NPASS Compound

Structure

CID158784 OpenBabel06191715532D 36 39 0 0 1 0 0 0 0 0999 V2000 -9.5263 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 29 1 0 0 0 0 4 29 1 0 0 0 0 6 35 1 0 0 0 0 7 10 1 0 0 0 0 7 17 2 0 0 0 0 8 9 2 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 21 1 0 0 0 0 11 18 2 0 0 0 0 11 20 1 0 0 0 0 12 19 2 0 0 0 0 12 22 1 0 0 0 0 13 19 1 0 0 0 0 13 23 2 0 0 0 0 14 18 1 0 0 0 0 14 25 2 0 0 0 0 15 20 1 0 0 0 0 15 26 1 0 0 0 0 16 24 1 0 0 0 0 16 30 1 0 0 0 0 20 27 2 0 0 0 0 21 22 2 0 0 0 0 21 23 1 0 0 0 0 22 31 1 0 0 0 0 23 32 1 0 0 0 0 24 28 1 0 0 0 0 24 33 1 1 0 0 0 25 27 1 0 0 0 0 25 35 1 0 0 0 0 26 29 1 0 0 0 0 26 30 1 1 0 0 0 27 36 1 0 0 0 0 28 29 1 0 0 0 0 28 34 1 1 0 0 0 30 5 1 1 0 0 0 30 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	494.27
Volume:	524.86
LogP:	5.772
LogD:	4.105
LogS:	-3.136
# Rotatable Bonds:	5
TPSA:	99.38
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.335
Synthetic Accessibility Score:	4.364
Fsp3:	0.467
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.048
MDCK Permeability:	1.1541114872670732e-05
Pgp-inhibitor:	0.985
Pgp-substrate:	0.935
Human Intestinal Absorption (HIA):	0.06
20% Bioavailability (F20%):	0.992
30% Bioavailability (F30%):	0.421

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.05
Plasma Protein Binding (PPB):	97.34381103515625%
Volume Distribution (VD):	0.729
Pgp-substrate:	4.295896530151367%

ADMET: Metabolism

CYP1A2-inhibitor:	0.363
CYP1A2-substrate:	0.452
CYP2C19-inhibitor:	0.196
CYP2C19-substrate:	0.101
CYP2C9-inhibitor:	0.504
CYP2C9-substrate:	0.902
CYP2D6-inhibitor:	0.324
CYP2D6-substrate:	0.263
CYP3A4-inhibitor:	0.228
CYP3A4-substrate:	0.227

ADMET: Excretion

Clearance (CL):	9.796
Half-life (T1/2):	0.259

ADMET: Toxicity

hERG Blockers:	0.603
Human Hepatotoxicity (H-HT):	0.596
Drug-inuced Liver Injury (DILI):	0.279
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.273
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.923
Carcinogencity:	0.025
Eye Corrosion:	0.003
Eye Irritation:	0.129
Respiratory Toxicity:	0.768

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC158784

Natural Product ID:	NPC158784
*Common Name:**	Schweinfurthin E
IUPAC Name:	(2S,3R,4aR,9aR)-7-[(E)-2-[3,5-dihydroxy-4-(3-methylbut-2-enyl)phenyl]ethenyl]-5-methoxy-1,1,4a-trimethyl-3,4,9,9a-tetrahydro-2H-xanthene-2,3-diol
Synonyms:	Schweinfurthin E
Standard InCHIKey:	IYHZCJNEODJYKB-DMCZWXATSA-N
Standard InCHI:	InChI=1S/C30H38O6/c1-17(2)7-10-21-22(31)12-19(13-23(21)32)9-8-18-11-20-15-26-29(3,4)28(34)24(33)16-30(26,5)36-27(20)25(14-18)35-6/h7-9,11-14,24,26,28,31-34H,10,15-16H2,1-6H3/b9-8+/t24-,26-,28-,30-/m1/s1
SMILES:	CC(=CCc1c(cc(/C=C/c2cc3C[C@@H]4C(C)(C)[C@@H]([C@@H](C[C@@]4(C)Oc3c(c2)OC)O)O)cc1O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL220472
PubChem CID:	16116472
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO27255	Macaranga alnifolia	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/0031-9422(92)80315-6]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11421757]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15974621]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	leaves	Krachong waterfall area, Trang Province, Thailand	2001-APR	PMID[15974621]
NPO27255	Macaranga alnifolia	Species	Euphorbiaceae	Eukaryota	n.a.	Madagascar rainforest	n.a.	PMID[17326683]
NPO27255	Macaranga alnifolia	Species	Euphorbiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[17326683]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[18844422]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18844422]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28972755]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27255	Macaranga alnifolia	Species	Euphorbiaceae	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	NP ID	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
EC50	2
GI50	58
IC50	1
Others	103

Activity Type	# Activity
Cell Line	161
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	=	3715.35	nM	PMID[473001]
NPT571	Cell Line	A2780cisR	Homo sapiens	IC50	=	260.0	nM	PMID[473001]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	=	2200.0	nM	PMID[473001]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	=	2200.0	nM	PMID[473001]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	=	2200.0	nM	PMID[473001]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	=	2200.0	nM	PMID[473001]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	<	10.0	nM	PMID[473001]
NPT112	Cell Line	MOLT-4	Homo sapiens	TGI	<	10.0	nM	PMID[473001]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	<	10.0	nM	PMID[473001]
NPT399	Cell Line	SF-295	Homo sapiens	TGI	<	10.0	nM	PMID[473001]
NPT376	Cell Line	A498	Homo sapiens	GI50	<	10.0	nM	PMID[473001]
NPT376	Cell Line	A498	Homo sapiens	TGI	<	10.0	nM	PMID[473001]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	<	10.0	nM	PMID[473001]
NPT308	Cell Line	CAKI-1	Homo sapiens	TGI	<	10.0	nM	PMID[473001]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	=	2137.96	nM	PMID[473001]
NPT81	Cell Line	A549	Homo sapiens	GI50	>	10.0	nM	PMID[473001]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	>	10.0	nM	PMID[473001]
NPT111	Cell Line	K562	Homo sapiens	GI50	>	10.0	nM	PMID[473001]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	>	10.0	nM	PMID[473001]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	>	10.0	nM	PMID[473001]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	>	10.0	nM	PMID[473001]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	LC50	>	100000.0	nM	PMID[473001]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	TGI	=	10000.0	nM	PMID[473001]
NPT111	Cell Line	K562	Homo sapiens	TGI	=	691.83	nM	PMID[473001]
NPT112	Cell Line	MOLT-4	Homo sapiens	LC50	>	100000.0	nM	PMID[473001]
NPT389	Cell Line	RPMI-8226	Homo sapiens	LC50	>	100000.0	nM	PMID[473001]
NPT389	Cell Line	RPMI-8226	Homo sapiens	TGI	=	52.48	nM	PMID[473001]
NPT81	Cell Line	A549	Homo sapiens	TGI	=	12589.25	nM	PMID[473001]
NPT81	Cell Line	A549	Homo sapiens	LC50	>	100000.0	nM	PMID[473001]
NPT394	Cell Line	EKVX	Homo sapiens	TGI	=	28183.83	nM	PMID[473001]
NPT394	Cell Line	EKVX	Homo sapiens	LC50	>	100000.0	nM	PMID[473001]
NPT391	Cell Line	HCC 2998	Homo sapiens	LC50	=	6456.54	nM	PMID[473001]
NPT379	Cell Line	HOP-62	Homo sapiens	TGI	=	75.86	nM	PMID[473001]
NPT379	Cell Line	HOP-62	Homo sapiens	LC50	=	7762.47	nM	PMID[473001]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	=	794.33	nM	PMID[473001]
NPT372	Cell Line	HOP-92	Homo sapiens	TGI	=	5128.61	nM	PMID[473001]
NPT372	Cell Line	HOP-92	Homo sapiens	LC50	>	100000.0	nM	PMID[473001]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	=	239.88	nM	PMID[473001]
NPT370	Cell Line	NCI-H23	Homo sapiens	TGI	=	2344.23	nM	PMID[473001]
NPT370	Cell Line	NCI-H23	Homo sapiens	LC50	=	13803.84	nM	PMID[473001]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	=	288.4	nM	PMID[473001]
NPT388	Cell Line	NCI-H322M	Homo sapiens	TGI	=	2238.72	nM	PMID[473001]
NPT388	Cell Line	NCI-H322M	Homo sapiens	LC50	=	13803.84	nM	PMID[473001]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	151.36	nM	PMID[473001]
NPT397	Cell Line	NCI-H460	Homo sapiens	TGI	>	100000.0	nM	PMID[473001]
NPT397	Cell Line	NCI-H460	Homo sapiens	LC50	>	100000.0	nM	PMID[473001]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	=	1995.26	nM	PMID[473001]
NPT455	Cell Line	NCI-H522	Homo sapiens	TGI	>	100000.0	nM	PMID[473001]
NPT455	Cell Line	NCI-H522	Homo sapiens	LC50	>	100000.0	nM	PMID[473001]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	=	1023.29	nM	PMID[473001]
NPT391	Cell Line	HCC 2998	Homo sapiens	TGI	=	2570.4	nM	PMID[473001]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	=	20.89	nM	PMID[473001]
NPT393	Cell Line	HCT-116	Homo sapiens	TGI	=	870.96	nM	PMID[473001]
NPT393	Cell Line	HCT-116	Homo sapiens	LC50	=	6918.31	nM	PMID[473001]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	=	602.56	nM	PMID[473001]
NPT148	Cell Line	HCT-15	Homo sapiens	TGI	=	3630.78	nM	PMID[473001]
NPT148	Cell Line	HCT-15	Homo sapiens	LC50	=	26915.35	nM	PMID[473001]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	1288.25	nM	PMID[473001]
NPT139	Cell Line	HT-29	Homo sapiens	LC50	>	100000.0	nM	PMID[473001]
NPT386	Cell Line	KM12	Homo sapiens	GI50	=	457.09	nM	PMID[473001]
NPT386	Cell Line	KM12	Homo sapiens	TGI	=	2238.72	nM	PMID[473001]
NPT386	Cell Line	KM12	Homo sapiens	LC50	=	9549.93	nM	PMID[473001]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	=	109.65	nM	PMID[473001]
NPT323	Cell Line	SW-620	Homo sapiens	TGI	=	2041.74	nM	PMID[473001]
NPT323	Cell Line	SW-620	Homo sapiens	LC50	>	100000.0	nM	PMID[473001]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	2630.27	nM	PMID[473001]
NPT395	Cell Line	SF-268	Homo sapiens	TGI	>	100000.0	nM	PMID[473001]
NPT395	Cell Line	SF-268	Homo sapiens	LC50	>	100000.0	nM	PMID[473001]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	>	10.0	nM	PMID[473001]
NPT399	Cell Line	SF-295	Homo sapiens	LC50	<	10.0	nM	PMID[473001]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	>	10.0	nM	PMID[473001]
NPT374	Cell Line	SF-539	Homo sapiens	TGI	=	158.49	nM	PMID[473001]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	=	10964.78	nM	PMID[473001]
NPT383	Cell Line	SNB-19	Homo sapiens	TGI	>	100000.0	nM	PMID[473001]
NPT383	Cell Line	SNB-19	Homo sapiens	LC50	>	100000.0	nM	PMID[473001]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	=	1737.8	nM	PMID[473001]
NPT392	Cell Line	SNB-75	Homo sapiens	TGI	=	19952.62	nM	PMID[473001]
NPT392	Cell Line	SNB-75	Homo sapiens	LC50	>	100000.0	nM	PMID[473001]
NPT380	Cell Line	U-251	Homo sapiens	GI50	>	10.0	nM	PMID[473001]
NPT380	Cell Line	U-251	Homo sapiens	TGI	=	3981.07	nM	PMID[473001]
NPT380	Cell Line	U-251	Homo sapiens	LC50	=	32359.37	nM	PMID[473001]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	=	645.65	nM	PMID[473001]
NPT390	Cell Line	LOX IMVI	Homo sapiens	TGI	=	2344.23	nM	PMID[473001]
NPT390	Cell Line	LOX IMVI	Homo sapiens	LC50	=	6165.95	nM	PMID[473001]
NPT387	Cell Line	M14	Homo sapiens	GI50	>	10.0	nM	PMID[473001]
NPT387	Cell Line	M14	Homo sapiens	TGI	=	288.4	nM	PMID[473001]
NPT387	Cell Line	M14	Homo sapiens	LC50	=	4265.8	nM	PMID[473001]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	TGI	>	100000.0	nM	PMID[473001]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	LC50	>	100000.0	nM	PMID[473001]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	=	371.54	nM	PMID[473001]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	TGI	=	5248.07	nM	PMID[473001]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	LC50	>	100000.0	nM	PMID[473001]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	=	660.69	nM	PMID[473001]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	TGI	=	2238.72	nM	PMID[473001]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	LC50	=	5623.41	nM	PMID[473001]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	=	165.96	nM	PMID[473001]
NPT403	Cell Line	UACC-257	Homo sapiens	TGI	=	3630.78	nM	PMID[473001]
NPT403	Cell Line	UACC-257	Homo sapiens	LC50	=	37153.52	nM	PMID[473001]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	>	10.0	nM	PMID[473001]
NPT398	Cell Line	UACC-62	Homo sapiens	TGI	=	371.54	nM	PMID[473001]
NPT398	Cell Line	UACC-62	Homo sapiens	LC50	=	4073.8	nM	PMID[473001]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	=	6165.95	nM	PMID[473001]
NPT377	Cell Line	OVCAR-3	Homo sapiens	TGI	=	8317.64	nM	PMID[473001]
NPT377	Cell Line	OVCAR-3	Homo sapiens	LC50	=	23988.33	nM	PMID[473001]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	=	575.44	nM	PMID[473001]
NPT456	Cell Line	OVCAR-4	Homo sapiens	TGI	=	9332.54	nM	PMID[473001]
NPT456	Cell Line	OVCAR-4	Homo sapiens	LC50	>	100000.0	nM	PMID[473001]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	=	2511.89	nM	PMID[473001]
NPT381	Cell Line	OVCAR-8	Homo sapiens	TGI	=	6760.83	nM	PMID[473001]
NPT381	Cell Line	OVCAR-8	Homo sapiens	LC50	>	100000.0	nM	PMID[473001]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	=	2754.23	nM	PMID[473001]
NPT146	Cell Line	SK-OV-3	Homo sapiens	TGI	=	10964.78	nM	PMID[473001]
NPT146	Cell Line	SK-OV-3	Homo sapiens	LC50	=	93325.43	nM	PMID[473001]
NPT401	Cell Line	786-0	Homo sapiens	GI50	>	10.0	nM	PMID[473001]
NPT401	Cell Line	786-0	Homo sapiens	TGI	=	1071.52	nM	PMID[473001]
NPT401	Cell Line	786-0	Homo sapiens	LC50	=	9772.37	nM	PMID[473001]
NPT376	Cell Line	A498	Homo sapiens	GI50	>	10.0	nM	PMID[473001]
NPT376	Cell Line	A498	Homo sapiens	LC50	>	100000.0	nM	PMID[473001]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	=	371.54	nM	PMID[473001]
NPT369	Cell Line	ACHN	Homo sapiens	TGI	=	3019.95	nM	PMID[473001]
NPT369	Cell Line	ACHN	Homo sapiens	LC50	=	13182.57	nM	PMID[473001]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	>	10.0	nM	PMID[473001]
NPT308	Cell Line	CAKI-1	Homo sapiens	LC50	=	549.54	nM	PMID[473001]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	=	2089.3	nM	PMID[473001]
NPT368	Cell Line	SN12C	Homo sapiens	TGI	=	7585.78	nM	PMID[473001]
NPT368	Cell Line	SN12C	Homo sapiens	LC50	=	34673.69	nM	PMID[473001]
NPT384	Cell Line	TK-10	Homo sapiens	TGI	=	2630.27	nM	PMID[473001]
NPT384	Cell Line	TK-10	Homo sapiens	LC50	=	18620.87	nM	PMID[473001]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	=	104.71	nM	PMID[473001]
NPT371	Cell Line	UO-31	Homo sapiens	TGI	>	100000.0	nM	PMID[473001]
NPT371	Cell Line	UO-31	Homo sapiens	LC50	>	100000.0	nM	PMID[473001]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	=	138.04	nM	PMID[473001]
NPT306	Cell Line	PC-3	Homo sapiens	TGI	=	9549.93	nM	PMID[473001]
NPT306	Cell Line	PC-3	Homo sapiens	LC50	=	47863.01	nM	PMID[473001]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	=	467.74	nM	PMID[473001]
NPT90	Cell Line	DU-145	Homo sapiens	TGI	=	14125.38	nM	PMID[473001]
NPT90	Cell Line	DU-145	Homo sapiens	LC50	=	72443.6	nM	PMID[473001]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	61.66	nM	PMID[473001]
NPT83	Cell Line	MCF7	Homo sapiens	TGI	=	26915.35	nM	PMID[473001]
NPT83	Cell Line	MCF7	Homo sapiens	LC50	>	100000.0	nM	PMID[473001]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	=	2238.72	nM	PMID[473001]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	TGI	=	6606.93	nM	PMID[473001]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	LC50	=	50118.72	nM	PMID[473001]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	TGI	=	3467.37	nM	PMID[473001]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	851.14	nM	PMID[473001]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	LC50	=	26302.68	nM	PMID[473001]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	=	1513.56	nM	PMID[473001]
NPT457	Cell Line	BT-549	Homo sapiens	TGI	=	13182.57	nM	PMID[473001]
NPT457	Cell Line	BT-549	Homo sapiens	LC50	>	100000.0	nM	PMID[473001]
NPT396	Cell Line	T47D	Homo sapiens	GI50	=	3235.94	nM	PMID[473001]
NPT396	Cell Line	T47D	Homo sapiens	TGI	>	100000.0	nM	PMID[473001]
NPT396	Cell Line	T47D	Homo sapiens	LC50	>	100000.0	nM	PMID[473001]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	=	123.03	nM	PMID[473001]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	TGI	=	1949.84	nM	PMID[473001]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	LC50	=	8709.64	nM	PMID[473001]
NPT81	Cell Line	A549	Homo sapiens	EC50	=	260.0	nM	PMID[473002]
NPT1535	Cell Line	U-87 MG	Homo sapiens	EC50	=	200.0	nM	PMID[473002]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	>	10.0	nM	PMID[473001]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	TGI	=	363.08	nM	PMID[473001]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	LC50	>	100000.0	nM	PMID[473001]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC158784 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	498
0.1-0.2	1531
0.2-0.3	3665
0.3-0.4	8686
0.4-0.5	9827
0.5-0.6	4146
0.6-0.7	7305
0.7-0.8	5769
0.8-0.85	915
0.85-0.9	318
0.9-0.95	29
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.993	High Similarity	NPC302915
0.993	High Similarity	NPC2745
0.9861	High Similarity	NPC325860
0.9861	High Similarity	NPC157783
0.986	High Similarity	NPC195561
0.9859	High Similarity	NPC212142
0.9448	High Similarity	NPC473876
0.9379	High Similarity	NPC474397
0.9375	High Similarity	NPC90645
0.9375	High Similarity	NPC472457
0.9324	High Similarity	NPC160196
0.931	High Similarity	NPC233980
0.9306	High Similarity	NPC473845
0.9241	High Similarity	NPC469557
0.9231	High Similarity	NPC35216
0.92	High Similarity	NPC80918
0.92	High Similarity	NPC188578
0.9172	High Similarity	NPC473108
0.9172	High Similarity	NPC50250
0.9167	High Similarity	NPC2613
0.9167	High Similarity	NPC475891
0.9167	High Similarity	NPC59841
0.9167	High Similarity	NPC204347
0.9167	High Similarity	NPC323126
0.9116	High Similarity	NPC21776
0.9116	High Similarity	NPC101376
0.9116	High Similarity	NPC16269
0.9097	High Similarity	NPC471389
0.9097	High Similarity	NPC265075
0.9091	High Similarity	NPC260741
0.9091	High Similarity	NPC471388
0.9091	High Similarity	NPC70682
0.9085	High Similarity	NPC472800
0.906	High Similarity	NPC477612
0.9048	High Similarity	NPC260397
0.9041	High Similarity	NPC469795
0.9041	High Similarity	NPC280092
0.9041	High Similarity	NPC45257
0.9041	High Similarity	NPC63879
0.9041	High Similarity	NPC93323
0.9041	High Similarity	NPC12641
0.9028	High Similarity	NPC259519
0.9028	High Similarity	NPC198038
0.9014	High Similarity	NPC61946
0.8993	High Similarity	NPC211561
0.898	High Similarity	NPC221318
0.898	High Similarity	NPC181615
0.8973	High Similarity	NPC102044
0.8973	High Similarity	NPC85264
0.8973	High Similarity	NPC47633
0.8973	High Similarity	NPC474104
0.8973	High Similarity	NPC477616
0.8966	High Similarity	NPC87725
0.8966	High Similarity	NPC178054
0.8966	High Similarity	NPC263261
0.8958	High Similarity	NPC127218
0.8958	High Similarity	NPC245207
0.8958	High Similarity	NPC184613
0.8958	High Similarity	NPC32630
0.8958	High Similarity	NPC319647
0.8958	High Similarity	NPC25966
0.8951	High Similarity	NPC248727
0.8951	High Similarity	NPC162659
0.8951	High Similarity	NPC227503
0.8951	High Similarity	NPC173660
0.8951	High Similarity	NPC302701
0.8951	High Similarity	NPC470802
0.8951	High Similarity	NPC306441
0.8951	High Similarity	NPC270456
0.8951	High Similarity	NPC265433
0.8951	High Similarity	NPC269091
0.8951	High Similarity	NPC474639
0.8951	High Similarity	NPC16435
0.8951	High Similarity	NPC230734
0.8919	High Similarity	NPC471608
0.8919	High Similarity	NPC112251
0.8904	High Similarity	NPC107161
0.8897	High Similarity	NPC184797
0.8897	High Similarity	NPC266197
0.8897	High Similarity	NPC291101
0.8897	High Similarity	NPC27495
0.8897	High Similarity	NPC309124
0.8897	High Similarity	NPC234568
0.8889	High Similarity	NPC276490
0.8889	High Similarity	NPC211549
0.8889	High Similarity	NPC474282
0.8889	High Similarity	NPC477938
0.8889	High Similarity	NPC103976
0.8889	High Similarity	NPC326797
0.8889	High Similarity	NPC102904
0.8889	High Similarity	NPC107551
0.8889	High Similarity	NPC176051
0.8881	High Similarity	NPC195022
0.8881	High Similarity	NPC164787
0.8881	High Similarity	NPC474206
0.8881	High Similarity	NPC112246
0.8881	High Similarity	NPC121812
0.8881	High Similarity	NPC151224
0.8881	High Similarity	NPC470356
0.8881	High Similarity	NPC94750
0.8881	High Similarity	NPC234333
0.8881	High Similarity	NPC260898
0.8881	High Similarity	NPC473413
0.8881	High Similarity	NPC112939
0.8881	High Similarity	NPC47398
0.8873	High Similarity	NPC263064
0.8859	High Similarity	NPC170103
0.8859	High Similarity	NPC204770
0.8859	High Similarity	NPC108811
0.8859	High Similarity	NPC236202
0.8859	High Similarity	NPC202742
0.8859	High Similarity	NPC82917
0.8859	High Similarity	NPC263940
0.8859	High Similarity	NPC70409
0.8859	High Similarity	NPC18185
0.8859	High Similarity	NPC58190
0.8859	High Similarity	NPC262911
0.8859	High Similarity	NPC294558
0.8844	High Similarity	NPC258083
0.8836	High Similarity	NPC71046
0.8836	High Similarity	NPC247291
0.8828	High Similarity	NPC232164
0.8828	High Similarity	NPC473739
0.8828	High Similarity	NPC6300
0.8828	High Similarity	NPC230124
0.8828	High Similarity	NPC236306
0.8828	High Similarity	NPC114171
0.8828	High Similarity	NPC475836
0.8828	High Similarity	NPC19869
0.8819	High Similarity	NPC327735
0.8819	High Similarity	NPC472334
0.8819	High Similarity	NPC68292
0.8819	High Similarity	NPC126101
0.8819	High Similarity	NPC472336
0.8819	High Similarity	NPC234952
0.8816	High Similarity	NPC21902
0.8811	High Similarity	NPC317380
0.8811	High Similarity	NPC478085
0.8808	High Similarity	NPC183380
0.8808	High Similarity	NPC469706
0.8808	High Similarity	NPC260781
0.8808	High Similarity	NPC218041
0.8808	High Similarity	NPC182368
0.8808	High Similarity	NPC145979
0.8808	High Similarity	NPC9933
0.8808	High Similarity	NPC469707
0.8808	High Similarity	NPC185955
0.8808	High Similarity	NPC225815
0.8808	High Similarity	NPC214326
0.88	High Similarity	NPC227516
0.88	High Similarity	NPC20757
0.8792	High Similarity	NPC324492
0.8792	High Similarity	NPC475872
0.8792	High Similarity	NPC96576
0.8792	High Similarity	NPC317053
0.8776	High Similarity	NPC186033
0.8776	High Similarity	NPC175838
0.8767	High Similarity	NPC34431
0.8767	High Similarity	NPC73505
0.8767	High Similarity	NPC308768
0.8767	High Similarity	NPC295719
0.8767	High Similarity	NPC254759
0.8767	High Similarity	NPC165026
0.8767	High Similarity	NPC160283
0.8767	High Similarity	NPC12668
0.8767	High Similarity	NPC22317
0.8759	High Similarity	NPC242715
0.8759	High Similarity	NPC266006
0.8759	High Similarity	NPC56329
0.8758	High Similarity	NPC78809
0.875	High Similarity	NPC327382
0.875	High Similarity	NPC313081
0.875	High Similarity	NPC472337
0.875	High Similarity	NPC256262
0.8742	High Similarity	NPC476969
0.8742	High Similarity	NPC44452
0.8741	High Similarity	NPC11060
0.8741	High Similarity	NPC92805
0.8741	High Similarity	NPC475840
0.8733	High Similarity	NPC327412
0.8733	High Similarity	NPC320970
0.8733	High Similarity	NPC328567
0.8733	High Similarity	NPC320671
0.8732	High Similarity	NPC103799
0.8716	High Similarity	NPC469630
0.8707	High Similarity	NPC311530
0.8701	High Similarity	NPC159922
0.8699	High Similarity	NPC220344
0.8699	High Similarity	NPC212942
0.8699	High Similarity	NPC292882
0.8699	High Similarity	NPC243996
0.8699	High Similarity	NPC105847
0.8699	High Similarity	NPC29868
0.8699	High Similarity	NPC22517
0.8699	High Similarity	NPC218131
0.8699	High Similarity	NPC243759
0.8699	High Similarity	NPC132804
0.8699	High Similarity	NPC79622
0.8699	High Similarity	NPC275061
0.8693	High Similarity	NPC226809

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC158784 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	396
0.1-0.2	866
0.2-0.3	1838
0.3-0.4	2708
0.4-0.5	1713
0.5-0.6	915
0.6-0.7	556
0.7-0.8	148
0.8-0.85	8
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8671	High Similarity	NPD1613	Approved
0.8671	High Similarity	NPD1612	Clinical (unspecified phase)
0.8531	High Similarity	NPD6410	Clinical (unspecified phase)
0.8531	High Similarity	NPD4907	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD3027	Phase 3
0.8456	Intermediate Similarity	NPD6674	Discontinued
0.8392	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8392	Intermediate Similarity	NPD4908	Phase 1
0.8333	Intermediate Similarity	NPD4625	Phase 3
0.8322	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD5844	Phase 1
0.8092	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD4749	Approved
0.8028	Intermediate Similarity	NPD1610	Phase 2
0.8	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD2861	Phase 2
0.7919	Intermediate Similarity	NPD3620	Phase 2
0.7919	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD7228	Approved
0.7895	Intermediate Similarity	NPD6100	Approved
0.7895	Intermediate Similarity	NPD6099	Approved
0.7888	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD37	Approved
0.7826	Intermediate Similarity	NPD1934	Approved
0.7805	Intermediate Similarity	NPD6234	Discontinued
0.7791	Intermediate Similarity	NPD4966	Approved
0.7791	Intermediate Similarity	NPD4967	Phase 2
0.7791	Intermediate Similarity	NPD4965	Approved
0.7784	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6166	Phase 2
0.7748	Intermediate Similarity	NPD5735	Approved
0.774	Intermediate Similarity	NPD8651	Approved
0.774	Intermediate Similarity	NPD6696	Suspended
0.7701	Intermediate Similarity	NPD4663	Approved
0.7692	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD1653	Approved
0.7683	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD4060	Phase 1
0.7657	Intermediate Similarity	NPD7906	Approved
0.7651	Intermediate Similarity	NPD5494	Approved
0.7633	Intermediate Similarity	NPD7473	Discontinued
0.7632	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD5124	Phase 1
0.7622	Intermediate Similarity	NPD1548	Phase 1
0.761	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD7199	Phase 2
0.7602	Intermediate Similarity	NPD7074	Phase 3
0.7561	Intermediate Similarity	NPD2801	Approved
0.756	Intermediate Similarity	NPD6232	Discontinued
0.756	Intermediate Similarity	NPD3051	Approved
0.7544	Intermediate Similarity	NPD7054	Approved
0.7529	Intermediate Similarity	NPD7311	Approved
0.7529	Intermediate Similarity	NPD4578	Approved
0.7529	Intermediate Similarity	NPD7310	Approved
0.7529	Intermediate Similarity	NPD7312	Approved
0.7529	Intermediate Similarity	NPD7313	Approved
0.7529	Intermediate Similarity	NPD4577	Approved
0.7515	Intermediate Similarity	NPD2970	Approved
0.7515	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD2969	Approved
0.7514	Intermediate Similarity	NPD7240	Approved
0.75	Intermediate Similarity	NPD8127	Discontinued
0.75	Intermediate Similarity	NPD7472	Approved
0.75	Intermediate Similarity	NPD6959	Discontinued
0.7486	Intermediate Similarity	NPD7309	Approved
0.7485	Intermediate Similarity	NPD4380	Phase 2
0.7471	Intermediate Similarity	NPD2489	Approved
0.7471	Intermediate Similarity	NPD7549	Discontinued
0.7471	Intermediate Similarity	NPD27	Approved
0.7467	Intermediate Similarity	NPD3018	Phase 2
0.7443	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD5327	Phase 3
0.7419	Intermediate Similarity	NPD4538	Approved
0.7419	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4536	Approved
0.7413	Intermediate Similarity	NPD6671	Approved
0.7413	Intermediate Similarity	NPD7157	Approved
0.7412	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD5283	Phase 1
0.7391	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7447	Phase 1
0.7389	Intermediate Similarity	NPD5762	Approved
0.7389	Intermediate Similarity	NPD5763	Approved
0.7371	Intermediate Similarity	NPD7808	Phase 3
0.7368	Intermediate Similarity	NPD7095	Approved
0.7361	Intermediate Similarity	NPD7340	Approved
0.7355	Intermediate Similarity	NPD6353	Approved
0.7355	Intermediate Similarity	NPD4097	Suspended
0.7353	Intermediate Similarity	NPD3787	Discontinued
0.7338	Intermediate Similarity	NPD4140	Approved
0.7333	Intermediate Similarity	NPD3094	Phase 2
0.7329	Intermediate Similarity	NPD7213	Phase 3
0.7329	Intermediate Similarity	NPD7212	Phase 2
0.7321	Intermediate Similarity	NPD7075	Discontinued
0.7321	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD2982	Phase 2
0.7315	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD2983	Phase 2
0.7314	Intermediate Similarity	NPD6559	Discontinued
0.7314	Intermediate Similarity	NPD7251	Discontinued
0.7297	Intermediate Similarity	NPD1091	Approved
0.7288	Intermediate Similarity	NPD8054	Approved
0.7288	Intermediate Similarity	NPD8053	Approved
0.7283	Intermediate Similarity	NPD3818	Discontinued
0.7278	Intermediate Similarity	NPD7266	Discontinued
0.7273	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5058	Phase 3
0.7262	Intermediate Similarity	NPD3882	Suspended
0.7261	Intermediate Similarity	NPD5588	Approved
0.7261	Intermediate Similarity	NPD5960	Phase 3
0.7257	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD6797	Phase 2
0.725	Intermediate Similarity	NPD4628	Phase 3
0.725	Intermediate Similarity	NPD7466	Approved
0.7248	Intermediate Similarity	NPD2981	Phase 2
0.7246	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD5929	Approved
0.7246	Intermediate Similarity	NPD7819	Suspended
0.7246	Intermediate Similarity	NPD8455	Phase 2
0.7246	Intermediate Similarity	NPD1465	Phase 2
0.7241	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6072	Discontinued
0.7229	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1511	Approved
0.7222	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7041	Phase 2
0.7219	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7831	Phase 2
0.7219	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7833	Phase 2
0.7212	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD3817	Phase 2
0.7197	Intermediate Similarity	NPD7097	Phase 1
0.7188	Intermediate Similarity	NPD5177	Phase 3
0.7188	Intermediate Similarity	NPD1652	Phase 2
0.7184	Intermediate Similarity	NPD3751	Discontinued
0.7181	Intermediate Similarity	NPD3092	Approved
0.7179	Intermediate Similarity	NPD3657	Discovery
0.7178	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7768	Phase 2
0.716	Intermediate Similarity	NPD7124	Phase 2
0.7153	Intermediate Similarity	NPD1398	Phase 1
0.7152	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7229	Phase 3
0.7151	Intermediate Similarity	NPD6071	Discontinued
0.7143	Intermediate Similarity	NPD3892	Phase 2
0.7143	Intermediate Similarity	NPD6331	Phase 2
0.7143	Intermediate Similarity	NPD7741	Discontinued
0.7143	Intermediate Similarity	NPD4110	Phase 3
0.7143	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD8312	Approved
0.7135	Intermediate Similarity	NPD8313	Approved
0.7134	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1512	Approved
0.7133	Intermediate Similarity	NPD228	Approved
0.7127	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD2424	Discontinued
0.7115	Intermediate Similarity	NPD2238	Phase 2
0.7108	Intermediate Similarity	NPD4005	Discontinued
0.7101	Intermediate Similarity	NPD2560	Approved
0.7101	Intermediate Similarity	NPD2563	Approved
0.7101	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2677	Approved
0.7097	Intermediate Similarity	NPD7985	Registered
0.7097	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7843	Approved
0.7073	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6355	Discontinued
0.7067	Intermediate Similarity	NPD3705	Approved
0.7066	Intermediate Similarity	NPD4675	Approved
0.7066	Intermediate Similarity	NPD6599	Discontinued
0.7066	Intermediate Similarity	NPD4678	Approved
0.7063	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4624	Approved
0.7047	Intermediate Similarity	NPD5125	Phase 3
0.7047	Intermediate Similarity	NPD5126	Approved
0.7045	Intermediate Similarity	NPD8156	Discontinued
0.7042	Intermediate Similarity	NPD2684	Approved
0.7037	Intermediate Similarity	NPD8166	Discontinued
0.7037	Intermediate Similarity	NPD7680	Approved
0.7037	Intermediate Similarity	NPD3750	Approved
0.7035	Intermediate Similarity	NPD4666	Phase 3
0.703	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3091	Approved
0.7024	Intermediate Similarity	NPD7411	Suspended
0.7021	Intermediate Similarity	NPD2494	Approved
0.7021	Intermediate Similarity	NPD2493	Approved
0.7019	Intermediate Similarity	NPD1549	Phase 2
0.7006	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1558	Phase 1
0.7	Intermediate Similarity	NPD4582	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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