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6-alpha-hydroxymaackiain
- Family: Plantae - Leguminosae/Fabaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Pterocarpin
| Canonical Smiles | Oc1ccc2c(c1)OCC1(C2Oc2c1cc1c(c2)OCO1)O |
|---|---|
| InChI | InChI=1S/C16H12O6/c17-8-1-2-9-11(3-8)19-6-16(18)10-4-13-14(21-7-20-13)5-12(10)22-15(9)16/h1-5,15,17-18H,6-7H2 |
| InChIKey | GLMPLZUBQDAZEN-UHFFFAOYSA-N |
| Formula | C16H12O6 |
| HBA | 6 |
| HBD | 2 |
| MW | 300.27 |
| Rotatable Bonds | 0 |
| TPSA | 77.38 |
| LogP | 1.83 |
| Number Rings | 5 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 22 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.25 |
| Exact Mass | 300.06 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Tephrosia rhodesica | Leguminosae/Fabaceae | Plantae | 556521 |
Showing of synonyms
6-alpha-hydroxymaackiain
6a-Hydroxyinermin
6alpha-Hydroxymaackiain
3,6a-Dihydroxy-8,9-methylenedioxypterocarpan
14602-93-8
5,7,11,19-tetraoxapentacyclo[10.8.0.02,10.04,8.013,18]icosa-2,4(8),9,13(18),14,16-hexaene-1,16-diol
5,7,11,19-tetraoxapentacyclo(10.8.0.02,10.04,8.013,18)icosa-2,4(8),9,13(18),14,16-hexaene-1,16-diol
6a-Hydroxymaackiain
6?-Hydroxymaackiain
SCHEMBL4726444
CHEBI:174859
LCA21844
LMPK12070133
AKOS032948949
XH161543
(+)-6a-Hydroxymaackiain
- Atilaw Y, Muiva-Mutisya L, et al. (2020). Prenylated Flavonoids from the Roots of Tephrosia rhodesica. Journal of natural products, 2020, 83(8), 2390–2398. [View]
No compound-protein relationship available.
SMILES: O1COc(c2)c1cc(c23)OC4C3COc5c4cccc5
Level: 0
Mol. Weight: 300.27 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.77
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.500
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.15
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.990
- Plasma Protein Binding
- 49.28
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 12.840
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.150
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.550
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.660
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- 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
- 3.800
- Rat (Acute)
- 1.950
- Rat (Chronic Oral)
- 1.260
- Fathead Minnow
- 4.500
- 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
- 419.420
- Hydration Free Energy
- -8.840
- Log(D) at pH=7.4
- 2.520
- Log(P)
- 1.93
- Log S
- -3.44
- Log(Vapor Pressure)
- -9.44
- Melting Point
- 232.48
- pKa Acid
- 9.43
- pKa Basic
- 1.8
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.9329 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.9248 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.9070 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.8875 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.8732 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8716 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8686 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.8683 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.8473 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.8408 |
| Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial | Q33862 | Q33862_ASCSU | Ascaris suum | 3 | 0.8295 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8282 |
| L-lactate dehydrogenase A chain | P04642 | LDHA_RAT | Rattus norvegicus | 3 | 0.8251 |
| Transthyretin | P02767 | TTHY_RAT | Rattus norvegicus | 3 | 0.8245 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8203 |
| Chalcone--flavanone isomerase 1 | P28012 | CFI1_MEDSA | Medicago sativa | 3 | 0.8187 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 3 | 0.8175 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8158 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8095 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8090 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 3 | 0.7969 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7955 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7915 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7882 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.7846 |
| Rhodopsin kinase GRK1 | P28327 | GRK1_BOVIN | Bos taurus | 3 | 0.7796 |
| Proto-oncogene tyrosine-protein kinase Src | P12931 | SRC_HUMAN | Homo sapiens | 3 | 0.7796 |
| cGMP-dependent protein kinase 1 | Q13976 | KGP1_HUMAN | Homo sapiens | 3 | 0.7796 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7739 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7728 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.7712 |
| IOMT 3 | Q06YR3 | Q06YR3_MEDTR | Medicago truncatula | 3 | 0.7702 |
| Gag-Pol polyprotein | O12158 | POL_HV192 | Human immunodeficiency virus type 1 group M subtype C | 3 | 0.7671 |
| Histone deacetylase 7 | Q8WUI4 | HDAC7_HUMAN | Homo sapiens | 3 | 0.7663 |
| Anthocyanidin 3-O-glucosyltransferase UFGT | P51094 | UFOG_VITVI | Vitis vinifera | 3 | 0.7654 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7636 |
| Beta-adrenergic receptor kinase 1 | P25098 | ARBK1_HUMAN | Homo sapiens | 3 | 0.7589 |
| DNA gyrase subunit A | P0AES5 | GYRA_SHIFL | Shigella flexneri | 3 | 0.7573 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7556 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7536 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7510 |
| Methylmalonyl-CoA decarboxylase | P52045 | SCPB_ECOLI | Escherichia coli | 3 | 0.7502 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7476 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 4 | 0.7473 |
| Vitamin D3 dihydroxylase | P18326 | CPXE_STRGO | Streptomyces griseolus | 3 | 0.7458 |
| Vitamin D3 dihydroxylase | P18326 | CPXE_STRGO | Streptomyces griseolus | 3 | 0.7452 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 4 | 0.7448 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.7408 |
| Calmodulin-domain protein kinase 1, putative | A3FQ16 | A3FQ16_CRYPI | Cryptosporidium parvum | 3 | 0.7387 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7381 |
| Nodulin-13 | P93330 | NOD13_MEDTR | Medicago truncatula | 3 | 0.7374 |
| 17beta-hydroxysteroid dehydrogenase | O93874 | O93874_COCLU | Cochliobolus lunatus | 3 | 0.7371 |
| Biotin carboxylase | P24182 | ACCC_ECOLI | Escherichia coli | 3 | 0.7369 |
| Formylmethanofuran--tetrahydromethanopterin formyltransferase | Q49610 | FTR_METKA | Methanopyrus kandleri | 3 | 0.7368 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7355 |
| Laminarinase | Q9WXN1 | Q9WXN1_THEMA | Thermotoga maritima | 3 | 0.7351 |
| Major pollen allergen Bet v 1-A | P15494 | BEV1A_BETPN | Betula pendula | 3 | 0.7349 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7334 |
| N-acetyltransferase domain-containing protein | Q9HV14 | Q9HV14_PSEAE | Pseudomonas aeruginosa | 3 | 0.7306 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7299 |
| Beta-lactamase | Q9L5C8 | Q9L5C8_ECOLX | Escherichia coli | 3 | 0.7284 |
| Calmodulin-like domain protein kinase | Q3HNM4 | Q3HNM4_EIMTE | Eimeria tenella | 4 | 0.7283 |
| Beta-lactamase | P00811 | AMPC_ECOLI | Escherichia coli | 3 | 0.7276 |
| Phosphodiesterase | Q8WQX9 | Q8WQX9_9TRYP | Trypanosoma brucei | 3 | 0.7269 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7269 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7263 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7258 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7227 |
| Methionine aminopeptidase 1 | P53582 | MAP11_HUMAN | Homo sapiens | 3 | 0.7182 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7142 |
| Catechol O-methyltransferase | P22734 | COMT_RAT | Rattus norvegicus | 3 | 0.7141 |
| Serine hydroxymethyltransferase | Q7SIB6 | Q7SIB6_GEOSE | Geobacillus stearothermophilus | 3 | 0.7089 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 2 | 0.7085 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7059 |
| Capsid protein VP1 | O56137 | O56137_9VIRU | Adeno-associated virus - 6 | 3 | 0.7053 |
| [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial | Q15119 | PDK2_HUMAN | Homo sapiens | 2 | 0.7025 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7024 |