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Record Information
Version2.0
Created at2022-09-06 22:41:57 UTC
Updated at2022-09-06 22:41:57 UTC
NP-MRD IDNP0239169
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3ar,6s,6ar,10s,12r,15r,15ar)-3-benzyl-1,6,12-trihydroxy-4,5,10,12-tetramethyl-11-oxo-3h,3ah,6h,6ah,9h,10h,15h-cycloundeca[d]isoindol-15-yl acetate
DescriptionCytochalasin C belongs to the class of organic compounds known as cytochalasans. These are fungal metabolites structurally characterized by the presence of an isoindolone nucleus fused to a macrocyclic ring, which can either a lactone, as in cytochalasin B, a carbonate, as in cytochalasin E, or a carbocycle, as in cytochalasin D, H, and K. (3ar,6s,6ar,10s,12r,15r,15ar)-3-benzyl-1,6,12-trihydroxy-4,5,10,12-tetramethyl-11-oxo-3h,3ah,6h,6ah,9h,10h,15h-cycloundeca[d]isoindol-15-yl acetate was first documented in 2019 (PMID: 31351910). Based on a literature review a small amount of articles have been published on Cytochalasin C (PMID: 33585752) (PMID: 33325741) (PMID: 33670169) (PMID: 33188275).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC30H37NO6
Average Mass507.6270 Da
Monoisotopic Mass507.26209 Da
IUPAC Name(6S,6aR,10S,12R,15R,15aR,15bR)-3-benzyl-1,6,12-trihydroxy-4,5,10,12-tetramethyl-11-oxo-3H,6H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca[e]isoindol-15-yl acetate
Traditional Name(6S,6aR,10S,12R,15R,15aR,15bR)-3-benzyl-1,6,12-trihydroxy-4,5,10,12-tetramethyl-11-oxo-3H,6H,6aH,9H,10H,15H,15bH-cycloundeca[e]isoindol-15-yl acetate
CAS Registry NumberNot Available
SMILES
C[C@H]1C\C=C/[C@H]2[C@H](O)C(C)=C(C)[C@H]3C(CC4=CC=CC=C4)N=C(O)[C@@]23[C@H](OC(C)=O)\C=C/[C@@](C)(O)C1=O
InChI Identifier
InChI=1S/C30H37NO6/c1-17-10-9-13-22-26(33)19(3)18(2)25-23(16-21-11-7-6-8-12-21)31-28(35)30(22,25)24(37-20(4)32)14-15-29(5,36)27(17)34/h6-9,11-15,17,22-26,33,36H,10,16H2,1-5H3,(H,31,35)/b13-9-,15-14-/t17-,22-,23?,24+,25-,26+,29+,30+/m0/s1
InChI KeyNAIODHJWOHMDJX-NGFXLRBHSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cytochalasans. These are fungal metabolites structurally characterized by the presence of an isoindolone nucleus fused to a macrocyclic ring, which can either a lactone, as in cytochalasin B, a carbonate, as in cytochalasin E, or a carbocycle, as in cytochalasin D, H, and K.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassCytochalasans
Sub ClassNot Available
Direct ParentCytochalasans
Alternative Parents
Substituents
  • Cytochalasan
  • Carbocyclic cytochalasan skeleton
  • Isoindolone
  • Isoindole or derivatives
  • Isoindole
  • Isoindoline
  • Benzenoid
  • 2-pyrrolidone
  • Pyrrolidone
  • Monocyclic benzene moiety
  • Acyloin
  • Tertiary alcohol
  • Pyrrolidine
  • Cyclic ketone
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Lactam
  • Ketone
  • Carboxylic acid ester
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.02ChemAxon
pKa (Strongest Acidic)3.11ChemAxon
pKa (Strongest Basic)5.46ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area116.42 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity142.85 m³·mol⁻¹ChemAxon
Polarizability53.91 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00011323
Chemspider ID21248059
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6440868
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Wang WX, Li ZH, He J, Feng T, Li J, Liu JK: Cytotoxic cytochalasans from fungus Xylaria longipes. Fitoterapia. 2019 Sep;137:104278. doi: 10.1016/j.fitote.2019.104278. Epub 2019 Jul 25. [PubMed:31351910 ]
  2. Kushwaha M, Qayum A, Jain SK, Singh J, Srivastava AK, Srivastava S, Sharma N, Abrol V, Malik R, Singh SK, Vishwakarma RA, Jaglan S: Tandem MS-Based Metabolite Profiling of 19,20-Epoxycytochalasin C Reveals the Importance of a Hydroxy Group at the C7 Position for Biological Activity. ACS Omega. 2021 Jan 25;6(5):3717-3726. doi: 10.1021/acsomega.0c05307. eCollection 2021 Feb 9. [PubMed:33585752 ]
  3. Zhang Q, Huang ZP, Zhao YY, Zhao Q, Chen JH, Ma WG, Zhang XM: Six 19,20-epoxycytochalasans from endophytic Diaporthe sp. RJ-47. Nat Prod Res. 2022 Jul;36(13):3375-3380. doi: 10.1080/14786419.2020.1859504. Epub 2020 Dec 16. [PubMed:33325741 ]
  4. Lambert C, Pourmoghaddam MJ, Cedeno-Sanchez M, Surup F, Khodaparast SA, Krisai-Greilhuber I, Voglmayr H, Stradal TEB, Stadler M: Resolution of the Hypoxylon fuscum Complex (Hypoxylaceae, Xylariales) and Discovery and Biological Characterization of Two of Its Prominent Secondary Metabolites. J Fungi (Basel). 2021 Feb 11;7(2):131. doi: 10.3390/jof7020131. [PubMed:33670169 ]
  5. Barthelemy M, Guerineau V, Genta-Jouve G, Roy M, Chave J, Guillot R, Pellissier L, Wolfender JL, Stien D, Eparvier V, Touboul D: Identification and dereplication of endophytic Colletotrichum strains by MALDI TOF mass spectrometry and molecular networking. Sci Rep. 2020 Nov 13;10(1):19788. doi: 10.1038/s41598-020-74852-w. [PubMed:33188275 ]
  6. LOTUS database [Link]