NP-MRD: Showing NP-Card for (4ar,8as)-4,4,7-trimethyl-4ah,5h,6h,8ah,9h-naphtho[2,3-b]furan (NP0259411)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-08 01:16:14 UTC

Updated at

2022-09-08 01:16:14 UTC

NP-MRD ID

NP0259411

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4ar,8as)-4,4,7-trimethyl-4ah,5h,6h,8ah,9h-naphtho[2,3-b]furan

Description

Furodysinin 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. Thus, furodysinin is considered to be an isoprenoid. (4ar,8as)-4,4,7-trimethyl-4ah,5h,6h,8ah,9h-naphtho[2,3-b]furan is found in Dysidea avara, Dysidea etheria, Felimare porterae and Lamellodysidea herbacea. (4ar,8as)-4,4,7-trimethyl-4ah,5h,6h,8ah,9h-naphtho[2,3-b]furan was first documented in 2009 (PMID: 19722506). Based on a literature review a small amount of articles have been published on Furodysinin (PMID: 24454572) (PMID: 34043935) (PMID: 26434109).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
    4.2508   -0.7127    0.2016 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8442   -0.4334   -0.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1779    0.5563    0.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7732    0.8777    0.0840 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0988    1.4061    1.3521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2385    1.8515    0.9090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9090    2.9557    1.0762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0807    2.8638    0.4736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1768    1.6238   -0.1210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9864    0.9700    0.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4065   -0.3584   -0.1418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2510   -0.9352   -1.2859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6013   -1.2729    1.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0109   -0.2166   -0.5831 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7474   -1.5409   -0.6229 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1448   -1.2538   -1.1894 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5203   -1.7942    0.0777 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9135   -0.0557   -0.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3757   -0.4257    1.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6575    1.1728    1.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8349    1.8004   -0.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7361    2.2437    1.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0439    0.6653    2.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8532    3.6113    0.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9734    1.1993   -0.6909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7236   -0.1059   -1.8570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5731   -1.4960   -1.9537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0604   -1.5592   -0.8750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6827   -1.5449    1.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1039   -2.2294    0.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2744   -0.8008    1.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0568    0.0718   -1.6808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8975   -1.9955    0.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2541   -2.1805   -1.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0347   -0.7055   -2.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6355   -2.2523   -1.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6 10  2  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 14 15  1  0
 15 16  1  0
 16  2  1  0
 14  4  1  0
  7  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  6
  5 22  1  0
  5 23  1  0
  9 25  1  0
  8 24  1  0
 12 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  6
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
M  END


  Mrv1652309082203162D          

 16 18  0  0  1  0            999 V2000
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3276   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   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
  4  3  1  6  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  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  6 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
  2 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0259411

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C[C@@H]2CC3=C(C=CO3)C(C)(C)[C@@H]2CC1

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O/c1-10-4-5-12-11(8-10)9-14-13(6-7-16-14)15(12,2)3/h6-8,11-12H,4-5,9H2,1-3H3/t11-,12-/m1/s1

> <INCHI_KEY>
OSSOIKJYWQAIQR-VXGBXAGGSA-N

> <FORMULA>
C15H20O

> <MOLECULAR_WEIGHT>
216.324

> <EXACT_MASS>
216.151415264

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
25.85529830489192

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aR,8aS)-4,4,7-trimethyl-4H,4aH,5H,6H,8aH,9H-naphtho[2,3-b]furan

> <JCHEM_LOGP>
3.797794657333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7523275494788595

> <JCHEM_POLAR_SURFACE_AREA>
13.14

> <JCHEM_REFRACTIVITY>
67.0044

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4aR,8aS)-4,4,7-trimethyl-4aH,5H,6H,8aH,9H-naphtho[2,3-b]furan

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.133  -0.294   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.038  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.133  -2.786   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.325  -4.260   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.345  -4.260   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    6   11                                                  
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11    4   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15    2                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O

Average Mass

216.3240 Da

Monoisotopic Mass

216.15142 Da

IUPAC Name

(4aR,8aS)-4,4,7-trimethyl-4H,4aH,5H,6H,8aH,9H-naphtho[2,3-b]furan

Traditional Name

(4aR,8aS)-4,4,7-trimethyl-4aH,5H,6H,8aH,9H-naphtho[2,3-b]furan

CAS Registry Number

Not Available

SMILES

CC1=C[C@@H]2CC3=C(C=CO3)C(C)(C)[C@@H]2CC1

InChI Identifier

InChI=1S/C15H20O/c1-10-4-5-12-11(8-10)9-14-13(6-7-16-14)15(12,2)3/h6-8,11-12H,4-5,9H2,1-3H3/t11-,12-/m1/s1

InChI Key

OSSOIKJYWQAIQR-VXGBXAGGSA-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
Dysidea avara	LOTUS Database	35616633
Dysidea etheria	LOTUS Database	35616633
Felimare porterae	LOTUS Database	35616633
Lamellodysidea herbacea	LOTUS Database	35616633

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
Benzofuran
Heteroaromatic compound
Furan
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organooxygen 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	3.8	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	13.14 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	67 m³·mol⁻¹	ChemAxon
Polarizability	25.86 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

C00021561

Chemspider ID

319758

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

360188

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Williams DE, Marques SO, Hajdu E, Peixinho S, Andersen RJ, Berlinck RG: Pyrodysinoic acid derivatives from the marine sponge Dysidea robusta. J Nat Prod. 2009 Sep;72(9):1691-4. doi: 10.1021/np900033v. [PubMed:19722506 ]
Mudianta IW, Challinor VL, Winters AE, Cheney KL, De Voss JJ, Garson MJ: Synthesis and determination of the absolute configuration of (-)-(5R,6Z)-dendrolasin-5-acetate from the nudibranch Hypselodoris jacksoni. Beilstein J Org Chem. 2013 Dec 23;9:2925-33. doi: 10.3762/bjoc.9.329. eCollection 2013 Dec 23. [PubMed:24454572 ]
Heidary Jamebozorgi F, Yousefzadi M, Firuzi O, Nazemi M, Zare S, Chandran JN, Schneider B, Baldwin IT, Jassbi AR: Cytotoxic furanosesquiterpenoids and steroids from Ircinia mutans sponges. Pharm Biol. 2021 Dec;59(1):575-583. doi: 10.1080/13880209.2021.1920620. [PubMed:34043935 ]
Cue NT, Anh Hle T, Hang DT, Nhiem NX, Dang NH, Nama NH, Yen PH, Thung do C, Thuc VK, Minh CV, Kiema PV: Sesquiterpenes from the Vietnamese Marine Sponge Dysidea fragilis. Nat Prod Commun. 2015 Aug;10(8):1341-2. [PubMed:26434109 ]
LOTUS database [Link]

Showing NP-Card for (4ar,8as)-4,4,7-trimethyl-4ah,5h,6h,8ah,9h-naphtho[2,3-b]furan (NP0259411)

MOL for NP0259411 ((4ar,8as)-4,4,7-trimethyl-4ah,5h,6h,8ah,9h-naphtho[2,3-b]furan)

3D MOL for NP0259411 ((4ar,8as)-4,4,7-trimethyl-4ah,5h,6h,8ah,9h-naphtho[2,3-b]furan)

3D SDF for NP0259411 ((4ar,8as)-4,4,7-trimethyl-4ah,5h,6h,8ah,9h-naphtho[2,3-b]furan)

3D-SDF for NP0259411 ((4ar,8as)-4,4,7-trimethyl-4ah,5h,6h,8ah,9h-naphtho[2,3-b]furan)

PDB for NP0259411 ((4ar,8as)-4,4,7-trimethyl-4ah,5h,6h,8ah,9h-naphtho[2,3-b]furan)

3D PDB for NP0259411 ((4ar,8as)-4,4,7-trimethyl-4ah,5h,6h,8ah,9h-naphtho[2,3-b]furan)

SMILES for NP0259411 ((4ar,8as)-4,4,7-trimethyl-4ah,5h,6h,8ah,9h-naphtho[2,3-b]furan)

INCHI for NP0259411 ((4ar,8as)-4,4,7-trimethyl-4ah,5h,6h,8ah,9h-naphtho[2,3-b]furan)

Structure for NP0259411 ((4ar,8as)-4,4,7-trimethyl-4ah,5h,6h,8ah,9h-naphtho[2,3-b]furan)

3D Structure for NP0259411 ((4ar,8as)-4,4,7-trimethyl-4ah,5h,6h,8ah,9h-naphtho[2,3-b]furan)