NP-MRD: Showing NP-Card for (3as,3br,5's,5ar,6r,7r,9as,9br,11as)-5'-methoxy-1,1,3a,9b-tetramethyl-6-(2-methylprop-1-en-1-yl)-2'-oxo-3b,4,5,5a,6,8,9,10,11,11a-decahydrospiro[cyclopenta[a]phenanthrene-7,3'-oxolane]-9a-carboxylic acid (NP0327664)

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Record Information

Version

2.0

Created at

2022-09-12 10:27:17 UTC

Updated at

2022-09-12 10:27:18 UTC

NP-MRD ID

NP0327664

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3as,3br,5's,5ar,6r,7r,9as,9br,11as)-5'-methoxy-1,1,3a,9b-tetramethyl-6-(2-methylprop-1-en-1-yl)-2'-oxo-3b,4,5,5a,6,8,9,10,11,11a-decahydrospiro[cyclopenta[a]phenanthrene-7,3'-oxolane]-9a-carboxylic acid

Description

Zizimauritic Acid B, also known as zizimauritate b, belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton. (3as,3br,5's,5ar,6r,7r,9as,9br,11as)-5'-methoxy-1,1,3a,9b-tetramethyl-6-(2-methylprop-1-en-1-yl)-2'-oxo-3b,4,5,5a,6,8,9,10,11,11a-decahydrospiro[cyclopenta[a]phenanthrene-7,3'-oxolane]-9a-carboxylic acid is found in Ziziphus mauritiana. Based on a literature review very few articles have been published on Zizimauritic Acid B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122212272D          

 35 39  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309122212272D          

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    2.3936   -1.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5326   -2.3358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4524    1.1017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2971    1.9120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1992    0.7511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  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  1  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  2  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
 20 23  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 15 26  1  0  0  0  0
  8 26  1  0  0  0  0
 26 27  1  6  0  0  0
 12 28  1  0  0  0  0
  5 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
  5 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
  3 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0327664

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1C[C@@]2(CC[C@@]3([C@H](CC[C@@H]4[C@@]5(C)C=CC(C)(C)[C@@H]5CC[C@@]34C)[C@H]2C=C(C)C)C(O)=O)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O5/c1-18(2)16-20-19-8-9-22-27(5)13-12-26(3,4)21(27)10-11-28(22,6)30(19,24(31)32)15-14-29(20)17-23(34-7)35-25(29)33/h12-13,16,19-23H,8-11,14-15,17H2,1-7H3,(H,31,32)/t19-,20-,21+,22-,23+,27+,28-,29-,30-/m1/s1

> <INCHI_KEY>
JMGZXHNRNKFZJQ-HSBMRLKVSA-N

> <FORMULA>
C30H44O5

> <MOLECULAR_WEIGHT>
484.677

> <EXACT_MASS>
484.318874517

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
55.00684484062258

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'R,2'S,3R,5S,6'R,7'R,10'R,11'S,15'S)-5-methoxy-1',11',14',14'-tetramethyl-6'-(2-methylprop-1-en-1-yl)-2-oxospiro[oxolane-3,5'-tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan]-12'-ene-2'-carboxylic acid

> <JCHEM_LOGP>
6.097087829333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.604155743109761

> <JCHEM_PKA_STRONGEST_BASIC>
-4.298670236146066

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
136.5979

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2'S,3R,5S,6'R,7'R,10'R,11'S,15'S)-5-methoxy-1',11',14',14'-tetramethyl-6'-(2-methylprop-1-en-1-yl)-2-oxospiro[oxolane-3,5'-tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan]-12'-ene-2'-carboxylic acid

> <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      12.111  -0.733   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.637  -1.179   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.514  -0.126   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.001  -0.416   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.258   0.933   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.660   2.352   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.132   2.544   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.202   1.316   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.604   2.735   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.480   3.789   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       4.534   3.963   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.800  -0.103   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.870  -1.330   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.342  -1.139   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.744   0.280   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.216   0.472   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.662  -1.002   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.949  -0.535   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.267   0.261   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.917   1.761   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.886   3.301   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.445   1.953   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.382   1.891   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.548   3.119   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.076   2.927   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.674   1.508   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.705   3.048   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.328  -0.294   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.926  -1.714   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.996  -2.941   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.468  -2.749   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.594  -4.360   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.311   2.057   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       8.021   3.569   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       9.705   1.402   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   35                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   28   33                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   12   26                                             
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8   13   28                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   26                                                  
CONECT   16   15   17   18   23                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   16   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   15    8   27                                             
CONECT   27   26                                                            
CONECT   28   12    5   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33    5   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    3                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
Zizimauritate b	Generator

Chemical Formula

C₃₀H₄₄O₅

Average Mass

484.6770 Da

Monoisotopic Mass

484.31887 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CO[C@@H]1C[C@@]2(CC[C@@]3([C@H](CC[C@@H]4[C@@]5(C)C=CC(C)(C)[C@@H]5CC[C@@]34C)[C@H]2C=C(C)C)C(O)=O)C(=O)O1

InChI Identifier

InChI=1S/C30H44O5/c1-18(2)16-20-19-8-9-22-27(5)13-12-26(3,4)21(27)10-11-28(22,6)30(19,24(31)32)15-14-29(20)17-23(34-7)35-25(29)33/h12-13,16,19-23H,8-11,14-15,17H2,1-7H3,(H,31,32)/t19-,20-,21+,22-,23+,27+,28-,29-,30-/m1/s1

InChI Key

JMGZXHNRNKFZJQ-HSBMRLKVSA-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
Ziziphus mauritiana	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
19-hydroxysteroid
19-oxosteroid
Hydroxysteroid
Oxosteroid
Dicarboxylic acid or derivatives
Gamma butyrolactone
Oxolane
Carboxylic acid ester
Lactone
Oxacycle
Carboxylic acid
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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

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

28666913

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71458402

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3as,3br,5's,5ar,6r,7r,9as,9br,11as)-5'-methoxy-1,1,3a,9b-tetramethyl-6-(2-methylprop-1-en-1-yl)-2'-oxo-3b,4,5,5a,6,8,9,10,11,11a-decahydrospiro[cyclopenta[a]phenanthrene-7,3'-oxolane]-9a-carboxylic acid (NP0327664)

MOL for NP0327664 ((3as,3br,5's,5ar,6r,7r,9as,9br,11as)-5'-methoxy-1,1,3a,9b-tetramethyl-6-(2-methylprop-1-en-1-yl)-2'-oxo-3b,4,5,5a,6,8,9,10,11,11a-decahydrospiro[cyclopenta[a]phenanthrene-7,3'-oxolane]-9a-carboxylic acid)

3D MOL for NP0327664 ((3as,3br,5's,5ar,6r,7r,9as,9br,11as)-5'-methoxy-1,1,3a,9b-tetramethyl-6-(2-methylprop-1-en-1-yl)-2'-oxo-3b,4,5,5a,6,8,9,10,11,11a-decahydrospiro[cyclopenta[a]phenanthrene-7,3'-oxolane]-9a-carboxylic acid)

3D SDF for NP0327664 ((3as,3br,5's,5ar,6r,7r,9as,9br,11as)-5'-methoxy-1,1,3a,9b-tetramethyl-6-(2-methylprop-1-en-1-yl)-2'-oxo-3b,4,5,5a,6,8,9,10,11,11a-decahydrospiro[cyclopenta[a]phenanthrene-7,3'-oxolane]-9a-carboxylic acid)

3D-SDF for NP0327664 ((3as,3br,5's,5ar,6r,7r,9as,9br,11as)-5'-methoxy-1,1,3a,9b-tetramethyl-6-(2-methylprop-1-en-1-yl)-2'-oxo-3b,4,5,5a,6,8,9,10,11,11a-decahydrospiro[cyclopenta[a]phenanthrene-7,3'-oxolane]-9a-carboxylic acid)

PDB for NP0327664 ((3as,3br,5's,5ar,6r,7r,9as,9br,11as)-5'-methoxy-1,1,3a,9b-tetramethyl-6-(2-methylprop-1-en-1-yl)-2'-oxo-3b,4,5,5a,6,8,9,10,11,11a-decahydrospiro[cyclopenta[a]phenanthrene-7,3'-oxolane]-9a-carboxylic acid)

3D PDB for NP0327664 ((3as,3br,5's,5ar,6r,7r,9as,9br,11as)-5'-methoxy-1,1,3a,9b-tetramethyl-6-(2-methylprop-1-en-1-yl)-2'-oxo-3b,4,5,5a,6,8,9,10,11,11a-decahydrospiro[cyclopenta[a]phenanthrene-7,3'-oxolane]-9a-carboxylic acid)

SMILES for NP0327664 ((3as,3br,5's,5ar,6r,7r,9as,9br,11as)-5'-methoxy-1,1,3a,9b-tetramethyl-6-(2-methylprop-1-en-1-yl)-2'-oxo-3b,4,5,5a,6,8,9,10,11,11a-decahydrospiro[cyclopenta[a]phenanthrene-7,3'-oxolane]-9a-carboxylic acid)

INCHI for NP0327664 ((3as,3br,5's,5ar,6r,7r,9as,9br,11as)-5'-methoxy-1,1,3a,9b-tetramethyl-6-(2-methylprop-1-en-1-yl)-2'-oxo-3b,4,5,5a,6,8,9,10,11,11a-decahydrospiro[cyclopenta[a]phenanthrene-7,3'-oxolane]-9a-carboxylic acid)

Structure for NP0327664 ((3as,3br,5's,5ar,6r,7r,9as,9br,11as)-5'-methoxy-1,1,3a,9b-tetramethyl-6-(2-methylprop-1-en-1-yl)-2'-oxo-3b,4,5,5a,6,8,9,10,11,11a-decahydrospiro[cyclopenta[a]phenanthrene-7,3'-oxolane]-9a-carboxylic acid)

3D Structure for NP0327664 ((3as,3br,5's,5ar,6r,7r,9as,9br,11as)-5'-methoxy-1,1,3a,9b-tetramethyl-6-(2-methylprop-1-en-1-yl)-2'-oxo-3b,4,5,5a,6,8,9,10,11,11a-decahydrospiro[cyclopenta[a]phenanthrene-7,3'-oxolane]-9a-carboxylic acid)