NP-MRD: Showing NP-Card for 11-hydroxy-12-methoxy-7,7,10a-trimethyl-1h,2h,5h,6h,6ah,8h,9h,10h-phenanthro[1,2-c]pyran-4-one (NP0299541)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 11:25:06 UTC

Updated at

2022-09-10 11:25:07 UTC

NP-MRD ID

NP0299541

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11-hydroxy-12-methoxy-7,7,10a-trimethyl-1h,2h,5h,6h,6ah,8h,9h,10h-phenanthro[1,2-c]pyran-4-one

Description

9-Hydroxy-8-methoxy-11,15,15-trimethyl-4-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]Octadeca-1,7,9-trien-3-one belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. 11-hydroxy-12-methoxy-7,7,10a-trimethyl-1h,2h,5h,6h,6ah,8h,9h,10h-phenanthro[1,2-c]pyran-4-one is found in Swartzia langsdorffii. 9-Hydroxy-8-methoxy-11,15,15-trimethyl-4-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]Octadeca-1,7,9-trien-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004191514072D          

 25 28  0  0  0  0            999 V2000
    0.7145    2.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    2.4393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7946    1.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048    1.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1449    2.1275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748    0.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347    0.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048   -0.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149   -0.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4709   -1.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4731   -0.7906    0.0000 C   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
    5.0352    1.0361    0.0000 C   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
    3.6850    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149    1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546   -1.1466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744   -0.2111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546    1.0361    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
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  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  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  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
  6 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
  7 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
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  3 25  1  0  0  0  0
 19 25  2  0  0  0  0
M  END


  Mrv1533004191514072D          

 25 28  0  0  0  0            999 V2000
    0.7145    2.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    2.4393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7946    1.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048    1.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1449    2.1275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748    0.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347    0.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048   -0.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149   -0.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4709   -1.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4731   -0.7906    0.0000 C   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
    5.0352    1.0361    0.0000 C   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
    3.6850    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149    1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546   -1.1466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744   -0.2111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546    1.0361    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
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  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  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  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
  6 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
  7 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
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  3 25  1  0  0  0  0
 19 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0299541

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C2=C(CCC3C(C)(C)CCCC23C)C2=C1CCOC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O4/c1-20(2)9-5-10-21(3)14(20)7-6-12-15-13(8-11-25-19(15)23)18(24-4)17(22)16(12)21/h14,22H,5-11H2,1-4H3

> <INCHI_KEY>
QAIIXQJPXUSTBS-UHFFFAOYSA-N

> <FORMULA>
C21H28O4

> <MOLECULAR_WEIGHT>
344.451

> <EXACT_MASS>
344.198759382

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
38.71603716547801

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-hydroxy-8-methoxy-11,15,15-trimethyl-4-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadeca-1(10),2(7),8-trien-3-one

> <ALOGPS_LOGP>
5.08

> <JCHEM_LOGP>
4.6941918613333335

> <ALOGPS_LOGS>
-4.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.643734422946645

> <JCHEM_PKA_STRONGEST_BASIC>
-4.776779678094344

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
97.31499999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.36e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-hydroxy-8-methoxy-11,15,15-trimethyl-4-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadeca-1(10),2(7),8-trien-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       1.334   4.844   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.846   4.553   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.350   3.098   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.862   2.807   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.870   3.971   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.366   1.352   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.358   0.188   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.862  -1.267   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.375  -1.558   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.383  -0.394   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.895  -0.685   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.346  -2.124   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.216  -1.476   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.903   0.479   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.399   1.934   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.887   2.225   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.879   1.061   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.375   2.516   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.846   0.479   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.838  -0.685   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.342  -2.140   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.326  -0.394   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.179   1.061   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.830   2.225   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.342   1.934   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   25                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   17                                                  
CONECT    7    6    8   19                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    6   10   18                                             
CONECT   18   17                                                            
CONECT   19    7   20   25                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24    3   19                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₈O₄

Average Mass

344.4510 Da

Monoisotopic Mass

344.19876 Da

IUPAC Name

9-hydroxy-8-methoxy-11,15,15-trimethyl-4-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadeca-1(10),2(7),8-trien-3-one

Traditional Name

9-hydroxy-8-methoxy-11,15,15-trimethyl-4-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadeca-1(10),2(7),8-trien-3-one

CAS Registry Number

Not Available

SMILES

COC1=C(O)C2=C(CCC3C(C)(C)CCCC23C)C2=C1CCOC2=O

InChI Identifier

InChI=1S/C21H28O4/c1-20(2)9-5-10-21(3)14(20)7-6-12-15-13(8-11-25-19(15)23)18(24-4)17(22)16(12)21/h14,22H,5-11H2,1-4H3

InChI Key

QAIIXQJPXUSTBS-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Swartzia langsdorffii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Phenanthrene
Naphthopyran
Benzopyran
Isochromane
2-benzopyran
Tetralin
Naphthalene
Anisole
Phenol ether
Alkyl aryl ether
Phenol
Benzenoid
Pyran
Carboxylic acid ester
Lactone
Oxacycle
Carboxylic acid derivative
Ether
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
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	5.08	ALOGPS
logP	4.69	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	9.64	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	97.32 m³·mol⁻¹	ChemAxon
Polarizability	38.72 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

72988695

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 11-hydroxy-12-methoxy-7,7,10a-trimethyl-1h,2h,5h,6h,6ah,8h,9h,10h-phenanthro[1,2-c]pyran-4-one (NP0299541)

MOL for NP0299541 (11-hydroxy-12-methoxy-7,7,10a-trimethyl-1h,2h,5h,6h,6ah,8h,9h,10h-phenanthro[1,2-c]pyran-4-one)

3D MOL for NP0299541 (11-hydroxy-12-methoxy-7,7,10a-trimethyl-1h,2h,5h,6h,6ah,8h,9h,10h-phenanthro[1,2-c]pyran-4-one)

3D SDF for NP0299541 (11-hydroxy-12-methoxy-7,7,10a-trimethyl-1h,2h,5h,6h,6ah,8h,9h,10h-phenanthro[1,2-c]pyran-4-one)

3D-SDF for NP0299541 (11-hydroxy-12-methoxy-7,7,10a-trimethyl-1h,2h,5h,6h,6ah,8h,9h,10h-phenanthro[1,2-c]pyran-4-one)

PDB for NP0299541 (11-hydroxy-12-methoxy-7,7,10a-trimethyl-1h,2h,5h,6h,6ah,8h,9h,10h-phenanthro[1,2-c]pyran-4-one)

3D PDB for NP0299541 (11-hydroxy-12-methoxy-7,7,10a-trimethyl-1h,2h,5h,6h,6ah,8h,9h,10h-phenanthro[1,2-c]pyran-4-one)

SMILES for NP0299541 (11-hydroxy-12-methoxy-7,7,10a-trimethyl-1h,2h,5h,6h,6ah,8h,9h,10h-phenanthro[1,2-c]pyran-4-one)

INCHI for NP0299541 (11-hydroxy-12-methoxy-7,7,10a-trimethyl-1h,2h,5h,6h,6ah,8h,9h,10h-phenanthro[1,2-c]pyran-4-one)

Structure for NP0299541 (11-hydroxy-12-methoxy-7,7,10a-trimethyl-1h,2h,5h,6h,6ah,8h,9h,10h-phenanthro[1,2-c]pyran-4-one)

3D Structure for NP0299541 (11-hydroxy-12-methoxy-7,7,10a-trimethyl-1h,2h,5h,6h,6ah,8h,9h,10h-phenanthro[1,2-c]pyran-4-one)