NP-MRD: Showing NP-Card for (4ar,5r,6r,6as,7r,11ar,11br)-4a,6-dihydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,9h,11ah-phenanthro[3,2-b]furan-5-yl benzoate (NP0144625)

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Record Information

Version

2.0

Created at

2022-09-01 23:38:32 UTC

Updated at

2022-09-01 23:38:32 UTC

NP-MRD ID

NP0144625

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4ar,5r,6r,6as,7r,11ar,11br)-4a,6-dihydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,9h,11ah-phenanthro[3,2-b]furan-5-yl benzoate

Description

Neocaesalpin R belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. (4ar,5r,6r,6as,7r,11ar,11br)-4a,6-dihydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,9h,11ah-phenanthro[3,2-b]furan-5-yl benzoate is found in Caesalpinia pulcherrima. (4ar,5r,6r,6as,7r,11ar,11br)-4a,6-dihydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,9h,11ah-phenanthro[3,2-b]furan-5-yl benzoate was first documented in 2009 (PMID: 19135690). Based on a literature review very few articles have been published on Neocaesalpin R (PMID: 26087554).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022201382D          

 32 36  0  0  1  0            999 V2000
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    4.7875   -0.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340    1.1139    0.0000 O   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


  Mrv1652309022201382D          

 32 36  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0144625

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1[C@@H]2[C@@H](O)[C@@H](OC(=O)C3=CC=CC=C3)[C@@]3(O)C(C)(C)CCC[C@]3(C)[C@H]2C=C2OCC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C27H34O5/c1-16-18-11-14-31-20(18)15-19-21(16)22(28)23(32-24(29)17-9-6-5-7-10-17)27(30)25(2,3)12-8-13-26(19,27)4/h5-7,9-11,15-16,19,21-23,28,30H,8,12-14H2,1-4H3/t16-,19-,21-,22+,23+,26+,27+/m0/s1

> <INCHI_KEY>
RSPQORSLBMMXNF-WVTZLOSNSA-N

> <FORMULA>
C27H34O5

> <MOLECULAR_WEIGHT>
438.564

> <EXACT_MASS>
438.240624195

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
48.917346075818614

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,7R,8R,9R,10S,11R)-7,9-dihydroxy-2,6,6,11-tetramethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12,16-dien-8-yl benzoate

> <ALOGPS_LOGP>
4.48

> <JCHEM_LOGP>
3.904370747999999

> <ALOGPS_LOGS>
-4.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.974025907705567

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.006108244273655

> <JCHEM_PKA_STRONGEST_BASIC>
-3.324934712657986

> <JCHEM_POLAR_SURFACE_AREA>
75.99

> <JCHEM_REFRACTIVITY>
123.7626

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.84e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,7R,8R,9R,10S,11R)-7,9-dihydroxy-2,6,6,11-tetramethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12,16-dien-8-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       6.928  -2.940   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.405  -1.492   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.398  -0.314   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.937  -0.264   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.365   1.215   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.090   2.079   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.874   1.134   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.358   1.405   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.366   0.228   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.889  -1.221   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.896  -2.398   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.419  -3.846   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.380  -2.127   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.387  -3.304   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.911  -4.752   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.427  -5.024   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.918  -5.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.441  -7.378   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.448  -8.556   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.068  -8.284   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.591  -6.836   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.598  -5.659   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.857  -0.678   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.864  -1.856   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.337  -1.947   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.176  -0.671   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.810   2.218   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.850   0.499   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.842   1.676   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    3    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   31                                                  
CONECT   10    9    2   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   23                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
CONECT   23   13   24   25   31                                             
CONECT   24   23                                                            
CONECT   25   23   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30    9   23   32                                             
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₄O₅

Average Mass

438.5640 Da

Monoisotopic Mass

438.24062 Da

IUPAC Name

(1R,2R,7R,8R,9R,10S,11R)-7,9-dihydroxy-2,6,6,11-tetramethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12,16-dien-8-yl benzoate

Traditional Name

(1R,2R,7R,8R,9R,10S,11R)-7,9-dihydroxy-2,6,6,11-tetramethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12,16-dien-8-yl benzoate

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@@H]2[C@@H](O)[C@@H](OC(=O)C3=CC=CC=C3)[C@@]3(O)C(C)(C)CCC[C@]3(C)[C@H]2C=C2OCC=C12

InChI Identifier

InChI=1S/C27H34O5/c1-16-18-11-14-31-20(18)15-19-21(16)22(28)23(32-24(29)17-9-6-5-7-10-17)27(30)25(2,3)12-8-13-26(19,27)4/h5-7,9-11,15-16,19,21-23,28,30H,8,12-14H2,1-4H3/t16-,19-,21-,22+,23+,26+,27+/m0/s1

InChI Key

RSPQORSLBMMXNF-WVTZLOSNSA-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
Caesalpinia pulcherrima	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Benzenoid
Monocyclic benzene moiety
Tertiary alcohol
Dihydrofuran
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	4.48	ALOGPS
logP	3.9	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	13.01	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	123.76 m³·mol⁻¹	ChemAxon
Polarizability	48.92 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

C00048490

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

102286694

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sun ZH, Ma GX, Tian Y, Yang JS, Yuan JQ, Xu XD: [Cassae-type diterpenes from seeds of Caesalpinia minax]. Zhongguo Zhong Yao Za Zhi. 2015 Mar;40(5):903-7. [PubMed:26087554 ]
Pranithanchai W, Karalai C, Ponglimanont C, Subhadhirasakul S, Chantrapromma K: Cassane diterpenoids from the stem of Caesalpinia pulcherrima. Phytochemistry. 2009 Jan;70(2):300-4. doi: 10.1016/j.phytochem.2008.12.006. Epub 2009 Jan 8. [PubMed:19135690 ]
LOTUS database [Link]

Showing NP-Card for (4ar,5r,6r,6as,7r,11ar,11br)-4a,6-dihydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,9h,11ah-phenanthro[3,2-b]furan-5-yl benzoate (NP0144625)

MOL for NP0144625 ((4ar,5r,6r,6as,7r,11ar,11br)-4a,6-dihydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,9h,11ah-phenanthro[3,2-b]furan-5-yl benzoate)

3D MOL for NP0144625 ((4ar,5r,6r,6as,7r,11ar,11br)-4a,6-dihydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,9h,11ah-phenanthro[3,2-b]furan-5-yl benzoate)

3D SDF for NP0144625 ((4ar,5r,6r,6as,7r,11ar,11br)-4a,6-dihydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,9h,11ah-phenanthro[3,2-b]furan-5-yl benzoate)

3D-SDF for NP0144625 ((4ar,5r,6r,6as,7r,11ar,11br)-4a,6-dihydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,9h,11ah-phenanthro[3,2-b]furan-5-yl benzoate)

PDB for NP0144625 ((4ar,5r,6r,6as,7r,11ar,11br)-4a,6-dihydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,9h,11ah-phenanthro[3,2-b]furan-5-yl benzoate)

3D PDB for NP0144625 ((4ar,5r,6r,6as,7r,11ar,11br)-4a,6-dihydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,9h,11ah-phenanthro[3,2-b]furan-5-yl benzoate)

SMILES for NP0144625 ((4ar,5r,6r,6as,7r,11ar,11br)-4a,6-dihydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,9h,11ah-phenanthro[3,2-b]furan-5-yl benzoate)

INCHI for NP0144625 ((4ar,5r,6r,6as,7r,11ar,11br)-4a,6-dihydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,9h,11ah-phenanthro[3,2-b]furan-5-yl benzoate)

Structure for NP0144625 ((4ar,5r,6r,6as,7r,11ar,11br)-4a,6-dihydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,9h,11ah-phenanthro[3,2-b]furan-5-yl benzoate)

3D Structure for NP0144625 ((4ar,5r,6r,6as,7r,11ar,11br)-4a,6-dihydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,9h,11ah-phenanthro[3,2-b]furan-5-yl benzoate)