NP-MRD: Showing NP-Card for (1s,2s,3r,5s,7r,9s,11s,12s,15r,16s)-3,5-dihydroxy-15-[(2r)-1-[(1r,2s,3s)-2-isopropyl-3-methylcyclopropyl]propan-2-yl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-14-one (NP0157102)

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Record Information

Version

2.0

Created at

2022-09-02 14:25:11 UTC

Updated at

2022-09-02 14:25:11 UTC

NP-MRD ID

NP0157102

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,3r,5s,7r,9s,11s,12s,15r,16s)-3,5-dihydroxy-15-[(2r)-1-[(1r,2s,3s)-2-isopropyl-3-methylcyclopropyl]propan-2-yl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-14-one

Description

(1S,2S,3R,5S,7R,9S,11S,12S,15R,16S)-3,5-dihydroxy-2,16-dimethyl-15-[(2R)-1-[(1R,2S,3S)-2-methyl-3-(propan-2-yl)cyclopropyl]propan-2-yl]-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]Octadecan-14-one belongs to the class of organic compounds known as gorgostanes and derivatives. These are steroids containing a gorgostane moiety, which a skeleton characterized by the presence. (1s,2s,3r,5s,7r,9s,11s,12s,15r,16s)-3,5-dihydroxy-15-[(2r)-1-[(1r,2s,3s)-2-isopropyl-3-methylcyclopropyl]propan-2-yl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-14-one is found in Persicaria nodosa. Based on a literature review very few articles have been published on (1S,2S,3R,5S,7R,9S,11S,12S,15R,16S)-3,5-dihydroxy-2,16-dimethyl-15-[(2R)-1-[(1R,2S,3S)-2-methyl-3-(propan-2-yl)cyclopropyl]propan-2-yl]-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]Octadecan-14-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022216252D          

 33 38  0  0  1  0            999 V2000
    7.6403    5.6266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.4448    4.2111    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    8.9134    3.5919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 32 33  1  1  0  0  0
M  END

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M  END


  Mrv1652309022216252D          

 33 38  0  0  1  0            999 V2000
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    2.5214    2.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0532    1.9404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3335    2.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1456    2.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6774    2.2309    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0373    2.9732    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
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 11  9  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 20 19  1  6  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  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 16 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 15 32  1  0  0  0  0
 11 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0157102

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@H]1[C@@H](C)[C@H]1C[C@@H](C)[C@H]1C(=O)C[C@H]2[C@@H]3C[C@@H]4O[C@@]44C[C@@H](O)C[C@@H](O)[C@]4(C)[C@H]3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C29H46O4/c1-14(2)25-16(4)18(25)9-15(3)26-22(31)12-21-19-11-24-29(33-24)13-17(30)10-23(32)28(29,6)20(19)7-8-27(21,26)5/h14-21,23-26,30,32H,7-13H2,1-6H3/t15-,16+,17+,18-,19-,20+,21+,23-,24+,25+,26+,27+,28+,29+/m1/s1

> <INCHI_KEY>
RSZFVFRVXKODEL-LHYMXLMTSA-N

> <FORMULA>
C29H46O4

> <MOLECULAR_WEIGHT>
458.683

> <EXACT_MASS>
458.339609961

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
55.07784786290552

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,3R,5S,7R,9S,11S,12S,15R,16S)-3,5-dihydroxy-2,16-dimethyl-15-[(2R)-1-[(1R,2S,3S)-2-methyl-3-(propan-2-yl)cyclopropyl]propan-2-yl]-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadecan-14-one

> <ALOGPS_LOGP>
3.27

> <JCHEM_LOGP>
4.099081811333332

> <ALOGPS_LOGS>
-4.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.285781711549735

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.418758076537738

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7650623197890933

> <JCHEM_POLAR_SURFACE_AREA>
70.06

> <JCHEM_REFRACTIVITY>
128.4842

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.31e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,3R,5S,7R,9S,11S,12S,15R,16S)-3,5-dihydroxy-15-[(2R)-1-[(1R,2S,3S)-2-isopropyl-3-methylcyclopropyl]propan-2-yl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadecan-14-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      14.262  10.503   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.317   9.287   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.791   9.498   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.897   7.861   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.113   6.916   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.638   6.705   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.686   6.335   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.741   5.119   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.216   5.330   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.635   6.757   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.270   4.114   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.698   2.635   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      12.147   2.112   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.424   1.771   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.208   2.716   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.692   2.445   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.169   0.996   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.653   0.725   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.137   0.454   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.660   1.903   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.144   1.632   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.151   2.809   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.365   2.538   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.675   4.257   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.191   4.528   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.714   5.977   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.183   3.351   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.707   4.799   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.699   3.622   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.222   5.071   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.738   5.342   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.731   4.164   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.403   5.550   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    7                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    4    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   32                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   32                                                  
CONECT   16   15   17   29                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18   20                                                       
CONECT   20   19   18   21   27                                             
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   20   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   16   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   15   11   33                                             
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₆O₄

Average Mass

458.6830 Da

Monoisotopic Mass

458.33961 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)[C@H]1[C@@H](C)[C@H]1C[C@@H](C)[C@H]1C(=O)C[C@H]2[C@@H]3C[C@@H]4O[C@@]44C[C@@H](O)C[C@@H](O)[C@]4(C)[C@H]3CC[C@]12C

InChI Identifier

InChI=1S/C29H46O4/c1-14(2)25-16(4)18(25)9-15(3)26-22(31)12-21-19-11-24-29(33-24)13-17(30)10-23(32)28(29,6)20(19)7-8-27(21,26)5/h14-21,23-26,30,32H,7-13H2,1-6H3/t15-,16+,17+,18-,19-,20+,21+,23-,24+,25+,26+,27+,28+,29+/m1/s1

InChI Key

RSZFVFRVXKODEL-LHYMXLMTSA-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
Polygonum nodosum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gorgostanes and derivatives. These are steroids containing a gorgostane moiety, which a skeleton characterized by the presence.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Gorgostanes and derivatives

Direct Parent

Gorgostanes and derivatives

Alternative Parents

Substituents

C24-propyl-sterol-skeleton
Gorgostane-skeleton
Triterpenoid
1-hydroxysteroid
Hydroxysteroid
5,6-epoxysteroid
Oxepane
Cyclic alcohol
Ketone
Cyclic ketone
Secondary alcohol
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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

163030153

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s,3r,5s,7r,9s,11s,12s,15r,16s)-3,5-dihydroxy-15-[(2r)-1-[(1r,2s,3s)-2-isopropyl-3-methylcyclopropyl]propan-2-yl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-14-one (NP0157102)

MOL for NP0157102 ((1s,2s,3r,5s,7r,9s,11s,12s,15r,16s)-3,5-dihydroxy-15-[(2r)-1-[(1r,2s,3s)-2-isopropyl-3-methylcyclopropyl]propan-2-yl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-14-one)

3D MOL for NP0157102 ((1s,2s,3r,5s,7r,9s,11s,12s,15r,16s)-3,5-dihydroxy-15-[(2r)-1-[(1r,2s,3s)-2-isopropyl-3-methylcyclopropyl]propan-2-yl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-14-one)

3D SDF for NP0157102 ((1s,2s,3r,5s,7r,9s,11s,12s,15r,16s)-3,5-dihydroxy-15-[(2r)-1-[(1r,2s,3s)-2-isopropyl-3-methylcyclopropyl]propan-2-yl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-14-one)

3D-SDF for NP0157102 ((1s,2s,3r,5s,7r,9s,11s,12s,15r,16s)-3,5-dihydroxy-15-[(2r)-1-[(1r,2s,3s)-2-isopropyl-3-methylcyclopropyl]propan-2-yl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-14-one)

PDB for NP0157102 ((1s,2s,3r,5s,7r,9s,11s,12s,15r,16s)-3,5-dihydroxy-15-[(2r)-1-[(1r,2s,3s)-2-isopropyl-3-methylcyclopropyl]propan-2-yl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-14-one)

3D PDB for NP0157102 ((1s,2s,3r,5s,7r,9s,11s,12s,15r,16s)-3,5-dihydroxy-15-[(2r)-1-[(1r,2s,3s)-2-isopropyl-3-methylcyclopropyl]propan-2-yl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-14-one)

SMILES for NP0157102 ((1s,2s,3r,5s,7r,9s,11s,12s,15r,16s)-3,5-dihydroxy-15-[(2r)-1-[(1r,2s,3s)-2-isopropyl-3-methylcyclopropyl]propan-2-yl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-14-one)

INCHI for NP0157102 ((1s,2s,3r,5s,7r,9s,11s,12s,15r,16s)-3,5-dihydroxy-15-[(2r)-1-[(1r,2s,3s)-2-isopropyl-3-methylcyclopropyl]propan-2-yl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-14-one)

Structure for NP0157102 ((1s,2s,3r,5s,7r,9s,11s,12s,15r,16s)-3,5-dihydroxy-15-[(2r)-1-[(1r,2s,3s)-2-isopropyl-3-methylcyclopropyl]propan-2-yl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-14-one)

3D Structure for NP0157102 ((1s,2s,3r,5s,7r,9s,11s,12s,15r,16s)-3,5-dihydroxy-15-[(2r)-1-[(1r,2s,3s)-2-isopropyl-3-methylcyclopropyl]propan-2-yl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-14-one)