NPASS Compound

Structure

NPC476143 OpenBabel07101718322D 24 30 0 0 1 0 0 0 0 0999 V2000 2.8517 -2.7393 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2617 -2.3986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2203 -2.6989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2418 -0.6291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1203 -0.8463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3337 -1.9110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4858 -2.4904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3401 -1.1372 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.3294 -2.1722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1219 -2.1908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7199 -1.6899 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.6866 -1.8394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5215 -0.5201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3372 -1.6476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2611 -0.4277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1310 -1.4504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5929 -1.0193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1327 -1.1559 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.7594 -1.4896 0.0000 N 0 5 0 0 0 0 0 0 0 0 0 0 4.7944 -0.9483 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 2.1602 -1.7250 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.4277 -2.6803 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6258 -0.9549 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1029 -2.5208 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 7 1 0 0 0 0 2 21 1 0 0 0 0 3 9 1 0 0 0 0 3 10 2 0 0 0 0 4 8 1 0 0 0 0 4 18 1 0 0 0 0 5 11 1 0 0 0 0 5 18 1 0 0 0 0 6 7 2 0 0 0 0 6 19 1 0 0 0 0 7 12 1 0 0 0 0 8 9 1 0 0 0 0 8 21 1 0 0 0 0 9 22 2 0 0 0 0 10 18 1 0 0 0 0 10 24 1 0 0 0 0 11 20 1 0 0 0 0 11 24 1 0 0 0 0 12 14 2 0 0 0 0 12 16 1 0 0 0 0 13 15 1 0 0 0 0 13 16 2 0 0 0 0 13 18 1 0 0 0 0 14 17 1 0 0 0 0 14 19 1 0 0 0 0 15 17 1 0 0 0 0 15 20 2 0 0 0 0 16 21 1 0 0 0 0 17 23 2 0 0 0 0 M CHG 2 19 -1 20 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	335.07
Volume:	310.614
LogP:	3.501
LogD:	1.91
LogS:	-4.741
# Rotatable Bonds:	0
TPSA:	68.36
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.646
Synthetic Accessibility Score:	6.717
Fsp3:	0.278
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.995
MDCK Permeability:	5.389640136854723e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.781
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	98.0101547241211%
Volume Distribution (VD):	0.729
Pgp-substrate:	2.2244372367858887%

ADMET: Metabolism

CYP1A2-inhibitor:	0.584
CYP1A2-substrate:	0.521
CYP2C19-inhibitor:	0.738
CYP2C19-substrate:	0.321
CYP2C9-inhibitor:	0.734
CYP2C9-substrate:	0.968
CYP2D6-inhibitor:	0.698
CYP2D6-substrate:	0.446
CYP3A4-inhibitor:	0.497
CYP3A4-substrate:	0.694

ADMET: Excretion

Clearance (CL):	4.544
Half-life (T1/2):	0.858

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.671
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.591
Rat Oral Acute Toxicity:	0.823
Maximum Recommended Daily Dose:	0.921
Skin Sensitization:	0.312
Carcinogencity:	0.894
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.88

Download Data

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

Natural Product: NPC476143

Natural Product ID:	NPC476143
*Common Name:**	Discorhabdin D
IUPAC Name:	n.a.
Synonyms:	Discorhabdin D
Standard InCHIKey:	YMKMUPNCQGYYIV-TYLCVAKFSA-N
Standard InCHI:	InChI=1S/C18H13N3O2S.C2HF3O2/c22-9-3-10-18-4-8(9)21-2-1-7-6-19-14-12(7)16(21)13(18)15(17(14)23)20-11(5-18)24-10;3-2(4,5)1(6)7/h3,6,8,11H,1-2,4-5H2,(H,19,20,23);(H,6,7)/t8-,11-,18-;/m0./s1
SMILES:	OC(=O)C(F)(F)F.O=C1C=C2S[C@H]3C[C@]42C[C@@H]1N1CCc2c5C1=C4C(=[NH+]3)C(=O)c5[n-]c2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL540660
PubChem CID:	45266485
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]
NPO32733	latrunculia sp.	Species	Latrunculiidae	Eukaryota	n.a.	Anita Bay, in Milford Sound, Fiordland, New Zealand, at a depth of ~22 m	2003-NOV	PMID[16378380]
NPO32733	latrunculia sp.	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20337497]
NPO32733	latrunculia sp.	Species	Latrunculiidae	Eukaryota	n.a.	New Zealand	n.a.	PMID[20860391]

☑ 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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	1600.0	nM	PMID[460938]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	595.0	nM	PMID[460939]

☑ 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 NPC476143 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	417
0.1-0.2	3084
0.2-0.3	21410
0.3-0.4	12055
0.4-0.5	3112
0.5-0.6	2242
0.6-0.7	328
0.7-0.8	26
0.8-0.85	7
0.85-0.9	10
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9613	High Similarity	NPC476252
0.9429	High Similarity	NPC469359
0.9115	High Similarity	NPC477416
0.8836	High Similarity	NPC469563
0.8698	High Similarity	NPC469578
0.8608	High Similarity	NPC220594
0.8608	High Similarity	NPC469562
0.8549	High Similarity	NPC469577
0.8549	High Similarity	NPC475410
0.8432	Intermediate Similarity	NPC474259
0.8432	Intermediate Similarity	NPC23476
0.8432	Intermediate Similarity	NPC477415
0.8211	Intermediate Similarity	NPC221726
0.8211	Intermediate Similarity	NPC477414
0.8211	Intermediate Similarity	NPC225622
0.7958	Intermediate Similarity	NPC268966
0.788	Intermediate Similarity	NPC262338
0.7861	Intermediate Similarity	NPC143075
0.7725	Intermediate Similarity	NPC182940
0.7632	Intermediate Similarity	NPC234403
0.7632	Intermediate Similarity	NPC79777
0.7624	Intermediate Similarity	NPC88115
0.7612	Intermediate Similarity	NPC106757
0.7538	Intermediate Similarity	NPC473628
0.7446	Intermediate Similarity	NPC474492
0.7411	Intermediate Similarity	NPC475874
0.7405	Intermediate Similarity	NPC470680
0.7405	Intermediate Similarity	NPC100104
0.7308	Intermediate Similarity	NPC473878
0.7301	Intermediate Similarity	NPC477418
0.7301	Intermediate Similarity	NPC477420
0.7286	Intermediate Similarity	NPC477413
0.7286	Intermediate Similarity	NPC469544
0.7268	Intermediate Similarity	NPC470679
0.7268	Intermediate Similarity	NPC217021
0.7143	Intermediate Similarity	NPC274981
0.712	Intermediate Similarity	NPC471655
0.7104	Intermediate Similarity	NPC100726
0.71	Intermediate Similarity	NPC103119
0.7015	Intermediate Similarity	NPC255909
0.6974	Remote Similarity	NPC186068
0.6973	Remote Similarity	NPC102664
0.695	Remote Similarity	NPC474258
0.6893	Remote Similarity	NPC292361
0.6881	Remote Similarity	NPC473946
0.6834	Remote Similarity	NPC477042
0.681	Remote Similarity	NPC98864
0.6791	Remote Similarity	NPC123906
0.6779	Remote Similarity	NPC167710
0.6772	Remote Similarity	NPC251391
0.6748	Remote Similarity	NPC216550
0.6734	Remote Similarity	NPC157583
0.6619	Remote Similarity	NPC78767
0.6619	Remote Similarity	NPC473814
0.6558	Remote Similarity	NPC473239
0.654	Remote Similarity	NPC74153
0.6524	Remote Similarity	NPC93390
0.6509	Remote Similarity	NPC477041
0.6509	Remote Similarity	NPC248782
0.6509	Remote Similarity	NPC477044
0.6495	Remote Similarity	NPC213914
0.6492	Remote Similarity	NPC313889
0.6477	Remote Similarity	NPC209362
0.6476	Remote Similarity	NPC473821
0.6474	Remote Similarity	NPC105811
0.6458	Remote Similarity	NPC70406
0.6455	Remote Similarity	NPC467188
0.6452	Remote Similarity	NPC175602
0.645	Remote Similarity	NPC302647
0.6445	Remote Similarity	NPC294693
0.6438	Remote Similarity	NPC61038
0.6432	Remote Similarity	NPC34837
0.6429	Remote Similarity	NPC47190
0.6422	Remote Similarity	NPC73994
0.6418	Remote Similarity	NPC477976
0.6408	Remote Similarity	NPC467063
0.6408	Remote Similarity	NPC477003
0.6404	Remote Similarity	NPC237188
0.6404	Remote Similarity	NPC284775
0.6402	Remote Similarity	NPC477045
0.6398	Remote Similarity	NPC326422
0.6395	Remote Similarity	NPC475635
0.6378	Remote Similarity	NPC80681
0.6377	Remote Similarity	NPC311282
0.6368	Remote Similarity	NPC195239
0.6368	Remote Similarity	NPC157828
0.6359	Remote Similarity	NPC138562
0.635	Remote Similarity	NPC70949
0.6338	Remote Similarity	NPC11445
0.633	Remote Similarity	NPC477043
0.6326	Remote Similarity	NPC474767
0.6324	Remote Similarity	NPC83774
0.6323	Remote Similarity	NPC207866
0.6321	Remote Similarity	NPC304203
0.6311	Remote Similarity	NPC191415
0.6308	Remote Similarity	NPC272483
0.6303	Remote Similarity	NPC476460
0.6293	Remote Similarity	NPC283219
0.6262	Remote Similarity	NPC61011
0.625	Remote Similarity	NPC123395
0.625	Remote Similarity	NPC46895
0.6233	Remote Similarity	NPC477417
0.6233	Remote Similarity	NPC477419
0.623	Remote Similarity	NPC476158
0.6225	Remote Similarity	NPC469529
0.6225	Remote Similarity	NPC203468
0.6225	Remote Similarity	NPC149155
0.6225	Remote Similarity	NPC110500
0.6224	Remote Similarity	NPC229055
0.6221	Remote Similarity	NPC252338
0.6221	Remote Similarity	NPC121327
0.6215	Remote Similarity	NPC202812
0.6214	Remote Similarity	NPC126709
0.6214	Remote Similarity	NPC248041
0.6214	Remote Similarity	NPC55772
0.6214	Remote Similarity	NPC11126
0.621	Remote Similarity	NPC317701
0.6205	Remote Similarity	NPC471193
0.6205	Remote Similarity	NPC110182
0.6205	Remote Similarity	NPC471194
0.6197	Remote Similarity	NPC472292
0.6195	Remote Similarity	NPC267885
0.6193	Remote Similarity	NPC74357
0.619	Remote Similarity	NPC19170
0.619	Remote Similarity	NPC235684
0.6186	Remote Similarity	NPC472293
0.618	Remote Similarity	NPC297862
0.6179	Remote Similarity	NPC469489
0.6172	Remote Similarity	NPC228835
0.6169	Remote Similarity	NPC233380
0.6169	Remote Similarity	NPC71132
0.6165	Remote Similarity	NPC145885
0.6165	Remote Similarity	NPC84827
0.6165	Remote Similarity	NPC14113
0.6164	Remote Similarity	NPC143977
0.6161	Remote Similarity	NPC17059
0.6157	Remote Similarity	NPC227582
0.6154	Remote Similarity	NPC472065
0.6147	Remote Similarity	NPC229893
0.6147	Remote Similarity	NPC476817
0.6146	Remote Similarity	NPC139763
0.6143	Remote Similarity	NPC472070
0.6143	Remote Similarity	NPC99939
0.6143	Remote Similarity	NPC308931
0.6139	Remote Similarity	NPC41717
0.6136	Remote Similarity	NPC98715
0.6135	Remote Similarity	NPC213468
0.6133	Remote Similarity	NPC318299
0.6132	Remote Similarity	NPC321708
0.6126	Remote Similarity	NPC225821
0.6126	Remote Similarity	NPC46225
0.6124	Remote Similarity	NPC102755
0.6123	Remote Similarity	NPC476161
0.6122	Remote Similarity	NPC216713
0.6119	Remote Similarity	NPC300183
0.6119	Remote Similarity	NPC265100
0.6114	Remote Similarity	NPC269270
0.6111	Remote Similarity	NPC128244
0.6111	Remote Similarity	NPC102592
0.6111	Remote Similarity	NPC79356
0.6108	Remote Similarity	NPC78020
0.6106	Remote Similarity	NPC317752
0.6101	Remote Similarity	NPC103361
0.6101	Remote Similarity	NPC472297
0.6101	Remote Similarity	NPC472296
0.6099	Remote Similarity	NPC258062
0.6099	Remote Similarity	NPC127677
0.6093	Remote Similarity	NPC472295
0.6093	Remote Similarity	NPC269886
0.6093	Remote Similarity	NPC472210
0.6093	Remote Similarity	NPC247735
0.6093	Remote Similarity	NPC81802
0.6091	Remote Similarity	NPC260900
0.6091	Remote Similarity	NPC328318
0.6091	Remote Similarity	NPC328596
0.6089	Remote Similarity	NPC82370
0.6089	Remote Similarity	NPC72956
0.6087	Remote Similarity	NPC111275
0.6087	Remote Similarity	NPC14686
0.6087	Remote Similarity	NPC248454
0.6081	Remote Similarity	NPC472064
0.6078	Remote Similarity	NPC91895
0.6071	Remote Similarity	NPC271862
0.6068	Remote Similarity	NPC476491
0.6066	Remote Similarity	NPC133003
0.6062	Remote Similarity	NPC153980
0.6062	Remote Similarity	NPC6865
0.6056	Remote Similarity	NPC75544
0.6056	Remote Similarity	NPC209917
0.6053	Remote Similarity	NPC177996
0.6053	Remote Similarity	NPC147983
0.6047	Remote Similarity	NPC272458
0.6041	Remote Similarity	NPC472260
0.6038	Remote Similarity	NPC62749
0.6036	Remote Similarity	NPC327592
0.6029	Remote Similarity	NPC471997
0.6027	Remote Similarity	NPC477004
0.6027	Remote Similarity	NPC284338
0.6027	Remote Similarity	NPC74413
0.6026	Remote Similarity	NPC477715

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 NPC476143 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	208
0.1-0.2	547
0.2-0.3	1187
0.3-0.4	2589
0.4-0.5	3058
0.5-0.6	1410
0.6-0.7	151
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
0.6802	Remote Similarity	NPD6173	Approved
0.6761	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD6044	Discontinued
0.6517	Remote Similarity	NPD3238	Discontinued
0.6502	Remote Similarity	NPD5473	Discontinued
0.6468	Remote Similarity	NPD4959	Approved
0.6468	Remote Similarity	NPD4960	Approved
0.6449	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD7661	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD4415	Approved
0.639	Remote Similarity	NPD3178	Discontinued
0.6382	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6068	Discontinued
0.6359	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD7027	Phase 3
0.6329	Remote Similarity	NPD7564	Discontinued
0.6329	Remote Similarity	NPD6178	Phase 3
0.6329	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6326	Remote Similarity	NPD2405	Phase 3
0.6313	Remote Similarity	NPD7187	Phase 2
0.6311	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.63	Remote Similarity	NPD6446	Discontinued
0.629	Remote Similarity	NPD3968	Approved
0.6273	Remote Similarity	NPD3410	Approved
0.6273	Remote Similarity	NPD3411	Phase 2
0.6268	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD4848	Phase 1
0.6262	Remote Similarity	NPD2307	Discontinued
0.6256	Remote Similarity	NPD750	Phase 2
0.6256	Remote Similarity	NPD5901	Discontinued
0.625	Remote Similarity	NPD2096	Phase 2
0.625	Remote Similarity	NPD2091	Phase 2
0.6244	Remote Similarity	NPD2753	Discontinued
0.6238	Remote Similarity	NPD4988	Discontinued
0.6227	Remote Similarity	NPD3967	Approved
0.6225	Remote Similarity	NPD482	Approved
0.6218	Remote Similarity	NPD1270	Approved
0.6216	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD7618	Phase 3
0.6215	Remote Similarity	NPD7619	Phase 3
0.6209	Remote Similarity	NPD7233	Approved
0.6209	Remote Similarity	NPD7234	Approved
0.6204	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD2094	Phase 2
0.6202	Remote Similarity	NPD2092	Phase 2
0.6202	Remote Similarity	NPD2095	Phase 2
0.6195	Remote Similarity	NPD3394	Approved
0.6195	Remote Similarity	NPD3393	Approved
0.6195	Remote Similarity	NPD3389	Approved
0.6193	Remote Similarity	NPD3890	Phase 2
0.6193	Remote Similarity	NPD3891	Phase 2
0.6193	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5809	Phase 3
0.6188	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD2479	Phase 3
0.6184	Remote Similarity	NPD2481	Approved
0.6182	Remote Similarity	NPD8169	Discontinued
0.6171	Remote Similarity	NPD7191	Phase 2
0.6167	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6165	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD3961	Discontinued
0.6158	Remote Similarity	NPD1573	Approved
0.6158	Remote Similarity	NPD1575	Approved
0.615	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.615	Remote Similarity	NPD2336	Approved
0.6146	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD5510	Approved
0.6143	Remote Similarity	NPD3856	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.614	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.614	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD5636	Discontinued
0.6136	Remote Similarity	NPD4304	Discovery
0.6131	Remote Similarity	NPD2213	Approved
0.6131	Remote Similarity	NPD2214	Approved
0.6126	Remote Similarity	NPD7562	Approved
0.6121	Remote Similarity	NPD4922	Phase 2
0.6119	Remote Similarity	NPD5017	Discontinued
0.6117	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD2290	Phase 3
0.6111	Remote Similarity	NPD2289	Phase 3
0.6109	Remote Similarity	NPD4906	Approved
0.6109	Remote Similarity	NPD4905	Approved
0.6109	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6109	Remote Similarity	NPD4903	Approved
0.61	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD2509	Approved
0.6099	Remote Similarity	NPD2510	Approved
0.6098	Remote Similarity	NPD4524	Discontinued
0.6093	Remote Similarity	NPD2717	Phase 2
0.6091	Remote Similarity	NPD7561	Approved
0.6091	Remote Similarity	NPD8073	Approved
0.6091	Remote Similarity	NPD4924	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD2720	Phase 1
0.6089	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.6081	Remote Similarity	NPD4904	Approved
0.6073	Remote Similarity	NPD4961	Approved
0.6073	Remote Similarity	NPD5043	Discontinued
0.607	Remote Similarity	NPD5400	Approved
0.6068	Remote Similarity	NPD4883	Approved
0.6061	Remote Similarity	NPD2809	Approved
0.6056	Remote Similarity	NPD2851	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD2850	Phase 1
0.6055	Remote Similarity	NPD4364	Phase 1
0.6053	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD3353	Approved
0.6049	Remote Similarity	NPD3609	Approved
0.6049	Remote Similarity	NPD3610	Approved
0.6045	Remote Similarity	NPD4963	Approved
0.6045	Remote Similarity	NPD4962	Approved
0.6044	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.604	Remote Similarity	NPD3583	Phase 2
0.604	Remote Similarity	NPD1545	Discontinued
0.604	Remote Similarity	NPD1631	Approved
0.6038	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD7026	Phase 2
0.6036	Remote Similarity	NPD6987	Phase 1
0.6036	Remote Similarity	NPD3947	Discontinued
0.6036	Remote Similarity	NPD4299	Phase 1
0.6035	Remote Similarity	NPD3794	Approved
0.6035	Remote Similarity	NPD3795	Approved
0.6029	Remote Similarity	NPD3927	Phase 2
0.6027	Remote Similarity	NPD6239	Discontinued
0.6027	Remote Similarity	NPD3425	Discontinued
0.6018	Remote Similarity	NPD3773	Approved
0.6018	Remote Similarity	NPD3774	Approved
0.6018	Remote Similarity	NPD5475	Discontinued
0.6018	Remote Similarity	NPD3775	Approved
0.6018	Remote Similarity	NPD6152	Phase 1
0.601	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6009	Remote Similarity	NPD3246	Discontinued
0.6009	Remote Similarity	NPD6156	Clinical (unspecified phase)
0.6009	Remote Similarity	NPD6752	Phase 1
0.6009	Remote Similarity	NPD6664	Approved
0.6009	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.6009	Remote Similarity	NPD6753	Phase 1
0.6	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6	Remote Similarity	NPD1977	Clinical (unspecified phase)
0.6	Remote Similarity	NPD201	Phase 2
0.6	Remote Similarity	NPD200	Phase 2
0.6	Remote Similarity	NPD4949	Discontinued
0.5991	Remote Similarity	NPD7195	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD8072	Approved
0.5991	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.599	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD2947	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD7175	Phase 1
0.598	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD6665	Discontinued
0.597	Remote Similarity	NPD704	Clinical (unspecified phase)
0.597	Remote Similarity	NPD1630	Approved
0.5969	Remote Similarity	NPD2896	Discontinued
0.5964	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.5964	Remote Similarity	NPD3379	Phase 2
0.5964	Remote Similarity	NPD3380	Phase 3
0.5964	Remote Similarity	NPD5426	Phase 3
0.5961	Remote Similarity	NPD5088	Discontinued
0.596	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.596	Remote Similarity	NPD510	Phase 1
0.5956	Remote Similarity	NPD7232	Discontinued
0.5956	Remote Similarity	NPD6487	Approved
0.5956	Remote Similarity	NPD6486	Approved
0.5956	Remote Similarity	NPD4882	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD7049	Clinical (unspecified phase)
0.5953	Remote Similarity	NPD4499	Approved
0.5951	Remote Similarity	NPD1343	Approved
0.595	Remote Similarity	NPD2893	Phase 3
0.5947	Remote Similarity	NPD206	Clinical (unspecified phase)
0.5947	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.5947	Remote Similarity	NPD3915	Approved
0.5947	Remote Similarity	NPD4417	Approved
0.5945	Remote Similarity	NPD2004	Clinical (unspecified phase)
0.5945	Remote Similarity	NPD460	Discontinued
0.5941	Remote Similarity	NPD4850	Phase 1
0.594	Remote Similarity	NPD5046	Discontinued
0.5939	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.5939	Remote Similarity	NPD7970	Approved
0.5938	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.5931	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.5928	Remote Similarity	NPD2912	Approved
0.5928	Remote Similarity	NPD2911	Approved
0.5926	Remote Similarity	NPD4918	Discontinued
0.5926	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.5924	Remote Similarity	NPD7552	Discontinued
0.5924	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD3918	Approved
0.5921	Remote Similarity	NPD3917	Approved
0.5917	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD7550	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD4427	Phase 2
0.5917	Remote Similarity	NPD7551	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