NP-MRD: Showing NP-Card for 3,4,9-trihydroxy-2-isopropyl-4b,8,8-trimethyl-6,7,8a,9-tetrahydro-5h-fluorene-1-carbaldehyde (NP0321997)

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Record Information

Version

2.0

Created at

2022-09-12 00:30:20 UTC

Updated at

2022-09-12 00:30:21 UTC

NP-MRD ID

NP0321997

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4,9-trihydroxy-2-isopropyl-4b,8,8-trimethyl-6,7,8a,9-tetrahydro-5h-fluorene-1-carbaldehyde

Description

5,6,9-Trihydroxy-1,1,4a-trimethyl-7-(propan-2-yl)-2,3,4,4a,9,9a-hexahydro-1H-fluorene-8-carbaldehyde belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 3,4,9-trihydroxy-2-isopropyl-4b,8,8-trimethyl-6,7,8a,9-tetrahydro-5h-fluorene-1-carbaldehyde is found in Salvia dichroantha. 5,6,9-Trihydroxy-1,1,4a-trimethyl-7-(propan-2-yl)-2,3,4,4a,9,9a-hexahydro-1H-fluorene-8-carbaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004171514572D          

 24 26  0  0  0  0            999 V2000
    5.3194    0.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7674    0.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0223   -0.7152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2575    1.6387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6435    1.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339   -0.6855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339   -1.5105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7686   -1.1370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2401   -0.8093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8570    1.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6633   -1.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4703   -1.3283    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  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  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
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 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
  9 20  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  0  0  0  0
 10 22  2  0  0  0  0
  4 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0321997

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=C(O)C(O)=C2C(C(O)C3C2(C)CCCC3(C)C)=C1C=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O4/c1-10(2)12-11(9-21)13-14(17(24)15(12)22)20(5)8-6-7-19(3,4)18(20)16(13)23/h9-10,16,18,22-24H,6-8H2,1-5H3

> <INCHI_KEY>
IIYLPCIYUBWRSS-UHFFFAOYSA-N

> <FORMULA>
C20H28O4

> <MOLECULAR_WEIGHT>
332.44

> <EXACT_MASS>
332.198759382

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
37.48313957999188

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,6,9-trihydroxy-1,1,4a-trimethyl-7-(propan-2-yl)-2,3,4,4a,9,9a-hexahydro-1H-fluorene-8-carbaldehyde

> <ALOGPS_LOGP>
3.77

> <JCHEM_LOGP>
4.065017828333332

> <ALOGPS_LOGS>
-3.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.383325045474773

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.03664167711988

> <JCHEM_PKA_STRONGEST_BASIC>
-3.250996356148458

> <JCHEM_POLAR_SURFACE_AREA>
77.75999999999999

> <JCHEM_REFRACTIVITY>
95.11009999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.34e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4,9-trihydroxy-2-isopropyl-4b,8,8-trimethyl-6,7,8a,9-tetrahydro-5H-fluorene-1-carbaldehyde

> <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       9.930   1.274   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.899   0.130   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.375  -1.335   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.393   0.450   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.917   1.914   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.947   3.059   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.410   2.235   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.935   3.699   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.380   1.090   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.856  -0.374   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.610  -1.280   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.610  -2.820   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.364  -0.374   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.858  -0.695   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.435  -2.122   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.448  -1.511   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.173   0.450   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.303   1.914   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.810   2.235   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.840   1.090   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.466   2.497   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.362  -0.695   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.838  -2.159   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.344  -2.479   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   22                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   20                                                  
CONECT   10    9   11   22                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   20                                                  
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    9   13   21                                             
CONECT   21   20                                                            
CONECT   22   10    4   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₈O₄

Average Mass

332.4400 Da

Monoisotopic Mass

332.19876 Da

IUPAC Name

5,6,9-trihydroxy-1,1,4a-trimethyl-7-(propan-2-yl)-2,3,4,4a,9,9a-hexahydro-1H-fluorene-8-carbaldehyde

Traditional Name

3,4,9-trihydroxy-2-isopropyl-4b,8,8-trimethyl-6,7,8a,9-tetrahydro-5H-fluorene-1-carbaldehyde

CAS Registry Number

Not Available

SMILES

CC(C)C1=C(O)C(O)=C2C(C(O)C3C2(C)CCCC3(C)C)=C1C=O

InChI Identifier

InChI=1S/C20H28O4/c1-10(2)12-11(9-21)13-14(17(24)15(12)22)20(5)8-6-7-19(3,4)18(20)16(13)23/h9-10,16,18,22-24H,6-8H2,1-5H3

InChI Key

IIYLPCIYUBWRSS-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Salvia dichroantha	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

Abeoabietane diterpenoid
Diterpenoid
Fluorene
Cumene
Indane
Aryl-aldehyde
Phenol
Benzenoid
Secondary alcohol
Polyol
Aldehyde
Organooxygen compound
Alcohol
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	3.77	ALOGPS
logP	4.07	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	8.04	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	95.11 m³·mol⁻¹	ChemAxon
Polarizability	37.48 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

78384812

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,4,9-trihydroxy-2-isopropyl-4b,8,8-trimethyl-6,7,8a,9-tetrahydro-5h-fluorene-1-carbaldehyde (NP0321997)

MOL for NP0321997 (3,4,9-trihydroxy-2-isopropyl-4b,8,8-trimethyl-6,7,8a,9-tetrahydro-5h-fluorene-1-carbaldehyde)

3D MOL for NP0321997 (3,4,9-trihydroxy-2-isopropyl-4b,8,8-trimethyl-6,7,8a,9-tetrahydro-5h-fluorene-1-carbaldehyde)

3D SDF for NP0321997 (3,4,9-trihydroxy-2-isopropyl-4b,8,8-trimethyl-6,7,8a,9-tetrahydro-5h-fluorene-1-carbaldehyde)

3D-SDF for NP0321997 (3,4,9-trihydroxy-2-isopropyl-4b,8,8-trimethyl-6,7,8a,9-tetrahydro-5h-fluorene-1-carbaldehyde)

PDB for NP0321997 (3,4,9-trihydroxy-2-isopropyl-4b,8,8-trimethyl-6,7,8a,9-tetrahydro-5h-fluorene-1-carbaldehyde)

3D PDB for NP0321997 (3,4,9-trihydroxy-2-isopropyl-4b,8,8-trimethyl-6,7,8a,9-tetrahydro-5h-fluorene-1-carbaldehyde)

SMILES for NP0321997 (3,4,9-trihydroxy-2-isopropyl-4b,8,8-trimethyl-6,7,8a,9-tetrahydro-5h-fluorene-1-carbaldehyde)

INCHI for NP0321997 (3,4,9-trihydroxy-2-isopropyl-4b,8,8-trimethyl-6,7,8a,9-tetrahydro-5h-fluorene-1-carbaldehyde)

Structure for NP0321997 (3,4,9-trihydroxy-2-isopropyl-4b,8,8-trimethyl-6,7,8a,9-tetrahydro-5h-fluorene-1-carbaldehyde)

3D Structure for NP0321997 (3,4,9-trihydroxy-2-isopropyl-4b,8,8-trimethyl-6,7,8a,9-tetrahydro-5h-fluorene-1-carbaldehyde)