NP-MRD: Showing NP-Card for (+)-epi-Fibrauretinoside A (NP0076511)

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Record Information

Version

1.0

Created at

2022-04-28 21:41:17 UTC

Updated at

2022-04-28 21:41:17 UTC

NP-MRD ID

NP0076511

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-epi-Fibrauretinoside A

Description

(1S,2S,4S,7S,8S,9S,12S,16S)-4-(furan-3-yl)-7,8-dihydroxy-2,16-dimethyl-12-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]Hexadec-13-en-6-one belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. (+)-epi-Fibrauretinoside A is found in Fibraurea tinctoria. It was first documented in 2022 (PMID: 35490355). Based on a literature review a significant number of articles have been published on (1S,2S,4S,7S,8S,9S,12S,16S)-4-(furan-3-yl)-7,8-dihydroxy-2,16-dimethyl-12-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]Hexadec-13-en-6-one (PMID: 35490354) (PMID: 35490353) (PMID: 35490352) (PMID: 35490351).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223412D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282223412D          

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   -2.5799    3.1638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4758    4.3900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1381    4.0469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1168    4.8315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  1  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
  3 12  1  0  0  0  0
  9 13  1  1  0  0  0
  8 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  7 18  1  0  0  0  0
 17 19  1  1  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 19 23  1  0  0  0  0
  8 24  1  6  0  0  0
  7 25  1  1  0  0  0
  4 26  1  6  0  0  0
  3 27  1  1  0  0  0
 28 27  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  6  0  0  0
 32 35  1  1  0  0  0
 31 36  1  6  0  0  0
 30 37  1  1  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0076511

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12[C@@H]3OC[C@]1(O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C=CC[C@H]2[C@]1(C)C[C@H](OC(=O)[C@@]1(O)[C@H]3O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O12/c1-23-8-13(12-5-7-34-10-12)37-22(32)26(23,33)19(31)20-24(2)15(23)4-3-6-25(24,11-35-20)38-21-18(30)17(29)16(28)14(9-27)36-21/h3,5-7,10,13-21,27-31,33H,4,8-9,11H2,1-2H3/t13-,14+,15-,16+,17-,18+,19-,20+,21-,23-,24-,25+,26-/m0/s1

> <INCHI_KEY>
KTLOXVIRNBVBRP-LLOICOAJSA-N

> <FORMULA>
C26H34O12

> <MOLECULAR_WEIGHT>
538.546

> <EXACT_MASS>
538.205026535

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
52.23737250040426

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,4S,7S,8S,9S,12S,16S)-4-(furan-3-yl)-7,8-dihydroxy-2,16-dimethyl-12-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,10-dioxatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadec-13-en-6-one

> <ALOGPS_LOGP>
-0.03

> <JCHEM_LOGP>
-1.1800491719999995

> <ALOGPS_LOGS>
-2.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.218220826825153

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.048317302349954

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8675050638938475

> <JCHEM_POLAR_SURFACE_AREA>
188.51

> <JCHEM_REFRACTIVITY>
125.20759999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.00e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4S,7S,8S,9S,12S,16S)-4-(furan-3-yl)-7,8-dihydroxy-2,16-dimethyl-12-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,10-dioxatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadec-13-en-6-one

> <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       1.479   4.553   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.335   3.522   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.655   2.016   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.120   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.264   2.570   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.944   4.077   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.787  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.453  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.120   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.655  -0.476   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.250   0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.453  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       7.454  -0.000   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.788   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.949   3.842   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.455   4.162   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      11.225   2.828   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.195   1.684   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.787  -1.540   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.842   3.079   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.526   0.914   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.851   2.336   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.327   3.801   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.297   4.945   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -0.773   6.410   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.279   6.730   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -3.309   5.586   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.834   4.121   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -3.864   2.976   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -4.816   5.906   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -2.755   8.195   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       0.258   7.554   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -0.218   9.019   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   12   27                                             
CONECT    4    3    5   10   26                                             
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   18   25                                             
CONECT    8    7    9   14   24                                             
CONECT    9    8   10   13                                                  
CONECT   10    9    4   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11    3                                                       
CONECT   13    9                                                            
CONECT   14    8   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17    7                                                       
CONECT   19   17   20   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   19                                                       
CONECT   24    8                                                            
CONECT   25    7                                                            
CONECT   26    4                                                            
CONECT   27    3   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   37                                                  
CONECT   31   30   32   36                                                  
CONECT   32   31   33   35                                                  
CONECT   33   32   28   34                                                  
CONECT   34   33                                                            
CONECT   35   32                                                            
CONECT   36   31                                                            
CONECT   37   30   38                                                       
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₄O₁₂

Average Mass

538.5460 Da

Monoisotopic Mass

538.20503 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@]12[C@@H]3OC[C@]1(O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C=CC[C@H]2[C@]1(C)C[C@H](OC(=O)[C@@]1(O)[C@H]3O)C1=COC=C1

InChI Identifier

InChI=1S/C26H34O12/c1-23-8-13(12-5-7-34-10-12)37-22(32)26(23,33)19(31)20-24(2)15(23)4-3-6-25(24,11-35-20)38-21-18(30)17(29)16(28)14(9-27)36-21/h3,5-7,10,13-21,27-31,33H,4,8-9,11H2,1-2H3/t13-,14+,15-,16+,17-,18+,19-,20+,21-,23-,24-,25+,26-/m0/s1

InChI Key

KTLOXVIRNBVBRP-LLOICOAJSA-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
Fibraurea tinctoria	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Naphthalene
Delta_valerolactone
Delta valerolactone
Pyran
Oxane
Monosaccharide
Heteroaromatic compound
Tetrahydrofuran
Tertiary alcohol
Furan
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Polyol
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	-0.03	ALOGPS
logP	-1.2	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	11.05	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	188.51 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	125.21 m³·mol⁻¹	ChemAxon
Polarizability	52.24 Å³	ChemAxon
Number of Rings	6	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

163067489

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Baumbusch J, Blakey EP, Carapellotti AM, Dohmen M, Fick DM, Kagan SH, Melendez-Torres GJ, Morgan BE, Munsterman E, Resnick B, Young HM: Nurses and the decade of healthy ageing: An unprecedented opportunity. Int J Older People Nurs. 2022 May;17(3):e12469. doi: 10.1111/opn.12469. [PubMed:35490355 ]
Hill NL, Bratlee-Whitaker E, Wion RK, Madrigal C, Bhargava S, Mogle J: Factors that influence the emotional impact of memory problems in older adults: A qualitative descriptive study. Int J Older People Nurs. 2022 May;17(3):e12439. doi: 10.1111/opn.12439. Epub 2021 Dec 8. [PubMed:35490354 ]
Polastri M, Loforte A, Swol J: "Racing team" or "orchestra" approach? Two different perspectives on providing care in emergency and critical settings. Artif Organs. 2022 May 1. doi: 10.1111/aor.14274. [PubMed:35490353 ]
Wei YF, Wang L, Xia ZY, Gou M, Sun ZY, Lv WF, Tang YQ: Microbial communities in crude oil phase and filter-graded aqueous phase from a Daqing oilfield after polymer flooding. J Appl Microbiol. 2022 May 1. doi: 10.1111/jam.15603. [PubMed:35490352 ]
Authors unspecified: CORRIGENDUM. Transbound Emerg Dis. 2022 May 1. doi: 10.1111/tbed.14572. [PubMed:35490351 ]

Showing NP-Card for (+)-epi-Fibrauretinoside A (NP0076511)

MOL for NP0076511 ((+)-epi-Fibrauretinoside A)

3D MOL for NP0076511 ((+)-epi-Fibrauretinoside A)

3D SDF for NP0076511 ((+)-epi-Fibrauretinoside A)

3D-SDF for NP0076511 ((+)-epi-Fibrauretinoside A)

PDB for NP0076511 ((+)-epi-Fibrauretinoside A)

3D PDB for NP0076511 ((+)-epi-Fibrauretinoside A)

SMILES for NP0076511 ((+)-epi-Fibrauretinoside A)

INCHI for NP0076511 ((+)-epi-Fibrauretinoside A)

Structure for NP0076511 ((+)-epi-Fibrauretinoside A)

3D Structure for NP0076511 ((+)-epi-Fibrauretinoside A)