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Record Information
Version1.0
Created at2022-06-29 17:29:04 UTC
Updated at2022-06-29 17:29:04 UTC
NP-MRD IDNP0138427
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-6alpha-hydroxy Cannabidiol
DescriptionSpeciofoline belongs to the class of organic compounds known as indolizidines. These are polycyclic compounds containing an indolizidine, which is a bicyclic heterocycle containing a saturated six-member ring fused to a saturated five-member ring, one of the bridging atoms being nitrogen. It was first documented in 2022 (PMID: 35850976). Based on a literature review a small amount of articles have been published on Speciofoline (PMID: 35850975) (PMID: 35850974) (PMID: 35850973) (PMID: 35850972) (PMID: 35850971) (PMID: 35850970).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC21H30O3
Average Mass330.4680 Da
Monoisotopic Mass330.21949 Da
IUPAC Namemethyl (2E)-2-[(3R,6'S,7'S,8'aR)-6'-ethyl-4-hydroxy-2-oxo-1,2,3',5',6',7',8',8'a-octahydro-2'H-spiro[indole-3,1'-indolizine]-7'-yl]-3-methoxyprop-2-enoate
Traditional Namemethyl (2E)-2-[(3R,6'S,7'S,8'aR)-6'-ethyl-4-hydroxy-2-oxo-3',5',6',7',8',8'a-hexahydro-1H,2'H-spiro[indole-3,1'-indolizine]-7'-yl]-3-methoxyprop-2-enoate
CAS Registry Number58940-28-6
SMILES
CCCCCC1=CC(O)=C([C@@H]2C=C(C)[C@@H](O)C[C@H]2C(C)=C)C(O)=C1
InChI Identifier
InChI=1S/C21H30O3/c1-5-6-7-8-15-10-19(23)21(20(24)11-15)17-9-14(4)18(22)12-16(17)13(2)3/h9-11,16-18,22-24H,2,5-8,12H2,1,3-4H3/t16-,17+,18-/m0/s1
InChI KeyYYLPAYRRVSQJRR-KSZLIROESA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indolizidines. These are polycyclic compounds containing an indolizidine, which is a bicyclic heterocycle containing a saturated six-member ring fused to a saturated five-member ring, one of the bridging atoms being nitrogen.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndolizidines
Sub ClassNot Available
Direct ParentIndolizidines
Alternative Parents
Substituents
  • Indole or derivatives
  • Dihydroindole
  • Indolizidine
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Aralkylamine
  • Piperidine
  • N-alkylpyrrolidine
  • Benzenoid
  • Pyrrolidine
  • Methyl ester
  • Vinylogous ester
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Amino acid or derivatives
  • Tertiary aliphatic amine
  • Lactam
  • Carboxylic acid ester
  • Azacycle
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • 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
logP2.64ALOGPS
logP1.04ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)8.84ChemAxon
pKa (Strongest Basic)10.25ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area88.1 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity109.99 m³·mol⁻¹ChemAxon
Polarizability42.44 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00025210
Chemspider ID103884424
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101297622
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Bravi CA, Dell'Oglio P, Mazzone E, Moschovas MC, Falagario U, Piazza P, Scarcella S, Bednarz C, Sarchi L, Tappero S, Knipper S, De Groote R, Sjoberg D, Schiavina R, Suardi N, Terrone C, Autorino R, Carrieri G, Galosi A, Galfano A, Briganti A, Montorsi F, Patel V, Vickers A, Mottrie A: The Surgical Learning Curve for Biochemical Recurrence After Robot-assisted Radical Prostatectomy. Eur Urol Oncol. 2022 Jul 15. pii: S2588-9311(22)00113-4. doi: 10.1016/j.euo.2022.06.010. [PubMed:35850976 ]
  2. Santiago T, Santos EJF, Ruaro B, Lepri G, Green L, Wildt M, Watanabe S, Lescoat A, Hesselstrand R, Del Galdo F, Pauling JD, Reeve LJ, D'Agostino MA, Matucci-Cerinic M, Iagnocco A, da Silva JAP: Recommendations for the execution and reporting of skin ultrasound in systemic sclerosis: an international collaboration under the WSF skin ultrasound group. RMD Open. 2022 Jul;8(2). pii: rmdopen-2022-002371. doi: 10.1136/rmdopen-2022-002371. [PubMed:35850975 ]
  3. Baraliakos X, Pournara E, Gossec L, Mease PJ, White R, O'Brien E, Schulz B, Marzo-Ortega H, Coates LC: Predictors of response to secukinumab in patients with psoriatic arthritis and axial manifestations: a post-hoc analysis of the MAXIMISE trial. RMD Open. 2022 Jul;8(2). pii: rmdopen-2022-002303. doi: 10.1136/rmdopen-2022-002303. [PubMed:35850974 ]
  4. van Zante A, Flanagan MB, Floyd AD, Johnson DN, Manucha V, McGrath CM, VandenBussche CJ, Griffith CC: High-risk human papillomavirus testing in cytology aspiration samples from the head and neck part 2: a survey of the American Society of Cytopathology community. J Am Soc Cytopathol. 2022 Sep-Oct;11(5):306-312. doi: 10.1016/j.jasc.2022.06.005. Epub 2022 Jun 22. [PubMed:35850973 ]
  5. Wise J: Record number of consultant physician jobs are unfilled, census shows. BMJ. 2022 Jul 18;378:o1782. doi: 10.1136/bmj.o1782. [PubMed:35850972 ]
  6. Li P, Jin C, Cui C, Cai P, Manohar SA, Jin L, Wei X, Pan S, Dixon RAF, Liu Q: Impact of family history of coronary artery disease on clinical outcomes in Takotsubo cardiomyopathy. J Investig Med. 2022 Jul 18. pii: jim-2021-002186. doi: 10.1136/jim-2021-002186. [PubMed:35850971 ]
  7. Ramon A, Torres AM, Milara J, Cascon J, Blasco P, Mateo J: eXtreme Gradient Boosting-based method to classify patients with COVID-19. J Investig Med. 2022 Jul 18. pii: jim-2021-002278. doi: 10.1136/jim-2021-002278. [PubMed:35850970 ]
  8. Rotimi DE, Olaolu TD, Adeyemi OS: Pharmacological action of quercetin against testicular dysfunction: A mini review. J Integr Med. 2022 Sep;20(5):396-401. doi: 10.1016/j.joim.2022.07.001. Epub 2022 Jul 8. [PubMed:35850969 ]
  9. Zhang Y, Zhong DL, Zheng YL, Li YX, Huang YJ, Jiang YJ, Jin RJ, Li J: Influence of electroacupuncture on ghrelin and the phosphoinositide 3-kinase/protein kinase B/endothelial nitric oxide synthase signaling pathway in spontaneously hypertensive rats. J Integr Med. 2022 Sep;20(5):432-441. doi: 10.1016/j.joim.2022.06.007. Epub 2022 Jun 30. [PubMed:35850968 ]
  10. Topaz O: Excimer Laser-Induced Adverse Coronary Events: Discerning the Merits and Shortcomings of the MAUDE Database Report. Cardiovasc Revasc Med. 2022 Oct;43:155-157. doi: 10.1016/j.carrev.2022.07.005. Epub 2022 Jul 11. [PubMed:35850967 ]