NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	823.95
Volume:	674.918
LogP:	5.825
LogD:	3.799
LogS:	-3.708
# Rotatable Bonds:	3
TPSA:	155.62
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	10
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.151
Synthetic Accessibility Score:	6.702
Fsp3:	0.167
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.658
MDCK Permeability:	1.530915869807359e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.122
Human Intestinal Absorption (HIA):	0.656
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	96.40984344482422%
Volume Distribution (VD):	0.256
Pgp-substrate:	2.7720465660095215%

ADMET: Metabolism

CYP1A2-inhibitor:	0.161
CYP1A2-substrate:	0.218
CYP2C19-inhibitor:	0.969
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.677
CYP2C9-substrate:	0.975
CYP2D6-inhibitor:	0.132
CYP2D6-substrate:	0.105
CYP3A4-inhibitor:	0.345
CYP3A4-substrate:	0.952

ADMET: Excretion

Clearance (CL):	1.244
Half-life (T1/2):	0.666

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.728
Drug-inuced Liver Injury (DILI):	0.924
AMES Toxicity:	0.552
Rat Oral Acute Toxicity:	0.991
Maximum Recommended Daily Dose:	0.966
Skin Sensitization:	0.872
Carcinogencity:	0.884
Eye Corrosion:	0.003
Eye Irritation:	0.047
Respiratory Toxicity:	0.762

Download Data

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

Natural Product: NPC477413

Natural Product ID:	NPC477413
*Common Name:**	Discorhabdin W
IUPAC Name:	n.a.
Synonyms:	Discorhabdin W
Standard InCHIKey:	QSBKYGUXDODRSD-OZBLHQGLSA-N
Standard InCHI:	InChI=1S/C36H22Br2N6O4S2.C2HF3O2/c37-17-11-35(3-7-41-31-25(35)27-23-15(1-5-39-27)13-43-29(23)33(31)47)21(9-19(17)45)49-50-22-10-20(46)18(38)12-36(22)4-8-42-32-26(36)28-24-16(2-6-40-28)14-44-30(24)34(32)48;3-2(4,5)1(6)7/h3-4,7-14,41-42,47-48H,1-2,5-6H2;(H,6,7)/t35-,36-;/m1./s1
SMILES:	C1CN=C2C3=C1C=NC3=C(C4=C2[C@]5(C=CN4)C=C(C(=O)C=C5SSC6=CC(=O)C(=C[C@]67C=CNC8=C7C9=NCCC1=C9C(=C8O)N=C1)Br)Br)O.C(=O)(C(F)(F)F)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509693
PubChem CID:	136117846
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds]

*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
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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	84	nM	PMID[16378380]

☑ 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 NPC477413 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	456
0.1-0.2	3486
0.2-0.3	20149
0.3-0.4	13152
0.4-0.5	2730
0.5-0.6	2176
0.6-0.7	498
0.7-0.8	32
0.8-0.85	15
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8511	High Similarity	NPC79777
0.8511	High Similarity	NPC234403
0.841	Intermediate Similarity	NPC225622
0.841	Intermediate Similarity	NPC221726
0.841	Intermediate Similarity	NPC477414
0.8358	Intermediate Similarity	NPC88115
0.8259	Intermediate Similarity	NPC106757
0.8256	Intermediate Similarity	NPC268966
0.822	Intermediate Similarity	NPC182940
0.8191	Intermediate Similarity	NPC262338
0.8154	Intermediate Similarity	NPC477415
0.8154	Intermediate Similarity	NPC23476
0.8154	Intermediate Similarity	NPC474259
0.8071	Intermediate Similarity	NPC475874
0.802	Intermediate Similarity	NPC473628
0.7824	Intermediate Similarity	NPC186068
0.7799	Intermediate Similarity	NPC143075
0.7644	Intermediate Similarity	NPC274981
0.7562	Intermediate Similarity	NPC469359
0.7525	Intermediate Similarity	NPC473946
0.7488	Intermediate Similarity	NPC167710
0.7487	Intermediate Similarity	NPC477042
0.7487	Intermediate Similarity	NPC474492
0.7447	Intermediate Similarity	NPC471655
0.7441	Intermediate Similarity	NPC317701
0.7427	Intermediate Similarity	NPC326422
0.7426	Intermediate Similarity	NPC474258
0.7387	Intermediate Similarity	NPC284775
0.7358	Intermediate Similarity	NPC470680
0.7358	Intermediate Similarity	NPC100104
0.7343	Intermediate Similarity	NPC304203
0.733	Intermediate Similarity	NPC476460
0.7286	Intermediate Similarity	NPC476143
0.7233	Intermediate Similarity	NPC103119
0.7212	Intermediate Similarity	NPC216550
0.7206	Intermediate Similarity	NPC477003
0.717	Intermediate Similarity	NPC477004
0.7129	Intermediate Similarity	NPC47190
0.7116	Intermediate Similarity	NPC476252
0.7108	Intermediate Similarity	NPC191415
0.7089	Intermediate Similarity	NPC237414
0.7087	Intermediate Similarity	NPC308931
0.7087	Intermediate Similarity	NPC99939
0.7083	Intermediate Similarity	NPC473878
0.7068	Intermediate Similarity	NPC100726
0.7067	Intermediate Similarity	NPC255909
0.7059	Intermediate Similarity	NPC470703
0.7056	Intermediate Similarity	NPC269203
0.7056	Intermediate Similarity	NPC166209
0.7056	Intermediate Similarity	NPC77241
0.7056	Intermediate Similarity	NPC13456
0.7056	Intermediate Similarity	NPC252338
0.7044	Intermediate Similarity	NPC157583
0.7042	Intermediate Similarity	NPC34837
0.7014	Intermediate Similarity	NPC470702
0.7014	Intermediate Similarity	NPC473218
0.7009	Intermediate Similarity	NPC201266
0.7009	Intermediate Similarity	NPC474318
0.7009	Intermediate Similarity	NPC220797
0.7009	Intermediate Similarity	NPC153123
0.7009	Intermediate Similarity	NPC475914
0.7009	Intermediate Similarity	NPC268744
0.7005	Intermediate Similarity	NPC469563
0.6991	Remote Similarity	NPC260900
0.6986	Remote Similarity	NPC116555
0.6972	Remote Similarity	NPC175602
0.6963	Remote Similarity	NPC477044
0.6963	Remote Similarity	NPC477041
0.6961	Remote Similarity	NPC237188
0.6959	Remote Similarity	NPC217021
0.6959	Remote Similarity	NPC470679
0.6941	Remote Similarity	NPC469577
0.6941	Remote Similarity	NPC475410
0.693	Remote Similarity	NPC74413
0.6916	Remote Similarity	NPC227582
0.6916	Remote Similarity	NPC475286
0.6916	Remote Similarity	NPC174281
0.6916	Remote Similarity	NPC74153
0.6909	Remote Similarity	NPC469578
0.6908	Remote Similarity	NPC102755
0.6904	Remote Similarity	NPC477420
0.6904	Remote Similarity	NPC477418
0.6898	Remote Similarity	NPC121327
0.6878	Remote Similarity	NPC61038
0.6875	Remote Similarity	NPC467063
0.6872	Remote Similarity	NPC324091
0.6853	Remote Similarity	NPC74357
0.6852	Remote Similarity	NPC136957
0.6852	Remote Similarity	NPC19696
0.6852	Remote Similarity	NPC477045
0.6847	Remote Similarity	NPC469562
0.6847	Remote Similarity	NPC220594
0.6842	Remote Similarity	NPC133003
0.6835	Remote Similarity	NPC143977
0.6832	Remote Similarity	NPC70949
0.6827	Remote Similarity	NPC117027
0.6822	Remote Similarity	NPC157828
0.6822	Remote Similarity	NPC195239
0.6814	Remote Similarity	NPC477715
0.6798	Remote Similarity	NPC471943
0.6791	Remote Similarity	NPC11445
0.6784	Remote Similarity	NPC477714
0.6776	Remote Similarity	NPC473821
0.6773	Remote Similarity	NPC477043
0.677	Remote Similarity	NPC470731
0.6756	Remote Similarity	NPC207866
0.6751	Remote Similarity	NPC251391
0.6746	Remote Similarity	NPC470205
0.6745	Remote Similarity	NPC321708
0.674	Remote Similarity	NPC477416
0.6733	Remote Similarity	NPC115232
0.6733	Remote Similarity	NPC71132
0.6713	Remote Similarity	NPC102592
0.6713	Remote Similarity	NPC476526
0.6713	Remote Similarity	NPC79356
0.6713	Remote Similarity	NPC48117
0.6713	Remote Similarity	NPC329765
0.6711	Remote Similarity	NPC110182
0.6711	Remote Similarity	NPC471194
0.6711	Remote Similarity	NPC473310
0.6711	Remote Similarity	NPC471193
0.671	Remote Similarity	NPC229893
0.6701	Remote Similarity	NPC467188
0.6701	Remote Similarity	NPC70406
0.67	Remote Similarity	NPC80681
0.6698	Remote Similarity	NPC17059
0.6696	Remote Similarity	NPC470732
0.6695	Remote Similarity	NPC474357
0.6695	Remote Similarity	NPC476491
0.6684	Remote Similarity	NPC123906
0.6684	Remote Similarity	NPC102664
0.6682	Remote Similarity	NPC78767
0.6682	Remote Similarity	NPC473814
0.6681	Remote Similarity	NPC470323
0.6667	Remote Similarity	NPC82370
0.6667	Remote Similarity	NPC151635
0.6667	Remote Similarity	NPC267811
0.6667	Remote Similarity	NPC473666
0.6667	Remote Similarity	NPC72956
0.6653	Remote Similarity	NPC935
0.6653	Remote Similarity	NPC267078
0.6651	Remote Similarity	NPC73994
0.665	Remote Similarity	NPC233380
0.665	Remote Similarity	NPC477611
0.665	Remote Similarity	NPC252572
0.665	Remote Similarity	NPC42372
0.6637	Remote Similarity	NPC153980
0.6637	Remote Similarity	NPC6865
0.6636	Remote Similarity	NPC292361
0.6636	Remote Similarity	NPC128244
0.6635	Remote Similarity	NPC110158
0.6633	Remote Similarity	NPC105811
0.6624	Remote Similarity	NPC70155
0.6623	Remote Similarity	NPC36405
0.6616	Remote Similarity	NPC472260
0.6603	Remote Similarity	NPC11126
0.6594	Remote Similarity	NPC472285
0.659	Remote Similarity	NPC294693
0.659	Remote Similarity	NPC93390
0.6589	Remote Similarity	NPC209917
0.6579	Remote Similarity	NPC291517
0.6577	Remote Similarity	NPC98715
0.6573	Remote Similarity	NPC476527
0.657	Remote Similarity	NPC161861
0.6567	Remote Similarity	NPC476817
0.6562	Remote Similarity	NPC46225
0.6562	Remote Similarity	NPC225821
0.656	Remote Similarity	NPC472293
0.6558	Remote Similarity	NPC231536
0.6557	Remote Similarity	NPC21429
0.6557	Remote Similarity	NPC228835
0.6555	Remote Similarity	NPC83774
0.6555	Remote Similarity	NPC59269
0.655	Remote Similarity	NPC209362
0.655	Remote Similarity	NPC471192
0.6545	Remote Similarity	NPC474767
0.6544	Remote Similarity	NPC19342
0.654	Remote Similarity	NPC475859
0.654	Remote Similarity	NPC475969
0.6538	Remote Similarity	NPC293216
0.6537	Remote Similarity	NPC269270
0.6535	Remote Similarity	NPC92796
0.6535	Remote Similarity	NPC135141
0.6533	Remote Similarity	NPC476524
0.6533	Remote Similarity	NPC476525
0.6533	Remote Similarity	NPC258062
0.6533	Remote Similarity	NPC127677
0.6527	Remote Similarity	NPC475635
0.6525	Remote Similarity	NPC191382
0.6525	Remote Similarity	NPC56109
0.6524	Remote Similarity	NPC213468
0.6522	Remote Similarity	NPC6982
0.652	Remote Similarity	NPC317105
0.6518	Remote Similarity	NPC472064
0.6514	Remote Similarity	NPC202812
0.6511	Remote Similarity	NPC909
0.6511	Remote Similarity	NPC475338
0.6509	Remote Similarity	NPC14686
0.6507	Remote Similarity	NPC474412
0.6504	Remote Similarity	NPC271862

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 NPC477413 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	229
0.1-0.2	628
0.2-0.3	1215
0.3-0.4	2707
0.4-0.5	2892
0.5-0.6	1331
0.6-0.7	148
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
0.7081	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD5473	Discontinued
0.6893	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.689	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD7564	Discontinued
0.6777	Remote Similarity	NPD4988	Discontinued
0.677	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6459	Phase 2
0.6744	Remote Similarity	NPD7618	Phase 3
0.6744	Remote Similarity	NPD7619	Phase 3
0.6731	Remote Similarity	NPD2479	Phase 3
0.6731	Remote Similarity	NPD2481	Approved
0.6713	Remote Similarity	NPD4848	Phase 1
0.67	Remote Similarity	NPD6446	Discontinued
0.6698	Remote Similarity	NPD3961	Discontinued
0.6697	Remote Similarity	NPD5901	Discontinued
0.6697	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6152	Phase 1
0.6667	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD4922	Phase 2
0.6651	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD2753	Discontinued
0.6622	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD2008	Discontinued
0.659	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD3238	Discontinued
0.6584	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD2172	Phase 1
0.6564	Remote Similarity	NPD2411	Approved
0.6548	Remote Similarity	NPD1270	Approved
0.6547	Remote Similarity	NPD5426	Phase 3
0.654	Remote Similarity	NPD3178	Discontinued
0.6537	Remote Similarity	NPD5198	Approved
0.6537	Remote Similarity	NPD5199	Approved
0.6537	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD2510	Approved
0.6533	Remote Similarity	NPD2509	Approved
0.653	Remote Similarity	NPD6664	Approved
0.6526	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD7781	Approved
0.6525	Remote Similarity	NPD7780	Approved
0.6516	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD4075	Phase 2
0.6504	Remote Similarity	NPD1600	Suspended
0.6491	Remote Similarity	NPD7454	Approved
0.6491	Remote Similarity	NPD7455	Approved
0.6486	Remote Similarity	NPD5017	Discontinued
0.6478	Remote Similarity	NPD3389	Approved
0.6478	Remote Similarity	NPD3394	Approved
0.6478	Remote Similarity	NPD3393	Approved
0.6476	Remote Similarity	NPD4051	Discontinued
0.6463	Remote Similarity	NPD5888	Phase 2
0.646	Remote Similarity	NPD2442	Approved
0.646	Remote Similarity	NPD2443	Approved
0.6457	Remote Similarity	NPD4924	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD2642	Approved
0.6456	Remote Similarity	NPD2639	Approved
0.6447	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD5855	Phase 3
0.6438	Remote Similarity	NPD5853	Phase 3
0.6432	Remote Similarity	NPD2095	Phase 2
0.6432	Remote Similarity	NPD3100	Discontinued
0.6432	Remote Similarity	NPD2092	Phase 2
0.6432	Remote Similarity	NPD2094	Phase 2
0.6429	Remote Similarity	NPD4304	Discovery
0.6429	Remote Similarity	NPD6044	Discontinued
0.6426	Remote Similarity	NPD7661	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD2640	Approved
0.6425	Remote Similarity	NPD1343	Approved
0.6425	Remote Similarity	NPD1982	Phase 1
0.6425	Remote Similarity	NPD2641	Approved
0.6418	Remote Similarity	NPD2837	Discontinued
0.6415	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD7027	Phase 3
0.6404	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD2096	Phase 2
0.6402	Remote Similarity	NPD2091	Phase 2
0.6396	Remote Similarity	NPD2405	Phase 3
0.6393	Remote Similarity	NPD460	Discontinued
0.639	Remote Similarity	NPD5400	Approved
0.6387	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD7187	Phase 2
0.6381	Remote Similarity	NPD482	Approved
0.6378	Remote Similarity	NPD1722	Approved
0.6373	Remote Similarity	NPD2213	Approved
0.6373	Remote Similarity	NPD2214	Approved
0.6372	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD3323	Discontinued
0.6359	Remote Similarity	NPD7175	Phase 1
0.6356	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD3905	Phase 3
0.6343	Remote Similarity	NPD7026	Phase 2
0.6335	Remote Similarity	NPD2290	Phase 3
0.6335	Remote Similarity	NPD2289	Phase 3
0.6332	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.633	Remote Similarity	NPD5686	Approved
0.633	Remote Similarity	NPD5685	Approved
0.633	Remote Similarity	NPD4499	Approved
0.6327	Remote Similarity	NPD4299	Phase 1
0.6321	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7665	Phase 2
0.6316	Remote Similarity	NPD7666	Phase 3
0.6316	Remote Similarity	NPD7191	Phase 2
0.6313	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD4883	Approved
0.6293	Remote Similarity	NPD7970	Approved
0.6293	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD2408	Discontinued
0.6287	Remote Similarity	NPD6173	Approved
0.6286	Remote Similarity	NPD3609	Approved
0.6286	Remote Similarity	NPD3610	Approved
0.6281	Remote Similarity	NPD7790	Approved
0.6281	Remote Similarity	NPD7791	Approved
0.6281	Remote Similarity	NPD7952	Approved
0.6281	Remote Similarity	NPD7951	Approved
0.6281	Remote Similarity	NPD7789	Approved
0.6281	Remote Similarity	NPD7953	Approved
0.6281	Remote Similarity	NPD7950	Approved
0.628	Remote Similarity	NPD3583	Phase 2
0.6279	Remote Similarity	NPD5106	Approved
0.6279	Remote Similarity	NPD5105	Approved
0.6279	Remote Similarity	NPD3319	Phase 1
0.6279	Remote Similarity	NPD3318	Approved
0.6279	Remote Similarity	NPD3320	Approved
0.6273	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD4913	Phase 3
0.6272	Remote Similarity	NPD1506	Discontinued
0.6272	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD6217	Discontinued
0.6267	Remote Similarity	NPD5809	Phase 3
0.6262	Remote Similarity	NPD1404	Approved
0.6262	Remote Similarity	NPD6595	Phase 3
0.6262	Remote Similarity	NPD1403	Approved
0.625	Remote Similarity	NPD5854	Approved
0.625	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6999	Discontinued
0.625	Remote Similarity	NPD6787	Phase 2
0.6244	Remote Similarity	NPD3506	Approved
0.6244	Remote Similarity	NPD3505	Approved
0.6239	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD2881	Approved
0.6239	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5818	Discontinued
0.6239	Remote Similarity	NPD2879	Approved
0.6232	Remote Similarity	NPD6771	Discontinued
0.6232	Remote Similarity	NPD1853	Clinical (unspecified phase)
0.6229	Remote Similarity	NPD6242	Discontinued
0.6226	Remote Similarity	NPD5065	Approved
0.6226	Remote Similarity	NPD4128	Approved
0.6226	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD7824	Approved
0.6215	Remote Similarity	NPD4079	Approved
0.6215	Remote Similarity	NPD4076	Approved
0.6213	Remote Similarity	NPD6470	Phase 3
0.6207	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD3891	Phase 2
0.6195	Remote Similarity	NPD3890	Phase 2
0.6193	Remote Similarity	NPD786	Approved
0.6188	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD6226	Phase 3
0.6184	Remote Similarity	NPD7207	Approved
0.6184	Remote Similarity	NPD6987	Phase 1
0.6184	Remote Similarity	NPD8115	Approved
0.6184	Remote Similarity	NPD8114	Approved
0.6184	Remote Similarity	NPD3947	Discontinued
0.6184	Remote Similarity	NPD7209	Approved
0.6184	Remote Similarity	NPD7208	Approved
0.6182	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD4524	Discontinued
0.6174	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD4181	Approved
0.6167	Remote Similarity	NPD8073	Approved
0.6167	Remote Similarity	NPD8289	Discontinued
0.6164	Remote Similarity	NPD8431	Approved
0.6164	Remote Similarity	NPD7470	Discontinued
0.6163	Remote Similarity	NPD6986	Phase 1
0.6161	Remote Similarity	NPD1573	Approved
0.6161	Remote Similarity	NPD5446	Phase 2
0.6161	Remote Similarity	NPD2880	Discontinued
0.6161	Remote Similarity	NPD1575	Approved
0.616	Remote Similarity	NPD1996	Discontinued
0.6157	Remote Similarity	NPD7010	Phase 3
0.6157	Remote Similarity	NPD3967	Approved
0.6157	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6157	Remote Similarity	NPD7957	Phase 1
0.6154	Remote Similarity	NPD2385	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