NPASS Compound

Structure

NPC475410 OpenBabel07101718322D 26 32 0 0 1 0 0 0 0 0999 V2000 -1.7112 2.0179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2715 -1.5299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8415 -1.2008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8816 -1.4909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9542 0.2991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1943 -0.7296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3412 -1.2894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7423 -0.9820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0104 -0.9999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5336 -0.5160 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5352 -0.6604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3757 0.6143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1638 -0.4751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0903 0.7035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7320 0.0180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0016 -0.2845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4109 0.1319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8608 0.5090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6056 -0.3225 0.0000 N 0 5 0 0 0 0 0 0 0 0 0 0 1.6056 0.2005 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 -0.9396 -0.5499 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 -2.6135 -1.4729 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4089 0.1942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8504 1.5089 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9374 -1.3188 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 3 1 0 0 0 0 2 7 1 0 0 0 0 3 22 1 0 0 0 0 4 8 1 0 0 0 0 4 9 2 0 0 0 0 6 7 2 0 0 0 0 6 20 1 0 0 0 0 7 11 1 0 0 0 0 8 23 2 0 0 0 0 9 19 1 0 0 0 0 9 26 1 0 0 0 0 10 5 1 6 0 0 0 10 21 1 0 0 0 0 10 26 1 0 0 0 0 11 13 2 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 12 16 2 0 0 0 0 12 19 1 0 0 0 0 13 17 1 0 0 0 0 13 20 1 0 0 0 0 14 17 1 0 0 0 0 14 21 2 0 0 0 0 15 8 1 6 0 0 0 15 18 1 0 0 0 0 15 22 1 0 0 0 0 16 22 1 0 0 0 0 17 24 2 0 0 0 0 18 19 1 0 0 0 0 18 25 1 0 0 0 0 19 5 1 6 0 0 0 M CHG 3 20 -1 21 1 22 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	364.08
Volume:	335.382
LogP:	-0.996
LogD:	0.324
LogS:	-2.148
# Rotatable Bonds:	1
TPSA:	75.73
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	7
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.696
Synthetic Accessibility Score:	7.579
Fsp3:	0.421
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.43
MDCK Permeability:	1.692692603683099e-05
Pgp-inhibitor:	0.03
Pgp-substrate:	0.679
Human Intestinal Absorption (HIA):	0.798
20% Bioavailability (F20%):	0.988
30% Bioavailability (F30%):	0.862

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.39
Plasma Protein Binding (PPB):	95.03231048583984%
Volume Distribution (VD):	0.651
Pgp-substrate:	2.866814613342285%

ADMET: Metabolism

CYP1A2-inhibitor:	0.743
CYP1A2-substrate:	0.879
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.28
CYP2C9-inhibitor:	0.022
CYP2C9-substrate:	0.06
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.141
CYP3A4-inhibitor:	0.017
CYP3A4-substrate:	0.648

ADMET: Excretion

Clearance (CL):	2.374
Half-life (T1/2):	0.195

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.977
Drug-inuced Liver Injury (DILI):	0.925
AMES Toxicity:	0.63
Rat Oral Acute Toxicity:	0.165
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.312
Carcinogencity:	0.908
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.936

Download Data

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

Natural Product: NPC475410

Natural Product ID:	NPC475410
*Common Name:**	TYPMFNKWGPMUPQ-ZPESZSCVSA-O
IUPAC Name:	n.a.
Synonyms:	1-Methoxydiscorhabdin D
Standard InCHIKey:	TYPMFNKWGPMUPQ-ZPESZSCVSA-O
Standard InCHI:	InChI=1S/C19H15N3O3S/c1-25-18-15-8(23)4-9-19(18)5-10(26-9)21-14-12(19)16-11-7(2-3-22(15)16)6-20-13(11)17(14)24/h4,6,10,15,18H,2-3,5H2,1H3,(H,20,21,24)/p+1/t10-,15+,18?,19+/m0/s1
SMILES:	COC1[C@H]2C(=O)C=C3[C@]41C[C@H](S3)[NH+]=C1C4=C3[N+]2CCc2c3c(C1=O)[n-]c2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505068
PubChem CID:	44584348
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	=	232.0	nM	PMID[512533]

☑ 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 NPC475410 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	349
0.1-0.2	2540
0.2-0.3	15465
0.3-0.4	17649
0.4-0.5	3438
0.5-0.6	2764
0.6-0.7	455
0.7-0.8	20
0.8-0.85	7
0.85-0.9	1
0.9-0.95	4
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469577
0.9626	High Similarity	NPC469578
0.9319	High Similarity	NPC469562
0.9319	High Similarity	NPC220594
0.9231	High Similarity	NPC477416
0.9158	High Similarity	NPC469563
0.9016	High Similarity	NPC469359
0.8549	High Similarity	NPC476143
0.8241	Intermediate Similarity	NPC476252
0.8083	Intermediate Similarity	NPC474259
0.8083	Intermediate Similarity	NPC477415
0.8083	Intermediate Similarity	NPC23476
0.801	Intermediate Similarity	NPC469544
0.799	Intermediate Similarity	NPC143075
0.7879	Intermediate Similarity	NPC221726
0.7879	Intermediate Similarity	NPC225622
0.7879	Intermediate Similarity	NPC477414
0.7727	Intermediate Similarity	NPC268966
0.7552	Intermediate Similarity	NPC262338
0.75	Intermediate Similarity	NPC182940
0.7416	Intermediate Similarity	NPC88115
0.7404	Intermediate Similarity	NPC106757
0.7327	Intermediate Similarity	NPC473628
0.7323	Intermediate Similarity	NPC79777
0.7323	Intermediate Similarity	NPC234403
0.7206	Intermediate Similarity	NPC475874
0.7188	Intermediate Similarity	NPC470680
0.7188	Intermediate Similarity	NPC100104
0.7135	Intermediate Similarity	NPC474492
0.7115	Intermediate Similarity	NPC292361
0.709	Intermediate Similarity	NPC473878
0.7053	Intermediate Similarity	NPC217021
0.7053	Intermediate Similarity	NPC470679
0.6979	Remote Similarity	NPC477418
0.6979	Remote Similarity	NPC477420
0.6941	Remote Similarity	NPC477413
0.6908	Remote Similarity	NPC103119
0.6895	Remote Similarity	NPC100726
0.6853	Remote Similarity	NPC274981
0.6852	Remote Similarity	NPC473239
0.6823	Remote Similarity	NPC471655
0.6776	Remote Similarity	NPC123395
0.6771	Remote Similarity	NPC102664
0.6763	Remote Similarity	NPC474258
0.6729	Remote Similarity	NPC477041
0.6729	Remote Similarity	NPC477044
0.67	Remote Similarity	NPC186068
0.6699	Remote Similarity	NPC473946
0.6667	Remote Similarity	NPC255909
0.6651	Remote Similarity	NPC98715
0.665	Remote Similarity	NPC477042
0.6636	Remote Similarity	NPC98864
0.6621	Remote Similarity	NPC477043
0.662	Remote Similarity	NPC477045
0.6605	Remote Similarity	NPC78767
0.6605	Remote Similarity	NPC473814
0.6598	Remote Similarity	NPC123906
0.6589	Remote Similarity	NPC195239
0.6589	Remote Similarity	NPC157828
0.6582	Remote Similarity	NPC251391
0.6561	Remote Similarity	NPC46225
0.6561	Remote Similarity	NPC225821
0.6558	Remote Similarity	NPC11445
0.6557	Remote Similarity	NPC469489
0.6555	Remote Similarity	NPC46895
0.6553	Remote Similarity	NPC63279
0.6545	Remote Similarity	NPC327592
0.6544	Remote Similarity	NPC103361
0.6544	Remote Similarity	NPC474767
0.6532	Remote Similarity	NPC258062
0.6532	Remote Similarity	NPC127677
0.6528	Remote Similarity	NPC167710
0.6525	Remote Similarity	NPC297642
0.6516	Remote Similarity	NPC317373
0.6516	Remote Similarity	NPC472065
0.6514	Remote Similarity	NPC121327
0.6512	Remote Similarity	NPC93390
0.6502	Remote Similarity	NPC61038
0.6495	Remote Similarity	NPC216550
0.649	Remote Similarity	NPC73994
0.649	Remote Similarity	NPC61011
0.6455	Remote Similarity	NPC328318
0.6455	Remote Similarity	NPC328596
0.6455	Remote Similarity	NPC143977
0.6452	Remote Similarity	NPC74153
0.6441	Remote Similarity	NPC165743
0.6441	Remote Similarity	NPC175602
0.6441	Remote Similarity	NPC472064
0.6436	Remote Similarity	NPC469813
0.6436	Remote Similarity	NPC476446
0.6436	Remote Similarity	NPC78375
0.6435	Remote Similarity	NPC294693
0.6435	Remote Similarity	NPC135950
0.6416	Remote Similarity	NPC87856
0.6416	Remote Similarity	NPC151976
0.6409	Remote Similarity	NPC300183
0.64	Remote Similarity	NPC213914
0.6394	Remote Similarity	NPC83774
0.6394	Remote Similarity	NPC157583
0.6393	Remote Similarity	NPC284338
0.6393	Remote Similarity	NPC81535
0.6389	Remote Similarity	NPC473821
0.6388	Remote Similarity	NPC207866
0.6388	Remote Similarity	NPC267965
0.6382	Remote Similarity	NPC209362
0.638	Remote Similarity	NPC260900
0.638	Remote Similarity	NPC472069
0.638	Remote Similarity	NPC472063
0.638	Remote Similarity	NPC472062
0.6368	Remote Similarity	NPC311282
0.6359	Remote Similarity	NPC302647
0.6356	Remote Similarity	NPC271862
0.6356	Remote Similarity	NPC472070
0.6356	Remote Similarity	NPC470730
0.6356	Remote Similarity	NPC477175
0.6355	Remote Similarity	NPC209917
0.6347	Remote Similarity	NPC248782
0.6344	Remote Similarity	NPC318299
0.6343	Remote Similarity	NPC472292
0.6333	Remote Similarity	NPC471997
0.6332	Remote Similarity	NPC132211
0.6329	Remote Similarity	NPC475859
0.6329	Remote Similarity	NPC477976
0.6329	Remote Similarity	NPC475969
0.6318	Remote Similarity	NPC74413
0.6318	Remote Similarity	NPC475635
0.6316	Remote Similarity	NPC317752
0.6313	Remote Similarity	NPC313889
0.6301	Remote Similarity	NPC106824
0.6294	Remote Similarity	NPC105811
0.629	Remote Similarity	NPC252338
0.6287	Remote Similarity	NPC477176
0.6287	Remote Similarity	NPC470729
0.6282	Remote Similarity	NPC266192
0.6281	Remote Similarity	NPC70406
0.6276	Remote Similarity	NPC467188
0.6273	Remote Similarity	NPC34837
0.6272	Remote Similarity	NPC471193
0.6272	Remote Similarity	NPC471194
0.6272	Remote Similarity	NPC110182
0.6266	Remote Similarity	NPC2395
0.6262	Remote Similarity	NPC118084
0.6261	Remote Similarity	NPC477177
0.6261	Remote Similarity	NPC204491
0.6261	Remote Similarity	NPC203614
0.6261	Remote Similarity	NPC474877
0.6256	Remote Similarity	NPC472293
0.6256	Remote Similarity	NPC472116
0.6255	Remote Similarity	NPC19170
0.625	Remote Similarity	NPC185742
0.625	Remote Similarity	NPC475847
0.6245	Remote Similarity	NPC297862
0.6245	Remote Similarity	NPC472291
0.6244	Remote Similarity	NPC472296
0.6244	Remote Similarity	NPC472297
0.6239	Remote Similarity	NPC472210
0.6239	Remote Similarity	NPC269886
0.6239	Remote Similarity	NPC472295
0.6239	Remote Similarity	NPC267343
0.6239	Remote Similarity	NPC81802
0.6239	Remote Similarity	NPC247735
0.6239	Remote Similarity	NPC216612
0.6238	Remote Similarity	NPC84827
0.6238	Remote Similarity	NPC145885
0.6238	Remote Similarity	NPC14113
0.6229	Remote Similarity	NPC267926
0.6227	Remote Similarity	NPC227582
0.622	Remote Similarity	NPC139763
0.6213	Remote Similarity	NPC476817
0.6208	Remote Similarity	NPC70155
0.6207	Remote Similarity	NPC281049
0.6207	Remote Similarity	NPC80681
0.6205	Remote Similarity	NPC138562
0.6204	Remote Similarity	NPC75544
0.6203	Remote Similarity	NPC57690
0.6201	Remote Similarity	NPC6865
0.6201	Remote Similarity	NPC153980
0.6201	Remote Similarity	NPC118940
0.6197	Remote Similarity	NPC163055
0.6193	Remote Similarity	NPC47190
0.619	Remote Similarity	NPC471192
0.6186	Remote Similarity	NPC141428
0.6184	Remote Similarity	NPC70949
0.6184	Remote Similarity	NPC123839
0.618	Remote Similarity	NPC269270
0.6175	Remote Similarity	NPC154339
0.6174	Remote Similarity	NPC475602
0.617	Remote Similarity	NPC478141
0.6168	Remote Similarity	NPC207851
0.6168	Remote Similarity	NPC467063
0.6168	Remote Similarity	NPC477003
0.6168	Remote Similarity	NPC228835
0.6167	Remote Similarity	NPC266249
0.6164	Remote Similarity	NPC326422
0.6164	Remote Similarity	NPC472285
0.6161	Remote Similarity	NPC248454
0.6161	Remote Similarity	NPC284775
0.6161	Remote Similarity	NPC237188
0.616	Remote Similarity	NPC472762
0.6157	Remote Similarity	NPC72956

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 NPC475410 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	188
0.1-0.2	530
0.2-0.3	944
0.3-0.4	2479
0.4-0.5	3214
0.5-0.6	1663
0.6-0.7	132
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
0.6933	Remote Similarity	NPD6173	Approved
0.682	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6068	Discontinued
0.6544	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6044	Discontinued
0.6476	Remote Similarity	NPD3394	Approved
0.6476	Remote Similarity	NPD3389	Approved
0.6476	Remote Similarity	NPD3393	Approved
0.6471	Remote Similarity	NPD8169	Discontinued
0.6457	Remote Similarity	NPD2509	Approved
0.6457	Remote Similarity	NPD2510	Approved
0.645	Remote Similarity	NPD2214	Approved
0.645	Remote Similarity	NPD2213	Approved
0.6425	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD946	Discontinued
0.6381	Remote Similarity	NPD3178	Discontinued
0.6376	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD1096	Discontinued
0.6293	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD2893	Phase 3
0.6256	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6229	Remote Similarity	NPD8289	Discontinued
0.6223	Remote Similarity	NPD1996	Discontinued
0.6222	Remote Similarity	NPD3967	Approved
0.6222	Remote Similarity	NPD7001	Phase 3
0.622	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD7027	Phase 3
0.6178	Remote Similarity	NPD3947	Discontinued
0.6174	Remote Similarity	NPD5888	Phase 2
0.6171	Remote Similarity	NPD7049	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD7564	Discontinued
0.6167	Remote Similarity	NPD4960	Approved
0.6167	Remote Similarity	NPD4959	Approved
0.6165	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.615	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD5043	Discontinued
0.614	Remote Similarity	NPD3968	Approved
0.6137	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD8272	Phase 2
0.6106	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD8114	Approved
0.6106	Remote Similarity	NPD8115	Approved
0.6101	Remote Similarity	NPD4499	Approved
0.6099	Remote Similarity	NPD6239	Discontinued
0.6095	Remote Similarity	NPD750	Phase 2
0.6093	Remote Similarity	NPD2096	Phase 2
0.6093	Remote Similarity	NPD2091	Phase 2
0.6091	Remote Similarity	NPD3006	Discontinued
0.6087	Remote Similarity	NPD5475	Discontinued
0.6087	Remote Similarity	NPD4417	Approved
0.6085	Remote Similarity	NPD2144	Approved
0.6085	Remote Similarity	NPD2753	Discontinued
0.6083	Remote Similarity	NPD4988	Discontinued
0.6079	Remote Similarity	NPD7010	Phase 3
0.6073	Remote Similarity	NPD1977	Clinical (unspecified phase)
0.6073	Remote Similarity	NPD2336	Approved
0.6071	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD7455	Approved
0.6061	Remote Similarity	NPD7454	Approved
0.6059	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD7234	Approved
0.6055	Remote Similarity	NPD7233	Approved
0.6053	Remote Similarity	NPD3410	Approved
0.6053	Remote Similarity	NPD3411	Phase 2
0.6053	Remote Similarity	NPD4415	Approved
0.605	Remote Similarity	NPD4703	Approved
0.605	Remote Similarity	NPD1270	Approved
0.605	Remote Similarity	NPD4702	Approved
0.6047	Remote Similarity	NPD2095	Phase 2
0.6047	Remote Similarity	NPD2094	Phase 2
0.6047	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD2092	Phase 2
0.6043	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD3238	Discontinued
0.6036	Remote Similarity	NPD4848	Phase 1
0.6036	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6035	Remote Similarity	NPD4906	Approved
0.6035	Remote Similarity	NPD4905	Approved
0.6035	Remote Similarity	NPD5426	Phase 3
0.6035	Remote Similarity	NPD4903	Approved
0.6035	Remote Similarity	NPD5901	Discontinued
0.6034	Remote Similarity	NPD2823	Clinical (unspecified phase)
0.6028	Remote Similarity	NPD5473	Discontinued
0.6027	Remote Similarity	NPD6999	Discontinued
0.6027	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD7666	Phase 3
0.6026	Remote Similarity	NPD7665	Phase 2
0.6019	Remote Similarity	NPD2511	Approved
0.6019	Remote Similarity	NPD7482	Phase 2
0.6019	Remote Similarity	NPD7483	Phase 2
0.6018	Remote Similarity	NPD7187	Phase 2
0.6017	Remote Similarity	NPD1659	Phase 1
0.6017	Remote Similarity	NPD6242	Discontinued
0.6009	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6009	Remote Similarity	NPD4904	Approved
0.6009	Remote Similarity	NPD3961	Discontinued
0.6009	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.6008	Remote Similarity	NPD7661	Clinical (unspecified phase)
0.6	Remote Similarity	NPD1575	Approved
0.6	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4429	Discontinued
0.6	Remote Similarity	NPD1573	Approved
0.6	Remote Similarity	NPD3038	Discontinued
0.6	Remote Similarity	NPD6479	Discontinued
0.5991	Remote Similarity	NPD7618	Phase 3
0.5991	Remote Similarity	NPD7619	Phase 3
0.5991	Remote Similarity	NPD7195	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD482	Approved
0.5991	Remote Similarity	NPD8072	Approved
0.5984	Remote Similarity	NPD7551	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD7550	Clinical (unspecified phase)
0.598	Remote Similarity	NPD751	Clinical (unspecified phase)
0.5973	Remote Similarity	NPD5017	Discontinued
0.5973	Remote Similarity	NPD7817	Phase 1
0.5973	Remote Similarity	NPD5259	Phase 3
0.5973	Remote Similarity	NPD7727	Phase 2
0.5972	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.5971	Remote Similarity	NPD1630	Approved
0.5969	Remote Similarity	NPD5461	Discontinued
0.5965	Remote Similarity	NPD6987	Phase 1
0.5964	Remote Similarity	NPD2307	Discontinued
0.5963	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD749	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD5443	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD2405	Phase 3
0.5956	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.5953	Remote Similarity	NPD2481	Approved
0.5953	Remote Similarity	NPD2479	Phase 3
0.5948	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD3915	Approved
0.5947	Remote Similarity	NPD8073	Approved
0.5947	Remote Similarity	NPD4924	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD4524	Discontinued
0.5939	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD5948	Phase 2
0.5931	Remote Similarity	NPD5510	Approved
0.5929	Remote Similarity	NPD4500	Approved
0.5929	Remote Similarity	NPD4501	Approved
0.5928	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD7552	Discontinued
0.5923	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.5923	Remote Similarity	NPD3917	Approved
0.5923	Remote Similarity	NPD3918	Approved
0.5922	Remote Similarity	NPD2582	Approved
0.5922	Remote Similarity	NPD2581	Approved
0.5919	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.5919	Remote Similarity	NPD4602	Approved
0.5915	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.5911	Remote Similarity	NPD7677	Discontinued
0.5909	Remote Similarity	NPD7780	Approved
0.5909	Remote Similarity	NPD2850	Phase 1
0.5909	Remote Similarity	NPD2851	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD7781	Approved
0.5907	Remote Similarity	NPD7404	Approved
0.5905	Remote Similarity	NPD4051	Discontinued
0.5905	Remote Similarity	NPD5636	Discontinued
0.5901	Remote Similarity	NPD6665	Discontinued
0.5896	Remote Similarity	NPD3609	Approved
0.5896	Remote Similarity	NPD3610	Approved
0.5896	Remote Similarity	NPD485	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD6226	Phase 3
0.589	Remote Similarity	NPD8326	Phase 3
0.589	Remote Similarity	NPD8325	Phase 3
0.589	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.589	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD6376	Discontinued
0.5887	Remote Similarity	NPD7191	Phase 2
0.5885	Remote Similarity	NPD5088	Discontinued
0.5885	Remote Similarity	NPD1631	Approved
0.5885	Remote Similarity	NPD6635	Approved
0.5885	Remote Similarity	NPD3583	Phase 2
0.5885	Remote Similarity	NPD1545	Discontinued
0.5882	Remote Similarity	NPD3321	Discontinued
0.588	Remote Similarity	NPD1643	Phase 3
0.588	Remote Similarity	NPD7470	Discontinued
0.588	Remote Similarity	NPD6152	Phase 1
0.5878	Remote Similarity	NPD4850	Phase 1
0.5877	Remote Similarity	NPD7561	Approved
0.5877	Remote Similarity	NPD5862	Discovery
0.5875	Remote Similarity	NPD6753	Phase 1
0.5875	Remote Similarity	NPD6752	Phase 1
0.5872	Remote Similarity	NPD5293	Phase 2
0.5872	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.587	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD4845	Discontinued
0.5868	Remote Similarity	NPD4086	Phase 1
0.5865	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.5861	Remote Similarity	NPD8372	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