NP-MRD: Showing NP-Card for (-)-spathulenol (NP0328752)

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Record Information

Version

2.0

Created at

2022-09-12 12:31:07 UTC

Updated at

2022-09-12 12:31:07 UTC

NP-MRD ID

NP0328752

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-spathulenol

Description

Ent-Spathulenol 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. (-)-spathulenol is found in Ageratum fastigiatum, Anastrophyllum auritum, Neoorthocaulis floerkei, Bazzania tridens, Bazzania trilobata, Bryopteris filicina, Calypogeia muelleriana, Conocephalum japonicum, Cunila microcephala, Diplophyllum serrulatum, Jackiella javanica, Lophocolea heterophylla, Pallenis spinosa, Plagiochila asplenioides, Plagiochila cristata, Plagiochila fasciculata, Plagiochila ovalifolia, Plagiochila parvifolia, Plagiochila porelloides, Plagiochila trabeculata, Pleurozia gigantea, Porella chilensis, Sanicula lamelligera, Scapania nemorea, Scapania uliginosa, Archilejeunea olivacea, Syzygiella tasmanica, Tetralophozia setiformis, Trichocoleopsis sacculata, Tritomaria quinquedentata, Tussilago farfara and Valeriana officinalis. Based on a literature review very few articles have been published on Ent-Spathulenol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
   -1.3386    3.3100    0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6542    2.2205    0.0676 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6599    2.4417   -0.5828 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7679    1.5889   -0.1225 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5479    0.5422    0.8594 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5501   -0.4878    0.6961 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5370   -0.1764   -0.2856 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3039    0.9615    0.3643 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6867    0.7776   -0.1886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8615   -0.7260    0.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5471   -1.2292   -0.4954 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1729   -2.5845    0.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8246   -1.3631   -1.8781 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8963   -0.8817    0.3645 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3192   -1.0263   -1.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7285   -1.6938    1.3209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2884    3.2221    0.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9377    4.3158    0.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8709    3.5465   -0.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4609    2.2897   -1.6864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5569    2.2998    0.2821 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2970    1.1954   -1.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8603    0.7751    1.9235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1187   -0.9463    1.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1702    0.2081   -1.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3704    0.8377    1.4646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4321    1.3764    0.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7394    0.9326   -1.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7371   -1.1352   -0.4084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8604   -0.8505    1.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9249   -2.9080    0.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2151   -3.3576   -0.7640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1806   -2.6241    0.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1961   -1.9459   -2.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3749   -2.1062   -1.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3666   -0.6390   -1.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6313   -0.5809   -1.7952 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7976   -1.4017    1.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6449   -2.7652    1.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5288   -1.4120    2.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 16  1  0
 14  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  6
 11  7  1  0
  7  6  1  0
  6 14  1  0
  6  5  1  0
  7  8  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
  5 23  1  1
  4 21  1  0
  4 22  1  0
  3 19  1  0
  3 20  1  0
  1 17  1  0
  1 18  1  0
  8 26  1  1
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 12 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
  7 25  1  6
  6 24  1  1
M  END


  Mrv1652309122214312D          

 16 18  0  0  1  0            999 V2000
    2.0737    1.8074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6618    1.2289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4382    1.5078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1404    1.0746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2395    0.2556    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6609   -0.3326    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8404   -0.2469    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3957    0.4480    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5974    0.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5487   -0.5837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3169   -0.8846    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1064   -1.6823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8901   -1.4779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4596   -0.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6095   -1.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2732   -0.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  6  0  0  0
  6  5  1  6  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  6  0  0  0
  6 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0328752

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)[C@H]2CCC(=C)[C@H]3CC[C@@](C)(O)[C@@H]3[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O/c1-9-5-6-11-13(14(11,2)3)12-10(9)7-8-15(12,4)16/h10-13,16H,1,5-8H2,2-4H3/t10-,11+,12+,13+,15-/m1/s1

> <INCHI_KEY>
FRMCCTDTYSRUBE-HYFYGGESSA-N

> <FORMULA>
C15H24O

> <MOLECULAR_WEIGHT>
220.356

> <EXACT_MASS>
220.182715393

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
26.7289970847603

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1aS,4aS,7R,7aS,7bS)-1,1,7-trimethyl-4-methylidene-decahydro-1H-cyclopropa[e]azulen-7-ol

> <JCHEM_LOGP>
2.8308566080000004

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.93392097088224

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6407029673361072

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
66.3775

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1aS,4aS,7R,7aS,7bS)-1,1,7-trimethyl-4-methylidene-octahydrocyclopropa[e]azulen-7-ol

> <JCHEM_VEBER_RULE>
1

$$$$

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       3.871   3.374   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.969   2.294   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.418   2.815   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.729   2.006   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.914   0.477   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.834  -0.621   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.302  -0.461   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.472   0.836   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.982   0.448   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.891  -1.090   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.325  -1.651   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.932  -3.140   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.395  -2.759   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.325  -1.007   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.604  -2.521   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.843  -1.262   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    2    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    7   12   13                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    6    5   15   16                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

View in JSmol

Synonyms

Value	Source
Spathulenol	MeSH

Chemical Formula

C₁₅H₂₄O

Average Mass

220.3560 Da

Monoisotopic Mass

220.18272 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1(C)[C@H]2CCC(=C)[C@H]3CC[C@@](C)(O)[C@@H]3[C@@H]12

InChI Identifier

InChI=1S/C15H24O/c1-9-5-6-11-13(14(11,2)3)12-10(9)7-8-15(12,4)16/h10-13,16H,1,5-8H2,2-4H3/t10-,11+,12+,13+,15-/m1/s1

InChI Key

FRMCCTDTYSRUBE-HYFYGGESSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ageratum fastigiatum	LOTUS Database	35616633
Anastrophyllum auritum	LOTUS Database	35616633
Barbilophozia floerkei	LOTUS Database	35616633
Bazzania tridens	LOTUS Database	35616633
Bazzania trilobata	LOTUS Database	35616633
Bryopteris filicina	LOTUS Database	35616633
Calypogeia muelleriana	LOTUS Database	35616633
Conocephalum supradecompositum	LOTUS Database	35616633
Cunila microcephala	LOTUS Database	35616633
Diplophyllum serrulatum	LOTUS Database	35616633
Jackiella javanica	LOTUS Database	35616633
Lophocolea heterophylla	LOTUS Database	35616633
Pallenis spinosa	LOTUS Database	35616633
Plagiochila asplenioides	LOTUS Database	35616633
Plagiochila cristata	LOTUS Database	35616633
Plagiochila fasciculata	LOTUS Database	35616633
Plagiochila ovalifolia	LOTUS Database	35616633
Plagiochila parvifolia	LOTUS Database	35616633
Plagiochila porelloides	LOTUS Database	35616633
Plagiochila trabeculata	LOTUS Database	35616633
Pleurozia gigantea	LOTUS Database	35616633
Porella chilensis	LOTUS Database	35616633
Sanicula lamelligera	LOTUS Database	35616633
Scapania nemorea	LOTUS Database	35616633
Scapania uliginosa	LOTUS Database	35616633
Spruceanthus olivaceus	LOTUS Database	35616633
Syzygiella tasmanica	LOTUS Database	35616633
Tetralophozia setiformis	LOTUS Database	35616633
Trichocoleopsis sacculata	LOTUS Database	35616633
Trilophozia quinquedentata	LOTUS Database	35616633
Tussilago farfara	LOTUS Database	35616633
Valeriana officinalis	LOTUS Database	35616633

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

sesquiterpenoid (CHEBI:67836 )

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00031765

Chemspider ID

26347272

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13854255

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (-)-spathulenol (NP0328752)

MOL for NP0328752 ((-)-spathulenol)

3D MOL for NP0328752 ((-)-spathulenol)

3D SDF for NP0328752 ((-)-spathulenol)

3D-SDF for NP0328752 ((-)-spathulenol)

PDB for NP0328752 ((-)-spathulenol)

3D PDB for NP0328752 ((-)-spathulenol)

SMILES for NP0328752 ((-)-spathulenol)

INCHI for NP0328752 ((-)-spathulenol)

Structure for NP0328752 ((-)-spathulenol)

3D Structure for NP0328752 ((-)-spathulenol)