ChemFOnt: Showing chemical card for {5,18-dihydroxy-1,14,21-trimethyl-25-methylidene-13,19,24,27-tetraoxo-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacos-8-en-7-yl}oxidanesulfonic acid (CFc000146645)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 23:26:22 UTC

Chemfont ID

CFc000146645

Molecule Identification

Common Name

{5,18-dihydroxy-1,14,21-trimethyl-25-methylidene-13,19,24,27-tetraoxo-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacos-8-en-7-yl}oxidanesulfonic acid

Definition

{5,18-dihydroxy-1,14,21-trimethyl-25-methylidene-13,19,24,27-tetraoxo-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacos-8-en-7-yl}oxidanesulfonic acid belongs to the class of organic compounds known as physalins and derivatives. These are steroidal constituents of Physalis plants which possess an unusual 13,14-seco-16,24-cyclo-steroidal ring skeleton (where the bond that is normally present between the 13 and 14 positions in other steroids is broken while a new bond between positions 16 and 24 is formed). Based on a literature review very few articles have been published on {5,18-dihydroxy-1,14,21-trimethyl-25-methylidene-13,19,24,27-tetraoxo-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacos-8-en-7-yl}oxidanesulfonic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
{5,18-dihydroxy-1,14,21-trimethyl-25-methylidene-13,19,24,27-tetraoxo-4,20,23-trioxaheptacyclo[20.3.1.1,.0,.0,.0,.0,]heptacos-8-en-7-yl}oxidanesulfonate	Generator
{5,18-dihydroxy-1,14,21-trimethyl-25-methylidene-13,19,24,27-tetraoxo-4,20,23-trioxaheptacyclo[20.3.1.1,.0,.0,.0,.0,]heptacos-8-en-7-yl}oxidanesulphonate	Generator
{5,18-dihydroxy-1,14,21-trimethyl-25-methylidene-13,19,24,27-tetraoxo-4,20,23-trioxaheptacyclo[20.3.1.1,.0,.0,.0,.0,]heptacos-8-en-7-yl}oxidanesulphonic acid	Generator
{5,18-dihydroxy-1,14,21-trimethyl-25-methylidene-13,19,24,27-tetraoxo-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacos-8-en-7-yl}oxidanesulfonate	Generator
{5,18-dihydroxy-1,14,21-trimethyl-25-methylidene-13,19,24,27-tetraoxo-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacos-8-en-7-yl}oxidanesulphonate	Generator
{5,18-dihydroxy-1,14,21-trimethyl-25-methylidene-13,19,24,27-tetraoxo-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacos-8-en-7-yl}oxidanesulphonic acid	Generator

Chemical Formula

C₂₈H₃₂O₁₃S

Average Molecular Weight

608.61

Monoisotopic Molecular Weight

608.156362264

IUPAC Name

{5,18-dihydroxy-1,14,21-trimethyl-25-methylidene-13,19,24,27-tetraoxo-4,20,23-trioxaheptacyclo[20.3.1.1^{2,5}.0^{3,18}.0^{3,21}.0^{6,15}.0^{9,14}]heptacos-8-en-7-yl}oxidanesulfonic acid

Traditional Name

{5,18-dihydroxy-1,14,21-trimethyl-25-methylidene-13,19,24,27-tetraoxo-4,20,23-trioxaheptacyclo[20.3.1.1^{2,5}.0^{3,18}.0^{3,21}.0^{6,15}.0^{9,14}]heptacos-8-en-7-yl}oxidanesulfonic acid

CAS Registry Number

Not Available

SMILES

CC12OC(=O)C3(O)CCC4C(C(OS(O)(=O)=O)C=C5CCCC(=O)C45C)C4(O)OC13C(C4=O)C1(C)CC2OC(=O)C1=C

InChI Identifier

InChI=1S/C28H32O13S/c1-12-21(31)38-17-11-23(12,2)19-20(30)27(34)18-14(8-9-26(33)22(32)39-25(17,4)28(19,26)41-27)24(3)13(6-5-7-16(24)29)10-15(18)40-42(35,36)37/h10,14-15,17-19,33-34H,1,5-9,11H2,2-4H3,(H,35,36,37)

InChI Key

QLCOVOBACNWJDL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as physalins and derivatives. These are steroidal constituents of Physalis plants which possess an unusual 13,14-seco-16,24-cyclo-steroidal ring skeleton (where the bond that is normally present between the 13 and 14 positions in other steroids is broken while a new bond between positions 16 and 24 is formed).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Physalins and derivatives

Direct Parent

Physalins and derivatives

Alternative Parents

Substituents

Physalin skeleton
Delta valerolactone
Delta_valerolactone
Dicarboxylic acid or derivatives
3-furanone
Gamma butyrolactone
Oxane
Sulfuric acid monoester
Sulfate-ester
Alkyl sulfate
Sulfuric acid ester
Cyclic alcohol
Organic sulfuric acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Lactone
Ketone
Hemiacetal
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Carbonyl group
Organic oxide
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.9 g/L	ALOGPS
logP	0.26	ALOGPS
logP	1.93	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	-1.6	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	200.03 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	137.29 m³·mol⁻¹	ChemAxon
Polarizability	56.75 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0166237

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for {5,18-dihydroxy-1,14,21-trimethyl-25-methylidene-13,19,24,27-tetraoxo-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacos-8-en-7-yl}oxidanesulfonic acid (CFc000146645)

MOL for CFc000146645 ({5,18-dihydroxy-1,14,21-trimethyl-25-methylidene-13,19,24,27-tetraoxo-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacos-8-en-7-yl}oxidanesulfonic acid)

3D MOL for CFc000146645 ({5,18-dihydroxy-1,14,21-trimethyl-25-methylidene-13,19,24,27-tetraoxo-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacos-8-en-7-yl}oxidanesulfonic acid)

3D SDF for CFc000146645 ({5,18-dihydroxy-1,14,21-trimethyl-25-methylidene-13,19,24,27-tetraoxo-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacos-8-en-7-yl}oxidanesulfonic acid)

3D-SDF for CFc000146645 ({5,18-dihydroxy-1,14,21-trimethyl-25-methylidene-13,19,24,27-tetraoxo-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacos-8-en-7-yl}oxidanesulfonic acid)

PDB for CFc000146645 ({5,18-dihydroxy-1,14,21-trimethyl-25-methylidene-13,19,24,27-tetraoxo-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacos-8-en-7-yl}oxidanesulfonic acid)

3D PDB for CFc000146645 ({5,18-dihydroxy-1,14,21-trimethyl-25-methylidene-13,19,24,27-tetraoxo-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacos-8-en-7-yl}oxidanesulfonic acid)

SMILES for CFc000146645 ({5,18-dihydroxy-1,14,21-trimethyl-25-methylidene-13,19,24,27-tetraoxo-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacos-8-en-7-yl}oxidanesulfonic acid)

INCHI for CFc000146645 ({5,18-dihydroxy-1,14,21-trimethyl-25-methylidene-13,19,24,27-tetraoxo-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacos-8-en-7-yl}oxidanesulfonic acid)

Structure for CFc000146645 ({5,18-dihydroxy-1,14,21-trimethyl-25-methylidene-13,19,24,27-tetraoxo-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacos-8-en-7-yl}oxidanesulfonic acid)

3D Structure for CFc000146645 ({5,18-dihydroxy-1,14,21-trimethyl-25-methylidene-13,19,24,27-tetraoxo-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacos-8-en-7-yl}oxidanesulfonic acid)