NPASS Compound

Structure

CID100767 OpenBabel06191715442D 24 25 0 0 0 0 0 0 0 0999 V2000 -1.7321 3.0000 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 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -3.8660 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 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 -0.0000 2.0000 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 2.5981 0.5000 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 1.7321 0.0000 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 2.5981 -2.5000 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 0.0000 -1.0000 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 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 20 1 0 0 0 0 5 20 1 0 0 0 0 6 7 2 0 0 0 0 6 12 1 0 0 0 0 7 13 1 0 0 0 0 8 9 1 0 0 0 0 8 14 1 0 0 0 0 9 16 1 0 0 0 0 10 13 1 0 0 0 0 10 15 2 0 0 0 0 11 15 1 0 0 0 0 12 14 2 0 0 0 0 13 17 2 0 0 0 0 14 17 1 0 0 0 0 15 18 1 0 0 0 0 16 20 1 0 0 0 0 16 21 2 0 0 0 0 17 19 1 0 0 0 0 18 19 1 0 0 0 0 18 22 2 0 0 0 0 19 23 2 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.17
Volume:	354.069
LogP:	4.004
LogD:	2.648
LogS:	-3.779
# Rotatable Bonds:	5
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.728
Synthetic Accessibility Score:	2.973
Fsp3:	0.35
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.798
MDCK Permeability:	1.600378345756326e-05
Pgp-inhibitor:	0.034
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.887
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	97.5888900756836%
Volume Distribution (VD):	0.573
Pgp-substrate:	2.537384510040283%

ADMET: Metabolism

CYP1A2-inhibitor:	0.924
CYP1A2-substrate:	0.943
CYP2C19-inhibitor:	0.344
CYP2C19-substrate:	0.241
CYP2C9-inhibitor:	0.652
CYP2C9-substrate:	0.821
CYP2D6-inhibitor:	0.519
CYP2D6-substrate:	0.669
CYP3A4-inhibitor:	0.186
CYP3A4-substrate:	0.231

ADMET: Excretion

Clearance (CL):	8.621
Half-life (T1/2):	0.857

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.158
Drug-inuced Liver Injury (DILI):	0.201
AMES Toxicity:	0.388
Rat Oral Acute Toxicity:	0.303
Maximum Recommended Daily Dose:	0.469
Skin Sensitization:	0.884
Carcinogencity:	0.349
Eye Corrosion:	0.003
Eye Irritation:	0.229
Respiratory Toxicity:	0.139

Download Data

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

Natural Product: NPC100767

Natural Product ID:	NPC100767
*Common Name:**	8-(4-Hydroxy-4-Methyl-3-Oxopentyl)-7-Methyl-3-Propan-2-Ylnaphthalene-1,2-Dione
IUPAC Name:	8-(4-hydroxy-4-methyl-3-oxopentyl)-7-methyl-3-propan-2-ylnaphthalene-1,2-dione
Synonyms:
Standard InCHIKey:	VDYQVYQVQLEJQY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H24O4/c1-11(2)15-10-13-7-6-12(3)14(17(13)19(23)18(15)22)8-9-16(21)20(4,5)24/h6-7,10-11,24H,8-9H2,1-5H3
SMILES:	CC(C)C1=Cc2ccc(C)c(CCC(=O)C(C)(C)O)c2C(=O)C1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453563
PubChem CID:	10381845
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0000153] Naphthoquinones

*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
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473439]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12141863]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	exudates	n.a.	n.a.	PMID[16441065]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	stems	n.a.	n.a.	PMID[18558745]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21824777]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	stems	n.a.	n.a.	PMID[25891102]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19148	Gouania tomentosa	Species	Gobiesocidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21396	Spongia vermicularis	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21056	Angelica keiskei	Species	Apiaceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	4600.0	nM	PMID[483391]
NPT515	Cell Line	SGC-7901	Homo sapiens	IC50	=	200.0	nM	PMID[483391]
NPT1179	Cell Line	MKN-28	Homo sapiens	IC50	=	300.0	nM	PMID[483391]

☑ 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 NPC100767 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	225
0.1-0.2	1155
0.2-0.3	2681
0.3-0.4	9335
0.4-0.5	15207
0.5-0.6	11155
0.6-0.7	2476
0.7-0.8	378
0.8-0.85	57
0.85-0.9	25
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9694	High Similarity	NPC247976
0.9515	High Similarity	NPC292834
0.902	High Similarity	NPC329282
0.8932	High Similarity	NPC172483
0.8879	High Similarity	NPC143768
0.8868	High Similarity	NPC474057
0.8776	High Similarity	NPC153885
0.8739	High Similarity	NPC318173
0.8738	High Similarity	NPC274443
0.8727	High Similarity	NPC469843
0.8704	High Similarity	NPC470253
0.8692	High Similarity	NPC265513
0.8687	High Similarity	NPC238219
0.8673	High Similarity	NPC133461
0.8649	High Similarity	NPC222968
0.8649	High Similarity	NPC323440
0.8649	High Similarity	NPC80605
0.8641	High Similarity	NPC244427
0.8641	High Similarity	NPC222390
0.8611	High Similarity	NPC186128
0.86	High Similarity	NPC260233
0.8586	High Similarity	NPC155232
0.8571	High Similarity	NPC134120
0.8545	High Similarity	NPC93181
0.8532	High Similarity	NPC93287
0.844	Intermediate Similarity	NPC218855
0.8431	Intermediate Similarity	NPC239185
0.84	Intermediate Similarity	NPC1682
0.84	Intermediate Similarity	NPC188844
0.8384	Intermediate Similarity	NPC173413
0.8381	Intermediate Similarity	NPC329556
0.8378	Intermediate Similarity	NPC217111
0.8378	Intermediate Similarity	NPC215419
0.8365	Intermediate Similarity	NPC225079
0.835	Intermediate Similarity	NPC75724
0.835	Intermediate Similarity	NPC49994
0.835	Intermediate Similarity	NPC134882
0.8318	Intermediate Similarity	NPC37914
0.8318	Intermediate Similarity	NPC185763
0.8318	Intermediate Similarity	NPC83409
0.83	Intermediate Similarity	NPC284475
0.8291	Intermediate Similarity	NPC318067
0.8291	Intermediate Similarity	NPC328107
0.8288	Intermediate Similarity	NPC471721
0.8288	Intermediate Similarity	NPC326664
0.8288	Intermediate Similarity	NPC130591
0.8288	Intermediate Similarity	NPC234637
0.8252	Intermediate Similarity	NPC156021
0.8252	Intermediate Similarity	NPC265220
0.8218	Intermediate Similarity	NPC323420
0.8214	Intermediate Similarity	NPC186933
0.8198	Intermediate Similarity	NPC471481
0.819	Intermediate Similarity	NPC476993
0.819	Intermediate Similarity	NPC109514
0.8182	Intermediate Similarity	NPC157778
0.8174	Intermediate Similarity	NPC476645
0.8174	Intermediate Similarity	NPC202015
0.8173	Intermediate Similarity	NPC145052
0.8163	Intermediate Similarity	NPC160339
0.8163	Intermediate Similarity	NPC307
0.8155	Intermediate Similarity	NPC219573
0.8155	Intermediate Similarity	NPC185208
0.8125	Intermediate Similarity	NPC67377
0.812	Intermediate Similarity	NPC167323
0.812	Intermediate Similarity	NPC269923
0.8108	Intermediate Similarity	NPC280789
0.8108	Intermediate Similarity	NPC66208
0.8081	Intermediate Similarity	NPC43945
0.8073	Intermediate Similarity	NPC203732
0.8073	Intermediate Similarity	NPC112903
0.8056	Intermediate Similarity	NPC471186
0.8053	Intermediate Similarity	NPC474095
0.8053	Intermediate Similarity	NPC274839
0.8039	Intermediate Similarity	NPC59677
0.8034	Intermediate Similarity	NPC472981
0.802	Intermediate Similarity	NPC277277
0.8019	Intermediate Similarity	NPC133809
0.8019	Intermediate Similarity	NPC136810
0.8019	Intermediate Similarity	NPC128248
0.8017	Intermediate Similarity	NPC204784
0.8	Intermediate Similarity	NPC192577
0.7983	Intermediate Similarity	NPC85511
0.7961	Intermediate Similarity	NPC34243
0.7961	Intermediate Similarity	NPC289883
0.7949	Intermediate Similarity	NPC105709
0.7946	Intermediate Similarity	NPC471189
0.7931	Intermediate Similarity	NPC472698
0.7931	Intermediate Similarity	NPC472697
0.79	Intermediate Similarity	NPC69057
0.7869	Intermediate Similarity	NPC478162
0.7869	Intermediate Similarity	NPC478165
0.7851	Intermediate Similarity	NPC123506
0.785	Intermediate Similarity	NPC112552
0.7838	Intermediate Similarity	NPC470252
0.7838	Intermediate Similarity	NPC318327
0.783	Intermediate Similarity	NPC329387
0.783	Intermediate Similarity	NPC317280
0.7826	Intermediate Similarity	NPC260886
0.7822	Intermediate Similarity	NPC477693
0.7822	Intermediate Similarity	NPC477704
0.7807	Intermediate Similarity	NPC196673
0.7798	Intermediate Similarity	NPC472222
0.7798	Intermediate Similarity	NPC472221
0.7797	Intermediate Similarity	NPC232958
0.7778	Intermediate Similarity	NPC304873
0.7778	Intermediate Similarity	NPC25458
0.7778	Intermediate Similarity	NPC320891
0.7767	Intermediate Similarity	NPC110704
0.7759	Intermediate Similarity	NPC158157
0.7757	Intermediate Similarity	NPC54647
0.775	Intermediate Similarity	NPC65627
0.7745	Intermediate Similarity	NPC418308
0.7739	Intermediate Similarity	NPC476357
0.7736	Intermediate Similarity	NPC240042
0.7736	Intermediate Similarity	NPC226041
0.7731	Intermediate Similarity	NPC476234
0.7724	Intermediate Similarity	NPC115797
0.7724	Intermediate Similarity	NPC51448
0.7714	Intermediate Similarity	NPC472880
0.7699	Intermediate Similarity	NPC137315
0.7699	Intermediate Similarity	NPC475002
0.7699	Intermediate Similarity	NPC95126
0.7699	Intermediate Similarity	NPC291799
0.7692	Intermediate Similarity	NPC268930
0.7685	Intermediate Similarity	NPC264728
0.7677	Intermediate Similarity	NPC215008
0.767	Intermediate Similarity	NPC86670
0.767	Intermediate Similarity	NPC70940
0.767	Intermediate Similarity	NPC19256
0.767	Intermediate Similarity	NPC274455
0.7658	Intermediate Similarity	NPC142326
0.7658	Intermediate Similarity	NPC94751
0.7658	Intermediate Similarity	NPC85560
0.7658	Intermediate Similarity	NPC244933
0.7653	Intermediate Similarity	NPC145053
0.7652	Intermediate Similarity	NPC241851
0.7652	Intermediate Similarity	NPC294458
0.7647	Intermediate Similarity	NPC267262
0.7647	Intermediate Similarity	NPC472680
0.7647	Intermediate Similarity	NPC153308
0.7647	Intermediate Similarity	NPC472679
0.7642	Intermediate Similarity	NPC474106
0.7642	Intermediate Similarity	NPC15837
0.7632	Intermediate Similarity	NPC471188
0.7623	Intermediate Similarity	NPC164014
0.7623	Intermediate Similarity	NPC295664
0.7603	Intermediate Similarity	NPC282577
0.76	Intermediate Similarity	NPC171460
0.7596	Intermediate Similarity	NPC476484
0.7593	Intermediate Similarity	NPC221825
0.7593	Intermediate Similarity	NPC217621
0.7586	Intermediate Similarity	NPC228936
0.7586	Intermediate Similarity	NPC470764
0.7573	Intermediate Similarity	NPC298115
0.757	Intermediate Similarity	NPC103048
0.7568	Intermediate Similarity	NPC105899
0.7561	Intermediate Similarity	NPC294050
0.7561	Intermediate Similarity	NPC328997
0.7551	Intermediate Similarity	NPC285716
0.7551	Intermediate Similarity	NPC190567
0.7551	Intermediate Similarity	NPC17408
0.7547	Intermediate Similarity	NPC172925
0.7545	Intermediate Similarity	NPC472691
0.7545	Intermediate Similarity	NPC474866
0.7545	Intermediate Similarity	NPC475939
0.7545	Intermediate Similarity	NPC255676
0.7545	Intermediate Similarity	NPC471829
0.7544	Intermediate Similarity	NPC133308
0.7542	Intermediate Similarity	NPC471553
0.7542	Intermediate Similarity	NPC61651
0.7541	Intermediate Similarity	NPC273683
0.7541	Intermediate Similarity	NPC472681
0.7525	Intermediate Similarity	NPC95965
0.7523	Intermediate Similarity	NPC472879
0.7521	Intermediate Similarity	NPC62138
0.7521	Intermediate Similarity	NPC135730
0.7521	Intermediate Similarity	NPC9274
0.752	Intermediate Similarity	NPC96024
0.75	Intermediate Similarity	NPC110420
0.75	Intermediate Similarity	NPC120393
0.75	Intermediate Similarity	NPC146239
0.75	Intermediate Similarity	NPC81135
0.75	Intermediate Similarity	NPC303967
0.75	Intermediate Similarity	NPC470648
0.75	Intermediate Similarity	NPC67585
0.75	Intermediate Similarity	NPC133302
0.75	Intermediate Similarity	NPC229242
0.748	Intermediate Similarity	NPC199273
0.7477	Intermediate Similarity	NPC249067
0.7477	Intermediate Similarity	NPC12695
0.7477	Intermediate Similarity	NPC469893
0.7476	Intermediate Similarity	NPC329064
0.746	Intermediate Similarity	NPC471832
0.7459	Intermediate Similarity	NPC307174
0.7458	Intermediate Similarity	NPC212891
0.7451	Intermediate Similarity	NPC164526
0.7449	Intermediate Similarity	NPC300205
0.7442	Intermediate Similarity	NPC474659
0.7442	Intermediate Similarity	NPC23894
0.744	Intermediate Similarity	NPC72667

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 NPC100767 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	213
0.1-0.2	923
0.2-0.3	1368
0.3-0.4	2913
0.4-0.5	2353
0.5-0.6	1146
0.6-0.7	187
0.7-0.8	36
0.8-0.85	10
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9231	High Similarity	NPD4141	Clinical (unspecified phase)
0.8431	Intermediate Similarity	NPD3495	Discontinued
0.84	Intermediate Similarity	NPD7631	Approved
0.8381	Intermediate Similarity	NPD1929	Approved
0.8381	Intermediate Similarity	NPD1930	Approved
0.8381	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.8317	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.83	Intermediate Similarity	NPD7609	Phase 3
0.8269	Intermediate Similarity	NPD2066	Phase 3
0.8113	Intermediate Similarity	NPD1932	Approved
0.8087	Intermediate Similarity	NPD7009	Phase 2
0.8081	Intermediate Similarity	NPD650	Approved
0.8	Intermediate Similarity	NPD2329	Discontinued
0.8	Intermediate Similarity	NPD7610	Discontinued
0.7895	Intermediate Similarity	NPD5951	Approved
0.7838	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7768	Intermediate Similarity	NPD1317	Discontinued
0.7731	Intermediate Similarity	NPD4879	Approved
0.7714	Intermediate Similarity	NPD1693	Approved
0.767	Intermediate Similarity	NPD1086	Approved
0.767	Intermediate Similarity	NPD1089	Approved
0.767	Intermediate Similarity	NPD1090	Approved
0.7647	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD800	Approved
0.7547	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD1088	Approved
0.748	Intermediate Similarity	NPD7961	Discontinued
0.7477	Intermediate Similarity	NPD1237	Approved
0.7438	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1087	Approved
0.7358	Intermediate Similarity	NPD1508	Approved
0.7355	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD942	Approved
0.7264	Intermediate Similarity	NPD1239	Approved
0.7248	Intermediate Similarity	NPD1566	Phase 3
0.7248	Intermediate Similarity	NPD1565	Approved
0.7248	Intermediate Similarity	NPD1564	Approved
0.7238	Intermediate Similarity	NPD5347	Phase 2
0.7238	Intermediate Similarity	NPD5346	Phase 2
0.7213	Intermediate Similarity	NPD2345	Approved
0.7188	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD4878	Approved
0.7156	Intermediate Similarity	NPD1843	Approved
0.7129	Intermediate Similarity	NPD226	Approved
0.7119	Intermediate Similarity	NPD6858	Approved
0.7119	Intermediate Similarity	NPD7094	Approved
0.7083	Intermediate Similarity	NPD3317	Approved
0.708	Intermediate Similarity	NPD6647	Phase 2
0.7054	Intermediate Similarity	NPD7008	Discontinued
0.7048	Intermediate Similarity	NPD4793	Discontinued
0.7018	Intermediate Similarity	NPD5909	Discontinued
0.7	Intermediate Similarity	NPD1989	Approved
0.6991	Remote Similarity	NPD2648	Phase 3
0.6991	Remote Similarity	NPD2193	Phase 2
0.699	Remote Similarity	NPD9491	Approved
0.6984	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD1563	Approved
0.6949	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD2932	Approved
0.6923	Remote Similarity	NPD2182	Approved
0.6909	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6049	Phase 2
0.6903	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1470	Approved
0.687	Remote Similarity	NPD164	Approved
0.6863	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.686	Remote Similarity	NPD690	Clinical (unspecified phase)
0.686	Remote Similarity	NPD2629	Approved
0.6855	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1245	Approved
0.6852	Remote Similarity	NPD9256	Approved
0.6852	Remote Similarity	NPD3672	Approved
0.6852	Remote Similarity	NPD3673	Approved
0.6852	Remote Similarity	NPD9258	Approved
0.6842	Remote Similarity	NPD2196	Discontinued
0.6835	Remote Similarity	NPD7236	Approved
0.6832	Remote Similarity	NPD227	Approved
0.6832	Remote Similarity	NPD225	Approved
0.6825	Remote Similarity	NPD1201	Approved
0.6818	Remote Similarity	NPD1202	Approved
0.68	Remote Similarity	NPD4199	Phase 3
0.68	Remote Similarity	NPD3019	Approved
0.6783	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD7084	Phase 3
0.6742	Remote Similarity	NPD6766	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD1246	Approved
0.6715	Remote Similarity	NPD2346	Discontinued
0.6714	Remote Similarity	NPD3300	Phase 2
0.6713	Remote Similarity	NPD7239	Suspended
0.6693	Remote Similarity	NPD6287	Discontinued
0.6692	Remote Similarity	NPD4980	Approved
0.6692	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3643	Approved
0.6667	Remote Similarity	NPD3971	Phase 1
0.6667	Remote Similarity	NPD5836	Discontinued
0.6667	Remote Similarity	NPD3644	Approved
0.6667	Remote Similarity	NPD3642	Approved
0.6642	Remote Similarity	NPD5404	Approved
0.6642	Remote Similarity	NPD5405	Approved
0.6642	Remote Similarity	NPD5408	Approved
0.6642	Remote Similarity	NPD5406	Approved
0.6638	Remote Similarity	NPD5765	Approved
0.6636	Remote Similarity	NPD9259	Approved
0.6636	Remote Similarity	NPD9257	Approved
0.6617	Remote Similarity	NPD5422	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD3026	Approved
0.6614	Remote Similarity	NPD3023	Approved
0.661	Remote Similarity	NPD6685	Approved
0.6602	Remote Similarity	NPD9490	Approved
0.6587	Remote Similarity	NPD3025	Approved
0.6587	Remote Similarity	NPD3024	Approved
0.6583	Remote Similarity	NPD664	Approved
0.6579	Remote Similarity	NPD9495	Approved
0.6571	Remote Similarity	NPD7003	Approved
0.6569	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD2799	Discontinued
0.6565	Remote Similarity	NPD2798	Approved
0.6562	Remote Similarity	NPD5618	Discontinued
0.6552	Remote Similarity	NPD2171	Approved
0.6549	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD6966	Discovery
0.6538	Remote Similarity	NPD1283	Approved
0.6538	Remote Similarity	NPD1876	Approved
0.6538	Remote Similarity	NPD4695	Discontinued
0.6535	Remote Similarity	NPD5306	Approved
0.6535	Remote Similarity	NPD5305	Approved
0.6532	Remote Similarity	NPD4198	Discontinued
0.6525	Remote Similarity	NPD2192	Approved
0.6525	Remote Similarity	NPD2197	Approved
0.6525	Remote Similarity	NPD1018	Approved
0.6525	Remote Similarity	NPD1677	Discontinued
0.6514	Remote Similarity	NPD1101	Approved
0.6512	Remote Similarity	NPD6637	Approved
0.6512	Remote Similarity	NPD3972	Approved
0.6504	Remote Similarity	NPD2650	Approved
0.6504	Remote Similarity	NPD2652	Approved
0.6504	Remote Similarity	NPD6010	Discontinued
0.6493	Remote Similarity	NPD3764	Approved
0.6481	Remote Similarity	NPD5280	Approved
0.6481	Remote Similarity	NPD5690	Phase 2
0.6481	Remote Similarity	NPD4694	Approved
0.6475	Remote Similarity	NPD9508	Approved
0.6462	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD5157	Phase 1
0.6462	Remote Similarity	NPD5159	Phase 2
0.6457	Remote Similarity	NPD4102	Approved
0.6457	Remote Similarity	NPD1651	Approved
0.6457	Remote Similarity	NPD4105	Approved
0.6446	Remote Similarity	NPD2067	Discontinued
0.6441	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD253	Approved
0.6434	Remote Similarity	NPD8165	Discontinued
0.6434	Remote Similarity	NPD4806	Approved
0.6434	Remote Similarity	NPD4807	Approved
0.6429	Remote Similarity	NPD6065	Approved
0.6423	Remote Similarity	NPD7635	Approved
0.6423	Remote Similarity	NPD5277	Phase 2
0.6412	Remote Similarity	NPD1574	Approved
0.6412	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD5048	Discontinued
0.6385	Remote Similarity	NPD3880	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD7082	Approved
0.6379	Remote Similarity	NPD7798	Approved
0.6379	Remote Similarity	NPD1238	Approved
0.6379	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD7077	Approved
0.6371	Remote Similarity	NPD7076	Approved
0.6371	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.637	Remote Similarity	NPD2846	Clinical (unspecified phase)
0.637	Remote Similarity	NPD2313	Discontinued
0.6364	Remote Similarity	NPD1164	Approved
0.6364	Remote Similarity	NPD1593	Approved
0.6357	Remote Similarity	NPD4106	Approved
0.6357	Remote Similarity	NPD4135	Approved
0.6357	Remote Similarity	NPD4136	Approved
0.6356	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD3357	Discontinued
0.6349	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD1099	Approved
0.6348	Remote Similarity	NPD1100	Approved
0.6343	Remote Similarity	NPD7055	Discontinued
0.6328	Remote Similarity	NPD5981	Approved
0.6319	Remote Similarity	NPD7390	Discontinued
0.6316	Remote Similarity	NPD4094	Approved
0.6316	Remote Similarity	NPD4814	Discontinued
0.6308	Remote Similarity	NPD1281	Approved
0.6296	Remote Similarity	NPD4197	Approved
0.6291	Remote Similarity	NPD7058	Phase 2
0.6291	Remote Similarity	NPD7057	Phase 3
0.6279	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3798	Phase 3
0.625	Remote Similarity	NPD4479	Discontinued
0.6241	Remote Similarity	NPD2343	Clinical (unspecified phase)

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