NP-MRD: Showing NP-Card for 22-hydroxy-16-(2-hydroxypropan-2-yl)-4,8,13-trimethyl-12,17-dioxatetracyclo[17.3.1.0³,⁷.0¹¹,¹³]tricosa-1(23),3,8,19,21-pentaen-18-one (NP0190862)

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Record Information

Version

2.0

Created at

2022-09-04 07:36:39 UTC

Updated at

2022-09-04 07:36:40 UTC

NP-MRD ID

NP0190862

Secondary Accession Numbers

None

Natural Product Identification

Common Name

22-hydroxy-16-(2-hydroxypropan-2-yl)-4,8,13-trimethyl-12,17-dioxatetracyclo[17.3.1.0³,⁷.0¹¹,¹³]tricosa-1(23),3,8,19,21-pentaen-18-one

Description

22-Hydroxy-16-(2-hydroxypropan-2-yl)-4,8,13-trimethyl-12,17-dioxatetracyclo[17.3.1.0³,⁷.0¹¹,¹³]Tricosa-1(22),3,8,19(23),20-pentaen-18-one belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. 22-hydroxy-16-(2-hydroxypropan-2-yl)-4,8,13-trimethyl-12,17-dioxatetracyclo[17.3.1.0³,⁷.0¹¹,¹³]tricosa-1(23),3,8,19,21-pentaen-18-one is found in Callophycus serratus. 22-Hydroxy-16-(2-hydroxypropan-2-yl)-4,8,13-trimethyl-12,17-dioxatetracyclo[17.3.1.0³,⁷.0¹¹,¹³]Tricosa-1(22),3,8,19(23),20-pentaen-18-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171519142D          

 32 35  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004171519142D          

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M  END
> <DATABASE_ID>
NP0190862

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2CC3=CC(=CC=C3O)C(=O)OC(CCC3(C)OC3CC=C(C)C2CC1)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C27H36O5/c1-16-7-11-24-27(5,32-24)13-12-23(26(3,4)30)31-25(29)18-8-10-22(28)19(14-18)15-21-17(2)6-9-20(16)21/h7-8,10,14,20,23-24,28,30H,6,9,11-13,15H2,1-5H3

> <INCHI_KEY>
XHVNCHKVWKNRKD-UHFFFAOYSA-N

> <FORMULA>
C27H36O5

> <MOLECULAR_WEIGHT>
440.58

> <EXACT_MASS>
440.256274259

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
47.75942174870899

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
22-hydroxy-16-(2-hydroxypropan-2-yl)-4,8,13-trimethyl-12,17-dioxatetracyclo[17.3.1.0³,⁷.0¹¹,¹³]tricosa-1(23),3,8,19,21-pentaen-18-one

> <ALOGPS_LOGP>
4.76

> <JCHEM_LOGP>
4.835741167666667

> <ALOGPS_LOGS>
-4.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.302045478360878

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.29732198556287

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1040854957234236

> <JCHEM_POLAR_SURFACE_AREA>
79.29

> <JCHEM_REFRACTIVITY>
126.38800000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.52e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
22-hydroxy-16-(2-hydroxypropan-2-yl)-4,8,13-trimethyl-12,17-dioxatetracyclo[17.3.1.0³,⁷.0¹¹,¹³]tricosa-1(23),3,8,19,21-pentaen-18-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      15.508   4.242   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.244   5.418   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.824   4.812   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.361   4.893   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.200   3.601   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.501   2.229   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.340   0.938   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.878   1.019   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.577   2.391   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.738   3.682   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      17.437   5.054   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      14.641  -0.434   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      15.480  -1.726   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      13.103  -0.515   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      12.264   0.776   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.726   0.696   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.888   1.987   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.350   1.906   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.430   0.369   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.812   1.826   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.511   3.198   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.210   4.570   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.748   4.651   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.447   6.023   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.608   7.315   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.985   6.104   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.954   7.301   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.392   6.749   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.565  -0.596   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.866  -1.968   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.193   0.103   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      12.938  -1.295   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   28                                                  
CONECT    3    2    4   26                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10                                                            
CONECT   12    7   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   29                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   18   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24    3   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27    2                                                       
CONECT   29   15   30   31   32                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   29                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₆O₅

Average Mass

440.5800 Da

Monoisotopic Mass

440.25627 Da

IUPAC Name

22-hydroxy-16-(2-hydroxypropan-2-yl)-4,8,13-trimethyl-12,17-dioxatetracyclo[17.3.1.0³,⁷.0¹¹,¹³]tricosa-1(23),3,8,19,21-pentaen-18-one

Traditional Name

22-hydroxy-16-(2-hydroxypropan-2-yl)-4,8,13-trimethyl-12,17-dioxatetracyclo[17.3.1.0³,⁷.0¹¹,¹³]tricosa-1(23),3,8,19,21-pentaen-18-one

CAS Registry Number

Not Available

SMILES

CC1=C2CC3=CC(=CC=C3O)C(=O)OC(CCC3(C)OC3CC=C(C)C2CC1)C(C)(C)O

InChI Identifier

InChI=1S/C27H36O5/c1-16-7-11-24-27(5,32-24)13-12-23(26(3,4)30)31-25(29)18-8-10-22(28)19(14-18)15-21-17(2)6-9-20(16)21/h7-8,10,14,20,23-24,28,30H,6,9,11-13,15H2,1-5H3

InChI Key

XHVNCHKVWKNRKD-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
Callophycus serratus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Tertiary alcohol
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Organic oxygen 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	4.76	ALOGPS
logP	4.84	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	8.3	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.29 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	126.39 m³·mol⁻¹	ChemAxon
Polarizability	47.76 Å³	ChemAxon
Number of Rings	4	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

73838024

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 22-hydroxy-16-(2-hydroxypropan-2-yl)-4,8,13-trimethyl-12,17-dioxatetracyclo[17.3.1.0³,⁷.0¹¹,¹³]tricosa-1(23),3,8,19,21-pentaen-18-one (NP0190862)

MOL for NP0190862 (22-hydroxy-16-(2-hydroxypropan-2-yl)-4,8,13-trimethyl-12,17-dioxatetracyclo[17.3.1.0³,⁷.0¹¹,¹³]tricosa-1(23),3,8,19,21-pentaen-18-one)

3D MOL for NP0190862 (22-hydroxy-16-(2-hydroxypropan-2-yl)-4,8,13-trimethyl-12,17-dioxatetracyclo[17.3.1.0³,⁷.0¹¹,¹³]tricosa-1(23),3,8,19,21-pentaen-18-one)

3D SDF for NP0190862 (22-hydroxy-16-(2-hydroxypropan-2-yl)-4,8,13-trimethyl-12,17-dioxatetracyclo[17.3.1.0³,⁷.0¹¹,¹³]tricosa-1(23),3,8,19,21-pentaen-18-one)

3D-SDF for NP0190862 (22-hydroxy-16-(2-hydroxypropan-2-yl)-4,8,13-trimethyl-12,17-dioxatetracyclo[17.3.1.0³,⁷.0¹¹,¹³]tricosa-1(23),3,8,19,21-pentaen-18-one)

PDB for NP0190862 (22-hydroxy-16-(2-hydroxypropan-2-yl)-4,8,13-trimethyl-12,17-dioxatetracyclo[17.3.1.0³,⁷.0¹¹,¹³]tricosa-1(23),3,8,19,21-pentaen-18-one)

3D PDB for NP0190862 (22-hydroxy-16-(2-hydroxypropan-2-yl)-4,8,13-trimethyl-12,17-dioxatetracyclo[17.3.1.0³,⁷.0¹¹,¹³]tricosa-1(23),3,8,19,21-pentaen-18-one)

SMILES for NP0190862 (22-hydroxy-16-(2-hydroxypropan-2-yl)-4,8,13-trimethyl-12,17-dioxatetracyclo[17.3.1.0³,⁷.0¹¹,¹³]tricosa-1(23),3,8,19,21-pentaen-18-one)

INCHI for NP0190862 (22-hydroxy-16-(2-hydroxypropan-2-yl)-4,8,13-trimethyl-12,17-dioxatetracyclo[17.3.1.0³,⁷.0¹¹,¹³]tricosa-1(23),3,8,19,21-pentaen-18-one)

Structure for NP0190862 (22-hydroxy-16-(2-hydroxypropan-2-yl)-4,8,13-trimethyl-12,17-dioxatetracyclo[17.3.1.0³,⁷.0¹¹,¹³]tricosa-1(23),3,8,19,21-pentaen-18-one)

3D Structure for NP0190862 (22-hydroxy-16-(2-hydroxypropan-2-yl)-4,8,13-trimethyl-12,17-dioxatetracyclo[17.3.1.0³,⁷.0¹¹,¹³]tricosa-1(23),3,8,19,21-pentaen-18-one)