NP-MRD: Showing NP-Card for 18-(3,4-dimethyl-5-oxooxolan-2-yl)-10,17-dihydroxy-4,17-dimethyl-19,21-dioxahexacyclo[11.6.1.1¹,¹⁵.0³,¹².0⁴,⁹.0¹⁶,²⁰]henicosa-6,8-dien-5-one (NP0202538)

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Record Information

Version

2.0

Created at

2022-09-04 21:46:14 UTC

Updated at

2022-09-04 21:46:14 UTC

NP-MRD ID

NP0202538

Secondary Accession Numbers

None

Natural Product Identification

Common Name

18-(3,4-dimethyl-5-oxooxolan-2-yl)-10,17-dihydroxy-4,17-dimethyl-19,21-dioxahexacyclo[11.6.1.1¹,¹⁵.0³,¹².0⁴,⁹.0¹⁶,²⁰]henicosa-6,8-dien-5-one

Description

18-(3,4-Dimethyl-5-oxooxolan-2-yl)-10,17-dihydroxy-4,17-dimethyl-19,21-dioxahexacyclo[11.6.1.1¹,¹⁵.0³,¹².0⁴,⁹.0¹⁶,²⁰]Henicosa-6,8-dien-5-one belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton. 18-(3,4-dimethyl-5-oxooxolan-2-yl)-10,17-dihydroxy-4,17-dimethyl-19,21-dioxahexacyclo[11.6.1.1¹,¹⁵.0³,¹².0⁴,⁹.0¹⁶,²⁰]henicosa-6,8-dien-5-one is found in Deprea subtriflora. 18-(3,4-Dimethyl-5-oxooxolan-2-yl)-10,17-dihydroxy-4,17-dimethyl-19,21-dioxahexacyclo[11.6.1.1¹,¹⁵.0³,¹².0⁴,⁹.0¹⁶,²⁰]Henicosa-6,8-dien-5-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171521052D          

 34 40  0  0  0  0            999 V2000
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M  END

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M  END


  Mrv1533004171521052D          

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 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 11 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 11 31  1  0  0  0  0
 26 31  1  0  0  0  0
 30 32  1  0  0  0  0
  9 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0202538

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C(C)C(=O)OC1C1OC23CC4C(CC(O)C5=CC=CC(=O)C45C)C4CC(O2)C(C34)C1(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C27H34O7/c1-11-12(2)24(30)32-22(11)23-26(4,31)21-18-9-14-13-8-17(28)15-6-5-7-19(29)25(15,3)16(13)10-27(33-18,34-23)20(14)21/h5-7,11-14,16-18,20-23,28,31H,8-10H2,1-4H3

> <INCHI_KEY>
GNNMCSRZHQSNEB-UHFFFAOYSA-N

> <FORMULA>
C27H34O7

> <MOLECULAR_WEIGHT>
470.562

> <EXACT_MASS>
470.230453435

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
50.36720522772013

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
18-(3,4-dimethyl-5-oxooxolan-2-yl)-10,17-dihydroxy-4,17-dimethyl-19,21-dioxahexacyclo[11.6.1.1¹,¹⁵.0³,¹².0⁴,⁹.0¹⁶,²⁰]henicosa-6,8-dien-5-one

> <ALOGPS_LOGP>
2.69

> <JCHEM_LOGP>
1.9361887349999998

> <ALOGPS_LOGS>
-3.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.612588764867759

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.593726705789553

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9898050878996063

> <JCHEM_POLAR_SURFACE_AREA>
102.29000000000002

> <JCHEM_REFRACTIVITY>
122.6256

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.30e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
18-(3,4-dimethyl-5-oxooxolan-2-yl)-10,17-dihydroxy-4,17-dimethyl-19,21-dioxahexacyclo[11.6.1.1¹,¹⁵.0³,¹².0⁴,⁹.0¹⁶,²⁰]henicosa-6,8-dien-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -1.812   5.831   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.505   6.646   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.396   8.182   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.574   9.173   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.099   8.553   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.677   9.980   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.913   7.246   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.922   6.067   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.293   4.573   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.768   4.109   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.585   2.474   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.307   2.624   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.314   1.372   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.666  -0.025   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.552  -1.285   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.086  -1.147   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.972  -2.407   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.734   0.250   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.267   0.387   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.915   1.784   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.029   3.044   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.495   2.906   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.609   4.166   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.848   1.509   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.962   2.769   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.082  -0.074   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.718  -0.749   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.694   0.451   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.372   1.845   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.072   2.117   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.475   1.347   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.217   3.485   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.194   2.868   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.024   4.396   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    2    9                                                  
CONECT    9    8   10   32                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   29   31                                             
CONECT   12   11   13                                                       
CONECT   13   12   14   24                                                  
CONECT   14   13   15   26                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   13   18   25                                             
CONECT   25   24                                                            
CONECT   26   14   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28   11                                                       
CONECT   30   28   31   32                                                  
CONECT   31   30   11   26                                                  
CONECT   32   30    9   33   34                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₄O₇

Average Mass

470.5620 Da

Monoisotopic Mass

470.23045 Da

IUPAC Name

18-(3,4-dimethyl-5-oxooxolan-2-yl)-10,17-dihydroxy-4,17-dimethyl-19,21-dioxahexacyclo[11.6.1.1¹,¹⁵.0³,¹².0⁴,⁹.0¹⁶,²⁰]henicosa-6,8-dien-5-one

Traditional Name

18-(3,4-dimethyl-5-oxooxolan-2-yl)-10,17-dihydroxy-4,17-dimethyl-19,21-dioxahexacyclo[11.6.1.1¹,¹⁵.0³,¹².0⁴,⁹.0¹⁶,²⁰]henicosa-6,8-dien-5-one

CAS Registry Number

Not Available

SMILES

CC1C(C)C(=O)OC1C1OC23CC4C(CC(O)C5=CC=CC(=O)C45C)C4CC(O2)C(C34)C1(C)O

InChI Identifier

InChI=1S/C27H34O7/c1-11-12(2)24(30)32-22(11)23-26(4,31)21-18-9-14-13-8-17(28)15-6-5-7-19(29)25(15,3)16(13)10-27(33-18,34-23)20(14)21/h5-7,11-14,16-18,20-23,28,31H,8-10H2,1-4H3

InChI Key

GNNMCSRZHQSNEB-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
Deprea subtriflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroidal glycosides

Alternative Parents

Substituents

Steroidal glycoside
Prostaglandin skeleton
Steroid lactone
Eicosanoid
20-hydroxysteroid
Hydroxysteroid
6-hydroxysteroid
1-oxosteroid
Oxosteroid
Naphthopyran
Naphthofuran
Iridoid-skeleton
Glycosyl compound
C-glycosyl compound
Naphthalene
Dioxepane
1,3-dioxepane
Ketal
Pyran
Oxane
Gamma butyrolactone
Fatty acyl
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Carboxylic acid ester
Secondary alcohol
Lactone
Ketone
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Acetal
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	2.69	ALOGPS
logP	1.94	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	13.59	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	102.29 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	122.63 m³·mol⁻¹	ChemAxon
Polarizability	50.37 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

73805208

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 18-(3,4-dimethyl-5-oxooxolan-2-yl)-10,17-dihydroxy-4,17-dimethyl-19,21-dioxahexacyclo[11.6.1.1¹,¹⁵.0³,¹².0⁴,⁹.0¹⁶,²⁰]henicosa-6,8-dien-5-one (NP0202538)

MOL for NP0202538 (18-(3,4-dimethyl-5-oxooxolan-2-yl)-10,17-dihydroxy-4,17-dimethyl-19,21-dioxahexacyclo[11.6.1.1¹,¹⁵.0³,¹².0⁴,⁹.0¹⁶,²⁰]henicosa-6,8-dien-5-one)

3D MOL for NP0202538 (18-(3,4-dimethyl-5-oxooxolan-2-yl)-10,17-dihydroxy-4,17-dimethyl-19,21-dioxahexacyclo[11.6.1.1¹,¹⁵.0³,¹².0⁴,⁹.0¹⁶,²⁰]henicosa-6,8-dien-5-one)

3D SDF for NP0202538 (18-(3,4-dimethyl-5-oxooxolan-2-yl)-10,17-dihydroxy-4,17-dimethyl-19,21-dioxahexacyclo[11.6.1.1¹,¹⁵.0³,¹².0⁴,⁹.0¹⁶,²⁰]henicosa-6,8-dien-5-one)

3D-SDF for NP0202538 (18-(3,4-dimethyl-5-oxooxolan-2-yl)-10,17-dihydroxy-4,17-dimethyl-19,21-dioxahexacyclo[11.6.1.1¹,¹⁵.0³,¹².0⁴,⁹.0¹⁶,²⁰]henicosa-6,8-dien-5-one)

PDB for NP0202538 (18-(3,4-dimethyl-5-oxooxolan-2-yl)-10,17-dihydroxy-4,17-dimethyl-19,21-dioxahexacyclo[11.6.1.1¹,¹⁵.0³,¹².0⁴,⁹.0¹⁶,²⁰]henicosa-6,8-dien-5-one)

3D PDB for NP0202538 (18-(3,4-dimethyl-5-oxooxolan-2-yl)-10,17-dihydroxy-4,17-dimethyl-19,21-dioxahexacyclo[11.6.1.1¹,¹⁵.0³,¹².0⁴,⁹.0¹⁶,²⁰]henicosa-6,8-dien-5-one)

SMILES for NP0202538 (18-(3,4-dimethyl-5-oxooxolan-2-yl)-10,17-dihydroxy-4,17-dimethyl-19,21-dioxahexacyclo[11.6.1.1¹,¹⁵.0³,¹².0⁴,⁹.0¹⁶,²⁰]henicosa-6,8-dien-5-one)

INCHI for NP0202538 (18-(3,4-dimethyl-5-oxooxolan-2-yl)-10,17-dihydroxy-4,17-dimethyl-19,21-dioxahexacyclo[11.6.1.1¹,¹⁵.0³,¹².0⁴,⁹.0¹⁶,²⁰]henicosa-6,8-dien-5-one)

Structure for NP0202538 (18-(3,4-dimethyl-5-oxooxolan-2-yl)-10,17-dihydroxy-4,17-dimethyl-19,21-dioxahexacyclo[11.6.1.1¹,¹⁵.0³,¹².0⁴,⁹.0¹⁶,²⁰]henicosa-6,8-dien-5-one)

3D Structure for NP0202538 (18-(3,4-dimethyl-5-oxooxolan-2-yl)-10,17-dihydroxy-4,17-dimethyl-19,21-dioxahexacyclo[11.6.1.1¹,¹⁵.0³,¹².0⁴,⁹.0¹⁶,²⁰]henicosa-6,8-dien-5-one)