NPASS Compound

Structure

CID323958 OpenBabel06191716172D 35 38 0 0 1 0 0 0 0 0999 V2000 -7.4519 -1.4858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5487 -1.2072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3438 -2.1159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9758 -3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2698 -3.5005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2016 -3.8033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7240 -4.0556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9963 -4.7108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9066 -2.7957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6594 -0.6263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4537 -1.5342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5909 -0.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3855 -1.8370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1347 -2.2398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5862 -0.2260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2484 -2.4432 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0661 -2.5422 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9313 -1.2819 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9297 -3.1477 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5210 -3.0981 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8616 -3.4505 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7260 -2.1894 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.1101 -1.8383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5171 0.0764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7942 -1.8866 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5892 -2.7953 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.3827 -1.1834 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -10.0410 -1.5358 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.7206 1.0338 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2444 -0.5785 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9793 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9793 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9793 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9793 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 4 9 1 0 0 0 0 4 16 1 0 0 0 0 5 6 1 0 0 0 0 5 17 1 0 0 0 0 7 8 1 0 0 0 0 7 20 1 0 0 0 0 8 21 1 0 0 0 0 9 23 1 0 0 0 0 10 12 1 0 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 11 22 1 0 0 0 0 12 25 1 0 0 0 0 13 26 1 0 0 0 0 14 17 1 0 0 0 0 14 18 1 0 0 0 0 15 24 1 0 0 0 0 15 27 1 0 0 0 0 16 1 1 1 0 0 0 16 20 1 0 0 0 0 17 25 1 1 0 0 0 18 34 1 1 0 0 0 19 6 1 1 0 0 0 19 21 1 0 0 0 0 19 22 1 0 0 0 0 20 26 1 6 0 0 0 21 26 1 6 0 0 0 22 25 1 6 0 0 0 23 27 2 3 0 0 0 23 28 1 0 0 0 0 24 29 2 0 0 0 0 24 30 1 0 0 0 0 25 2 1 6 0 0 0 26 3 1 6 0 0 0 31 35 1 0 0 0 0 32 35 2 0 0 0 0 33 35 2 0 0 0 0 34 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	513.28
Volume:	509.791
LogP:	2.508
LogD:	4.004
LogS:	-1.764
# Rotatable Bonds:	9
TPSA:	130.0
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.409
Synthetic Accessibility Score:	4.41
Fsp3:	0.923
Lipinski Rule-of-5:	Accepted
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:	-5.368
MDCK Permeability:	4.219086349621648e-06
Pgp-inhibitor:	0.831
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.584
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	95.90164947509766%
Volume Distribution (VD):	0.595
Pgp-substrate:	2.3582913875579834%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.234
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.382
CYP2C9-inhibitor:	0.047
CYP2C9-substrate:	0.869
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.151
CYP3A4-inhibitor:	0.022
CYP3A4-substrate:	0.037

ADMET: Excretion

Clearance (CL):	1.739
Half-life (T1/2):	0.713

ADMET: Toxicity

hERG Blockers:	0.35
Human Hepatotoxicity (H-HT):	0.587
Drug-inuced Liver Injury (DILI):	0.124
AMES Toxicity:	0.268
Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.42
Skin Sensitization:	0.972
Carcinogencity:	0.254
Eye Corrosion:	0.366
Eye Irritation:	0.067
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC323958

Natural Product ID:	NPC323958
*Common Name:**	Glycolithocholate-3-Sulfate
IUPAC Name:	2-[[(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3-sulfooxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]acetic acid
Synonyms:
Standard InCHIKey:	FHXBAFXQVZOILS-OETIFKLTSA-N
Standard InCHI:	InChI=1S/C26H43NO7S/c1-16(4-9-23(28)27-15-24(29)30)20-7-8-21-19-6-5-17-14-18(34-35(31,32)33)10-12-25(17,2)22(19)11-13-26(20,21)3/h16-22H,4-15H2,1-3H3,(H,27,28)(H,29,30)(H,31,32,33)/t16-,17-,18-,19+,20-,21+,22+,25+,26-/m1/s1
SMILES:	OC(=O)CN=C(CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC[C@H]2[C@]1(C)CC[C@H](C2)OS(=O)(=O)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2074584
PubChem CID:	72222
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0001124] Glycinated bile acids and derivatives

*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

☑ 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
Ki	1
Others	3

Activity Type	# Activity
Individual Protein	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2850	Individual Protein	Multidrug resistance associated protein	Homo sapiens	Activity	=	29.0	%	PMID[494491]
NPT1028	Individual Protein	Multidrug resistance-associated protein 4	Homo sapiens	IC50	=	10000.0	nM	PMID[494492]
NPT1594	Individual Protein	Multidrug resistance-associated protein 1	Homo sapiens	Ki	=	1400.0	nM	PMID[494493]
NPT957	Individual Protein	Multidrug resistance-associated protein 7	Homo sapiens	Activity	=	41.8	%	PMID[494490]

☑ 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 NPC323958 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	113
0.1-0.2	2270
0.2-0.3	18930
0.3-0.4	10441
0.4-0.5	6059
0.5-0.6	4167
0.6-0.7	669
0.7-0.8	34
0.8-0.85	7
0.85-0.9	1
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9383	High Similarity	NPC323180
0.9268	High Similarity	NPC175419
0.9048	High Similarity	NPC321340
0.9048	High Similarity	NPC171698
0.9048	High Similarity	NPC270957
0.9048	High Similarity	NPC119633
0.8295	Intermediate Similarity	NPC320478
0.8202	Intermediate Similarity	NPC283751
0.8202	Intermediate Similarity	NPC317363
0.8022	Intermediate Similarity	NPC159390
0.8022	Intermediate Similarity	NPC133995
0.8022	Intermediate Similarity	NPC247891
0.7882	Intermediate Similarity	NPC329117
0.7614	Intermediate Similarity	NPC192456
0.7326	Intermediate Similarity	NPC478105
0.7241	Intermediate Similarity	NPC4209
0.7209	Intermediate Similarity	NPC167702
0.7209	Intermediate Similarity	NPC280026
0.7176	Intermediate Similarity	NPC478103
0.7159	Intermediate Similarity	NPC317913
0.7159	Intermediate Similarity	NPC207010
0.7159	Intermediate Similarity	NPC212453
0.7126	Intermediate Similarity	NPC212733
0.7115	Intermediate Similarity	NPC478053
0.7079	Intermediate Similarity	NPC185465
0.7079	Intermediate Similarity	NPC171426
0.7079	Intermediate Similarity	NPC34046
0.7079	Intermediate Similarity	NPC80089
0.7079	Intermediate Similarity	NPC324700
0.7079	Intermediate Similarity	NPC224802
0.7073	Intermediate Similarity	NPC477603
0.7037	Intermediate Similarity	NPC114891
0.7011	Intermediate Similarity	NPC478130
0.7	Intermediate Similarity	NPC476176
0.7	Intermediate Similarity	NPC320144
0.7	Intermediate Similarity	NPC80891
0.7	Intermediate Similarity	NPC201276
0.7	Intermediate Similarity	NPC220379
0.6979	Remote Similarity	NPC271974
0.6979	Remote Similarity	NPC247312
0.6977	Remote Similarity	NPC126642
0.6966	Remote Similarity	NPC298168
0.6966	Remote Similarity	NPC143133
0.6923	Remote Similarity	NPC261616
0.6914	Remote Similarity	NPC218585
0.6914	Remote Similarity	NPC71460
0.6914	Remote Similarity	NPC148174
0.6905	Remote Similarity	NPC475172
0.6889	Remote Similarity	NPC471045
0.6857	Remote Similarity	NPC258130
0.6854	Remote Similarity	NPC473916
0.6854	Remote Similarity	NPC477601
0.6854	Remote Similarity	NPC477602
0.6848	Remote Similarity	NPC12933
0.6848	Remote Similarity	NPC73515
0.6848	Remote Similarity	NPC109533
0.6848	Remote Similarity	NPC190940
0.6786	Remote Similarity	NPC142712
0.6782	Remote Similarity	NPC156277
0.6782	Remote Similarity	NPC469940
0.6782	Remote Similarity	NPC320549
0.6782	Remote Similarity	NPC151018
0.6782	Remote Similarity	NPC58057
0.6778	Remote Similarity	NPC171658
0.6774	Remote Similarity	NPC30583
0.6774	Remote Similarity	NPC121121
0.6774	Remote Similarity	NPC60018
0.6774	Remote Similarity	NPC289486
0.6774	Remote Similarity	NPC61107
0.6774	Remote Similarity	NPC477286
0.6774	Remote Similarity	NPC154043
0.6774	Remote Similarity	NPC202688
0.6774	Remote Similarity	NPC286719
0.6747	Remote Similarity	NPC69149
0.6747	Remote Similarity	NPC281540
0.6747	Remote Similarity	NPC118937
0.6747	Remote Similarity	NPC159654
0.6747	Remote Similarity	NPC167995
0.6744	Remote Similarity	NPC252032
0.6744	Remote Similarity	NPC107919
0.6744	Remote Similarity	NPC476734
0.6744	Remote Similarity	NPC469941
0.6744	Remote Similarity	NPC319671
0.6744	Remote Similarity	NPC66407
0.6742	Remote Similarity	NPC186851
0.6739	Remote Similarity	NPC206735
0.6706	Remote Similarity	NPC48079
0.6706	Remote Similarity	NPC473230
0.6706	Remote Similarity	NPC475884
0.6705	Remote Similarity	NPC232112
0.6702	Remote Similarity	NPC477285
0.6702	Remote Similarity	NPC246956
0.6702	Remote Similarity	NPC111582
0.6698	Remote Similarity	NPC36497
0.6667	Remote Similarity	NPC41577
0.6667	Remote Similarity	NPC232925
0.6667	Remote Similarity	NPC63588
0.6667	Remote Similarity	NPC58631
0.6667	Remote Similarity	NPC251201
0.6667	Remote Similarity	NPC473276
0.6667	Remote Similarity	NPC192192
0.6667	Remote Similarity	NPC473537
0.6667	Remote Similarity	NPC474380
0.6667	Remote Similarity	NPC477929
0.6632	Remote Similarity	NPC319909
0.6632	Remote Similarity	NPC473336
0.6632	Remote Similarity	NPC471044
0.663	Remote Similarity	NPC52951
0.6629	Remote Similarity	NPC472945
0.6629	Remote Similarity	NPC472944
0.6629	Remote Similarity	NPC254340
0.6629	Remote Similarity	NPC74639
0.6629	Remote Similarity	NPC272359
0.6629	Remote Similarity	NPC477930
0.6628	Remote Similarity	NPC472741
0.6607	Remote Similarity	NPC165396
0.6602	Remote Similarity	NPC252564
0.6602	Remote Similarity	NPC475249
0.6593	Remote Similarity	NPC477918
0.6593	Remote Similarity	NPC477919
0.6593	Remote Similarity	NPC180199
0.6591	Remote Similarity	NPC252182
0.6591	Remote Similarity	NPC473552
0.6591	Remote Similarity	NPC100586
0.6591	Remote Similarity	NPC477822
0.6591	Remote Similarity	NPC127094
0.6591	Remote Similarity	NPC324984
0.6591	Remote Similarity	NPC323900
0.6591	Remote Similarity	NPC477823
0.6591	Remote Similarity	NPC109457
0.6591	Remote Similarity	NPC187471
0.6591	Remote Similarity	NPC477821
0.6591	Remote Similarity	NPC470071
0.6591	Remote Similarity	NPC1340
0.6591	Remote Similarity	NPC157422
0.6588	Remote Similarity	NPC44122
0.6588	Remote Similarity	NPC42060
0.6588	Remote Similarity	NPC477931
0.6588	Remote Similarity	NPC268736
0.6577	Remote Similarity	NPC106479
0.6566	Remote Similarity	NPC312637
0.6562	Remote Similarity	NPC266651
0.6559	Remote Similarity	NPC477851
0.6559	Remote Similarity	NPC474714
0.6556	Remote Similarity	NPC472311
0.6556	Remote Similarity	NPC97534
0.6556	Remote Similarity	NPC477934
0.6556	Remote Similarity	NPC273366
0.6556	Remote Similarity	NPC174964
0.6556	Remote Similarity	NPC195155
0.6552	Remote Similarity	NPC129829
0.6552	Remote Similarity	NPC6120
0.6552	Remote Similarity	NPC64466
0.6552	Remote Similarity	NPC213178
0.6552	Remote Similarity	NPC254037
0.6552	Remote Similarity	NPC196197
0.6552	Remote Similarity	NPC470830
0.6552	Remote Similarity	NPC477820
0.6552	Remote Similarity	NPC327728
0.6552	Remote Similarity	NPC299948
0.6552	Remote Similarity	NPC131892
0.6552	Remote Similarity	NPC241085
0.6549	Remote Similarity	NPC471120
0.6549	Remote Similarity	NPC471117
0.6545	Remote Similarity	NPC66862
0.6543	Remote Similarity	NPC476735
0.6538	Remote Similarity	NPC201712
0.6526	Remote Similarity	NPC5280
0.6526	Remote Similarity	NPC15821
0.6522	Remote Similarity	NPC199965
0.6522	Remote Similarity	NPC476732
0.6522	Remote Similarity	NPC478128
0.6517	Remote Similarity	NPC153719
0.6517	Remote Similarity	NPC470610
0.6512	Remote Similarity	NPC476928
0.6505	Remote Similarity	NPC240650
0.6495	Remote Similarity	NPC103782
0.6495	Remote Similarity	NPC114378
0.6495	Remote Similarity	NPC168231
0.6495	Remote Similarity	NPC155531
0.6495	Remote Similarity	NPC472272
0.6495	Remote Similarity	NPC477283
0.6495	Remote Similarity	NPC215968
0.6495	Remote Similarity	NPC302111
0.6495	Remote Similarity	NPC2783
0.6491	Remote Similarity	NPC471118
0.6491	Remote Similarity	NPC471121
0.6484	Remote Similarity	NPC477933
0.6484	Remote Similarity	NPC472486
0.6484	Remote Similarity	NPC472487
0.6484	Remote Similarity	NPC477932
0.6484	Remote Similarity	NPC475742
0.6484	Remote Similarity	NPC5767
0.6477	Remote Similarity	NPC282454
0.6477	Remote Similarity	NPC108131
0.6477	Remote Similarity	NPC477850
0.6477	Remote Similarity	NPC231945
0.6476	Remote Similarity	NPC475518
0.6458	Remote Similarity	NPC299963
0.6455	Remote Similarity	NPC72753

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 NPC323958 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	77
0.1-0.2	1591
0.2-0.3	5202
0.3-0.4	1616
0.4-0.5	428
0.5-0.6	185
0.6-0.7	38
0.7-0.8	11
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8022	Intermediate Similarity	NPD6700	Approved
0.8022	Intermediate Similarity	NPD6701	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD6703	Approved
0.7742	Intermediate Similarity	NPD6702	Approved
0.7551	Intermediate Similarity	NPD8418	Phase 2
0.7241	Intermediate Similarity	NPD6117	Approved
0.7209	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD6116	Phase 1
0.7079	Intermediate Similarity	NPD6114	Approved
0.7079	Intermediate Similarity	NPD6697	Approved
0.7079	Intermediate Similarity	NPD6115	Approved
0.7079	Intermediate Similarity	NPD6118	Approved
0.7037	Intermediate Similarity	NPD8298	Phase 2
0.6824	Remote Similarity	NPD6705	Phase 1
0.6782	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7920	Phase 3
0.6667	Remote Similarity	NPD7919	Phase 3
0.6602	Remote Similarity	NPD8088	Phase 1
0.6591	Remote Similarity	NPD6081	Approved
0.6552	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5364	Discontinued
0.6477	Remote Similarity	NPD4787	Phase 1
0.6437	Remote Similarity	NPD5360	Phase 3
0.6437	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD4224	Phase 2
0.6392	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.633	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD1448	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD7991	Discontinued
0.6292	Remote Similarity	NPD4244	Approved
0.6292	Remote Similarity	NPD4245	Approved
0.6292	Remote Similarity	NPD4789	Approved
0.6222	Remote Similarity	NPD5777	Approved
0.6196	Remote Similarity	NPD3702	Approved
0.6196	Remote Similarity	NPD3703	Phase 2
0.618	Remote Similarity	NPD3698	Phase 2
0.6176	Remote Similarity	NPD8035	Phase 2
0.6176	Remote Similarity	NPD8034	Phase 2
0.6126	Remote Similarity	NPD8174	Phase 2
0.6092	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD6920	Discontinued
0.6064	Remote Similarity	NPD8143	Approved
0.6064	Remote Similarity	NPD8144	Approved
0.6055	Remote Similarity	NPD7986	Approved
0.6055	Remote Similarity	NPD7912	Approved
0.6055	Remote Similarity	NPD7911	Approved
0.6055	Remote Similarity	NPD7987	Approved
0.6044	Remote Similarity	NPD4758	Discontinued
0.6042	Remote Similarity	NPD6928	Phase 2
0.6042	Remote Similarity	NPD7525	Registered
0.6	Remote Similarity	NPD4776	Phase 2
0.6	Remote Similarity	NPD3671	Phase 1
0.6	Remote Similarity	NPD8308	Discontinued
0.6	Remote Similarity	NPD4777	Suspended
0.5946	Remote Similarity	NPD8040	Discontinued
0.5938	Remote Similarity	NPD5354	Approved
0.5897	Remote Similarity	NPD7754	Approved
0.5897	Remote Similarity	NPD7755	Approved
0.5893	Remote Similarity	NPD7989	Approved
0.5893	Remote Similarity	NPD7990	Approved
0.5841	Remote Similarity	NPD6415	Discontinued
0.581	Remote Similarity	NPD6399	Phase 3
0.58	Remote Similarity	NPD3668	Phase 3
0.5785	Remote Similarity	NPD6909	Approved
0.5785	Remote Similarity	NPD6908	Approved
0.578	Remote Similarity	NPD6404	Discontinued
0.5755	Remote Similarity	NPD5771	Approved
0.5714	Remote Similarity	NPD3724	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD3187	Discontinued
0.5688	Remote Similarity	NPD7638	Approved
0.5684	Remote Similarity	NPD7339	Approved
0.5684	Remote Similarity	NPD6942	Approved
0.5667	Remote Similarity	NPD2263	Discontinued
0.566	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD3725	Approved
0.5652	Remote Similarity	NPD3726	Approved
0.5644	Remote Similarity	NPD4786	Approved
0.5641	Remote Similarity	NPD8078	Approved
0.5641	Remote Similarity	NPD8077	Approved
0.5636	Remote Similarity	NPD7640	Approved
0.5636	Remote Similarity	NPD7639	Approved
0.5607	Remote Similarity	NPD5707	Approved

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