NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	664.46
Volume:	696.861
LogP:	4.656
LogD:	4.135
LogS:	-4.227
# Rotatable Bonds:	9
TPSA:	156.91
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.192
Synthetic Accessibility Score:	5.457
Fsp3:	0.921
Lipinski Rule-of-5:	Rejected
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:	-5.589
MDCK Permeability:	7.15191890776623e-06
Pgp-inhibitor:	0.945
Pgp-substrate:	0.021
Human Intestinal Absorption (HIA):	0.056
20% Bioavailability (F20%):	0.369
30% Bioavailability (F30%):	0.879

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	91.76815795898438%
Volume Distribution (VD):	1.01
Pgp-substrate:	2.851299524307251%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.232
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.891
CYP2C9-inhibitor:	0.062
CYP2C9-substrate:	0.205
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.104
CYP3A4-inhibitor:	0.073
CYP3A4-substrate:	0.269

ADMET: Excretion

Clearance (CL):	1.274
Half-life (T1/2):	0.227

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.283
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.076
Rat Oral Acute Toxicity:	0.076
Maximum Recommended Daily Dose:	0.554
Skin Sensitization:	0.029
Carcinogencity:	0.022
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC477069

Natural Product ID:	NPC477069
*Common Name:**	Eryloside R
IUPAC Name:	(3S,5R,10S,13R,14S)-17-[(2R)-5-hydroxy-5,6,6-trimethylheptan-2-yl]-4,4,10,13-tetramethyl-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-14-carboxylic acid
Synonyms:	eryloside R
Standard InCHIKey:	NXKGSQRELSNVBS-VEZGTMCQSA-N
Standard InCHI:	InChI=1S/C38H64O9/c1-21(12-18-37(9,45)33(2,3)4)22-14-19-38(32(43)44)24-10-11-26-34(5,6)27(15-16-35(26,7)23(24)13-17-36(22,38)8)47-31-30(42)29(41)28(40)25(20-39)46-31/h21-22,25-31,39-42,45H,10-20H2,1-9H3,(H,43,44)/t21-,22?,25-,26+,27+,28+,29+,30-,31+,35-,36-,37?,38+/m1/s1
SMILES:	C[C@H](CCC(C)(C(C)(C)C)O)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)C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44445472
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 NPC477069 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	244
0.1-0.2	1611
0.2-0.3	5202
0.3-0.4	11502
0.4-0.5	9571
0.5-0.6	5728
0.6-0.7	5336
0.7-0.8	3151
0.8-0.85	278
0.85-0.9	47
0.9-0.95	15
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477070
0.9804	High Similarity	NPC477073
0.9615	High Similarity	NPC477074
0.9519	High Similarity	NPC233003
0.9515	High Similarity	NPC129340
0.951	High Similarity	NPC195708
0.9429	High Similarity	NPC251309
0.9417	High Similarity	NPC265655
0.9238	High Similarity	NPC263827
0.9238	High Similarity	NPC285410
0.9238	High Similarity	NPC292196
0.9238	High Similarity	NPC250481
0.9159	High Similarity	NPC473882
0.9159	High Similarity	NPC220293
0.9159	High Similarity	NPC116024
0.9143	High Similarity	NPC475317
0.9143	High Similarity	NPC475243
0.9143	High Similarity	NPC52241
0.9143	High Similarity	NPC154856
0.9143	High Similarity	NPC90630
0.9135	High Similarity	NPC295389
0.9048	High Similarity	NPC475364
0.9029	High Similarity	NPC223741
0.9	High Similarity	NPC477071
0.8972	High Similarity	NPC474265
0.8972	High Similarity	NPC210420
0.8972	High Similarity	NPC130427
0.8972	High Similarity	NPC477253
0.8962	High Similarity	NPC27551
0.8962	High Similarity	NPC114961
0.8962	High Similarity	NPC101450
0.8952	High Similarity	NPC285576
0.8942	High Similarity	NPC162033
0.8919	High Similarity	NPC471406
0.8909	High Similarity	NPC291564
0.8899	High Similarity	NPC244127
0.8879	High Similarity	NPC190837
0.8868	High Similarity	NPC118225
0.8868	High Similarity	NPC137917
0.8857	High Similarity	NPC293512
0.8839	High Similarity	NPC129434
0.8839	High Similarity	NPC202051
0.8829	High Similarity	NPC232258
0.8818	High Similarity	NPC477252
0.8807	High Similarity	NPC474557
0.8796	High Similarity	NPC195132
0.8796	High Similarity	NPC64106
0.8796	High Similarity	NPC37739
0.8796	High Similarity	NPC212968
0.8796	High Similarity	NPC125923
0.8796	High Similarity	NPC46388
0.8796	High Similarity	NPC65590
0.8796	High Similarity	NPC161434
0.8785	High Similarity	NPC269095
0.8785	High Similarity	NPC274507
0.8785	High Similarity	NPC220984
0.8785	High Similarity	NPC78046
0.8774	High Similarity	NPC88744
0.8762	High Similarity	NPC473199
0.8727	High Similarity	NPC279638
0.8716	High Similarity	NPC269315
0.8716	High Similarity	NPC47063
0.8716	High Similarity	NPC271138
0.8716	High Similarity	NPC138334
0.8716	High Similarity	NPC73455
0.8716	High Similarity	NPC260665
0.8716	High Similarity	NPC189884
0.8716	High Similarity	NPC200944
0.8716	High Similarity	NPC204458
0.8704	High Similarity	NPC473481
0.8704	High Similarity	NPC272242
0.8704	High Similarity	NPC269466
0.8704	High Similarity	NPC30397
0.8704	High Similarity	NPC108748
0.8704	High Similarity	NPC211798
0.8704	High Similarity	NPC191763
0.8704	High Similarity	NPC235841
0.8704	High Similarity	NPC297208
0.8692	High Similarity	NPC167383
0.8692	High Similarity	NPC57362
0.8692	High Similarity	NPC237503
0.8692	High Similarity	NPC218853
0.8692	High Similarity	NPC473844
0.8692	High Similarity	NPC240125
0.8692	High Similarity	NPC91583
0.8692	High Similarity	NPC306746
0.8692	High Similarity	NPC204407
0.8692	High Similarity	NPC51947
0.8654	High Similarity	NPC94919
0.8636	High Similarity	NPC74727
0.8624	High Similarity	NPC128925
0.8624	High Similarity	NPC256798
0.8624	High Similarity	NPC116794
0.8611	High Similarity	NPC174679
0.8611	High Similarity	NPC476882
0.8611	High Similarity	NPC476885
0.8611	High Similarity	NPC474589
0.8611	High Similarity	NPC75747
0.8611	High Similarity	NPC270667
0.8611	High Similarity	NPC90856
0.8611	High Similarity	NPC279554
0.8611	High Similarity	NPC164194
0.8611	High Similarity	NPC29069
0.8611	High Similarity	NPC68419
0.8611	High Similarity	NPC199457
0.8611	High Similarity	NPC476883
0.8611	High Similarity	NPC108709
0.8611	High Similarity	NPC102914
0.8611	High Similarity	NPC476886
0.8611	High Similarity	NPC475296
0.8611	High Similarity	NPC56713
0.8611	High Similarity	NPC136877
0.8611	High Similarity	NPC476887
0.8611	High Similarity	NPC7870
0.8611	High Similarity	NPC250956
0.8611	High Similarity	NPC110139
0.8611	High Similarity	NPC127056
0.8611	High Similarity	NPC476880
0.8611	High Similarity	NPC476884
0.8611	High Similarity	NPC59804
0.8611	High Similarity	NPC476881
0.8609	High Similarity	NPC130229
0.8598	High Similarity	NPC38217
0.8598	High Similarity	NPC472988
0.8598	High Similarity	NPC28198
0.8598	High Similarity	NPC284807
0.8598	High Similarity	NPC258323
0.8598	High Similarity	NPC177246
0.8598	High Similarity	NPC476123
0.8585	High Similarity	NPC210178
0.8584	High Similarity	NPC476849
0.8571	High Similarity	NPC218513
0.8571	High Similarity	NPC45475
0.8571	High Similarity	NPC239293
0.8571	High Similarity	NPC55954
0.8559	High Similarity	NPC160415
0.8559	High Similarity	NPC58448
0.8545	High Similarity	NPC258885
0.8545	High Similarity	NPC102619
0.8545	High Similarity	NPC124296
0.8532	High Similarity	NPC204392
0.8532	High Similarity	NPC114188
0.8532	High Similarity	NPC91838
0.8532	High Similarity	NPC31839
0.8532	High Similarity	NPC179434
0.8532	High Similarity	NPC1876
0.8532	High Similarity	NPC275668
0.8532	High Similarity	NPC164419
0.8532	High Similarity	NPC240734
0.8532	High Similarity	NPC11035
0.8522	High Similarity	NPC41129
0.8519	High Similarity	NPC125361
0.8519	High Similarity	NPC127853
0.8519	High Similarity	NPC246205
0.8519	High Similarity	NPC51925
0.8519	High Similarity	NPC43976
0.8519	High Similarity	NPC296761
0.8519	High Similarity	NPC8431
0.8519	High Similarity	NPC154085
0.8505	High Similarity	NPC283849
0.8505	High Similarity	NPC234160
0.8505	High Similarity	NPC473538
0.8491	Intermediate Similarity	NPC187400
0.8491	Intermediate Similarity	NPC31430
0.8491	Intermediate Similarity	NPC470885
0.8491	Intermediate Similarity	NPC221562
0.8491	Intermediate Similarity	NPC85593
0.8482	Intermediate Similarity	NPC68175
0.8476	Intermediate Similarity	NPC470053
0.8476	Intermediate Similarity	NPC154452
0.8476	Intermediate Similarity	NPC471119
0.8476	Intermediate Similarity	NPC136816
0.8476	Intermediate Similarity	NPC296879
0.8468	Intermediate Similarity	NPC472274
0.8468	Intermediate Similarity	NPC475633
0.8455	Intermediate Similarity	NPC174836
0.8455	Intermediate Similarity	NPC276093
0.8455	Intermediate Similarity	NPC139894
0.8455	Intermediate Similarity	NPC471967
0.8455	Intermediate Similarity	NPC475504
0.8455	Intermediate Similarity	NPC473373
0.8455	Intermediate Similarity	NPC102439
0.8455	Intermediate Similarity	NPC473383
0.8455	Intermediate Similarity	NPC475516
0.8455	Intermediate Similarity	NPC292677
0.8455	Intermediate Similarity	NPC470543
0.8455	Intermediate Similarity	NPC101744
0.8455	Intermediate Similarity	NPC104071
0.8455	Intermediate Similarity	NPC1046
0.8455	Intermediate Similarity	NPC80843
0.8455	Intermediate Similarity	NPC139044
0.8455	Intermediate Similarity	NPC469946
0.8455	Intermediate Similarity	NPC243572
0.8455	Intermediate Similarity	NPC471383
0.8455	Intermediate Similarity	NPC257468
0.8455	Intermediate Similarity	NPC48249
0.8455	Intermediate Similarity	NPC79718
0.8455	Intermediate Similarity	NPC104400
0.8455	Intermediate Similarity	NPC109079
0.8455	Intermediate Similarity	NPC324875

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 NPC477069 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	215
0.1-0.2	2008
0.2-0.3	3955
0.3-0.4	1911
0.4-0.5	548
0.5-0.6	246
0.6-0.7	194
0.7-0.8	72
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
0.8868	High Similarity	NPD8132	Clinical (unspecified phase)
0.8319	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD8133	Approved
0.8165	Intermediate Similarity	NPD6412	Phase 2
0.8067	Intermediate Similarity	NPD7507	Approved
0.7881	Intermediate Similarity	NPD8033	Approved
0.7869	Intermediate Similarity	NPD7319	Approved
0.7797	Intermediate Similarity	NPD8294	Approved
0.7797	Intermediate Similarity	NPD8377	Approved
0.7787	Intermediate Similarity	NPD7736	Approved
0.7778	Intermediate Similarity	NPD7327	Approved
0.7778	Intermediate Similarity	NPD7328	Approved
0.7768	Intermediate Similarity	NPD6686	Approved
0.775	Intermediate Similarity	NPD8328	Phase 3
0.7731	Intermediate Similarity	NPD8335	Approved
0.7731	Intermediate Similarity	NPD8380	Approved
0.7731	Intermediate Similarity	NPD8378	Approved
0.7731	Intermediate Similarity	NPD8379	Approved
0.7731	Intermediate Similarity	NPD8296	Approved
0.7712	Intermediate Similarity	NPD7516	Approved
0.7705	Intermediate Similarity	NPD8293	Discontinued
0.7583	Intermediate Similarity	NPD7503	Approved
0.7521	Intermediate Similarity	NPD6370	Approved
0.75	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8297	Approved
0.75	Intermediate Similarity	NPD6882	Approved
0.7438	Intermediate Similarity	NPD8513	Phase 3
0.7438	Intermediate Similarity	NPD8516	Approved
0.7438	Intermediate Similarity	NPD8517	Approved
0.7438	Intermediate Similarity	NPD8515	Approved
0.7398	Intermediate Similarity	NPD7492	Approved
0.7395	Intermediate Similarity	NPD6009	Approved
0.7391	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD6399	Phase 3
0.7355	Intermediate Similarity	NPD6319	Approved
0.7355	Intermediate Similarity	NPD6059	Approved
0.7355	Intermediate Similarity	NPD6054	Approved
0.7339	Intermediate Similarity	NPD6616	Approved
0.729	Intermediate Similarity	NPD8034	Phase 2
0.729	Intermediate Similarity	NPD8035	Phase 2
0.7288	Intermediate Similarity	NPD4632	Approved
0.7281	Intermediate Similarity	NPD5739	Approved
0.7281	Intermediate Similarity	NPD6675	Approved
0.7281	Intermediate Similarity	NPD6402	Approved
0.7281	Intermediate Similarity	NPD7128	Approved
0.728	Intermediate Similarity	NPD7078	Approved
0.725	Intermediate Similarity	NPD7115	Discovery
0.7241	Intermediate Similarity	NPD6372	Approved
0.7241	Intermediate Similarity	NPD6373	Approved
0.7179	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD6881	Approved
0.7155	Intermediate Similarity	NPD6899	Approved
0.7155	Intermediate Similarity	NPD7320	Approved
0.7154	Intermediate Similarity	NPD6015	Approved
0.7154	Intermediate Similarity	NPD6016	Approved
0.7119	Intermediate Similarity	NPD6650	Approved
0.7119	Intermediate Similarity	NPD6649	Approved
0.7119	Intermediate Similarity	NPD8130	Phase 1
0.7097	Intermediate Similarity	NPD5988	Approved
0.7069	Intermediate Similarity	NPD5701	Approved
0.7069	Intermediate Similarity	NPD5697	Approved
0.7064	Intermediate Similarity	NPD8171	Discontinued
0.7054	Intermediate Similarity	NPD7638	Approved
0.7048	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD6067	Discontinued
0.7034	Intermediate Similarity	NPD6883	Approved
0.7034	Intermediate Similarity	NPD7290	Approved
0.7034	Intermediate Similarity	NPD7102	Approved
0.7	Intermediate Similarity	NPD7748	Approved
0.6991	Remote Similarity	NPD7640	Approved
0.6991	Remote Similarity	NPD7639	Approved
0.6983	Remote Similarity	NPD6008	Approved
0.6975	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6617	Approved
0.6975	Remote Similarity	NPD6869	Approved
0.6975	Remote Similarity	NPD6847	Approved
0.6964	Remote Similarity	NPD6083	Phase 2
0.6964	Remote Similarity	NPD6084	Phase 2
0.6964	Remote Similarity	NPD7902	Approved
0.6952	Remote Similarity	NPD4786	Approved
0.6949	Remote Similarity	NPD6012	Approved
0.6949	Remote Similarity	NPD6013	Approved
0.6949	Remote Similarity	NPD6014	Approved
0.6937	Remote Similarity	NPD5695	Phase 3
0.6923	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7604	Phase 2
0.6885	Remote Similarity	NPD6940	Discontinued
0.688	Remote Similarity	NPD5983	Phase 2
0.687	Remote Similarity	NPD7632	Discontinued
0.6864	Remote Similarity	NPD6011	Approved
0.6864	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6115	Approved
0.6863	Remote Similarity	NPD6697	Approved
0.6863	Remote Similarity	NPD6118	Approved
0.6863	Remote Similarity	NPD6114	Approved
0.6833	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6033	Approved
0.6818	Remote Similarity	NPD6411	Approved
0.6818	Remote Similarity	NPD7515	Phase 2
0.6814	Remote Similarity	NPD4755	Approved
0.6797	Remote Similarity	NPD6336	Discontinued
0.6789	Remote Similarity	NPD5328	Approved
0.6765	Remote Similarity	NPD6116	Phase 1
0.6762	Remote Similarity	NPD3667	Approved
0.6757	Remote Similarity	NPD4202	Approved
0.675	Remote Similarity	NPD4634	Approved
0.6744	Remote Similarity	NPD8074	Phase 3
0.6698	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD3669	Approved
0.6696	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5286	Approved
0.6696	Remote Similarity	NPD5285	Approved
0.6696	Remote Similarity	NPD4700	Approved
0.6696	Remote Similarity	NPD4696	Approved
0.6696	Remote Similarity	NPD7900	Approved
0.6694	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6117	Approved
0.6667	Remote Similarity	NPD3618	Phase 1
0.6667	Remote Similarity	NPD6079	Approved
0.6639	Remote Similarity	NPD6053	Discontinued
0.6636	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6101	Approved
0.6613	Remote Similarity	NPD6274	Approved
0.6609	Remote Similarity	NPD5696	Approved
0.6587	Remote Similarity	NPD7100	Approved
0.6587	Remote Similarity	NPD7101	Approved
0.6581	Remote Similarity	NPD5224	Approved
0.6581	Remote Similarity	NPD5226	Approved
0.6581	Remote Similarity	NPD4633	Approved
0.6581	Remote Similarity	NPD5211	Phase 2
0.6581	Remote Similarity	NPD5225	Approved
0.6577	Remote Similarity	NPD46	Approved
0.6577	Remote Similarity	NPD6698	Approved
0.6571	Remote Similarity	NPD7525	Registered
0.6555	Remote Similarity	NPD4767	Approved
0.6555	Remote Similarity	NPD4768	Approved
0.6545	Remote Similarity	NPD5737	Approved
0.6545	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6672	Approved
0.6525	Remote Similarity	NPD5174	Approved
0.6525	Remote Similarity	NPD5175	Approved
0.6518	Remote Similarity	NPD5284	Approved
0.6518	Remote Similarity	NPD5281	Approved
0.6514	Remote Similarity	NPD6409	Approved
0.6514	Remote Similarity	NPD7146	Approved
0.6514	Remote Similarity	NPD7521	Approved
0.6514	Remote Similarity	NPD5330	Approved
0.6514	Remote Similarity	NPD6684	Approved
0.6514	Remote Similarity	NPD7334	Approved
0.6509	Remote Similarity	NPD1780	Approved
0.6509	Remote Similarity	NPD1779	Approved
0.6508	Remote Similarity	NPD6335	Approved
0.6496	Remote Similarity	NPD5223	Approved
0.6493	Remote Similarity	NPD8449	Approved
0.6491	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD4753	Phase 2
0.6484	Remote Similarity	NPD6909	Approved
0.6484	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6908	Approved
0.6471	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5141	Approved
0.6466	Remote Similarity	NPD4225	Approved
0.646	Remote Similarity	NPD5779	Approved
0.646	Remote Similarity	NPD5778	Approved
0.6455	Remote Similarity	NPD7524	Approved
0.6446	Remote Similarity	NPD4729	Approved
0.6446	Remote Similarity	NPD4730	Approved
0.6444	Remote Similarity	NPD8450	Suspended
0.6439	Remote Similarity	NPD8337	Approved
0.6439	Remote Similarity	NPD8336	Approved
0.6435	Remote Similarity	NPD5222	Approved
0.6435	Remote Similarity	NPD5221	Approved
0.6435	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD4697	Phase 3
0.6434	Remote Similarity	NPD8080	Discontinued
0.6429	Remote Similarity	NPD6317	Approved
0.6415	Remote Similarity	NPD6928	Phase 2
0.6415	Remote Similarity	NPD4748	Discontinued
0.6396	Remote Similarity	NPD6903	Approved
0.6387	Remote Similarity	NPD4754	Approved
0.6379	Remote Similarity	NPD5173	Approved
0.6378	Remote Similarity	NPD6313	Approved
0.6378	Remote Similarity	NPD6314	Approved
0.6372	Remote Similarity	NPD7983	Approved
0.6372	Remote Similarity	NPD6050	Approved
0.6372	Remote Similarity	NPD7637	Suspended
0.637	Remote Similarity	NPD8338	Approved
0.6364	Remote Similarity	NPD6098	Approved
0.6364	Remote Similarity	NPD5279	Phase 3
0.6357	Remote Similarity	NPD6921	Approved
0.6355	Remote Similarity	NPD4139	Approved
0.6355	Remote Similarity	NPD4692	Approved
0.6349	Remote Similarity	NPD6868	Approved
0.6343	Remote Similarity	NPD5956	Approved
0.6341	Remote Similarity	NPD5250	Approved
0.6341	Remote Similarity	NPD5251	Approved
0.6341	Remote Similarity	NPD5249	Phase 3
0.6341	Remote Similarity	NPD5248	Approved
0.6341	Remote Similarity	NPD5247	Approved
0.6339	Remote Similarity	NPD6080	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