NP-MRD: Showing NP-Card for 15-hydroxy-15-{4-hydroxy-4,5-dimethyl-3-oxo-2-oxabicyclo[3.2.1]octan-7-yl}-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one (NP0190997)

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Record Information

Version

2.0

Created at

2022-09-04 07:47:25 UTC

Updated at

2022-09-04 07:47:25 UTC

NP-MRD ID

NP0190997

Secondary Accession Numbers

None

Natural Product Identification

Common Name

15-hydroxy-15-{4-hydroxy-4,5-dimethyl-3-oxo-2-oxabicyclo[3.2.1]octan-7-yl}-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one

Description

15-Hydroxy-15-{4-hydroxy-4,5-dimethyl-3-oxo-2-oxabicyclo[3.2.1]Octan-7-yl}-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]Octadecan-3-one belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton. 15-hydroxy-15-{4-hydroxy-4,5-dimethyl-3-oxo-2-oxabicyclo[3.2.1]octan-7-yl}-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one is found in Dunalia solanacea. 15-Hydroxy-15-{4-hydroxy-4,5-dimethyl-3-oxo-2-oxabicyclo[3.2.1]Octan-7-yl}-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]Octadecan-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231515472D          

 34 40  0  0  0  0            999 V2000
    7.3342    4.2903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7973    1.6806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004231515472D          

 34 40  0  0  0  0            999 V2000
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  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 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
 20 22  1  0  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
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 22 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 18 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 13 33  1  0  0  0  0
 17 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0190997

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CC(OC(=O)C1(C)O)C(C2)C1(O)CCC2C3CC4OC44CCCC(=O)C4(C)C3CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H40O6/c1-23-13-18(19(14-23)33-22(30)26(23,4)31)27(32)11-8-16-15-12-21-28(34-21)9-5-6-20(29)25(28,3)17(15)7-10-24(16,27)2/h15-19,21,31-32H,5-14H2,1-4H3

> <INCHI_KEY>
PFSSPHXISVKZBM-UHFFFAOYSA-N

> <FORMULA>
C28H40O6

> <MOLECULAR_WEIGHT>
472.622

> <EXACT_MASS>
472.282489008

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
52.315464014139856

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
15-hydroxy-15-{4-hydroxy-4,5-dimethyl-3-oxo-2-oxabicyclo[3.2.1]octan-7-yl}-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one

> <ALOGPS_LOGP>
2.88

> <JCHEM_LOGP>
3.1924853803333333

> <ALOGPS_LOGS>
-5.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.105799751030169

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.193129685725937

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1923739017856203

> <JCHEM_POLAR_SURFACE_AREA>
96.36000000000001

> <JCHEM_REFRACTIVITY>
123.48809999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.59e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-hydroxy-15-{4-hydroxy-4,5-dimethyl-3-oxo-2-oxabicyclo[3.2.1]octan-7-yl}-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      13.691   8.009   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.617   6.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.570   4.688   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.688   3.137   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      14.227   3.064   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      15.243   4.221   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      16.726   3.808   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      14.972   5.737   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.493   5.974   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      15.674   7.107   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      11.786   4.385   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.200   5.869   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.270   4.114   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      10.159   5.650   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      10.698   2.635   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.424   1.771   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.208   2.716   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.692   2.445   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.169   0.996   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.653   0.725   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.137   0.454   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.660   1.903   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.144   1.632   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.151   2.809   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.675   4.257   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.191   4.528   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.714   5.977   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.183   3.351   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.707   4.799   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.699   3.622   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.222   5.071   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.738   5.342   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.731   4.164   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.403   5.550   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8   12                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    2    9   10                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    4   12   13                                                  
CONECT   12   11    2                                                       
CONECT   13   11   14   15   33                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   33                                                  
CONECT   18   17   19   30                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20   22                                                       
CONECT   22   21   20   23   28                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   22   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   18   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   13   17   34                                             
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₀O₆

Average Mass

472.6220 Da

Monoisotopic Mass

472.28249 Da

IUPAC Name

15-hydroxy-15-{4-hydroxy-4,5-dimethyl-3-oxo-2-oxabicyclo[3.2.1]octan-7-yl}-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one

Traditional Name

15-hydroxy-15-{4-hydroxy-4,5-dimethyl-3-oxo-2-oxabicyclo[3.2.1]octan-7-yl}-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one

CAS Registry Number

Not Available

SMILES

CC12CC(OC(=O)C1(C)O)C(C2)C1(O)CCC2C3CC4OC44CCCC(=O)C4(C)C3CCC12C

InChI Identifier

InChI=1S/C28H40O6/c1-23-13-18(19(14-23)33-22(30)26(23,4)31)27(32)11-8-16-15-12-21-28(34-21)9-5-6-20(29)25(28,3)17(15)7-10-24(16,27)2/h15-19,21,31-32H,5-14H2,1-4H3

InChI Key

PFSSPHXISVKZBM-UHFFFAOYSA-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
Saracha nigribaccata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Steroid lactones

Alternative Parents

Substituents

Steroid lactone
Estrane-skeleton
5,6-epoxysteroid
Caprolactone
Delta valerolactone
Delta_valerolactone
Oxepane
Oxane
Tertiary alcohol
Cyclic alcohol
Carboxylic acid ester
Ketone
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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
logP	2.88	ALOGPS
logP	3.19	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	12.19	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	96.36 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	123.49 m³·mol⁻¹	ChemAxon
Polarizability	52.32 Å³	ChemAxon
Number of Rings	7	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 15-hydroxy-15-{4-hydroxy-4,5-dimethyl-3-oxo-2-oxabicyclo[3.2.1]octan-7-yl}-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one (NP0190997)

MOL for NP0190997 (15-hydroxy-15-{4-hydroxy-4,5-dimethyl-3-oxo-2-oxabicyclo[3.2.1]octan-7-yl}-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

3D MOL for NP0190997 (15-hydroxy-15-{4-hydroxy-4,5-dimethyl-3-oxo-2-oxabicyclo[3.2.1]octan-7-yl}-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

3D SDF for NP0190997 (15-hydroxy-15-{4-hydroxy-4,5-dimethyl-3-oxo-2-oxabicyclo[3.2.1]octan-7-yl}-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

3D-SDF for NP0190997 (15-hydroxy-15-{4-hydroxy-4,5-dimethyl-3-oxo-2-oxabicyclo[3.2.1]octan-7-yl}-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

PDB for NP0190997 (15-hydroxy-15-{4-hydroxy-4,5-dimethyl-3-oxo-2-oxabicyclo[3.2.1]octan-7-yl}-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

3D PDB for NP0190997 (15-hydroxy-15-{4-hydroxy-4,5-dimethyl-3-oxo-2-oxabicyclo[3.2.1]octan-7-yl}-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

SMILES for NP0190997 (15-hydroxy-15-{4-hydroxy-4,5-dimethyl-3-oxo-2-oxabicyclo[3.2.1]octan-7-yl}-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

INCHI for NP0190997 (15-hydroxy-15-{4-hydroxy-4,5-dimethyl-3-oxo-2-oxabicyclo[3.2.1]octan-7-yl}-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

Structure for NP0190997 (15-hydroxy-15-{4-hydroxy-4,5-dimethyl-3-oxo-2-oxabicyclo[3.2.1]octan-7-yl}-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

3D Structure for NP0190997 (15-hydroxy-15-{4-hydroxy-4,5-dimethyl-3-oxo-2-oxabicyclo[3.2.1]octan-7-yl}-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)