NP-MRD: Showing NP-Card for methyl 5-(acetyloxy)-4a-hydroxy-4,4,11b-trimethyl-1-oxo-2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylate (NP0218346)

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Record Information

Version

2.0

Created at

2022-09-05 18:58:44 UTC

Updated at

2022-09-05 18:58:44 UTC

NP-MRD ID

NP0218346

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 5-(acetyloxy)-4a-hydroxy-4,4,11b-trimethyl-1-oxo-2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylate

Description

Methyl 8-(acetyloxy)-7-hydroxy-2,6,6-trimethyl-3-oxo-15-oxatetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]Heptadeca-12(16),13-diene-11-carboxylate belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Methyl 8-(acetyloxy)-7-hydroxy-2,6,6-trimethyl-3-oxo-15-oxatetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]Heptadeca-12(16),13-diene-11-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241503452D          

 30 33  0  0  0  0            999 V2000
    3.6930    2.0836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9733    1.3077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7855    1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3173    1.7932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0658    0.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8779    0.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4097    0.8721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2218    0.7268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7536    1.3576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4733    2.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6612    2.2787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0052    2.7642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5021   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0339    0.5816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3142   -0.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3162    0.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1271   -0.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5945   -0.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0627   -1.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2506   -1.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7188   -2.0864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9703   -0.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4385   -1.3105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1582   -0.5346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6264   -1.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8142   -1.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1629   -1.5264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4801   -1.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7094   -0.2709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5339   -0.2441    0.0000 C   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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  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
  8 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
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
  6 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
  5 30  1  0  0  0  0
 26 30  2  0  0  0  0
M  END


  Mrv1533004241503452D          

 30 33  0  0  0  0            999 V2000
    3.6930    2.0836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9733    1.3077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7855    1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3173    1.7932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0658    0.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8779    0.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4097    0.8721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2218    0.7268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7536    1.3576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4733    2.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6612    2.2787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0052    2.7642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5021   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0339    0.5816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3142   -0.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3162    0.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1271   -0.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5945   -0.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0627   -1.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2506   -1.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7188   -2.0864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9703   -0.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4385   -1.3105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1582   -0.5346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6264   -1.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8142   -1.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1629   -1.5264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4801   -1.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7094   -0.2709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5339   -0.2441    0.0000 C   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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  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
  8 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
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
  6 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
  5 30  1  0  0  0  0
 26 30  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0218346

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1C2CC(OC(C)=O)C3(O)C(C)(C)CCC(=O)C3(C)C2CC2=C1C=CO2

> <INCHI_IDENTIFIER>
InChI=1S/C23H30O7/c1-12(24)30-18-10-14-15(11-16-13(7-9-29-16)19(14)20(26)28-5)22(4)17(25)6-8-21(2,3)23(18,22)27/h7,9,14-15,18-19,27H,6,8,10-11H2,1-5H3

> <INCHI_KEY>
FGVVZVPAVGZHMX-UHFFFAOYSA-N

> <FORMULA>
C23H30O7

> <MOLECULAR_WEIGHT>
418.486

> <EXACT_MASS>
418.199153306

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
44.281485344083066

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 8-(acetyloxy)-7-hydroxy-2,6,6-trimethyl-3-oxo-15-oxatetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadeca-12(16),13-diene-11-carboxylate

> <ALOGPS_LOGP>
2.39

> <JCHEM_LOGP>
2.280036488666666

> <ALOGPS_LOGS>
-3.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.277406281757933

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.994274307378607

> <JCHEM_PKA_STRONGEST_BASIC>
-2.904723952934964

> <JCHEM_POLAR_SURFACE_AREA>
103.04

> <JCHEM_REFRACTIVITY>
106.16719999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.71e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 8-(acetyloxy)-7-hydroxy-2,6,6-trimethyl-3-oxo-15-oxatetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadeca-12(16),13-diene-11-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       6.894   3.889   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.417   2.441   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.933   2.170   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.926   3.347   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.456   0.722   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.972   0.451   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.965   1.628   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.481   1.357   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      14.473   2.534   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      13.950   3.982   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      12.434   4.254   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      14.943   5.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.004  -0.092   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      14.997   1.086   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      15.520  -0.363   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.524   1.177   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.037  -0.099   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.043  -1.811   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.050  -2.988   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.534  -2.717   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.542  -3.895   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      13.011  -1.269   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.019  -2.446   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.495  -0.998   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.503  -2.175   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.987  -1.904   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.771  -2.849   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.496  -1.985   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.924  -0.506   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.463  -0.456   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   30                                                  
CONECT    6    5    7   24                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    8   14   15   22                                             
CONECT   14   13                                                            
CONECT   15   13   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   13   23   24                                             
CONECT   23   22                                                            
CONECT   24   22    6   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   30                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29    5   26                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
Methyl 8-(acetyloxy)-7-hydroxy-2,6,6-trimethyl-3-oxo-15-oxatetracyclo[8.7.0.0,.0,]heptadeca-12(16),13-diene-11-carboxylic acid	Generator
Methyl 8-(acetyloxy)-7-hydroxy-2,6,6-trimethyl-3-oxo-15-oxatetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadeca-12(16),13-diene-11-carboxylic acid	Generator

Chemical Formula

C₂₃H₃₀O₇

Average Mass

418.4860 Da

Monoisotopic Mass

418.19915 Da

IUPAC Name

methyl 8-(acetyloxy)-7-hydroxy-2,6,6-trimethyl-3-oxo-15-oxatetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadeca-12(16),13-diene-11-carboxylate

Traditional Name

methyl 8-(acetyloxy)-7-hydroxy-2,6,6-trimethyl-3-oxo-15-oxatetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadeca-12(16),13-diene-11-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1C2CC(OC(C)=O)C3(O)C(C)(C)CCC(=O)C3(C)C2CC2=C1C=CO2

InChI Identifier

InChI=1S/C23H30O7/c1-12(24)30-18-10-14-15(11-16-13(7-9-29-16)19(14)20(26)28-5)22(4)17(25)6-8-21(2,3)23(18,22)27/h7,9,14-15,18-19,27H,6,8,10-11H2,1-5H3

InChI Key

FGVVZVPAVGZHMX-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Naphthofuran
Benzofuran
Dicarboxylic acid or derivatives
Cyclic alcohol
Heteroaromatic compound
Furan
Methyl ester
Tertiary alcohol
Carboxylic acid ester
Ketone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
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	2.39	ALOGPS
logP	2.28	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	12.99	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	103.04 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	106.17 m³·mol⁻¹	ChemAxon
Polarizability	44.28 Å³	ChemAxon
Number of Rings	4	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

72762829

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 5-(acetyloxy)-4a-hydroxy-4,4,11b-trimethyl-1-oxo-2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylate (NP0218346)

MOL for NP0218346 (methyl 5-(acetyloxy)-4a-hydroxy-4,4,11b-trimethyl-1-oxo-2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylate)

3D MOL for NP0218346 (methyl 5-(acetyloxy)-4a-hydroxy-4,4,11b-trimethyl-1-oxo-2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylate)

3D SDF for NP0218346 (methyl 5-(acetyloxy)-4a-hydroxy-4,4,11b-trimethyl-1-oxo-2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylate)

3D-SDF for NP0218346 (methyl 5-(acetyloxy)-4a-hydroxy-4,4,11b-trimethyl-1-oxo-2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylate)

PDB for NP0218346 (methyl 5-(acetyloxy)-4a-hydroxy-4,4,11b-trimethyl-1-oxo-2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylate)

3D PDB for NP0218346 (methyl 5-(acetyloxy)-4a-hydroxy-4,4,11b-trimethyl-1-oxo-2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylate)

SMILES for NP0218346 (methyl 5-(acetyloxy)-4a-hydroxy-4,4,11b-trimethyl-1-oxo-2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylate)

INCHI for NP0218346 (methyl 5-(acetyloxy)-4a-hydroxy-4,4,11b-trimethyl-1-oxo-2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylate)

Structure for NP0218346 (methyl 5-(acetyloxy)-4a-hydroxy-4,4,11b-trimethyl-1-oxo-2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylate)

3D Structure for NP0218346 (methyl 5-(acetyloxy)-4a-hydroxy-4,4,11b-trimethyl-1-oxo-2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylate)