NPASS Compound

Natural Product: NPC475112

Natural Product ID	NPC475112
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Sid506289
IUPAC Name	3,8-dimethyl-3-(4-methylpent-3-enyl)-11H-pyrano[3,2-a]carbazol-9-ol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL498436
PubChem CID	375148
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000210] Carbazoles

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 51 54 0 0 0 0 0 0 0 0999 V2000 -7.6897 0.2700 1.5757 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5058 0.1804 0.6817 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2659 -0.0220 1.2540 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1701 -0.1042 0.4147 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3274 0.0151 -0.9600 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5949 0.2199 -1.5175 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6895 0.3026 -0.6869 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9789 0.5044 -1.1626 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1049 -0.1044 -1.5090 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.2000 -0.2928 -0.5248 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8316 -0.2984 0.6954 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1053 -0.4766 1.8622 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7383 -0.6508 1.8125 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0740 -0.6501 0.6007 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8108 -0.4721 -0.5431 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1338 -0.4680 -1.8270 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1629 -0.6325 -1.8858 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0122 -0.8283 -0.6976 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3008 -0.8230 0.5183 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7699 -2.1237 -0.9028 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9685 0.3580 -0.6324 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8820 0.2283 0.5724 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7866 1.4186 0.5723 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1078 1.2944 0.4976 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6635 -0.0847 0.4130 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0345 2.4403 0.4944 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4067 0.9848 1.1325 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2068 -0.7076 1.6425 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4248 0.6631 2.5856 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1118 -0.1179 2.3095 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7088 0.3118 -2.5888 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2248 0.0435 -2.0288 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8339 -0.0674 -2.5147 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6468 -0.4735 2.7984 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1575 -0.7905 2.7060 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7493 -0.3234 -2.7249 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6450 -0.6264 -2.8432 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1824 -2.5260 0.0492 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1239 -2.8982 -1.3500 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6425 -1.9859 -1.5755 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5481 0.4925 -1.5443 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3383 1.2552 -0.4684 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4535 -0.7160 0.5769 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3112 0.2735 1.5175 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4038 2.4304 0.6332 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3634 -0.7119 1.2919 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7709 -0.0788 0.3349 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2947 -0.5236 -0.5370 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3197 2.7802 -0.5257 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6072 3.3230 1.0044 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9991 2.1803 1.0033 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 2 0 5 6 1 0 6 7 2 0 7 8 1 0 5 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 1 0 18 20 1 0 18 21 1 0 21 22 1 0 22 23 1 0 23 24 2 3 24 25 1 0 24 26 1 0 7 2 1 0 11 4 1 0 15 10 1 0 19 14 1 0 1 27 1 0 1 28 1 0 1 29 1 0 3 30 1 0 6 31 1 0 8 32 1 0 9 33 1 0 12 34 1 0 13 35 1 0 16 36 1 0 17 37 1 0 20 38 1 0 20 39 1 0 20 40 1 0 21 41 1 0 21 42 1 0 22 43 1 0 22 44 1 0 23 45 1 0 25 46 1 0 25 47 1 0 25 48 1 0 26 49 1 0 26 50 1 0 26 51 1 0 M END

Standard InCHIKey	WWXYBSVWYPHUPZ-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C23H25NO2/c1-14(2)6-5-10-23(4)11-9-17-21(26-23)8-7-16-18-12-15(3)20(25)13-19(18)24-22(16)17/h6-9,11-13,24-25H,5,10H2,1-4H3
SMILES	CC1=CC2=C(C=C1O)NC3=C2C=CC4=C3C=CC(O4)(C)CCC=C(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	347.19	Volume:	379.624 ? Van der Waals volume.
Dense:	0.915	LogP:	6.235 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.516 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.611 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	21.0
TPSA:	45.25 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.55	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.514	Fsp³:	0.304
MCE-18:	73.6 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.989	Fluc inhibitor:	0.393 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.955 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.851 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.013	Promiscuous compounds:	0.219

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.971	MDCK Permeability:	-4.651
Pgp-inhibitor:	0.373	Pgp-substrate:	0.044
PAMPA:	0.426 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.068	30% Bioavailability (F30%):	0.139
50% Bioavailability (F50%):	0.883

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.692	MRP1:	0.979
Plasma Protein Binding (PPB):	98.302%	Volume Distribution (VD):	0.427
Fu:	1.538% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.988	BCRP inhibitor:	0.522
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.742	CYP1A2-substrate:	0.655
CYP2C19-inhibitor:	0.976	CYP2C19-substrate:	0.033
CYP2C9-inhibitor:	0.913	CYP2C9-substrate:	0.22
CYP2D6-inhibitor:	0.993	CYP2D6-substrate:	0.548
CYP3A4-inhibitor:	0.433	CYP3A4-substrate:	0.76
CYP2B6-substrate:	0.001	CYP2C8-inhibitor:	0.999
HLM stability:	0.601 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

5.828

Half-life (T1/2):

0.625

ADMET: Toxicity

hERG Blockers:	0.5	hERG Blockers (10um):	0.706
Human Hepatotoxicity (H-HT):	0.743	Drug-induced Liver Injury (DILI):	0.668
AMES Toxicity:	0.751	Rat Oral Acute Toxicity:	0.603
Maximum Recommended Daily Dose:	0.648	Skin Sensitization:	0.769
Carcinogencity:	0.754	Eye Corrosion:	0.0
Eye Irritation:	0.858	Respiratory Toxicity:	0.957
Drug-induced Neurotoxicity:	0.848	Ototoxicity:	0.711
Hematotoxicity:	0.457	Drug-induced Nephrotoxicity:	0.734
Genotoxicity:	0.215	RPMI-8226 Immunitoxicity:	0.138
A549 Cytotoxicity:	0.525	Hek293 Cytotoxicity:	0.607
BCF:	2.063 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	4.934 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.656 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.205 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO3118	Murraya euchrestifolia	Species	Rutaceae	Eukaryota	stem bark;fruit	n.a.	n.a.	PMID[10924160]
NPO3118	Murraya euchrestifolia	Species	Rutaceae	Eukaryota	root bark	Kuantaochi, Nantou Hsien, Taiwan	n.a.	PMID[10924160]
NPO3118	Murraya euchrestifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3118	Murraya euchrestifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3118	Murraya euchrestifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3118	Murraya euchrestifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Potency	38
EC50	5
GI50	96
AC50	2

Activity Type	# Activity
Individual protein	29
Cell line	89
Organism	4
Protein-protein interaction	1
Non-molecular	8
Others	10

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT282	Individual protein	MAP kinase ERK2	Homo sapiens	Potency	=	25118.9	nM	PMID[17970595]
NPT1416	Individual protein	Neuropeptide S receptor	Homo sapiens	Potency	=	25118.9	nM	PMID[22608675]
NPT1254	Individual protein	Streptokinase A	Streptococcus pyogenes serotype M1	EC50	=	3035.0	nM	DOI[10.6019/CHEMBL1201861]
NPT1005	Individual protein	Tumor susceptibility gene 101 protein	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[19733087]
NPT154	Individual protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	19952.6	nM	PMID[23398362]
NPT10	Individual protein	Geminin	Homo sapiens	Potency	n.a.	18356.4	nM	PMID[12141872]
NPT101	Individual protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	12589.3	nM	DrugMatrix in vivo data: Hematology
NPT159	Individual protein	Aberrant vpr protein	Human immunodeficiency virus 1	Potency	n.a.	56234.1	nM	PMID[19459694]
NPT1043	Individual protein	Glycoprotein hormones alpha chain	Homo sapiens	Potency	n.a.	28183.8	nM	PubChem BioAssay data set
NPT160	Individual protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	14125.4	nM	PMID[25050881]
NPT531	Individual protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	31622.8	nM	PMID[21868221]
NPT531	Individual protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	35481.3	nM	PMID[25064350]
NPT803	Individual protein	Flap endonuclease 1	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[16472241]
NPT54	Individual protein	Nonstructural protein 1	Influenza A virus	Potency	=	8912.5	nM	PMID[20921306]
NPT524	Individual protein	Serine-protein kinase ATM	Homo sapiens	Potency	=	28183.8	nM	PMID[24547740]
NPT484	Individual protein	Luciferin 4-monooxygenase	Photinus pyralis	Potency	n.a.	26854.5	nM	PMID[16499321]
NPT446	Individual protein	Rap guanine nucleotide exchange factor 3	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[8254346]
NPT51	Individual protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	12589.3	nM	DOI[10.6019/CHEMBL1201861]
NPT51	Individual protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	22387.2	nM	PMID[8699183]
NPT51	Individual protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	28183.8	nM	PMID[23734721]
NPT60	Individual protein	Lysosomal alpha-glucosidase	Homo sapiens	Potency	=	39810.7	nM	PMID[17420206]
NPT63	Individual protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[22705001]
NPT478	Individual protein	Ataxin-2	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[23268694]
NPT861	Individual protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	29092.9	nM	PubChem BioAssay data set
NPT920	Individual protein	Alpha-synuclein	Homo sapiens	Potency	n.a.	35481.3	nM	DrugMatrix in vivo data: Hematology
NPT442	Individual protein	Ferritin light chain	Equus caballus	Potency	=	12589.3	nM	PMID[12014950]
NPT197	Protein-protein interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	3162.3	nM	DrugMatrix in vivo data: Pathology
NPT532	Individual protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[20593839]
NPT64	Individual protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	20587.8	nM	DrugMatrix in vivo data: Pathology
NPT49	Individual protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	3.5	nM	PMID[18197599]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT404	Cell line	CCRF-CEM	Homo sapiens	GI50	=	5011.87	nM	PMID[17850214]
NPT111	Cell line	K562	Homo sapiens	GI50	=	5623.41	nM	DOI[10.6019/CHEMBL1201861]
NPT112	Cell line	MOLT-4	Homo sapiens	GI50	=	4168.69	nM	PubChem BioAssay data set
NPT385	Cell line	SR	Homo sapiens	GI50	=	5495.41	nM	PubChem BioAssay data set
NPT81	Cell line	A549	Homo sapiens	GI50	=	6606.93	nM	PubChem BioAssay data set
NPT379	Cell line	HOP-62	Homo sapiens	GI50	=	4786.3	nM	PubChem BioAssay data set
NPT372	Cell line	HOP-92	Homo sapiens	GI50	=	4265.8	nM	PubChem BioAssay data set
NPT405	Cell line	NCI-H226	Homo sapiens	GI50	=	7079.46	nM	DOI[10.6019/CHEMBL1201861]
NPT388	Cell line	NCI-H322M	Homo sapiens	GI50	=	6606.93	nM	PubChem BioAssay data set
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	=	4677.35	nM	PMID[11384245]
NPT455	Cell line	NCI-H522	Homo sapiens	GI50	=	3890.45	nM	PMID[11384245]
NPT572	Cell line	DMS-273	Homo sapiens	GI50	=	5011.87	nM	PMID[2542558]
NPT579	Cell line	DLD-1	Homo sapiens	GI50	=	8912.51	nM	PMID[2542558]
NPT391	Cell line	HCC 2998	Homo sapiens	GI50	=	4677.35	nM	PMID[2542558]
NPT393	Cell line	HCT-116	Homo sapiens	GI50	=	8709.64	nM	PMID[2542558]
NPT148	Cell line	HCT-15	Homo sapiens	GI50	=	5011.87	nM	PMID[2542558]
NPT139	Cell line	HT-29	Homo sapiens	GI50	=	4897.79	nM	PMID[20061160]
NPT386	Cell line	KM12	Homo sapiens	GI50	=	4786.3	nM	PubChem BioAssay data set
NPT575	Cell line	KM-20L2	Homo sapiens	GI50	=	5248.07	nM	PubChem BioAssay data set
NPT323	Cell line	SW-620	Homo sapiens	GI50	=	4677.35	nM	PubChem BioAssay data set
NPT395	Cell line	SF-268	Homo sapiens	GI50	=	5011.87	nM	PubChem BioAssay data set
NPT374	Cell line	SF-539	Homo sapiens	GI50	=	4570.88	nM	PMID[21381696]
NPT383	Cell line	SNB-19	Homo sapiens	GI50	=	25118.86	nM	PubChem BioAssay data set
NPT392	Cell line	SNB-75	Homo sapiens	GI50	=	12882.5	nM	PubChem BioAssay data set
NPT380	Cell line	U-251	Homo sapiens	GI50	=	4570.88	nM	PMID[21381696]
NPT390	Cell line	LOX IMVI	Homo sapiens	GI50	=	4570.88	nM	PubChem BioAssay data set
NPT375	Cell line	Malme-3M	Homo sapiens	GI50	=	5248.07	nM	PubChem BioAssay data set
NPT387	Cell line	M14	Homo sapiens	GI50	=	3890.45	nM	PMID[25913865]
NPT573	Cell line	M19-MEL	Homo sapiens	GI50	=	6918.31	nM	PMID[25913865]
NPT147	Cell line	SK-MEL-2	Homo sapiens	GI50	=	6456.54	nM	PMID[25913865]
NPT373	Cell line	SK-MEL-5	Homo sapiens	GI50	=	4897.79	nM	PMID[25913865]
NPT398	Cell line	UACC-62	Homo sapiens	GI50	=	9332.54	nM	PMID[25913865]
NPT401	Cell line	786-0	Homo sapiens	GI50	=	4265.8	nM	PMID[19738007]
NPT369	Cell line	ACHN	Homo sapiens	GI50	=	6760.83	nM	PMID[17249727]
NPT406	Cell line	RXF 393	Homo sapiens	GI50	=	5248.07	nM	PMID[17249727]
NPT368	Cell line	SN12C	Homo sapiens	GI50	=	4677.35	nM	PMID[17279798]
NPT384	Cell line	TK-10	Homo sapiens	GI50	=	16595.87	nM	PMID[17279798]
NPT65	Cell line	HepG2	Homo sapiens	Potency	n.a.	15848.9	nM	PMID[17846127]
NPT368	Cell line	SN12C	Homo sapiens	GI50	n.a.	4623.81	nM	PMID[14695798]
NPT369	Cell line	ACHN	Homo sapiens	GI50	n.a.	6823.39	nM	PMID[17060530]
NPT371	Cell line	UO-31	Homo sapiens	GI50	n.a.	2500.35	nM	PMID[25136754]
NPT372	Cell line	HOP-92	Homo sapiens	GI50	n.a.	4216.97	nM	PMID[19115838]
NPT116	Cell line	HL-60	Homo sapiens	GI50	n.a.	9484.18	nM	PMID[18834112]
NPT374	Cell line	SF-539	Homo sapiens	GI50	n.a.	4591.98	nM	DrugMatrix in vitro pharmacology data
NPT375	Cell line	Malme-3M	Homo sapiens	GI50	n.a.	5199.96	nM	PMID[23683594]
NPT373	Cell line	SK-MEL-5	Homo sapiens	GI50	n.a.	4841.72	nM	PMID[22901896]
NPT111	Cell line	K562	Homo sapiens	GI50	n.a.	5649.37	nM	PMID[19805572]
NPT377	Cell line	OVCAR-3	Homo sapiens	GI50	n.a.	4753.35	nM	PMID[16643028]
NPT112	Cell line	MOLT-4	Homo sapiens	GI50	n.a.	4168.69	nM	PubChem BioAssay data set
NPT379	Cell line	HOP-62	Homo sapiens	GI50	n.a.	4742.42	nM	DrugMatrix in vitro pharmacology data
NPT380	Cell line	U-251	Homo sapiens	GI50	n.a.	4528.98	nM	Open TG-GATES in vivo data: Hematology
NPT381	Cell line	OVCAR-8	Homo sapiens	GI50	n.a.	3810.66	nM	PMID[24117130]
NPT382	Cell line	OVCAR-5	Homo sapiens	GI50	n.a.	19364.22	nM	PMID[24389510]
NPT572	Cell line	DMS-273	Homo sapiens	GI50	n.a.	4954.5	nM	PMID[18077425]
NPT383	Cell line	SNB-19	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[22582991]
NPT384	Cell line	TK-10	Homo sapiens	GI50	n.a.	16672.47	nM	PMID[20070106]
NPT385	Cell line	SR	Homo sapiens	GI50	n.a.	5546.26	nM	PMID[8377014]
NPT323	Cell line	SW-620	Homo sapiens	GI50	n.a.	4677.35	nM	PubChem BioAssay data set
NPT573	Cell line	M19-MEL	Homo sapiens	GI50	n.a.	6982.32	nM	DrugMatrix in vivo data: Pathology
NPT386	Cell line	KM12	Homo sapiens	GI50	n.a.	4742.42	nM	PMID[12502320]
NPT455	Cell line	NCI-H522	Homo sapiens	GI50	n.a.	3863.67	nM	PMID[3210015]
NPT574	Cell line	XF498	Homo sapiens	GI50	n.a.	2500.35	nM	PMID[17958396]
NPT387	Cell line	M14	Homo sapiens	GI50	n.a.	3917.42	nM	PMID[22552195]
NPT388	Cell line	NCI-H322M	Homo sapiens	GI50	n.a.	6668.07	nM	PMID[22694318]
NPT389	Cell line	RPMI-8226	Homo sapiens	GI50	n.a.	6591.74	nM	DrugMatrix in vivo data: Pathology
NPT390	Cell line	LOX IMVI	Homo sapiens	GI50	n.a.	4528.98	nM	PMID[12027740]
NPT456	Cell line	OVCAR-4	Homo sapiens	GI50	n.a.	7943.28	nM	PMID[8411013]
NPT147	Cell line	SK-MEL-2	Homo sapiens	GI50	n.a.	6471.43	nM	PMID[21489802]
NPT575	Cell line	KM-20L2	Homo sapiens	GI50	n.a.	5223.96	nM	DOI[10.6019/CHEMBL1201861]
NPT81	Cell line	A549	Homo sapiens	GI50	n.a.	6591.74	nM	PMID[18166016]
NPT391	Cell line	HCC 2998	Homo sapiens	GI50	n.a.	4623.81	nM	PMID[19029333]
NPT148	Cell line	HCT-15	Homo sapiens	GI50	n.a.	4965.92	nM	PubChem BioAssay data set
NPT393	Cell line	HCT-116	Homo sapiens	GI50	n.a.	8790.23	nM	PMID[19596869]
NPT395	Cell line	SF-268	Homo sapiens	GI50	n.a.	5058.25	nM	PMID[19128860]
NPT146	Cell line	SK-OV-3	Homo sapiens	GI50	n.a.	2500.35	nM	DOI[10.1007/s00044-008-9135-y]
NPT731	Cell line	LXFL 529	Homo sapiens	GI50	n.a.	5152.29	nM	PMID[25871261]
NPT576	Cell line	DMS-114	Homo sapiens	GI50	n.a.	7144.96	nM	PMID[23434131]
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	n.a.	4731.51	nM	PMID[9249968]
NPT398	Cell line	UACC-62	Homo sapiens	GI50	n.a.	9397.23	nM	PMID[1602298]
NPT458	Cell line	IGROV-1	Homo sapiens	GI50	n.a.	2500.35	nM	DOI[10.1016/S0960-894X(97)10154-8]
NPT401	Cell line	786-0	Homo sapiens	GI50	n.a.	4265.8	nM	PMID[19738007]
NPT578	Cell line	SNB-78	Homo sapiens	GI50	n.a.	13031.67	nM	PMID[19928832]
NPT579	Cell line	DLD-1	Homo sapiens	GI50	n.a.	8892.01	nM	PubChem BioAssay data set
NPT404	Cell line	CCRF-CEM	Homo sapiens	GI50	n.a.	4965.92	nM	DOI[10.6019/CHEMBL1201861]
NPT405	Cell line	NCI-H226	Homo sapiens	GI50	n.a.	7014.55	nM	PMID[18293924]
NPT139	Cell line	HT-29	Homo sapiens	GI50	n.a.	4897.79	nM	PMID[20061160]
NPT170	Cell line	SK-MEL-28	Homo sapiens	GI50	n.a.	2500.35	nM	PMID[17043131]
NPT406	Cell line	RXF 393	Homo sapiens	GI50	n.a.	5272.3	nM	PubChem BioAssay data set
NPT407	Cell line	COLO 205	Homo sapiens	GI50	n.a.	2500.35	nM	PMID[11170682]
NPT174	Organism	Streptococcus	Streptococcus	EC50	=	6722.0	nM	PMID[24973030]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	18526.0	nM	PMID[21090801]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	9285.0	nM	PubChem BioAssay data set
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	GI50	=	9549.93	nM	PMID[10924160]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	GI50	=	6606.93	nM	PMID[10924160]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	GI50	=	5128.61	nM	PMID[10924160]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	GI50	=	7079.46	nM	PMID[10924160]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	GI50	=	4786.3	nM	PMID[10924160]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	GI50	=	7943.28	nM	PMID[10924160]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	GI50	=	19498.45	nM	PMID[10924160]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	GI50	=	3801.89	nM	PMID[10924160]
NPT1252	Organism	Streptococcus sp. 'group A'	Streptococcus sp. 'group A'	EC50	=	2312.0	nM	PMID[17958396]
NPT2	Others	Unspecified	n.a.	Potency	=	29092.9	nM	PMID[19534474]
NPT2	Others	Unspecified	n.a.	EC50	=	19600.0	nM	PMID[24437979]
NPT2	Others	Unspecified	n.a.	AC50	=	2903.0	nM	PMID[19132934]
NPT2	Others	Unspecified	n.a.	EC50	>	80000.0	nM	PMID[25756299]
NPT2	Others	Unspecified	n.a.	AC50	=	3585.0	nM	PMID[15026054]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	14125.4	nM	PMID[18955526]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	10000.0	nM	DOI[10.1007/s00044-012-0253-1]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	31622.8	nM	PMID[24480359]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	29092.9	nM	PMID[19534474]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC475112 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	12256
0.1-0.2	35098
0.2-0.3	2314
0.3-0.4	131
0.4-0.5	48
0.5-0.6	9
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.7273	Intermediate Similarity	NPC70259
0.6027	Remote Similarity	NPC475085
0.589	Remote Similarity	NPC70956
0.5652	Remote Similarity	NPC243834
0.5467	Remote Similarity	NPC72211
0.5309	Remote Similarity	NPC484121
0.5303	Remote Similarity	NPC600875
0.5286	Remote Similarity	NPC291535
0.527	Remote Similarity	NPC205934
0.527	Remote Similarity	NPC267766
0.5238	Remote Similarity	NPC484125

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC475112 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3385
0.1-0.2	5728
0.2-0.3	36
0.3-0.4	1
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data