NPASS Compound

Structure

NPC471951 OpenBabel07101718332D 51 60 0 0 1 0 0 0 0 0999 V2000 -1.4384 3.1143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4384 1.4303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1054 -0.8741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8620 3.7306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0751 -2.6481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5410 0.3140 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8894 -0.5937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2332 -3.1342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0751 -1.6759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5807 0.4661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2775 -1.3492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3912 -2.6481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2141 -2.9060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9523 2.2723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2332 -1.1897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9688 -0.2895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3173 -1.1971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3912 -1.6759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4265 0.6495 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1825 0.1892 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7463 -1.2795 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0641 -0.1371 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1635 -2.0859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4667 -0.2706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7039 2.2723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0200 1.3000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2033 -1.9338 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0310 -0.2387 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9979 -0.3404 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0200 2.2723 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7039 1.3000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4270 -0.4227 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5617 -1.8090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.6686 -1.0253 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.1452 -1.0262 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8620 2.7584 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7754 -1.3304 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8620 0.8139 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.6224 -3.4015 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3775 0.8516 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1317 1.1601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8604 -3.9013 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1183 0.6371 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5459 2.7584 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8220 0.8139 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4227 -1.4270 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 0.8620 2.7584 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1.7039 2.2723 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 0.8010 0.0842 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -0.5069 -0.6259 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 35 1 0 0 0 0 4 36 1 0 0 0 0 5 8 2 0 0 0 0 5 9 1 0 0 0 0 6 7 2 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 9 15 2 0 0 0 0 10 16 2 0 0 0 0 11 17 2 0 0 0 0 12 18 2 0 0 0 0 13 39 1 0 0 0 0 14 30 1 0 0 0 0 15 18 1 0 0 0 0 16 17 1 0 0 0 0 16 29 1 0 0 0 0 17 33 1 0 0 0 0 18 34 1 0 0 0 0 19 28 1 1 0 0 0 19 31 1 0 0 0 0 19 40 1 0 0 0 0 20 29 1 1 0 0 0 20 32 1 0 0 0 0 20 41 1 0 0 0 0 21 29 1 1 0 0 0 21 33 1 0 0 0 0 21 37 1 0 0 0 0 22 28 1 6 0 0 0 22 34 1 0 0 0 0 22 38 1 0 0 0 0 23 27 1 0 0 0 0 23 37 1 0 0 0 0 23 42 2 0 0 0 0 24 35 1 0 0 0 0 24 43 2 0 0 0 0 25 36 1 0 0 0 0 25 44 2 0 0 0 0 26 30 1 0 0 0 0 26 38 1 0 0 0 0 26 45 2 0 0 0 0 27 13 1 1 0 0 0 27 35 1 0 0 0 0 27 46 1 0 0 0 0 28 15 1 6 0 0 0 28 29 1 0 0 0 0 30 36 1 0 0 0 0 30 47 1 6 0 0 0 31 25 1 1 0 0 0 31 38 1 0 0 0 0 31 48 1 0 0 0 0 32 24 1 1 0 0 0 32 37 1 0 0 0 0 32 49 1 0 0 0 0 46 50 1 0 0 0 0 47 48 1 0 0 0 0 49 51 1 0 0 0 0 50 51 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	804.07
Volume:	688.665
LogP:	3.588
LogD:	2.171
LogS:	-4.074
# Rotatable Bonds:	3
TPSA:	165.99
# H-Bond Aceptor:	13
# H-Bond Donor:	5
# Rings:	12
# Heavy Atoms:	19

MedChem Properties

QED Drug-Likeness Score:	0.287
Synthetic Accessibility Score:	6.169
Fsp3:	0.5
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.097
MDCK Permeability:	1.2575877917697653e-05
Pgp-inhibitor:	0.498
Pgp-substrate:	0.066
Human Intestinal Absorption (HIA):	0.71
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.51
Plasma Protein Binding (PPB):	77.1817855834961%
Volume Distribution (VD):	1.055
Pgp-substrate:	6.016720294952393%

ADMET: Metabolism

CYP1A2-inhibitor:	0.069
CYP1A2-substrate:	0.073
CYP2C19-inhibitor:	0.993
CYP2C19-substrate:	0.945
CYP2C9-inhibitor:	0.944
CYP2C9-substrate:	0.105
CYP2D6-inhibitor:	0.771
CYP2D6-substrate:	0.062
CYP3A4-inhibitor:	0.951
CYP3A4-substrate:	0.988

ADMET: Excretion

Clearance (CL):	7.232
Half-life (T1/2):	0.005

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.137
Drug-inuced Liver Injury (DILI):	0.986
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.97
Maximum Recommended Daily Dose:	0.757
Skin Sensitization:	0.92
Carcinogencity:	0.863
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.797

Download Data

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

Natural Product: NPC471951

Natural Product ID:	NPC471951
*Common Name:**	HEIXSBSYEOOAIS-ZHZVSBHWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HEIXSBSYEOOAIS-ZHZVSBHWSA-N
Standard InCHI:	InChI=1S/C32H32N6O7S6/c1-14(2)30-26(45)38-22-28(15-9-5-8-12-18(15)34-22,19(40)31(38,48-47-30)25(44)36(30)4)29-16-10-6-7-11-17(16)33-21(29)37-23(42)27(13-39)35(3)24(43)32(37,20(29)41)49-51-50-46-27/h5-12,14,19-22,33-34,39-41H,13H2,1-4H3/t19-,20-,21-,22+,27-,28+,29?,30-,31-,32-/m0/s1
SMILES:	OC[C@@]12SSSS[C@@]3(C(=O)N1C)N(C2=O)[C@@H]1Nc2c(C1([C@@H]3O)[C@@]13c4ccccc4N[C@@H]1N1[C@@]4([C@H]3O)SS[C@@](C1=O)(N(C4=O)C)C(C)C)cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3309896
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001733] Pyrroloindoles

*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
NPO32810	preussia typharum	Species	Sporormiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23046341]
NPO32810	preussia typharum	Species	Sporormiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24893224]

☑ 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	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	43.1	nM	PMID[483028]

☑ 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 NPC471951 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	316
0.1-0.2	1650
0.2-0.3	7619
0.3-0.4	24296
0.4-0.5	6179
0.5-0.6	2238
0.6-0.7	334
0.7-0.8	44
0.8-0.85	0
0.85-0.9	4
0.9-0.95	14
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471946
0.9838	High Similarity	NPC477174
0.9733	High Similarity	NPC471950
0.9733	High Similarity	NPC471945
0.9628	High Similarity	NPC475259
0.9572	High Similarity	NPC477180
0.9572	High Similarity	NPC254850
0.9572	High Similarity	NPC477178
0.9572	High Similarity	NPC477181
0.9521	High Similarity	NPC470490
0.9521	High Similarity	NPC477173
0.9519	High Similarity	NPC477179
0.9471	High Similarity	NPC470488
0.9424	High Similarity	NPC475359
0.9424	High Similarity	NPC191817
0.9319	High Similarity	NPC470491
0.8877	High Similarity	NPC128582
0.8866	High Similarity	NPC470489
0.7895	Intermediate Similarity	NPC242269
0.7844	Intermediate Similarity	NPC477177
0.7844	Intermediate Similarity	NPC475859
0.7844	Intermediate Similarity	NPC475969
0.7806	Intermediate Similarity	NPC307396
0.7798	Intermediate Similarity	NPC470730
0.7798	Intermediate Similarity	NPC477175
0.7796	Intermediate Similarity	NPC276085
0.7756	Intermediate Similarity	NPC471436
0.7727	Intermediate Similarity	NPC165743
0.77	Intermediate Similarity	NPC276430
0.7602	Intermediate Similarity	NPC474877
0.7557	Intermediate Similarity	NPC470729
0.7557	Intermediate Similarity	NPC477176
0.7534	Intermediate Similarity	NPC63279
0.75	Intermediate Similarity	NPC297642
0.746	Intermediate Similarity	NPC222029
0.745	Intermediate Similarity	NPC259626
0.74	Intermediate Similarity	NPC2933
0.7358	Intermediate Similarity	NPC471124
0.735	Intermediate Similarity	NPC256288
0.7347	Intermediate Similarity	NPC285622
0.7291	Intermediate Similarity	NPC229484
0.7285	Intermediate Similarity	NPC312942
0.7285	Intermediate Similarity	NPC327095
0.7277	Intermediate Similarity	NPC297862
0.7264	Intermediate Similarity	NPC329833
0.726	Intermediate Similarity	NPC162440
0.7255	Intermediate Similarity	NPC292675
0.7252	Intermediate Similarity	NPC40455
0.7248	Intermediate Similarity	NPC470731
0.7241	Intermediate Similarity	NPC473615
0.724	Intermediate Similarity	NPC471122
0.7202	Intermediate Similarity	NPC309531
0.7202	Intermediate Similarity	NPC472102
0.7178	Intermediate Similarity	NPC477159
0.7156	Intermediate Similarity	NPC471663
0.7143	Intermediate Similarity	NPC19170
0.7113	Intermediate Similarity	NPC68650
0.7105	Intermediate Similarity	NPC66936
0.71	Intermediate Similarity	NPC476441
0.7098	Intermediate Similarity	NPC476817
0.7092	Intermediate Similarity	NPC472106
0.7014	Intermediate Similarity	NPC90967
0.7014	Intermediate Similarity	NPC470732
0.7005	Intermediate Similarity	NPC284706
0.699	Remote Similarity	NPC472101
0.699	Remote Similarity	NPC286871
0.699	Remote Similarity	NPC472120
0.699	Remote Similarity	NPC176983
0.6989	Remote Similarity	NPC470301
0.6965	Remote Similarity	NPC475097
0.6959	Remote Similarity	NPC472538
0.6946	Remote Similarity	NPC14812
0.6934	Remote Similarity	NPC472541
0.6934	Remote Similarity	NPC472542
0.6933	Remote Similarity	NPC474896
0.6915	Remote Similarity	NPC476425
0.6915	Remote Similarity	NPC473743
0.6912	Remote Similarity	NPC225400
0.6903	Remote Similarity	NPC31097
0.69	Remote Similarity	NPC472118
0.6889	Remote Similarity	NPC272174
0.6887	Remote Similarity	NPC472539
0.6887	Remote Similarity	NPC470787
0.6887	Remote Similarity	NPC472540
0.6884	Remote Similarity	NPC472115
0.6884	Remote Similarity	NPC472114
0.6881	Remote Similarity	NPC470786
0.6881	Remote Similarity	NPC471155
0.6878	Remote Similarity	NPC476428
0.6869	Remote Similarity	NPC106118
0.6854	Remote Similarity	NPC471199
0.6849	Remote Similarity	NPC270241
0.6837	Remote Similarity	NPC475489
0.6832	Remote Similarity	NPC473880
0.6828	Remote Similarity	NPC253987
0.682	Remote Similarity	NPC295548
0.6818	Remote Similarity	NPC472117
0.681	Remote Similarity	NPC105055
0.681	Remote Similarity	NPC22689
0.68	Remote Similarity	NPC214960
0.68	Remote Similarity	NPC279527
0.6798	Remote Similarity	NPC470548
0.6786	Remote Similarity	NPC29285
0.678	Remote Similarity	NPC475094
0.6774	Remote Similarity	NPC471123
0.6771	Remote Similarity	NPC473006
0.6761	Remote Similarity	NPC34717
0.6756	Remote Similarity	NPC471197
0.6751	Remote Similarity	NPC113946
0.6751	Remote Similarity	NPC469898
0.6749	Remote Similarity	NPC214626
0.6749	Remote Similarity	NPC251212
0.6749	Remote Similarity	NPC177261
0.6749	Remote Similarity	NPC139085
0.6748	Remote Similarity	NPC166169
0.6748	Remote Similarity	NPC286994
0.6742	Remote Similarity	NPC223791
0.6742	Remote Similarity	NPC107077
0.6737	Remote Similarity	NPC301501
0.6736	Remote Similarity	NPC109787
0.673	Remote Similarity	NPC473298
0.6726	Remote Similarity	NPC471198
0.6714	Remote Similarity	NPC181928
0.6699	Remote Similarity	NPC476095
0.6697	Remote Similarity	NPC285192
0.6667	Remote Similarity	NPC162860
0.6667	Remote Similarity	NPC475420
0.6653	Remote Similarity	NPC478028
0.6653	Remote Similarity	NPC469452
0.6652	Remote Similarity	NPC248601
0.6652	Remote Similarity	NPC223242
0.665	Remote Similarity	NPC476326
0.6639	Remote Similarity	NPC469450
0.6633	Remote Similarity	NPC473003
0.6619	Remote Similarity	NPC52262
0.6602	Remote Similarity	NPC469900
0.6601	Remote Similarity	NPC475248
0.6601	Remote Similarity	NPC63047
0.6601	Remote Similarity	NPC473000
0.6599	Remote Similarity	NPC478076
0.6598	Remote Similarity	NPC329932
0.6597	Remote Similarity	NPC478029
0.6596	Remote Similarity	NPC139373
0.6583	Remote Similarity	NPC469451
0.6577	Remote Similarity	NPC54420
0.655	Remote Similarity	NPC469902
0.655	Remote Similarity	NPC219397
0.6548	Remote Similarity	NPC473002
0.6546	Remote Similarity	NPC264589
0.6538	Remote Similarity	NPC99043
0.6538	Remote Similarity	NPC218594
0.6537	Remote Similarity	NPC355
0.6531	Remote Similarity	NPC318086
0.6531	Remote Similarity	NPC473329
0.6528	Remote Similarity	NPC221687
0.6526	Remote Similarity	NPC469560
0.6522	Remote Similarity	NPC320147
0.6507	Remote Similarity	NPC477714
0.65	Remote Similarity	NPC104345
0.6493	Remote Similarity	NPC302235
0.649	Remote Similarity	NPC473001
0.649	Remote Similarity	NPC260075
0.6485	Remote Similarity	NPC85651
0.6485	Remote Similarity	NPC131977
0.6485	Remote Similarity	NPC99632
0.6485	Remote Similarity	NPC282339
0.6485	Remote Similarity	NPC469741
0.6485	Remote Similarity	NPC472121
0.6479	Remote Similarity	NPC285841
0.6471	Remote Similarity	NPC155143
0.6471	Remote Similarity	NPC473005
0.6468	Remote Similarity	NPC36495
0.6468	Remote Similarity	NPC469901
0.6463	Remote Similarity	NPC15384
0.6463	Remote Similarity	NPC244425
0.645	Remote Similarity	NPC324850
0.6444	Remote Similarity	NPC477160
0.6439	Remote Similarity	NPC469904
0.6438	Remote Similarity	NPC52557
0.6436	Remote Similarity	NPC225319
0.6436	Remote Similarity	NPC315368
0.6432	Remote Similarity	NPC145754
0.6425	Remote Similarity	NPC475506
0.6425	Remote Similarity	NPC471512
0.6422	Remote Similarity	NPC97100
0.6422	Remote Similarity	NPC473375
0.641	Remote Similarity	NPC122886
0.6391	Remote Similarity	NPC477715
0.6391	Remote Similarity	NPC238945
0.638	Remote Similarity	NPC138830
0.6379	Remote Similarity	NPC265592
0.6379	Remote Similarity	NPC275134
0.6376	Remote Similarity	NPC478157
0.6371	Remote Similarity	NPC69843
0.6364	Remote Similarity	NPC281049
0.6364	Remote Similarity	NPC171317
0.6364	Remote Similarity	NPC129624
0.6359	Remote Similarity	NPC472103
0.6355	Remote Similarity	NPC478077
0.6351	Remote Similarity	NPC472999

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 NPC471951 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	523
0.2-0.3	734
0.3-0.4	2423
0.4-0.5	4012
0.5-0.6	1231
0.6-0.7	58
0.7-0.8	1
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
0.77	Intermediate Similarity	NPD8240	Discontinued
0.6837	Remote Similarity	NPD8630	Approved
0.6821	Remote Similarity	NPD5743	Approved
0.6821	Remote Similarity	NPD5742	Approved
0.6821	Remote Similarity	NPD5741	Approved
0.6769	Remote Similarity	NPD4121	Phase 3
0.6769	Remote Similarity	NPD4120	Approved
0.6765	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6879	Phase 2
0.6748	Remote Similarity	NPD6878	Phase 2
0.6699	Remote Similarity	NPD6557	Phase 2
0.6635	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD3625	Discontinued
0.6561	Remote Similarity	NPD8115	Approved
0.6561	Remote Similarity	NPD8114	Approved
0.655	Remote Similarity	NPD7599	Phase 2
0.6538	Remote Similarity	NPD5774	Approved
0.6538	Remote Similarity	NPD5775	Approved
0.6533	Remote Similarity	NPD7595	Discontinued
0.6502	Remote Similarity	NPD8322	Phase 2
0.65	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.648	Remote Similarity	NPD5942	Approved
0.648	Remote Similarity	NPD5941	Approved
0.6477	Remote Similarity	NPD5024	Approved
0.6465	Remote Similarity	NPD8402	Approved
0.6465	Remote Similarity	NPD8400	Approved
0.6465	Remote Similarity	NPD8401	Approved
0.6441	Remote Similarity	NPD7824	Approved
0.6429	Remote Similarity	NPD7950	Approved
0.6429	Remote Similarity	NPD7789	Approved
0.6429	Remote Similarity	NPD7951	Approved
0.6429	Remote Similarity	NPD7790	Approved
0.6429	Remote Similarity	NPD7791	Approved
0.6429	Remote Similarity	NPD7953	Approved
0.6429	Remote Similarity	NPD7952	Approved
0.6356	Remote Similarity	NPD7731	Approved
0.6356	Remote Similarity	NPD7730	Approved
0.6355	Remote Similarity	NPD7600	Phase 2
0.6351	Remote Similarity	NPD7817	Phase 1
0.6344	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6314	Remote Similarity	NPD8289	Discontinued
0.6313	Remote Similarity	NPD4682	Phase 2
0.6298	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD7105	Phase 1
0.6283	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.628	Remote Similarity	NPD7890	Discontinued
0.6271	Remote Similarity	NPD7271	Approved
0.6269	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD4976	Discontinued
0.6261	Remote Similarity	NPD7781	Approved
0.6261	Remote Similarity	NPD7780	Approved
0.6256	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7968	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD7970	Approved
0.6233	Remote Similarity	NPD4600	Approved
0.6233	Remote Similarity	NPD4601	Approved
0.6227	Remote Similarity	NPD4602	Approved
0.6218	Remote Similarity	NPD6358	Phase 2
0.6214	Remote Similarity	NPD3790	Phase 2
0.619	Remote Similarity	NPD5997	Discontinued
0.6179	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD7683	Discontinued
0.6162	Remote Similarity	NPD7785	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD6805	Discontinued
0.6161	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.615	Remote Similarity	NPD4432	Discontinued
0.6136	Remote Similarity	NPD7570	Approved
0.6136	Remote Similarity	NPD7569	Approved
0.6133	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD7727	Phase 2
0.6123	Remote Similarity	NPD8272	Phase 2
0.6119	Remote Similarity	NPD5748	Phase 2
0.6111	Remote Similarity	NPD5918	Discontinued
0.6092	Remote Similarity	NPD7716	Approved
0.6092	Remote Similarity	NPD7717	Approved
0.6091	Remote Similarity	NPD5076	Approved
0.6091	Remote Similarity	NPD5077	Approved
0.6082	Remote Similarity	NPD6073	Approved
0.6081	Remote Similarity	NPD7944	Discontinued
0.608	Remote Similarity	NPD8250	Phase 2
0.6073	Remote Similarity	NPD8025	Phase 2
0.6073	Remote Similarity	NPD7444	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD5856	Discontinued
0.6068	Remote Similarity	NPD4514	Approved
0.6061	Remote Similarity	NPD6301	Phase 2
0.6053	Remote Similarity	NPD6644	Discontinued
0.6052	Remote Similarity	NPD7557	Clinical (unspecified phase)
0.6051	Remote Similarity	NPD6295	Approved
0.6051	Remote Similarity	NPD6294	Approved
0.6049	Remote Similarity	NPD6395	Phase 2
0.6049	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD3989	Phase 3
0.6044	Remote Similarity	NPD7308	Discontinued
0.6043	Remote Similarity	NPD8271	Discontinued
0.6042	Remote Similarity	NPD5581	Approved
0.6038	Remote Similarity	NPD7854	Phase 2
0.6034	Remote Similarity	NPD7470	Discontinued
0.6021	Remote Similarity	NPD5263	Approved
0.6019	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD3990	Phase 3
0.6	Remote Similarity	NPD8173	Phase 2
0.6	Remote Similarity	NPD8172	Phase 2
0.5991	Remote Similarity	NPD7973	Discontinued
0.5991	Remote Similarity	NPD7252	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD6238	Discontinued
0.5991	Remote Similarity	NPD6200	Clinical (unspecified phase)
0.5989	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD8169	Discontinued
0.598	Remote Similarity	NPD2820	Phase 3
0.598	Remote Similarity	NPD8315	Phase 1
0.5979	Remote Similarity	NPD5182	Approved
0.5979	Remote Similarity	NPD6792	Phase 3
0.5979	Remote Similarity	NPD5184	Approved
0.5979	Remote Similarity	NPD5185	Approved
0.5974	Remote Similarity	NPD7666	Phase 3
0.5974	Remote Similarity	NPD7665	Phase 2
0.5973	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.5971	Remote Similarity	NPD1663	Discontinued
0.597	Remote Similarity	NPD3509	Approved
0.597	Remote Similarity	NPD3510	Approved
0.5953	Remote Similarity	NPD5600	Discontinued
0.5951	Remote Similarity	NPD5639	Clinical (unspecified phase)
0.595	Remote Similarity	NPD6164	Phase 2
0.595	Remote Similarity	NPD6165	Phase 2
0.5946	Remote Similarity	NPD5042	Phase 1
0.5941	Remote Similarity	NPD2426	Clinical (unspecified phase)
0.5939	Remote Similarity	NPD7205	Discontinued
0.5938	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD7543	Phase 2
0.5931	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.593	Remote Similarity	NPD2365	Approved
0.5926	Remote Similarity	NPD6368	Clinical (unspecified phase)
0.5924	Remote Similarity	NPD7168	Phase 3
0.592	Remote Similarity	NPD8323	Discontinued
0.5919	Remote Similarity	NPD6665	Discontinued
0.5918	Remote Similarity	NPD5725	Approved
0.5917	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.5915	Remote Similarity	NPD8094	Discontinued
0.5915	Remote Similarity	NPD3824	Phase 1
0.5913	Remote Similarity	NPD4393	Approved
0.5913	Remote Similarity	NPD5426	Phase 3
0.5913	Remote Similarity	NPD33	Approved
0.5909	Remote Similarity	NPD7711	Discontinued
0.5907	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.5907	Remote Similarity	NPD4091	Approved
0.5901	Remote Similarity	NPD7617	Discontinued
0.59	Remote Similarity	NPD5265	Approved
0.59	Remote Similarity	NPD5264	Approved
0.5899	Remote Similarity	NPD6833	Clinical (unspecified phase)
0.5899	Remote Similarity	NPD4329	Approved
0.5899	Remote Similarity	NPD4330	Approved
0.5899	Remote Similarity	NPD3227	Phase 2
0.5897	Remote Similarity	NPD4153	Approved
0.5897	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.5894	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.5894	Remote Similarity	NPD7091	Discontinued
0.5894	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.5892	Remote Similarity	NPD7820	Phase 3
0.5891	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.589	Remote Similarity	NPD7482	Phase 2
0.589	Remote Similarity	NPD7483	Phase 2
0.5888	Remote Similarity	NPD7593	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD4126	Approved
0.5888	Remote Similarity	NPD5318	Discontinued
0.5887	Remote Similarity	NPD7001	Phase 3
0.5885	Remote Similarity	NPD3040	Approved
0.5882	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6891	Phase 2
0.5882	Remote Similarity	NPD6483	Approved
0.5882	Remote Similarity	NPD6484	Approved
0.588	Remote Similarity	NPD3996	Approved
0.588	Remote Similarity	NPD3449	Discontinued
0.588	Remote Similarity	NPD3991	Approved
0.588	Remote Similarity	NPD4317	Approved
0.588	Remote Similarity	NPD3993	Approved
0.588	Remote Similarity	NPD3792	Approved
0.588	Remote Similarity	NPD3992	Approved
0.588	Remote Similarity	NPD3995	Approved
0.588	Remote Similarity	NPD7432	Phase 2
0.588	Remote Similarity	NPD4092	Approved
0.588	Remote Similarity	NPD3994	Approved
0.588	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.588	Remote Similarity	NPD4520	Approved
0.5875	Remote Similarity	NPD7726	Phase 1
0.5874	Remote Similarity	NPD6659	Phase 2
0.5874	Remote Similarity	NPD2327	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.5867	Remote Similarity	NPD7618	Phase 3
0.5867	Remote Similarity	NPD7619	Phase 3
0.5865	Remote Similarity	NPD6596	Phase 2
0.5864	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD6518	Discontinued
0.586	Remote Similarity	NPD7662	Clinical (unspecified phase)
0.586	Remote Similarity	NPD5466	Approved
0.586	Remote Similarity	NPD6613	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD7995	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data