NP-MRD: Showing NP-Card for 10-hydroxy-1,14,18,18-tetramethyl-7-oxo-2,6-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10-trien-17-yl acetate (NP0324381)

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Record Information

Version

2.0

Created at

2022-09-12 04:25:27 UTC

Updated at

2022-09-12 04:25:27 UTC

NP-MRD ID

NP0324381

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10-hydroxy-1,14,18,18-tetramethyl-7-oxo-2,6-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10-trien-17-yl acetate

Description

10-Hydroxy-1,14,18,18-tetramethyl-7-oxo-2,6-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]Henicosa-3,8,10-trien-17-yl acetate belongs to the class of organic compounds known as isoflavanols. These are polycyclic compounds containing a hydroxylated isoflavan skeleton. 10-hydroxy-1,14,18,18-tetramethyl-7-oxo-2,6-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10-trien-17-yl acetate is found in Stachybotrys kampalensis. Based on a literature review very few articles have been published on 10-hydroxy-1,14,18,18-tetramethyl-7-oxo-2,6-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]Henicosa-3,8,10-trien-17-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122206252D          

 31 35  0  0  0  0            999 V2000
   -1.4691   -3.9705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6442   -3.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2426   -4.7037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2209   -3.2749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6040   -3.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0274   -2.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8523   -2.5919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2538   -3.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6772   -2.6044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0788   -3.3251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5021   -2.6170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3270   -2.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7503   -1.9214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3487   -1.2007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5752   -1.9340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9768   -2.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5535   -3.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7286   -3.3502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3052   -4.0583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4803   -4.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8819   -4.7664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0570   -4.7539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2321   -4.7413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8305   -4.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0056   -4.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
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M  END

     RDKit          3D

 63 67  0  0  0  0  0  0  0  0999 V2000
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   -5.1159    0.4117    1.7279 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4095    0.8603   -0.4705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9246    1.5678   -1.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1846    2.0880   -1.3137 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4973    1.7650   -0.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5627    2.1039    0.5657 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8186   -1.3649    0.1320 C   0  0  2  0  0  0  0  0  0  0  0  0
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 31 63  1  0
M  END


  Mrv1652309122206252D          

 31 35  0  0  0  0            999 V2000
   -1.4691   -3.9705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6442   -3.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2426   -4.7037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0274   -2.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0324381

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CCC2(C)C(CCC3(C)OC4=C5COC(=O)C5=CC(O)=C4CC23)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C25H32O6/c1-13(26)30-20-7-8-24(4)18(23(20,2)3)6-9-25(5)19(24)11-15-17(27)10-14-16(21(15)31-25)12-29-22(14)28/h10,18-20,27H,6-9,11-12H2,1-5H3

> <INCHI_KEY>
BOVRDZLKBBUXQQ-UHFFFAOYSA-N

> <FORMULA>
C25H32O6

> <MOLECULAR_WEIGHT>
428.525

> <EXACT_MASS>
428.21988875

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
47.302072453925554

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-hydroxy-1,14,18,18-tetramethyl-7-oxo-2,6-dioxapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-3,8,10-trien-17-yl acetate

> <JCHEM_LOGP>
4.213537641666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.504350717883352

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.885204446187943

> <JCHEM_PKA_STRONGEST_BASIC>
-4.902687024875381

> <JCHEM_POLAR_SURFACE_AREA>
82.06

> <JCHEM_REFRACTIVITY>
114.50679999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
10-hydroxy-1,14,18,18-tetramethyl-7-oxo-2,6-dioxapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-3,8,10-trien-17-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.742  -7.412   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.202  -7.435   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.453  -8.780   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -0.412  -6.113   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.128  -6.137   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.918  -4.815   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.458  -4.838   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.207  -6.183   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.997  -4.862   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.747  -6.207   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.537  -4.885   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.077  -4.908   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.867  -3.587   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.118  -2.241   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      10.407  -3.610   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.157  -4.955   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.366  -6.277   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.827  -6.254   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.036  -7.575   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.497  -7.552   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.246  -8.897   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.706  -8.874   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.167  -8.850   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.417  -7.505   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.877  -7.482   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.800  -9.020   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.559  -8.278   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.379  -7.437   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      12.796  -6.832   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      12.658  -5.298   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      13.818  -4.285   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   25                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   24                                             
CONECT    9    8                                                            
CONECT   10    8   11   20                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   30                                                  
CONECT   17   16   18   28                                                  
CONECT   18   17   12   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   10   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    8   25                                                  
CONECT   25   24    5   26   27                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   17   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   16   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Value	Source
10-Hydroxy-1,14,18,18-tetramethyl-7-oxo-2,6-dioxapentacyclo[11.8.0.0,.0,.0,]henicosa-3,8,10-trien-17-yl acetic acid	Generator

Chemical Formula

C₂₅H₃₂O₆

Average Mass

428.5250 Da

Monoisotopic Mass

428.21989 Da

IUPAC Name

10-hydroxy-1,14,18,18-tetramethyl-7-oxo-2,6-dioxapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-3,8,10-trien-17-yl acetate

Traditional Name

10-hydroxy-1,14,18,18-tetramethyl-7-oxo-2,6-dioxapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-3,8,10-trien-17-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CCC2(C)C(CCC3(C)OC4=C5COC(=O)C5=CC(O)=C4CC23)C1(C)C

InChI Identifier

InChI=1S/C25H32O6/c1-13(26)30-20-7-8-24(4)18(23(20,2)3)6-9-25(5)19(24)11-15-17(27)10-14-16(21(15)31-25)12-29-22(14)28/h10,18-20,27H,6-9,11-12H2,1-5H3

InChI Key

BOVRDZLKBBUXQQ-UHFFFAOYSA-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
Stachybotrys kampalensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavanols. These are polycyclic compounds containing a hydroxylated isoflavan skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavans

Direct Parent

Isoflavanols

Alternative Parents

Substituents

Isoflavanol
Dibenzopyran
Xanthene
Naphthopyran
Chromane
Isobenzofuranone
Benzopyran
Naphthalene
1-benzopyran
Phthalide
Isocoumaran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Pyran
Dicarboxylic acid or derivatives
Lactone
Carboxylic acid ester
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Hydrocarbon derivative
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	4.21	ChemAxon
pKa (Strongest Acidic)	8.89	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	114.51 m³·mol⁻¹	ChemAxon
Polarizability	47.3 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

162860685

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 10-hydroxy-1,14,18,18-tetramethyl-7-oxo-2,6-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10-trien-17-yl acetate (NP0324381)

MOL for NP0324381 (10-hydroxy-1,14,18,18-tetramethyl-7-oxo-2,6-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10-trien-17-yl acetate)

3D MOL for NP0324381 (10-hydroxy-1,14,18,18-tetramethyl-7-oxo-2,6-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10-trien-17-yl acetate)

3D SDF for NP0324381 (10-hydroxy-1,14,18,18-tetramethyl-7-oxo-2,6-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10-trien-17-yl acetate)

3D-SDF for NP0324381 (10-hydroxy-1,14,18,18-tetramethyl-7-oxo-2,6-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10-trien-17-yl acetate)

PDB for NP0324381 (10-hydroxy-1,14,18,18-tetramethyl-7-oxo-2,6-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10-trien-17-yl acetate)

3D PDB for NP0324381 (10-hydroxy-1,14,18,18-tetramethyl-7-oxo-2,6-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10-trien-17-yl acetate)

SMILES for NP0324381 (10-hydroxy-1,14,18,18-tetramethyl-7-oxo-2,6-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10-trien-17-yl acetate)

INCHI for NP0324381 (10-hydroxy-1,14,18,18-tetramethyl-7-oxo-2,6-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10-trien-17-yl acetate)

Structure for NP0324381 (10-hydroxy-1,14,18,18-tetramethyl-7-oxo-2,6-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10-trien-17-yl acetate)

3D Structure for NP0324381 (10-hydroxy-1,14,18,18-tetramethyl-7-oxo-2,6-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10-trien-17-yl acetate)