NP-MRD: Showing NP-Card for Atractylenolide I (NP0137192)

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Record Information

Version

2.0

Created at

2022-05-30 16:44:36 UTC

Updated at

2022-05-30 16:44:36 UTC

NP-MRD ID

NP0137192

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Atractylenolide I

Description

Atractylenolide I belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Atractylenolide I was first documented in 2022 (PMID: 35378415). Based on a literature review a small amount of articles have been published on Atractylenolide I (PMID: 35354423) (PMID: 35235139) (PMID: 35126160).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
   -1.3896   -2.5170   -0.5385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4163   -1.2548   -0.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1732   -1.0346    1.1468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2556    0.3833    1.5534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2446    1.2844    0.3472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9368    1.1662   -0.4219 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0408    2.1259   -1.5908 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1004    1.7000    0.4894 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2924    1.1778    0.6702 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3852    1.5315    1.4722 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3845    0.6095    1.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5071    0.6477    1.8303 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9028   -0.3683    0.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7289   -1.5143   -0.2019 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6771   -0.0171   -0.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7426   -0.6407   -0.9890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6796   -0.2377   -0.8681 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8919   -3.3443   -0.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8588   -2.7522   -1.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7567   -1.6443    1.9976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2133   -1.4402    0.9769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2148    0.5542    2.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4372    0.6070    2.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3277    2.3421    0.6719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034    1.0429   -0.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9279    2.7774   -1.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1484    2.7879   -1.6672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1357    1.5189   -2.4992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1377    2.5879    1.0506 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8097   -1.2607   -0.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5460   -2.4352    0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4367   -1.7820   -1.2513 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0958   -0.5345   -2.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8075   -1.7568   -0.8147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1265   -0.3102   -1.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  6
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  9 15  1  0
  6 17  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  6
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
M  END


  Mrv1652305302218442D          

 17 19  0  0  0  0            999 V2000
    1.5983   -0.4834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -1.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -2.6029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5433   -1.9354    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
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0137192

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2CC3C(=C)CCCC3(C)C=C2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h8,12H,1,4-7H2,2-3H3

> <INCHI_KEY>
ZTVSGQPHMUYCRS-UHFFFAOYSA-N

> <FORMULA>
C15H18O2

> <MOLECULAR_WEIGHT>
230.307

> <EXACT_MASS>
230.13067982

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
26.112137950694745

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,8a-dimethyl-5-methylidene-2H,4H,4aH,5H,6H,7H,8H,8aH-naphtho[2,3-b]furan-2-one

> <JCHEM_LOGP>
3.0020809539999993

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.010557037842069

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
68.4197

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3,8a-dimethyl-5-methylidene-4H,4aH,6H,7H,8H-naphtho[2,3-b]furan-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 30-MAY-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-MAY-22         0                                  
HETATM    1  C   UNK     0       2.983  -0.902   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.459  -2.367   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.925  -0.533   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.591  -5.923   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.459  -4.859   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.554  -3.613   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.014  -3.613   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    5   12   13                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    3   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15    2   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₂

Average Mass

230.3070 Da

Monoisotopic Mass

230.13068 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1=C2CC3C(=C)CCCC3(C)C=C2OC1=O

InChI Identifier

InChI=1S/C15H18O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h8,12H,1,4-7H2,2-3H3

InChI Key

ZTVSGQPHMUYCRS-UHFFFAOYSA-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 naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
2-furanone
Dihydrofuran
Enol ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
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

External Links

HMDB ID

HMDB0248706

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00012887

Chemspider ID

34560784

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14448072

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chen Z, Zhou L, Ge Y, Chen J, Du W, Xiao L, Tong P, Huang J, Shan L, Efferth T: Fuzi decoction ameliorates pain and cartilage degeneration of osteoarthritic rats through PI3K-Akt signaling pathway and its clinical retrospective evidence. Phytomedicine. 2022 Jun;100:154071. doi: 10.1016/j.phymed.2022.154071. Epub 2022 Mar 20. [PubMed:35378415 ]
Britza SM, Musgrave IF, Byard RW: Implications for herbal polypharmacy: coumarin-induced hepatotoxicity increased through common herbal phytochemicals astragaloside IV and atractylenolide I. Toxicol Mech Methods. 2022 Oct;32(8):606-615. doi: 10.1080/15376516.2022.2057267. Epub 2022 Mar 30. [PubMed:35354423 ]
Han Y, Bai C, He XM, Ren QL: P2X7 receptor involved in antitumor activity of atractylenolide I in human cervical cancer cells. Purinergic Signal. 2022 Mar 2. pii: 10.1007/s11302-022-09854-6. doi: 10.1007/s11302-022-09854-6. [PubMed:35235139 ]
Du Z, Ma Z, Lai S, Ding Q, Hu Z, Yang W, Qian Q, Zhu L, Dou X, Li S: Atractylenolide I Ameliorates Acetaminophen-Induced Acute Liver Injury via the TLR4/MAPKs/NF-kappaB Signaling Pathways. Front Pharmacol. 2022 Jan 21;13:797499. doi: 10.3389/fphar.2022.797499. eCollection 2022. [PubMed:35126160 ]

Showing NP-Card for Atractylenolide I (NP0137192)

MOL for NP0137192 (Atractylenolide I)

3D MOL for NP0137192 (Atractylenolide I)

3D SDF for NP0137192 (Atractylenolide I)

3D-SDF for NP0137192 (Atractylenolide I)

PDB for NP0137192 (Atractylenolide I)

3D PDB for NP0137192 (Atractylenolide I)

SMILES for NP0137192 (Atractylenolide I)

INCHI for NP0137192 (Atractylenolide I)

Structure for NP0137192 (Atractylenolide I)

3D Structure for NP0137192 (Atractylenolide I)