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Paulownin

Family: Plantae - Bignoniaceae
Kingdom: Plantae
Class: Lignan

Canonical Smiles	O[C@]12CO[C@@H]([C@H]1CO[C@@H]2c1ccc2c(c1)OCO2)c1ccc2c(c1)OCO2
InChI	InChI=1S/C20H18O7/c21-20-8-23-18(11-1-3-14-16(5-11)26-9-24-14)13(20)7-22-19(20)12-2-4-15-17(6-12)27-10-25-15/h1-6,13,18-19,21H,7-10H2/t13-,18-,19-,20-/m1/s1
InChIKey	CAQZFLPWHBKTTR-WNISUXOKSA-N
Formula	C₂₀H₁₈O₇
HBA	7
HBD	1
MW	370.36
Rotatable Bonds	2
TPSA	75.61
LogP	2.33
Number Rings	6
Number Aromatic Rings	2
Heavy Atom Count	27
Formal Charge	0
Fraction CSP3	0.4
Exact Mass	370.11
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Kigelia africana	Bignoniaceae	Plantae	—

Showing of synonyms

Sidjui LS, Melong RR, et al. (2015). Triterpenes and Lignans from Kigelia africana. J App Pharm Sci, 2015, 5 (Suppl 2), 001-006. [View]

Pubchem: 3084131

Cas: 13040-46-5

Gnps: CCMSLIB00004714198

Zinc: ZINC000005037439

Nmrshiftdb2: 70128129

Chembl: CHEMBL479911

Comptox: DTXSID10156507

No compound-protein relationship available.

SMILES: O1COc(c12)ccc(c2)C3OCC(C34)C(OC4)c(c5)ccc(c56)OCO6

Level: 2

Mol. Weight: 370.36 g/mol

SMILES: O1COc(c12)ccc(c2)C3OCC(C34)COC4

Level: 1

Mol. Weight: 370.36 g/mol

SMILES: O1COc(c12)cccc2

Level: 0

Mol. Weight: 370.36 g/mol

SMILES: C1OCC(C12)COC2

Level: 0

Mol. Weight: 370.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.04
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.360
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.1

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.220
Plasma Protein Binding: 74.46
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: Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 15.320
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.130
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.390
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.300
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: -23.830
Rat (Acute): 2.240
Rat (Chronic Oral): 1.220
Fathead Minnow: 4.270
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 471.760
Hydration Free Energy: -5.530
Log(D) at pH=7.4: 2.830
Log(P): 3.1
Log S: -4.22
Log(Vapor Pressure): -9.86
Melting Point: 142.2
pKa Acid: 9.58
pKa Basic: 1.45

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.9114
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.9088
Glycogen phosphorylase, liver form	P06737	PYGL_HUMAN	Homo sapiens	4	0.8995
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.8809
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8776
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.8776
Aldehyde dehydrogenase, mitochondrial	P05091	ALDH2_HUMAN	Homo sapiens	4	0.8765
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8687
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.8621
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.8576
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8561
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.8551
Lysozyme C II	P11941	LYSC2_ONCMY	Oncorhynchus mykiss	3	0.8549
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8417
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.8386
ALK tyrosine kinase receptor	Q9UM73	ALK_HUMAN	Homo sapiens	3	0.8369
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.8348
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8339
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.8327
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.8311
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8236
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8166
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8151
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8057
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8006
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7993
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7992
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	P0AF12	MTNN_ECOLI	Escherichia coli	3	0.7984
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.7893
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7792
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7784
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7780
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7754
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9QYJ6	PDE10_RAT	Rattus norvegicus	3	0.7719
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7707
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7693
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7683
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.7683
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7678
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7670
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7622
Mitogen-activated protein kinase 14	P47811	MK14_MOUSE	Mus musculus	4	0.7621
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.7596
Phosphodiesterase	Q8WQX9	Q8WQX9_9TRYP	Trypanosoma brucei	4	0.7565
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7551
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7535
Matrilysin	P09237	MMP7_HUMAN	Homo sapiens	3	0.7531
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7518
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.7518
Matrix metalloproteinase-20	O60882	MMP20_HUMAN	Homo sapiens	3	0.7448
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	2	0.7443
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7423
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	2	0.7423
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7395
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7392
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7391
Beta-lactamase	Q79MP6	Q79MP6_PSEAI	Pseudomonas aeruginosa	2	0.7375
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.7371
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7365
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7345
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	2	0.7337
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7305
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7288
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7266
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7265
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7265
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7258
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.7257
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7248
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	2	0.7240
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7204
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	4	0.7202
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7193
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7188
Beta-adrenergic receptor kinase 1	P25098	ARBK1_HUMAN	Homo sapiens	3	0.7184
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	2	0.7169
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7156
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.7131
Cyclin-dependent kinase 8	P49336	CDK8_HUMAN	Homo sapiens	3	0.7118
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	2	0.7112
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7110
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	4	0.7099
Aminopeptidase N	P04825	AMPN_ECOLI	Escherichia coli	3	0.7093
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	2	0.7066
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7059
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7056
Decaprenylphosphoryl-beta-D-ribose oxidase	I6X8C4	I6X8C4_MYCTU	Mycobacterium tuberculosis	3	0.7052
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7041
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7033
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	2	0.7029
Aspartokinase 1, chloroplastic	Q9LYU8	AK1_ARATH	Arabidopsis thaliana	3	0.7020
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7018
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.7007
Phosphoenolpyruvate carboxykinase [GTP]	P9WIH3	PCKG_MYCTU	Mycobacterium tuberculosis	3	0.7005

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