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Rautandiol B

Family: Plantae - Leguminosae/Fabaceae
Kingdom: Plantae
Class: Pterocarpan

Canonical Smiles	Oc1ccc2c(c1)O[C@@H]1[C@H]2COc2c1cc1CC(Oc1c2)C(O)(C)C
InChI	InChI=1S/C20H20O5/c1-20(2,22)18-6-10-5-13-16(8-15(10)24-18)23-9-14-12-4-3-11(21)7-17(12)25-19(13)14/h3-5,7-8,14,18-19,21-22H,6,9H2,1-2H3/t14-,18?,19-/m0/s1
InChIKey	WZYPWKAIYULRHF-CJESRSHOSA-N
Formula	C₂₀H₂₀O₅
HBA	5
HBD	2
MW	340.38
Rotatable Bonds	1
TPSA	68.15
LogP	3.08
Number Rings	5
Number Aromatic Rings	2
Heavy Atom Count	25
Formal Charge	0
Fraction CSP3	0.4
Exact Mass	340.13
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: 11551842

Nmrshiftdb2: 70120614

Chembl: CHEMBL479479

No compound-protein relationship available.

SMILES: c1cccc(c12)OC3C2COc4c3cc5c(c4)OCC5

Level: 0

Mol. Weight: 340.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.83
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.540
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.91

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.020
Plasma Protein Binding: 73.15
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: Non-Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 11.490
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.590
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.130
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.330
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: Toxic
T. Pyriformis: -1.030
Rat (Acute): 2.090
Rat (Chronic Oral): 1.580
Fathead Minnow: 4.550
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 446.370
Hydration Free Energy: -8.720
Log(D) at pH=7.4: 3.030
Log(P): 2.92
Log S: -3.98
Log(Vapor Pressure): -9.25
Melting Point: 226.23
pKa Acid: 10.41
pKa Basic: 6.65

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9542
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9542
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.8851
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.8851
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8701
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8701
11-beta-hydroxysteroid dehydrogenase 1	P50172	DHI1_MOUSE	Mus musculus	3	0.8669
11-beta-hydroxysteroid dehydrogenase 1	P50172	DHI1_MOUSE	Mus musculus	3	0.8669
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	3	0.8645
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	3	0.8645
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.8637
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.8637
Beta-2-microglobulin	P61769	B2MG_HUMAN	Homo sapiens	3	0.8590
Beta-2-microglobulin	P61769	B2MG_HUMAN	Homo sapiens	3	0.8590
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8468
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8468
Matrix metalloproteinase-9	P14780	MMP9_HUMAN	Homo sapiens	3	0.8441
Matrix metalloproteinase-9	P14780	MMP9_HUMAN	Homo sapiens	3	0.8441
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.8245
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.8245
Sulfotransferase 1A1	P50225	ST1A1_HUMAN	Homo sapiens	3	0.8234
Sulfotransferase 1A1	P50225	ST1A1_HUMAN	Homo sapiens	3	0.8234
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8228
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8228
Enoyl-ACP reductase	Q9BH77	Q9BH77_PLAFA	Plasmodium falciparum	3	0.8206
Enoyl-ACP reductase	Q9BH77	Q9BH77_PLAFA	Plasmodium falciparum	3	0.8206
TetR family transcriptional regulator	Q58L87	Q58L87_MYCSM	Mycolicibacterium smegmatis	3	0.8171
TetR family transcriptional regulator	Q58L87	Q58L87_MYCSM	Mycolicibacterium smegmatis	3	0.8171
Reaction center protein L chain	P0C0Y7	RCEH_RHOSH	Rhodobacter sphaeroides	3	0.8140
Reaction center protein L chain	P0C0Y7	RCEH_RHOSH	Rhodobacter sphaeroides	3	0.8140
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.8063
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.8063
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.7826
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.7826
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7825
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7825
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7811
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7811
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7789
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7789
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.7782
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.7782
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.7767
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.7767
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7727
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7727
Japanin	M1MR49	M1MR49_RHIAP	Rhipicephalus appendiculatus	3	0.7640
Japanin	M1MR49	M1MR49_RHIAP	Rhipicephalus appendiculatus	3	0.7640
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7623
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7623
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.7464
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.7464
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7461
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7461
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7443
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7443
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7431
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7431
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7428
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7428
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7424
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7424
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7418
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7418
Calmodulin	P62157	CALM_BOVIN	Bos taurus	3	0.7368
Calmodulin	P62157	CALM_BOVIN	Bos taurus	3	0.7368
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7358
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7358
Tau-tubulin kinase 1	Q5TCY1	TTBK1_HUMAN	Homo sapiens	3	0.7343
Tau-tubulin kinase 1	Q5TCY1	TTBK1_HUMAN	Homo sapiens	3	0.7343
NADPH-dependent 7-cyano-7-deazaguanine reductase	Q9KTK0	QUEF_VIBCH	Vibrio cholerae serotype O1	3	0.7319
NADPH-dependent 7-cyano-7-deazaguanine reductase	Q9KTK0	QUEF_VIBCH	Vibrio cholerae serotype O1	3	0.7319
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7308
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7308
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7283
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7283
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7275
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7275
Transthyretin	Q9PTT3	Q9PTT3_SPAAU	Sparus aurata	3	0.7271
Transthyretin	Q9PTT3	Q9PTT3_SPAAU	Sparus aurata	3	0.7271
Ribosome-inactivating protein alpha-trichosanthin	P09989	RIPT_TRIKI	Trichosanthes kirilowii	3	0.7245
Ribosome-inactivating protein alpha-trichosanthin	P09989	RIPT_TRIKI	Trichosanthes kirilowii	3	0.7245
Cytochrome P450 130	P9WPN5	CP130_MYCTU	Mycobacterium tuberculosis	3	0.7245
Cytochrome P450 130	P9WPN5	CP130_MYCTU	Mycobacterium tuberculosis	3	0.7245
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7239
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7239
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	4	0.7239
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	4	0.7239
Cytidylate kinase	Q5SL35	KCY_THET8	Thermus thermophilus	3	0.7233
Cytidylate kinase	Q5SL35	KCY_THET8	Thermus thermophilus	3	0.7233
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	2	0.7230
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	2	0.7230
Nuclear receptor coactivator 2	Q15596	NCOA2_HUMAN	Homo sapiens	3	0.7222
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7222
Nuclear receptor coactivator 2	Q15596	NCOA2_HUMAN	Homo sapiens	3	0.7222
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7222
N-acetyltransferase domain-containing protein	Q9HV14	Q9HV14_PSEAE	Pseudomonas aeruginosa	3	0.7213
N-acetyltransferase domain-containing protein	Q9HV14	Q9HV14_PSEAE	Pseudomonas aeruginosa	3	0.7213
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7213
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7213
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7190
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7190
Cholesterol oxidase	P22637	CHOD_BREST	Brevibacterium sterolicum	3	0.7147
Cholesterol oxidase	P22637	CHOD_BREST	Brevibacterium sterolicum	3	0.7147
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7146
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7146
Retinol-binding protein 4	P18902	RET4_BOVIN	Bos taurus	3	0.7120
Retinol-binding protein 4	P18902	RET4_BOVIN	Bos taurus	3	0.7120
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.7102
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.7102
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7076
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7076
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7064
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7064
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7046
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7046
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7036
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7036
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7031
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7031
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7028
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7028
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	3	0.7018
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	3	0.7018
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7018
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7018
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7011
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7011
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7007
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7007

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