NP-MRD: Showing NP-Card for Confertiflorin (NP0051857)

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Record Information

Version

2.0

Created at

2022-04-27 23:03:57 UTC

Updated at

2022-04-27 23:03:57 UTC

NP-MRD ID

NP0051857

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Confertiflorin

Description

Confertiflorin belongs to the class of organic compounds known as ambrosanolides and secoambrosanolides. These are sesquiterpene lactones from the Ambrosia family, with a backbone derivative of azuleno[6,5-b]furan-2-one (ambrosanolides) or azuleno[4,5-b]furan-2-one (secoambrosanolides). Confertiflorin is found in Ambrosia confertiflora. Confertiflorin was first documented in 1989 (PMID: 24272182). Based on a literature review very few articles have been published on Confertiflorin.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 46  0  0  0  0  0  0  0  0999 V2000
    2.6721    3.0755    0.0880 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4714    2.6352   -0.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3873    3.2578   -0.9307 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4803    4.3935   -1.4788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7209    2.3895   -0.9254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5484    1.6499    0.2936 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8878    1.3084    0.2536 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3250    0.2932   -0.7135 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9326   -0.7842    0.0112 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2280   -1.1860   -0.1617 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8060   -2.3031    0.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9536   -0.5935   -0.9996 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2780   -0.3010   -1.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4683   -1.3460   -0.8005 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5012   -1.9555   -1.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9501   -0.8293    0.4855 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0079   -1.6542    1.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6173   -0.6970    2.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0231    0.6237    1.9019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9709    1.5364    2.6798 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5103    0.5594    0.4748 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7593    0.6829   -0.3750 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9813    4.0361   -0.2701 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3644    2.4890    0.6641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6733    2.4398    1.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2384    1.1213    1.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1421    0.6726   -1.3961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3346   -2.3872    1.6089 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7287   -3.2747    0.0700 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8860   -2.0475    0.8067 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8207   -0.8681   -2.4034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3644    0.4110   -2.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2843   -2.1645   -0.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0780   -2.7730   -1.2405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9364   -2.4346   -2.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.1882   -2.1971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0768   -0.7999    1.2039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8025   -2.0104    0.5063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5855   -2.5486    1.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4090   -1.0508    3.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7198   -0.6384    2.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3478   -0.2420   -0.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4218    1.4699    0.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5663    1.0324   -1.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 13  1  0
 13  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  6 21  1  0
 21 22  1  6
 21 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 16 14  1  0
  2  7  1  0
 19 21  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 14 33  1  1
 13 31  1  0
 13 32  1  0
  8 27  1  6
 11 28  1  0
 11 29  1  0
 11 30  1  0
  7 26  1  1
  6 25  1  1
  1 23  1  0
  1 24  1  0
 22 42  1  0
 22 43  1  0
 22 44  1  0
 16 37  1  1
 17 38  1  0
 17 39  1  0
 18 40  1  0
 18 41  1  0
M  END


  Mrv1652304282201032D          

 22 24  0  0  1  0            999 V2000
    2.0090    2.2026    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4946    1.5576    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6696    1.5576    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1552    2.2026    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3388    3.0069    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0821    3.3648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8254    3.0069    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4704    3.5213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3062    3.5213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1833    4.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8283    4.8514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5847    4.6385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6172    1.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3057    2.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5802    1.0885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2252    0.5741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2151    0.8690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9491    0.8690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6592    0.0966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7444    1.0885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7814    1.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1037    0.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  6  0  0  0
  5  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  4 13  1  6  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  3 17  1  6  0  0  0
  2 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
  1 21  1  6  0  0  0
  2 22  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0051857

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C[C@H](OC(C)=O)[C@@H]2[C@@H](OC(=O)C2=C)[C@@]2(C)[C@H]1CCC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O5/c1-8-7-12(21-10(3)18)14-9(2)16(20)22-15(14)17(4)11(8)5-6-13(17)19/h8,11-12,14-15H,2,5-7H2,1,3-4H3/t8-,11-,12-,14+,15+,17-/m0/s1

> <INCHI_KEY>
VWBKXLDATRBPOE-VICSMPQUSA-N

> <FORMULA>
C17H22O5

> <MOLECULAR_WEIGHT>
306.358

> <EXACT_MASS>
306.146723808

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
31.869161803804392

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4S,6S,6aS,9aR,9bR)-6,9a-dimethyl-3-methylidene-2,9-dioxo-dodecahydroazuleno[4,5-b]furan-4-yl acetate

> <ALOGPS_LOGP>
1.38

> <JCHEM_LOGP>
2.2902088420000006

> <ALOGPS_LOGS>
-3.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.576540080231837

> <JCHEM_PKA_STRONGEST_BASIC>
-6.58014826081256

> <JCHEM_POLAR_SURFACE_AREA>
69.67000000000002

> <JCHEM_REFRACTIVITY>
77.68130000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
confertiflorin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       3.750   4.111   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.790   2.907   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.250   2.907   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.290   4.111   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.632   5.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.020   6.281   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.407   5.613   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.611   6.573   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.572   6.573   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.342   8.096   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.546   9.056   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.091   8.658   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.152   3.570   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.437   4.419   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.083   2.032   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.287   1.072   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.402   1.622   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.638   1.622   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.097   0.180   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.123   2.032   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.192   3.570   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.060   1.551   0.000  0.00  0.00           C+0
CONECT    1    2    7   21                                                  
CONECT    2    1    3   18   22                                             
CONECT    3    2    4   17                                                  
CONECT    4    3    5   13                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    1    8                                                  
CONECT    8    7                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    4   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    3                                                       
CONECT   18    2   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20    1                                                       
CONECT   22    2                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
(+)-Confertiflorin	Kegg

Chemical Formula

C₁₇H₂₂O₅

Average Mass

306.3580 Da

Monoisotopic Mass

306.14672 Da

IUPAC Name

(3aR,4S,6S,6aS,9aR,9bR)-6,9a-dimethyl-3-methylidene-2,9-dioxo-dodecahydroazuleno[4,5-b]furan-4-yl acetate

Traditional Name

confertiflorin

CAS Registry Number

Not Available

SMILES

C[C@H]1C[C@H](OC(C)=O)[C@@H]2[C@@H](OC(=O)C2=C)[C@@]2(C)[C@H]1CCC2=O

InChI Identifier

InChI=1S/C17H22O5/c1-8-7-12(21-10(3)18)14-9(2)16(20)22-15(14)17(4)11(8)5-6-13(17)19/h8,11-12,14-15H,2,5-7H2,1,3-4H3/t8-,11-,12-,14+,15+,17-/m0/s1

InChI Key

VWBKXLDATRBPOE-VICSMPQUSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ambrosia confertiflora	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ambrosanolides and secoambrosanolides. These are sesquiterpene lactones from the Ambrosia family, with a backbone derivative of azuleno[6,5-b]furan-2-one (ambrosanolides) or azuleno[4,5-b]furan-2-one (secoambrosanolides).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Ambrosanolides and secoambrosanolides

Alternative Parents

Substituents

Ambrosanolide
Pseudoguaiane sesquiterpenoid
Sesquiterpenoid
Dicarboxylic acid or derivatives
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Lactone
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

sesquiterpene lactone (CHEBI:3854 )
Sesquiterpenoids (C15) (C09374 )

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	1.38	ALOGPS
logP	2.29	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	19.58	ChemAxon
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	69.67 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	77.68 m³·mol⁻¹	ChemAxon
Polarizability	31.87 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

C00003235

Chemspider ID

256799

KEGG Compound ID

C09374

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

291096

PDB ID

Not Available

ChEBI ID

3854

Good Scents ID

Not Available

References

General References

Fischer NH, Weidenhamer JD, Bradow JM: Inhibition and promotion of germination by several sesquiterpenes. J Chem Ecol. 1989 Jun;15(6):1785-93. doi: 10.1007/BF01012266. [PubMed:24272182 ]

Showing NP-Card for Confertiflorin (NP0051857)

MOL for NP0051857 (Confertiflorin)

3D MOL for NP0051857 (Confertiflorin)

3D SDF for NP0051857 (Confertiflorin)

3D-SDF for NP0051857 (Confertiflorin)

PDB for NP0051857 (Confertiflorin)

3D PDB for NP0051857 (Confertiflorin)

SMILES for NP0051857 (Confertiflorin)

INCHI for NP0051857 (Confertiflorin)

Structure for NP0051857 (Confertiflorin)

3D Structure for NP0051857 (Confertiflorin)