NP-MRD: Showing NP-Card for (+)-Ferruginol (NP0052009)

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Record Information

Version

2.0

Created at

2022-04-27 23:12:07 UTC

Updated at

2022-04-27 23:12:07 UTC

NP-MRD ID

NP0052009

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Ferruginol

Description

Ferruginol belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (+)-Ferruginol is found in Amentotaxus formosana, Callitris japonica, Calocedrus formosana, Calocedrus macrolepis, Cephalotaxus harringtonia var.drupacea, Chamaecyparis formosensis, Chamaecyparis lawsoniana, Chamaecyparis obtusa, Chamaecyparis pisifera, Cryptomeria japonica, Cryptomeria japonica D.DON., Cupressus sempervirens, Fraxinus mandshurica, Harpagophytum procumbens , Isodon serra, Juniperus chinensis, Juniperus communis, Juniperus excelsa , Juniperus formosana, Juniperus formosana Hay.var.concolor Hay, Juniperus procera, Juniperus rigida, Podocarpus ferrugineus , Premna herbacea, Premna serratifolia, Prumnopitys andina, Prumnopitys ferruginea, Salvia amplexicaulis, Salvia amplexicaulis Lam., Salvia apiana, Salvia argentea , Salvia blepharochaena Hedge and Hub.Mor., Salvia blepharochlaena, Salvia bracteata Banks and Sol., Salvia broussonetii, Salvia caespitosa, Salvia caespitosa Montbret and Aucher ex.Bentham, Salvia candidissima, Salvia ceratophylla L., Salvia cyanescens, Salvia deserta, Salvia eriophora, Salvia eriophora Boiss and Kotschy, Salvia fruticosa, Salvia hypargeia, Salvia kronenburgii, Salvia lanigera, Salvia limbata, Salvia microstegia, Salvia miltiorrhiza , Salvia montbretii, Salvia multicaulis , Salvia munzii, Salvia napifolia, Salvia prionitis, Salvia przewalskii , Salvia recognita, Salvia recognita Fisch.et Mey., Rosmarinus officinalis , Salvia sahendica, Salvia sclarea, Salvia staminea, Salvia syriaca, Salvia syriaca L., Salvia tomentosa, Salvia trijuga, Salvia virgata, Salvia viridis L. , Salvia wiedemannii, Salvia yunnanensis, Salvinia molesta, Scutellaria baicalensis, Sequoia sempervirens, Taiwania cryptomerioides, Tetraclinis articulata, Teucrium polium, Thuja occidentalis, Thuja plicata, Thuja standishii, Thujopsis dolabrata, Torreya nucifera, Torreya nucifera var.radicans , Trogopterus xanthipes and Vitex rotundifolia. (+)-Ferruginol was first documented in 2020 (PMID: 33295481). Based on a literature review a significant number of articles have been published on ferruginol (PMID: 34133748) (PMID: 32972338) (PMID: 33568294) (PMID: 33673350) (PMID: 34946537) (PMID: 34899332).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 51 53  0  0  0  0  0  0  0  0999 V2000
    5.2899   -0.2896    1.7127 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6155   -0.0606    0.4001 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2855   -0.5314   -0.8331 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1380   -0.1599    0.4459 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3492    0.8638    0.9233 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9733    0.8544    0.7078 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3672   -0.1618    0.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1829   -1.1857   -0.4397 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5222   -1.2110   -0.2497 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3160   -2.2449   -0.7109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0612   -0.2093   -0.2518 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2265    0.1990   -1.7115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4688   -1.6673   -0.0682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8739   -1.9165    0.2819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5512   -0.9076    1.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2527    0.5194    0.6274 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0491    1.4214    1.5222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8899    0.5922   -0.7250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7849    0.6546    0.7080 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2319    2.0301    0.8457 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2214    2.0346    1.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7758   -1.3111    1.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0956    0.4085    1.9480 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4879   -0.2904    2.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7673    1.1291    0.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4297   -1.5960   -0.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3315   -0.0520   -0.8551 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7680   -0.0684   -1.7194 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8414    1.6435    1.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7765   -2.0382   -1.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8960   -3.0321   -1.2041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5800   -0.6677   -2.3500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1956    0.3947   -2.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7544    1.1365   -1.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7979   -2.2014    0.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2564   -2.1754   -1.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9214   -2.8966    0.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5244   -2.1450   -0.5820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1617   -0.9362    2.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6483   -1.0932    1.0867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4891    2.2665    0.9165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5303    1.8577    2.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9445    0.8973    1.9315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6418   -0.2034   -1.4166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9990    0.3968   -0.5080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9220    1.6054   -1.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5195    0.1771    1.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4730    2.6444   -0.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7520    2.5010    1.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3955    2.0579    2.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6749    2.9668    0.8223 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  7 11  1  0
 11 12  1  6
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
  9  4  1  0
 19 11  1  0
 21  6  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  6
  3 26  1  0
  3 27  1  0
  3 28  1  0
  5 29  1  0
  8 30  1  0
 10 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  1
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
M  END


  Mrv1652304282201122D          

 21 23  0  0  1  0            999 V2000
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3016   -0.7392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6308   -1.1265    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
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  6  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  7 14  1  0  0  0  0
 13 15  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  5 19  1  6  0  0  0
  3 20  1  0  0  0  0
  3 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0052009

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=CC2=C(C=C1O)[C@@]1(C)CCCC(C)(C)[C@@H]1CC2

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O/c1-13(2)15-11-14-7-8-18-19(3,4)9-6-10-20(18,5)16(14)12-17(15)21/h11-13,18,21H,6-10H2,1-5H3/t18-,20+/m0/s1

> <INCHI_KEY>
QXNWVJOHUAQHLM-AZUAARDMSA-N

> <FORMULA>
C20H30O

> <MOLECULAR_WEIGHT>
286.459

> <EXACT_MASS>
286.229665586

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
35.681051894408846

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4bS,8aS)-4b,8,8-trimethyl-2-(propan-2-yl)-4b,5,6,7,8,8a,9,10-octahydrophenanthren-3-ol

> <ALOGPS_LOGP>
6.56

> <JCHEM_LOGP>
6.253506807333332

> <ALOGPS_LOGS>
-5.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.802586943766016

> <JCHEM_PKA_STRONGEST_BASIC>
-5.198803611605848

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
89.7077

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.19e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ferruginol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.746   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.516  -0.564   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.516   2.104   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.030  -1.380   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.777  -2.103   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   20   21                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   19                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   14                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13    7                                                       
CONECT   15   13                                                            
CONECT   16   12   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    5                                                            
CONECT   20    3                                                            
CONECT   21    3                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
12-Hydroxyabieta-8,11,13-triene	ChEBI
8,11,13-Abietatrien-12-ol	ChEBI
Abieta-8,11,13-trien-12-ol	Kegg

Chemical Formula

C₂₀H₃₀O

Average Mass

286.4590 Da

Monoisotopic Mass

286.22967 Da

IUPAC Name

(4bS,8aS)-4b,8,8-trimethyl-2-(propan-2-yl)-4b,5,6,7,8,8a,9,10-octahydrophenanthren-3-ol

Traditional Name

ferruginol

CAS Registry Number

Not Available

SMILES

CC(C)C1=CC2=C(C=C1O)[C@@]1(C)CCCC(C)(C)[C@@H]1CC2

InChI Identifier

InChI=1S/C20H30O/c1-13(2)15-11-14-7-8-18-19(3,4)9-6-10-20(18,5)16(14)12-17(15)21/h11-13,18,21H,6-10H2,1-5H3/t18-,20+/m0/s1

InChI Key

QXNWVJOHUAQHLM-AZUAARDMSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Amentotaxus formosana	LOTUS Database	35616633
Callitris japonica	Plant	KNApSAcK
Calocedrus formosana	LOTUS Database	35616633
Calocedrus macrolepis	LOTUS Database	35616633
Cephalotaxus harringtonia var.drupacea	Plant	KNApSAcK
Chamaecyparis formosensis	Plant	KNApSAcK
Chamaecyparis lawsoniana	LOTUS Database	35616633
Chamaecyparis obtusa	LOTUS Database	35616633
Chamaecyparis pisifera	LOTUS Database	35616633
Cryptomeria japonica	LOTUS Database	35616633
Cryptomeria japonica D.DON.	Plant	KNApSAcK
Cupressus sempervirens	LOTUS Database	35616633
Fraxinus mandshurica	LOTUS Database	35616633
Harpagophytum procumbens	Plant	KNApSAcK
Isodon serra	LOTUS Database	35616633
Juniperus chinensis	LOTUS Database	35616633
Juniperus communis	LOTUS Database	35616633
Juniperus excelsa	Plant	KNApSAcK
Juniperus formosana	LOTUS Database	35616633
Juniperus formosana Hay.var.concolor Hay	Plant	KNApSAcK
Juniperus procera	LOTUS Database	35616633
Juniperus rigida	Plant	KNApSAcK
Podocarpus ferrugineus	Plant	KNApSAcK
Premna herbacea	LOTUS Database	35616633
Premna serratifolia	LOTUS Database	35616633
Prumnopitys andina	LOTUS Database	35616633
Prumnopitys ferruginea	LOTUS Database	35616633
Salvia amplexicaulis	LOTUS Database	35616633
Salvia amplexicaulis Lam.	Plant	KNApSAcK
Salvia apiana	LOTUS Database	35616633
Salvia argentea	Plant	KNApSAcK
Salvia blepharochaena Hedge and Hub.Mor.	Plant	KNApSAcK
Salvia blepharochlaena	Plant	KNApSAcK
Salvia bracteata Banks and Sol.	Plant	KNApSAcK
Salvia broussonetii	LOTUS Database	35616633
Salvia caespitosa	LOTUS Database	35616633
Salvia caespitosa Montbret and Aucher ex.Bentham	Plant	KNApSAcK
Salvia candidissima	LOTUS Database	35616633
Salvia ceratophylla L.	Plant	KNApSAcK
Salvia cyanescens	LOTUS Database	35616633
Salvia deserta	LOTUS Database	35616633
Salvia eriophora	LOTUS Database	35616633
Salvia eriophora Boiss and Kotschy	Plant	KNApSAcK
Salvia fruticosa	LOTUS Database	35616633
Salvia hypargeia	LOTUS Database	35616633
Salvia kronenburgii	LOTUS Database	35616633
Salvia lanigera	LOTUS Database	35616633
Salvia limbata	LOTUS Database	35616633
Salvia microstegia	LOTUS Database	35616633
Salvia miltiorrhiza	Plant	KNApSAcK
Salvia montbretii	LOTUS Database	35616633
Salvia multicaulis	Plant	KNApSAcK
Salvia munzii	LOTUS Database	35616633
Salvia napifolia	LOTUS Database	35616633
Salvia prionitis	LOTUS Database	35616633
Salvia przewalskii	Plant	KNApSAcK
Salvia recognita	LOTUS Database	35616633
Salvia recognita Fisch.et Mey.	Plant	KNApSAcK
Salvia rosmarinus	Plant	KNApSAcK
Salvia sahendica	LOTUS Database	35616633
Salvia sclarea	LOTUS Database	35616633
Salvia staminea	Plant	KNApSAcK
Salvia syriaca	LOTUS Database	35616633
Salvia syriaca L.	Plant	KNApSAcK
Salvia tomentosa	LOTUS Database	35616633
Salvia trijuga	Plant	KNApSAcK
Salvia virgata	LOTUS Database	35616633
Salvia viridis L.	Plant	KNApSAcK
Salvia wiedemannii	LOTUS Database	35616633
Salvia Yunnanensis	LOTUS Database	35616633
Salvinia molesta	LOTUS Database	35616633
Scutellaria baicalensis	LOTUS Database	35616633
Sequoia sempervirens	LOTUS Database	35616633
Taiwania cryptomerioides	Plant	KNApSAcK
Tetraclinis articulata	Plant	KNApSAcK
Teucrium polium	LOTUS Database	35616633
Thuja occidentalis	LOTUS Database	35616633
Thuja plicata	LOTUS Database	35616633
Thuja standishii	Plant	KNApSAcK
Thujopsis dolabrata	LOTUS Database	35616633
Torreya nucifera	LOTUS Database	35616633
Torreya nucifera var.radicans	Plant	KNApSAcK
Trogopterus xanthipes	LOTUS Database	35616633
Vitex rotundifolia	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

Diterpenoid
Abietane diterpenoid
Phenanthrene
Hydrophenanthrene
Tetralin
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

phenols (CHEBI:78274 )
abietane diterpenoid (CHEBI:78274 )
carbotricyclic compound (CHEBI:78274 )
meroterpenoid (CHEBI:78274 )
Abietanes (C09092 )

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	6.56	ALOGPS
logP	6.25	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	10.8	ChemAxon
pKa (Strongest Basic)	-5.2	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	1	ChemAxon
Refractivity	89.71 m³·mol⁻¹	ChemAxon
Polarizability	35.68 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

Not Available

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Ferruginol

METLIN ID

Not Available

PubChem Compound

442027

PDB ID

Not Available

ChEBI ID

78274

Good Scents ID

rw1588191

References

General References

Yang R, Du Z, Qiu T, Sun J, Shen Y, Huang L: Discovery and Functional Characterization of a Diverse Diterpene Synthase Family in the Medicinal Herb Isodon lophanthoides var. Gerardiana. Plant Cell Physiol. 2021 Jun 16. pii: 6300649. doi: 10.1093/pcp/pcab089. [PubMed:34133748 ]
Sadeer NB, Mahomoodally MF: Antibiotic Potentiation of Natural Products: A Promising Target to Fight Pathogenic Bacteria. Curr Drug Targets. 2021;22(5):555-572. doi: 10.2174/1389450121666200924113740. [PubMed:32972338 ]
Ma LT, Wang CH, Hon CY, Lee YR, Chu FH: Discovery and characterization of diterpene synthases in Chamaecyparis formosensis Matsum. which participated in an unprecedented diterpenoid biosynthesis route in conifer. Plant Sci. 2021 Mar;304:110790. doi: 10.1016/j.plantsci.2020.110790. Epub 2020 Dec 9. [PubMed:33568294 ]
Gonzalez-Cardenete MA, Rivas F, Basset R, Stadler M, Hering S, Padron JM, Zaragoza RJ, Dea-Ayuela MA: Biological Profiling of Semisynthetic C19-Functionalized Ferruginol and Sugiol Analogues. Antibiotics (Basel). 2021 Feb 12;10(2). pii: antibiotics10020184. doi: 10.3390/antibiotics10020184. [PubMed:33673350 ]
Salih AM, Al-Qurainy F, Nadeem M, Tarroum M, Khan S, Shaikhaldein HO, Al-Hashimi A, Alfagham A, Alkahtani J: Optimization Method for Phenolic Compounds Extraction from Medicinal Plant (Juniperus procera) and Phytochemicals Screening. Molecules. 2021 Dec 9;26(24). pii: molecules26247454. doi: 10.3390/molecules26247454. [PubMed:34946537 ]
Li W, Cao J, Wang X, Zhang Y, Sun Q, Jiang Y, Yao J, Li C, Wang Y, Wang W: Ferruginol Restores SIRT1-PGC-1alpha-Mediated Mitochondrial Biogenesis and Fatty Acid Oxidation for the Treatment of DOX-Induced Cardiotoxicity. Front Pharmacol. 2021 Nov 24;12:773834. doi: 10.3389/fphar.2021.773834. eCollection 2021. [PubMed:34899332 ]
Wang X, Cao G, Ding D, Li F, Zhao X, Wang J, Yang Y: Ferruginol prevents degeneration of dopaminergic neurons by enhancing clearance of alpha-synuclein in neuronal cells. Fitoterapia. 2022 Jan;156:105066. doi: 10.1016/j.fitote.2021.105066. Epub 2021 Oct 20. [PubMed:34678438 ]
Akdeniz M, Yener I, Dincel D, Firat M, Karatas Degirmenci D, Ertas A: Determination of fingerprints contents of different extracts and parts of six endemic Salvia taxa by GC-MS: Source species for valuable compounds with drug or drug potential. Biomed Chromatogr. 2022 Feb;36(2):e5263. doi: 10.1002/bmc.5263. Epub 2021 Nov 18. [PubMed:34647633 ]
Kentsop RAD, Iobbi V, Donadio G, Ruffoni B, De Tommasi N, Bisio A: Abietane Diterpenoids from the Hairy Roots of Salvia corrugata. Molecules. 2021 Aug 25;26(17). pii: molecules26175144. doi: 10.3390/molecules26175144. [PubMed:34500582 ]
Jassbi AR, Hadavand Mirzaei H, Firuzi O, Pirhadi S, Asadollahi M, Chandran JN, Schneider B: Cytotoxic abietane-type diterpenoids from roots of Salvia spinosa and their in Silico pharmacophore modeling. Nat Prod Res. 2021 Jul 22:1-6. doi: 10.1080/14786419.2021.1952202. [PubMed:34289771 ]
Sousa FTG, Nunes C, Romano CM, Sabino EC, Gonzalez-Cardenete MA: Anti-Zika virus activity of several abietane-type ferruginol analogues. Rev Inst Med Trop Sao Paulo. 2020 Dec 7;62:e97. doi: 10.1590/S1678-9946202062097. eCollection 2020. [PubMed:33295481 ]
Salih AM, Al-Qurainy F, Khan S, Tarroum M, Nadeem M, Shaikhaldein HO, Alabdallah NM, Alansi S, Alshameri A: Mass propagation of Juniperus procera Hoechst. Ex Endl. From seedling and screening of bioactive compounds in shoot and callus extract. BMC Plant Biol. 2021 Apr 21;21(1):192. doi: 10.1186/s12870-021-02946-2. [PubMed:33882830 ]
Luo G, Zhou J, Li G, Hu N, Xia X, Zhou H: Retracted: Ferruginol Diterpenoid Selectively Inhibits Human Thyroid Cancer Growth by Inducing Mitochondrial Dependent Apoptosis, Endogenous Reactive Oxygen Species (ROS) Production, Mitochondrial Membrane Potential Loss and Suppression of Mitogen-Activated Protein Kinase (MAPK) and PI3K/AKT Signaling Pathways. Med Sci Monit. 2021 Mar 25;27:e932341. doi: 10.12659/MSM.932341. [PubMed:33762565 ]
Xiong WD, Gong J, Xing C: [Retracted] Ferruginol exhibits anticancer effects in OVCAR3 human ovary cancer cells by inducing apoptosis, inhibition of cancer cell migration and G2/M phase cell cycle arrest. Mol Med Rep. 2021 Apr;23(4). pii: 229. doi: 10.3892/mmr.2021.11868. Epub 2021 Feb 4. [PubMed:33537814 ]
Zhang X, Li X, Wang C, Li H, Wang L, Chen Y, Feng J, Ali Alharbi S, Deng Y: Ameliorative effect of ferruginol on isoprenaline hydrochloride-induced myocardial infarction in rats. Environ Toxicol. 2021 Feb;36(2):249-256. doi: 10.1002/tox.23030. Epub 2020 Sep 18. [PubMed:32946155 ]

Showing NP-Card for (+)-Ferruginol (NP0052009)

MOL for NP0052009 ((+)-Ferruginol)

3D MOL for NP0052009 ((+)-Ferruginol)

3D SDF for NP0052009 ((+)-Ferruginol)

3D-SDF for NP0052009 ((+)-Ferruginol)

PDB for NP0052009 ((+)-Ferruginol)

3D PDB for NP0052009 ((+)-Ferruginol)

SMILES for NP0052009 ((+)-Ferruginol)

INCHI for NP0052009 ((+)-Ferruginol)

Structure for NP0052009 ((+)-Ferruginol)

3D Structure for NP0052009 ((+)-Ferruginol)