NP-MRD: Showing NP-Card for 4-O-alpha-Cadinylangolensin (NP0056822)

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Record Information

Version

2.0

Created at

2022-04-28 02:28:06 UTC

Updated at

2022-04-28 02:28:07 UTC

NP-MRD ID

NP0056822

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-O-alpha-Cadinylangolensin

Description

(2S)-1-(4-{[(1S,4R,4aS,8aR)-1,6-dimethyl-4-(propan-2-yl)-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl]oxy}-2-hydroxyphenyl)-2-(4-methoxyphenyl)propan-1-one belongs to the class of organic compounds known as alpha-methyldeoxybenzoin flavonoids. These are flavonoids with a structure based on a 1,2-diphenyl-2-propan-2-one. 4-O-alpha-Cadinylangolensin is found in Pterocarpus angolensis . Based on a literature review very few articles have been published on (2S)-1-(4-{[(1S,4R,4aS,8aR)-1,6-dimethyl-4-(propan-2-yl)-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl]oxy}-2-hydroxyphenyl)-2-(4-methoxyphenyl)propan-1-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282204282D          

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M  END

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 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 10 19  1  6  0  0  0
  1 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 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
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  6  0  0  0
 29 31  1  0  0  0  0
 24 32  1  1  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 21 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0056822

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)[C@H](C)C(=O)C1=CC=C(O[C@@]2(C)CC[C@H](C(C)C)[C@H]3C=C(C)CC[C@@H]23)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C31H40O4/c1-19(2)25-15-16-31(5,28-14-7-20(3)17-27(25)28)35-24-12-13-26(29(32)18-24)30(33)21(4)22-8-10-23(34-6)11-9-22/h8-13,17-19,21,25,27-28,32H,7,14-16H2,1-6H3/t21-,25+,27+,28+,31-/m0/s1

> <INCHI_KEY>
RVLYYCCWEKBFCF-ACWYNDPRSA-N

> <FORMULA>
C31H40O4

> <MOLECULAR_WEIGHT>
476.657

> <EXACT_MASS>
476.292659768

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
54.53424897966654

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-1-(4-{[(1S,4R,4aS,8aR)-1,6-dimethyl-4-(propan-2-yl)-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl]oxy}-2-hydroxyphenyl)-2-(4-methoxyphenyl)propan-1-one

> <ALOGPS_LOGP>
6.91

> <JCHEM_LOGP>
7.996608602333334

> <ALOGPS_LOGS>
-6.24

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.8361657077606

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.997962164881885

> <JCHEM_PKA_STRONGEST_BASIC>
-4.5575146644458515

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
141.8337

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.77e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-1-(4-{[(1S,4R,4aS,8aR)-4-isopropyl-1,6-dimethyl-3,4,4a,7,8,8a-hexahydro-2H-naphthalen-1-yl]oxy}-2-hydroxyphenyl)-2-(4-methoxyphenyl)propan-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       0.463   2.627   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.053   2.894   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.580   4.341   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.590   5.521   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.926   5.254   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.453   3.807   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.916   6.433   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.117   6.968   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.634   7.236   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.127   8.148   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.654   9.595   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.170   9.862   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.697  11.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.707  12.489   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.191  12.222   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.336  10.775   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.234  13.936   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.244  15.116   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.390   7.881   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.990   1.180   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.990   1.180   0.000  0.00  0.00           C+0
CONECT    1    2    6   20                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5                                                            
CONECT    8    4    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   19                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17   14   18                                                       
CONECT   18   17                                                            
CONECT   19   10                                                            
CONECT   20    1   21                                                       
CONECT   21   20   22   26   35                                             
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   32                                                  
CONECT   25   24   26   30                                                  
CONECT   26   25   21   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29   25                                                       
CONECT   31   29                                                            
CONECT   32   24   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   21                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₄₀O₄

Average Mass

476.6570 Da

Monoisotopic Mass

476.29266 Da

IUPAC Name

(2S)-1-(4-{[(1S,4R,4aS,8aR)-1,6-dimethyl-4-(propan-2-yl)-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl]oxy}-2-hydroxyphenyl)-2-(4-methoxyphenyl)propan-1-one

Traditional Name

(2S)-1-(4-{[(1S,4R,4aS,8aR)-4-isopropyl-1,6-dimethyl-3,4,4a,7,8,8a-hexahydro-2H-naphthalen-1-yl]oxy}-2-hydroxyphenyl)-2-(4-methoxyphenyl)propan-1-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)[C@H](C)C(=O)C1=CC=C(O[C@@]2(C)CC[C@H](C(C)C)[C@H]3C=C(C)CC[C@@H]23)C=C1O

InChI Identifier

InChI=1S/C31H40O4/c1-19(2)25-15-16-31(5,28-14-7-20(3)17-27(25)28)35-24-12-13-26(29(32)18-24)30(33)21(4)22-8-10-23(34-6)11-9-22/h8-13,17-19,21,25,27-28,32H,7,14-16H2,1-6H3/t21-,25+,27+,28+,31-/m0/s1

InChI Key

RVLYYCCWEKBFCF-ACWYNDPRSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Pterocarpus angolensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha-methyldeoxybenzoin flavonoids. These are flavonoids with a structure based on a 1,2-diphenyl-2-propan-2-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Alpha-methyldeoxybenzoin flavonoids

Sub Class

Not Available

Direct Parent

Alpha-methyldeoxybenzoin flavonoids

Alternative Parents

Substituents

Alpha-methyldeoxybenzoin flavonoid
Sesquiterpenoid
Cadinane sesquiterpenoid
Stilbene
Alkyl-phenylketone
Phenylketone
Phenylpropane
Phenoxy compound
Methoxybenzene
Aryl alkyl ketone
Aryl ketone
Phenol ether
Benzoyl
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	6.91	ALOGPS
logP	8	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	9	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	141.83 m³·mol⁻¹	ChemAxon
Polarizability	54.53 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

162928173

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4-O-alpha-Cadinylangolensin (NP0056822)

MOL for NP0056822 (4-O-alpha-Cadinylangolensin)

3D MOL for NP0056822 (4-O-alpha-Cadinylangolensin)

3D SDF for NP0056822 (4-O-alpha-Cadinylangolensin)

3D-SDF for NP0056822 (4-O-alpha-Cadinylangolensin)

PDB for NP0056822 (4-O-alpha-Cadinylangolensin)

3D PDB for NP0056822 (4-O-alpha-Cadinylangolensin)

SMILES for NP0056822 (4-O-alpha-Cadinylangolensin)

INCHI for NP0056822 (4-O-alpha-Cadinylangolensin)

Structure for NP0056822 (4-O-alpha-Cadinylangolensin)

3D Structure for NP0056822 (4-O-alpha-Cadinylangolensin)