NP-MRD: Showing NP-Card for (1s,3ar,3bs,7s,9ar,9br,11r,11ar)-1-[(1s)-1-(acetyloxy)ethyl]-1,3a,3b,7-tetrahydroxy-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl (2e)-2-methylbut-2-enoate (NP0199153)

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Record Information

Version

2.0

Created at

2022-09-04 17:44:09 UTC

Updated at

2022-09-04 17:44:09 UTC

NP-MRD ID

NP0199153

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3ar,3bs,7s,9ar,9br,11r,11ar)-1-[(1s)-1-(acetyloxy)ethyl]-1,3a,3b,7-tetrahydroxy-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl (2e)-2-methylbut-2-enoate

Description

Kidjoladinin belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. (1s,3ar,3bs,7s,9ar,9br,11r,11ar)-1-[(1s)-1-(acetyloxy)ethyl]-1,3a,3b,7-tetrahydroxy-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl (2e)-2-methylbut-2-enoate is found in Marsdenia tomentosa. Based on a literature review very few articles have been published on Kidjoladinin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042219442D          

 36 39  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309042219442D          

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    1.7243   -2.0040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0046   -1.2281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4728   -0.5974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8167   -1.0829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 21  1  0  0  0  0
 10 21  1  0  0  0  0
 21 22  1  1  0  0  0
 11 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  6  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 27 35  1  0  0  0  0
  8 35  1  0  0  0  0
 23 35  1  0  0  0  0
 35 36  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0199153

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(/C)C(=O)O[C@@H]1C[C@@H]2[C@@]3(C)CC[C@H](O)CC3=CC[C@@]2(O)[C@@]2(O)CC[C@@](O)([C@H](C)OC(C)=O)[C@@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H42O8/c1-7-16(2)23(31)36-22-15-21-24(5)10-9-20(30)14-19(24)8-11-27(21,33)28(34)13-12-26(32,25(22,28)6)17(3)35-18(4)29/h7-8,17,20-22,30,32-34H,9-15H2,1-6H3/b16-7+/t17-,20-,21+,22+,24-,25+,26+,27-,28+/m0/s1

> <INCHI_KEY>
KBGNVCDJNMDNAZ-VOLNUIOOSA-N

> <FORMULA>
C28H42O8

> <MOLECULAR_WEIGHT>
506.636

> <EXACT_MASS>
506.287968312

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
54.524073808072764

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5S,10S,11R,14S,15R,16R)-14-[(1S)-1-(acetyloxy)ethyl]-5,10,11,14-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-16-yl (2E)-2-methylbut-2-enoate

> <JCHEM_LOGP>
1.7869323139999986

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.474550092347332

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.795190934548376

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3972417631967353

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
133.40390000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,10S,11R,14S,15R,16R)-14-[(1S)-1-(acetyloxy)ethyl]-5,10,11,14-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-16-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       6.166 -11.668   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.690 -10.220   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.206  -9.949   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.198 -11.126   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.729  -8.500   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      10.245  -8.229   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       7.736  -7.323   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.313  -1.800   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.679  -1.713   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.839  -6.183   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.211  -4.918   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.688  -6.367   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.219  -3.741   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.742  -2.292   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.749  -1.115   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.258  -2.021   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   35                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   21                                                  
CONECT   11   10   12   13   23                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   15   10   22                                             
CONECT   22   21                                                            
CONECT   23   11   24   25   35                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29   35                                             
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   27    8   23   36                                             
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₂O₈

Average Mass

506.6360 Da

Monoisotopic Mass

506.28797 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C\C=C(/C)C(=O)O[C@@H]1C[C@@H]2[C@@]3(C)CC[C@H](O)CC3=CC[C@@]2(O)[C@@]2(O)CC[C@@](O)([C@H](C)OC(C)=O)[C@@]12C

InChI Identifier

InChI=1S/C28H42O8/c1-7-16(2)23(31)36-22-15-21-24(5)10-9-20(30)14-19(24)8-11-27(21,33)28(34)13-12-26(32,25(22,28)6)17(3)35-18(4)29/h7-8,17,20-22,30,32-34H,9-15H2,1-6H3/b16-7+/t17-,20-,21+,22+,24-,25+,26+,27-,28+/m0/s1

InChI Key

KBGNVCDJNMDNAZ-VOLNUIOOSA-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
Marsdenia tomentosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents

Substituents

Progestogin-skeleton
Steroid ester
3-hydroxy-delta-5-steroid
3-hydroxysteroid
17-hydroxysteroid
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Hydroxysteroid
14-hydroxysteroid
Delta-5-steroid
Dicarboxylic acid or derivatives
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Polyol
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Alcohol
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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

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

101316800

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3ar,3bs,7s,9ar,9br,11r,11ar)-1-[(1s)-1-(acetyloxy)ethyl]-1,3a,3b,7-tetrahydroxy-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl (2e)-2-methylbut-2-enoate (NP0199153)

MOL for NP0199153 ((1s,3ar,3bs,7s,9ar,9br,11r,11ar)-1-[(1s)-1-(acetyloxy)ethyl]-1,3a,3b,7-tetrahydroxy-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl (2e)-2-methylbut-2-enoate)

3D MOL for NP0199153 ((1s,3ar,3bs,7s,9ar,9br,11r,11ar)-1-[(1s)-1-(acetyloxy)ethyl]-1,3a,3b,7-tetrahydroxy-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl (2e)-2-methylbut-2-enoate)

3D SDF for NP0199153 ((1s,3ar,3bs,7s,9ar,9br,11r,11ar)-1-[(1s)-1-(acetyloxy)ethyl]-1,3a,3b,7-tetrahydroxy-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl (2e)-2-methylbut-2-enoate)

3D-SDF for NP0199153 ((1s,3ar,3bs,7s,9ar,9br,11r,11ar)-1-[(1s)-1-(acetyloxy)ethyl]-1,3a,3b,7-tetrahydroxy-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl (2e)-2-methylbut-2-enoate)

PDB for NP0199153 ((1s,3ar,3bs,7s,9ar,9br,11r,11ar)-1-[(1s)-1-(acetyloxy)ethyl]-1,3a,3b,7-tetrahydroxy-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl (2e)-2-methylbut-2-enoate)

3D PDB for NP0199153 ((1s,3ar,3bs,7s,9ar,9br,11r,11ar)-1-[(1s)-1-(acetyloxy)ethyl]-1,3a,3b,7-tetrahydroxy-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl (2e)-2-methylbut-2-enoate)

SMILES for NP0199153 ((1s,3ar,3bs,7s,9ar,9br,11r,11ar)-1-[(1s)-1-(acetyloxy)ethyl]-1,3a,3b,7-tetrahydroxy-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl (2e)-2-methylbut-2-enoate)

INCHI for NP0199153 ((1s,3ar,3bs,7s,9ar,9br,11r,11ar)-1-[(1s)-1-(acetyloxy)ethyl]-1,3a,3b,7-tetrahydroxy-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl (2e)-2-methylbut-2-enoate)

Structure for NP0199153 ((1s,3ar,3bs,7s,9ar,9br,11r,11ar)-1-[(1s)-1-(acetyloxy)ethyl]-1,3a,3b,7-tetrahydroxy-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl (2e)-2-methylbut-2-enoate)

3D Structure for NP0199153 ((1s,3ar,3bs,7s,9ar,9br,11r,11ar)-1-[(1s)-1-(acetyloxy)ethyl]-1,3a,3b,7-tetrahydroxy-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl (2e)-2-methylbut-2-enoate)