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12-hydroxyrotenone

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)c1C[C@@H](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-CGYQNGNCSA-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	Neorautanenia mitis	Leguminosae/Fabaceae	Plantae	167620

Showing of synonyms

Sakurai Y, Sakurai N, et al. (2006). Rautandiols A and B, pterocarpans and cytotoxic constituents from Neorautanenia mitis.. Journal of Natural Products,2006,69(3),397-399. [View] [PubMed]

Pubchem: 161176

Cas: 16431-42-8

Zinc: ZINC000005158429

Nmrshiftdb2: 80002946

CPRiL: 294781

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

Level: 0

Mol. Weight: 410.42 g/mol

Cytotoxic

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: 83.26
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: 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: 1.100
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.510
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 6.800
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: -50.930
Rat (Acute): 3.000
Rat (Chronic Oral): 1.970
Fathead Minnow: 4.800
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 455.980
Hydration Free Energy: -4.090
Log(D) at pH=7.4: 2.750
Log(P): 3.34
Log S: -4.0
Log(Vapor Pressure): -8.86
Melting Point: 211.13
pKa Acid: 8.33
pKa Basic: 1.83

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8981
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8981
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.8527
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.8527
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8523
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8523
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8435
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8435
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.8366
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.8366
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8300
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8300
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.8278
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.8278
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8204
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8204
Nuclear receptor ROR-gamma	P51449	RORG_HUMAN	Homo sapiens	3	0.8184
Nuclear receptor ROR-gamma	P51449	RORG_HUMAN	Homo sapiens	3	0.8184
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8157
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8157
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.8134
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.8134
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.8019
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.8019
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7845
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7845
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7822
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7822
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7744
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7744
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7720
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7720
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.7707
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.7707
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.7610
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.7610
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	3	0.7588
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	3	0.7588
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7550
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7550
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7528
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7528
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	4	0.7452
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	4	0.7452
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.7367
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.7367
Beta-elicitin cinnamomin	P15569	ELIB_PHYCI	Phytophthora cinnamomi	3	0.7283
Beta-elicitin cinnamomin	P15569	ELIB_PHYCI	Phytophthora cinnamomi	3	0.7283
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7244
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7244
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7228
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7228
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7209
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7209
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.7202
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.7202
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	3	0.7166
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	3	0.7166
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	2	0.7106
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	2	0.7106
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	2	0.7103
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	2	0.7103
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7101
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7101
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7082
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7082
Aldehyde dehydrogenase, mitochondrial	P05091	ALDH2_HUMAN	Homo sapiens	4	0.7063
Aldehyde dehydrogenase, mitochondrial	P05091	ALDH2_HUMAN	Homo sapiens	4	0.7063
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.7058
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.7058
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7053
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7053
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	4	0.7018
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	4	0.7018
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	3	0.7001
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	3	0.7001

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