NPASS Compound

Structure

NPC469982 OpenBabel07101718322D 27 30 0 0 1 0 0 0 0 0999 V2000 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8225 2.4074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2086 -0.2100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9711 -0.0384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9879 -2.0035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5487 -1.3518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1431 -1.8437 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 0.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4506 0.4423 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 1.8786 2.0771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4200 -0.3805 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 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 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 2.2647 -0.5403 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8592 -1.0321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.1206 2.7294 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 0.2990 1.8456 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 1.6927 1.0945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 2 0 0 0 0 2 13 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 20 1 0 0 0 0 7 21 1 0 0 0 0 8 16 1 0 0 0 0 9 14 1 0 0 0 0 9 17 1 0 0 0 0 10 15 1 0 0 0 0 10 18 1 0 0 0 0 11 20 1 0 0 0 0 11 27 1 0 0 0 0 12 14 1 0 0 0 0 12 19 1 0 0 0 0 13 23 2 0 0 0 0 13 27 1 0 0 0 0 14 8 1 1 0 0 0 15 20 1 6 0 0 0 15 21 1 0 0 0 0 16 21 1 6 0 0 0 16 22 1 0 0 0 0 17 22 1 6 0 0 0 17 24 1 0 0 0 0 18 22 1 0 0 0 0 18 25 2 0 0 0 0 19 22 1 1 0 0 0 19 26 1 0 0 0 0 20 3 1 1 0 0 0 21 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	376.22
Volume:	390.884
LogP:	2.154
LogD:	1.765
LogS:	-3.778
# Rotatable Bonds:	3
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.572
Synthetic Accessibility Score:	6.126
Fsp3:	0.818
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:	-4.833
MDCK Permeability:	2.912409763666801e-05
Pgp-inhibitor:	0.089
Pgp-substrate:	0.983
Human Intestinal Absorption (HIA):	0.088
20% Bioavailability (F20%):	0.122
30% Bioavailability (F30%):	0.162

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.935
Plasma Protein Binding (PPB):	52.55549240112305%
Volume Distribution (VD):	0.936
Pgp-substrate:	52.74992752075195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.177
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.631
CYP2C9-inhibitor:	0.038
CYP2C9-substrate:	0.075
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.137
CYP3A4-inhibitor:	0.299
CYP3A4-substrate:	0.219

ADMET: Excretion

Clearance (CL):	3.433
Half-life (T1/2):	0.653

ADMET: Toxicity

hERG Blockers:	0.335
Human Hepatotoxicity (H-HT):	0.433
Drug-inuced Liver Injury (DILI):	0.434
AMES Toxicity:	0.361
Rat Oral Acute Toxicity:	0.979
Maximum Recommended Daily Dose:	0.998
Skin Sensitization:	0.666
Carcinogencity:	0.295
Eye Corrosion:	0.248
Eye Irritation:	0.465
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC469982

Natural Product ID:	NPC469982
*Common Name:**	Eriocatisin A
IUPAC Name:	n.a.
Synonyms:	Eriocatisin A
Standard InCHIKey:	BYVWPVXIWCZURJ-LKYQUMQOSA-N
Standard InCHI:	InChI=1S/C22H32O5/c1-12-14-8-16-21(4)7-5-6-20(3,11-27-13(2)23)15(21)10-18(25)22(16,19(12)26)17(24)9-14/h14-17,19,24,26H,1,5-11H2,2-4H3/t14-,15-,16+,17-,19-,20+,21-,22?/m1/s1
SMILES:	CC(=O)OCC1(CCCC2(C1CC(=O)C34C2CC(CC3O)C(=C)C4O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1641886
PubChem CID:	53321795
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003401] Villanovane, atisane, trachylobane or helvifulvane diterpenoids [CHEMONTID:0002738] Atisane diterpenoids

*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
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17020288]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[20949916]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[20949916]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22624550]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	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
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	10000.0	nM	PMID[536085]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[536085]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	>	10000.0	nM	PMID[536085]

☑ 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 NPC469982 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	257
0.1-0.2	1876
0.2-0.3	5627
0.3-0.4	11733
0.4-0.5	10810
0.5-0.6	6061
0.6-0.7	4249
0.7-0.8	1924
0.8-0.85	149
0.85-0.9	10
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8696	High Similarity	NPC198054
0.8646	High Similarity	NPC37047
0.8646	High Similarity	NPC41971
0.8646	High Similarity	NPC180733
0.8602	High Similarity	NPC471902
0.8602	High Similarity	NPC199543
0.8602	High Similarity	NPC287118
0.8602	High Similarity	NPC473690
0.8586	High Similarity	NPC37600
0.8557	High Similarity	NPC253886
0.8557	High Similarity	NPC121218
0.8557	High Similarity	NPC46848
0.8557	High Similarity	NPC75941
0.8556	High Similarity	NPC83242
0.8556	High Similarity	NPC187545
0.8526	High Similarity	NPC329910
0.8511	High Similarity	NPC47853
0.8495	Intermediate Similarity	NPC6255
0.8495	Intermediate Similarity	NPC476934
0.8495	Intermediate Similarity	NPC471588
0.8495	Intermediate Similarity	NPC475416
0.8495	Intermediate Similarity	NPC471901
0.8478	Intermediate Similarity	NPC213832
0.8478	Intermediate Similarity	NPC57954
0.8469	Intermediate Similarity	NPC286519
0.8469	Intermediate Similarity	NPC214946
0.8469	Intermediate Similarity	NPC88203
0.8469	Intermediate Similarity	NPC246736
0.8469	Intermediate Similarity	NPC275990
0.8469	Intermediate Similarity	NPC76866
0.8469	Intermediate Similarity	NPC148628
0.8469	Intermediate Similarity	NPC304832
0.8454	Intermediate Similarity	NPC287676
0.8454	Intermediate Similarity	NPC94906
0.8438	Intermediate Similarity	NPC476878
0.8438	Intermediate Similarity	NPC476879
0.8421	Intermediate Similarity	NPC263135
0.8421	Intermediate Similarity	NPC288906
0.8421	Intermediate Similarity	NPC470229
0.8421	Intermediate Similarity	NPC470232
0.8404	Intermediate Similarity	NPC244356
0.8404	Intermediate Similarity	NPC224060
0.84	Intermediate Similarity	NPC295366
0.8384	Intermediate Similarity	NPC95899
0.8384	Intermediate Similarity	NPC469985
0.837	Intermediate Similarity	NPC471900
0.837	Intermediate Similarity	NPC16377
0.8367	Intermediate Similarity	NPC163963
0.8367	Intermediate Similarity	NPC52899
0.8367	Intermediate Similarity	NPC295276
0.8367	Intermediate Similarity	NPC289148
0.8351	Intermediate Similarity	NPC78427
0.8351	Intermediate Similarity	NPC472028
0.8351	Intermediate Similarity	NPC474793
0.8351	Intermediate Similarity	NPC38471
0.8351	Intermediate Similarity	NPC162459
0.8351	Intermediate Similarity	NPC98837
0.8351	Intermediate Similarity	NPC20479
0.8351	Intermediate Similarity	NPC471038
0.8351	Intermediate Similarity	NPC38296
0.8351	Intermediate Similarity	NPC28864
0.8351	Intermediate Similarity	NPC16911
0.8333	Intermediate Similarity	NPC317573
0.8333	Intermediate Similarity	NPC98874
0.8333	Intermediate Similarity	NPC237938
0.8333	Intermediate Similarity	NPC219535
0.8316	Intermediate Similarity	NPC159365
0.8316	Intermediate Similarity	NPC475118
0.8316	Intermediate Similarity	NPC474529
0.8316	Intermediate Similarity	NPC470386
0.8316	Intermediate Similarity	NPC78580
0.8316	Intermediate Similarity	NPC23621
0.8316	Intermediate Similarity	NPC470385
0.8316	Intermediate Similarity	NPC184006
0.83	Intermediate Similarity	NPC47281
0.8298	Intermediate Similarity	NPC288833
0.8298	Intermediate Similarity	NPC211403
0.8298	Intermediate Similarity	NPC324341
0.8298	Intermediate Similarity	NPC198242
0.8298	Intermediate Similarity	NPC228784
0.8298	Intermediate Similarity	NPC282616
0.8298	Intermediate Similarity	NPC966
0.8298	Intermediate Similarity	NPC155120
0.8298	Intermediate Similarity	NPC475708
0.8298	Intermediate Similarity	NPC250753
0.8283	Intermediate Similarity	NPC476890
0.8283	Intermediate Similarity	NPC170615
0.8283	Intermediate Similarity	NPC124544
0.828	Intermediate Similarity	NPC194642
0.8265	Intermediate Similarity	NPC293866
0.8265	Intermediate Similarity	NPC293890
0.8261	Intermediate Similarity	NPC33768
0.8261	Intermediate Similarity	NPC269360
0.8261	Intermediate Similarity	NPC264005
0.8247	Intermediate Similarity	NPC10864
0.8247	Intermediate Similarity	NPC470425
0.8247	Intermediate Similarity	NPC26413
0.8247	Intermediate Similarity	NPC253586
0.8247	Intermediate Similarity	NPC189880
0.8242	Intermediate Similarity	NPC201655
0.8229	Intermediate Similarity	NPC98639
0.8229	Intermediate Similarity	NPC210214
0.8229	Intermediate Similarity	NPC148523
0.8229	Intermediate Similarity	NPC474727
0.8229	Intermediate Similarity	NPC195715
0.8229	Intermediate Similarity	NPC23241
0.8222	Intermediate Similarity	NPC471037
0.8218	Intermediate Similarity	NPC200957
0.8218	Intermediate Similarity	NPC138908
0.8218	Intermediate Similarity	NPC50535
0.8211	Intermediate Similarity	NPC86368
0.8211	Intermediate Similarity	NPC294263
0.82	Intermediate Similarity	NPC476889
0.82	Intermediate Similarity	NPC90177
0.82	Intermediate Similarity	NPC87927
0.82	Intermediate Similarity	NPC139347
0.82	Intermediate Similarity	NPC478057
0.8191	Intermediate Similarity	NPC172361
0.8191	Intermediate Similarity	NPC169933
0.8191	Intermediate Similarity	NPC86372
0.8182	Intermediate Similarity	NPC476888
0.8182	Intermediate Similarity	NPC39683
0.8182	Intermediate Similarity	NPC71706
0.8182	Intermediate Similarity	NPC236585
0.8182	Intermediate Similarity	NPC93744
0.8172	Intermediate Similarity	NPC474719
0.8172	Intermediate Similarity	NPC4309
0.8163	Intermediate Similarity	NPC89099
0.8163	Intermediate Similarity	NPC58942
0.8163	Intermediate Similarity	NPC477653
0.8163	Intermediate Similarity	NPC260149
0.8163	Intermediate Similarity	NPC174663
0.8163	Intermediate Similarity	NPC164349
0.8155	Intermediate Similarity	NPC154906
0.8152	Intermediate Similarity	NPC12774
0.8152	Intermediate Similarity	NPC322159
0.8152	Intermediate Similarity	NPC2783
0.8144	Intermediate Similarity	NPC223169
0.8144	Intermediate Similarity	NPC476318
0.8144	Intermediate Similarity	NPC29410
0.8144	Intermediate Similarity	NPC219353
0.8144	Intermediate Similarity	NPC200054
0.8144	Intermediate Similarity	NPC13949
0.8144	Intermediate Similarity	NPC470387
0.8144	Intermediate Similarity	NPC476327
0.8144	Intermediate Similarity	NPC234564
0.8137	Intermediate Similarity	NPC176949
0.8137	Intermediate Similarity	NPC166993
0.8137	Intermediate Similarity	NPC201908
0.8125	Intermediate Similarity	NPC272635
0.8125	Intermediate Similarity	NPC277399
0.8125	Intermediate Similarity	NPC169751
0.8125	Intermediate Similarity	NPC222047
0.8119	Intermediate Similarity	NPC474281
0.8119	Intermediate Similarity	NPC84928
0.8119	Intermediate Similarity	NPC98603
0.8105	Intermediate Similarity	NPC470230
0.81	Intermediate Similarity	NPC40918
0.8085	Intermediate Similarity	NPC471043
0.8085	Intermediate Similarity	NPC130520
0.8085	Intermediate Similarity	NPC270768
0.8085	Intermediate Similarity	NPC61543
0.8085	Intermediate Similarity	NPC474700
0.8085	Intermediate Similarity	NPC225585
0.8085	Intermediate Similarity	NPC293048
0.8085	Intermediate Similarity	NPC127689
0.8085	Intermediate Similarity	NPC281524
0.8085	Intermediate Similarity	NPC59263
0.8085	Intermediate Similarity	NPC234346
0.8085	Intermediate Similarity	NPC121798
0.8085	Intermediate Similarity	NPC263393
0.8081	Intermediate Similarity	NPC108371
0.8081	Intermediate Similarity	NPC473576
0.8081	Intermediate Similarity	NPC477655
0.8081	Intermediate Similarity	NPC475156
0.8065	Intermediate Similarity	NPC259009
0.8065	Intermediate Similarity	NPC4643
0.8065	Intermediate Similarity	NPC158141
0.8065	Intermediate Similarity	NPC134197
0.8065	Intermediate Similarity	NPC173089
0.8065	Intermediate Similarity	NPC57469
0.8061	Intermediate Similarity	NPC89225
0.8058	Intermediate Similarity	NPC112895
0.8058	Intermediate Similarity	NPC218123
0.8058	Intermediate Similarity	NPC273155
0.8058	Intermediate Similarity	NPC231278
0.8043	Intermediate Similarity	NPC292553
0.8043	Intermediate Similarity	NPC294438
0.8043	Intermediate Similarity	NPC264317
0.8043	Intermediate Similarity	NPC164424
0.8041	Intermediate Similarity	NPC266899
0.8041	Intermediate Similarity	NPC41070
0.8041	Intermediate Similarity	NPC205173
0.8041	Intermediate Similarity	NPC266431
0.8041	Intermediate Similarity	NPC473240
0.8039	Intermediate Similarity	NPC80566
0.8039	Intermediate Similarity	NPC28791
0.8039	Intermediate Similarity	NPC4115
0.8021	Intermediate Similarity	NPC214756
0.8021	Intermediate Similarity	NPC295643

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 NPC469982 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	251
0.1-0.2	2293
0.2-0.3	3807
0.3-0.4	1833
0.4-0.5	558
0.5-0.6	253
0.6-0.7	141
0.7-0.8	14
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
0.8043	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7938	Intermediate Similarity	NPD7748	Approved
0.7917	Intermediate Similarity	NPD8035	Phase 2
0.7917	Intermediate Similarity	NPD8034	Phase 2
0.7917	Intermediate Similarity	NPD7515	Phase 2
0.7714	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD7902	Approved
0.7549	Intermediate Similarity	NPD7640	Approved
0.7549	Intermediate Similarity	NPD7639	Approved
0.7475	Intermediate Similarity	NPD5779	Approved
0.7475	Intermediate Similarity	NPD5778	Approved
0.7451	Intermediate Similarity	NPD7638	Approved
0.74	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD7900	Approved
0.7374	Intermediate Similarity	NPD6411	Approved
0.7283	Intermediate Similarity	NPD6697	Approved
0.7283	Intermediate Similarity	NPD6114	Approved
0.7283	Intermediate Similarity	NPD6115	Approved
0.7283	Intermediate Similarity	NPD6118	Approved
0.7241	Intermediate Similarity	NPD8328	Phase 3
0.72	Intermediate Similarity	NPD7637	Suspended
0.7196	Intermediate Similarity	NPD6675	Approved
0.7196	Intermediate Similarity	NPD6402	Approved
0.7196	Intermediate Similarity	NPD5739	Approved
0.7196	Intermediate Similarity	NPD7128	Approved
0.7172	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6101	Approved
0.7168	Intermediate Similarity	NPD7115	Discovery
0.7168	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD6399	Phase 3
0.7075	Intermediate Similarity	NPD7632	Discontinued
0.7071	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD6117	Approved
0.7064	Intermediate Similarity	NPD7320	Approved
0.7064	Intermediate Similarity	NPD6881	Approved
0.7064	Intermediate Similarity	NPD6899	Approved
0.7054	Intermediate Similarity	NPD8133	Approved
0.7021	Intermediate Similarity	NPD7645	Phase 2
0.7019	Intermediate Similarity	NPD6083	Phase 2
0.7019	Intermediate Similarity	NPD6084	Phase 2
0.7	Intermediate Similarity	NPD5328	Approved
0.7	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6372	Approved
0.7	Intermediate Similarity	NPD6373	Approved
0.6989	Remote Similarity	NPD6116	Phase 1
0.6972	Remote Similarity	NPD5701	Approved
0.6972	Remote Similarity	NPD5697	Approved
0.6957	Remote Similarity	NPD3703	Phase 2
0.6952	Remote Similarity	NPD4225	Approved
0.6942	Remote Similarity	NPD7319	Approved
0.6937	Remote Similarity	NPD7290	Approved
0.6937	Remote Similarity	NPD7102	Approved
0.6937	Remote Similarity	NPD6883	Approved
0.6923	Remote Similarity	NPD6921	Approved
0.6907	Remote Similarity	NPD4788	Approved
0.6875	Remote Similarity	NPD8130	Phase 1
0.6875	Remote Similarity	NPD6650	Approved
0.6875	Remote Similarity	NPD6617	Approved
0.6875	Remote Similarity	NPD6869	Approved
0.6875	Remote Similarity	NPD6649	Approved
0.6875	Remote Similarity	NPD6847	Approved
0.6869	Remote Similarity	NPD7146	Approved
0.6869	Remote Similarity	NPD6684	Approved
0.6869	Remote Similarity	NPD7334	Approved
0.6869	Remote Similarity	NPD3618	Phase 1
0.6869	Remote Similarity	NPD6409	Approved
0.6869	Remote Similarity	NPD5330	Approved
0.6869	Remote Similarity	NPD7521	Approved
0.6863	Remote Similarity	NPD6079	Approved
0.686	Remote Similarity	NPD7736	Approved
0.6848	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD6014	Approved
0.6847	Remote Similarity	NPD6012	Approved
0.6847	Remote Similarity	NPD6013	Approved
0.6838	Remote Similarity	NPD6319	Approved
0.6837	Remote Similarity	NPD4786	Approved
0.6818	Remote Similarity	NPD6412	Phase 2
0.6814	Remote Similarity	NPD6882	Approved
0.6814	Remote Similarity	NPD8297	Approved
0.6804	Remote Similarity	NPD3667	Approved
0.68	Remote Similarity	NPD3573	Approved
0.6759	Remote Similarity	NPD5211	Phase 2
0.6757	Remote Similarity	NPD6686	Approved
0.6757	Remote Similarity	NPD6011	Approved
0.675	Remote Similarity	NPD7492	Approved
0.6733	Remote Similarity	NPD5737	Approved
0.6733	Remote Similarity	NPD6903	Approved
0.6733	Remote Similarity	NPD6672	Approved
0.6726	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD4755	Approved
0.6695	Remote Similarity	NPD6059	Approved
0.6695	Remote Similarity	NPD6054	Approved
0.6694	Remote Similarity	NPD6616	Approved
0.6694	Remote Similarity	NPD7507	Approved
0.6667	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD3666	Approved
0.6667	Remote Similarity	NPD3665	Phase 1
0.6639	Remote Similarity	NPD8293	Discontinued
0.6639	Remote Similarity	NPD7078	Approved
0.6637	Remote Similarity	NPD4634	Approved
0.6637	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5141	Approved
0.6636	Remote Similarity	NPD5696	Approved
0.663	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.663	Remote Similarity	NPD5777	Approved
0.663	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD4632	Approved
0.6604	Remote Similarity	NPD4697	Phase 3
0.6604	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5222	Approved
0.6604	Remote Similarity	NPD5221	Approved
0.6593	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD6370	Approved
0.6577	Remote Similarity	NPD6008	Approved
0.6574	Remote Similarity	NPD5286	Approved
0.6574	Remote Similarity	NPD4700	Approved
0.6574	Remote Similarity	NPD5285	Approved
0.6574	Remote Similarity	NPD4696	Approved
0.6566	Remote Similarity	NPD6695	Phase 3
0.6542	Remote Similarity	NPD5173	Approved
0.6538	Remote Similarity	NPD7983	Approved
0.6535	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4245	Approved
0.6522	Remote Similarity	NPD4244	Approved
0.6509	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD4753	Phase 2
0.65	Remote Similarity	NPD6015	Approved
0.65	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6016	Approved
0.6496	Remote Similarity	NPD6868	Approved
0.6496	Remote Similarity	NPD6274	Approved
0.6476	Remote Similarity	NPD4202	Approved
0.6471	Remote Similarity	NPD7100	Approved
0.6471	Remote Similarity	NPD7101	Approved
0.6465	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD5226	Approved
0.6455	Remote Similarity	NPD5224	Approved
0.6455	Remote Similarity	NPD4633	Approved
0.6455	Remote Similarity	NPD5225	Approved
0.6452	Remote Similarity	NPD6081	Approved
0.6449	Remote Similarity	NPD7614	Phase 1
0.6449	Remote Similarity	NPD7839	Suspended
0.6446	Remote Similarity	NPD5988	Approved
0.6444	Remote Similarity	NPD4224	Phase 2
0.6441	Remote Similarity	NPD6009	Approved
0.6429	Remote Similarity	NPD7525	Registered
0.6421	Remote Similarity	NPD3702	Approved
0.6413	Remote Similarity	NPD3698	Phase 2
0.6396	Remote Similarity	NPD5175	Approved
0.6396	Remote Similarity	NPD5174	Approved
0.6393	Remote Similarity	NPD7604	Phase 2
0.6392	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD7327	Approved
0.6387	Remote Similarity	NPD7328	Approved
0.6387	Remote Similarity	NPD6335	Approved
0.6373	Remote Similarity	NPD6098	Approved
0.6373	Remote Similarity	NPD5786	Approved
0.6372	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5223	Approved
0.6364	Remote Similarity	NPD5983	Phase 2
0.6364	Remote Similarity	NPD6909	Approved
0.6364	Remote Similarity	NPD6908	Approved
0.6355	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6904	Approved
0.6346	Remote Similarity	NPD6080	Approved
0.6346	Remote Similarity	NPD6673	Approved
0.6344	Remote Similarity	NPD4789	Approved
0.6337	Remote Similarity	NPD3668	Phase 3
0.6333	Remote Similarity	NPD7516	Approved
0.6327	Remote Similarity	NPD6929	Approved
0.6311	Remote Similarity	NPD7750	Discontinued
0.6311	Remote Similarity	NPD7524	Approved
0.6303	Remote Similarity	NPD6317	Approved
0.63	Remote Similarity	NPD4269	Approved
0.63	Remote Similarity	NPD6435	Approved
0.63	Remote Similarity	NPD4270	Approved
0.6296	Remote Similarity	NPD7732	Phase 3
0.629	Remote Similarity	NPD6336	Discontinued
0.6286	Remote Similarity	NPD5785	Approved
0.6283	Remote Similarity	NPD4768	Approved
0.6283	Remote Similarity	NPD4767	Approved
0.6275	Remote Similarity	NPD1694	Approved
0.6263	Remote Similarity	NPD6931	Approved
0.6263	Remote Similarity	NPD6930	Phase 2
0.6263	Remote Similarity	NPD4695	Discontinued
0.625	Remote Similarity	NPD6313	Approved
0.625	Remote Similarity	NPD6314	Approved
0.625	Remote Similarity	NPD4754	Approved
0.6239	Remote Similarity	NPD6053	Discontinued
0.6238	Remote Similarity	NPD7154	Phase 3
0.623	Remote Similarity	NPD8380	Approved
0.623	Remote Similarity	NPD8379	Approved
0.623	Remote Similarity	NPD8513	Phase 3
0.623	Remote Similarity	NPD8516	Approved
0.623	Remote Similarity	NPD8515	Approved
0.623	Remote Similarity	NPD8378	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