NPASS Compound

Structure

NPC469359 OpenBabel07101719242D 24 30 0 0 1 0 0 0 0 0999 V2000 0.6681 -0.9800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0981 -0.6509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0581 -0.9410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0788 1.0589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8938 0.8490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1339 -0.1797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2808 -0.7395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7923 0.5679 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8027 -0.4320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9292 -0.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4732 0.0340 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4749 -0.1105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3154 1.1642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1035 0.0748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0299 1.2535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9380 0.2654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3505 0.6818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9396 0.5499 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5452 0.2274 0.0000 N 0 5 0 0 0 0 0 0 0 0 0 0 2.5452 0.7504 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 -1.6739 -0.9230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3485 0.7441 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8770 -0.7689 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 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 5 1 6 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 18 4 1 6 0 0 0 M CHG 3 19 -1 20 1 21 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	859.51
Volume:	879.84
LogP:	2.019
LogD:	1.451
LogS:	-2.595
# Rotatable Bonds:	15
TPSA:	292.42
# H-Bond Aceptor:	18
# H-Bond Donor:	10
# Rings:	2
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.052
Synthetic Accessibility Score:	5.971
Fsp3:	0.674
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.982
MDCK Permeability:	8.701073238626122e-05
Pgp-inhibitor:	0.984
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.986
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.089
Plasma Protein Binding (PPB):	55.57331466674805%
Volume Distribution (VD):	0.587
Pgp-substrate:	26.726112365722656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.007
CYP2C19-inhibitor:	0.042
CYP2C19-substrate:	0.037
CYP2C9-inhibitor:	0.072
CYP2C9-substrate:	0.272
CYP2D6-inhibitor:	0.113
CYP2D6-substrate:	0.07
CYP3A4-inhibitor:	0.116
CYP3A4-substrate:	0.016

ADMET: Excretion

Clearance (CL):	1.052
Half-life (T1/2):	0.876

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.999
Drug-inuced Liver Injury (DILI):	0.89
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.556
Skin Sensitization:	0.255
Carcinogencity:	0.066
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC469359

Natural Product ID:	NPC469359
*Common Name:**	QYJUINXANIOBKV-YSTSUOIISA-O
IUPAC Name:	n.a.
Synonyms:	(+)-Discorhabdin D
Standard InCHIKey:	QYJUINXANIOBKV-YSTSUOIISA-O
Standard InCHI:	InChI=1S/C18H13N3O2S/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/h3,6,8,11H,1-2,4-5H2,(H,19,20,23)/p+1/t8?,11-,18-/m0/s1
SMILES:	O=C1c2[n-]cc3c2C2=C4C1=[NH+][C@H]1SC5=CC(=O)C([N+]2CC3)C[C@@]45C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1076784
PubChem CID:	44584254
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
NPO33184	sceptrella sp.	Species	Latrunculiidae	Eukaryota	n.a.	Korean	n.a.	PMID[20055495]

☑ 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
MIC	6

Activity Type	# Activity
Cell Line	1
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	6100.0	nM	PMID[569800]
NPT1190	Organism	Salmonella enterica	Salmonella enterica	MIC	>	100.0	ug.mL-1	PMID[569800]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[569800]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[569800]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	100.0	ug.mL-1	PMID[569800]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	6.25	ug.mL-1	PMID[569800]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	25.0	ug.mL-1	PMID[569800]

☑ 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 NPC469359 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	545
0.1-0.2	4623
0.2-0.3	22690
0.3-0.4	9319
0.4-0.5	2887
0.5-0.6	2129
0.6-0.7	441
0.7-0.8	36
0.8-0.85	7
0.85-0.9	12
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9429	High Similarity	NPC476143
0.9116	High Similarity	NPC469563
0.9061	High Similarity	NPC476252
0.9016	High Similarity	NPC475410
0.9016	High Similarity	NPC469577
0.8967	High Similarity	NPC469578
0.8914	High Similarity	NPC23476
0.8914	High Similarity	NPC474259
0.8914	High Similarity	NPC477415
0.8871	High Similarity	NPC220594
0.8871	High Similarity	NPC469562
0.8667	High Similarity	NPC477414
0.8667	High Similarity	NPC225622
0.8667	High Similarity	NPC221726
0.8594	High Similarity	NPC477416
0.8398	Intermediate Similarity	NPC268966
0.8333	Intermediate Similarity	NPC262338
0.8156	Intermediate Similarity	NPC182940
0.8083	Intermediate Similarity	NPC143075
0.8056	Intermediate Similarity	NPC79777
0.8056	Intermediate Similarity	NPC234403
0.8021	Intermediate Similarity	NPC88115
0.801	Intermediate Similarity	NPC106757
0.7874	Intermediate Similarity	NPC474492
0.7829	Intermediate Similarity	NPC470680
0.7829	Intermediate Similarity	NPC100104
0.7754	Intermediate Similarity	NPC473628
0.7733	Intermediate Similarity	NPC473878
0.7688	Intermediate Similarity	NPC470679
0.7688	Intermediate Similarity	NPC217021
0.7619	Intermediate Similarity	NPC475874
0.7562	Intermediate Similarity	NPC477413
0.7542	Intermediate Similarity	NPC274981
0.7529	Intermediate Similarity	NPC471655
0.7514	Intermediate Similarity	NPC100726
0.7474	Intermediate Similarity	NPC103119
0.7389	Intermediate Similarity	NPC469544
0.7371	Intermediate Similarity	NPC102664
0.7351	Intermediate Similarity	NPC186068
0.7202	Intermediate Similarity	NPC255909
0.7196	Intermediate Similarity	NPC477042
0.7175	Intermediate Similarity	NPC123906
0.7162	Intermediate Similarity	NPC477420
0.7162	Intermediate Similarity	NPC477418
0.7151	Intermediate Similarity	NPC251391
0.7135	Intermediate Similarity	NPC474258
0.7121	Intermediate Similarity	NPC167710
0.7092	Intermediate Similarity	NPC216550
0.7062	Intermediate Similarity	NPC473946
0.6985	Remote Similarity	NPC292361
0.6911	Remote Similarity	NPC157583
0.6851	Remote Similarity	NPC313889
0.6833	Remote Similarity	NPC105811
0.6816	Remote Similarity	NPC467188
0.6813	Remote Similarity	NPC70406
0.6782	Remote Similarity	NPC473814
0.6782	Remote Similarity	NPC78767
0.6753	Remote Similarity	NPC73994
0.6749	Remote Similarity	NPC34837
0.6736	Remote Similarity	NPC284775
0.6736	Remote Similarity	NPC237188
0.6735	Remote Similarity	NPC477003
0.6735	Remote Similarity	NPC467063
0.672	Remote Similarity	NPC80681
0.6716	Remote Similarity	NPC326422
0.67	Remote Similarity	NPC74153
0.6684	Remote Similarity	NPC70949
0.6683	Remote Similarity	NPC93390
0.6667	Remote Similarity	NPC213914
0.6667	Remote Similarity	NPC477044
0.6667	Remote Similarity	NPC477041
0.665	Remote Similarity	NPC98864
0.6649	Remote Similarity	NPC83774
0.6649	Remote Similarity	NPC209362
0.6634	Remote Similarity	NPC473821
0.6634	Remote Similarity	NPC304203
0.6633	Remote Similarity	NPC191415
0.6617	Remote Similarity	NPC476460
0.6603	Remote Similarity	NPC175602
0.6601	Remote Similarity	NPC294693
0.6588	Remote Similarity	NPC61038
0.6584	Remote Similarity	NPC47190
0.6582	Remote Similarity	NPC61011
0.6559	Remote Similarity	NPC229055
0.6555	Remote Similarity	NPC473239
0.6553	Remote Similarity	NPC477045
0.6546	Remote Similarity	NPC469529
0.6533	Remote Similarity	NPC475635
0.6524	Remote Similarity	NPC74357
0.652	Remote Similarity	NPC195239
0.652	Remote Similarity	NPC157828
0.6507	Remote Similarity	NPC138562
0.6507	Remote Similarity	NPC317701
0.6492	Remote Similarity	NPC71132
0.6492	Remote Similarity	NPC233380
0.6488	Remote Similarity	NPC11445
0.6482	Remote Similarity	NPC46895
0.6476	Remote Similarity	NPC477043
0.6465	Remote Similarity	NPC207866
0.645	Remote Similarity	NPC99939
0.645	Remote Similarity	NPC308931
0.6445	Remote Similarity	NPC472065
0.6442	Remote Similarity	NPC121327
0.644	Remote Similarity	NPC265100
0.6432	Remote Similarity	NPC102755
0.6408	Remote Similarity	NPC128244
0.6394	Remote Similarity	NPC474767
0.6392	Remote Similarity	NPC91895
0.6381	Remote Similarity	NPC143977
0.6368	Remote Similarity	NPC472064
0.6368	Remote Similarity	NPC133003
0.6364	Remote Similarity	NPC252338
0.6364	Remote Similarity	NPC472260
0.6364	Remote Similarity	NPC11126
0.6359	Remote Similarity	NPC302647
0.6346	Remote Similarity	NPC248782
0.6343	Remote Similarity	NPC471194
0.6343	Remote Similarity	NPC471193
0.6343	Remote Similarity	NPC110182
0.6341	Remote Similarity	NPC272458
0.6333	Remote Similarity	NPC65408
0.6321	Remote Similarity	NPC115232
0.6321	Remote Similarity	NPC42372
0.6318	Remote Similarity	NPC228835
0.6316	Remote Similarity	NPC477004
0.6316	Remote Similarity	NPC284338
0.6316	Remote Similarity	NPC193740
0.6316	Remote Similarity	NPC123395
0.6313	Remote Similarity	NPC291517
0.6305	Remote Similarity	NPC17059
0.6303	Remote Similarity	NPC472062
0.6303	Remote Similarity	NPC472069
0.6303	Remote Similarity	NPC472063
0.6303	Remote Similarity	NPC260900
0.6298	Remote Similarity	NPC227582
0.6294	Remote Similarity	NPC139763
0.6287	Remote Similarity	NPC311282
0.6277	Remote Similarity	NPC216713
0.6274	Remote Similarity	NPC98715
0.6269	Remote Similarity	NPC470205
0.6269	Remote Similarity	NPC271797
0.6269	Remote Similarity	NPC21174
0.6262	Remote Similarity	NPC472292
0.6256	Remote Similarity	NPC300183
0.625	Remote Similarity	NPC136002
0.625	Remote Similarity	NPC19170
0.6244	Remote Similarity	NPC477976
0.6244	Remote Similarity	NPC324091
0.6239	Remote Similarity	NPC297862
0.6238	Remote Similarity	NPC237414
0.6238	Remote Similarity	NPC81535
0.6238	Remote Similarity	NPC74413
0.6231	Remote Similarity	NPC248454
0.6231	Remote Similarity	NPC84827
0.6231	Remote Similarity	NPC145885
0.6231	Remote Similarity	NPC14113
0.6226	Remote Similarity	NPC328318
0.6226	Remote Similarity	NPC328596
0.6224	Remote Similarity	NPC471943
0.6221	Remote Similarity	NPC477419
0.6221	Remote Similarity	NPC477417
0.6221	Remote Similarity	NPC72956
0.622	Remote Similarity	NPC106824
0.622	Remote Similarity	NPC272483
0.6212	Remote Similarity	NPC293216
0.6205	Remote Similarity	NPC476817
0.6193	Remote Similarity	NPC473218
0.6193	Remote Similarity	NPC6865
0.6193	Remote Similarity	NPC470702
0.6193	Remote Similarity	NPC153980
0.6186	Remote Similarity	NPC46225
0.6186	Remote Similarity	NPC225821
0.6186	Remote Similarity	NPC478184
0.6183	Remote Similarity	NPC469525
0.6176	Remote Similarity	NPC118084
0.6172	Remote Similarity	NPC472293
0.6171	Remote Similarity	NPC269270
0.6168	Remote Similarity	NPC327592
0.6165	Remote Similarity	NPC469489
0.6164	Remote Similarity	NPC470703
0.6162	Remote Similarity	NPC161861
0.6162	Remote Similarity	NPC252572
0.6158	Remote Similarity	NPC281094
0.6158	Remote Similarity	NPC21429
0.6158	Remote Similarity	NPC200214
0.6157	Remote Similarity	NPC116555
0.6157	Remote Similarity	NPC127677
0.6157	Remote Similarity	NPC258062
0.6154	Remote Similarity	NPC81802
0.6154	Remote Similarity	NPC269886
0.6154	Remote Similarity	NPC247735
0.6154	Remote Similarity	NPC472210
0.6154	Remote Similarity	NPC472295
0.6143	Remote Similarity	NPC14686
0.614	Remote Similarity	NPC317373
0.6134	Remote Similarity	NPC242116
0.6134	Remote Similarity	NPC214106
0.6131	Remote Similarity	NPC203468
0.6131	Remote Similarity	NPC110500
0.6131	Remote Similarity	NPC149155

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 NPC469359 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	252
0.1-0.2	607
0.2-0.3	1236
0.3-0.4	2469
0.4-0.5	2954
0.5-0.6	1437
0.6-0.7	193
0.7-0.8	2
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
0.7037	Intermediate Similarity	NPD6044	Discontinued
0.6881	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.672	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD6173	Approved
0.665	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.665	Remote Similarity	NPD7564	Discontinued
0.665	Remote Similarity	NPD7027	Phase 3
0.6582	Remote Similarity	NPD5473	Discontinued
0.6571	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD4848	Phase 1
0.6564	Remote Similarity	NPD2753	Discontinued
0.6557	Remote Similarity	NPD1270	Approved
0.655	Remote Similarity	NPD4988	Discontinued
0.6535	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD3238	Discontinued
0.6497	Remote Similarity	NPD2479	Phase 3
0.6497	Remote Similarity	NPD2481	Approved
0.648	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD5636	Discontinued
0.6455	Remote Similarity	NPD2214	Approved
0.6455	Remote Similarity	NPD2213	Approved
0.6439	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.641	Remote Similarity	NPD4524	Discontinued
0.6394	Remote Similarity	NPD2405	Phase 3
0.6387	Remote Similarity	NPD5400	Approved
0.6381	Remote Similarity	NPD4924	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6446	Discontinued
0.6364	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD7619	Phase 3
0.6359	Remote Similarity	NPD3610	Approved
0.6359	Remote Similarity	NPD7618	Phase 3
0.6359	Remote Similarity	NPD3609	Approved
0.6355	Remote Similarity	NPD2851	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD2850	Phase 1
0.6355	Remote Similarity	NPD6068	Discontinued
0.6354	Remote Similarity	NPD3583	Phase 2
0.6354	Remote Similarity	NPD1545	Discontinued
0.6351	Remote Similarity	NPD4304	Discovery
0.6337	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD200	Phase 2
0.6333	Remote Similarity	NPD201	Phase 2
0.633	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD4960	Approved
0.6308	Remote Similarity	NPD4959	Approved
0.6305	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6305	Remote Similarity	NPD3961	Discontinued
0.63	Remote Similarity	NPD3178	Discontinued
0.63	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6152	Phase 1
0.6278	Remote Similarity	NPD7661	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD206	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD7175	Phase 1
0.6262	Remote Similarity	NPD4922	Phase 2
0.6262	Remote Similarity	NPD4415	Approved
0.6256	Remote Similarity	NPD3393	Approved
0.6256	Remote Similarity	NPD3394	Approved
0.6256	Remote Similarity	NPD1343	Approved
0.6256	Remote Similarity	NPD3389	Approved
0.6244	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD8169	Discontinued
0.6238	Remote Similarity	NPD7049	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD2720	Phase 1
0.6237	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.6227	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD6771	Discontinued
0.6215	Remote Similarity	NPD3967	Approved
0.6203	Remote Similarity	NPD1004	Phase 2
0.6203	Remote Similarity	NPD1005	Phase 2
0.6193	Remote Similarity	NPD991	Phase 2
0.6193	Remote Similarity	NPD992	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD5105	Approved
0.6188	Remote Similarity	NPD5106	Approved
0.6188	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD4075	Phase 2
0.6179	Remote Similarity	NPD3891	Phase 2
0.6179	Remote Similarity	NPD3890	Phase 2
0.6178	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD7026	Phase 2
0.6173	Remote Similarity	NPD2640	Approved
0.6173	Remote Similarity	NPD2641	Approved
0.6173	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD4299	Phase 1
0.6168	Remote Similarity	NPD5901	Discontinued
0.6165	Remote Similarity	NPD5685	Approved
0.6165	Remote Similarity	NPD5686	Approved
0.6162	Remote Similarity	NPD750	Phase 2
0.6157	Remote Similarity	NPD2509	Approved
0.6157	Remote Similarity	NPD2510	Approved
0.615	Remote Similarity	NPD7187	Phase 2
0.6146	Remote Similarity	NPD2770	Discontinued
0.6143	Remote Similarity	NPD6664	Approved
0.6134	Remote Similarity	NPD5315	Discontinued
0.6131	Remote Similarity	NPD482	Approved
0.6131	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD3968	Approved
0.6124	Remote Similarity	NPD5853	Phase 3
0.6124	Remote Similarity	NPD5855	Phase 3
0.6119	Remote Similarity	NPD7195	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD704	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD3411	Phase 2
0.6111	Remote Similarity	NPD3410	Approved
0.6105	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD5017	Discontinued
0.6099	Remote Similarity	NPD5199	Approved
0.6099	Remote Similarity	NPD5198	Approved
0.6093	Remote Similarity	NPD5426	Phase 3
0.6091	Remote Similarity	NPD5888	Phase 2
0.6091	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD3927	Phase 2
0.6087	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.6085	Remote Similarity	NPD2548	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD2091	Phase 2
0.6078	Remote Similarity	NPD2096	Phase 2
0.6077	Remote Similarity	NPD460	Discontinued
0.6075	Remote Similarity	NPD4510	Discontinued
0.6075	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6073	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6073	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD3246	Discontinued
0.6068	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD1573	Approved
0.6061	Remote Similarity	NPD1575	Approved
0.6058	Remote Similarity	NPD2336	Approved
0.6054	Remote Similarity	NPD9599	Approved
0.605	Remote Similarity	NPD4883	Approved
0.6047	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6045	Remote Similarity	NPD7455	Approved
0.6045	Remote Similarity	NPD7454	Approved
0.6045	Remote Similarity	NPD9583	Approved
0.6043	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD2061	Approved
0.6041	Remote Similarity	NPD2639	Approved
0.6041	Remote Similarity	NPD2642	Approved
0.6038	Remote Similarity	NPD4364	Phase 1
0.6037	Remote Similarity	NPD4913	Phase 3
0.6032	Remote Similarity	NPD4703	Approved
0.6032	Remote Similarity	NPD4702	Approved
0.6031	Remote Similarity	NPD1630	Approved
0.6029	Remote Similarity	NPD2094	Phase 2
0.6029	Remote Similarity	NPD2092	Phase 2
0.6029	Remote Similarity	NPD2095	Phase 2
0.6028	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6027	Remote Similarity	NPD4051	Discontinued
0.6027	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6021	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.602	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD2290	Phase 3
0.6019	Remote Similarity	NPD2289	Phase 3
0.6019	Remote Similarity	NPD3947	Discontinued
0.6018	Remote Similarity	NPD6787	Phase 2
0.6011	Remote Similarity	NPD792	Discontinued
0.6011	Remote Similarity	NPD175	Clinical (unspecified phase)
0.601	Remote Similarity	NPD4499	Approved
0.601	Remote Similarity	NPD2413	Phase 2
0.6009	Remote Similarity	NPD6999	Discontinued
0.6009	Remote Similarity	NPD7665	Phase 2
0.6009	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6009	Remote Similarity	NPD6459	Phase 2
0.6009	Remote Similarity	NPD7666	Phase 3
0.6009	Remote Similarity	NPD7191	Phase 2
0.6	Remote Similarity	NPD1404	Approved
0.6	Remote Similarity	NPD3100	Discontinued
0.6	Remote Similarity	NPD1403	Approved
0.6	Remote Similarity	NPD4417	Approved
0.5991	Remote Similarity	NPD2008	Discontinued
0.5983	Remote Similarity	NPD946	Discontinued
0.5982	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD3856	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD5510	Approved
0.598	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.5973	Remote Similarity	NPD2411	Approved
0.597	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD5986	Approved
0.5965	Remote Similarity	NPD5987	Approved
0.5963	Remote Similarity	NPD3905	Phase 3
0.5962	Remote Similarity	NPD465	Clinical (unspecified phase)
0.5961	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.5961	Remote Similarity	NPD3078	Approved
0.5961	Remote Similarity	NPD3079	Approved
0.5961	Remote Similarity	NPD3077	Approved
0.5961	Remote Similarity	NPD3076	Approved
0.596	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD272	Approved
0.5955	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD981	Phase 2
0.5945	Remote Similarity	NPD4906	Approved
0.5945	Remote Similarity	NPD4905	Approved
0.5945	Remote Similarity	NPD6987	Phase 1
0.5945	Remote Similarity	NPD8272	Phase 2
0.5945	Remote Similarity	NPD3247	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