NP-MRD: Showing NP-Card for Wulfenioidin D (NP0333091)

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Record Information

Version

2.0

Created at

2024-05-08 23:24:11 UTC

Updated at

2024-09-03 04:21:10 UTC

NP-MRD ID

NP0333091

Natural Product DOI

https://doi.org/10.57994/2390

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Wulfenioidin D

Description

Wulfenioidin D belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Wulfenioidin D was first documented in 2023 (PMID: 37737089). Based on a literature review very few articles have been published on Wulfenioidin D.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01212302002D          

 22 24  0  0  1  0            999 V2000
    0.5284   -2.0872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2084   -1.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5504   -2.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6302   -1.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8508   -0.2365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6495   -0.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2277   -0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0264   -0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2470    0.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6046   -1.0006    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9071   -0.2331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7305   -0.2835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2554    0.3530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9666    1.1258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0691    0.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9370   -1.0823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2411   -1.5255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7045   -1.3848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3840   -1.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5853   -2.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0071   -1.4135    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7865   -2.2085    0.0000 H   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
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 10  8  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 10 17  1  1  0  0  0
 16 18  2  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  0  0  0  0
 21  7  1  0  0  0  0
 21  2  1  0  0  0  0
 21 22  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0333091

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@]3(OC(=O)C(=C3)C(C)C)C(C)=C1CCCC2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C19H28O2/c1-12(2)15-11-19(21-17(15)20)10-8-16-14(13(19)3)7-6-9-18(16,4)5/h11-12,16H,6-10H2,1-5H3/t16-,19-/m1/s1

> <INCHI_KEY>
SFYGGSVIOYHDHZ-VQIMIIECSA-N

> <FORMULA>
C19H28O2

> <MOLECULAR_WEIGHT>
288.431

> <EXACT_MASS>
288.208930142

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
34.16185292146983

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,4'aS)-1',5',5'-trimethyl-4-(propan-2-yl)-4',4'a,5',6',7',8'-hexahydro-3'H,5H-spiro[furan-2,2'-naphthalen]-5-one

> <JCHEM_LOGP>
4.966998171333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.908497283773561

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
86.15659999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,4'aS)-4-isopropyl-1',5',5'-trimethyl-3',4',4'a,6',7',8'-hexahydrospiro[furan-2,2'-naphthalen]-5-one

> <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       0.986  -3.896   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.256  -3.024   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.894  -4.425   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.176  -1.925   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.588  -0.441   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.079  -0.056   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.158  -1.155   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.649  -0.769   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.061   0.715   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.729  -1.868   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.293  -0.435   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.830  -0.529   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.810   0.659   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.271   2.101   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.329   0.404   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.216  -2.020   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.917  -2.848   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      10.648  -2.585   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.317  -3.352   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.826  -3.737   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.747  -2.639   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0       3.335  -4.122   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    4   21                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   21                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   17   19                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   12   17   18                                                  
CONECT   17   16   10                                                       
CONECT   18   16                                                            
CONECT   19   10   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    7    2   22                                             
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₈O₂

Average Mass

288.4310 Da

Monoisotopic Mass

288.20893 Da

IUPAC Name

(2R,4'aS)-1',5',5'-trimethyl-4-(propan-2-yl)-4',4'a,5',6',7',8'-hexahydro-3'H,5H-spiro[furan-2,2'-naphthalen]-5-one

Traditional Name

(2R,4'aS)-4-isopropyl-1',5',5'-trimethyl-3',4',4'a,6',7',8'-hexahydrospiro[furan-2,2'-naphthalen]-5-one

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@]3(OC(=O)C(=C3)C(C)C)C(C)=C1CCCC2(C)C

InChI Identifier

InChI=1S/C19H28O2/c1-12(2)15-11-19(21-17(15)20)10-8-16-14(13(19)3)7-6-9-18(16,4)5/h11-12,16H,6-10H2,1-5H3/t16-,19-/m1/s1

InChI Key

SFYGGSVIOYHDHZ-VQIMIIECSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)	393439209@qq.com and liumf@scut.edu.cn	Not Available	Not Available	2024-05-08	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	2024-05-08	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)	393439209@qq.com and liumf@scut.edu.cn	Not Available	Not Available	2024-05-08	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	2024-05-08	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)	393439209@qq.com and liumf@scut.edu.cn	Not Available	Not Available	2024-05-08	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	2024-05-08	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	393439209@qq.com and liumf@scut.edu.cn	Not Available	Not Available	2024-05-08	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	2024-05-08	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, 400.152200825, CDCl₃, simulated)	Not Available	Not Available	Not Available	2024-05-08	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
wulfenioides		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Farsesane sesquiterpenoid
Sesquiterpenoid
Fatty alcohol ester
Fatty acid ester
Fatty acyl
2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Dihydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	4.97	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	86.16 m³·mol⁻¹	ChemAxon
Polarizability	34.16 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

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 D (NP0333091)

MOL for NP0333091 (Wulfenioidin D)

3D MOL for NP0333091 (Wulfenioidin D)

3D SDF for NP0333091 (Wulfenioidin D)

3D-SDF for NP0333091 (Wulfenioidin D)

PDB for NP0333091 (Wulfenioidin D)

3D PDB for NP0333091 (Wulfenioidin D)

SMILES for NP0333091 (Wulfenioidin D)

INCHI for NP0333091 (Wulfenioidin D)

Structure for NP0333091 (Wulfenioidin D)

3D Structure for NP0333091 (Wulfenioidin D)