NP-MRD: Showing NP-Card for (1r,3ar,3br,7r)-1,7-dihydroxy-1-[(2s)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6-tetramethyl-dodecahydro-2h-cyclopenta[a]phenanthren-9a-yl (NP0170524)

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Record Information

Version

2.0

Created at

2022-09-03 06:42:24 UTC

Updated at

2022-09-03 06:42:24 UTC

NP-MRD ID

NP0170524

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3ar,3br,7r)-1,7-dihydroxy-1-[(2s)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6-tetramethyl-dodecahydro-2h-cyclopenta[a]phenanthren-9a-yl

Description

(1r,3ar,3br,7r)-1,7-dihydroxy-1-[(2s)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6-tetramethyl-dodecahydro-2h-cyclopenta[a]phenanthren-9a-yl is found in Cleome amblyocarpa.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032208422D          

 33 37  0  0  1  0            999 V2000
   -0.3944    0.4309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3676   -0.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1922   -0.4204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3408   -1.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9921   -1.7246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7118   -2.5005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0532   -3.2965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3420   -1.6812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  8 10  1  6  0  0  0
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 13 14  1  0  0  0  0
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 17 18  1  0  0  0  0
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 21 22  1  0  0  0  0
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 23 25  1  0  0  0  0
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 29 30  1  0  0  0  0
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 19 31  1  0  0  0  0
 14 31  1  0  0  0  0
 31 32  1  6  0  0  0
  8 33  1  0  0  0  0
  5 33  1  0  0  0  0
M  RAD  1  20   2
M  END

     RDKit          3D

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M  RAD  1  20   2
M  END


  Mrv1652309032208422D          

 33 37  0  0  1  0            999 V2000
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  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  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  6  0  0  0
 10 11  1  1  0  0  0
 10 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 10 16  1  0  0  0  0
 16 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
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 20 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 19 31  1  0  0  0  0
 14 31  1  0  0  0  0
 31 32  1  6  0  0  0
  8 33  1  0  0  0  0
  5 33  1  0  0  0  0
M  RAD  1  20   2
M  END
> <DATABASE_ID>
NP0170524

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)C1CC[C@](C)(O1)[C@@]1(O)CC[C@]2(C)C1CCC1[C]3CC[C@@H](O)C(C)(C)C3CC[C@@]21C

> <INCHI_IDENTIFIER>
InChI=1S/C29H49O4/c1-24(2)19-12-14-26(5)20(18(19)8-11-22(24)30)9-10-21-27(26,6)16-17-29(21,32)28(7)15-13-23(33-28)25(3,4)31/h19-23,30-32H,8-17H2,1-7H3/t19?,20?,21?,22-,23?,26-,27-,28+,29-/m1/s1

> <INCHI_KEY>
JEDNLJZPCBQXBM-XAZQRVJJSA-N

> <FORMULA>
C29H49O4

> <MOLECULAR_WEIGHT>
461.707

> <EXACT_MASS>
461.363085058

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
55.00111107071275

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5R,10R,11R,14R)-5,14-dihydroxy-14-[(2S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,6,10,11-tetramethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-2-yl

> <ALOGPS_LOGP>
4.76

> <JCHEM_LOGP>
3.7468999999999997

> <ALOGPS_LOGS>
-5.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.384713975131671

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.431175076986275

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8264828916908481

> <JCHEM_POLAR_SURFACE_AREA>
69.92

> <JCHEM_REFRACTIVITY>
130.6304

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.00e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5R,10R,11R,14R)-5,14-dihydroxy-14-[(2S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,6,10,11-tetramethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-2-yl

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.736   0.804   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.686  -0.735   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.853  -0.685   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.225  -0.785   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.636  -2.274   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.852  -3.219   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.329  -4.668   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       0.099  -6.154   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.726  -4.889   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.838  -3.353   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.298  -6.368   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.573  -7.232   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.789  -6.287   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.158  -7.782   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.266  -4.839   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.258  -3.661   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.774  -3.932   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.297  -5.381   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.813  -5.652   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.806  -4.474   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.322  -4.746   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.845  -6.194   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      12.361  -6.465   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.853  -7.371   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.184  -8.144   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.322  -8.817   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.337  -7.100   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.344  -8.277   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.828  -8.006   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.305  -6.558   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.724  -7.984   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.638  -3.138   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6   33                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   33                                             
CONECT    9    8                                                            
CONECT   10    8   11   12   16                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   31                                             
CONECT   15   14                                                            
CONECT   16   14   10   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   31                                                  
CONECT   20   19   21   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   20   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   19   14   32                                             
CONECT   32   31                                                            
CONECT   33    8    5                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₉O₄

Average Mass

461.7070 Da

Monoisotopic Mass

461.36309 Da

IUPAC Name

(5R,10R,11R,14R)-5,14-dihydroxy-14-[(2S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,6,10,11-tetramethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-2-yl

Traditional Name

(5R,10R,11R,14R)-5,14-dihydroxy-14-[(2S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,6,10,11-tetramethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-2-yl

CAS Registry Number

Not Available

SMILES

CC(C)(O)C1CC[C@](C)(O1)[C@@]1(O)CC[C@]2(C)C1CCC1[C]3CC[C@@H](O)C(C)(C)C3CC[C@@]21C

InChI Identifier

InChI=1S/C29H49O4/c1-24(2)19-12-14-26(5)20(18(19)8-11-22(24)30)9-10-21-27(26,6)16-17-29(21,32)28(7)15-13-23(33-28)25(3,4)31/h19-23,30-32H,8-17H2,1-7H3/t19?,20?,21?,22-,23?,26-,27-,28+,29-/m1/s1

InChI Key

JEDNLJZPCBQXBM-XAZQRVJJSA-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
Cleome amblyocarpa	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	4.76	ALOGPS
logP	3.75	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	13.43	ChemAxon
pKa (Strongest Basic)	-0.83	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.92 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	130.63 m³·mol⁻¹	ChemAxon
Polarizability	55 Å³	ChemAxon
Number of Rings	5	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

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3ar,3br,7r)-1,7-dihydroxy-1-[(2s)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6-tetramethyl-dodecahydro-2h-cyclopenta[a]phenanthren-9a-yl (NP0170524)

MOL for NP0170524 ((1r,3ar,3br,7r)-1,7-dihydroxy-1-[(2s)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6-tetramethyl-dodecahydro-2h-cyclopenta[a]phenanthren-9a-yl)

3D MOL for NP0170524 ((1r,3ar,3br,7r)-1,7-dihydroxy-1-[(2s)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6-tetramethyl-dodecahydro-2h-cyclopenta[a]phenanthren-9a-yl)

3D SDF for NP0170524 ((1r,3ar,3br,7r)-1,7-dihydroxy-1-[(2s)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6-tetramethyl-dodecahydro-2h-cyclopenta[a]phenanthren-9a-yl)

3D-SDF for NP0170524 ((1r,3ar,3br,7r)-1,7-dihydroxy-1-[(2s)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6-tetramethyl-dodecahydro-2h-cyclopenta[a]phenanthren-9a-yl)

PDB for NP0170524 ((1r,3ar,3br,7r)-1,7-dihydroxy-1-[(2s)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6-tetramethyl-dodecahydro-2h-cyclopenta[a]phenanthren-9a-yl)

3D PDB for NP0170524 ((1r,3ar,3br,7r)-1,7-dihydroxy-1-[(2s)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6-tetramethyl-dodecahydro-2h-cyclopenta[a]phenanthren-9a-yl)

SMILES for NP0170524 ((1r,3ar,3br,7r)-1,7-dihydroxy-1-[(2s)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6-tetramethyl-dodecahydro-2h-cyclopenta[a]phenanthren-9a-yl)

INCHI for NP0170524 ((1r,3ar,3br,7r)-1,7-dihydroxy-1-[(2s)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6-tetramethyl-dodecahydro-2h-cyclopenta[a]phenanthren-9a-yl)

Structure for NP0170524 ((1r,3ar,3br,7r)-1,7-dihydroxy-1-[(2s)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6-tetramethyl-dodecahydro-2h-cyclopenta[a]phenanthren-9a-yl)

3D Structure for NP0170524 ((1r,3ar,3br,7r)-1,7-dihydroxy-1-[(2s)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6-tetramethyl-dodecahydro-2h-cyclopenta[a]phenanthren-9a-yl)