NP-MRD: Showing NP-Card for agarsenone (NP0043501)

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Record Information

Version

1.0

Created at

2021-06-21 00:53:40 UTC

Updated at

2021-06-30 00:19:13 UTC

NP-MRD ID

NP0043501

Secondary Accession Numbers

None

Natural Product Identification

Common Name

agarsenone

Provided By

JEOL Database JEOL Logo

Description

(5S,8R)-1,5,8-trimethyl-4H,5H,6H,7H,8H,9H-naphtho[2,1-b]furan-6-one belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. agarsenone is found in Commiphora erythraea. It was first documented in 2002 (PMID: 29437326). Based on a literature review a significant number of articles have been published on (5S,8R)-1,5,8-trimethyl-4H,5H,6H,7H,8H,9H-naphtho[2,1-b]furan-6-one (PMID: 27466641) (PMID: 27253005) (PMID: 26389468) (PMID: 26389426) (PMID: 26389424) (PMID: 26389377).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306222119252D          

 17 19  0  0  1  0            999 V2000
    5.2150    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7804    1.1137    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9558    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5212    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9112   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4766   -0.9900    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6520   -0.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2620   -0.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6966    0.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1640    1.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4002    0.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4608   -0.0406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3606    1.8953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8666   -1.7170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7358   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1258   -1.0415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1704    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  8 12  1  0  0  0  0
 10 13  1  0  0  0  0
  6 14  1  1  0  0  0
  5 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  2 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043501

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC(=O)C2=C(C1)C1=C(C[C@@H]2C)OC=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O2/c1-8-4-11-14(12(16)5-8)9(2)6-13-15(11)10(3)7-17-13/h7-9H,4-6H2,1-3H3/t8-,9+/m1/s1

> <INCHI_KEY>
ZYFISEHWAGWCRY-BDAKNGLRSA-N

> <FORMULA>
C15H18O2

> <MOLECULAR_WEIGHT>
230.307

> <EXACT_MASS>
230.13067982

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
26.459516348428004

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,8R)-1,5,8-trimethyl-4H,5H,6H,7H,8H,9H-naphtho[2,1-b]furan-6-one

> <ALOGPS_LOGP>
3.10

> <JCHEM_LOGP>
3.4389610740000003

> <ALOGPS_LOGS>
-3.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7040636764491794

> <JCHEM_POLAR_SURFACE_AREA>
30.21

> <JCHEM_REFRACTIVITY>
67.9971

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S,8R)-1,5,8-trimethyl-4H,5H,7H,8H,9H-naphtho[2,1-b]furan-6-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 22-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-21         0                                  
HETATM    1  C   UNK     0       9.735   3.388   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.923   2.079   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.384   2.127   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.573   0.818   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.301  -0.539   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.490  -1.848   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.950  -1.800   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.222  -0.443   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.034   0.866   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.039   2.042   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.614   1.460   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.727  -0.076   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.406   3.538   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.218  -3.205   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.840  -0.587   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.568  -1.944   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.651   0.722   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6   15                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11    8                                                       
CONECT   13   10                                                            
CONECT   14    6                                                            
CONECT   15    5   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    2                                                       
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

(5S,8R)-1,5,8-trimethyl-4H,5H,6H,7H,8H,9H-naphtho[2,1-b]furan-6-one

Traditional Name

(5S,8R)-1,5,8-trimethyl-4H,5H,7H,8H,9H-naphtho[2,1-b]furan-6-one

CAS Registry Number

Not Available

SMILES

[H]C1=C(C2=C(O1)C([H])([H])[C@@]([H])(C1=C2C([H])([H])[C@@]([H])(C([H])([H])[H])C([H])([H])C1=O)C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C15H18O2/c1-8-4-11-14(12(16)5-8)9(2)6-13-15(11)10(3)7-17-13/h7-9H,4-6H2,1-3H3/t8-,9+/m1/s1

InChI Key

ZYFISEHWAGWCRY-BDAKNGLRSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Benzene-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Benzene-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Commiphora erythraea	JEOL database	Santoro, S., et al, J. Nat. Prod. 76, 1254 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Cadinane sesquiterpenoid
Naphthofuran
Cyclohexenone
Heteroaromatic compound
Furan
Ketone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	3.1	ALOGPS
logP	3.44	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	30.21 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68 m³·mol⁻¹	ChemAxon
Polarizability	26.46 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

29784864

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71745332

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Authors unspecified: Childhood Cancer Genomics (PDQ(R)): Health Professional Version. 2002. [PubMed:27466641 ]
Authors unspecified: Thyroid Cancer Screening (PDQ(R)): Patient Version. 2002. [PubMed:29437326 ]
Authors unspecified: Childhood Vascular Tumors Treatment (PDQ(R)): Patient Version. 2002. [PubMed:27253005 ]
Authors unspecified: Stomach (Gastric) Cancer Prevention (PDQ(R)): Patient Version. 2002. [PubMed:26389468 ]
Authors unspecified: Childhood Central Nervous System Atypical Teratoid/Rhabdoid Tumor Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389426 ]
Authors unspecified: Cancer Prevention Overview (PDQ(R)): Patient Version. 2002. [PubMed:26389424 ]
Authors unspecified: Acute Myeloid Leukemia Treatment (PDQ(R)): Patient Version. 2002. [PubMed:26389377 ]
Authors unspecified: Cervical Cancer Prevention (PDQ(R)): Patient Version. 2002. [PubMed:26389339 ]
Authors unspecified: Pheochromocytoma and Paraganglioma Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389312 ]
Authors unspecified: Prostate Cancer Screening (PDQ(R)): Patient Version. 2002. [PubMed:26389306 ]
Santoro, S., et al. (2013). Santoro, S., et al, J. Nat. Prod. 76, 1254 (2013). J. Nat. Prod..

Showing NP-Card for agarsenone (NP0043501)

MOL for NP0043501 (agarsenone)

3D MOL for NP0043501 (agarsenone)

3D SDF for NP0043501 (agarsenone)

3D-SDF for NP0043501 (agarsenone)

PDB for NP0043501 (agarsenone)

3D PDB for NP0043501 (agarsenone)

SMILES for NP0043501 (agarsenone)

INCHI for NP0043501 (agarsenone)

Structure for NP0043501 (agarsenone)

3D Structure for NP0043501 (agarsenone)