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Helvolic acid

CAT: 0804-HY-N6728Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N6728Size:1 mg
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Description
Helvolic acid (Fumigacin) is an antibiotic isolated from Xylaria sp, active against the Gram-positive bacteria[1].
CAS Number
29400-42-8
Product Name Alternative
Fumigacin
UNSPSC
12352211
Target
Antibiotic; Bacterial
Type
Natural Products
Related Pathways
Anti-infection
Applications
COVID-19-immunoregulation
Field of Research
Infection
Assay Protocol
https://www.medchemexpress.com/helvolic-acid.html
Purity
99.06
Solubility
DMSO : 10 mg/mL (ultrasonic; warming)
Smiles
C[C@@H]([C@]1([H])[C@H](OC(C)=O)C([C@]([C@@](C[C@@H]/2OC(C)=O)3C)4C)=O)C(C=C[C@]1(C)[C@]4([H])CC[C@@]3([H])C2=C(C(O)=O)/CC/C=C(C)\C)=O
Molecular Formula
C33H44O8
Molecular Weight
568.70
References & Citations
[1]Ratnaweera PB, et al. Helvolic acid, an antibacterial nortriterpenoid from a fungal endophyte, Xylaria sp. of orchid Anoectochilus setaceus endemic to Sri Lanka. Mycology. 2014 Mar;5 (1) :23-28. Epub 2014 Mar 25.
Shipping Conditions
Blue Ice
Storage Conditions
-20°C (Powder, protect from light, stored under nitrogen)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Helvolic Acid

Helvolic acid is a steroid C-21 acid having a 29-nordammarane skeleton substituted with an acetoxy group at C-16 and oxo groups at C-3 and -7, with double bonds at C-1, -17(20) and -24. It has a role as a mycotoxin, an antibacterial agent and a fungal metabolite. It is a 3-oxo-Delta(1) steroid, a monocarboxylic acid, an acetate ester and a steroid acid. It is a conjugate acid of a helvolate. It derives from a hydride of a dammarane.

CAS Number29400-42-8
PubChem CID3002143
IUPAC Name(2Z)-2-[(4S,5S,6S,8S,9S,10R,13R,14S,16S)-6,16-diacetyloxy-4,8,10,14-tetramethyl-3,7-dioxo-5,6,9,11,12,13,15,16-octahydro-4H-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoic acid
Molecular FormulaC33H44O8
Molecular Weight568.7
XLogP5.1
Topological Polar Surface Area124
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count8
Rotatable Bond Count8
Heavy Atom Count41
Formal Charge0
Complexity1270
SMILES
C[C@H]1[C@@H]2[C@@H](C(=O)[C@]3([C@H]([C@]2(C=CC1=O)C)CC[C@@H]\4[C@@]3(C[C@@H](/C4=C(/CCC=C(C)C)\C(=O)O)OC(=O)C)C)C)OC(=O)C
InChI
InChI=1S/C33H44O8/c1-17(2)10-9-11-21(30(38)39)26-22-12-13-25-31(6)15-14-23(36)18(3)27(31)28(41-20(5)35)29(37)33(25,8)32(22,7)16-24(26)40-19(4)34/h10,14-15,18,22,24-25,27-28H,9,11-13,16H2,1-8H3,(H,38,39)/b26-21-/t18-,22+,24+,25+,27-,28+,31-,32+,33-/m1/s1
InChIKey
MDFZYGLOIJNNRM-OAJDADRGSA-N
Chemical Structure
2D Structure
2D structure of Helvolic Acid
CAS: 29400-42-8
CID: 3002143
Formula: C33H44O8
MW: 568.7
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight568.7
XLogP35.1
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count8
Rotatable Bond Count8
Exact Mass568.30361836
Monoisotopic Mass568.30361836
Topological Polar Surface Area124 Ų
Heavy Atom Count41
Formal Charge0
Complexity1270
Isotope Atom Count0
Defined Atom Stereocenter Count9
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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