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Heliosupine
- Family: Plantae - Boraginaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Pyrrolizidine Alkaloid
| Canonical Smiles | C/C=C(\C(=O)O[C@H]1CCN2[C@@H]1C(=CC2)COC(=O)[C@@](C(O)(C)C)([C@@H](O)C)O)/C |
|---|---|
| InChI | InChI=1S/C20H31NO7/c1-6-12(2)17(23)28-15-8-10-21-9-7-14(16(15)21)11-27-18(24)20(26,13(3)22)19(4,5)25/h6-7,13,15-16,22,25-26H,8-11H2,1-5H3/b12-6-/t13-,15-,16+,20+/m0/s1 |
| InChIKey | HRSGCYGUWHGOPY-UKLMUADPSA-N |
| Formula | C20H31NO7 |
| HBA | 8 |
| HBD | 3 |
| MW | 397.47 |
| Rotatable Bonds | 7 |
| TPSA | 116.53 |
| LogP | 0.3 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 28 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.7 |
| Exact Mass | 397.21 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Paracaryum rugulosum | Boraginaceae | Plantae | 1288242 |
Showing of synonyms
Heliosupine
Cynoglossofin
Cynoglossophine
Heliosupin
Cynoglossofine
32728-78-2
7-Angelyl-9-echimidinylheliotridine
UNII-XW15Z680DP
CYNOGLOSSOPHIN
XW15Z680DP
NSC 136054
CHEBI:5641
NSC-136054
(1S,7aR)-7-[({(2S)-2,3-dihydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoyl}oxy)methyl]-2,3,5,7a-tetrahydro-1H-pyrrolo[1,2-a]pyrrol-1-yl (2Z)-2-methylbut-2-enoate
D-ERYTHRO-PENTITOL, 1,5-DIDEOXY-4-C-METHYL-3-C-((((1S,7AR)-2,3,5,7A-TETRAHYDRO-1-(((2Z)-2-METHYL-1-OXO-2-BUTEN-1-YL)OXY)-1H-PYRROLIZIN-7-YL)METHOXY)CARBONYL)-
DTXSID501020054
(1S,7aR)-7-((((2S)-2,3-dihydroxy-2-((1S)-1-hydroxyethyl)-3-methylbutanoyl)oxy)methyl)-2,3,5,7a-tetrahydro-1H-pyrrolo(1,2-a)pyrrol-1-yl (2Z)-2-methylbut-2-enoate
DTXCID701477902
[(7S,8R)-7-[(Z)-2-methylbut-2-enoyl]oxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-2,3-dihydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoate
HELIOSUPINE [MI]
GLXC-17471
MSK163491
DA-64094
1ST163491
HY-124140
CS-0084459
NS00094179
Q27106842
2-Butenoic acid, 2-methyl-, 7-((2,3-dihydroxy-2-(1-hydroxyethyl)-3-methyl-1-oxobutoxy)methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl ester (VAN)
- 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]
Pubchem:
5281732
Cas:
32728-78-2
Zinc:
ZINC000056871320
Kegg Ligand:
C10319
Chebi:
5641
Nmrshiftdb2:
60026165
Metabolights:
MTBLC5641
No compound-protein relationship available.
SMILES: C1=CCN(C12)CCC2
Level: 0
Mol. Weight: 397.47 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.0
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.86
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.28
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.42
- Plasma Protein Binding
- 47.86
- 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
- 4.65
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.86
- Biodegradation
- Toxic
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.62
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- 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
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -9.71
- Rat (Acute)
- 4.04
- Rat (Chronic Oral)
- 2.15
- Fathead Minnow
- 4.02
- 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
- 391.75
- Hydration Free Energy
- -10.08
- Log(D) at pH=7.4
- 1.15
- Log(P)
- 0.73
- Log S
- -1.66
- Log(Vapor Pressure)
- -8.41
- Melting Point
- 141.76
- pKa Acid
- 7.08
- pKa Basic
- 7.27
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.8380 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.8380 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8233 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8233 |
| Trichothecene 15-O-acetyltransferase TRI3 | Q9C1B7 | TRI3_FUSSP | Fusarium sporotrichioides | 3 | 0.7837 |
| Trichothecene 15-O-acetyltransferase TRI3 | Q9C1B7 | TRI3_FUSSP | Fusarium sporotrichioides | 3 | 0.7837 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 4 | 0.7835 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 4 | 0.7835 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7680 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7680 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 4 | 0.7572 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 4 | 0.7572 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7463 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7463 |
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 3 | 0.7416 |
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 3 | 0.7416 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7388 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7388 |
| Corticosteroid-binding globulin | P31211 | CBG_RAT | Rattus norvegicus | 3 | 0.7385 |
| Corticosteroid-binding globulin | P31211 | CBG_RAT | Rattus norvegicus | 3 | 0.7385 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7333 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7333 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7313 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7313 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7243 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7243 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7218 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7218 |
| 4,4'-diapophytoene synthase | A9JQL9 | CRTM_STAAU | Staphylococcus aureus | 2 | 0.7189 |
| 4,4'-diapophytoene synthase | A9JQL9 | CRTM_STAAU | Staphylococcus aureus | 2 | 0.7189 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7173 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7173 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7104 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7104 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7057 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7057 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7055 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7055 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 2 | 0.7037 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 2 | 0.7037 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7030 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7030 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 3 | 0.7028 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 3 | 0.7028 |