NP-MRD: Showing NP-Card for (1r,4s,4as,7r,8ar)-1,4a-dimethyl-7-(prop-1-en-2-yl)-4-[(4s)-5,7,8-trimethoxy-2-phenyl-4h-chromen-4-yl]-octahydronaphthalen-1-ol (NP0163027)

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Record Information

Version

2.0

Created at

2022-09-02 21:33:44 UTC

Updated at

2022-09-02 21:33:44 UTC

NP-MRD ID

NP0163027

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4s,4as,7r,8ar)-1,4a-dimethyl-7-(prop-1-en-2-yl)-4-[(4s)-5,7,8-trimethoxy-2-phenyl-4h-chromen-4-yl]-octahydronaphthalen-1-ol

Description

Fissistigmatin B belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. Based on a literature review very few articles have been published on Fissistigmatin B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022223332D          

 38 42  0  0  1  0            999 V2000
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  4 38  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309022223332D          

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    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2461   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1855   -2.2820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  6  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  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  1  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 31  2  0  0  0  0
 20 31  1  0  0  0  0
 10 31  1  0  0  0  0
  9 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  1  0  0  0
 34 37  1  0  0  0  0
  7 37  1  0  0  0  0
 37 38  1  6  0  0  0
  4 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0163027

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OC)=C2[C@H](C=C(OC2=C1OC)C1=CC=CC=C1)[C@@H]1CC[C@@](C)(O)[C@@H]2C[C@@H](CC[C@@]12C)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C33H42O5/c1-20(2)22-13-15-32(3)24(14-16-33(4,34)28(32)17-22)23-18-25(21-11-9-8-10-12-21)38-31-29(23)26(35-5)19-27(36-6)30(31)37-7/h8-12,18-19,22-24,28,34H,1,13-17H2,2-7H3/t22-,23-,24+,28-,32+,33-/m1/s1

> <INCHI_KEY>
HPOVGYSBSUHODS-GXZJPLRGSA-N

> <FORMULA>
C33H42O5

> <MOLECULAR_WEIGHT>
518.694

> <EXACT_MASS>
518.303224452

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
59.035657452442564

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4S,4aS,7R,8aR)-1,4a-dimethyl-7-(prop-1-en-2-yl)-4-[(4S)-5,7,8-trimethoxy-2-phenyl-4H-chromen-4-yl]-decahydronaphthalen-1-ol

> <ALOGPS_LOGP>
7.64

> <JCHEM_LOGP>
6.109858117000002

> <ALOGPS_LOGS>
-6.48

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.4609548077678559

> <JCHEM_POLAR_SURFACE_AREA>
57.150000000000006

> <JCHEM_REFRACTIVITY>
151.97510000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.74e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4S,4aS,7R,8aR)-1,4a-dimethyl-7-(prop-1-en-2-yl)-4-[(4S)-5,7,8-trimethoxy-2-phenyl-4H-chromen-4-yl]-octahydronaphthalen-1-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.669   4.620   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      13.337   6.160   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      14.670   6.930   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.670   3.850   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      16.004   4.620   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      16.004   6.160   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.670   2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      13.337   0.000   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.659  -4.260   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       9.680  -4.260   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   38                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   37                                             
CONECT    8    7                                                            
CONECT    9    7   10   32                                                  
CONECT   10    9   11   31                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19   12   20                                                       
CONECT   20   19   21   31                                                  
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28   20   10                                                  
CONECT   32    9   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36   37                                             
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   34    7   38                                                  
CONECT   38   37    4                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₄₂O₅

Average Mass

518.6940 Da

Monoisotopic Mass

518.30322 Da

IUPAC Name

(1R,4S,4aS,7R,8aR)-1,4a-dimethyl-7-(prop-1-en-2-yl)-4-[(4S)-5,7,8-trimethoxy-2-phenyl-4H-chromen-4-yl]-decahydronaphthalen-1-ol

Traditional Name

(1R,4S,4aS,7R,8aR)-1,4a-dimethyl-7-(prop-1-en-2-yl)-4-[(4S)-5,7,8-trimethoxy-2-phenyl-4H-chromen-4-yl]-octahydronaphthalen-1-ol

CAS Registry Number

Not Available

SMILES

COC1=CC(OC)=C2[C@H](C=C(OC2=C1OC)C1=CC=CC=C1)[C@@H]1CC[C@@](C)(O)[C@@H]2C[C@@H](CC[C@@]12C)C(C)=C

InChI Identifier

InChI=1S/C33H42O5/c1-20(2)22-13-15-32(3)24(14-16-33(4,34)28(32)17-22)23-18-25(21-11-9-8-10-12-21)38-31-29(23)26(35-5)19-27(36-6)30(31)37-7/h8-12,18-19,22-24,28,34H,1,13-17H2,2-7H3/t22-,23-,24+,28-,32+,33-/m1/s1

InChI Key

HPOVGYSBSUHODS-GXZJPLRGSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

8-O-methylated flavonoids

Alternative Parents

Substituents

5-methoxyflavonoid-skeleton
7-methoxyflavonoid-skeleton
8-methoxyflavonoid-skeleton
Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid
Sesquiterpenoid
Benzopyran
1-benzopyran
Anisole
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Cyclic alcohol
Tertiary alcohol
Ether
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
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	7.64	ALOGPS
logP	6.11	ChemAxon
logS	-6.5	ALOGPS
pKa (Strongest Basic)	-0.46	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	57.15 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	151.98 m³·mol⁻¹	ChemAxon
Polarizability	59.04 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	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

10230422

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15886360

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,4s,4as,7r,8ar)-1,4a-dimethyl-7-(prop-1-en-2-yl)-4-[(4s)-5,7,8-trimethoxy-2-phenyl-4h-chromen-4-yl]-octahydronaphthalen-1-ol (NP0163027)

MOL for NP0163027 ((1r,4s,4as,7r,8ar)-1,4a-dimethyl-7-(prop-1-en-2-yl)-4-[(4s)-5,7,8-trimethoxy-2-phenyl-4h-chromen-4-yl]-octahydronaphthalen-1-ol)

3D MOL for NP0163027 ((1r,4s,4as,7r,8ar)-1,4a-dimethyl-7-(prop-1-en-2-yl)-4-[(4s)-5,7,8-trimethoxy-2-phenyl-4h-chromen-4-yl]-octahydronaphthalen-1-ol)

3D SDF for NP0163027 ((1r,4s,4as,7r,8ar)-1,4a-dimethyl-7-(prop-1-en-2-yl)-4-[(4s)-5,7,8-trimethoxy-2-phenyl-4h-chromen-4-yl]-octahydronaphthalen-1-ol)

3D-SDF for NP0163027 ((1r,4s,4as,7r,8ar)-1,4a-dimethyl-7-(prop-1-en-2-yl)-4-[(4s)-5,7,8-trimethoxy-2-phenyl-4h-chromen-4-yl]-octahydronaphthalen-1-ol)

PDB for NP0163027 ((1r,4s,4as,7r,8ar)-1,4a-dimethyl-7-(prop-1-en-2-yl)-4-[(4s)-5,7,8-trimethoxy-2-phenyl-4h-chromen-4-yl]-octahydronaphthalen-1-ol)

3D PDB for NP0163027 ((1r,4s,4as,7r,8ar)-1,4a-dimethyl-7-(prop-1-en-2-yl)-4-[(4s)-5,7,8-trimethoxy-2-phenyl-4h-chromen-4-yl]-octahydronaphthalen-1-ol)

SMILES for NP0163027 ((1r,4s,4as,7r,8ar)-1,4a-dimethyl-7-(prop-1-en-2-yl)-4-[(4s)-5,7,8-trimethoxy-2-phenyl-4h-chromen-4-yl]-octahydronaphthalen-1-ol)

INCHI for NP0163027 ((1r,4s,4as,7r,8ar)-1,4a-dimethyl-7-(prop-1-en-2-yl)-4-[(4s)-5,7,8-trimethoxy-2-phenyl-4h-chromen-4-yl]-octahydronaphthalen-1-ol)

Structure for NP0163027 ((1r,4s,4as,7r,8ar)-1,4a-dimethyl-7-(prop-1-en-2-yl)-4-[(4s)-5,7,8-trimethoxy-2-phenyl-4h-chromen-4-yl]-octahydronaphthalen-1-ol)

3D Structure for NP0163027 ((1r,4s,4as,7r,8ar)-1,4a-dimethyl-7-(prop-1-en-2-yl)-4-[(4s)-5,7,8-trimethoxy-2-phenyl-4h-chromen-4-yl]-octahydronaphthalen-1-ol)