NP-MRD: Showing NP-Card for 22beta-Hydroxystellatogenin (NP0070741)

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Record Information

Version

2.0

Created at

2022-04-28 16:11:15 UTC

Updated at

2022-04-28 16:11:15 UTC

NP-MRD ID

NP0070741

Secondary Accession Numbers

None

Natural Product Identification

Common Name

22beta-Hydroxystellatogenin

Description

(1S,4R,5R,8S,10S,13R,14R,17R,18R,19S,20R,23S)-10,23-dihydroxy-19-(2-hydroxypropan-2-yl)-4,5,9,9,13-pentamethyl-21-oxahexacyclo[18.2.1.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]Tricosan-22-one belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 22beta-Hydroxystellatogenin is found in Stenocereus eruca. Based on a literature review very few articles have been published on (1S,4R,5R,8S,10S,13R,14R,17R,18R,19S,20R,23S)-10,23-dihydroxy-19-(2-hydroxypropan-2-yl)-4,5,9,9,13-pentamethyl-21-oxahexacyclo[18.2.1.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]Tricosan-22-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282218112D          

 35 40  0  0  1  0            999 V2000
    0.3934   -0.7588    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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  6 19  1  0  0  0  0
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  7 34  1  1  0  0  0
  6 35  1  6  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282218112D          

 35 40  0  0  1  0            999 V2000
    0.3934   -0.7588    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.6977   -2.6421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3068   -2.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8775   -1.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6679   -0.3268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2959    1.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0056    0.7581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4098    0.6357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8936    0.6838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  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
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  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  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 19 18  1  6  0  0  0
  6 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20  3  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  1 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
  3 24  1  1  0  0  0
 24 25  2  0  0  0  0
 21 26  1  6  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
 15 30  1  1  0  0  0
 12 31  1  1  0  0  0
 11 32  1  0  0  0  0
 11 33  1  0  0  0  0
  7 34  1  1  0  0  0
  6 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0070741

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)[C@@H]1[C@H]2OC(=O)[C@]3(CC[C@]4(C)[C@H](CC[C@@H]5[C@@]6(C)CC[C@H](O)C(C)(C)[C@H]6CC[C@@]45C)[C@H]13)[C@@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O5/c1-25(2)17-10-13-29(7)18(27(17,5)12-11-19(25)31)9-8-16-20-21(26(3,4)34)22-23(32)30(20,24(33)35-22)15-14-28(16,29)6/h16-23,31-32,34H,8-15H2,1-7H3/t16-,17-,18-,19+,20-,21+,22-,23-,27+,28-,29-,30+/m1/s1

> <INCHI_KEY>
SXBAXCRSULAGTP-FYEFDZMZSA-N

> <FORMULA>
C30H48O5

> <MOLECULAR_WEIGHT>
488.709

> <EXACT_MASS>
488.350174646

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
55.9587804259239

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4R,5R,8S,10S,13R,14R,17R,18R,19S,20R,23S)-10,23-dihydroxy-19-(2-hydroxypropan-2-yl)-4,5,9,9,13-pentamethyl-21-oxahexacyclo[18.2.1.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tricosan-22-one

> <ALOGPS_LOGP>
4.49

> <JCHEM_LOGP>
3.9945371136666674

> <ALOGPS_LOGS>
-5.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.989696771102302

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.443645325569655

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351216292468545

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
133.8931

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.93e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4R,5R,8S,10S,13R,14R,17R,18R,19S,20R,23S)-10,23-dihydroxy-19-(2-hydroxypropan-2-yl)-4,5,9,9,13-pentamethyl-21-oxahexacyclo[18.2.1.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tricosan-22-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       0.734  -1.416   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.096  -2.136   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.452  -0.707   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.271   0.724   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.809   0.994   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.748  -0.224   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.278  -0.053   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.896   1.358   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.426   1.528   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.339   0.288   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.870   0.459   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.783  -0.781   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.166  -2.192   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.635  -2.363   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.722  -1.122   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.191  -1.293   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.574  -2.704   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.044  -2.875   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.130  -1.635   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.500  -1.892   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.463  -3.089   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.947  -2.429   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.133  -0.609   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.408   0.403   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.520   1.939   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.804  -4.591   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.145  -6.093   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.302  -4.932   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.306  -4.250   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.105  -2.533   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      14.313  -0.610   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      11.752   1.995   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.077   1.415   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.365   1.187   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.401   1.276   0.000  0.00  0.00           C+0
CONECT    1    2    3   22                                                  
CONECT    2    1                                                            
CONECT    3    1    4   20   24                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   19   35                                             
CONECT    7    6    8   16   34                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12   32   33                                             
CONECT   12   11   13   31                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10   16   30                                             
CONECT   16   15    7   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    6   20                                                  
CONECT   20   19    3   21                                                  
CONECT   21   20   22   26                                                  
CONECT   22   21    1   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23    3   25                                                  
CONECT   25   24                                                            
CONECT   26   21   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26                                                            
CONECT   30   15                                                            
CONECT   31   12                                                            
CONECT   32   11                                                            
CONECT   33   11                                                            
CONECT   34    7                                                            
CONECT   35    6                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₈O₅

Average Mass

488.7090 Da

Monoisotopic Mass

488.35017 Da

IUPAC Name

(1S,4R,5R,8S,10S,13R,14R,17R,18R,19S,20R,23S)-10,23-dihydroxy-19-(2-hydroxypropan-2-yl)-4,5,9,9,13-pentamethyl-21-oxahexacyclo[18.2.1.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tricosan-22-one

Traditional Name

(1S,4R,5R,8S,10S,13R,14R,17R,18R,19S,20R,23S)-10,23-dihydroxy-19-(2-hydroxypropan-2-yl)-4,5,9,9,13-pentamethyl-21-oxahexacyclo[18.2.1.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tricosan-22-one

CAS Registry Number

Not Available

SMILES

CC(C)(O)[C@@H]1[C@H]2OC(=O)[C@]3(CC[C@]4(C)[C@H](CC[C@@H]5[C@@]6(C)CC[C@H](O)C(C)(C)[C@H]6CC[C@@]45C)[C@H]13)[C@@H]2O

InChI Identifier

InChI=1S/C30H48O5/c1-25(2)17-10-13-29(7)18(27(17,5)12-11-19(25)31)9-8-16-20-21(26(3,4)34)22-23(32)30(20,24(33)35-22)15-14-28(16,29)6/h16-23,31-32,34H,8-15H2,1-7H3/t16-,17-,18-,19+,20-,21+,22-,23-,27+,28-,29-,30+/m1/s1

InChI Key

SXBAXCRSULAGTP-FYEFDZMZSA-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
Stenocereus eruca	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
17-hydroxysteroid
Hydroxysteroid
Steroid
Naphthopyran
Naphthalene
Delta_valerolactone
Delta valerolactone
Pyran
Oxane
Gamma butyrolactone
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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
logP	4.49	ALOGPS
logP	3.99	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	13.44	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	133.89 m³·mol⁻¹	ChemAxon
Polarizability	55.96 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

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

163045974

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 22beta-Hydroxystellatogenin (NP0070741)

MOL for NP0070741 (22beta-Hydroxystellatogenin)

3D MOL for NP0070741 (22beta-Hydroxystellatogenin)

3D SDF for NP0070741 (22beta-Hydroxystellatogenin)

3D-SDF for NP0070741 (22beta-Hydroxystellatogenin)

PDB for NP0070741 (22beta-Hydroxystellatogenin)

3D PDB for NP0070741 (22beta-Hydroxystellatogenin)

SMILES for NP0070741 (22beta-Hydroxystellatogenin)

INCHI for NP0070741 (22beta-Hydroxystellatogenin)

Structure for NP0070741 (22beta-Hydroxystellatogenin)

3D Structure for NP0070741 (22beta-Hydroxystellatogenin)