NP-MRD: Showing NP-Card for Territrem A (NP0078779)

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Record Information

Version

2.0

Created at

2022-04-28 23:50:51 UTC

Updated at

2022-04-28 23:50:51 UTC

NP-MRD ID

NP0078779

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Territrem A

Description

TERRITREMA(RG) 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. Territrem A is found in Aspergillus terreus . Based on a literature review very few articles have been published on TERRITREMA(RG).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201502D          

 37 42  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304292201502D          

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M  END
> <DATABASE_ID>
NP0078779

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC2=C1OCO2)C1=CC2=C(C[C@@]3(O)[C@@](C)(CC[C@@]4(O)C(C)(C)C=CC(=O)[C@]34C)O2)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C28H30O9/c1-24(2)7-6-21(29)26(4)27(24,31)9-8-25(3)28(26,32)13-16-18(37-25)12-17(36-23(16)30)15-10-19(33-5)22-20(11-15)34-14-35-22/h6-7,10-12,31-32H,8-9,13-14H2,1-5H3/t25-,26+,27-,28-/m1/s1

> <INCHI_KEY>
LCJHAHVVYAVVPA-JUDWXZBOSA-N

> <FORMULA>
C28H30O9

> <MOLECULAR_WEIGHT>
510.539

> <EXACT_MASS>
510.188982546

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
53.47971729071117

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5aR,7aR,11aS,11bS)-7a,11b-dihydroxy-3-(7-methoxy-2H-1,3-benzodioxol-5-yl)-5a,8,8,11a-tetramethyl-1,5a,6,7,7a,8,11,11a,11b,12-decahydro-2,5-dioxatetraphene-1,11-dione

> <ALOGPS_LOGP>
2.30

> <JCHEM_LOGP>
2.4436512230000003

> <ALOGPS_LOGS>
-4.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.871524456862971

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.890721426108875

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3658431139009384

> <JCHEM_POLAR_SURFACE_AREA>
120.75000000000001

> <JCHEM_REFRACTIVITY>
133.18359999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.53e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5aR,7aR,11aS,11bS)-7a,11b-dihydroxy-3-(7-methoxy-2H-1,3-benzodioxol-5-yl)-5a,8,8,11a-tetramethyl-7,12-dihydro-6H-2,5-dioxatetraphene-1,11-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      14.260  12.853   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.926  13.623   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      14.260  11.313   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.593  10.543   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.927  11.313   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.927  12.853   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.593  13.623   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.466  11.259   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.743  10.007   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.593   9.003   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.260   8.233   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.926   9.003   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.926  10.543   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.592  11.313   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.259  10.543   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.259   9.003   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      11.592   8.233   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.925   8.233   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.591   9.003   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.591  10.543   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.925  11.313   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.925  12.853   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.258   8.233   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.924   9.003   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.590   8.233   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.590   6.693   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.924   5.923   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.258   6.693   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.924   4.383   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.126   6.217   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.220   7.463   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.126   8.709   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      12.926  12.083   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      12.926   7.463   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      16.927   9.773   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      13.633  12.720   0.000  0.00  0.00           C+0
CONECT    1    2    3    7                                                  
CONECT    2    1                                                            
CONECT    3    1    4   13   37                                             
CONECT    4    3    5   10   36                                             
CONECT    5    4    6    8    9                                             
CONECT    6    5    7                                                       
CONECT    7    6    1                                                       
CONECT    8    5                                                            
CONECT    9    5                                                            
CONECT   10    4   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17   35                                             
CONECT   13   12    3   14   34                                             
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   12                                                       
CONECT   18   16   19                                                       
CONECT   19   18   20   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20   15   22                                                  
CONECT   22   21                                                            
CONECT   23   19   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   33                                                  
CONECT   26   25   27   31                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27   23                                                       
CONECT   29   27   30                                                       
CONECT   30   29                                                            
CONECT   31   26   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   25                                                       
CONECT   34   13                                                            
CONECT   35   12                                                            
CONECT   36    4                                                            
CONECT   37    3                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₀O₉

Average Mass

510.5390 Da

Monoisotopic Mass

510.18898 Da

IUPAC Name

(5aR,7aR,11aS,11bS)-7a,11b-dihydroxy-3-(7-methoxy-2H-1,3-benzodioxol-5-yl)-5a,8,8,11a-tetramethyl-1,5a,6,7,7a,8,11,11a,11b,12-decahydro-2,5-dioxatetraphene-1,11-dione

Traditional Name

(5aR,7aR,11aS,11bS)-7a,11b-dihydroxy-3-(7-methoxy-2H-1,3-benzodioxol-5-yl)-5a,8,8,11a-tetramethyl-7,12-dihydro-6H-2,5-dioxatetraphene-1,11-dione

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC2=C1OCO2)C1=CC2=C(C[C@@]3(O)[C@@](C)(CC[C@@]4(O)C(C)(C)C=CC(=O)[C@]34C)O2)C(=O)O1

InChI Identifier

InChI=1S/C28H30O9/c1-24(2)7-6-21(29)26(4)27(24,31)9-8-25(3)28(26,32)13-16-18(37-25)12-17(36-23(16)30)15-10-19(33-5)22-20(11-15)34-14-35-22/h6-7,10-12,31-32H,8-9,13-14H2,1-5H3/t25-,26+,27-,28-/m1/s1

InChI Key

LCJHAHVVYAVVPA-JUDWXZBOSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Aspergillus terreus	Fungi	KNApSAcK

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
Benzodioxole
Anisole
Alkyl aryl ether
Cyclohexenone
Pyranone
Benzenoid
Pyran
Cyclic alcohol
Heteroaromatic compound
Vinylogous ester
Tertiary alcohol
Lactone
Ketone
Ether
Acetal
Oxacycle
Alcohol
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Organic oxide
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	2.3	ALOGPS
logP	2.44	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	12.89	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	120.75 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	133.18 m³·mol⁻¹	ChemAxon
Polarizability	53.48 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

23326729

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44559227

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Territrem A (NP0078779)

MOL for NP0078779 (Territrem A)

3D MOL for NP0078779 (Territrem A)

3D SDF for NP0078779 (Territrem A)

3D-SDF for NP0078779 (Territrem A)

PDB for NP0078779 (Territrem A)

3D PDB for NP0078779 (Territrem A)

SMILES for NP0078779 (Territrem A)

INCHI for NP0078779 (Territrem A)

Structure for NP0078779 (Territrem A)

3D Structure for NP0078779 (Territrem A)