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(-)-maackiain
- Family: Plantae - Leguminosae/Fabaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Pterocarpan
| Canonical Smiles | C1[C@@H]2[C@H](C3=C(O1)C=C(C=C3)O)OC4=CC5=C(C=C24)OCO5 |
|---|---|
| InChI | InChI=1S/C16H12O5/c17-8-1-2-9-12(3-8)18-6-11-10-4-14-15(20-7-19-14)5-13(10)21-16(9)11/h1-5,11,16-17H,6-7H2/t11-,16-/m0/s1 |
| InChIKey | HUKSJTUUSUGIDC-ZBEGNZNMSA-N |
| Formula | C16H12O5 |
| HBA | 5 |
| HBD | 1 |
| MW | 284.27 |
| Rotatable Bonds | 0 |
| TPSA | 57.15 |
| LogP | 2.73 |
| Number Rings | 5 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 21 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.25 |
| Exact Mass | 284.07 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Ononis angustissima | Leguminosae/Fabaceae | Plantae | 672159 |
| 2 | Tephrosia rhodesica | Leguminosae/Fabaceae | Plantae | 556521 |
Showing of synonyms
(-)-maackiain
Maackiain
2035-15-6
L-Maackiain
Maackiaine
CHEBI:99
Trifolirhizin aglycone
TF360D25IJ
(6ar,12ar)-6a,12a-dihydro-6h-[1,3]dioxolo[5,6][1]benzofuro[3,2-c]chromen-3-ol
3-Hydroxy-8,9-methylenedioxypterocarpan
UNII-TF360D25IJ
(-)-(6aR,12aR)-maackiain
DTXSID40904139
6H-(1,3)Dioxolo(5,6)benzofuro(3,2-c)(1)benzopyran-3-ol, 6a,12a-dihydro-, (6aR-cis)-
(6aR,12aR)-3-hydroxy-8,9-methylenedioxypterocarpane
(6aR,12aR)-6a,12a-Dihydro-6H-[1,3]dioxolo[4',5':5,6]benzofuro[3,2-c]chromen-3-ol
(1R,12R)-5,7,11,19-tetraoxapentacyclo[10.8.0.02,10.04,8.013,18]icosa-2,4(8),9,13(18),14,16-hexaen-16-ol
6H-[1,3]Dioxolo[4',5':5,6]benzofuro[3,2-c][1]benzopyran-3-ol, 6a,12a-dihydro-, (6aR,12aR)-
6H-[1,3]Dioxolo[4',5':5,6]benzofuro[3,2-c][1]benzopyran-3-ol, 6a,12a-dihydro-, (6aR-cis)-
6H-[1,3]Dioxolo[4',5':5,6]benzofuro[3,2-c][1]benzopyran-3-ol, 6a.alpha.,12a.alpha.-dihydro-, (-)-
6a,12a-Dihydro-6H-(1,3)dioxolo(5,6)benzofuro(3,2-c)(1)benzopyran-3-ol
(6aR,12aR)-6a,12a-Dihydro-6H-(1,3)dioxolo(4',5':5,6)benzofuro(3,2-c)chromen-3-ol
(6aR,12aR)-6a,12a-dihydro-6H-(1,3)dioxolo(5,6)(1)benzofuro(3,2-c)chromen-3-ol
(1R,12R)-5,7,11,19-tetraoxapentacyclo(10.8.0.02,10.04,8.013,18)icosa-2,4(8),9,13(18),14,16-hexaen-16-ol
6H-(1,3)Dioxolo(4',5':5,6)benzofuro(3,2-c)(1)benzopyran-3-ol, 6a,12a-dihydro-, (6aR,12aR)-
6H-(1,3)Dioxolo(4',5':5,6)benzofuro(3,2-c)(1)benzopyran-3-ol, 6a,12a-dihydro-, (6aR-cis)-
DTXCID701332023
6H-(1,3)Dioxolo(4',5':5,6)benzofuro(3,2-c)(1)benzopyran-3-ol, 6aalpha,12aalpha-dihydro-, (-)-
6a,12a-dihydro-6h-(1,3)dioxolo(5,6)(1)benzofuro(3,2-c)chromen-3-ol
6a,12a-dihydro-6h-[1,3]dioxolo[5,6][1]benzofuro[3,2-c]chromen-3-ol
Huksjtuusugidc-zbegnznmsa-n
Inermin
Inermine
(+/-)-Maackiain
(-?)?-Maackiain
6H-[1,3]Dioxolo[5,6]benzofuro[3,2-c][1]benzopyran-3-ol, 6a,12a-dihydro-, (6aR,12aR)-
MFCD00270457
ST077155
(-?)?-Maackiain (Standard)
CHEMBL334918
(-)-Maackiain , HPLC Grade
HY-N6051R
HY-N6051
BDBM50535076
LMPK12070050
AKOS003673403
FM73808
DA-59408
MS-24036
XM167289
XM167290
CS-0032251
D85120
Q27105234
(1R,12R)-5,7,11,19-tetraoxapentacyclo[10.8.0.0?,??.0?,?.0??,??]icosa-2,4(8),9,13,15,17-hexaen-16-ol
- Ghribi L, Waffo-Téguo P, et al. (2015). Isolation and structure elucidation of bioactive compounds from the roots of the Tunisian Ononis angustissimaL.. Bioorganic & medicinal chemistry letters, 2015, 25(18), 3825-30. [View] [PubMed]
- 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]
Pubchem:
91510
Cas:
2035-15-6
Gnps:
CCMSLIB00006459890
Zinc:
ZINC000000899884
Kegg Ligand:
C10502
Chebi:
99
Nmrshiftdb2:
60031693
Chembl:
CHEMBL334918
Bindingdb:
50535076
CPRiL:
78291
SMILES: O1COc(c2)c1cc(c23)OC4C3COc5c4cccc5
Level: 0
Mol. Weight: 284.27 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.85
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.52
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.92
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.2
- Plasma Protein Binding
- 79.83
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- 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
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 13.73
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.22
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.78
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.82
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- 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
- Toxic
- T. Pyriformis
- 3.45
- Rat (Acute)
- 1.9
- Rat (Chronic Oral)
- 1.26
- Fathead Minnow
- 4.58
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 434.78
- Hydration Free Energy
- -8.3
- Log(D) at pH=7.4
- 3.27
- Log(P)
- 2.83
- Log S
- -4.64
- Log(Vapor Pressure)
- -9.2
- Melting Point
- 202.67
- pKa Acid
- 10.1
- pKa Basic
- 3.83
No predicted protein targets found for this compound.