NPASS Compound

Natural Product: NPC276661

Natural Product ID	NPC276661
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FJHBVJOVLFPMQE-QFIPXVFZSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	104842
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 49 53 0 0 0 0 0 0 0 0999 V2000 4.6449 -0.3606 -2.2718 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8694 0.7901 -1.6969 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0103 0.4254 -0.5659 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6155 0.2051 0.6785 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9799 0.3223 0.8457 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5233 0.0928 2.0952 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6734 -0.2486 3.1405 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3115 -0.3639 2.9671 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7522 -0.1338 1.7064 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4227 -0.2413 1.5113 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8365 -0.0282 0.3077 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5484 -0.0813 -0.1453 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7528 -0.3694 0.4944 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9382 -0.3446 -0.1997 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9316 -0.0329 -1.5341 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2022 0.0103 -2.3394 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1759 -0.8592 -1.8038 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2601 -1.0115 -0.4354 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3531 -1.4985 0.0054 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1914 -0.6535 0.5109 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5509 0.5570 1.3461 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8245 0.3634 2.1267 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9760 -1.7591 1.3502 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7248 0.2478 -2.1406 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7274 0.5347 -3.3736 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5606 0.2205 -1.4459 N 0 0 0 0 0 0 0 0 0 0 0 0 0.7697 0.4880 -1.9345 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6490 0.3120 -0.7511 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8894 0.2068 2.2759 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6541 -1.2592 -1.6387 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2815 -0.6781 -3.2773 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6894 0.0147 -2.4488 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5258 1.6412 -1.3669 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2237 1.1759 -2.5400 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6195 0.5943 -0.0100 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0894 -0.4265 4.1074 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6528 -0.6296 3.7803 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7638 -0.6159 1.5477 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9790 -0.3718 -3.3755 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5487 1.0407 -2.4074 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6830 0.8007 1.9708 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6699 1.4119 0.6195 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6406 0.8867 1.6074 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0440 -0.7038 2.2645 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6978 0.8895 3.1134 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2234 -2.5695 0.8453 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0625 -0.1599 -2.7861 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7624 1.5625 -2.2760 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4595 0.6066 1.5464 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 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 17 18 1 0 18 19 2 0 18 20 1 0 20 21 1 0 21 22 1 0 20 23 1 1 15 24 1 0 24 25 2 0 24 26 1 0 26 27 1 0 27 28 1 0 6 29 1 0 28 3 1 0 9 4 1 0 28 11 2 0 26 12 1 0 20 14 1 0 1 30 1 0 1 31 1 0 1 32 1 0 2 33 1 0 2 34 1 0 5 35 1 0 7 36 1 0 8 37 1 0 13 38 1 0 16 39 1 0 16 40 1 0 21 41 1 0 21 42 1 0 22 43 1 0 22 44 1 0 22 45 1 0 23 46 1 0 27 47 1 0 27 48 1 0 29 49 1 0 M END

Standard InCHIKey	FJHBVJOVLFPMQE-QFIPXVFZSA-N
Standard InCHI	InChI=1S/C22H20N2O5/c1-3-12-13-7-11(25)5-6-17(13)23-19-14(12)9-24-18(19)8-16-15(20(24)26)10-29-21(27)22(16,28)4-2/h5-8,25,28H,3-4,9-10H2,1-2H3/t22-/m0/s1
SMILES	CCc1c2cc(ccc2nc2-c3cc4c(COC(=O)[C@@]4(CC)O)c(=O)n3Cc12)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	392.14	Volume:	388.502 ? Van der Waals volume.
Dense:	1.009	LogP:	1.045 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.306 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.581 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	27.0
TPSA:	101.65 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.508	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.403	Fsp³:	0.318
MCE-18:	96.207 ? 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:	0.431	Fluc inhibitor:	0.322 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.993 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.395 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.005	Promiscuous compounds:	0.561

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.154	MDCK Permeability:	-4.794
Pgp-inhibitor:	0.001	Pgp-substrate:	0.996
PAMPA:	0.944 ? 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):	0.002
20% Bioavailability (F20%):	0.885	30% Bioavailability (F30%):	0.903
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.58	MRP1:	0.862
Plasma Protein Binding (PPB):	98.893%	Volume Distribution (VD):	-0.198
Fu:	0.619% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.863
OATP1B3 inhibitor:	0.491	BCRP inhibitor:	0.837
BSEP inhibitor:	0.646

ADMET: Metabolism

CYP1A2-inhibitor:	0.834	CYP1A2-substrate:	0.007
CYP2C19-inhibitor:	0.345	CYP2C19-substrate:	0.537
CYP2C9-inhibitor:	0.041	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.878
CYP3A4-inhibitor:	0.007	CYP3A4-substrate:	0.003
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.916
HLM stability:	0.995 ? 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):

6.822

Half-life (T1/2):

1.029

ADMET: Toxicity

hERG Blockers:	0.109	hERG Blockers (10um):	0.269
Human Hepatotoxicity (H-HT):	0.977	Drug-induced Liver Injury (DILI):	0.94
AMES Toxicity:	0.984	Rat Oral Acute Toxicity:	0.732
Maximum Recommended Daily Dose:	0.995	Skin Sensitization:	0.993
Carcinogencity:	0.991	Eye Corrosion:	0.0
Eye Irritation:	0.003	Respiratory Toxicity:	0.455
Drug-induced Neurotoxicity:	0.965	Ototoxicity:	0.773
Hematotoxicity:	0.959	Drug-induced Nephrotoxicity:	0.985
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.736
A549 Cytotoxicity:	0.845	Hek293 Cytotoxicity:	0.985
BCF:	1.273 ? 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:	4.167 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.071 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.904 ? 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
NPO25727	Tabernaemontana divaricata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23944995]
NPO25727	Tabernaemontana divaricata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26231157]
NPO25727	Tabernaemontana divaricata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30169038]
NPO25727	Tabernaemontana divaricata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25727	Tabernaemontana divaricata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25727	Tabernaemontana divaricata	Species	Apocynaceae	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
Activity	22
Ratio	5
CC50	1
IC50	139
Inhibition	15
EC50	2
Ki	1
Ratio IC50	6
GI50	23
IG50	1
Stability	1
pKa	1
IC50 relative	1

Activity Type	# Activity
Individual protein	22
Cell line	152
Organism	14
No target	4
Unchecked	2
Single protein	3
Non-molecular	13
Others	8

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT143	Individual protein	DNA topoisomerase I	Homo sapiens	Ratio	=	1.0	n.a.	PMID[9632364]
NPT143	Individual protein	DNA topoisomerase I	Homo sapiens	CC50	=	800.0	nM	PMID[1846923]
NPT204	Individual protein	Acetylcholinesterase	Homo sapiens	Inhibition	=	13.0	%	PMID[11334569]
NPT143	Individual protein	DNA topoisomerase I	Homo sapiens	EC50	=	320.0	nM	PMID[15454230]
NPT143	Individual protein	DNA topoisomerase I	Homo sapiens	EC50	=	70.0	nM	PMID[15454230]
NPT143	Individual protein	DNA topoisomerase I	Homo sapiens	IC50	=	5500.0	nM	PMID[19254843]
NPT109	Individual protein	Cytochrome P450 3A4	Homo sapiens	Ki	=	26000.0	nM	PMID[16248836]
NPT1422	Individual protein	ATP-binding cassette sub-family G member 2	Homo sapiens	Activity	=	40.0	%	PMID[12920197]
NPT1422	Individual protein	ATP-binding cassette sub-family G member 2	Homo sapiens	IC50	=	176.0	nM	PMID[15059881]
NPT143	Individual protein	DNA topoisomerase I	Homo sapiens	Inhibition	=	1.0	%	PMID[23578545]
NPT143	Individual protein	DNA topoisomerase I	Homo sapiens	IC50	=	1000.0	nM	PMID[33492141]
NPT73	Individual protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Activity	=	50.0	%	PMID[14977862]
NPT73	Individual protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Activity	=	50.0	%	PMID[15608127]
NPT73	Individual protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Activity	=	85.0	%	PMID[14977862]
NPT73	Individual protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Activity	=	85.0	%	PMID[15608127]
NPT20556	Single protein	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	25.05	%	DOI[10.6019/CHEMBL4495564]
NPT20556	Single protein	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	9.29	%	DOI[10.6019/CHEMBL4495564]
NPT20556	Single protein	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.04081	%	DOI[10.6019/CHEMBL4495564]
NPT692	Individual protein	Histone deacetylase 6	Homo sapiens	Inhibition	=	19.63	%	HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators
NPT692	Individual protein	Histone deacetylase 6	Homo sapiens	Inhibition	=	0.05	%	HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators
NPT901	Individual protein	UDP-glucuronosyltransferase 1-1	Homo sapiens	Inhibition	=	40.0	%	PMID[21030469]
NPT901	Individual protein	UDP-glucuronosyltransferase 1-1	Homo sapiens	IC50	=	360000.0	nM	PMID[21030469]
NPT604	Individual protein	Serum albumin	Homo sapiens	Activity	=	1.7	n.a.	PMID[8289200]
NPT604	Individual protein	Serum albumin	Homo sapiens	Activity	=	1.4	n.a.	PMID[8289200]
NPT4451	Individual protein	DNA topoisomerase I	Mus musculus	IC50	=	4000.0	nM	PMID[11334569]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell line	P388	Mus musculus	IC50	=	0.00144	ug.mL-1	PMID[9632364]
NPT4454	Cell line	HOC-21 cell line	n.a.	IC50	=	0.0412	ug.mL-1	PMID[9632364]
NPT3558	Cell line	QG-56	n.a.	IC50	=	0.0009	ug.mL-1	PMID[9632364]
NPT137	Cell line	L1210	Mus musculus	IC50	=	8.9	nM	PMID[1846923]
NPT1183	Cell line	WiDr	Homo sapiens	IC50	=	14.0	nM	PMID[11334569]
NPT81	Cell line	A549	Homo sapiens	IC50	=	16.0	nM	PMID[11334569]
NPT1097	Cell line	MKN-45	Homo sapiens	IC50	=	8.0	nM	PMID[11334569]
NPT146	Cell line	SK-OV-3	Homo sapiens	IC50	=	11.0	nM	PMID[11334569]
NPT2058	Cell line	NCI-H128	Homo sapiens	IC50	=	6.0	nM	PMID[11334569]
NPT134	Cell line	SK-BR-3	Homo sapiens	IC50	=	4.0	nM	PMID[11334569]
NPT168	Cell line	P388	Mus musculus	IC50	=	0.00693	ug.mL-1	PMID[7932525]
NPT4454	Cell line	HOC-21 cell line	n.a.	IC50	=	0.1231	ug.mL-1	PMID[7932525]
NPT3558	Cell line	QG-56	n.a.	IC50	=	0.00317	ug.mL-1	PMID[7932525]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	27.3	nM	PMID[12617927]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	22.0	nM	PMID[10498216]
NPT146	Cell line	SK-OV-3	Homo sapiens	IC50	=	720.0	nM	PMID[10498216]
NPT90	Cell line	DU-145	Homo sapiens	IC50	=	13.0	nM	PMID[10498216]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	370.0	nM	PMID[10498216]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	25.7	nM	PMID[15454230]
NPT306	Cell line	PC-3	Homo sapiens	IC50	=	35.6	nM	PMID[15454230]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	38.8	nM	PMID[15454230]
NPT306	Cell line	PC-3	Homo sapiens	IC50	=	35.3	nM	PMID[15454230]
NPT397	Cell line	NCI-H460	Homo sapiens	IC50	=	210.0	nM	PMID[15501036]
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	19.0	nM	PMID[15913996]
NPT181	Cell line	Bel-7402	Homo sapiens	IC50	=	13.0	nM	PMID[15913996]
NPT181	Cell line	Bel-7402	Homo sapiens	IC50	=	3190.0	nM	PMID[15808456]
NPT393	Cell line	HCT-116	Homo sapiens	IC50	=	7.0	nM	PMID[15808456]
NPT397	Cell line	NCI-H460	Homo sapiens	IC50	=	80.0	nM	PMID[16913706]
NPT90	Cell line	DU-145	Homo sapiens	IC50	=	4.0	nM	PMID[18276141]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	12.0	nM	PMID[18276141]
NPT397	Cell line	NCI-H460	Homo sapiens	IC50	=	220.0	nM	PMID[18424133]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	670.0	nM	PMID[18424133]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	11500.0	nM	PMID[18424133]
NPT139	Cell line	HT-29	Homo sapiens	Ratio IC50	=	17.0	n.a.	PMID[18424133]
NPT397	Cell line	NCI-H460	Homo sapiens	IC50	=	220.0	nM	PMID[18434153]
NPT393	Cell line	HCT-116	Homo sapiens	IC50	=	0.55	nM	PMID[19254843]
NPT3558	Cell line	QG-56	n.a.	IC50	=	2.8	nM	PMID[19254843]
NPT397	Cell line	NCI-H460	Homo sapiens	IC50	=	3.3	nM	PMID[19254843]
NPT3859	Cell line	PC-6	Homo sapiens	IC50	=	5.1	nM	PMID[19254843]
NPT3859	Cell line	PC-6	Homo sapiens	IC50	=	0.43	nM	PMID[19254843]
NPT3859	Cell line	PC-6	Homo sapiens	Ratio IC50	=	12.0	n.a.	PMID[19254843]
NPT397	Cell line	NCI-H460	Homo sapiens	IC50	=	130.0	nM	PMID[19530720]
NPT81	Cell line	A549	Homo sapiens	IC50	=	80.0	nM	PMID[18986807]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	120.0	nM	PMID[18986807]
NPT81	Cell line	A549	Homo sapiens	IC50	=	88.0	nM	PMID[19541483]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	170.0	nM	PMID[19541483]
NPT81	Cell line	A549	Homo sapiens	IC50	=	47.0	nM	PMID[21470864]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	5.9	nM	PMID[21470864]
NPT306	Cell line	PC-3	Homo sapiens	IC50	=	2.6	nM	PMID[22959246]
NPT179	Cell line	A2780	Homo sapiens	IC50	=	9.0	nM	PMID[22959246]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	30.0	nM	PMID[23578545]
NPT90	Cell line	DU-145	Homo sapiens	IC50	=	30.0	nM	PMID[23578545]
NPT137	Cell line	L1210	Mus musculus	IC50	=	40.0	nM	PMID[23578545]
NPT90	Cell line	DU-145	Homo sapiens	IC50	=	110.0	nM	PMID[23622981]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	106.67	nM	PMID[24529870]
NPT393	Cell line	HCT-116	Homo sapiens	IC50	=	31.0	nM	PMID[24529870]
NPT81	Cell line	A549	Homo sapiens	IC50	=	2.72	nM	PMID[24529870]
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	=	176.0	nM	PMID[24529870]
NPT393	Cell line	HCT-116	Homo sapiens	IC50	=	166.0	nM	PMID[24529870]
NPT81	Cell line	A549	Homo sapiens	IC50	=	259.0	nM	PMID[24529870]
NPT71	Cell line	HEK293	Homo sapiens	IG50	=	0.005	uM	PMID[25272055]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	18.54	nM	PMID[25835359]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	54.0	nM	PMID[27060760]
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	=	1970.0	nM	PMID[27060760]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	515.0	nM	PMID[27060760]
NPT380	Cell line	U-251	Homo sapiens	IC50	=	21.0	nM	PMID[27060760]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	3710.0	nM	PMID[28350997]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	2740.0	nM	PMID[28350997]
NPT397	Cell line	NCI-H460	Homo sapiens	Ratio IC50	=	0.83	n.a.	PMID[28350997]
NPT397	Cell line	NCI-H460	Homo sapiens	IC50	=	50.0	nM	PMID[28350997]
NPT397	Cell line	NCI-H460	Homo sapiens	IC50	=	60.0	nM	PMID[28350997]
NPT139	Cell line	HT-29	Homo sapiens	Ratio IC50	=	0.74	n.a.	PMID[28350997]
NPT397	Cell line	NCI-H460	Homo sapiens	IC50	=	50.0	nM	PMID[28740613]
NPT397	Cell line	NCI-H460	Homo sapiens	IC50	=	47.0	nM	PMID[28740613]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	96.0	nM	PMID[28740613]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	119.0	nM	PMID[28740613]
NPT139	Cell line	HT-29	Homo sapiens	Ratio IC50	=	0.82	n.a.	PMID[28740613]
NPT81	Cell line	A549	Homo sapiens	IC50	=	200.0	nM	PMID[30169038]
NPT83	Cell line	MCF7	Homo sapiens	IC50	<	0.1	nM	PMID[30169038]
NPT393	Cell line	HCT-116	Homo sapiens	IC50	=	0.78	nM	PMID[30115492]
NPT81	Cell line	A549	Homo sapiens	IC50	=	1.62	nM	PMID[30115492]
NPT83	Cell line	MCF7	Homo sapiens	GI50	=	3.0	nM	PMID[30553626]
NPT380	Cell line	U-251	Homo sapiens	GI50	=	2.8	nM	PMID[30553626]
NPT393	Cell line	HCT-116	Homo sapiens	GI50	=	23.0	nM	PMID[30553626]
NPT455	Cell line	NCI-H522	Homo sapiens	GI50	=	3.7	nM	PMID[30553626]
NPT390	Cell line	LOX IMVI	Homo sapiens	GI50	=	5.3	nM	PMID[30553626]
NPT146	Cell line	SK-OV-3	Homo sapiens	GI50	=	23.0	nM	PMID[30553626]
NPT369	Cell line	ACHN	Homo sapiens	GI50	=	5.9	nM	PMID[30553626]
NPT1179	Cell line	MKN-28	Homo sapiens	GI50	=	110.0	nM	PMID[30553626]
NPT90	Cell line	DU-145	Homo sapiens	GI50	=	4.3	nM	PMID[30553626]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	480.0	nM	PMID[30600208]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	1250.0	nM	PMID[30600208]
NPT81	Cell line	A549	Homo sapiens	IC50	=	11.0	nM	PMID[32352777]
NPT393	Cell line	HCT-116	Homo sapiens	IC50	=	4.0	nM	PMID[32352777]
NPT783	Cell line	MIA PaCa-2	Homo sapiens	IC50	=	13.0	nM	PMID[32352777]
NPT2309	Cell line	CAPAN-1	Homo sapiens	IC50	=	8.0	nM	PMID[32352777]
NPT81	Cell line	A549	Homo sapiens	IC50	=	6600.0	nM	PMID[30935798]
NPT393	Cell line	HCT-116	Homo sapiens	IC50	<	1000.0	nM	PMID[30935798]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	13100.0	nM	PMID[30935798]
NPT2174	Cell line	TE-8	Homo sapiens	IC50	<	1000.0	nM	PMID[30935798]
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	2400.0	nM	PMID[30935798]
NPT15	Cell line	Jurkat	Homo sapiens	IC50	<	1000.0	nM	PMID[30935798]
NPT71	Cell line	HEK293	Homo sapiens	IC50	<	1000.0	nM	PMID[30935798]
NPT171	Cell line	MRC5	Homo sapiens	IC50	=	15300.0	nM	PMID[30935798]
NPT139	Cell line	HT-29	Homo sapiens	Ratio	=	0.866	n.a.	PMID[27305384]
NPT139	Cell line	HT-29	Homo sapiens	Ratio	=	2.039	n.a.	PMID[27305384]
NPT139	Cell line	HT-29	Homo sapiens	Ratio	=	7.395	n.a.	PMID[27305384]
NPT1091	Cell line	RPMI-7951	Homo sapiens	IC50	=	260.0	nM	PMID[32435422]
NPT2344	Cell line	SK-MEL-24	Homo sapiens	IC50	=	480.0	nM	PMID[32435422]
NPT1086	Cell line	SK-HEP1	Homo sapiens	IC50	=	300.0	nM	PMID[32832017]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	300.0	nM	PMID[32832017]
NPT2245	Cell line	SiHa	Homo sapiens	IC50	=	300.0	nM	PMID[32832017]
NPT81	Cell line	A549	Homo sapiens	IC50	=	300.0	nM	PMID[32832017]
NPT81	Cell line	A549	Homo sapiens	IC50	=	18.0	nM	PMID[32650182]
NPT393	Cell line	HCT-116	Homo sapiens	IC50	=	10.0	nM	PMID[32650182]
NPT114	Cell line	LoVo	Homo sapiens	IC50	=	301.0	nM	PMID[32650182]
NPT407	Cell line	COLO 205	Homo sapiens	IC50	=	220.0	nM	PMID[32650182]
NPT80	Cell line	Raji	Homo sapiens	IC50	=	5.0	nM	PMID[32650182]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	145.0	nM	PMID[32650182]
NPT2341	Cell line	NCI-H1975	Homo sapiens	IC50	=	810.0	nM	PMID[32650182]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	2.81	%	PMID[32650182]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	2.91	%	PMID[32650182]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	8.29	%	PMID[32650182]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	3.11	%	PMID[32650182]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	7.12	%	PMID[32650182]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	24.42	%	PMID[32650182]
NPT82	Cell line	MDA-MB-231	Homo sapiens	GI50	=	512.0	nM	PMID[33492141]
NPT393	Cell line	HCT-116	Homo sapiens	GI50	=	20.0	nM	PMID[33492141]
NPT3467	Cell line	SJRH30	Homo sapiens	GI50	=	9.3	nM	PMID[33492141]
NPT376	Cell line	A498	Homo sapiens	GI50	=	220.0	nM	PMID[33492141]
NPT858	Cell line	LNCaP	Homo sapiens	GI50	=	12.2	nM	PMID[33492141]
NPT405	Cell line	NCI-H226	Homo sapiens	GI50	=	277.0	nM	PMID[33492141]
NPT81	Cell line	A549	Homo sapiens	IC50	=	28.0	nM	PMID[34048881]
NPT2615	Cell line	HEK-293T	Homo sapiens	IC50	=	14.2	nM	PMID[34963283]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	430.0	nM	PMID[37413981]
NPT81	Cell line	A549	Homo sapiens	IC50	=	3.8	nM	PMID[34963283]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	660.0	nM	PMID[34048881]
NPT407	Cell line	COLO 205	Homo sapiens	IC50	=	0.75	nM	PMID[37413981]
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	2.0	nM	PMID[34048881]
NPT65	Cell line	HepG2	Homo sapiens	IC50 relative	=	200.0	nM	ECBD screening data for assay EOS300108
NPT165	Cell line	HeLa	Homo sapiens	IC50	>	1000.0	nM	PMID[35059132]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	349.0	nM	PMID[35059132]
NPT393	Cell line	HCT-116	Homo sapiens	IC50	=	55.1	nM	PMID[32679451]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	20.0	nM	PMID[34048881]
NPT393	Cell line	HCT-116	Homo sapiens	IC50	=	54.93	nM	PMID[37413981]
NPT81	Cell line	A549	Homo sapiens	IC50	=	45.4	nM	PMID[32679451]
NPT81	Cell line	A549	Homo sapiens	IC50	=	11.9	nM	PMID[34963283]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-28.1	%	DOI[10.21203/rs.3.rs-23951/v1]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.02	%	DOI[10.6019/CHEMBL4495565]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.12	%	DOI[10.6019/CHEMBL4495565]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.08	%	DOI[10.6019/CHEMBL4495565]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	DOI[10.6019/CHEMBL4651402]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	DOI[10.6019/CHEMBL4651402]
NPT28833	No target	No relevant target	n.a.	Stability	n.a.	n.a.	%	PMID[38360419]
NPT28833	No target	No relevant target	n.a.	Activity	=	25.0	%	PMID[38360419]
NPT28833	No target	No relevant target	n.a.	pKa	=	9.2	n.a.	PMID[34963283]
NPT28833	No target	No relevant target	n.a.	Activity	~	25.0	%	PMID[38360419]
NPT28438	Unchecked	Unchecked	n.a.	GI50	=	1710.0	nM	PMID[29016119]
NPT28438	Unchecked	Unchecked	n.a.	GI50	=	86.0	nM	PMID[29016119]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	177.0	mg	PMID[11334569]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	27.0	mg	PMID[11334569]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	80.0	nM	PMID[11563925]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	6.0	nM	PMID[18276141]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	4.0	nM	PMID[19303306]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	46.0	nM	PMID[19303306]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	300.0	nM	PMID[19303306]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	GI50	=	66.0	nM	PMID[20884089]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	4.28	nM	PMID[25835359]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	30.0	nM	PMID[27060760]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	8.0	nM	PMID[27060760]
NPT20904	Cell line	Hep 3B2	Homo sapiens	GI50	=	177.0	nM	PMID[33492141]
NPT21742	Cell line	L02	Homo sapiens	IC50	=	18.0	nM	PMID[32352777]
NPT2	Others	Unspecified	n.a.	IC50	=	5.0	nM	PMID[11052802]
NPT2	Others	Unspecified	n.a.	IC50	=	50.0	nM	PMID[11052802]
NPT2	Others	Unspecified	n.a.	IC50	=	3.3	nM	PMID[15913996]
NPT2	Others	Unspecified	n.a.	IC50	=	22.0	nM	PMID[15913996]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	1.06	n.a.	PMID[28740613]
NPT2	Others	Unspecified	n.a.	IC50	=	510.0	nM	PMID[32435422]
NPT25892	Cell line	16HBE14o-	Homo sapiens	IC50	=	300.0	nM	PMID[32832017]
NPT24179	Cell line	MDCK-II	Canis lupus familiaris	GI50	=	139.0	nM	PMID[33454462]
NPT2	Others	Unspecified	n.a.	GI50	=	2830.0	nM	PMID[33492141]
NPT2	Others	Unspecified	n.a.	Ratio	=	142.0	n.a.	PMID[33492141]
NPT21740	Cell line	CCD-841CoN	Homo sapiens	IC50	=	4980.0	nM	PMID[34048881]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT605	Organism	Homo sapiens	Homo sapiens	Activity	=	13.0	%	PMID[8355258]
NPT605	Organism	Homo sapiens	Homo sapiens	Activity	=	38.0	%	PMID[8355258]
NPT605	Organism	Homo sapiens	Homo sapiens	Activity	=	24.0	%	PMID[8355258]
NPT605	Organism	Homo sapiens	Homo sapiens	Activity	=	1.7	n.a.	PMID[8355258]
NPT605	Organism	Homo sapiens	Homo sapiens	Activity	=	1.4	n.a.	PMID[8355258]

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 NPC276661 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	17897
0.1-0.2	31019
0.2-0.3	927
0.3-0.4	5
0.4-0.5	2
0.5-0.6	3
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
0.7436	Intermediate Similarity	NPC316181
0.7436	Intermediate Similarity	NPC151781
0.6988	Remote Similarity	NPC74562
0.6071	Remote Similarity	NPC192674
0.6024	Remote Similarity	NPC129909
0.596	Remote Similarity	NPC197381
0.5952	Remote Similarity	NPC608071
0.5814	Remote Similarity	NPC128115

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC276661 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3846
0.1-0.2	5232
0.2-0.3	48
0.3-0.4	3
0.4-0.5	3
0.5-0.6	6
0.6-0.7	10
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD4897	Phase 2
0.6988	Remote Similarity	NPD6261	Phase 2
0.6667	Remote Similarity	NPD6249	Phase 3
0.6591	Remote Similarity	NPD6248	Phase 2
0.6437	Remote Similarity	NPD5507	Phase 4
0.6364	Remote Similarity	NPD5506	Approved
0.6111	Remote Similarity	NPD6206	Phase 2
0.6071	Remote Similarity	NPD3800	Phase 2
0.6024	Remote Similarity	NPD3785	Pre-clinical
0.6022	Remote Similarity	NPD5487	Phase 1
0.6	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD5835	Phase 3
0.596	Remote Similarity	NPD7797	Phase 4
0.59	Remote Similarity	NPD7796	Approved
0.567	Remote Similarity	NPD5834	Phase 3
0.5618	Remote Similarity	NPD3777	Phase 3
0.5354	Remote Similarity	NPD7025	Phase 2

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