NP-MRD: Showing NP-Card for levopimaradienol (NP0267777)

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Record Information

Version

2.0

Created at

2022-09-08 12:39:38 UTC

Updated at

2022-09-08 12:39:38 UTC

NP-MRD ID

NP0267777

Secondary Accession Numbers

None

Natural Product Identification

Common Name

levopimaradienol

Description

Levopimaradienol belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Thus, levopimaradienol is considered to be an isoprenoid. levopimaradienol is found in Larix gmelinii. levopimaradienol was first documented in 2005 (PMID: 15911762). Based on a literature review very few articles have been published on levopimaradienol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 53 55  0  0  0  0  0  0  0  0999 V2000
    4.9999   -0.1896    1.6892 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5570    0.7237    0.5678 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5833    0.8121   -0.5135 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2396    0.2700    0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9274   -0.0402   -1.1210 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6081   -0.4908   -1.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6004   -0.6823   -0.5601 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9770   -0.3168    0.7814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1679    0.1123    1.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0053   -0.3872    1.9286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1554    0.4932    1.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7149   -0.2471    0.2131 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1347    0.1522   -0.0092 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4134    1.5993    0.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9593   -0.6455    1.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3007   -0.3201    0.8594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6066   -0.2808   -1.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8059   -1.4701   -1.8544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3602   -1.1906   -1.9868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8033   -0.2112   -0.9518 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6544    1.0955   -1.6400 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1448   -0.7797    2.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7910   -0.8477    1.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4291    0.4500    2.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4042    1.7658    0.9762 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5926    0.8994   -0.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6191   -0.1630   -1.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4854    1.6806   -1.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7618    0.0551   -1.8552 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8362   -1.4137   -2.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3105    0.2745   -2.3787 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4358   -1.8329   -0.5049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4033    0.3746    2.1394 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3851   -0.0189    2.8654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3401   -1.4362    2.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8793    0.5605    2.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6998    1.4635    1.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7486   -1.3228    0.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9330    2.0555   -0.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1206    1.7512    1.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5155    2.1837    0.5903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7773   -1.7340    0.8519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6810   -0.3649    2.0420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3612    0.4360    0.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5927    0.5521   -2.1117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6691   -0.6280   -1.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2213   -1.7150   -2.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0448   -2.3225   -1.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8132   -2.1498   -1.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0999   -0.8611   -3.0137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5694    0.9177   -2.7319 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2479    1.6084   -1.2473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5267    1.7757   -1.5427 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  1  0
  7  8  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  1
 13 15  1  0
 15 16  1  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  6
  8  9  2  0
  9  4  1  0
 20  7  1  0
 20 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  1
 10 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  1
 14 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 21 51  1  0
 21 52  1  0
 21 53  1  0
  9 33  1  0
M  END


  Mrv1652309082214392D          

 21 23  0  0  1  0            999 V2000
    5.2520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -0.3020    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    1.1270    0.0000 C   0  0  0  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
    2.3645    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    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
    2.3645   -1.0164    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
    1.1270   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4452   -1.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4733   -0.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6165   -1.3966    0.0000 O   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
    1.5395    0.4125    0.0000 C   0  0  2  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
  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
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  6  0  0  0
 15 16  1  0  0  0  0
 13 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
  7 20  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0267777

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=CC[C@H]2C(CC[C@H]3[C@](C)(CO)CCC[C@]23C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O/c1-14(2)15-6-8-17-16(12-15)7-9-18-19(3,13-21)10-5-11-20(17,18)4/h6,12,14,17-18,21H,5,7-11,13H2,1-4H3/t17-,18-,19-,20+/m0/s1

> <INCHI_KEY>
CYOURYOZWLIJFB-LWYYNNOASA-N

> <FORMULA>
C20H32O

> <MOLECULAR_WEIGHT>
288.475

> <EXACT_MASS>
288.24531565

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
36.105430565021564

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1R,4aR,4bS,10aR)-1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,4b,5,9,10,10a-decahydrophenanthren-1-yl]methanol

> <JCHEM_LOGP>
4.480101304666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.592336961581896

> <JCHEM_PKA_STRONGEST_BASIC>
-1.227511813004078

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
91.2717

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
levopimaradienol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.804  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.724   2.104   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       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.724  -0.564   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       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.831  -2.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.883  -1.090   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.151  -2.607   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   20                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    4                                                       
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14   15   17                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15                                                            
CONECT   17   13   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    7   12   21                                             
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
[(1R,4AR,4BS,10ar)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,4b,5,9,10,10a-decahydrophenanthren-1-yl]methanol	ChEBI
Levopimaradien-18-ol	ChEBI
Levopimarol	ChEBI
Abieta-8(14),12-dien-18-ol	Kegg

Chemical Formula

C₂₀H₃₂O

Average Mass

288.4750 Da

Monoisotopic Mass

288.24532 Da

IUPAC Name

[(1R,4aR,4bS,10aR)-1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,4b,5,9,10,10a-decahydrophenanthren-1-yl]methanol

Traditional Name

levopimaradienol

CAS Registry Number

Not Available

SMILES

CC(C)C1=CC[C@H]2C(CC[C@H]3[C@](C)(CO)CCC[C@]23C)=C1

InChI Identifier

InChI=1S/C20H32O/c1-14(2)15-6-8-17-16(12-15)7-9-18-19(3,13-21)10-5-11-20(17,18)4/h6,12,14,17-18,21H,5,7-11,13H2,1-4H3/t17-,18-,19-,20+/m0/s1

InChI Key

CYOURYOZWLIJFB-LWYYNNOASA-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
Larix gmelini	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
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

abietane diterpenoid (CHEBI:52482 )
carbotricyclic compound (CHEBI:52482 )
Abietane diterpenoids (LMPR0104050008 )

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	4.48	ChemAxon
pKa (Strongest Acidic)	18.59	ChemAxon
pKa (Strongest Basic)	-1.2	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	2	ChemAxon
Refractivity	91.27 m³·mol⁻¹	ChemAxon
Polarizability	36.11 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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

391689

KEGG Compound ID

C11883

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

443475

PDB ID

Not Available

ChEBI ID

52482

Good Scents ID

Not Available

References

General References

Ro DK, Arimura G, Lau SY, Piers E, Bohlmann J: Loblolly pine abietadienol/abietadienal oxidase PtAO (CYP720B1) is a multifunctional, multisubstrate cytochrome P450 monooxygenase. Proc Natl Acad Sci U S A. 2005 May 31;102(22):8060-5. doi: 10.1073/pnas.0500825102. Epub 2005 May 23. [PubMed:15911762 ]
LOTUS database [Link]

Showing NP-Card for levopimaradienol (NP0267777)

MOL for NP0267777 (levopimaradienol)

3D MOL for NP0267777 (levopimaradienol)

3D SDF for NP0267777 (levopimaradienol)

3D-SDF for NP0267777 (levopimaradienol)

PDB for NP0267777 (levopimaradienol)

3D PDB for NP0267777 (levopimaradienol)

SMILES for NP0267777 (levopimaradienol)

INCHI for NP0267777 (levopimaradienol)

Structure for NP0267777 (levopimaradienol)

3D Structure for NP0267777 (levopimaradienol)