NP-MRD: Showing NP-Card for (1s,3r,3ar,5ar,5br,7ar,11as,11br,12r,13ar,13br)-1,3,12-trihydroxy-1-(2-hydroxypropan-2-yl)-3a,5a,5b,8,8,11a-hexamethyl-tetradecahydrocyclopenta[a]chrysen-9-one (NP0241365)

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Record Information

Version

2.0

Created at

2022-09-07 01:25:32 UTC

Updated at

2022-09-07 01:25:32 UTC

NP-MRD ID

NP0241365

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3r,3ar,5ar,5br,7ar,11as,11br,12r,13ar,13br)-1,3,12-trihydroxy-1-(2-hydroxypropan-2-yl)-3a,5a,5b,8,8,11a-hexamethyl-tetradecahydrocyclopenta[a]chrysen-9-one

Description

(1R,2R,5R,6R,8S,9R,10R,12R,13R,14S,19R)-6,8,12-trihydroxy-8-(2-hydroxypropan-2-yl)-1,2,5,14,18,18-hexamethylpentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]Henicosan-17-one belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (1s,3r,3ar,5ar,5br,7ar,11as,11br,12r,13ar,13br)-1,3,12-trihydroxy-1-(2-hydroxypropan-2-yl)-3a,5a,5b,8,8,11a-hexamethyl-tetradecahydrocyclopenta[a]chrysen-9-one is found in Salvia wagneriana. Based on a literature review very few articles have been published on (1R,2R,5R,6R,8S,9R,10R,12R,13R,14S,19R)-6,8,12-trihydroxy-8-(2-hydroxypropan-2-yl)-1,2,5,14,18,18-hexamethylpentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]Henicosan-17-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072203252D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309072203252D          

 35 39  0  0  1  0            999 V2000
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   -0.4114   -0.2717    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2633   -0.7464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8130   -0.9923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2146   -1.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5337   -0.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0923   -1.3939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1701    0.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0964    0.8741    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7178    1.4167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2921    1.0579    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7871    1.7179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1095    1.7785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9344    1.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3577    1.0830    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2590    1.9020    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
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 15 13  1  1  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  1  0  0  0
 21 23  1  6  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 21 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 20 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 19 34  1  0  0  0  0
 13 34  1  0  0  0  0
 34 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0241365

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)[C@]1(O)C[C@@H](O)[C@]2(C)CC[C@]3(C)[C@H](C[C@@H](O)[C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O5/c1-24(2)19-9-12-29(8)23(26(19,5)11-10-20(24)32)18(31)15-17-22-27(6,13-14-28(17,29)7)21(33)16-30(22,35)25(3,4)34/h17-19,21-23,31,33-35H,9-16H2,1-8H3/t17-,18-,19+,21-,22-,23-,26+,27+,28-,29-,30+/m1/s1

> <INCHI_KEY>
RYBVPBNFSNLVFT-UUNSELIWSA-N

> <FORMULA>
C30H50O5

> <MOLECULAR_WEIGHT>
490.725

> <EXACT_MASS>
490.36582471

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
57.08691662228783

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5R,6R,8S,9R,10R,12R,13R,14S,19R)-6,8,12-trihydroxy-8-(2-hydroxypropan-2-yl)-1,2,5,14,18,18-hexamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-17-one

> <JCHEM_LOGP>
3.350296867666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.520473573995762

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.308031824765067

> <JCHEM_PKA_STRONGEST_BASIC>
-0.2845892529771131

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
136.5061

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5R,6R,8S,9R,10R,12R,13R,14S,19R)-6,8,12-trihydroxy-8-(2-hydroxypropan-2-yl)-1,2,5,14,18,18-hexamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-17-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      10.133   2.664   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.694   2.115   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.403   3.628   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.484   0.793   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      11.024   0.817   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.734  -0.552   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.194  -0.575   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.404   0.747   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.655  -0.599   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.154   2.092   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.364   3.414   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.824   3.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.074   2.045   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.284   3.367   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.864   0.723   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.115  -0.622   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.905  -1.944   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.575  -0.645   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.785   0.676   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.245   0.653   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.768  -0.507   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.492  -1.393   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.518  -1.852   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.267  -3.198   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.863  -1.103   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.172  -2.602   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.184   0.098   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.047   1.632   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -3.207   2.645   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -0.545   1.975   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.469   3.207   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.204   3.320   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.744   3.343   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.534   2.022   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.350   3.550   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   10                                             
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   15                                             
CONECT    9    8                                                            
CONECT   10    8    2   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   34                                             
CONECT   14   13                                                            
CONECT   15   13    8   16                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   34                                                  
CONECT   20   19   21   30                                                  
CONECT   21   20   22   23   27                                             
CONECT   22   21                                                            
CONECT   23   21   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23                                                            
CONECT   27   21   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   20   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   19   13   35                                             
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₅₀O₅

Average Mass

490.7250 Da

Monoisotopic Mass

490.36582 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)(O)[C@]1(O)C[C@@H](O)[C@]2(C)CC[C@]3(C)[C@H](C[C@@H](O)[C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12

InChI Identifier

InChI=1S/C30H50O5/c1-24(2)19-9-12-29(8)23(26(19,5)11-10-20(24)32)18(31)15-17-22-27(6,13-14-28(17,29)7)21(33)16-30(22,35)25(3,4)34/h17-19,21-23,31,33-35H,9-16H2,1-8H3/t17-,18-,19+,21-,22-,23-,26+,27+,28-,29-,30+/m1/s1

InChI Key

RYBVPBNFSNLVFT-UUNSELIWSA-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
Salvia wagneriana	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
6-hydroxysteroid
15-hydroxysteroid
Hydroxysteroid
17-hydroxysteroid
Steroid
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Ketone
Cyclic ketone
Polyol
Organic oxygen compound
Organooxygen compound
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxide
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

12110562

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3r,3ar,5ar,5br,7ar,11as,11br,12r,13ar,13br)-1,3,12-trihydroxy-1-(2-hydroxypropan-2-yl)-3a,5a,5b,8,8,11a-hexamethyl-tetradecahydrocyclopenta[a]chrysen-9-one (NP0241365)

MOL for NP0241365 ((1s,3r,3ar,5ar,5br,7ar,11as,11br,12r,13ar,13br)-1,3,12-trihydroxy-1-(2-hydroxypropan-2-yl)-3a,5a,5b,8,8,11a-hexamethyl-tetradecahydrocyclopenta[a]chrysen-9-one)

3D MOL for NP0241365 ((1s,3r,3ar,5ar,5br,7ar,11as,11br,12r,13ar,13br)-1,3,12-trihydroxy-1-(2-hydroxypropan-2-yl)-3a,5a,5b,8,8,11a-hexamethyl-tetradecahydrocyclopenta[a]chrysen-9-one)

3D SDF for NP0241365 ((1s,3r,3ar,5ar,5br,7ar,11as,11br,12r,13ar,13br)-1,3,12-trihydroxy-1-(2-hydroxypropan-2-yl)-3a,5a,5b,8,8,11a-hexamethyl-tetradecahydrocyclopenta[a]chrysen-9-one)

3D-SDF for NP0241365 ((1s,3r,3ar,5ar,5br,7ar,11as,11br,12r,13ar,13br)-1,3,12-trihydroxy-1-(2-hydroxypropan-2-yl)-3a,5a,5b,8,8,11a-hexamethyl-tetradecahydrocyclopenta[a]chrysen-9-one)

PDB for NP0241365 ((1s,3r,3ar,5ar,5br,7ar,11as,11br,12r,13ar,13br)-1,3,12-trihydroxy-1-(2-hydroxypropan-2-yl)-3a,5a,5b,8,8,11a-hexamethyl-tetradecahydrocyclopenta[a]chrysen-9-one)

3D PDB for NP0241365 ((1s,3r,3ar,5ar,5br,7ar,11as,11br,12r,13ar,13br)-1,3,12-trihydroxy-1-(2-hydroxypropan-2-yl)-3a,5a,5b,8,8,11a-hexamethyl-tetradecahydrocyclopenta[a]chrysen-9-one)

SMILES for NP0241365 ((1s,3r,3ar,5ar,5br,7ar,11as,11br,12r,13ar,13br)-1,3,12-trihydroxy-1-(2-hydroxypropan-2-yl)-3a,5a,5b,8,8,11a-hexamethyl-tetradecahydrocyclopenta[a]chrysen-9-one)

INCHI for NP0241365 ((1s,3r,3ar,5ar,5br,7ar,11as,11br,12r,13ar,13br)-1,3,12-trihydroxy-1-(2-hydroxypropan-2-yl)-3a,5a,5b,8,8,11a-hexamethyl-tetradecahydrocyclopenta[a]chrysen-9-one)

Structure for NP0241365 ((1s,3r,3ar,5ar,5br,7ar,11as,11br,12r,13ar,13br)-1,3,12-trihydroxy-1-(2-hydroxypropan-2-yl)-3a,5a,5b,8,8,11a-hexamethyl-tetradecahydrocyclopenta[a]chrysen-9-one)

3D Structure for NP0241365 ((1s,3r,3ar,5ar,5br,7ar,11as,11br,12r,13ar,13br)-1,3,12-trihydroxy-1-(2-hydroxypropan-2-yl)-3a,5a,5b,8,8,11a-hexamethyl-tetradecahydrocyclopenta[a]chrysen-9-one)