NP-MRD: Showing NP-Card for methyl 6-hydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylidene-1,4,5,8-tetraoxo-4ah,9h,10h,10bh,11h-phenanthro[1,2-c]pyran-2-carboxylate (NP0232683)

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Record Information

Version

2.0

Created at

2022-09-06 13:59:44 UTC

Updated at

2022-09-06 13:59:44 UTC

NP-MRD ID

NP0232683

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 6-hydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylidene-1,4,5,8-tetraoxo-4ah,9h,10h,10bh,11h-phenanthro[1,2-c]pyran-2-carboxylate

Description

Methyl 17-hydroxy-1,5,7,11,15,15-hexamethyl-8-methylidene-3,6,14,18-tetraoxo-4-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]Octadec-16-ene-5-carboxylate belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton. methyl 6-hydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylidene-1,4,5,8-tetraoxo-4ah,9h,10h,10bh,11h-phenanthro[1,2-c]pyran-2-carboxylate is found in Mallotus nudiflorus. Methyl 17-hydroxy-1,5,7,11,15,15-hexamethyl-8-methylidene-3,6,14,18-tetraoxo-4-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]Octadec-16-ene-5-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261503392D          

 34 37  0  0  0  0            999 V2000
    6.7597    1.8841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0389    1.4828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0260    0.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7340    0.2343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8256   -0.3836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352    1.0361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550    1.9716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6850   -1.6143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1449    2.1275    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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  5 19  1  0  0  0  0
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 33 34  2  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004261503392D          

 34 37  0  0  0  0            999 V2000
    6.7597    1.8841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0232683

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1(C)OC(=O)C2C3(C)C(CC(=C)C2(C)C1=O)C1(C)CCC(=O)C(C)(C)C1=C(O)C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O8/c1-12-11-13-23(4)10-9-14(27)22(2,3)16(23)15(28)18(29)25(13,6)17-19(30)34-26(7,21(32)33-8)20(31)24(12,17)5/h13,17,28H,1,9-11H2,2-8H3

> <INCHI_KEY>
GTEJJXOFLPCZGJ-UHFFFAOYSA-N

> <FORMULA>
C26H32O8

> <MOLECULAR_WEIGHT>
472.534

> <EXACT_MASS>
472.20971799

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
48.503355518137745

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 17-hydroxy-1,5,7,11,15,15-hexamethyl-8-methylidene-3,6,14,18-tetraoxo-4-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadec-16-ene-5-carboxylate

> <ALOGPS_LOGP>
2.56

> <JCHEM_LOGP>
3.645116135999999

> <ALOGPS_LOGS>
-4.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.461759517492535

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.500366587842775

> <JCHEM_PKA_STRONGEST_BASIC>
-4.010199654473394

> <JCHEM_POLAR_SURFACE_AREA>
124.04000000000002

> <JCHEM_REFRACTIVITY>
121.28489999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.63e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 17-hydroxy-1,5,7,11,15,15-hexamethyl-8-methylidene-3,6,14,18-tetraoxo-4-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadec-16-ene-5-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0      12.618   3.517   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      11.273   2.768   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.249   1.228   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      12.570   0.437   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.903   0.479   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.874  -0.716   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.399   1.934   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       7.887   2.225   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       7.383   3.680   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.879   1.061   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.366   1.352   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.375   2.516   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.358   0.188   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.862  -1.267   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.375  -1.558   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.879  -3.013   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.383  -0.394   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.887  -1.849   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.895  -0.685   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.399  -2.140   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.846   0.479   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.350  -0.976   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.838  -0.685   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.326  -0.394   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.179   1.061   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.691   1.352   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.830   2.225   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.492   3.016   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.379   3.664   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.342   1.934   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.350   3.098   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.846   4.553   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.862   2.807   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.870   3.971   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7   19                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   17                                                  
CONECT   11   10   12   13   33                                             
CONECT   12   11                                                            
CONECT   13   11   14   21                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   10   18   19                                             
CONECT   18   17                                                            
CONECT   19   17    5   20                                                  
CONECT   20   19                                                            
CONECT   21   13   22   23   30                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27   21   31                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   11   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
Methyl 17-hydroxy-1,5,7,11,15,15-hexamethyl-8-methylidene-3,6,14,18-tetraoxo-4-oxatetracyclo[8.8.0.0,.0,]octadec-16-ene-5-carboxylic acid	Generator
Methyl 17-hydroxy-1,5,7,11,15,15-hexamethyl-8-methylidene-3,6,14,18-tetraoxo-4-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadec-16-ene-5-carboxylic acid	Generator

Chemical Formula

C₂₆H₃₂O₈

Average Mass

472.5340 Da

Monoisotopic Mass

472.20972 Da

IUPAC Name

methyl 17-hydroxy-1,5,7,11,15,15-hexamethyl-8-methylidene-3,6,14,18-tetraoxo-4-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadec-16-ene-5-carboxylate

Traditional Name

methyl 17-hydroxy-1,5,7,11,15,15-hexamethyl-8-methylidene-3,6,14,18-tetraoxo-4-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadec-16-ene-5-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1(C)OC(=O)C2C3(C)C(CC(=C)C2(C)C1=O)C1(C)CCC(=O)C(C)(C)C1=C(O)C3=O

InChI Identifier

InChI=1S/C26H32O8/c1-12-11-13-23(4)10-9-14(27)22(2,3)16(23)15(28)18(29)25(13,6)17-19(30)34-26(7,21(32)33-8)20(31)24(12,17)5/h13,17,28H,1,9-11H2,2-8H3

InChI Key

GTEJJXOFLPCZGJ-UHFFFAOYSA-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
Trewia nudiflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Steroid lactones

Alternative Parents

Substituents

Steroid lactone
18-oxosteroid
17-oxosteroid
Oxosteroid
Hydroxysteroid
6-hydroxysteroid
Naphthopyran
Naphthalene
Alpha-acyloxy ketone
Delta valerolactone
Delta_valerolactone
Cyclohexenone
Pyran
Oxane
Dicarboxylic acid or derivatives
Methyl ester
Cyclic ketone
Lactone
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Enol
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aldehyde
Organooxygen compound
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	2.56	ALOGPS
logP	3.65	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	8.5	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	124.04 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	121.28 m³·mol⁻¹	ChemAxon
Polarizability	48.5 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

73002548

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 6-hydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylidene-1,4,5,8-tetraoxo-4ah,9h,10h,10bh,11h-phenanthro[1,2-c]pyran-2-carboxylate (NP0232683)

MOL for NP0232683 (methyl 6-hydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylidene-1,4,5,8-tetraoxo-4ah,9h,10h,10bh,11h-phenanthro[1,2-c]pyran-2-carboxylate)

3D MOL for NP0232683 (methyl 6-hydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylidene-1,4,5,8-tetraoxo-4ah,9h,10h,10bh,11h-phenanthro[1,2-c]pyran-2-carboxylate)

3D SDF for NP0232683 (methyl 6-hydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylidene-1,4,5,8-tetraoxo-4ah,9h,10h,10bh,11h-phenanthro[1,2-c]pyran-2-carboxylate)

3D-SDF for NP0232683 (methyl 6-hydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylidene-1,4,5,8-tetraoxo-4ah,9h,10h,10bh,11h-phenanthro[1,2-c]pyran-2-carboxylate)

PDB for NP0232683 (methyl 6-hydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylidene-1,4,5,8-tetraoxo-4ah,9h,10h,10bh,11h-phenanthro[1,2-c]pyran-2-carboxylate)

3D PDB for NP0232683 (methyl 6-hydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylidene-1,4,5,8-tetraoxo-4ah,9h,10h,10bh,11h-phenanthro[1,2-c]pyran-2-carboxylate)

SMILES for NP0232683 (methyl 6-hydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylidene-1,4,5,8-tetraoxo-4ah,9h,10h,10bh,11h-phenanthro[1,2-c]pyran-2-carboxylate)

INCHI for NP0232683 (methyl 6-hydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylidene-1,4,5,8-tetraoxo-4ah,9h,10h,10bh,11h-phenanthro[1,2-c]pyran-2-carboxylate)

Structure for NP0232683 (methyl 6-hydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylidene-1,4,5,8-tetraoxo-4ah,9h,10h,10bh,11h-phenanthro[1,2-c]pyran-2-carboxylate)

3D Structure for NP0232683 (methyl 6-hydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylidene-1,4,5,8-tetraoxo-4ah,9h,10h,10bh,11h-phenanthro[1,2-c]pyran-2-carboxylate)