NP-MRD: Showing NP-Card for 10-(hepta-1,3,5-trien-1-yl)-2,4-dihydroxy-6-methyl-7,11-dioxatricyclo[7.6.1.0¹²,¹⁶]hexadeca-9,13-diene-8,15-dione (NP0221878)

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Record Information

Version

2.0

Created at

2022-09-05 23:33:55 UTC

Updated at

2022-09-05 23:33:55 UTC

NP-MRD ID

NP0221878

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10-(hepta-1,3,5-trien-1-yl)-2,4-dihydroxy-6-methyl-7,11-dioxatricyclo[7.6.1.0¹²,¹⁶]hexadeca-9,13-diene-8,15-dione

Description

10-(Hepta-1,3,5-trien-1-yl)-2,4-dihydroxy-6-methyl-7,11-dioxatricyclo[7.6.1.0¹²,¹⁶]Hexadeca-9,13-diene-8,15-dione belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. 10-(hepta-1,3,5-trien-1-yl)-2,4-dihydroxy-6-methyl-7,11-dioxatricyclo[7.6.1.0¹²,¹⁶]hexadeca-9,13-diene-8,15-dione is found in Colletotrichum fragariae. Based on a literature review very few articles have been published on 10-(hepta-1,3,5-trien-1-yl)-2,4-dihydroxy-6-methyl-7,11-dioxatricyclo[7.6.1.0¹²,¹⁶]Hexadeca-9,13-diene-8,15-dione.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062201332D          

 28 30  0  0  0  0            999 V2000
    5.5896    6.9158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1056    6.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4423    5.4945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9584    4.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2951    4.0731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8112    3.4049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1479    2.6518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6639    1.9836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9091    1.1391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6374    0.7516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1759    0.0677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3372    1.1886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0655    0.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7653    1.2381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0941   -0.0234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3943   -0.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4229   -1.2849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6660   -0.0729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9663   -0.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9948   -1.3344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2379   -0.1224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4963   -0.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4386   -1.3069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8125   -0.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8702    0.8006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6118    1.1620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8394    1.9550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2093    0.7021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  4  3  1  4  0  0  0
  4  5  2  0  0  0  0
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 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
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  8 27  1  0  0  0  0
 26 28  1  0  0  0  0
  9 28  1  0  0  0  0
 21 28  1  0  0  0  0
M  END


  Mrv1652309062201332D          

 28 30  0  0  0  0            999 V2000
    5.5896    6.9158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1056    6.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4423    5.4945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9584    4.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2951    4.0731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8112    3.4049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1479    2.6518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6639    1.9836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9091    1.1391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6374    0.7516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1759    0.0677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3372    1.1886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0655    0.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7653    1.2381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0941   -0.0234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3943   -0.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4229   -1.2849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6660   -0.0729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9663   -0.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9948   -1.3344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2379   -0.1224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4963   -0.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4386   -1.3069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8125   -0.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8702    0.8006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6118    1.1620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8394    1.9550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2093    0.7021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  4  3  1  4  0  0  0
  4  5  2  0  0  0  0
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 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
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  8 27  1  0  0  0  0
 26 28  1  0  0  0  0
  9 28  1  0  0  0  0
 21 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0221878

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=CC=CC=CC1=C2C3C(O1)C=CC(=O)C3C(O)CC(O)CC(C)OC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H26O6/c1-3-4-5-6-7-8-17-21-20-18(28-17)10-9-15(24)19(20)16(25)12-14(23)11-13(2)27-22(21)26/h3-10,13-14,16,18-20,23,25H,11-12H2,1-2H3

> <INCHI_KEY>
PSMAZPOSNHLCII-UHFFFAOYSA-N

> <FORMULA>
C22H26O6

> <MOLECULAR_WEIGHT>
386.444

> <EXACT_MASS>
386.172938557

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
42.49974980748616

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-(hepta-1,3,5-trien-1-yl)-2,4-dihydroxy-6-methyl-7,11-dioxatricyclo[7.6.1.0^{12,16}]hexadeca-9,13-diene-8,15-dione

> <JCHEM_LOGP>
1.560497834999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.055975685230386

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.40914612902607

> <JCHEM_PKA_STRONGEST_BASIC>
-2.75862416656131

> <JCHEM_POLAR_SURFACE_AREA>
93.06000000000002

> <JCHEM_REFRACTIVITY>
109.9152

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
10-(hepta-1,3,5-trien-1-yl)-2,4-dihydroxy-6-methyl-7,11-dioxatricyclo[7.6.1.0^{12,16}]hexadeca-9,13-diene-8,15-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      10.434  12.909   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.531  11.662   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.159  10.256   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.256   9.009   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.884   7.603   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.981   6.356   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.609   4.950   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.706   3.703   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.164   2.126   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.523   1.403   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.662   0.126   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      11.829   2.219   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      13.189   1.495   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.495   2.311   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.242  -0.044   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.936  -0.859   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      11.989  -2.399   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.577  -0.136   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.270  -0.952   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.324  -2.491   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.911  -0.229   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.526  -0.903   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.419  -2.440   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.250  -0.042   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.358   1.494   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.742   2.169   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.167   3.649   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.857   1.311   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   27                                                  
CONECT    9    8   10   28                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   28                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26    8                                                       
CONECT   28   26    9   21                                                  
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₆O₆

Average Mass

386.4440 Da

Monoisotopic Mass

386.17294 Da

IUPAC Name

10-(hepta-1,3,5-trien-1-yl)-2,4-dihydroxy-6-methyl-7,11-dioxatricyclo[7.6.1.0^{12,16}]hexadeca-9,13-diene-8,15-dione

Traditional Name

10-(hepta-1,3,5-trien-1-yl)-2,4-dihydroxy-6-methyl-7,11-dioxatricyclo[7.6.1.0^{12,16}]hexadeca-9,13-diene-8,15-dione

CAS Registry Number

Not Available

SMILES

CC=CC=CC=CC1=C2C3C(O1)C=CC(=O)C3C(O)CC(O)CC(C)OC2=O

InChI Identifier

InChI=1S/C22H26O6/c1-3-4-5-6-7-8-17-21-20-18(28-17)10-9-15(24)19(20)16(25)12-14(23)11-13(2)27-22(21)26/h3-10,13-14,16,18-20,23,25H,11-12H2,1-2H3

InChI Key

PSMAZPOSNHLCII-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Colletotrichum fragariae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Dihydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous ester
Carboxylic acid ester
Secondary alcohol
Lactone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Alcohol
Hydrocarbon derivative
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	1.56	ChemAxon
pKa (Strongest Acidic)	13.41	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	109.92 m³·mol⁻¹	ChemAxon
Polarizability	42.5 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

85225576

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 10-(hepta-1,3,5-trien-1-yl)-2,4-dihydroxy-6-methyl-7,11-dioxatricyclo[7.6.1.0¹²,¹⁶]hexadeca-9,13-diene-8,15-dione (NP0221878)

MOL for NP0221878 (10-(hepta-1,3,5-trien-1-yl)-2,4-dihydroxy-6-methyl-7,11-dioxatricyclo[7.6.1.0¹²,¹⁶]hexadeca-9,13-diene-8,15-dione)

3D MOL for NP0221878 (10-(hepta-1,3,5-trien-1-yl)-2,4-dihydroxy-6-methyl-7,11-dioxatricyclo[7.6.1.0¹²,¹⁶]hexadeca-9,13-diene-8,15-dione)

3D SDF for NP0221878 (10-(hepta-1,3,5-trien-1-yl)-2,4-dihydroxy-6-methyl-7,11-dioxatricyclo[7.6.1.0¹²,¹⁶]hexadeca-9,13-diene-8,15-dione)

3D-SDF for NP0221878 (10-(hepta-1,3,5-trien-1-yl)-2,4-dihydroxy-6-methyl-7,11-dioxatricyclo[7.6.1.0¹²,¹⁶]hexadeca-9,13-diene-8,15-dione)

PDB for NP0221878 (10-(hepta-1,3,5-trien-1-yl)-2,4-dihydroxy-6-methyl-7,11-dioxatricyclo[7.6.1.0¹²,¹⁶]hexadeca-9,13-diene-8,15-dione)

3D PDB for NP0221878 (10-(hepta-1,3,5-trien-1-yl)-2,4-dihydroxy-6-methyl-7,11-dioxatricyclo[7.6.1.0¹²,¹⁶]hexadeca-9,13-diene-8,15-dione)

SMILES for NP0221878 (10-(hepta-1,3,5-trien-1-yl)-2,4-dihydroxy-6-methyl-7,11-dioxatricyclo[7.6.1.0¹²,¹⁶]hexadeca-9,13-diene-8,15-dione)

INCHI for NP0221878 (10-(hepta-1,3,5-trien-1-yl)-2,4-dihydroxy-6-methyl-7,11-dioxatricyclo[7.6.1.0¹²,¹⁶]hexadeca-9,13-diene-8,15-dione)

Structure for NP0221878 (10-(hepta-1,3,5-trien-1-yl)-2,4-dihydroxy-6-methyl-7,11-dioxatricyclo[7.6.1.0¹²,¹⁶]hexadeca-9,13-diene-8,15-dione)

3D Structure for NP0221878 (10-(hepta-1,3,5-trien-1-yl)-2,4-dihydroxy-6-methyl-7,11-dioxatricyclo[7.6.1.0¹²,¹⁶]hexadeca-9,13-diene-8,15-dione)