6-hydroxy-6a,12a-dehydrodeguelin - Compound Card

6-hydroxy-6a,12a-dehydrodeguelin

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6-hydroxy-6a,12a-dehydrodeguelin

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Rotenoid
Canonical Smiles COc1cc2c(cc1OC)oc(=O)c1c2c(=O)c2c(o1)c1C=CC(Oc1cc2)(C)C
InChI InChI=1S/C23H18O7/c1-23(2)8-7-11-14(30-23)6-5-12-19(24)18-13-9-16(26-3)17(27-4)10-15(13)28-22(25)21(18)29-20(11)12/h5-10H,1-4H3
InChIKey NWWVDLRRSGQBKO-UHFFFAOYSA-N
Formula C23H18O7
HBA 7
HBD 0
MW 406.39
Rotatable Bonds 2
TPSA 88.11
LogP 4.25
Number Rings 5
Number Aromatic Rings 4
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.22
Exact Mass 406.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Millettia duchesnei Leguminosae/Fabaceae Plantae 2708899
2 Millettia duchesnei Leguminosae/Fabaceae Plantae 2708899

Showing of synonyms

  • Ngandeu F, Bezabih M, et al. (2008). Rotenoid derivatives and other constituents of the twigs of Millettia duchesnei De Wild. Planta Med. 2008, 74-PB76. [View]
  • Ngandeu F, Bezabih M, et al. (2008). Rotenoid derivatives and other constituents of the twigs of Millettia duchesnei.. Phytochemistry,2008, 69(1), 258-263. [View] [PubMed]
Pubchem: 135019234
Nmrshiftdb2: 70044844

No compound-protein relationship available.

Structure

SMILES: c1cccc(c1c23)oc(=O)c3oc4c(c2=O)ccc5c4C=CCO5

Level: 0

Mol. Weight: 406.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.81
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.420
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.77

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.670
Plasma Protein Binding
81.17
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.340
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.430
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.890
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.310
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
Safe
T. Pyriformis
-32.850
Rat (Acute)
2.940
Rat (Chronic Oral)
1.660
Fathead Minnow
5.890
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
552.100
Hydration Free Energy
-4.460
Log(D) at pH=7.4
2.660
Log(P)
4.21
Log S
-5.74
Log(Vapor Pressure)
-9.49
Melting Point
259.84
pKa Acid
7.48
pKa Basic
3.02
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9154
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9136
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9063
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8887
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8621
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8560
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8553
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8344
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8286
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8271
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8253
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8215
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8116
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.8001
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7979
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7814
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7783
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7758
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7692
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7672
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7639
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7624
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7593
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7565
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7540
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7540
Reductase homolog Q9ZGC1 Q9ZGC1_STRCY Streptomyces cyanogenus 4 0.7479
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7418
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7418
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7396
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7360
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7341
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7338
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7242
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7198
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7173
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7104
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7094
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7018
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7004

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