NP-MRD: Showing NP-Card for (1r,3as,5ar,7r,9ar,11ar)-1-[(3r)-3,6-dihydroxy-6-methylheptan-2-yl]-3a,7,8,8-tetrahydroxy-9a,11a-dimethyl-1h,2h,3h,5ah,6h,7h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one (NP0143163)

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Record Information

Version

2.0

Created at

2022-09-01 21:51:29 UTC

Updated at

2022-09-01 21:51:29 UTC

NP-MRD ID

NP0143163

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3as,5ar,7r,9ar,11ar)-1-[(3r)-3,6-dihydroxy-6-methylheptan-2-yl]-3a,7,8,8-tetrahydroxy-9a,11a-dimethyl-1h,2h,3h,5ah,6h,7h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one

Description

2-Hydroxyecdysone belongs to the class of organic compounds known as pentahydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing five hydroxyl groups. (1r,3as,5ar,7r,9ar,11ar)-1-[(3r)-3,6-dihydroxy-6-methylheptan-2-yl]-3a,7,8,8-tetrahydroxy-9a,11a-dimethyl-1h,2h,3h,5ah,6h,7h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one is found in Ajuga reptans. (1r,3as,5ar,7r,9ar,11ar)-1-[(3r)-3,6-dihydroxy-6-methylheptan-2-yl]-3a,7,8,8-tetrahydroxy-9a,11a-dimethyl-1h,2h,3h,5ah,6h,7h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one was first documented in 2011 (PMID: 20364407). Based on a literature review very few articles have been published on 2-hydroxyecdysone.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309012223512D          

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M  END

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M  END


  Mrv1652309012223512D          

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    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  2  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  1  0  0  0  0
  3  4  1  1  0  0  0
  3  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
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 11  2  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 20 18  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 20 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 16 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 11 33  1  0  0  0  0
 14 33  1  0  0  0  0
 33 34  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0143163

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC([C@H](O)CCC(C)(C)O)[C@H]1CC[C@@]2(O)C3=CC(=O)[C@@H]4C[C@@H](O)C(O)(O)C[C@]4(C)C3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O7/c1-15(20(28)8-9-23(2,3)31)16-7-11-26(32)18-12-21(29)19-13-22(30)27(33,34)14-24(19,4)17(18)6-10-25(16,26)5/h12,15-17,19-20,22,28,30-34H,6-11,13-14H2,1-5H3/t15?,16-,17?,19+,20-,22-,24-,25-,26-/m1/s1

> <INCHI_KEY>
ZPYFUHDVFWMGNK-TUYYTXBPSA-N

> <FORMULA>
C27H44O7

> <MOLECULAR_WEIGHT>
480.642

> <EXACT_MASS>
480.308703757

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
54.17555394921343

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,5R,7R,11S,14R,15R)-14-[(3R)-3,6-dihydroxy-6-methylheptan-2-yl]-4,4,5,11-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

> <ALOGPS_LOGP>
1.37

> <JCHEM_LOGP>
1.2728227319999992

> <ALOGPS_LOGS>
-3.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.860406560462845

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.030973600253356

> <JCHEM_PKA_STRONGEST_BASIC>
-2.627362688414686

> <JCHEM_POLAR_SURFACE_AREA>
138.45

> <JCHEM_REFRACTIVITY>
129.0024

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.57e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,5R,7R,11S,14R,15R)-14-[(3R)-3,6-dihydroxy-6-methylheptan-2-yl]-4,4,5,11-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 01-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-SEP-22         0                                  
HETATM    1  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.676  -4.226   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.312  -6.868   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.786  -6.657   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.159  -7.873   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.104  -9.089   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.057  -8.818   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.375  -6.928   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.159  -1.754   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.868   0.190   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      15.840  -5.054   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      14.327  -6.330   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11    2   12   33                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   33                                             
CONECT   15   14                                                            
CONECT   16   14   17   30                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24   28                                                       
CONECT   28   27   20   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   16   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   11   14   34                                             
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₄O₇

Average Mass

480.6420 Da

Monoisotopic Mass

480.30870 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC([C@H](O)CCC(C)(C)O)[C@H]1CC[C@@]2(O)C3=CC(=O)[C@@H]4C[C@@H](O)C(O)(O)C[C@]4(C)C3CC[C@]12C

InChI Identifier

InChI=1S/C27H44O7/c1-15(20(28)8-9-23(2,3)31)16-7-11-26(32)18-12-21(29)19-13-22(30)27(33,34)14-24(19,4)17(18)6-10-25(16,26)5/h12,15-17,19-20,22,28,30-34H,6-11,13-14H2,1-5H3/t15?,16-,17?,19+,20-,22-,24-,25-,26-/m1/s1

InChI Key

ZPYFUHDVFWMGNK-TUYYTXBPSA-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
Ajuga reptans	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentahydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing five hydroxyl groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Pentahydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Pentahydroxy bile acid, alcohol, or derivatives
Cholesterol-skeleton
Cholesterol
Cholestane-skeleton
Ecdysteroid
25-hydroxysteroid
Prostaglandin skeleton
22-hydroxysteroid
Eicosanoid
6-oxosteroid
3-beta-hydroxysteroid
Oxosteroid
Hydroxysteroid
14-hydroxysteroid
2-hydroxysteroid
3-hydroxysteroid
3-hydroxy-delta-7-steroid
Delta-7-steroid
Cyclohexenone
Fatty acyl
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Ketone
Polyol
Carbonyl hydrate
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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

67166900

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

129723467

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zou FM, Lou DS, Zhu YH, Wang SP, Jin BR, Gui ZZ: Expression profiles of glutathione S-transferase genes in larval midgut of Bombyx mori exposed to insect hormones. Mol Biol Rep. 2011 Jan;38(1):639-47. doi: 10.1007/s11033-010-0150-y. Epub 2010 Apr 4. [PubMed:20364407 ]
LOTUS database [Link]

Showing NP-Card for (1r,3as,5ar,7r,9ar,11ar)-1-[(3r)-3,6-dihydroxy-6-methylheptan-2-yl]-3a,7,8,8-tetrahydroxy-9a,11a-dimethyl-1h,2h,3h,5ah,6h,7h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one (NP0143163)

MOL for NP0143163 ((1r,3as,5ar,7r,9ar,11ar)-1-[(3r)-3,6-dihydroxy-6-methylheptan-2-yl]-3a,7,8,8-tetrahydroxy-9a,11a-dimethyl-1h,2h,3h,5ah,6h,7h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

3D MOL for NP0143163 ((1r,3as,5ar,7r,9ar,11ar)-1-[(3r)-3,6-dihydroxy-6-methylheptan-2-yl]-3a,7,8,8-tetrahydroxy-9a,11a-dimethyl-1h,2h,3h,5ah,6h,7h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

3D SDF for NP0143163 ((1r,3as,5ar,7r,9ar,11ar)-1-[(3r)-3,6-dihydroxy-6-methylheptan-2-yl]-3a,7,8,8-tetrahydroxy-9a,11a-dimethyl-1h,2h,3h,5ah,6h,7h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

3D-SDF for NP0143163 ((1r,3as,5ar,7r,9ar,11ar)-1-[(3r)-3,6-dihydroxy-6-methylheptan-2-yl]-3a,7,8,8-tetrahydroxy-9a,11a-dimethyl-1h,2h,3h,5ah,6h,7h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

PDB for NP0143163 ((1r,3as,5ar,7r,9ar,11ar)-1-[(3r)-3,6-dihydroxy-6-methylheptan-2-yl]-3a,7,8,8-tetrahydroxy-9a,11a-dimethyl-1h,2h,3h,5ah,6h,7h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

3D PDB for NP0143163 ((1r,3as,5ar,7r,9ar,11ar)-1-[(3r)-3,6-dihydroxy-6-methylheptan-2-yl]-3a,7,8,8-tetrahydroxy-9a,11a-dimethyl-1h,2h,3h,5ah,6h,7h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

SMILES for NP0143163 ((1r,3as,5ar,7r,9ar,11ar)-1-[(3r)-3,6-dihydroxy-6-methylheptan-2-yl]-3a,7,8,8-tetrahydroxy-9a,11a-dimethyl-1h,2h,3h,5ah,6h,7h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

INCHI for NP0143163 ((1r,3as,5ar,7r,9ar,11ar)-1-[(3r)-3,6-dihydroxy-6-methylheptan-2-yl]-3a,7,8,8-tetrahydroxy-9a,11a-dimethyl-1h,2h,3h,5ah,6h,7h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

Structure for NP0143163 ((1r,3as,5ar,7r,9ar,11ar)-1-[(3r)-3,6-dihydroxy-6-methylheptan-2-yl]-3a,7,8,8-tetrahydroxy-9a,11a-dimethyl-1h,2h,3h,5ah,6h,7h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

3D Structure for NP0143163 ((1r,3as,5ar,7r,9ar,11ar)-1-[(3r)-3,6-dihydroxy-6-methylheptan-2-yl]-3a,7,8,8-tetrahydroxy-9a,11a-dimethyl-1h,2h,3h,5ah,6h,7h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)