NP-MRD: Showing NP-Card for (1r,6r,7r,10s,11s,14s,16r,17r,18s)-11-(furan-3-yl)-18-hydroxy-6,10,17,20,20-pentamethyl-2,12,15,19-tetraoxahexacyclo[16.2.1.0¹,⁶.0⁷,¹⁷.0¹⁰,¹⁶.0¹⁴,¹⁶]henicos-4-ene-3,13,21-trione (NP0318696)

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Record Information

Version

2.0

Created at

2022-09-11 19:20:33 UTC

Updated at

2022-09-11 19:20:34 UTC

NP-MRD ID

NP0318696

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,6r,7r,10s,11s,14s,16r,17r,18s)-11-(furan-3-yl)-18-hydroxy-6,10,17,20,20-pentamethyl-2,12,15,19-tetraoxahexacyclo[16.2.1.0¹,⁶.0⁷,¹⁷.0¹⁰,¹⁶.0¹⁴,¹⁶]henicos-4-ene-3,13,21-trione

Description

(1R,6R,7R,10S,11R,14S,16R,17R,18S)-11-(furan-3-yl)-18-hydroxy-6,10,17,20,20-pentamethyl-2,12,15,19-tetraoxahexacyclo[16.2.1.0¹,⁶.0⁷,¹⁷.0¹⁰,¹⁶.0¹⁴,¹⁶]Henicos-4-ene-3,13,21-trione 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. (1r,6r,7r,10s,11s,14s,16r,17r,18s)-11-(furan-3-yl)-18-hydroxy-6,10,17,20,20-pentamethyl-2,12,15,19-tetraoxahexacyclo[16.2.1.0¹,⁶.0⁷,¹⁷.0¹⁰,¹⁶.0¹⁴,¹⁶]henicos-4-ene-3,13,21-trione is found in Harrisonia perforata. Based on a literature review very few articles have been published on (1R,6R,7R,10S,11R,14S,16R,17R,18S)-11-(furan-3-yl)-18-hydroxy-6,10,17,20,20-pentamethyl-2,12,15,19-tetraoxahexacyclo[16.2.1.0¹,⁶.0⁷,¹⁷.0¹⁰,¹⁶.0¹⁴,¹⁶]Henicos-4-ene-3,13,21-trione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112221202D          

 35 41  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv1652309112221202D          

 35 41  0  0  1  0            999 V2000
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 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 23 27  2  0  0  0  0
 22 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  1  0  0  0
 33 32  1  1  0  0  0
 31 33  1  0  0  0  0
 20 33  1  0  0  0  0
 33 34  1  0  0  0  0
 17 34  1  0  0  0  0
  5 34  1  0  0  0  0
 34 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0318696

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)O[C@]2(O)C(=O)[C@]11OC(=O)C=C[C@]1(C)[C@H]1CC[C@@]3(C)[C@@H](OC(=O)[C@H]4O[C@@]34[C@]21C)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H28O9/c1-20(2)25-19(29)26(30,35-20)23(5)14(21(25,3)10-7-15(27)33-25)6-9-22(4)16(13-8-11-31-12-13)32-18(28)17-24(22,23)34-17/h7-8,10-12,14,16-17,30H,6,9H2,1-5H3/t14-,16+,17-,21-,22+,23-,24-,25+,26-/m1/s1

> <INCHI_KEY>
BJMYIAUNRHAYSL-SFJVXEAASA-N

> <FORMULA>
C26H28O9

> <MOLECULAR_WEIGHT>
484.501

> <EXACT_MASS>
484.173332482

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
47.192646197603764

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,6R,7R,10S,11R,14S,16R,17R,18S)-11-(furan-3-yl)-18-hydroxy-6,10,17,20,20-pentamethyl-2,12,15,19-tetraoxahexacyclo[16.2.1.0^{1,6}.0^{7,17}.0^{10,16}.0^{14,16}]henicos-4-ene-3,13,21-trione

> <JCHEM_LOGP>
3.5218383279999994

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.801516041707515

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8612668484405472

> <JCHEM_POLAR_SURFACE_AREA>
124.80000000000001

> <JCHEM_REFRACTIVITY>
116.7

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,6R,7R,10S,11R,14S,16R,17R,18S)-11-(furan-3-yl)-18-hydroxy-6,10,17,20,20-pentamethyl-2,12,15,19-tetraoxahexacyclo[16.2.1.0^{1,6}.0^{7,17}.0^{10,16}.0^{14,16}]henicos-4-ene-3,13,21-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      12.469   1.402   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.930   1.463   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.178   2.983   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.364   1.920   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.456   0.584   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.070   1.255   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       9.756   0.112   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.310  -1.362   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      11.070  -0.210   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      12.659  -0.118   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      13.610  -1.352   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      15.137  -1.151   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      13.014  -2.780   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.483  -2.994   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.528  -1.765   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.028  -3.221   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.955  -2.164   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.435  -3.613   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.919  -3.887   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.924  -2.712   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.404  -4.161   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.409  -2.986   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.888  -4.435   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.755  -5.708   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.812  -6.926   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.363  -6.405   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.410  -4.866   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.414  -1.810   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.935  -0.361   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.940   0.814   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.450  -0.087   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.965   0.187   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.445  -1.263   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.960  -0.989   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.816   0.545   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    9                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7   34                                             
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7    2   10   15                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    9   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18   34                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22   33                                             
CONECT   21   20                                                            
CONECT   22   20   23   28                                                  
CONECT   23   22   24   27                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   23                                                       
CONECT   28   22   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31   33                                                       
CONECT   33   32   31   20   34                                             
CONECT   34   33   17    5   35                                             
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₈O₉

Average Mass

484.5010 Da

Monoisotopic Mass

484.17333 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1(C)O[C@]2(O)C(=O)[C@]11OC(=O)C=C[C@]1(C)[C@H]1CC[C@@]3(C)[C@@H](OC(=O)[C@H]4O[C@@]34[C@]21C)C1=COC=C1

InChI Identifier

InChI=1S/C26H28O9/c1-20(2)25-19(29)26(30,35-20)23(5)14(21(25,3)10-7-15(27)33-25)6-9-22(4)16(13-8-11-31-12-13)32-18(28)17-24(22,23)34-17/h7-8,10-12,14,16-17,30H,6,9H2,1-5H3/t14-,16+,17-,21-,22+,23-,24-,25+,26-/m1/s1

InChI Key

BJMYIAUNRHAYSL-SFJVXEAASA-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
Harrisonia perforata	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
Naphthalene
1,4-dioxepane
Delta valerolactone
Dihydropyranone
Dioxepane
Delta_valerolactone
Alpha-acyloxy ketone
Oxepane
Dicarboxylic acid or derivatives
3-furanone
Monosaccharide
Oxane
Pyran
Tetrahydrofuran
Enoate ester
Cyclic alcohol
Heteroaromatic compound
Furan
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Hemiacetal
Ketone
Lactone
Ether
Oxirane
Dialkyl ether
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
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

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

163187912

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,6r,7r,10s,11s,14s,16r,17r,18s)-11-(furan-3-yl)-18-hydroxy-6,10,17,20,20-pentamethyl-2,12,15,19-tetraoxahexacyclo[16.2.1.0¹,⁶.0⁷,¹⁷.0¹⁰,¹⁶.0¹⁴,¹⁶]henicos-4-ene-3,13,21-trione (NP0318696)

MOL for NP0318696 ((1r,6r,7r,10s,11s,14s,16r,17r,18s)-11-(furan-3-yl)-18-hydroxy-6,10,17,20,20-pentamethyl-2,12,15,19-tetraoxahexacyclo[16.2.1.0¹,⁶.0⁷,¹⁷.0¹⁰,¹⁶.0¹⁴,¹⁶]henicos-4-ene-3,13,21-trione)

3D MOL for NP0318696 ((1r,6r,7r,10s,11s,14s,16r,17r,18s)-11-(furan-3-yl)-18-hydroxy-6,10,17,20,20-pentamethyl-2,12,15,19-tetraoxahexacyclo[16.2.1.0¹,⁶.0⁷,¹⁷.0¹⁰,¹⁶.0¹⁴,¹⁶]henicos-4-ene-3,13,21-trione)

3D SDF for NP0318696 ((1r,6r,7r,10s,11s,14s,16r,17r,18s)-11-(furan-3-yl)-18-hydroxy-6,10,17,20,20-pentamethyl-2,12,15,19-tetraoxahexacyclo[16.2.1.0¹,⁶.0⁷,¹⁷.0¹⁰,¹⁶.0¹⁴,¹⁶]henicos-4-ene-3,13,21-trione)

3D-SDF for NP0318696 ((1r,6r,7r,10s,11s,14s,16r,17r,18s)-11-(furan-3-yl)-18-hydroxy-6,10,17,20,20-pentamethyl-2,12,15,19-tetraoxahexacyclo[16.2.1.0¹,⁶.0⁷,¹⁷.0¹⁰,¹⁶.0¹⁴,¹⁶]henicos-4-ene-3,13,21-trione)

PDB for NP0318696 ((1r,6r,7r,10s,11s,14s,16r,17r,18s)-11-(furan-3-yl)-18-hydroxy-6,10,17,20,20-pentamethyl-2,12,15,19-tetraoxahexacyclo[16.2.1.0¹,⁶.0⁷,¹⁷.0¹⁰,¹⁶.0¹⁴,¹⁶]henicos-4-ene-3,13,21-trione)

3D PDB for NP0318696 ((1r,6r,7r,10s,11s,14s,16r,17r,18s)-11-(furan-3-yl)-18-hydroxy-6,10,17,20,20-pentamethyl-2,12,15,19-tetraoxahexacyclo[16.2.1.0¹,⁶.0⁷,¹⁷.0¹⁰,¹⁶.0¹⁴,¹⁶]henicos-4-ene-3,13,21-trione)

SMILES for NP0318696 ((1r,6r,7r,10s,11s,14s,16r,17r,18s)-11-(furan-3-yl)-18-hydroxy-6,10,17,20,20-pentamethyl-2,12,15,19-tetraoxahexacyclo[16.2.1.0¹,⁶.0⁷,¹⁷.0¹⁰,¹⁶.0¹⁴,¹⁶]henicos-4-ene-3,13,21-trione)

INCHI for NP0318696 ((1r,6r,7r,10s,11s,14s,16r,17r,18s)-11-(furan-3-yl)-18-hydroxy-6,10,17,20,20-pentamethyl-2,12,15,19-tetraoxahexacyclo[16.2.1.0¹,⁶.0⁷,¹⁷.0¹⁰,¹⁶.0¹⁴,¹⁶]henicos-4-ene-3,13,21-trione)

Structure for NP0318696 ((1r,6r,7r,10s,11s,14s,16r,17r,18s)-11-(furan-3-yl)-18-hydroxy-6,10,17,20,20-pentamethyl-2,12,15,19-tetraoxahexacyclo[16.2.1.0¹,⁶.0⁷,¹⁷.0¹⁰,¹⁶.0¹⁴,¹⁶]henicos-4-ene-3,13,21-trione)

3D Structure for NP0318696 ((1r,6r,7r,10s,11s,14s,16r,17r,18s)-11-(furan-3-yl)-18-hydroxy-6,10,17,20,20-pentamethyl-2,12,15,19-tetraoxahexacyclo[16.2.1.0¹,⁶.0⁷,¹⁷.0¹⁰,¹⁶.0¹⁴,¹⁶]henicos-4-ene-3,13,21-trione)