NP-MRD: Showing NP-Card for (4as,12s,12as)-3-acetyl-4,4a,6,7,12,12a-hexahydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-1,12-dihydrotetracene-2,5-dione (NP0304567)

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Record Information

Version

2.0

Created at

2022-09-10 19:45:13 UTC

Updated at

2022-09-10 19:45:13 UTC

NP-MRD ID

NP0304567

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4as,12s,12as)-3-acetyl-4,4a,6,7,12,12a-hexahydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-1,12-dihydrotetracene-2,5-dione

Description

Hypomycetin belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position. (4as,12s,12as)-3-acetyl-4,4a,6,7,12,12a-hexahydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-1,12-dihydrotetracene-2,5-dione is found in Hypomyces aurantius. Based on a literature review very few articles have been published on Hypomycetin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102221452D          

 36 39  0  0  1  0            999 V2000
    7.1447   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  8  9  1  0  0  0  0
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  7 18  1  0  0  0  0
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M  END

     RDKit          3D

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   -4.5024    3.9520    0.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309102221452D          

 36 39  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0304567

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(O)=C3C(=O)[C@]4(O)C(O)=C(C(C)=O)C(=O)C[C@]4(O)[C@@H](O)C3=C(CC=C(C)C)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H26O10/c1-10(2)5-6-13-14-7-12(36-4)8-15(28)18(14)21(30)20-19(13)22(31)25(34)9-16(29)17(11(3)27)23(32)26(25,35)24(20)33/h5,7-8,22,28,30-32,34-35H,6,9H2,1-4H3/t22-,25-,26+/m0/s1

> <INCHI_KEY>
YRQJWWGXADJAPA-UCGXPXSYSA-N

> <FORMULA>
C26H26O10

> <MOLECULAR_WEIGHT>
498.484

> <EXACT_MASS>
498.152597037

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
50.091440393651176

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4aS,12S,12aS)-3-acetyl-4,4a,6,7,12,12a-hexahydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-1,2,4a,5,12,12a-hexahydrotetracene-2,5-dione

> <JCHEM_LOGP>
1.6905046786666673

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.643049106758108

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.4588452305192705

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7394345385364494

> <JCHEM_POLAR_SURFACE_AREA>
181.81999999999996

> <JCHEM_REFRACTIVITY>
129.04759999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(4aS,12S,12aS)-3-acetyl-4,4a,6,7,12,12a-hexahydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-1,12-dihydrotetracene-2,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      13.337  -0.000   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.667  -1.540   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       2.667   3.080   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   18                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   35                                                  
CONECT   11   10   12   20                                                  
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   12    7   19                                                  
CONECT   19   18    3                                                       
CONECT   20   11   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24   33                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   31                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   27   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   22   34   35                                             
CONECT   34   33                                                            
CONECT   35   33   10   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₆O₁₀

Average Mass

498.4840 Da

Monoisotopic Mass

498.15260 Da

IUPAC Name

(4aS,12S,12aS)-3-acetyl-4,4a,6,7,12,12a-hexahydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-1,2,4a,5,12,12a-hexahydrotetracene-2,5-dione

Traditional Name

(4aS,12S,12aS)-3-acetyl-4,4a,6,7,12,12a-hexahydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-1,12-dihydrotetracene-2,5-dione

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(O)=C3C(=O)[C@]4(O)C(O)=C(C(C)=O)C(=O)C[C@]4(O)[C@@H](O)C3=C(CC=C(C)C)C2=C1

InChI Identifier

InChI=1S/C26H26O10/c1-10(2)5-6-13-14-7-12(36-4)8-15(28)18(14)21(30)20-19(13)22(31)25(34)9-16(29)17(11(3)27)23(32)26(25,35)24(20)33/h5,7-8,22,28,30-32,34-35H,6,9H2,1-4H3/t22-,25-,26+/m0/s1

InChI Key

YRQJWWGXADJAPA-UCGXPXSYSA-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
Hypomyces aurantius	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Naphthols and derivatives

Direct Parent

Naphthols and derivatives

Alternative Parents

Substituents

1-naphthol
Tetralin
Phenol ether
Aryl ketone
Aryl alkyl ketone
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Cyclohexenone
Tertiary alcohol
Vinylogous acid
1,2-diol
Cyclic ketone
Ketone
Secondary alcohol
Enol
Ether
Polyol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organic oxide
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	1.69	ChemAxon
pKa (Strongest Acidic)	0.46	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	181.82 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	129.05 m³·mol⁻¹	ChemAxon
Polarizability	50.09 Å³	ChemAxon
Number of Rings	4	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

8942947

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10767630

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4as,12s,12as)-3-acetyl-4,4a,6,7,12,12a-hexahydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-1,12-dihydrotetracene-2,5-dione (NP0304567)

MOL for NP0304567 ((4as,12s,12as)-3-acetyl-4,4a,6,7,12,12a-hexahydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-1,12-dihydrotetracene-2,5-dione)

3D MOL for NP0304567 ((4as,12s,12as)-3-acetyl-4,4a,6,7,12,12a-hexahydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-1,12-dihydrotetracene-2,5-dione)

3D SDF for NP0304567 ((4as,12s,12as)-3-acetyl-4,4a,6,7,12,12a-hexahydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-1,12-dihydrotetracene-2,5-dione)

3D-SDF for NP0304567 ((4as,12s,12as)-3-acetyl-4,4a,6,7,12,12a-hexahydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-1,12-dihydrotetracene-2,5-dione)

PDB for NP0304567 ((4as,12s,12as)-3-acetyl-4,4a,6,7,12,12a-hexahydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-1,12-dihydrotetracene-2,5-dione)

3D PDB for NP0304567 ((4as,12s,12as)-3-acetyl-4,4a,6,7,12,12a-hexahydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-1,12-dihydrotetracene-2,5-dione)

SMILES for NP0304567 ((4as,12s,12as)-3-acetyl-4,4a,6,7,12,12a-hexahydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-1,12-dihydrotetracene-2,5-dione)

INCHI for NP0304567 ((4as,12s,12as)-3-acetyl-4,4a,6,7,12,12a-hexahydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-1,12-dihydrotetracene-2,5-dione)

Structure for NP0304567 ((4as,12s,12as)-3-acetyl-4,4a,6,7,12,12a-hexahydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-1,12-dihydrotetracene-2,5-dione)

3D Structure for NP0304567 ((4as,12s,12as)-3-acetyl-4,4a,6,7,12,12a-hexahydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-1,12-dihydrotetracene-2,5-dione)