NPASS Compound

Structure

NPC469983 OpenBabel07101718322D 34 38 0 0 1 0 0 0 0 0999 V2000 2.6078 -1.6329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5712 -4.4388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9552 -0.0676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7897 -2.2651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2601 -0.5784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4020 -0.7883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7264 0.7154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5179 -0.5599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1370 -2.5494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0982 -0.8083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3555 -4.1545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0982 -1.0263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4658 0.0886 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6103 -0.8334 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4376 -1.2740 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.5133 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0058 -0.4844 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4013 -1.5314 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1316 -0.7359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0058 -1.8804 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.4013 0.3201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0801 -1.6047 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9018 0.2058 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4013 -0.8334 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8793 0.3395 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0650 -4.8149 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -1.3818 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5048 -1.4753 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0058 -2.8497 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1856 1.2651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5726 -3.2098 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3394 -1.6295 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6103 -1.5314 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 10 2 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 6 15 1 0 0 0 0 6 16 1 0 0 0 0 7 13 1 0 0 0 0 8 25 1 0 0 0 0 9 22 1 0 0 0 0 9 31 1 0 0 0 0 10 13 1 0 0 0 0 10 19 1 0 0 0 0 11 26 2 0 0 0 0 11 31 1 0 0 0 0 12 27 2 0 0 0 0 12 32 1 0 0 0 0 13 5 1 1 0 0 0 14 5 1 1 0 0 0 14 17 1 0 0 0 0 14 33 1 0 0 0 0 15 22 1 6 0 0 0 15 32 1 0 0 0 0 16 24 1 1 0 0 0 16 34 1 0 0 0 0 17 23 1 1 0 0 0 17 24 1 0 0 0 0 18 20 1 0 0 0 0 18 22 1 6 0 0 0 18 24 1 0 0 0 0 19 23 1 0 0 0 0 19 28 2 0 0 0 0 20 29 1 0 0 0 0 20 33 1 0 0 0 0 21 23 1 0 0 0 0 21 30 2 0 0 0 0 21 34 1 0 0 0 0 22 4 1 1 0 0 0 23 7 1 1 0 0 0 24 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	478.18
Volume:	455.598
LogP:	0.865
LogD:	0.234
LogS:	-3.249
# Rotatable Bonds:	6
TPSA:	145.66
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.25
Synthetic Accessibility Score:	6.62
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.626
MDCK Permeability:	5.365520701161586e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.981
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.334
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.209
Plasma Protein Binding (PPB):	30.88298225402832%
Volume Distribution (VD):	0.623
Pgp-substrate:	58.38558578491211%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.107
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.178
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.035
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.064
CYP3A4-inhibitor:	0.479
CYP3A4-substrate:	0.249

ADMET: Excretion

Clearance (CL):	2.311
Half-life (T1/2):	0.505

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.266
Drug-inuced Liver Injury (DILI):	0.352
AMES Toxicity:	0.5
Rat Oral Acute Toxicity:	0.295
Maximum Recommended Daily Dose:	0.506
Skin Sensitization:	0.158
Carcinogencity:	0.281
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.929

Download Data

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

Natural Product: NPC469983

Natural Product ID:	NPC469983
*Common Name:**	WSLLKHLHBNYZFR-UVAFYJSGSA-N
IUPAC Name:	n.a.
Synonyms:	3alpha-Acetoxymaoesin A
Standard InCHIKey:	WSLLKHLHBNYZFR-UVAFYJSGSA-N
Standard InCHI:	InChI=1S/C24H30O10/c1-10-13-5-14-17-23(7-13,19(10)28)21(30)34-16-6-15(32-12(3)27)22(4,9-31-11(2)26)18(20(29)33-14)24(16,17)8-25/h13-18,20,25,29H,1,5-9H2,2-4H3/t13-,14-,15-,16-,17-,18-,20?,22-,23+,24+/m1/s1
SMILES:	OC[C@@]12[C@H]3C[C@H]([C@@]([C@H]1C(O)O[C@H]1[C@@H]2[C@@]2(C(=O)O3)C[C@@H](C1)C(=C)C2=O)(C)COC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1641892
PubChem CID:	53319173
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene 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
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[469494]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[469494]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	>	10000.0	nM	PMID[469494]

☑ 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 NPC469983 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	269
0.1-0.2	1955
0.2-0.3	6224
0.3-0.4	10060
0.4-0.5	10572
0.5-0.6	6006
0.6-0.7	4624
0.7-0.8	2587
0.8-0.85	231
0.85-0.9	151
0.9-0.95	16
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.99	High Similarity	NPC232133
0.9412	High Similarity	NPC61071
0.9412	High Similarity	NPC88833
0.9412	High Similarity	NPC96333
0.9327	High Similarity	NPC85391
0.9307	High Similarity	NPC139347
0.93	High Similarity	NPC14634
0.9245	High Similarity	NPC132668
0.9223	High Similarity	NPC469746
0.9216	High Similarity	NPC101842
0.9216	High Similarity	NPC202793
0.9143	High Similarity	NPC49730
0.9143	High Similarity	NPC137104
0.9143	High Similarity	NPC474786
0.9143	High Similarity	NPC98069
0.9143	High Similarity	NPC320383
0.9135	High Similarity	NPC473410
0.9135	High Similarity	NPC471094
0.9135	High Similarity	NPC469984
0.9126	High Similarity	NPC164600
0.9126	High Similarity	NPC103172
0.9118	High Similarity	NPC96217
0.9109	High Similarity	NPC236585
0.9074	High Similarity	NPC88945
0.9057	High Similarity	NPC213320
0.9057	High Similarity	NPC329953
0.9048	High Similarity	NPC469744
0.9048	High Similarity	NPC274827
0.9048	High Similarity	NPC131903
0.9038	High Similarity	NPC471474
0.902	High Similarity	NPC275990
0.8972	High Similarity	NPC473397
0.8972	High Similarity	NPC474927
0.8962	High Similarity	NPC471476
0.8952	High Similarity	NPC63841
0.8952	High Similarity	NPC469729
0.8952	High Similarity	NPC469733
0.8942	High Similarity	NPC307660
0.8942	High Similarity	NPC12823
0.8942	High Similarity	NPC130511
0.8942	High Similarity	NPC56656
0.8922	High Similarity	NPC148279
0.8922	High Similarity	NPC46848
0.8911	High Similarity	NPC474793
0.8899	High Similarity	NPC229752
0.8879	High Similarity	NPC63244
0.8868	High Similarity	NPC102741
0.8857	High Similarity	NPC186054
0.8846	High Similarity	NPC474558
0.8835	High Similarity	NPC309388
0.8835	High Similarity	NPC475803
0.8824	High Similarity	NPC267921
0.8818	High Similarity	NPC473304
0.8818	High Similarity	NPC78836
0.8796	High Similarity	NPC471244
0.8796	High Similarity	NPC473352
0.8785	High Similarity	NPC255655
0.8785	High Similarity	NPC124053
0.8785	High Similarity	NPC473324
0.8785	High Similarity	NPC471093
0.8774	High Similarity	NPC89860
0.8774	High Similarity	NPC189663
0.8762	High Similarity	NPC4115
0.8762	High Similarity	NPC138908
0.8762	High Similarity	NPC200957
0.8738	High Similarity	NPC471790
0.8725	High Similarity	NPC26270
0.8725	High Similarity	NPC20479
0.8725	High Similarity	NPC38471
0.8725	High Similarity	NPC98837
0.8725	High Similarity	NPC28864
0.8725	High Similarity	NPC471038
0.8725	High Similarity	NPC38296
0.8725	High Similarity	NPC89099
0.8725	High Similarity	NPC162459
0.8716	High Similarity	NPC94141
0.8716	High Similarity	NPC471252
0.8704	High Similarity	NPC122339
0.8704	High Similarity	NPC29505
0.8692	High Similarity	NPC118721
0.8692	High Similarity	NPC252679
0.8679	High Similarity	NPC176949
0.8679	High Similarity	NPC201908
0.8679	High Similarity	NPC166993
0.8667	High Similarity	NPC244247
0.8654	High Similarity	NPC148628
0.8654	High Similarity	NPC88203
0.8654	High Similarity	NPC76866
0.8654	High Similarity	NPC304832
0.8654	High Similarity	NPC246736
0.8654	High Similarity	NPC214946
0.8654	High Similarity	NPC286519
0.8641	High Similarity	NPC293866
0.8636	High Similarity	NPC17165
0.8627	High Similarity	NPC96839
0.8627	High Similarity	NPC10864
0.8624	High Similarity	NPC145625
0.8624	High Similarity	NPC157929
0.8624	High Similarity	NPC473303
0.8624	High Similarity	NPC471245
0.8614	High Similarity	NPC470232
0.8598	High Similarity	NPC273155
0.8598	High Similarity	NPC55973
0.8585	High Similarity	NPC285927
0.8571	High Similarity	NPC122811
0.8571	High Similarity	NPC87927
0.8558	High Similarity	NPC52899
0.8558	High Similarity	NPC289148
0.8558	High Similarity	NPC163963
0.8545	High Similarity	NPC320118
0.8545	High Similarity	NPC194273
0.8545	High Similarity	NPC73986
0.8532	High Similarity	NPC471251
0.8529	High Similarity	NPC200054
0.8529	High Similarity	NPC329910
0.8529	High Similarity	NPC29410
0.8515	High Similarity	NPC470385
0.8515	High Similarity	NPC470386
0.8515	High Similarity	NPC475118
0.8505	High Similarity	NPC67745
0.8505	High Similarity	NPC471461
0.8491	Intermediate Similarity	NPC84928
0.8491	Intermediate Similarity	NPC13149
0.8491	Intermediate Similarity	NPC301787
0.8468	Intermediate Similarity	NPC243354
0.8462	Intermediate Similarity	NPC470388
0.8462	Intermediate Similarity	NPC287676
0.8455	Intermediate Similarity	NPC476964
0.844	Intermediate Similarity	NPC98633
0.844	Intermediate Similarity	NPC130302
0.8431	Intermediate Similarity	NPC98639
0.8431	Intermediate Similarity	NPC470229
0.8426	Intermediate Similarity	NPC231278
0.8426	Intermediate Similarity	NPC218123
0.8426	Intermediate Similarity	NPC112895
0.8411	Intermediate Similarity	NPC295366
0.8411	Intermediate Similarity	NPC222833
0.8396	Intermediate Similarity	NPC209298
0.8396	Intermediate Similarity	NPC277074
0.8396	Intermediate Similarity	NPC216114
0.8381	Intermediate Similarity	NPC252614
0.8378	Intermediate Similarity	NPC471248
0.8378	Intermediate Similarity	NPC285086
0.8365	Intermediate Similarity	NPC16911
0.8365	Intermediate Similarity	NPC78427
0.8364	Intermediate Similarity	NPC471243
0.8364	Intermediate Similarity	NPC56025
0.8364	Intermediate Similarity	NPC274833
0.8364	Intermediate Similarity	NPC11035
0.8364	Intermediate Similarity	NPC270586
0.835	Intermediate Similarity	NPC193785
0.835	Intermediate Similarity	NPC470387
0.835	Intermediate Similarity	NPC13949
0.8349	Intermediate Similarity	NPC8431
0.8349	Intermediate Similarity	NPC471250
0.8333	Intermediate Similarity	NPC471246
0.8333	Intermediate Similarity	NPC47853
0.8318	Intermediate Similarity	NPC98603
0.8317	Intermediate Similarity	NPC250753
0.8317	Intermediate Similarity	NPC198242
0.8317	Intermediate Similarity	NPC211403
0.8288	Intermediate Similarity	NPC207845
0.8288	Intermediate Similarity	NPC472719
0.8288	Intermediate Similarity	NPC470543
0.8241	Intermediate Similarity	NPC37600
0.8235	Intermediate Similarity	NPC294263
0.8224	Intermediate Similarity	NPC159442
0.8214	Intermediate Similarity	NPC146563
0.8208	Intermediate Similarity	NPC121218
0.8208	Intermediate Similarity	NPC253886
0.8208	Intermediate Similarity	NPC39683
0.82	Intermediate Similarity	NPC56413
0.8198	Intermediate Similarity	NPC272242
0.819	Intermediate Similarity	NPC470478
0.819	Intermediate Similarity	NPC109059
0.819	Intermediate Similarity	NPC288
0.8182	Intermediate Similarity	NPC51947
0.8182	Intermediate Similarity	NPC473844
0.8155	Intermediate Similarity	NPC41649
0.8155	Intermediate Similarity	NPC101233
0.8155	Intermediate Similarity	NPC289539
0.8155	Intermediate Similarity	NPC129004
0.8155	Intermediate Similarity	NPC153775
0.8155	Intermediate Similarity	NPC91772
0.8155	Intermediate Similarity	NPC111524
0.8155	Intermediate Similarity	NPC292374
0.8155	Intermediate Similarity	NPC104371
0.8155	Intermediate Similarity	NPC261333
0.8155	Intermediate Similarity	NPC215271
0.8155	Intermediate Similarity	NPC29247
0.8148	Intermediate Similarity	NPC88469
0.8148	Intermediate Similarity	NPC96268
0.8148	Intermediate Similarity	NPC47281
0.8142	Intermediate Similarity	NPC54395
0.8137	Intermediate Similarity	NPC470230
0.8137	Intermediate Similarity	NPC476934
0.8136	Intermediate Similarity	NPC469842
0.8136	Intermediate Similarity	NPC469841
0.8131	Intermediate Similarity	NPC471254
0.8131	Intermediate Similarity	NPC170615

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 NPC469983 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	266
0.1-0.2	2362
0.2-0.3	3946
0.3-0.4	1652
0.4-0.5	468
0.5-0.6	245
0.6-0.7	145
0.7-0.8	64
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7899	Intermediate Similarity	NPD8328	Phase 3
0.7739	Intermediate Similarity	NPD8133	Approved
0.7724	Intermediate Similarity	NPD7319	Approved
0.7692	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD7736	Approved
0.7544	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD6370	Approved
0.75	Intermediate Similarity	NPD6882	Approved
0.75	Intermediate Similarity	NPD6319	Approved
0.748	Intermediate Similarity	NPD7507	Approved
0.7456	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD8034	Phase 2
0.7453	Intermediate Similarity	NPD8035	Phase 2
0.7419	Intermediate Similarity	NPD8293	Discontinued
0.7414	Intermediate Similarity	NPD6650	Approved
0.7414	Intermediate Similarity	NPD6649	Approved
0.7398	Intermediate Similarity	NPD7492	Approved
0.7391	Intermediate Similarity	NPD6373	Approved
0.7391	Intermediate Similarity	NPD6372	Approved
0.7368	Intermediate Similarity	NPD5697	Approved
0.7368	Intermediate Similarity	NPD6412	Phase 2
0.7355	Intermediate Similarity	NPD6054	Approved
0.7339	Intermediate Similarity	NPD6616	Approved
0.7304	Intermediate Similarity	NPD6686	Approved
0.7304	Intermediate Similarity	NPD6899	Approved
0.7304	Intermediate Similarity	NPD6881	Approved
0.7295	Intermediate Similarity	NPD6015	Approved
0.7295	Intermediate Similarity	NPD6016	Approved
0.7281	Intermediate Similarity	NPD6675	Approved
0.7281	Intermediate Similarity	NPD7128	Approved
0.7281	Intermediate Similarity	NPD5739	Approved
0.7281	Intermediate Similarity	NPD6402	Approved
0.728	Intermediate Similarity	NPD7078	Approved
0.725	Intermediate Similarity	NPD6009	Approved
0.7241	Intermediate Similarity	NPD6014	Approved
0.7241	Intermediate Similarity	NPD6013	Approved
0.7241	Intermediate Similarity	NPD6012	Approved
0.7236	Intermediate Similarity	NPD5988	Approved
0.7217	Intermediate Similarity	NPD5701	Approved
0.7213	Intermediate Similarity	NPD6059	Approved
0.7212	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD8297	Approved
0.7193	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7102	Approved
0.7179	Intermediate Similarity	NPD7290	Approved
0.7179	Intermediate Similarity	NPD6883	Approved
0.7155	Intermediate Similarity	NPD7320	Approved
0.7155	Intermediate Similarity	NPD6011	Approved
0.7143	Intermediate Similarity	NPD4632	Approved
0.713	Intermediate Similarity	NPD6008	Approved
0.7119	Intermediate Similarity	NPD6847	Approved
0.7119	Intermediate Similarity	NPD8130	Phase 1
0.7119	Intermediate Similarity	NPD6869	Approved
0.7119	Intermediate Similarity	NPD6617	Approved
0.7064	Intermediate Similarity	NPD6399	Phase 3
0.7049	Intermediate Similarity	NPD7328	Approved
0.7049	Intermediate Similarity	NPD7327	Approved
0.7034	Intermediate Similarity	NPD4634	Approved
0.7016	Intermediate Similarity	NPD8296	Approved
0.7016	Intermediate Similarity	NPD8380	Approved
0.7016	Intermediate Similarity	NPD8378	Approved
0.7016	Intermediate Similarity	NPD8379	Approved
0.7016	Intermediate Similarity	NPD8335	Approved
0.6992	Remote Similarity	NPD7516	Approved
0.6991	Remote Similarity	NPD5285	Approved
0.6991	Remote Similarity	NPD5286	Approved
0.6991	Remote Similarity	NPD4696	Approved
0.6972	Remote Similarity	NPD6079	Approved
0.6967	Remote Similarity	NPD7115	Discovery
0.6964	Remote Similarity	NPD7902	Approved
0.6964	Remote Similarity	NPD4755	Approved
0.6944	Remote Similarity	NPD5328	Approved
0.6935	Remote Similarity	NPD8294	Approved
0.6935	Remote Similarity	NPD8377	Approved
0.6903	Remote Similarity	NPD7638	Approved
0.6885	Remote Similarity	NPD6274	Approved
0.688	Remote Similarity	NPD8516	Approved
0.688	Remote Similarity	NPD8515	Approved
0.688	Remote Similarity	NPD8517	Approved
0.688	Remote Similarity	NPD5983	Phase 2
0.688	Remote Similarity	NPD8513	Phase 3
0.688	Remote Similarity	NPD8033	Approved
0.688	Remote Similarity	NPD6921	Approved
0.6875	Remote Similarity	NPD5222	Approved
0.6875	Remote Similarity	NPD4697	Phase 3
0.6875	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5221	Approved
0.687	Remote Similarity	NPD5224	Approved
0.687	Remote Similarity	NPD5211	Phase 2
0.687	Remote Similarity	NPD5225	Approved
0.687	Remote Similarity	NPD5226	Approved
0.687	Remote Similarity	NPD4633	Approved
0.6847	Remote Similarity	NPD7748	Approved
0.6842	Remote Similarity	NPD7639	Approved
0.6842	Remote Similarity	NPD4700	Approved
0.6842	Remote Similarity	NPD7640	Approved
0.6833	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD3618	Phase 1
0.6818	Remote Similarity	NPD7515	Phase 2
0.6814	Remote Similarity	NPD5173	Approved
0.681	Remote Similarity	NPD5174	Approved
0.681	Remote Similarity	NPD5175	Approved
0.6783	Remote Similarity	NPD5223	Approved
0.6772	Remote Similarity	NPD7604	Phase 2
0.6759	Remote Similarity	NPD3573	Approved
0.6752	Remote Similarity	NPD5141	Approved
0.675	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD7503	Approved
0.6723	Remote Similarity	NPD4729	Approved
0.6723	Remote Similarity	NPD4730	Approved
0.672	Remote Similarity	NPD7101	Approved
0.672	Remote Similarity	NPD7100	Approved
0.6699	Remote Similarity	NPD6697	Approved
0.6699	Remote Similarity	NPD6114	Approved
0.6699	Remote Similarity	NPD6115	Approved
0.6699	Remote Similarity	NPD6118	Approved
0.6696	Remote Similarity	NPD7900	Approved
0.6696	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD4768	Approved
0.6695	Remote Similarity	NPD4767	Approved
0.6694	Remote Similarity	NPD6317	Approved
0.6692	Remote Similarity	NPD6033	Approved
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD6411	Approved
0.6667	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6336	Discontinued
0.664	Remote Similarity	NPD6314	Approved
0.664	Remote Similarity	NPD6335	Approved
0.664	Remote Similarity	NPD6313	Approved
0.6614	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD6868	Approved
0.6612	Remote Similarity	NPD5247	Approved
0.6612	Remote Similarity	NPD5249	Phase 3
0.6612	Remote Similarity	NPD5251	Approved
0.6612	Remote Similarity	NPD5250	Approved
0.6612	Remote Similarity	NPD5248	Approved
0.6609	Remote Similarity	NPD4225	Approved
0.6609	Remote Similarity	NPD5696	Approved
0.6607	Remote Similarity	NPD4202	Approved
0.6602	Remote Similarity	NPD6116	Phase 1
0.6583	Remote Similarity	NPD5128	Approved
0.6569	Remote Similarity	NPD3703	Phase 2
0.6542	Remote Similarity	NPD4788	Approved
0.6525	Remote Similarity	NPD4754	Approved
0.6514	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6067	Discontinued
0.6505	Remote Similarity	NPD6117	Approved
0.65	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD5695	Phase 3
0.6486	Remote Similarity	NPD6101	Approved
0.6486	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6908	Approved
0.6484	Remote Similarity	NPD6909	Approved
0.6481	Remote Similarity	NPD4786	Approved
0.6449	Remote Similarity	NPD3667	Approved
0.6441	Remote Similarity	NPD7632	Discontinued
0.6423	Remote Similarity	NPD5217	Approved
0.6423	Remote Similarity	NPD5215	Approved
0.6423	Remote Similarity	NPD5216	Approved
0.6396	Remote Similarity	NPD5737	Approved
0.6396	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD6672	Approved
0.6389	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD3669	Approved
0.6377	Remote Similarity	NPD6334	Approved
0.6377	Remote Similarity	NPD6333	Approved
0.6372	Remote Similarity	NPD7637	Suspended
0.6364	Remote Similarity	NPD6409	Approved
0.6364	Remote Similarity	NPD5330	Approved
0.6364	Remote Similarity	NPD6684	Approved
0.6364	Remote Similarity	NPD7146	Approved
0.6364	Remote Similarity	NPD7334	Approved
0.6364	Remote Similarity	NPD7521	Approved
0.6356	Remote Similarity	NPD1700	Approved
0.6355	Remote Similarity	NPD1780	Approved
0.6355	Remote Similarity	NPD1779	Approved
0.6348	Remote Similarity	NPD4629	Approved
0.6348	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD5210	Approved
0.6348	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD5169	Approved
0.6341	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD5135	Approved
0.6339	Remote Similarity	NPD4753	Phase 2
0.633	Remote Similarity	NPD3665	Phase 1
0.633	Remote Similarity	NPD3666	Approved
0.633	Remote Similarity	NPD3133	Approved
0.6316	Remote Similarity	NPD8171	Discontinued
0.6316	Remote Similarity	NPD5779	Approved
0.6316	Remote Similarity	NPD8337	Approved
0.6316	Remote Similarity	NPD5778	Approved
0.6316	Remote Similarity	NPD8336	Approved
0.6311	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD5168	Approved
0.629	Remote Similarity	NPD5127	Approved
0.6261	Remote Similarity	NPD5282	Discontinued
0.625	Remote Similarity	NPD8338	Approved
0.625	Remote Similarity	NPD3702	Approved
0.625	Remote Similarity	NPD6903	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