Ipomine - Compound Card

Ipomine

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Ipomine

Structure
Zoomed Structure
  • Family: Plantae - Convolvulaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Hexahydroindolizine Alkaloid
Canonical Smiles O=C(OC[C@H]1O[C@@H](Oc2ccc(cc2)C2=C(C)CC3N(C2)CCC3)[C@@H]([C@H]([C@@H]1O)O)O)/C=C/c1ccc(cc1)O
InChI InChI=1S/C30H35NO8/c1-18-15-21-3-2-14-31(21)16-24(18)20-7-11-23(12-8-20)38-30-29(36)28(35)27(34)25(39-30)17-37-26(33)13-6-19-4-9-22(32)10-5-19/h4-13,21,25,27-30,32,34-36H,2-3,14-17H2,1H3/b13-6+/t21?,25-,27-,28+,29-,30-/m1/s1
InChIKey FBTXNMRYXWHMAF-ANRLJBPOSA-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: 101593049

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=CC(=O)OCC2CCCC(O2)Oc(cc3)ccc3C(=CC4)CN(C45)CCC5

Level: 3

Mol. Weight: 537.61 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OCC2CCCC(O2)Oc3ccccc3

Level: 2

Mol. Weight: 537.61 g/mol

Structure

SMILES: C1CCN(C12)CC(=CC2)c3ccc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 537.61 g/mol

Structure

SMILES: O1CCCCC1COC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 537.61 g/mol

Structure

SMILES: C1CCN(C12)CC(=CC2)c3ccccc3

Level: 1

Mol. Weight: 537.61 g/mol

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 537.61 g/mol

Structure

SMILES: C1CCN(C12)CC=CC2

Level: 0

Mol. Weight: 537.61 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 537.61 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 537.61 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.6
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.68
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
0.81

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.12
Plasma Protein Binding
73.27
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
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
12.38
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.53
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.51
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
8.25
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
-4265.71
Rat (Acute)
2.57
Rat (Chronic Oral)
3.48
Fathead Minnow
12.22
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
447.89
Hydration Free Energy
-2.96
Log(D) at pH=7.4
3.1
Log(P)
2.96
Log S
-3.78
Log(Vapor Pressure)
-10.03
Melting Point
190.53
pKa Acid
6.91
pKa Basic
7.1
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.9331
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8831
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8791
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8771
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8550
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8452
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8420
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.8342
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8235
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8079
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8001
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7956
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7951
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7922
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7855
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7726
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7721
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7689
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7598
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7501
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7482
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7449
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7449
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7401
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7401
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7380
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7365
Acyl-CoA:acyl-CoA alkyltransferase Q8PDX2 OLEA_XANCP Xanthomonas campestris pv. campestris 3 0.7361
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7318
Caffeoyl-CoA O-methyltransferase Q40313 CAMT_MEDSA Medicago sativa 3 0.7281
Virulence sensor histidine kinase PhoQ P0DM80 PHOQ_SALTY Salmonella typhimurium 3 0.7252
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7245
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7244
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7229
Probable bifunctional SAT/APS kinase O67174 SATC_AQUAE Aquifex aeolicus 3 0.7222
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7219
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7215
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7193
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7134
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7105
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7101
Aminopeptidase N P15145 AMPN_PIG Sus scrofa 2 0.7098
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7081
Small heat shock protein StHsp14.0 Q970D9 Q970D9_SULTO Sulfurisphaera tokodaii 3 0.7079
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7060
Kynurenine--oxoglutarate transaminase 1 Q16773 KAT1_HUMAN Homo sapiens 2 0.7054
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7051
Nuclear receptor subfamily 5 group A member 2 O00482 NR5A2_HUMAN Homo sapiens 3 0.7033
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7029
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7028
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7008
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7005
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7002

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