NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	928.54
Volume:	923.029
LogP:	3.166
LogD:	2.631
LogS:	-3.548
# Rotatable Bonds:	13
TPSA:	274.75
# H-Bond Aceptor:	17
# H-Bond Donor:	10
# Rings:	7
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.126
Synthetic Accessibility Score:	6.391
Fsp3:	0.938
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:	-5.82
MDCK Permeability:	3.1088959076441824e-05
Pgp-inhibitor:	0.966
Pgp-substrate:	0.866
Human Intestinal Absorption (HIA):	0.95
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039
Plasma Protein Binding (PPB):	85.16341400146484%
Volume Distribution (VD):	0.407
Pgp-substrate:	7.24859094619751%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.114
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.469
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.027
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.073
CYP3A4-inhibitor:	0.025
CYP3A4-substrate:	0.054

ADMET: Excretion

Clearance (CL):	0.769
Half-life (T1/2):	0.494

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.228
Drug-inuced Liver Injury (DILI):	0.012
AMES Toxicity:	0.094
Rat Oral Acute Toxicity:	0.088
Maximum Recommended Daily Dose:	0.483
Skin Sensitization:	0.07
Carcinogencity:	0.017
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.94

Download Data

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

Natural Product: NPC477074

Natural Product ID:	NPC477074
*Common Name:**	(3S,5R,10S,13R,14S)-3-[(2S,3R,4S,5S)-5-hydroxy-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-17-[(2R)-5-hydroxy-5,6,6-trimethylheptan-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
IUPAC Name:	(3S,5R,10S,13R,14S)-3-[(2S,3R,4S,5S)-5-hydroxy-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-17-[(2R)-5-hydroxy-5,6,6-trimethylheptan-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 V
Standard InCHIKey:	LBXIYXJRXVQHDD-YLOMQMFTSA-N
Standard InCHI:	InChI=1S/C48H80O17/c1-23(12-18-47(9,59)43(2,3)4)24-14-19-48(42(57)58)26-10-11-30-44(5,6)31(15-16-45(30,7)25(26)13-17-46(24,48)8)63-41-38(65-40-36(56)34(54)33(53)29(20-49)62-40)37(28(51)22-61-41)64-39-35(55)32(52)27(50)21-60-39/h23-24,27-41,49-56,59H,10-22H2,1-9H3,(H,57,58)/t23-,24?,27-,28+,29-,30+,31+,32+,33+,34+,35-,36-,37+,38-,39+,40+,41+,45-,46-,47?,48+/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](CO5)O)O[C@H]6[C@@H]([C@H]([C@@H](CO6)O)O)O)O[C@H]7[C@@H]([C@H]([C@H]([C@H](O7)CO)O)O)O)C)C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44445477
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 NPC477074 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	279
0.1-0.2	1904
0.2-0.3	5671
0.3-0.4	12647
0.4-0.5	8741
0.5-0.6	5621
0.6-0.7	4493
0.7-0.8	2441
0.8-0.85	574
0.85-0.9	307
0.9-0.95	13
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9808	High Similarity	NPC477073
0.9615	High Similarity	NPC477069
0.9615	High Similarity	NPC477070
0.9528	High Similarity	NPC233003
0.9439	High Similarity	NPC251309
0.9174	High Similarity	NPC473882
0.9159	High Similarity	NPC129340
0.9151	High Similarity	NPC195708
0.9091	High Similarity	NPC279638
0.9065	High Similarity	NPC265655
0.8991	High Similarity	NPC210420
0.8991	High Similarity	NPC474265
0.8957	High Similarity	NPC130229
0.8919	High Similarity	NPC160415
0.8919	High Similarity	NPC58448
0.8909	High Similarity	NPC124296
0.8909	High Similarity	NPC258885
0.8899	High Similarity	NPC285410
0.8899	High Similarity	NPC250481
0.8899	High Similarity	NPC91838
0.8899	High Similarity	NPC240734
0.8899	High Similarity	NPC1876
0.8899	High Similarity	NPC204392
0.8899	High Similarity	NPC292196
0.8899	High Similarity	NPC263827
0.8899	High Similarity	NPC275668
0.8839	High Similarity	NPC477252
0.8839	High Similarity	NPC68175
0.8829	High Similarity	NPC116024
0.8829	High Similarity	NPC474557
0.8829	High Similarity	NPC220293
0.8818	High Similarity	NPC104400
0.8818	High Similarity	NPC292677
0.8818	High Similarity	NPC471383
0.8818	High Similarity	NPC195132
0.8818	High Similarity	NPC475504
0.8818	High Similarity	NPC469946
0.8818	High Similarity	NPC101744
0.8818	High Similarity	NPC257468
0.8818	High Similarity	NPC79718
0.8818	High Similarity	NPC161434
0.8818	High Similarity	NPC104071
0.8818	High Similarity	NPC102439
0.8818	High Similarity	NPC473373
0.8818	High Similarity	NPC109079
0.8818	High Similarity	NPC10320
0.8818	High Similarity	NPC324875
0.8818	High Similarity	NPC276093
0.8818	High Similarity	NPC475516
0.8818	High Similarity	NPC139044
0.8818	High Similarity	NPC477253
0.8807	High Similarity	NPC154856
0.8807	High Similarity	NPC475243
0.8807	High Similarity	NPC52241
0.8807	High Similarity	NPC90630
0.8807	High Similarity	NPC269095
0.8807	High Similarity	NPC78046
0.8807	High Similarity	NPC475317
0.8796	High Similarity	NPC295389
0.8796	High Similarity	NPC285576
0.8783	High Similarity	NPC156789
0.8783	High Similarity	NPC131824
0.8761	High Similarity	NPC291564
0.8761	High Similarity	NPC475899
0.8761	High Similarity	NPC36831
0.875	High Similarity	NPC161674
0.875	High Similarity	NPC146652
0.875	High Similarity	NPC471384
0.8739	High Similarity	NPC146563
0.8739	High Similarity	NPC174720
0.8739	High Similarity	NPC46665
0.8739	High Similarity	NPC47063
0.8739	High Similarity	NPC251263
0.8739	High Similarity	NPC473826
0.8739	High Similarity	NPC96641
0.8739	High Similarity	NPC114287
0.8739	High Similarity	NPC151543
0.8739	High Similarity	NPC309714
0.8739	High Similarity	NPC73318
0.8739	High Similarity	NPC138334
0.8739	High Similarity	NPC473343
0.8739	High Similarity	NPC219180
0.8739	High Similarity	NPC166422
0.8739	High Similarity	NPC189884
0.8739	High Similarity	NPC323341
0.8739	High Similarity	NPC134835
0.8739	High Similarity	NPC475287
0.8739	High Similarity	NPC133818
0.8739	High Similarity	NPC475467
0.8739	High Similarity	NPC192600
0.8739	High Similarity	NPC241909
0.8739	High Similarity	NPC163183
0.8739	High Similarity	NPC295823
0.8739	High Similarity	NPC114304
0.8739	High Similarity	NPC150400
0.8739	High Similarity	NPC155410
0.8739	High Similarity	NPC204458
0.8727	High Similarity	NPC164419
0.8727	High Similarity	NPC65167
0.8727	High Similarity	NPC473481
0.8727	High Similarity	NPC30397
0.8727	High Similarity	NPC190837
0.8727	High Similarity	NPC211798
0.8727	High Similarity	NPC235841
0.8727	High Similarity	NPC108748
0.8727	High Similarity	NPC297208
0.8716	High Similarity	NPC475364
0.8716	High Similarity	NPC137917
0.8716	High Similarity	NPC473844
0.8716	High Similarity	NPC51947
0.8707	High Similarity	NPC228701
0.8707	High Similarity	NPC160084
0.8707	High Similarity	NPC256983
0.8704	High Similarity	NPC190395
0.8704	High Similarity	NPC287269
0.8696	High Similarity	NPC475182
0.8696	High Similarity	NPC129434
0.8692	High Similarity	NPC223741
0.8684	High Similarity	NPC232258
0.8684	High Similarity	NPC477071
0.8684	High Similarity	NPC477464
0.8673	High Similarity	NPC136768
0.8673	High Similarity	NPC110633
0.8673	High Similarity	NPC148417
0.8661	High Similarity	NPC65105
0.8661	High Similarity	NPC41061
0.8661	High Similarity	NPC469782
0.8661	High Similarity	NPC224381
0.8661	High Similarity	NPC305981
0.8661	High Similarity	NPC309907
0.8661	High Similarity	NPC4328
0.8661	High Similarity	NPC227551
0.8661	High Similarity	NPC76972
0.8661	High Similarity	NPC476068
0.8661	High Similarity	NPC471550
0.8661	High Similarity	NPC54636
0.8661	High Similarity	NPC469821
0.8661	High Similarity	NPC43550
0.8661	High Similarity	NPC60557
0.8661	High Similarity	NPC161717
0.8661	High Similarity	NPC100639
0.8661	High Similarity	NPC250247
0.8661	High Similarity	NPC79643
0.8661	High Similarity	NPC475160
0.8661	High Similarity	NPC204414
0.8661	High Similarity	NPC71065
0.8661	High Similarity	NPC475486
0.8661	High Similarity	NPC298034
0.8661	High Similarity	NPC294453
0.8661	High Similarity	NPC473714
0.8661	High Similarity	NPC67857
0.8661	High Similarity	NPC236638
0.8661	High Similarity	NPC119592
0.8661	High Similarity	NPC123199
0.8661	High Similarity	NPC293330
0.8661	High Similarity	NPC70809
0.8661	High Similarity	NPC471385
0.8661	High Similarity	NPC475140
0.8661	High Similarity	NPC261506
0.8661	High Similarity	NPC57484
0.8661	High Similarity	NPC202828
0.8661	High Similarity	NPC164389
0.8661	High Similarity	NPC54395
0.8649	High Similarity	NPC65590
0.8649	High Similarity	NPC46388
0.8649	High Similarity	NPC139894
0.8649	High Similarity	NPC212968
0.8649	High Similarity	NPC125923
0.8649	High Similarity	NPC473383
0.8649	High Similarity	NPC128925
0.8649	High Similarity	NPC130427
0.8649	High Similarity	NPC37739
0.8649	High Similarity	NPC256798
0.8649	High Similarity	NPC64106
0.8636	High Similarity	NPC474589
0.8636	High Similarity	NPC270667
0.8636	High Similarity	NPC90856
0.8636	High Similarity	NPC164194
0.8636	High Similarity	NPC279554
0.8636	High Similarity	NPC101450
0.8636	High Similarity	NPC29069
0.8636	High Similarity	NPC127056
0.8636	High Similarity	NPC114961
0.8636	High Similarity	NPC475296
0.8636	High Similarity	NPC56713
0.8636	High Similarity	NPC220984
0.8636	High Similarity	NPC136877
0.8636	High Similarity	NPC27551
0.8636	High Similarity	NPC274507
0.8636	High Similarity	NPC59804
0.8636	High Similarity	NPC174679
0.8632	High Similarity	NPC473474
0.8632	High Similarity	NPC248202
0.8624	High Similarity	NPC38217
0.8624	High Similarity	NPC472988
0.8624	High Similarity	NPC88744
0.8611	High Similarity	NPC309448
0.8611	High Similarity	NPC162033
0.8609	High Similarity	NPC153673
0.8609	High Similarity	NPC37860

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 NPC477074 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	260
0.1-0.2	2223
0.2-0.3	3964
0.3-0.4	1745
0.4-0.5	477
0.5-0.6	274
0.6-0.7	167
0.7-0.8	36
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8716	High Similarity	NPD8132	Clinical (unspecified phase)
0.8571	High Similarity	NPD8133	Approved
0.8348	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7983	Intermediate Similarity	NPD8294	Approved
0.7983	Intermediate Similarity	NPD8377	Approved
0.7934	Intermediate Similarity	NPD8328	Phase 3
0.7917	Intermediate Similarity	NPD8033	Approved
0.7917	Intermediate Similarity	NPD8379	Approved
0.7917	Intermediate Similarity	NPD8296	Approved
0.7917	Intermediate Similarity	NPD8378	Approved
0.7917	Intermediate Similarity	NPD8335	Approved
0.7917	Intermediate Similarity	NPD8380	Approved
0.7876	Intermediate Similarity	NPD6412	Phase 2
0.7805	Intermediate Similarity	NPD7507	Approved
0.7699	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD8513	Phase 3
0.7623	Intermediate Similarity	NPD8517	Approved
0.7623	Intermediate Similarity	NPD8515	Approved
0.7623	Intermediate Similarity	NPD8516	Approved
0.7619	Intermediate Similarity	NPD7319	Approved
0.754	Intermediate Similarity	NPD7736	Approved
0.7521	Intermediate Similarity	NPD7328	Approved
0.7521	Intermediate Similarity	NPD7327	Approved
0.75	Intermediate Similarity	NPD6686	Approved
0.748	Intermediate Similarity	NPD7503	Approved
0.746	Intermediate Similarity	NPD8293	Discontinued
0.7459	Intermediate Similarity	NPD7516	Approved
0.728	Intermediate Similarity	NPD6370	Approved
0.7273	Intermediate Similarity	NPD8171	Discontinued
0.725	Intermediate Similarity	NPD6882	Approved
0.725	Intermediate Similarity	NPD8297	Approved
0.7167	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD7492	Approved
0.7154	Intermediate Similarity	NPD6009	Approved
0.7143	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6319	Approved
0.712	Intermediate Similarity	NPD6059	Approved
0.712	Intermediate Similarity	NPD6054	Approved
0.7117	Intermediate Similarity	NPD6399	Phase 3
0.7109	Intermediate Similarity	NPD6616	Approved
0.7054	Intermediate Similarity	NPD7078	Approved
0.7049	Intermediate Similarity	NPD4632	Approved
0.7034	Intermediate Similarity	NPD7128	Approved
0.7034	Intermediate Similarity	NPD6402	Approved
0.7034	Intermediate Similarity	NPD5739	Approved
0.7034	Intermediate Similarity	NPD6675	Approved
0.7027	Intermediate Similarity	NPD8035	Phase 2
0.7027	Intermediate Similarity	NPD8034	Phase 2
0.7016	Intermediate Similarity	NPD7115	Discovery
0.7	Intermediate Similarity	NPD6372	Approved
0.7	Intermediate Similarity	NPD6373	Approved
0.6942	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD6016	Approved
0.6929	Remote Similarity	NPD6015	Approved
0.6917	Remote Similarity	NPD7320	Approved
0.6917	Remote Similarity	NPD6899	Approved
0.6917	Remote Similarity	NPD6881	Approved
0.6903	Remote Similarity	NPD7748	Approved
0.6885	Remote Similarity	NPD8130	Phase 1
0.6885	Remote Similarity	NPD6649	Approved
0.6885	Remote Similarity	NPD6650	Approved
0.6875	Remote Similarity	NPD5988	Approved
0.687	Remote Similarity	NPD7902	Approved
0.6833	Remote Similarity	NPD5701	Approved
0.6833	Remote Similarity	NPD5697	Approved
0.6822	Remote Similarity	NPD6067	Discontinued
0.681	Remote Similarity	NPD7638	Approved
0.6803	Remote Similarity	NPD6883	Approved
0.6803	Remote Similarity	NPD7102	Approved
0.6803	Remote Similarity	NPD7290	Approved
0.6789	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD7640	Approved
0.6752	Remote Similarity	NPD7639	Approved
0.675	Remote Similarity	NPD6008	Approved
0.6748	Remote Similarity	NPD6869	Approved
0.6748	Remote Similarity	NPD6847	Approved
0.6748	Remote Similarity	NPD6617	Approved
0.6741	Remote Similarity	NPD8450	Suspended
0.6726	Remote Similarity	NPD7515	Phase 2
0.6724	Remote Similarity	NPD6084	Phase 2
0.6724	Remote Similarity	NPD6083	Phase 2
0.6721	Remote Similarity	NPD6014	Approved
0.6721	Remote Similarity	NPD6013	Approved
0.6721	Remote Similarity	NPD6012	Approved
0.6697	Remote Similarity	NPD4786	Approved
0.6696	Remote Similarity	NPD5695	Phase 3
0.6694	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD8074	Phase 3
0.6667	Remote Similarity	NPD5983	Phase 2
0.6667	Remote Similarity	NPD6940	Discontinued
0.6667	Remote Similarity	NPD8449	Approved
0.6639	Remote Similarity	NPD6011	Approved
0.6639	Remote Similarity	NPD7632	Discontinued
0.6639	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD6033	Approved
0.6614	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7900	Approved
0.6606	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD3669	Approved
0.6604	Remote Similarity	NPD6114	Approved
0.6604	Remote Similarity	NPD6697	Approved
0.6604	Remote Similarity	NPD6118	Approved
0.6604	Remote Similarity	NPD6115	Approved
0.6591	Remote Similarity	NPD6336	Discontinued
0.6581	Remote Similarity	NPD4755	Approved
0.6579	Remote Similarity	NPD6411	Approved
0.6549	Remote Similarity	NPD5328	Approved
0.6532	Remote Similarity	NPD4634	Approved
0.6522	Remote Similarity	NPD4202	Approved
0.6514	Remote Similarity	NPD3667	Approved
0.6509	Remote Similarity	NPD6116	Phase 1
0.6471	Remote Similarity	NPD5285	Approved
0.6471	Remote Similarity	NPD5286	Approved
0.6471	Remote Similarity	NPD4700	Approved
0.6471	Remote Similarity	NPD4696	Approved
0.6435	Remote Similarity	NPD6079	Approved
0.6429	Remote Similarity	NPD3618	Phase 1
0.6429	Remote Similarity	NPD6053	Discontinued
0.6422	Remote Similarity	NPD1779	Approved
0.6422	Remote Similarity	NPD1780	Approved
0.6415	Remote Similarity	NPD6117	Approved
0.6412	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD6274	Approved
0.6404	Remote Similarity	NPD6101	Approved
0.6404	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD5696	Approved
0.6385	Remote Similarity	NPD7100	Approved
0.6385	Remote Similarity	NPD7101	Approved
0.637	Remote Similarity	NPD8337	Approved
0.637	Remote Similarity	NPD8336	Approved
0.6364	Remote Similarity	NPD5224	Approved
0.6364	Remote Similarity	NPD8080	Discontinued
0.6364	Remote Similarity	NPD4633	Approved
0.6364	Remote Similarity	NPD5211	Phase 2
0.6364	Remote Similarity	NPD5225	Approved
0.6364	Remote Similarity	NPD5226	Approved
0.6348	Remote Similarity	NPD46	Approved
0.6348	Remote Similarity	NPD6698	Approved
0.6341	Remote Similarity	NPD4767	Approved
0.6341	Remote Similarity	NPD4768	Approved
0.633	Remote Similarity	NPD7525	Registered
0.6316	Remote Similarity	NPD5737	Approved
0.6316	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6672	Approved
0.6311	Remote Similarity	NPD5174	Approved
0.6311	Remote Similarity	NPD5175	Approved
0.6308	Remote Similarity	NPD6335	Approved
0.6301	Remote Similarity	NPD7625	Phase 1
0.6293	Remote Similarity	NPD5284	Approved
0.6293	Remote Similarity	NPD5281	Approved
0.6288	Remote Similarity	NPD6909	Approved
0.6288	Remote Similarity	NPD6908	Approved
0.6283	Remote Similarity	NPD7334	Approved
0.6283	Remote Similarity	NPD5330	Approved
0.6283	Remote Similarity	NPD7146	Approved
0.6283	Remote Similarity	NPD7521	Approved
0.6283	Remote Similarity	NPD6684	Approved
0.6283	Remote Similarity	NPD6409	Approved
0.6281	Remote Similarity	NPD5223	Approved
0.6271	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD4753	Phase 2
0.626	Remote Similarity	NPD5141	Approved
0.625	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4225	Approved
0.624	Remote Similarity	NPD4730	Approved
0.624	Remote Similarity	NPD4729	Approved
0.6239	Remote Similarity	NPD5779	Approved
0.6239	Remote Similarity	NPD5778	Approved
0.6231	Remote Similarity	NPD6317	Approved
0.6228	Remote Similarity	NPD7524	Approved
0.6226	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD4697	Phase 3
0.6218	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD5221	Approved
0.6218	Remote Similarity	NPD5222	Approved
0.6187	Remote Similarity	NPD8338	Approved
0.6183	Remote Similarity	NPD6314	Approved
0.6183	Remote Similarity	NPD6313	Approved
0.6182	Remote Similarity	NPD4748	Discontinued
0.6182	Remote Similarity	NPD6928	Phase 2
0.6179	Remote Similarity	NPD4754	Approved
0.6174	Remote Similarity	NPD6903	Approved
0.6167	Remote Similarity	NPD5173	Approved
0.6165	Remote Similarity	NPD6921	Approved
0.6159	Remote Similarity	NPD5956	Approved
0.6154	Remote Similarity	NPD7983	Approved
0.6154	Remote Similarity	NPD6050	Approved
0.6154	Remote Similarity	NPD6868	Approved
0.6154	Remote Similarity	NPD7637	Suspended
0.6142	Remote Similarity	NPD5248	Approved
0.6142	Remote Similarity	NPD5250	Approved
0.6142	Remote Similarity	NPD5251	Approved
0.6142	Remote Similarity	NPD5247	Approved
0.6142	Remote Similarity	NPD5249	Phase 3
0.614	Remote Similarity	NPD6098	Approved
0.614	Remote Similarity	NPD5279	Phase 3
0.6126	Remote Similarity	NPD4692	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