Betulinic acid

Betulinic acid
Compound Structure:
Synonyms: betulinic acid;472-15-1;Betulic acid;Mairin;Lupatic Acid;als-357;CCRIS 6748;NSC 113090;3-Hydroxylup-20(29)-en-28-oic acid;EINECS 207-448-8;beta-betulinic acid;3beta-Hydroxy-20(29)-lupaene-28-oic acid;NSC 677578
Compound ID: NMPC-668
PubChem ID:

64971

Molecular Formula: C30H48O3
Canonical SMILES: CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)O)C)C(=O)O
InChIKey: QGJZLNKBHJESQX-FZFNOLFKSA-N
About the compound:

Betulinic acid is a pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-carboxy substituents. It is found in the bark and other plant parts of several species of plants including Syzygium claviflorum. It exhibits anti-HIV, antimalarial, antineoplastic and anti-inflammatory properties. It has a role as an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor, an anti-HIV agent, an antimalarial, an anti-inflammatory agent, an antineoplastic agent and a plant metabolite. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It derives from a hydride of a lupane. Betulinic Acid has been used in trials studying the treatment of Dysplastic Nevus Syndrome. GHS Hazard Statements Not Classified Reported as not meeting GHS hazard criteria by 29 of 30 companies (only ~ 3.3% companies provided GHS information). For more detailed information, please visit ECHA C&L website. Betulinic acid is a pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-carboxy substituents. It is found in the bark and other plant parts of several species of plants including Syzygium claviflorum. It exhibits anti-HIV, antimalarial, antineoplastic and anti-inflammatory properties. It has a role as an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor, an anti-HIV agent, an antimalarial, an anti-inflammatory agent, an antineoplastic agent and a plant metabolite. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It derives from a hydride of a lupane. Betulinic Acid has been used in trials studying the treatment of Dysplastic Nevus Syndrome.

GHS Hazard Statements

Not Classified

Reported as not meeting GHS hazard criteria by 29 of 30 companies (only ~ 3.3% companies provided GHS information). For more detailed information, please visit ECHA C&L website.


Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

456.7 g/mol

XLogP3-AA

8.2

Hydrogen Bond Donor Count

2

Hydrogen Bond Acceptor Count

3

Rotatable Bond Count

2

Exact Mass

456.36034539 g/mol

Monoisotopic Mass

456.36034539 g/mol

Topological Polar Surface Area

57.5²

Heavy Atom Count

33

Formal Charge

0

Complexity

861

Isotope Atom Count

0

Defined Atom Stereocenter Count

10

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

Solid

Boiling Point

316 - 318 °C

Source: PubChem

Source Species: Glossonema boveanum
Nauclea latifolia
Parinari curatellaefolia
Syzygium guineense
Uapaca guineensis
Momordica balsamina
Leptadenia hastata
Maesobotrya barteri
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