NPASS Compound

Structure

CID111323 OpenBabel06191715462D 37 40 0 0 1 0 0 0 0 0999 V2000 5.0858 -3.1738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1814 -2.8806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2974 3.8398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1512 3.3467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5027 0.4573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0231 -2.3562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6493 2.8540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8249 2.3784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3211 -1.7361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2510 -1.5378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2966 0.9502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6470 0.9516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8241 -0.4761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4733 2.3779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4731 1.4263 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1204 1.4258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6473 0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8246 1.4267 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6846 -1.0299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6484 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8244 -0.4756 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1206 2.3775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8876 -2.2440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2971 2.8536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6487 0.9506 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8249 -1.4263 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9744 0.9324 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5017 -0.4922 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9778 -0.1255 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5024 -0.4938 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9663 2.8652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8174 -2.0458 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1188 -2.0629 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 9 10 1 0 0 0 0 9 16 2 0 0 0 0 10 20 1 0 0 0 0 11 12 2 0 0 0 0 11 21 1 0 0 0 0 12 25 1 0 0 0 0 13 17 1 0 0 0 0 13 18 2 0 0 0 0 14 19 1 0 0 0 0 14 27 1 0 0 0 0 15 22 1 0 0 0 0 15 28 1 0 0 0 0 16 17 1 0 0 0 0 16 26 1 0 0 0 0 17 29 1 6 0 0 0 18 24 1 0 0 0 0 18 31 1 0 0 0 0 19 23 1 0 0 0 0 19 32 1 1 0 0 0 20 27 1 1 0 0 0 20 29 1 0 0 0 0 21 30 1 0 0 0 0 21 33 2 0 0 0 0 22 29 1 0 0 0 0 22 34 2 0 0 0 0 23 28 1 6 0 0 0 23 30 1 0 0 0 0 24 26 1 0 0 0 0 24 35 2 0 0 0 0 25 36 1 0 0 0 0 27 28 1 1 0 0 0 28 6 1 6 0 0 0 29 7 1 6 0 0 0 30 8 1 1 0 0 0 30 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	514.29
Volume:	538.923
LogP:	2.142
LogD:	2.344
LogS:	-4.395
# Rotatable Bonds:	4
TPSA:	128.97
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.299
Synthetic Accessibility Score:	5.526
Fsp3:	0.733
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.024
MDCK Permeability:	2.493041210982483e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.032
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.969
Plasma Protein Binding (PPB):	63.91881561279297%
Volume Distribution (VD):	0.407
Pgp-substrate:	22.60041618347168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.681
CYP2C19-inhibitor:	0.044
CYP2C19-substrate:	0.788
CYP2C9-inhibitor:	0.068
CYP2C9-substrate:	0.229
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.077
CYP3A4-inhibitor:	0.854
CYP3A4-substrate:	0.675

ADMET: Excretion

Clearance (CL):	4.11
Half-life (T1/2):	0.235

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.177
Drug-inuced Liver Injury (DILI):	0.086
AMES Toxicity:	0.055
Rat Oral Acute Toxicity:	0.476
Maximum Recommended Daily Dose:	0.439
Skin Sensitization:	0.245
Carcinogencity:	0.756
Eye Corrosion:	0.005
Eye Irritation:	0.016
Respiratory Toxicity:	0.885

Download Data

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

Natural Product: NPC111323

Natural Product ID:	NPC111323
*Common Name:**	Cucurbitacin I
IUPAC Name:	(8S,9R,10R,13R,14S,16R,17R)-17-[(E,2R)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,16-dihydroxy-4,4,9,13,14-pentamethyl-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthrene-3,11-dione
Synonyms:	NSC-521777
Standard InCHIKey:	NISPVUDLMHQFRQ-MKIKIEMVSA-N
Standard InCHI:	InChI=1S/C30H42O7/c1-25(2,36)12-11-21(33)30(8,37)23-19(32)14-27(5)20-10-9-16-17(13-18(31)24(35)26(16,3)4)29(20,7)22(34)15-28(23,27)6/h9,11-13,17,19-20,23,31-32,36-37H,10,14-15H2,1-8H3/b12-11+/t17-,19-,20+,23+,27+,28-,29+,30+/m1/s1
SMILES:	CC(C)(/C=C/C(=O)[C@@](C)([C@H]1[C@@H](C[C@@]2(C)[C@@H]3CC=C4[C@@H](C=C(C(=O)C4(C)C)O)[C@]3(C)C(=O)C[C@]12C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL387737
PubChem CID:	5281321
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001686] Cucurbitacins

*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
NPO40156	Hemsleya endecaphylla	Species	Cucurbitaceae	Eukaryota	Tubers	n.a.	n.a.	PMID[18088099]
NPO32449	eleaocarpus chinensis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22239601]
NPO21876	Trichosanthes cucumeroides	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33269591]
NPO32650	conobea scoparioides	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7852999]
NPO16511	Iberis amara	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21876	Trichosanthes cucumeroides	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16511	Iberis amara	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21876	Trichosanthes cucumeroides	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21876	Trichosanthes cucumeroides	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16511	Iberis amara	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21876	Trichosanthes cucumeroides	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16511	Iberis amara	Species	Brassicaceae	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	3
GI50	130
IC50	13
Others	12

Activity Type	# Activity
Cell Line	145
Individual Protein	1
NON-MOLECULAR	5
Organism	1
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1452	Cell Line	C8166	Homo sapiens	CC50	=	14.4	ug.mL-1	PMID[570171]
NPT4306	Cell Line	JY	Homo sapiens	Inhibition	=	34.0	%	PMID[570172]
NPT4306	Cell Line	JY	Homo sapiens	Inhibition	=	63.0	%	PMID[570172]
NPT4306	Cell Line	JY	Homo sapiens	Inhibition	=	58.0	%	PMID[570172]
NPT2536	Individual Protein	Leukocyte adhesion glycoprotein LFA-1 alpha	Homo sapiens	IC50	=	950.0	nM	PMID[570172]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	0.3	nM	PMID[570174]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	0.1	nM	PMID[570174]
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	=	0.47	nM	PMID[570174]
NPT65	Cell Line	HepG2	Homo sapiens	EC50	=	3160.0	nM	PMID[570175]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	15800.0	nM	PMID[570175]
NPT65	Cell Line	HepG2	Homo sapiens	Inhibition	=	74.0	%	PMID[570175]
NPT65	Cell Line	HepG2	Homo sapiens	Ratio IC50/EC50	=	5.0	n.a.	PMID[570175]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	40.0	%	PMID[570175]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	10.0	nM	PMID[570176]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	1901.08	nM	PMID[570176]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	430.53	nM	PMID[570177]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	1510.08	nM	PMID[570176]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	2376.84	nM	PMID[570176]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	267.92	nM	PMID[570177]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	1327.39	nM	PMID[570177]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	195.43	nM	PMID[570177]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	254.68	nM	PMID[570177]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	2415.46	nM	PMID[570176]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	683.91	nM	PMID[570176]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	265.46	nM	PMID[570177]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	549.54	nM	PMID[570176]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	874.98	nM	PMID[570176]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	253.51	nM	PMID[570177]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	10.0	nM	PMID[570176]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	1336.6	nM	PMID[570176]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	535.8	nM	PMID[570176]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	309.74	nM	PMID[570177]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	328.85	nM	PMID[570177]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	522.4	nM	PMID[570176]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	841.4	nM	PMID[570176]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	503.5	nM	PMID[570177]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	189.23	nM	PMID[570177]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	1879.32	nM	PMID[570176]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	395.37	nM	PMID[570177]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	1610.65	nM	PMID[570177]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	783.43	nM	PMID[570176]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	126.47	nM	PMID[570176]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	2685.34	nM	PMID[570176]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	442.59	nM	PMID[570177]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	228.56	nM	PMID[570177]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	1300.17	nM	PMID[570177]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	1256.03	nM	PMID[570176]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	3026.91	nM	PMID[570177]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	2128.14	nM	PMID[570176]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	3235.94	nM	PMID[570176]
NPT572	Cell Line	DMS-273	Homo sapiens	GI50	n.a.	243.22	nM	PMID[570177]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	22.28	nM	PMID[570176]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	1221.8	nM	PMID[570176]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	407.38	nM	PMID[570177]
NPT572	Cell Line	DMS-273	Homo sapiens	GI50	n.a.	217.77	nM	PMID[570176]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	644.17	nM	PMID[570176]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	1047.13	nM	PMID[570176]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	410.2	nM	PMID[570177]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	359.75	nM	PMID[570177]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	334.2	nM	PMID[570177]
NPT573	Cell Line	M19-MEL	Homo sapiens	GI50	n.a.	2786.12	nM	PMID[570176]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	540.75	nM	PMID[570176]
NPT573	Cell Line	M19-MEL	Homo sapiens	GI50	n.a.	928.97	nM	PMID[570177]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	1527.57	nM	PMID[570176]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	1896.71	nM	PMID[570176]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	1124.6	nM	PMID[570177]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	277.97	nM	PMID[570177]
NPT574	Cell Line	XF498	Homo sapiens	GI50	n.a.	283.79	nM	PMID[570177]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	548.28	nM	PMID[570176]
NPT574	Cell Line	XF498	Homo sapiens	GI50	n.a.	329.61	nM	PMID[570176]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	303.39	nM	PMID[570177]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	4216.97	nM	PMID[570176]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	281.19	nM	PMID[570176]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	3944.57	nM	PMID[570177]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	318.42	nM	PMID[570177]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	1729.82	nM	PMID[570176]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	429.54	nM	PMID[570176]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	304.79	nM	PMID[570177]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	238.23	nM	PMID[570177]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	14.69	nM	PMID[570176]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	441.57	nM	PMID[570176]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	n.a.	481.95	nM	PMID[570176]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	236.59	nM	PMID[570177]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	n.a.	318.42	nM	PMID[570177]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	1506.61	nM	PMID[570176]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	493.17	nM	PMID[570176]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	306.9	nM	PMID[570177]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	271.02	nM	PMID[570177]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	1520.55	nM	PMID[570176]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	72.11	nM	PMID[570177]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	630.96	nM	PMID[570176]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	363.08	nM	PMID[570177]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	609.54	nM	PMID[570176]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	272.9	nM	PMID[570177]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	974.99	nM	PMID[570177]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	475.34	nM	PMID[570176]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	251.19	nM	PMID[570177]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	1270.57	nM	PMID[570176]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	24.49	nM	PMID[570176]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	23.77	nM	PMID[570176]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	357.27	nM	PMID[570177]
NPT576	Cell Line	DMS-114	Homo sapiens	GI50	n.a.	1210.6	nM	PMID[570176]
NPT731	Cell Line	LXFL 529	Homo sapiens	GI50	n.a.	338.84	nM	PMID[570177]
NPT576	Cell Line	DMS-114	Homo sapiens	GI50	n.a.	698.23	nM	PMID[570177]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	933.25	nM	PMID[570176]
NPT731	Cell Line	LXFL 529	Homo sapiens	GI50	n.a.	512.86	nM	PMID[570176]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	287.74	nM	PMID[570177]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	103.75	nM	PMID[570176]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	543.25	nM	PMID[570176]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	805.38	nM	PMID[570176]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	606.74	nM	PMID[570177]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	217.27	nM	PMID[570177]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	10.0	nM	PMID[570176]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	435.51	nM	PMID[570176]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	269.77	nM	PMID[570177]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	939.72	nM	PMID[570176]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	274.79	nM	PMID[570177]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	1599.56	nM	PMID[570176]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	48.53	nM	PMID[570176]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	225.94	nM	PMID[570177]
NPT577	Cell Line	RXF 631	Homo sapiens	GI50	n.a.	372.39	nM	PMID[570177]
NPT577	Cell Line	RXF 631	Homo sapiens	GI50	n.a.	535.8	nM	PMID[570176]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	508.16	nM	PMID[570176]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	324.34	nM	PMID[570177]
NPT578	Cell Line	SNB-78	Homo sapiens	GI50	n.a.	303.39	nM	PMID[570177]
NPT578	Cell Line	SNB-78	Homo sapiens	GI50	n.a.	528.45	nM	PMID[570176]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	554.63	nM	PMID[570176]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	511.68	nM	PMID[570176]
NPT579	Cell Line	DLD-1	Homo sapiens	GI50	n.a.	291.07	nM	PMID[570177]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	252.93	nM	PMID[570177]
NPT579	Cell Line	DLD-1	Homo sapiens	GI50	n.a.	1116.86	nM	PMID[570176]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	538.27	nM	PMID[570176]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	1406.05	nM	PMID[570176]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	321.37	nM	PMID[570177]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	251.77	nM	PMID[570177]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	209.41	nM	PMID[570177]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	623.73	nM	PMID[570176]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	1786.49	nM	PMID[570176]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	224.91	nM	PMID[570177]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	306.2	nM	PMID[570177]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	439.54	nM	PMID[570176]
NPT732	Cell Line	HOP-18	Homo sapiens	GI50	n.a.	602.56	nM	PMID[570176]
NPT732	Cell Line	HOP-18	Homo sapiens	GI50	n.a.	275.42	nM	PMID[570177]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	190.0	nM	PMID[570178]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	60.7	nM	PMID[570179]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	140.0	nM	PMID[570180]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	0.7	ug.mL-1	PMID[570171]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	20.6	n.a.	PMID[570171]
NPT2	Others	Unspecified		Inhibition	=	20.5	%	PMID[570172]
NPT2	Others	Unspecified		Inhibition	=	15.3	%	PMID[570172]
NPT2	Others	Unspecified		Inhibition	=	60.5	%	PMID[570172]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	<	400.0	nM	PMID[570173]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	20.0	nM	PMID[570175]
NPT27	Others	Unspecified		IC50	=	3600.0	nM	PMID[570175]
NPT2	Others	Unspecified		Ratio IC50/EC50	=	150.0	n.a.	PMID[570175]

☑ 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 NPC111323 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	186
0.1-0.2	1129
0.2-0.3	4442
0.3-0.4	10319
0.4-0.5	11955
0.5-0.6	7743
0.6-0.7	5214
0.7-0.8	1470
0.8-0.85	196
0.85-0.9	36
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9688	High Similarity	NPC87351
0.9588	High Similarity	NPC311612
0.93	High Similarity	NPC185
0.9278	High Similarity	NPC474720
0.9263	High Similarity	NPC472932
0.9118	High Similarity	NPC214644
0.9038	High Similarity	NPC221144
0.898	High Similarity	NPC197386
0.89	High Similarity	NPC473424
0.8854	High Similarity	NPC472930
0.8824	High Similarity	NPC257353
0.8788	High Similarity	NPC147954
0.8776	High Similarity	NPC249954
0.8738	High Similarity	NPC43285
0.8738	High Similarity	NPC58370
0.8713	High Similarity	NPC204450
0.8713	High Similarity	NPC195290
0.87	High Similarity	NPC144956
0.8679	High Similarity	NPC100267
0.8679	High Similarity	NPC475524
0.8673	High Similarity	NPC259286
0.866	High Similarity	NPC472942
0.8654	High Similarity	NPC65941
0.8627	High Similarity	NPC236390
0.8627	High Similarity	NPC249187
0.8627	High Similarity	NPC247957
0.8614	High Similarity	NPC302537
0.8614	High Similarity	NPC163372
0.8611	High Similarity	NPC148458
0.86	High Similarity	NPC166745
0.86	High Similarity	NPC235464
0.8586	High Similarity	NPC49371
0.8571	High Similarity	NPC304495
0.8571	High Similarity	NPC470257
0.8544	High Similarity	NPC137657
0.8542	High Similarity	NPC310010
0.8542	High Similarity	NPC2983
0.8542	High Similarity	NPC123912
0.8542	High Similarity	NPC477943
0.8542	High Similarity	NPC326627
0.8532	High Similarity	NPC471854
0.8529	High Similarity	NPC308726
0.8529	High Similarity	NPC119601
0.8529	High Similarity	NPC477915
0.8515	High Similarity	NPC287833
0.85	High Similarity	NPC18509
0.8485	Intermediate Similarity	NPC174948
0.8485	Intermediate Similarity	NPC469995
0.8485	Intermediate Similarity	NPC318282
0.8485	Intermediate Similarity	NPC173875
0.8476	Intermediate Similarity	NPC295244
0.8469	Intermediate Similarity	NPC69454
0.8469	Intermediate Similarity	NPC474736
0.8469	Intermediate Similarity	NPC233118
0.8462	Intermediate Similarity	NPC149047
0.8454	Intermediate Similarity	NPC320026
0.8454	Intermediate Similarity	NPC69622
0.8426	Intermediate Similarity	NPC108721
0.8426	Intermediate Similarity	NPC73300
0.8416	Intermediate Similarity	NPC10364
0.84	Intermediate Similarity	NPC328371
0.84	Intermediate Similarity	NPC471463
0.8384	Intermediate Similarity	NPC8993
0.8381	Intermediate Similarity	NPC475060
0.8381	Intermediate Similarity	NPC83744
0.8381	Intermediate Similarity	NPC475294
0.8381	Intermediate Similarity	NPC472925
0.8381	Intermediate Similarity	NPC477916
0.8381	Intermediate Similarity	NPC220229
0.8367	Intermediate Similarity	NPC475806
0.8367	Intermediate Similarity	NPC63748
0.8365	Intermediate Similarity	NPC209502
0.8365	Intermediate Similarity	NPC235889
0.8365	Intermediate Similarity	NPC72255
0.8365	Intermediate Similarity	NPC204833
0.8364	Intermediate Similarity	NPC239273
0.8351	Intermediate Similarity	NPC76879
0.8333	Intermediate Similarity	NPC205899
0.8333	Intermediate Similarity	NPC154072
0.8333	Intermediate Similarity	NPC51370
0.8318	Intermediate Similarity	NPC37116
0.8317	Intermediate Similarity	NPC107243
0.8317	Intermediate Similarity	NPC18319
0.8316	Intermediate Similarity	NPC474083
0.8302	Intermediate Similarity	NPC329417
0.8302	Intermediate Similarity	NPC177064
0.8302	Intermediate Similarity	NPC217201
0.8288	Intermediate Similarity	NPC311554
0.8288	Intermediate Similarity	NPC257457
0.8286	Intermediate Similarity	NPC50692
0.8286	Intermediate Similarity	NPC49958
0.8286	Intermediate Similarity	NPC260268
0.8286	Intermediate Similarity	NPC302607
0.8286	Intermediate Similarity	NPC60681
0.8286	Intermediate Similarity	NPC476027
0.8286	Intermediate Similarity	NPC152695
0.8286	Intermediate Similarity	NPC48733
0.8286	Intermediate Similarity	NPC202167
0.8286	Intermediate Similarity	NPC296945
0.8286	Intermediate Similarity	NPC85829
0.8286	Intermediate Similarity	NPC171137
0.8286	Intermediate Similarity	NPC150531
0.8286	Intermediate Similarity	NPC214264
0.8286	Intermediate Similarity	NPC319077
0.8286	Intermediate Similarity	NPC97202
0.8286	Intermediate Similarity	NPC181265
0.8283	Intermediate Similarity	NPC474807
0.8283	Intermediate Similarity	NPC125180
0.8283	Intermediate Similarity	NPC250575
0.8283	Intermediate Similarity	NPC25750
0.8283	Intermediate Similarity	NPC243866
0.8269	Intermediate Similarity	NPC191892
0.8269	Intermediate Similarity	NPC26478
0.8265	Intermediate Similarity	NPC129913
0.8265	Intermediate Similarity	NPC48010
0.8252	Intermediate Similarity	NPC472924
0.8252	Intermediate Similarity	NPC476223
0.8252	Intermediate Similarity	NPC224720
0.8252	Intermediate Similarity	NPC476240
0.8252	Intermediate Similarity	NPC99411
0.8241	Intermediate Similarity	NPC43775
0.8241	Intermediate Similarity	NPC472928
0.8235	Intermediate Similarity	NPC471717
0.8229	Intermediate Similarity	NPC118648
0.8229	Intermediate Similarity	NPC469994
0.8229	Intermediate Similarity	NPC327115
0.8229	Intermediate Similarity	NPC475022
0.8229	Intermediate Similarity	NPC222613
0.8224	Intermediate Similarity	NPC11710
0.8224	Intermediate Similarity	NPC241927
0.8224	Intermediate Similarity	NPC258543
0.8218	Intermediate Similarity	NPC456
0.8218	Intermediate Similarity	NPC96859
0.8218	Intermediate Similarity	NPC305483
0.8218	Intermediate Similarity	NPC328162
0.8218	Intermediate Similarity	NPC155676
0.8218	Intermediate Similarity	NPC117133
0.8218	Intermediate Similarity	NPC472941
0.8211	Intermediate Similarity	NPC473246
0.8208	Intermediate Similarity	NPC91034
0.8208	Intermediate Similarity	NPC44063
0.82	Intermediate Similarity	NPC292793
0.8198	Intermediate Similarity	NPC472934
0.819	Intermediate Similarity	NPC152091
0.8182	Intermediate Similarity	NPC19114
0.8182	Intermediate Similarity	NPC473998
0.8182	Intermediate Similarity	NPC472978
0.8182	Intermediate Similarity	NPC168027
0.8182	Intermediate Similarity	NPC185936
0.8173	Intermediate Similarity	NPC185530
0.8173	Intermediate Similarity	NPC56498
0.8165	Intermediate Similarity	NPC191620
0.8163	Intermediate Similarity	NPC31985
0.8163	Intermediate Similarity	NPC474245
0.8163	Intermediate Similarity	NPC86319
0.8163	Intermediate Similarity	NPC473999
0.8163	Intermediate Similarity	NPC275740
0.8163	Intermediate Similarity	NPC309603
0.8163	Intermediate Similarity	NPC1015
0.8155	Intermediate Similarity	NPC327431
0.8155	Intermediate Similarity	NPC476274
0.8144	Intermediate Similarity	NPC317590
0.8144	Intermediate Similarity	NPC136548
0.8144	Intermediate Similarity	NPC58063
0.8137	Intermediate Similarity	NPC57416
0.8137	Intermediate Similarity	NPC43747
0.8125	Intermediate Similarity	NPC469948
0.8125	Intermediate Similarity	NPC471224
0.8125	Intermediate Similarity	NPC474218
0.8119	Intermediate Similarity	NPC271195
0.8119	Intermediate Similarity	NPC37646
0.8119	Intermediate Similarity	NPC180950
0.8119	Intermediate Similarity	NPC241156
0.81	Intermediate Similarity	NPC206810
0.8095	Intermediate Similarity	NPC251017
0.8095	Intermediate Similarity	NPC117185
0.8095	Intermediate Similarity	NPC55872
0.8091	Intermediate Similarity	NPC472929
0.8081	Intermediate Similarity	NPC171441
0.8077	Intermediate Similarity	NPC470184
0.8073	Intermediate Similarity	NPC231589
0.8073	Intermediate Similarity	NPC214797
0.8073	Intermediate Similarity	NPC118860
0.8061	Intermediate Similarity	NPC143767
0.8061	Intermediate Similarity	NPC131470
0.8061	Intermediate Similarity	NPC471722
0.8058	Intermediate Similarity	NPC103051
0.8056	Intermediate Similarity	NPC2766
0.8053	Intermediate Similarity	NPC472933
0.8041	Intermediate Similarity	NPC51014
0.8041	Intermediate Similarity	NPC474778
0.8041	Intermediate Similarity	NPC474733
0.8041	Intermediate Similarity	NPC472974
0.8041	Intermediate Similarity	NPC31564
0.8041	Intermediate Similarity	NPC145879
0.8041	Intermediate Similarity	NPC474732
0.8041	Intermediate Similarity	NPC20688
0.8041	Intermediate Similarity	NPC94666
0.8039	Intermediate Similarity	NPC40765
0.8039	Intermediate Similarity	NPC192428

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 NPC111323 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1425
0.2-0.3	3865
0.3-0.4	2532
0.4-0.5	684
0.5-0.6	187
0.6-0.7	138
0.7-0.8	119
0.8-0.85	33
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.89	High Similarity	NPD5211	Phase 2
0.8725	High Similarity	NPD5141	Approved
0.87	High Similarity	NPD5286	Approved
0.87	High Similarity	NPD4696	Approved
0.87	High Similarity	NPD5285	Approved
0.8673	High Similarity	NPD5210	Approved
0.8673	High Similarity	NPD4629	Approved
0.8542	High Similarity	NPD4753	Phase 2
0.8529	High Similarity	NPD5225	Approved
0.8529	High Similarity	NPD5224	Approved
0.8529	High Similarity	NPD4633	Approved
0.8529	High Similarity	NPD5226	Approved
0.85	High Similarity	NPD4755	Approved
0.8447	Intermediate Similarity	NPD5175	Approved
0.8447	Intermediate Similarity	NPD5174	Approved
0.8431	Intermediate Similarity	NPD5223	Approved
0.8421	Intermediate Similarity	NPD5690	Phase 2
0.8333	Intermediate Similarity	NPD4700	Approved
0.8302	Intermediate Similarity	NPD6881	Approved
0.8302	Intermediate Similarity	NPD6899	Approved
0.8241	Intermediate Similarity	NPD6649	Approved
0.8241	Intermediate Similarity	NPD6650	Approved
0.8218	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8218	Intermediate Similarity	NPD5221	Approved
0.8218	Intermediate Similarity	NPD5222	Approved
0.8208	Intermediate Similarity	NPD5697	Approved
0.8182	Intermediate Similarity	NPD6079	Approved
0.8148	Intermediate Similarity	NPD6883	Approved
0.8148	Intermediate Similarity	NPD7102	Approved
0.8148	Intermediate Similarity	NPD7290	Approved
0.8137	Intermediate Similarity	NPD6083	Phase 2
0.8137	Intermediate Similarity	NPD5173	Approved
0.8137	Intermediate Similarity	NPD6084	Phase 2
0.8131	Intermediate Similarity	NPD4730	Approved
0.8131	Intermediate Similarity	NPD4729	Approved
0.8125	Intermediate Similarity	NPD5329	Approved
0.8119	Intermediate Similarity	NPD5695	Phase 3
0.8113	Intermediate Similarity	NPD5739	Approved
0.8113	Intermediate Similarity	NPD6675	Approved
0.8113	Intermediate Similarity	NPD6402	Approved
0.8113	Intermediate Similarity	NPD7128	Approved
0.8073	Intermediate Similarity	NPD6847	Approved
0.8073	Intermediate Similarity	NPD6869	Approved
0.8073	Intermediate Similarity	NPD8130	Phase 1
0.8073	Intermediate Similarity	NPD6617	Approved
0.8056	Intermediate Similarity	NPD6372	Approved
0.8056	Intermediate Similarity	NPD6373	Approved
0.8056	Intermediate Similarity	NPD6012	Approved
0.8056	Intermediate Similarity	NPD6013	Approved
0.8056	Intermediate Similarity	NPD6014	Approved
0.8041	Intermediate Similarity	NPD4694	Approved
0.8041	Intermediate Similarity	NPD5279	Phase 3
0.8041	Intermediate Similarity	NPD5280	Approved
0.8039	Intermediate Similarity	NPD4697	Phase 3
0.8021	Intermediate Similarity	NPD3133	Approved
0.8021	Intermediate Similarity	NPD3665	Phase 1
0.8021	Intermediate Similarity	NPD3666	Approved
0.8021	Intermediate Similarity	NPD4197	Approved
0.8	Intermediate Similarity	NPD6882	Approved
0.8	Intermediate Similarity	NPD8297	Approved
0.7982	Intermediate Similarity	NPD5249	Phase 3
0.7982	Intermediate Similarity	NPD5251	Approved
0.7982	Intermediate Similarity	NPD5250	Approved
0.7982	Intermediate Similarity	NPD5247	Approved
0.7982	Intermediate Similarity	NPD4634	Approved
0.7982	Intermediate Similarity	NPD5248	Approved
0.798	Intermediate Similarity	NPD5328	Approved
0.7963	Intermediate Similarity	NPD7320	Approved
0.7963	Intermediate Similarity	NPD5128	Approved
0.7963	Intermediate Similarity	NPD6011	Approved
0.7944	Intermediate Similarity	NPD4768	Approved
0.7944	Intermediate Similarity	NPD4767	Approved
0.7925	Intermediate Similarity	NPD4754	Approved
0.7909	Intermediate Similarity	NPD5215	Approved
0.7909	Intermediate Similarity	NPD5216	Approved
0.7909	Intermediate Similarity	NPD5217	Approved
0.7885	Intermediate Similarity	NPD5696	Approved
0.787	Intermediate Similarity	NPD5701	Approved
0.7835	Intermediate Similarity	NPD4786	Approved
0.7822	Intermediate Similarity	NPD5284	Approved
0.7822	Intermediate Similarity	NPD5281	Approved
0.7818	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD5135	Approved
0.7818	Intermediate Similarity	NPD5169	Approved
0.7812	Intermediate Similarity	NPD4223	Phase 3
0.7812	Intermediate Similarity	NPD4221	Approved
0.7748	Intermediate Similarity	NPD5127	Approved
0.7745	Intermediate Similarity	NPD4202	Approved
0.7732	Intermediate Similarity	NPD4788	Approved
0.7677	Intermediate Similarity	NPD3618	Phase 1
0.7629	Intermediate Similarity	NPD3667	Approved
0.7611	Intermediate Similarity	NPD4632	Approved
0.7604	Intermediate Similarity	NPD4695	Discontinued
0.7589	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7101	Approved
0.7586	Intermediate Similarity	NPD7100	Approved
0.7565	Intermediate Similarity	NPD7115	Discovery
0.7544	Intermediate Similarity	NPD5167	Approved
0.7521	Intermediate Similarity	NPD6054	Approved
0.75	Intermediate Similarity	NPD4693	Phase 3
0.75	Intermediate Similarity	NPD4690	Approved
0.75	Intermediate Similarity	NPD5091	Approved
0.75	Intermediate Similarity	NPD5205	Approved
0.75	Intermediate Similarity	NPD4689	Approved
0.75	Intermediate Similarity	NPD4195	Approved
0.75	Intermediate Similarity	NPD4688	Approved
0.75	Intermediate Similarity	NPD4138	Approved
0.75	Intermediate Similarity	NPD6335	Approved
0.75	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD6274	Approved
0.7477	Intermediate Similarity	NPD5168	Approved
0.7476	Intermediate Similarity	NPD5694	Approved
0.7476	Intermediate Similarity	NPD6050	Approved
0.7451	Intermediate Similarity	NPD6673	Approved
0.7451	Intermediate Similarity	NPD6904	Approved
0.7451	Intermediate Similarity	NPD6080	Approved
0.7414	Intermediate Similarity	NPD6009	Approved
0.7414	Intermediate Similarity	NPD6317	Approved
0.7404	Intermediate Similarity	NPD6399	Phase 3
0.7404	Intermediate Similarity	NPD5133	Approved
0.74	Intermediate Similarity	NPD5363	Approved
0.7396	Intermediate Similarity	NPD3617	Approved
0.7395	Intermediate Similarity	NPD6370	Approved
0.7379	Intermediate Similarity	NPD5692	Phase 3
0.7379	Intermediate Similarity	NPD5785	Approved
0.7373	Intermediate Similarity	NPD6319	Approved
0.7368	Intermediate Similarity	NPD6053	Discontinued
0.7353	Intermediate Similarity	NPD6672	Approved
0.7353	Intermediate Similarity	NPD4518	Approved
0.7353	Intermediate Similarity	NPD5737	Approved
0.735	Intermediate Similarity	NPD6314	Approved
0.735	Intermediate Similarity	NPD6313	Approved
0.7327	Intermediate Similarity	NPD6409	Approved
0.7327	Intermediate Similarity	NPD6684	Approved
0.7327	Intermediate Similarity	NPD7146	Approved
0.7327	Intermediate Similarity	NPD4519	Discontinued
0.7327	Intermediate Similarity	NPD4623	Approved
0.7327	Intermediate Similarity	NPD7521	Approved
0.7327	Intermediate Similarity	NPD7334	Approved
0.7327	Intermediate Similarity	NPD5330	Approved
0.7311	Intermediate Similarity	NPD6016	Approved
0.7311	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD6015	Approved
0.7308	Intermediate Similarity	NPD5693	Phase 1
0.7273	Intermediate Similarity	NPD7492	Approved
0.725	Intermediate Similarity	NPD5988	Approved
0.7227	Intermediate Similarity	NPD6059	Approved
0.7213	Intermediate Similarity	NPD6616	Approved
0.7212	Intermediate Similarity	NPD5207	Approved
0.7212	Intermediate Similarity	NPD4096	Approved
0.719	Intermediate Similarity	NPD7604	Phase 2
0.7184	Intermediate Similarity	NPD6903	Approved
0.7184	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6868	Approved
0.7172	Intermediate Similarity	NPD4139	Approved
0.7172	Intermediate Similarity	NPD4692	Approved
0.7167	Intermediate Similarity	NPD5983	Phase 2
0.7167	Intermediate Similarity	NPD6908	Approved
0.7167	Intermediate Similarity	NPD6909	Approved
0.7157	Intermediate Similarity	NPD6098	Approved
0.7157	Intermediate Similarity	NPD5786	Approved
0.7154	Intermediate Similarity	NPD7078	Approved
0.7143	Intermediate Similarity	NPD4522	Approved
0.7143	Intermediate Similarity	NPD6008	Approved
0.7129	Intermediate Similarity	NPD3668	Phase 3
0.7115	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD4269	Approved
0.71	Intermediate Similarity	NPD4270	Approved
0.7097	Intermediate Similarity	NPD7736	Approved
0.7087	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6412	Phase 2
0.7073	Intermediate Similarity	NPD6336	Discontinued
0.7059	Intermediate Similarity	NPD1696	Phase 3
0.7041	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5362	Discontinued
0.701	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7640	Approved
0.7	Intermediate Similarity	NPD7639	Approved
0.6981	Remote Similarity	NPD6411	Approved
0.6981	Remote Similarity	NPD7515	Phase 2
0.6979	Remote Similarity	NPD4785	Approved
0.6979	Remote Similarity	NPD4784	Approved
0.6944	Remote Similarity	NPD5654	Approved
0.693	Remote Similarity	NPD6614	Approved
0.6916	Remote Similarity	NPD5778	Approved
0.6916	Remote Similarity	NPD5779	Approved
0.6909	Remote Similarity	NPD7638	Approved
0.6907	Remote Similarity	NPD7339	Approved
0.6907	Remote Similarity	NPD6942	Approved
0.69	Remote Similarity	NPD4819	Approved
0.69	Remote Similarity	NPD5368	Approved
0.69	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.69	Remote Similarity	NPD4820	Approved
0.69	Remote Similarity	NPD4252	Approved
0.69	Remote Similarity	NPD4821	Approved
0.69	Remote Similarity	NPD4822	Approved
0.688	Remote Similarity	NPD8293	Discontinued
0.6857	Remote Similarity	NPD5208	Approved
0.6852	Remote Similarity	NPD5282	Discontinued

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