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1-cinnamoyltrichilinin

Family: Plantae - Meliaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Tetranortriterpene

Canonical Smiles	O=C(O[C@H]1C[C@@H](OC(=O)C)[C@@]2([C@H]3[C@@]1(C)[C@H]1C[C@H](OC(=O)C)[C@@]4(C(=CC[C@H]4c4ccoc4)[C@@]1([C@@H]([C@@H]3OC2)O)C)C)C)/C=C/c1ccccc1
InChI	InChI=1S/C39H46O9/c1-22(40)46-29-19-31(48-32(42)15-12-24-10-8-7-9-11-24)39(6)28-18-30(47-23(2)41)37(4)26(25-16-17-44-20-25)13-14-27(37)38(28,5)35(43)33-34(39)36(29,3)21-45-33/h7-12,14-17,20,26,28-31,33-35,43H,13,18-19,21H2,1-6H3/b15-12+/t26-,28-,29+,30-,31-,33+,34-,35+,36+,37-,38-,39-/m0/s1
InChIKey	DGVWCAONVNVPRJ-PSAXZYJKSA-N
Formula	C₃₉H₄₆O₉
HBA	9
HBD	1
MW	658.79
Rotatable Bonds	6
TPSA	121.5
LogP	6.02
Number Rings	7
Number Aromatic Rings	2
Heavy Atom Count	48
Formal Charge	0
Fraction CSP3	0.56
Exact Mass	658.31
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Melia volkensii	Meliaceae	Plantae	643111

Showing of synonyms

Rajab MS, Bentley MD. (1988). Tetranortriterpenes from Melia volkensii.. Journal of Natural Products,1988,51(5),840-844. [View] [PubMed]

Pubchem: 100945034

Cas: 117869-72-4

Zinc: ZINC000255205577

No compound-protein relationship available.

SMILES: c1ccccc1C=CC(=O)OC(C23)CCC(CO4)C2C4CC5C3CCC(C5=6)C(CC6)c7ccoc7

Level: 2

Mol. Weight: 658.79 g/mol

SMILES: c1ccccc1C=CC(=O)OC2CCC(COC3CC45)C3C2C5CCC(C4=6)CCC6

Level: 1

Mol. Weight: 658.79 g/mol

SMILES: c1occc1C(CC2)C(C=23)CCC4C3CC5C6C(CO5)CCCC46

Level: 1

Mol. Weight: 658.79 g/mol

SMILES: C1CCC(C=12)CCC3C2CC4C5C(CO4)CCCC35

Level: 0

Mol. Weight: 658.79 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 658.79 g/mol

SMILES: c1ccoc1

Level: 0

Mol. Weight: 658.79 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.69
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -3.61
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 167.27

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.16
Plasma Protein Binding: 94.82
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Inhibitor
OATP1B3: Inhibitor

Excretion

Clearance: 10.2
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.57
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.03
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 9.03
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Toxic
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -307655.85
Rat (Acute): 4.04
Rat (Chronic Oral): 3.05
Fathead Minnow: 399.78
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 30220.13
Hydration Free Energy: -2.92
Log(D) at pH=7.4: 4.85
Log(P): 5.11
Log S: -6.27
Log(Vapor Pressure): -980.2
Melting Point: 192.08
pKa Acid: 6.02
pKa Basic: 3.63

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	3	0.8924
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	3	0.8924
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.8024
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.8024
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7682
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7682
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7623
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7623
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	2	0.7534
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	2	0.7534
Annexin A5	P08758	ANXA5_HUMAN	Homo sapiens	3	0.7420
Annexin A5	P08758	ANXA5_HUMAN	Homo sapiens	3	0.7420
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7405
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7405
Polymerase acidic protein	P03433	PA_I34A1	Influenza A virus	2	0.7193
Polymerase acidic protein	P03433	PA_I34A1	Influenza A virus	2	0.7193
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7128
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7128
Tryptase alpha/beta-1	Q15661	TRYB1_HUMAN	Homo sapiens	3	0.7095
Tryptase alpha/beta-1	Q15661	TRYB1_HUMAN	Homo sapiens	3	0.7095
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	2	0.7063
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	2	0.7063

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