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 (2e)-3-phenylprop-2-enoate (NP0168896)

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Record Information

Version

2.0

Created at

2022-09-03 04:45:59 UTC

Updated at

2022-09-03 04:45:59 UTC

NP-MRD ID

NP0168896

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 (2e)-3-phenylprop-2-enoate

Description

Neocaesalpin P 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 (2e)-3-phenylprop-2-enoate 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 (2e)-3-phenylprop-2-enoate was first documented in 2009 (PMID: 19413105). Based on a literature review a small amount of articles have been published on Neocaesalpin P (PMID: 26087554) (PMID: 19135690).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032206462D          

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M  END

     RDKit          3D

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  Mrv1652309032206462D          

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 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
 13 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 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
  9 33  1  0  0  0  0
 25 33  1  0  0  0  0
 33 34  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0168896

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O5/c1-18-20-13-16-33-22(20)17-21-24(18)25(31)26(29(32)27(2,3)14-8-15-28(21,29)4)34-23(30)12-11-19-9-6-5-7-10-19/h5-7,9-13,17-18,21,24-26,31-32H,8,14-16H2,1-4H3/b12-11+/t18-,21-,24-,25+,26+,28+,29+/m0/s1

> <INCHI_KEY>
UDSHSKLWXBXHPZ-PSGKSZDDSA-N

> <FORMULA>
C29H36O5

> <MOLECULAR_WEIGHT>
464.602

> <EXACT_MASS>
464.256274259

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
52.413990410542546

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <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 (2E)-3-phenylprop-2-enoate

> <ALOGPS_LOGP>
5.25

> <JCHEM_LOGP>
4.442961617333332

> <ALOGPS_LOGS>
-4.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.97405599212209

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.006138410360265

> <JCHEM_PKA_STRONGEST_BASIC>
-3.324921516559078

> <JCHEM_POLAR_SURFACE_AREA>
75.99

> <JCHEM_REFRACTIVITY>
133.50830000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.44e-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 (2E)-3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-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       0.972 -10.004   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.021 -11.181   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.537 -10.910   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.060  -9.462   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.068  -8.284   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.857  -0.678   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.864  -1.856   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.337  -1.947   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.176  -0.671   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.810   2.218   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.850   0.499   0.000  0.00  0.00           C+0
HETATM   34  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   33                                                  
CONECT   10    9    2   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   25                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   19                                                       
CONECT   25   13   26   27   33                                             
CONECT   26   25                                                            
CONECT   27   25   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32    9   25   34                                             
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₆O₅

Average Mass

464.6020 Da

Monoisotopic Mass

464.25627 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 (2E)-3-phenylprop-2-enoate

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 (2E)-3-phenylprop-2-enoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C29H36O5/c1-18-20-13-16-33-22(20)17-21-24(18)25(31)26(29(32)27(2,3)14-8-15-28(21,29)4)34-23(30)12-11-19-9-6-5-7-10-19/h5-7,9-13,17-18,21,24-26,31-32H,8,14-16H2,1-4H3/b12-11+/t18-,21-,24-,25+,26+,28+,29+/m0/s1

InChI Key

UDSHSKLWXBXHPZ-PSGKSZDDSA-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
Cinnamic acid ester
Cinnamic acid or derivatives
Styrene
Fatty acid ester
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
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
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	5.25	ALOGPS
logP	4.44	ChemAxon
logS	-4.9	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	4	ChemAxon
Refractivity	133.51 m³·mol⁻¹	ChemAxon
Polarizability	52.41 Å³	ChemAxon
Number of Rings	5	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

C00048488

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

102286692

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ata A, Udenigwe CC, Gale EM, Samarasekera R: Minor chemical constituents of Caesalpinia bonduc. Nat Prod Commun. 2009 Mar;4(3):311-4. [PubMed:19413105 ]
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 (2e)-3-phenylprop-2-enoate (NP0168896)

MOL for NP0168896 ((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 (2e)-3-phenylprop-2-enoate)

3D MOL for NP0168896 ((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 (2e)-3-phenylprop-2-enoate)

3D SDF for NP0168896 ((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 (2e)-3-phenylprop-2-enoate)

3D-SDF for NP0168896 ((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 (2e)-3-phenylprop-2-enoate)

PDB for NP0168896 ((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 (2e)-3-phenylprop-2-enoate)

3D PDB for NP0168896 ((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 (2e)-3-phenylprop-2-enoate)

SMILES for NP0168896 ((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 (2e)-3-phenylprop-2-enoate)

INCHI for NP0168896 ((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 (2e)-3-phenylprop-2-enoate)

Structure for NP0168896 ((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 (2e)-3-phenylprop-2-enoate)

3D Structure for NP0168896 ((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 (2e)-3-phenylprop-2-enoate)