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Voacamine

Family: Plantae - Apocynaceae
Kingdom: Plantae
Class: Alkaloid
- Subclass: Indole Alkaloid

Canonical Smiles	COC(=O)C1[C@H]2C[C@H](c3cc4[nH]c5c(c4cc3OC)CCN3C4[C@@]5(C[C@@H](C[C@H]4CC)C3)C(=O)OC)c3c(C[C@@H]1N(C/C/2=C/C)C)c1ccccc1[nH]3
InChI	InChI=1S/C43H52N4O5/c1-7-24-15-23-20-43(42(49)52-6)39-27(13-14-47(21-23)40(24)43)29-19-36(50-4)30(17-34(29)45-39)31-16-28-25(8-2)22-46(3)35(37(28)41(48)51-5)18-32-26-11-9-10-12-33(26)44-38(31)32/h8-12,17,19,23-24,28,31,35,37,40,44-45H,7,13-16,18,20-22H2,1-6H3/b25-8-/t23-,24-,28+,31-,35+,37?,40?,43+/m1/s1
InChIKey	VCMIRXRRQJNZJT-PVEFNOMSSA-N
Formula	C₄₃H₅₂N₄O₅
HBA	7
HBD	2
MW	704.91
Rotatable Bonds	5
TPSA	99.89
LogP	6.49
Number Rings	10
Number Aromatic Rings	4
Heavy Atom Count	52
Formal Charge	0
Fraction CSP3	0.53
Exact Mass	704.39
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Hedranthera barteri	Apocynaceae	Plantae	141540

Showing of synonyms

Agwada V, Patel MB, et al. (1970). Die Alkaloide aus Hedranthera barteri (Hook. f.) Pichonl. 139. Mitteilung uber die Alkaloide. Helvetica Chimica Acta,1970,53(7),1567-1577. [View]

Pubchem: 11953931

Nmrshiftdb2: 60029740

Drugbank: DB04877

CPRiL: 276627

SMILES: c1cccc2[nH]c(c3c12)C(CC4C(=C)CNC(C4)C3)c(cc5)cc6[nH]c(c7c56)C8C9N(CC7)CC(C8)CC9

Level: 1

Mol. Weight: 704.91 g/mol

SMILES: c1cccc2[nH]c(c3c12)C4C5N(CC3)CC(C4)CC5

Level: 0

Mol. Weight: 704.91 g/mol

SMILES: C1C(C2)NCC(=C)C1CCc(c2c34)[nH]c3cccc4

Level: 0

Mol. Weight: 704.91 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.86
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: 17.410
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 3028.99

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.270
Plasma Protein Binding: 79.45
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 12.140
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -74.220
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -1.560
Liver Injury II: Safe
hERG Blockers: Toxic
Daphnia Maga: 5.500
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -5495964.680
Rat (Acute): 2.800
Rat (Chronic Oral): 2.360
Fathead Minnow: 6940.140
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 614674.280
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 5.540
Log(P): 5.93
Log S: -5.78
Log(Vapor Pressure): -20182.01
Melting Point: 276.31
pKa Acid: -109.23
pKa Basic: 6.04

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8326
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8326
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8225
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8225
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8128
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8128
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8065
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8065
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.7985
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.7985
Carbonic anhydrase 13	Q8N1Q1	CAH13_HUMAN	Homo sapiens	3	0.7924
Carbonic anhydrase 13	Q8N1Q1	CAH13_HUMAN	Homo sapiens	3	0.7924
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7809
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7809
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7692
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7692
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	2	0.7633
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	2	0.7633
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7611
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7611
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7549
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7549
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7547
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7547
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	P0AF12	MTNN_ECOLI	Escherichia coli	3	0.7483
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	P0AF12	MTNN_ECOLI	Escherichia coli	3	0.7483
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.7448
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.7448
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7417
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7417
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.7389
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.7389
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	2	0.7368
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	2	0.7368
Gag-Pol polyprotein	P03369	POL_HV1A2	Human immunodeficiency virus type 1 group M subtype B	3	0.7355
Gag-Pol polyprotein	P03369	POL_HV1A2	Human immunodeficiency virus type 1 group M subtype B	3	0.7355
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7348
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7348
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7337
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7337
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7319
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7319
O-GlcNAcase BT_4395	Q89ZI2	OGA_BACTN	Bacteroides thetaiotaomicron	4	0.7255
O-GlcNAcase BT_4395	Q89ZI2	OGA_BACTN	Bacteroides thetaiotaomicron	4	0.7255
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7187
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7187
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7162
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7162
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7149
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7149
Annexin A5	P08758	ANXA5_HUMAN	Homo sapiens	3	0.7146
Annexin A5	P08758	ANXA5_HUMAN	Homo sapiens	3	0.7146
AcsD	Q93AT8	Q93AT8_DICCH	Dickeya chrysanthemi	3	0.7082
AcsD	Q93AT8	Q93AT8_DICCH	Dickeya chrysanthemi	3	0.7082
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7011
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7011

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