12-alpha-hydroxyrotenone - Compound Card

12-alpha-hydroxyrotenone

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12-alpha-hydroxyrotenone

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Rotenoid
Canonical Smiles COc1cc2c(cc1OC)OC[C@@H]1[C@@]2(O)C(=O)c2c(O1)c1CC(Oc1cc2)C(=C)C
InChI InChI=1S/C23H22O7/c1-11(2)16-7-13-15(29-16)6-5-12-21(13)30-20-10-28-17-9-19(27-4)18(26-3)8-14(17)23(20,25)22(12)24/h5-6,8-9,16,20,25H,1,7,10H2,2-4H3/t16?,20-,23-/m1/s1
InChIKey JFVKWCYZKMUTLH-JRAJRYKFSA-N
Formula C23H22O7
HBA 7
HBD 1
MW 410.42
Rotatable Bonds 3
TPSA 83.45
LogP 2.81
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.35
Exact Mass 410.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Millettia dura Leguminosae/Fabaceae Plantae 62119

Showing of synonyms

  • Buyinza D, Chalo DM, et al. (2020). Flavonoids and Isoflavonoids of Millettia dura and Millettia ferruginea: Phytochemical review and chemotaxonomic values. Biochemical Systematics and Ecology, 2020, 91, 104053. [View]
Pubchem: 12315065

No compound-protein relationship available.

Structure

SMILES: C1COc(c12)ccc3c2OC4C(C3=O)c5c(OC4)cccc5

Level: 0

Mol. Weight: 410.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.87
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.670
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.99

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.280
Plasma Protein Binding
80.0
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
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.050
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.160
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.520
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.820
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
-49.120
Rat (Acute)
2.990
Rat (Chronic Oral)
1.970
Fathead Minnow
4.870
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
453.640
Hydration Free Energy
-4.090
Log(D) at pH=7.4
2.750
Log(P)
3.39
Log S
-4.0
Log(Vapor Pressure)
-8.79
Melting Point
209.42
pKa Acid
8.32
pKa Basic
1.82
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9507
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8953
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8271
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8165
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8150
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8109
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8012
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7965
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7945
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7831
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7755
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7598
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7577
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7530
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7488
Beta-elicitin cinnamomin P15569 ELIB_PHYCI Phytophthora cinnamomi 3 0.7480
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7370
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7269
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7252
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7250
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7242
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 4 0.7206
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7189
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7171
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7166
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7153
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7107
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7102
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7052
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7048
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7042
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7036
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7007

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