NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	502.13
Volume:	468.913
LogP:	0.895
LogD:	0.386
LogS:	-3.078
# Rotatable Bonds:	9
TPSA:	146.41
# H-Bond Aceptor:	11
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.193
Synthetic Accessibility Score:	4.354
Fsp3:	0.261
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.662
MDCK Permeability:	8.162698577507399e-06
Pgp-inhibitor:	0.008
Pgp-substrate:	0.117
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.251

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.178
Plasma Protein Binding (PPB):	79.21755981445312%
Volume Distribution (VD):	0.684
Pgp-substrate:	23.719377517700195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.463
CYP1A2-substrate:	0.673
CYP2C19-inhibitor:	0.082
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.044
CYP2C9-substrate:	0.799
CYP2D6-inhibitor:	0.776
CYP2D6-substrate:	0.588
CYP3A4-inhibitor:	0.596
CYP3A4-substrate:	0.13

ADMET: Excretion

Clearance (CL):	5.072
Half-life (T1/2):	0.395

ADMET: Toxicity

hERG Blockers:	0.595
Human Hepatotoxicity (H-HT):	0.977
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.278
Rat Oral Acute Toxicity:	0.746
Maximum Recommended Daily Dose:	0.961
Skin Sensitization:	0.539
Carcinogencity:	0.918
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.945

Download Data

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

Natural Product: NPC477805

Natural Product ID:	NPC477805
*Common Name:**	sodium;[(E)-2-[2-[(3,4-dihydroxyphenyl)-[4-[2-(dimethylamino)ethyl]imidazol-1-yl]methyl]-1,3-benzodioxol-5-yl]ethenyl] sulfate
IUPAC Name:	sodium;[(E)-2-[2-[(3,4-dihydroxyphenyl)-[4-[2-(dimethylamino)ethyl]imidazol-1-yl]methyl]-1,3-benzodioxol-5-yl]ethenyl] sulfate
Synonyms:
Standard InCHIKey:	GRGCVQDWSDWNMW-VRTOBVRTSA-M
Standard InCHI:	InChI=1S/C23H25N3O8S.Na/c1-25(2)9-7-17-13-26(14-24-17)22(16-4-5-18(27)19(28)12-16)23-33-20-6-3-15(11-21(20)34-23)8-10-32-35(29,30)31;/h3-6,8,10-14,22-23,27-28H,7,9H2,1-2H3,(H,29,30,31);/q;+1/p-1/b10-8+;
SMILES:	CN(C)CCC1=CN(C=N1)C(C2OC3=C(O2)C=C(C=C3)/C=C/OS(=O)(=O)[O-])C4=CC(=C(C=C4)O)O.[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	23672575
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	Vanuatu islands	n.a.	PMID[10924170]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11277766]
NPO20237	Poecillastra wondoensis	Species	Vulcanellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640526]
NPO20237	Poecillastra wondoensis	Species	Vulcanellidae	Eukaryota	n.a.	depth of 25 m off the shore of Keomun Island, Korea	2004-AUG	PMID[18407691]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	depth of 25 m off the shore of Keomun Island, Korea	2004-AUG	PMID[18407691]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18990572]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8326327]
NPO20237	Poecillastra wondoensis	Species	Vulcanellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	>	200	ug/ml	PMID[18407691]
NPT2	Others	Unspecified		IC50	>	200	ug/ml	PMID[18407691]

☑ 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 NPC477805 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	552
0.1-0.2	4009
0.2-0.3	13002
0.3-0.4	7086
0.4-0.5	12749
0.5-0.6	4687
0.6-0.7	556
0.7-0.8	50
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477796
1.0	High Similarity	NPC477795
1.0	High Similarity	NPC477806
0.8214	Intermediate Similarity	NPC308906
0.8044	Intermediate Similarity	NPC12100
0.7902	Intermediate Similarity	NPC242923
0.7749	Intermediate Similarity	NPC17305
0.7739	Intermediate Similarity	NPC136924
0.7716	Intermediate Similarity	NPC46970
0.765	Intermediate Similarity	NPC35761
0.7627	Intermediate Similarity	NPC237978
0.7563	Intermediate Similarity	NPC160666
0.7468	Intermediate Similarity	NPC467439
0.7379	Intermediate Similarity	NPC472068
0.732	Intermediate Similarity	NPC472067
0.732	Intermediate Similarity	NPC472031
0.732	Intermediate Similarity	NPC472066
0.7276	Intermediate Similarity	NPC471614
0.7225	Intermediate Similarity	NPC477019
0.7156	Intermediate Similarity	NPC280638
0.7143	Intermediate Similarity	NPC250178
0.7112	Intermediate Similarity	NPC135549
0.7112	Intermediate Similarity	NPC313189
0.7101	Intermediate Similarity	NPC473822
0.7076	Intermediate Similarity	NPC266931
0.7073	Intermediate Similarity	NPC96584
0.7073	Intermediate Similarity	NPC255800
0.7061	Intermediate Similarity	NPC201508
0.704	Intermediate Similarity	NPC99891
0.7034	Intermediate Similarity	NPC296482
0.7034	Intermediate Similarity	NPC96405
0.7034	Intermediate Similarity	NPC171409
0.7034	Intermediate Similarity	NPC53069
0.7034	Intermediate Similarity	NPC202605
0.7034	Intermediate Similarity	NPC112206
0.7034	Intermediate Similarity	NPC202768
0.7024	Intermediate Similarity	NPC472434
0.702	Intermediate Similarity	NPC476996
0.702	Intermediate Similarity	NPC476998
0.698	Remote Similarity	NPC476994
0.698	Remote Similarity	NPC476997
0.696	Remote Similarity	NPC30540
0.6958	Remote Similarity	NPC204446
0.6939	Remote Similarity	NPC323244
0.6926	Remote Similarity	NPC234197
0.6916	Remote Similarity	NPC133140
0.6916	Remote Similarity	NPC195268
0.6901	Remote Similarity	NPC54066
0.688	Remote Similarity	NPC295228
0.6878	Remote Similarity	NPC290689
0.6853	Remote Similarity	NPC476995
0.6844	Remote Similarity	NPC122463
0.6844	Remote Similarity	NPC118121
0.6838	Remote Similarity	NPC475774
0.6827	Remote Similarity	NPC328924
0.682	Remote Similarity	NPC251160
0.681	Remote Similarity	NPC476582
0.681	Remote Similarity	NPC4071
0.681	Remote Similarity	NPC476578
0.6809	Remote Similarity	NPC210256
0.6794	Remote Similarity	NPC472436
0.6792	Remote Similarity	NPC149471
0.6792	Remote Similarity	NPC271215
0.6762	Remote Similarity	NPC174049
0.6758	Remote Similarity	NPC284141
0.6757	Remote Similarity	NPC56271
0.675	Remote Similarity	NPC316981
0.6749	Remote Similarity	NPC173080
0.6745	Remote Similarity	NPC171393
0.6745	Remote Similarity	NPC295452
0.6743	Remote Similarity	NPC472435
0.6737	Remote Similarity	NPC36229
0.6737	Remote Similarity	NPC476581
0.6737	Remote Similarity	NPC16452
0.6736	Remote Similarity	NPC288349
0.673	Remote Similarity	NPC150447
0.6721	Remote Similarity	NPC46451
0.6709	Remote Similarity	NPC474145
0.6709	Remote Similarity	NPC475841
0.6706	Remote Similarity	NPC217554
0.6706	Remote Similarity	NPC223223
0.6695	Remote Similarity	NPC469589
0.6681	Remote Similarity	NPC54537
0.668	Remote Similarity	NPC23614
0.668	Remote Similarity	NPC469792
0.668	Remote Similarity	NPC100079
0.668	Remote Similarity	NPC39092
0.6667	Remote Similarity	NPC113369
0.6667	Remote Similarity	NPC8022
0.6667	Remote Similarity	NPC188420
0.6667	Remote Similarity	NPC470799
0.6641	Remote Similarity	NPC210296
0.6627	Remote Similarity	NPC11408
0.6612	Remote Similarity	NPC26679
0.6612	Remote Similarity	NPC471603
0.6611	Remote Similarity	NPC474595
0.661	Remote Similarity	NPC31930
0.6601	Remote Similarity	NPC220852
0.6588	Remote Similarity	NPC473183
0.6587	Remote Similarity	NPC21461
0.6587	Remote Similarity	NPC476999
0.6578	Remote Similarity	NPC314882
0.6565	Remote Similarity	NPC77878
0.6561	Remote Similarity	NPC469554
0.6557	Remote Similarity	NPC235076
0.6553	Remote Similarity	NPC127085
0.6545	Remote Similarity	NPC469594
0.6541	Remote Similarity	NPC478006
0.6534	Remote Similarity	NPC110151
0.6527	Remote Similarity	NPC274291
0.6527	Remote Similarity	NPC264166
0.6527	Remote Similarity	NPC165349
0.6527	Remote Similarity	NPC118832
0.6527	Remote Similarity	NPC329708
0.6527	Remote Similarity	NPC47059
0.6524	Remote Similarity	NPC226202
0.6523	Remote Similarity	NPC285343
0.6519	Remote Similarity	NPC315467
0.6518	Remote Similarity	NPC213530
0.6518	Remote Similarity	NPC193267
0.6516	Remote Similarity	NPC474594
0.651	Remote Similarity	NPC253675
0.651	Remote Similarity	NPC473184
0.6506	Remote Similarity	NPC280272
0.6502	Remote Similarity	NPC183537
0.65	Remote Similarity	NPC472111
0.65	Remote Similarity	NPC471736
0.6498	Remote Similarity	NPC25897
0.6494	Remote Similarity	NPC478009
0.6488	Remote Similarity	NPC185782
0.6484	Remote Similarity	NPC108342
0.6481	Remote Similarity	NPC314056
0.648	Remote Similarity	NPC130570
0.6479	Remote Similarity	NPC129897
0.6478	Remote Similarity	NPC204385
0.6475	Remote Similarity	NPC203168
0.6468	Remote Similarity	NPC107160
0.6468	Remote Similarity	NPC187145
0.6464	Remote Similarity	NPC51854
0.6461	Remote Similarity	NPC219664
0.6459	Remote Similarity	NPC189903
0.6459	Remote Similarity	NPC182907
0.6458	Remote Similarity	NPC475070
0.6454	Remote Similarity	NPC125597
0.6452	Remote Similarity	NPC148409
0.6449	Remote Similarity	NPC471080
0.6449	Remote Similarity	NPC476287
0.6449	Remote Similarity	NPC469592
0.6447	Remote Similarity	NPC206201
0.6446	Remote Similarity	NPC82548
0.6444	Remote Similarity	NPC199277
0.6444	Remote Similarity	NPC135887
0.6443	Remote Similarity	NPC314954
0.6441	Remote Similarity	NPC224928
0.644	Remote Similarity	NPC148124
0.6436	Remote Similarity	NPC478011
0.6434	Remote Similarity	NPC166722
0.6431	Remote Similarity	NPC101543
0.6429	Remote Similarity	NPC176538
0.6426	Remote Similarity	NPC9729
0.6422	Remote Similarity	NPC472289
0.6417	Remote Similarity	NPC245816
0.6417	Remote Similarity	NPC223427
0.6417	Remote Similarity	NPC476138
0.6413	Remote Similarity	NPC314176
0.641	Remote Similarity	NPC478013
0.6406	Remote Similarity	NPC172222
0.6406	Remote Similarity	NPC477633
0.6404	Remote Similarity	NPC318068
0.64	Remote Similarity	NPC99724
0.64	Remote Similarity	NPC310118
0.6395	Remote Similarity	NPC28945
0.6393	Remote Similarity	NPC5145
0.6382	Remote Similarity	NPC162530
0.6382	Remote Similarity	NPC236668
0.6381	Remote Similarity	NPC208898
0.6379	Remote Similarity	NPC308392
0.6374	Remote Similarity	NPC478010
0.6371	Remote Similarity	NPC267928
0.6371	Remote Similarity	NPC473513
0.6357	Remote Similarity	NPC74619
0.6356	Remote Similarity	NPC146976
0.6352	Remote Similarity	NPC174758
0.6345	Remote Similarity	NPC50548
0.6342	Remote Similarity	NPC22481
0.634	Remote Similarity	NPC26543
0.6339	Remote Similarity	NPC248903
0.6336	Remote Similarity	NPC15406
0.6336	Remote Similarity	NPC316756
0.6335	Remote Similarity	NPC473317
0.6333	Remote Similarity	NPC232727
0.6329	Remote Similarity	NPC473053
0.6329	Remote Similarity	NPC251090
0.6322	Remote Similarity	NPC470500
0.6322	Remote Similarity	NPC81175
0.6318	Remote Similarity	NPC478012
0.6318	Remote Similarity	NPC18487
0.6318	Remote Similarity	NPC277351
0.6316	Remote Similarity	NPC228040
0.6314	Remote Similarity	NPC307963

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 NPC477805 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	246
0.1-0.2	715
0.2-0.3	930
0.3-0.4	1739
0.4-0.5	2882
0.5-0.6	2053
0.6-0.7	554
0.7-0.8	30
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8261	Intermediate Similarity	NPD4080	Discontinued
0.7706	Intermediate Similarity	NPD6856	Discontinued
0.76	Intermediate Similarity	NPD2060	Approved
0.7576	Intermediate Similarity	NPD2530	Phase 2
0.7552	Intermediate Similarity	NPD5920	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD5107	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7980	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5703	Discontinued
0.7448	Intermediate Similarity	NPD6708	Discontinued
0.7418	Intermediate Similarity	NPD2929	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD3590	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD6643	Discontinued
0.7341	Intermediate Similarity	NPD8442	Discontinued
0.7325	Intermediate Similarity	NPD3838	Phase 3
0.7284	Intermediate Similarity	NPD949	Phase 1
0.7276	Intermediate Similarity	NPD6536	Approved
0.7276	Intermediate Similarity	NPD6537	Approved
0.7251	Intermediate Similarity	NPD6243	Phase 3
0.7251	Intermediate Similarity	NPD6244	Phase 3
0.721	Intermediate Similarity	NPD4131	Phase 3
0.7198	Intermediate Similarity	NPD7706	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD1287	Phase 2
0.7172	Intermediate Similarity	NPD7705	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD6473	Phase 1
0.7126	Intermediate Similarity	NPD6743	Phase 2
0.7126	Intermediate Similarity	NPD6742	Phase 2
0.7115	Intermediate Similarity	NPD6216	Approved
0.7082	Intermediate Similarity	NPD5529	Phase 1
0.7082	Intermediate Similarity	NPD5528	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD1954	Phase 1
0.7037	Intermediate Similarity	NPD7051	Phase 3
0.7037	Intermediate Similarity	NPD7050	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD3254	Phase 1
0.7034	Intermediate Similarity	NPD3255	Phase 1
0.7034	Intermediate Similarity	NPD3816	Phase 1
0.7034	Intermediate Similarity	NPD3815	Phase 1
0.7017	Intermediate Similarity	NPD5612	Discontinued
0.7012	Intermediate Similarity	NPD5833	Phase 1
0.7011	Intermediate Similarity	NPD5949	Phase 3
0.7004	Intermediate Similarity	NPD4306	Phase 1
0.7	Intermediate Similarity	NPD5905	Phase 1
0.7	Intermediate Similarity	NPD4555	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6501	Approved
0.7	Intermediate Similarity	NPD6500	Approved
0.6989	Remote Similarity	NPD8421	Discontinued
0.6985	Remote Similarity	NPD3343	Phase 3
0.696	Remote Similarity	NPD2414	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6223	Clinical (unspecified phase)
0.693	Remote Similarity	NPD2769	Approved
0.693	Remote Similarity	NPD978	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD4132	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4996	Approved
0.6923	Remote Similarity	NPD4995	Approved
0.692	Remote Similarity	NPD7758	Approved
0.692	Remote Similarity	NPD7757	Approved
0.6917	Remote Similarity	NPD7620	Phase 2
0.6916	Remote Similarity	NPD3924	Approved
0.6916	Remote Similarity	NPD3921	Approved
0.6916	Remote Similarity	NPD3922	Approved
0.6916	Remote Similarity	NPD3923	Approved
0.6914	Remote Similarity	NPD4916	Discontinued
0.6894	Remote Similarity	NPD7452	Approved
0.6894	Remote Similarity	NPD7453	Approved
0.6894	Remote Similarity	NPD6023	Discontinued
0.6894	Remote Similarity	NPD2886	Approved
0.6894	Remote Similarity	NPD7222	Phase 2
0.6894	Remote Similarity	NPD2885	Approved
0.6883	Remote Similarity	NPD4925	Approved
0.688	Remote Similarity	NPD5459	Phase 2
0.6875	Remote Similarity	NPD3886	Phase 1
0.6875	Remote Similarity	NPD5644	Phase 1
0.6867	Remote Similarity	NPD6494	Phase 2
0.6865	Remote Similarity	NPD4858	Phase 2
0.685	Remote Similarity	NPD7068	Approved
0.685	Remote Similarity	NPD7067	Approved
0.684	Remote Similarity	NPD722	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD6450	Phase 2
0.6833	Remote Similarity	NPD6528	Phase 1
0.6828	Remote Similarity	NPD5018	Phase 3
0.6827	Remote Similarity	NPD6814	Phase 3
0.6816	Remote Similarity	NPD6197	Approved
0.6807	Remote Similarity	NPD4048	Approved
0.6805	Remote Similarity	NPD6772	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD6460	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7486	Phase 1
0.679	Remote Similarity	NPD3514	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD3938	Phase 1
0.6782	Remote Similarity	NPD5911	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD8049	Phase 2
0.6778	Remote Similarity	NPD2540	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD2599	Approved
0.6771	Remote Similarity	NPD2600	Approved
0.6771	Remote Similarity	NPD2601	Approved
0.6769	Remote Similarity	NPD5539	Phase 2
0.6769	Remote Similarity	NPD6569	Phase 2
0.6768	Remote Similarity	NPD5116	Phase 1
0.6767	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5008	Approved
0.6745	Remote Similarity	NPD5051	Phase 1
0.674	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD5567	Approved
0.6734	Remote Similarity	NPD1882	Phase 2
0.6734	Remote Similarity	NPD8292	Phase 2
0.6732	Remote Similarity	NPD7117	Phase 2
0.6725	Remote Similarity	NPD4148	Approved
0.6721	Remote Similarity	NPD5829	Phase 2
0.6721	Remote Similarity	NPD3763	Approved
0.6719	Remote Similarity	NPD6573	Phase 3
0.6719	Remote Similarity	NPD6572	Phase 2
0.6718	Remote Similarity	NPD6482	Phase 1
0.6704	Remote Similarity	NPD7684	Approved
0.6704	Remote Similarity	NPD7682	Approved
0.6693	Remote Similarity	NPD7943	Suspended
0.6692	Remote Similarity	NPD6207	Discovery
0.668	Remote Similarity	NPD5045	Phase 2
0.668	Remote Similarity	NPD6202	Discontinued
0.668	Remote Similarity	NPD8512	Phase 3
0.6667	Remote Similarity	NPD6327	Phase 1
0.6667	Remote Similarity	NPD7112	Discontinued
0.6667	Remote Similarity	NPD4551	Phase 2
0.6667	Remote Similarity	NPD3397	Phase 2
0.6667	Remote Similarity	NPD1231	Phase 3
0.6654	Remote Similarity	NPD5802	Phase 2
0.6654	Remote Similarity	NPD7588	Discontinued
0.6653	Remote Similarity	NPD5868	Approved
0.6642	Remote Similarity	NPD6228	Discontinued
0.664	Remote Similarity	NPD2535	Discontinued
0.664	Remote Similarity	NPD6601	Approved
0.664	Remote Similarity	NPD6600	Approved
0.664	Remote Similarity	NPD2757	Phase 2
0.6638	Remote Similarity	NPD2152	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7198	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD7169	Suspended
0.6628	Remote Similarity	NPD7967	Discontinued
0.6628	Remote Similarity	NPD6774	Approved
0.6628	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD1273	Discontinued
0.6627	Remote Similarity	NPD6605	Phase 3
0.6627	Remote Similarity	NPD6750	Phase 2
0.6626	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD6877	Discontinued
0.6623	Remote Similarity	NPD996	Phase 2
0.6623	Remote Similarity	NPD994	Phase 2
0.6619	Remote Similarity	NPD8525	Approved
0.6618	Remote Similarity	NPD6175	Phase 3
0.6615	Remote Similarity	NPD4876	Phase 3
0.6615	Remote Similarity	NPD4875	Phase 3
0.6615	Remote Similarity	NPD5007	Approved
0.6614	Remote Similarity	NPD7938	Suspended
0.6609	Remote Similarity	NPD5582	Discontinued
0.6608	Remote Similarity	NPD8524	Approved
0.6604	Remote Similarity	NPD7273	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD8288	Phase 2
0.6604	Remote Similarity	NPD8287	Phase 1
0.6602	Remote Similarity	NPD5908	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD7558	Phase 2
0.66	Remote Similarity	NPD6326	Phase 2
0.6596	Remote Similarity	NPD3541	Clinical (unspecified phase)
0.659	Remote Similarity	NPD5998	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD4440	Clinical (unspecified phase)
0.6586	Remote Similarity	NPD1258	Discontinued
0.6586	Remote Similarity	NPD3042	Approved
0.6586	Remote Similarity	NPD3043	Approved
0.6578	Remote Similarity	NPD443	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD7898	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD7897	Phase 3
0.6576	Remote Similarity	NPD6848	Phase 1
0.6573	Remote Similarity	NPD6036	Suspended
0.6571	Remote Similarity	NPD5080	Phase 2
0.6569	Remote Similarity	NPD6754	Phase 3
0.6567	Remote Similarity	NPD4418	Discontinued
0.6564	Remote Similarity	NPD6230	Discontinued
0.6561	Remote Similarity	NPD2984	Phase 2
0.6548	Remote Similarity	NPD1900	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD1197	Approved
0.6542	Remote Similarity	NPD1392	Approved
0.654	Remote Similarity	NPD7859	Phase 2
0.6538	Remote Similarity	NPD8375	Approved
0.6531	Remote Similarity	NPD8510	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD5079	Phase 2
0.653	Remote Similarity	NPD5870	Clinical (unspecified phase)
0.653	Remote Similarity	NPD5869	Phase 2
0.6527	Remote Similarity	NPD31	Approved
0.6527	Remote Similarity	NPD4034	Approved
0.6527	Remote Similarity	NPD4036	Approved
0.6527	Remote Similarity	NPD4122	Approved
0.6527	Remote Similarity	NPD32	Approved
0.6527	Remote Similarity	NPD4039	Approved
0.6527	Remote Similarity	NPD4038	Approved
0.6527	Remote Similarity	NPD4035	Approved
0.6527	Remote Similarity	NPD4033	Approved
0.6527	Remote Similarity	NPD4037	Approved
0.6525	Remote Similarity	NPD4548	Discontinued
0.6523	Remote Similarity	NPD5805	Approved
0.6522	Remote Similarity	NPD3002	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD8105	Discontinued
0.6518	Remote Similarity	NPD3875	Discontinued
0.6516	Remote Similarity	NPD5944	Phase 1

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