NP-MRD: Showing NP-Card for (2r,4r,7s,8s,9e,12s)-7,8,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0²,⁴]nonadeca-1(19),9,15,17-tetraen-14-one (NP0299175)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 10:51:35 UTC

Updated at

2022-09-10 10:51:35 UTC

NP-MRD ID

NP0299175

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,4r,7s,8s,9e,12s)-7,8,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0²,⁴]nonadeca-1(19),9,15,17-tetraen-14-one

Description

Aigialomycin C belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. (2r,4r,7s,8s,9e,12s)-7,8,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0²,⁴]nonadeca-1(19),9,15,17-tetraen-14-one is found in Aigialus parvus. Based on a literature review very few articles have been published on Aigialomycin C.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309102212512D          

 26 28  0  0  1  0            999 V2000
    6.4203   -0.0108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7049   -0.4217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9914   -0.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9933    0.8175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2798    1.2317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2818    2.0567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5644    0.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5625   -0.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2760   -0.4183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2028   -0.7466    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3238   -1.5627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5566   -1.2595    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7518   -1.4412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9479   -1.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3041   -0.7398    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3421   -1.2527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0521    0.0043    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8771    0.0062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3076    0.7467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3095    1.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9557    2.0846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    2.2663    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7624    3.0913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5644    2.0809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2082    1.5650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8544    2.0778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 12 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
  7 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END


  Mrv1652309102212512D          

 26 28  0  0  1  0            999 V2000
    6.4203   -0.0108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7049   -0.4217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9914   -0.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9933    0.8175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2798    1.2317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2818    2.0567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5644    0.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5625   -0.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2760   -0.4183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2028   -0.7466    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3238   -1.5627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5566   -1.2595    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7518   -1.4412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9479   -1.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3041   -0.7398    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3421   -1.2527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0521    0.0043    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8771    0.0062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3076    0.7467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3095    1.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9557    2.0846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    2.2663    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7624    3.0913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5644    2.0809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2082    1.5650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8544    2.0778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 12 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
  7 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0299175

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(=C1)[C@H]1O[C@@H]1CC[C@H](O)[C@@H](O)\C=C\C[C@H](C)OC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H24O7/c1-10-4-3-5-13(20)14(21)6-7-16-18(26-16)12-8-11(24-2)9-15(22)17(12)19(23)25-10/h3,5,8-10,13-14,16,18,20-22H,4,6-7H2,1-2H3/b5-3+/t10-,13-,14-,16+,18+/m0/s1

> <INCHI_KEY>
IDIVCUJKNPAADU-UDMGXPKMSA-N

> <FORMULA>
C19H24O7

> <MOLECULAR_WEIGHT>
364.394

> <EXACT_MASS>
364.152203113

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
37.95871524186032

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,4R,7S,8S,9E,12S)-7,8,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0^{2,4}]nonadeca-1(15),9,16,18-tetraen-14-one

> <JCHEM_LOGP>
2.1668516113333327

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.668169223824417

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.47520515634423

> <JCHEM_PKA_STRONGEST_BASIC>
-3.171802572014455

> <JCHEM_POLAR_SURFACE_AREA>
108.75

> <JCHEM_REFRACTIVITY>
94.42429999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,4R,7S,8S,9E,12S)-7,8,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0^{2,4}]nonadeca-1(15),9,16,18-tetraen-14-one

> <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      11.985  -0.020   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.649  -0.787   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.317  -0.014   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.321   1.526   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.989   2.299   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.993   3.839   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.654   1.532   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.650  -0.008   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.982  -0.781   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.979  -1.394   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.204  -2.917   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.772  -2.351   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.270  -2.690   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.769  -2.344   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.568  -1.381   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.639  -2.338   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.097   0.008   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.637   0.012   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.574   1.394   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.578   2.934   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.784   3.891   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.286   4.230   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.290   5.770   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.787   3.884   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.989   2.921   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.195   3.879   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   25                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    3                                                       
CONECT   10    8   11   12                                                  
CONECT   11   10   12                                                       
CONECT   12   11   10   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24    7   26                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₄O₇

Average Mass

364.3940 Da

Monoisotopic Mass

364.15220 Da

IUPAC Name

(2R,4R,7S,8S,9E,12S)-7,8,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0^{2,4}]nonadeca-1(15),9,16,18-tetraen-14-one

Traditional Name

(2R,4R,7S,8S,9E,12S)-7,8,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0^{2,4}]nonadeca-1(15),9,16,18-tetraen-14-one

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(=C1)[C@H]1O[C@@H]1CC[C@H](O)[C@@H](O)\C=C\C[C@H](C)OC2=O

InChI Identifier

InChI=1S/C19H24O7/c1-10-4-3-5-13(20)14(21)6-7-16-18(26-16)12-8-11(24-2)9-15(22)17(12)19(23)25-10/h3,5,8-10,13-14,16,18,20-22H,4,6-7H2,1-2H3/b5-3+/t10-,13-,14-,16+,18+/m0/s1

InChI Key

IDIVCUJKNPAADU-UDMGXPKMSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aigialus parvus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Vinylogous acid
1,2-diol
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Dialkyl ether
Oxirane
Ether
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organooxygen 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	2.17	ChemAxon
pKa (Strongest Acidic)	9.48	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	108.75 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	94.42 m³·mol⁻¹	ChemAxon
Polarizability	37.96 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

10242999

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11079019

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,4r,7s,8s,9e,12s)-7,8,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0²,⁴]nonadeca-1(19),9,15,17-tetraen-14-one (NP0299175)

MOL for NP0299175 ((2r,4r,7s,8s,9e,12s)-7,8,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0²,⁴]nonadeca-1(19),9,15,17-tetraen-14-one)

3D MOL for NP0299175 ((2r,4r,7s,8s,9e,12s)-7,8,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0²,⁴]nonadeca-1(19),9,15,17-tetraen-14-one)

3D SDF for NP0299175 ((2r,4r,7s,8s,9e,12s)-7,8,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0²,⁴]nonadeca-1(19),9,15,17-tetraen-14-one)

3D-SDF for NP0299175 ((2r,4r,7s,8s,9e,12s)-7,8,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0²,⁴]nonadeca-1(19),9,15,17-tetraen-14-one)

PDB for NP0299175 ((2r,4r,7s,8s,9e,12s)-7,8,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0²,⁴]nonadeca-1(19),9,15,17-tetraen-14-one)

3D PDB for NP0299175 ((2r,4r,7s,8s,9e,12s)-7,8,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0²,⁴]nonadeca-1(19),9,15,17-tetraen-14-one)

SMILES for NP0299175 ((2r,4r,7s,8s,9e,12s)-7,8,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0²,⁴]nonadeca-1(19),9,15,17-tetraen-14-one)

INCHI for NP0299175 ((2r,4r,7s,8s,9e,12s)-7,8,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0²,⁴]nonadeca-1(19),9,15,17-tetraen-14-one)

Structure for NP0299175 ((2r,4r,7s,8s,9e,12s)-7,8,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0²,⁴]nonadeca-1(19),9,15,17-tetraen-14-one)

3D Structure for NP0299175 ((2r,4r,7s,8s,9e,12s)-7,8,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0²,⁴]nonadeca-1(19),9,15,17-tetraen-14-one)