NP-MRD: Showing NP-Card for (+)-Jaborosalactol 18 (NP0079956)

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Record Information

Version

2.0

Created at

2022-04-29 01:01:16 UTC

Updated at

2022-04-29 01:01:16 UTC

NP-MRD ID

NP0079956

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Jaborosalactol 18

Description

(1S,2R,3R,6R,8S,12R,13S,16R,17R,18R)-2,17-dihydroxy-18-[(1S,2R,4R,6S)-2-hydroxy-1,6-dimethyl-3,7-dioxabicyclo[4.1.0]Heptan-4-yl]-12,16-dimethyl-7-oxahexacyclo[15.2.1.0²,¹⁶.0³,¹³.0⁶,⁸.0⁶,¹²]Icos-9-en-11-one belongs to the class of organic compounds known as steroids and steroid derivatives. Steroids and steroid derivatives are compounds based on the cyclopenta[a]phenanthrene carbon skeleton, partially or completely hydrogenated; there are usually methyl groups at C-10 and C-13, and often an alkyl group at C-17. By extension, one or more bond scissions, ring expansions and/or ring contractions of the skeleton may have occurred. (+)-Jaborosalactol 18 is found in Jaborosa bergii. Based on a literature review very few articles have been published on (1S,2R,3R,6R,8S,12R,13S,16R,17R,18R)-2,17-dihydroxy-18-[(1S,2R,4R,6S)-2-hydroxy-1,6-dimethyl-3,7-dioxabicyclo[4.1.0]Heptan-4-yl]-12,16-dimethyl-7-oxahexacyclo[15.2.1.0²,¹⁶.0³,¹³.0⁶,⁸.0⁶,¹²]Icos-9-en-11-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292203012D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304292203012D          

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  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  8 15  1  6  0  0  0
 13 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
 12 19  1  0  0  0  0
 19 20  1  6  0  0  0
 16 20  1  0  0  0  0
 17 21  1  6  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 25 27  1  0  0  0  0
 24 27  1  0  0  0  0
 25 28  1  6  0  0  0
 24 29  1  6  0  0  0
 23 30  1  1  0  0  0
 16 31  1  6  0  0  0
 13 32  1  6  0  0  0
 12 33  1  1  0  0  0
  5 34  1  6  0  0  0
  4 35  1  6  0  0  0
  3 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0079956

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12C[C@@H](O[C@@H](O)[C@@]1(C)O2)[C@H]1C[C@H]2C[C@]1(O)[C@@]1(C)CC[C@H]3[C@@H](CC[C@]45O[C@H]4C=CC(=O)[C@]35C)[C@]21O

> <INCHI_IDENTIFIER>
InChI=1S/C28H38O7/c1-22-9-7-15-16(8-10-27-20(34-27)6-5-19(29)24(15,27)3)28(22,32)14-11-17(26(22,31)12-14)18-13-23(2)25(4,35-23)21(30)33-18/h5-6,14-18,20-21,30-32H,7-13H2,1-4H3/t14-,15-,16+,17+,18+,20-,21+,22+,23-,24-,25+,26+,27-,28+/m0/s1

> <INCHI_KEY>
OWTUMHZPOZYQQH-VFBYRXHCSA-N

> <FORMULA>
C28H38O7

> <MOLECULAR_WEIGHT>
486.605

> <EXACT_MASS>
486.261753564

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
52.6538046062

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,3R,6R,8S,12R,13S,16R,17R,18R)-2,17-dihydroxy-18-[(1S,2R,4R,6S)-2-hydroxy-1,6-dimethyl-3,7-dioxabicyclo[4.1.0]heptan-4-yl]-12,16-dimethyl-7-oxahexacyclo[15.2.1.0^{2,16}.0^{3,13}.0^{6,8}.0^{6,12}]icos-9-en-11-one

> <ALOGPS_LOGP>
1.90

> <JCHEM_LOGP>
1.8419968229999992

> <ALOGPS_LOGS>
-3.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.667945249097052

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.167888820880238

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2324836935378807

> <JCHEM_POLAR_SURFACE_AREA>
112.05000000000001

> <JCHEM_REFRACTIVITY>
124.99589999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3R,6R,8S,12R,13S,16R,17R,18R)-2,17-dihydroxy-18-[(1S,2R,4R,6S)-2-hydroxy-1,6-dimethyl-3,7-dioxabicyclo[4.1.0]heptan-4-yl]-12,16-dimethyl-7-oxahexacyclo[15.2.1.0^{2,16}.0^{3,13}.0^{6,8}.0^{6,12}]icos-9-en-11-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       0.302  -0.374   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.172   1.091   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.859   2.235   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.365   1.914   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.840   0.449   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.809  -0.695   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.284  -2.160   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.346   0.128   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.377   1.272   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.902   2.736   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.396   3.058   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.883   0.950   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.358  -0.515   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.327  -1.658   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.821  -1.337   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.864  -0.836   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.896   0.308   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.421   1.773   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.914   2.094   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.023   0.510   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.402  -0.013   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      12.433   1.131   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      13.939   0.810   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.414  -0.655   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.383  -1.799   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.877  -1.478   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      14.889  -2.120   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      13.062  -3.305   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      15.879  -0.180   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      14.970   1.953   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       9.339  -2.301   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       7.833  -1.979   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       6.408   2.415   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       3.315  -1.016   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.890   3.379   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   35                                                  
CONECT    4    3    5   11   35                                             
CONECT    5    4    6    8   34                                             
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9   15                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10    4                                                       
CONECT   12    9   13   19   33                                             
CONECT   13   12   14   16   32                                             
CONECT   14   13   15                                                       
CONECT   15   14    8                                                       
CONECT   16   13   17   20   31                                             
CONECT   17   16   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18   12   20                                                  
CONECT   20   19   16                                                       
CONECT   21   17   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   30                                                  
CONECT   24   23   25   27   29                                             
CONECT   25   24   26   27   28                                             
CONECT   26   25   21                                                       
CONECT   27   25   24                                                       
CONECT   28   25                                                            
CONECT   29   24                                                            
CONECT   30   23                                                            
CONECT   31   16                                                            
CONECT   32   13                                                            
CONECT   33   12                                                            
CONECT   34    5                                                            
CONECT   35    4    3                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₈O₇

Average Mass

486.6050 Da

Monoisotopic Mass

486.26175 Da

IUPAC Name

(1S,2R,3R,6R,8S,12R,13S,16R,17R,18R)-2,17-dihydroxy-18-[(1S,2R,4R,6S)-2-hydroxy-1,6-dimethyl-3,7-dioxabicyclo[4.1.0]heptan-4-yl]-12,16-dimethyl-7-oxahexacyclo[15.2.1.0^{2,16}.0^{3,13}.0^{6,8}.0^{6,12}]icos-9-en-11-one

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@]12C[C@@H](O[C@@H](O)[C@@]1(C)O2)[C@H]1C[C@H]2C[C@]1(O)[C@@]1(C)CC[C@H]3[C@@H](CC[C@]45O[C@H]4C=CC(=O)[C@]35C)[C@]21O

InChI Identifier

InChI=1S/C28H38O7/c1-22-9-7-15-16(8-10-27-20(34-27)6-5-19(29)24(15,27)3)28(22,32)14-11-17(26(22,31)12-14)18-13-23(2)25(4,35-23)21(30)33-18/h5-6,14-18,20-21,30-32H,7-13H2,1-4H3/t14-,15-,16+,17+,18+,20-,21+,22+,23-,24-,25+,26+,27-,28+/m0/s1

InChI Key

OWTUMHZPOZYQQH-VFBYRXHCSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Jaborosa bergii	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroids and steroid derivatives. Steroids and steroid derivatives are compounds based on the cyclopenta[a]phenanthrene carbon skeleton, partially or completely hydrogenated; there are usually methyl groups at C-10 and C-13, and often an alkyl group at C-17. By extension, one or more bond scissions, ring expansions and/or ring contractions of the skeleton may have occurred.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Not Available

Direct Parent

Steroids and steroid derivatives

Alternative Parents

Substituents

Steroid
Norbornane monoterpenoid
Monoterpenoid
Cyclohexenone
Dioxepane
1,4-dioxepane
Oxane
Tertiary alcohol
Cyclic alcohol
Ketone
Hemiacetal
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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
logP	1.9	ALOGPS
logP	1.84	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	11.17	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	112.05 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	125 m³·mol⁻¹	ChemAxon
Polarizability	52.65 Å³	ChemAxon
Number of Rings	8	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

163105449

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Jaborosalactol 18 (NP0079956)

MOL for NP0079956 ((+)-Jaborosalactol 18)

3D MOL for NP0079956 ((+)-Jaborosalactol 18)

3D SDF for NP0079956 ((+)-Jaborosalactol 18)

3D-SDF for NP0079956 ((+)-Jaborosalactol 18)

PDB for NP0079956 ((+)-Jaborosalactol 18)

3D PDB for NP0079956 ((+)-Jaborosalactol 18)

SMILES for NP0079956 ((+)-Jaborosalactol 18)

INCHI for NP0079956 ((+)-Jaborosalactol 18)

Structure for NP0079956 ((+)-Jaborosalactol 18)

3D Structure for NP0079956 ((+)-Jaborosalactol 18)