Natural Product (NP) Details

General Information of the NP (ID: NP6132)
Name
Betulin
Synonyms
Betulin; 473-98-3; Betulinol; Betuline; Trochol; Betulol; Lup-20(29)-ene-3beta,28-diol; Lup-20(29)-ene-3b,28-diol; UNII-6W70HN7X7O; NSC 4644; 6W70HN7X7O; CHEBI:3086; (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(Hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-ol; Betulinic alcohol; NSC-4644; MFCD00016802; Lup-20(30)-ene-3beta,28-diol; (1R,2R,5S,8R,9R,10R,13R,14R,17S,19R)-5-(hydroxymethyl)-1,2,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-17-ol; (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(hydroxymethyl)-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol; SR-05000002167; EINECS 207-475-5; NSC4644; AI3-62999; NSC692218; Lup-20(29)-ene-3,28-diol, (3beta)-; (3beta)-lup-20(29)-ene-3,28-diol; Betulin, 23; Betulin, >=98%; Prestwick3_000990; Betulinol (obsol pound(c); Betulin, analytical standard; BSPBio_001059; ARONIS24303; CHEMBL23236; SCHEMBL131739; BPBio1_001165; MEGxp0_001726; ACon1_000091; BDBM23207; DTXSID101019934; HMS2098E21; EX-A3354; HY-N0083; ZINC3978650; s4754; SBB080743; Lup-20(29)-ene-3 ,28-diol; AKOS005267212; ACN-035289; CCG-208619; CS-6156; GS-3254; LMPR0106140005; NSC-692218; NCGC00168803-01; NCGC00168803-02; NCGC00168803-04; AB00513988; B0803; N1290; V0184; (3.beta.)-Lup-20(29)-ene-3,28-diol; C08618; Lup-20(29)-ene-3,28-diol, (3-beta)-; S-1793; 473B983; Q419726; Q-100501; SR-05000002167-2; SR-05000002167-3; BRD-K64874225-001-01-3; NCGC00168803-04_C30H50O2_Lup-20(29)-ene-3,28-diol, (3beta)-; (1R,2R,5S,8R,9R,10R,13R,14R,17S,19R)-5-(hydroxymethyl)-1,2,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0(2),(1)?.0?,?.0(1)?,(1)?]henicosan-17-ol; (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3 a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-ol; (5S,17S,1R,2R,8R,9R,10R,13R,14R,19R)-5-(hydroxymethyl)-1,2,14,18,18-pentamethy l-8-(1-methylvinyl)pentacyclo[11.8.0.0<2,10>.0<5,9>.0<14,19>]henicosan-17-ol
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Species Origin Betula pendula ...     Click to Show/Hide
Betula pendula
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Fagales
Family: Betulaceae
Genus: Betula
Species: Betula pendula
Disease Acute lymphoblastic leukemia [ICD-11: 2B33] Investigative [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -5.04
 
MDCK Permeability
 -4.907
 
PAMPA
 -
 
HIA
 - - -
 
Distribution
VDss
 -0.007
 
PPB
 93.2%
 
BBB
 +++
 
Metabolism
CYP1A2 inhibitor
 - - -
CYP1A2 substrate
 - - -
CYP2C19 inhibitor
 - - -
CYP2C19 substrate
 +++
CYP2C9 inhibitor
 - -
CYP2C9 substrate
 - - -
CYP2D6 inhibitor
 - - -
CYP2D6 substrate
 +
CYP3A4 inhibitor
 - - -
CYP3A4 substrate
 - -
CYP2B6 inhibitor
 +++
CYP2B6 substrate
 - - -
CYP2C8 inhibitor
 +++
HLM Stability
 -
 
Excretion
CLplasma
 9.901
 
T1/2
 0.722
Toxicity
DILI
 -
 
Rat Oral Acute Toxicity
 - -
 
FDAMDD
 +
 
Respiratory
 +++
 
Human Hepatotoxicity
 +
 
Ototoxicity
 -
 
Drug-induced Nephrotoxicity
 ++
 
Drug-induced Neurotoxicity
 - -
 
Hematotoxicity
 +
 
Genotoxicity
 +
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C30H50O2
PubChem CID
72326
Canonical SMILES
CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)O)C)CO
InChI
1S/C30H50O2/c1-19(2)20-10-15-30(18-31)17-16-28(6)21(25(20)30)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h20-25,31-32H,1,8-18H2,2-7H3/t20-,21+,22-,23+,24-,25+,27-,28+,29+,30+/m0/s1
InChIKey
FVWJYYTZTCVBKE-ROUWMTJPSA-N
CAS Number
CAS 473-98-3
ChEBI ID
CHEBI:3086
Herb ID
HBIN018374
SymMap ID
SMIT01296
TTD Drug ID
D05KJY
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Sorafenib      Renal cell carcinoma     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression SREBF1  Molecule Info 
Pathway MAP
                    In-vitro Model Hep-G2 CVCL_0027 Hepatocellular carcinoma Homo sapiens
Huh-7 CVCL_0336 Adult hepatocellular carcinoma Homo sapiens
SMMC-7721 CVCL_0534 Hepatocellular carcinoma Homo sapiens
BEL-7402 CVCL_5492 Human hepatocellular carcinoma Homo sapiens
MHCC97-L CVCL_4973 Adult hepatocellular carcinoma Homo sapiens
MHCC97-H CVCL_4972 Adult hepatocellular carcinoma Homo sapiens
                    In-vivo Model To establish the animal model, HCC cells were injected subcutaneously into nude mice.
                    Experimental
                    Result(s)		 SREBP-1 inhibitor Betulin enhances the antitumor effect of Sorafenib on hepatocellular carcinoma via restricting cellular glycolytic activity.
          Acyclovir      Virus infection     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Vero CVCL_0059 Healthy Chlorocebus sabaeus
                    Experimental
                    Result(s)		 Strong and moderate synergistic antiviral effects were observed for betulin and ACV against HSV-1 when the concentrations of ACV and betulin were higher than 0.068 and 0.4 microg/ml, respectively.
Target and Pathway
Target(s) Myophosphorylase (PYGM)  Molecule Info  [4]
References
Reference 1 Plant extracts and betulin from Ligaria cuneifolia inhibit P-glycoprotein function in leukemia cells. Food Chem Toxicol. 2021 Jan;147:111922.
Reference 2 SREBP-1 inhibitor Betulin enhances the antitumor effect of Sorafenib on hepatocellular carcinoma via restricting cellular glycolytic activity. Cell Death Dis. 2019 Sep 11;10(9):672.
Reference 3 The synergistic effects of betulin with acyclovir against herpes simplex viruses. Antiviral Res. 2004 Nov;64(2):127-30.
Reference 4 Naturally occurring pentacyclic triterpenes as inhibitors of glycogen phosphorylase: synthesis, structure-activity relationships, and X-ray crystal... J Med Chem. 2008 Jun 26;51(12):3540-54.
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