NP-MRD: Showing NP-Card for (4s,8s,10r,18r,19r)-18-(furan-3-yl)-10-hydroxy-4,9,9,19-tetramethyl-5,17-dioxa-2-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,11,14-tetraene-6,16-dione (NP0280099)

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Record Information

Version

2.0

Created at

2022-09-09 05:43:14 UTC

Updated at

2022-09-09 05:43:14 UTC

NP-MRD ID

NP0280099

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4s,8s,10r,18r,19r)-18-(furan-3-yl)-10-hydroxy-4,9,9,19-tetramethyl-5,17-dioxa-2-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,11,14-tetraene-6,16-dione

Description

Xylogranatin F belongs to the class of organic compounds known as acridines. These are organic compounds containing the acridine moiety, a linear tricyclic heterocycle which consists of two benzene rings joined by a pyridine ring. (4s,8s,10r,18r,19r)-18-(furan-3-yl)-10-hydroxy-4,9,9,19-tetramethyl-5,17-dioxa-2-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,11,14-tetraene-6,16-dione is found in Xylocarpus granatum. (4s,8s,10r,18r,19r)-18-(furan-3-yl)-10-hydroxy-4,9,9,19-tetramethyl-5,17-dioxa-2-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,11,14-tetraene-6,16-dione was first documented in 2020 (PMID: 32125044). Based on a literature review very few articles have been published on Xylogranatin F.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092207432D          

 33 38  0  0  1  0            999 V2000
    5.6402   -1.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8607   -0.9535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7298   -1.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2623   -0.2329    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0666   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1403    0.7726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8484    1.1959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3816    1.0967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8390    0.4752    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4920    1.2237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5908    1.1708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6125   -0.2580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6342   -1.6868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309092207432D          

 33 38  0  0  1  0            999 V2000
    5.6402   -1.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8607   -0.9535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0280099

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12OC(=O)C[C@H]1C(C)(C)[C@@H](O)C1=CC3=C(CC[C@@]4(C)[C@@H](OC(=O)C=C34)C3=COC=C3)N=C21

> <INCHI_IDENTIFIER>
InChI=1S/C26H27NO6/c1-24(2)18-11-20(29)33-26(18,4)21-15(22(24)30)9-14-16-10-19(28)32-23(13-6-8-31-12-13)25(16,3)7-5-17(14)27-21/h6,8-10,12,18,22-23,30H,5,7,11H2,1-4H3/t18-,22-,23-,25+,26-/m0/s1

> <INCHI_KEY>
XKLARMZOADMPPA-VTJGNRCXSA-N

> <FORMULA>
C26H27NO6

> <MOLECULAR_WEIGHT>
449.503

> <EXACT_MASS>
449.183837593

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
47.62014931059939

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S,8S,10R,18R,19R)-18-(furan-3-yl)-10-hydroxy-4,9,9,19-tetramethyl-5,17-dioxa-2-azapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-1(13),2,11,14-tetraene-6,16-dione

> <JCHEM_LOGP>
3.2683773699999987

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.723147935219657

> <JCHEM_PKA_STRONGEST_BASIC>
3.317443022675502

> <JCHEM_POLAR_SURFACE_AREA>
98.86000000000001

> <JCHEM_REFRACTIVITY>
117.59849999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4S,8S,10R,18R,19R)-18-(furan-3-yl)-10-hydroxy-4,9,9,19-tetramethyl-5,17-dioxa-2-azapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-1(13),2,11,14-tetraene-6,16-dione

> <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      10.528  -2.285   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.073  -1.780   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.829  -3.300   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.823  -0.435   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.324  -0.092   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.462   1.442   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      12.784   2.232   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      10.046   2.047   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.033   0.887   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.385   2.284   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.493   0.864   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       6.703   2.185   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       5.163   2.162   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.413   0.817   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.204  -0.505   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.743  -0.482   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.534  -1.803   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.784  -3.149   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.874   0.793   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.124  -0.552   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.584  -0.575   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.166  -1.920   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -0.206   0.747   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.543   2.092   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.247   3.414   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.781   3.551   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.124   5.053   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.802   5.843   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.358   4.830   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.083   2.115   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.293   3.437   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.833   3.460   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.373   3.484   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   17                                             
CONECT    3    2                                                            
CONECT    4    2    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8    4   10   11                                             
CONECT   10    9                                                            
CONECT   11    9   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   33                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11   17                                                  
CONECT   17   16    2   18                                                  
CONECT   18   17                                                            
CONECT   19   14   20   30                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   30                                                  
CONECT   25   24   26   29                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   25                                                       
CONECT   30   24   19   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   13                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₇NO₆

Average Mass

449.5030 Da

Monoisotopic Mass

449.18384 Da

IUPAC Name

(4S,8S,10R,18R,19R)-18-(furan-3-yl)-10-hydroxy-4,9,9,19-tetramethyl-5,17-dioxa-2-azapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-1(13),2,11,14-tetraene-6,16-dione

Traditional Name

(4S,8S,10R,18R,19R)-18-(furan-3-yl)-10-hydroxy-4,9,9,19-tetramethyl-5,17-dioxa-2-azapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-1(13),2,11,14-tetraene-6,16-dione

CAS Registry Number

Not Available

SMILES

C[C@]12OC(=O)C[C@H]1C(C)(C)[C@@H](O)C1=CC3=C(CC[C@@]4(C)[C@@H](OC(=O)C=C34)C3=COC=C3)N=C21

InChI Identifier

InChI=1S/C26H27NO6/c1-24(2)18-11-20(29)33-26(18,4)21-15(22(24)30)9-14-16-10-19(28)32-23(13-6-8-31-12-13)25(16,3)7-5-17(14)27-21/h6,8-10,12,18,22-23,30H,5,7,11H2,1-4H3/t18-,22-,23-,25+,26-/m0/s1

InChI Key

XKLARMZOADMPPA-VTJGNRCXSA-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

Species Name	Source	Reference
Xylocarpus granatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acridines. These are organic compounds containing the acridine moiety, a linear tricyclic heterocycle which consists of two benzene rings joined by a pyridine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Acridines

Alternative Parents

Substituents

Acridine
Dihydropyranone
Dicarboxylic acid or derivatives
Gamma butyrolactone
Pyran
Pyridine
Furan
Oxolane
Heteroaromatic compound
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Azacycle
Oxacycle
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
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	3.27	ChemAxon
pKa (Strongest Acidic)	13.72	ChemAxon
pKa (Strongest Basic)	3.32	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	98.86 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	117.6 m³·mol⁻¹	ChemAxon
Polarizability	47.62 Å³	ChemAxon
Number of Rings	6	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

C00048912

Chemspider ID

27023678

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24786717

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu Y, Holt TA, Kutateladze A, Newhouse TR: Stereochemical revision of xylogranatin F by GIAO and DU8+ NMR calculations. Chirality. 2020 May;32(5):515-523. doi: 10.1002/chir.23189. Epub 2020 Mar 3. [PubMed:32125044 ]
LOTUS database [Link]

Showing NP-Card for (4s,8s,10r,18r,19r)-18-(furan-3-yl)-10-hydroxy-4,9,9,19-tetramethyl-5,17-dioxa-2-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,11,14-tetraene-6,16-dione (NP0280099)

MOL for NP0280099 ((4s,8s,10r,18r,19r)-18-(furan-3-yl)-10-hydroxy-4,9,9,19-tetramethyl-5,17-dioxa-2-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,11,14-tetraene-6,16-dione)

3D MOL for NP0280099 ((4s,8s,10r,18r,19r)-18-(furan-3-yl)-10-hydroxy-4,9,9,19-tetramethyl-5,17-dioxa-2-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,11,14-tetraene-6,16-dione)

3D SDF for NP0280099 ((4s,8s,10r,18r,19r)-18-(furan-3-yl)-10-hydroxy-4,9,9,19-tetramethyl-5,17-dioxa-2-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,11,14-tetraene-6,16-dione)

3D-SDF for NP0280099 ((4s,8s,10r,18r,19r)-18-(furan-3-yl)-10-hydroxy-4,9,9,19-tetramethyl-5,17-dioxa-2-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,11,14-tetraene-6,16-dione)

PDB for NP0280099 ((4s,8s,10r,18r,19r)-18-(furan-3-yl)-10-hydroxy-4,9,9,19-tetramethyl-5,17-dioxa-2-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,11,14-tetraene-6,16-dione)

3D PDB for NP0280099 ((4s,8s,10r,18r,19r)-18-(furan-3-yl)-10-hydroxy-4,9,9,19-tetramethyl-5,17-dioxa-2-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,11,14-tetraene-6,16-dione)

SMILES for NP0280099 ((4s,8s,10r,18r,19r)-18-(furan-3-yl)-10-hydroxy-4,9,9,19-tetramethyl-5,17-dioxa-2-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,11,14-tetraene-6,16-dione)

INCHI for NP0280099 ((4s,8s,10r,18r,19r)-18-(furan-3-yl)-10-hydroxy-4,9,9,19-tetramethyl-5,17-dioxa-2-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,11,14-tetraene-6,16-dione)

Structure for NP0280099 ((4s,8s,10r,18r,19r)-18-(furan-3-yl)-10-hydroxy-4,9,9,19-tetramethyl-5,17-dioxa-2-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,11,14-tetraene-6,16-dione)

3D Structure for NP0280099 ((4s,8s,10r,18r,19r)-18-(furan-3-yl)-10-hydroxy-4,9,9,19-tetramethyl-5,17-dioxa-2-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,11,14-tetraene-6,16-dione)