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Intermedine
- Family: Plantae - Boraginaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Pyrrolizidine Alkaloid
| Canonical Smiles | O[C@@H]1CCN2[C@@H]1C(=CC2)COC(=O)[C@@]([C@H](O)C)(C(C)C)O |
|---|---|
| InChI | InChI=1S/C15H25NO5/c1-9(2)15(20,10(3)17)14(19)21-8-11-4-6-16-7-5-12(18)13(11)16/h4,9-10,12-13,17-18,20H,5-8H2,1-3H3/t10-,12-,13-,15+/m1/s1 |
| InChIKey | SFVVQRJOGUKCEG-OPQSFPLASA-N |
| Formula | C15H25NO5 |
| HBA | 6 |
| HBD | 3 |
| MW | 299.37 |
| Rotatable Bonds | 5 |
| TPSA | 90.23 |
| LogP | -0.33 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 21 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.8 |
| Exact Mass | 299.17 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Trichodesma africanum | Boraginaceae | Plantae | 379304 |
| 2 | Anchusa hispida | Boraginaceae | Plantae | 170551 |
| 3 | Lappula spinocarpos | Boraginaceae | Plantae | 1245804 |
Showing of synonyms
Intermedine
(+)-Intermedine
3'-EPI-LYCOPSAMINE
INTERMEDINE, (+)-
10285-06-0
Intermedina
Intermedinum
9-(+)-Trachelanthylretronecine
DLC9FEP81A
[(7R,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-2-hydroxy-2-[(1R)-1-hydroxyethyl]-3-methylbutanoate
[(1R,7aR)-1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolo[1,2-a]pyrrol-7-yl]methyl (2S,3R)-2,3-dihydroxy-2-isopropylbutanoate
1414-01-3
UNII-DLC9FEP81A
C15H25NO5
Butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, [(1R,7aR)-2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl]methyl ester, (2S,3R)-
Butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, (2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl ester, [1R-[1a,7(2S*,3R*),7ass]]-
Intermedine (7CI,8CI)
MFCD09970420
Intermedine, HPLC Grade
SCHEMBL23464
(+)-Intermedine (Standard)
CHEBI:5941
MSK14165
Intermedine 100 microg/mL in Water
AKOS040756430
HY-113845R
(2S,3R)-2,3-Dihydroxy-2-(1-methylethyl)butanoic Acid [(1R,7aR)-2,3,5,7a-Tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl]methyl Ester
1ST14165
Butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, ((1R,7aR)-2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl ester, (2S,3R)-
Butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, (2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl ester, (1R-(1alpha,7(2S*,3R*),7abeta))-
DA-54348
MS-24309
XI161638
HY-113845
CS-0062945
NS00067002
G13669
Q27106936
((1R,7aR)-1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl)methyl (2S,3R)-2,3-dihydroxy-2-isopropylbutanoate
BUTANOIC ACID, 2,3-DIHYDROXY-2-(1-METHYLETHYL)-, (2,3,5,7A-TETRAHYDRO-1-HYDROXY-1H-PYRROLIZIN-7-YL)METHYL ESTER, (1R-(1.ALPHA.,7(2S*,3R*),7A.BETA.))-
- El-Shazly A, El-Domiaty M, et al. (1998). Pyrrolizidine alkaloids in members of the Boraginaceae from Sinai (Egypt). Biochemical Systematics and Ecology,1998,26(6),619-636. [View]
CPRiL:
54390
SMILES: C1=CCN(C12)CCC2
Level: 0
Mol. Weight: 299.37 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.19
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.7
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.62
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.27
- Plasma Protein Binding
- 25.24
- 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
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 3.42
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.6
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.29
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 8.26
- 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
- -2.62
- Rat (Acute)
- 3.55
- Rat (Chronic Oral)
- 2.16
- Fathead Minnow
- 3.63
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 347.62
- Hydration Free Energy
- -14.35
- Log(D) at pH=7.4
- 0.32
- Log(P)
- 0.19
- Log S
- -1.11
- Log(Vapor Pressure)
- -7.62
- Melting Point
- 131.75
- pKa Acid
- 6.31
- pKa Basic
- 7.57
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 3 | 0.9499 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 3 | 0.9499 |
| Prolyl tripeptidyl peptidase | Q7MUW6 | PTP_PORGI | Porphyromonas gingivalis | 3 | 0.9090 |
| Prolyl tripeptidyl peptidase | Q7MUW6 | PTP_PORGI | Porphyromonas gingivalis | 3 | 0.9090 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8762 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8762 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.8564 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.8564 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 3 | 0.8539 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 3 | 0.8539 |
| Gag-Pol polyprotein | P0C6F2 | POL_HV1LW | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.8033 |
| Gag-Pol polyprotein | P0C6F2 | POL_HV1LW | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.8033 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7999 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7999 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.7862 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.7862 |
| Cytochrome P450 | Q93H81 | Q93H81_STRAX | Streptomyces avermitilis | 3 | 0.7833 |
| Cytochrome P450 | Q93H81 | Q93H81_STRAX | Streptomyces avermitilis | 3 | 0.7833 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7804 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7804 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 3 | 0.7725 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 3 | 0.7725 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7602 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7602 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7599 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7599 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7593 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7593 |
| Gastrotropin | Q6IMW5 | Q6IMW5_DANRE | Danio rerio | 3 | 0.7561 |
| Gastrotropin | Q6IMW5 | Q6IMW5_DANRE | Danio rerio | 3 | 0.7561 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7560 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7560 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7550 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7550 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7498 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7498 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7451 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7451 |
| Cyclomaltodextrin glucanotransferase | P05618 | CDGT_BACS0 | Bacillus sp | 3 | 0.7414 |
| Cyclomaltodextrin glucanotransferase | P05618 | CDGT_BACS0 | Bacillus sp | 3 | 0.7414 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7362 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7362 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7359 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7359 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.7311 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.7311 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7297 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7297 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7288 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7288 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 2 | 0.7204 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 2 | 0.7204 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 3 | 0.7140 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 3 | 0.7140 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 2 | 0.7061 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 2 | 0.7061 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7020 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7020 |