIC>
-2.834781952244069

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
99.79299999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.91e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-(hydroxymethyl)-4,4,12b-trimethyl-1,2,3,4a,5,6-hexahydrotetraphene-8,11-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       4.140  -2.442   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.660  -2.686   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.636  -1.146   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.156  -4.141   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.164  -5.305   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.677  -5.014   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.181  -3.559   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.189  -4.723   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.172  -2.395   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.677  -0.940   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.189  -0.649   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.197  -1.813   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.709  -1.522   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.717  -2.686   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.230  -2.395   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      14.734  -0.940   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      15.238  -3.559   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.734  -5.014   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.221  -5.305   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      12.717  -6.760   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      12.213  -4.141   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.701  -4.432   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.693  -3.268   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.750  -3.268   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      17.254  -1.813   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    9                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   23                                             
CONECT    8    7                                                            
CONECT    9    7    2   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   23                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   14   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22    7   12                                                  
CONECT   24   17   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₆O₃

Average Mass

338.4470 Da

Monoisotopic Mass

338.18819 Da

IUPAC Name

9-(hydroxymethyl)-4,4,12b-trimethyl-1,2,3,4,4a,5,6,8,11,12b-decahydrotetraphene-8,11-dione

Traditional Name

9-(hydroxymethyl)-4,4,12b-trimethyl-1,2,3,4a,5,6-hexahydrotetraphene-8,11-dione

CAS Registry Number

Not Available

SMILES

CC1(C)CCCC2(C)C1CCC1=CC3=C(C=C21)C(=O)C=C(CO)C3=O

InChI Identifier

InChI=1S/C22H26O3/c1-21(2)7-4-8-22(3)17-11-15-16(9-13(17)5-6-19(21)22)20(25)14(12-23)10-18(15)24/h9-11,19,23H,4-8,12H2,1-3H3

InChI Key

FTPYFKFDSUGCPB-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Phyllosticta spinarum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Abietane diterpenoid
Diterpenoid
Anthraquinone
1,4-anthraquinone
Phenanthrene
Tetralin
Naphthalene
Quinone
Aryl ketone
Benzenoid
Ketone
Primary alcohol
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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	4.19	ALOGPS
logP	3.95	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	11.4	ChemAxon
pKa (Strongest Basic)	-2.8	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	99.79 m³·mol⁻¹	ChemAxon
Polarizability	39.01 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

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 9-(hydroxymethyl)-4,4,12b-trimethyl-1,2,3,4a,5,6-hexahydrotetraphene-8,11-dione (NP0218742)

MOL for NP0218742 (9-(hydroxymethyl)-4,4,12b-trimethyl-1,2,3,4a,5,6-hexahydrotetraphene-8,11-dione)

3D MOL for NP0218742 (9-(hydroxymethyl)-4,4,12b-trimethyl-1,2,3,4a,5,6-hexahydrotetraphene-8,11-dione)

3D SDF for NP0218742 (9-(hydroxymethyl)-4,4,12b-trimethyl-1,2,3,4a,5,6-hexahydrotetraphene-8,11-dione)

3D-SDF for NP0218742 (9-(hydroxymethyl)-4,4,12b-trimethyl-1,2,3,4a,5,6-hexahydrotetraphene-8,11-dione)

PDB for NP0218742 (9-(hydroxymethyl)-4,4,12b-trimethyl-1,2,3,4a,5,6-hexahydrotetraphene-8,11-dione)

3D PDB for NP0218742 (9-(hydroxymethyl)-4,4,12b-trimethyl-1,2,3,4a,5,6-hexahydrotetraphene-8,11-dione)

SMILES for NP0218742 (9-(hydroxymethyl)-4,4,12b-trimethyl-1,2,3,4a,5,6-hexahydrotetraphene-8,11-dione)

INCHI for NP0218742 (9-(hydroxymethyl)-4,4,12b-trimethyl-1,2,3,4a,5,6-hexahydrotetraphene-8,11-dione)

Structure for NP0218742 (9-(hydroxymethyl)-4,4,12b-trimethyl-1,2,3,4a,5,6-hexahydrotetraphene-8,11-dione)

3D Structure for NP0218742 (9-(hydroxymethyl)-4,4,12b-trimethyl-1,2,3,4a,5,6-hexahydrotetraphene-8,11-dione)