NP-MRD: Showing NP-Card for (1r)-5-{2-[(3r,5ar,6r,7s,9ar)-3,7-dihydroxy-2,2,5a,7-tetramethyl-hexahydro-3h-1-benzoxepin-6-yl]ethyl}-1-hydroxy-1,4,4-trimethyl-2,3,3a,5,8,8a-hexahydroazulene-6-carbaldehyde (NP0291550)

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Record Information

Version

2.0

Created at

2022-09-09 22:41:27 UTC

Updated at

2022-09-09 22:41:28 UTC

NP-MRD ID

NP0291550

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r)-5-{2-[(3r,5ar,6r,7s,9ar)-3,7-dihydroxy-2,2,5a,7-tetramethyl-hexahydro-3h-1-benzoxepin-6-yl]ethyl}-1-hydroxy-1,4,4-trimethyl-2,3,3a,5,8,8a-hexahydroazulene-6-carbaldehyde

Description

CHEMBL226197 belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (1r)-5-{2-[(3r,5ar,6r,7s,9ar)-3,7-dihydroxy-2,2,5a,7-tetramethyl-hexahydro-3h-1-benzoxepin-6-yl]ethyl}-1-hydroxy-1,4,4-trimethyl-2,3,3a,5,8,8a-hexahydroazulene-6-carbaldehyde is found in Callyspongia siphonella. Based on a literature review very few articles have been published on CHEMBL226197.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102200412D          

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M  END

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M  END


  Mrv1652309102200412D          

 35 38  0  0  1  0            999 V2000
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    9.4207   -1.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8332   -2.5641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2378   -2.5930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4335   -2.7766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7885   -2.2622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7885   -1.4372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0038   -1.1822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5189   -1.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0038   -2.5171    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3966   -3.0755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1669   -3.3258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  1  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 13 22  1  0  0  0  0
  7 22  1  0  0  0  0
 22 23  1  1  0  0  0
  4 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 24 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 29 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0291550

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]1(O)CCC2C1CC=C(C=O)C(CC[C@H]1[C@@](C)(O)CC[C@H]3OC(C)(C)[C@H](O)CC[C@]13C)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O5/c1-26(2)20(19(18-31)8-9-22-21(26)12-16-29(22,6)33)10-11-23-28(5)15-13-24(32)27(3,4)35-25(28)14-17-30(23,7)34/h8,18,20-25,32-34H,9-17H2,1-7H3/t20?,21?,22?,23-,24-,25-,28-,29-,30+/m1/s1

> <INCHI_KEY>
BDNMFPOVAWCGRX-NXHAIPTASA-N

> <FORMULA>
C30H50O5

> <MOLECULAR_WEIGHT>
490.725

> <EXACT_MASS>
490.36582471

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
57.00072935057045

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R)-5-{2-[(3R,5aR,6R,7S,9aR)-3,7-dihydroxy-2,2,5a,7-tetramethyl-decahydro-1-benzoxepin-6-yl]ethyl}-1-hydroxy-1,4,4-trimethyl-1,2,3,3a,4,5,8,8a-octahydroazulene-6-carbaldehyde

> <JCHEM_LOGP>
3.9270259966666687

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.83497618417502

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.939860724032158

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7362737334011354

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
139.85880000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R)-5-{2-[(3R,5aR,6R,7S,9aR)-3,7-dihydroxy-2,2,5a,7-tetramethyl-hexahydro-3H-1-benzoxepin-6-yl]ethyl}-1-hydroxy-1,4,4-trimethyl-2,3,3a,5,8,8a-hexahydroazulene-6-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      14.544  -0.335   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.876  -1.723   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.672  -0.762   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.377  -2.065   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.337  -0.861   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.860  -1.091   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.820   0.113   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.258   1.547   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.944   0.744   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      17.239   2.701   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      19.218   2.751   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.741   2.521   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.303   1.088   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      22.843   1.088   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      23.803  -0.116   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      24.764   1.088   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      25.191  -0.784   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      23.461  -1.618   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      24.665  -2.578   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      22.073  -2.286   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      20.686  -1.618   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      20.343  -0.116   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      19.296  -1.245   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.045  -3.453   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.585  -3.453   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      18.355  -4.786   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      15.377  -4.840   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.876  -5.183   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.672  -4.223   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.672  -2.683   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.207  -2.207   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.302  -3.453   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.207  -4.699   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.074  -5.741   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      11.512  -6.208   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   30                                             
CONECT    3    2                                                            
CONECT    4    2    5   24                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   22                                                  
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   22                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   13    7   23                                             
CONECT   23   22                                                            
CONECT   24    4   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   33                                                  
CONECT   30   29    2   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   29   34   35                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₅₀O₅

Average Mass

490.7250 Da

Monoisotopic Mass

490.36582 Da

IUPAC Name

(1R)-5-{2-[(3R,5aR,6R,7S,9aR)-3,7-dihydroxy-2,2,5a,7-tetramethyl-decahydro-1-benzoxepin-6-yl]ethyl}-1-hydroxy-1,4,4-trimethyl-1,2,3,3a,4,5,8,8a-octahydroazulene-6-carbaldehyde

Traditional Name

(1R)-5-{2-[(3R,5aR,6R,7S,9aR)-3,7-dihydroxy-2,2,5a,7-tetramethyl-hexahydro-3H-1-benzoxepin-6-yl]ethyl}-1-hydroxy-1,4,4-trimethyl-2,3,3a,5,8,8a-hexahydroazulene-6-carbaldehyde

CAS Registry Number

Not Available

SMILES

C[C@@]1(O)CCC2C1CC=C(C=O)C(CC[C@H]1[C@@](C)(O)CC[C@H]3OC(C)(C)[C@H](O)CC[C@]13C)C2(C)C

InChI Identifier

InChI=1S/C30H50O5/c1-26(2)20(19(18-31)8-9-22-21(26)12-16-29(22,6)33)10-11-23-28(5)15-13-24(32)27(3,4)35-25(28)14-17-30(23,7)34/h8,18,20-25,32-34H,9-17H2,1-7H3/t20?,21?,22?,23-,24-,25-,28-,29-,30+/m1/s1

InChI Key

BDNMFPOVAWCGRX-NXHAIPTASA-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
Callyspongia siphonella	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Oxepane
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Organoheterocyclic compound
Ether
Dialkyl ether
Oxacycle
Organic oxide
Aldehyde
Organic oxygen compound
Organooxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
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	3.93	ChemAxon
pKa (Strongest Acidic)	13.94	ChemAxon
pKa (Strongest Basic)	-0.74	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	139.86 m³·mol⁻¹	ChemAxon
Polarizability	57 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

Not Available

Chemspider ID

20568297

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16736856

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r)-5-{2-[(3r,5ar,6r,7s,9ar)-3,7-dihydroxy-2,2,5a,7-tetramethyl-hexahydro-3h-1-benzoxepin-6-yl]ethyl}-1-hydroxy-1,4,4-trimethyl-2,3,3a,5,8,8a-hexahydroazulene-6-carbaldehyde (NP0291550)

MOL for NP0291550 ((1r)-5-{2-[(3r,5ar,6r,7s,9ar)-3,7-dihydroxy-2,2,5a,7-tetramethyl-hexahydro-3h-1-benzoxepin-6-yl]ethyl}-1-hydroxy-1,4,4-trimethyl-2,3,3a,5,8,8a-hexahydroazulene-6-carbaldehyde)

3D MOL for NP0291550 ((1r)-5-{2-[(3r,5ar,6r,7s,9ar)-3,7-dihydroxy-2,2,5a,7-tetramethyl-hexahydro-3h-1-benzoxepin-6-yl]ethyl}-1-hydroxy-1,4,4-trimethyl-2,3,3a,5,8,8a-hexahydroazulene-6-carbaldehyde)

3D SDF for NP0291550 ((1r)-5-{2-[(3r,5ar,6r,7s,9ar)-3,7-dihydroxy-2,2,5a,7-tetramethyl-hexahydro-3h-1-benzoxepin-6-yl]ethyl}-1-hydroxy-1,4,4-trimethyl-2,3,3a,5,8,8a-hexahydroazulene-6-carbaldehyde)

3D-SDF for NP0291550 ((1r)-5-{2-[(3r,5ar,6r,7s,9ar)-3,7-dihydroxy-2,2,5a,7-tetramethyl-hexahydro-3h-1-benzoxepin-6-yl]ethyl}-1-hydroxy-1,4,4-trimethyl-2,3,3a,5,8,8a-hexahydroazulene-6-carbaldehyde)

PDB for NP0291550 ((1r)-5-{2-[(3r,5ar,6r,7s,9ar)-3,7-dihydroxy-2,2,5a,7-tetramethyl-hexahydro-3h-1-benzoxepin-6-yl]ethyl}-1-hydroxy-1,4,4-trimethyl-2,3,3a,5,8,8a-hexahydroazulene-6-carbaldehyde)

3D PDB for NP0291550 ((1r)-5-{2-[(3r,5ar,6r,7s,9ar)-3,7-dihydroxy-2,2,5a,7-tetramethyl-hexahydro-3h-1-benzoxepin-6-yl]ethyl}-1-hydroxy-1,4,4-trimethyl-2,3,3a,5,8,8a-hexahydroazulene-6-carbaldehyde)

SMILES for NP0291550 ((1r)-5-{2-[(3r,5ar,6r,7s,9ar)-3,7-dihydroxy-2,2,5a,7-tetramethyl-hexahydro-3h-1-benzoxepin-6-yl]ethyl}-1-hydroxy-1,4,4-trimethyl-2,3,3a,5,8,8a-hexahydroazulene-6-carbaldehyde)

INCHI for NP0291550 ((1r)-5-{2-[(3r,5ar,6r,7s,9ar)-3,7-dihydroxy-2,2,5a,7-tetramethyl-hexahydro-3h-1-benzoxepin-6-yl]ethyl}-1-hydroxy-1,4,4-trimethyl-2,3,3a,5,8,8a-hexahydroazulene-6-carbaldehyde)

Structure for NP0291550 ((1r)-5-{2-[(3r,5ar,6r,7s,9ar)-3,7-dihydroxy-2,2,5a,7-tetramethyl-hexahydro-3h-1-benzoxepin-6-yl]ethyl}-1-hydroxy-1,4,4-trimethyl-2,3,3a,5,8,8a-hexahydroazulene-6-carbaldehyde)

3D Structure for NP0291550 ((1r)-5-{2-[(3r,5ar,6r,7s,9ar)-3,7-dihydroxy-2,2,5a,7-tetramethyl-hexahydro-3h-1-benzoxepin-6-yl]ethyl}-1-hydroxy-1,4,4-trimethyl-2,3,3a,5,8,8a-hexahydroazulene-6-carbaldehyde)