NP-MRD: Showing NP-Card for 3-[12-(3-hydroxyprop-1-en-2-yl)-4,8-dimethyl-5-[1-(4-methylfuran-2-yl)propan-2-yl]tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid (NP0202563)

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Record Information

Version

2.0

Created at

2022-09-04 21:48:12 UTC

Updated at

2022-09-04 21:48:12 UTC

NP-MRD ID

NP0202563

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[12-(3-hydroxyprop-1-en-2-yl)-4,8-dimethyl-5-[1-(4-methylfuran-2-yl)propan-2-yl]tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid

Description

3-[12-(3-Hydroxyprop-1-en-2-yl)-4,8-dimethyl-5-[1-(4-methylfuran-2-yl)propan-2-yl]tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]Tetradecan-13-yl]propanoic acid belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 3-[12-(3-hydroxyprop-1-en-2-yl)-4,8-dimethyl-5-[1-(4-methylfuran-2-yl)propan-2-yl]tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid is found in Gardenia obtusifolia. 3-[12-(3-Hydroxyprop-1-en-2-yl)-4,8-dimethyl-5-[1-(4-methylfuran-2-yl)propan-2-yl]tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]Tetradecan-13-yl]propanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251505432D          

 34 38  0  0  0  0            999 V2000
    4.4349    2.4627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0349    3.4717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004251505432D          

 34 38  0  0  0  0            999 V2000
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  4  9  2  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
 15 30  1  0  0  0  0
 23 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
 10 33  1  0  0  0  0
 13 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0202563

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CC1=CC(C)=CO1)C1CCC2(C)C3CCC(C(=C)CO)C4(CCC(O)=O)CC34CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O4/c1-19-14-22(34-17-19)15-20(2)23-8-10-28(5)25-7-6-24(21(3)16-31)29(11-9-26(32)33)18-30(25,29)13-12-27(23,28)4/h14,17,20,23-25,31H,3,6-13,15-16,18H2,1-2,4-5H3,(H,32,33)

> <INCHI_KEY>
BMUQIRNIOOTLBR-UHFFFAOYSA-N

> <FORMULA>
C30H44O4

> <MOLECULAR_WEIGHT>
468.678

> <EXACT_MASS>
468.323959897

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
55.209181710221756

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[12-(3-hydroxyprop-1-en-2-yl)-4,8-dimethyl-5-[1-(4-methylfuran-2-yl)propan-2-yl]tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid

> <ALOGPS_LOGP>
5.38

> <JCHEM_LOGP>
5.774481097333333

> <ALOGPS_LOGS>
-5.01

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.896403905552294

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.756579446958975

> <JCHEM_PKA_STRONGEST_BASIC>
-1.8979004448441588

> <JCHEM_POLAR_SURFACE_AREA>
70.67

> <JCHEM_REFRACTIVITY>
134.14289999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.61e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[12-(3-hydroxyprop-1-en-2-yl)-4,8-dimethyl-5-[1-(4-methylfuran-2-yl)propan-2-yl]tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       8.279   4.597   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.107   3.299   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.645   3.367   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.356   4.733   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      10.668   6.111   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      11.765   7.191   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.132   6.480   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.510   7.168   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.878   4.961   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.396   1.932   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.084   0.554   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.986  -0.526   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.620   0.185   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.527  -1.352   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.178  -0.355   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.924  -1.874   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.482  -2.414   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.293  -1.435   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.851  -1.975   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.598  -3.494   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.338  -0.997   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.780  -1.537   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.547   0.084   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.028   0.337   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.488   1.779   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.031   2.033   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.010   0.844   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -1.571   3.475   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.800   1.603   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.989   0.624   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.242   2.143   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.684   2.683   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.873   1.704   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.284   3.188   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7    4                                                       
CONECT   10    2   11   33                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   33                                             
CONECT   14   13                                                            
CONECT   15   13   16   30                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21                                                            
CONECT   23   18   24   29   30                                             
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   23   30                                                       
CONECT   30   29   15   23   31                                             
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   10   13   34                                             
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Value	Source
3-[12-(3-Hydroxyprop-1-en-2-yl)-4,8-dimethyl-5-[1-(4-methylfuran-2-yl)propan-2-yl]tetracyclo[7.5.0.0,.0,]tetradecan-13-yl]propanoate	Generator
3-[12-(3-Hydroxyprop-1-en-2-yl)-4,8-dimethyl-5-[1-(4-methylfuran-2-yl)propan-2-yl]tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoate	Generator

Chemical Formula

C₃₀H₄₄O₄

Average Mass

468.6780 Da

Monoisotopic Mass

468.32396 Da

IUPAC Name

3-[12-(3-hydroxyprop-1-en-2-yl)-4,8-dimethyl-5-[1-(4-methylfuran-2-yl)propan-2-yl]tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid

Traditional Name

3-[12-(3-hydroxyprop-1-en-2-yl)-4,8-dimethyl-5-[1-(4-methylfuran-2-yl)propan-2-yl]tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid

CAS Registry Number

Not Available

SMILES

CC(CC1=CC(C)=CO1)C1CCC2(C)C3CCC(C(=C)CO)C4(CCC(O)=O)CC34CCC12C

InChI Identifier

InChI=1S/C30H44O4/c1-19-14-22(34-17-19)15-20(2)23-8-10-28(5)25-7-6-24(21(3)16-31)29(11-9-26(32)33)18-30(25,29)13-12-27(23,28)4/h14,17,20,23-25,31H,3,6-13,15-16,18H2,1-2,4-5H3,(H,32,33)

InChI Key

BMUQIRNIOOTLBR-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
Gardenia obtusifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Pinguisane sesquiterpenoid
Carbocyclic fatty acid
Hydroxy fatty acid
Fatty acyl
Furan
Heteroaromatic compound
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Primary alcohol
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
logP	5.38	ALOGPS
logP	5.77	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.76	ChemAxon
pKa (Strongest Basic)	-1.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70.67 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	134.14 m³·mol⁻¹	ChemAxon
Polarizability	55.21 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-[12-(3-hydroxyprop-1-en-2-yl)-4,8-dimethyl-5-[1-(4-methylfuran-2-yl)propan-2-yl]tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid (NP0202563)

MOL for NP0202563 (3-[12-(3-hydroxyprop-1-en-2-yl)-4,8-dimethyl-5-[1-(4-methylfuran-2-yl)propan-2-yl]tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid)

3D MOL for NP0202563 (3-[12-(3-hydroxyprop-1-en-2-yl)-4,8-dimethyl-5-[1-(4-methylfuran-2-yl)propan-2-yl]tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid)

3D SDF for NP0202563 (3-[12-(3-hydroxyprop-1-en-2-yl)-4,8-dimethyl-5-[1-(4-methylfuran-2-yl)propan-2-yl]tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid)

3D-SDF for NP0202563 (3-[12-(3-hydroxyprop-1-en-2-yl)-4,8-dimethyl-5-[1-(4-methylfuran-2-yl)propan-2-yl]tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid)

PDB for NP0202563 (3-[12-(3-hydroxyprop-1-en-2-yl)-4,8-dimethyl-5-[1-(4-methylfuran-2-yl)propan-2-yl]tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid)

3D PDB for NP0202563 (3-[12-(3-hydroxyprop-1-en-2-yl)-4,8-dimethyl-5-[1-(4-methylfuran-2-yl)propan-2-yl]tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid)

SMILES for NP0202563 (3-[12-(3-hydroxyprop-1-en-2-yl)-4,8-dimethyl-5-[1-(4-methylfuran-2-yl)propan-2-yl]tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid)

INCHI for NP0202563 (3-[12-(3-hydroxyprop-1-en-2-yl)-4,8-dimethyl-5-[1-(4-methylfuran-2-yl)propan-2-yl]tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid)

Structure for NP0202563 (3-[12-(3-hydroxyprop-1-en-2-yl)-4,8-dimethyl-5-[1-(4-methylfuran-2-yl)propan-2-yl]tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid)

3D Structure for NP0202563 (3-[12-(3-hydroxyprop-1-en-2-yl)-4,8-dimethyl-5-[1-(4-methylfuran-2-yl)propan-2-yl]tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid)