NPASS Compound

Structure

CID73644 OpenBabel06191715412D 39 43 0 0 1 0 0 0 0 0999 V2000 -0.0568 -2.0477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7099 4.1028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5503 0.4545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8484 -2.8454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5392 -1.2938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9967 3.9194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3767 4.2741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4805 4.6733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4791 3.2984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6867 4.0968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6853 2.7218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8501 2.4533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7003 2.9441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7002 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2493 1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8501 -0.4908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3998 0.9809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6990 0.9810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8501 -1.4713 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6062 4.5018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7891 3.1210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8501 1.4718 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7002 0.9809 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5503 2.4533 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.9810 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2494 2.4533 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6990 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8501 -0.4908 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3999 2.9441 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9953 2.5445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5503 1.4717 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7459 -1.8702 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.0991 2.9437 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.7087 5.4775 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5669 -0.5007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0977 1.5688 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3999 3.9252 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 21 1 0 0 0 0 5 34 1 0 0 0 0 6 34 1 0 0 0 0 7 35 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 2 0 0 0 0 11 22 2 0 0 0 0 12 22 1 0 0 0 0 13 14 1 0 0 0 0 14 25 1 0 0 0 0 15 17 1 0 0 0 0 15 24 1 0 0 0 0 16 18 1 0 0 0 0 16 27 1 0 0 0 0 17 33 1 0 0 0 0 18 32 1 0 0 0 0 19 26 1 0 0 0 0 19 28 1 0 0 0 0 20 1 1 6 0 0 0 20 29 1 0 0 0 0 20 34 1 0 0 0 0 21 36 2 0 0 0 0 21 39 1 0 0 0 0 22 31 1 0 0 0 0 23 13 1 6 0 0 0 23 24 1 0 0 0 0 23 26 1 0 0 0 0 24 32 1 1 0 0 0 25 30 1 0 0 0 0 25 32 1 1 0 0 0 26 33 1 1 0 0 0 27 30 1 0 0 0 0 27 35 1 6 0 0 0 28 29 1 0 0 0 0 28 37 1 1 0 0 0 29 33 1 1 0 0 0 30 39 1 1 0 0 0 31 35 1 0 0 0 0 31 38 2 0 0 0 0 32 3 1 1 0 0 0 33 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	538.38
Volume:	580.514
LogP:	4.362
LogD:	4.593
LogS:	-4.507
# Rotatable Bonds:	7
TPSA:	70.08
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.519
Synthetic Accessibility Score:	4.775
Fsp3:	0.758
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.781
MDCK Permeability:	2.3931197574711405e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.725
Human Intestinal Absorption (HIA):	0.071
20% Bioavailability (F20%):	0.136
30% Bioavailability (F30%):	0.534

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.162
Plasma Protein Binding (PPB):	68.7542724609375%
Volume Distribution (VD):	1.732
Pgp-substrate:	20.85740089416504%

ADMET: Metabolism

CYP1A2-inhibitor:	0.072
CYP1A2-substrate:	0.142
CYP2C19-inhibitor:	0.04
CYP2C19-substrate:	0.96
CYP2C9-inhibitor:	0.253
CYP2C9-substrate:	0.063
CYP2D6-inhibitor:	0.909
CYP2D6-substrate:	0.851
CYP3A4-inhibitor:	0.859
CYP3A4-substrate:	0.726

ADMET: Excretion

Clearance (CL):	4.817
Half-life (T1/2):	0.559

ADMET: Toxicity

hERG Blockers:	0.904
Human Hepatotoxicity (H-HT):	0.816
Drug-inuced Liver Injury (DILI):	0.861
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.878
Maximum Recommended Daily Dose:	0.019
Skin Sensitization:	0.912
Carcinogencity:	0.183
Eye Corrosion:	0.019
Eye Irritation:	0.035
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC73644

Natural Product ID:	NPC73644
*Common Name:**	[(3R,4R,5R,8R,9S,10R,13S,14S,16S,17S)-3-[Benzoyl(Methyl)Amino]-17-[(1S)-1-(Dimethylamino)Ethyl]-16-Hydroxy-10,13-Dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-Tetradecahydro-1H-Cyclopenta[A]Phenanthren-4-Yl] Acetate
IUPAC Name:	[(3R,4R,5R,8R,9S,10R,13S,14S,16S,17S)-3-[benzoyl(methyl)amino]-17-[(1S)-1-(dimethylamino)ethyl]-16-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-4-yl] acetate
Synonyms:
Standard InCHIKey:	CEFWIVSCALJZMU-XBZOXOFBSA-N
Standard InCHI:	InChI=1S/C33H50N2O4/c1-20(34(5)6)29-28(37)19-26-23-13-14-25-30(39-21(2)36)27(35(7)31(38)22-11-9-8-10-12-22)16-18-32(25,3)24(23)15-17-33(26,29)4/h8-12,20,23-30,37H,13-19H2,1-7H3/t20-,23+,24-,25-,26-,27+,28-,29-,30+,32+,33-/m0/s1
SMILES:	C[C@@H]([C@H]1[C@H](C[C@H]2[C@@H]3CC[C@H]4[C@H]([C@@H](CC[C@]4(C)[C@H]3CC[C@]12C)N(C)C(=O)c1ccccc1)OC(=O)C)O)N(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3391994
PubChem CID:	10626238
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001194] Oxosteroids [CHEMONTID:0003060] 16-oxosteroids

*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
NPO26156	Mahurea palustris	Species	Calophyllaceae	Eukaryota	leaves	French Guiana	1996-OCT	PMID[16038535]
NPO26204	Arisaema curvatum	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26204	Arisaema curvatum	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26423	Scaevola racemigera	Species	Goodeniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26446	Lecanora frustulosa	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23047	Streptomyces griseoviridis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO18582	Cosmospora butyri	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26372	Sarcandra hainanensis	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25707	Euchaeta russelli	Species	Euchaetidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23214	Drosera congolana	Species	Droseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26556	Pterocephalus pinardi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26673	Casearia ilicifolia	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26156	Mahurea palustris	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26204	Arisaema curvatum	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26471	Lenormandia smithiae	Species	Rhodomelaceae	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	57

Activity Type	# Activity
Cell Line	57

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[492328]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	89536.48	nM	PMID[492328]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT572	Cell Line	DMS-273	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	76913.04	nM	PMID[492328]
NPT573	Cell Line	M19-MEL	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT574	Cell Line	XF498	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT731	Cell Line	LXFL 529	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT576	Cell Line	DMS-114	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT578	Cell Line	SNB-78	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT579	Cell Line	DLD-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]
NPT732	Cell Line	HOP-18	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[492328]

☑ 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 NPC73644 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	202
0.1-0.2	923
0.2-0.3	2110
0.3-0.4	7914
0.4-0.5	22837
0.5-0.6	7508
0.6-0.7	1144
0.7-0.8	56
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9	High Similarity	NPC475427
0.7959	Intermediate Similarity	NPC79698
0.7879	Intermediate Similarity	NPC476750
0.7751	Intermediate Similarity	NPC476749
0.7697	Intermediate Similarity	NPC126458
0.7647	Intermediate Similarity	NPC473962
0.7349	Intermediate Similarity	NPC275839
0.7333	Intermediate Similarity	NPC470274
0.7317	Intermediate Similarity	NPC94602
0.7279	Intermediate Similarity	NPC473573
0.7258	Intermediate Similarity	NPC36607
0.7211	Intermediate Similarity	NPC246904
0.7189	Intermediate Similarity	NPC205
0.7189	Intermediate Similarity	NPC184195
0.7189	Intermediate Similarity	NPC166521
0.7189	Intermediate Similarity	NPC124690
0.7189	Intermediate Similarity	NPC172769
0.7189	Intermediate Similarity	NPC281470
0.7161	Intermediate Similarity	NPC105114
0.7161	Intermediate Similarity	NPC239990
0.7161	Intermediate Similarity	NPC89923
0.7161	Intermediate Similarity	NPC152850
0.7161	Intermediate Similarity	NPC71933
0.716	Intermediate Similarity	NPC161069
0.7117	Intermediate Similarity	NPC475128
0.7097	Intermediate Similarity	NPC136453
0.7063	Intermediate Similarity	NPC203486
0.7048	Intermediate Similarity	NPC473541
0.7043	Intermediate Similarity	NPC163578
0.7043	Intermediate Similarity	NPC108276
0.7025	Intermediate Similarity	NPC157311
0.7025	Intermediate Similarity	NPC475138
0.7019	Intermediate Similarity	NPC478140
0.7006	Intermediate Similarity	NPC212799
0.7005	Intermediate Similarity	NPC475316
0.7005	Intermediate Similarity	NPC473486
0.6989	Remote Similarity	NPC40539
0.6988	Remote Similarity	NPC260194
0.6988	Remote Similarity	NPC138775
0.6981	Remote Similarity	NPC44805
0.6981	Remote Similarity	NPC8761
0.6965	Remote Similarity	NPC223590
0.6957	Remote Similarity	NPC126516
0.6957	Remote Similarity	NPC470631
0.6957	Remote Similarity	NPC35390
0.6957	Remote Similarity	NPC48929
0.6957	Remote Similarity	NPC473781
0.695	Remote Similarity	NPC473837
0.6931	Remote Similarity	NPC140311
0.6919	Remote Similarity	NPC93343
0.6894	Remote Similarity	NPC132847
0.689	Remote Similarity	NPC263493
0.689	Remote Similarity	NPC269398
0.6886	Remote Similarity	NPC475578
0.6886	Remote Similarity	NPC328824
0.6875	Remote Similarity	NPC72915
0.6875	Remote Similarity	NPC475489
0.6875	Remote Similarity	NPC253738
0.6867	Remote Similarity	NPC209509
0.6867	Remote Similarity	NPC473922
0.6867	Remote Similarity	NPC5620
0.6863	Remote Similarity	NPC106593
0.6854	Remote Similarity	NPC30171
0.6852	Remote Similarity	NPC329913
0.6835	Remote Similarity	NPC473220
0.6835	Remote Similarity	NPC470753
0.6832	Remote Similarity	NPC313663
0.6829	Remote Similarity	NPC473667
0.6818	Remote Similarity	NPC472679
0.6818	Remote Similarity	NPC472680
0.6807	Remote Similarity	NPC476978
0.6807	Remote Similarity	NPC471516
0.6786	Remote Similarity	NPC135121
0.6772	Remote Similarity	NPC470765
0.677	Remote Similarity	NPC246913
0.675	Remote Similarity	NPC69496
0.6747	Remote Similarity	NPC139326
0.6746	Remote Similarity	NPC246412
0.6731	Remote Similarity	NPC213126
0.6731	Remote Similarity	NPC317474
0.6731	Remote Similarity	NPC169485
0.6731	Remote Similarity	NPC291027
0.6731	Remote Similarity	NPC84281
0.673	Remote Similarity	NPC171007
0.673	Remote Similarity	NPC190849
0.6728	Remote Similarity	NPC233910
0.6728	Remote Similarity	NPC245836
0.6707	Remote Similarity	NPC471264
0.6707	Remote Similarity	NPC471265
0.6706	Remote Similarity	NPC476757
0.6706	Remote Similarity	NPC129666
0.6702	Remote Similarity	NPC327699
0.6702	Remote Similarity	NPC221687
0.6687	Remote Similarity	NPC213969
0.6687	Remote Similarity	NPC472678
0.6687	Remote Similarity	NPC472656
0.6687	Remote Similarity	NPC165726
0.6685	Remote Similarity	NPC11149
0.6683	Remote Similarity	NPC476496
0.6667	Remote Similarity	NPC98424
0.6667	Remote Similarity	NPC97100
0.6667	Remote Similarity	NPC470278
0.6667	Remote Similarity	NPC470884
0.6667	Remote Similarity	NPC477217
0.6667	Remote Similarity	NPC275576
0.6667	Remote Similarity	NPC201244
0.6667	Remote Similarity	NPC92784
0.6667	Remote Similarity	NPC476133
0.6667	Remote Similarity	NPC473375
0.6667	Remote Similarity	NPC178662
0.6647	Remote Similarity	NPC197682
0.6647	Remote Similarity	NPC105717
0.6646	Remote Similarity	NPC472681
0.6645	Remote Similarity	NPC202015
0.6633	Remote Similarity	NPC475223
0.6631	Remote Similarity	NPC52262
0.663	Remote Similarity	NPC203005
0.6629	Remote Similarity	NPC217801
0.6627	Remote Similarity	NPC239762
0.6627	Remote Similarity	NPC163392
0.6627	Remote Similarity	NPC153007
0.6625	Remote Similarity	NPC169913
0.6625	Remote Similarity	NPC470648
0.661	Remote Similarity	NPC225319
0.6608	Remote Similarity	NPC473602
0.6606	Remote Similarity	NPC127741
0.6604	Remote Similarity	NPC474847
0.6601	Remote Similarity	NPC9274
0.6599	Remote Similarity	NPC246983
0.6599	Remote Similarity	NPC475448
0.6599	Remote Similarity	NPC474695
0.659	Remote Similarity	NPC122590
0.6588	Remote Similarity	NPC145113
0.6587	Remote Similarity	NPC168113
0.6584	Remote Similarity	NPC40488
0.6581	Remote Similarity	NPC310467
0.6579	Remote Similarity	NPC471623
0.6564	Remote Similarity	NPC246079
0.6557	Remote Similarity	NPC278272
0.6557	Remote Similarity	NPC120667
0.6554	Remote Similarity	NPC235460
0.6552	Remote Similarity	NPC279442
0.655	Remote Similarity	NPC94687
0.655	Remote Similarity	NPC470579
0.655	Remote Similarity	NPC476495
0.655	Remote Similarity	NPC106840
0.6548	Remote Similarity	NPC176226
0.6548	Remote Similarity	NPC248287
0.6548	Remote Similarity	NPC234548
0.6548	Remote Similarity	NPC473440
0.6545	Remote Similarity	NPC293377
0.6545	Remote Similarity	NPC260045
0.6545	Remote Similarity	NPC76785
0.6545	Remote Similarity	NPC9687
0.6545	Remote Similarity	NPC471754
0.6545	Remote Similarity	NPC475336
0.6545	Remote Similarity	NPC475598
0.6545	Remote Similarity	NPC273907
0.6545	Remote Similarity	NPC474787
0.6545	Remote Similarity	NPC317882
0.6545	Remote Similarity	NPC471629
0.6545	Remote Similarity	NPC473400
0.6545	Remote Similarity	NPC206211
0.6545	Remote Similarity	NPC151706
0.6545	Remote Similarity	NPC90194
0.6545	Remote Similarity	NPC118099
0.6545	Remote Similarity	NPC475318
0.6545	Remote Similarity	NPC474855
0.6545	Remote Similarity	NPC49577
0.6545	Remote Similarity	NPC306001
0.6545	Remote Similarity	NPC473300
0.6545	Remote Similarity	NPC79465
0.6545	Remote Similarity	NPC474811
0.6545	Remote Similarity	NPC453583
0.6545	Remote Similarity	NPC275170
0.6545	Remote Similarity	NPC324251
0.6545	Remote Similarity	NPC476102
0.6541	Remote Similarity	NPC285394
0.6529	Remote Similarity	NPC262077
0.6527	Remote Similarity	NPC307357
0.6527	Remote Similarity	NPC476259
0.6527	Remote Similarity	NPC475373
0.6527	Remote Similarity	NPC268841
0.6527	Remote Similarity	NPC46098
0.6516	Remote Similarity	NPC169328
0.6513	Remote Similarity	NPC473558
0.6512	Remote Similarity	NPC2501
0.651	Remote Similarity	NPC33372
0.651	Remote Similarity	NPC67246
0.65	Remote Similarity	NPC326895
0.65	Remote Similarity	NPC472106
0.65	Remote Similarity	NPC472574
0.6497	Remote Similarity	NPC190663
0.6497	Remote Similarity	NPC471512
0.6495	Remote Similarity	NPC215892
0.6495	Remote Similarity	NPC321072
0.6495	Remote Similarity	NPC242662
0.6495	Remote Similarity	NPC191193
0.6494	Remote Similarity	NPC286551
0.6491	Remote Similarity	NPC225648

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 NPC73644 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	135
0.1-0.2	461
0.2-0.3	815
0.3-0.4	1902
0.4-0.5	3607
0.5-0.6	1907
0.6-0.7	314
0.7-0.8	9
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7862	Intermediate Similarity	NPD8165	Discontinued
0.7657	Intermediate Similarity	NPD8658	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7962	Phase 2
0.7293	Intermediate Similarity	NPD7683	Discontinued
0.7255	Intermediate Similarity	NPD6792	Phase 3
0.7233	Intermediate Similarity	NPD6817	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6295	Approved
0.7188	Intermediate Similarity	NPD6294	Approved
0.7143	Intermediate Similarity	NPD7795	Phase 2
0.7107	Intermediate Similarity	NPD6623	Phase 3
0.7091	Intermediate Similarity	NPD7295	Approved
0.7083	Intermediate Similarity	NPD7606	Phase 3
0.7076	Intermediate Similarity	NPD7011	Discontinued
0.7062	Intermediate Similarity	NPD7997	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7478	Approved
0.6988	Remote Similarity	NPD8323	Discontinued
0.6988	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7961	Discontinued
0.6928	Remote Similarity	NPD7487	Discontinued
0.6923	Remote Similarity	NPD2634	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5581	Approved
0.6867	Remote Similarity	NPD7082	Approved
0.6846	Remote Similarity	NPD7094	Approved
0.6846	Remote Similarity	NPD6858	Approved
0.6832	Remote Similarity	NPD7714	Approved
0.6832	Remote Similarity	NPD7715	Approved
0.6826	Remote Similarity	NPD7259	Approved
0.6805	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD6345	Approved
0.6797	Remote Similarity	NPD6343	Approved
0.679	Remote Similarity	NPD8416	Discontinued
0.678	Remote Similarity	NPD7793	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD2820	Phase 3
0.6755	Remote Similarity	NPD4766	Approved
0.675	Remote Similarity	NPD2613	Approved
0.6748	Remote Similarity	NPD8643	Discontinued
0.6746	Remote Similarity	NPD7236	Approved
0.6743	Remote Similarity	NPD7599	Phase 2
0.6731	Remote Similarity	NPD2609	Approved
0.6731	Remote Similarity	NPD4217	Approved
0.6731	Remote Similarity	NPD4218	Approved
0.6731	Remote Similarity	NPD2608	Approved
0.6731	Remote Similarity	NPD3624	Phase 2
0.6731	Remote Similarity	NPD3131	Approved
0.6731	Remote Similarity	NPD2612	Approved
0.6731	Remote Similarity	NPD2611	Approved
0.6731	Remote Similarity	NPD4216	Approved
0.6731	Remote Similarity	NPD4215	Approved
0.6731	Remote Similarity	NPD3132	Approved
0.6731	Remote Similarity	NPD2610	Approved
0.6728	Remote Similarity	NPD3087	Approved
0.6728	Remote Similarity	NPD2573	Approved
0.6728	Remote Similarity	NPD3615	Approved
0.6728	Remote Similarity	NPD3614	Approved
0.6728	Remote Similarity	NPD2570	Approved
0.6728	Remote Similarity	NPD2566	Approved
0.6728	Remote Similarity	NPD3089	Approved
0.6728	Remote Similarity	NPD3088	Approved
0.6728	Remote Similarity	NPD4746	Phase 3
0.6728	Remote Similarity	NPD2574	Discontinued
0.6728	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD4745	Approved
0.6728	Remote Similarity	NPD2571	Approved
0.6728	Remote Similarity	NPD3616	Approved
0.6728	Remote Similarity	NPD3090	Approved
0.6709	Remote Similarity	NPD1482	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD2365	Approved
0.6707	Remote Similarity	NPD6073	Approved
0.6707	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7600	Phase 2
0.6702	Remote Similarity	NPD7693	Approved
0.6688	Remote Similarity	NPD2584	Suspended
0.6686	Remote Similarity	NPD8239	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7602	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7854	Phase 2
0.6684	Remote Similarity	NPD7497	Discontinued
0.6667	Remote Similarity	NPD2846	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4576	Approved
0.6667	Remote Similarity	NPD4574	Approved
0.6649	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7239	Suspended
0.6647	Remote Similarity	NPD7720	Phase 2
0.6647	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD4686	Approved
0.6646	Remote Similarity	NPD4677	Discontinued
0.6646	Remote Similarity	NPD4684	Phase 3
0.6646	Remote Similarity	NPD4685	Phase 3
0.6626	Remote Similarity	NPD8118	Discontinued
0.6626	Remote Similarity	NPD7713	Phase 3
0.6623	Remote Similarity	NPD5991	Approved
0.6623	Remote Similarity	NPD5990	Approved
0.6623	Remote Similarity	NPD7610	Discontinued
0.6623	Remote Similarity	NPD2607	Approved
0.6623	Remote Similarity	NPD6065	Approved
0.6606	Remote Similarity	NPD5725	Approved
0.6606	Remote Similarity	NPD8173	Phase 2
0.6606	Remote Similarity	NPD8172	Phase 2
0.6605	Remote Similarity	NPD4738	Phase 2
0.6605	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD7511	Approved
0.6587	Remote Similarity	NPD7512	Approved
0.6587	Remote Similarity	NPD7939	Discontinued
0.6584	Remote Similarity	NPD4177	Approved
0.6584	Remote Similarity	NPD4175	Approved
0.6579	Remote Similarity	NPD8435	Approved
0.6579	Remote Similarity	NPD8361	Approved
0.6579	Remote Similarity	NPD8360	Approved
0.6571	Remote Similarity	NPD8417	Discontinued
0.6571	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD4705	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD4214	Discontinued
0.6562	Remote Similarity	NPD5653	Discontinued
0.6548	Remote Similarity	NPD4152	Approved
0.6541	Remote Similarity	NPD3549	Approved
0.6541	Remote Similarity	NPD5157	Phase 1
0.6541	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD3550	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD5159	Phase 2
0.6541	Remote Similarity	NPD3547	Approved
0.6536	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD7105	Phase 1
0.6529	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7177	Discontinued
0.6514	Remote Similarity	NPD5086	Approved
0.6512	Remote Similarity	NPD6631	Clinical (unspecified phase)
0.651	Remote Similarity	NPD8146	Phase 2
0.6506	Remote Similarity	NPD6544	Discontinued
0.6503	Remote Similarity	NPD6039	Approved
0.65	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5578	Approved
0.6497	Remote Similarity	NPD3589	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD6485	Discontinued
0.6485	Remote Similarity	NPD4153	Approved
0.6481	Remote Similarity	NPD3626	Phase 3
0.6481	Remote Similarity	NPD5759	Approved
0.6471	Remote Similarity	NPD2650	Approved
0.6471	Remote Similarity	NPD2652	Approved
0.6471	Remote Similarity	NPD3598	Phase 3
0.6462	Remote Similarity	NPD8485	Approved
0.646	Remote Similarity	NPD6564	Approved
0.646	Remote Similarity	NPD6565	Approved
0.646	Remote Similarity	NPD6563	Approved
0.6458	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD5579	Approved
0.6456	Remote Similarity	NPD5576	Approved
0.6452	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD7679	Phase 2
0.645	Remote Similarity	NPD8161	Suspended
0.6442	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD8069	Phase 3
0.6429	Remote Similarity	NPD3648	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD4233	Approved
0.6424	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD4234	Approved
0.6415	Remote Similarity	NPD7437	Approved
0.6415	Remote Similarity	NPD7436	Approved
0.6415	Remote Similarity	NPD5618	Discontinued
0.6413	Remote Similarity	NPD6894	Phase 1
0.6413	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD7510	Approved
0.6407	Remote Similarity	NPD8125	Discontinued
0.6402	Remote Similarity	NPD2754	Discontinued
0.6398	Remote Similarity	NPD2199	Approved
0.6398	Remote Similarity	NPD2198	Approved
0.6398	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD7810	Phase 3
0.6396	Remote Similarity	NPD7811	Phase 3
0.6395	Remote Similarity	NPD8131	Suspended
0.6395	Remote Similarity	NPD6552	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD5119	Approved
0.6386	Remote Similarity	NPD5121	Approved
0.6386	Remote Similarity	NPD5120	Approved
0.6381	Remote Similarity	NPD6997	Phase 2
0.638	Remote Similarity	NPD3661	Approved
0.638	Remote Similarity	NPD7084	Phase 3
0.638	Remote Similarity	NPD3662	Phase 3
0.638	Remote Similarity	NPD3663	Approved
0.638	Remote Similarity	NPD3664	Approved
0.638	Remote Similarity	NPD5204	Approved
0.6379	Remote Similarity	NPD5942	Approved
0.6379	Remote Similarity	NPD5941	Approved
0.6375	Remote Similarity	NPD7814	Approved
0.6369	Remote Similarity	NPD6852	Discontinued
0.6369	Remote Similarity	NPD4479	Discontinued
0.6369	Remote Similarity	NPD7009	Phase 2
0.6364	Remote Similarity	NPD4619	Approved
0.6364	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4621	Approved
0.6364	Remote Similarity	NPD8315	Phase 1
0.6359	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD6609	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD3519	Discontinued
0.6346	Remote Similarity	NPD5162	Approved
0.6343	Remote Similarity	NPD6144	Discontinued
0.6343	Remote Similarity	NPD6273	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