NP-MRD: Showing NP-Card for Palustrol (NP0047085)

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Record Information

Version

2.0

Created at

2022-03-17 20:34:23 UTC

Updated at

2022-03-17 20:34:23 UTC

NP-MRD ID

NP0047085

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Palustrol

Description

Palustrol belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. Palustrol is found in Actinodium cunninghamii, Angelica gigas, Artemisia lagocephala, Artemisia lagopus, Austrobaileya scandens, Austromyrtus dulcis, Baccharis dracunculifolia, Baccharis genistelloides , Bazzania trilobata, Bouchardatia neurococca, Cyperus rotundus, Eucalyptus fasciculosa, Eucalyptus stoatei, Acca sellowiana, Guarea macrophylla, Guarea macrophylla ssp.tuberculata, Helichrysum stoechas, Humulus lupulus, Kunzea salina, Larix kaempferi, Ledum palustre L. , Lepicolea ochroleuca, Melaleuca alternifolia, Melaleuca leucadendra, Melaleuca leucadendron , Micromeria sinaica, Ozothamnus pholidotus, Phagnalon sordidum, Pinus koraiensis , Psiadia altissima, Renealmia chrysotrycha , Rhododendron groenlandicum, Rhododendron mucronulatum, Salvia absconditiflora and Salvia syriaca. Palustrol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241221202D          

 16 18  0  0  0  0            999 V2000
    0.8678    0.2817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4294   -0.3226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6955    0.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4719    0.7372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1740    0.3040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2732   -0.5150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6946   -1.1032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8741   -1.0176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3506   -1.6552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5824   -1.3544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6311   -0.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5587   -2.4535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4932   -1.3101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6432   -2.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3069   -1.4467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1073    1.0368    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  1  0  0  0  0
  7  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
  2 11  1  0  0  0  0
  9 12  1  0  0  0  0
  7 13  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  3 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047085

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC2(O)C1C1C(CCC2C)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H26O/c1-9-7-8-15(16)10(2)5-6-11-13(12(9)15)14(11,3)4/h9-13,16H,5-8H2,1-4H3

> <INCHI_KEY>
QWRTXOOFEHOROQ-UHFFFAOYSA-N

> <FORMULA>
C15H26O

> <MOLECULAR_WEIGHT>
222.3663

> <EXACT_MASS>
222.198365454

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
27.506177833797512

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,1,2,5-tetramethyl-decahydro-1H-cyclopropa[e]azulen-4a-ol

> <ALOGPS_LOGP>
3.25

> <JCHEM_LOGP>
3.3344098789999994

> <ALOGPS_LOGS>
-4.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.07033419983746303

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
66.446

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.74e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,1,2,5-tetramethyl-octahydro-1aH-cyclopropa[e]azulen-4a-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       1.620   0.526   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.668  -0.602   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.165   0.855   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.614   1.376   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.925   0.567   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.110  -0.961   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.030  -2.059   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.498  -1.900   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.521  -3.090   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.087  -2.528   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.178  -0.991   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.910  -4.580   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.521  -2.446   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.801  -3.960   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.040  -2.701   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.067   1.935   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8   11                                             
CONECT    3    2    4   16                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    2    9                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10    2                                                       
CONECT   12    9                                                            
CONECT   13    7    6   14   15                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    3                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₆O

Average Mass

222.3663 Da

Monoisotopic Mass

222.19837 Da

IUPAC Name

1,1,2,5-tetramethyl-decahydro-1H-cyclopropa[e]azulen-4a-ol

Traditional Name

1,1,2,5-tetramethyl-octahydro-1aH-cyclopropa[e]azulen-4a-ol

CAS Registry Number

Not Available

SMILES

CC1CCC2(O)C1C1C(CCC2C)C1(C)C

InChI Identifier

InChI=1S/C15H26O/c1-9-7-8-15(16)10(2)5-6-11-13(12(9)15)14(11,3)4/h9-13,16H,5-8H2,1-4H3

InChI Key

QWRTXOOFEHOROQ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Actinodium cunninghamii	LOTUS Database	35616633
Angelica gigas	LOTUS Database	35616633
Artemisia lagocephala	LOTUS Database	35616633
Artemisia lagopus	LOTUS Database	35616633
Austrobaileya scandens	LOTUS Database	35616633
Austromyrtus dulcis	LOTUS Database	35616633
Baccharis dracunculifolia	LOTUS Database	35616633
Baccharis genistelloides	Plant	KNApSAcK
Bazzania trilobata	LOTUS Database	35616633
Bouchardatia neurococca	LOTUS Database	35616633
Cyperus rotundus	LOTUS Database	35616633
Eucalyptus fasciculosa	LOTUS Database	35616633
Eucalyptus stoatei	LOTUS Database	35616633
Feijoa sellowiana	Plant	KNApSAcK
Guarea macrophylla	LOTUS Database	35616633
Guarea macrophylla ssp.tuberculata	Plant	KNApSAcK
Helichrysum stoechas	LOTUS Database	35616633
Humulus lupulus	LOTUS Database	35616633
Kunzea salina	LOTUS Database	35616633
Larix kaempferi	LOTUS Database	35616633
Ledum palustre	Plant	KNApSAcK
Lepicolea ochroleuca	LOTUS Database	35616633
Melaleuca alternifolia	LOTUS Database	35616633
Melaleuca leucadendra	LOTUS Database	35616633
Melaleuca leucadendron	Plant	KNApSAcK
Micromeria sinaica	LOTUS Database	35616633
Ozothamnus pholidotus	LOTUS Database	35616633
Phagnalon sordidum	Plant	KNApSAcK
Pinus koraiensis	Plant	KNApSAcK
Psiadia altissima	LOTUS Database	35616633
Renealmia chrysotrycha	Plant	KNApSAcK
Rhododendron groenlandicum	LOTUS Database	35616633
Rhododendron mucronulatum	LOTUS Database	35616633
Salvia absconditiflora	LOTUS Database	35616633
Salvia syriaca	LOTUS Database	35616633
Syzygium aromaticum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

5,10-cycloaromadendrane sesquiterpenoids

Alternative Parents

Substituents

5,10-cycloaromadendrane sesquiterpenoid
Guaiane sesquiterpenoid
Tertiary alcohol
Cyclic alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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	3.25	ALOGPS
logP	3.33	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	-0.07	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	66.45 m³·mol⁻¹	ChemAxon
Polarizability	27.51 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB007221

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

110745

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Palustrol (NP0047085)

MOL for NP0047085 (Palustrol)

3D MOL for NP0047085 (Palustrol)

3D SDF for NP0047085 (Palustrol)

3D-SDF for NP0047085 (Palustrol)

PDB for NP0047085 (Palustrol)

3D PDB for NP0047085 (Palustrol)

SMILES for NP0047085 (Palustrol)

INCHI for NP0047085 (Palustrol)

Structure for NP0047085 (Palustrol)

3D Structure for NP0047085 (Palustrol)