NP-MRD: Showing NP-Card for (3s,6r)-6-[(1r,3as,3bs,5ar,7s,9as,11ar)-7-methoxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,3bh,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylheptane-2,3-diol (NP0228380)

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Record Information

Version

2.0

Created at

2022-09-06 08:00:49 UTC

Updated at

2022-09-06 08:00:49 UTC

NP-MRD ID

NP0228380

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,6r)-6-[(1r,3as,3bs,5ar,7s,9as,11ar)-7-methoxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,3bh,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylheptane-2,3-diol

Description

(3S,6R)-6-[(2S,5S,7R,10S,11S,14R,15R)-5-methoxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-1(17)-en-14-yl]-2-methylheptane-2,3-diol belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (3s,6r)-6-[(1r,3as,3bs,5ar,7s,9as,11ar)-7-methoxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,3bh,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylheptane-2,3-diol is found in Pinus luchuensis, Pinus monticola and Pinus yunnanensis. Based on a literature review very few articles have been published on (3S,6R)-6-[(2S,5S,7R,10S,11S,14R,15R)-5-methoxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-1(17)-en-14-yl]-2-methylheptane-2,3-diol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062210002D          

 34 37  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv1652309062210002D          

 34 37  0  0  1  0            999 V2000
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    6.6175   -0.3186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4347   -0.4315    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7456   -1.1957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9411    0.2198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4474    0.8712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5924   -0.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2897    0.7262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168   -2.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -2.7639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826   -2.2576    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4850   -3.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705   -2.4028    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5902   -3.1787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -3.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -2.6932    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4342   -2.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5510   -3.6551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1776   -3.3919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  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  1  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 11 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28  8  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 31 30  1  1  0  0  0
  6 31  1  0  0  0  0
 31 32  1  0  0  0  0
  3 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0228380

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1CC[C@@]2(C)[C@@H](CC[C@@H]3C2=CC[C@]2(C)[C@H](CC[C@@]32C)[C@H](C)CC[C@H](O)C(C)(C)O)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C31H54O3/c1-20(10-13-25(32)28(4,5)33)21-14-18-31(8)23-11-12-24-27(2,3)26(34-9)16-17-29(24,6)22(23)15-19-30(21,31)7/h15,20-21,23-26,32-33H,10-14,16-19H2,1-9H3/t20-,21-,23-,24+,25+,26+,29-,30-,31+/m1/s1

> <INCHI_KEY>
YKYJNGIGJFWUTD-HICJHRPVSA-N

> <FORMULA>
C31H54O3

> <MOLECULAR_WEIGHT>
474.77

> <EXACT_MASS>
474.407295599

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
88

> <JCHEM_AVERAGE_POLARIZABILITY>
59.6675080619146

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,6R)-6-[(2S,5S,7R,10S,11S,14R,15R)-5-methoxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(17)-en-14-yl]-2-methylheptane-2,3-diol

> <JCHEM_LOGP>
6.253018038666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.32511173350403

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.849642779283329

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0890278698781266

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
141.9101

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6R)-6-[(2S,5S,7R,10S,11S,14R,15R)-5-methoxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(17)-en-14-yl]-2-methylheptane-2,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.221  -5.841   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.698  -4.392   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.182  -4.121   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.341  -2.673   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.857  -2.402   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.850  -3.579   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.373  -2.131   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.366  -3.308   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.889  -1.859   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.405  -1.588   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.398  -2.766   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.069  -1.380   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.937  -2.816   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.882  -1.600   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.302  -0.173   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.407  -1.811   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.353  -0.595   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.878  -0.805   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      14.458  -2.232   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      14.823   0.410   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.769   1.626   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.039  -0.535   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      13.608   1.356   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.365  -4.295   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.090  -5.159   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.874  -4.214   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.505  -5.709   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.358  -4.485   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.835  -5.934   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.319  -6.205   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.326  -5.027   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.810  -5.298   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.028  -6.823   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.332  -6.332   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   32                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   31                                             
CONECT    7    6                                                            
CONECT    8    6    9   28                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   26                                             
CONECT   12   11                                                            
CONECT   13   11   14   24                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20                                                            
CONECT   24   13   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   11   27   28                                             
CONECT   27   26                                                            
CONECT   28   26    8   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30    6   32                                                  
CONECT   32   31    3   33   34                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₅₄O₃

Average Mass

474.7700 Da

Monoisotopic Mass

474.40730 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CO[C@H]1CC[C@@]2(C)[C@@H](CC[C@@H]3C2=CC[C@]2(C)[C@H](CC[C@@]32C)[C@H](C)CC[C@H](O)C(C)(C)O)C1(C)C

InChI Identifier

InChI=1S/C31H54O3/c1-20(10-13-25(32)28(4,5)33)21-14-18-31(8)23-11-12-24-27(2,3)26(34-9)16-17-29(24,6)22(23)15-19-30(21,31)7/h15,20-21,23-26,32-33H,10-14,16-19H2,1-9H3/t20-,21-,23-,24+,25+,26+,29-,30-,31+/m1/s1

InChI Key

YKYJNGIGJFWUTD-HICJHRPVSA-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
Pinus luchuensis	LOTUS Database	35616633
Pinus monticola	LOTUS Database	35616633
Pinus yunnanensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
25-hydroxysteroid
Dihydroxy bile acid, alcohol, or derivatives
24-hydroxysteroid
Cholane-skeleton
Hydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
14-alpha-methylsteroid
Steroid
Tertiary alcohol
Secondary alcohol
1,2-diol
Ether
Dialkyl ether
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organooxygen compound
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

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

162939471

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s,6r)-6-[(1r,3as,3bs,5ar,7s,9as,11ar)-7-methoxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,3bh,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylheptane-2,3-diol (NP0228380)

MOL for NP0228380 ((3s,6r)-6-[(1r,3as,3bs,5ar,7s,9as,11ar)-7-methoxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,3bh,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylheptane-2,3-diol)

3D MOL for NP0228380 ((3s,6r)-6-[(1r,3as,3bs,5ar,7s,9as,11ar)-7-methoxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,3bh,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylheptane-2,3-diol)

3D SDF for NP0228380 ((3s,6r)-6-[(1r,3as,3bs,5ar,7s,9as,11ar)-7-methoxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,3bh,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylheptane-2,3-diol)

3D-SDF for NP0228380 ((3s,6r)-6-[(1r,3as,3bs,5ar,7s,9as,11ar)-7-methoxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,3bh,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylheptane-2,3-diol)

PDB for NP0228380 ((3s,6r)-6-[(1r,3as,3bs,5ar,7s,9as,11ar)-7-methoxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,3bh,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylheptane-2,3-diol)

3D PDB for NP0228380 ((3s,6r)-6-[(1r,3as,3bs,5ar,7s,9as,11ar)-7-methoxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,3bh,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylheptane-2,3-diol)

SMILES for NP0228380 ((3s,6r)-6-[(1r,3as,3bs,5ar,7s,9as,11ar)-7-methoxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,3bh,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylheptane-2,3-diol)

INCHI for NP0228380 ((3s,6r)-6-[(1r,3as,3bs,5ar,7s,9as,11ar)-7-methoxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,3bh,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylheptane-2,3-diol)

Structure for NP0228380 ((3s,6r)-6-[(1r,3as,3bs,5ar,7s,9as,11ar)-7-methoxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,3bh,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylheptane-2,3-diol)

3D Structure for NP0228380 ((3s,6r)-6-[(1r,3as,3bs,5ar,7s,9as,11ar)-7-methoxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,3bh,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylheptane-2,3-diol)