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Record Information
Version1.0
Created at2022-09-05 23:25:16 UTC
Updated at2022-09-05 23:25:16 UTC
NP-MRD IDNP0221762
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-hydroxy-3-methyl-5-{[(2r,6e,10e)-2,3,15,19,23,27,31,35,39-nonahydroxy-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-6,10,42-trien-1-yl]oxy}-5-oxopentanoic acid
DescriptionGymnopilin A-11 belongs to the class of organic compounds known as polyterpenoids. These are terpenoids consisting of more than eight isoprene units. 3-hydroxy-3-methyl-5-{[(2r,6e,10e)-2,3,15,19,23,27,31,35,39-nonahydroxy-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-6,10,42-trien-1-yl]oxy}-5-oxopentanoic acid is found in Phaeolepiota aurea. It was first documented in 2022 (PMID: 36075691). Based on a literature review a significant number of articles have been published on Gymnopilin A-11 (PMID: 36075690) (PMID: 36075689) (PMID: 36075688) (PMID: 36075687).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC61H114O14
Average Mass1071.5690 Da
Monoisotopic Mass1070.82086 Da
IUPAC Name3-hydroxy-3-methyl-5-{[(2R,6E,10E)-2,3,15,19,23,27,31,35,39-nonahydroxy-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-6,10,42-trien-1-yl]oxy}-5-oxopentanoic acid
Traditional Name3-hydroxy-3-methyl-5-{[(2R,6E,10E)-2,3,15,19,23,27,31,35,39-nonahydroxy-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-6,10,42-trien-1-yl]oxy}-5-oxopentanoic acid
CAS Registry NumberNot Available
SMILES
CC(C)=CCCC(C)(O)CCCC(C)(O)CCCC(C)(O)CCCC(C)(O)CCCC(C)(O)CCCC(C)(O)CCCC(C)(O)CCC\C(C)=C\CC\C(C)=C\CCC(C)(O)[C@H](O)COC(=O)CC(C)(O)CC(O)=O
InChI Identifier
InChI=1S/C61H114O14/c1-47(2)24-15-29-53(5,66)31-18-33-55(7,68)35-20-37-57(9,70)39-22-41-59(11,72)42-23-40-58(10,71)38-21-36-56(8,69)34-19-32-54(6,67)30-16-27-48(3)25-14-26-49(4)28-17-43-61(13,74)50(62)46-75-52(65)45-60(12,73)44-51(63)64/h24-25,28,50,62,66-74H,14-23,26-27,29-46H2,1-13H3,(H,63,64)/b48-25+,49-28+/t50-,53?,54?,55?,56?,57?,58?,59?,60?,61?/m1/s1
InChI KeyKQIRIQJSMCHCHB-ZRFWGTCCSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Phaeolepiota aureaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as polyterpenoids. These are terpenoids consisting of more than eight isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassPolyterpenoids
Direct ParentPolyterpenoids
Alternative Parents
Substituents
  • Polyterpenoid
  • Fatty alcohol
  • Methyl-branched fatty acid
  • Short-chain hydroxy acid
  • Hydroxy fatty acid
  • Fatty acid ester
  • Branched fatty acid
  • Fatty acyl
  • Dicarboxylic acid or derivatives
  • Tertiary alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Polyol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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
logP8.54ChemAxon
pKa (Strongest Acidic)3.75ChemAxon
pKa (Strongest Basic)-0.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area265.9 ŲChemAxon
Rotatable Bond Count45ChemAxon
Refractivity304.53 m³·mol⁻¹ChemAxon
Polarizability128.91 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
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 IDNot Available
Chemspider ID78445195
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound139586121
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Abioye AI, Sudfeld CR, Hughes MD, Aboud S, Muhihi A, Ulenga N, Nagu TJ, Wang M, Mugusi F, Fawzi WW: Iron status among HIV-infected adults during the first year of antiretroviral therapy in Tanzania. HIV Med. 2022 Sep 8. doi: 10.1111/hiv.13396. [PubMed:36075691 ]
  2. Authors unspecified: Resources Round-up. Altern Lab Anim. 2022 Sep 8:2611929221121256. doi: 10.1177/02611929221121256. [PubMed:36075690 ]
  3. Kim JU, Khan W, Arowoshola L, Ahmad M: Correspondence. Eur Heart J Qual Care Clin Outcomes. 2022 Aug 26. pii: 6677390. doi: 10.1093/ehjqcco/qcac051. [PubMed:36075689 ]
  4. DaVault L: Field Amputations Facilitated by a Surgical Extraction Team. Am Surg. 2022 Sep 8:31348221114521. doi: 10.1177/00031348221114521. [PubMed:36075688 ]
  5. Szanyi J, Walles JK, Tesfaye F, Gudeta AN, Bjorkman P: Intrauterine HIV exposure is associated with linear growth restriction among Ethiopian children in the first 18 months of life. Trop Med Int Health. 2022 Sep;27(9):823-830. doi: 10.1111/tmi.13805. Epub 2022 Aug 17. [PubMed:36075687 ]
  6. LOTUS database [Link]