NP-MRD: Showing NP-Card for (12s)-3,10,17-trihydroxy-7,7,21,21-tetramethyl-12-(prop-1-en-2-yl)-8,20,26-trioxahexacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁶,²⁵.0¹⁹,²⁴]hexacosa-1(14),2,4(9),5,10,16,18,22,24-nonaen-15-one (NP0281681)

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Record Information

Version

2.0

Created at

2022-09-09 08:10:39 UTC

Updated at

2022-09-09 08:10:39 UTC

NP-MRD ID

NP0281681

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(12s)-3,10,17-trihydroxy-7,7,21,21-tetramethyl-12-(prop-1-en-2-yl)-8,20,26-trioxahexacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁶,²⁵.0¹⁹,²⁴]hexacosa-1(14),2,4(9),5,10,16,18,22,24-nonaen-15-one

Description

(12S)-3,10,17-trihydroxy-7,7,21,21-tetramethyl-12-(prop-1-en-2-yl)-8,20,26-trioxahexacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁶,²⁵.0¹⁹,²⁴]Hexacosa-1(14),2(11),3,5,9,16(25),17,19(24),22-nonaen-15-one belongs to the class of organic compounds known as pyranoxanthones. These are organic aromatic compounds containing a pyran or a hydrogenated derivative fused to a xanthone ring system. (12s)-3,10,17-trihydroxy-7,7,21,21-tetramethyl-12-(prop-1-en-2-yl)-8,20,26-trioxahexacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁶,²⁵.0¹⁹,²⁴]hexacosa-1(14),2,4(9),5,10,16,18,22,24-nonaen-15-one is found in Artocarpus altilis. Based on a literature review very few articles have been published on (12S)-3,10,17-trihydroxy-7,7,21,21-tetramethyl-12-(prop-1-en-2-yl)-8,20,26-trioxahexacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁶,²⁵.0¹⁹,²⁴]Hexacosa-1(14),2(11),3,5,9,16(25),17,19(24),22-nonaen-15-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092210102D          

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M  END

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M  END


  Mrv1652309092210102D          

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 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
  6 16  1  0  0  0  0
 16 17  2  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  2  0  0  0  0
 10 23  1  0  0  0  0
  7 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 24 31  1  0  0  0  0
  4 31  1  0  0  0  0
 28 32  1  0  0  0  0
 32 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
 36 37  2  0  0  0  0
 27 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0281681

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)[C@@H]1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O)C3=C(OC(C)(C)C=C3)C(O)=C12

> <INCHI_IDENTIFIER>
InChI=1S/C30H28O7/c1-13(2)16-11-17-24(33)21-18(31)12-19-14(7-9-29(3,4)36-19)26(21)35-27(17)22-20(16)25(34)28-15(23(22)32)8-10-30(5,6)37-28/h7-10,12,16,31-32,34H,1,11H2,2-6H3/t16-/m0/s1

> <INCHI_KEY>
JVLAUHJNDLMVDW-INIZCTEOSA-N

> <FORMULA>
C30H28O7

> <MOLECULAR_WEIGHT>
500.547

> <EXACT_MASS>
500.183503242

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
54.658379658085806

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(12S)-3,10,17-trihydroxy-7,7,21,21-tetramethyl-12-(prop-1-en-2-yl)-8,20,26-trioxahexacyclo[12.12.0.0^{2,11}.0^{4,9}.0^{16,25}.0^{19,24}]hexacosa-1(14),2,4(9),5,10,16,18,22,24-nonaen-15-one

> <JCHEM_LOGP>
5.624142960333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.600942597966476

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.525755636950934

> <JCHEM_PKA_STRONGEST_BASIC>
-4.590157028083831

> <JCHEM_POLAR_SURFACE_AREA>
105.45000000000002

> <JCHEM_REFRACTIVITY>
142.77249999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(12S)-3,10,17-trihydroxy-7,7,21,21-tetramethyl-12-(prop-1-en-2-yl)-8,20,26-trioxahexacyclo[12.12.0.0^{2,11}.0^{4,9}.0^{16,25}.0^{19,24}]hexacosa-1(14),2,4(9),5,10,16,18,22,24-nonaen-15-one

> <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       1.334  -4.783   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.813  -5.210   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.183  -6.705   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.923  -4.142   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.403  -4.569   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.512  -3.501   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.142  -2.006   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.252  -0.938   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.732  -1.366   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.841  -0.298   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.321  -0.725   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.691  -2.220   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.581  -3.288   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      10.951  -4.783   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.101  -2.861   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.992  -3.928   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.362  -5.423   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      12.431   0.343   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      12.061   1.838   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.597   1.942   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.224   3.369   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.581   2.265   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.471   1.197   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.663  -1.579   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.293  -0.084   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.403   0.984   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.813   0.343   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.704  -0.725   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.073  -2.220   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.964  -3.288   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.553  -2.647   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.224  -0.298   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -0.146   1.197   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.554   0.573   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.005   2.475   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.964   2.265   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.443   1.838   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   31                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   16                                                  
CONECT    7    6    8   24                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11   23                                                  
CONECT   11   10   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    9   16                                                  
CONECT   16   15    6   17                                                  
CONECT   17   16                                                            
CONECT   18   11   19                                                       
CONECT   19   18   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19   23                                                       
CONECT   23   22   10                                                       
CONECT   24    7   25   31                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   37                                                  
CONECT   28   27   29   32                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   24    4                                                  
CONECT   32   28   33                                                       
CONECT   33   32   34   35   36                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   33   37                                                       
CONECT   37   36   27                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₈O₇

Average Mass

500.5470 Da

Monoisotopic Mass

500.18350 Da

IUPAC Name

(12S)-3,10,17-trihydroxy-7,7,21,21-tetramethyl-12-(prop-1-en-2-yl)-8,20,26-trioxahexacyclo[12.12.0.0^{2,11}.0^{4,9}.0^{16,25}.0^{19,24}]hexacosa-1(14),2,4(9),5,10,16,18,22,24-nonaen-15-one

Traditional Name

(12S)-3,10,17-trihydroxy-7,7,21,21-tetramethyl-12-(prop-1-en-2-yl)-8,20,26-trioxahexacyclo[12.12.0.0^{2,11}.0^{4,9}.0^{16,25}.0^{19,24}]hexacosa-1(14),2,4(9),5,10,16,18,22,24-nonaen-15-one

CAS Registry Number

Not Available

SMILES

CC(=C)[C@@H]1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O)C3=C(OC(C)(C)C=C3)C(O)=C12

InChI Identifier

InChI=1S/C30H28O7/c1-13(2)16-11-17-24(33)21-18(31)12-19-14(7-9-29(3,4)36-19)26(21)35-27(17)22-20(16)25(34)28-15(23(22)32)8-10-30(5,6)37-28/h7-10,12,16,31-32,34H,1,11H2,2-6H3/t16-/m0/s1

InChI Key

JVLAUHJNDLMVDW-INIZCTEOSA-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
Artocarpus altilis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoxanthones. These are organic aromatic compounds containing a pyran or a hydrogenated derivative fused to a xanthone ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Pyranoxanthones

Alternative Parents

Substituents

Pyranoxanthone
Naphthopyranone
Pyranochromene
Naphthopyran
2,2-dimethyl-1-benzopyran
1-naphthol
Chromone
Naphthalene
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Alkyl aryl ether
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Oxacycle
Polyol
Ether
Organic oxygen compound
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	5.62	ChemAxon
pKa (Strongest Acidic)	7.53	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	142.77 m³·mol⁻¹	ChemAxon
Polarizability	54.66 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

154496197

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (12s)-3,10,17-trihydroxy-7,7,21,21-tetramethyl-12-(prop-1-en-2-yl)-8,20,26-trioxahexacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁶,²⁵.0¹⁹,²⁴]hexacosa-1(14),2,4(9),5,10,16,18,22,24-nonaen-15-one (NP0281681)

MOL for NP0281681 ((12s)-3,10,17-trihydroxy-7,7,21,21-tetramethyl-12-(prop-1-en-2-yl)-8,20,26-trioxahexacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁶,²⁵.0¹⁹,²⁴]hexacosa-1(14),2,4(9),5,10,16,18,22,24-nonaen-15-one)

3D MOL for NP0281681 ((12s)-3,10,17-trihydroxy-7,7,21,21-tetramethyl-12-(prop-1-en-2-yl)-8,20,26-trioxahexacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁶,²⁵.0¹⁹,²⁴]hexacosa-1(14),2,4(9),5,10,16,18,22,24-nonaen-15-one)

3D SDF for NP0281681 ((12s)-3,10,17-trihydroxy-7,7,21,21-tetramethyl-12-(prop-1-en-2-yl)-8,20,26-trioxahexacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁶,²⁵.0¹⁹,²⁴]hexacosa-1(14),2,4(9),5,10,16,18,22,24-nonaen-15-one)

3D-SDF for NP0281681 ((12s)-3,10,17-trihydroxy-7,7,21,21-tetramethyl-12-(prop-1-en-2-yl)-8,20,26-trioxahexacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁶,²⁵.0¹⁹,²⁴]hexacosa-1(14),2,4(9),5,10,16,18,22,24-nonaen-15-one)

PDB for NP0281681 ((12s)-3,10,17-trihydroxy-7,7,21,21-tetramethyl-12-(prop-1-en-2-yl)-8,20,26-trioxahexacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁶,²⁵.0¹⁹,²⁴]hexacosa-1(14),2,4(9),5,10,16,18,22,24-nonaen-15-one)

3D PDB for NP0281681 ((12s)-3,10,17-trihydroxy-7,7,21,21-tetramethyl-12-(prop-1-en-2-yl)-8,20,26-trioxahexacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁶,²⁵.0¹⁹,²⁴]hexacosa-1(14),2,4(9),5,10,16,18,22,24-nonaen-15-one)

SMILES for NP0281681 ((12s)-3,10,17-trihydroxy-7,7,21,21-tetramethyl-12-(prop-1-en-2-yl)-8,20,26-trioxahexacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁶,²⁵.0¹⁹,²⁴]hexacosa-1(14),2,4(9),5,10,16,18,22,24-nonaen-15-one)

INCHI for NP0281681 ((12s)-3,10,17-trihydroxy-7,7,21,21-tetramethyl-12-(prop-1-en-2-yl)-8,20,26-trioxahexacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁶,²⁵.0¹⁹,²⁴]hexacosa-1(14),2,4(9),5,10,16,18,22,24-nonaen-15-one)

Structure for NP0281681 ((12s)-3,10,17-trihydroxy-7,7,21,21-tetramethyl-12-(prop-1-en-2-yl)-8,20,26-trioxahexacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁶,²⁵.0¹⁹,²⁴]hexacosa-1(14),2,4(9),5,10,16,18,22,24-nonaen-15-one)

3D Structure for NP0281681 ((12s)-3,10,17-trihydroxy-7,7,21,21-tetramethyl-12-(prop-1-en-2-yl)-8,20,26-trioxahexacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁶,²⁵.0¹⁹,²⁴]hexacosa-1(14),2,4(9),5,10,16,18,22,24-nonaen-15-one)