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Ipalbidine

Family: Plantae - Convolvulaceae
Kingdom: Plantae
Class: Alkaloid
- Subclass: Hexahydroindolizine Alkaloid

Canonical Smiles	OCC1OC(Oc2ccc(cc2)C2=C(C)C3N(CC2)CCC3)C(C(C1OC(=O)/C=C/c1ccc(cc1)O)O)O
InChI	InChI=1S/C30H35NO8/c1-18-23(14-16-31-15-2-3-24(18)31)20-7-11-22(12-8-20)37-30-28(36)27(35)29(25(17-32)38-30)39-26(34)13-6-19-4-9-21(33)10-5-19/h4-13,24-25,27-30,32-33,35-36H,2-3,14-17H2,1H3/b13-6+
InChIKey	UGYJLQLOPSQPDU-AWNIVKPZSA-N
Formula	C₃₀H₃₅NO₈
HBA	9
HBD	4
MW	537.61
Rotatable Bonds	7
TPSA	128.92
LogP	2.48
Number Rings	5
Number Aromatic Rings	2
Heavy Atom Count	39
Formal Charge	0
Fraction CSP3	0.43
Exact Mass	537.24
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ipomoea muricata	Convolvulaceae	Plantae	231710

Showing of synonyms

Dawidar AM, Winternitz F, et al. (1977). Structure of Ipomine, a new alkaloid from Ipomea muricata Jacq. Tetrahedron,1977,33(14),1733-1734. [View]

Pubchem: 161520

Cas: 26294-41-7

CPRiL: 327382

SMILES: c1ccccc1C=CC(=O)OC2CCC(OC2)Oc(cc3)ccc3C(=C4)CCN(C45)CCC5

Level: 3

Mol. Weight: 537.61 g/mol

SMILES: c1ccccc1C=CC(=O)OC2CCC(OC2)Oc3ccccc3

Level: 2

Mol. Weight: 537.61 g/mol

SMILES: C1CCN(C12)CCC(=C2)c3ccc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 537.61 g/mol

SMILES: C1OCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 537.61 g/mol

SMILES: C1CCN(C12)CCC(=C2)c3ccccc3

Level: 1

Mol. Weight: 537.61 g/mol

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 537.61 g/mol

SMILES: C1CCN(C12)CCC=C2

Level: 0

Mol. Weight: 537.61 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 537.61 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 537.61 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.44
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.73
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 0.79

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.03
Plasma Protein Binding: 10.47
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 12.54
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.96
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.5
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 7.73
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
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: -4569.45
Rat (Acute): 2.59
Rat (Chronic Oral): 3.43
Fathead Minnow: 13.39
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 424.99
Hydration Free Energy: -2.93
Log(D) at pH=7.4: 2.81
Log(P): 2.73
Log S: -3.65
Log(Vapor Pressure): -9.13
Melting Point: 186.79
pKa Acid: 6.6
pKa Basic: 6.52

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.9332
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8836
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8694
Gastrotropin	Q6IMW5	Q6IMW5_DANRE	Danio rerio	3	0.8530
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8486
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8457
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8379
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8351
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.8317
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8256
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8190
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.8179
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8119
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.8052
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.8045
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7977
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.7937
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7929
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7895
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7882
Purine nucleoside phosphorylase	Q8I3X4	Q8I3X4_PLAF7	Plasmodium falciparum	3	0.7871
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7787
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.7774
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	4	0.7708
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7692
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7645
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.7643
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.7593
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7590
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7554
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7533
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7515
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7453
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7435
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7428
Threonine--tRNA ligase	P0A8M3	SYT_ECOLI	Escherichia coli	3	0.7422
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7402
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7397
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7388
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7382
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7359
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7324
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7291
Probable bifunctional SAT/APS kinase	O67174	SATC_AQUAE	Aquifex aeolicus	3	0.7271
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7266
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7263
Ephrin type-A receptor 2	P29317	EPHA2_HUMAN	Homo sapiens	3	0.7262
GMP reductase	Q81JJ9	GUAC_BACAN	Bacillus anthracis	2	0.7254
Ribonuclease TTHA0252	Q5SLP1	RNSE_THET8	Thermus thermophilus	3	0.7245
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7242
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7225
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7205
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7204
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7186
Nucleoside 2-deoxyribosyltransferase	Q8RLY5	Q8RLY5_LACHE	Lactobacillus helveticus	3	0.7130
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7113
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7081
Adenosine 5'-monophosphoramidase HINT1	P49773	HINT1_HUMAN	Homo sapiens	3	0.7081
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7074
Neprilysin	P08049	NEP_RABIT	Oryctolagus cuniculus	4	0.7060
Multidrug efflux pump subunit AcrB	P31224	ACRB_ECOLI	Escherichia coli	3	0.7059
Isoleucine--tRNA ligase	P56690	SYI_THET8	Thermus thermophilus	3	0.7055
Proto-oncogene tyrosine-protein kinase receptor Ret	P07949	RET_HUMAN	Homo sapiens	3	0.7054
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	2	0.7054
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7053
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7050
Kynurenine--oxoglutarate transaminase 1	Q16773	KAT1_HUMAN	Homo sapiens	2	0.7046
Ethylene receptor 1	P49333	ETR1_ARATH	Arabidopsis thaliana	3	0.7044
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7023
Anthranilate phosphoribosyltransferase	P00500	TRPD_ACIAD	Acinetobacter baylyi	2	0.7022
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7012
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	2	0.7008
Purine nucleoside phosphorylase DeoD-type	B1JL34	DEOD_YERPY	Yersinia pseudotuberculosis serotype O:3	2	0.7008

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