NP-MRD: Showing NP-Card for Wulfenioidin I (NP0333096)

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Record Information

Version

2.0

Created at

2024-05-09 00:12:29 UTC

Updated at

2024-09-03 04:21:11 UTC

NP-MRD ID

NP0333096

Natural Product DOI

https://doi.org/10.57994/2395

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Wulfenioidin I

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01212302492D          

 24 27  0  0  1  0            999 V2000
    1.3448   -0.4864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1630   -0.3804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9164    0.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1254   -1.2045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8203   -1.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5528   -1.2696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5904   -0.4455    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2853   -0.8901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8955   -0.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9331    0.8233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6656    1.2028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3606    0.7582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0931    1.1377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7880    0.6930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5205    1.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5581    1.8967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2155    0.6279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7504   -0.1311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3377   -0.7105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9681   -1.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3476   -2.1807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1524   -1.3246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0179   -0.5106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3229   -0.0660    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
  7  6  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  2  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
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 14 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 18 23  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 12 24  1  0  0  0  0
  7 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333096

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=C2N=C(C)OC2=C2C(CCC3C(C)(C)CCC[C@]23C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H31NO/c1-13(2)16-12-15-8-9-17-21(4,5)10-7-11-22(17,6)18(15)20-19(16)23-14(3)24-20/h12-13,17H,7-11H2,1-6H3/t17?,22-/m0/s1

> <INCHI_KEY>
LBBJGNCNTGNGEH-UGNFMNBCSA-N

> <FORMULA>
C22H31NO

> <MOLECULAR_WEIGHT>
325.496

> <EXACT_MASS>
325.240564622

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
40.2392612515768

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(11aS)-2,8,8,11a-tetramethyl-4-(propan-2-yl)-6H,7H,7aH,8H,9H,10H,11H,11aH-phenanthro[3,4-d][1,3]oxazole

> <JCHEM_LOGP>
6.026756450333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
1.7748834454905338

> <JCHEM_POLAR_SURFACE_AREA>
26.03

> <JCHEM_REFRACTIVITY>
98.8326

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(11aS)-4-isopropyl-2,8,8,11a-tetramethyl-6H,7H,7aH,9H,10H,11H-phenanthro[3,4-d][1,3]oxazole

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 21-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JAN-23         0                                  
HETATM    1  C   UNK     0       2.510  -0.908   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.038  -0.710   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.577   0.760   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.967  -2.248   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.265  -3.078   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.632  -2.370   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.702  -0.832   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.999  -1.662   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.405  -0.002   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.475   1.537   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.843   2.245   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.140   1.415   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.507   2.124   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.804   1.294   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.172   2.002   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.242   3.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.469   1.172   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.734  -0.245   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      11.830  -1.326   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      11.141  -2.703   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.849  -4.071   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.618  -2.473   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.367  -0.953   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.069  -0.123   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    9                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   24                                             
CONECT    8    7                                                            
CONECT    9    7    2   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   24                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   14   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   18   22   24                                                  
CONECT   24   23   12    7                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₁NO

Average Mass

325.4960 Da

Monoisotopic Mass

325.24056 Da

IUPAC Name

(11aS)-2,8,8,11a-tetramethyl-4-(propan-2-yl)-6H,7H,7aH,8H,9H,10H,11H,11aH-phenanthro[3,4-d][1,3]oxazole

Traditional Name

(11aS)-4-isopropyl-2,8,8,11a-tetramethyl-6H,7H,7aH,9H,10H,11H-phenanthro[3,4-d][1,3]oxazole

CAS Registry Number

Not Available

SMILES

CC(C)C1=C2N=C(C)OC2=C2C(CCC3C(C)(C)CCC[C@]23C)=C1

InChI Identifier

InChI=1S/C22H31NO/c1-13(2)16-12-15-8-9-17-21(4,5)10-7-11-22(17,6)18(15)20-19(16)23-14(3)24-20/h12-13,17H,7-11H2,1-6H3/t17?,22-/m0/s1

InChI Key

LBBJGNCNTGNGEH-UGNFMNBCSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	393439209@qq.com and liumf@scut.edu.cn	Not Available	Not Available	2024-05-09	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)	393439209@qq.com and liumf@scut.edu.cn	Not Available	Not Available	2024-05-09	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	393439209@qq.com and liumf@scut.edu.cn	Not Available	Not Available	2024-05-09	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	393439209@qq.com and liumf@scut.edu.cn	Not Available	Not Available	2024-05-09	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	393439209@qq.com and liumf@scut.edu.cn	Not Available	Not Available	2024-05-09	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)	393439209@qq.com and liumf@scut.edu.cn	Not Available	Not Available	2024-05-09	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)	393439209@qq.com and liumf@scut.edu.cn	Not Available	Not Available	2024-05-09	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)	393439209@qq.com and liumf@scut.edu.cn	Not Available	Not Available	2024-05-09	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400.15247109, CDCl₃, simulated)	Not Available	Not Available	Not Available	2024-05-09	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
wulfenioides		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	6.03	ChemAxon
pKa (Strongest Basic)	1.77	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.03 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	98.83 m³·mol⁻¹	ChemAxon
Polarizability	40.24 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

Tu WC, Huang YX, Li B, Jiang YJ, Yang QY, Zeb MA, Yang PY, Wang HJ, Li XL, Xiao WL, Zheng CB, Liu MF: Wulfenioidins D-N, Structurally Diverse Diterpenoids with Anti-Zika Virus Activity Isolated from Orthosiphon wulfenioides. J Nat Prod. 2023 Oct 27;86(10):2348-2359. doi: 10.1021/acs.jnatprod.3c00543. Epub 2023 Sep 22. [PubMed:37737089 ]

Showing NP-Card for Wulfenioidin I (NP0333096)

MOL for NP0333096 (Wulfenioidin I)

3D MOL for NP0333096 (Wulfenioidin I)

3D SDF for NP0333096 (Wulfenioidin I)

3D-SDF for NP0333096 (Wulfenioidin I)

PDB for NP0333096 (Wulfenioidin I)

3D PDB for NP0333096 (Wulfenioidin I)

SMILES for NP0333096 (Wulfenioidin I)

INCHI for NP0333096 (Wulfenioidin I)

Structure for NP0333096 (Wulfenioidin I)

3D Structure for NP0333096 (Wulfenioidin I)