NPASS Compound

Structure

NPC98603 OpenBabel07101718282D 31 34 0 0 1 0 0 0 0 0999 V2000 2.1874 1.2195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4533 -2.5962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0394 -2.6323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3548 -1.8635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3225 -1.8490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1925 0.9858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4139 0.0361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8052 0.3755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6918 1.0481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6191 -1.0362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2669 0.9205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2842 -2.0998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8059 -2.1610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2102 1.5518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2174 -0.6788 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5983 0.3575 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4244 -0.6607 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0104 -0.6968 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4839 1.4893 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9678 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2991 0.9205 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8261 -1.0182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2070 0.0181 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1295 -2.5711 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6368 -2.6574 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5503 2.4579 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5367 -0.7830 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1400 1.5186 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2697 -1.1321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8204 -1.1932 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 2 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 22 1 0 0 0 0 5 22 1 0 0 0 0 7 8 1 0 0 0 0 7 17 1 0 0 0 0 8 23 1 0 0 0 0 9 14 1 0 0 0 0 9 16 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 12 25 2 0 0 0 0 12 30 1 0 0 0 0 13 26 2 0 0 0 0 13 31 1 0 0 0 0 14 19 1 0 0 0 0 14 27 2 0 0 0 0 15 22 1 0 0 0 0 15 23 1 6 0 0 0 16 23 1 6 0 0 0 16 24 1 0 0 0 0 17 22 1 0 0 0 0 17 30 1 1 0 0 0 18 24 1 6 0 0 0 18 31 1 0 0 0 0 19 11 1 1 0 0 0 19 21 1 0 0 0 0 20 28 2 0 0 0 0 21 24 1 6 0 0 0 21 29 1 0 0 0 0 23 6 1 6 0 0 0 24 20 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.21
Volume:	437.784
LogP:	2.415
LogD:	1.607
LogS:	-3.599
# Rotatable Bonds:	4
TPSA:	103.81
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.488
Synthetic Accessibility Score:	5.902
Fsp3:	0.792
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.962
MDCK Permeability:	5.8719408116303384e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.054
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.051
30% Bioavailability (F30%):	0.837

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.864
Plasma Protein Binding (PPB):	45.822837829589844%
Volume Distribution (VD):	0.54
Pgp-substrate:	57.219322204589844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.06
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.697
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.082
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.107
CYP3A4-inhibitor:	0.296
CYP3A4-substrate:	0.48

ADMET: Excretion

Clearance (CL):	6.803
Half-life (T1/2):	0.361

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.249
Drug-inuced Liver Injury (DILI):	0.767
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.957
Maximum Recommended Daily Dose:	0.927
Skin Sensitization:	0.102
Carcinogencity:	0.366
Eye Corrosion:	0.927
Eye Irritation:	0.087
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC98603

Natural Product ID:	NPC98603
*Common Name:**	7-O-Acetylpseurata C
IUPAC Name:	n.a.
Synonyms:	7-O-Acetylpseurata C
Standard InCHIKey:	ZJTQVLHYMFFVCC-DCMYVXTHSA-N
Standard InCHI:	InChI=1S/C24H32O7/c1-11-19-14(27)9-16-23(6)8-7-17(30-12(2)25)22(4,5)15(23)10-18(31-13(3)26)24(16,20(11)28)21(19)29/h15-19,21,29H,1,7-10H2,2-6H3/t15-,16+,17+,18-,19-,21-,23-,24+/m1/s1
SMILES:	C=C1[C@@H]2C(=O)C[C@H]3[C@]4(C)CC[C@@H](C(C)(C)[C@H]4C[C@H]([C@@]3(C1=O)[C@@H]2O)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL550161
PubChem CID:	44179019
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane 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
NPO24459	Isodon pharicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19425589]
NPO24459	Isodon pharicus	Species	Lamiaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[29286250]
NPO24459	Isodon pharicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24459	Isodon pharicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24459	Isodon pharicus	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2678	Cell Line	NB-4	Homo sapiens	IC50	>	10000.0	nM	PMID[540350]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[540350]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	IC50	>	10000.0	nM	PMID[540350]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	10000.0	nM	PMID[540350]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[540350]

☑ 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 NPC98603 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	240
0.1-0.2	1720
0.2-0.3	5676
0.3-0.4	9635
0.4-0.5	11035
0.5-0.6	6474
0.6-0.7	5467
0.7-0.8	2054
0.8-0.85	231
0.85-0.9	81
0.9-0.95	63
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
0.9896	High Similarity	NPC216114
0.9794	High Similarity	NPC84928
0.9688	High Similarity	NPC52899
0.9688	High Similarity	NPC289148
0.9688	High Similarity	NPC163963
0.9588	High Similarity	NPC286519
0.9588	High Similarity	NPC76866
0.9588	High Similarity	NPC304832
0.9588	High Similarity	NPC88203
0.9588	High Similarity	NPC148628
0.9588	High Similarity	NPC214946
0.9588	High Similarity	NPC246736
0.9583	High Similarity	NPC287676
0.949	High Similarity	NPC87927
0.9479	High Similarity	NPC16911
0.9479	High Similarity	NPC78427
0.9394	High Similarity	NPC474558
0.9286	High Similarity	NPC46848
0.9278	High Similarity	NPC471038
0.9271	High Similarity	NPC329910
0.9271	High Similarity	NPC140242
0.9271	High Similarity	NPC470387
0.9271	High Similarity	NPC13949
0.9192	High Similarity	NPC275990
0.9184	High Similarity	NPC293866
0.9167	High Similarity	NPC210214
0.9167	High Similarity	NPC470229
0.9167	High Similarity	NPC470232
0.9118	High Similarity	NPC112895
0.9118	High Similarity	NPC218123
0.9118	High Similarity	NPC231278
0.9091	High Similarity	NPC471790
0.9082	High Similarity	NPC20479
0.9082	High Similarity	NPC162459
0.9082	High Similarity	NPC38471
0.9082	High Similarity	NPC98837
0.9082	High Similarity	NPC38296
0.9082	High Similarity	NPC28864
0.9082	High Similarity	NPC474793
0.9082	High Similarity	NPC89099
0.9072	High Similarity	NPC200054
0.9072	High Similarity	NPC29410
0.9062	High Similarity	NPC64006
0.9062	High Similarity	NPC47853
0.9062	High Similarity	NPC470386
0.9062	High Similarity	NPC475118
0.9062	High Similarity	NPC470385
0.902	High Similarity	NPC176949
0.902	High Similarity	NPC201908
0.901	High Similarity	NPC202793
0.9	High Similarity	NPC475803
0.9	High Similarity	NPC309388
0.899	High Similarity	NPC156324
0.899	High Similarity	NPC55503
0.898	High Similarity	NPC10864
0.8969	High Similarity	NPC98639
0.8958	High Similarity	NPC294263
0.8958	High Similarity	NPC181594
0.8958	High Similarity	NPC144739
0.8932	High Similarity	NPC273155
0.8922	High Similarity	NPC138908
0.8922	High Similarity	NPC200957
0.8922	High Similarity	NPC37600
0.8922	High Similarity	NPC4115
0.8911	High Similarity	NPC139347
0.8911	High Similarity	NPC209298
0.8911	High Similarity	NPC277074
0.8911	High Similarity	NPC470310
0.8911	High Similarity	NPC122811
0.89	High Similarity	NPC71706
0.89	High Similarity	NPC295276
0.89	High Similarity	NPC236585
0.8866	High Similarity	NPC292374
0.8866	High Similarity	NPC91772
0.8866	High Similarity	NPC129004
0.8866	High Similarity	NPC289539
0.8866	High Similarity	NPC104371
0.8866	High Similarity	NPC215271
0.8866	High Similarity	NPC29247
0.8866	High Similarity	NPC261333
0.8866	High Similarity	NPC111524
0.8866	High Similarity	NPC153775
0.8866	High Similarity	NPC101233
0.8857	High Similarity	NPC329953
0.8854	High Similarity	NPC299185
0.8854	High Similarity	NPC211403
0.8854	High Similarity	NPC470230
0.8854	High Similarity	NPC476168
0.8854	High Similarity	NPC250753
0.8854	High Similarity	NPC198242
0.8835	High Similarity	NPC166993
0.8824	High Similarity	NPC96268
0.8824	High Similarity	NPC13149
0.88	High Similarity	NPC470388
0.8776	High Similarity	NPC84018
0.8776	High Similarity	NPC231060
0.8776	High Similarity	NPC138245
0.8774	High Similarity	NPC473352
0.8762	High Similarity	NPC471093
0.875	High Similarity	NPC261994
0.875	High Similarity	NPC180849
0.875	High Similarity	NPC470378
0.875	High Similarity	NPC149761
0.875	High Similarity	NPC80401
0.875	High Similarity	NPC211224
0.8738	High Similarity	NPC222833
0.8738	High Similarity	NPC295366
0.8738	High Similarity	NPC12823
0.8725	High Similarity	NPC96217
0.8725	High Similarity	NPC159442
0.8713	High Similarity	NPC253886
0.8713	High Similarity	NPC121218
0.8713	High Similarity	NPC252614
0.8713	High Similarity	NPC148279
0.8692	High Similarity	NPC471252
0.8687	High Similarity	NPC264979
0.8687	High Similarity	NPC135548
0.8687	High Similarity	NPC104568
0.8679	High Similarity	NPC29505
0.8679	High Similarity	NPC470281
0.8673	High Similarity	NPC302008
0.8673	High Similarity	NPC191094
0.8646	High Similarity	NPC471043
0.8641	High Similarity	NPC301787
0.8627	High Similarity	NPC170615
0.8614	High Similarity	NPC267921
0.8614	High Similarity	NPC94906
0.8598	High Similarity	NPC474927
0.8586	High Similarity	NPC266431
0.8571	High Similarity	NPC59170
0.8571	High Similarity	NPC59350
0.8571	High Similarity	NPC55973
0.8571	High Similarity	NPC469733
0.8571	High Similarity	NPC469729
0.8571	High Similarity	NPC63841
0.8571	High Similarity	NPC82138
0.8558	High Similarity	NPC265127
0.8544	High Similarity	NPC469985
0.8529	High Similarity	NPC14634
0.8529	High Similarity	NPC75941
0.8529	High Similarity	NPC60947
0.8515	High Similarity	NPC472028
0.8515	High Similarity	NPC26270
0.8505	High Similarity	NPC94650
0.8505	High Similarity	NPC213320
0.85	High Similarity	NPC234564
0.8491	Intermediate Similarity	NPC469744
0.8491	Intermediate Similarity	NPC102741
0.8476	Intermediate Similarity	NPC88833
0.8476	Intermediate Similarity	NPC67745
0.8476	Intermediate Similarity	NPC471246
0.8476	Intermediate Similarity	NPC469746
0.8476	Intermediate Similarity	NPC471461
0.8476	Intermediate Similarity	NPC96333
0.8476	Intermediate Similarity	NPC186054
0.8469	Intermediate Similarity	NPC278106
0.8462	Intermediate Similarity	NPC47281
0.8455	Intermediate Similarity	NPC473304
0.8447	Intermediate Similarity	NPC124544
0.8447	Intermediate Similarity	NPC272472
0.8438	Intermediate Similarity	NPC165895
0.8438	Intermediate Similarity	NPC153604
0.8438	Intermediate Similarity	NPC259009
0.8438	Intermediate Similarity	NPC174619
0.8431	Intermediate Similarity	NPC180733
0.8431	Intermediate Similarity	NPC127408
0.8431	Intermediate Similarity	NPC41971
0.8431	Intermediate Similarity	NPC291785
0.8431	Intermediate Similarity	NPC37047
0.8431	Intermediate Similarity	NPC108371
0.8426	Intermediate Similarity	NPC473397
0.8426	Intermediate Similarity	NPC471245
0.8426	Intermediate Similarity	NPC40608
0.8416	Intermediate Similarity	NPC96839
0.8416	Intermediate Similarity	NPC253586
0.8411	Intermediate Similarity	NPC320383
0.8411	Intermediate Similarity	NPC137104
0.8411	Intermediate Similarity	NPC474786
0.8411	Intermediate Similarity	NPC473324
0.84	Intermediate Similarity	NPC263135
0.84	Intermediate Similarity	NPC288906
0.84	Intermediate Similarity	NPC29112
0.8396	Intermediate Similarity	NPC189663
0.8396	Intermediate Similarity	NPC232133
0.8396	Intermediate Similarity	NPC89860
0.8396	Intermediate Similarity	NPC471094
0.8396	Intermediate Similarity	NPC473410
0.8396	Intermediate Similarity	NPC469984
0.8384	Intermediate Similarity	NPC244356
0.8384	Intermediate Similarity	NPC224060
0.8381	Intermediate Similarity	NPC50535
0.8381	Intermediate Similarity	NPC28791
0.8365	Intermediate Similarity	NPC266
0.8364	Intermediate Similarity	NPC88945
0.835	Intermediate Similarity	NPC39683
0.8349	Intermediate Similarity	NPC471248
0.8349	Intermediate Similarity	NPC52634
0.8349	Intermediate Similarity	NPC132668
0.8333	Intermediate Similarity	NPC109059
0.8333	Intermediate Similarity	NPC122339

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 NPC98603 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	226
0.1-0.2	2122
0.2-0.3	3963
0.3-0.4	1817
0.4-0.5	546
0.5-0.6	218
0.6-0.7	158
0.7-0.8	100
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
0.7921	Intermediate Similarity	NPD8034	Phase 2
0.7921	Intermediate Similarity	NPD8035	Phase 2
0.7838	Intermediate Similarity	NPD6649	Approved
0.7838	Intermediate Similarity	NPD6650	Approved
0.7818	Intermediate Similarity	NPD6372	Approved
0.7818	Intermediate Similarity	NPD6373	Approved
0.7727	Intermediate Similarity	NPD6881	Approved
0.7727	Intermediate Similarity	NPD6899	Approved
0.7706	Intermediate Similarity	NPD6402	Approved
0.7706	Intermediate Similarity	NPD7128	Approved
0.7706	Intermediate Similarity	NPD6675	Approved
0.7706	Intermediate Similarity	NPD5739	Approved
0.7677	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD6399	Phase 3
0.7636	Intermediate Similarity	NPD5697	Approved
0.7607	Intermediate Similarity	NPD6319	Approved
0.7589	Intermediate Similarity	NPD6883	Approved
0.7589	Intermediate Similarity	NPD7290	Approved
0.7589	Intermediate Similarity	NPD7102	Approved
0.7568	Intermediate Similarity	NPD7320	Approved
0.7545	Intermediate Similarity	NPD6008	Approved
0.7522	Intermediate Similarity	NPD8130	Phase 1
0.7522	Intermediate Similarity	NPD6617	Approved
0.7522	Intermediate Similarity	NPD6869	Approved
0.7522	Intermediate Similarity	NPD6847	Approved
0.75	Intermediate Similarity	NPD7492	Approved
0.75	Intermediate Similarity	NPD6013	Approved
0.75	Intermediate Similarity	NPD6012	Approved
0.75	Intermediate Similarity	NPD6014	Approved
0.7477	Intermediate Similarity	NPD7638	Approved
0.7477	Intermediate Similarity	NPD5701	Approved
0.7459	Intermediate Similarity	NPD7736	Approved
0.7458	Intermediate Similarity	NPD6054	Approved
0.7456	Intermediate Similarity	NPD8297	Approved
0.7456	Intermediate Similarity	NPD6882	Approved
0.7438	Intermediate Similarity	NPD6616	Approved
0.7411	Intermediate Similarity	NPD6011	Approved
0.7411	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7639	Approved
0.7407	Intermediate Similarity	NPD7640	Approved
0.7404	Intermediate Similarity	NPD6079	Approved
0.7391	Intermediate Similarity	NPD4632	Approved
0.7383	Intermediate Similarity	NPD7902	Approved
0.7379	Intermediate Similarity	NPD5328	Approved
0.7377	Intermediate Similarity	NPD7078	Approved
0.735	Intermediate Similarity	NPD7115	Discovery
0.7333	Intermediate Similarity	NPD6370	Approved
0.732	Intermediate Similarity	NPD6697	Approved
0.732	Intermediate Similarity	NPD6118	Approved
0.732	Intermediate Similarity	NPD6115	Approved
0.732	Intermediate Similarity	NPD6114	Approved
0.7315	Intermediate Similarity	NPD5696	Approved
0.7311	Intermediate Similarity	NPD6059	Approved
0.73	Intermediate Similarity	NPD4788	Approved
0.729	Intermediate Similarity	NPD4697	Phase 3
0.7281	Intermediate Similarity	NPD4634	Approved
0.7264	Intermediate Similarity	NPD7748	Approved
0.725	Intermediate Similarity	NPD6015	Approved
0.725	Intermediate Similarity	NPD6016	Approved
0.7248	Intermediate Similarity	NPD5285	Approved
0.7248	Intermediate Similarity	NPD5286	Approved
0.7248	Intermediate Similarity	NPD4696	Approved
0.7238	Intermediate Similarity	NPD7515	Phase 2
0.7236	Intermediate Similarity	NPD8293	Discontinued
0.7222	Intermediate Similarity	NPD6083	Phase 2
0.7222	Intermediate Similarity	NPD4755	Approved
0.7222	Intermediate Similarity	NPD6084	Phase 2
0.7217	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD6009	Approved
0.719	Intermediate Similarity	NPD5988	Approved
0.7131	Intermediate Similarity	NPD7604	Phase 2
0.7131	Intermediate Similarity	NPD8328	Phase 3
0.713	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5222	Approved
0.713	Intermediate Similarity	NPD5221	Approved
0.712	Intermediate Similarity	NPD7319	Approved
0.7119	Intermediate Similarity	NPD6274	Approved
0.7117	Intermediate Similarity	NPD5225	Approved
0.7117	Intermediate Similarity	NPD4633	Approved
0.7117	Intermediate Similarity	NPD5224	Approved
0.7117	Intermediate Similarity	NPD5211	Phase 2
0.7117	Intermediate Similarity	NPD5226	Approved
0.7113	Intermediate Similarity	NPD6117	Approved
0.7107	Intermediate Similarity	NPD5983	Phase 2
0.7103	Intermediate Similarity	NPD7900	Approved
0.7103	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4700	Approved
0.7087	Intermediate Similarity	NPD3618	Phase 1
0.7083	Intermediate Similarity	NPD7101	Approved
0.7083	Intermediate Similarity	NPD7100	Approved
0.7075	Intermediate Similarity	NPD6411	Approved
0.7064	Intermediate Similarity	NPD5173	Approved
0.7059	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4786	Approved
0.7054	Intermediate Similarity	NPD5174	Approved
0.7054	Intermediate Similarity	NPD5175	Approved
0.7041	Intermediate Similarity	NPD6116	Phase 1
0.7037	Intermediate Similarity	NPD4629	Approved
0.7037	Intermediate Similarity	NPD5210	Approved
0.7027	Intermediate Similarity	NPD5223	Approved
0.7016	Intermediate Similarity	NPD7507	Approved
0.7016	Intermediate Similarity	NPD6336	Discontinued
0.701	Intermediate Similarity	NPD3703	Phase 2
0.7	Intermediate Similarity	NPD4225	Approved
0.7	Intermediate Similarity	NPD6335	Approved
0.6991	Remote Similarity	NPD5141	Approved
0.6975	Remote Similarity	NPD6868	Approved
0.6964	Remote Similarity	NPD7632	Discontinued
0.6952	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD8133	Approved
0.6923	Remote Similarity	NPD6409	Approved
0.6923	Remote Similarity	NPD5330	Approved
0.6923	Remote Similarity	NPD7521	Approved
0.6923	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6684	Approved
0.6923	Remote Similarity	NPD7146	Approved
0.6923	Remote Similarity	NPD7334	Approved
0.6917	Remote Similarity	NPD6317	Approved
0.6907	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6101	Approved
0.6881	Remote Similarity	NPD5695	Phase 3
0.6881	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6412	Phase 2
0.6863	Remote Similarity	NPD3667	Approved
0.686	Remote Similarity	NPD6313	Approved
0.686	Remote Similarity	NPD6314	Approved
0.6852	Remote Similarity	NPD5778	Approved
0.6852	Remote Similarity	NPD5779	Approved
0.6852	Remote Similarity	NPD4202	Approved
0.6829	Remote Similarity	NPD6909	Approved
0.6829	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6908	Approved
0.681	Remote Similarity	NPD5128	Approved
0.681	Remote Similarity	NPD4730	Approved
0.681	Remote Similarity	NPD4729	Approved
0.6792	Remote Similarity	NPD6903	Approved
0.6792	Remote Similarity	NPD6672	Approved
0.6792	Remote Similarity	NPD5737	Approved
0.6783	Remote Similarity	NPD4768	Approved
0.6783	Remote Similarity	NPD4767	Approved
0.6772	Remote Similarity	NPD6033	Approved
0.6759	Remote Similarity	NPD7637	Suspended
0.6754	Remote Similarity	NPD4754	Approved
0.6731	Remote Similarity	NPD3665	Phase 1
0.6731	Remote Similarity	NPD3666	Approved
0.6731	Remote Similarity	NPD3133	Approved
0.6729	Remote Similarity	NPD4753	Phase 2
0.6723	Remote Similarity	NPD6053	Discontinued
0.6701	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6081	Approved
0.6701	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD3573	Approved
0.6695	Remote Similarity	NPD5248	Approved
0.6695	Remote Similarity	NPD5249	Phase 3
0.6695	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD5247	Approved
0.6695	Remote Similarity	NPD5250	Approved
0.6695	Remote Similarity	NPD5251	Approved
0.6694	Remote Similarity	NPD6921	Approved
0.6667	Remote Similarity	NPD6686	Approved
0.6639	Remote Similarity	NPD5216	Approved
0.6639	Remote Similarity	NPD5217	Approved
0.6639	Remote Similarity	NPD5215	Approved
0.661	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5786	Approved
0.6577	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6904	Approved
0.6574	Remote Similarity	NPD6673	Approved
0.6574	Remote Similarity	NPD6080	Approved
0.6567	Remote Similarity	NPD6334	Approved
0.6567	Remote Similarity	NPD6333	Approved
0.6555	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD5135	Approved
0.6555	Remote Similarity	NPD5169	Approved
0.6555	Remote Similarity	NPD6371	Approved
0.6552	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD5777	Approved
0.6525	Remote Similarity	NPD5168	Approved
0.6514	Remote Similarity	NPD5785	Approved
0.6505	Remote Similarity	NPD7525	Registered
0.65	Remote Similarity	NPD3702	Approved
0.65	Remote Similarity	NPD5127	Approved
0.6495	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6001	Approved
0.6455	Remote Similarity	NPD5281	Approved
0.6455	Remote Similarity	NPD5284	Approved
0.6452	Remote Similarity	NPD7327	Approved
0.6452	Remote Similarity	NPD7328	Approved
0.6449	Remote Similarity	NPD6098	Approved
0.6442	Remote Similarity	NPD5369	Approved
0.6441	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD1700	Approved
0.6429	Remote Similarity	NPD8033	Approved
0.6429	Remote Similarity	NPD4245	Approved
0.6429	Remote Similarity	NPD4244	Approved
0.6415	Remote Similarity	NPD3668	Phase 3
0.64	Remote Similarity	NPD7516	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