NP-MRD: Showing NP-Card for {2-[3-(furan-3-yl)propyl]-6-methyl-8-[(1s,6r)-1,2,6-trimethylcyclohex-2-en-1-yl]oct-5-en-1-yl}oxysulfonic acid (NP0280939)

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Record Information

Version

2.0

Created at

2022-09-09 06:59:59 UTC

Updated at

2022-09-09 06:59:59 UTC

NP-MRD ID

NP0280939

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{2-[3-(furan-3-yl)propyl]-6-methyl-8-[(1s,6r)-1,2,6-trimethylcyclohex-2-en-1-yl]oct-5-en-1-yl}oxysulfonic acid

Description

({2-[3-(Furan-3-yl)propyl]-6-methyl-8-[(1S,6R)-1,2,6-trimethylcyclohex-2-en-1-yl]oct-5-en-1-yl}oxy)sulfonic acid belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. It was first documented in 1993 (PMID: 36137062). Based on a literature review a significant number of articles have been published on ({2-[3-(furan-3-yl)propyl]-6-methyl-8-[(1S,6R)-1,2,6-trimethylcyclohex-2-en-1-yl]oct-5-en-1-yl}oxy)sulfonic acid (PMID: 36137063) (PMID: 36137748) (PMID: 36137747) (PMID: 36137746) (PMID: 36137745) (PMID: 36137744).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092209002D          

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M  END

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M  END
> <DATABASE_ID>
NP0280939

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CCC=C(C)[C@@]1(C)CCC(C)=CCCC(CCCC1=COC=C1)COS(O)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H40O5S/c1-20(14-16-25(4)21(2)9-6-10-22(25)3)8-5-11-23(19-30-31(26,27)28)12-7-13-24-15-17-29-18-24/h8-9,15,17-18,22-23H,5-7,10-14,16,19H2,1-4H3,(H,26,27,28)/t22-,23?,25-/m1/s1

> <INCHI_KEY>
GCCDIQCRJHCDFR-VJBIEYCASA-N

> <FORMULA>
C25H40O5S

> <MOLECULAR_WEIGHT>
452.65

> <EXACT_MASS>
452.259645562

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
51.897583583293795

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
({2-[3-(furan-3-yl)propyl]-6-methyl-8-[(1S,6R)-1,2,6-trimethylcyclohex-2-en-1-yl]oct-5-en-1-yl}oxy)sulfonic acid

> <JCHEM_LOGP>
5.475839473269062

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.569307779430348

> <JCHEM_PKA_STRONGEST_BASIC>
-2.799471559652316

> <JCHEM_POLAR_SURFACE_AREA>
76.74

> <JCHEM_REFRACTIVITY>
126.98599999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
{2-[3-(furan-3-yl)propyl]-6-methyl-8-[(1S,6R)-1,2,6-trimethylcyclohex-2-en-1-yl]oct-5-en-1-yl}oxysulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       0.956  -4.516   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.956  -6.056   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.290  -6.826   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.623  -6.056   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.957  -6.826   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.291  -6.056   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.624  -6.826   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.958  -6.056   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.292  -6.826   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.626  -6.056   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.786  -4.524   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.293  -4.204   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      14.063  -5.538   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      13.032  -6.682   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.291  -4.516   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.624  -3.746   0.000  0.00  0.00           O+0
HETATM   17  S   UNK     0       7.624  -2.206   0.000  0.00  0.00           S+0
HETATM   18  O   UNK     0       6.084  -2.206   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       7.624  -0.666   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       9.164  -2.206   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.378  -6.826   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.711  -6.056   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.711  -4.516   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.195  -4.783   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.228  -4.783   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.755  -6.230   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.218  -3.604   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.691  -2.157   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.174  -1.889   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.185  -3.069   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.332  -2.801   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15    6   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17                                                            
CONECT   21    2   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25   30                                             
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   23   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

View in JSmol

Synonyms

Value	Source
({2-[3-(furan-3-yl)propyl]-6-methyl-8-[(1S,6R)-1,2,6-trimethylcyclohex-2-en-1-yl]oct-5-en-1-yl}oxy)sulfonate	Generator
({2-[3-(furan-3-yl)propyl]-6-methyl-8-[(1S,6R)-1,2,6-trimethylcyclohex-2-en-1-yl]oct-5-en-1-yl}oxy)sulphonate	Generator
({2-[3-(furan-3-yl)propyl]-6-methyl-8-[(1S,6R)-1,2,6-trimethylcyclohex-2-en-1-yl]oct-5-en-1-yl}oxy)sulphonic acid	Generator

Chemical Formula

C₂₅H₄₀O₅S

Average Mass

452.6500 Da

Monoisotopic Mass

452.25965 Da

IUPAC Name

({2-[3-(furan-3-yl)propyl]-6-methyl-8-[(1S,6R)-1,2,6-trimethylcyclohex-2-en-1-yl]oct-5-en-1-yl}oxy)sulfonic acid

Traditional Name

{2-[3-(furan-3-yl)propyl]-6-methyl-8-[(1S,6R)-1,2,6-trimethylcyclohex-2-en-1-yl]oct-5-en-1-yl}oxysulfonic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]1CCC=C(C)[C@@]1(C)CCC(C)=CCCC(CCCC1=COC=C1)COS(O)(=O)=O

InChI Identifier

InChI=1S/C25H40O5S/c1-20(14-16-25(4)21(2)9-6-10-22(25)3)8-5-11-23(19-30-31(26,27)28)12-7-13-24-15-17-29-18-24/h8-9,15,17-18,22-23H,5-7,10-14,16,19H2,1-4H3,(H,26,27,28)/t22-,23?,25-/m1/s1

InChI Key

GCCDIQCRJHCDFR-VJBIEYCASA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Sulfuric acid ester
Alkyl sulfate
Sulfate-ester
Sulfuric acid monoester
Heteroaromatic compound
Organic sulfuric acid or derivatives
Furan
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.48	ChemAxon
pKa (Strongest Acidic)	-1.6	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	76.74 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	126.99 m³·mol⁻¹	ChemAxon
Polarizability	51.9 Å³	ChemAxon
Number of Rings	2	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

163036421

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Salisbury L, Baraitser L: Depressing time: Waiting, melancholia, and the psychoanalytic practice of care. 2020. [PubMed:36137063 ]
Heimer G, Neuser S, Ben-Zeev B, Ebrahimi-Fakhari D: TECPR2-Related Hereditary Sensory and Autonomic Neuropathy with Intellectual Disability. 1993. [PubMed:36137062 ]
Tibbe D, Ferle P, Krisp C, Nampoothiri S, Mirzaa G, Assaf M, Parikh S, Kutsche K, Kreienkamp HJ: Regulation of Liprin-alpha phase separation by CASK is disrupted by a mutation in its CaM kinase domain. Life Sci Alliance. 2022 Sep 22;5(10). pii: 5/10/e202201512. doi: 10.26508/lsa.202201512. Print 2022 Oct. [PubMed:36137748 ]
Sengupta R, Mihelc EM, Angel S, Lanman JK, Kuhn RJ, Stahelin RV: Contribution of the Golgi apparatus in morphogenesis of a virus-induced cytopathic vacuolar system. Life Sci Alliance. 2022 Sep 22;5(10). pii: 5/10/e202000887. doi: 10.26508/lsa.202000887. Print 2022 Oct. [PubMed:36137747 ]
Cui Y, Peng S, Czaplicki L, Yang T: Protecting minors from tobacco products: public interest litigation enables enforcement in China. Tob Control. 2022 Sep 22. pii: tc-2022-057615. doi: 10.1136/tc-2022-057615. [PubMed:36137746 ]
Kneihsl M, Hinteregger N, Nistl O, Deutschmann H, Horner S, Poltrum B, Fandler-Hofler S, Hatab I, Haidegger M, Pinter D, Pichler A, Willeit K, Knoflach M, Enzinger C, Gattringer T: Post-reperfusion hyperperfusion after endovascular stroke treatment: a prospective comparative study of TCD versus MRI. J Neurointerv Surg. 2022 Sep 22. pii: jnis-2022-019213. doi: 10.1136/jnis-2022-019213. [PubMed:36137745 ]
Yusuf H, Rasheed A, Kim H, Conrad MB, Hetts SW: Identifying racial disparities in hereditary hemorrhagic telangiectasia. J Neurointerv Surg. 2022 Sep 22. pii: jnis-2022-019162. doi: 10.1136/jnis-2022-019162. [PubMed:36137744 ]
Housley SB, Monteiro A, Khawar WI, Donnelly BM, Lian MX, Fritz AG, Waqas M, Cappuzzo JM, Snyder KV, Siddiqui AH, Levy EI, Davies JM: Volumetric resolution of chronic subdural hematomas treated with surgical evacuation versus middle meningeal artery embolization during immediate, early, and late follow up: propensity-score matched cohorts. J Neurointerv Surg. 2022 Sep 22. pii: jnis-2022-019427. doi: 10.1136/jnis-2022-019427. [PubMed:36137743 ]
Thornhill MH, Crum A, Campbell R, Stone T, Lee EC, Bradburn M, Fibisan V, Dayer M, Prendergast BD, Lockhart P, Baddour L, Nicoll J: Temporal association between invasive procedures and infective endocarditis. Heart. 2022 Sep 22. pii: heartjnl-2022-321519. doi: 10.1136/heartjnl-2022-321519. [PubMed:36137742 ]
Plantone D, Locci S, Bergantini L, Manco C, Cortese R, Meocci M, Cavallaro D, d'Alessandro M, Bargagli E, De Stefano N: Brain neuronal and glial damage during acute COVID-19 infection in absence of clinical neurological manifestations. J Neurol Neurosurg Psychiatry. 2022 Sep 22. pii: jnnp-2022-329933. doi: 10.1136/jnnp-2022-329933. [PubMed:36137741 ]
LOTUS database [Link]

Showing NP-Card for {2-[3-(furan-3-yl)propyl]-6-methyl-8-[(1s,6r)-1,2,6-trimethylcyclohex-2-en-1-yl]oct-5-en-1-yl}oxysulfonic acid (NP0280939)

MOL for NP0280939 ({2-[3-(furan-3-yl)propyl]-6-methyl-8-[(1s,6r)-1,2,6-trimethylcyclohex-2-en-1-yl]oct-5-en-1-yl}oxysulfonic acid)

3D MOL for NP0280939 ({2-[3-(furan-3-yl)propyl]-6-methyl-8-[(1s,6r)-1,2,6-trimethylcyclohex-2-en-1-yl]oct-5-en-1-yl}oxysulfonic acid)

3D SDF for NP0280939 ({2-[3-(furan-3-yl)propyl]-6-methyl-8-[(1s,6r)-1,2,6-trimethylcyclohex-2-en-1-yl]oct-5-en-1-yl}oxysulfonic acid)

3D-SDF for NP0280939 ({2-[3-(furan-3-yl)propyl]-6-methyl-8-[(1s,6r)-1,2,6-trimethylcyclohex-2-en-1-yl]oct-5-en-1-yl}oxysulfonic acid)

PDB for NP0280939 ({2-[3-(furan-3-yl)propyl]-6-methyl-8-[(1s,6r)-1,2,6-trimethylcyclohex-2-en-1-yl]oct-5-en-1-yl}oxysulfonic acid)

3D PDB for NP0280939 ({2-[3-(furan-3-yl)propyl]-6-methyl-8-[(1s,6r)-1,2,6-trimethylcyclohex-2-en-1-yl]oct-5-en-1-yl}oxysulfonic acid)

SMILES for NP0280939 ({2-[3-(furan-3-yl)propyl]-6-methyl-8-[(1s,6r)-1,2,6-trimethylcyclohex-2-en-1-yl]oct-5-en-1-yl}oxysulfonic acid)

INCHI for NP0280939 ({2-[3-(furan-3-yl)propyl]-6-methyl-8-[(1s,6r)-1,2,6-trimethylcyclohex-2-en-1-yl]oct-5-en-1-yl}oxysulfonic acid)

Structure for NP0280939 ({2-[3-(furan-3-yl)propyl]-6-methyl-8-[(1s,6r)-1,2,6-trimethylcyclohex-2-en-1-yl]oct-5-en-1-yl}oxysulfonic acid)

3D Structure for NP0280939 ({2-[3-(furan-3-yl)propyl]-6-methyl-8-[(1s,6r)-1,2,6-trimethylcyclohex-2-en-1-yl]oct-5-en-1-yl}oxysulfonic acid)