NPASS Compound

Structure

NPC476252 OpenBabel07101719242D 25 31 0 0 1 0 0 0 0 0999 V2000 2.8483 -3.5679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2596 -3.2280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2183 -3.5277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1141 -1.6790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3293 -2.7414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4811 -3.3195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3293 -3.0020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1180 -3.0206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7124 -2.5208 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.6814 -2.6700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5167 -1.3536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3306 -2.4786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2546 -1.2614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3401 -1.9694 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.1270 -2.2818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5857 -1.8517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2397 -1.4623 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.1287 -1.9879 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.2505 -0.4297 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 3.7541 -2.3210 0.0000 N 0 5 0 0 0 0 0 0 0 0 0 0 4.7868 -1.7809 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.1583 -2.5559 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.4297 -3.5091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6164 -1.7874 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0968 -3.3499 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 6 1 0 0 0 0 2 22 1 0 0 0 0 3 7 1 0 0 0 0 3 8 2 0 0 0 0 4 9 1 0 0 0 0 4 18 1 0 0 0 0 5 6 2 0 0 0 0 5 20 1 0 0 0 0 6 10 1 0 0 0 0 7 14 1 0 0 0 0 7 23 2 0 0 0 0 8 18 1 0 0 0 0 8 25 1 0 0 0 0 9 21 1 0 0 0 0 9 25 1 0 0 0 0 10 12 2 0 0 0 0 10 15 1 0 0 0 0 11 13 1 0 0 0 0 11 15 2 0 0 0 0 11 18 1 0 0 0 0 12 16 1 0 0 0 0 12 20 1 0 0 0 0 13 16 1 0 0 0 0 13 21 2 0 0 0 0 14 17 1 0 0 0 0 14 22 1 0 0 0 0 15 22 1 0 0 0 0 16 24 2 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 M CHG 2 19 1 20 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	350.08
Volume:	321.61
LogP:	1.654
LogD:	1.061
LogS:	-3.616
# Rotatable Bonds:	0
TPSA:	94.38
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	7
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.543
Synthetic Accessibility Score:	6.866
Fsp3:	0.278
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.596
MDCK Permeability:	2.1536527583521092e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.931
Human Intestinal Absorption (HIA):	0.035
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.053

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.037
Plasma Protein Binding (PPB):	92.45354461669922%
Volume Distribution (VD):	1.131
Pgp-substrate:	4.905285835266113%

ADMET: Metabolism

CYP1A2-inhibitor:	0.245
CYP1A2-substrate:	0.266
CYP2C19-inhibitor:	0.432
CYP2C19-substrate:	0.17
CYP2C9-inhibitor:	0.425
CYP2C9-substrate:	0.843
CYP2D6-inhibitor:	0.281
CYP2D6-substrate:	0.4
CYP3A4-inhibitor:	0.444
CYP3A4-substrate:	0.674

ADMET: Excretion

Clearance (CL):	7.311
Half-life (T1/2):	0.791

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.475
Drug-inuced Liver Injury (DILI):	0.624
AMES Toxicity:	0.499
Rat Oral Acute Toxicity:	0.637
Maximum Recommended Daily Dose:	0.919
Skin Sensitization:	0.467
Carcinogencity:	0.865
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.888

Download Data

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

Natural Product: NPC476252

Natural Product ID:	NPC476252
*Common Name:**	IWNXNXVLBBLBNW-IHSOURIASA-N
IUPAC Name:	n.a.
Synonyms:	1-Aminodiscorhabdin D
Standard InCHIKey:	IWNXNXVLBBLBNW-IHSOURIASA-N
Standard InCHI:	InChI=1S/C18H14N4O2S.C2HF3O2/c19-17-14-7(23)3-8-18(17)4-9(25-8)21-13-11(18)15-10-6(1-2-22(14)15)5-20-12(10)16(13)24;3-2(4,5)1(6)7/h3,5,9,14,17H,1-2,4,19H2,(H,20,21,24);(H,6,7)/t9-,14+,17?,18+;/m0./s1
SMILES:	OC(=O)C(F)(F)F.O=C1C=C2S[C@H]3C[C@]42C([C@@H]1N1CCc2c5C1=C4C(=N3)C(=O)c5[n-]c2)[NH3+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL558630
PubChem CID:	45266491
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001626] Phenanthrolines

*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
NPO32524	latrunculid sponges	Species	n.a.	n.a.	n.a.	South African	n.a.	PMID[15332840]

☑ 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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	119.0	nM	PMID[556063]

☑ 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 NPC476252 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	3344
0.2-0.3	22271
0.3-0.4	10986
0.4-0.5	3076
0.5-0.6	2220
0.6-0.7	328
0.7-0.8	25
0.8-0.85	12
0.85-0.9	3
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9613	High Similarity	NPC476143
0.9061	High Similarity	NPC469359
0.8788	High Similarity	NPC477416
0.8513	High Similarity	NPC469563
0.8384	Intermediate Similarity	NPC469578
0.83	Intermediate Similarity	NPC220594
0.83	Intermediate Similarity	NPC469562
0.8241	Intermediate Similarity	NPC475410
0.8241	Intermediate Similarity	NPC469577
0.8115	Intermediate Similarity	NPC477415
0.8115	Intermediate Similarity	NPC23476
0.8115	Intermediate Similarity	NPC474259
0.7908	Intermediate Similarity	NPC225622
0.7908	Intermediate Similarity	NPC221726
0.7908	Intermediate Similarity	NPC477414
0.7665	Intermediate Similarity	NPC268966
0.7585	Intermediate Similarity	NPC143075
0.7579	Intermediate Similarity	NPC262338
0.7436	Intermediate Similarity	NPC182940
0.7356	Intermediate Similarity	NPC88115
0.7347	Intermediate Similarity	NPC234403
0.7347	Intermediate Similarity	NPC79777
0.7343	Intermediate Similarity	NPC106757
0.7293	Intermediate Similarity	NPC477418
0.7293	Intermediate Similarity	NPC477420
0.7264	Intermediate Similarity	NPC473628
0.7249	Intermediate Similarity	NPC474492
0.7211	Intermediate Similarity	NPC470680
0.7211	Intermediate Similarity	NPC100104
0.7166	Intermediate Similarity	NPC217021
0.7166	Intermediate Similarity	NPC470679
0.7143	Intermediate Similarity	NPC475874
0.7116	Intermediate Similarity	NPC477413
0.7112	Intermediate Similarity	NPC473878
0.7037	Intermediate Similarity	NPC469544
0.701	Intermediate Similarity	NPC103119
0.6959	Remote Similarity	NPC274981
0.6927	Remote Similarity	NPC255909
0.6915	Remote Similarity	NPC100726
0.6842	Remote Similarity	NPC471655
0.6789	Remote Similarity	NPC102664
0.6777	Remote Similarity	NPC167710
0.673	Remote Similarity	NPC292361
0.6729	Remote Similarity	NPC98864
0.6716	Remote Similarity	NPC186068
0.6702	Remote Similarity	NPC123906
0.6699	Remote Similarity	NPC474258
0.6684	Remote Similarity	NPC251391
0.6667	Remote Similarity	NPC216550
0.6635	Remote Similarity	NPC473946
0.6585	Remote Similarity	NPC477042
0.6569	Remote Similarity	NPC157583
0.6512	Remote Similarity	NPC248782
0.6505	Remote Similarity	NPC73994
0.6495	Remote Similarity	NPC313889
0.649	Remote Similarity	NPC467063
0.6484	Remote Similarity	NPC473239
0.6413	Remote Similarity	NPC476158
0.6411	Remote Similarity	NPC477003
0.6408	Remote Similarity	NPC83774
0.6402	Remote Similarity	NPC326422
0.639	Remote Similarity	NPC469529
0.6389	Remote Similarity	NPC473814
0.6389	Remote Similarity	NPC78767
0.6378	Remote Similarity	NPC70406
0.6376	Remote Similarity	NPC121327
0.6372	Remote Similarity	NPC294693
0.6364	Remote Similarity	NPC138562
0.6364	Remote Similarity	NPC317701
0.6355	Remote Similarity	NPC70949
0.6346	Remote Similarity	NPC61011
0.6333	Remote Similarity	NPC46895
0.6332	Remote Similarity	NPC213914
0.6318	Remote Similarity	NPC143977
0.6316	Remote Similarity	NPC191415
0.6313	Remote Similarity	NPC74153
0.6313	Remote Similarity	NPC209362
0.6308	Remote Similarity	NPC105811
0.6296	Remote Similarity	NPC202812
0.6296	Remote Similarity	NPC93390
0.6289	Remote Similarity	NPC467188
0.6284	Remote Similarity	NPC477041
0.6284	Remote Similarity	NPC477044
0.6284	Remote Similarity	NPC34837
0.6283	Remote Similarity	NPC471194
0.6283	Remote Similarity	NPC471193
0.6267	Remote Similarity	NPC128244
0.6262	Remote Similarity	NPC477976
0.625	Remote Similarity	NPC304203
0.625	Remote Similarity	NPC237188
0.625	Remote Similarity	NPC473821
0.625	Remote Similarity	NPC284775
0.6239	Remote Similarity	NPC477417
0.6239	Remote Similarity	NPC477419
0.6233	Remote Similarity	NPC476460
0.6233	Remote Similarity	NPC175602
0.6226	Remote Similarity	NPC99939
0.6226	Remote Similarity	NPC308931
0.6226	Remote Similarity	NPC311282
0.6223	Remote Similarity	NPC229893
0.6222	Remote Similarity	NPC61038
0.6219	Remote Similarity	NPC80681
0.6214	Remote Similarity	NPC302647
0.6204	Remote Similarity	NPC47190
0.6197	Remote Similarity	NPC19170
0.6193	Remote Similarity	NPC79356
0.6193	Remote Similarity	NPC102592
0.6192	Remote Similarity	NPC475635
0.6186	Remote Similarity	NPC469489
0.6186	Remote Similarity	NPC297862
0.6182	Remote Similarity	NPC477045
0.6182	Remote Similarity	NPC123395
0.6182	Remote Similarity	NPC474767
0.6176	Remote Similarity	NPC233380
0.6167	Remote Similarity	NPC72956
0.6164	Remote Similarity	NPC272483
0.6161	Remote Similarity	NPC472065
0.6154	Remote Similarity	NPC476817
0.615	Remote Similarity	NPC133003
0.615	Remote Similarity	NPC472070
0.6147	Remote Similarity	NPC195239
0.6147	Remote Similarity	NPC157828
0.6143	Remote Similarity	NPC143325
0.6143	Remote Similarity	NPC11126
0.614	Remote Similarity	NPC110182
0.614	Remote Similarity	NPC6865
0.614	Remote Similarity	NPC153980
0.6132	Remote Similarity	NPC102755
0.613	Remote Similarity	NPC177996
0.613	Remote Similarity	NPC147983
0.6129	Remote Similarity	NPC272458
0.6129	Remote Similarity	NPC472292
0.6119	Remote Similarity	NPC472116
0.6119	Remote Similarity	NPC472293
0.6119	Remote Similarity	NPC11445
0.6116	Remote Similarity	NPC477043
0.6114	Remote Similarity	NPC207866
0.6103	Remote Similarity	NPC228835
0.6093	Remote Similarity	NPC17059
0.6091	Remote Similarity	NPC469736
0.6089	Remote Similarity	NPC472064
0.6087	Remote Similarity	NPC91895
0.6081	Remote Similarity	NPC252338
0.6076	Remote Similarity	NPC469720
0.6076	Remote Similarity	NPC476491
0.607	Remote Similarity	NPC229055
0.6066	Remote Similarity	NPC283219
0.6066	Remote Similarity	NPC55772
0.6061	Remote Similarity	NPC471192
0.6054	Remote Similarity	NPC471944
0.6052	Remote Similarity	NPC269270
0.605	Remote Similarity	NPC472260
0.6049	Remote Similarity	NPC265100
0.6047	Remote Similarity	NPC62749
0.604	Remote Similarity	NPC74357
0.6037	Remote Similarity	NPC324091
0.6036	Remote Similarity	NPC472297
0.6036	Remote Similarity	NPC472296
0.6036	Remote Similarity	NPC81535
0.6036	Remote Similarity	NPC477004
0.6036	Remote Similarity	NPC284338
0.6034	Remote Similarity	NPC477715
0.6027	Remote Similarity	NPC472295
0.6027	Remote Similarity	NPC81802
0.6027	Remote Similarity	NPC247735
0.6027	Remote Similarity	NPC472063
0.6027	Remote Similarity	NPC472069
0.6027	Remote Similarity	NPC269886
0.6027	Remote Similarity	NPC472210
0.6027	Remote Similarity	NPC472062
0.6027	Remote Similarity	NPC57398
0.6026	Remote Similarity	NPC14686
0.6019	Remote Similarity	NPC71132
0.6018	Remote Similarity	NPC227582
0.6018	Remote Similarity	NPC106824
0.6017	Remote Similarity	NPC63279
0.6009	Remote Similarity	NPC477714
0.6	Remote Similarity	NPC203468
0.6	Remote Similarity	NPC110500
0.6	Remote Similarity	NPC139763
0.6	Remote Similarity	NPC318299
0.6	Remote Similarity	NPC473218
0.6	Remote Similarity	NPC149155
0.6	Remote Similarity	NPC470702
0.5992	Remote Similarity	NPC297642
0.5991	Remote Similarity	NPC474916
0.5991	Remote Similarity	NPC321708
0.5991	Remote Similarity	NPC248041
0.5991	Remote Similarity	NPC126709
0.5991	Remote Similarity	NPC470731
0.599	Remote Similarity	NPC41717
0.5975	Remote Similarity	NPC312942
0.5975	Remote Similarity	NPC327095
0.5975	Remote Similarity	NPC253987
0.5974	Remote Similarity	NPC317752
0.5974	Remote Similarity	NPC470703
0.5972	Remote Similarity	NPC235684
0.5972	Remote Similarity	NPC267885
0.5972	Remote Similarity	NPC476419
0.5971	Remote Similarity	NPC21174

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 NPC476252 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	215
0.1-0.2	559
0.2-0.3	1241
0.3-0.4	2608
0.4-0.5	2955
0.5-0.6	1415
0.6-0.7	157
0.7-0.8	0
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
0.6875	Remote Similarity	NPD6173	Approved
0.6837	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD6044	Discontinued
0.6575	Remote Similarity	NPD4415	Approved
0.6558	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD4959	Approved
0.6545	Remote Similarity	NPD4960	Approved
0.6442	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD3238	Discontinued
0.6435	Remote Similarity	NPD7661	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD3968	Approved
0.6351	Remote Similarity	NPD3410	Approved
0.6351	Remote Similarity	NPD3411	Phase 2
0.6343	Remote Similarity	NPD7027	Phase 3
0.633	Remote Similarity	NPD2405	Phase 3
0.6316	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD3967	Approved
0.6305	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD7619	Phase 3
0.6296	Remote Similarity	NPD7618	Phase 3
0.6284	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD3891	Phase 2
0.6273	Remote Similarity	NPD3890	Phase 2
0.6273	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD5017	Discontinued
0.6268	Remote Similarity	NPD2481	Approved
0.6268	Remote Similarity	NPD2479	Phase 3
0.6268	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD5473	Discontinued
0.6267	Remote Similarity	NPD2307	Discontinued
0.6261	Remote Similarity	NPD4905	Approved
0.6261	Remote Similarity	NPD4903	Approved
0.6261	Remote Similarity	NPD4906	Approved
0.6256	Remote Similarity	NPD6178	Phase 3
0.6244	Remote Similarity	NPD7187	Phase 2
0.6233	Remote Similarity	NPD4904	Approved
0.6222	Remote Similarity	NPD3856	Clinical (unspecified phase)
0.6217	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD6068	Discontinued
0.6209	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD4922	Phase 2
0.6193	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6193	Remote Similarity	NPD2289	Phase 3
0.6193	Remote Similarity	NPD4848	Phase 1
0.6193	Remote Similarity	NPD2290	Phase 3
0.6188	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD8169	Discontinued
0.6179	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD2753	Discontinued
0.6168	Remote Similarity	NPD4988	Discontinued
0.6168	Remote Similarity	NPD3246	Discontinued
0.6168	Remote Similarity	NPD3961	Discontinued
0.6167	Remote Similarity	NPD6152	Phase 1
0.6165	Remote Similarity	NPD1573	Approved
0.6165	Remote Similarity	NPD1575	Approved
0.6161	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD3178	Discontinued
0.6157	Remote Similarity	NPD2336	Approved
0.6157	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4961	Approved
0.615	Remote Similarity	NPD5510	Approved
0.6146	Remote Similarity	NPD6446	Discontinued
0.6142	Remote Similarity	NPD1270	Approved
0.613	Remote Similarity	NPD3353	Approved
0.6126	Remote Similarity	NPD4963	Approved
0.6126	Remote Similarity	NPD4962	Approved
0.6116	Remote Similarity	NPD5901	Discontinued
0.6114	Remote Similarity	NPD6787	Phase 2
0.6106	Remote Similarity	NPD7191	Phase 2
0.6106	Remote Similarity	NPD750	Phase 2
0.6106	Remote Similarity	NPD7232	Discontinued
0.6106	Remote Similarity	NPD4524	Discontinued
0.6104	Remote Similarity	NPD3805	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD7564	Discontinued
0.6101	Remote Similarity	NPD2004	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD4924	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD6156	Clinical (unspecified phase)
0.6085	Remote Similarity	NPD6752	Phase 1
0.6085	Remote Similarity	NPD6753	Phase 1
0.6077	Remote Similarity	NPD4883	Approved
0.6077	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.607	Remote Similarity	NPD7195	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD7552	Discontinued
0.6065	Remote Similarity	NPD7234	Approved
0.6065	Remote Similarity	NPD7233	Approved
0.6063	Remote Similarity	NPD2947	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD3389	Approved
0.6061	Remote Similarity	NPD3394	Approved
0.6061	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD3393	Approved
0.6059	Remote Similarity	NPD2214	Approved
0.6059	Remote Similarity	NPD2213	Approved
0.6058	Remote Similarity	NPD7550	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD7551	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD1631	Approved
0.6047	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD7026	Phase 2
0.6047	Remote Similarity	NPD5809	Phase 3
0.6044	Remote Similarity	NPD6987	Phase 1
0.6036	Remote Similarity	NPD3425	Discontinued
0.6036	Remote Similarity	NPD7049	Clinical (unspecified phase)
0.6035	Remote Similarity	NPD7666	Phase 3
0.6035	Remote Similarity	NPD7665	Phase 2
0.6035	Remote Similarity	NPD4882	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6028	Remote Similarity	NPD2091	Phase 2
0.6028	Remote Similarity	NPD2096	Phase 2
0.6027	Remote Similarity	NPD3773	Approved
0.6027	Remote Similarity	NPD8073	Approved
0.6027	Remote Similarity	NPD3774	Approved
0.6027	Remote Similarity	NPD3775	Approved
0.6026	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6025	Remote Similarity	NPD2893	Phase 3
0.6018	Remote Similarity	NPD6664	Approved
0.6018	Remote Similarity	NPD6260	Discontinued
0.6017	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD7970	Approved
0.6017	Remote Similarity	NPD5046	Discontinued
0.6009	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6	Remote Similarity	NPD482	Approved
0.6	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD4364	Phase 1
0.5991	Remote Similarity	NPD2851	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD7562	Approved
0.5991	Remote Similarity	NPD2850	Phase 1
0.599	Remote Similarity	NPD5636	Discontinued
0.599	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD4051	Discontinued
0.5982	Remote Similarity	NPD6665	Discontinued
0.5982	Remote Similarity	NPD3288	Approved
0.5981	Remote Similarity	NPD2092	Phase 2
0.5981	Remote Similarity	NPD2095	Phase 2
0.5981	Remote Similarity	NPD2094	Phase 2
0.598	Remote Similarity	NPD1630	Approved
0.5973	Remote Similarity	NPD4299	Phase 1
0.5973	Remote Similarity	NPD3947	Discontinued
0.5973	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.5971	Remote Similarity	NPD3583	Phase 2
0.597	Remote Similarity	NPD510	Phase 1
0.5965	Remote Similarity	NPD6487	Approved
0.5965	Remote Similarity	NPD2510	Approved
0.5965	Remote Similarity	NPD6486	Approved
0.5965	Remote Similarity	NPD2509	Approved
0.5962	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD3927	Phase 2
0.5957	Remote Similarity	NPD4417	Approved
0.5956	Remote Similarity	NPD7561	Approved
0.5955	Remote Similarity	NPD460	Discontinued
0.5955	Remote Similarity	NPD2717	Phase 2
0.5953	Remote Similarity	NPD2417	Approved
0.5953	Remote Similarity	NPD2416	Approved
0.5951	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD8242	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.5945	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.5942	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.5942	Remote Similarity	NPD2720	Phase 1
0.5939	Remote Similarity	NPD1600	Suspended
0.5938	Remote Similarity	NPD2912	Approved
0.5938	Remote Similarity	NPD5043	Discontinued
0.5938	Remote Similarity	NPD2911	Approved
0.5936	Remote Similarity	NPD1977	Clinical (unspecified phase)
0.5936	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.5931	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.5931	Remote Similarity	NPD6954	Phase 2
0.5929	Remote Similarity	NPD4304	Discovery
0.5929	Remote Similarity	NPD8072	Approved
0.5928	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.5924	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.5923	Remote Similarity	NPD7167	Discontinued
0.5923	Remote Similarity	NPD7543	Phase 2
0.5922	Remote Similarity	NPD5400	Approved
0.5922	Remote Similarity	NPD6771	Discontinued
0.592	Remote Similarity	NPD4887	Discontinued
0.5919	Remote Similarity	NPD4397	Phase 1
0.5918	Remote Similarity	NPD7677	Discontinued
0.5917	Remote Similarity	NPD7175	Phase 1
0.5915	Remote Similarity	NPD5198	Approved
0.5915	Remote Similarity	NPD5199	Approved
0.5915	Remote Similarity	NPD7404	Approved
0.5914	Remote Similarity	NPD5461	Discontinued
0.5913	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.5911	Remote Similarity	NPD2809	Approved
0.5905	Remote Similarity	NPD485	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD5888	Phase 2
0.5905	Remote Similarity	NPD3795	Approved
0.5905	Remote Similarity	NPD3794	Approved
0.5903	Remote Similarity	NPD8272	Phase 2
0.5903	Remote Similarity	NPD3379	Phase 2
0.5903	Remote Similarity	NPD3380	Phase 3
0.5896	Remote Similarity	NPD749	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD6459	Phase 2
0.5894	Remote Similarity	NPD1545	Discontinued
0.5893	Remote Similarity	NPD6999	Discontinued

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