NP-MRD: Showing NP-Card for Strophiofimbrin B (NP0331591)

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Record Information

Version

2.0

Created at

2023-04-18 16:00:18 UTC

Updated at

2024-09-03 04:16:12 UTC

NP-MRD ID

NP0331591

Natural Product DOI

https://doi.org/10.57994/0571

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Strophiofimbrin B

Description

Strophiofimbrin B belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Strophiofimbrin B was first documented in 2023 (PMID: 37043752). Based on a literature review very few articles have been published on Strophiofimbrin B.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304182318002D          

 24 26  0  0  1  0            999 V2000
   -0.4664   -2.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1849   -1.6253    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5427   -1.2363    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2433   -1.6719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9708   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2164   -2.4964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5696   -0.4117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1311    0.0238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8855   -1.1897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9080   -0.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5668    0.1316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3658   -0.0738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7034   -0.8266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5281   -0.8491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9599   -0.1461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3253   -1.5599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8219   -2.2186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5163   -1.7215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2055   -2.4857    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6410   -3.1863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4656   -3.1594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9012   -3.8601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2520   -3.9139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3826   -2.4262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  2  0  0  0  0
  9 18  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  2  0  0  0  0
 19 24  1  0  0  0  0
  2 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331591

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@H]1C[C@]2(C)[C@H](CCC3=CC=C(OC)C(=O)C1=C23)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O4/c1-11(2)14-8-6-12-7-9-15(23-4)18(21)16-13(19(22)24-5)10-20(14,3)17(12)16/h7,9,13-14H,1,6,8,10H2,2-5H3/t13-,14-,20-/m1/s1

> <INCHI_KEY>
FGKGWRYXQACBGI-ARGWCVDVSA-N

> <FORMULA>
C20H24O4

> <MOLECULAR_WEIGHT>
328.408

> <EXACT_MASS>
328.167459253

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
36.34292961340602

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2R,4R,5R)-11-methoxy-4-methyl-12-oxo-5-(prop-1-en-2-yl)tricyclo[6.4.1.0^{4,13}]trideca-1(13),8,10-triene-2-carboxylate

> <JCHEM_LOGP>
2.6709490166666674

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.799524939143487

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
94.89729999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2R,4R,5R)-11-methoxy-4-methyl-12-oxo-5-(prop-1-en-2-yl)tricyclo[6.4.1.0^{4,13}]trideca-1(13),8,10-triene-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-23         0                                  
HETATM    1  C   UNK     0      -0.871  -3.979   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.345  -3.034   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.013  -2.308   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.321  -3.121   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.679  -2.395   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.271  -4.660   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.063  -0.769   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.245   0.045   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.653  -2.221   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.695  -0.681   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.925   0.246   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.416  -0.138   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.046  -1.543   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.586  -1.585   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.392  -0.273   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.341  -2.912   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.268  -4.141   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.830  -3.213   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.250  -4.640   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.063  -5.948   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.602  -5.898   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.415  -7.205   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.337  -7.306   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.714  -4.529   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9   24                                             
CONECT    3    2    4    7                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    3    8                                                       
CONECT    8    7   10                                                       
CONECT    9    2   10   18                                                  
CONECT   10    9    8   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18    9   16   19                                                  
CONECT   19   18   20   24                                                  
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20                                                            
CONECT   24   19    2                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₄

Average Mass

328.4080 Da

Monoisotopic Mass

328.16746 Da

IUPAC Name

methyl (2R,4R,5R)-11-methoxy-4-methyl-12-oxo-5-(prop-1-en-2-yl)tricyclo[6.4.1.0^{4,13}]trideca-1(13),8,10-triene-2-carboxylate

Traditional Name

methyl (2R,4R,5R)-11-methoxy-4-methyl-12-oxo-5-(prop-1-en-2-yl)tricyclo[6.4.1.0^{4,13}]trideca-1(13),8,10-triene-2-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@H]1C[C@]2(C)[C@H](CCC3=CC=C(OC)C(=O)C1=C23)C(C)=C

InChI Identifier

InChI=1S/C20H24O4/c1-11(2)14-8-6-12-7-9-15(23-4)18(21)16-13(19(22)24-5)10-20(14,3)17(12)16/h7,9,13-14H,1,6,8,10H2,2-5H3/t13-,14-,20-/m1/s1

InChI Key

FGKGWRYXQACBGI-ARGWCVDVSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CD3OD, experimental)	houljiang@126.com	Not Available	Not Available	2023-04-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	houljiang@126.com	Not Available	Not Available	2023-04-18	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.2, CD₃OD, simulated)	houljiang@126.com	Not Available	houlijiang	2024-05-14	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
fimbricalyx		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Farsesane sesquiterpenoid
Sesquiterpenoid
Tropone
Gamma-keto acid
Fatty acid ester
Alkyl aryl ether
Fatty acyl
Alpha-branched alpha,beta-unsaturated-ketone
Keto acid
Alpha,beta-unsaturated ketone
Methyl ester
Enone
Acryloyl-group
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	2.67	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	94.9 m³·mol⁻¹	ChemAxon
Polarizability	36.34 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jiang HL, Zhang YY, Mao HY, Zhang Y, Cao YX, Yu HY, Dong XY, Tao L, Yang CS: Strophiofimbrins A and B: Two Rearranged Norditerpenoids with Novel Tricyclic Carbon Skeletons from Strophioblachia fimbricalyx. J Org Chem. 2023 May 5;88(9):5936-5943. doi: 10.1021/acs.joc.3c00301. Epub 2023 Apr 12. [PubMed:37043752 ]

Showing NP-Card for Strophiofimbrin B (NP0331591)

MOL for NP0331591 (Strophiofimbrin B)

3D MOL for NP0331591 (Strophiofimbrin B)

3D SDF for NP0331591 (Strophiofimbrin B)

3D-SDF for NP0331591 (Strophiofimbrin B)

PDB for NP0331591 (Strophiofimbrin B)

3D PDB for NP0331591 (Strophiofimbrin B)

SMILES for NP0331591 (Strophiofimbrin B)

INCHI for NP0331591 (Strophiofimbrin B)

Structure for NP0331591 (Strophiofimbrin B)

3D Structure for NP0331591 (Strophiofimbrin B)