Showing chemical card for 6-({8-acetyl-12-ethyl-5,6-dimethoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6-trien-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid (CFc000143059)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 23:20:13 UTC

Chemfont ID

CFc000143059

Molecule Identification

Common Name

6-({8-acetyl-12-ethyl-5,6-dimethoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6-trien-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

Definition

6-({8-acetyl-12-ethyl-5,6-dimethoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6-trien-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid belongs to the class of organic compounds known as aspidospermatan-type alkaloids. These are tryptophan-derived alkaloids that are derived from the fusion of tryptamine and a terpene unit (generally either 9 or 10 carbons). Aspidospermine and aspidospermidine (along with tabersonine) are the archetypical members of the Aspidosperma alkaloids. 6-({8-acetyl-12-ethyl-5,6-dimethoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6-trien-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid is a very strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

MOL for CFc000143059 (6-({8-acetyl-12-ethyl-5,6-dimethoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6-trien-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

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3D MOL for CFc000143059 (6-({8-acetyl-12-ethyl-5,6-dimethoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6-trien-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

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3D SDF for CFc000143059 (6-({8-acetyl-12-ethyl-5,6-dimethoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6-trien-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

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3D-SDF for CFc000143059 (6-({8-acetyl-12-ethyl-5,6-dimethoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6-trien-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

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PDB for CFc000143059 (6-({8-acetyl-12-ethyl-5,6-dimethoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6-trien-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

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3D PDB for CFc000143059 (6-({8-acetyl-12-ethyl-5,6-dimethoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6-trien-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

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SMILES for CFc000143059 (6-({8-acetyl-12-ethyl-5,6-dimethoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6-trien-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

CCC12CCCN3CCC4(C(CC1)N(C(C)=O)C1=C(OC)C(OC)=C(OC5OC(C(O)C(O)C5O)C(O)=O)C=C41)C23

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INCHI for CFc000143059 (6-({8-acetyl-12-ethyl-5,6-dimethoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6-trien-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

InChI=1S/C29H40N2O10/c1-5-28-8-6-11-30-12-10-29(27(28)30)15-13-16(40-26-21(35)19(33)20(34)24(41-26)25(36)37)22(38-3)23(39-4)18(15)31(14(2)32)17(29)7-9-28/h13,17,19-21,24,26-27,33-35H,5-12H2,1-4H3,(H,36,37)

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Structure for CFc000143059 (6-({8-acetyl-12-ethyl-5,6-dimethoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6-trien-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

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3D Structure for CFc000143059 (6-({8-acetyl-12-ethyl-5,6-dimethoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6-trien-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

Synonyms

Value	Source
6-({8-acetyl-12-ethyl-5,6-dimethoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6-trien-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylate	Generator

Chemical Formula

C₂₉H₄₀N₂O₁₀

Average Molecular Weight

576.643

Monoisotopic Molecular Weight

576.268295496

IUPAC Name

6-({8-acetyl-12-ethyl-5,6-dimethoxy-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6-trien-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

6-({8-acetyl-12-ethyl-5,6-dimethoxy-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6-trien-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CCC12CCCN3CCC4(C(CC1)N(C(C)=O)C1=C(OC)C(OC)=C(OC5OC(C(O)C(O)C5O)C(O)=O)C=C41)C23

InChI Identifier

InChI=1S/C29H40N2O10/c1-5-28-8-6-11-30-12-10-29(27(28)30)15-13-16(40-26-21(35)19(33)20(34)24(41-26)25(36)37)22(38-3)23(39-4)18(15)31(14(2)32)17(29)7-9-28/h13,17,19-21,24,26-27,33-35H,5-12H2,1-4H3,(H,36,37)

InChI Key

PARCWYIBWCCJED-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aspidospermatan-type alkaloids. These are tryptophan-derived alkaloids that are derived from the fusion of tryptamine and a terpene unit (generally either 9 or 10 carbons). Aspidospermine and aspidospermidine (along with tabersonine) are the archetypical members of the Aspidosperma alkaloids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aspidospermatan-type alkaloids

Sub Class

Not Available

Direct Parent

Aspidospermatan-type alkaloids

Alternative Parents

Plumeran-type alkaloids
Phenolic glycosides
O-glucuronides
Carbazoles
Hexoses
O-glycosyl compounds
Quinolidines
Indolizidines
Anisoles
Alkyl aryl ethers
Aralkylamines
Beta hydroxy acids and derivatives
Oxanes
Piperidines
N-alkylpyrrolidines
Pyrans
Acetamides
Tertiary carboxylic acid amides
Amino acids
Trialkylamines
Secondary alcohols
Monocarboxylic acids and derivatives
Acetals
Azacyclic compounds
Polyols
Oxacyclic compounds
Carboxylic acids
Carbonyl compounds
Organic oxides
Organopnictogen compounds
Hydrocarbon derivatives

Substituents

Aspidosperma alkaloid
Plumeran-type alkaloid
Phenolic glycoside
O-glucuronide
1-o-glucuronide
Glucuronic acid or derivatives
Carbazole
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Quinolidine
Indole or derivatives
Indolizidine
Anisole
Alkyl aryl ether
Aralkylamine
Beta-hydroxy acid
Hydroxy acid
N-alkylpyrrolidine
Oxane
Pyran
Benzenoid
Piperidine
Monosaccharide
Acetamide
Tertiary carboxylic acid amide
Pyrrolidine
Amino acid
Tertiary aliphatic amine
Amino acid or derivatives
Tertiary amine
Secondary alcohol
Carboxamide group
Acetal
Oxacycle
Azacycle
Carboxylic acid derivative
Carboxylic acid
Ether
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carbonyl group
Alcohol
Organic nitrogen compound
Amine
Organic oxygen compound
Organopnictogen compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.24 g/L	ALOGPS
logP	1.45	ALOGPS
logP	-2.4	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	2.49	ChemAxon
pKa (Strongest Basic)	9.43	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	158.46 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	142.73 m³·mol⁻¹	ChemAxon
Polarizability	60.3 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0162651

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available