NP-MRD: Showing NP-Card for (1s,3as,5ar,7r,8s,9as,9br,11ar)-3a,7,8,9b-tetrahydroxy-9a,11a-dimethyl-1-[(2r,3s)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1h,2h,3h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-5-one (NP0329210)

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Record Information

Version

2.0

Created at

2022-09-12 13:23:49 UTC

Updated at

2022-09-12 13:23:50 UTC

NP-MRD ID

NP0329210

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

9Beta,20-dihydroxyecdysone 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. (1s,3as,5ar,7r,8s,9as,9br,11ar)-3a,7,8,9b-tetrahydroxy-9a,11a-dimethyl-1-[(2r,3s)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1h,2h,3h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-5-one is found in Silene italica. (1s,3as,5ar,7r,8s,9as,9br,11ar)-3a,7,8,9b-tetrahydroxy-9a,11a-dimethyl-1-[(2r,3s)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1h,2h,3h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-5-one was first documented in 2004 (PMID: 15219788). Based on a literature review very few articles have been published on 9beta,20-dihydroxyecdysone.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122215232D          

 35 38  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309122215232D          

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    6.3292   -2.0807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5766   -3.0487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  1  0  0  0
 12  9  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 21 19  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 17 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 12 34  1  0  0  0  0
 15 34  1  0  0  0  0
 34 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0329210

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)CC[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@]3(O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O8/c1-22(2,32)8-7-21(31)25(5,33)19-6-9-26(34)20-13-16(28)15-12-17(29)18(30)14-24(15,4)27(20,35)11-10-23(19,26)3/h13,15,17-19,21,29-35H,6-12,14H2,1-5H3/t15-,17+,18-,19-,21-,23+,24-,25+,26+,27-/m0/s1

> <INCHI_KEY>
AHHRNGCAWAPZKG-KEBLQTTMSA-N

> <FORMULA>
C27H44O8

> <MOLECULAR_WEIGHT>
496.641

> <EXACT_MASS>
496.303618377

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
54.54108354826728

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-0.39353010033333413

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.538640103706854

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.09221659552301

> <JCHEM_PKA_STRONGEST_BASIC>
-2.627423734269491

> <JCHEM_POLAR_SURFACE_AREA>
158.68

> <JCHEM_REFRACTIVITY>
130.24989999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4S,5R,7R,11S,14S,15R)-1,4,5,11-tetrahydroxy-2,15-dimethyl-14-[(2R,3S)-2,3,6-trihydroxy-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-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      -1.685  -7.663   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.159  -7.873   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.370  -9.399   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.051  -6.348   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.366  -8.084   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.312  -6.868   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.837  -7.079   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.417  -8.505   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.998  -6.808   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.566  -4.918   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.159  -1.754   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      11.868   0.190   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      15.316  -5.967   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  O   UNK     0      10.410  -5.691   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9   13   34                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   34                                             
CONECT   16   15                                                            
CONECT   17   15   18   30                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   28                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   21   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   17   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   12   15   35                                             
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
9b,20-Dihydroxyecdysone	Generator
9Β,20-dihydroxyecdysone	Generator

Chemical Formula

C₂₇H₄₄O₈

Average Mass

496.6410 Da

Monoisotopic Mass

496.30362 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)(O)CC[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@]3(O)CC[C@]12C

InChI Identifier

InChI=1S/C27H44O8/c1-22(2,32)8-7-21(31)25(5,33)19-6-9-26(34)20-13-16(28)15-12-17(29)18(30)14-24(15,4)27(20,35)11-10-23(19,26)3/h13,15,17-19,21,29-35H,6-12,14H2,1-5H3/t15-,17+,18-,19-,21-,23+,24-,25+,26+,27-/m0/s1

InChI Key

AHHRNGCAWAPZKG-KEBLQTTMSA-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
Silene italica	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
Cholesterol
Cholesterol-skeleton
Cholestane-skeleton
Ecdysteroid
25-hydroxysteroid
Hydroxy bile acid, alcohol, or derivatives
22-hydroxysteroid
20-hydroxysteroid
3-hydroxy-delta-7-steroid
2-hydroxysteroid
3-beta-hydroxysteroid
Oxosteroid
6-oxosteroid
Hydroxysteroid
3-hydroxysteroid
14-hydroxysteroid
Delta-7-steroid
Cyclohexenone
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Ketone
Polyol
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
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

102332532

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Simon A, Pongracz Z, Toth G, Mak M, Mathe I, Bathori M: A new ecdysteroid with unique 9beta-OH and four other ecdysteroids from Silene italica ssp. nemoralis. Steroids. 2004 Jun;69(6):389-94. doi: 10.1016/j.steroids.2004.03.009. [PubMed:15219788 ]
LOTUS database [Link]

Showing NP-Card for (1s,3as,5ar,7r,8s,9as,9br,11ar)-3a,7,8,9b-tetrahydroxy-9a,11a-dimethyl-1-[(2r,3s)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1h,2h,3h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-5-one (NP0329210)

MOL for NP0329210 ((1s,3as,5ar,7r,8s,9as,9br,11ar)-3a,7,8,9b-tetrahydroxy-9a,11a-dimethyl-1-[(2r,3s)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1h,2h,3h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-5-one)

3D MOL for NP0329210 ((1s,3as,5ar,7r,8s,9as,9br,11ar)-3a,7,8,9b-tetrahydroxy-9a,11a-dimethyl-1-[(2r,3s)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1h,2h,3h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-5-one)

3D SDF for NP0329210 ((1s,3as,5ar,7r,8s,9as,9br,11ar)-3a,7,8,9b-tetrahydroxy-9a,11a-dimethyl-1-[(2r,3s)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1h,2h,3h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-5-one)

3D-SDF for NP0329210 ((1s,3as,5ar,7r,8s,9as,9br,11ar)-3a,7,8,9b-tetrahydroxy-9a,11a-dimethyl-1-[(2r,3s)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1h,2h,3h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-5-one)

PDB for NP0329210 ((1s,3as,5ar,7r,8s,9as,9br,11ar)-3a,7,8,9b-tetrahydroxy-9a,11a-dimethyl-1-[(2r,3s)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1h,2h,3h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-5-one)

3D PDB for NP0329210 ((1s,3as,5ar,7r,8s,9as,9br,11ar)-3a,7,8,9b-tetrahydroxy-9a,11a-dimethyl-1-[(2r,3s)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1h,2h,3h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-5-one)

SMILES for NP0329210 ((1s,3as,5ar,7r,8s,9as,9br,11ar)-3a,7,8,9b-tetrahydroxy-9a,11a-dimethyl-1-[(2r,3s)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1h,2h,3h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-5-one)

INCHI for NP0329210 ((1s,3as,5ar,7r,8s,9as,9br,11ar)-3a,7,8,9b-tetrahydroxy-9a,11a-dimethyl-1-[(2r,3s)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1h,2h,3h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-5-one)

Structure for NP0329210 ((1s,3as,5ar,7r,8s,9as,9br,11ar)-3a,7,8,9b-tetrahydroxy-9a,11a-dimethyl-1-[(2r,3s)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1h,2h,3h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-5-one)

3D Structure for NP0329210 ((1s,3as,5ar,7r,8s,9as,9br,11ar)-3a,7,8,9b-tetrahydroxy-9a,11a-dimethyl-1-[(2r,3s)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1h,2h,3h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-5-one)