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Rautandiol A

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

Canonical Smiles	Oc1ccc2c(c1)O[C@@H]1[C@H]2COc2c1cc1CC(O)C(Oc1c2)(C)C
InChI	InChI=1S/C20H20O5/c1-20(2)18(22)6-10-5-13-16(8-15(10)25-20)23-9-14-12-4-3-11(21)7-17(12)24-19(13)14/h3-5,7-8,14,18-19,21-22H,6,9H2,1-2H3/t14-,18?,19-/m0/s1
InChIKey	MGXPFABBMNBNJN-CJESRSHOSA-N
Formula	C₂₀H₂₀O₅
HBA	5
HBD	2
MW	340.38
Rotatable Bonds	0
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: 11674519

Nmrshiftdb2: 70120714

Chembl: CHEMBL517074

No compound-protein relationship available.

SMILES: c1cccc(c12)OC3C2COc4c3cc5c(c4)OCCC5

Level: 0

Mol. Weight: 340.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.71
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.500
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.25

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.090
Plasma Protein Binding: 74.98
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: 11.100
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.510
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.100
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 5.800
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -0.530
Rat (Acute): 2.160
Rat (Chronic Oral): 1.840
Fathead Minnow: 4.510
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 444.480
Hydration Free Energy: -9.060
Log(D) at pH=7.4: 3.310
Log(P): 3.46
Log S: -4.41
Log(Vapor Pressure): -8.91
Melting Point: 206.1
pKa Acid: 10.1
pKa Basic: 5.44

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	0.9540
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9540
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.9364
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.9364
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9172
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9172
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8923
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8923
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8818
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8818
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8364
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8364
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8222
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8222
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.8173
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.8173
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.8113
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.8113
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8109
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8109
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	3	0.8060
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	3	0.8060
Sulfotransferase 1A1	P50225	ST1A1_HUMAN	Homo sapiens	3	0.8049
Sulfotransferase 1A1	P50225	ST1A1_HUMAN	Homo sapiens	3	0.8049
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.8013
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.8013
Apoptosis regulator Bcl-2	P10415	BCL2_HUMAN	Homo sapiens	3	0.8011
Apoptosis regulator Bcl-2	P10415	BCL2_HUMAN	Homo sapiens	3	0.8011
Beta-2-microglobulin	P61769	B2MG_HUMAN	Homo sapiens	3	0.7902
Beta-2-microglobulin	P61769	B2MG_HUMAN	Homo sapiens	3	0.7902
TetR family transcriptional regulator	Q58L87	Q58L87_MYCSM	Mycolicibacterium smegmatis	3	0.7863
TetR family transcriptional regulator	Q58L87	Q58L87_MYCSM	Mycolicibacterium smegmatis	3	0.7863
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.7803
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.7803
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7722
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7722
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7691
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7691
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7682
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7682
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7560
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7560
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	4	0.7527
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	4	0.7527
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7518
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7518
Aldehyde dehydrogenase, dimeric NADP-preferring	P30838	AL3A1_HUMAN	Homo sapiens	3	0.7502
Aldehyde dehydrogenase, dimeric NADP-preferring	P30838	AL3A1_HUMAN	Homo sapiens	3	0.7502
Dihydrofolate reductase	Q83AB2	Q83AB2_COXBU	Coxiella burnetii	3	0.7495
Dihydrofolate reductase	Q83AB2	Q83AB2_COXBU	Coxiella burnetii	3	0.7495
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7461
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7461
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7447
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7447
Nuclear receptor coactivator 2	Q15596	NCOA2_HUMAN	Homo sapiens	3	0.7434
Nuclear receptor coactivator 2	Q15596	NCOA2_HUMAN	Homo sapiens	3	0.7434
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7396
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7396
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7394
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7394
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	4	0.7389
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	4	0.7389
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7377
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7377
Transthyretin	Q9PTT3	Q9PTT3_SPAAU	Sparus aurata	3	0.7328
Transthyretin	Q9PTT3	Q9PTT3_SPAAU	Sparus aurata	3	0.7328
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7284
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7284
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7272
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7272
Cholesterol oxidase	P22637	CHOD_BREST	Brevibacterium sterolicum	3	0.7246
Cholesterol oxidase	P22637	CHOD_BREST	Brevibacterium sterolicum	3	0.7246
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7239
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7239
Cytidylate kinase	Q5SL35	KCY_THET8	Thermus thermophilus	3	0.7232
Cytidylate kinase	Q5SL35	KCY_THET8	Thermus thermophilus	3	0.7232
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7203
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7203
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	3	0.7201
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	3	0.7201
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7194
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7194
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7192
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7192
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7192
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7192
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	3	0.7186
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	3	0.7186
N-acetyltransferase domain-containing protein	Q9HV14	Q9HV14_PSEAE	Pseudomonas aeruginosa	3	0.7179
N-acetyltransferase domain-containing protein	Q9HV14	Q9HV14_PSEAE	Pseudomonas aeruginosa	3	0.7179
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.7153
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.7153
Ribosome-inactivating protein alpha-trichosanthin	P09989	RIPT_TRIKI	Trichosanthes kirilowii	3	0.7144
Ribosome-inactivating protein alpha-trichosanthin	P09989	RIPT_TRIKI	Trichosanthes kirilowii	3	0.7144
NADPH-dependent 7-cyano-7-deazaguanine reductase	Q9KTK0	QUEF_VIBCH	Vibrio cholerae serotype O1	3	0.7143
NADPH-dependent 7-cyano-7-deazaguanine reductase	Q9KTK0	QUEF_VIBCH	Vibrio cholerae serotype O1	3	0.7143
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7129
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7129
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.7125
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.7125
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7124
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7124
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	3	0.7115
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	3	0.7115
Dihydrofolate reductase	P22906	DYR_CANAX	Candida albicans	3	0.7080
Dihydrofolate reductase	P22906	DYR_CANAX	Candida albicans	3	0.7080
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7071
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7071
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	2	0.7048
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	2	0.7048
Holliday junction branch migration complex subunit RuvB	Q9PMT7	RUVB_CAMJE	Campylobacter jejuni subsp. jejuni serotype O:2	2	0.7042
Holliday junction branch migration complex subunit RuvB	Q9PMT7	RUVB_CAMJE	Campylobacter jejuni subsp. jejuni serotype O:2	2	0.7042
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7033
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7033
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7031
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7031
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	2	0.7021
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	2	0.7021
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7011
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7011

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