NP-MRD: Showing NP-Card for 1-(hydroxymethyl)-6,6-dimethyl-1h,2h,7h,8h,9h-phenanthro[1,2-b]furan-10,11-dione (NP0281562)

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Record Information

Version

2.0

Created at

2022-09-09 07:59:13 UTC

Updated at

2022-09-09 07:59:14 UTC

NP-MRD ID

NP0281562

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(hydroxymethyl)-6,6-dimethyl-1h,2h,7h,8h,9h-phenanthro[1,2-b]furan-10,11-dione

Description

14-(Hydroxymethyl)-6,6-dimethyl-12-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-1(10),2(7),8,11(15)-tetraene-16,17-dione belongs to the class of organic compounds known as 11-oxosteroids. These are steroid derivatives carrying a C=O group at the 11-position of the steroid skeleton. 1-(hydroxymethyl)-6,6-dimethyl-1h,2h,7h,8h,9h-phenanthro[1,2-b]furan-10,11-dione is found in Salvia munzii. 14-(Hydroxymethyl)-6,6-dimethyl-12-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-1(10),2(7),8,11(15)-tetraene-16,17-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241515282D          

 23 26  0  0  0  0            999 V2000
   -0.2793   -3.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342   -2.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7182   -3.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976   -2.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -1.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -1.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266   -1.9173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -1.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -0.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0872   -0.3654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7114   -0.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -1.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826   -2.2576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -2.7639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168   -2.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -1.5084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939   -0.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9830   -0.0929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705   -2.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902   -3.1787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -3.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -2.6932    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 20  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
  2 23  1  0  0  0  0
  7 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0281562

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCCC2=C3C(=O)C(=O)C4=C(OCC4CO)C3=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C19H20O4/c1-19(2)7-3-4-11-13(19)6-5-12-15(11)17(22)16(21)14-10(8-20)9-23-18(12)14/h5-6,10,20H,3-4,7-9H2,1-2H3

> <INCHI_KEY>
RLHQXRPMHRPPEA-UHFFFAOYSA-N

> <FORMULA>
C19H20O4

> <MOLECULAR_WEIGHT>
312.365

> <EXACT_MASS>
312.136159124

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
34.292180448840014

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
14-(hydroxymethyl)-6,6-dimethyl-12-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1,7,9,11(15)-tetraene-16,17-dione

> <ALOGPS_LOGP>
3.14

> <JCHEM_LOGP>
2.4967686163333327

> <ALOGPS_LOGS>
-4.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.32710561803469

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6555510764733903

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
88.2414

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.03e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-(hydroxymethyl)-6,6-dimethyl-12-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1,7,9,11(15)-tetraene-16,17-dione

> <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      -0.521  -6.072   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.810  -5.298   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.341  -6.744   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.182  -4.121   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.341  -2.673   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.857  -2.402   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.850  -3.579   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.366  -3.308   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.889  -1.859   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.896  -0.682   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.405  -1.588   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.928  -0.140   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.398  -2.766   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.874  -4.214   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.090  -5.159   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.365  -4.295   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.937  -2.816   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.882  -1.600   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.302  -0.173   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.358  -4.485   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.835  -5.934   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.319  -6.205   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.326  -5.027   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   23                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   23                                                  
CONECT    8    7    9   20                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   17                                                  
CONECT   14   13   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   13   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   14    8   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22    2    7                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₀O₄

Average Mass

312.3650 Da

Monoisotopic Mass

312.13616 Da

IUPAC Name

14-(hydroxymethyl)-6,6-dimethyl-12-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1,7,9,11(15)-tetraene-16,17-dione

Traditional Name

14-(hydroxymethyl)-6,6-dimethyl-12-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1,7,9,11(15)-tetraene-16,17-dione

CAS Registry Number

Not Available

SMILES

CC1(C)CCCC2=C3C(=O)C(=O)C4=C(OCC4CO)C3=CC=C12

InChI Identifier

InChI=1S/C19H20O4/c1-19(2)7-3-4-11-13(19)6-5-12-15(11)17(22)16(21)14-10(8-20)9-23-18(12)14/h5-6,10,20H,3-4,7-9H2,1-2H3

InChI Key

RLHQXRPMHRPPEA-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Salvia munzii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 11-oxosteroids. These are steroid derivatives carrying a C=O group at the 11-position of the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Oxosteroids

Direct Parent

11-oxosteroids

Alternative Parents

Substituents

20-hydroxysteroid
Diterpenoid
Tanshinone skeleton
Hydroxysteroid
11-oxosteroid
Delta-5-steroid
Delta-7-steroid
15-oxasteroid
Phenanthrene
Naphthofuran
Naphthoquinone
Tetralin
Naphthalene
Aryl ketone
Quinone
Benzenoid
Vinylogous ester
Dihydrofuran
Ketone
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Primary alcohol
Carbonyl group
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	3.14	ALOGPS
logP	2.5	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	15.33	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	88.24 m³·mol⁻¹	ChemAxon
Polarizability	34.29 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-(hydroxymethyl)-6,6-dimethyl-1h,2h,7h,8h,9h-phenanthro[1,2-b]furan-10,11-dione (NP0281562)

MOL for NP0281562 (1-(hydroxymethyl)-6,6-dimethyl-1h,2h,7h,8h,9h-phenanthro[1,2-b]furan-10,11-dione)

3D MOL for NP0281562 (1-(hydroxymethyl)-6,6-dimethyl-1h,2h,7h,8h,9h-phenanthro[1,2-b]furan-10,11-dione)

3D SDF for NP0281562 (1-(hydroxymethyl)-6,6-dimethyl-1h,2h,7h,8h,9h-phenanthro[1,2-b]furan-10,11-dione)

3D-SDF for NP0281562 (1-(hydroxymethyl)-6,6-dimethyl-1h,2h,7h,8h,9h-phenanthro[1,2-b]furan-10,11-dione)

PDB for NP0281562 (1-(hydroxymethyl)-6,6-dimethyl-1h,2h,7h,8h,9h-phenanthro[1,2-b]furan-10,11-dione)

3D PDB for NP0281562 (1-(hydroxymethyl)-6,6-dimethyl-1h,2h,7h,8h,9h-phenanthro[1,2-b]furan-10,11-dione)

SMILES for NP0281562 (1-(hydroxymethyl)-6,6-dimethyl-1h,2h,7h,8h,9h-phenanthro[1,2-b]furan-10,11-dione)

INCHI for NP0281562 (1-(hydroxymethyl)-6,6-dimethyl-1h,2h,7h,8h,9h-phenanthro[1,2-b]furan-10,11-dione)

Structure for NP0281562 (1-(hydroxymethyl)-6,6-dimethyl-1h,2h,7h,8h,9h-phenanthro[1,2-b]furan-10,11-dione)

3D Structure for NP0281562 (1-(hydroxymethyl)-6,6-dimethyl-1h,2h,7h,8h,9h-phenanthro[1,2-b]furan-10,11-dione)