NP-MRD: Showing NP-Card for methyl 4,14-dihydroxy-1,1,4a,6a,12b-pentamethyl-2h,3h,4h,4bh,5h,6h,12h,12ah,13h,14h,14ah-naphtho[2,1-a]xanthene-10-carboxylate (NP0159309)

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Record Information

Version

1.0

Created at

2022-09-02 17:02:36 UTC

Updated at

2022-09-02 17:02:37 UTC

NP-MRD ID

NP0159309

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 4,14-dihydroxy-1,1,4a,6a,12b-pentamethyl-2h,3h,4h,4bh,5h,6h,12h,12ah,13h,14h,14ah-naphtho[2,1-a]xanthene-10-carboxylate

Description

Methyl 16,21-dihydroxy-1,11,15,19,19-pentamethyl-10-oxapentacyclo[12.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]Docosa-4(9),5,7-triene-6-carboxylate belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring. methyl 4,14-dihydroxy-1,1,4a,6a,12b-pentamethyl-2h,3h,4h,4bh,5h,6h,12h,12ah,13h,14h,14ah-naphtho[2,1-a]xanthene-10-carboxylate is found in Tolypothrix nodosa. It was first documented in 2022 (PMID: 36055769). Based on a literature review a significant number of articles have been published on methyl 16,21-dihydroxy-1,11,15,19,19-pentamethyl-10-oxapentacyclo[12.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]Docosa-4(9),5,7-triene-6-carboxylate (PMID: 36055768) (PMID: 36055767) (PMID: 36055766) (PMID: 36055765).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022219022D          

 33 37  0  0  0  0            999 V2000
    8.4427   -1.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8482   -0.5028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0555   -0.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8574   -1.5324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4611   -0.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6592    0.6413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0648    1.2133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2721    0.9845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0740    0.1837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6868    0.5269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0832    2.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2905    1.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4979    1.6710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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 17 31  1  0  0  0  0
 31 32  1  0  0  0  0
 13 33  1  0  0  0  0
  8 33  1  0  0  0  0
M  END

     RDKit          3D

 73 77  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652309022219022D          

 33 37  0  0  0  0            999 V2000
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 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 23 31  1  0  0  0  0
 17 31  1  0  0  0  0
 31 32  1  0  0  0  0
 13 33  1  0  0  0  0
  8 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0159309

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CC=C2OC3(C)CCC4C(C)(CC(O)C5C(C)(C)CCC(O)C45C)C3CC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H40O5/c1-25(2)11-10-22(30)28(5)20-9-12-27(4)21(26(20,3)15-18(29)23(25)28)14-17-13-16(24(31)32-6)7-8-19(17)33-27/h7-8,13,18,20-23,29-30H,9-12,14-15H2,1-6H3

> <INCHI_KEY>
NQNQLGPYASRQND-UHFFFAOYSA-N

> <FORMULA>
C28H40O5

> <MOLECULAR_WEIGHT>
456.623

> <EXACT_MASS>
456.287574388

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
52.764771741308834

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 16,21-dihydroxy-1,11,15,19,19-pentamethyl-10-oxapentacyclo[12.8.0.0^{2,11}.0^{4,9}.0^{15,20}]docosa-4,6,8-triene-6-carboxylate

> <ALOGPS_LOGP>
4.22

> <JCHEM_LOGP>
4.515482194666668

> <ALOGPS_LOGS>
-5.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.109988143514787

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.477687875679734

> <JCHEM_PKA_STRONGEST_BASIC>
-2.845287933901073

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
127.38440000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.01e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 16,21-dihydroxy-1,11,15,19,19-pentamethyl-10-oxapentacyclo[12.8.0.0^{2,11}.0^{4,9}.0^{15,20}]docosa-4,6,8-triene-6-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      15.760  -2.006   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      14.650  -0.938   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      13.170  -1.366   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      12.800  -2.861   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      12.061  -0.298   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.431   1.197   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.321   2.265   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.841   1.838   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.471   0.343   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.581  -0.725   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.992  -0.084   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.882   0.984   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.252   2.478   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.622   3.973   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.142   3.546   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.663   3.119   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.293   1.624   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.403   0.556   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.512  -0.511   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.033  -0.938   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.553  -1.366   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.183  -2.861   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.443  -0.298   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.964  -0.725   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.641  -2.108   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.280  -1.632   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.146   0.343   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.224   1.838   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.704   2.265   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.073   3.760   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.813   1.197   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.183   2.692   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       8.732   2.906   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   33                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    5                                                       
CONECT   11    9   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14   15   33                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   31                                                  
CONECT   18   17   12   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   31                                                  
CONECT   24   23   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   23   17   32                                             
CONECT   32   31                                                            
CONECT   33   13    8                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
Methyl 16,21-dihydroxy-1,11,15,19,19-pentamethyl-10-oxapentacyclo[12.8.0.0,.0,.0,]docosa-4(9),5,7-triene-6-carboxylic acid	Generator

Chemical Formula

C₂₈H₄₀O₅

Average Mass

456.6230 Da

Monoisotopic Mass

456.28757 Da

IUPAC Name

methyl 16,21-dihydroxy-1,11,15,19,19-pentamethyl-10-oxapentacyclo[12.8.0.0^{2,11}.0^{4,9}.0^{15,20}]docosa-4,6,8-triene-6-carboxylate

Traditional Name

methyl 16,21-dihydroxy-1,11,15,19,19-pentamethyl-10-oxapentacyclo[12.8.0.0^{2,11}.0^{4,9}.0^{15,20}]docosa-4,6,8-triene-6-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CC=C2OC3(C)CCC4C(C)(CC(O)C5C(C)(C)CCC(O)C45C)C3CC2=C1

InChI Identifier

InChI=1S/C28H40O5/c1-25(2)11-10-22(30)28(5)20-9-12-27(4)21(26(20,3)15-18(29)23(25)28)14-17-13-16(24(31)32-6)7-8-19(17)33-27/h7-8,13,18,20-23,29-30H,9-12,14-15H2,1-6H3

InChI Key

NQNQLGPYASRQND-UHFFFAOYSA-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
Tolypothrix nodosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthenes

Alternative Parents

Substituents

Naphthopyran
Xanthene
Naphthalene
Alkyl aryl ether
Pyran
Benzenoid
Cyclic alcohol
Methyl ester
Carboxylic acid ester
Secondary alcohol
Oxacycle
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen 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	4.22	ALOGPS
logP	4.52	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	14.48	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	127.38 m³·mol⁻¹	ChemAxon
Polarizability	52.76 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

78172843

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Pays E, Radwanska M, Magez S: The Pathogenesis of African Trypanosomiasis. Annu Rev Pathol. 2022 Sep 2. doi: 10.1146/annurev-pathmechdis-031621-025153. [PubMed:36055769 ]
Khan K, Van Aken O: The colonisation of land was a likely driving force for the evolution of mitochondrial retrograde signalling in plants. J Exp Bot. 2022 Sep 3. pii: 6687801. doi: 10.1093/jxb/erac351. [PubMed:36055768 ]
Authors unspecified: Erratum. Br J Dermatol. 2022 Sep;187(3):451. doi: 10.1111/bjd.21748. [PubMed:36055767 ]
Authors unspecified: BAD and BPG guidelines for narrowband ultraviolet B phototherapy 2022. Br J Dermatol. 2022 Sep;187(3):vi. doi: 10.1111/bjd.21734. [PubMed:36055766 ]
Sprecher E: What do rare and common have in common? Br J Dermatol. 2022 Sep;187(3):279-280. doi: 10.1111/bjd.21632. [PubMed:36055765 ]
LOTUS database [Link]

Showing NP-Card for methyl 4,14-dihydroxy-1,1,4a,6a,12b-pentamethyl-2h,3h,4h,4bh,5h,6h,12h,12ah,13h,14h,14ah-naphtho[2,1-a]xanthene-10-carboxylate (NP0159309)

MOL for NP0159309 (methyl 4,14-dihydroxy-1,1,4a,6a,12b-pentamethyl-2h,3h,4h,4bh,5h,6h,12h,12ah,13h,14h,14ah-naphtho[2,1-a]xanthene-10-carboxylate)

3D MOL for NP0159309 (methyl 4,14-dihydroxy-1,1,4a,6a,12b-pentamethyl-2h,3h,4h,4bh,5h,6h,12h,12ah,13h,14h,14ah-naphtho[2,1-a]xanthene-10-carboxylate)

3D SDF for NP0159309 (methyl 4,14-dihydroxy-1,1,4a,6a,12b-pentamethyl-2h,3h,4h,4bh,5h,6h,12h,12ah,13h,14h,14ah-naphtho[2,1-a]xanthene-10-carboxylate)

3D-SDF for NP0159309 (methyl 4,14-dihydroxy-1,1,4a,6a,12b-pentamethyl-2h,3h,4h,4bh,5h,6h,12h,12ah,13h,14h,14ah-naphtho[2,1-a]xanthene-10-carboxylate)

PDB for NP0159309 (methyl 4,14-dihydroxy-1,1,4a,6a,12b-pentamethyl-2h,3h,4h,4bh,5h,6h,12h,12ah,13h,14h,14ah-naphtho[2,1-a]xanthene-10-carboxylate)

3D PDB for NP0159309 (methyl 4,14-dihydroxy-1,1,4a,6a,12b-pentamethyl-2h,3h,4h,4bh,5h,6h,12h,12ah,13h,14h,14ah-naphtho[2,1-a]xanthene-10-carboxylate)

SMILES for NP0159309 (methyl 4,14-dihydroxy-1,1,4a,6a,12b-pentamethyl-2h,3h,4h,4bh,5h,6h,12h,12ah,13h,14h,14ah-naphtho[2,1-a]xanthene-10-carboxylate)

INCHI for NP0159309 (methyl 4,14-dihydroxy-1,1,4a,6a,12b-pentamethyl-2h,3h,4h,4bh,5h,6h,12h,12ah,13h,14h,14ah-naphtho[2,1-a]xanthene-10-carboxylate)

Structure for NP0159309 (methyl 4,14-dihydroxy-1,1,4a,6a,12b-pentamethyl-2h,3h,4h,4bh,5h,6h,12h,12ah,13h,14h,14ah-naphtho[2,1-a]xanthene-10-carboxylate)

3D Structure for NP0159309 (methyl 4,14-dihydroxy-1,1,4a,6a,12b-pentamethyl-2h,3h,4h,4bh,5h,6h,12h,12ah,13h,14h,14ah-naphtho[2,1-a]xanthene-10-carboxylate)