NP-MRD: Showing NP-Card for (1r,6s,11s,16s,19r)-6-(furan-3-yl)-2,18,19,20-tetrahydroxy-7,17,17-trimethyl-5,13,21-trioxahexacyclo[17.2.1.0¹,¹⁰.0²,⁷.0¹¹,¹⁶.0¹¹,²⁰]docosane-4,14-dione (NP0258524)

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Record Information

Version

2.0

Created at

2022-09-08 00:01:19 UTC

Updated at

2022-09-08 00:01:19 UTC

NP-MRD ID

NP0258524

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,6s,11s,16s,19r)-6-(furan-3-yl)-2,18,19,20-tetrahydroxy-7,17,17-trimethyl-5,13,21-trioxahexacyclo[17.2.1.0¹,¹⁰.0²,⁷.0¹¹,¹⁶.0¹¹,²⁰]docosane-4,14-dione

Description

Anthothecanolide belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. (1r,6s,11s,16s,19r)-6-(furan-3-yl)-2,18,19,20-tetrahydroxy-7,17,17-trimethyl-5,13,21-trioxahexacyclo[17.2.1.0¹,¹⁰.0²,⁷.0¹¹,¹⁶.0¹¹,²⁰]docosane-4,14-dione is found in Khaya anthotheca. (1r,6s,11s,16s,19r)-6-(furan-3-yl)-2,18,19,20-tetrahydroxy-7,17,17-trimethyl-5,13,21-trioxahexacyclo[17.2.1.0¹,¹⁰.0²,⁷.0¹¹,¹⁶.0¹¹,²⁰]docosane-4,14-dione was first documented in 2005 (PMID: 15893779). Based on a literature review very few articles have been published on Anthothecanolide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082202012D          

 36 42  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309082202012D          

 36 42  0  0  1  0            999 V2000
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 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 19 18  1  6  0  0  0
  2 19  1  0  0  0  0
 13 19  1  0  0  0  0
 13 20  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 26 30  2  0  0  0  0
 25 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 23 35  1  0  0  0  0
  9 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0258524

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C(O)[C@]2(O)C[C@@]34OC2(O)[C@]2(COC(=O)C[C@@H]12)C3CCC1(C)[C@@H](OC(=O)CC41O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O10/c1-20(2)15-8-16(27)34-12-22(15)14-4-6-21(3)18(13-5-7-33-10-13)35-17(28)9-25(21,31)24(14)11-23(30,19(20)29)26(22,32)36-24/h5,7,10,14-15,18-19,29-32H,4,6,8-9,11-12H2,1-3H3/t14?,15-,18-,19?,21?,22+,23+,24+,25?,26?/m0/s1

> <INCHI_KEY>
LXWTWJGKNFFMCZ-LFXXVLHOSA-N

> <FORMULA>
C26H32O10

> <MOLECULAR_WEIGHT>
504.532

> <EXACT_MASS>
504.19954723

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
50.10703336850527

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,6R,11S,16S,19R)-6-(furan-3-yl)-2,18,19,20-tetrahydroxy-7,17,17-trimethyl-5,13,21-trioxahexacyclo[17.2.1.0^{1,10}.0^{2,7}.0^{11,16}.0^{11,20}]docosane-4,14-dione

> <JCHEM_LOGP>
0.02769487966666545

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.508662122959773

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.48927692526878

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8763554412742476

> <JCHEM_POLAR_SURFACE_AREA>
155.89

> <JCHEM_REFRACTIVITY>
118.19460000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,6R,11S,16S,19R)-6-(furan-3-yl)-2,18,19,20-tetrahydroxy-7,17,17-trimethyl-5,13,21-trioxahexacyclo[17.2.1.0^{1,10}.0^{2,7}.0^{11,16}.0^{11,20}]docosane-4,14-dione

> <JCHEM_VEBER_RULE>
0

$$$$

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       1.600  -1.725   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.442  -0.436   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.020   0.157   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.622  -1.562   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.139  -3.024   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.261  -1.359   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.546  -2.873   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       7.231  -0.855   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.924   0.829   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.355  -0.950   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.035   0.008   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.572  -0.471   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.329   1.398   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.590   2.995   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.705   4.272   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.221   3.932   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.173   5.060   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.759   2.435   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.780   1.144   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.772   1.963   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.759   3.631   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.019   4.418   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.270   3.546   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.383   5.082   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.649   4.233   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.743   5.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.555   6.750   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.120   8.183   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      10.657   8.088   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      11.042   6.597   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      10.933   3.383   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      10.838   1.846   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      12.122   0.996   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       9.460   1.159   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.176   2.009   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       8.307   0.475   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   19                                             
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8   11                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   20   35                                             
CONECT   10    9   11                                                       
CONECT   11   10    6   12   13                                             
CONECT   12   11                                                            
CONECT   13   11   14   19   20                                             
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18    2   13                                                  
CONECT   20   13    9   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25   35                                             
CONECT   24   23                                                            
CONECT   25   23   26   31                                                  
CONECT   26   25   27   30                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   26                                                       
CONECT   31   25   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   23    9   36                                             
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₂O₁₀

Average Mass

504.5320 Da

Monoisotopic Mass

504.19955 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1(C)C(O)[C@]2(O)C[C@@]34OC2(O)[C@]2(COC(=O)C[C@@H]12)C3CCC1(C)[C@@H](OC(=O)CC41O)C1=COC=C1

InChI Identifier

InChI=1S/C26H32O10/c1-20(2)15-8-16(27)34-12-22(15)14-4-6-21(3)18(13-5-7-33-10-13)35-17(28)9-25(21,31)24(14)11-23(30,19(20)29)26(22,32)36-24/h5,7,10,14-15,18-19,29-32H,4,6,8-9,11-12H2,1-3H3/t14?,15-,18-,19?,21?,22+,23+,24+,25?,26?/m0/s1

InChI Key

LXWTWJGKNFFMCZ-LFXXVLHOSA-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
Khaya anthotheca	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Mexicanolide
Limonoid skeleton
Naphthopyran
Naphthalene
Delta_valerolactone
Delta valerolactone
Pyran
Oxane
Dicarboxylic acid or derivatives
Heteroaromatic compound
Tetrahydrofuran
Tertiary alcohol
Furan
Cyclic alcohol
Secondary alcohol
Lactone
Hemiacetal
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00035213

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

101740599

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tchimene MK, Tane P, Ngamga D, Connolly JD, Farrugia LJ: Four tetranortriterpenoids from the stem bark of Khaya anthotheca. Phytochemistry. 2005 May;66(10):1088-93. doi: 10.1016/j.phytochem.2005.03.028. [PubMed:15893779 ]
LOTUS database [Link]

Showing NP-Card for (1r,6s,11s,16s,19r)-6-(furan-3-yl)-2,18,19,20-tetrahydroxy-7,17,17-trimethyl-5,13,21-trioxahexacyclo[17.2.1.0¹,¹⁰.0²,⁷.0¹¹,¹⁶.0¹¹,²⁰]docosane-4,14-dione (NP0258524)

MOL for NP0258524 ((1r,6s,11s,16s,19r)-6-(furan-3-yl)-2,18,19,20-tetrahydroxy-7,17,17-trimethyl-5,13,21-trioxahexacyclo[17.2.1.0¹,¹⁰.0²,⁷.0¹¹,¹⁶.0¹¹,²⁰]docosane-4,14-dione)

3D MOL for NP0258524 ((1r,6s,11s,16s,19r)-6-(furan-3-yl)-2,18,19,20-tetrahydroxy-7,17,17-trimethyl-5,13,21-trioxahexacyclo[17.2.1.0¹,¹⁰.0²,⁷.0¹¹,¹⁶.0¹¹,²⁰]docosane-4,14-dione)

3D SDF for NP0258524 ((1r,6s,11s,16s,19r)-6-(furan-3-yl)-2,18,19,20-tetrahydroxy-7,17,17-trimethyl-5,13,21-trioxahexacyclo[17.2.1.0¹,¹⁰.0²,⁷.0¹¹,¹⁶.0¹¹,²⁰]docosane-4,14-dione)

3D-SDF for NP0258524 ((1r,6s,11s,16s,19r)-6-(furan-3-yl)-2,18,19,20-tetrahydroxy-7,17,17-trimethyl-5,13,21-trioxahexacyclo[17.2.1.0¹,¹⁰.0²,⁷.0¹¹,¹⁶.0¹¹,²⁰]docosane-4,14-dione)

PDB for NP0258524 ((1r,6s,11s,16s,19r)-6-(furan-3-yl)-2,18,19,20-tetrahydroxy-7,17,17-trimethyl-5,13,21-trioxahexacyclo[17.2.1.0¹,¹⁰.0²,⁷.0¹¹,¹⁶.0¹¹,²⁰]docosane-4,14-dione)

3D PDB for NP0258524 ((1r,6s,11s,16s,19r)-6-(furan-3-yl)-2,18,19,20-tetrahydroxy-7,17,17-trimethyl-5,13,21-trioxahexacyclo[17.2.1.0¹,¹⁰.0²,⁷.0¹¹,¹⁶.0¹¹,²⁰]docosane-4,14-dione)

SMILES for NP0258524 ((1r,6s,11s,16s,19r)-6-(furan-3-yl)-2,18,19,20-tetrahydroxy-7,17,17-trimethyl-5,13,21-trioxahexacyclo[17.2.1.0¹,¹⁰.0²,⁷.0¹¹,¹⁶.0¹¹,²⁰]docosane-4,14-dione)

INCHI for NP0258524 ((1r,6s,11s,16s,19r)-6-(furan-3-yl)-2,18,19,20-tetrahydroxy-7,17,17-trimethyl-5,13,21-trioxahexacyclo[17.2.1.0¹,¹⁰.0²,⁷.0¹¹,¹⁶.0¹¹,²⁰]docosane-4,14-dione)

Structure for NP0258524 ((1r,6s,11s,16s,19r)-6-(furan-3-yl)-2,18,19,20-tetrahydroxy-7,17,17-trimethyl-5,13,21-trioxahexacyclo[17.2.1.0¹,¹⁰.0²,⁷.0¹¹,¹⁶.0¹¹,²⁰]docosane-4,14-dione)

3D Structure for NP0258524 ((1r,6s,11s,16s,19r)-6-(furan-3-yl)-2,18,19,20-tetrahydroxy-7,17,17-trimethyl-5,13,21-trioxahexacyclo[17.2.1.0¹,¹⁰.0²,⁷.0¹¹,¹⁶.0¹¹,²⁰]docosane-4,14-dione)