NP-MRD: Showing NP-Card for Sacrone B (NP0333137)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2024-05-11 07:27:16 UTC

Updated at

2024-05-13 01:12:41 UTC

NP-MRD ID

NP0333137

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sacrone B

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01232310032D          

 23 24  0  0  1  0            999 V2000
   -1.0432   -1.5316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6071   -0.8314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2175   -0.8590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6537   -0.1587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2675   -0.7099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3031    0.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2653    0.5691    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8734    1.2974    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4410    2.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6770    1.4841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4663    1.2440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9025    1.9443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5142    2.6722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0298    0.6415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2165   -0.1621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9764   -0.9514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3739   -1.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622   -2.2428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5703   -1.7017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7810   -1.4616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5592    0.5968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9954   -0.1035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8199   -0.0759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  7  4  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  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  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
  7 21  1  1  0  0  0
 21 22  1  0  0  0  0
  2 22  1  0  0  0  0
 22 23  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0333137

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2CC\C(C)=C/CC\C(C=O)=C/[C@H](O)[C@H](CC1=O)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O3/c1-13-6-5-7-15(12-21)10-19(23)17-11-18(22)14(2)16(9-8-13)20(17,3)4/h6,10,12,17,19,23H,5,7-9,11H2,1-4H3/b13-6-,15-10+/t17-,19-/m0/s1

> <INCHI_KEY>
AAIXKPFFTVDBKX-QIXJKMEFSA-N

> <FORMULA>
C20H28O3

> <MOLECULAR_WEIGHT>
316.441

> <EXACT_MASS>
316.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
35.78682110634318

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,3E,7Z)-2-hydroxy-8,12,15,15-tetramethyl-13-oxobicyclo[9.3.1]pentadeca-3,7,11-triene-4-carbaldehyde

> <JCHEM_LOGP>
3.29036782

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.48242434575676

> <JCHEM_PKA_STRONGEST_BASIC>
-3.025186399743516

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
94.98439999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3E,7Z)-2-hydroxy-8,12,15,15-tetramethyl-13-oxobicyclo[9.3.1]pentadeca-3,7,11-triene-4-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-JAN-23         0                                  
HETATM    1  C   UNK     0      -1.947  -2.859   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.133  -1.552   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.406  -1.603   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.220  -0.296   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.366  -1.325   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.432   0.654   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.495   1.062   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.630   2.422   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.823   3.733   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.130   2.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.604   2.322   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.418   3.629   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.693   4.988   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.656   1.197   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.004  -0.303   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.556  -1.776   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.431  -2.828   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.156  -4.187   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.931  -3.176   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.458  -2.728   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.044   1.114   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.858  -0.193   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -3.397  -0.142   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4   20                                                  
CONECT    4    3    5    6    7                                             
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    4    8   21                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19    3                                                       
CONECT   21    7   22                                                       
CONECT   22   21    2   23                                                  
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₈O₃

Average Mass

316.4410 Da

Monoisotopic Mass

316.20384 Da

IUPAC Name

(1R,2S,3E,7Z)-2-hydroxy-8,12,15,15-tetramethyl-13-oxobicyclo[9.3.1]pentadeca-3,7,11-triene-4-carbaldehyde

Traditional Name

(1R,2S,3E,7Z)-2-hydroxy-8,12,15,15-tetramethyl-13-oxobicyclo[9.3.1]pentadeca-3,7,11-triene-4-carbaldehyde

CAS Registry Number

Not Available

SMILES

CC1=C2CC\C(C)=C/CC\C(C=O)=C/[C@H](O)[C@H](CC1=O)C2(C)C

InChI Identifier

InChI=1S/C20H28O3/c1-13-6-5-7-15(12-21)10-19(23)17-11-18(22)14(2)16(9-8-13)20(17,3)4/h6,10,12,17,19,23H,5,7-9,11H2,1-4H3/b13-6-,15-10+/t17-,19-/m0/s1

InChI Key

AAIXKPFFTVDBKX-QIXJKMEFSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	zbyqcy@163.com	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	zbyqcy@163.com	Not Available	Not Available	2024-05-11	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	zbyqcy@163.com	Not Available	Not Available	2024-05-11	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	zbyqcy@163.com	Not Available	Not Available	2024-05-11	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	zbyqcy@163.com	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	zbyqcy@163.com	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	zbyqcy@163.com	Not Available	Not Available	2024-05-11	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
sacra		Not Available

Chemical Taxonomy

Classification

Not classified

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	3.29	ChemAxon
pKa (Strongest Acidic)	14.48	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	94.98 m³·mol⁻¹	ChemAxon
Polarizability	35.79 Å³	ChemAxon
Number of Rings	2	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

Not Available

References

General References

Yuan Z, Liu D, Zhang B, Cao S, Yao T, Zhao Q, Qiu F, Zhao F: New verticillane-diterpenoid as potent NF-kappaB inhibitor isolated from the gum resin of Boswellia sacra. Fitoterapia. 2023 Apr;166:105460. doi: 10.1016/j.fitote.2023.105460. Epub 2023 Feb 16. [PubMed:36801349 ]

Showing NP-Card for Sacrone B (NP0333137)

MOL for NP0333137 (Sacrone B)

3D MOL for NP0333137 (Sacrone B)

3D SDF for NP0333137 (Sacrone B)

3D-SDF for NP0333137 (Sacrone B)

PDB for NP0333137 (Sacrone B)

3D PDB for NP0333137 (Sacrone B)

SMILES for NP0333137 (Sacrone B)

INCHI for NP0333137 (Sacrone B)

Structure for NP0333137 (Sacrone B)

3D Structure for NP0333137 (Sacrone B)