NPASS Compound

Structure

NPC164148 OpenBabel07101718182D 25 26 0 0 0 0 0 0 0 0999 V2000 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 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 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 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 1 14 1 0 0 0 0 2 15 1 0 0 0 0 3 23 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 14 1 0 0 0 0 6 15 2 0 0 0 0 7 8 2 0 0 0 0 7 16 1 0 0 0 0 8 20 1 0 0 0 0 9 10 1 0 0 0 0 9 14 2 0 0 0 0 10 24 1 0 0 0 0 11 16 2 0 0 0 0 11 18 1 0 0 0 0 12 17 2 0 0 0 0 12 19 1 0 0 0 0 13 15 1 0 0 0 0 13 21 1 0 0 0 0 16 17 1 0 0 0 0 17 25 1 0 0 0 0 18 19 2 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 20 22 2 0 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.16
Volume:	362.859
LogP:	2.438
LogD:	2.922
LogS:	-3.996
# Rotatable Bonds:	8
TPSA:	68.9
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.582
Synthetic Accessibility Score:	2.692
Fsp3:	0.35
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.748
MDCK Permeability:	2.080287413264159e-05
Pgp-inhibitor:	0.018
Pgp-substrate:	0.614
Human Intestinal Absorption (HIA):	0.078
20% Bioavailability (F20%):	0.833
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.076
Plasma Protein Binding (PPB):	96.78591918945312%
Volume Distribution (VD):	0.367
Pgp-substrate:	1.3374041318893433%

ADMET: Metabolism

CYP1A2-inhibitor:	0.915
CYP1A2-substrate:	0.948
CYP2C19-inhibitor:	0.662
CYP2C19-substrate:	0.402
CYP2C9-inhibitor:	0.377
CYP2C9-substrate:	0.752
CYP2D6-inhibitor:	0.714
CYP2D6-substrate:	0.915
CYP3A4-inhibitor:	0.394
CYP3A4-substrate:	0.378

ADMET: Excretion

Clearance (CL):	9.358
Half-life (T1/2):	0.879

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.159
Drug-inuced Liver Injury (DILI):	0.562
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.44
Skin Sensitization:	0.911
Carcinogencity:	0.408
Eye Corrosion:	0.005
Eye Irritation:	0.422
Respiratory Toxicity:	0.065

Download Data

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

Natural Product: NPC164148

Natural Product ID:	NPC164148
*Common Name:**	Artekeiskeanol B
IUPAC Name:	7-[(2E,6Z)-8-hydroxy-3,7-dimethylocta-2,6-dienoxy]-6-methoxychromen-2-one
Synonyms:
Standard InCHIKey:	TVDKTNHSAAVHMX-XQKUNLABSA-N
Standard InCHI:	InChI=1S/C20H24O5/c1-14(5-4-6-15(2)13-21)9-10-24-19-12-17-16(11-18(19)23-3)7-8-20(22)25-17/h6-9,11-12,21H,4-5,10,13H2,1-3H3/b14-9+,15-6-
SMILES:	C/C(=CCOc1cc2c(ccc(=O)o2)cc1OC)/CC/C=C(/C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454286
PubChem CID:	10925981
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO3948	Artemisia keiskeana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520232]
NPO3948	Artemisia keiskeana	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT140	Organism	Artemia	Artemia	LC50	=	70.0	ug.mL-1	PMID[475241]

☑ 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 NPC164148 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	374
0.1-0.2	1609
0.2-0.3	4501
0.3-0.4	9754
0.4-0.5	8300
0.5-0.6	3855
0.6-0.7	5394
0.7-0.8	5184
0.8-0.85	2537
0.85-0.9	1091
0.9-0.95	92
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC43500
0.9701	High Similarity	NPC300611
0.9618	High Similarity	NPC241341
0.9618	High Similarity	NPC36437
0.9618	High Similarity	NPC233018
0.9559	High Similarity	NPC138212
0.9552	High Similarity	NPC13067
0.9542	High Similarity	NPC137669
0.9478	High Similarity	NPC52086
0.9478	High Similarity	NPC139548
0.9478	High Similarity	NPC76336
0.9478	High Similarity	NPC148835
0.9478	High Similarity	NPC95162
0.9478	High Similarity	NPC20511
0.9403	High Similarity	NPC126682
0.9403	High Similarity	NPC82271
0.9394	High Similarity	NPC319969
0.9389	High Similarity	NPC240722
0.9389	High Similarity	NPC19242
0.9389	High Similarity	NPC244799
0.9353	High Similarity	NPC205361
0.9313	High Similarity	NPC123127
0.9313	High Similarity	NPC27239
0.9286	High Similarity	NPC15577
0.9254	High Similarity	NPC309953
0.9254	High Similarity	NPC92830
0.9248	High Similarity	NPC5423
0.9225	High Similarity	NPC205727
0.9225	High Similarity	NPC120426
0.9225	High Similarity	NPC21184
0.9225	High Similarity	NPC294522
0.922	High Similarity	NPC96294
0.9185	High Similarity	NPC472521
0.9179	High Similarity	NPC26673
0.9161	High Similarity	NPC213197
0.9155	High Similarity	NPC176903
0.9155	High Similarity	NPC30688
0.9149	High Similarity	NPC476347
0.9143	High Similarity	NPC476450
0.9137	High Similarity	NPC256555
0.9137	High Similarity	NPC7439
0.9137	High Similarity	NPC91492
0.9137	High Similarity	NPC34245
0.9137	High Similarity	NPC110067
0.913	High Similarity	NPC279851
0.913	High Similarity	NPC472520
0.9118	High Similarity	NPC286843
0.9104	High Similarity	NPC245120
0.9104	High Similarity	NPC137949
0.9091	High Similarity	NPC114740
0.9085	High Similarity	NPC476348
0.9085	High Similarity	NPC187398
0.9071	High Similarity	NPC471763
0.9051	High Similarity	NPC20796
0.9044	High Similarity	NPC234865
0.9037	High Similarity	NPC472522
0.9037	High Similarity	NPC277021
0.903	High Similarity	NPC73738
0.9021	High Similarity	NPC313334
0.9021	High Similarity	NPC212670
0.9021	High Similarity	NPC206264
0.9015	High Similarity	NPC121740
0.9015	High Similarity	NPC258567
0.9015	High Similarity	NPC224774
0.9014	High Similarity	NPC178129
0.9014	High Similarity	NPC231149
0.9	High Similarity	NPC236419
0.8986	High Similarity	NPC270256
0.8978	High Similarity	NPC26954
0.8978	High Similarity	NPC38099
0.8978	High Similarity	NPC167517
0.8971	High Similarity	NPC111635
0.8971	High Similarity	NPC474600
0.8966	High Similarity	NPC163598
0.8966	High Similarity	NPC120774
0.8966	High Similarity	NPC264875
0.8951	High Similarity	NPC139839
0.8947	High Similarity	NPC469453
0.8947	High Similarity	NPC474616
0.8939	High Similarity	NPC127604
0.8929	High Similarity	NPC469564
0.8913	High Similarity	NPC476171
0.8905	High Similarity	NPC240915
0.8897	High Similarity	NPC474810
0.8897	High Similarity	NPC31849
0.8889	High Similarity	NPC29734
0.8881	High Similarity	NPC52740
0.8881	High Similarity	NPC41844
0.8881	High Similarity	NPC48315
0.8872	High Similarity	NPC474670
0.8872	High Similarity	NPC194841
0.8865	High Similarity	NPC230157
0.8864	High Similarity	NPC27352
0.8849	High Similarity	NPC279573
0.8849	High Similarity	NPC151946
0.8841	High Similarity	NPC471719
0.8832	High Similarity	NPC7163
0.8832	High Similarity	NPC50896
0.8832	High Similarity	NPC147030
0.8832	High Similarity	NPC204353
0.8832	High Similarity	NPC326600
0.8832	High Similarity	NPC309744
0.8819	High Similarity	NPC48366
0.8819	High Similarity	NPC93924
0.8815	High Similarity	NPC113098
0.8815	High Similarity	NPC476399
0.8806	High Similarity	NPC474651
0.8806	High Similarity	NPC474623
0.8806	High Similarity	NPC109275
0.8803	High Similarity	NPC185127
0.8779	High Similarity	NPC288238
0.8779	High Similarity	NPC270326
0.8777	High Similarity	NPC474886
0.8777	High Similarity	NPC155963
0.8777	High Similarity	NPC38874
0.8768	High Similarity	NPC472525
0.8768	High Similarity	NPC73071
0.8768	High Similarity	NPC472337
0.875	High Similarity	NPC267336
0.875	High Similarity	NPC142530
0.875	High Similarity	NPC272650
0.875	High Similarity	NPC147317
0.8732	High Similarity	NPC6568
0.8731	High Similarity	NPC474821
0.8725	High Similarity	NPC284810
0.8723	High Similarity	NPC152771
0.8723	High Similarity	NPC195357
0.8714	High Similarity	NPC211110
0.8707	High Similarity	NPC476352
0.8707	High Similarity	NPC215060
0.8705	High Similarity	NPC472336
0.8705	High Similarity	NPC472334
0.8702	High Similarity	NPC310373
0.8699	High Similarity	NPC477381
0.8696	High Similarity	NPC180716
0.8696	High Similarity	NPC224475
0.8696	High Similarity	NPC62366
0.8696	High Similarity	NPC213173
0.869	High Similarity	NPC478237
0.8686	High Similarity	NPC194277
0.8686	High Similarity	NPC123954
0.8681	High Similarity	NPC287275
0.8676	High Similarity	NPC214860
0.8667	High Similarity	NPC210674
0.8657	High Similarity	NPC474632
0.8652	High Similarity	NPC267291
0.8652	High Similarity	NPC312881
0.8649	High Similarity	NPC150442
0.8643	High Similarity	NPC184861
0.8643	High Similarity	NPC294456
0.8643	High Similarity	NPC232246
0.8643	High Similarity	NPC105493
0.8643	High Similarity	NPC212124
0.8643	High Similarity	NPC225106
0.8643	High Similarity	NPC281014
0.8643	High Similarity	NPC153818
0.8643	High Similarity	NPC126206
0.8639	High Similarity	NPC477379
0.8636	High Similarity	NPC194626
0.8633	High Similarity	NPC252095
0.8633	High Similarity	NPC195022
0.8633	High Similarity	NPC311430
0.8633	High Similarity	NPC224941
0.8626	High Similarity	NPC199023
0.8626	High Similarity	NPC180006
0.8626	High Similarity	NPC163200
0.8626	High Similarity	NPC235190
0.8623	High Similarity	NPC168059
0.8623	High Similarity	NPC469449
0.8623	High Similarity	NPC229442
0.8611	High Similarity	NPC125617
0.8603	High Similarity	NPC202582
0.8603	High Similarity	NPC222004
0.8603	High Similarity	NPC210623
0.8603	High Similarity	NPC470258
0.8603	High Similarity	NPC273295
0.8603	High Similarity	NPC3439
0.8603	High Similarity	NPC190629
0.8603	High Similarity	NPC218856
0.8603	High Similarity	NPC285339
0.8603	High Similarity	NPC226788
0.8603	High Similarity	NPC45824
0.8592	High Similarity	NPC224876
0.8592	High Similarity	NPC83375
0.8592	High Similarity	NPC287286
0.8591	High Similarity	NPC8712
0.8582	High Similarity	NPC58279
0.8582	High Similarity	NPC471388
0.8582	High Similarity	NPC300326
0.8581	High Similarity	NPC470264
0.8581	High Similarity	NPC176186
0.8581	High Similarity	NPC169404
0.8581	High Similarity	NPC53587
0.8571	High Similarity	NPC37468
0.8571	High Similarity	NPC471664
0.8571	High Similarity	NPC471665
0.8571	High Similarity	NPC188380
0.8571	High Similarity	NPC224543
0.8571	High Similarity	NPC173660
0.8571	High Similarity	NPC78746

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 NPC164148 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	330
0.1-0.2	942
0.2-0.3	1977
0.3-0.4	2537
0.4-0.5	1804
0.5-0.6	997
0.6-0.7	392
0.7-0.8	120
0.8-0.85	40
0.85-0.9	10
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9021	High Similarity	NPD1653	Approved
0.8421	Intermediate Similarity	NPD422	Phase 1
0.8207	Intermediate Similarity	NPD1652	Phase 2
0.8201	Intermediate Similarity	NPD3027	Phase 3
0.8176	Intermediate Similarity	NPD5844	Phase 1
0.8156	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8156	Intermediate Similarity	NPD1613	Approved
0.8105	Intermediate Similarity	NPD2801	Approved
0.8099	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD5124	Phase 1
0.8074	Intermediate Similarity	NPD3496	Discontinued
0.8052	Intermediate Similarity	NPD3817	Phase 2
0.8	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD7549	Discontinued
0.7972	Intermediate Similarity	NPD447	Suspended
0.7929	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD5402	Approved
0.7806	Intermediate Similarity	NPD1934	Approved
0.7801	Intermediate Similarity	NPD3018	Phase 2
0.7771	Intermediate Similarity	NPD3882	Suspended
0.7758	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD230	Phase 1
0.7721	Intermediate Similarity	NPD1548	Phase 1
0.7669	Intermediate Similarity	NPD3818	Discontinued
0.7643	Intermediate Similarity	NPD2982	Phase 2
0.7643	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD2983	Phase 2
0.7643	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD6799	Approved
0.7632	Intermediate Similarity	NPD1511	Approved
0.7626	Intermediate Similarity	NPD1091	Approved
0.7622	Intermediate Similarity	NPD7054	Approved
0.7622	Intermediate Similarity	NPD4908	Phase 1
0.7622	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD3225	Approved
0.7584	Intermediate Similarity	NPD7266	Discontinued
0.758	Intermediate Similarity	NPD37	Approved
0.7578	Intermediate Similarity	NPD7199	Phase 2
0.7576	Intermediate Similarity	NPD7472	Approved
0.7571	Intermediate Similarity	NPD2981	Phase 2
0.7562	Intermediate Similarity	NPD919	Approved
0.7557	Intermediate Similarity	NPD1358	Approved
0.755	Intermediate Similarity	NPD3750	Approved
0.755	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD3686	Approved
0.7548	Intermediate Similarity	NPD3687	Approved
0.7547	Intermediate Similarity	NPD4965	Approved
0.7547	Intermediate Similarity	NPD4966	Approved
0.7547	Intermediate Similarity	NPD4967	Phase 2
0.7546	Intermediate Similarity	NPD6166	Phase 2
0.7546	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD4060	Phase 1
0.7533	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1465	Phase 2
0.7532	Intermediate Similarity	NPD1512	Approved
0.7518	Intermediate Similarity	NPD5536	Phase 2
0.7517	Intermediate Similarity	NPD1551	Phase 2
0.7517	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD2935	Discontinued
0.7516	Intermediate Similarity	NPD5494	Approved
0.7516	Intermediate Similarity	NPD4357	Discontinued
0.75	Intermediate Similarity	NPD6190	Approved
0.75	Intermediate Similarity	NPD1610	Phase 2
0.7484	Intermediate Similarity	NPD5403	Approved
0.7482	Intermediate Similarity	NPD1778	Approved
0.747	Intermediate Similarity	NPD7074	Phase 3
0.7468	Intermediate Similarity	NPD6801	Discontinued
0.744	Intermediate Similarity	NPD7808	Phase 3
0.7434	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD4628	Phase 3
0.7431	Intermediate Similarity	NPD2861	Phase 2
0.7425	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD6797	Phase 2
0.7423	Intermediate Similarity	NPD6232	Discontinued
0.7421	Intermediate Similarity	NPD7819	Suspended
0.7421	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD2797	Approved
0.7405	Intermediate Similarity	NPD9697	Approved
0.7403	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1296	Phase 2
0.7394	Intermediate Similarity	NPD4749	Approved
0.7391	Intermediate Similarity	NPD7075	Discontinued
0.7391	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7251	Discontinued
0.7378	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD3705	Approved
0.7372	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6671	Approved
0.7365	Intermediate Similarity	NPD4340	Discontinued
0.7362	Intermediate Similarity	NPD8127	Discontinued
0.7362	Intermediate Similarity	NPD1247	Approved
0.7357	Intermediate Similarity	NPD4626	Approved
0.7355	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD5401	Approved
0.7348	Intermediate Similarity	NPD3134	Approved
0.7347	Intermediate Similarity	NPD6233	Phase 2
0.7346	Intermediate Similarity	NPD6234	Discontinued
0.7342	Intermediate Similarity	NPD4380	Phase 2
0.7342	Intermediate Similarity	NPD4678	Approved
0.7342	Intermediate Similarity	NPD4675	Approved
0.7342	Intermediate Similarity	NPD6599	Discontinued
0.7333	Intermediate Similarity	NPD3748	Approved
0.7333	Intermediate Similarity	NPD228	Approved
0.7324	Intermediate Similarity	NPD9717	Approved
0.7296	Intermediate Similarity	NPD7411	Suspended
0.7293	Intermediate Similarity	NPD290	Approved
0.7289	Intermediate Similarity	NPD7473	Discontinued
0.7286	Intermediate Similarity	NPD1357	Approved
0.7286	Intermediate Similarity	NPD5691	Approved
0.7285	Intermediate Similarity	NPD2796	Approved
0.7279	Intermediate Similarity	NPD3268	Approved
0.7273	Intermediate Similarity	NPD2219	Phase 1
0.7267	Intermediate Similarity	NPD5353	Approved
0.7255	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1933	Approved
0.7241	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2684	Approved
0.7237	Intermediate Similarity	NPD5763	Approved
0.7237	Intermediate Similarity	NPD3540	Phase 1
0.7237	Intermediate Similarity	NPD5762	Approved
0.7226	Intermediate Similarity	NPD5283	Phase 1
0.7222	Intermediate Similarity	NPD7768	Phase 2
0.7219	Intermediate Similarity	NPD7033	Discontinued
0.7219	Intermediate Similarity	NPD1510	Phase 2
0.7211	Intermediate Similarity	NPD4625	Phase 3
0.7208	Intermediate Similarity	NPD4110	Phase 3
0.7208	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6653	Approved
0.7195	Intermediate Similarity	NPD5677	Discontinued
0.719	Intermediate Similarity	NPD1549	Phase 2
0.719	Intermediate Similarity	NPD2424	Discontinued
0.7176	Intermediate Similarity	NPD6559	Discontinued
0.7172	Intermediate Similarity	NPD1203	Approved
0.7171	Intermediate Similarity	NPD3539	Phase 1
0.7162	Intermediate Similarity	NPD411	Approved
0.7162	Intermediate Similarity	NPD6798	Discontinued
0.7153	Intermediate Similarity	NPD7843	Approved
0.7153	Intermediate Similarity	NPD5535	Approved
0.7152	Intermediate Similarity	NPD920	Approved
0.7143	Intermediate Similarity	NPD6674	Discontinued
0.7143	Intermediate Similarity	NPD6832	Phase 2
0.7143	Intermediate Similarity	NPD7228	Approved
0.7134	Intermediate Similarity	NPD2534	Approved
0.7134	Intermediate Similarity	NPD2533	Approved
0.7134	Intermediate Similarity	NPD2532	Approved
0.7133	Intermediate Similarity	NPD1611	Approved
0.7133	Intermediate Similarity	NPD6355	Discontinued
0.7124	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD7157	Approved
0.7105	Intermediate Similarity	NPD4308	Phase 3
0.7103	Intermediate Similarity	NPD8651	Approved
0.7095	Intermediate Similarity	NPD7095	Approved
0.709	Intermediate Similarity	NPD968	Approved
0.7081	Intermediate Similarity	NPD5090	Approved
0.7081	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5089	Approved
0.7076	Intermediate Similarity	NPD7038	Approved
0.7076	Intermediate Similarity	NPD7039	Approved
0.7075	Intermediate Similarity	NPD9494	Approved
0.7073	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD5297	Approved
0.7067	Intermediate Similarity	NPD4140	Approved
0.7067	Intermediate Similarity	NPD1240	Approved
0.7066	Intermediate Similarity	NPD5242	Approved
0.7059	Intermediate Similarity	NPD6032	Approved
0.7051	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD1048	Approved
0.7042	Intermediate Similarity	NPD5585	Approved
0.7042	Intermediate Similarity	NPD9268	Approved
0.7041	Intermediate Similarity	NPD3751	Discontinued
0.7032	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1243	Approved
0.7029	Intermediate Similarity	NPD6843	Phase 3
0.7029	Intermediate Similarity	NPD6842	Approved
0.7029	Intermediate Similarity	NPD6841	Approved
0.7025	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD4123	Phase 3
0.7014	Intermediate Similarity	NPD1535	Discovery
0.7013	Intermediate Similarity	NPD6005	Phase 3
0.7013	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6004	Phase 3
0.7013	Intermediate Similarity	NPD6002	Phase 3
0.7013	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1375	Discontinued
0.7007	Intermediate Similarity	NPD1019	Discontinued
0.7006	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6666	Approved
0.7006	Intermediate Similarity	NPD6667	Approved
0.7	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7685	Pre-registration

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