NP-MRD: Showing NP-Card for [(3s,4as,6as,7s,10ar,10bs)-3,4a,7,10a-tetramethyl-7-({[(2z)-2-methylbut-2-enoyl]oxy}methyl)-octahydro-1h-naphtho[2,1-b]pyran-3-yl]acetic acid (NP0173671)

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Record Information

Version

1.0

Created at

2022-09-03 10:50:49 UTC

Updated at

2022-09-03 10:50:50 UTC

NP-MRD ID

NP0173671

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(3s,4as,6as,7s,10ar,10bs)-3,4a,7,10a-tetramethyl-7-({[(2z)-2-methylbut-2-enoyl]oxy}methyl)-octahydro-1h-naphtho[2,1-b]pyran-3-yl]acetic acid

Description

2-[(3S,4aS,6aS,7S,10aR,10bS)-3,4a,7,10a-tetramethyl-7-({[(2Z)-2-methylbut-2-enoyl]oxy}methyl)-dodecahydro-1H-naphtho[2,1-b]pyran-3-yl]acetic acid belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. [(3s,4as,6as,7s,10ar,10bs)-3,4a,7,10a-tetramethyl-7-({[(2z)-2-methylbut-2-enoyl]oxy}methyl)-octahydro-1h-naphtho[2,1-b]pyran-3-yl]acetic acid is found in Olearia teretifolia. It was first documented in 2022 (PMID: 36057450). Based on a literature review a significant number of articles have been published on 2-[(3S,4aS,6aS,7S,10aR,10bS)-3,4a,7,10a-tetramethyl-7-({[(2Z)-2-methylbut-2-enoyl]oxy}methyl)-dodecahydro-1H-naphtho[2,1-b]pyran-3-yl]acetic acid (PMID: 36057449) (PMID: 36057448) (PMID: 36057447) (PMID: 36057446).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032212502D          

 30 32  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309032212502D          

 30 32  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0173671

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(\C)C(=O)OC[C@@]1(C)CCC[C@]2(C)[C@@H]1CC[C@]1(C)O[C@](C)(CC(O)=O)CC[C@@H]21

> <INCHI_IDENTIFIER>
InChI=1S/C25H40O5/c1-7-17(2)21(28)29-16-22(3)11-8-12-24(5)18(22)10-14-25(6)19(24)9-13-23(4,30-25)15-20(26)27/h7,18-19H,8-16H2,1-6H3,(H,26,27)/b17-7-/t18-,19+,22-,23+,24-,25+/m1/s1

> <INCHI_KEY>
ZKBZRVVQDYSKMH-GMANOVGDSA-N

> <FORMULA>
C25H40O5

> <MOLECULAR_WEIGHT>
420.59

> <EXACT_MASS>
420.287574388

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
48.61389743880711

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(3S,4aS,6aS,7S,10aR,10bS)-3,4a,7,10a-tetramethyl-7-({[(2Z)-2-methylbut-2-enoyl]oxy}methyl)-dodecahydro-1H-naphtho[2,1-b]pyran-3-yl]acetic acid

> <ALOGPS_LOGP>
4.98

> <JCHEM_LOGP>
5.414474060666665

> <ALOGPS_LOGS>
-5.68

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.490383463827447

> <JCHEM_PKA_STRONGEST_BASIC>
-4.210708674856137

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
116.69859999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.87e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(3S,4aS,6aS,7S,10aR,10bS)-3,4a,7,10a-tetramethyl-7-({[(2Z)-2-methylbut-2-enoyl]oxy}methyl)-octahydro-1H-naphtho[2,1-b]pyran-3-yl]acetic acid

> <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      13.692  -1.681   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.424  -0.164   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.977   0.363   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.710   1.879   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.798  -0.627   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      11.065  -2.144   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       9.351  -0.100   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.171  -1.090   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.456  -2.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -1.897   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.564  -0.564   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.386  -0.220   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.386   1.760   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.119   3.276   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.298   4.266   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.329   3.803   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   16                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   30                                             
CONECT   15   14                                                            
CONECT   16   14    9   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21   30                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24   28                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   22   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   19   14                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Value	Source
2-[(3S,4AS,6as,7S,10ar,10BS)-3,4a,7,10a-tetramethyl-7-({[(2Z)-2-methylbut-2-enoyl]oxy}methyl)-dodecahydro-1H-naphtho[2,1-b]pyran-3-yl]acetate	Generator

Chemical Formula

C₂₅H₄₀O₅

Average Mass

420.5900 Da

Monoisotopic Mass

420.28757 Da

IUPAC Name

2-[(3S,4aS,6aS,7S,10aR,10bS)-3,4a,7,10a-tetramethyl-7-({[(2Z)-2-methylbut-2-enoyl]oxy}methyl)-dodecahydro-1H-naphtho[2,1-b]pyran-3-yl]acetic acid

Traditional Name

[(3S,4aS,6aS,7S,10aR,10bS)-3,4a,7,10a-tetramethyl-7-({[(2Z)-2-methylbut-2-enoyl]oxy}methyl)-octahydro-1H-naphtho[2,1-b]pyran-3-yl]acetic acid

CAS Registry Number

Not Available

SMILES

C\C=C(\C)C(=O)OC[C@@]1(C)CCC[C@]2(C)[C@@H]1CC[C@]1(C)O[C@](C)(CC(O)=O)CC[C@@H]21

InChI Identifier

InChI=1S/C25H40O5/c1-7-17(2)21(28)29-16-22(3)11-8-12-24(5)18(22)10-14-25(6)19(24)9-13-23(4,30-25)15-20(26)27/h7,18-19H,8-16H2,1-6H3,(H,26,27)/b17-7-/t18-,19+,22-,23+,24-,25+/m1/s1

InChI Key

ZKBZRVVQDYSKMH-GMANOVGDSA-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
Olearia teretifolia	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
Polycyclic triterpenoid
Naphthopyran
Naphthalene
Fatty acid ester
Dicarboxylic acid or derivatives
Oxane
Pyran
Fatty acyl
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Ether
Dialkyl ether
Carboxylic acid
Organoheterocyclic compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	4.98	ALOGPS
logP	5.41	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	4.49	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	116.7 m³·mol⁻¹	ChemAxon
Polarizability	48.61 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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

162933886

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Micalizzi E, Vaudano AE, Ballerini A, Talami F, Giovannini G, Turchi G, Cioclu MC, Giunta L, Meletti S: Ictal Apnea: a prospective monocentric study in patients with epilepsy. Eur J Neurol. 2022 Sep 3. doi: 10.1111/ene.15547. [PubMed:36057450 ]
Jiang S, Guo P, Heo HY, Zhang Y, Wu J, Jin Y, Laterra J, Eberhart CG, Lim M, Blakeley JO: Radiomics analysis of amide proton transfer-weighted and structural MR images for treatment response assessment in malignant gliomas. NMR Biomed. 2022 Sep 3:e4824. doi: 10.1002/nbm.4824. [PubMed:36057449 ]
Agarwal K, Saikia P, Podder I: Metabolic syndrome and Dyslipidemia in xanthelasma palpebrarum and associated risk-factors- a case-control study. J Cosmet Dermatol. 2022 Sep 3. doi: 10.1111/jocd.15353. [PubMed:36057448 ]
Lebel V, Argiropoulos N, Robins S, Charbonneau L, Feeley N: Family-centred care and breastfeeding self-efficacy determined how ready mothers were for their infants to be discharged from a neonatal intensive care unit. Acta Paediatr. 2022 Sep 3. doi: 10.1111/apa.16538. [PubMed:36057447 ]
Park JI, Kim SJ, Kim YJ, Lee SJ: Protective role of Caesalpinia sappan extract and its main component brazilin against blue light-induced damage in human fibroblasts. J Cosmet Dermatol. 2022 Sep 3. doi: 10.1111/jocd.15354. [PubMed:36057446 ]
LOTUS database [Link]

Showing NP-Card for [(3s,4as,6as,7s,10ar,10bs)-3,4a,7,10a-tetramethyl-7-({[(2z)-2-methylbut-2-enoyl]oxy}methyl)-octahydro-1h-naphtho[2,1-b]pyran-3-yl]acetic acid (NP0173671)

MOL for NP0173671 ([(3s,4as,6as,7s,10ar,10bs)-3,4a,7,10a-tetramethyl-7-({[(2z)-2-methylbut-2-enoyl]oxy}methyl)-octahydro-1h-naphtho[2,1-b]pyran-3-yl]acetic acid)

3D MOL for NP0173671 ([(3s,4as,6as,7s,10ar,10bs)-3,4a,7,10a-tetramethyl-7-({[(2z)-2-methylbut-2-enoyl]oxy}methyl)-octahydro-1h-naphtho[2,1-b]pyran-3-yl]acetic acid)

3D SDF for NP0173671 ([(3s,4as,6as,7s,10ar,10bs)-3,4a,7,10a-tetramethyl-7-({[(2z)-2-methylbut-2-enoyl]oxy}methyl)-octahydro-1h-naphtho[2,1-b]pyran-3-yl]acetic acid)

3D-SDF for NP0173671 ([(3s,4as,6as,7s,10ar,10bs)-3,4a,7,10a-tetramethyl-7-({[(2z)-2-methylbut-2-enoyl]oxy}methyl)-octahydro-1h-naphtho[2,1-b]pyran-3-yl]acetic acid)

PDB for NP0173671 ([(3s,4as,6as,7s,10ar,10bs)-3,4a,7,10a-tetramethyl-7-({[(2z)-2-methylbut-2-enoyl]oxy}methyl)-octahydro-1h-naphtho[2,1-b]pyran-3-yl]acetic acid)

3D PDB for NP0173671 ([(3s,4as,6as,7s,10ar,10bs)-3,4a,7,10a-tetramethyl-7-({[(2z)-2-methylbut-2-enoyl]oxy}methyl)-octahydro-1h-naphtho[2,1-b]pyran-3-yl]acetic acid)

SMILES for NP0173671 ([(3s,4as,6as,7s,10ar,10bs)-3,4a,7,10a-tetramethyl-7-({[(2z)-2-methylbut-2-enoyl]oxy}methyl)-octahydro-1h-naphtho[2,1-b]pyran-3-yl]acetic acid)

INCHI for NP0173671 ([(3s,4as,6as,7s,10ar,10bs)-3,4a,7,10a-tetramethyl-7-({[(2z)-2-methylbut-2-enoyl]oxy}methyl)-octahydro-1h-naphtho[2,1-b]pyran-3-yl]acetic acid)

Structure for NP0173671 ([(3s,4as,6as,7s,10ar,10bs)-3,4a,7,10a-tetramethyl-7-({[(2z)-2-methylbut-2-enoyl]oxy}methyl)-octahydro-1h-naphtho[2,1-b]pyran-3-yl]acetic acid)

3D Structure for NP0173671 ([(3s,4as,6as,7s,10ar,10bs)-3,4a,7,10a-tetramethyl-7-({[(2z)-2-methylbut-2-enoyl]oxy}methyl)-octahydro-1h-naphtho[2,1-b]pyran-3-yl]acetic acid)