NPASS Compound

Structure

NPC473041 OpenBabel07101718192D 27 31 0 0 1 0 0 0 0 0999 V2000 1.4635 -1.6151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4249 -3.5670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4947 -5.0052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5642 -1.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5883 -1.1517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7516 -0.6687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7391 0.0781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8507 0.4578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5917 -1.4762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7516 -2.6009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3108 -1.7129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6822 -0.3671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8206 -1.1294 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1911 -1.3657 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5883 -2.1178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9149 -1.1517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9961 -0.8532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9149 -2.1178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4283 -1.6348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1725 -0.9506 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4619 -3.3322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4631 -1.6781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9961 -2.4164 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 2.4278 -3.3132 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4249 -2.6009 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9953 -4.1782 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 5 6 2 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 7 8 1 0 0 0 0 7 17 1 0 0 0 0 8 24 1 0 0 0 0 9 14 1 0 0 0 0 10 15 2 0 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 12 24 1 0 0 0 0 13 9 1 6 0 0 0 14 4 1 1 0 0 0 14 20 1 0 0 0 0 15 26 1 0 0 0 0 16 17 1 0 0 0 0 16 18 2 0 0 0 0 17 19 2 0 0 0 0 18 23 1 0 0 0 0 19 22 1 0 0 0 0 19 23 1 0 0 0 0 20 22 1 1 0 0 0 20 24 1 0 0 0 0 21 25 2 0 0 0 0 21 27 1 0 0 0 0 22 21 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	368.21
Volume:	381.468
LogP:	4.022
LogD:	4.037
LogS:	-3.749
# Rotatable Bonds:	4
TPSA:	54.56
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.845
Synthetic Accessibility Score:	5.057
Fsp3:	0.591
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.086
MDCK Permeability:	1.8505937987356447e-05
Pgp-inhibitor:	0.089
Pgp-substrate:	0.97
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.812
30% Bioavailability (F30%):	0.799

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.988
Plasma Protein Binding (PPB):	82.37743377685547%
Volume Distribution (VD):	1.791
Pgp-substrate:	12.950626373291016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.848
CYP1A2-substrate:	0.96
CYP2C19-inhibitor:	0.801
CYP2C19-substrate:	0.893
CYP2C9-inhibitor:	0.337
CYP2C9-substrate:	0.8
CYP2D6-inhibitor:	0.94
CYP2D6-substrate:	0.918
CYP3A4-inhibitor:	0.928
CYP3A4-substrate:	0.823

ADMET: Excretion

Clearance (CL):	11.215
Half-life (T1/2):	0.138

ADMET: Toxicity

hERG Blockers:	0.831
Human Hepatotoxicity (H-HT):	0.449
Drug-inuced Liver Injury (DILI):	0.243
AMES Toxicity:	0.317
Rat Oral Acute Toxicity:	0.978
Maximum Recommended Daily Dose:	0.949
Skin Sensitization:	0.138
Carcinogencity:	0.876
Eye Corrosion:	0.003
Eye Irritation:	0.032
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC473041

Natural Product ID:	NPC473041
*Common Name:**	Isovoacangine
IUPAC Name:	n.a.
Synonyms:	Isovoacangine
Standard InCHIKey:	FPUHKQMDWMVBRI-RUGRQLENSA-N
Standard InCHI:	InChI=1S/C22H28N2O3/c1-4-14-9-13-11-22(21(25)27-3)19-17(7-8-24(12-13)20(14)22)16-6-5-15(26-2)10-18(16)23-19/h5-6,10,13-14,20,23H,4,7-9,11-12H2,1-3H3/t13-,14-,20-,22+/m0/s1
SMILES:	CC[C@H]1C[C@H]2C[C@]3(c4c(CCN(C2)[C@@H]13)c1ccc(cc1[nH]4)OC)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL360427
PubChem CID:	44393473
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002748] Ibogan-type alkaloids

*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
NPO32495	tabernaemontana calcarea	Species	Apocynaceae	Eukaryota	n.a.	Madagascar rainforest	n.a.	PMID[12713407]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18778099]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18778099]
NPO25727	Tabernaemontana divaricata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23944995]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[24773071]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	stem-bark	Pahang, Malaysia	2003-JUN	PMID[25919190]
NPO25727	Tabernaemontana divaricata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26231157]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26918761]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27077800]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29319316]
NPO25727	Tabernaemontana divaricata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30169038]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30869890]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32356659]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25727	Tabernaemontana divaricata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25727	Tabernaemontana divaricata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
EC50	1
IC50	10

Activity Type	# Activity
Cell Line	9
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[495106]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	9.4	ug.mL-1	PMID[495107]
NPT2615	Cell Line	HEK-293T	Homo sapiens	IC50	>	40000.0	nM	PMID[495108]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	35600.0	nM	PMID[495108]
NPT2170	Cell Line	RKO	Homo sapiens	IC50	>	40000.0	nM	PMID[495108]
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	11200.0	nM	PMID[495108]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	24400.0	nM	PMID[495108]
NPT165	Cell Line	HeLa	Homo sapiens	EC50	>	40000.0	nM	PMID[495109]
NPT2	Others	Unspecified		IC50	=	6000.0	nM	PMID[495108]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	40000.0	nM	PMID[495108]

☑ 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 NPC473041 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	428
0.1-0.2	2037
0.2-0.3	9597
0.3-0.4	9257
0.4-0.5	15302
0.5-0.6	3313
0.6-0.7	2155
0.7-0.8	504
0.8-0.85	48
0.85-0.9	39
0.9-0.95	14
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9495	High Similarity	NPC96321
0.9394	High Similarity	NPC330009
0.9275	High Similarity	NPC473105
0.9171	High Similarity	NPC329747
0.9045	High Similarity	NPC471304
0.899	High Similarity	NPC311906
0.8977	High Similarity	NPC81939
0.8952	High Similarity	NPC475720
0.8952	High Similarity	NPC474192
0.8935	High Similarity	NPC475666
0.8916	High Similarity	NPC469928
0.885	High Similarity	NPC475910
0.8732	High Similarity	NPC148183
0.8732	High Similarity	NPC152768
0.8705	High Similarity	NPC329858
0.8704	High Similarity	NPC475816
0.8667	High Similarity	NPC21638
0.8614	High Similarity	NPC4687
0.8599	High Similarity	NPC305984
0.8539	High Similarity	NPC473540
0.8513	High Similarity	NPC314333
0.85	High Similarity	NPC329793
0.8498	Intermediate Similarity	NPC478078
0.8468	Intermediate Similarity	NPC17437
0.8447	Intermediate Similarity	NPC87413
0.8409	Intermediate Similarity	NPC477066
0.8371	Intermediate Similarity	NPC478081
0.8371	Intermediate Similarity	NPC477067
0.8371	Intermediate Similarity	NPC478082
0.8341	Intermediate Similarity	NPC249583
0.8333	Intermediate Similarity	NPC169402
0.8325	Intermediate Similarity	NPC116238
0.8294	Intermediate Similarity	NPC303658
0.8287	Intermediate Similarity	NPC471762
0.8263	Intermediate Similarity	NPC60621
0.8256	Intermediate Similarity	NPC84478
0.8241	Intermediate Similarity	NPC55493
0.8235	Intermediate Similarity	NPC162730
0.823	Intermediate Similarity	NPC264176
0.8213	Intermediate Similarity	NPC39679
0.819	Intermediate Similarity	NPC478074
0.8166	Intermediate Similarity	NPC478080
0.8155	Intermediate Similarity	NPC285558
0.8146	Intermediate Similarity	NPC474116
0.8143	Intermediate Similarity	NPC310211
0.8143	Intermediate Similarity	NPC308137
0.8131	Intermediate Similarity	NPC174760
0.8131	Intermediate Similarity	NPC472099
0.8128	Intermediate Similarity	NPC72211
0.8128	Intermediate Similarity	NPC306376
0.8119	Intermediate Similarity	NPC66777
0.8116	Intermediate Similarity	NPC300156
0.8109	Intermediate Similarity	NPC471303
0.8093	Intermediate Similarity	NPC198503
0.8079	Intermediate Similarity	NPC243834
0.8079	Intermediate Similarity	NPC70956
0.8057	Intermediate Similarity	NPC472098
0.8047	Intermediate Similarity	NPC150239
0.8045	Intermediate Similarity	NPC260434
0.8043	Intermediate Similarity	NPC329982
0.8037	Intermediate Similarity	NPC194740
0.803	Intermediate Similarity	NPC70259
0.8019	Intermediate Similarity	NPC469592
0.8019	Intermediate Similarity	NPC471080
0.8018	Intermediate Similarity	NPC122436
0.8	Intermediate Similarity	NPC241024
0.798	Intermediate Similarity	NPC205934
0.798	Intermediate Similarity	NPC131017
0.798	Intermediate Similarity	NPC43787
0.7953	Intermediate Similarity	NPC247803
0.7953	Intermediate Similarity	NPC46561
0.7946	Intermediate Similarity	NPC184680
0.7944	Intermediate Similarity	NPC3207
0.7933	Intermediate Similarity	NPC162484
0.7923	Intermediate Similarity	NPC232727
0.7923	Intermediate Similarity	NPC476044
0.7923	Intermediate Similarity	NPC267423
0.7917	Intermediate Similarity	NPC208084
0.7911	Intermediate Similarity	NPC470785
0.7911	Intermediate Similarity	NPC470784
0.7911	Intermediate Similarity	NPC101350
0.791	Intermediate Similarity	NPC196251
0.791	Intermediate Similarity	NPC111602
0.791	Intermediate Similarity	NPC63199
0.791	Intermediate Similarity	NPC102338
0.789	Intermediate Similarity	NPC144452
0.7885	Intermediate Similarity	NPC291535
0.7885	Intermediate Similarity	NPC475112
0.7885	Intermediate Similarity	NPC475085
0.7877	Intermediate Similarity	NPC167860
0.7877	Intermediate Similarity	NPC123976
0.787	Intermediate Similarity	NPC469594
0.7867	Intermediate Similarity	NPC235685
0.7857	Intermediate Similarity	NPC45190
0.785	Intermediate Similarity	NPC39500
0.7844	Intermediate Similarity	NPC280799
0.783	Intermediate Similarity	NPC284685
0.7828	Intermediate Similarity	NPC157931
0.7821	Intermediate Similarity	NPC478083
0.7819	Intermediate Similarity	NPC195788
0.7819	Intermediate Similarity	NPC237901
0.7803	Intermediate Similarity	NPC474688
0.7798	Intermediate Similarity	NPC323969
0.7788	Intermediate Similarity	NPC214428
0.7783	Intermediate Similarity	NPC469734
0.7778	Intermediate Similarity	NPC74969
0.7778	Intermediate Similarity	NPC170114
0.7773	Intermediate Similarity	NPC476106
0.775	Intermediate Similarity	NPC176127
0.7745	Intermediate Similarity	NPC22476
0.7743	Intermediate Similarity	NPC473187
0.7741	Intermediate Similarity	NPC88923
0.7741	Intermediate Similarity	NPC100734
0.7741	Intermediate Similarity	NPC315634
0.7738	Intermediate Similarity	NPC179287
0.7736	Intermediate Similarity	NPC193777
0.7731	Intermediate Similarity	NPC470549
0.7723	Intermediate Similarity	NPC160381
0.7721	Intermediate Similarity	NPC475778
0.7718	Intermediate Similarity	NPC276517
0.7714	Intermediate Similarity	NPC295898
0.7713	Intermediate Similarity	NPC274640
0.7706	Intermediate Similarity	NPC184408
0.7703	Intermediate Similarity	NPC312870
0.7703	Intermediate Similarity	NPC294909
0.7703	Intermediate Similarity	NPC254240
0.7703	Intermediate Similarity	NPC128265
0.7703	Intermediate Similarity	NPC199851
0.7692	Intermediate Similarity	NPC260909
0.7689	Intermediate Similarity	NPC277350
0.7678	Intermediate Similarity	NPC223427
0.7678	Intermediate Similarity	NPC476098
0.7675	Intermediate Similarity	NPC131486
0.7674	Intermediate Similarity	NPC23294
0.7671	Intermediate Similarity	NPC193267
0.7671	Intermediate Similarity	NPC213530
0.7664	Intermediate Similarity	NPC201697
0.7653	Intermediate Similarity	NPC477065
0.7636	Intermediate Similarity	NPC225279
0.7636	Intermediate Similarity	NPC477533
0.7633	Intermediate Similarity	NPC474121
0.7628	Intermediate Similarity	NPC303951
0.7628	Intermediate Similarity	NPC11464
0.7628	Intermediate Similarity	NPC234999
0.7627	Intermediate Similarity	NPC303374
0.7623	Intermediate Similarity	NPC319232
0.7623	Intermediate Similarity	NPC24370
0.7621	Intermediate Similarity	NPC39370
0.7611	Intermediate Similarity	NPC473186
0.761	Intermediate Similarity	NPC472112
0.7608	Intermediate Similarity	NPC52557
0.76	Intermediate Similarity	NPC72980
0.7596	Intermediate Similarity	NPC13880
0.7594	Intermediate Similarity	NPC134848
0.7593	Intermediate Similarity	NPC187501
0.7593	Intermediate Similarity	NPC208284
0.7589	Intermediate Similarity	NPC118559
0.7589	Intermediate Similarity	NPC304307
0.7589	Intermediate Similarity	NPC261251
0.7589	Intermediate Similarity	NPC124920
0.7589	Intermediate Similarity	NPC473185
0.7589	Intermediate Similarity	NPC34580
0.7586	Intermediate Similarity	NPC94943
0.7585	Intermediate Similarity	NPC472295
0.7585	Intermediate Similarity	NPC269886
0.7585	Intermediate Similarity	NPC244543
0.7585	Intermediate Similarity	NPC247735
0.7585	Intermediate Similarity	NPC472210
0.7585	Intermediate Similarity	NPC81802
0.7581	Intermediate Similarity	NPC469743
0.7581	Intermediate Similarity	NPC469589
0.7574	Intermediate Similarity	NPC133609
0.7573	Intermediate Similarity	NPC92111
0.7573	Intermediate Similarity	NPC191489
0.757	Intermediate Similarity	NPC321428
0.7568	Intermediate Similarity	NPC280272
0.7564	Intermediate Similarity	NPC91868
0.7564	Intermediate Similarity	NPC63971
0.7559	Intermediate Similarity	NPC470930
0.7559	Intermediate Similarity	NPC185742
0.7559	Intermediate Similarity	NPC475847
0.7558	Intermediate Similarity	NPC48353
0.7558	Intermediate Similarity	NPC94157
0.7556	Intermediate Similarity	NPC100547
0.7555	Intermediate Similarity	NPC6786
0.7548	Intermediate Similarity	NPC19692
0.7548	Intermediate Similarity	NPC220151
0.7547	Intermediate Similarity	NPC199277
0.7547	Intermediate Similarity	NPC135887
0.7545	Intermediate Similarity	NPC214142
0.7542	Intermediate Similarity	NPC189079
0.7538	Intermediate Similarity	NPC189812
0.7538	Intermediate Similarity	NPC329688
0.7537	Intermediate Similarity	NPC190007
0.7536	Intermediate Similarity	NPC472113
0.7536	Intermediate Similarity	NPC79129
0.7536	Intermediate Similarity	NPC195461
0.7536	Intermediate Similarity	NPC249150
0.7536	Intermediate Similarity	NPC49196
0.7536	Intermediate Similarity	NPC81654

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 NPC473041 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	245
0.1-0.2	600
0.2-0.3	762
0.3-0.4	1358
0.4-0.5	2641
0.5-0.6	2422
0.6-0.7	978
0.7-0.8	138
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8636	High Similarity	NPD4118	Clinical (unspecified phase)
0.8513	High Similarity	NPD4499	Approved
0.8468	Intermediate Similarity	NPD8358	Approved
0.8213	Intermediate Similarity	NPD5658	Approved
0.8037	Intermediate Similarity	NPD5632	Approved
0.8017	Intermediate Similarity	NPD8363	Approved
0.8017	Intermediate Similarity	NPD8364	Approved
0.795	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7928	Intermediate Similarity	NPD4885	Approved
0.789	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7864	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.783	Intermediate Similarity	NPD7955	Approved
0.783	Intermediate Similarity	NPD7956	Approved
0.7819	Intermediate Similarity	NPD8467	Approved
0.7819	Intermediate Similarity	NPD8465	Approved
0.7819	Intermediate Similarity	NPD8466	Approved
0.7808	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7773	Intermediate Similarity	NPD3003	Approved
0.7767	Intermediate Similarity	NPD5512	Phase 3
0.7741	Intermediate Similarity	NPD7803	Approved
0.7731	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD4418	Discontinued
0.7717	Intermediate Similarity	NPD6242	Discontinued
0.7703	Intermediate Similarity	NPD4501	Approved
0.7703	Intermediate Similarity	NPD4500	Approved
0.77	Intermediate Similarity	NPD2916	Discontinued
0.7692	Intermediate Similarity	NPD8460	Approved
0.7692	Intermediate Similarity	NPD8426	Approved
0.7692	Intermediate Similarity	NPD8459	Approved
0.7692	Intermediate Similarity	NPD8425	Approved
0.7686	Intermediate Similarity	NPD6790	Phase 1
0.7682	Intermediate Similarity	NPD5482	Discontinued
0.7679	Intermediate Similarity	NPD4952	Phase 3
0.7674	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD8429	Approved
0.7673	Intermediate Similarity	NPD8428	Approved
0.7673	Intermediate Similarity	NPD8427	Approved
0.7668	Intermediate Similarity	NPD3259	Approved
0.7642	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD8016	Phase 3
0.7642	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7577	Intermediate Similarity	NPD4373	Phase 2
0.7573	Intermediate Similarity	NPD7708	Approved
0.7571	Intermediate Similarity	NPD1768	Approved
0.7569	Intermediate Similarity	NPD5293	Phase 2
0.756	Intermediate Similarity	NPD5003	Discontinued
0.7548	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD4601	Approved
0.7536	Intermediate Similarity	NPD4600	Approved
0.7511	Intermediate Similarity	NPD7194	Discontinued
0.7511	Intermediate Similarity	NPD7994	Phase 2
0.75	Intermediate Similarity	NPD1038	Approved
0.75	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7489	Intermediate Similarity	NPD5902	Approved
0.7489	Intermediate Similarity	NPD5903	Approved
0.7488	Intermediate Similarity	NPD5429	Discontinued
0.7464	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7454	Intermediate Similarity	NPD2509	Approved
0.7454	Intermediate Similarity	NPD2510	Approved
0.7445	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD8403	Phase 1
0.743	Intermediate Similarity	NPD6176	Phase 1
0.7412	Intermediate Similarity	NPD6962	Phase 2
0.7407	Intermediate Similarity	NPD7452	Approved
0.7407	Intermediate Similarity	NPD7453	Approved
0.7397	Intermediate Similarity	NPD7069	Discontinued
0.7395	Intermediate Similarity	NPD4795	Phase 2
0.7387	Intermediate Similarity	NPD6985	Discontinued
0.7382	Intermediate Similarity	NPD7417	Discontinued
0.7376	Intermediate Similarity	NPD3394	Approved
0.7376	Intermediate Similarity	NPD3393	Approved
0.7376	Intermediate Similarity	NPD3389	Approved
0.7371	Intermediate Similarity	NPD484	Approved
0.7364	Intermediate Similarity	NPD8489	Phase 1
0.7359	Intermediate Similarity	NPD3006	Discontinued
0.7357	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD6770	Approved
0.7352	Intermediate Similarity	NPD7470	Discontinued
0.7352	Intermediate Similarity	NPD5416	Discontinued
0.7349	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6550	Discontinued
0.733	Intermediate Similarity	NPD4889	Approved
0.7327	Intermediate Similarity	NPD1392	Approved
0.7327	Intermediate Similarity	NPD7222	Phase 2
0.7315	Intermediate Similarity	NPD5901	Discontinued
0.7309	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7309	Intermediate Similarity	NPD4429	Discontinued
0.7306	Intermediate Similarity	NPD5450	Discontinued
0.7294	Intermediate Similarity	NPD6376	Discontinued
0.7293	Intermediate Similarity	NPD5479	Discontinued
0.7292	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1739	Approved
0.729	Intermediate Similarity	NPD1740	Approved
0.7277	Intermediate Similarity	NPD6517	Phase 3
0.7273	Intermediate Similarity	NPD7558	Phase 2
0.7273	Intermediate Similarity	NPD2564	Approved
0.7273	Intermediate Similarity	NPD2565	Phase 2
0.726	Intermediate Similarity	NPD4506	Discontinued
0.7257	Intermediate Similarity	NPD5488	Discontinued
0.7252	Intermediate Similarity	NPD3257	Approved
0.7241	Intermediate Similarity	NPD6963	Approved
0.7241	Intermediate Similarity	NPD6964	Approved
0.7238	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD5913	Phase 3
0.7237	Intermediate Similarity	NPD7426	Phase 1
0.7232	Intermediate Similarity	NPD7395	Discontinued
0.7232	Intermediate Similarity	NPD3354	Phase 2
0.722	Intermediate Similarity	NPD5612	Discontinued
0.7212	Intermediate Similarity	NPD5256	Discontinued
0.721	Intermediate Similarity	NPD7853	Phase 2
0.7209	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD6716	Phase 1
0.7202	Intermediate Similarity	NPD7174	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD8091	Phase 3
0.72	Intermediate Similarity	NPD3258	Approved
0.7198	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6220	Phase 3
0.7185	Intermediate Similarity	NPD8359	Phase 2
0.7184	Intermediate Similarity	NPD4203	Approved
0.7184	Intermediate Similarity	NPD4204	Approved
0.7179	Intermediate Similarity	NPD4368	Phase 2
0.7177	Intermediate Similarity	NPD4948	Discontinued
0.7174	Intermediate Similarity	NPD5559	Phase 2
0.7174	Intermediate Similarity	NPD5014	Discontinued
0.7171	Intermediate Similarity	NPD3920	Phase 2
0.717	Intermediate Similarity	NPD802	Phase 2
0.7168	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD5930	Phase 3
0.7163	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD3825	Phase 3
0.7162	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD3947	Discontinued
0.715	Intermediate Similarity	NPD7948	Phase 1
0.7143	Intermediate Similarity	NPD5669	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6228	Discontinued
0.7129	Intermediate Similarity	NPD1326	Approved
0.7129	Intermediate Similarity	NPD1325	Approved
0.7123	Intermediate Similarity	NPD5530	Phase 1
0.7119	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD4502	Phase 2
0.71	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4511	Phase 1
0.7094	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD8255	Phase 2
0.7087	Intermediate Similarity	NPD7603	Discontinued
0.7085	Intermediate Similarity	NPD3816	Phase 1
0.7085	Intermediate Similarity	NPD3815	Phase 1
0.7079	Intermediate Similarity	NPD2844	Phase 3
0.7074	Intermediate Similarity	NPD7548	Discontinued
0.7074	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2187	Approved
0.7059	Intermediate Similarity	NPD2189	Approved
0.7056	Intermediate Similarity	NPD6590	Discontinued
0.7056	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD8102	Discontinued
0.7054	Intermediate Similarity	NPD4558	Phase 2
0.7045	Intermediate Similarity	NPD5601	Phase 2
0.7044	Intermediate Similarity	NPD5186	Approved
0.7044	Intermediate Similarity	NPD5183	Approved
0.7043	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD3922	Approved
0.7042	Intermediate Similarity	NPD3923	Approved
0.7042	Intermediate Similarity	NPD8100	Phase 3
0.7042	Intermediate Similarity	NPD3921	Approved
0.7042	Intermediate Similarity	NPD3924	Approved
0.704	Intermediate Similarity	NPD5067	Phase 2
0.704	Intermediate Similarity	NPD5475	Discontinued
0.704	Intermediate Similarity	NPD5066	Phase 2
0.7039	Intermediate Similarity	NPD7284	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD5805	Approved
0.7025	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6238	Discontinued
0.7009	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5866	Approved
0.7008	Intermediate Similarity	NPD8463	Approved
0.7005	Intermediate Similarity	NPD4548	Discontinued
0.7	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD5022	Discontinued
0.6996	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD6988	Phase 1
0.6986	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD4328	Approved
0.6977	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6251	Discontinued
0.6974	Remote Similarity	NPD3402	Phase 1
0.6971	Remote Similarity	NPD5473	Discontinued
0.6963	Remote Similarity	NPD6569	Phase 2
0.6955	Remote Similarity	NPD6991	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