NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	412.98
Volume:	335.817
LogP:	3.473
LogD:	2.409
LogS:	-4.003
# Rotatable Bonds:	0
TPSA:	77.48
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.57
Synthetic Accessibility Score:	6.248
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.128
MDCK Permeability:	1.4147977708489634e-05
Pgp-inhibitor:	0.103
Pgp-substrate:	0.05
Human Intestinal Absorption (HIA):	0.212
20% Bioavailability (F20%):	0.687
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	98.67670440673828%
Volume Distribution (VD):	0.458
Pgp-substrate:	1.721785545349121%

ADMET: Metabolism

CYP1A2-inhibitor:	0.937
CYP1A2-substrate:	0.744
CYP2C19-inhibitor:	0.898
CYP2C19-substrate:	0.12
CYP2C9-inhibitor:	0.902
CYP2C9-substrate:	0.921
CYP2D6-inhibitor:	0.809
CYP2D6-substrate:	0.244
CYP3A4-inhibitor:	0.46
CYP3A4-substrate:	0.363

ADMET: Excretion

Clearance (CL):	3.554
Half-life (T1/2):	0.62

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.841
Drug-inuced Liver Injury (DILI):	0.932
AMES Toxicity:	0.964
Rat Oral Acute Toxicity:	0.971
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.628
Carcinogencity:	0.955
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.938

Download Data

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

Natural Product: NPC477414

Natural Product ID:	NPC477414
*Common Name:**	Discorhabdin B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UKSNLLKPYVGHFN-VOJFVSQTSA-N
Standard InCHI:	InChI=1S/C18H12BrN3O2S/c19-8-4-18-5-11(25-10(18)3-9(8)23)22-16-13(18)14-12-7(1-2-20-14)6-21-15(12)17(16)24/h3-4,6,11,22,24H,1-2,5H2/t11-,18-/m0/s1
SMILES:	C1CN=C2C3=C1C=NC3=C(C4=C2[C@@]56C[C@@H](N4)SC5=CC(=O)C(=C6)Br)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	135409044
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	=	87	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 NPC477414 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	435
0.1-0.2	3331
0.2-0.3	21973
0.3-0.4	11686
0.4-0.5	2814
0.5-0.6	2037
0.6-0.7	374
0.7-0.8	26
0.8-0.85	7
0.85-0.9	9
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC221726
1.0	High Similarity	NPC225622
0.9593	High Similarity	NPC23476
0.9593	High Similarity	NPC474259
0.9593	High Similarity	NPC477415
0.9244	High Similarity	NPC79777
0.9244	High Similarity	NPC234403
0.9153	High Similarity	NPC268966
0.9086	High Similarity	NPC143075
0.8914	High Similarity	NPC182940
0.8895	High Similarity	NPC262338
0.8674	High Similarity	NPC473628
0.8667	High Similarity	NPC469359
0.8525	High Similarity	NPC475874
0.8475	Intermediate Similarity	NPC186068
0.8429	Intermediate Similarity	NPC88115
0.8421	Intermediate Similarity	NPC106757
0.841	Intermediate Similarity	NPC477413
0.8211	Intermediate Similarity	NPC476143
0.8182	Intermediate Similarity	NPC274981
0.8011	Intermediate Similarity	NPC474258
0.7977	Intermediate Similarity	NPC471655
0.7959	Intermediate Similarity	NPC469563
0.7926	Intermediate Similarity	NPC473946
0.791	Intermediate Similarity	NPC474492
0.7908	Intermediate Similarity	NPC476252
0.7879	Intermediate Similarity	NPC469577
0.7879	Intermediate Similarity	NPC475410
0.7839	Intermediate Similarity	NPC469578
0.7765	Intermediate Similarity	NPC100104
0.7765	Intermediate Similarity	NPC470680
0.7761	Intermediate Similarity	NPC469562
0.7761	Intermediate Similarity	NPC220594
0.7701	Intermediate Similarity	NPC477042
0.7557	Intermediate Similarity	NPC100726
0.7536	Intermediate Similarity	NPC477416
0.7374	Intermediate Similarity	NPC473878
0.7354	Intermediate Similarity	NPC477418
0.7354	Intermediate Similarity	NPC477420
0.7339	Intermediate Similarity	NPC475635
0.7333	Intermediate Similarity	NPC217021
0.7333	Intermediate Similarity	NPC470679
0.7318	Intermediate Similarity	NPC102664
0.7245	Intermediate Similarity	NPC103119
0.7225	Intermediate Similarity	NPC284775
0.7164	Intermediate Similarity	NPC167710
0.7129	Intermediate Similarity	NPC477041
0.7129	Intermediate Similarity	NPC477044
0.7079	Intermediate Similarity	NPC74153
0.7053	Intermediate Similarity	NPC175602
0.705	Intermediate Similarity	NPC47190
0.7041	Intermediate Similarity	NPC477003
0.7015	Intermediate Similarity	NPC304203
0.7015	Intermediate Similarity	NPC473821
0.701	Intermediate Similarity	NPC477045
0.701	Intermediate Similarity	NPC477004
0.7	Intermediate Similarity	NPC476460
0.6985	Remote Similarity	NPC255909
0.6984	Remote Similarity	NPC71132
0.6952	Remote Similarity	NPC61038
0.694	Remote Similarity	NPC123906
0.6931	Remote Similarity	NPC326422
0.6923	Remote Similarity	NPC477043
0.6919	Remote Similarity	NPC251391
0.6845	Remote Similarity	NPC74357
0.6829	Remote Similarity	NPC78767
0.6829	Remote Similarity	NPC473814
0.6822	Remote Similarity	NPC207866
0.6814	Remote Similarity	NPC294693
0.6806	Remote Similarity	NPC233380
0.6798	Remote Similarity	NPC216550
0.6794	Remote Similarity	NPC317701
0.678	Remote Similarity	NPC292361
0.6768	Remote Similarity	NPC191415
0.6763	Remote Similarity	NPC237414
0.6742	Remote Similarity	NPC291517
0.6732	Remote Similarity	NPC93390
0.6719	Remote Similarity	NPC115232
0.6701	Remote Similarity	NPC157583
0.6698	Remote Similarity	NPC473218
0.6698	Remote Similarity	NPC110182
0.6698	Remote Similarity	NPC470702
0.6685	Remote Similarity	NPC467188
0.6684	Remote Similarity	NPC70406
0.6683	Remote Similarity	NPC153123
0.6683	Remote Similarity	NPC201266
0.6683	Remote Similarity	NPC475914
0.6683	Remote Similarity	NPC220797
0.6683	Remote Similarity	NPC268744
0.6683	Remote Similarity	NPC474318
0.6667	Remote Similarity	NPC475286
0.6667	Remote Similarity	NPC174281
0.6667	Remote Similarity	NPC308931
0.6667	Remote Similarity	NPC302647
0.6667	Remote Similarity	NPC470703
0.6667	Remote Similarity	NPC99939
0.6651	Remote Similarity	NPC13456
0.6651	Remote Similarity	NPC166209
0.6651	Remote Similarity	NPC77241
0.6651	Remote Similarity	NPC269203
0.6651	Remote Similarity	NPC252338
0.665	Remote Similarity	NPC157828
0.665	Remote Similarity	NPC195239
0.6649	Remote Similarity	NPC70949
0.6632	Remote Similarity	NPC42372
0.6631	Remote Similarity	NPC313889
0.6618	Remote Similarity	NPC11445
0.6617	Remote Similarity	NPC110158
0.6616	Remote Similarity	NPC237188
0.6615	Remote Similarity	NPC471943
0.6613	Remote Similarity	NPC105811
0.6603	Remote Similarity	NPC19696
0.6603	Remote Similarity	NPC136957
0.6597	Remote Similarity	NPC80681
0.6596	Remote Similarity	NPC216713
0.6588	Remote Similarity	NPC260900
0.6587	Remote Similarity	NPC227582
0.6569	Remote Similarity	NPC209917
0.6567	Remote Similarity	NPC102755
0.6557	Remote Similarity	NPC138562
0.655	Remote Similarity	NPC73994
0.6544	Remote Similarity	NPC471193
0.6544	Remote Similarity	NPC471194
0.6544	Remote Similarity	NPC469544
0.6533	Remote Similarity	NPC248454
0.6526	Remote Similarity	NPC209362
0.6524	Remote Similarity	NPC74413
0.652	Remote Similarity	NPC17059
0.6515	Remote Similarity	NPC293216
0.6502	Remote Similarity	NPC133003
0.65	Remote Similarity	NPC11126
0.649	Remote Similarity	NPC202812
0.6476	Remote Similarity	NPC34837
0.6464	Remote Similarity	NPC23215
0.6462	Remote Similarity	NPC2414
0.6462	Remote Similarity	NPC98864
0.6459	Remote Similarity	NPC329765
0.6459	Remote Similarity	NPC48117
0.6459	Remote Similarity	NPC476526
0.6458	Remote Similarity	NPC213914
0.6456	Remote Similarity	NPC324091
0.6453	Remote Similarity	NPC228835
0.645	Remote Similarity	NPC83774
0.6441	Remote Similarity	NPC269270
0.6435	Remote Similarity	NPC116555
0.6432	Remote Similarity	NPC469529
0.6429	Remote Similarity	NPC272483
0.6422	Remote Similarity	NPC72956
0.6421	Remote Similarity	NPC470823
0.6418	Remote Similarity	NPC213468
0.6414	Remote Similarity	NPC6982
0.6413	Remote Similarity	NPC14686
0.6404	Remote Similarity	NPC117027
0.6404	Remote Similarity	NPC163055
0.6402	Remote Similarity	NPC98715
0.6394	Remote Similarity	NPC472292
0.6393	Remote Similarity	NPC6865
0.6393	Remote Similarity	NPC153980
0.6387	Remote Similarity	NPC200214
0.6386	Remote Similarity	NPC61011
0.6382	Remote Similarity	NPC252572
0.6381	Remote Similarity	NPC472293
0.6377	Remote Similarity	NPC154339
0.6373	Remote Similarity	NPC467063
0.6372	Remote Similarity	NPC473239
0.6368	Remote Similarity	NPC14113
0.6368	Remote Similarity	NPC84827
0.6368	Remote Similarity	NPC145885
0.6359	Remote Similarity	NPC214106
0.6355	Remote Similarity	NPC470677
0.6354	Remote Similarity	NPC229055
0.635	Remote Similarity	NPC203468
0.635	Remote Similarity	NPC110500
0.635	Remote Similarity	NPC149155
0.6349	Remote Similarity	NPC471957
0.6344	Remote Similarity	NPC129412
0.6344	Remote Similarity	NPC101130
0.6344	Remote Similarity	NPC58268
0.6344	Remote Similarity	NPC114033
0.6338	Remote Similarity	NPC121327
0.6337	Remote Similarity	NPC283219
0.6337	Remote Similarity	NPC248041
0.6337	Remote Similarity	NPC126709
0.6337	Remote Similarity	NPC55772
0.6335	Remote Similarity	NPC472260
0.6332	Remote Similarity	NPC469976
0.6332	Remote Similarity	NPC54214
0.6329	Remote Similarity	NPC321708
0.6324	Remote Similarity	NPC470205
0.6321	Remote Similarity	NPC474389
0.6318	Remote Similarity	NPC151635
0.6318	Remote Similarity	NPC267885
0.6313	Remote Similarity	NPC46225
0.6313	Remote Similarity	NPC225821
0.6313	Remote Similarity	NPC78020
0.6311	Remote Similarity	NPC476527
0.6308	Remote Similarity	NPC300183
0.6306	Remote Similarity	NPC471192
0.6304	Remote Similarity	NPC470323
0.6303	Remote Similarity	NPC179701

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 NPC477414 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	218
0.1-0.2	601
0.2-0.3	1254
0.3-0.4	2789
0.4-0.5	2941
0.5-0.6	1239
0.6-0.7	108
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
0.6954	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6044	Discontinued
0.6717	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD3178	Discontinued
0.6633	Remote Similarity	NPD5473	Discontinued
0.6573	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4848	Phase 1
0.6533	Remote Similarity	NPD2753	Discontinued
0.6526	Remote Similarity	NPD5901	Discontinued
0.652	Remote Similarity	NPD4988	Discontinued
0.652	Remote Similarity	NPD3961	Discontinued
0.651	Remote Similarity	NPD2213	Approved
0.651	Remote Similarity	NPD2214	Approved
0.6485	Remote Similarity	NPD5105	Approved
0.6485	Remote Similarity	NPD5106	Approved
0.6482	Remote Similarity	NPD3238	Discontinued
0.6473	Remote Similarity	NPD4922	Phase 2
0.6473	Remote Similarity	NPD6173	Approved
0.6429	Remote Similarity	NPD2639	Approved
0.6429	Remote Similarity	NPD2642	Approved
0.6429	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD3610	Approved
0.6414	Remote Similarity	NPD3609	Approved
0.6406	Remote Similarity	NPD276	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4075	Phase 2
0.6396	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD2481	Approved
0.6386	Remote Similarity	NPD2479	Phase 3
0.6373	Remote Similarity	NPD7564	Discontinued
0.6368	Remote Similarity	NPD2172	Phase 1
0.6359	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.635	Remote Similarity	NPD482	Approved
0.6349	Remote Similarity	NPD1270	Approved
0.6347	Remote Similarity	NPD6152	Phase 1
0.6333	Remote Similarity	NPD7619	Phase 3
0.6333	Remote Similarity	NPD7618	Phase 3
0.6318	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD3100	Discontinued
0.6313	Remote Similarity	NPD2640	Approved
0.6313	Remote Similarity	NPD2641	Approved
0.6308	Remote Similarity	NPD1404	Approved
0.6308	Remote Similarity	NPD1403	Approved
0.6303	Remote Similarity	NPD7027	Phase 3
0.6301	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD2405	Phase 3
0.6287	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD4924	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD2008	Discontinued
0.6267	Remote Similarity	NPD1996	Discontinued
0.6263	Remote Similarity	NPD1005	Phase 2
0.6263	Remote Similarity	NPD1004	Phase 2
0.6263	Remote Similarity	NPD6446	Discontinued
0.6262	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD1600	Suspended
0.6244	Remote Similarity	NPD2095	Phase 2
0.6244	Remote Similarity	NPD2094	Phase 2
0.6244	Remote Similarity	NPD2092	Phase 2
0.6244	Remote Similarity	NPD2411	Approved
0.6244	Remote Similarity	NPD1545	Discontinued
0.6244	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD3393	Approved
0.6233	Remote Similarity	NPD3389	Approved
0.6233	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD3394	Approved
0.6232	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.623	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6219	Remote Similarity	NPD4524	Discontinued
0.6214	Remote Similarity	NPD2096	Phase 2
0.6214	Remote Similarity	NPD2091	Phase 2
0.621	Remote Similarity	NPD2509	Approved
0.621	Remote Similarity	NPD2510	Approved
0.6209	Remote Similarity	NPD460	Discontinued
0.6197	Remote Similarity	NPD6664	Approved
0.6193	Remote Similarity	NPD5400	Approved
0.6188	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD7661	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD5636	Discontinued
0.6175	Remote Similarity	NPD4304	Discovery
0.6168	Remote Similarity	NPD465	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD198	Clinical (unspecified phase)
0.615	Remote Similarity	NPD5199	Approved
0.615	Remote Similarity	NPD2290	Phase 3
0.615	Remote Similarity	NPD2289	Phase 3
0.615	Remote Similarity	NPD1343	Approved
0.615	Remote Similarity	NPD5198	Approved
0.6142	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD6459	Phase 2
0.6133	Remote Similarity	NPD5818	Discontinued
0.6131	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD8073	Approved
0.6127	Remote Similarity	NPD3505	Approved
0.6127	Remote Similarity	NPD3506	Approved
0.6119	Remote Similarity	NPD1573	Approved
0.6119	Remote Similarity	NPD1575	Approved
0.6117	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6101	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD7195	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD4076	Approved
0.6098	Remote Similarity	NPD4079	Approved
0.6095	Remote Similarity	NPD2850	Phase 1
0.6095	Remote Similarity	NPD2851	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD1630	Approved
0.6087	Remote Similarity	NPD3320	Approved
0.6087	Remote Similarity	NPD3319	Phase 1
0.6087	Remote Similarity	NPD3318	Approved
0.6085	Remote Similarity	NPD1722	Approved
0.6083	Remote Similarity	NPD3891	Phase 2
0.6083	Remote Similarity	NPD3890	Phase 2
0.6081	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.608	Remote Similarity	NPD3583	Phase 2
0.6075	Remote Similarity	NPD206	Clinical (unspecified phase)
0.6073	Remote Similarity	NPD8272	Phase 2
0.6073	Remote Similarity	NPD5426	Phase 3
0.6066	Remote Similarity	NPD4499	Approved
0.6066	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD786	Approved
0.6063	Remote Similarity	NPD6376	Discontinued
0.6059	Remote Similarity	NPD750	Phase 2
0.6055	Remote Similarity	NPD7187	Phase 2
0.6053	Remote Similarity	NPD6242	Discontinued
0.6049	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD4128	Approved
0.6028	Remote Similarity	NPD5853	Phase 3
0.6028	Remote Similarity	NPD5855	Phase 3
0.6027	Remote Similarity	NPD7454	Approved
0.6027	Remote Similarity	NPD7455	Approved
0.6027	Remote Similarity	NPD8072	Approved
0.6019	Remote Similarity	NPD1982	Phase 1
0.6019	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.601	Remote Similarity	NPD704	Clinical (unspecified phase)
0.601	Remote Similarity	NPD3347	Clinical (unspecified phase)
0.6009	Remote Similarity	NPD5017	Discontinued
0.6009	Remote Similarity	NPD4051	Discontinued
0.6009	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3323	Discontinued
0.6	Remote Similarity	NPD6987	Phase 1
0.6	Remote Similarity	NPD4299	Phase 1
0.6	Remote Similarity	NPD1631	Approved
0.6	Remote Similarity	NPD3947	Discontinued
0.6	Remote Similarity	NPD6217	Discontinued
0.6	Remote Similarity	NPD5888	Phase 2
0.5991	Remote Similarity	NPD5685	Approved
0.5991	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD5686	Approved
0.5991	Remote Similarity	NPD7049	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD3915	Approved
0.5982	Remote Similarity	NPD4417	Approved
0.5982	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.5973	Remote Similarity	NPD7970	Approved
0.5973	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD2770	Discontinued
0.5972	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.597	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.597	Remote Similarity	NPD2720	Phase 1
0.5969	Remote Similarity	NPD2837	Discontinued
0.5957	Remote Similarity	NPD200	Phase 2
0.5957	Remote Similarity	NPD201	Phase 2
0.5956	Remote Similarity	NPD3917	Approved
0.5956	Remote Similarity	NPD3918	Approved
0.5956	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.5951	Remote Similarity	NPD4883	Approved
0.595	Remote Similarity	NPD5315	Discontinued
0.5946	Remote Similarity	NPD1506	Discontinued
0.5943	Remote Similarity	NPD6068	Discontinued
0.5943	Remote Similarity	NPD7175	Phase 1
0.594	Remote Similarity	NPD5415	Approved
0.5926	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.5924	Remote Similarity	NPD7026	Phase 2
0.5924	Remote Similarity	NPD5809	Phase 3
0.5922	Remote Similarity	NPD7402	Clinical (unspecified phase)
0.5919	Remote Similarity	NPD2443	Approved
0.5919	Remote Similarity	NPD7191	Phase 2
0.5919	Remote Similarity	NPD2442	Approved
0.5918	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD3927	Phase 2
0.5911	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.5911	Remote Similarity	NPD2413	Phase 2
0.5911	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD2879	Approved
0.5909	Remote Similarity	NPD2881	Approved
0.5902	Remote Similarity	NPD991	Phase 2
0.5902	Remote Similarity	NPD992	Clinical (unspecified phase)
0.5901	Remote Similarity	NPD3967	Approved
0.5901	Remote Similarity	NPD7010	Phase 3
0.5896	Remote Similarity	NPD6632	Clinical (unspecified phase)
0.5896	Remote Similarity	NPD3246	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data