NP-MRD: Showing NP-Card for Makisterone A (NP0076829)

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Record Information

Version

2.0

Created at

2022-04-28 22:01:05 UTC

Updated at

2022-04-28 22:01:05 UTC

NP-MRD ID

NP0076829

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Makisterone A

Description

Makisterone A belongs to the class of organic compounds known as hydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing at least hydroxyl group. Makisterone A is found in Ajuga iva, Centaurea melitensis, Chenopodium quinoa, Dacrydium intermedium, Fibraurea tinctoria, Lepidothamnus intermedius, Penstemon venustus, Podocarpus macrophyllus , Rhaponticum carthamoides , Taxus cuspidata and Tinospora cordifolia. Makisterone A was first documented in 2012 (PMID: 22888532). Based on a literature review a small amount of articles have been published on Makisterone A (PMID: 30953617) (PMID: 26395481) (PMID: 23933119).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292200012D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304292200012D          

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  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 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
  7 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 18  1  0  0  0  0
 16 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 22 27  1  6  0  0  0
 20 28  1  1  0  0  0
 19 29  1  1  0  0  0
 19 30  1  1  0  0  0
 13 31  1  6  0  0  0
 12 32  1  1  0  0  0
  5 33  1  6  0  0  0
  2 34  1  6  0  0  0
  1 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0076829

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](C[C@@H](O)[C@](C)(O)[C@H]1CC[C@@]2(O)C3=CC(=O)[C@@H]4C[C@@H](O)[C@@H](O)C[C@]4(C)[C@H]3CC[C@]12C)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C28H46O7/c1-15(24(2,3)33)11-23(32)27(6,34)22-8-10-28(35)17-12-19(29)18-13-20(30)21(31)14-25(18,4)16(17)7-9-26(22,28)5/h12,15-16,18,20-23,30-35H,7-11,13-14H2,1-6H3/t15-,16+,18+,20-,21+,22+,23-,25-,26-,27-,28-/m1/s1

> <INCHI_KEY>
IJRBORPEVKCEQD-JMQWOFAPSA-N

> <FORMULA>
C28H46O7

> <MOLECULAR_WEIGHT>
494.669

> <EXACT_MASS>
494.324353821

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
55.493486497157704

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,4S,5R,7R,11S,14S,15R)-4,5,11-trihydroxy-2,15-dimethyl-14-[(2R,3R,5R)-2,3,6-trihydroxy-5,6-dimethylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

> <ALOGPS_LOGP>
1.46

> <JCHEM_LOGP>
0.9748350309999997

> <ALOGPS_LOGS>
-3.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.728177391453784

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.252352731816146

> <JCHEM_PKA_STRONGEST_BASIC>
-2.766854303607209

> <JCHEM_POLAR_SURFACE_AREA>
138.45000000000002

> <JCHEM_REFRACTIVITY>
133.34740000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.99e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4S,5R,7R,11S,14S,15R)-4,5,11-trihydroxy-2,15-dimethyl-14-[(2R,3R,5R)-2,3,6-trihydroxy-5,6-dimethylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       7.929   4.020   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.452   2.572   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.459   1.394   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.943   1.666   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.420   3.114   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.413   4.291   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.904   3.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.911   2.208   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.434   0.759   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.950   0.488   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.474  -0.960   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.395   2.479   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.872   3.927   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.865   5.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.381   4.833   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.667   3.877   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.095   2.398   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.179   1.534   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.612   5.093   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.557   6.309   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.083   6.098   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.028   7.314   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.554   7.103   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -8.079   6.893   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.343   5.578   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -6.764   8.629   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -4.448   8.740   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.977   7.735   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.828   4.148   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -0.396   6.038   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.200   5.313   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.764   0.984   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.897   4.562   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       9.968   2.301   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       8.921   5.197   0.000  0.00  0.00           O+0
CONECT    1    2    6   35                                                  
CONECT    2    1    3   34                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   33                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   15                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    8   13   18   32                                             
CONECT   13   12   14   16   31                                             
CONECT   14   13   15                                                       
CONECT   15   14    7                                                       
CONECT   16   13   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17   12                                                       
CONECT   19   16   20   29   30                                             
CONECT   20   19   21   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23                                                            
CONECT   27   22                                                            
CONECT   28   20                                                            
CONECT   29   19                                                            
CONECT   30   19                                                            
CONECT   31   13                                                            
CONECT   32   12                                                            
CONECT   33    5                                                            
CONECT   34    2                                                            
CONECT   35    1                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₆O₇

Average Mass

494.6690 Da

Monoisotopic Mass

494.32435 Da

IUPAC Name

(1R,2R,4S,5R,7R,11S,14S,15R)-4,5,11-trihydroxy-2,15-dimethyl-14-[(2R,3R,5R)-2,3,6-trihydroxy-5,6-dimethylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

Traditional Name

(1R,2R,4S,5R,7R,11S,14S,15R)-4,5,11-trihydroxy-2,15-dimethyl-14-[(2R,3R,5R)-2,3,6-trihydroxy-5,6-dimethylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

CAS Registry Number

Not Available

SMILES

C[C@H](C[C@@H](O)[C@](C)(O)[C@H]1CC[C@@]2(O)C3=CC(=O)[C@@H]4C[C@@H](O)[C@@H](O)C[C@]4(C)[C@H]3CC[C@]12C)C(C)(C)O

InChI Identifier

InChI=1S/C28H46O7/c1-15(24(2,3)33)11-23(32)27(6,34)22-8-10-28(35)17-12-19(29)18-13-20(30)21(31)14-25(18,4)16(17)7-9-26(22,28)5/h12,15-16,18,20-23,30-35H,7-11,13-14H2,1-6H3/t15-,16+,18+,20-,21+,22+,23-,25-,26-,27-,28-/m1/s1

InChI Key

IJRBORPEVKCEQD-JMQWOFAPSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Ajuga iva	LOTUS Database	35616633
Centaurea melitensis	LOTUS Database	35616633
Chenopodium quinoa	LOTUS Database	35616633
Dacrydium intermedium	Plant	KNApSAcK
Fibraurea tinctoria	Plant	KNApSAcK
Lepidothamnus intermedius	LOTUS Database	35616633
Penstemon venustus	LOTUS Database	35616633
Podocarpus macrophyllus	Plant	KNApSAcK
Rhaponticum carthamoides	Plant	KNApSAcK
Taxus cuspidata	Plant	KNApSAcK
Tinospora cordifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing at least hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Hydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Hexahydroxy bile acid, alcohol, or derivatives
Ergosterol-skeleton
Ergostane-skeleton
Ecdysteroid
25-hydroxysteroid
Hydroxy bile acid, alcohol, or derivatives
22-hydroxysteroid
20-hydroxysteroid
3-hydroxy-delta-7-steroid
3-hydroxysteroid
6-oxosteroid
2-hydroxysteroid
14-hydroxysteroid
3-beta-hydroxysteroid
Hydroxysteroid
Oxosteroid
Delta-7-steroid
Cyclohexenone
Cyclic alcohol
Tertiary alcohol
Ketone
Secondary alcohol
Polyol
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

steroid (CHEBI:80775 )

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	1.46	ALOGPS
logP	0.97	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	13.25	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	138.45 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	133.35 m³·mol⁻¹	ChemAxon
Polarizability	55.49 Å³	ChemAxon
Number of Rings	4	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

C00039714

Chemspider ID

23311579

KEGG Compound ID

C16874

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12312690

PDB ID

Not Available

ChEBI ID

80775

Good Scents ID

Not Available

References

General References

Sadati N, Jenett-Siems K, Siems K, Ardekani MR, Hadjiakhoondi A, Akbarzadeh T, Ostad SN, Khanavi M: Major constituents and cytotoxic effects of Ajuga chamaecistus ssp. tomentella. Z Naturforsch C J Biosci. 2012 May-Jun;67(5-6):275-81. doi: 10.1515/znc-2012-5-606. [PubMed:22888532 ]
Corby-Harris V, Snyder L, Meador C: Fat body lipolysis connects poor nutrition to hypopharyngeal gland degradation in Apis mellifera. J Insect Physiol. 2019 Jul;116:1-9. doi: 10.1016/j.jinsphys.2019.04.001. Epub 2019 Apr 3. [PubMed:30953617 ]
Lavrynenko O, Rodenfels J, Carvalho M, Dye NA, Lafont R, Eaton S, Shevchenko A: The ecdysteroidome of Drosophila: influence of diet and development. Development. 2015 Nov 1;142(21):3758-68. doi: 10.1242/dev.124982. Epub 2015 Sep 22. [PubMed:26395481 ]
Saleem M, Musaddiq S, Riaz N, Zubair M, Ashraf M, Nasar R, Jabbar A: Ecdysteroids from the flowers of Aerva javanica. Steroids. 2013 Nov;78(11):1098-102. doi: 10.1016/j.steroids.2013.07.012. Epub 2013 Aug 8. [PubMed:23933119 ]

Showing NP-Card for Makisterone A (NP0076829)

MOL for NP0076829 (Makisterone A)

3D MOL for NP0076829 (Makisterone A)

3D SDF for NP0076829 (Makisterone A)

3D-SDF for NP0076829 (Makisterone A)

PDB for NP0076829 (Makisterone A)

3D PDB for NP0076829 (Makisterone A)

SMILES for NP0076829 (Makisterone A)

INCHI for NP0076829 (Makisterone A)

Structure for NP0076829 (Makisterone A)

3D Structure for NP0076829 (Makisterone A)