NPASS Compound

Structure

NPC476095 OpenBabel07101719252D 45 56 0 0 1 0 0 0 0 0999 V2000 3.0581 -2.1553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4917 1.4320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5610 -2.0818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0447 -1.1763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0033 0.5971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6271 0.3611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5575 -1.6689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6931 -0.8139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6232 -1.0200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5766 0.8915 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9626 -1.9364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7085 -1.4585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0941 -0.6386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0187 -0.2527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7292 -1.7230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4324 -1.0369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6800 -1.6686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3223 0.7585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0700 -2.0070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3491 -1.1995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4627 -1.1376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1902 -0.6984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0689 -1.1237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1768 0.2806 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5920 0.2468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4335 -1.5550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3468 -1.5772 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6580 -0.9282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4993 -0.9061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4811 0.2574 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4386 -2.0585 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3540 -0.5609 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1832 -0.4422 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7932 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4678 -1.1294 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5609 -0.5609 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4541 0.5472 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7960 -1.6930 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1834 -1.0928 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4945 -0.7216 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 0.7165 -1.6051 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -0.5609 -1.3540 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9024 -0.6430 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.1577 -1.1896 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 4 1 0 0 0 0 2 5 1 0 0 0 0 3 44 1 0 0 0 0 4 22 2 0 0 0 0 5 23 2 0 0 0 0 6 8 2 0 0 0 0 6 10 1 0 0 0 0 7 9 2 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 10 25 2 0 0 0 0 11 26 2 0 0 0 0 12 28 2 0 0 0 0 13 29 2 0 0 0 0 14 16 1 0 0 0 0 14 37 1 0 0 0 0 15 17 1 0 0 0 0 15 38 1 0 0 0 0 16 40 1 0 0 0 0 17 41 1 0 0 0 0 18 30 1 0 0 0 0 19 27 1 0 0 0 0 19 31 1 0 0 0 0 20 22 1 0 0 0 0 20 40 1 0 0 0 0 21 23 1 0 0 0 0 21 41 1 0 0 0 0 22 24 1 0 0 0 0 23 27 1 0 0 0 0 24 18 1 1 0 0 0 24 32 1 0 0 0 0 25 28 1 0 0 0 0 25 37 1 0 0 0 0 26 29 1 0 0 0 0 26 38 1 0 0 0 0 27 39 1 6 0 0 0 28 42 1 0 0 0 0 29 43 1 0 0 0 0 30 37 1 6 0 0 0 30 40 1 0 0 0 0 31 38 1 6 0 0 0 31 41 1 0 0 0 0 32 33 1 0 0 0 0 32 34 1 0 0 0 0 33 37 1 0 0 0 0 33 42 1 0 0 0 0 34 43 1 0 0 0 0 34 45 1 0 0 0 0 35 38 1 0 0 0 0 35 39 1 0 0 0 0 35 43 1 0 0 0 0 36 39 1 0 0 0 0 36 42 1 0 0 0 0 36 45 1 0 0 0 0 39 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	600.35
Volume:	620.898
LogP:	4.793
LogD:	4.819
LogS:	-4.824
# Rotatable Bonds:	1
TPSA:	31.42
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	12
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.427
Synthetic Accessibility Score:	7.735
Fsp3:	0.59
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:	-5.068
MDCK Permeability:	2.1710600776714273e-05
Pgp-inhibitor:	0.983
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.648
20% Bioavailability (F20%):	0.987
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.313
Plasma Protein Binding (PPB):	71.91545104980469%
Volume Distribution (VD):	2.172
Pgp-substrate:	7.573182106018066%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.095
CYP2C19-inhibitor:	0.133
CYP2C19-substrate:	0.93
CYP2C9-inhibitor:	0.051
CYP2C9-substrate:	0.068
CYP2D6-inhibitor:	0.839
CYP2D6-substrate:	0.505
CYP3A4-inhibitor:	0.885
CYP3A4-substrate:	0.921

ADMET: Excretion

Clearance (CL):	11.003
Half-life (T1/2):	0.139

ADMET: Toxicity

hERG Blockers:	0.904
Human Hepatotoxicity (H-HT):	0.995
Drug-inuced Liver Injury (DILI):	0.575
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.966
Maximum Recommended Daily Dose:	0.996
Skin Sensitization:	0.588
Carcinogencity:	0.143
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC476095

Natural Product ID:	NPC476095
*Common Name:**	VNSZXMDTMMDDED-MYPRUQHWSA-N
IUPAC Name:	n.a.
Synonyms:	16-Methoxyisomatopensine
Standard InCHIKey:	VNSZXMDTMMDDED-MYPRUQHWSA-N
Standard InCHI:	InChI=1S/C39H44N4O2/c1-4-22-20-40-16-14-37-25-10-6-8-12-28(25)42-33(37)32(24(22)18-30(37)40)34-43-29-13-9-7-11-26(29)38-15-17-41-21-23(5-2)27(19-31(38)41)39(44-3,35(38)43)36(42)45-34/h4-13,24,27,30-36H,14-21H2,1-3H3/b22-4+,23-5+/t24-,27-,30-,31-,32-,33-,34+,35+,36+,37+,38+,39+/m0/s1
SMILES:	CC=C1CN2CCC34C2CC1C5C3N(C6C7(C8CC9C1(C7N(C5O6)C2=CC=CC=C21)CCN9CC8=CC)OC)C1=CC=CC=C41
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL525959
PubChem CID:	44559868
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002749] Strychnos 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
NPO26292	Strychnos matopensis	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398531]

☑ 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
IC50	4
Others	6

Activity Type	# Activity
Cell Line	1
Organism	6
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	24500.0	nM	PMID[453442]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	122.0	nM	PMID[453442]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1540.0	nM	PMID[453442]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	540.0	nM	PMID[453442]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	2530.0	nM	PMID[453442]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	2840.0	nM	PMID[453442]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	9520.0	nM	PMID[453442]
NPT2	Others	Unspecified		Ratio IC50	=	15.9	n.a.	PMID[453442]
NPT2	Others	Unspecified		Ratio IC50	=	45.3	n.a.	PMID[453442]
NPT2	Others	Unspecified		Ratio IC50	=	200.0	n.a.	PMID[453442]

☑ 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 NPC476095 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	448
0.1-0.2	1796
0.2-0.3	6428
0.3-0.4	23450
0.4-0.5	7905
0.5-0.6	2244
0.6-0.7	354
0.7-0.8	62
0.8-0.85	6
0.85-0.9	1
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9412	High Similarity	NPC285841
0.9146	High Similarity	NPC475420
0.8988	High Similarity	NPC473880
0.8343	Intermediate Similarity	NPC320147
0.8333	Intermediate Similarity	NPC473743
0.7978	Intermediate Similarity	NPC475097
0.7884	Intermediate Similarity	NPC162440
0.7513	Intermediate Similarity	NPC329833
0.7341	Intermediate Similarity	NPC264589
0.7268	Intermediate Similarity	NPC63047
0.7268	Intermediate Similarity	NPC475248
0.7241	Intermediate Similarity	NPC469735
0.7231	Intermediate Similarity	NPC221687
0.7188	Intermediate Similarity	NPC181928
0.7182	Intermediate Similarity	NPC225319
0.7175	Intermediate Similarity	NPC206592
0.7158	Intermediate Similarity	NPC256288
0.7151	Intermediate Similarity	NPC214626
0.7151	Intermediate Similarity	NPC251212
0.7151	Intermediate Similarity	NPC139085
0.7143	Intermediate Similarity	NPC282339
0.7143	Intermediate Similarity	NPC85651
0.7143	Intermediate Similarity	NPC286994
0.7143	Intermediate Similarity	NPC99632
0.712	Intermediate Similarity	NPC2933
0.711	Intermediate Similarity	NPC131977
0.7107	Intermediate Similarity	NPC97100
0.7107	Intermediate Similarity	NPC473375
0.7098	Intermediate Similarity	NPC229484
0.7086	Intermediate Similarity	NPC116519
0.7083	Intermediate Similarity	NPC259626
0.7079	Intermediate Similarity	NPC475763
0.707	Intermediate Similarity	NPC223242
0.7062	Intermediate Similarity	NPC292675
0.7049	Intermediate Similarity	NPC469741
0.7047	Intermediate Similarity	NPC473615
0.7026	Intermediate Similarity	NPC105055
0.7026	Intermediate Similarity	NPC22689
0.7015	Intermediate Similarity	NPC471512
0.7006	Intermediate Similarity	NPC469740
0.7005	Intermediate Similarity	NPC139373
0.699	Remote Similarity	NPC126066
0.6978	Remote Similarity	NPC113946
0.697	Remote Similarity	NPC34717
0.6923	Remote Similarity	NPC477157
0.6923	Remote Similarity	NPC477156
0.6908	Remote Similarity	NPC475422
0.6907	Remote Similarity	NPC52262
0.69	Remote Similarity	NPC90967
0.6897	Remote Similarity	NPC52801
0.6893	Remote Similarity	NPC471945
0.6893	Remote Similarity	NPC87755
0.6893	Remote Similarity	NPC471950
0.6892	Remote Similarity	NPC469450
0.6882	Remote Similarity	NPC472106
0.6859	Remote Similarity	NPC260075
0.6853	Remote Similarity	NPC473298
0.6847	Remote Similarity	NPC301501
0.683	Remote Similarity	NPC469451
0.683	Remote Similarity	NPC469452
0.6818	Remote Similarity	NPC25401
0.6818	Remote Similarity	NPC470483
0.6812	Remote Similarity	NPC475259
0.681	Remote Similarity	NPC475602
0.6798	Remote Similarity	NPC138830
0.678	Remote Similarity	NPC477179
0.6774	Remote Similarity	NPC472120
0.6774	Remote Similarity	NPC472101
0.677	Remote Similarity	NPC329932
0.676	Remote Similarity	NPC472100
0.675	Remote Similarity	NPC470485
0.6748	Remote Similarity	NPC477178
0.6748	Remote Similarity	NPC477180
0.6748	Remote Similarity	NPC477181
0.6748	Remote Similarity	NPC254850
0.6721	Remote Similarity	NPC478076
0.6715	Remote Similarity	NPC470490
0.6705	Remote Similarity	NPC243162
0.6702	Remote Similarity	NPC476425
0.6699	Remote Similarity	NPC471951
0.6699	Remote Similarity	NPC471946
0.6667	Remote Similarity	NPC472115
0.6667	Remote Similarity	NPC475359
0.6667	Remote Similarity	NPC472114
0.6667	Remote Similarity	NPC191817
0.6649	Remote Similarity	NPC29285
0.6633	Remote Similarity	NPC159963
0.6631	Remote Similarity	NPC477158
0.663	Remote Similarity	NPC212799
0.6589	Remote Similarity	NPC251936
0.6574	Remote Similarity	NPC288110
0.6564	Remote Similarity	NPC321211
0.6556	Remote Similarity	NPC311330
0.6555	Remote Similarity	NPC477173
0.6555	Remote Similarity	NPC477174
0.6553	Remote Similarity	NPC67904
0.6546	Remote Similarity	NPC203202
0.6546	Remote Similarity	NPC476441
0.6546	Remote Similarity	NPC264482
0.6545	Remote Similarity	NPC33507
0.6543	Remote Similarity	NPC248117
0.6526	Remote Similarity	NPC159815
0.6524	Remote Similarity	NPC476493
0.6524	Remote Similarity	NPC470488
0.6516	Remote Similarity	NPC476492
0.65	Remote Similarity	NPC14994
0.6489	Remote Similarity	NPC160113
0.6489	Remote Similarity	NPC193410
0.6489	Remote Similarity	NPC476220
0.648	Remote Similarity	NPC22082
0.648	Remote Similarity	NPC133261
0.648	Remote Similarity	NPC186284
0.6474	Remote Similarity	NPC313757
0.6473	Remote Similarity	NPC475489
0.6443	Remote Similarity	NPC242269
0.6436	Remote Similarity	NPC61013
0.6435	Remote Similarity	NPC472027
0.6435	Remote Similarity	NPC234772
0.6429	Remote Similarity	NPC473781
0.6429	Remote Similarity	NPC476326
0.6429	Remote Similarity	NPC35390
0.6429	Remote Similarity	NPC470631
0.6429	Remote Similarity	NPC470484
0.6421	Remote Similarity	NPC286871
0.6421	Remote Similarity	NPC176983
0.6421	Remote Similarity	NPC472117
0.6419	Remote Similarity	NPC473757
0.6418	Remote Similarity	NPC21425
0.6415	Remote Similarity	NPC470491
0.6409	Remote Similarity	NPC162748
0.6406	Remote Similarity	NPC214960
0.6406	Remote Similarity	NPC279527
0.64	Remote Similarity	NPC307396
0.64	Remote Similarity	NPC473486
0.64	Remote Similarity	NPC322621
0.64	Remote Similarity	NPC475316
0.6395	Remote Similarity	NPC471564
0.6394	Remote Similarity	NPC127178
0.6393	Remote Similarity	NPC318525
0.6393	Remote Similarity	NPC10653
0.6391	Remote Similarity	NPC469722
0.6382	Remote Similarity	NPC477159
0.6382	Remote Similarity	NPC472104
0.6376	Remote Similarity	NPC304837
0.6376	Remote Similarity	NPC476258
0.6373	Remote Similarity	NPC167724
0.6373	Remote Similarity	NPC224970
0.6373	Remote Similarity	NPC223595
0.6372	Remote Similarity	NPC127996
0.6368	Remote Similarity	NPC201424
0.6368	Remote Similarity	NPC472102
0.6368	Remote Similarity	NPC81229
0.6368	Remote Similarity	NPC473458
0.6368	Remote Similarity	NPC309531
0.6368	Remote Similarity	NPC255229
0.6364	Remote Similarity	NPC187827
0.6364	Remote Similarity	NPC472105
0.6359	Remote Similarity	NPC96901
0.6355	Remote Similarity	NPC128582
0.6354	Remote Similarity	NPC477155
0.6351	Remote Similarity	NPC231924
0.6347	Remote Similarity	NPC222046
0.6345	Remote Similarity	NPC477187
0.6345	Remote Similarity	NPC186669
0.634	Remote Similarity	NPC469915
0.6333	Remote Similarity	NPC130251
0.6324	Remote Similarity	NPC276430
0.6316	Remote Similarity	NPC154922
0.6316	Remote Similarity	NPC36495
0.6316	Remote Similarity	NPC469461
0.6313	Remote Similarity	NPC218594
0.6313	Remote Similarity	NPC6974
0.6313	Remote Similarity	NPC99043
0.6308	Remote Similarity	NPC126492
0.6295	Remote Similarity	NPC470126
0.6295	Remote Similarity	NPC471513
0.629	Remote Similarity	NPC318086
0.629	Remote Similarity	NPC471506
0.6289	Remote Similarity	NPC469462
0.6284	Remote Similarity	NPC472103
0.6276	Remote Similarity	NPC477185
0.6276	Remote Similarity	NPC285622
0.6267	Remote Similarity	NPC253580
0.6267	Remote Similarity	NPC473006
0.6264	Remote Similarity	NPC145754
0.6263	Remote Similarity	NPC285941
0.6263	Remote Similarity	NPC123241
0.6262	Remote Similarity	NPC473178
0.6262	Remote Similarity	NPC302001
0.6257	Remote Similarity	NPC66936
0.6257	Remote Similarity	NPC243756
0.6256	Remote Similarity	NPC473837
0.6256	Remote Similarity	NPC472118
0.6256	Remote Similarity	NPC473005
0.625	Remote Similarity	NPC476428
0.625	Remote Similarity	NPC293458
0.6244	Remote Similarity	NPC140311
0.6243	Remote Similarity	NPC473297
0.6239	Remote Similarity	NPC120239
0.6237	Remote Similarity	NPC109787

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 NPC476095 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	233
0.1-0.2	629
0.2-0.3	708
0.3-0.4	2339
0.4-0.5	3986
0.5-0.6	1199
0.6-0.7	48
0.7-0.8	8
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
0.7529	Intermediate Similarity	NPD8401	Approved
0.7529	Intermediate Similarity	NPD8402	Approved
0.7529	Intermediate Similarity	NPD8400	Approved
0.7056	Intermediate Similarity	NPD5743	Approved
0.7056	Intermediate Similarity	NPD5741	Approved
0.7056	Intermediate Similarity	NPD5742	Approved
0.7	Intermediate Similarity	NPD4121	Phase 3
0.7	Intermediate Similarity	NPD4120	Approved
0.6414	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD6070	Approved
0.6386	Remote Similarity	NPD6069	Approved
0.6377	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD7487	Discontinued
0.6333	Remote Similarity	NPD6606	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD8240	Discontinued
0.6321	Remote Similarity	NPD6037	Discontinued
0.63	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD5600	Discontinued
0.6262	Remote Similarity	NPD7262	Phase 1
0.6239	Remote Similarity	NPD7824	Approved
0.6205	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6193	Remote Similarity	NPD4365	Phase 2
0.6178	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6171	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.6157	Remote Similarity	NPD7790	Approved
0.6157	Remote Similarity	NPD7953	Approved
0.6157	Remote Similarity	NPD7950	Approved
0.6157	Remote Similarity	NPD7951	Approved
0.6157	Remote Similarity	NPD7789	Approved
0.6157	Remote Similarity	NPD7952	Approved
0.6157	Remote Similarity	NPD7791	Approved
0.615	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.615	Remote Similarity	NPD7731	Approved
0.615	Remote Similarity	NPD7730	Approved
0.615	Remote Similarity	NPD6978	Phase 2
0.6139	Remote Similarity	NPD7252	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD7271	Approved
0.6131	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD6455	Phase 3
0.6105	Remote Similarity	NPD5579	Approved
0.6105	Remote Similarity	NPD5576	Approved
0.6098	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD8630	Approved
0.6092	Remote Similarity	NPD6025	Phase 1
0.608	Remote Similarity	NPD5938	Phase 3
0.6077	Remote Similarity	NPD4602	Approved
0.6067	Remote Similarity	NPD6489	Phase 3
0.6064	Remote Similarity	NPD5881	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD7633	Discontinued
0.6061	Remote Similarity	NPD4116	Approved
0.6057	Remote Similarity	NPD6320	Approved
0.605	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD5318	Discontinued
0.6041	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6041	Remote Similarity	NPD3983	Phase 3
0.6038	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.603	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.601	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.601	Remote Similarity	NPD8060	Phase 1
0.601	Remote Similarity	NPD5913	Phase 3
0.6	Remote Similarity	NPD1721	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7606	Phase 3
0.5992	Remote Similarity	NPD7921	Approved
0.599	Remote Similarity	NPD7479	Phase 2
0.5989	Remote Similarity	NPD7785	Clinical (unspecified phase)
0.5989	Remote Similarity	NPD7295	Approved
0.5972	Remote Similarity	NPD5582	Discontinued
0.5967	Remote Similarity	NPD5182	Approved
0.5967	Remote Similarity	NPD5185	Approved
0.5967	Remote Similarity	NPD5184	Approved
0.5966	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.5961	Remote Similarity	NPD6879	Phase 2
0.5961	Remote Similarity	NPD6878	Phase 2
0.5961	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.5953	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.595	Remote Similarity	NPD7854	Phase 2
0.5946	Remote Similarity	NPD7073	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD8358	Approved
0.5939	Remote Similarity	NPD4796	Discontinued
0.5938	Remote Similarity	NPD6357	Discontinued
0.5934	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.5933	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.5928	Remote Similarity	NPD1769	Discontinued
0.5926	Remote Similarity	NPD7478	Approved
0.5913	Remote Similarity	NPD8025	Phase 2
0.5904	Remote Similarity	NPD5932	Phase 3
0.5904	Remote Similarity	NPD6622	Phase 1
0.5904	Remote Similarity	NPD5931	Phase 3
0.5904	Remote Similarity	NPD5595	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD5933	Phase 3
0.5902	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.59	Remote Similarity	NPD3975	Discontinued
0.5899	Remote Similarity	NPD5993	Phase 1
0.5882	Remote Similarity	NPD6301	Phase 2
0.5882	Remote Similarity	NPD5629	Discontinued
0.5882	Remote Similarity	NPD7082	Approved
0.5879	Remote Similarity	NPD6379	Discontinued
0.5879	Remote Similarity	NPD7890	Discontinued
0.5871	Remote Similarity	NPD5997	Discontinued
0.5867	Remote Similarity	NPD6524	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD8020	Approved
0.5865	Remote Similarity	NPD4951	Discontinued
0.5865	Remote Similarity	NPD8021	Approved
0.586	Remote Similarity	NPD2093	Discontinued
0.5857	Remote Similarity	NPD8364	Approved
0.5857	Remote Similarity	NPD8363	Approved
0.5851	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD7259	Approved
0.585	Remote Similarity	NPD5531	Discontinued
0.5844	Remote Similarity	NPD7781	Approved
0.5844	Remote Similarity	NPD7780	Approved
0.5843	Remote Similarity	NPD8467	Approved
0.5843	Remote Similarity	NPD8465	Approved
0.5843	Remote Similarity	NPD8466	Approved
0.5838	Remote Similarity	NPD19	Approved
0.5838	Remote Similarity	NPD5657	Phase 3
0.5838	Remote Similarity	NPD1742	Approved
0.5838	Remote Similarity	NPD1743	Approved
0.5833	Remote Similarity	NPD8352	Phase 1
0.5833	Remote Similarity	NPD8353	Approved
0.5833	Remote Similarity	NPD8355	Approved
0.583	Remote Similarity	NPD5891	Approved
0.5825	Remote Similarity	NPD7962	Phase 2
0.5824	Remote Similarity	NPD2913	Approved
0.5824	Remote Similarity	NPD2914	Approved
0.582	Remote Similarity	NPD5060	Phase 1
0.5816	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD7599	Phase 2
0.5815	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.5815	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD4644	Clinical (unspecified phase)
0.581	Remote Similarity	NPD5758	Clinical (unspecified phase)
0.581	Remote Similarity	NPD6281	Approved
0.581	Remote Similarity	NPD7247	Discontinued
0.581	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.5808	Remote Similarity	NPD7717	Approved
0.5808	Remote Similarity	NPD7716	Approved
0.5808	Remote Similarity	NPD7734	Approved
0.5799	Remote Similarity	NPD2039	Approved
0.5799	Remote Similarity	NPD2038	Approved
0.5792	Remote Similarity	NPD7200	Approved
0.5792	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.5792	Remote Similarity	NPD7593	Clinical (unspecified phase)
0.5792	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.5787	Remote Similarity	NPD4601	Approved
0.5787	Remote Similarity	NPD7600	Phase 2
0.5787	Remote Similarity	NPD4600	Approved
0.5775	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD8354	Approved
0.5773	Remote Similarity	NPD7222	Phase 2
0.5769	Remote Similarity	NPD6227	Discontinued
0.5763	Remote Similarity	NPD519	Approved
0.5763	Remote Similarity	NPD7249	Approved
0.5763	Remote Similarity	NPD7250	Approved
0.5756	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.5753	Remote Similarity	NPD8425	Approved
0.5753	Remote Similarity	NPD6644	Discontinued
0.5753	Remote Similarity	NPD8426	Approved
0.5753	Remote Similarity	NPD8459	Approved
0.5753	Remote Similarity	NPD8460	Approved
0.5751	Remote Similarity	NPD3329	Clinical (unspecified phase)
0.5749	Remote Similarity	NPD5596	Phase 2
0.5749	Remote Similarity	NPD8281	Discontinued
0.5743	Remote Similarity	NPD5680	Clinical (unspecified phase)
0.5731	Remote Similarity	NPD5181	Approved
0.5731	Remote Similarity	NPD5179	Approved
0.5731	Remote Similarity	NPD5180	Approved
0.5728	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.5722	Remote Similarity	NPD8315	Phase 1
0.5721	Remote Similarity	NPD5862	Discovery
0.5721	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.5721	Remote Similarity	NPD4520	Approved
0.5721	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.5721	Remote Similarity	NPD7726	Phase 1
0.5721	Remote Similarity	NPD7877	Suspended
0.572	Remote Similarity	NPD8428	Approved
0.572	Remote Similarity	NPD8429	Approved
0.572	Remote Similarity	NPD8427	Approved
0.5714	Remote Similarity	NPD7454	Approved
0.5714	Remote Similarity	NPD7455	Approved
0.5714	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4430	Phase 2
0.5707	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.5707	Remote Similarity	NPD7275	Approved
0.5707	Remote Similarity	NPD8156	Discontinued
0.5706	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.57	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.57	Remote Similarity	NPD4550	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD1405	Approved
0.5699	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.5694	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.5694	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.5693	Remote Similarity	NPD7474	Suspended
0.5691	Remote Similarity	NPD6789	Approved
0.5688	Remote Similarity	NPD6307	Clinical (unspecified phase)
0.5687	Remote Similarity	NPD7444	Clinical (unspecified phase)

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