NP-MRD: Showing NP-Card for (2s,6r)-6-[(3s,7r,11s)-11-hydroxy-3-methyl-10-oxo-2-oxatricyclo[7.4.0.0³,⁷]trideca-1(9),5-dien-6-yl]-2-methylheptanoic acid (NP0225148)

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Record Information

Version

2.0

Created at

2022-09-06 03:47:18 UTC

Updated at

2022-09-06 03:47:18 UTC

NP-MRD ID

NP0225148

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,6r)-6-[(3s,7r,11s)-11-hydroxy-3-methyl-10-oxo-2-oxatricyclo[7.4.0.0³,⁷]trideca-1(9),5-dien-6-yl]-2-methylheptanoic acid

Description

(2S,6R)-6-[(3S,7R,11S)-11-hydroxy-3-methyl-10-oxo-2-oxatricyclo[7.4.0.0³,⁷]Trideca-1(9),5-dien-6-yl]-2-methylheptanoic acid belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (2s,6r)-6-[(3s,7r,11s)-11-hydroxy-3-methyl-10-oxo-2-oxatricyclo[7.4.0.0³,⁷]trideca-1(9),5-dien-6-yl]-2-methylheptanoic acid is found in Alternaria alternata and Maytenus hookeri. Based on a literature review very few articles have been published on (2S,6R)-6-[(3S,7R,11S)-11-hydroxy-3-methyl-10-oxo-2-oxatricyclo[7.4.0.0³,⁷]Trideca-1(9),5-dien-6-yl]-2-methylheptanoic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062205472D          

 26 28  0  0  1  0            999 V2000
   -0.2461    0.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2461   -0.4209    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9605   -0.8334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6750   -0.4209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3895   -0.8334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1039   -0.4209    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1039    0.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8184   -0.8334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5721   -0.4978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1241   -1.1109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7116   -1.8254    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5321   -1.9116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9666   -2.6100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4145   -3.2231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6076   -3.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3526   -2.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9047   -1.6539    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0555   -3.6647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2486   -3.4931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3105   -4.4493    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7584   -5.0624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1174   -4.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6695   -4.0077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4684   -0.8334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1829   -0.4209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4684   -1.6584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17  8  1  1  0  0  0
 11 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 14 23  1  0  0  0  0
  2 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
M  END


  Mrv1652309062205472D          

 26 28  0  0  1  0            999 V2000
   -0.2461    0.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2461   -0.4209    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9605   -0.8334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6750   -0.4209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3895   -0.8334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1039   -0.4209    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1039    0.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8184   -0.8334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5721   -0.4978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1241   -1.1109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7116   -1.8254    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5321   -1.9116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9666   -2.6100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4145   -3.2231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6076   -3.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3526   -2.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9047   -1.6539    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0555   -3.6647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2486   -3.4931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3105   -4.4493    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7584   -5.0624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1174   -4.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6695   -4.0077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4684   -0.8334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1829   -0.4209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4684   -1.6584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17  8  1  1  0  0  0
 11 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 14 23  1  0  0  0  0
  2 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0225148

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](CCC[C@@H](C)C1=CC[C@]2(C)OC3=C(C[C@H]12)C(=O)[C@@H](O)CC3)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O5/c1-12(5-4-6-13(2)20(24)25)14-9-10-21(3)16(14)11-15-18(26-21)8-7-17(22)19(15)23/h9,12-13,16-17,22H,4-8,10-11H2,1-3H3,(H,24,25)/t12-,13+,16-,17+,21+/m1/s1

> <INCHI_KEY>
ODMZDQKUHYGKKN-ZRXLEYOVSA-N

> <FORMULA>
C21H30O5

> <MOLECULAR_WEIGHT>
362.466

> <EXACT_MASS>
362.209324066

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
40.192421258326014

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,6R)-6-[(3S,7R,11S)-11-hydroxy-3-methyl-10-oxo-2-oxatricyclo[7.4.0.0^{3,7}]trideca-1(9),5-dien-6-yl]-2-methylheptanoic acid

> <JCHEM_LOGP>
3.0025786966666668

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.371739924487365

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.570285544999357

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5109802514661466

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
100.29939999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,6R)-6-[(3S,7R,11S)-11-hydroxy-3-methyl-10-oxo-2-oxatricyclo[7.4.0.0^{3,7}]trideca-1(9),5-dien-6-yl]-2-methylheptanoic acid

> <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      -0.459   0.754   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.459  -0.786   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.793  -1.556   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.127  -0.786   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.460  -1.556   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.794  -0.786   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.794   0.754   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -7.128  -1.556   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.535  -0.929   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -9.565  -2.074   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.795  -3.407   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -10.327  -3.568   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -9.271  -4.872   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -8.240  -6.016   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.734  -5.696   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.258  -4.232   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -7.289  -3.087   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.704  -6.841   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.197  -6.521   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -6.180  -8.305   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -5.149  -9.450   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -7.686  -8.626   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -8.716  -7.481   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.874  -1.556   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.208  -0.786   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.874  -3.096   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   24                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   17                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   17                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16    8   11                                                  
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   14                                                       
CONECT   24    2   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
(2S,6R)-6-[(3S,7R,11S)-11-Hydroxy-3-methyl-10-oxo-2-oxatricyclo[7.4.0.0,]trideca-1(9),5-dien-6-yl]-2-methylheptanoate	Generator

Chemical Formula

C₂₁H₃₀O₅

Average Mass

362.4660 Da

Monoisotopic Mass

362.20932 Da

IUPAC Name

(2S,6R)-6-[(3S,7R,11S)-11-hydroxy-3-methyl-10-oxo-2-oxatricyclo[7.4.0.0^{3,7}]trideca-1(9),5-dien-6-yl]-2-methylheptanoic acid

Traditional Name

(2S,6R)-6-[(3S,7R,11S)-11-hydroxy-3-methyl-10-oxo-2-oxatricyclo[7.4.0.0^{3,7}]trideca-1(9),5-dien-6-yl]-2-methylheptanoic acid

CAS Registry Number

Not Available

SMILES

C[C@@H](CCC[C@@H](C)C1=CC[C@]2(C)OC3=C(C[C@H]12)C(=O)[C@@H](O)CC3)C(O)=O

InChI Identifier

InChI=1S/C21H30O5/c1-12(5-4-6-13(2)20(24)25)14-9-10-21(3)16(14)11-15-18(26-21)8-7-17(22)19(15)23/h9,12-13,16-17,22H,4-8,10-11H2,1-3H3,(H,24,25)/t12-,13+,16-,17+,21+/m1/s1

InChI Key

ODMZDQKUHYGKKN-ZRXLEYOVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alternaria alternata	LOTUS Database	35616633
Maytenus hookeri	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Medium-chain fatty acid
Branched fatty acid
Heterocyclic fatty acid
Cyclohexenone
Hydroxy fatty acid
Methyl-branched fatty acid
Fatty acyl
Vinylogous ester
Ketone
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
Alcohol
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	3	ChemAxon
pKa (Strongest Acidic)	4.57	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	100.3 m³·mol⁻¹	ChemAxon
Polarizability	40.19 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	Yes	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

163004964

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,6r)-6-[(3s,7r,11s)-11-hydroxy-3-methyl-10-oxo-2-oxatricyclo[7.4.0.0³,⁷]trideca-1(9),5-dien-6-yl]-2-methylheptanoic acid (NP0225148)

MOL for NP0225148 ((2s,6r)-6-[(3s,7r,11s)-11-hydroxy-3-methyl-10-oxo-2-oxatricyclo[7.4.0.0³,⁷]trideca-1(9),5-dien-6-yl]-2-methylheptanoic acid)

3D MOL for NP0225148 ((2s,6r)-6-[(3s,7r,11s)-11-hydroxy-3-methyl-10-oxo-2-oxatricyclo[7.4.0.0³,⁷]trideca-1(9),5-dien-6-yl]-2-methylheptanoic acid)

3D SDF for NP0225148 ((2s,6r)-6-[(3s,7r,11s)-11-hydroxy-3-methyl-10-oxo-2-oxatricyclo[7.4.0.0³,⁷]trideca-1(9),5-dien-6-yl]-2-methylheptanoic acid)

3D-SDF for NP0225148 ((2s,6r)-6-[(3s,7r,11s)-11-hydroxy-3-methyl-10-oxo-2-oxatricyclo[7.4.0.0³,⁷]trideca-1(9),5-dien-6-yl]-2-methylheptanoic acid)

PDB for NP0225148 ((2s,6r)-6-[(3s,7r,11s)-11-hydroxy-3-methyl-10-oxo-2-oxatricyclo[7.4.0.0³,⁷]trideca-1(9),5-dien-6-yl]-2-methylheptanoic acid)

3D PDB for NP0225148 ((2s,6r)-6-[(3s,7r,11s)-11-hydroxy-3-methyl-10-oxo-2-oxatricyclo[7.4.0.0³,⁷]trideca-1(9),5-dien-6-yl]-2-methylheptanoic acid)

SMILES for NP0225148 ((2s,6r)-6-[(3s,7r,11s)-11-hydroxy-3-methyl-10-oxo-2-oxatricyclo[7.4.0.0³,⁷]trideca-1(9),5-dien-6-yl]-2-methylheptanoic acid)

INCHI for NP0225148 ((2s,6r)-6-[(3s,7r,11s)-11-hydroxy-3-methyl-10-oxo-2-oxatricyclo[7.4.0.0³,⁷]trideca-1(9),5-dien-6-yl]-2-methylheptanoic acid)

Structure for NP0225148 ((2s,6r)-6-[(3s,7r,11s)-11-hydroxy-3-methyl-10-oxo-2-oxatricyclo[7.4.0.0³,⁷]trideca-1(9),5-dien-6-yl]-2-methylheptanoic acid)

3D Structure for NP0225148 ((2s,6r)-6-[(3s,7r,11s)-11-hydroxy-3-methyl-10-oxo-2-oxatricyclo[7.4.0.0³,⁷]trideca-1(9),5-dien-6-yl]-2-methylheptanoic acid)