NP-MRD: Showing NP-Card for 1-{7-[(5-amino-4-methoxy-6-methyloxan-2-yl)oxy]-3,3a-dihydroxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}ethanone (NP0202860)

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Record Information

Version

2.0

Created at

2022-09-04 22:10:38 UTC

Updated at

2022-09-04 22:10:38 UTC

NP-MRD ID

NP0202860

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-{7-[(5-amino-4-methoxy-6-methyloxan-2-yl)oxy]-3,3a-dihydroxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}ethanone

Description

1-{5-[(5-Amino-4-methoxy-6-methyloxan-2-yl)oxy]-11,12-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-14-yl}ethan-1-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. 1-{7-[(5-amino-4-methoxy-6-methyloxan-2-yl)oxy]-3,3a-dihydroxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}ethanone is found in Holarrhena curtisii. 1-{5-[(5-Amino-4-methoxy-6-methyloxan-2-yl)oxy]-11,12-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-14-yl}ethan-1-one is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261502342D          

 35 39  0  0  0  0            999 V2000
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M  END

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M  END


  Mrv1533004261502342D          

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    0.4342   -2.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939   -0.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9830   -0.0929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1111   -0.9700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6582   -3.7596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9385   -4.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4067   -5.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7507   -4.6807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0310   -5.4566    0.0000 N   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 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
 15 16  1  0  0  0  0
 15 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
 19 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 12 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 10 26  1  0  0  0  0
 26 27  1  0  0  0  0
  7 27  1  0  0  0  0
 17 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
  5 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
  3 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0202860

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1CC(OC2CCC3(C)C4CCC5(C)C(CC(O)C5(O)C4CC=C3C2)C(C)=O)OC(C)C1N

> <INCHI_IDENTIFIER>
InChI=1S/C28H45NO6/c1-15(30)21-13-23(31)28(32)20-7-6-17-12-18(35-24-14-22(33-5)25(29)16(2)34-24)8-10-26(17,3)19(20)9-11-27(21,28)4/h6,16,18-25,31-32H,7-14,29H2,1-5H3

> <INCHI_KEY>
SFUVPIJMDPWZBZ-UHFFFAOYSA-N

> <FORMULA>
C28H45NO6

> <MOLECULAR_WEIGHT>
491.669

> <EXACT_MASS>
491.324688173

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
56.29947799770026

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-{5-[(5-amino-4-methoxy-6-methyloxan-2-yl)oxy]-11,12-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl}ethan-1-one

> <ALOGPS_LOGP>
1.69

> <JCHEM_LOGP>
2.138065901666665

> <ALOGPS_LOGS>
-4.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.820644396794222

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.20296640046633

> <JCHEM_PKA_STRONGEST_BASIC>
9.13334035271087

> <JCHEM_POLAR_SURFACE_AREA>
111.24000000000001

> <JCHEM_REFRACTIVITY>
132.33689999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-{5-[(5-amino-4-methoxy-6-methyloxan-2-yl)oxy]-11,12-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl}ethanone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0      -6.300  -9.279   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.777  -7.831   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.261  -7.560   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.737  -6.112   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.221  -5.841   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.698  -4.392   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.182  -4.121   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.341  -2.673   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.857  -2.402   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.850  -3.579   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.373  -2.131   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.366  -3.308   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.889  -1.859   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.405  -1.588   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.398  -2.766   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.069  -1.380   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.937  -2.816   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.365  -4.295   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.090  -5.159   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.040  -6.698   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.874  -4.214   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.505  -5.709   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.358  -4.485   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.835  -5.934   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.319  -6.205   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.326  -5.027   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.810  -5.298   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.882  -1.600   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.302  -0.173   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      11.407  -1.811   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.229  -7.018   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -1.752  -8.466   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.759  -9.644   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.268  -8.737   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0      -3.791 -10.186   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   31                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   27                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   26                                             
CONECT   11   10                                                            
CONECT   12   10   13   23                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   21                                             
CONECT   16   15                                                            
CONECT   17   15   18   28                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   15   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   12   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   10   27                                                  
CONECT   27   26    7                                                       
CONECT   28   17   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31    5   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32    3   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₅NO₆

Average Mass

491.6690 Da

Monoisotopic Mass

491.32469 Da

IUPAC Name

1-{5-[(5-amino-4-methoxy-6-methyloxan-2-yl)oxy]-11,12-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl}ethan-1-one

Traditional Name

1-{5-[(5-amino-4-methoxy-6-methyloxan-2-yl)oxy]-11,12-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl}ethanone

CAS Registry Number

Not Available

SMILES

COC1CC(OC2CCC3(C)C4CCC5(C)C(CC(O)C5(O)C4CC=C3C2)C(C)=O)OC(C)C1N

InChI Identifier

InChI=1S/C28H45NO6/c1-15(30)21-13-23(31)28(32)20-7-6-17-12-18(35-24-14-22(33-5)25(29)16(2)34-24)8-10-26(17,3)19(20)9-11-27(21,28)4/h6,16,18-25,31-32H,7-14,29H2,1-5H3

InChI Key

SFUVPIJMDPWZBZ-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
Holarrhena curtisii	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
20-oxosteroid
Pregnane-skeleton
Aminoglycoside core
14-hydroxysteroid
15-hydroxysteroid
Hydroxysteroid
Oxosteroid
Delta-5-steroid
Amino saccharide
Oxane
Tertiary alcohol
Cyclic alcohol
1,2-diol
Secondary alcohol
Ketone
Organoheterocyclic compound
Oxacycle
Acetal
Dialkyl ether
Ether
Primary amine
Organic oxide
Organopnictogen compound
Hydrocarbon derivative
Primary aliphatic amine
Organic oxygen compound
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Amine
Alcohol
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	1.69	ALOGPS
logP	2.14	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	13.2	ChemAxon
pKa (Strongest Basic)	9.13	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.24 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	132.34 m³·mol⁻¹	ChemAxon
Polarizability	56.3 Å³	ChemAxon
Number of Rings	5	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

85209979

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-{7-[(5-amino-4-methoxy-6-methyloxan-2-yl)oxy]-3,3a-dihydroxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}ethanone (NP0202860)

MOL for NP0202860 (1-{7-[(5-amino-4-methoxy-6-methyloxan-2-yl)oxy]-3,3a-dihydroxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}ethanone)

3D MOL for NP0202860 (1-{7-[(5-amino-4-methoxy-6-methyloxan-2-yl)oxy]-3,3a-dihydroxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}ethanone)

3D SDF for NP0202860 (1-{7-[(5-amino-4-methoxy-6-methyloxan-2-yl)oxy]-3,3a-dihydroxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}ethanone)

3D-SDF for NP0202860 (1-{7-[(5-amino-4-methoxy-6-methyloxan-2-yl)oxy]-3,3a-dihydroxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}ethanone)

PDB for NP0202860 (1-{7-[(5-amino-4-methoxy-6-methyloxan-2-yl)oxy]-3,3a-dihydroxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}ethanone)

3D PDB for NP0202860 (1-{7-[(5-amino-4-methoxy-6-methyloxan-2-yl)oxy]-3,3a-dihydroxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}ethanone)

SMILES for NP0202860 (1-{7-[(5-amino-4-methoxy-6-methyloxan-2-yl)oxy]-3,3a-dihydroxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}ethanone)

INCHI for NP0202860 (1-{7-[(5-amino-4-methoxy-6-methyloxan-2-yl)oxy]-3,3a-dihydroxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}ethanone)

Structure for NP0202860 (1-{7-[(5-amino-4-methoxy-6-methyloxan-2-yl)oxy]-3,3a-dihydroxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}ethanone)

3D Structure for NP0202860 (1-{7-[(5-amino-4-methoxy-6-methyloxan-2-yl)oxy]-3,3a-dihydroxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}ethanone)