NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	895.53
Volume:	902.433
LogP:	3.235
LogD:	2.897
LogS:	-3.145
# Rotatable Bonds:	16
TPSA:	251.0
# H-Bond Aceptor:	16
# H-Bond Donor:	8
# Rings:	6
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.092
Synthetic Accessibility Score:	6.146
Fsp3:	0.894
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:	-6.004
MDCK Permeability:	4.35846668551676e-05
Pgp-inhibitor:	0.933
Pgp-substrate:	0.28
Human Intestinal Absorption (HIA):	0.844
20% Bioavailability (F20%):	0.184
30% Bioavailability (F30%):	0.965

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	82.75926208496094%
Volume Distribution (VD):	0.631
Pgp-substrate:	5.1594462394714355%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.084
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.56
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.022
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.051
CYP3A4-inhibitor:	0.079
CYP3A4-substrate:	0.304

ADMET: Excretion

Clearance (CL):	1.151
Half-life (T1/2):	0.594

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.257
Drug-inuced Liver Injury (DILI):	0.092
AMES Toxicity:	0.106
Rat Oral Acute Toxicity:	0.047
Maximum Recommended Daily Dose:	0.045
Skin Sensitization:	0.014
Carcinogencity:	0.016
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.634

Download Data

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

Natural Product: NPC477072

Natural Product ID:	NPC477072
*Common Name:**	eryloside F6
IUPAC Name:	(3S,5R,10S,13R,14S)-3-[(2R,3R,4S,5R,6R)-3-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-[(2R)-5-acetyloxy-5,6-dimethylheptan-2-yl]-4,4,10,13-tetramethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-14-carboxylic acid
Synonyms:	eryloside F6
Standard InCHIKey:	WMOIUTVCNAQFAG-AVWNVJDJSA-N
Standard InCHI:	InChI=1S/C47H77NO15/c1-23(2)46(10,63-26(5)52)19-13-24(3)27-15-20-47(42(57)58)29-11-12-32-43(6,7)33(16-17-44(32,8)28(29)14-18-45(27,47)9)61-41-39(38(56)36(54)31(22-50)60-41)62-40-34(48-25(4)51)37(55)35(53)30(21-49)59-40/h23-24,27,30-41,49-50,53-56H,11-22H2,1-10H3,(H,48,51)(H,57,58)/t24-,27?,30-,31-,32+,33+,34-,35-,36+,37-,38+,39-,40+,41+,44-,45-,46?,47+/m1/s1
SMILES:	C[C@H](CCC(C)(C(C)C)OC(=O)C)C1CC[C@@]2([C@@]1(CCC3=C2CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O[C@H]5[C@@H]([C@H]([C@H]([C@H](O5)CO)O)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)NC(=O)C)C)C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44445475
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO19149	Erylus goffrilleri	Species	Geodiidae	Eukaryota	n.a.	Arresife-Seko Reef (at depths of 1520 m), Cuba	1998-FEB	PMID[18004814]
NPO19149	Erylus goffrilleri	Species	Geodiidae	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
NPT1490	Cell Line	Ehrlich	Mus musculus	IC50	=	20000	nM	PMID[18004814]

☑ 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 NPC477072 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	151
0.1-0.2	1108
0.2-0.3	5120
0.3-0.4	15329
0.4-0.5	10326
0.5-0.6	6707
0.6-0.7	3410
0.7-0.8	481
0.8-0.85	36
0.85-0.9	24
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9154	High Similarity	NPC265908
0.9008	High Similarity	NPC302276
0.9008	High Similarity	NPC180770
0.8984	High Similarity	NPC73829
0.8984	High Similarity	NPC119794
0.8906	High Similarity	NPC475472
0.8872	High Similarity	NPC162910
0.8846	High Similarity	NPC235772
0.8846	High Similarity	NPC75318
0.8846	High Similarity	NPC280941
0.8779	High Similarity	NPC145899
0.8769	High Similarity	NPC76999
0.8741	High Similarity	NPC298469
0.8741	High Similarity	NPC141669
0.8667	High Similarity	NPC475152
0.8667	High Similarity	NPC475584
0.8667	High Similarity	NPC475394
0.8657	High Similarity	NPC172365
0.8657	High Similarity	NPC82931
0.8657	High Similarity	NPC210729
0.8647	High Similarity	NPC200788
0.8647	High Similarity	NPC243680
0.8615	High Similarity	NPC139585
0.8603	High Similarity	NPC475892
0.8603	High Similarity	NPC193579
0.8561	High Similarity	NPC36463
0.8561	High Similarity	NPC298005
0.8406	Intermediate Similarity	NPC214821
0.8406	Intermediate Similarity	NPC298067
0.8361	Intermediate Similarity	NPC477073
0.8286	Intermediate Similarity	NPC61717
0.8286	Intermediate Similarity	NPC244380
0.8226	Intermediate Similarity	NPC477074
0.8201	Intermediate Similarity	NPC284625
0.8201	Intermediate Similarity	NPC69176
0.8197	Intermediate Similarity	NPC477070
0.8197	Intermediate Similarity	NPC477069
0.8145	Intermediate Similarity	NPC233003
0.814	Intermediate Similarity	NPC469943
0.8125	Intermediate Similarity	NPC265699
0.8125	Intermediate Similarity	NPC475527
0.808	Intermediate Similarity	NPC251309
0.8069	Intermediate Similarity	NPC113620
0.8069	Intermediate Similarity	NPC475599
0.8069	Intermediate Similarity	NPC187497
0.8069	Intermediate Similarity	NPC100612
0.8069	Intermediate Similarity	NPC174336
0.7969	Intermediate Similarity	NPC471118
0.7969	Intermediate Similarity	NPC471121
0.7891	Intermediate Similarity	NPC471120
0.7891	Intermediate Similarity	NPC471117
0.7874	Intermediate Similarity	NPC473882
0.784	Intermediate Similarity	NPC129340
0.7823	Intermediate Similarity	NPC195708
0.776	Intermediate Similarity	NPC265655
0.7717	Intermediate Similarity	NPC210420
0.7717	Intermediate Similarity	NPC474265
0.7638	Intermediate Similarity	NPC285410
0.7638	Intermediate Similarity	NPC292196
0.7638	Intermediate Similarity	NPC263827
0.7638	Intermediate Similarity	NPC250481
0.7622	Intermediate Similarity	NPC803
0.7615	Intermediate Similarity	NPC477252
0.7597	Intermediate Similarity	NPC116024
0.7597	Intermediate Similarity	NPC220293
0.7597	Intermediate Similarity	NPC474557
0.7591	Intermediate Similarity	NPC201359
0.7578	Intermediate Similarity	NPC195132
0.7578	Intermediate Similarity	NPC161434
0.7578	Intermediate Similarity	NPC477253
0.7559	Intermediate Similarity	NPC475317
0.7559	Intermediate Similarity	NPC154856
0.7559	Intermediate Similarity	NPC52241
0.7559	Intermediate Similarity	NPC475243
0.7559	Intermediate Similarity	NPC78046
0.7559	Intermediate Similarity	NPC90630
0.7559	Intermediate Similarity	NPC269095
0.7557	Intermediate Similarity	NPC291564
0.754	Intermediate Similarity	NPC295389
0.754	Intermediate Similarity	NPC285576
0.7538	Intermediate Similarity	NPC279638
0.7519	Intermediate Similarity	NPC129434
0.7519	Intermediate Similarity	NPC47063
0.7519	Intermediate Similarity	NPC204458
0.7519	Intermediate Similarity	NPC189884
0.7519	Intermediate Similarity	NPC138334
0.75	Intermediate Similarity	NPC473481
0.75	Intermediate Similarity	NPC297208
0.75	Intermediate Similarity	NPC477071
0.75	Intermediate Similarity	NPC108748
0.75	Intermediate Similarity	NPC30397
0.75	Intermediate Similarity	NPC211798
0.75	Intermediate Similarity	NPC232258
0.75	Intermediate Similarity	NPC190837
0.75	Intermediate Similarity	NPC235841
0.7481	Intermediate Similarity	NPC130229
0.748	Intermediate Similarity	NPC51947
0.748	Intermediate Similarity	NPC137917
0.748	Intermediate Similarity	NPC473844
0.748	Intermediate Similarity	NPC475364
0.7447	Intermediate Similarity	NPC297058
0.7444	Intermediate Similarity	NPC471406
0.7442	Intermediate Similarity	NPC130427
0.7442	Intermediate Similarity	NPC65590
0.7442	Intermediate Similarity	NPC46388
0.7442	Intermediate Similarity	NPC37739
0.7442	Intermediate Similarity	NPC212968
0.7442	Intermediate Similarity	NPC64106
0.7442	Intermediate Similarity	NPC125923
0.7442	Intermediate Similarity	NPC128925
0.7442	Intermediate Similarity	NPC256798
0.744	Intermediate Similarity	NPC223741
0.7422	Intermediate Similarity	NPC475296
0.7422	Intermediate Similarity	NPC114961
0.7422	Intermediate Similarity	NPC29069
0.7422	Intermediate Similarity	NPC90856
0.7422	Intermediate Similarity	NPC164194
0.7422	Intermediate Similarity	NPC279554
0.7422	Intermediate Similarity	NPC274507
0.7422	Intermediate Similarity	NPC220984
0.7422	Intermediate Similarity	NPC270667
0.7422	Intermediate Similarity	NPC127056
0.7422	Intermediate Similarity	NPC27551
0.7422	Intermediate Similarity	NPC56713
0.7422	Intermediate Similarity	NPC136877
0.7422	Intermediate Similarity	NPC101450
0.7422	Intermediate Similarity	NPC59804
0.7422	Intermediate Similarity	NPC174679
0.7422	Intermediate Similarity	NPC474589
0.7405	Intermediate Similarity	NPC160415
0.7405	Intermediate Similarity	NPC244127
0.7405	Intermediate Similarity	NPC58448
0.7402	Intermediate Similarity	NPC88744
0.7402	Intermediate Similarity	NPC472988
0.7402	Intermediate Similarity	NPC38217
0.7388	Intermediate Similarity	NPC202051
0.7385	Intermediate Similarity	NPC258885
0.7385	Intermediate Similarity	NPC124296
0.7385	Intermediate Similarity	NPC269315
0.7385	Intermediate Similarity	NPC271138
0.7381	Intermediate Similarity	NPC162033
0.7364	Intermediate Similarity	NPC91838
0.7364	Intermediate Similarity	NPC275668
0.7364	Intermediate Similarity	NPC179434
0.7364	Intermediate Similarity	NPC114188
0.7364	Intermediate Similarity	NPC191763
0.7364	Intermediate Similarity	NPC1876
0.7364	Intermediate Similarity	NPC204392
0.7364	Intermediate Similarity	NPC11035
0.7364	Intermediate Similarity	NPC240734
0.7364	Intermediate Similarity	NPC164419
0.7348	Intermediate Similarity	NPC68175
0.7344	Intermediate Similarity	NPC57362
0.7344	Intermediate Similarity	NPC154085
0.7344	Intermediate Similarity	NPC204407
0.7344	Intermediate Similarity	NPC43976
0.7344	Intermediate Similarity	NPC237503
0.7344	Intermediate Similarity	NPC118225
0.7344	Intermediate Similarity	NPC91583
0.7344	Intermediate Similarity	NPC240125
0.7344	Intermediate Similarity	NPC125361
0.7344	Intermediate Similarity	NPC51925
0.7344	Intermediate Similarity	NPC296761
0.7344	Intermediate Similarity	NPC167383
0.7344	Intermediate Similarity	NPC306746
0.7333	Intermediate Similarity	NPC131824
0.7333	Intermediate Similarity	NPC156789
0.7323	Intermediate Similarity	NPC234160
0.7323	Intermediate Similarity	NPC293512
0.7308	Intermediate Similarity	NPC102439
0.7308	Intermediate Similarity	NPC116794
0.7308	Intermediate Similarity	NPC471383
0.7308	Intermediate Similarity	NPC10320
0.7308	Intermediate Similarity	NPC79718
0.7308	Intermediate Similarity	NPC473383
0.7308	Intermediate Similarity	NPC1046
0.7308	Intermediate Similarity	NPC324875
0.7308	Intermediate Similarity	NPC292677
0.7308	Intermediate Similarity	NPC470543
0.7308	Intermediate Similarity	NPC276093
0.7308	Intermediate Similarity	NPC101744
0.7308	Intermediate Similarity	NPC104400
0.7308	Intermediate Similarity	NPC109079
0.7308	Intermediate Similarity	NPC139044
0.7308	Intermediate Similarity	NPC469946
0.7308	Intermediate Similarity	NPC104071
0.7308	Intermediate Similarity	NPC257468
0.7308	Intermediate Similarity	NPC139894
0.7308	Intermediate Similarity	NPC80843
0.7308	Intermediate Similarity	NPC475516
0.7308	Intermediate Similarity	NPC473373
0.7308	Intermediate Similarity	NPC475504
0.7302	Intermediate Similarity	NPC470885
0.7302	Intermediate Similarity	NPC187400
0.7302	Intermediate Similarity	NPC221562
0.7293	Intermediate Similarity	NPC36831
0.7293	Intermediate Similarity	NPC475632
0.7293	Intermediate Similarity	NPC86020
0.7293	Intermediate Similarity	NPC475899
0.7293	Intermediate Similarity	NPC18233

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 NPC477072 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	111
0.1-0.2	837
0.2-0.3	3547
0.3-0.4	3260
0.4-0.5	875
0.5-0.6	397
0.6-0.7	119
0.7-0.8	4
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
0.748	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD8174	Phase 2
0.7121	Intermediate Similarity	NPD8133	Approved
0.709	Intermediate Similarity	NPD8137	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD8449	Approved
0.6954	Remote Similarity	NPD7625	Phase 1
0.695	Remote Similarity	NPD8337	Approved
0.695	Remote Similarity	NPD8336	Approved
0.6944	Remote Similarity	NPD8450	Suspended
0.6889	Remote Similarity	NPD6940	Discontinued
0.6884	Remote Similarity	NPD8033	Approved
0.6884	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.685	Remote Similarity	NPD8418	Phase 2
0.6835	Remote Similarity	NPD8080	Discontinued
0.6812	Remote Similarity	NPD8377	Approved
0.6812	Remote Similarity	NPD8294	Approved
0.6809	Remote Similarity	NPD7507	Approved
0.6794	Remote Similarity	NPD6412	Phase 2
0.6786	Remote Similarity	NPD8328	Phase 3
0.6763	Remote Similarity	NPD8379	Approved
0.6763	Remote Similarity	NPD8296	Approved
0.6763	Remote Similarity	NPD8380	Approved
0.6763	Remote Similarity	NPD8335	Approved
0.6763	Remote Similarity	NPD8378	Approved
0.6759	Remote Similarity	NPD8338	Approved
0.6757	Remote Similarity	NPD6334	Approved
0.6757	Remote Similarity	NPD6333	Approved
0.6667	Remote Similarity	NPD8307	Discontinued
0.6667	Remote Similarity	NPD7319	Approved
0.6643	Remote Similarity	NPD8074	Phase 3
0.6621	Remote Similarity	NPD8390	Approved
0.6621	Remote Similarity	NPD8392	Approved
0.6621	Remote Similarity	NPD8391	Approved
0.662	Remote Similarity	NPD8342	Approved
0.662	Remote Similarity	NPD8341	Approved
0.662	Remote Similarity	NPD8340	Approved
0.662	Remote Similarity	NPD8299	Approved
0.6597	Remote Similarity	NPD7736	Approved
0.6573	Remote Similarity	NPD8451	Approved
0.6547	Remote Similarity	NPD7328	Approved
0.6547	Remote Similarity	NPD7327	Approved
0.6541	Remote Similarity	NPD8140	Approved
0.6528	Remote Similarity	NPD8448	Approved
0.6528	Remote Similarity	NPD8293	Discontinued
0.6525	Remote Similarity	NPD8516	Approved
0.6525	Remote Similarity	NPD7503	Approved
0.6525	Remote Similarity	NPD8517	Approved
0.6525	Remote Similarity	NPD8515	Approved
0.6525	Remote Similarity	NPD8513	Phase 3
0.6519	Remote Similarity	NPD6421	Discontinued
0.6519	Remote Similarity	NPD8087	Discontinued
0.6515	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD6914	Discontinued
0.65	Remote Similarity	NPD7516	Approved
0.6493	Remote Similarity	NPD6686	Approved
0.6444	Remote Similarity	NPD8305	Approved
0.6444	Remote Similarity	NPD8306	Approved
0.6439	Remote Similarity	NPD8275	Approved
0.6439	Remote Similarity	NPD8276	Approved
0.6408	Remote Similarity	NPD6908	Approved
0.6408	Remote Similarity	NPD6909	Approved
0.6364	Remote Similarity	NPD8086	Approved
0.6364	Remote Similarity	NPD8139	Approved
0.6364	Remote Similarity	NPD8082	Approved
0.6364	Remote Similarity	NPD6370	Approved
0.6364	Remote Similarity	NPD8085	Approved
0.6364	Remote Similarity	NPD8084	Approved
0.6364	Remote Similarity	NPD8138	Approved
0.6364	Remote Similarity	NPD8083	Approved
0.6343	Remote Similarity	NPD8393	Approved
0.6338	Remote Similarity	NPD8346	Approved
0.6338	Remote Similarity	NPD8345	Approved
0.6338	Remote Similarity	NPD8347	Approved
0.6312	Remote Similarity	NPD7641	Discontinued
0.6304	Remote Similarity	NPD8297	Approved
0.6304	Remote Similarity	NPD6882	Approved
0.6291	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD7492	Approved
0.6269	Remote Similarity	NPD8081	Approved
0.6259	Remote Similarity	NPD8298	Phase 2
0.6241	Remote Similarity	NPD6009	Approved
0.6233	Remote Similarity	NPD6616	Approved
0.6225	Remote Similarity	NPD8415	Approved
0.6224	Remote Similarity	NPD6319	Approved
0.6224	Remote Similarity	NPD6054	Approved
0.6224	Remote Similarity	NPD6059	Approved
0.6207	Remote Similarity	NPD7830	Approved
0.6207	Remote Similarity	NPD7122	Discontinued
0.6207	Remote Similarity	NPD7604	Phase 2
0.6207	Remote Similarity	NPD7829	Approved
0.6204	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7078	Approved
0.6181	Remote Similarity	NPD6921	Approved
0.6143	Remote Similarity	NPD4632	Approved
0.6127	Remote Similarity	NPD7115	Discovery
0.6124	Remote Similarity	NPD8171	Discontinued
0.6124	Remote Similarity	NPD6399	Phase 3
0.6119	Remote Similarity	NPD7140	Approved
0.6119	Remote Similarity	NPD7139	Approved
0.6119	Remote Similarity	NPD7141	Clinical (unspecified phase)
0.6115	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD6675	Approved
0.6103	Remote Similarity	NPD6402	Approved
0.6103	Remote Similarity	NPD5357	Phase 1
0.6103	Remote Similarity	NPD7128	Approved
0.6103	Remote Similarity	NPD5739	Approved
0.6096	Remote Similarity	NPD7642	Approved
0.6093	Remote Similarity	NPD6845	Suspended
0.6087	Remote Similarity	NPD6373	Approved
0.6087	Remote Similarity	NPD6941	Approved
0.6087	Remote Similarity	NPD6372	Approved
0.6071	Remote Similarity	NPD6430	Approved
0.6071	Remote Similarity	NPD6429	Approved
0.6069	Remote Similarity	NPD8444	Approved
0.6069	Remote Similarity	NPD6016	Approved
0.6069	Remote Similarity	NPD6015	Approved
0.6047	Remote Similarity	NPD8035	Phase 2
0.6047	Remote Similarity	NPD8034	Phase 2
0.6043	Remote Similarity	NPD6420	Discontinued
0.6043	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6027	Remote Similarity	NPD5988	Approved
0.6026	Remote Similarity	NPD7260	Phase 2
0.6014	Remote Similarity	NPD7320	Approved
0.6014	Remote Similarity	NPD6899	Approved
0.6014	Remote Similarity	NPD6881	Approved
0.6	Remote Similarity	NPD8130	Phase 1
0.6	Remote Similarity	NPD6650	Approved
0.6	Remote Similarity	NPD1447	Phase 3
0.6	Remote Similarity	NPD1446	Phase 3
0.6	Remote Similarity	NPD6649	Approved
0.5986	Remote Similarity	NPD6067	Discontinued
0.5985	Remote Similarity	NPD6428	Approved
0.5956	Remote Similarity	NPD1407	Approved
0.5954	Remote Similarity	NPD7748	Approved
0.5942	Remote Similarity	NPD5697	Approved
0.5942	Remote Similarity	NPD5701	Approved
0.594	Remote Similarity	NPD7902	Approved
0.5938	Remote Similarity	NPD618	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD7290	Approved
0.5929	Remote Similarity	NPD7102	Approved
0.5929	Remote Similarity	NPD6883	Approved
0.5896	Remote Similarity	NPD2255	Approved
0.5896	Remote Similarity	NPD7638	Approved
0.5887	Remote Similarity	NPD6617	Approved
0.5887	Remote Similarity	NPD6847	Approved
0.5887	Remote Similarity	NPD6869	Approved
0.5882	Remote Similarity	NPD8301	Approved
0.5882	Remote Similarity	NPD8300	Approved
0.5878	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.587	Remote Similarity	NPD6008	Approved
0.587	Remote Similarity	NPD6920	Discontinued
0.5864	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.5857	Remote Similarity	NPD6014	Approved
0.5857	Remote Similarity	NPD6013	Approved
0.5857	Remote Similarity	NPD6012	Approved
0.5854	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.5852	Remote Similarity	NPD7639	Approved
0.5852	Remote Similarity	NPD6404	Discontinued
0.5852	Remote Similarity	NPD7640	Approved
0.585	Remote Similarity	NPD8266	Approved
0.585	Remote Similarity	NPD5983	Phase 2
0.585	Remote Similarity	NPD8269	Approved
0.585	Remote Similarity	NPD8268	Approved
0.585	Remote Similarity	NPD8267	Approved
0.5846	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5828	Remote Similarity	NPD6033	Approved
0.5827	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5821	Remote Similarity	NPD6084	Phase 2
0.5821	Remote Similarity	NPD6083	Phase 2
0.5814	Remote Similarity	NPD4264	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD7515	Phase 2
0.5801	Remote Similarity	NPD8407	Phase 2
0.58	Remote Similarity	NPD6336	Discontinued
0.5789	Remote Similarity	NPD5695	Phase 3
0.5789	Remote Similarity	NPD7991	Discontinued
0.5786	Remote Similarity	NPD8384	Approved
0.5786	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5786	Remote Similarity	NPD6011	Approved
0.5775	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5774	Remote Similarity	NPD8417	Discontinued
0.5769	Remote Similarity	NPD3716	Discontinued
0.5766	Remote Similarity	NPD7632	Discontinued
0.5748	Remote Similarity	NPD4786	Approved
0.5738	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.5722	Remote Similarity	NPD8368	Discontinued
0.5714	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7900	Approved
0.5714	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.5705	Remote Similarity	NPD6436	Phase 3
0.5704	Remote Similarity	NPD4755	Approved
0.5704	Remote Similarity	NPD4634	Approved
0.5695	Remote Similarity	NPD8273	Phase 1
0.5684	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD6411	Approved
0.5676	Remote Similarity	NPD7147	Phase 3
0.5676	Remote Similarity	NPD8435	Approved
0.5676	Remote Similarity	NPD8361	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