NPASS Compound

Structure

NPC472846 OpenBabel07101718332D 47 54 0 0 1 0 0 0 0 0999 V2000 -6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6759 -4.2239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3506 -4.6778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6019 0.8226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1596 -4.0900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9328 1.5657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5629 -4.2710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2929 -0.1285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0551 -3.0955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9546 1.3578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6674 -3.2765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 -0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1416 -2.6887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6456 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4765 -2.6887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4546 -2.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1237 -2.1535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1674 -1.7377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9546 -3.7627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0373 -2.5602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.1674 -1.7377 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.9328 -3.5547 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5479 -4.6762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9033 -2.0602 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 35 1 0 0 0 0 2 37 1 0 0 0 0 3 44 1 0 0 0 0 4 6 2 0 0 0 0 4 8 1 0 0 0 0 5 7 2 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 8 15 2 0 0 0 0 9 16 2 0 0 0 0 10 17 2 0 0 0 0 11 19 2 0 0 0 0 12 20 1 0 0 0 0 12 22 1 0 0 0 0 13 18 1 0 0 0 0 13 45 1 0 0 0 0 14 46 1 0 0 0 0 15 17 1 0 0 0 0 15 23 1 0 0 0 0 16 19 1 0 0 0 0 16 24 1 0 0 0 0 17 36 1 0 0 0 0 18 20 1 0 0 0 0 18 35 1 1 0 0 0 19 38 1 0 0 0 0 20 39 1 6 0 0 0 21 14 1 6 0 0 0 21 31 1 0 0 0 0 21 47 1 0 0 0 0 22 45 1 0 0 0 0 22 46 1 1 0 0 0 23 25 2 0 0 0 0 23 27 1 0 0 0 0 24 26 2 0 0 0 0 24 28 1 0 0 0 0 25 26 1 0 0 0 0 25 32 1 0 0 0 0 26 33 1 0 0 0 0 27 28 2 0 0 0 0 27 36 1 0 0 0 0 28 38 1 0 0 0 0 29 30 1 0 0 0 0 29 31 1 0 0 0 0 29 40 1 6 0 0 0 30 34 1 0 0 0 0 30 41 1 1 0 0 0 31 44 1 1 0 0 0 32 37 1 0 0 0 0 32 42 2 0 0 0 0 33 37 1 0 0 0 0 33 43 2 0 0 0 0 34 38 1 6 0 0 0 34 47 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	644.25
Volume:	622.266
LogP:	2.153
LogD:	2.519
LogS:	-6.816
# Rotatable Bonds:	6
TPSA:	167.74
# H-Bond Aceptor:	13
# H-Bond Donor:	5
# Rings:	8
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.173
Synthetic Accessibility Score:	4.896
Fsp3:	0.412
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:	-5.895
MDCK Permeability:	5.103572675579926e-06
Pgp-inhibitor:	0.043
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.91
20% Bioavailability (F20%):	0.88
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.215
Plasma Protein Binding (PPB):	88.7446517944336%
Volume Distribution (VD):	1.205
Pgp-substrate:	6.722238540649414%

ADMET: Metabolism

CYP1A2-inhibitor:	0.063
CYP1A2-substrate:	0.98
CYP2C19-inhibitor:	0.077
CYP2C19-substrate:	0.749
CYP2C9-inhibitor:	0.295
CYP2C9-substrate:	0.076
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.166
CYP3A4-inhibitor:	0.2
CYP3A4-substrate:	0.803

ADMET: Excretion

Clearance (CL):	3.792
Half-life (T1/2):	0.046

ADMET: Toxicity

hERG Blockers:	0.559
Human Hepatotoxicity (H-HT):	0.661
Drug-inuced Liver Injury (DILI):	0.976
AMES Toxicity:	0.862
Rat Oral Acute Toxicity:	0.054
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.701
Carcinogencity:	0.738
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.907

Download Data

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

Natural Product: NPC472846

Natural Product ID:	NPC472846
*Common Name:**	WMXBPIZAQBGEPB-RXBINXNASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WMXBPIZAQBGEPB-RXBINXNASA-N
Standard InCHI:	InChI=1S/C34H36N4O9/c1-35-18-13-45-22(12-20(18)39)46-14-21-31(44-3)29(40)30(41)34(47-21)38-19-11-7-5-9-16(19)24-26-25(32(42)37(2)33(26)43)23-15-8-4-6-10-17(15)36-27(23)28(24)38/h4-11,18,20-22,29-31,34-36,39-41H,12-14H2,1-3H3/t18-,20-,21+,22-,29+,30+,31+,34+/m0/s1
SMILES:	CNC1COC(CC1O)OCC2C(C(C(C(O2)N3C4=CC=CC=C4C5=C6C(=C7C8=CC=CC=C8NC7=C53)C(=O)N(C6=O)C)O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3589064
PubChem CID:	10930283
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000210] Carbazoles [CHEMONTID:0001865] Pyrrolocarbazoles [CHEMONTID:0001866] Indolocarbazoles

*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
NPO33195	actinomadura melliaura atcc 39691	Species	Thermomonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26091285]

☑ 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
MIC	4
Others	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	Activity	=	16.6	%	PMID[567746]
NPT306	Cell Line	PC-3	Homo sapiens	Activity	=	36.4	%	PMID[567746]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	29.4	%	PMID[567746]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	120000.0	nM	PMID[567746]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	60000.0	nM	PMID[567746]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	120000.0	nM	PMID[567746]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	120000.0	nM	PMID[567746]

☑ 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 NPC472846 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	436
0.1-0.2	2208
0.2-0.3	11769
0.3-0.4	19245
0.4-0.5	5037
0.5-0.6	2797
0.6-0.7	1132
0.7-0.8	66
0.8-0.85	1
0.85-0.9	3
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9419	High Similarity	NPC472845
0.9295	High Similarity	NPC472207
0.8755	High Similarity	NPC472843
0.8701	High Similarity	NPC472842
0.85	High Similarity	NPC107836
0.7882	Intermediate Similarity	NPC1203
0.7654	Intermediate Similarity	NPC191382
0.7654	Intermediate Similarity	NPC56109
0.7573	Intermediate Similarity	NPC174788
0.7566	Intermediate Similarity	NPC45048
0.7531	Intermediate Similarity	NPC313884
0.7531	Intermediate Similarity	NPC98371
0.7528	Intermediate Similarity	NPC279589
0.7449	Intermediate Similarity	NPC155444
0.7397	Intermediate Similarity	NPC52254
0.7384	Intermediate Similarity	NPC162860
0.7375	Intermediate Similarity	NPC478157
0.7355	Intermediate Similarity	NPC82070
0.7347	Intermediate Similarity	NPC475271
0.7344	Intermediate Similarity	NPC476114
0.7333	Intermediate Similarity	NPC31700
0.7311	Intermediate Similarity	NPC478158
0.7311	Intermediate Similarity	NPC477548
0.73	Intermediate Similarity	NPC54420
0.7284	Intermediate Similarity	NPC281049
0.7262	Intermediate Similarity	NPC57453
0.7222	Intermediate Similarity	NPC263937
0.7222	Intermediate Similarity	NPC94428
0.722	Intermediate Similarity	NPC75634
0.716	Intermediate Similarity	NPC33949
0.7143	Intermediate Similarity	NPC477714
0.712	Intermediate Similarity	NPC476492
0.712	Intermediate Similarity	NPC476491
0.7102	Intermediate Similarity	NPC477715
0.7075	Intermediate Similarity	NPC132329
0.707	Intermediate Similarity	NPC478029
0.705	Intermediate Similarity	NPC471564
0.702	Intermediate Similarity	NPC274842
0.7012	Intermediate Similarity	NPC477065
0.7008	Intermediate Similarity	NPC89987
0.6996	Remote Similarity	NPC473800
0.6992	Remote Similarity	NPC478028
0.6987	Remote Similarity	NPC476874
0.6987	Remote Similarity	NPC470205
0.6984	Remote Similarity	NPC475258
0.698	Remote Similarity	NPC236424
0.698	Remote Similarity	NPC306644
0.698	Remote Similarity	NPC70155
0.697	Remote Similarity	NPC476493
0.6955	Remote Similarity	NPC223791
0.6955	Remote Similarity	NPC107077
0.6953	Remote Similarity	NPC325976
0.6951	Remote Similarity	NPC313640
0.6942	Remote Similarity	NPC474905
0.6939	Remote Similarity	NPC244856
0.6935	Remote Similarity	NPC160898
0.6929	Remote Similarity	NPC472844
0.692	Remote Similarity	NPC471506
0.6917	Remote Similarity	NPC193761
0.6917	Remote Similarity	NPC155143
0.6912	Remote Similarity	NPC478009
0.6912	Remote Similarity	NPC478010
0.6911	Remote Similarity	NPC54744
0.6902	Remote Similarity	NPC475969
0.6902	Remote Similarity	NPC475859
0.6895	Remote Similarity	NPC312645
0.6895	Remote Similarity	NPC249428
0.6888	Remote Similarity	NPC476115
0.6877	Remote Similarity	NPC909
0.6877	Remote Similarity	NPC475338
0.6875	Remote Similarity	NPC475506
0.6868	Remote Similarity	NPC14812
0.6865	Remote Similarity	NPC64216
0.6863	Remote Similarity	NPC470730
0.6863	Remote Similarity	NPC477175
0.6857	Remote Similarity	NPC475422
0.6844	Remote Similarity	NPC87755
0.684	Remote Similarity	NPC478006
0.6833	Remote Similarity	NPC81654
0.6833	Remote Similarity	NPC313985
0.6833	Remote Similarity	NPC249150
0.6833	Remote Similarity	NPC49196
0.6833	Remote Similarity	NPC79129
0.6833	Remote Similarity	NPC195461
0.6829	Remote Similarity	NPC320968
0.6827	Remote Similarity	NPC472285
0.6826	Remote Similarity	NPC91179
0.682	Remote Similarity	NPC149708
0.682	Remote Similarity	NPC171317
0.6816	Remote Similarity	NPC314882
0.6815	Remote Similarity	NPC477979
0.6811	Remote Similarity	NPC475424
0.6811	Remote Similarity	NPC472762
0.6811	Remote Similarity	NPC79107
0.6809	Remote Similarity	NPC165743
0.68	Remote Similarity	NPC473310
0.6797	Remote Similarity	NPC326363
0.6792	Remote Similarity	NPC100321
0.6789	Remote Similarity	NPC234999
0.6774	Remote Similarity	NPC89508
0.677	Remote Similarity	NPC474877
0.6754	Remote Similarity	NPC131273
0.6754	Remote Similarity	NPC473441
0.6752	Remote Similarity	NPC315467
0.675	Remote Similarity	NPC50503
0.675	Remote Similarity	NPC473640
0.6749	Remote Similarity	NPC317701
0.6741	Remote Similarity	NPC476514
0.6737	Remote Similarity	NPC324091
0.6737	Remote Similarity	NPC469470
0.6737	Remote Similarity	NPC469501
0.6735	Remote Similarity	NPC244741
0.6734	Remote Similarity	NPC475778
0.6732	Remote Similarity	NPC477176
0.6732	Remote Similarity	NPC470729
0.6722	Remote Similarity	NPC293917
0.672	Remote Similarity	NPC472027
0.6719	Remote Similarity	NPC474896
0.6718	Remote Similarity	NPC63279
0.6716	Remote Similarity	NPC472436
0.6709	Remote Similarity	NPC472097
0.6707	Remote Similarity	NPC472291
0.6707	Remote Similarity	NPC234078
0.6707	Remote Similarity	NPC221100
0.6706	Remote Similarity	NPC476818
0.6705	Remote Similarity	NPC477177
0.6705	Remote Similarity	NPC282033
0.6702	Remote Similarity	NPC260909
0.6695	Remote Similarity	NPC195314
0.6695	Remote Similarity	NPC175474
0.6694	Remote Similarity	NPC277350
0.6693	Remote Similarity	NPC31097
0.6693	Remote Similarity	NPC79386
0.6692	Remote Similarity	NPC297642
0.668	Remote Similarity	NPC272174
0.668	Remote Similarity	NPC469743
0.668	Remote Similarity	NPC63031
0.6679	Remote Similarity	NPC472434
0.6679	Remote Similarity	NPC473565
0.6667	Remote Similarity	NPC94541
0.6667	Remote Similarity	NPC470843
0.6667	Remote Similarity	NPC69843
0.6667	Remote Similarity	NPC115282
0.6653	Remote Similarity	NPC470731
0.6653	Remote Similarity	NPC126066
0.6653	Remote Similarity	NPC471192
0.6653	Remote Similarity	NPC17059
0.664	Remote Similarity	NPC314957
0.664	Remote Similarity	NPC229348
0.6639	Remote Similarity	NPC227582
0.6639	Remote Similarity	NPC476073
0.6634	Remote Similarity	NPC470901
0.6626	Remote Similarity	NPC312870
0.6626	Remote Similarity	NPC128265
0.6626	Remote Similarity	NPC199851
0.6626	Remote Similarity	NPC252338
0.6626	Remote Similarity	NPC294909
0.6626	Remote Similarity	NPC254240
0.6625	Remote Similarity	NPC85066
0.6625	Remote Similarity	NPC181502
0.6624	Remote Similarity	NPC472109
0.6624	Remote Similarity	NPC139291
0.6624	Remote Similarity	NPC472110
0.6624	Remote Similarity	NPC213629
0.6624	Remote Similarity	NPC472108
0.6619	Remote Similarity	NPC195788
0.6619	Remote Similarity	NPC237901
0.6612	Remote Similarity	NPC131887
0.6612	Remote Similarity	NPC165599
0.6612	Remote Similarity	NPC52557
0.6611	Remote Similarity	NPC472113
0.6607	Remote Similarity	NPC478011
0.6607	Remote Similarity	NPC478012
0.6605	Remote Similarity	NPC472435
0.6602	Remote Similarity	NPC229893
0.66	Remote Similarity	NPC6865
0.66	Remote Similarity	NPC153980
0.66	Remote Similarity	NPC31385
0.66	Remote Similarity	NPC75726
0.66	Remote Similarity	NPC110602
0.6599	Remote Similarity	NPC323927
0.6598	Remote Similarity	NPC300183
0.6594	Remote Similarity	NPC263117
0.6594	Remote Similarity	NPC242872
0.6594	Remote Similarity	NPC125181
0.6593	Remote Similarity	NPC153400
0.6592	Remote Similarity	NPC310618
0.659	Remote Similarity	NPC323752
0.6587	Remote Similarity	NPC36405
0.6587	Remote Similarity	NPC251936
0.6585	Remote Similarity	NPC473376
0.6584	Remote Similarity	NPC314176
0.6584	Remote Similarity	NPC74413
0.6578	Remote Similarity	NPC184680
0.6576	Remote Similarity	NPC19170
0.6574	Remote Similarity	NPC475602
0.6574	Remote Similarity	NPC473757
0.6571	Remote Similarity	NPC162730
0.6571	Remote Similarity	NPC474116
0.6569	Remote Similarity	NPC191489

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 NPC472846 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	218
0.1-0.2	567
0.2-0.3	1023
0.3-0.4	2508
0.4-0.5	2756
0.5-0.6	1685
0.6-0.7	362
0.7-0.8	28
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8678	High Similarity	NPD7772	Phase 3
0.832	Intermediate Similarity	NPD7181	Phase 3
0.8041	Intermediate Similarity	NPD7921	Approved
0.7852	Intermediate Similarity	NPD6456	Discontinued
0.7746	Intermediate Similarity	NPD7789	Approved
0.7746	Intermediate Similarity	NPD7951	Approved
0.7746	Intermediate Similarity	NPD7790	Approved
0.7746	Intermediate Similarity	NPD7950	Approved
0.7746	Intermediate Similarity	NPD7791	Approved
0.7746	Intermediate Similarity	NPD7952	Approved
0.7746	Intermediate Similarity	NPD7953	Approved
0.7654	Intermediate Similarity	NPD7781	Approved
0.7654	Intermediate Similarity	NPD7780	Approved
0.7613	Intermediate Similarity	NPD6978	Phase 2
0.7613	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD7730	Approved
0.7541	Intermediate Similarity	NPD7731	Approved
0.7531	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD6995	Phase 1
0.752	Intermediate Similarity	NPD7688	Phase 1
0.748	Intermediate Similarity	NPD7824	Approved
0.7459	Intermediate Similarity	NPD7271	Approved
0.7458	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD6717	Clinical (unspecified phase)
0.7276	Intermediate Similarity	NPD7716	Approved
0.7276	Intermediate Similarity	NPD7717	Approved
0.7254	Intermediate Similarity	NPD6455	Phase 3
0.7227	Intermediate Similarity	NPD8322	Phase 2
0.7208	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7073	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD7454	Approved
0.7149	Intermediate Similarity	NPD7455	Approved
0.7143	Intermediate Similarity	NPD8115	Approved
0.7143	Intermediate Similarity	NPD8114	Approved
0.7078	Intermediate Similarity	NPD8093	Discontinued
0.7023	Intermediate Similarity	NPD7769	Phase 3
0.7017	Intermediate Similarity	NPD7727	Phase 2
0.6969	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD8374	Phase 3
0.6901	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7001	Phase 3
0.6895	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD8329	Phase 3
0.6875	Remote Similarity	NPD3746	Discontinued
0.6867	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6858	Remote Similarity	NPD7770	Phase 3
0.6846	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD8317	Phase 2
0.6836	Remote Similarity	NPD8316	Phase 2
0.6835	Remote Similarity	NPD7944	Discontinued
0.6833	Remote Similarity	NPD4601	Approved
0.6833	Remote Similarity	NPD4600	Approved
0.6811	Remote Similarity	NPD8289	Discontinued
0.6805	Remote Similarity	NPD7817	Phase 1
0.68	Remote Similarity	NPD7878	Phase 2
0.679	Remote Similarity	NPD5426	Phase 3
0.6789	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD8094	Discontinued
0.6771	Remote Similarity	NPD8524	Approved
0.6762	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD7957	Phase 1
0.6758	Remote Similarity	NPD7887	Approved
0.6758	Remote Similarity	NPD7888	Approved
0.6741	Remote Similarity	NPD7776	Approved
0.6735	Remote Similarity	NPD8421	Discontinued
0.6735	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD7398	Approved
0.6729	Remote Similarity	NPD7397	Approved
0.6722	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD8375	Approved
0.6707	Remote Similarity	NPD7665	Phase 2
0.6707	Remote Similarity	NPD7666	Phase 3
0.6702	Remote Similarity	NPD8460	Approved
0.6702	Remote Similarity	NPD8459	Approved
0.6694	Remote Similarity	NPD7470	Discontinued
0.6694	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD7767	Approved
0.6692	Remote Similarity	NPD8250	Phase 2
0.6692	Remote Similarity	NPD7502	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.668	Remote Similarity	NPD8119	Discontinued
0.668	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8371	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6654	Remote Similarity	NPD5807	Phase 2
0.6653	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.664	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD6142	Phase 3
0.6627	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD4501	Approved
0.6626	Remote Similarity	NPD4500	Approved
0.6624	Remote Similarity	NPD3318	Approved
0.6624	Remote Similarity	NPD3319	Phase 1
0.6624	Remote Similarity	NPD3320	Approved
0.6623	Remote Similarity	NPD5021	Discontinued
0.6619	Remote Similarity	NPD8467	Approved
0.6619	Remote Similarity	NPD8466	Approved
0.6619	Remote Similarity	NPD8465	Approved
0.6613	Remote Similarity	NPD5835	Phase 3
0.6613	Remote Similarity	NPD5834	Phase 3
0.6604	Remote Similarity	NPD7860	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD8468	Phase 2
0.6589	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6615	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD8363	Approved
0.6583	Remote Similarity	NPD8364	Approved
0.6582	Remote Similarity	NPD8431	Approved
0.657	Remote Similarity	NPD6664	Approved
0.6569	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD7708	Approved
0.656	Remote Similarity	NPD8429	Approved
0.656	Remote Similarity	NPD8428	Approved
0.656	Remote Similarity	NPD8427	Approved
0.6556	Remote Similarity	NPD4602	Approved
0.6548	Remote Similarity	NPD7970	Approved
0.6548	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD6716	Phase 1
0.654	Remote Similarity	NPD5809	Phase 3
0.654	Remote Similarity	NPD6986	Phase 1
0.6536	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD7803	Approved
0.6531	Remote Similarity	NPD5017	Discontinued
0.6531	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.653	Remote Similarity	NPD8291	Clinical (unspecified phase)
0.653	Remote Similarity	NPD5488	Discontinued
0.6526	Remote Similarity	NPD8426	Approved
0.6526	Remote Similarity	NPD8425	Approved
0.6518	Remote Similarity	NPD8272	Phase 2
0.6516	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD6999	Discontinued
0.6509	Remote Similarity	NPD6531	Approved
0.6509	Remote Similarity	NPD6530	Approved
0.6508	Remote Similarity	NPD7557	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD8325	Phase 3
0.6496	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD8326	Phase 3
0.6494	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD4885	Approved
0.6488	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD8523	Approved
0.6479	Remote Similarity	NPD5821	Approved
0.6473	Remote Similarity	NPD7956	Approved
0.6473	Remote Similarity	NPD7955	Approved
0.6471	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD8097	Phase 3
0.6468	Remote Similarity	NPD7656	Approved
0.6468	Remote Similarity	NPD8096	Phase 3
0.6468	Remote Similarity	NPD7657	Approved
0.6466	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD5482	Discontinued
0.6456	Remote Similarity	NPD7564	Discontinued
0.6454	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6987	Phase 1
0.6452	Remote Similarity	NPD8098	Approved
0.6452	Remote Similarity	NPD5901	Discontinued
0.6449	Remote Similarity	NPD6249	Phase 2
0.6449	Remote Similarity	NPD6248	Phase 2
0.6447	Remote Similarity	NPD8463	Approved
0.6445	Remote Similarity	NPD6770	Approved
0.6442	Remote Similarity	NPD7576	Discontinued
0.644	Remote Similarity	NPD2509	Approved
0.644	Remote Similarity	NPD2510	Approved
0.644	Remote Similarity	NPD2442	Approved
0.644	Remote Similarity	NPD2443	Approved
0.6429	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD7711	Discontinued
0.642	Remote Similarity	NPD7619	Phase 3
0.642	Remote Similarity	NPD7618	Phase 3
0.642	Remote Similarity	NPD6210	Phase 3
0.6411	Remote Similarity	NPD8072	Approved
0.6403	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD4051	Discontinued
0.6387	Remote Similarity	NPD7483	Phase 2
0.6387	Remote Similarity	NPD8370	Discontinued
0.6387	Remote Similarity	NPD7482	Phase 2
0.6382	Remote Similarity	NPD7308	Discontinued
0.6379	Remote Similarity	NPD8525	Approved
0.6378	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD6840	Approved
0.6375	Remote Similarity	NPD8423	Phase 2
0.6375	Remote Similarity	NPD8399	Phase 1
0.6371	Remote Similarity	NPD8073	Approved
0.6371	Remote Similarity	NPD7187	Phase 2
0.637	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6367	Remote Similarity	NPD8256	Approved
0.6367	Remote Similarity	NPD8258	Clinical (unspecified phase)
0.6367	Remote Similarity	NPD8257	Approved
0.636	Remote Similarity	NPD7603	Discontinued
0.6345	Remote Similarity	NPD5487	Phase 1

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