NP-MRD: Showing NP-Card for 1-(2,6-dihydroxy-6-methylhept-4-en-2-yl)-3a,3b,6,6,9a-pentamethyl-dodecahydrocyclopenta[a]phenanthrene-1,7,11-triol (NP0209610)

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Record Information

Version

2.0

Created at

2022-09-05 07:05:06 UTC

Updated at

2022-09-05 07:05:06 UTC

NP-MRD ID

NP0209610

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(2,6-dihydroxy-6-methylhept-4-en-2-yl)-3a,3b,6,6,9a-pentamethyl-dodecahydrocyclopenta[a]phenanthrene-1,7,11-triol

Description

14-(2,6-Dihydroxy-6-methylhept-4-en-2-yl)-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecane-5,14,16-triol belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 1-(2,6-dihydroxy-6-methylhept-4-en-2-yl)-3a,3b,6,6,9a-pentamethyl-dodecahydrocyclopenta[a]phenanthrene-1,7,11-triol is found in Betula pendula. 14-(2,6-Dihydroxy-6-methylhept-4-en-2-yl)-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecane-5,14,16-triol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191522172D          

 35 38  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004191522172D          

 35 38  0  0  0  0            999 V2000
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    4.1858   -3.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9055   -2.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7176   -2.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5297   -2.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8100   -3.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6221   -3.4634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2782   -3.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9917   -4.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9942   -4.7234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4661   -3.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9343   -4.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1221   -4.2891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8418   -3.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5309   -4.2774    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
  5  2  1  4  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
 22 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 15 34  1  0  0  0  0
 21 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0209610

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)C=CCC(C)(O)C1(O)CCC2(C)C1C(O)CC1C3(C)CCC(O)C(C)(C)C3CCC21C

> <INCHI_IDENTIFIER>
InChI=1S/C30H52O5/c1-24(2,33)12-9-13-29(8,34)30(35)17-16-28(7)23(30)19(31)18-21-26(5)14-11-22(32)25(3,4)20(26)10-15-27(21,28)6/h9,12,19-23,31-35H,10-11,13-18H2,1-8H3

> <INCHI_KEY>
XLMGQIWAQRLJOD-UHFFFAOYSA-N

> <FORMULA>
C30H52O5

> <MOLECULAR_WEIGHT>
492.741

> <EXACT_MASS>
492.381474774

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
58.14403161098706

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14-(2,6-dihydroxy-6-methylhept-4-en-2-yl)-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14,16-triol

> <ALOGPS_LOGP>
3.80

> <JCHEM_LOGP>
3.220599096666668

> <ALOGPS_LOGS>
-4.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.501894383169763

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.249863617986769

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7636092301899565

> <JCHEM_POLAR_SURFACE_AREA>
101.15

> <JCHEM_REFRACTIVITY>
140.5369

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.21e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-(2,6-dihydroxy-6-methylhept-4-en-2-yl)-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14,16-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      -5.800  -7.607   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.807  -6.430   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.630  -7.423   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -5.984  -5.437   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -3.814  -5.253   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.298  -5.524   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.306  -4.346   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.210  -4.618   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.061  -6.133   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.482  -3.102   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.726  -4.889   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.838  -3.353   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.298  -6.368   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.573  -7.232   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.789  -6.287   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.158  -7.782   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.266  -4.839   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.258  -3.661   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.735  -2.213   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.774  -3.932   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.297  -5.381   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.813  -5.652   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.290  -4.203   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.806  -4.474   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.322  -4.746   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.845  -6.194   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      12.361  -6.465   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       9.853  -7.371   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.184  -8.144   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.322  -8.817   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.337  -7.100   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.344  -8.277   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.828  -8.006   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.305  -6.558   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.724  -7.984   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12   13   17                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   34                                             
CONECT   16   15                                                            
CONECT   17   15   11   18                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   34                                                  
CONECT   22   21   23   24   31                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28   22   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   15   21   35                                             
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₅₂O₅

Average Mass

492.7410 Da

Monoisotopic Mass

492.38147 Da

IUPAC Name

14-(2,6-dihydroxy-6-methylhept-4-en-2-yl)-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14,16-triol

Traditional Name

14-(2,6-dihydroxy-6-methylhept-4-en-2-yl)-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14,16-triol

CAS Registry Number

Not Available

SMILES

CC(C)(O)C=CCC(C)(O)C1(O)CCC2(C)C1C(O)CC1C3(C)CCC(O)C(C)(C)C3CCC21C

InChI Identifier

InChI=1S/C30H52O5/c1-24(2,33)12-9-13-29(8,34)30(35)17-16-28(7)23(30)19(31)18-21-26(5)14-11-22(32)25(3,4)20(26)10-15-27(21,28)6/h9,12,19-23,31-35H,10-11,13-18H2,1-8H3

InChI Key

XLMGQIWAQRLJOD-UHFFFAOYSA-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
Betula pendula	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
20-hydroxysteroid
3-hydroxysteroid
12-hydroxysteroid
17-hydroxysteroid
Hydroxysteroid
Steroid
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Polyol
Alcohol
Hydrocarbon derivative
Organic oxygen compound
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
logP	3.8	ALOGPS
logP	3.22	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	13.25	ChemAxon
pKa (Strongest Basic)	-0.76	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	101.15 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	140.54 m³·mol⁻¹	ChemAxon
Polarizability	58.14 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-(2,6-dihydroxy-6-methylhept-4-en-2-yl)-3a,3b,6,6,9a-pentamethyl-dodecahydrocyclopenta[a]phenanthrene-1,7,11-triol (NP0209610)

MOL for NP0209610 (1-(2,6-dihydroxy-6-methylhept-4-en-2-yl)-3a,3b,6,6,9a-pentamethyl-dodecahydrocyclopenta[a]phenanthrene-1,7,11-triol)

3D MOL for NP0209610 (1-(2,6-dihydroxy-6-methylhept-4-en-2-yl)-3a,3b,6,6,9a-pentamethyl-dodecahydrocyclopenta[a]phenanthrene-1,7,11-triol)

3D SDF for NP0209610 (1-(2,6-dihydroxy-6-methylhept-4-en-2-yl)-3a,3b,6,6,9a-pentamethyl-dodecahydrocyclopenta[a]phenanthrene-1,7,11-triol)

3D-SDF for NP0209610 (1-(2,6-dihydroxy-6-methylhept-4-en-2-yl)-3a,3b,6,6,9a-pentamethyl-dodecahydrocyclopenta[a]phenanthrene-1,7,11-triol)

PDB for NP0209610 (1-(2,6-dihydroxy-6-methylhept-4-en-2-yl)-3a,3b,6,6,9a-pentamethyl-dodecahydrocyclopenta[a]phenanthrene-1,7,11-triol)

3D PDB for NP0209610 (1-(2,6-dihydroxy-6-methylhept-4-en-2-yl)-3a,3b,6,6,9a-pentamethyl-dodecahydrocyclopenta[a]phenanthrene-1,7,11-triol)

SMILES for NP0209610 (1-(2,6-dihydroxy-6-methylhept-4-en-2-yl)-3a,3b,6,6,9a-pentamethyl-dodecahydrocyclopenta[a]phenanthrene-1,7,11-triol)

INCHI for NP0209610 (1-(2,6-dihydroxy-6-methylhept-4-en-2-yl)-3a,3b,6,6,9a-pentamethyl-dodecahydrocyclopenta[a]phenanthrene-1,7,11-triol)

Structure for NP0209610 (1-(2,6-dihydroxy-6-methylhept-4-en-2-yl)-3a,3b,6,6,9a-pentamethyl-dodecahydrocyclopenta[a]phenanthrene-1,7,11-triol)

3D Structure for NP0209610 (1-(2,6-dihydroxy-6-methylhept-4-en-2-yl)-3a,3b,6,6,9a-pentamethyl-dodecahydrocyclopenta[a]phenanthrene-1,7,11-triol)