ANPDB

Select a section from the left sidebar

Norcowanin

Family: Plantae - Guttiferae
Kingdom: Plantae
Class: Xanthone

Canonical Smiles	C/C(=C\Cc1c(O)c(O)cc2c1c(=O)c1c(o2)cc(c(c1O)CC=C(C)C)O)/CCC=C(C)C
InChI	InChI=1S/C28H32O6/c1-15(2)7-6-8-17(5)10-12-19-24-22(14-21(30)26(19)31)34-23-13-20(29)18(11-9-16(3)4)27(32)25(23)28(24)33/h7,9-10,13-14,29-32H,6,8,11-12H2,1-5H3/b17-10+
InChIKey	YACCKSNWKYYRID-LICLKQGHSA-N
Formula	C₂₈H₃₂O₆
HBA	6
HBD	4
MW	464.56
Rotatable Bonds	7
TPSA	111.13
LogP	6.51
Number Rings	3
Number Aromatic Rings	3
Heavy Atom Count	34
Formal Charge	0
Fraction CSP3	0.32
Exact Mass	464.22
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Allanblackia monticola	Guttiferae	Plantae	1508190
2	Allanblackia floribunda	Guttiferae	Plantae	469914

Showing of synonyms

Azebaze AG, Teinkela JE, et al. (2015). Antiplasmodial activity of some phenolic compounds from Cameroonians Allanblackia.. African health sciences,2015, 15(3), 835-840. [View] [PubMed]
Menasria F, Azebaze AG, et al. (2008). Apoptotic effects on B-cell chronic lymphocytic leukemia (B-CLL) cells of heterocyclic compounds isolated from Guttiferaes.. Leukemia research,2008, 32(12), 1914-1926. [View] [PubMed]

Pubchem: 11518330

Cas: 158511-56-9

Zinc: ZINC000013393282

Nmrshiftdb2: 60080165

Chembl: CHEMBL463409

CPRiL: 413627

SMILES: c1cccc(c12)oc3c(c2=O)cccc3

Level: 0

Mol. Weight: 464.56 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp): -5.67
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.0
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.64

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.0
Plasma Protein Binding: 52.98
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: Inhibitor
CYP 2C9 Substrate: Substrate
CYP 2D6 Inhibitor: Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 4.81
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.08
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.56
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 7.31
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -106.92
Rat (Acute): 2.15
Rat (Chronic Oral): 3.01
Fathead Minnow: 6.23
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 547.77
Hydration Free Energy: -3.38
Log(D) at pH=7.4: 3.43
Log(P): 8.18
Log S: -6.07
Log(Vapor Pressure): -9.89
Melting Point: 184.64
pKa Acid: 7.62
pKa Basic: 7.39

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9178
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9146
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.9064
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.9045
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8981
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8976
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8937
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8866
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.8838
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8824
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	4	0.8746
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8651
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8644
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8637
3'-5' exoribonuclease Rv2179c	P9WJ73	EXRBN_MYCTU	Mycobacterium tuberculosis	3	0.8636
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8569
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8527
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.8499
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.8494
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.8484
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8461
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.8440
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8374
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.8356
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8327
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8242
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8237
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8218
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8192
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8192
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.8127
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8111
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	4	0.8066
Dihydroflavonol 4-reductase	P51110	DFRA_VITVI	Vitis vinifera	4	0.8041
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.8016
Dihydroflavonol 4-reductase	P51110	DFRA_VITVI	Vitis vinifera	4	0.8012
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7997
Nucleoside permease	Q9KPL5	Q9KPL5_VIBCH	Vibrio cholerae serotype O1	4	0.7974
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.7967
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7964
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7963
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7951
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7946
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7946
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	5	0.7921
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7855
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	4	0.7843
EbrA repressor	Q79SH7	Q79SH7_STRLI	Streptomyces lividans	3	0.7832
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7828
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B	Q13370	PDE3B_HUMAN	Homo sapiens	4	0.7825
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7797
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7788
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7786
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7776
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7753
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7752
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7745
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7736
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7728
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7727
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7726
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7713
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7711
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7702
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7683
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	2	0.7681
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7672
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7664
Sodium-dependent dopamine transporter	Q7K4Y6	DAT_DROME	Drosophila melanogaster	2	0.7619
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7616
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7587
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7577
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	2	0.7558
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	4	0.7536
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7533
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	4	0.7500
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	3	0.7492
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7490
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7488
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.7482
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	4	0.7459
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7453
TetR family transcriptional regulator	Q58L87	Q58L87_MYCSM	Mycolicibacterium smegmatis	3	0.7452
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7452
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7433
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7428
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7428
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7404
Vitamin D(3) 25-hydroxylase	C4B644	CPVDH_PSEAH	Pseudonocardia autotrophica	3	0.7373
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7365
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7364
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	4	0.7363
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7363
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7359
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7354
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.7353
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.7345
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	4	0.7337
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7330
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7300
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7295
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A	Q13946	PDE7A_HUMAN	Homo sapiens	4	0.7283
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7283
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7274
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7274
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7267
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7266
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.7247
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7247
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	3	0.7245
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7235
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7226
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7194
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7186
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7160
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7157
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7148
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7138
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7133
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7122
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7120
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7111
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7107
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7105
Serine/threonine-protein kinase Nek2	P51955	NEK2_HUMAN	Homo sapiens	3	0.7103
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7094
NAD(P)H dehydrogenase (quinone)	Q9I509	NQOR_PSEAE	Pseudomonas aeruginosa	5	0.7093
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7072
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.7063
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7062
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7060
Peripheral plasma membrane protein CASK	O14936	CSKP_HUMAN	Homo sapiens	3	0.7059
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7033
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7030
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7022
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	4	0.7019

Download SDF