NPASS Compound

Natural Product: NPC128115

Natural Product ID	NPC128115
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	XVMZDZFTCKLZTF-NRFANRHFSA-N
IUPAC Name	n.a.
Synonyms	NSC-176323
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL522112
PubChem CID	123617
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000240] Camptothecins

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 46 50 0 0 0 0 0 0 0 0999 V2000 -5.8359 -0.7571 -1.7560 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5704 -1.0569 -0.9881 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0571 0.2738 -0.4267 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8071 0.0799 0.3494 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5779 0.2632 -0.2285 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4126 0.0728 0.5297 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9632 0.2310 0.0508 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7592 -0.0575 1.1372 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1224 0.0221 0.9392 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6919 0.3704 -0.2735 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8252 0.6511 -1.3360 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3802 0.9995 -2.5501 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7410 1.0827 -2.7611 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5632 0.7962 -1.6804 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0497 0.4462 -0.4580 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9161 0.1734 0.5764 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3070 0.2228 0.4894 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4978 0.5729 -1.1412 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8937 -0.3949 2.2916 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4571 -0.2868 1.8167 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6696 -0.4740 2.4099 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6631 -0.8082 3.6090 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8188 -0.2903 1.6767 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1231 -0.5015 2.3497 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0551 0.3993 1.8222 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0643 0.8398 0.5060 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9028 1.7001 0.0985 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8761 1.1376 -1.4997 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7092 -0.7325 -1.0857 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9714 -1.4342 -2.6234 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7225 0.2685 -2.1825 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7219 -1.7933 -0.1794 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8400 -1.4741 -1.7042 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5399 0.5514 -1.2600 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7964 -0.1963 1.7663 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7369 1.2220 -3.3898 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1585 1.3567 -3.7170 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6328 0.8724 -1.8855 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7824 0.3481 1.4979 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6634 -0.7588 0.1075 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6758 1.0735 -0.1466 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1200 -1.3948 2.7123 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0128 0.3251 3.1295 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0178 -0.3624 3.4507 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4469 -1.5660 2.2159 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4289 0.6863 -2.2593 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 11 18 2 0 8 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 3 28 1 6 26 3 1 0 23 4 2 0 20 6 1 0 18 7 1 0 15 10 1 0 1 29 1 0 1 30 1 0 1 31 1 0 2 32 1 0 2 33 1 0 5 34 1 0 9 35 1 0 12 36 1 0 13 37 1 0 14 38 1 0 17 39 1 0 17 40 1 0 17 41 1 0 19 42 1 0 19 43 1 0 24 44 1 0 24 45 1 0 28 46 1 0 M END

Standard InCHIKey	XVMZDZFTCKLZTF-NRFANRHFSA-N
Standard InCHI	InChI=1S/C21H18N2O5/c1-3-21(26)14-8-16-18-11(7-12-15(22-18)5-4-6-17(12)27-2)9-23(16)19(24)13(14)10-28-20(21)25/h4-8,26H,3,9-10H2,1-2H3/t21-/m0/s1
SMILES	CC[C@@]1(c2cc3-c4c(cc5c(cccc5OC)n4)Cn3c(=O)c2COC1=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	378.12	Volume:	371.206 ? Van der Waals volume.
Dense:	1.019	LogP:	1.472 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.893 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.895 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	27.0
TPSA:	90.65 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.537	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.225	Fsp³:	0.286
MCE-18:	93.444 ? 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:	0.252	Fluc inhibitor:	0.407 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.988 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.196 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.003	Promiscuous compounds:	0.545

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.084	MDCK Permeability:	-4.717
Pgp-inhibitor:	0.005	Pgp-substrate:	0.896
PAMPA:	0.969 ? 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%):	0.087	30% Bioavailability (F30%):	0.039
50% Bioavailability (F50%):	0.959

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.27	MRP1:	0.568
Plasma Protein Binding (PPB):	98.802%	Volume Distribution (VD):	-0.093
Fu:	1.07% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.811
OATP1B3 inhibitor:	0.137	BCRP inhibitor:	0.984
BSEP inhibitor:	0.995

ADMET: Metabolism

CYP1A2-inhibitor:	0.506	CYP1A2-substrate:	0.003
CYP2C19-inhibitor:	0.008	CYP2C19-substrate:	0.008
CYP2C9-inhibitor:	0.007	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.245
CYP3A4-inhibitor:	0.314	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.474
HLM stability:	0.759 ? 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):

7.176

Half-life (T1/2):

1.306

ADMET: Toxicity

hERG Blockers:	0.107	hERG Blockers (10um):	0.191
Human Hepatotoxicity (H-HT):	0.978	Drug-induced Liver Injury (DILI):	0.892
AMES Toxicity:	0.98	Rat Oral Acute Toxicity:	0.75
Maximum Recommended Daily Dose:	0.992	Skin Sensitization:	0.909
Carcinogencity:	0.992	Eye Corrosion:	0.0
Eye Irritation:	0.003	Respiratory Toxicity:	0.219
Drug-induced Neurotoxicity:	0.972	Ototoxicity:	0.749
Hematotoxicity:	0.985	Drug-induced Nephrotoxicity:	0.996
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.768
A549 Cytotoxicity:	0.409	Hek293 Cytotoxicity:	0.941
BCF:	1.14 ? 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:	3.962 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.075 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.786 ? 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
NPO12582	Camptotheca acuminata	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1111/j.1399-3054.2000.1100409.x]
NPO15805	Didymochlaena truncatula	Species	Didymochlaenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499333]
NPO11919	Hyrtios reticulatus	Species	Thorectidae	Eukaryota	n.a.	Papua New Guinea	n.a.	PMID[20000782]
NPO12582	Camptotheca acuminata	Species	Nyssaceae	Eukaryota	n.a.	xylem	n.a.	PMID[21348469]
NPO11919	Hyrtios reticulatus	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22695182]
NPO12582	Camptotheca acuminata	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3735324]
NPO4695	Ervatamia heyneana	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[521817]
NPO9517	Dictyota ciliolata	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11919	Hyrtios reticulatus	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20173	Aristolochia triangularis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12582	Camptotheca acuminata	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20173	Aristolochia triangularis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12582	Camptotheca acuminata	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4695	Ervatamia heyneana	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO12582	Camptotheca acuminata	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4695	Ervatamia heyneana	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO20173	Aristolochia triangularis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12582	Camptotheca acuminata	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12582	Camptotheca acuminata	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20173	Aristolochia triangularis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28756	Malayopython reticulatus	Species	Pythonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9517	Dictyota ciliolata	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17428	Mimusops manilkara	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20391	Podospora decipiens	Species	Lasiosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15805	Didymochlaena truncatula	Species	Didymochlaenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13888	Austrocylindropuntia cylindrica	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20915	Hippospongia gossypina	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1666	Radopholus similis	Species	Pratylenchidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18941	Teucrium canadense	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16944	Schizopelte californica	Species	Opegraphaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13851	Garberia heterophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11919	Hyrtios reticulatus	Species	Thorectidae	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
ED50	2
IC50	1
GI50	70

Activity Type	# Activity
Cell line	73

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
NPT91	Cell line	KB	Homo sapiens	ED50	=	0.17	ug ml-1	PMID[521817]
NPT168	Cell line	P388	Mus musculus	ED50	=	0.53	ug ml-1	PMID[521817]
NPT179	Cell line	A2780	Homo sapiens	IC50	=	0.02	ug.mL-1	PMID[16499333]
NPT368	Cell line	SN12C	Homo sapiens	GI50	n.a.	100.0	nM	PubChem BioAssay data set
NPT367	Cell line	MDA-N	Homo sapiens	GI50	n.a.	1000.0	nM	PubChem BioAssay data set
NPT369	Cell line	ACHN	Homo sapiens	GI50	n.a.	100.0	nM	PubChem BioAssay data set
NPT370	Cell line	NCI-H23	Homo sapiens	GI50	n.a.	100.0	nM	PubChem BioAssay data set
NPT371	Cell line	UO-31	Homo sapiens	GI50	n.a.	101.39	nM	PubChem BioAssay data set
NPT372	Cell line	HOP-92	Homo sapiens	GI50	n.a.	43.25	nM	PubChem BioAssay data set
NPT116	Cell line	HL-60	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT90	Cell line	DU-145	Homo sapiens	GI50	n.a.	1000.0	nM	PubChem BioAssay data set
NPT373	Cell line	SK-MEL-5	Homo sapiens	GI50	n.a.	116.41	nM	PubChem BioAssay data set
NPT374	Cell line	SF-539	Homo sapiens	GI50	n.a.	100.0	nM	PubChem BioAssay data set
NPT375	Cell line	Malme-3M	Homo sapiens	GI50	n.a.	348.34	nM	PubChem BioAssay data set
NPT111	Cell line	K562	Homo sapiens	GI50	n.a.	171.4	nM	PubChem BioAssay data set
NPT376	Cell line	A498	Homo sapiens	GI50	n.a.	599.79	nM	PubChem BioAssay data set
NPT377	Cell line	OVCAR-3	Homo sapiens	GI50	n.a.	521.19	nM	PubChem BioAssay data set
NPT112	Cell line	MOLT-4	Homo sapiens	GI50	n.a.	139.96	nM	PubChem BioAssay data set
NPT378	Cell line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	1671.09	nM	PubChem BioAssay data set
NPT379	Cell line	HOP-62	Homo sapiens	GI50	n.a.	100.0	nM	PubChem BioAssay data set
NPT380	Cell line	U-251	Homo sapiens	GI50	n.a.	100.0	nM	PubChem BioAssay data set
NPT381	Cell line	OVCAR-8	Homo sapiens	GI50	n.a.	132.13	nM	PubChem BioAssay data set
NPT382	Cell line	OVCAR-5	Homo sapiens	GI50	n.a.	416.87	nM	PubChem BioAssay data set
NPT82	Cell line	MDA-MB-231	Homo sapiens	GI50	n.a.	6011.74	nM	PubChem BioAssay data set
NPT383	Cell line	SNB-19	Homo sapiens	GI50	n.a.	100.0	nM	PubChem BioAssay data set
NPT572	Cell line	DMS-273	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT385	Cell line	SR	Homo sapiens	GI50	n.a.	100.0	nM	PubChem BioAssay data set
NPT384	Cell line	TK-10	Homo sapiens	GI50	n.a.	3741.11	nM	PubChem BioAssay data set
NPT323	Cell line	SW-620	Homo sapiens	GI50	n.a.	196.34	nM	PubChem BioAssay data set
NPT573	Cell line	M19-MEL	Homo sapiens	GI50	n.a.	55.98	nM	PubChem BioAssay data set
NPT386	Cell line	KM12	Homo sapiens	GI50	n.a.	866.96	nM	PubChem BioAssay data set
NPT455	Cell line	NCI-H522	Homo sapiens	GI50	n.a.	144.88	nM	PubChem BioAssay data set
NPT387	Cell line	M14	Homo sapiens	GI50	n.a.	199.53	nM	PubChem BioAssay data set
NPT574	Cell line	XF498	Homo sapiens	GI50	n.a.	94.19	nM	PubChem BioAssay data set
NPT388	Cell line	NCI-H322M	Homo sapiens	GI50	n.a.	794.33	nM	PubChem BioAssay data set
NPT389	Cell line	RPMI-8226	Homo sapiens	GI50	n.a.	15.81	nM	PubChem BioAssay data set
NPT456	Cell line	OVCAR-4	Homo sapiens	GI50	n.a.	1059.25	nM	PubChem BioAssay data set
NPT390	Cell line	LOX IMVI	Homo sapiens	GI50	n.a.	100.0	nM	PubChem BioAssay data set
NPT457	Cell line	BT-549	Homo sapiens	GI50	n.a.	4943.11	nM	PubChem BioAssay data set
NPT147	Cell line	SK-MEL-2	Homo sapiens	GI50	n.a.	833.68	nM	PubChem BioAssay data set
NPT575	Cell line	KM-20L2	Homo sapiens	GI50	n.a.	62.23	nM	PubChem BioAssay data set
NPT391	Cell line	HCC 2998	Homo sapiens	GI50	n.a.	3845.92	nM	PubChem BioAssay data set
NPT81	Cell line	A549	Homo sapiens	GI50	n.a.	115.88	nM	PubChem BioAssay data set
NPT392	Cell line	SNB-75	Homo sapiens	GI50	n.a.	62.23	nM	PubChem BioAssay data set
NPT393	Cell line	HCT-116	Homo sapiens	GI50	n.a.	134.28	nM	PubChem BioAssay data set
NPT148	Cell line	HCT-15	Homo sapiens	GI50	n.a.	805.38	nM	PubChem BioAssay data set
NPT394	Cell line	EKVX	Homo sapiens	GI50	n.a.	2041.74	nM	PubChem BioAssay data set
NPT395	Cell line	SF-268	Homo sapiens	GI50	n.a.	100.0	nM	PubChem BioAssay data set
NPT306	Cell line	PC-3	Homo sapiens	GI50	n.a.	1531.09	nM	PubChem BioAssay data set
NPT83	Cell line	MCF7	Homo sapiens	GI50	n.a.	1000.0	nM	PubChem BioAssay data set
NPT731	Cell line	LXFL 529	Homo sapiens	GI50	n.a.	492.04	nM	PubChem BioAssay data set
NPT576	Cell line	DMS-114	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT146	Cell line	SK-OV-3	Homo sapiens	GI50	n.a.	117.22	nM	PubChem BioAssay data set
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	n.a.	100.0	nM	PubChem BioAssay data set
NPT396	Cell line	T47D	Homo sapiens	GI50	n.a.	19.45	nM	PubChem BioAssay data set
NPT398	Cell line	UACC-62	Homo sapiens	GI50	n.a.	100.0	nM	PubChem BioAssay data set
NPT308	Cell line	CAKI-1	Homo sapiens	GI50	n.a.	100.0	nM	PubChem BioAssay data set
NPT399	Cell line	SF-295	Homo sapiens	GI50	n.a.	100.0	nM	PubChem BioAssay data set
NPT400	Cell line	MDA-MB-435	Homo sapiens	GI50	n.a.	233.35	nM	PubChem BioAssay data set
NPT458	Cell line	IGROV-1	Homo sapiens	GI50	n.a.	466.66	nM	PubChem BioAssay data set
NPT577	Cell line	RXF 631	Homo sapiens	GI50	n.a.	62.81	nM	PubChem BioAssay data set
NPT401	Cell line	786-0	Homo sapiens	GI50	n.a.	210.86	nM	PubChem BioAssay data set
NPT402	Cell line	Hs-578T	Homo sapiens	GI50	n.a.	12764.39	nM	PubChem BioAssay data set
NPT403	Cell line	UACC-257	Homo sapiens	GI50	n.a.	558.47	nM	PubChem BioAssay data set
NPT578	Cell line	SNB-78	Homo sapiens	GI50	n.a.	1071.52	nM	PubChem BioAssay data set
NPT404	Cell line	CCRF-CEM	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT579	Cell line	DLD-1	Homo sapiens	GI50	n.a.	269.77	nM	PubChem BioAssay data set
NPT139	Cell line	HT-29	Homo sapiens	GI50	n.a.	404.58	nM	PubChem BioAssay data set
NPT405	Cell line	NCI-H226	Homo sapiens	GI50	n.a.	266.69	nM	PubChem BioAssay data set
NPT170	Cell line	SK-MEL-28	Homo sapiens	GI50	n.a.	1244.51	nM	PubChem BioAssay data set
NPT406	Cell line	RXF 393	Homo sapiens	GI50	n.a.	307.61	nM	PubChem BioAssay data set
NPT407	Cell line	COLO 205	Homo sapiens	GI50	n.a.	1207.81	nM	PubChem BioAssay data set
NPT732	Cell line	HOP-18	Homo sapiens	GI50	n.a.	42.46	nM	PubChem BioAssay data set

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 NPC128115 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	16327
0.1-0.2	32364
0.2-0.3	1153
0.3-0.4	2
0.4-0.5	3
0.5-0.6	3
0.6-0.7	3
0.7-0.8	2
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
0.76	Intermediate Similarity	NPC608071
0.7467	Intermediate Similarity	NPC129909
0.7273	Intermediate Similarity	NPC192674
0.675	Remote Similarity	NPC316181
0.675	Remote Similarity	NPC151781
0.6353	Remote Similarity	NPC74562
0.5814	Remote Similarity	NPC276661
0.5176	Remote Similarity	NPC14325
0.5176	Remote Similarity	NPC28848

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC128115 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3028
0.1-0.2	6018
0.2-0.3	78
0.3-0.4	3
0.4-0.5	7
0.5-0.6	9
0.6-0.7	4
0.7-0.8	2
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
0.7467	Intermediate Similarity	NPD3785	Pre-clinical
0.7273	Intermediate Similarity	NPD3800	Phase 2
0.6914	Remote Similarity	NPD3777	Phase 3
0.6395	Remote Similarity	NPD5507	Phase 4
0.6322	Remote Similarity	NPD5506	Approved
0.622	Remote Similarity	NPD4334	Discontinued
0.5977	Remote Similarity	NPD6261	Phase 2
0.5814	Remote Similarity	NPD4897	Phase 2
0.5714	Remote Similarity	NPD6206	Phase 2
0.5714	Remote Similarity	NPD6249	Phase 3
0.5652	Remote Similarity	NPD6248	Phase 2
0.5474	Remote Similarity	NPD5487	Phase 1
0.5455	Remote Similarity	NPD4315	Phase 2
0.5152	Remote Similarity	NPD7025	Phase 2
0.5104	Remote Similarity	NPD5835	Phase 3

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