NPASS Compound

Natural Product: NPC123202

Natural Product ID	NPC123202
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5,8-Dihydroxy-6-Methoxy-2-Methylbenzo[G]Chromen-4-One
IUPAC Name	5,8-dihydroxy-6-methoxy-2-methylbenzo[g]chromen-4-one
Synonyms	TMC-256A1
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL252106
PubChem CID	10038860
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans [CHEMONTID:0001641] Naphthopyranones

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 32 34 0 0 0 0 0 0 0 0999 V2000 -3.9384 -2.2116 0.2974 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6521 -1.6769 0.2281 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3490 -0.3658 -0.0398 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3258 0.5760 -0.2734 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9671 1.8884 -0.5397 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9763 2.7916 -0.7661 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6347 2.2409 -0.5687 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6340 1.3017 -0.3349 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9970 -0.0030 -0.0704 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0134 -0.9310 0.1605 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4107 -2.2355 0.4238 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3202 -0.5799 0.1318 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6831 0.7258 -0.1329 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7074 1.6724 -0.3674 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9566 1.0355 -0.1548 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8915 0.1477 0.0658 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5992 -1.1709 0.3357 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2826 -1.5576 0.3725 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9003 -2.7268 0.6076 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3331 0.5868 0.0222 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5692 -1.7672 -0.4842 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8543 -3.3058 0.0756 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3953 -2.0650 1.3185 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3502 0.2486 -0.2391 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8640 3.7685 -0.6017 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3377 3.2647 -0.7758 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7646 -2.5464 1.3042 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9505 2.7050 -0.5783 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3718 -1.9040 0.5179 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4152 1.5478 0.5906 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6358 0.6997 -1.0243 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9868 -0.1535 0.4992 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 1 0 5 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 1 0 10 12 2 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 16 20 1 0 9 3 1 0 18 12 1 0 14 8 1 0 1 21 1 0 1 22 1 0 1 23 1 0 4 24 1 0 6 25 1 0 7 26 1 0 11 27 1 0 14 28 1 0 17 29 1 0 20 30 1 0 20 31 1 0 20 32 1 0 M END

Standard InCHIKey	KLKFLNXANXGSIT-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C15H12O5/c1-7-3-10(17)14-12(20-7)5-8-4-9(16)6-11(19-2)13(8)15(14)18/h3-6,16,18H,1-2H3
SMILES	COc1cc(O)cc2c1c(O)c1c(c2)oc(cc1=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	272.07	Volume:	267.823 ? Van der Waals volume.
Dense:	1.016	LogP:	2.218 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.09 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.255 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	17.0
TPSA:	79.9 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	2.0	Rings:	3.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.666	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.631	Fsp³:	0.133
MCE-18:	18.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.269	Fluc inhibitor:	0.088 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.519 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.554 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.389	Promiscuous compounds:	0.444

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.983	MDCK Permeability:	-4.813
Pgp-inhibitor:	0.014	Pgp-substrate:	0.069
PAMPA:	0.378 ? 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%):	0.124	30% Bioavailability (F30%):	0.106
50% Bioavailability (F50%):	0.795

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.101	MRP1:	0.983
Plasma Protein Binding (PPB):	96.827%	Volume Distribution (VD):	-0.02
Fu:	3.04% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.99	BCRP inhibitor:	0.003
BSEP inhibitor:	0.965

ADMET: Metabolism

CYP1A2-inhibitor:	0.606	CYP1A2-substrate:	0.424
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.018
CYP2C9-inhibitor:	0.851	CYP2C9-substrate:	0.26
CYP2D6-inhibitor:	0.978	CYP2D6-substrate:	0.02
CYP3A4-inhibitor:	0.008	CYP3A4-substrate:	0.053
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.827
HLM stability:	0.144 ? 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):

3.925

Half-life (T1/2):

1.026

ADMET: Toxicity

hERG Blockers:	0.095	hERG Blockers (10um):	0.48
Human Hepatotoxicity (H-HT):	0.549	Drug-induced Liver Injury (DILI):	0.816
AMES Toxicity:	0.748	Rat Oral Acute Toxicity:	0.571
Maximum Recommended Daily Dose:	0.799	Skin Sensitization:	0.575
Carcinogencity:	0.758	Eye Corrosion:	0.173
Eye Irritation:	0.993	Respiratory Toxicity:	0.925
Drug-induced Neurotoxicity:	0.191	Ototoxicity:	0.147
Hematotoxicity:	0.222	Drug-induced Nephrotoxicity:	0.209
Genotoxicity:	0.911	RPMI-8226 Immunitoxicity:	0.113
A549 Cytotoxicity:	0.274	Hek293 Cytotoxicity:	0.504
BCF:	0.897 ? 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:	3.532 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.373 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.942 ? 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
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[ 19156306]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(01)88611-1]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/np058103o]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/JR9620000040]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1080/00021369.1966.10858561]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1080/00021369.1972.10860562]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1080/00021369.1985.10867263]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[10695672]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12458767]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542363]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	sponge-derived	n.a.	PMID[15387655]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387655]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15556711]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15620260]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17653510]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17827758]
NPO9478	Comantheria rotula	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[17844994]
NPO18382	Phyllanthus piscatorum	Species	Leiothrichidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20014861]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20028011]
NPO32950	crinoids	Class	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20627559]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21176790]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21543515]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21774474]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	latex	n.a.	PMID[21854017]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21854017]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22921072]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24684908]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25044953]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25062661]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25293978]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26040782]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26132344]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26414728]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27245874]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32159958]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6073032]
NPO17416	Santolina oblongifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8988605]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	mycelium	n.a.	Database[Article]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17416	Santolina oblongifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14911	Shorea disticha	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19657	Ursus arctos	Species	Ursidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18382	Phyllanthus piscatorum	Species	Leiothrichidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18382	Phyllanthus piscatorum	Species	Leiothrichidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19657	Ursus arctos	Species	Ursidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19657	Ursus arctos	Species	Ursidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19657	Ursus arctos	Species	Ursidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22369	Papaver heterophyllum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3293	Pertusaria lutescens	Species	Pertusariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9478	Comantheria rotula	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO17416	Santolina oblongifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18382	Phyllanthus piscatorum	Species	Leiothrichidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14911	Shorea disticha	Species	Dipterocarpaceae	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
IC50	8
GI50	57
TGI	56

Activity Type	# Activity
Cell line	113
Others	5
Protein family	1
Non-molecular	2

Molecular-level activity

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

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	=	30199.52	nM	PMID[17844994]
NPT404	Cell line	CCRF-CEM	Homo sapiens	TGI	=	100000.0	nM	PMID[17844994]
NPT116	Cell line	HL-60	Homo sapiens	GI50	=	20892.96	nM	PMID[17844994]
NPT116	Cell line	HL-60	Homo sapiens	TGI	=	41686.94	nM	PMID[17844994]
NPT111	Cell line	K562	Homo sapiens	GI50	=	14791.08	nM	PMID[17844994]
NPT111	Cell line	K562	Homo sapiens	TGI	=	48977.88	nM	PMID[17844994]
NPT112	Cell line	MOLT-4	Homo sapiens	GI50	=	17782.79	nM	PMID[17844994]
NPT112	Cell line	MOLT-4	Homo sapiens	TGI	=	51286.14	nM	PMID[17844994]
NPT385	Cell line	SR	Homo sapiens	GI50	=	15135.61	nM	PMID[17844994]
NPT385	Cell line	SR	Homo sapiens	TGI	=	41686.94	nM	PMID[17844994]
NPT81	Cell line	A549	Homo sapiens	GI50	=	29512.09	nM	PMID[17844994]
NPT81	Cell line	A549	Homo sapiens	TGI	>	100000.0	nM	PMID[17844994]
NPT394	Cell line	EKVX	Homo sapiens	GI50	=	37153.52	nM	PMID[17844994]
NPT394	Cell line	EKVX	Homo sapiens	TGI	>	100000.0	nM	PMID[17844994]
NPT372	Cell line	HOP-92	Homo sapiens	GI50	=	30902.95	nM	PMID[17844994]
NPT372	Cell line	HOP-92	Homo sapiens	TGI	>	100000.0	nM	PMID[17844994]
NPT405	Cell line	NCI-H226	Homo sapiens	GI50	=	22387.21	nM	PMID[17844994]
NPT405	Cell line	NCI-H226	Homo sapiens	TGI	>	100000.0	nM	PMID[17844994]
NPT370	Cell line	NCI-H23	Homo sapiens	GI50	=	24547.09	nM	PMID[17844994]
NPT370	Cell line	NCI-H23	Homo sapiens	TGI	=	83176.38	nM	PMID[17844994]
NPT388	Cell line	NCI-H322M	Homo sapiens	GI50	=	26915.35	nM	PMID[17844994]
NPT388	Cell line	NCI-H322M	Homo sapiens	TGI	=	95499.26	nM	PMID[17844994]
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	=	19054.61	nM	PMID[17844994]
NPT397	Cell line	NCI-H460	Homo sapiens	TGI	=	50118.72	nM	PMID[17844994]
NPT455	Cell line	NCI-H522	Homo sapiens	GI50	=	2187.76	nM	PMID[17844994]
NPT455	Cell line	NCI-H522	Homo sapiens	TGI	=	22908.68	nM	PMID[17844994]
NPT407	Cell line	COLO 205	Homo sapiens	GI50	=	20417.38	nM	PMID[17844994]
NPT407	Cell line	COLO 205	Homo sapiens	TGI	=	54954.09	nM	PMID[17844994]
NPT148	Cell line	HCT-15	Homo sapiens	GI50	=	23442.29	nM	PMID[17844994]
NPT148	Cell line	HCT-15	Homo sapiens	TGI	=	70794.58	nM	PMID[17844994]
NPT139	Cell line	HT-29	Homo sapiens	GI50	=	29512.09	nM	PMID[17844994]
NPT139	Cell line	HT-29	Homo sapiens	TGI	>	100000.0	nM	PMID[17844994]
NPT386	Cell line	KM12	Homo sapiens	GI50	=	18620.87	nM	PMID[17844994]
NPT386	Cell line	KM12	Homo sapiens	TGI	=	39810.72	nM	PMID[17844994]
NPT323	Cell line	SW-620	Homo sapiens	GI50	=	295.12	nM	PMID[17844994]
NPT323	Cell line	SW-620	Homo sapiens	TGI	=	16982.44	nM	PMID[17844994]
NPT395	Cell line	SF-268	Homo sapiens	GI50	=	30199.52	nM	PMID[17844994]
NPT395	Cell line	SF-268	Homo sapiens	TGI	>	100000.0	nM	PMID[17844994]
NPT399	Cell line	SF-295	Homo sapiens	GI50	=	30199.52	nM	PMID[17844994]
NPT399	Cell line	SF-295	Homo sapiens	TGI	>	100000.0	nM	PMID[17844994]
NPT374	Cell line	SF-539	Homo sapiens	GI50	=	27542.29	nM	PMID[17844994]
NPT374	Cell line	SF-539	Homo sapiens	TGI	=	87096.36	nM	PMID[17844994]
NPT383	Cell line	SNB-19	Homo sapiens	GI50	=	32359.37	nM	PMID[17844994]
NPT383	Cell line	SNB-19	Homo sapiens	TGI	>	100000.0	nM	PMID[17844994]
NPT392	Cell line	SNB-75	Homo sapiens	GI50	=	46773.51	nM	PMID[17844994]
NPT392	Cell line	SNB-75	Homo sapiens	TGI	>	100000.0	nM	PMID[17844994]
NPT380	Cell line	U-251	Homo sapiens	GI50	=	33113.11	nM	PMID[17844994]
NPT380	Cell line	U-251	Homo sapiens	TGI	>	100000.0	nM	PMID[17844994]
NPT390	Cell line	LOX IMVI	Homo sapiens	GI50	=	18197.01	nM	PMID[17844994]
NPT390	Cell line	LOX IMVI	Homo sapiens	TGI	=	52480.75	nM	PMID[17844994]
NPT375	Cell line	Malme-3M	Homo sapiens	GI50	=	35481.34	nM	PMID[17844994]
NPT375	Cell line	Malme-3M	Homo sapiens	TGI	=	95499.26	nM	PMID[17844994]
NPT387	Cell line	M14	Homo sapiens	GI50	=	19952.62	nM	PMID[17844994]
NPT387	Cell line	M14	Homo sapiens	TGI	=	45708.82	nM	PMID[17844994]
NPT147	Cell line	SK-MEL-2	Homo sapiens	GI50	=	4897.79	nM	PMID[17844994]
NPT147	Cell line	SK-MEL-2	Homo sapiens	TGI	=	35481.34	nM	PMID[17844994]
NPT170	Cell line	SK-MEL-28	Homo sapiens	GI50	=	23988.33	nM	PMID[17844994]
NPT170	Cell line	SK-MEL-28	Homo sapiens	TGI	=	63095.73	nM	PMID[17844994]
NPT373	Cell line	SK-MEL-5	Homo sapiens	GI50	=	457.09	nM	PMID[17844994]
NPT373	Cell line	SK-MEL-5	Homo sapiens	TGI	=	12022.64	nM	PMID[17844994]
NPT403	Cell line	UACC-257	Homo sapiens	GI50	=	45708.82	nM	PMID[17844994]
NPT403	Cell line	UACC-257	Homo sapiens	TGI	>	100000.0	nM	PMID[17844994]
NPT398	Cell line	UACC-62	Homo sapiens	GI50	=	29512.09	nM	PMID[17844994]
NPT398	Cell line	UACC-62	Homo sapiens	TGI	>	100000.0	nM	PMID[17844994]
NPT391	Cell line	HCC 2998	Homo sapiens	GI50	=	24547.09	nM	PMID[17844994]
NPT391	Cell line	HCC 2998	Homo sapiens	TGI	=	64565.42	nM	PMID[17844994]
NPT393	Cell line	HCT-116	Homo sapiens	GI50	=	14454.4	nM	PMID[17844994]
NPT393	Cell line	HCT-116	Homo sapiens	TGI	=	30199.52	nM	PMID[17844994]
NPT456	Cell line	OVCAR-4	Homo sapiens	GI50	=	45708.82	nM	PMID[17844994]
NPT456	Cell line	OVCAR-4	Homo sapiens	TGI	>	100000.0	nM	PMID[17844994]
NPT382	Cell line	OVCAR-5	Homo sapiens	GI50	=	46773.51	nM	PMID[17844994]
NPT382	Cell line	OVCAR-5	Homo sapiens	TGI	>	100000.0	nM	PMID[17844994]
NPT381	Cell line	OVCAR-8	Homo sapiens	GI50	=	27542.29	nM	PMID[17844994]
NPT381	Cell line	OVCAR-8	Homo sapiens	TGI	>	100000.0	nM	PMID[17844994]
NPT146	Cell line	SK-OV-3	Homo sapiens	GI50	=	31622.78	nM	PMID[17844994]
NPT146	Cell line	SK-OV-3	Homo sapiens	TGI	>	100000.0	nM	PMID[17844994]
NPT458	Cell line	IGROV-1	Homo sapiens	GI50	=	436.52	nM	PMID[17844994]
NPT458	Cell line	IGROV-1	Homo sapiens	TGI	=	23442.29	nM	PMID[17844994]
NPT401	Cell line	786-0	Homo sapiens	GI50	=	19952.62	nM	PMID[17844994]
NPT401	Cell line	786-0	Homo sapiens	TGI	=	50118.72	nM	PMID[17844994]
NPT376	Cell line	A498	Homo sapiens	GI50	=	616.6	nM	PMID[17844994]
NPT376	Cell line	A498	Homo sapiens	TGI	=	11748.98	nM	PMID[17844994]
NPT369	Cell line	ACHN	Homo sapiens	GI50	=	16982.44	nM	PMID[17844994]
NPT369	Cell line	ACHN	Homo sapiens	TGI	>	100000.0	nM	PMID[17844994]
NPT308	Cell line	CAKI-1	Homo sapiens	GI50	=	42657.95	nM	PMID[17844994]
NPT308	Cell line	CAKI-1	Homo sapiens	TGI	>	100000.0	nM	PMID[17844994]
NPT406	Cell line	RXF 393	Homo sapiens	GI50	=	20417.38	nM	PMID[17844994]
NPT406	Cell line	RXF 393	Homo sapiens	TGI	=	53703.18	nM	PMID[17844994]
NPT368	Cell line	SN12C	Homo sapiens	GI50	=	32359.37	nM	PMID[17844994]
NPT368	Cell line	SN12C	Homo sapiens	TGI	>	100000.0	nM	PMID[17844994]
NPT384	Cell line	TK-10	Homo sapiens	GI50	=	20417.38	nM	PMID[17844994]
NPT384	Cell line	TK-10	Homo sapiens	TGI	=	61659.5	nM	PMID[17844994]
NPT371	Cell line	UO-31	Homo sapiens	GI50	=	5128.61	nM	PMID[17844994]
NPT371	Cell line	UO-31	Homo sapiens	TGI	=	37153.52	nM	PMID[17844994]
NPT306	Cell line	PC-3	Homo sapiens	GI50	=	32359.37	nM	PMID[17844994]
NPT306	Cell line	PC-3	Homo sapiens	TGI	>	100000.0	nM	PMID[17844994]
NPT90	Cell line	DU-145	Homo sapiens	GI50	=	21877.62	nM	PMID[17844994]
NPT90	Cell line	DU-145	Homo sapiens	TGI	=	70794.58	nM	PMID[17844994]
NPT83	Cell line	MCF7	Homo sapiens	GI50	=	31622.78	nM	PMID[17844994]
NPT83	Cell line	MCF7	Homo sapiens	TGI	>	100000.0	nM	PMID[17844994]
NPT378	Cell line	NCI/ADR-RES	Homo sapiens	GI50	=	22387.21	nM	PMID[17844994]
NPT378	Cell line	NCI/ADR-RES	Homo sapiens	TGI	>	100000.0	nM	PMID[17844994]
NPT82	Cell line	MDA-MB-231	Homo sapiens	GI50	=	17782.79	nM	PMID[17844994]
NPT82	Cell line	MDA-MB-231	Homo sapiens	TGI	>	100000.0	nM	PMID[17844994]
NPT402	Cell line	Hs-578T	Homo sapiens	GI50	=	588.84	nM	PMID[17844994]
NPT400	Cell line	MDA-MB-435	Homo sapiens	GI50	=	27542.29	nM	PMID[17844994]
NPT400	Cell line	MDA-MB-435	Homo sapiens	TGI	>	100000.0	nM	PMID[17844994]
NPT457	Cell line	BT-549	Homo sapiens	GI50	=	20417.38	nM	PMID[17844994]
NPT457	Cell line	BT-549	Homo sapiens	TGI	>	100000.0	nM	PMID[17844994]
NPT396	Cell line	T47D	Homo sapiens	GI50	=	17782.79	nM	PMID[17844994]
NPT396	Cell line	T47D	Homo sapiens	TGI	>	100000.0	nM	PMID[17844994]
NPT81	Cell line	A549	Homo sapiens	IC50	>	20000.0	nM	PMID[34156846]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	TGI	=	91201.08	nM	PMID[17844994]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	GI50	<	100000.0	nM	PMID[17844994]
NPT2	Others	Unspecified	n.a.	IC50	=	900.0	nM	PMID[17844994]
NPT21802	Protein family	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	3400.0	nM	PMID[17844994]
NPT2	Others	Unspecified	n.a.	IC50	=	2500.0	nM	PMID[17844994]
NPT2	Others	Unspecified	n.a.	IC50	=	3300.0	nM	PMID[17844994]
NPT2	Others	Unspecified	n.a.	IC50	=	44000.0	nM	PMID[15620260]
NPT2	Others	Unspecified	n.a.	IC50	=	80000.0	nM	PMID[15620260]

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 NPC123202 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	28663
0.1-0.2	17358
0.2-0.3	3530
0.3-0.4	256
0.4-0.5	32
0.5-0.6	14
0.6-0.7	3
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
0.7321	Intermediate Similarity	NPC158338
0.7037	Intermediate Similarity	NPC7025
0.6607	Remote Similarity	NPC27221
0.6316	Remote Similarity	NPC7943
0.625	Remote Similarity	NPC22005
0.5763	Remote Similarity	NPC256672
0.5692	Remote Similarity	NPC604351
0.5652	Remote Similarity	NPC611282
0.5593	Remote Similarity	NPC294965
0.5571	Remote Similarity	NPC611333
0.5455	Remote Similarity	NPC31872
0.5441	Remote Similarity	NPC189552
0.5286	Remote Similarity	NPC26760
0.5273	Remote Similarity	NPC55557
0.5273	Remote Similarity	NPC125920
0.5179	Remote Similarity	NPC30647
0.5179	Remote Similarity	NPC61871
0.5167	Remote Similarity	NPC100985
0.5135	Remote Similarity	NPC259905

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC123202 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4907
0.1-0.2	4129
0.2-0.3	112
0.3-0.4	2
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