NPASS Compound

Structure

NPC188793 OpenBabel07101719512D 26 29 0 0 1 0 0 0 0 0999 V2000 5.1902 0.2750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2604 -2.6472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1264 -2.1472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1974 1.7549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2162 1.9481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4635 -0.7818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1687 0.1738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3168 0.7620 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7293 1.0747 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3944 -1.1472 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4094 0.3417 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2604 -0.6472 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2604 -1.6472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 6 7 1 0 0 0 0 6 10 1 0 0 0 0 7 12 1 0 0 0 0 8 9 1 0 0 0 0 9 21 1 0 0 0 0 10 1 1 1 0 0 0 10 14 1 0 0 0 0 11 2 1 6 0 0 0 11 16 1 0 0 0 0 11 25 1 0 0 0 0 12 14 1 0 0 0 0 12 21 1 1 0 0 0 13 8 1 6 0 0 0 13 15 1 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 15 20 1 0 0 0 0 16 17 1 0 0 0 0 16 22 1 0 0 0 0 17 18 1 0 0 0 0 17 23 1 0 0 0 0 18 19 1 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 19 26 1 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	368.26
Volume:	381.497
LogP:	4.218
LogD:	4.328
LogS:	-3.852
# Rotatable Bonds:	2
TPSA:	79.15
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.697
Synthetic Accessibility Score:	4.817
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.797
MDCK Permeability:	2.6434703613631427e-05
Pgp-inhibitor:	0.926
Pgp-substrate:	0.962
Human Intestinal Absorption (HIA):	0.035
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.269

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.051
Plasma Protein Binding (PPB):	95.1413803100586%
Volume Distribution (VD):	1.367
Pgp-substrate:	3.3827428817749023%

ADMET: Metabolism

CYP1A2-inhibitor:	0.042
CYP1A2-substrate:	0.823
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.872
CYP2C9-inhibitor:	0.036
CYP2C9-substrate:	0.067
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.262
CYP3A4-inhibitor:	0.027
CYP3A4-substrate:	0.227

ADMET: Excretion

Clearance (CL):	3.196
Half-life (T1/2):	0.547

ADMET: Toxicity

hERG Blockers:	0.266
Human Hepatotoxicity (H-HT):	0.146
Drug-inuced Liver Injury (DILI):	0.192
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.36
Maximum Recommended Daily Dose:	0.009
Skin Sensitization:	0.745
Carcinogencity:	0.037
Eye Corrosion:	0.15
Eye Irritation:	0.078
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC188793

Natural Product ID:	NPC188793
*Common Name:**	4-O-(Beta-D-Fucopyranosyl)-4-Alloaromadendrol
IUPAC Name:	(2S,3R,4S,5R,6R)-2-[[(1aR,4R,4aS,7R,7aS,7bS)-1,1,4,7-tetramethyl-2,3,4a,5,6,7,7a,7b-octahydro-1aH-cyclopropa[e]azulen-4-yl]oxy]-6-methyloxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	WKAWIUQHIDXDJS-HIIPOPSRSA-N
Standard InCHI:	InChI=1S/C21H36O5/c1-10-6-7-12-14(10)15-13(20(15,3)4)8-9-21(12,5)26-19-18(24)17(23)16(22)11(2)25-19/h10-19,22-24H,6-9H2,1-5H3/t10-,11-,12+,13-,14-,15-,16+,17+,18-,19+,21-/m1/s1
SMILES:	C[C@H]1O[C@@H](O[C@]2(C)CC[C@@H]3[C@H]([C@H]4[C@@H]2CC[C@H]4C)C3(C)C)[C@@H]([C@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518241
PubChem CID:	44567053
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides

*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
NPO17716	Calendula arvensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1965654]
NPO17716	Calendula arvensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17716	Calendula arvensis	Species	Asteraceae	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
Others	7

Activity Type	# Activity
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT195	Organism	Vesicular stomatitis virus	Vesicular stomatitis virus	Activity	=	73.0	%	PMID[547884]
NPT195	Organism	Vesicular stomatitis virus	Vesicular stomatitis virus	Activity	=	19.0	%	PMID[547884]
NPT195	Organism	Vesicular stomatitis virus	Vesicular stomatitis virus	Activity	=	8.0	%	PMID[547884]
NPT195	Organism	Vesicular stomatitis virus	Vesicular stomatitis virus	MIC50	=	14.0	ug.mL-1	PMID[547884]
NPT2517	Organism	Human rhinovirus 1B	Human rhinovirus 1B	Activity	=	0.0	%	PMID[547884]

☑ 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 NPC188793 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	452
0.1-0.2	4918
0.2-0.3	15654
0.3-0.4	9158
0.4-0.5	7427
0.5-0.6	4106
0.6-0.7	911
0.7-0.8	65
0.8-0.85	2
0.85-0.9	0
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9467	High Similarity	NPC216941
0.9342	High Similarity	NPC475849
0.9221	High Similarity	NPC474266
0.8625	High Similarity	NPC474156
0.8312	Intermediate Similarity	NPC279575
0.8228	Intermediate Similarity	NPC170595
0.8158	Intermediate Similarity	NPC470660
0.8158	Intermediate Similarity	NPC470659
0.8072	Intermediate Similarity	NPC290612
0.8056	Intermediate Similarity	NPC199937
0.8052	Intermediate Similarity	NPC308489
0.7922	Intermediate Similarity	NPC248427
0.7889	Intermediate Similarity	NPC474182
0.7882	Intermediate Similarity	NPC472396
0.7882	Intermediate Similarity	NPC43912
0.7882	Intermediate Similarity	NPC140446
0.7875	Intermediate Similarity	NPC272841
0.7875	Intermediate Similarity	NPC177343
0.7791	Intermediate Similarity	NPC470009
0.7753	Intermediate Similarity	NPC30687
0.7753	Intermediate Similarity	NPC151214
0.7753	Intermediate Similarity	NPC191915
0.7753	Intermediate Similarity	NPC175
0.7733	Intermediate Similarity	NPC477754
0.7733	Intermediate Similarity	NPC477761
0.7733	Intermediate Similarity	NPC477758
0.7733	Intermediate Similarity	NPC477760
0.7733	Intermediate Similarity	NPC477759
0.7717	Intermediate Similarity	NPC130792
0.7701	Intermediate Similarity	NPC131466
0.7701	Intermediate Similarity	NPC82955
0.7667	Intermediate Similarity	NPC473064
0.7667	Intermediate Similarity	NPC473067
0.7667	Intermediate Similarity	NPC473065
0.7662	Intermediate Similarity	NPC471879
0.764	Intermediate Similarity	NPC473726
0.7614	Intermediate Similarity	NPC279329
0.76	Intermediate Similarity	NPC477751
0.76	Intermediate Similarity	NPC477752
0.76	Intermediate Similarity	NPC477756
0.76	Intermediate Similarity	NPC477764
0.7595	Intermediate Similarity	NPC166250
0.759	Intermediate Similarity	NPC473257
0.7586	Intermediate Similarity	NPC281004
0.7582	Intermediate Similarity	NPC476510
0.7582	Intermediate Similarity	NPC252056
0.7582	Intermediate Similarity	NPC142264
0.7528	Intermediate Similarity	NPC229801
0.7528	Intermediate Similarity	NPC59006
0.7528	Intermediate Similarity	NPC36372
0.7528	Intermediate Similarity	NPC293609
0.7528	Intermediate Similarity	NPC307167
0.7528	Intermediate Similarity	NPC210759
0.75	Intermediate Similarity	NPC233649
0.75	Intermediate Similarity	NPC102725
0.75	Intermediate Similarity	NPC228059
0.75	Intermediate Similarity	NPC470028
0.75	Intermediate Similarity	NPC473472
0.747	Intermediate Similarity	NPC66766
0.747	Intermediate Similarity	NPC117137
0.7467	Intermediate Similarity	NPC165069
0.7444	Intermediate Similarity	NPC167644
0.7444	Intermediate Similarity	NPC277774
0.7444	Intermediate Similarity	NPC311246
0.7416	Intermediate Similarity	NPC65550
0.7416	Intermediate Similarity	NPC223143
0.7416	Intermediate Similarity	NPC473542
0.7412	Intermediate Similarity	NPC470070
0.7412	Intermediate Similarity	NPC241959
0.7397	Intermediate Similarity	NPC472026
0.7375	Intermediate Similarity	NPC138273
0.7363	Intermediate Similarity	NPC477224
0.7363	Intermediate Similarity	NPC305418
0.7363	Intermediate Similarity	NPC45959
0.7363	Intermediate Similarity	NPC252253
0.7363	Intermediate Similarity	NPC309866
0.7363	Intermediate Similarity	NPC113500
0.7363	Intermediate Similarity	NPC473503
0.7363	Intermediate Similarity	NPC3538
0.7356	Intermediate Similarity	NPC471411
0.7356	Intermediate Similarity	NPC470657
0.7356	Intermediate Similarity	NPC471410
0.734	Intermediate Similarity	NPC470030
0.7333	Intermediate Similarity	NPC5632
0.7333	Intermediate Similarity	NPC149966
0.7333	Intermediate Similarity	NPC476702
0.7333	Intermediate Similarity	NPC473830
0.7333	Intermediate Similarity	NPC476668
0.7333	Intermediate Similarity	NPC204881
0.7333	Intermediate Similarity	NPC473637
0.7326	Intermediate Similarity	NPC166279
0.7324	Intermediate Similarity	NPC148424
0.7312	Intermediate Similarity	NPC475207
0.7303	Intermediate Similarity	NPC20822
0.7283	Intermediate Similarity	NPC477494
0.7283	Intermediate Similarity	NPC94582
0.7283	Intermediate Similarity	NPC57964
0.7283	Intermediate Similarity	NPC469710
0.7283	Intermediate Similarity	NPC474399
0.7283	Intermediate Similarity	NPC92196
0.7283	Intermediate Similarity	NPC215570
0.7273	Intermediate Similarity	NPC210658
0.7273	Intermediate Similarity	NPC161928
0.7273	Intermediate Similarity	NPC31349
0.7263	Intermediate Similarity	NPC108227
0.7263	Intermediate Similarity	NPC476838
0.7263	Intermediate Similarity	NPC476839
0.7263	Intermediate Similarity	NPC472081
0.7263	Intermediate Similarity	NPC476512
0.7262	Intermediate Similarity	NPC186588
0.7253	Intermediate Similarity	NPC477547
0.7253	Intermediate Similarity	NPC137004
0.7253	Intermediate Similarity	NPC172838
0.7253	Intermediate Similarity	NPC88962
0.7253	Intermediate Similarity	NPC249204
0.7253	Intermediate Similarity	NPC297348
0.7253	Intermediate Similarity	NPC177834
0.7253	Intermediate Similarity	NPC144790
0.7253	Intermediate Similarity	NPC325828
0.7253	Intermediate Similarity	NPC250393
0.7253	Intermediate Similarity	NPC476669
0.7253	Intermediate Similarity	NPC48339
0.7253	Intermediate Similarity	NPC149400
0.7253	Intermediate Similarity	NPC141769
0.7253	Intermediate Similarity	NPC477451
0.7253	Intermediate Similarity	NPC234352
0.7209	Intermediate Similarity	NPC2572
0.7209	Intermediate Similarity	NPC29342
0.7204	Intermediate Similarity	NPC304011
0.7204	Intermediate Similarity	NPC237071
0.7204	Intermediate Similarity	NPC473287
0.7204	Intermediate Similarity	NPC203434
0.7204	Intermediate Similarity	NPC238796
0.7204	Intermediate Similarity	NPC472989
0.7204	Intermediate Similarity	NPC139271
0.7204	Intermediate Similarity	NPC156377
0.7195	Intermediate Similarity	NPC107963
0.7191	Intermediate Similarity	NPC128475
0.7188	Intermediate Similarity	NPC470029
0.7188	Intermediate Similarity	NPC310138
0.7188	Intermediate Similarity	NPC114700
0.7188	Intermediate Similarity	NPC134967
0.7174	Intermediate Similarity	NPC475436
0.7174	Intermediate Similarity	NPC24960
0.7174	Intermediate Similarity	NPC473851
0.7174	Intermediate Similarity	NPC217205
0.7174	Intermediate Similarity	NPC312678
0.7174	Intermediate Similarity	NPC473774
0.7174	Intermediate Similarity	NPC294686
0.7174	Intermediate Similarity	NPC253268
0.7174	Intermediate Similarity	NPC291203
0.7174	Intermediate Similarity	NPC131693
0.7174	Intermediate Similarity	NPC264101
0.7174	Intermediate Similarity	NPC179859
0.7174	Intermediate Similarity	NPC174024
0.7174	Intermediate Similarity	NPC291547
0.7174	Intermediate Similarity	NPC471464
0.7174	Intermediate Similarity	NPC475325
0.7174	Intermediate Similarity	NPC222731
0.7162	Intermediate Similarity	NPC475412
0.716	Intermediate Similarity	NPC472944
0.716	Intermediate Similarity	NPC472945
0.7159	Intermediate Similarity	NPC471240
0.7159	Intermediate Similarity	NPC268633
0.7159	Intermediate Similarity	NPC472745
0.7159	Intermediate Similarity	NPC64862
0.7159	Intermediate Similarity	NPC107603
0.7158	Intermediate Similarity	NPC41843
0.7143	Intermediate Similarity	NPC235051
0.7143	Intermediate Similarity	NPC48463
0.7128	Intermediate Similarity	NPC477223
0.7128	Intermediate Similarity	NPC477222
0.7128	Intermediate Similarity	NPC274200
0.7126	Intermediate Similarity	NPC227260
0.7126	Intermediate Similarity	NPC18953
0.7113	Intermediate Similarity	NPC476837
0.7113	Intermediate Similarity	NPC97260
0.7113	Intermediate Similarity	NPC139181
0.7097	Intermediate Similarity	NPC473610
0.7097	Intermediate Similarity	NPC211354
0.7097	Intermediate Similarity	NPC107962
0.7097	Intermediate Similarity	NPC19400
0.7097	Intermediate Similarity	NPC206003
0.7097	Intermediate Similarity	NPC6295
0.7097	Intermediate Similarity	NPC475351
0.7097	Intermediate Similarity	NPC473727
0.7097	Intermediate Similarity	NPC107188
0.7093	Intermediate Similarity	NPC475388
0.7093	Intermediate Similarity	NPC470611
0.7083	Intermediate Similarity	NPC31346
0.7073	Intermediate Similarity	NPC472952
0.7073	Intermediate Similarity	NPC131584
0.7073	Intermediate Similarity	NPC139765
0.7073	Intermediate Similarity	NPC472950
0.7059	Intermediate Similarity	NPC16449
0.7053	Intermediate Similarity	NPC473638
0.7051	Intermediate Similarity	NPC179823
0.7045	Intermediate Similarity	NPC232044
0.7045	Intermediate Similarity	NPC273290
0.7027	Intermediate Similarity	NPC475968

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 NPC188793 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	537
0.1-0.2	4668
0.2-0.3	2756
0.3-0.4	629
0.4-0.5	410
0.5-0.6	136
0.6-0.7	14
0.7-0.8	0
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
0.7253	Intermediate Similarity	NPD8171	Discontinued
0.6951	Remote Similarity	NPD1810	Approved
0.6951	Remote Similarity	NPD1811	Approved
0.686	Remote Similarity	NPD6928	Phase 2
0.679	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD2267	Suspended
0.6585	Remote Similarity	NPD2254	Approved
0.6585	Remote Similarity	NPD2687	Approved
0.6585	Remote Similarity	NPD2686	Approved
0.6535	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD2269	Approved
0.6463	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD371	Approved
0.6438	Remote Similarity	NPD889	Approved
0.6438	Remote Similarity	NPD887	Approved
0.6438	Remote Similarity	NPD895	Approved
0.6438	Remote Similarity	NPD894	Approved
0.6389	Remote Similarity	NPD904	Phase 3
0.6389	Remote Similarity	NPD905	Approved
0.6264	Remote Similarity	NPD3669	Approved
0.6264	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6412	Phase 2
0.6216	Remote Similarity	NPD891	Phase 3
0.6216	Remote Similarity	NPD888	Phase 3
0.6216	Remote Similarity	NPD892	Phase 3
0.6216	Remote Similarity	NPD893	Approved
0.6216	Remote Similarity	NPD890	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.617	Remote Similarity	NPD7524	Approved
0.6076	Remote Similarity	NPD6123	Approved
0.6055	Remote Similarity	NPD8133	Approved
0.6022	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD7328	Approved
0.5982	Remote Similarity	NPD7327	Approved
0.5946	Remote Similarity	NPD6940	Discontinued
0.5929	Remote Similarity	NPD7516	Approved
0.5915	Remote Similarity	NPD8999	Phase 3
0.5915	Remote Similarity	NPD8993	Phase 1
0.5915	Remote Similarity	NPD8998	Phase 2
0.5915	Remote Similarity	NPD8997	Approved
0.5915	Remote Similarity	NPD9000	Phase 3
0.5914	Remote Similarity	NPD6695	Phase 3
0.59	Remote Similarity	NPD7991	Discontinued
0.5889	Remote Similarity	NPD4238	Approved
0.5889	Remote Similarity	NPD4802	Phase 2
0.5888	Remote Similarity	NPD8174	Phase 2
0.5888	Remote Similarity	NPD6686	Approved
0.5877	Remote Similarity	NPD8294	Approved
0.5877	Remote Similarity	NPD8377	Approved
0.5826	Remote Similarity	NPD8380	Approved
0.5826	Remote Similarity	NPD8378	Approved
0.5826	Remote Similarity	NPD8379	Approved
0.5826	Remote Similarity	NPD8335	Approved
0.5826	Remote Similarity	NPD8296	Approved
0.5826	Remote Similarity	NPD7503	Approved
0.5826	Remote Similarity	NPD8033	Approved
0.5753	Remote Similarity	NPD8966	Approved
0.5753	Remote Similarity	NPD8965	Approved
0.5732	Remote Similarity	NPD847	Phase 1
0.5714	Remote Similarity	NPD8082	Approved
0.5714	Remote Similarity	NPD7346	Approved
0.5714	Remote Similarity	NPD8139	Approved
0.5714	Remote Similarity	NPD8086	Approved
0.5714	Remote Similarity	NPD8085	Approved
0.5714	Remote Similarity	NPD6115	Approved
0.5714	Remote Similarity	NPD8084	Approved
0.5714	Remote Similarity	NPD8083	Approved
0.5714	Remote Similarity	NPD6118	Approved
0.5714	Remote Similarity	NPD6697	Approved
0.5714	Remote Similarity	NPD6114	Approved
0.5714	Remote Similarity	NPD8138	Approved
0.5699	Remote Similarity	NPD1779	Approved
0.5699	Remote Similarity	NPD1780	Approved
0.5688	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.567	Remote Similarity	NPD7750	Discontinued
0.5667	Remote Similarity	NPD6933	Approved
0.566	Remote Similarity	NPD8276	Approved
0.566	Remote Similarity	NPD8275	Approved
0.5636	Remote Similarity	NPD6371	Approved
0.5632	Remote Similarity	NPD4787	Phase 1
0.563	Remote Similarity	NPD7507	Approved
0.5607	Remote Similarity	NPD8081	Approved
0.5604	Remote Similarity	NPD6116	Phase 1

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