NP-MRD: Showing NP-Card for (1r,19r)-10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1¹,¹⁹.0²,¹¹.0³,⁸.0¹⁷,²²]tricosa-2(11),4,9,13,15,17(22)-hexaen-12-one (NP0327516)

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Record Information

Version

2.0

Created at

2022-09-12 10:09:33 UTC

Updated at

2022-09-12 10:09:33 UTC

NP-MRD ID

NP0327516

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,19r)-10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1¹,¹⁹.0²,¹¹.0³,⁸.0¹⁷,²²]tricosa-2(11),4,9,13,15,17(22)-hexaen-12-one

Description

Kenganthranol D 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,19r)-10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1¹,¹⁹.0²,¹¹.0³,⁸.0¹⁷,²²]tricosa-2(11),4,9,13,15,17(22)-hexaen-12-one is found in Harungana madagascariensis. (1r,19r)-10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1¹,¹⁹.0²,¹¹.0³,⁸.0¹⁷,²²]tricosa-2(11),4,9,13,15,17(22)-hexaen-12-one was first documented in 2007 (PMID: 17352491). Based on a literature review very few articles have been published on kenganthranol D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122212092D          

 36 41  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309122212092D          

 36 41  0  0  1  0            999 V2000
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  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 16 27  1  0  0  0  0
 27 28  1  0  0  0  0
 17 29  1  0  0  0  0
 10 29  1  0  0  0  0
 29 30  1  6  0  0  0
 31 30  1  6  0  0  0
 31 32  1  0  0  0  0
  9 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
 29 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0327516

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C(C)C2=C3C(=C1O)C(=O)C1=C(C4C=CC(C)(C)OC4C=C1O)[C@]31O[C@H](C2)C(C)(C)O1

> <INCHI_IDENTIFIER>
InChI=1S/C30H34O6/c1-14(2)8-9-16-15(3)18-12-21-29(6,7)36-30(35-21)24-17-10-11-28(4,5)34-20(17)13-19(31)22(24)27(33)23(25(18)30)26(16)32/h8,10-11,13,17,20-21,31-32H,9,12H2,1-7H3/t17?,20?,21-,30-/m1/s1

> <INCHI_KEY>
XBJUOMGRRJXLNS-PKKCWRPDSA-N

> <FORMULA>
C30H34O6

> <MOLECULAR_WEIGHT>
490.596

> <EXACT_MASS>
490.235538815

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
55.29116397209171

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,19R)-10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1^{1,19}.0^{2,11}.0^{3,8}.0^{17,22}]tricosa-2(11),4,9,13,15,17(22)-hexaen-12-one

> <JCHEM_LOGP>
5.785335083666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.714887596938794

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.480298742042644

> <JCHEM_PKA_STRONGEST_BASIC>
-3.887683219946028

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
141.75900000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,19R)-10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1^{1,19}.0^{2,11}.0^{3,8}.0^{17,22}]tricosa-2(11),4,9,13,15,17(22)-hexaen-12-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -6.527  -2.521   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.463  -1.407   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.896   0.071   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.967  -1.771   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.904  -0.657   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.407  -1.021   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.972  -2.520   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.061  -3.610   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.534  -2.954   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.632  -1.780   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.158  -0.288   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.345   0.098   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.770   1.578   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.172   0.915   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.654   2.365   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.691   0.632   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.193  -0.824   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.705  -1.117   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.206  -2.573   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.718  -2.867   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.728  -1.704   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.697  -2.901   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.075  -0.958   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.226  -0.248   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.715   0.045   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.213   1.501   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.701   1.795   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.200   3.251   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.260  -2.133   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.945  -3.469   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.778  -4.817   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.184  -4.499   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.398  -4.610   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.445  -6.149   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.934  -4.711   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.666  -2.974   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   32                                                  
CONECT   10    9   11   29                                                  
CONECT   11   10   12   14                                                  
CONECT   12   11    6   13                                                  
CONECT   13   12                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   27                                                  
CONECT   17   16   18   29                                                  
CONECT   18   17   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21   25                                                       
CONECT   25   24   18   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   16   28                                                  
CONECT   28   27                                                            
CONECT   29   17   10   30   36                                             
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31    9                                                       
CONECT   33   31   34   35   36                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   33   29                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₄O₆

Average Mass

490.5960 Da

Monoisotopic Mass

490.23554 Da

IUPAC Name

(1R,19R)-10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1^{1,19}.0^{2,11}.0^{3,8}.0^{17,22}]tricosa-2(11),4,9,13,15,17(22)-hexaen-12-one

Traditional Name

(1R,19R)-10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1^{1,19}.0^{2,11}.0^{3,8}.0^{17,22}]tricosa-2(11),4,9,13,15,17(22)-hexaen-12-one

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C(C)C2=C3C(=C1O)C(=O)C1=C(C4C=CC(C)(C)OC4C=C1O)[C@]31O[C@H](C2)C(C)(C)O1

InChI Identifier

InChI=1S/C30H34O6/c1-14(2)8-9-16-15(3)18-12-21-29(6,7)36-30(35-21)24-17-10-11-28(4,5)34-20(17)13-19(31)22(24)27(33)23(25(18)30)26(16)32/h8,10-11,13,17,20-21,31-32H,9,12H2,1-7H3/t17?,20?,21-,30-/m1/s1

InChI Key

XBJUOMGRRJXLNS-PKKCWRPDSA-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
Harungana madagascariensis	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
Benzopyran
Isochromane
Naphthalene
2-benzopyran
Aryl ketone
Ketal
Benzenoid
Pyran
Vinylogous acid
Meta-dioxolane
Ketone
Ether
Enol
Dialkyl ether
Acetal
Oxacycle
Organic oxygen compound
Aldehyde
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	5.79	ChemAxon
pKa (Strongest Acidic)	7.48	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	141.76 m³·mol⁻¹	ChemAxon
Polarizability	55.29 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	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

23281711

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44421665

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kouam SF, Yapna DB, Krohn K, Ngadjui BT, Ngoupayo J, Choudhary MI, Schulz B: Antimicrobial prenylated anthracene derivatives from the leaves of Harungana madagascariensis. J Nat Prod. 2007 Apr;70(4):600-3. doi: 10.1021/np060556l. Epub 2007 Mar 13. [PubMed:17352491 ]
LOTUS database [Link]

Showing NP-Card for (1r,19r)-10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1¹,¹⁹.0²,¹¹.0³,⁸.0¹⁷,²²]tricosa-2(11),4,9,13,15,17(22)-hexaen-12-one (NP0327516)

MOL for NP0327516 ((1r,19r)-10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1¹,¹⁹.0²,¹¹.0³,⁸.0¹⁷,²²]tricosa-2(11),4,9,13,15,17(22)-hexaen-12-one)

3D MOL for NP0327516 ((1r,19r)-10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1¹,¹⁹.0²,¹¹.0³,⁸.0¹⁷,²²]tricosa-2(11),4,9,13,15,17(22)-hexaen-12-one)

3D SDF for NP0327516 ((1r,19r)-10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1¹,¹⁹.0²,¹¹.0³,⁸.0¹⁷,²²]tricosa-2(11),4,9,13,15,17(22)-hexaen-12-one)

3D-SDF for NP0327516 ((1r,19r)-10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1¹,¹⁹.0²,¹¹.0³,⁸.0¹⁷,²²]tricosa-2(11),4,9,13,15,17(22)-hexaen-12-one)

PDB for NP0327516 ((1r,19r)-10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1¹,¹⁹.0²,¹¹.0³,⁸.0¹⁷,²²]tricosa-2(11),4,9,13,15,17(22)-hexaen-12-one)

3D PDB for NP0327516 ((1r,19r)-10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1¹,¹⁹.0²,¹¹.0³,⁸.0¹⁷,²²]tricosa-2(11),4,9,13,15,17(22)-hexaen-12-one)

SMILES for NP0327516 ((1r,19r)-10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1¹,¹⁹.0²,¹¹.0³,⁸.0¹⁷,²²]tricosa-2(11),4,9,13,15,17(22)-hexaen-12-one)

INCHI for NP0327516 ((1r,19r)-10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1¹,¹⁹.0²,¹¹.0³,⁸.0¹⁷,²²]tricosa-2(11),4,9,13,15,17(22)-hexaen-12-one)

Structure for NP0327516 ((1r,19r)-10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1¹,¹⁹.0²,¹¹.0³,⁸.0¹⁷,²²]tricosa-2(11),4,9,13,15,17(22)-hexaen-12-one)

3D Structure for NP0327516 ((1r,19r)-10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1¹,¹⁹.0²,¹¹.0³,⁸.0¹⁷,²²]tricosa-2(11),4,9,13,15,17(22)-hexaen-12-one)