NP-MRD: Showing NP-Card for (1s,3ar,3br,5ar,7r,8r,9ar,9br,11ar)-3a,7,8-trihydroxy-9a,11a-dimethyl-1-[(2r,3s,4r)-2,3,6-trihydroxy-4,6-dimethylheptan-2-yl]-dodecahydro-1h-cyclopenta[a]phenanthren-5-one (NP0185664)

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Record Information

Version

2.0

Created at

2022-09-04 01:09:59 UTC

Updated at

2022-09-04 01:10:00 UTC

NP-MRD ID

NP0185664

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3ar,3br,5ar,7r,8r,9ar,9br,11ar)-3a,7,8-trihydroxy-9a,11a-dimethyl-1-[(2r,3s,4r)-2,3,6-trihydroxy-4,6-dimethylheptan-2-yl]-dodecahydro-1h-cyclopenta[a]phenanthren-5-one

Description

(1s,3ar,3br,5ar,7r,8r,9ar,9br,11ar)-3a,7,8-trihydroxy-9a,11a-dimethyl-1-[(2r,3s,4r)-2,3,6-trihydroxy-4,6-dimethylheptan-2-yl]-dodecahydro-1h-cyclopenta[a]phenanthren-5-one is found in Rhaponticum integrifolium. Based on a literature review very few articles have been published on (1R,2R,4R,5R,7R,10R,11R,14S,15R)-4,5,11-trihydroxy-2,15-dimethyl-14-[(2R,3S,4R)-2,3,6-trihydroxy-4,6-dimethylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-8-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042203102D          

 35 38  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv1652309042203102D          

 35 38  0  0  1  0            999 V2000
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    7.6731   -2.5662    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2049   -3.1969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  1  0  0  0
 13 10  1  1  0  0  0
 13 14  1  0  0  0  0
 14 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
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 22 20  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 22 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 18 31  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 13 34  1  0  0  0  0
 16 34  1  0  0  0  0
 34 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0185664

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C28H48O7/c1-15(13-24(2,3)33)23(32)27(6,34)22-8-10-28(35)17-11-19(29)18-12-20(30)21(31)14-25(18,4)16(17)7-9-26(22,28)5/h15-18,20-23,30-35H,7-14H2,1-6H3/t15-,16-,17-,18+,20-,21-,22+,23+,25-,26-,27-,28-/m1/s1

> <INCHI_KEY>
VROYHCMGMRXPPB-GNAUFETFSA-N

> <FORMULA>
C28H48O7

> <MOLECULAR_WEIGHT>
496.685

> <EXACT_MASS>
496.340003886

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
55.32258440144689

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,4R,5R,7R,10R,11R,14S,15R)-4,5,11-trihydroxy-2,15-dimethyl-14-[(2R,3S,4R)-2,3,6-trihydroxy-4,6-dimethylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-8-one

> <JCHEM_LOGP>
0.9427156359999991

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.820003430431235

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.28656498384709

> <JCHEM_PKA_STRONGEST_BASIC>
-2.631168181499218

> <JCHEM_POLAR_SURFACE_AREA>
138.45000000000002

> <JCHEM_REFRACTIVITY>
132.5977

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4R,5R,7R,10R,11R,14S,15R)-4,5,11-trihydroxy-2,15-dimethyl-14-[(2R,3S,4R)-2,3,6-trihydroxy-4,6-dimethylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       1.731  -5.442   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.312  -6.868   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.366  -8.084   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.159  -7.873   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.685  -7.663   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.370  -9.399   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.051  -6.348   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.837  -7.079   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.417  -8.505   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.998  -6.808   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.566  -4.918   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.159  -1.754   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      11.868   0.190   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      15.316  -5.967   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6    7                                             
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    4                                                            
CONECT    8    2    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10   14   34                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   34                                             
CONECT   17   16                                                            
CONECT   18   16   19   31                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   29                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   22   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   18   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   13   16   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

C₂₈H₄₈O₇

Average Mass

496.6850 Da

Monoisotopic Mass

496.34000 Da

IUPAC Name

(1R,2R,4R,5R,7R,10R,11R,14S,15R)-4,5,11-trihydroxy-2,15-dimethyl-14-[(2R,3S,4R)-2,3,6-trihydroxy-4,6-dimethylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-8-one

Traditional Name

(1R,2R,4R,5R,7R,10R,11R,14S,15R)-4,5,11-trihydroxy-2,15-dimethyl-14-[(2R,3S,4R)-2,3,6-trihydroxy-4,6-dimethylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-8-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C28H48O7/c1-15(13-24(2,3)33)23(32)27(6,34)22-8-10-28(35)17-11-19(29)18-12-20(30)21(31)14-25(18,4)16(17)7-9-26(22,28)5/h15-18,20-23,30-35H,7-14H2,1-6H3/t15-,16-,17-,18+,20-,21-,22+,23+,25-,26-,27-,28-/m1/s1

InChI Key

VROYHCMGMRXPPB-GNAUFETFSA-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
Rhaponticum integrifolium	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	0.94	ChemAxon
pKa (Strongest Acidic)	13.29	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	138.45 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	132.6 m³·mol⁻¹	ChemAxon
Polarizability	55.32 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

162944467

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3ar,3br,5ar,7r,8r,9ar,9br,11ar)-3a,7,8-trihydroxy-9a,11a-dimethyl-1-[(2r,3s,4r)-2,3,6-trihydroxy-4,6-dimethylheptan-2-yl]-dodecahydro-1h-cyclopenta[a]phenanthren-5-one (NP0185664)

MOL for NP0185664 ((1s,3ar,3br,5ar,7r,8r,9ar,9br,11ar)-3a,7,8-trihydroxy-9a,11a-dimethyl-1-[(2r,3s,4r)-2,3,6-trihydroxy-4,6-dimethylheptan-2-yl]-dodecahydro-1h-cyclopenta[a]phenanthren-5-one)

3D MOL for NP0185664 ((1s,3ar,3br,5ar,7r,8r,9ar,9br,11ar)-3a,7,8-trihydroxy-9a,11a-dimethyl-1-[(2r,3s,4r)-2,3,6-trihydroxy-4,6-dimethylheptan-2-yl]-dodecahydro-1h-cyclopenta[a]phenanthren-5-one)

3D SDF for NP0185664 ((1s,3ar,3br,5ar,7r,8r,9ar,9br,11ar)-3a,7,8-trihydroxy-9a,11a-dimethyl-1-[(2r,3s,4r)-2,3,6-trihydroxy-4,6-dimethylheptan-2-yl]-dodecahydro-1h-cyclopenta[a]phenanthren-5-one)

3D-SDF for NP0185664 ((1s,3ar,3br,5ar,7r,8r,9ar,9br,11ar)-3a,7,8-trihydroxy-9a,11a-dimethyl-1-[(2r,3s,4r)-2,3,6-trihydroxy-4,6-dimethylheptan-2-yl]-dodecahydro-1h-cyclopenta[a]phenanthren-5-one)

PDB for NP0185664 ((1s,3ar,3br,5ar,7r,8r,9ar,9br,11ar)-3a,7,8-trihydroxy-9a,11a-dimethyl-1-[(2r,3s,4r)-2,3,6-trihydroxy-4,6-dimethylheptan-2-yl]-dodecahydro-1h-cyclopenta[a]phenanthren-5-one)

3D PDB for NP0185664 ((1s,3ar,3br,5ar,7r,8r,9ar,9br,11ar)-3a,7,8-trihydroxy-9a,11a-dimethyl-1-[(2r,3s,4r)-2,3,6-trihydroxy-4,6-dimethylheptan-2-yl]-dodecahydro-1h-cyclopenta[a]phenanthren-5-one)

SMILES for NP0185664 ((1s,3ar,3br,5ar,7r,8r,9ar,9br,11ar)-3a,7,8-trihydroxy-9a,11a-dimethyl-1-[(2r,3s,4r)-2,3,6-trihydroxy-4,6-dimethylheptan-2-yl]-dodecahydro-1h-cyclopenta[a]phenanthren-5-one)

INCHI for NP0185664 ((1s,3ar,3br,5ar,7r,8r,9ar,9br,11ar)-3a,7,8-trihydroxy-9a,11a-dimethyl-1-[(2r,3s,4r)-2,3,6-trihydroxy-4,6-dimethylheptan-2-yl]-dodecahydro-1h-cyclopenta[a]phenanthren-5-one)

Structure for NP0185664 ((1s,3ar,3br,5ar,7r,8r,9ar,9br,11ar)-3a,7,8-trihydroxy-9a,11a-dimethyl-1-[(2r,3s,4r)-2,3,6-trihydroxy-4,6-dimethylheptan-2-yl]-dodecahydro-1h-cyclopenta[a]phenanthren-5-one)

3D Structure for NP0185664 ((1s,3ar,3br,5ar,7r,8r,9ar,9br,11ar)-3a,7,8-trihydroxy-9a,11a-dimethyl-1-[(2r,3s,4r)-2,3,6-trihydroxy-4,6-dimethylheptan-2-yl]-dodecahydro-1h-cyclopenta[a]phenanthren-5-one)