NP-MRD: Showing NP-Card for Scalarafuran (NP0081685)

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Record Information

Version

2.0

Created at

2022-04-29 02:44:23 UTC

Updated at

2022-04-29 02:44:23 UTC

NP-MRD ID

NP0081685

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Scalarafuran

Description

Scalarafuran belongs to the class of organic compounds known as scalarane sesterterpenoids. These are sesterterpenoids with a structure based on the scalarane backbone. Scalarane is a tetracyclic compound, which is similar the homoandrostane with five methyl groups at the 4-, 4-, 8-, 17-, 17a-positions. Scalarafuran is found in Hyrtios erectus and Hyrtios gumminae. Scalarafuran was first documented in 2007 (PMID: 18000710). Based on a literature review a small amount of articles have been published on Scalarafuran (PMID: 30487463) (PMID: 21800844).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292204442D          

 31 35  0  0  1  0            999 V2000
    4.0141    0.4627    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6125   -0.2580    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0358   -0.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8607   -0.9535    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2623   -0.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8390    0.4752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3816    1.0967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1403    0.7726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0666   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2840   -1.6617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1089   -1.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5323   -2.3572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5105   -0.9284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7876   -0.2705    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3643    0.4376    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7659    1.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5908    1.1708    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9924    1.8915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5394    0.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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  2 14  1  0  0  0  0
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  1 17  1  0  0  0  0
 17 18  1  1  0  0  0
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M  END

     RDKit          3D

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   -2.2727   -0.6991    0.4172 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.8499   -1.1837    1.7563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3154   -0.9570    1.8643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6505    0.4789    1.6538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0741    1.0814    0.4137 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1685    2.6075    0.5945 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6379    0.7554    0.2890 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.0236   -0.1616   -0.5282 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.8430   -4.2046    0.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6435   -2.1694    2.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5872   -0.0284    1.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304292204442D          

 31 35  0  0  1  0            999 V2000
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    3.6125   -0.2580    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    6.1089   -1.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5323   -2.3572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5105   -0.9284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7876   -0.2705    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.7659    1.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5908    1.1708    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9924    1.8915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5394    0.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1378   -0.2956    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5611   -1.0037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3129   -0.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1104    0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2912    1.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2966   -1.1330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9410    1.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2109   -0.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4157    1.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 25 26  1  0  0  0  0
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 14 30  1  1  0  0  0
  1 31  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0081685

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1C[C@H]2[C@]3(C)CC[C@H]4C(C)(C)CCC[C@]4(C)[C@H]3C[C@@H](O)[C@]2(C)C2=COC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O4/c1-16(28)31-19-12-22-26(5)11-8-20-24(2,3)9-7-10-25(20,4)21(26)13-23(29)27(22,6)18-15-30-14-17(18)19/h14-15,19-23,29H,7-13H2,1-6H3/t19-,20-,21+,22-,23+,25-,26+,27+/m0/s1

> <INCHI_KEY>
JRKYCNUZXAQLDW-PVRRMCBNSA-N

> <FORMULA>
C27H40O4

> <MOLECULAR_WEIGHT>
428.613

> <EXACT_MASS>
428.292659768

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
49.567227599734

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,4S,10S,11R,13R,14S,19S)-11-hydroxy-1,10,14,18,18-pentamethyl-7-oxapentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosa-5,8-dien-4-yl acetate

> <ALOGPS_LOGP>
5.52

> <JCHEM_LOGP>
5.0308052550000015

> <ALOGPS_LOGS>
-4.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.476059345729634

> <JCHEM_PKA_STRONGEST_BASIC>
-2.842801778304699

> <JCHEM_POLAR_SURFACE_AREA>
59.67

> <JCHEM_REFRACTIVITY>
120.1761

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.11e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4S,10S,11R,13R,14S,19S)-11-hydroxy-1,10,14,18,18-pentamethyl-7-oxapentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosa-5,8-dien-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       7.493   0.864   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.743  -0.482   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.534  -1.803   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.073  -1.780   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.823  -0.435   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.033   0.887   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.046   2.047   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      11.462   1.442   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      11.324  -0.092   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.864  -3.102   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      11.403  -3.078   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.194  -4.400   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      12.153  -1.733   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.204  -0.505   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.413   0.817   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.163   2.162   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.703   2.185   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.452   3.531   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.874   0.793   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.124  -0.552   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.914  -1.874   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.454  -1.850   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.584  -0.575   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.206   0.747   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.543   2.092   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.083   2.115   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.554  -2.115   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.709  -1.411   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.623   2.139   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.994  -1.827   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.243   2.209   0.000  0.00  0.00           C+0
CONECT    1    2    6   17   31                                             
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    5                                                       
CONECT   10    4   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    2   15   22   30                                             
CONECT   15   14   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16    1   18                                                  
CONECT   18   17                                                            
CONECT   19   15   20   26   29                                             
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21   14                                                       
CONECT   23   20   24   27   28                                             
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   19                                                       
CONECT   27   23                                                            
CONECT   28   23                                                            
CONECT   29   19                                                            
CONECT   30   14                                                            
CONECT   31    1                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₀O₄

Average Mass

428.6130 Da

Monoisotopic Mass

428.29266 Da

IUPAC Name

(1R,2S,4S,10S,11R,13R,14S,19S)-11-hydroxy-1,10,14,18,18-pentamethyl-7-oxapentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosa-5,8-dien-4-yl acetate

Traditional Name

(1R,2S,4S,10S,11R,13R,14S,19S)-11-hydroxy-1,10,14,18,18-pentamethyl-7-oxapentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosa-5,8-dien-4-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1C[C@H]2[C@]3(C)CC[C@H]4C(C)(C)CCC[C@]4(C)[C@H]3C[C@@H](O)[C@]2(C)C2=COC=C12

InChI Identifier

InChI=1S/C27H40O4/c1-16(28)31-19-12-22-26(5)11-8-20-24(2,3)9-7-10-25(20,4)21(26)13-23(29)27(22,6)18-15-30-14-17(18)19/h14-15,19-23,29H,7-13H2,1-6H3/t19-,20-,21+,22-,23+,25-,26+,27+/m0/s1

InChI Key

JRKYCNUZXAQLDW-PVRRMCBNSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Hyrtios erectus	LOTUS Database	35616633
Hyrtios gumminae	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as scalarane sesterterpenoids. These are sesterterpenoids with a structure based on the scalarane backbone. Scalarane is a tetracyclic compound, which is similar the homoandrostane with five methyl groups at the 4-, 4-, 8-, 17-, 17a-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Scalarane sesterterpenoids

Alternative Parents

Substituents

Scalarane sesterterpenoid
Cyclic alcohol
Furan
Heteroaromatic compound
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
Alcohol
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	5.52	ALOGPS
logP	5.03	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	14.48	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59.67 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	120.18 m³·mol⁻¹	ChemAxon
Polarizability	49.57 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	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

C00043621

Chemspider ID

24658419

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46882346

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kaweetripob W, Mahidol C, Tuntiwachwuttikul P, Ruchirawat S, Prawat H: Cytotoxic Sesterterpenes from Thai Marine Sponge Hyrtios erectus. Mar Drugs. 2018 Nov 28;16(12). pii: md16120474. doi: 10.3390/md16120474. [PubMed:30487463 ]
Chen XB, Yuan QJ, Wang J, Hua SK, Ren J, Zeng BB: Synthesis of the scalarane sesterterpenoid 16-deacetoxy-12-epi-scalarafuranacetate. J Org Chem. 2011 Sep 2;76(17):7216-21. doi: 10.1021/jo2008127. Epub 2011 Aug 9. [PubMed:21800844 ]
Manzo E, Gavagnin M, Somerville MJ, Mao SC, Ciavatta ML, Mollo E, Schupp PJ, Garson MJ, Guo YW, Cimino G: Chemistry of Glossodoris nudibranchs: specific occurrence of 12-keto scalaranes. J Chem Ecol. 2007 Dec;33(12):2325-36. doi: 10.1007/s10886-007-9387-x. Epub 2007 Nov 15. [PubMed:18000710 ]

Showing NP-Card for Scalarafuran (NP0081685)

MOL for NP0081685 (Scalarafuran)

3D MOL for NP0081685 (Scalarafuran)

3D SDF for NP0081685 (Scalarafuran)

3D-SDF for NP0081685 (Scalarafuran)

PDB for NP0081685 (Scalarafuran)

3D PDB for NP0081685 (Scalarafuran)

SMILES for NP0081685 (Scalarafuran)

INCHI for NP0081685 (Scalarafuran)

Structure for NP0081685 (Scalarafuran)

3D Structure for NP0081685 (Scalarafuran)