NP-MRD: Showing NP-Card for (2z,6r)-6-[(2r,4as,4bs,7r,8s,9as)-8-(2-carboxyethyl)-7-(2-hydroxypropan-2-yl)-4a,8-dimethyl-1-methylidene-2,3,4,4b,5,6,7,9a-octahydrofluoren-2-yl]-2-methylhept-2-enoic acid (NP0269440)

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Record Information

Version

2.0

Created at

2022-09-08 14:55:30 UTC

Updated at

2022-09-08 14:55:31 UTC

NP-MRD ID

NP0269440

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2z,6r)-6-[(2r,4as,4bs,7r,8s,9as)-8-(2-carboxyethyl)-7-(2-hydroxypropan-2-yl)-4a,8-dimethyl-1-methylidene-2,3,4,4b,5,6,7,9a-octahydrofluoren-2-yl]-2-methylhept-2-enoic acid

Description

CHEMBL3593375 belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (2z,6r)-6-[(2r,4as,4bs,7r,8s,9as)-8-(2-carboxyethyl)-7-(2-hydroxypropan-2-yl)-4a,8-dimethyl-1-methylidene-2,3,4,4b,5,6,7,9a-octahydrofluoren-2-yl]-2-methylhept-2-enoic acid is found in Kadsura coccinea. Based on a literature review very few articles have been published on CHEMBL3593375.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082216552D          

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M  END

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M  END


  Mrv1652309082216552D          

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    3.8053   -4.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9883   -5.0525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3132   -5.5878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1085   -2.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4410   -3.0712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7736   -2.5862    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 26 33  1  0  0  0  0
 18 33  1  6  0  0  0
 33 34  2  0  0  0  0
 35 34  1  1  0  0  0
  2 35  1  0  0  0  0
 16 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0269440

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CC\C=C(\C)C(O)=O)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@@H](C(C)(C)O)[C@](C)(CCC(O)=O)C3=C[C@H]2C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O5/c1-18(9-8-10-19(2)27(33)34)21-13-15-29(6)22-11-12-25(28(4,5)35)30(7,16-14-26(31)32)24(22)17-23(29)20(21)3/h10,17-18,21-23,25,35H,3,8-9,11-16H2,1-2,4-7H3,(H,31,32)(H,33,34)/b19-10-/t18-,21-,22-,23+,25+,29+,30-/m1/s1

> <INCHI_KEY>
SCRHXYJKBNGZOH-HGIOFNIASA-N

> <FORMULA>
C30H46O5

> <MOLECULAR_WEIGHT>
486.693

> <EXACT_MASS>
486.334524581

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
57.25330480930788

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z,6R)-6-[(2R,4aS,4bS,7R,8S,9aS)-8-(2-carboxyethyl)-7-(2-hydroxypropan-2-yl)-4a,8-dimethyl-1-methylidene-2,3,4,4a,4b,5,6,7,8,9a-decahydro-1H-fluoren-2-yl]-2-methylhept-2-enoic acid

> <JCHEM_LOGP>
5.707004904666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.182854081147601

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.5723678096794105

> <JCHEM_PKA_STRONGEST_BASIC>
-0.637521344418115

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
140.21660000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2Z,6R)-6-[(2R,4aS,4bS,7R,8S,9aS)-8-(2-carboxyethyl)-7-(2-hydroxypropan-2-yl)-4a,8-dimethyl-1-methylidene-2,3,4,4b,5,6,7,9a-octahydrofluoren-2-yl]-2-methylhept-2-enoic acid

> <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       1.328  -6.612   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.804  -5.148   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.774  -4.003   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.732  -4.324   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.208  -5.788   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.763  -3.179   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.269  -3.499   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.300  -2.355   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.806  -2.675   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.837  -1.531   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.282  -4.140   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -7.788  -4.460   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -5.251  -5.284   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.250  -2.539   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.756  -2.219   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.787  -3.363   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.413  -1.956   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.327  -3.363   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.357  -2.219   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.863  -2.539   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.339  -4.003   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.846  -4.324   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.352  -4.644   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.525  -5.830   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      10.166  -2.817   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.309  -5.148   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.615  -5.964   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.732  -6.576   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.680  -7.789   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.103  -9.217   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.578  -9.431   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       8.051 -10.431   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.802  -4.828   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.557  -5.733   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.311  -4.828   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    3   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   35                                             
CONECT   17   16                                                            
CONECT   18   16   19   33                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22                                                            
CONECT   26   21   27   28   33                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   26   18   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34    2   16                                                  
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₆O₅

Average Mass

486.6930 Da

Monoisotopic Mass

486.33452 Da

IUPAC Name

(2Z,6R)-6-[(2R,4aS,4bS,7R,8S,9aS)-8-(2-carboxyethyl)-7-(2-hydroxypropan-2-yl)-4a,8-dimethyl-1-methylidene-2,3,4,4a,4b,5,6,7,8,9a-decahydro-1H-fluoren-2-yl]-2-methylhept-2-enoic acid

Traditional Name

(2Z,6R)-6-[(2R,4aS,4bS,7R,8S,9aS)-8-(2-carboxyethyl)-7-(2-hydroxypropan-2-yl)-4a,8-dimethyl-1-methylidene-2,3,4,4b,5,6,7,9a-octahydrofluoren-2-yl]-2-methylhept-2-enoic acid

CAS Registry Number

Not Available

SMILES

C[C@H](CC\C=C(\C)C(O)=O)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@@H](C(C)(C)O)[C@](C)(CCC(O)=O)C3=C[C@H]2C1=C

InChI Identifier

InChI=1S/C30H46O5/c1-18(9-8-10-19(2)27(33)34)21-13-15-29(6)22-11-12-25(28(4,5)35)30(7,16-14-26(31)32)24(22)17-23(29)20(21)3/h10,17-18,21-23,25,35H,3,8-9,11-16H2,1-2,4-7H3,(H,31,32)(H,33,34)/b19-10-/t18-,21-,22-,23+,25+,29+,30-/m1/s1

InChI Key

SCRHXYJKBNGZOH-HGIOFNIASA-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
Kadsura coccinea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Abeoabietane diterpenoid
Diterpenoid
Carbocyclic fatty acid
Medium-chain hydroxy acid
Medium-chain fatty acid
Branched fatty acid
Hydroxy fatty acid
Methyl-branched fatty acid
Fatty acyl
Dicarboxylic acid or derivatives
Unsaturated fatty acid
Fatty acid
Tertiary alcohol
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	5.71	ChemAxon
pKa (Strongest Acidic)	4.57	ChemAxon
pKa (Strongest Basic)	-0.64	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	140.22 m³·mol⁻¹	ChemAxon
Polarizability	57.25 Å³	ChemAxon
Number of Rings	3	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

59003936

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122181861

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2z,6r)-6-[(2r,4as,4bs,7r,8s,9as)-8-(2-carboxyethyl)-7-(2-hydroxypropan-2-yl)-4a,8-dimethyl-1-methylidene-2,3,4,4b,5,6,7,9a-octahydrofluoren-2-yl]-2-methylhept-2-enoic acid (NP0269440)

MOL for NP0269440 ((2z,6r)-6-[(2r,4as,4bs,7r,8s,9as)-8-(2-carboxyethyl)-7-(2-hydroxypropan-2-yl)-4a,8-dimethyl-1-methylidene-2,3,4,4b,5,6,7,9a-octahydrofluoren-2-yl]-2-methylhept-2-enoic acid)

3D MOL for NP0269440 ((2z,6r)-6-[(2r,4as,4bs,7r,8s,9as)-8-(2-carboxyethyl)-7-(2-hydroxypropan-2-yl)-4a,8-dimethyl-1-methylidene-2,3,4,4b,5,6,7,9a-octahydrofluoren-2-yl]-2-methylhept-2-enoic acid)

3D SDF for NP0269440 ((2z,6r)-6-[(2r,4as,4bs,7r,8s,9as)-8-(2-carboxyethyl)-7-(2-hydroxypropan-2-yl)-4a,8-dimethyl-1-methylidene-2,3,4,4b,5,6,7,9a-octahydrofluoren-2-yl]-2-methylhept-2-enoic acid)

3D-SDF for NP0269440 ((2z,6r)-6-[(2r,4as,4bs,7r,8s,9as)-8-(2-carboxyethyl)-7-(2-hydroxypropan-2-yl)-4a,8-dimethyl-1-methylidene-2,3,4,4b,5,6,7,9a-octahydrofluoren-2-yl]-2-methylhept-2-enoic acid)

PDB for NP0269440 ((2z,6r)-6-[(2r,4as,4bs,7r,8s,9as)-8-(2-carboxyethyl)-7-(2-hydroxypropan-2-yl)-4a,8-dimethyl-1-methylidene-2,3,4,4b,5,6,7,9a-octahydrofluoren-2-yl]-2-methylhept-2-enoic acid)

3D PDB for NP0269440 ((2z,6r)-6-[(2r,4as,4bs,7r,8s,9as)-8-(2-carboxyethyl)-7-(2-hydroxypropan-2-yl)-4a,8-dimethyl-1-methylidene-2,3,4,4b,5,6,7,9a-octahydrofluoren-2-yl]-2-methylhept-2-enoic acid)

SMILES for NP0269440 ((2z,6r)-6-[(2r,4as,4bs,7r,8s,9as)-8-(2-carboxyethyl)-7-(2-hydroxypropan-2-yl)-4a,8-dimethyl-1-methylidene-2,3,4,4b,5,6,7,9a-octahydrofluoren-2-yl]-2-methylhept-2-enoic acid)

INCHI for NP0269440 ((2z,6r)-6-[(2r,4as,4bs,7r,8s,9as)-8-(2-carboxyethyl)-7-(2-hydroxypropan-2-yl)-4a,8-dimethyl-1-methylidene-2,3,4,4b,5,6,7,9a-octahydrofluoren-2-yl]-2-methylhept-2-enoic acid)

Structure for NP0269440 ((2z,6r)-6-[(2r,4as,4bs,7r,8s,9as)-8-(2-carboxyethyl)-7-(2-hydroxypropan-2-yl)-4a,8-dimethyl-1-methylidene-2,3,4,4b,5,6,7,9a-octahydrofluoren-2-yl]-2-methylhept-2-enoic acid)

3D Structure for NP0269440 ((2z,6r)-6-[(2r,4as,4bs,7r,8s,9as)-8-(2-carboxyethyl)-7-(2-hydroxypropan-2-yl)-4a,8-dimethyl-1-methylidene-2,3,4,4b,5,6,7,9a-octahydrofluoren-2-yl]-2-methylhept-2-enoic acid)