NP-MRD: Showing NP-Card for Alisol B 23-acetate (NP0073354)

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Record Information

Version

2.0

Created at

2022-04-28 18:37:29 UTC

Updated at

2022-04-28 18:37:29 UTC

NP-MRD ID

NP0073354

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Alisol B 23-acetate

Description

Alisol B 23-acetate, also known as 23-acetylalisol b, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Alisol B 23-acetate is found in Alisma plantago-aquatica and Alisma orientale. Alisol B 23-acetate was first documented in 2021 (PMID: 34742934). Based on a literature review a small amount of articles have been published on Alisol B 23-acetate (PMID: 35028165) (PMID: 34569253) (PMID: 34371964) (PMID: 34284288).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282220372D          

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M  END

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   -2.1873    3.2668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6810    2.6155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0046    3.1540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4586    2.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9990    2.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111    2.5893    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3429    3.2200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9451    0.5269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2487    0.4185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6232    2.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6077    0.1935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8792   -0.0697    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
  2  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
  1  7  1  0  0  0  0
  8  6  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  6  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 19 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 17 29  1  6  0  0  0
 13 30  1  0  0  0  0
 30 31  1  0  0  0  0
  8 31  1  0  0  0  0
 31 32  1  6  0  0  0
 12 33  1  6  0  0  0
  9 34  1  1  0  0  0
  6 35  1  6  0  0  0
  4 36  1  0  0  0  0
  4 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0073354

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](C[C@H](OC(C)=O)[C@H]1OC1(C)C)C1=C2C[C@H](O)[C@H]3[C@@]4(C)CCC(=O)C(C)(C)[C@@H]4CC[C@]3(C)[C@@]2(C)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C32H50O5/c1-18(16-23(36-19(2)33)27-29(5,6)37-27)20-10-14-31(8)21(20)17-22(34)26-30(7)13-12-25(35)28(3,4)24(30)11-15-32(26,31)9/h18,22-24,26-27,34H,10-17H2,1-9H3/t18-,22+,23+,24+,26+,27-,30+,31+,32+/m1/s1

> <INCHI_KEY>
NLOAQXKIIGTTRE-JSWHPQHOSA-N

> <FORMULA>
C32H50O5

> <MOLECULAR_WEIGHT>
514.747

> <EXACT_MASS>
514.36582471

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
59.96840488615716

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R)-1-[(2R)-3,3-dimethyloxiran-2-yl]-3-[(1S,2S,7R,10S,11R,17S)-17-hydroxy-2,6,6,10,11-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-14-en-14-yl]butyl acetate

> <ALOGPS_LOGP>
5.33

> <JCHEM_LOGP>
5.348921994666666

> <ALOGPS_LOGS>
-5.45

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.937443439935873

> <JCHEM_PKA_STRONGEST_BASIC>
-0.3393025498405756

> <JCHEM_POLAR_SURFACE_AREA>
76.13

> <JCHEM_REFRACTIVITY>
144.66540000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.82e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R)-1-[(2R)-3,3-dimethyloxiran-2-yl]-3-[(1S,2S,7R,10S,11R,17S)-17-hydroxy-2,6,6,10,11-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-14-en-14-yl]butyl acetate

> <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       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  O   UNK     0       9.968   2.301   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       7.459   1.394   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.943   1.666   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.420   3.114   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.413   4.291   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.904   3.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.911   2.208   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.434   0.759   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.950   0.488   0.000  0.00  0.00           C+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      -0.667   3.877   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.095   2.398   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.179   1.534   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.612   5.093   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.032   6.519   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.977   7.735   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.397   9.162   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.607  10.687   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.181  10.107   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -3.079  11.141   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.684  12.225   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -3.503   7.525   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -4.083   6.098   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -3.138   4.882   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -5.609   5.887   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.723   4.026   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.865   5.104   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.381   4.833   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.374   6.011   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.764   0.984   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.331   0.781   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.897   4.562   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.601   0.361   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.241  -0.130   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   36   37                                             
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8   35                                             
CONECT    7    6    1                                                       
CONECT    8    6    9   31                                                  
CONECT    9    8   10   12   34                                             
CONECT   10    9   11                                                       
CONECT   11   10    5                                                       
CONECT   12    9   13   16   33                                             
CONECT   13   12   14   30                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15   12                                                       
CONECT   17   14   18   29                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   22   23   24                                             
CONECT   22   21   20                                                       
CONECT   23   21                                                            
CONECT   24   21                                                            
CONECT   25   19   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   17                                                            
CONECT   30   13   31                                                       
CONECT   31   30    8   32                                                  
CONECT   32   31                                                            
CONECT   33   12                                                            
CONECT   34    9                                                            
CONECT   35    6                                                            
CONECT   36    4                                                            
CONECT   37    4                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Value	Source
Alisol b 23-acetic acid	Generator
23-Acetylalisol b	MeSH

Chemical Formula

C₃₂H₅₀O₅

Average Mass

514.7470 Da

Monoisotopic Mass

514.36582 Da

IUPAC Name

(1S,3R)-1-[(2R)-3,3-dimethyloxiran-2-yl]-3-[(1S,2S,7R,10S,11R,17S)-17-hydroxy-2,6,6,10,11-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-14-en-14-yl]butyl acetate

Traditional Name

(1S,3R)-1-[(2R)-3,3-dimethyloxiran-2-yl]-3-[(1S,2S,7R,10S,11R,17S)-17-hydroxy-2,6,6,10,11-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-14-en-14-yl]butyl acetate

CAS Registry Number

Not Available

SMILES

C[C@H](C[C@H](OC(C)=O)[C@H]1OC1(C)C)C1=C2C[C@H](O)[C@H]3[C@@]4(C)CCC(=O)C(C)(C)[C@@H]4CC[C@]3(C)[C@@]2(C)CC1

InChI Identifier

InChI=1S/C32H50O5/c1-18(16-23(36-19(2)33)27-29(5,6)37-27)20-10-14-31(8)21(20)17-22(34)26-30(7)13-12-25(35)28(3,4)24(30)11-15-32(26,31)9/h18,22-24,26-27,34H,10-17H2,1-9H3/t18-,22+,23+,24+,26+,27-,30+,31+,32+/m1/s1

InChI Key

NLOAQXKIIGTTRE-JSWHPQHOSA-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
Alisma plantago-aquatica	LOTUS Database	35616633
Alisma plantago-aquatica subsp. Orientale	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
Steroid ester
3-oxosteroid
Hydroxysteroid
Oxosteroid
11-beta-hydroxysteroid
11-hydroxysteroid
3-oxo-5-alpha-steroid
Steroid
Cyclic alcohol
Cyclic ketone
Carboxylic acid ester
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxide
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organooxygen compound
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	5.33	ALOGPS
logP	5.35	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	19.94	ChemAxon
pKa (Strongest Basic)	-0.34	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	76.13 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	144.67 m³·mol⁻¹	ChemAxon
Polarizability	59.97 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00033624

Chemspider ID

24534152

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14036811

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chang XY, Wu JS, Zhang FQ, Li ZZ, Jin WY, Wang JX, Wang WH, Shi Y: A Strategy for Screening the Lipid-Lowering Components in Alismatis Rhizoma Decoction Based on Spectrum-Effect Analysis. J Anal Methods Chem. 2022 Jan 4;2022:2363242. doi: 10.1155/2022/2363242. eCollection 2022. [PubMed:35028165 ]
Xia F, Xiang S, Chen Z, Song L, Li Y, Liao Z, Ge B, Zhou B: The probiotic effects of AB23A on high-fat-diet-induced non-alcoholic fatty liver disease in mice may be associated with suppressing the serum levels of lipopolysaccharides and branched-chain amino acids. Arch Biochem Biophys. 2021 Dec 15;714:109080. doi: 10.1016/j.abb.2021.109080. Epub 2021 Nov 4. [PubMed:34742934 ]
Luan ZL, Ming WH, Sun XW, Zhang C, Zhou Y, Zheng F, Yang YL, Guan YF, Zhang XY: A naturally occurring FXR agonist, alisol B 23-acetate, protects against renal ischemia-reperfusion injury. Am J Physiol Renal Physiol. 2021 Nov 1;321(5):F617-F628. doi: 10.1152/ajprenal.00193.2021. Epub 2021 Sep 27. [PubMed:34569253 ]
Jang E, Lee JH: Promising Anticancer Activities of Alismatis rhizome and Its Triterpenes via p38 and PI3K/Akt/mTOR Signaling Pathways. Nutrients. 2021 Jul 18;13(7). pii: nu13072455. doi: 10.3390/nu13072455. [PubMed:34371964 ]
Sun Y, Long J, Chen W, Sun Y, Zhou L, Zhang L, Zeng H, Yuan D: Alisol B 23-acetate, a new promoter for cholesterol efflux from dendritic cells, alleviates dyslipidemia and inflammation in advanced atherosclerotic mice. Int Immunopharmacol. 2021 Oct;99:107956. doi: 10.1016/j.intimp.2021.107956. Epub 2021 Jul 18. [PubMed:34284288 ]

Showing NP-Card for Alisol B 23-acetate (NP0073354)

MOL for NP0073354 (Alisol B 23-acetate)

3D MOL for NP0073354 (Alisol B 23-acetate)

3D SDF for NP0073354 (Alisol B 23-acetate)

3D-SDF for NP0073354 (Alisol B 23-acetate)

PDB for NP0073354 (Alisol B 23-acetate)

3D PDB for NP0073354 (Alisol B 23-acetate)

SMILES for NP0073354 (Alisol B 23-acetate)

INCHI for NP0073354 (Alisol B 23-acetate)

Structure for NP0073354 (Alisol B 23-acetate)

3D Structure for NP0073354 (Alisol B 23-acetate)