NP-MRD: Showing NP-Card for (8r)-1,5,8-trimethyl-7h,8h,9h-naphtho[2,1-b]furan-6-one (NP0248568)

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Record Information

Version

2.0

Created at

2022-09-07 10:52:15 UTC

Updated at

2022-09-07 10:52:16 UTC

NP-MRD ID

NP0248568

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(8r)-1,5,8-trimethyl-7h,8h,9h-naphtho[2,1-b]furan-6-one

Description

Myrrhone belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (8r)-1,5,8-trimethyl-7h,8h,9h-naphtho[2,1-b]furan-6-one is found in Commiphora myrrha. (8r)-1,5,8-trimethyl-7h,8h,9h-naphtho[2,1-b]furan-6-one was first documented in 2020 (PMID: 32365391). Based on a literature review a small amount of articles have been published on Myrrhone (PMID: 35745024) (PMID: 35582102) (PMID: 35983967) (PMID: 35075958).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
   -0.8765   -3.4953    0.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0517   -2.0038    0.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2608   -1.4405    0.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4184   -0.0496    0.4580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4549    0.7040    0.7527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1733    1.9776    0.6801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8471    2.0549    0.3082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0856    3.3048    0.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3551    0.7752    0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1417    0.1928   -0.1797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0183   -1.1777   -0.2322 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2780   -1.8135   -0.5929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5458   -3.0252   -0.4437 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3127   -0.9290   -1.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3159    0.4301   -0.5370 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7671    0.2387    0.9127 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9686    1.0957   -0.4826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5693   -3.8327   -1.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8858   -3.9362    0.1684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2270   -3.8655    0.8193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0797   -2.0805    0.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8467    2.8268    0.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8344    4.1527    0.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5287    3.3567   -0.8418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4878    3.6049    1.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3239   -1.3281   -1.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0499   -0.7843   -2.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0729    1.0844   -1.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3906   -0.6513    0.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3759    1.1121    1.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8917    0.0947    1.5760 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0245    1.9240    0.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7888    1.4833   -1.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 14  1  0
 14 12  1  0
 12 13  2  0
 12 11  1  0
 11  2  2  0
  2  1  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 17  1  0
 17 15  1  0
 10 11  1  0
  9  4  1  0
 16 29  1  0
 16 30  1  0
 16 31  1  0
 15 28  1  6
 14 26  1  0
 14 27  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  6 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
 17 32  1  0
 17 33  1  0
M  END


  Mrv1652309072212522D          

 17 19  0  0  1  0            999 V2000
    1.1937   -1.7170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4083   -0.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983   -0.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995   -0.0406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6601    0.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963    1.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996    1.8953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637    0.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5391    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3245   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655   -1.0415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799    1.1137    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1547    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1045    1.1395    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
  3  4  2  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
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  2 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 10 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0248568

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC(=O)C2=C(C)C=C3OC=C(C)C3=C2C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O2/c1-8-4-11-14(12(16)5-8)9(2)6-13-15(11)10(3)7-17-13/h6-8H,4-5H2,1-3H3/t8-/m1/s1

> <INCHI_KEY>
SHEOKDCVBGTHJG-MRVPVSSYSA-N

> <FORMULA>
C15H16O2

> <MOLECULAR_WEIGHT>
228.291

> <EXACT_MASS>
228.115029755

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
25.650105337206544

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
3.7541099439999996

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.199529490834298

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7794040495697647

> <JCHEM_POLAR_SURFACE_AREA>
30.21

> <JCHEM_REFRACTIVITY>
67.79880000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       2.228  -3.205   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.956  -1.848   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.495  -1.800   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.223  -0.443   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.719  -0.076   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.832   1.460   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.406   2.042   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.039   3.538   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.412   0.866   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.873   0.818   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.145  -0.539   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.606  -0.587   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.122  -1.944   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.206   0.722   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.522   2.079   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.289   3.388   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.062   2.127   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7    4   10                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10    2   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   10                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₆O₂

Average Mass

228.2910 Da

Monoisotopic Mass

228.11503 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

C[C@H]1CC(=O)C2=C(C)C=C3OC=C(C)C3=C2C1

InChI Identifier

InChI=1S/C15H16O2/c1-8-4-11-14(12(16)5-8)9(2)6-13-15(11)10(3)7-17-13/h6-8H,4-5H2,1-3H3/t8-/m1/s1

InChI Key

SHEOKDCVBGTHJG-MRVPVSSYSA-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

Species Name	Source	Reference
Commiphora myrrha	LOTUS Database	35616633

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

Cadinane sesquiterpenoid
Sesquiterpenoid
Naphthofuran
Tetralin
Benzofuran
Aryl ketone
Aryl alkyl ketone
Benzenoid
Heteroaromatic compound
Furan
Ketone
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
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	3.75	ChemAxon
pKa (Strongest Acidic)	17.2	ChemAxon
pKa (Strongest Basic)	-2.8	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	67.8 m³·mol⁻¹	ChemAxon
Polarizability	25.65 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

C00034610

Chemspider ID

113061961

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

134715234

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Greve HL, Kaiser M, Schmidt TJ: Investigation of Antiplasmodial Effects of Terpenoid Compounds Isolated from Myrrh. Planta Med. 2020 Jun;86(9):643-654. doi: 10.1055/a-1157-9463. Epub 2020 May 4. [PubMed:32365391 ]
Ulrich J, Stiltz S, St-Gelais A, El Gaafary M, Simmet T, Syrovets T, Schmiech M: Phytochemical Composition of Commiphora Oleogum Resins and Their Cytotoxicity against Skin Cancer Cells. Molecules. 2022 Jun 17;27(12):3903. doi: 10.3390/molecules27123903. [PubMed:35745024 ]
Teng YJ, Deng Z, Ouyang ZG, Zhou Q, Mei S, Fan XX, Wu YR, Long HP, Fang LY, Yin DL, Zhang BY, Guo YM, Zhu WH, Huang Z, Zheng P, Ning DM, Tian XF: Xihuang pills induce apoptosis in hepatocellular carcinoma by suppressing phosphoinositide 3-kinase/protein kinase-B/mechanistic target of rapamycin pathway. World J Gastrointest Oncol. 2022 Apr 15;14(4):872-886. doi: 10.4251/wjgo.v14.i4.872. [PubMed:35582102 ]
Sun Z, Zhan X: Myrrhone inhibits the progression of hepatic fibrosis by regulating the abnormal activation of hepatic stellate cells. J Biochem Mol Toxicol. 2022 Nov;36(11):e23177. doi: 10.1002/jbt.23177. Epub 2022 Aug 19. [PubMed:35983967 ]
Xu N, Nyamdavaa E, Yu J, Xiao H, Liu J, Li S, Xu L: A new benzofuran compound from the resinous exudates of Commiphora myrrha. Nat Prod Res. 2023 May;37(9):1416-1420. doi: 10.1080/14786419.2021.2011272. Epub 2022 Jan 25. [PubMed:35075958 ]
LOTUS database [Link]

Showing NP-Card for (8r)-1,5,8-trimethyl-7h,8h,9h-naphtho[2,1-b]furan-6-one (NP0248568)

MOL for NP0248568 ((8r)-1,5,8-trimethyl-7h,8h,9h-naphtho[2,1-b]furan-6-one)

3D MOL for NP0248568 ((8r)-1,5,8-trimethyl-7h,8h,9h-naphtho[2,1-b]furan-6-one)

3D SDF for NP0248568 ((8r)-1,5,8-trimethyl-7h,8h,9h-naphtho[2,1-b]furan-6-one)

3D-SDF for NP0248568 ((8r)-1,5,8-trimethyl-7h,8h,9h-naphtho[2,1-b]furan-6-one)

PDB for NP0248568 ((8r)-1,5,8-trimethyl-7h,8h,9h-naphtho[2,1-b]furan-6-one)

3D PDB for NP0248568 ((8r)-1,5,8-trimethyl-7h,8h,9h-naphtho[2,1-b]furan-6-one)

SMILES for NP0248568 ((8r)-1,5,8-trimethyl-7h,8h,9h-naphtho[2,1-b]furan-6-one)

INCHI for NP0248568 ((8r)-1,5,8-trimethyl-7h,8h,9h-naphtho[2,1-b]furan-6-one)

Structure for NP0248568 ((8r)-1,5,8-trimethyl-7h,8h,9h-naphtho[2,1-b]furan-6-one)

3D Structure for NP0248568 ((8r)-1,5,8-trimethyl-7h,8h,9h-naphtho[2,1-b]furan-6-one)