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Haemanthamine
- Family: Plantae - Amaryllidaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Amaryllidaceae Alkaloid
| Canonical Smiles | CO[C@@H]1C=C[C@]23[C@H](C1)N(C[C@@H]2O)Cc1c3cc2OCOc2c1 |
|---|---|
| InChI | InChI=1S/C17H19NO4/c1-20-11-2-3-17-12-6-14-13(21-9-22-14)4-10(12)7-18(8-16(17)19)15(17)5-11/h2-4,6,11,15-16,19H,5,7-9H2,1H3/t11-,15+,16+,17+/m1/s1 |
| InChIKey | YGPRSGKVLATIHT-HSHDSVGOSA-N |
| Formula | C17H19NO4 |
| HBA | 5 |
| HBD | 1 |
| MW | 301.34 |
| Rotatable Bonds | 1 |
| TPSA | 51.16 |
| LogP | 1.19 |
| Number Rings | 5 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 22 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.53 |
| Exact Mass | 301.13 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Narcissus tazetta | Amaryllidaceae | Plantae | 54860 |
Showing of synonyms
Haemanthamine
(+)-Haemanthamine
3-Epicrinamine
Hemeanthamin
Natalensine
Hemanthamine
Natalensin
4abeta,5alpha,11balpha-Crinan-12-ol, 1,2-didehydro-3beta-methoxy-, (12R)-
NSC 403140
Crinan-11-ol, 1,2-didehydro-3-methoxy-, (3beta,5alpha,11R,13beta,19alpha)-
3Epicrinamine
4abeta,5alpha,11balphaCrinan12ol, 1,2didehydro3betamethoxy, (12R)
4abeta,5alpha,11balphaCrinan12ol, 1,2didehydro3betamethoxy, (12R) (8CI)
Crinan11ol, 1,2didehydro3methoxy, (3beta,5alpha,11R,13beta,19alpha)
4abeta,5alpha,11balpha-Crinan-12-ol, 1,2-didehydro-3beta-methoxy-, (12R)-(8CI)
Crinan-11-ol, 1,2-didehydro-3-methoxy-, (3beta,5alpha,11R,13beta,19alpha)-(9CI)
Crinan11ol, 1,2didehydro3methoxy, (3beta,5alpha,11R,13beta,19alpha) (9CI)
466-75-1
Haemanthamin
NSC403140
CHEBI:5600
CHEMBL401114
3H,6H-5,11b-Ethano[1,3]dioxolo[4,5-j]phenanthridin-12-ol, 4,4a-dihydro-3-methoxy-, (3S,4aS,5S,11bS,12R)-
NSC-403140
(1S,13S,15S,18R)-15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.01,13.02,10.04,8]nonadeca-2,4(8),9,16-tetraen-18-ol
VBL6HZX2ZB
3-epi-Crinamine
Natalensine (+)-Haemanthamine
SCHEMBL19915195
DTXSID30963614
BDBM50221069
AKOS040733354
HY-114489A
DA-64005
MS-24341
NCI60_003793
XH175863
CS-0124035
NS00094181
C08527
G16057
Q27106819
(3beta,5alpha,11R,13beta,19alpha)-1,2-Didehydro-3-methoxycrinan-11-ol
4a.beta.,11b.alpha.-Crinan-12-ol, 1,2-didehydro-3.beta.-methoxy-, (12R)-
Crinan-11-ol,2-didehydro-3-methoxy-, (3.beta.,5.alpha.,11R,13.beta.,19.alpha.)-
Crinan-18-ol,2-didehydro-3-methoxy-, (3.beta.,5.beta.,6.alpha.,17.alpha.,18R)-
(3S,4aS,5S,11bS,12R)-4,4a-Dihydro-3-methoxy-3H,6H-5,11b-ethano[1,3]dioxolo[4,5-j]phenanthridin-12-ol
HN8
- Abdallah OM. (1993). Narcisine, an alkaloid from Narcissus tazetta. Phytochemistry,1993,34(5),1447-1448. [View]
Pubchem:
441593
Cas:
466-75-1
Zinc:
ZINC000002004156
Kegg Ligand:
C08527
Chebi:
5600
Metabolights:
MTBLC5600
Chembl:
CHEMBL401114
Pdb Ligand:
HN8
Bindingdb:
50221069
CPRiL:
118937
SMILES: O1COc(c2)c1cc3c2CN(CC4)C(C345)CCC=C5
Level: 0
Mol. Weight: 301.34 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.76
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.590
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.42
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.580
- Plasma Protein Binding
- 32.47
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-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
- Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 7.800
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.820
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.020
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 7.190
- 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
- -3.670
- Rat (Acute)
- 3.020
- Rat (Chronic Oral)
- 1.540
- Fathead Minnow
- 4.010
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 376.690
- Hydration Free Energy
- -8.490
- Log(D) at pH=7.4
- 1.510
- Log(P)
- 1.24
- Log S
- -1.53
- Log(Vapor Pressure)
- -7.95
- Melting Point
- 181.46
- pKa Acid
- 9.37
- pKa Basic
- 6.84
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Norsolorinic acid synthase | Q12053 | AFLC_ASPPU | Aspergillus parasiticus | 3 | 0.9670 |
| Norsolorinic acid synthase | Q12053 | AFLC_ASPPU | Aspergillus parasiticus | 3 | 0.9670 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.8901 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.8901 |
| Proton-gated ion channel | Q7NDN8 | GLIC_GLOVI | Gloeobacter violaceus | 3 | 0.8882 |
| Proton-gated ion channel | Q7NDN8 | GLIC_GLOVI | Gloeobacter violaceus | 3 | 0.8882 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8659 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8659 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.8540 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.8540 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8509 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8509 |
| Steroid 21-hydroxylase | P08686 | CP21A_HUMAN | Homo sapiens | 3 | 0.8479 |
| Steroid 21-hydroxylase | P08686 | CP21A_HUMAN | Homo sapiens | 3 | 0.8479 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.8367 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.8367 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8246 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8246 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 3 | 0.8238 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 3 | 0.8238 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.8224 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.8224 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.8201 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.8201 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8161 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8161 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.8147 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.8147 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8121 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8121 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 3 | 0.8074 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 3 | 0.8074 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.8072 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.8072 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7897 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7897 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7850 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7850 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7838 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7838 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7712 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7712 |
| Odorant binding protein ASP1 | Q8WRW5 | Q8WRW5_APIME | Apis mellifera | 3 | 0.7708 |
| Odorant binding protein ASP1 | Q8WRW5 | Q8WRW5_APIME | Apis mellifera | 3 | 0.7708 |
| Na(+):neurotransmitter symporter (Snf family) | O67854 | O67854_AQUAE | Aquifex aeolicus | 3 | 0.7687 |
| Na(+):neurotransmitter symporter (Snf family) | O67854 | O67854_AQUAE | Aquifex aeolicus | 3 | 0.7687 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 3 | 0.7575 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 3 | 0.7575 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7556 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7556 |
| HLA class I histocompatibility antigen, B alpha chain | P01889 | HLAB_HUMAN | Homo sapiens | 3 | 0.7549 |
| HLA class I histocompatibility antigen, B alpha chain | P01889 | HLAB_HUMAN | Homo sapiens | 3 | 0.7549 |
| Sulfotransferase 1A1 | P50225 | ST1A1_HUMAN | Homo sapiens | 2 | 0.7497 |
| Sulfotransferase 1A1 | P50225 | ST1A1_HUMAN | Homo sapiens | 2 | 0.7497 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.7481 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.7481 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7386 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7386 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7332 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7332 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7318 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7318 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7302 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7302 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7288 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7288 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7279 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7279 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7277 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7277 |
| N-acetyltransferase domain-containing protein | Q9HV14 | Q9HV14_PSEAE | Pseudomonas aeruginosa | 3 | 0.7276 |
| N-acetyltransferase domain-containing protein | Q9HV14 | Q9HV14_PSEAE | Pseudomonas aeruginosa | 3 | 0.7276 |
| High affinity 3',5'-cyclic-AMP phosphodiesterase 7A | Q13946 | PDE7A_HUMAN | Homo sapiens | 3 | 0.7243 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7243 |
| High affinity 3',5'-cyclic-AMP phosphodiesterase 7A | Q13946 | PDE7A_HUMAN | Homo sapiens | 3 | 0.7243 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7243 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 2 | 0.7230 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 2 | 0.7230 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7100 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7100 |
| cGMP-specific 3',5'-cyclic phosphodiesterase | O76074 | PDE5A_HUMAN | Homo sapiens | 3 | 0.7080 |
| cGMP-specific 3',5'-cyclic phosphodiesterase | O76074 | PDE5A_HUMAN | Homo sapiens | 3 | 0.7080 |