NP-MRD: Showing NP-Card for 4-{3a-hydroxy-7-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-9a-(hydroxymethyl)-11a-methyl-tetradecahydrocyclopenta[a]phenanthren-1-yl}-5h-furan-2-one (NP0322364)

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Record Information

Version

2.0

Created at

2022-09-12 01:05:47 UTC

Updated at

2022-09-12 01:05:48 UTC

NP-MRD ID

NP0322364

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-{3a-hydroxy-7-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-9a-(hydroxymethyl)-11a-methyl-tetradecahydrocyclopenta[a]phenanthren-1-yl}-5h-furan-2-one

Description

110187-24-1, Also known as maquiroside a, belongs to the class of organic compounds known as cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety. 4-{3a-hydroxy-7-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-9a-(hydroxymethyl)-11a-methyl-tetradecahydrocyclopenta[a]phenanthren-1-yl}-5h-furan-2-one is found in Maquira calophylla and Maquira sclerophylla. Based on a literature review very few articles have been published on 110187-24-1.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122203052D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309122203052D          

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    1.2889   -1.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6061   -2.0484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5793   -2.8729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0452   -1.5420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2351   -0.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6708    0.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8685    1.4085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0117    2.1096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2920    2.8855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7602    3.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1041    3.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3844    3.8066    0.0000 O   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
 11 12  1  0  0  0  0
 10 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
 16 17  1  0  0  0  0
 10 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
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 23 28  1  0  0  0  0
 22 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 16 31  1  0  0  0  0
 20 31  1  0  0  0  0
 31 32  1  0  0  0  0
 13 33  1  0  0  0  0
  7 33  1  0  0  0  0
  5 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
  3 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0322364

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1CC(OC2CCC3(CO)C(CCC4C3CCC3(C)C(CCC43O)C3=CC(=O)OC3)C2)OC(C)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O8/c1-17-27(33)24(35-3)14-26(37-17)38-20-6-10-29(16-31)19(13-20)4-5-23-22(29)7-9-28(2)21(8-11-30(23,28)34)18-12-25(32)36-15-18/h12,17,19-24,26-27,31,33-34H,4-11,13-16H2,1-3H3

> <INCHI_KEY>
FXZKDRVSINFUOY-UHFFFAOYSA-N

> <FORMULA>
C30H46O8

> <MOLECULAR_WEIGHT>
534.69

> <EXACT_MASS>
534.319268441

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
60.561132229716975

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-{11-hydroxy-5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-2-(hydroxymethyl)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
2.6064223179999995

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.215145389046487

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.182635822274399

> <JCHEM_PKA_STRONGEST_BASIC>
0.2697281109158163

> <JCHEM_POLAR_SURFACE_AREA>
114.68000000000002

> <JCHEM_REFRACTIVITY>
139.52539999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4-{11-hydroxy-5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-2-(hydroxymethyl)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      18.160   6.199   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      17.636   4.751   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      16.120   4.480   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.597   3.032   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.081   2.761   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.480  -2.127   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.978  -1.480   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.406  -2.959   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.131  -3.824   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.081  -5.363   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -0.084  -2.878   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.439  -1.430   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.355   2.629   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      13.089   3.938   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      13.612   5.386   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      12.619   6.564   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      15.128   5.657   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      15.651   7.106   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   37                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   34                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   33                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   13   17                                             
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   33                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   31                                                  
CONECT   17   16   10   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22   31                                             
CONECT   21   20                                                            
CONECT   22   20   23   29                                                  
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   23                                                       
CONECT   29   22   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   16   20   32                                             
CONECT   32   31                                                            
CONECT   33   13    7                                                       
CONECT   34    5   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35    3   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

View in JSmol

Synonyms

Value	Source
Maquiroside a	MeSH

Chemical Formula

C₃₀H₄₆O₈

Average Mass

534.6900 Da

Monoisotopic Mass

534.31927 Da

IUPAC Name

4-{11-hydroxy-5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-2-(hydroxymethyl)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}-2,5-dihydrofuran-2-one

Traditional Name

4-{11-hydroxy-5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-2-(hydroxymethyl)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}-5H-furan-2-one

CAS Registry Number

Not Available

SMILES

COC1CC(OC2CCC3(CO)C(CCC4C3CCC3(C)C(CCC43O)C3=CC(=O)OC3)C2)OC(C)C1O

InChI Identifier

InChI=1S/C30H46O8/c1-17-27(33)24(35-3)14-26(37-17)38-20-6-10-29(16-31)19(13-20)4-5-23-22(29)7-9-28(2)21(8-11-30(23,28)34)18-12-25(32)36-15-18/h12,17,19-24,26-27,31,33-34H,4-11,13-16H2,1-3H3

InChI Key

FXZKDRVSINFUOY-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
Maquira calophylla	LOTUS Database	35616633
Maquira sclerophylla	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Cardenolide glycosides and derivatives

Alternative Parents

Substituents

Cardanolide-glycoside
Steroidal glycoside
19-hydroxysteroid
14-hydroxysteroid
Hydroxysteroid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
2-furanone
Monosaccharide
Oxane
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Lactone
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Primary alcohol
Hydrocarbon derivative
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	2.61	ChemAxon
pKa (Strongest Acidic)	7.18	ChemAxon
pKa (Strongest Basic)	0.27	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	114.68 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	139.53 m³·mol⁻¹	ChemAxon
Polarizability	60.56 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

143670

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163813

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-{3a-hydroxy-7-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-9a-(hydroxymethyl)-11a-methyl-tetradecahydrocyclopenta[a]phenanthren-1-yl}-5h-furan-2-one (NP0322364)

MOL for NP0322364 (4-{3a-hydroxy-7-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-9a-(hydroxymethyl)-11a-methyl-tetradecahydrocyclopenta[a]phenanthren-1-yl}-5h-furan-2-one)

3D MOL for NP0322364 (4-{3a-hydroxy-7-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-9a-(hydroxymethyl)-11a-methyl-tetradecahydrocyclopenta[a]phenanthren-1-yl}-5h-furan-2-one)

3D SDF for NP0322364 (4-{3a-hydroxy-7-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-9a-(hydroxymethyl)-11a-methyl-tetradecahydrocyclopenta[a]phenanthren-1-yl}-5h-furan-2-one)

3D-SDF for NP0322364 (4-{3a-hydroxy-7-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-9a-(hydroxymethyl)-11a-methyl-tetradecahydrocyclopenta[a]phenanthren-1-yl}-5h-furan-2-one)

PDB for NP0322364 (4-{3a-hydroxy-7-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-9a-(hydroxymethyl)-11a-methyl-tetradecahydrocyclopenta[a]phenanthren-1-yl}-5h-furan-2-one)

3D PDB for NP0322364 (4-{3a-hydroxy-7-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-9a-(hydroxymethyl)-11a-methyl-tetradecahydrocyclopenta[a]phenanthren-1-yl}-5h-furan-2-one)

SMILES for NP0322364 (4-{3a-hydroxy-7-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-9a-(hydroxymethyl)-11a-methyl-tetradecahydrocyclopenta[a]phenanthren-1-yl}-5h-furan-2-one)

INCHI for NP0322364 (4-{3a-hydroxy-7-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-9a-(hydroxymethyl)-11a-methyl-tetradecahydrocyclopenta[a]phenanthren-1-yl}-5h-furan-2-one)

Structure for NP0322364 (4-{3a-hydroxy-7-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-9a-(hydroxymethyl)-11a-methyl-tetradecahydrocyclopenta[a]phenanthren-1-yl}-5h-furan-2-one)

3D Structure for NP0322364 (4-{3a-hydroxy-7-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-9a-(hydroxymethyl)-11a-methyl-tetradecahydrocyclopenta[a]phenanthren-1-yl}-5h-furan-2-one)