NPASS Compound

Structure

NPC94650 OpenBabel07101719152D 28 31 0 0 1 0 0 0 0 0999 V2000 1.4576 2.1380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4762 2.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8709 1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3709 0.2141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2424 1.5801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2472 2.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8709 1.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6236 1.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2472 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0646 1.2185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4702 2.6351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2472 0.7201 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6236 -0.3600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5775 0.3600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2650 1.0088 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5630 1.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.7201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9195 -0.3930 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0896 0.9960 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8709 1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6236 1.0801 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 -1.2232 3.2930 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6236 -1.3600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8885 1.7907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3405 2.1440 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1420 -1.3680 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6634 1.6539 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 20 1 0 0 0 0 4 20 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 20 1 0 0 0 0 8 21 1 0 0 0 0 9 12 1 0 0 0 0 9 13 1 0 0 0 0 10 19 1 0 0 0 0 11 23 2 0 0 0 0 11 28 1 0 0 0 0 12 20 1 0 0 0 0 12 21 1 6 0 0 0 13 24 2 0 0 0 0 14 10 1 1 0 0 0 14 15 1 0 0 0 0 14 18 1 0 0 0 0 15 16 1 0 0 0 0 15 25 1 6 0 0 0 16 17 1 0 0 0 0 16 26 1 1 0 0 0 17 21 1 6 0 0 0 17 22 1 0 0 0 0 18 22 1 1 0 0 0 18 27 1 0 0 0 0 19 22 1 6 0 0 0 19 28 1 0 0 0 0 21 5 1 6 0 0 0 22 13 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.22
Volume:	399.674
LogP:	2.197
LogD:	1.923
LogS:	-3.357
# Rotatable Bonds:	2
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.463
Synthetic Accessibility Score:	6.226
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:	-4.858
MDCK Permeability:	5.445948045235127e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.876
Human Intestinal Absorption (HIA):	0.042
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.253
Plasma Protein Binding (PPB):	57.52826690673828%
Volume Distribution (VD):	0.711
Pgp-substrate:	48.65833282470703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.133
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.702
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.263
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.177
CYP3A4-inhibitor:	0.039
CYP3A4-substrate:	0.079

ADMET: Excretion

Clearance (CL):	2.778
Half-life (T1/2):	0.67

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.519
Drug-inuced Liver Injury (DILI):	0.265
AMES Toxicity:	0.094
Rat Oral Acute Toxicity:	0.929
Maximum Recommended Daily Dose:	0.672
Skin Sensitization:	0.289
Carcinogencity:	0.135
Eye Corrosion:	0.16
Eye Irritation:	0.04
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: NPC94650

Natural Product ID:	NPC94650
*Common Name:**	Isoscoparin F
IUPAC Name:	n.a.
Synonyms:	Isoscoparin F
Standard InCHIKey:	BCMXEXLNZDMRBV-CCFKJOQPSA-N
Standard InCHI:	InChI=1S/C22H32O6/c1-10-14-15(25)16(26)17-21(5)8-6-7-20(3,4)12(21)9-13(24)22(17,18(14)27)19(10)28-11(2)23/h12,14-19,25-27H,1,6-9H2,2-5H3/t12-,14-,15-,16+,17+,18-,19-,21-,22+/m1/s1
SMILES:	C=C1[C@@H]2[C@H]([C@@H]([C@H]3[C@]4(C)CCCC(C)(C)[C@H]4CC(=O)[C@]3([C@@H]2O)[C@@H]1OC(=O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL564818
PubChem CID:	25209066
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
NPO18028	Isodon scoparius	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19072209]
NPO18028	Isodon scoparius	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28654256]
NPO18028	Isodon scoparius	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	=	2200.0	nM	PMID[567777]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	9900.0	nM	PMID[567777]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	IC50	=	9200.0	nM	PMID[567777]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	10000.0	nM	PMID[567777]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	3900.0	nM	PMID[567777]

☑ 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 NPC94650 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	261
0.1-0.2	1749
0.2-0.3	5161
0.3-0.4	8412
0.4-0.5	12335
0.5-0.6	6307
0.6-0.7	5924
0.7-0.8	2147
0.8-0.85	324
0.85-0.9	69
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9327	High Similarity	NPC231278
0.9327	High Similarity	NPC112895
0.9327	High Similarity	NPC218123
0.932	High Similarity	NPC295366
0.932	High Similarity	NPC37600
0.9216	High Similarity	NPC170615
0.8962	High Similarity	NPC273155
0.8952	High Similarity	NPC28791
0.8942	High Similarity	NPC87927
0.8932	High Similarity	NPC121218
0.8932	High Similarity	NPC253886
0.8868	High Similarity	NPC166993
0.8868	High Similarity	NPC86852
0.8868	High Similarity	NPC251824
0.8846	High Similarity	NPC148628
0.8846	High Similarity	NPC88203
0.8846	High Similarity	NPC76866
0.8846	High Similarity	NPC304832
0.8846	High Similarity	NPC286519
0.8846	High Similarity	NPC246736
0.8846	High Similarity	NPC214946
0.8774	High Similarity	NPC138908
0.8774	High Similarity	NPC200957
0.8762	High Similarity	NPC209298
0.8762	High Similarity	NPC277074
0.875	High Similarity	NPC46848
0.875	High Similarity	NPC52899
0.875	High Similarity	NPC289148
0.875	High Similarity	NPC163963
0.8727	High Similarity	NPC471252
0.8716	High Similarity	NPC56025
0.8716	High Similarity	NPC29505
0.8679	High Similarity	NPC301787
0.8679	High Similarity	NPC47281
0.8667	High Similarity	NPC275990
0.8654	High Similarity	NPC291785
0.8654	High Similarity	NPC127408
0.8654	High Similarity	NPC470388
0.8654	High Similarity	NPC287676
0.8636	High Similarity	NPC40608
0.8624	High Similarity	NPC471093
0.8598	High Similarity	NPC222833
0.8598	High Similarity	NPC50535
0.8585	High Similarity	NPC469985
0.8585	High Similarity	NPC122811
0.8571	High Similarity	NPC295276
0.8558	High Similarity	NPC162459
0.8558	High Similarity	NPC20479
0.8558	High Similarity	NPC471038
0.8558	High Similarity	NPC16911
0.8558	High Similarity	NPC38471
0.8558	High Similarity	NPC38296
0.8558	High Similarity	NPC98837
0.8558	High Similarity	NPC28864
0.8558	High Similarity	NPC78427
0.8529	High Similarity	NPC3359
0.8505	High Similarity	NPC84928
0.8505	High Similarity	NPC98603
0.8496	Intermediate Similarity	NPC473304
0.8487	Intermediate Similarity	NPC231529
0.8476	Intermediate Similarity	NPC293866
0.8468	Intermediate Similarity	NPC473397
0.8468	Intermediate Similarity	NPC474927
0.8462	Intermediate Similarity	NPC274793
0.8462	Intermediate Similarity	NPC170978
0.8455	Intermediate Similarity	NPC124053
0.844	Intermediate Similarity	NPC55973
0.844	Intermediate Similarity	NPC208461
0.844	Intermediate Similarity	NPC63841
0.844	Intermediate Similarity	NPC289702
0.8431	Intermediate Similarity	NPC199543
0.8411	Intermediate Similarity	NPC216114
0.8396	Intermediate Similarity	NPC471790
0.8396	Intermediate Similarity	NPC252614
0.8396	Intermediate Similarity	NPC39683
0.8393	Intermediate Similarity	NPC471248
0.8381	Intermediate Similarity	NPC474793
0.8381	Intermediate Similarity	NPC89099
0.8378	Intermediate Similarity	NPC471251
0.8378	Intermediate Similarity	NPC213320
0.8378	Intermediate Similarity	NPC329953
0.8365	Intermediate Similarity	NPC256227
0.8365	Intermediate Similarity	NPC13949
0.8365	Intermediate Similarity	NPC200054
0.8365	Intermediate Similarity	NPC329910
0.8365	Intermediate Similarity	NPC29410
0.8364	Intermediate Similarity	NPC118721
0.8364	Intermediate Similarity	NPC102741
0.8364	Intermediate Similarity	NPC252679
0.8364	Intermediate Similarity	NPC471250
0.835	Intermediate Similarity	NPC280804
0.8349	Intermediate Similarity	NPC471461
0.8349	Intermediate Similarity	NPC78966
0.8349	Intermediate Similarity	NPC67745
0.8349	Intermediate Similarity	NPC284732
0.8349	Intermediate Similarity	NPC201908
0.8349	Intermediate Similarity	NPC176949
0.8349	Intermediate Similarity	NPC186054
0.8333	Intermediate Similarity	NPC130840
0.8333	Intermediate Similarity	NPC55296
0.8333	Intermediate Similarity	NPC13149
0.8318	Intermediate Similarity	NPC177701
0.8305	Intermediate Similarity	NPC469790
0.8304	Intermediate Similarity	NPC473303
0.8304	Intermediate Similarity	NPC476964
0.8304	Intermediate Similarity	NPC471245
0.8304	Intermediate Similarity	NPC473352
0.8302	Intermediate Similarity	NPC108371
0.8302	Intermediate Similarity	NPC180733
0.8302	Intermediate Similarity	NPC37047
0.8302	Intermediate Similarity	NPC41971
0.8302	Intermediate Similarity	NPC94906
0.8291	Intermediate Similarity	NPC269642
0.8288	Intermediate Similarity	NPC473324
0.8288	Intermediate Similarity	NPC474786
0.8288	Intermediate Similarity	NPC85391
0.8288	Intermediate Similarity	NPC320383
0.8288	Intermediate Similarity	NPC137104
0.8286	Intermediate Similarity	NPC10864
0.8276	Intermediate Similarity	NPC154491
0.8276	Intermediate Similarity	NPC251226
0.8276	Intermediate Similarity	NPC268530
0.8273	Intermediate Similarity	NPC189663
0.8273	Intermediate Similarity	NPC469984
0.8273	Intermediate Similarity	NPC471094
0.8273	Intermediate Similarity	NPC89860
0.8273	Intermediate Similarity	NPC473410
0.8273	Intermediate Similarity	NPC37628
0.8273	Intermediate Similarity	NPC211224
0.8269	Intermediate Similarity	NPC138245
0.8269	Intermediate Similarity	NPC84018
0.8269	Intermediate Similarity	NPC231060
0.8269	Intermediate Similarity	NPC210214
0.8269	Intermediate Similarity	NPC470229
0.8269	Intermediate Similarity	NPC470232
0.8269	Intermediate Similarity	NPC98639
0.8257	Intermediate Similarity	NPC4115
0.8252	Intermediate Similarity	NPC472496
0.8252	Intermediate Similarity	NPC476189
0.8252	Intermediate Similarity	NPC26046
0.8246	Intermediate Similarity	NPC88945
0.8241	Intermediate Similarity	NPC470310
0.8241	Intermediate Similarity	NPC72842
0.8241	Intermediate Similarity	NPC61442
0.8241	Intermediate Similarity	NPC139347
0.8241	Intermediate Similarity	NPC99510
0.823	Intermediate Similarity	NPC132668
0.8224	Intermediate Similarity	NPC236585
0.8224	Intermediate Similarity	NPC75941
0.8224	Intermediate Similarity	NPC49532
0.8214	Intermediate Similarity	NPC122339
0.8214	Intermediate Similarity	NPC470311
0.8214	Intermediate Similarity	NPC157476
0.8214	Intermediate Similarity	NPC470281
0.8208	Intermediate Similarity	NPC472028
0.8208	Intermediate Similarity	NPC469986
0.8205	Intermediate Similarity	NPC4021
0.8205	Intermediate Similarity	NPC159456
0.8198	Intermediate Similarity	NPC131903
0.8198	Intermediate Similarity	NPC274827
0.819	Intermediate Similarity	NPC306797
0.819	Intermediate Similarity	NPC169270
0.819	Intermediate Similarity	NPC230513
0.819	Intermediate Similarity	NPC104568
0.819	Intermediate Similarity	NPC234564
0.819	Intermediate Similarity	NPC475041
0.819	Intermediate Similarity	NPC111834
0.819	Intermediate Similarity	NPC292718
0.8182	Intermediate Similarity	NPC471246
0.8182	Intermediate Similarity	NPC471474
0.8174	Intermediate Similarity	NPC78836
0.8174	Intermediate Similarity	NPC470171
0.8173	Intermediate Similarity	NPC29247
0.8173	Intermediate Similarity	NPC104371
0.8173	Intermediate Similarity	NPC129004
0.8173	Intermediate Similarity	NPC101233
0.8173	Intermediate Similarity	NPC289539
0.8173	Intermediate Similarity	NPC191094
0.8173	Intermediate Similarity	NPC475118
0.8173	Intermediate Similarity	NPC153775
0.8173	Intermediate Similarity	NPC470385
0.8173	Intermediate Similarity	NPC47853
0.8173	Intermediate Similarity	NPC91772
0.8173	Intermediate Similarity	NPC302008
0.8173	Intermediate Similarity	NPC111524
0.8173	Intermediate Similarity	NPC261333
0.8173	Intermediate Similarity	NPC470386
0.8173	Intermediate Similarity	NPC292374
0.8173	Intermediate Similarity	NPC215271
0.8165	Intermediate Similarity	NPC474558
0.8165	Intermediate Similarity	NPC202793
0.8165	Intermediate Similarity	NPC96268
0.8158	Intermediate Similarity	NPC300051
0.8158	Intermediate Similarity	NPC243354
0.8148	Intermediate Similarity	NPC309388
0.8148	Intermediate Similarity	NPC124544
0.8148	Intermediate Similarity	NPC31085
0.8148	Intermediate Similarity	NPC475803
0.8142	Intermediate Similarity	NPC471244
0.8142	Intermediate Similarity	NPC280782

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 NPC94650 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	253
0.1-0.2	2114
0.2-0.3	3855
0.3-0.4	1884
0.4-0.5	552
0.5-0.6	260
0.6-0.7	170
0.7-0.8	61
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.844	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD7319	Approved
0.7607	Intermediate Similarity	NPD8133	Approved
0.7603	Intermediate Similarity	NPD6921	Approved
0.7545	Intermediate Similarity	NPD7638	Approved
0.7521	Intermediate Similarity	NPD6319	Approved
0.75	Intermediate Similarity	NPD7507	Approved
0.7477	Intermediate Similarity	NPD7639	Approved
0.7477	Intermediate Similarity	NPD8034	Phase 2
0.7477	Intermediate Similarity	NPD8035	Phase 2
0.7477	Intermediate Similarity	NPD7640	Approved
0.7456	Intermediate Similarity	NPD6675	Approved
0.7456	Intermediate Similarity	NPD6402	Approved
0.7456	Intermediate Similarity	NPD7128	Approved
0.7456	Intermediate Similarity	NPD5739	Approved
0.7417	Intermediate Similarity	NPD7115	Discovery
0.7414	Intermediate Similarity	NPD6373	Approved
0.7414	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD6372	Approved
0.7328	Intermediate Similarity	NPD6881	Approved
0.7328	Intermediate Similarity	NPD7320	Approved
0.7328	Intermediate Similarity	NPD6899	Approved
0.7311	Intermediate Similarity	NPD4632	Approved
0.7304	Intermediate Similarity	NPD6008	Approved
0.7295	Intermediate Similarity	NPD7516	Approved
0.7288	Intermediate Similarity	NPD6649	Approved
0.7288	Intermediate Similarity	NPD6650	Approved
0.728	Intermediate Similarity	NPD7492	Approved
0.7248	Intermediate Similarity	NPD6399	Phase 3
0.7244	Intermediate Similarity	NPD7736	Approved
0.7241	Intermediate Similarity	NPD5697	Approved
0.7241	Intermediate Similarity	NPD5701	Approved
0.7238	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD6054	Approved
0.7236	Intermediate Similarity	NPD6059	Approved
0.7227	Intermediate Similarity	NPD8297	Approved
0.7222	Intermediate Similarity	NPD6616	Approved
0.7213	Intermediate Similarity	NPD7328	Approved
0.7213	Intermediate Similarity	NPD7327	Approved
0.7203	Intermediate Similarity	NPD7102	Approved
0.7203	Intermediate Similarity	NPD7290	Approved
0.7203	Intermediate Similarity	NPD4634	Approved
0.7203	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD6883	Approved
0.7165	Intermediate Similarity	NPD7078	Approved
0.7165	Intermediate Similarity	NPD8293	Discontinued
0.7143	Intermediate Similarity	NPD6617	Approved
0.7143	Intermediate Similarity	NPD8130	Phase 1
0.7143	Intermediate Similarity	NPD6847	Approved
0.7143	Intermediate Similarity	NPD6869	Approved
0.7131	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6370	Approved
0.7119	Intermediate Similarity	NPD6013	Approved
0.7119	Intermediate Similarity	NPD6014	Approved
0.7119	Intermediate Similarity	NPD6012	Approved
0.7105	Intermediate Similarity	NPD1700	Approved
0.7083	Intermediate Similarity	NPD6053	Discontinued
0.7083	Intermediate Similarity	NPD6882	Approved
0.708	Intermediate Similarity	NPD4225	Approved
0.7063	Intermediate Similarity	NPD8328	Phase 3
0.7043	Intermediate Similarity	NPD7632	Discontinued
0.704	Intermediate Similarity	NPD6016	Approved
0.704	Intermediate Similarity	NPD6015	Approved
0.704	Intermediate Similarity	NPD8033	Approved
0.7034	Intermediate Similarity	NPD6011	Approved
0.7	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD6009	Approved
0.6991	Remote Similarity	NPD4755	Approved
0.6984	Remote Similarity	NPD5988	Approved
0.6975	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD6412	Phase 2
0.6929	Remote Similarity	NPD7604	Phase 2
0.6917	Remote Similarity	NPD6371	Approved
0.6905	Remote Similarity	NPD5983	Phase 2
0.6905	Remote Similarity	NPD8378	Approved
0.6905	Remote Similarity	NPD8335	Approved
0.6905	Remote Similarity	NPD8380	Approved
0.6905	Remote Similarity	NPD8296	Approved
0.6905	Remote Similarity	NPD8379	Approved
0.6897	Remote Similarity	NPD5211	Phase 2
0.6893	Remote Similarity	NPD6697	Approved
0.6893	Remote Similarity	NPD6118	Approved
0.6893	Remote Similarity	NPD6114	Approved
0.6893	Remote Similarity	NPD6115	Approved
0.6891	Remote Similarity	NPD6686	Approved
0.687	Remote Similarity	NPD4700	Approved
0.687	Remote Similarity	NPD5285	Approved
0.687	Remote Similarity	NPD5286	Approved
0.687	Remote Similarity	NPD4696	Approved
0.6842	Remote Similarity	NPD6084	Phase 2
0.6842	Remote Similarity	NPD6083	Phase 2
0.6842	Remote Similarity	NPD7902	Approved
0.6825	Remote Similarity	NPD8294	Approved
0.6825	Remote Similarity	NPD8377	Approved
0.6822	Remote Similarity	NPD6336	Discontinued
0.6818	Remote Similarity	NPD5328	Approved
0.6796	Remote Similarity	NPD6116	Phase 1
0.678	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.678	Remote Similarity	NPD5141	Approved
0.6774	Remote Similarity	NPD6274	Approved
0.6752	Remote Similarity	NPD5224	Approved
0.6752	Remote Similarity	NPD4633	Approved
0.6752	Remote Similarity	NPD5225	Approved
0.6752	Remote Similarity	NPD5226	Approved
0.6746	Remote Similarity	NPD7100	Approved
0.6746	Remote Similarity	NPD7101	Approved
0.6729	Remote Similarity	NPD4788	Approved
0.6726	Remote Similarity	NPD7748	Approved
0.6718	Remote Similarity	NPD6033	Approved
0.6699	Remote Similarity	NPD6117	Approved
0.6696	Remote Similarity	NPD6411	Approved
0.6696	Remote Similarity	NPD7637	Suspended
0.6696	Remote Similarity	NPD7515	Phase 2
0.6696	Remote Similarity	NPD6079	Approved
0.6695	Remote Similarity	NPD5175	Approved
0.6695	Remote Similarity	NPD5174	Approved
0.6667	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD5223	Approved
0.6667	Remote Similarity	NPD4786	Approved
0.6641	Remote Similarity	NPD8515	Approved
0.6641	Remote Similarity	NPD6908	Approved
0.6641	Remote Similarity	NPD6909	Approved
0.6641	Remote Similarity	NPD8516	Approved
0.6641	Remote Similarity	NPD8517	Approved
0.6641	Remote Similarity	NPD8513	Phase 3
0.6638	Remote Similarity	NPD5696	Approved
0.6637	Remote Similarity	NPD4202	Approved
0.6637	Remote Similarity	NPD5778	Approved
0.6637	Remote Similarity	NPD5779	Approved
0.6609	Remote Similarity	NPD4697	Phase 3
0.6602	Remote Similarity	NPD3703	Phase 2
0.6587	Remote Similarity	NPD6317	Approved
0.6583	Remote Similarity	NPD4768	Approved
0.6583	Remote Similarity	NPD4767	Approved
0.6579	Remote Similarity	NPD7900	Approved
0.6579	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD4754	Approved
0.6545	Remote Similarity	NPD7146	Approved
0.6545	Remote Similarity	NPD7521	Approved
0.6545	Remote Similarity	NPD3618	Phase 1
0.6545	Remote Similarity	NPD7334	Approved
0.6545	Remote Similarity	NPD6684	Approved
0.6545	Remote Similarity	NPD5330	Approved
0.6545	Remote Similarity	NPD6409	Approved
0.6535	Remote Similarity	NPD6314	Approved
0.6535	Remote Similarity	NPD6313	Approved
0.6525	Remote Similarity	NPD5344	Discontinued
0.6522	Remote Similarity	NPD5695	Phase 3
0.6522	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD6101	Approved
0.6512	Remote Similarity	NPD7503	Approved
0.6512	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD3667	Approved
0.6481	Remote Similarity	NPD6435	Approved
0.6475	Remote Similarity	NPD5128	Approved
0.6475	Remote Similarity	NPD4730	Approved
0.6475	Remote Similarity	NPD4729	Approved
0.6466	Remote Similarity	NPD5221	Approved
0.6466	Remote Similarity	NPD5222	Approved
0.6466	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.646	Remote Similarity	NPD5785	Approved
0.6429	Remote Similarity	NPD6903	Approved
0.641	Remote Similarity	NPD5173	Approved
0.6404	Remote Similarity	NPD7983	Approved
0.6404	Remote Similarity	NPD5693	Phase 1
0.6396	Remote Similarity	NPD5786	Approved
0.6393	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD8074	Phase 3
0.6378	Remote Similarity	NPD6868	Approved
0.6372	Remote Similarity	NPD4753	Phase 2
0.6371	Remote Similarity	NPD5250	Approved
0.6371	Remote Similarity	NPD5251	Approved
0.6371	Remote Similarity	NPD5247	Approved
0.6371	Remote Similarity	NPD5248	Approved
0.6371	Remote Similarity	NPD5249	Phase 3
0.6364	Remote Similarity	NPD3665	Phase 1
0.6364	Remote Similarity	NPD3133	Approved
0.6364	Remote Similarity	NPD3666	Approved
0.6339	Remote Similarity	NPD7524	Approved
0.632	Remote Similarity	NPD5215	Approved
0.632	Remote Similarity	NPD5216	Approved
0.632	Remote Similarity	NPD5217	Approved
0.6316	Remote Similarity	NPD46	Approved
0.6316	Remote Similarity	NPD6698	Approved
0.6311	Remote Similarity	NPD5777	Approved
0.6311	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5368	Approved
0.6296	Remote Similarity	NPD7525	Registered
0.6288	Remote Similarity	NPD6067	Discontinued
0.6286	Remote Similarity	NPD3702	Approved
0.6286	Remote Similarity	NPD6334	Approved
0.6286	Remote Similarity	NPD6333	Approved
0.6283	Remote Similarity	NPD6672	Approved
0.6283	Remote Similarity	NPD5737	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