NPASS Compound

Structure

CID84568 OpenBabel06191715422D 30 33 0 0 1 0 0 0 0 0999 V2000 -0.8660 2.5000 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 -1.7321 3.0000 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 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 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 -3.4641 -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 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 3 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 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -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 2 2 0 0 0 0 1 3 1 0 0 0 0 2 9 1 0 0 0 0 3 11 2 0 0 0 0 4 8 2 0 0 0 0 4 10 1 0 0 0 0 5 8 1 0 0 0 0 5 12 2 0 0 0 0 6 8 1 0 0 0 0 6 22 1 0 0 0 0 7 13 1 0 0 0 0 7 23 1 0 0 0 0 9 14 1 0 0 0 0 9 15 2 0 0 0 0 10 14 1 0 0 0 0 10 16 2 0 0 0 0 11 15 1 0 0 0 0 11 24 1 0 0 0 0 12 16 1 0 0 0 0 12 25 1 0 0 0 0 13 17 1 0 0 0 0 13 30 1 0 0 0 0 14 21 1 0 0 0 0 15 18 1 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 17 26 1 0 0 0 0 18 27 2 0 0 0 0 19 20 1 0 0 0 0 19 28 1 0 0 0 0 20 21 1 0 0 0 0 20 29 1 0 0 0 0 21 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	418.13
Volume:	398.203
LogP:	0.561
LogD:	0.654
LogS:	-3.694
# Rotatable Bonds:	3
TPSA:	171.07
# H-Bond Aceptor:	9
# H-Bond Donor:	8
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.275
Synthetic Accessibility Score:	4.104
Fsp3:	0.333
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:	-5.888
MDCK Permeability:	4.4861230890091974e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.999
20% Bioavailability (F20%):	0.828
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.068
Plasma Protein Binding (PPB):	91.8758773803711%
Volume Distribution (VD):	1.133
Pgp-substrate:	10.45447826385498%

ADMET: Metabolism

CYP1A2-inhibitor:	0.059
CYP1A2-substrate:	0.036
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.24
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.174
CYP3A4-inhibitor:	0.018
CYP3A4-substrate:	0.015

ADMET: Excretion

Clearance (CL):	2.325
Half-life (T1/2):	0.5

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.058
Drug-inuced Liver Injury (DILI):	0.914
AMES Toxicity:	0.716
Rat Oral Acute Toxicity:	0.048
Maximum Recommended Daily Dose:	0.01
Skin Sensitization:	0.68
Carcinogencity:	0.036
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.041

Download Data

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

Natural Product: NPC84568

Natural Product ID:	NPC84568
*Common Name:**	1,8-Dihydroxy-3-(Hydroxymethyl)-10-[3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]-10H-Anthracen-9-One
IUPAC Name:	1,8-dihydroxy-3-(hydroxymethyl)-10-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-10H-anthracen-9-one
Synonyms:
Standard InCHIKey:	AFHJQYHRLPMKHU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H22O9/c22-6-8-4-10-14(21-20(29)19(28)17(26)13(7-23)30-21)9-2-1-3-11(24)15(9)18(27)16(10)12(25)5-8/h1-5,13-14,17,19-26,28-29H,6-7H2
SMILES:	OCc1cc(O)c2c(c1)C(C1OC(CO)C(C(C1O)O)O)c1c(C2=O)c(O)ccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL123026
PubChem CID:	313325
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes

*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
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	Flowers	Tantempango, Hidalgo, Mexico	2019-May	DOI[10.1007/s11130-020-00822-2]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16297615]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[18543151]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24358188]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8778246]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14763	Aloe ferox	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14763	Aloe ferox	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14763	Aloe ferox	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14763	Aloe ferox	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2837	Aloe spicata	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2997	Aloe africana	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25238	Rheum coreanum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14763	Aloe ferox	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25238	Rheum coreanum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2997	Aloe africana	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7632	Rheum tanguticum	Species	Polygonaceae	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
GI50	115
IC50	1
Potency	4

Activity Type	# Activity
Cell Line	115
NON-MOLECULAR	4
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	43954.16	nM	PMID[493386]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	10000.0	nM	PMID[493385]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493385]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[493386]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	1058.4	nM	PMID[493387]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	1677.4	nM	PMID[493387]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	749.3	nM	PMID[493387]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	1882.1	nM	PMID[493387]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	<	30000.0	nM	PMID[493388]

☑ 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 NPC84568 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	373
0.1-0.2	1240
0.2-0.3	2687
0.3-0.4	6500
0.4-0.5	11347
0.5-0.6	5883
0.6-0.7	7191
0.7-0.8	6962
0.8-0.85	437
0.85-0.9	55
0.9-0.95	16
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC48130
1.0	High Similarity	NPC218866
1.0	High Similarity	NPC300684
0.9928	High Similarity	NPC170055
0.9714	High Similarity	NPC285122
0.9384	High Similarity	NPC205172
0.9384	High Similarity	NPC209393
0.932	High Similarity	NPC174599
0.932	High Similarity	NPC82190
0.932	High Similarity	NPC192219
0.9257	High Similarity	NPC283480
0.9257	High Similarity	NPC148323
0.9189	High Similarity	NPC266469
0.9189	High Similarity	NPC3449
0.9133	High Similarity	NPC53139
0.9067	High Similarity	NPC206641
0.9067	High Similarity	NPC208651
0.9054	High Similarity	NPC474533
0.9054	High Similarity	NPC474534
0.8954	High Similarity	NPC97637
0.8954	High Similarity	NPC187934
0.8867	High Similarity	NPC474622
0.8867	High Similarity	NPC474621
0.8784	High Similarity	NPC94781
0.8776	High Similarity	NPC120536
0.8759	High Similarity	NPC85310
0.8742	High Similarity	NPC470408
0.8742	High Similarity	NPC474824
0.8742	High Similarity	NPC182921
0.8742	High Similarity	NPC218870
0.8725	High Similarity	NPC280753
0.8725	High Similarity	NPC44378
0.8725	High Similarity	NPC478219
0.8718	High Similarity	NPC478022
0.8718	High Similarity	NPC478020
0.8714	High Similarity	NPC70622
0.871	High Similarity	NPC212099
0.871	High Similarity	NPC101116
0.8649	High Similarity	NPC472134
0.8639	High Similarity	NPC244691
0.8636	High Similarity	NPC314795
0.863	High Similarity	NPC474961
0.863	High Similarity	NPC469520
0.8627	High Similarity	NPC474861
0.8609	High Similarity	NPC205918
0.86	High Similarity	NPC477221
0.8591	High Similarity	NPC215593
0.8591	High Similarity	NPC472135
0.859	High Similarity	NPC278329
0.859	High Similarity	NPC146837
0.859	High Similarity	NPC216752
0.8571	High Similarity	NPC199253
0.8571	High Similarity	NPC136588
0.8562	High Similarity	NPC106519
0.8562	High Similarity	NPC314257
0.8562	High Similarity	NPC91019
0.8553	High Similarity	NPC478220
0.8543	High Similarity	NPC315520
0.8542	High Similarity	NPC305060
0.8533	High Similarity	NPC142846
0.8533	High Similarity	NPC106524
0.8533	High Similarity	NPC290695
0.8521	High Similarity	NPC52407
0.8521	High Similarity	NPC314048
0.8514	High Similarity	NPC103910
0.8506	High Similarity	NPC478027
0.8506	High Similarity	NPC478223
0.8503	High Similarity	NPC135524
0.8503	High Similarity	NPC257644
0.85	High Similarity	NPC478021
0.8497	Intermediate Similarity	NPC472211
0.8493	Intermediate Similarity	NPC315578
0.8487	Intermediate Similarity	NPC227485
0.8481	Intermediate Similarity	NPC178281
0.8477	Intermediate Similarity	NPC120171
0.8472	Intermediate Similarity	NPC315275
0.8467	Intermediate Similarity	NPC290194
0.8467	Intermediate Similarity	NPC119767
0.8467	Intermediate Similarity	NPC162751
0.8467	Intermediate Similarity	NPC52161
0.8462	Intermediate Similarity	NPC472262
0.8462	Intermediate Similarity	NPC161964
0.8462	Intermediate Similarity	NPC287604
0.8447	Intermediate Similarity	NPC294501
0.8446	Intermediate Similarity	NPC471682
0.844	Intermediate Similarity	NPC31799
0.8435	Intermediate Similarity	NPC305845
0.8435	Intermediate Similarity	NPC204045
0.8429	Intermediate Similarity	NPC767
0.8429	Intermediate Similarity	NPC247250
0.8425	Intermediate Similarity	NPC26924
0.8425	Intermediate Similarity	NPC190457
0.8425	Intermediate Similarity	NPC86744
0.8421	Intermediate Similarity	NPC477914
0.8421	Intermediate Similarity	NPC177308
0.8421	Intermediate Similarity	NPC124478
0.8406	Intermediate Similarity	NPC173978
0.84	Intermediate Similarity	NPC136878
0.84	Intermediate Similarity	NPC147250
0.84	Intermediate Similarity	NPC470570
0.84	Intermediate Similarity	NPC314437
0.8395	Intermediate Similarity	NPC203751
0.8395	Intermediate Similarity	NPC85368
0.8395	Intermediate Similarity	NPC199357
0.8392	Intermediate Similarity	NPC115458
0.8389	Intermediate Similarity	NPC471906
0.8389	Intermediate Similarity	NPC79627
0.8389	Intermediate Similarity	NPC29932
0.8387	Intermediate Similarity	NPC208152
0.8387	Intermediate Similarity	NPC78492
0.8385	Intermediate Similarity	NPC298778
0.8378	Intermediate Similarity	NPC137649
0.8377	Intermediate Similarity	NPC478218
0.8375	Intermediate Similarity	NPC225419
0.8375	Intermediate Similarity	NPC474024
0.8367	Intermediate Similarity	NPC3218
0.8367	Intermediate Similarity	NPC169452
0.8367	Intermediate Similarity	NPC225243
0.8367	Intermediate Similarity	NPC181560
0.8366	Intermediate Similarity	NPC209846
0.8366	Intermediate Similarity	NPC328740
0.8366	Intermediate Similarity	NPC289774
0.8366	Intermediate Similarity	NPC477276
0.8366	Intermediate Similarity	NPC477897
0.8356	Intermediate Similarity	NPC197666
0.8356	Intermediate Similarity	NPC126739
0.8355	Intermediate Similarity	NPC89442
0.8354	Intermediate Similarity	NPC478229
0.8354	Intermediate Similarity	NPC473961
0.8345	Intermediate Similarity	NPC272268
0.8345	Intermediate Similarity	NPC191976
0.8344	Intermediate Similarity	NPC3718
0.8344	Intermediate Similarity	NPC472055
0.8344	Intermediate Similarity	NPC470810
0.8344	Intermediate Similarity	NPC474345
0.8344	Intermediate Similarity	NPC284495
0.8344	Intermediate Similarity	NPC184326
0.8344	Intermediate Similarity	NPC292863
0.8333	Intermediate Similarity	NPC5029
0.8333	Intermediate Similarity	NPC478160
0.8333	Intermediate Similarity	NPC271385
0.8333	Intermediate Similarity	NPC471683
0.8333	Intermediate Similarity	NPC111536
0.8333	Intermediate Similarity	NPC474630
0.8333	Intermediate Similarity	NPC12070
0.8333	Intermediate Similarity	NPC183441
0.8333	Intermediate Similarity	NPC34482
0.8333	Intermediate Similarity	NPC30432
0.8333	Intermediate Similarity	NPC76128
0.8323	Intermediate Similarity	NPC259905
0.8323	Intermediate Similarity	NPC222455
0.8323	Intermediate Similarity	NPC474501
0.8323	Intermediate Similarity	NPC68727
0.8323	Intermediate Similarity	NPC478133
0.8322	Intermediate Similarity	NPC17843
0.8322	Intermediate Similarity	NPC293545
0.8322	Intermediate Similarity	NPC58685
0.8322	Intermediate Similarity	NPC451542
0.8322	Intermediate Similarity	NPC296752
0.8322	Intermediate Similarity	NPC174905
0.8322	Intermediate Similarity	NPC313047
0.8322	Intermediate Similarity	NPC295712
0.8322	Intermediate Similarity	NPC474203
0.8322	Intermediate Similarity	NPC100242
0.8313	Intermediate Similarity	NPC178851
0.8313	Intermediate Similarity	NPC43319
0.8313	Intermediate Similarity	NPC178173
0.8312	Intermediate Similarity	NPC244583
0.8312	Intermediate Similarity	NPC150123
0.8312	Intermediate Similarity	NPC10807
0.8312	Intermediate Similarity	NPC87708
0.8312	Intermediate Similarity	NPC470337
0.8312	Intermediate Similarity	NPC56232
0.8312	Intermediate Similarity	NPC161881
0.8312	Intermediate Similarity	NPC113608
0.8312	Intermediate Similarity	NPC470338
0.8312	Intermediate Similarity	NPC268992
0.8312	Intermediate Similarity	NPC51824
0.8311	Intermediate Similarity	NPC477275
0.8302	Intermediate Similarity	NPC290160
0.8299	Intermediate Similarity	NPC138099
0.8299	Intermediate Similarity	NPC242994
0.8298	Intermediate Similarity	NPC282923
0.8298	Intermediate Similarity	NPC48248
0.8293	Intermediate Similarity	NPC324220
0.8293	Intermediate Similarity	NPC475246
0.8293	Intermediate Similarity	NPC102053
0.8293	Intermediate Similarity	NPC289876
0.8293	Intermediate Similarity	NPC312630
0.8291	Intermediate Similarity	NPC472261
0.8291	Intermediate Similarity	NPC137232
0.8291	Intermediate Similarity	NPC142252
0.8291	Intermediate Similarity	NPC18380
0.8288	Intermediate Similarity	NPC301915
0.8288	Intermediate Similarity	NPC261292
0.8288	Intermediate Similarity	NPC245923
0.8282	Intermediate Similarity	NPC472054
0.828	Intermediate Similarity	NPC470339
0.828	Intermediate Similarity	NPC324736
0.828	Intermediate Similarity	NPC53545

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 NPC84568 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	318
0.1-0.2	776
0.2-0.3	1466
0.3-0.4	2639
0.4-0.5	2236
0.5-0.6	1146
0.6-0.7	433
0.7-0.8	127
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8421	Intermediate Similarity	NPD4380	Phase 2
0.8321	Intermediate Similarity	NPD1201	Approved
0.8267	Intermediate Similarity	NPD7390	Discontinued
0.8253	Intermediate Similarity	NPD8150	Discontinued
0.8214	Intermediate Similarity	NPD1470	Approved
0.8212	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD8313	Approved
0.8182	Intermediate Similarity	NPD8312	Approved
0.8176	Intermediate Similarity	NPD6959	Discontinued
0.8095	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD5404	Approved
0.8041	Intermediate Similarity	NPD5408	Approved
0.8041	Intermediate Similarity	NPD5405	Approved
0.8041	Intermediate Similarity	NPD5406	Approved
0.8025	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD7473	Discontinued
0.7975	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD6166	Phase 2
0.7901	Intermediate Similarity	NPD6232	Discontinued
0.7885	Intermediate Similarity	NPD3226	Approved
0.7875	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD1934	Approved
0.7843	Intermediate Similarity	NPD3300	Phase 2
0.7799	Intermediate Similarity	NPD7819	Suspended
0.7771	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD5844	Phase 1
0.7764	Intermediate Similarity	NPD7075	Discontinued
0.7759	Intermediate Similarity	NPD6534	Approved
0.7759	Intermediate Similarity	NPD6535	Approved
0.7701	Intermediate Similarity	NPD6213	Phase 3
0.7701	Intermediate Similarity	NPD6212	Phase 3
0.7701	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD6781	Approved
0.764	Intermediate Similarity	NPD6776	Approved
0.764	Intermediate Similarity	NPD6778	Approved
0.764	Intermediate Similarity	NPD6779	Approved
0.764	Intermediate Similarity	NPD6780	Approved
0.764	Intermediate Similarity	NPD6782	Approved
0.764	Intermediate Similarity	NPD6777	Approved
0.7633	Intermediate Similarity	NPD6559	Discontinued
0.7632	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD2346	Discontinued
0.763	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD7700	Phase 2
0.7627	Intermediate Similarity	NPD7699	Phase 2
0.7619	Intermediate Similarity	NPD7074	Phase 3
0.7593	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD943	Approved
0.7582	Intermediate Similarity	NPD1549	Phase 2
0.7578	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD8320	Phase 1
0.7569	Intermediate Similarity	NPD8319	Approved
0.7562	Intermediate Similarity	NPD7411	Suspended
0.7561	Intermediate Similarity	NPD5494	Approved
0.756	Intermediate Similarity	NPD7054	Approved
0.7531	Intermediate Similarity	NPD5402	Approved
0.7516	Intermediate Similarity	NPD6801	Discontinued
0.7516	Intermediate Similarity	NPD2532	Approved
0.7516	Intermediate Similarity	NPD2533	Approved
0.7516	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2534	Approved
0.7515	Intermediate Similarity	NPD7472	Approved
0.7514	Intermediate Similarity	NPD7435	Discontinued
0.75	Intermediate Similarity	NPD1510	Phase 2
0.75	Intermediate Similarity	NPD3818	Discontinued
0.7484	Intermediate Similarity	NPD4628	Phase 3
0.7471	Intermediate Similarity	NPD6797	Phase 2
0.7469	Intermediate Similarity	NPD2801	Approved
0.7452	Intermediate Similarity	NPD1511	Approved
0.7436	Intermediate Similarity	NPD6190	Approved
0.7427	Intermediate Similarity	NPD7251	Discontinued
0.7421	Intermediate Similarity	NPD5403	Approved
0.7418	Intermediate Similarity	NPD7698	Approved
0.7418	Intermediate Similarity	NPD7697	Approved
0.7418	Intermediate Similarity	NPD7696	Phase 3
0.7386	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD7808	Phase 3
0.7384	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD7871	Phase 2
0.7377	Intermediate Similarity	NPD7870	Phase 2
0.7376	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1607	Approved
0.7363	Intermediate Similarity	NPD6823	Phase 2
0.7358	Intermediate Similarity	NPD1512	Approved
0.7355	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD7701	Phase 2
0.7338	Intermediate Similarity	NPD2935	Discontinued
0.7329	Intermediate Similarity	NPD7458	Discontinued
0.7326	Intermediate Similarity	NPD7801	Approved
0.7317	Intermediate Similarity	NPD3817	Phase 2
0.7308	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD5401	Approved
0.7294	Intermediate Similarity	NPD3751	Discontinued
0.7284	Intermediate Similarity	NPD6599	Discontinued
0.7283	Intermediate Similarity	NPD4954	Approved
0.7283	Intermediate Similarity	NPD5028	Approved
0.7283	Intermediate Similarity	NPD5034	Approved
0.7283	Intermediate Similarity	NPD5026	Approved
0.7283	Intermediate Similarity	NPD4955	Approved
0.7283	Intermediate Similarity	NPD36	Approved
0.7273	Intermediate Similarity	NPD7874	Approved
0.7273	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3882	Suspended
0.7267	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD3787	Discontinued
0.7257	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD1240	Approved
0.7229	Intermediate Similarity	NPD3749	Approved
0.7226	Intermediate Similarity	NPD2796	Approved
0.7226	Intermediate Similarity	NPD6100	Approved
0.7226	Intermediate Similarity	NPD6099	Approved
0.7225	Intermediate Similarity	NPD5030	Phase 2
0.7219	Intermediate Similarity	NPD8151	Discontinued
0.7219	Intermediate Similarity	NPD3764	Approved
0.7216	Intermediate Similarity	NPD5038	Approved
0.7216	Intermediate Similarity	NPD5037	Approved
0.7172	Intermediate Similarity	NPD3019	Approved
0.7169	Intermediate Similarity	NPD7768	Phase 2
0.7161	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD5036	Approved
0.7152	Intermediate Similarity	NPD3750	Approved
0.7152	Intermediate Similarity	NPD1465	Phase 2
0.7152	Intermediate Similarity	NPD8166	Discontinued
0.7152	Intermediate Similarity	NPD8455	Phase 2
0.7152	Intermediate Similarity	NPD7003	Approved
0.7151	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7783	Phase 2
0.7143	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD6799	Approved
0.7119	Intermediate Similarity	NPD8434	Phase 2
0.7115	Intermediate Similarity	NPD1551	Phase 2
0.7114	Intermediate Similarity	NPD3094	Phase 2
0.7114	Intermediate Similarity	NPD1164	Approved
0.7105	Intermediate Similarity	NPD2313	Discontinued
0.7093	Intermediate Similarity	NPD7177	Discontinued
0.7093	Intermediate Similarity	NPD7228	Approved
0.7091	Intermediate Similarity	NPD37	Approved
0.7089	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6234	Discontinued
0.7075	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD7266	Discontinued
0.7067	Intermediate Similarity	NPD2798	Approved
0.7067	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD4965	Approved
0.7066	Intermediate Similarity	NPD4966	Approved
0.7066	Intermediate Similarity	NPD4967	Phase 2
0.7059	Intermediate Similarity	NPD5710	Approved
0.7059	Intermediate Similarity	NPD5711	Approved
0.7059	Intermediate Similarity	NPD6663	Approved
0.7055	Intermediate Similarity	NPD2932	Approved
0.7051	Intermediate Similarity	NPD2799	Discontinued
0.7039	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6273	Approved
0.702	Intermediate Similarity	NPD5736	Approved
0.7006	Intermediate Similarity	NPD2438	Suspended
0.6978	Remote Similarity	NPD2342	Discontinued
0.6972	Remote Similarity	NPD7635	Approved
0.6959	Remote Similarity	NPD3092	Approved
0.695	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5035	Approved
0.6943	Remote Similarity	NPD7033	Discontinued
0.6939	Remote Similarity	NPD5125	Phase 3
0.6939	Remote Similarity	NPD5126	Approved
0.6937	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD3400	Discontinued
0.6932	Remote Similarity	NPD5029	Approved
0.6932	Remote Similarity	NPD5031	Approved
0.6932	Remote Similarity	NPD7685	Pre-registration
0.6932	Remote Similarity	NPD5027	Approved
0.6928	Remote Similarity	NPD4625	Phase 3
0.6923	Remote Similarity	NPD6651	Approved
0.6919	Remote Similarity	NPD8285	Discontinued
0.6904	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4060	Phase 1
0.6901	Remote Similarity	NPD7199	Phase 2
0.6897	Remote Similarity	NPD7799	Discontinued
0.6893	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6844	Discontinued
0.6885	Remote Similarity	NPD4360	Phase 2
0.6885	Remote Similarity	NPD4363	Phase 3
0.6883	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5951	Approved
0.6875	Remote Similarity	NPD6674	Discontinued
0.6875	Remote Similarity	NPD2800	Approved
0.6871	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD230	Phase 1
0.6855	Remote Similarity	NPD2344	Approved
0.6852	Remote Similarity	NPD7236	Approved
0.6848	Remote Similarity	NPD7239	Suspended
0.6845	Remote Similarity	NPD5760	Phase 2
0.6845	Remote Similarity	NPD5761	Phase 2
0.6835	Remote Similarity	NPD3748	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