NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	1064.5
Volume:	996.12
LogP:	-0.009
LogD:	0.072
LogS:	-2.415
# Rotatable Bonds:	11
TPSA:	375.52
# H-Bond Aceptor:	24
# H-Bond Donor:	14
# Rings:	10
# Heavy Atoms:	24

MedChem Properties

QED Drug-Likeness Score:	0.088
Synthetic Accessibility Score:	7.325
Fsp3:	0.96
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.515
MDCK Permeability:	0.00031500295153819025
Pgp-inhibitor:	0.001
Pgp-substrate:	0.796
Human Intestinal Absorption (HIA):	0.999
20% Bioavailability (F20%):	0.985
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.087
Plasma Protein Binding (PPB):	57.52153778076172%
Volume Distribution (VD):	-0.222
Pgp-substrate:	12.773177146911621%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.05
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.069
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.004
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.048
CYP3A4-inhibitor:	0.01
CYP3A4-substrate:	0.002

ADMET: Excretion

Clearance (CL):	0.189
Half-life (T1/2):	0.766

ADMET: Toxicity

hERG Blockers:	0.385
Human Hepatotoxicity (H-HT):	0.146
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.097
Rat Oral Acute Toxicity:	0.218
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.909
Carcinogencity:	0.055
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.459

Download Data

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

Natural Product: NPC477810

Natural Product ID:	NPC477810
*Common Name:**	(2R,3R,4R,5S,6S)-6-[(2S,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(1R,2R,4S,6R,7S,8R,9R,12S,13R,16S)-2-hydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl]oxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-4-yl]oxyoxane-2,3,4,5-tetrol
IUPAC Name:	(2R,3R,4R,5S,6S)-6-[(2S,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(1R,2R,4S,6R,7S,8R,9R,12S,13R,16S)-2-hydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl]oxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-4-yl]oxyoxane-2,3,4,5-tetrol
Synonyms:
Standard InCHIKey:	LNVBVOXSCKNFOD-PARUKXMISA-N
Standard InCHI:	InChI=1S/C50H80O24/c1-19-7-12-50(65-18-19)20(2)29-25(74-50)14-49(64)24-6-5-21-13-22(8-10-47(21,3)23(24)9-11-48(29,49)4)66-43-38(62)34(58)39(28(17-53)69-43)70-46-41(72-44-36(60)32(56)30(54)26(15-51)67-44)40(31(55)27(16-52)68-46)71-45-37(61)33(57)35(59)42(63)73-45/h5,19-20,22-46,51-64H,6-18H2,1-4H3/t19?,20-,22-,23-,24+,25-,26+,27+,28+,29-,30+,31+,32-,33+,34+,35+,36+,37-,38+,39-,40-,41+,42+,43+,44-,45-,46-,47-,48+,49+,50+/m0/s1
SMILES:	C[C@H]1[C@H]2[C@H](C[C@@]3([C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4(CC[C@@H](C5)O[C@H]6[C@@H]([C@H]([C@H]([C@H](O6)CO)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O[C@@H]8[C@H]([C@@H]([C@H]([C@@H](O8)O)O)O)O)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)O)O)C)C)O)O[C@]11CCC(CO1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44575243
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins

*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
NPO9935	Polygonatum sibiricum	Species	Asparagaceae	Eukaryota	rhizomes	Kangwon Province of Korea	2002-MAY	PMID[16562835]
NPO9935	Polygonatum sibiricum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9935	Polygonatum sibiricum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9935	Polygonatum sibiricum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9935	Polygonatum sibiricum	Species	Asparagaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	17600	nM	PMID[16562835]

☑ 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 NPC477810 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	315
0.1-0.2	2247
0.2-0.3	7294
0.3-0.4	13969
0.4-0.5	8202
0.5-0.6	5355
0.6-0.7	3008
0.7-0.8	1348
0.8-0.85	544
0.85-0.9	234
0.9-0.95	108
0.95-1	73

Similarity Score	Similarity Level	Natural Product ID
0.9626	High Similarity	NPC32707
0.9626	High Similarity	NPC167183
0.9623	High Similarity	NPC263359
0.9623	High Similarity	NPC31896
0.9623	High Similarity	NPC244431
0.9623	High Similarity	NPC32361
0.9623	High Similarity	NPC210569
0.9623	High Similarity	NPC19888
0.9619	High Similarity	NPC222202
0.9619	High Similarity	NPC224314
0.9619	High Similarity	NPC87998
0.9619	High Similarity	NPC269297
0.9619	High Similarity	NPC477811
0.9619	High Similarity	NPC23808
0.9533	High Similarity	NPC79900
0.9528	High Similarity	NPC13193
0.9528	High Similarity	NPC475247
0.9528	High Similarity	NPC294129
0.9528	High Similarity	NPC477032
0.9528	High Similarity	NPC197231
0.9528	High Similarity	NPC477028
0.9528	High Similarity	NPC124677
0.9528	High Similarity	NPC476547
0.9524	High Similarity	NPC309278
0.9524	High Similarity	NPC22779
0.9524	High Similarity	NPC73243
0.9524	High Similarity	NPC208383
0.9524	High Similarity	NPC475333
0.9524	High Similarity	NPC224098
0.9524	High Similarity	NPC232054
0.9524	High Similarity	NPC218571
0.9524	High Similarity	NPC171073
0.9524	High Similarity	NPC248746
0.9524	High Similarity	NPC477809
0.9524	High Similarity	NPC84956
0.9524	High Similarity	NPC150372
0.9524	High Similarity	NPC470433
0.9524	High Similarity	NPC244086
0.9524	High Similarity	NPC194207
0.9524	High Similarity	NPC46190
0.9524	High Similarity	NPC102016
0.9524	High Similarity	NPC475550
0.9524	High Similarity	NPC95051
0.9524	High Similarity	NPC300557
0.9524	High Similarity	NPC249265
0.9524	High Similarity	NPC302057
0.9524	High Similarity	NPC6806
0.9429	High Similarity	NPC98696
0.9358	High Similarity	NPC477030
0.9358	High Similarity	NPC477029
0.9352	High Similarity	NPC476693
0.9352	High Similarity	NPC476671
0.934	High Similarity	NPC40440
0.934	High Similarity	NPC475670
0.934	High Similarity	NPC306131
0.934	High Similarity	NPC477027
0.934	High Similarity	NPC70204
0.934	High Similarity	NPC42482
0.934	High Similarity	NPC477026
0.9333	High Similarity	NPC190395
0.9333	High Similarity	NPC283829
0.9333	High Similarity	NPC94272
0.9333	High Similarity	NPC161676
0.9333	High Similarity	NPC14704
0.9333	High Similarity	NPC113044
0.9333	High Similarity	NPC470432
0.9333	High Similarity	NPC305423
0.9333	High Similarity	NPC230507
0.9273	High Similarity	NPC20979
0.9273	High Similarity	NPC477807
0.9266	High Similarity	NPC477808
0.9266	High Similarity	NPC208832
0.9266	High Similarity	NPC11548
0.9259	High Similarity	NPC308140
0.9259	High Similarity	NPC254255
0.9259	High Similarity	NPC42171
0.9252	High Similarity	NPC247037
0.9245	High Similarity	NPC220427
0.9245	High Similarity	NPC6931
0.9245	High Similarity	NPC476540
0.9245	High Similarity	NPC476539
0.9245	High Similarity	NPC476538
0.9245	High Similarity	NPC476541
0.9245	High Similarity	NPC159005
0.9238	High Similarity	NPC242748
0.9238	High Similarity	NPC181845
0.9238	High Similarity	NPC309448
0.9196	High Similarity	NPC475358
0.9196	High Similarity	NPC473566
0.9182	High Similarity	NPC63609
0.9182	High Similarity	NPC477031
0.9174	High Similarity	NPC476546
0.9159	High Similarity	NPC476835
0.9151	High Similarity	NPC208650
0.9151	High Similarity	NPC226642
0.9151	High Similarity	NPC63368
0.9151	High Similarity	NPC14946
0.9143	High Similarity	NPC187400
0.9143	High Similarity	NPC221562
0.9143	High Similarity	NPC470885
0.9083	High Similarity	NPC112274
0.9074	High Similarity	NPC141433
0.9065	High Similarity	NPC180183
0.9065	High Similarity	NPC246124
0.9057	High Similarity	NPC194842
0.9057	High Similarity	NPC208477
0.9057	High Similarity	NPC473476
0.9057	High Similarity	NPC69737
0.9057	High Similarity	NPC26798
0.9057	High Similarity	NPC269627
0.9057	High Similarity	NPC152584
0.9057	High Similarity	NPC160816
0.9057	High Similarity	NPC127801
0.9057	High Similarity	NPC208594
0.9057	High Similarity	NPC474569
0.9057	High Similarity	NPC473923
0.9027	High Similarity	NPC198325
0.9027	High Similarity	NPC207243
0.9027	High Similarity	NPC233391
0.9018	High Similarity	NPC10366
0.9018	High Similarity	NPC476692
0.9018	High Similarity	NPC476691
0.9	High Similarity	NPC51154
0.9	High Similarity	NPC469347
0.9	High Similarity	NPC469348
0.9	High Similarity	NPC307642
0.8991	High Similarity	NPC13190
0.8972	High Similarity	NPC473469
0.8972	High Similarity	NPC181467
0.8962	High Similarity	NPC474464
0.8957	High Similarity	NPC202261
0.8957	High Similarity	NPC106589
0.8938	High Similarity	NPC195560
0.8938	High Similarity	NPC229962
0.8929	High Similarity	NPC476690
0.8929	High Similarity	NPC100048
0.8889	High Similarity	NPC7213
0.8879	High Similarity	NPC474015
0.887	High Similarity	NPC43842
0.8868	High Similarity	NPC473020
0.8868	High Similarity	NPC131479
0.8868	High Similarity	NPC16520
0.8868	High Similarity	NPC213190
0.8868	High Similarity	NPC8039
0.8868	High Similarity	NPC211879
0.8868	High Similarity	NPC157659
0.8868	High Similarity	NPC31907
0.8868	High Similarity	NPC472252
0.8868	High Similarity	NPC189852
0.8868	High Similarity	NPC475701
0.8868	High Similarity	NPC245280
0.8868	High Similarity	NPC120123
0.8868	High Similarity	NPC286969
0.8868	High Similarity	NPC114874
0.8868	High Similarity	NPC155010
0.886	High Similarity	NPC50689
0.885	High Similarity	NPC475357
0.8839	High Similarity	NPC148965
0.8839	High Similarity	NPC146652
0.8829	High Similarity	NPC144068
0.8818	High Similarity	NPC470748
0.8818	High Similarity	NPC114188
0.8818	High Similarity	NPC92710
0.8807	High Similarity	NPC157530
0.8807	High Similarity	NPC14630
0.8807	High Similarity	NPC250089
0.8793	High Similarity	NPC295133
0.8793	High Similarity	NPC256983
0.8793	High Similarity	NPC257207
0.8785	High Similarity	NPC273879
0.8785	High Similarity	NPC165033
0.8785	High Similarity	NPC475365
0.8774	High Similarity	NPC272015
0.8774	High Similarity	NPC136816
0.8774	High Similarity	NPC288694
0.8774	High Similarity	NPC159036
0.8774	High Similarity	NPC312553
0.8772	High Similarity	NPC476085
0.8772	High Similarity	NPC473633
0.8739	High Similarity	NPC472716
0.8727	High Similarity	NPC470867
0.8716	High Similarity	NPC51172
0.8716	High Similarity	NPC295980
0.8716	High Similarity	NPC125324
0.8716	High Similarity	NPC128123
0.8716	High Similarity	NPC49032
0.8707	High Similarity	NPC94072
0.8707	High Similarity	NPC305771
0.8707	High Similarity	NPC169816
0.8707	High Similarity	NPC15918
0.8704	High Similarity	NPC173859
0.8704	High Similarity	NPC470512
0.8696	High Similarity	NPC476670
0.8692	High Similarity	NPC123796
0.8692	High Similarity	NPC16573
0.8684	High Similarity	NPC475403
0.8684	High Similarity	NPC160888
0.8679	High Similarity	NPC47566
0.8679	High Similarity	NPC309425
0.8679	High Similarity	NPC88000

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 NPC477810 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	259
0.1-0.2	2409
0.2-0.3	4344
0.3-0.4	1386
0.4-0.5	395
0.5-0.6	236
0.6-0.7	91
0.7-0.8	17
0.8-0.85	10
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8462	Intermediate Similarity	NPD8033	Approved
0.8376	Intermediate Similarity	NPD8377	Approved
0.8376	Intermediate Similarity	NPD8294	Approved
0.8305	Intermediate Similarity	NPD8296	Approved
0.8305	Intermediate Similarity	NPD8335	Approved
0.8305	Intermediate Similarity	NPD8380	Approved
0.8305	Intermediate Similarity	NPD8379	Approved
0.8305	Intermediate Similarity	NPD8378	Approved
0.8019	Intermediate Similarity	NPD8171	Discontinued
0.7899	Intermediate Similarity	NPD7327	Approved
0.7899	Intermediate Similarity	NPD7328	Approved
0.7874	Intermediate Similarity	NPD8450	Suspended
0.7833	Intermediate Similarity	NPD7516	Approved
0.7795	Intermediate Similarity	NPD8449	Approved
0.7712	Intermediate Similarity	NPD8133	Approved
0.7705	Intermediate Similarity	NPD7503	Approved
0.7652	Intermediate Similarity	NPD6412	Phase 2
0.746	Intermediate Similarity	NPD7507	Approved
0.736	Intermediate Similarity	NPD6370	Approved
0.7344	Intermediate Similarity	NPD7736	Approved
0.7328	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD7319	Approved
0.7266	Intermediate Similarity	NPD8293	Discontinued
0.7227	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6059	Approved
0.72	Intermediate Similarity	NPD6054	Approved
0.7165	Intermediate Similarity	NPD8328	Phase 3
0.7097	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD8515	Approved
0.7008	Intermediate Similarity	NPD8517	Approved
0.7008	Intermediate Similarity	NPD6016	Approved
0.7008	Intermediate Similarity	NPD8516	Approved
0.7008	Intermediate Similarity	NPD6015	Approved
0.6977	Remote Similarity	NPD7492	Approved
0.6953	Remote Similarity	NPD5988	Approved
0.6923	Remote Similarity	NPD6616	Approved
0.6899	Remote Similarity	NPD6067	Discontinued
0.6887	Remote Similarity	NPD7525	Registered
0.6887	Remote Similarity	NPD6928	Phase 2
0.6875	Remote Similarity	NPD8513	Phase 3
0.687	Remote Similarity	NPD7078	Approved
0.6774	Remote Similarity	NPD8297	Approved
0.6774	Remote Similarity	NPD6882	Approved
0.6757	Remote Similarity	NPD7524	Approved
0.6721	Remote Similarity	NPD6686	Approved
0.6694	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD6009	Approved
0.6692	Remote Similarity	NPD6033	Approved
0.6667	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6319	Approved
0.6636	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7645	Phase 2
0.6607	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD7625	Phase 1
0.6587	Remote Similarity	NPD4632	Approved
0.6585	Remote Similarity	NPD7320	Approved
0.6571	Remote Similarity	NPD7339	Approved
0.6571	Remote Similarity	NPD6942	Approved
0.6557	Remote Similarity	NPD6008	Approved
0.6557	Remote Similarity	NPD5739	Approved
0.6557	Remote Similarity	NPD6675	Approved
0.6557	Remote Similarity	NPD6402	Approved
0.6557	Remote Similarity	NPD7128	Approved
0.6545	Remote Similarity	NPD6695	Phase 3
0.6532	Remote Similarity	NPD6373	Approved
0.6532	Remote Similarity	NPD6372	Approved
0.6471	Remote Similarity	NPD7638	Approved
0.646	Remote Similarity	NPD7750	Discontinued
0.6452	Remote Similarity	NPD6881	Approved
0.6452	Remote Similarity	NPD6899	Approved
0.6429	Remote Similarity	NPD8130	Phase 1
0.6429	Remote Similarity	NPD6650	Approved
0.6429	Remote Similarity	NPD6649	Approved
0.6417	Remote Similarity	NPD7639	Approved
0.6417	Remote Similarity	NPD7640	Approved
0.6387	Remote Similarity	NPD4755	Approved
0.6371	Remote Similarity	NPD5697	Approved
0.6371	Remote Similarity	NPD5701	Approved
0.6355	Remote Similarity	NPD6933	Approved
0.6349	Remote Similarity	NPD7290	Approved
0.6349	Remote Similarity	NPD7102	Approved
0.6349	Remote Similarity	NPD6883	Approved
0.6349	Remote Similarity	NPD4634	Approved
0.6325	Remote Similarity	NPD6399	Phase 3
0.6325	Remote Similarity	NPD4202	Approved
0.6321	Remote Similarity	NPD4784	Approved
0.6321	Remote Similarity	NPD4785	Approved
0.6308	Remote Similarity	NPD7115	Discovery
0.6299	Remote Similarity	NPD6869	Approved
0.6299	Remote Similarity	NPD6617	Approved
0.6299	Remote Similarity	NPD6847	Approved
0.6286	Remote Similarity	NPD4243	Approved
0.6281	Remote Similarity	NPD5286	Approved
0.6281	Remote Similarity	NPD4700	Approved
0.6281	Remote Similarity	NPD4696	Approved
0.6281	Remote Similarity	NPD5285	Approved
0.6273	Remote Similarity	NPD6931	Approved
0.6273	Remote Similarity	NPD4748	Discontinued
0.6273	Remote Similarity	NPD6930	Phase 2
0.627	Remote Similarity	NPD6012	Approved
0.627	Remote Similarity	NPD6014	Approved
0.627	Remote Similarity	NPD6013	Approved
0.6269	Remote Similarity	NPD7604	Phase 2
0.625	Remote Similarity	NPD6083	Phase 2
0.625	Remote Similarity	NPD6084	Phase 2
0.6241	Remote Similarity	NPD5983	Phase 2
0.6232	Remote Similarity	NPD5956	Approved
0.623	Remote Similarity	NPD4159	Approved
0.6218	Remote Similarity	NPD7991	Discontinued
0.6195	Remote Similarity	NPD4786	Approved
0.619	Remote Similarity	NPD6011	Approved
0.6182	Remote Similarity	NPD6929	Approved
0.6179	Remote Similarity	NPD4633	Approved
0.6179	Remote Similarity	NPD5225	Approved
0.6179	Remote Similarity	NPD5211	Phase 2
0.6179	Remote Similarity	NPD5226	Approved
0.6179	Remote Similarity	NPD5224	Approved
0.6176	Remote Similarity	NPD6336	Discontinued
0.6172	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD6926	Approved
0.6168	Remote Similarity	NPD6924	Approved
0.616	Remote Similarity	NPD4767	Approved
0.616	Remote Similarity	NPD4768	Approved
0.6147	Remote Similarity	NPD6932	Approved
0.6134	Remote Similarity	NPD7748	Approved
0.6129	Remote Similarity	NPD5175	Approved
0.6129	Remote Similarity	NPD5174	Approved
0.6124	Remote Similarity	NPD6053	Discontinued
0.6116	Remote Similarity	NPD7902	Approved
0.6102	Remote Similarity	NPD8034	Phase 2
0.6102	Remote Similarity	NPD8035	Phase 2
0.6102	Remote Similarity	NPD7087	Discontinued
0.6098	Remote Similarity	NPD5223	Approved
0.6083	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.608	Remote Similarity	NPD5141	Approved
0.6068	Remote Similarity	NPD5328	Approved
0.6068	Remote Similarity	NPD6051	Approved
0.6068	Remote Similarity	NPD4753	Phase 2
0.6066	Remote Similarity	NPD4225	Approved
0.6063	Remote Similarity	NPD4730	Approved
0.6063	Remote Similarity	NPD4729	Approved
0.6036	Remote Similarity	NPD6683	Phase 2
0.6019	Remote Similarity	NPD1810	Approved
0.6019	Remote Similarity	NPD1811	Approved
0.6018	Remote Similarity	NPD3667	Approved
0.6017	Remote Similarity	NPD3168	Discontinued
0.6016	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6014	Remote Similarity	NPD8074	Phase 3
0.6	Remote Similarity	NPD4754	Approved
0.6	Remote Similarity	NPD6893	Approved
0.6	Remote Similarity	NPD5776	Phase 2
0.6	Remote Similarity	NPD6925	Approved
0.5985	Remote Similarity	NPD6274	Approved
0.5982	Remote Similarity	NPD7509	Discontinued
0.5982	Remote Similarity	NPD7514	Phase 3
0.597	Remote Similarity	NPD7100	Approved
0.597	Remote Similarity	NPD7101	Approved
0.5969	Remote Similarity	NPD5250	Approved
0.5969	Remote Similarity	NPD5251	Approved
0.5969	Remote Similarity	NPD5248	Approved
0.5969	Remote Similarity	NPD5247	Approved
0.5969	Remote Similarity	NPD5249	Phase 3
0.5966	Remote Similarity	NPD6079	Approved
0.5966	Remote Similarity	NPD7515	Phase 2
0.5963	Remote Similarity	NPD5275	Approved
0.5963	Remote Similarity	NPD4190	Phase 3
0.595	Remote Similarity	NPD5695	Phase 3
0.5948	Remote Similarity	NPD3618	Phase 1
0.5946	Remote Similarity	NPD7145	Approved
0.5943	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD5128	Approved
0.5935	Remote Similarity	NPD5696	Approved
0.592	Remote Similarity	NPD7632	Discontinued
0.5913	Remote Similarity	NPD3666	Approved
0.5913	Remote Similarity	NPD3133	Approved
0.5913	Remote Similarity	NPD3665	Phase 1
0.5896	Remote Similarity	NPD6335	Approved
0.5893	Remote Similarity	NPD4195	Approved
0.5882	Remote Similarity	NPD6909	Approved
0.5882	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6908	Approved
0.5868	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD7900	Approved
0.5862	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5857	Remote Similarity	NPD8336	Approved
0.5857	Remote Similarity	NPD8337	Approved
0.5847	Remote Similarity	NPD6903	Approved
0.5847	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5846	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD7332	Phase 2
0.584	Remote Similarity	NPD5344	Discontinued
0.5833	Remote Similarity	NPD7152	Approved
0.5833	Remote Similarity	NPD7637	Suspended
0.5833	Remote Similarity	NPD7151	Approved
0.5833	Remote Similarity	NPD7150	Approved
0.5821	Remote Similarity	NPD6317	Approved
0.582	Remote Similarity	NPD4629	Approved
0.582	Remote Similarity	NPD5210	Approved
0.5814	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD6684	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