NPASS Compound

Structure

CID41122 OpenBabel06191715372D 44 50 0 0 1 0 0 0 0 0999 V2000 2.3267 4.1833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3267 -1.6770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9515 -1.6145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7332 -1.9382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7464 1.9972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5847 2.3927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1812 4.6147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4547 2.8392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3580 3.0470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9229 3.6901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0199 -0.8857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1725 1.7415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5986 -0.5053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1725 2.7182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3636 1.0446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1529 3.3281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0113 4.0785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3267 0.2764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1013 -0.9852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6349 1.2531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5866 1.7002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6447 3.7986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3267 1.2531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4012 -0.5747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9312 3.5923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4808 1.7415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9398 0.4970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4808 2.7182 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0071 3.4516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6786 4.1376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4808 -0.2120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6349 0.2764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5959 -0.9307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3611 0.1166 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3904 -0.4657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6903 -0.0553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5585 0.1860 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.3267 3.2066 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.2699 2.5109 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4808 -1.1887 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0196 -1.7193 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5807 -0.3610 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3504 3.9695 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 38 1 0 0 0 0 2 40 1 0 0 0 0 3 41 1 0 0 0 0 4 42 1 0 0 0 0 5 8 1 0 0 0 0 5 21 2 0 0 0 0 6 9 2 0 0 0 0 6 21 1 0 0 0 0 7 10 2 0 0 0 0 7 22 1 0 0 0 0 8 25 2 0 0 0 0 9 25 1 0 0 0 0 10 29 1 0 0 0 0 11 13 1 0 0 0 0 11 24 1 0 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 37 1 0 0 0 0 14 38 1 0 0 0 0 15 21 1 0 0 0 0 15 27 1 0 0 0 0 16 22 1 0 0 0 0 17 22 2 0 0 0 0 17 30 1 0 0 0 0 18 23 2 0 0 0 0 18 31 1 0 0 0 0 19 24 2 0 0 0 0 19 33 1 0 0 0 0 20 26 2 0 0 0 0 20 32 1 0 0 0 0 23 26 1 0 0 0 0 24 34 1 0 0 0 0 25 43 1 0 0 0 0 26 28 1 0 0 0 0 27 34 1 0 0 0 0 27 37 2 0 0 0 0 28 16 1 1 0 0 0 28 38 1 0 0 0 0 29 30 2 0 0 0 0 29 39 1 0 0 0 0 30 43 1 0 0 0 0 31 32 2 0 0 0 0 31 40 1 0 0 0 0 32 44 1 0 0 0 0 33 35 2 0 0 0 0 33 41 1 0 0 0 0 34 36 2 0 0 0 0 35 36 1 0 0 0 0 35 42 1 0 0 0 0 36 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	592.26
Volume:	611.778
LogP:	6.079
LogD:	3.859
LogS:	-7.047
# Rotatable Bonds:	3
TPSA:	81.98
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	8
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.284
Synthetic Accessibility Score:	5.632
Fsp3:	0.306
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.826
MDCK Permeability:	1.857494680734817e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.955
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.031
30% Bioavailability (F30%):	0.933

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.265
Plasma Protein Binding (PPB):	95.16092681884766%
Volume Distribution (VD):	0.617
Pgp-substrate:	2.2791521549224854%

ADMET: Metabolism

CYP1A2-inhibitor:	0.088
CYP1A2-substrate:	0.955
CYP2C19-inhibitor:	0.158
CYP2C19-substrate:	0.919
CYP2C9-inhibitor:	0.096
CYP2C9-substrate:	0.65
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.932
CYP3A4-inhibitor:	0.107
CYP3A4-substrate:	0.943

ADMET: Excretion

Clearance (CL):	7.921
Half-life (T1/2):	0.18

ADMET: Toxicity

hERG Blockers:	0.918
Human Hepatotoxicity (H-HT):	0.045
Drug-inuced Liver Injury (DILI):	0.753
AMES Toxicity:	0.147
Rat Oral Acute Toxicity:	0.445
Maximum Recommended Daily Dose:	0.983
Skin Sensitization:	0.769
Carcinogencity:	0.044
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.613

Download Data

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

Natural Product: NPC41122

Natural Product ID:	NPC41122
*Common Name:**	FKHCVUFZOFEROS-MUUNZHRXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FKHCVUFZOFEROS-MUUNZHRXSA-N
Standard InCHI:	InChI=1S/C36H36N2O6/c1-38-14-12-23-18-31(40-2)32-20-26(23)28(38)16-22-7-10-29(39)30(17-22)43-25-8-5-21(6-9-25)15-27-34-24(11-13-37-27)19-33(41-3)35(42-4)36(34)44-32/h5-10,17-20,28,39H,11-16H2,1-4H3/t28-/m1/s1
SMILES:	COc1cc2CCN([C@H]3c2cc1Oc1c2C(=NCCc2cc(c1OC)OC)Cc1ccc(Oc2cc(C3)ccc2O)cc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1967074
PubChem CID:	6711179
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	DOI[10.1016/S0040-4039(99)00339-1]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[10746886]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[10757718]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	root bark	Kunming, Yunnan, China	n.a.	PMID[10757718]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757718]
NPO11351	Stephania japonica	Species	Menispermaceae	Eukaryota	Aerial parts	n.a.	n.a.	PMID[20426456]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22256754]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[22256754]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[23252270]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2534610]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Europe PMC[535601]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8328267]
NPO11351	Stephania japonica	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9392886]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	Database[Article]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11351	Stephania japonica	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[Phytochemistry, 2000, 53, 715-722.]
NPO11351	Stephania japonica	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11351	Stephania japonica	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	root bark	n.a.	n.a.	Database[Title]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	root bark	Kunming, Yunnan, China	n.a.	Database[Title]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11351	Stephania japonica	Species	Menispermaceae	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	59

Activity Type	# Activity
Cell Line	59

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	16634.13	nM	PMID[450352]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	22908.68	nM	PMID[450352]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	23120.65	nM	PMID[450352]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	19098.53	nM	PMID[450352]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	13551.89	nM	PMID[450352]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	13995.87	nM	PMID[450352]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	25351.29	nM	PMID[450352]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	12218.0	nM	PMID[450352]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	14757.07	nM	PMID[450352]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	601.17	nM	PMID[450352]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	12735.03	nM	PMID[450352]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	22029.26	nM	PMID[450352]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	11885.02	nM	PMID[450352]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	17741.89	nM	PMID[450352]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	13583.13	nM	PMID[450352]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	22335.72	nM	PMID[450352]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	16032.45	nM	PMID[450352]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	17418.07	nM	PMID[450352]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	45603.69	nM	PMID[450352]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	12941.96	nM	PMID[450352]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	23442.29	nM	PMID[450352]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	5741.16	nM	PMID[450352]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	20606.3	nM	PMID[450352]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	17258.38	nM	PMID[450352]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	15031.42	nM	PMID[450352]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	10690.55	nM	PMID[450352]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	18407.72	nM	PMID[450352]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	16255.49	nM	PMID[450352]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	16330.52	nM	PMID[450352]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	16106.46	nM	PMID[450352]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	12589.25	nM	PMID[450352]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	12473.84	nM	PMID[450352]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	16749.43	nM	PMID[450352]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	13365.96	nM	PMID[450352]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	37497.3	nM	PMID[450352]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	14125.38	nM	PMID[450352]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	12022.64	nM	PMID[450352]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	12189.9	nM	PMID[450352]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	23227.37	nM	PMID[450352]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	22594.36	nM	PMID[450352]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	25763.21	nM	PMID[450352]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	13243.42	nM	PMID[450352]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	48640.72	nM	PMID[450352]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	15595.53	nM	PMID[450352]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	21037.78	nM	PMID[450352]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	16672.47	nM	PMID[450352]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	20558.91	nM	PMID[450352]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	19364.22	nM	PMID[450352]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	18450.15	nM	PMID[450352]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	25351.29	nM	PMID[450352]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	17619.76	nM	PMID[450352]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	10447.2	nM	PMID[450352]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	15995.58	nM	PMID[450352]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	29991.63	nM	PMID[450352]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	10814.34	nM	PMID[450352]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	22594.36	nM	PMID[450352]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	16710.91	nM	PMID[450352]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	10023.05	nM	PMID[450352]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	13489.63	nM	PMID[450352]

☑ 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 NPC41122 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	379
0.1-0.2	1903
0.2-0.3	9678
0.3-0.4	8242
0.4-0.5	6253
0.5-0.6	9959
0.6-0.7	5182
0.7-0.8	878
0.8-0.85	110
0.85-0.9	43
0.9-0.95	36
0.95-1	34

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC318805
0.977	High Similarity	NPC234318
0.9769	High Similarity	NPC85381
0.9588	High Similarity	NPC195538
0.9532	High Similarity	NPC476202
0.9422	High Similarity	NPC249996
0.936	High Similarity	NPC286119
0.9306	High Similarity	NPC223690
0.9306	High Similarity	NPC49075
0.9306	High Similarity	NPC328155
0.9306	High Similarity	NPC42663
0.9306	High Similarity	NPC311973
0.9306	High Similarity	NPC90998
0.9306	High Similarity	NPC30779
0.9306	High Similarity	NPC258657
0.9306	High Similarity	NPC7715
0.9306	High Similarity	NPC15414
0.9306	High Similarity	NPC290005
0.9306	High Similarity	NPC54654
0.9306	High Similarity	NPC285931
0.9306	High Similarity	NPC279228
0.9306	High Similarity	NPC239824
0.9306	High Similarity	NPC104196
0.9306	High Similarity	NPC290582
0.9306	High Similarity	NPC185639
0.9306	High Similarity	NPC181796
0.9306	High Similarity	NPC271013
0.9306	High Similarity	NPC8836
0.9306	High Similarity	NPC217748
0.9306	High Similarity	NPC182052
0.9306	High Similarity	NPC222661
0.9306	High Similarity	NPC251735
0.9306	High Similarity	NPC229373
0.9253	High Similarity	NPC274716
0.9253	High Similarity	NPC254441
0.9253	High Similarity	NPC167116
0.9148	High Similarity	NPC212237
0.9148	High Similarity	NPC116465
0.9096	High Similarity	NPC22115
0.9096	High Similarity	NPC275680
0.9045	High Similarity	NPC175890
0.9045	High Similarity	NPC11296
0.9045	High Similarity	NPC82457
0.9045	High Similarity	NPC274661
0.9045	High Similarity	NPC48490
0.9045	High Similarity	NPC206900
0.8994	High Similarity	NPC191132
0.8994	High Similarity	NPC60295
0.8983	High Similarity	NPC95426
0.8983	High Similarity	NPC16357
0.8983	High Similarity	NPC302245
0.8944	High Similarity	NPC24260
0.8944	High Similarity	NPC478093
0.8933	High Similarity	NPC139783
0.8933	High Similarity	NPC65312
0.8902	High Similarity	NPC276890
0.8902	High Similarity	NPC76682
0.8902	High Similarity	NPC317145
0.8902	High Similarity	NPC10908
0.8902	High Similarity	NPC198498
0.8902	High Similarity	NPC63646
0.8902	High Similarity	NPC317439
0.8902	High Similarity	NPC115284
0.8902	High Similarity	NPC227060
0.8895	High Similarity	NPC473589
0.8895	High Similarity	NPC30182
0.8895	High Similarity	NPC478092
0.8895	High Similarity	NPC478091
0.8851	High Similarity	NPC12424
0.8851	High Similarity	NPC41376
0.8851	High Similarity	NPC129518
0.8851	High Similarity	NPC251580
0.8786	High Similarity	NPC83198
0.8786	High Similarity	NPC204908
0.8779	High Similarity	NPC317272
0.8779	High Similarity	NPC240841
0.8779	High Similarity	NPC250846
0.8779	High Similarity	NPC42549
0.8779	High Similarity	NPC256012
0.8779	High Similarity	NPC268503
0.875	High Similarity	NPC293093
0.8689	High Similarity	NPC256124
0.8678	High Similarity	NPC66573
0.8671	High Similarity	NPC264850
0.8671	High Similarity	NPC13916
0.8656	High Similarity	NPC475654
0.8652	High Similarity	NPC243454
0.8652	High Similarity	NPC475479
0.8636	High Similarity	NPC190783
0.8636	High Similarity	NPC232386
0.8636	High Similarity	NPC152680
0.8613	High Similarity	NPC24465
0.8603	High Similarity	NPC239584
0.8556	High Similarity	NPC299990
0.8556	High Similarity	NPC73492
0.8533	High Similarity	NPC476565
0.8508	High Similarity	NPC302275
0.8478	Intermediate Similarity	NPC223236
0.8478	Intermediate Similarity	NPC259350
0.8475	Intermediate Similarity	NPC108434
0.8475	Intermediate Similarity	NPC475215
0.8475	Intermediate Similarity	NPC239775
0.8421	Intermediate Similarity	NPC107602
0.8418	Intermediate Similarity	NPC168753
0.8418	Intermediate Similarity	NPC118274
0.8372	Intermediate Similarity	NPC247639
0.8372	Intermediate Similarity	NPC25084
0.8371	Intermediate Similarity	NPC231371
0.8325	Intermediate Similarity	NPC254581
0.8324	Intermediate Similarity	NPC281581
0.8315	Intermediate Similarity	NPC14507
0.8315	Intermediate Similarity	NPC47077
0.8289	Intermediate Similarity	NPC471113
0.8286	Intermediate Similarity	NPC50380
0.8286	Intermediate Similarity	NPC179250
0.828	Intermediate Similarity	NPC475597
0.828	Intermediate Similarity	NPC473716
0.8276	Intermediate Similarity	NPC216816
0.8276	Intermediate Similarity	NPC329837
0.8246	Intermediate Similarity	NPC127402
0.8242	Intermediate Similarity	NPC474507
0.8208	Intermediate Similarity	NPC249797
0.8208	Intermediate Similarity	NPC184026
0.8208	Intermediate Similarity	NPC469817
0.8208	Intermediate Similarity	NPC295691
0.8208	Intermediate Similarity	NPC276588
0.8208	Intermediate Similarity	NPC278799
0.8208	Intermediate Similarity	NPC5238
0.8208	Intermediate Similarity	NPC39701
0.8208	Intermediate Similarity	NPC172765
0.8208	Intermediate Similarity	NPC127674
0.8208	Intermediate Similarity	NPC189266
0.8208	Intermediate Similarity	NPC110416
0.8208	Intermediate Similarity	NPC54379
0.8208	Intermediate Similarity	NPC2413
0.8208	Intermediate Similarity	NPC193949
0.8208	Intermediate Similarity	NPC207757
0.8208	Intermediate Similarity	NPC204828
0.8202	Intermediate Similarity	NPC474931
0.8202	Intermediate Similarity	NPC81218
0.8202	Intermediate Similarity	NPC158376
0.8202	Intermediate Similarity	NPC117188
0.8202	Intermediate Similarity	NPC205421
0.8202	Intermediate Similarity	NPC306555
0.8202	Intermediate Similarity	NPC145832
0.8202	Intermediate Similarity	NPC12053
0.8192	Intermediate Similarity	NPC212794
0.8192	Intermediate Similarity	NPC13504
0.8192	Intermediate Similarity	NPC253043
0.8192	Intermediate Similarity	NPC136508
0.8192	Intermediate Similarity	NPC477563
0.8192	Intermediate Similarity	NPC306843
0.8192	Intermediate Similarity	NPC96603
0.8192	Intermediate Similarity	NPC78222
0.8192	Intermediate Similarity	NPC196447
0.8182	Intermediate Similarity	NPC60186
0.8176	Intermediate Similarity	NPC428
0.8176	Intermediate Similarity	NPC147390
0.8176	Intermediate Similarity	NPC246587
0.8176	Intermediate Similarity	NPC24233
0.8176	Intermediate Similarity	NPC135538
0.8176	Intermediate Similarity	NPC476571
0.8155	Intermediate Similarity	NPC201508
0.8146	Intermediate Similarity	NPC68328
0.8136	Intermediate Similarity	NPC475393
0.8136	Intermediate Similarity	NPC324144
0.8132	Intermediate Similarity	NPC173416
0.8132	Intermediate Similarity	NPC148709
0.8132	Intermediate Similarity	NPC476577
0.8129	Intermediate Similarity	NPC477565
0.8129	Intermediate Similarity	NPC103379
0.8125	Intermediate Similarity	NPC119649
0.8125	Intermediate Similarity	NPC235143
0.8125	Intermediate Similarity	NPC230956
0.8125	Intermediate Similarity	NPC205255
0.8125	Intermediate Similarity	NPC271388
0.8118	Intermediate Similarity	NPC179825
0.8118	Intermediate Similarity	NPC191376
0.8118	Intermediate Similarity	NPC321505
0.8081	Intermediate Similarity	NPC220858
0.8081	Intermediate Similarity	NPC192768
0.8081	Intermediate Similarity	NPC97221
0.8081	Intermediate Similarity	NPC88249
0.8081	Intermediate Similarity	NPC151895
0.8079	Intermediate Similarity	NPC79402
0.8079	Intermediate Similarity	NPC80759
0.8077	Intermediate Similarity	NPC96584
0.8077	Intermediate Similarity	NPC255800
0.8068	Intermediate Similarity	NPC221864
0.8066	Intermediate Similarity	NPC10871
0.8045	Intermediate Similarity	NPC90984
0.8035	Intermediate Similarity	NPC476568
0.8034	Intermediate Similarity	NPC1229
0.8023	Intermediate Similarity	NPC27410
0.8023	Intermediate Similarity	NPC166014
0.8012	Intermediate Similarity	NPC476151
0.8011	Intermediate Similarity	NPC195766
0.8011	Intermediate Similarity	NPC206736
0.8	Intermediate Similarity	NPC185838
0.797	Intermediate Similarity	NPC82056

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 NPC41122 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	199
0.1-0.2	727
0.2-0.3	1116
0.3-0.4	1976
0.4-0.5	2654
0.5-0.6	1737
0.6-0.7	636
0.7-0.8	98
0.8-0.85	1
0.85-0.9	1
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9306	High Similarity	NPD8054	Approved
0.9306	High Similarity	NPD8053	Approved
0.8902	High Similarity	NPD8251	Approved
0.8902	High Similarity	NPD8252	Approved
0.8902	High Similarity	NPD8099	Discontinued
0.8851	High Similarity	NPD8156	Discontinued
0.8034	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.8021	Intermediate Similarity	NPD8095	Phase 1
0.7966	Intermediate Similarity	NPD6788	Approved
0.7931	Intermediate Similarity	NPD4005	Discontinued
0.7926	Intermediate Similarity	NPD7906	Approved
0.7849	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD4584	Approved
0.7784	Intermediate Similarity	NPD4678	Approved
0.7784	Intermediate Similarity	NPD4675	Approved
0.7772	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7747	Intermediate Similarity	NPD6071	Discontinued
0.7722	Intermediate Similarity	NPD7831	Phase 2
0.7722	Intermediate Similarity	NPD7833	Phase 2
0.7722	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD4055	Discovery
0.7717	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7713	Intermediate Similarity	NPD7312	Approved
0.7713	Intermediate Similarity	NPD7313	Approved
0.7713	Intermediate Similarity	NPD7310	Approved
0.7713	Intermediate Similarity	NPD7311	Approved
0.7701	Intermediate Similarity	NPD7447	Phase 1
0.7672	Intermediate Similarity	NPD7309	Approved
0.7663	Intermediate Similarity	NPD27	Approved
0.7663	Intermediate Similarity	NPD2489	Approved
0.765	Intermediate Similarity	NPD3051	Approved
0.7647	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4577	Approved
0.7619	Intermediate Similarity	NPD4578	Approved
0.7609	Intermediate Similarity	NPD2969	Approved
0.7609	Intermediate Similarity	NPD2970	Approved
0.7592	Intermediate Similarity	NPD4663	Approved
0.7572	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD7213	Phase 3
0.7543	Intermediate Similarity	NPD7212	Phase 2
0.7542	Intermediate Similarity	NPD4773	Phase 2
0.7542	Intermediate Similarity	NPD4772	Phase 2
0.7527	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD2560	Approved
0.7514	Intermediate Similarity	NPD2563	Approved
0.75	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7298	Approved
0.75	Intermediate Similarity	NPD4123	Phase 3
0.7474	Intermediate Similarity	NPD7549	Discontinued
0.7461	Intermediate Similarity	NPD7291	Discontinued
0.7459	Intermediate Similarity	NPD5772	Approved
0.7459	Intermediate Similarity	NPD4010	Discontinued
0.7459	Intermediate Similarity	NPD5773	Approved
0.7382	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD2898	Approved
0.7348	Intermediate Similarity	NPD6072	Discontinued
0.7345	Intermediate Similarity	NPD2421	Approved
0.7345	Intermediate Similarity	NPD2420	Approved
0.733	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD3692	Discontinued
0.7318	Intermediate Similarity	NPD2122	Discontinued
0.7318	Intermediate Similarity	NPD6031	Approved
0.7318	Intermediate Similarity	NPD6030	Approved
0.7308	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1424	Approved
0.7294	Intermediate Similarity	NPD2674	Phase 3
0.7288	Intermediate Similarity	NPD7124	Phase 2
0.7283	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD5677	Discontinued
0.7238	Intermediate Similarity	NPD4017	Approved
0.7238	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD5241	Discontinued
0.7228	Intermediate Similarity	NPD3450	Approved
0.7228	Intermediate Similarity	NPD2493	Approved
0.7228	Intermediate Similarity	NPD3452	Approved
0.7228	Intermediate Similarity	NPD2494	Approved
0.7219	Intermediate Similarity	NPD7802	Discontinued
0.7212	Intermediate Similarity	NPD7827	Phase 1
0.7211	Intermediate Similarity	NPD7493	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD2490	Approved
0.7208	Intermediate Similarity	NPD2488	Approved
0.7196	Intermediate Similarity	NPD4481	Phase 3
0.7191	Intermediate Similarity	NPD3845	Phase 1
0.7189	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD6331	Phase 2
0.7158	Intermediate Similarity	NPD5089	Approved
0.7158	Intermediate Similarity	NPD5090	Approved
0.715	Intermediate Similarity	NPD6997	Phase 2
0.7136	Intermediate Similarity	NPD7263	Phase 2
0.7135	Intermediate Similarity	NPD3145	Approved
0.7135	Intermediate Similarity	NPD3144	Approved
0.7128	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD4582	Approved
0.7122	Intermediate Similarity	NPD4583	Approved
0.7114	Intermediate Similarity	NPD7034	Discontinued
0.7109	Intermediate Similarity	NPD7047	Phase 3
0.7093	Intermediate Similarity	NPD7477	Discontinued
0.7073	Intermediate Similarity	NPD4002	Approved
0.7073	Intermediate Similarity	NPD4004	Approved
0.7072	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD6377	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7153	Discontinued
0.7059	Intermediate Similarity	NPD8070	Approved
0.7059	Intermediate Similarity	NPD5604	Discontinued
0.7049	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD5718	Phase 2
0.7033	Intermediate Similarity	NPD3640	Phase 3
0.7033	Intermediate Similarity	NPD3641	Approved
0.7033	Intermediate Similarity	NPD3639	Approved
0.703	Intermediate Similarity	NPD2973	Approved
0.703	Intermediate Similarity	NPD2975	Approved
0.703	Intermediate Similarity	NPD2974	Approved
0.7022	Intermediate Similarity	NPD5177	Phase 3
0.702	Intermediate Similarity	NPD6841	Approved
0.702	Intermediate Similarity	NPD6843	Phase 3
0.702	Intermediate Similarity	NPD6842	Approved
0.7018	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7773	Phase 2
0.7	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4474	Approved
0.6994	Remote Similarity	NPD4475	Approved
0.699	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD6748	Discontinued
0.6983	Remote Similarity	NPD7466	Approved
0.6979	Remote Similarity	NPD3489	Phase 3
0.6978	Remote Similarity	NPD7526	Approved
0.6978	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD52	Approved
0.6973	Remote Similarity	NPD7438	Suspended
0.6959	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1613	Approved
0.6954	Remote Similarity	NPD6851	Approved
0.6954	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6853	Approved
0.695	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD8149	Discontinued
0.6947	Remote Similarity	NPD6107	Approved
0.6942	Remote Similarity	NPD5005	Approved
0.6942	Remote Similarity	NPD5006	Approved
0.6932	Remote Similarity	NPD2200	Suspended
0.6927	Remote Similarity	NPD4580	Approved
0.6923	Remote Similarity	NPD6297	Approved
0.6919	Remote Similarity	NPD4908	Phase 1
0.691	Remote Similarity	NPD3656	Approved
0.6907	Remote Similarity	NPD6042	Phase 2
0.6907	Remote Similarity	NPD42	Phase 2
0.6904	Remote Similarity	NPD2971	Approved
0.6904	Remote Similarity	NPD2968	Approved
0.6904	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD6090	Discontinued
0.6882	Remote Similarity	NPD3778	Approved
0.6878	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4083	Discontinued
0.6872	Remote Similarity	NPD3920	Phase 2
0.6863	Remote Similarity	NPD4605	Approved
0.6863	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD4604	Approved
0.6854	Remote Similarity	NPD2161	Phase 2
0.6852	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD2219	Phase 1
0.685	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD5722	Discontinued
0.684	Remote Similarity	NPD8153	Approved
0.684	Remote Similarity	NPD8152	Approved
0.6839	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD6111	Discontinued
0.6836	Remote Similarity	NPD6895	Approved
0.6836	Remote Similarity	NPD6896	Approved
0.6833	Remote Similarity	NPD3060	Approved
0.6832	Remote Similarity	NPD3922	Approved
0.6832	Remote Similarity	NPD3923	Approved
0.6832	Remote Similarity	NPD3921	Approved
0.6832	Remote Similarity	NPD3924	Approved
0.6831	Remote Similarity	NPD7019	Approved
0.6831	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD7020	Approved
0.6829	Remote Similarity	NPD4420	Approved
0.6823	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD2843	Phase 2
0.6816	Remote Similarity	NPD2845	Phase 2
0.6813	Remote Similarity	NPD6666	Approved
0.6813	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6667	Approved
0.6811	Remote Similarity	NPD5267	Discontinued
0.681	Remote Similarity	NPD7222	Phase 2
0.6809	Remote Similarity	NPD2977	Approved
0.6809	Remote Similarity	NPD4585	Approved
0.6809	Remote Similarity	NPD2978	Approved
0.6809	Remote Similarity	NPD7169	Suspended
0.6806	Remote Similarity	NPD6746	Phase 2

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