NP-MRD: Showing NP-Card for 12beta,16alpha,20-Trihydroxy-17-scalaren-19,20-olide (NP0081489)

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Record Information

Version

2.0

Created at

2022-04-29 02:30:01 UTC

Updated at

2022-04-29 02:30:01 UTC

NP-MRD ID

NP0081489

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12beta,16alpha,20-Trihydroxy-17-scalaren-19,20-olide

Description

(1R,2S,4R,6R,10S,11R,13R,14S,19S)-4,6,11-trihydroxy-1,10,14,18,18-pentamethyl-7-oxapentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]Henicos-5(9)-en-8-one 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. 12beta,16alpha,20-Trihydroxy-17-scalaren-19,20-olide is found in Hyrtios gumminae. Based on a literature review very few articles have been published on (1R,2S,4R,6R,10S,11R,13R,14S,19S)-4,6,11-trihydroxy-1,10,14,18,18-pentamethyl-7-oxapentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]Henicos-5(9)-en-8-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292204302D          

 30 34  0  0  1  0            999 V2000
    6.4186    1.1332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9953    0.4250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3969   -0.2956    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2218   -0.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6451    0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2435    1.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2380   -1.1330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9147   -0.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9736   -1.0037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1487   -0.9912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7471   -0.2705    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1704    0.4376    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7688    1.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9439    1.1708    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5206    0.4627    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9222   -0.2580    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.2724   -0.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6957    0.4752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1530    1.0967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3368    1.9009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3943    0.7726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8467   -0.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1190    1.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3238   -0.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 14 28  1  6  0  0  0
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  2 30  1  6  0  0  0
M  END

     RDKit          3D

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    2.5564   -0.2532    0.7194 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304292204302D          

 30 34  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0081489

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H]2C[C@@H](O)[C@@]2(C)[C@H]1C[C@@H](O)C1=C2C(=O)O[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H38O5/c1-22(2)8-6-9-23(3)14(22)7-10-24(4)15(23)12-17(27)25(5)16(24)11-13(26)18-19(25)21(29)30-20(18)28/h13-17,20,26-28H,6-12H2,1-5H3/t13-,14+,15-,16+,17-,20-,23+,24-,25-/m1/s1

> <INCHI_KEY>
XOOYWQIVYHRNAO-URHBTJLDSA-N

> <FORMULA>
C25H38O5

> <MOLECULAR_WEIGHT>
418.574

> <EXACT_MASS>
418.271924324

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
47.44781633635239

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,4R,6R,10S,11R,13R,14S,19S)-4,6,11-trihydroxy-1,10,14,18,18-pentamethyl-7-oxapentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicos-5(9)-en-8-one

> <ALOGPS_LOGP>
2.85

> <JCHEM_LOGP>
3.2606491376666664

> <ALOGPS_LOGS>
-4.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.160983942668054

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.304419316810723

> <JCHEM_PKA_STRONGEST_BASIC>
-2.970628301717314

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
113.28719999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.15e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4R,6R,10S,11R,13R,14S,19S)-4,6,11-trihydroxy-1,10,14,18,18-pentamethyl-7-oxapentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicos-5(9)-en-8-one

> <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      11.981   2.115   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.191   0.793   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.941  -0.552   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.481  -0.575   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.271   0.747   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.521   2.092   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.511  -2.115   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.774  -1.411   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.151  -1.874   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.611  -1.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.861  -0.505   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.651   0.817   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.902   2.162   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.362   2.185   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.572   0.864   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.321  -0.482   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.531  -1.803   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.991  -1.780   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.242  -0.435   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.032   0.887   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.019   2.047   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.362   3.548   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.603   1.442   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.740  -0.092   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.580  -1.105   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       4.201  -3.102   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.822   2.209   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.612   3.531   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.071  -1.827   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.442   2.139   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   12   30                                             
CONECT    3    2    4    9                                                  
CONECT    4    3    5    7    8                                             
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4                                                            
CONECT    8    4                                                            
CONECT    9    3   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16   29                                             
CONECT   12   11    2   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   28                                                  
CONECT   15   14   16   20   27                                             
CONECT   16   15   11   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   26                                                  
CONECT   19   18   20   24                                                  
CONECT   20   19   15   21                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   19   25                                                  
CONECT   25   24                                                            
CONECT   26   18                                                            
CONECT   27   15                                                            
CONECT   28   14                                                            
CONECT   29   11                                                            
CONECT   30    2                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₈O₅

Average Mass

418.5740 Da

Monoisotopic Mass

418.27192 Da

IUPAC Name

(1R,2S,4R,6R,10S,11R,13R,14S,19S)-4,6,11-trihydroxy-1,10,14,18,18-pentamethyl-7-oxapentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicos-5(9)-en-8-one

Traditional Name

(1R,2S,4R,6R,10S,11R,13R,14S,19S)-4,6,11-trihydroxy-1,10,14,18,18-pentamethyl-7-oxapentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicos-5(9)-en-8-one

CAS Registry Number

Not Available

SMILES

CC1(C)CCC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H]2C[C@@H](O)[C@@]2(C)[C@H]1C[C@@H](O)C1=C2C(=O)O[C@H]1O

InChI Identifier

InChI=1S/C25H38O5/c1-22(2)8-6-9-23(3)14(22)7-10-24(4)15(23)12-17(27)25(5)16(24)11-13(26)18-19(25)21(29)30-20(18)28/h13-17,20,26-28H,6-12H2,1-5H3/t13-,14+,15-,16+,17-,20-,23+,24-,25-/m1/s1

InChI Key

XOOYWQIVYHRNAO-URHBTJLDSA-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 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
Steroid lactone
7-hydroxysteroid
17-hydroxysteroid
Hydroxysteroid
12-hydroxysteroid
Steroid
16-oxasteroid
2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Dihydrofuran
Cyclic alcohol
Secondary alcohol
Lactone
Hemiacetal
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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
logP	2.85	ALOGPS
logP	3.26	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	11.3	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	113.29 m³·mol⁻¹	ChemAxon
Polarizability	47.45 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163106593

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 12beta,16alpha,20-Trihydroxy-17-scalaren-19,20-olide (NP0081489)

MOL for NP0081489 (12beta,16alpha,20-Trihydroxy-17-scalaren-19,20-olide)

3D MOL for NP0081489 (12beta,16alpha,20-Trihydroxy-17-scalaren-19,20-olide)

3D SDF for NP0081489 (12beta,16alpha,20-Trihydroxy-17-scalaren-19,20-olide)

3D-SDF for NP0081489 (12beta,16alpha,20-Trihydroxy-17-scalaren-19,20-olide)

PDB for NP0081489 (12beta,16alpha,20-Trihydroxy-17-scalaren-19,20-olide)

3D PDB for NP0081489 (12beta,16alpha,20-Trihydroxy-17-scalaren-19,20-olide)

SMILES for NP0081489 (12beta,16alpha,20-Trihydroxy-17-scalaren-19,20-olide)

INCHI for NP0081489 (12beta,16alpha,20-Trihydroxy-17-scalaren-19,20-olide)

Structure for NP0081489 (12beta,16alpha,20-Trihydroxy-17-scalaren-19,20-olide)

3D Structure for NP0081489 (12beta,16alpha,20-Trihydroxy-17-scalaren-19,20-olide)