NPASS Compound

Structure

NPC106479 OpenBabel07101718192D 33 37 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 4.4689 -2.3002 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 2.3709 -0.2141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9097 -0.7141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9586 -1.0231 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 1.2472 -2.1603 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 0.6236 0.3600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2650 -1.0088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9195 0.3930 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 -1.0646 -1.2185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6029 -1.8002 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 -0.5630 -1.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2472 -0.7201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8709 -1.8002 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9097 0.2859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3709 -0.2141 0.0000 C 0 0 2 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 -0.0896 -0.9960 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 1.8709 -1.0801 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9586 0.5949 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.6029 -0.8002 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 6.7187 0.8737 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 3.3709 -0.2141 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7369 -2.3002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 2 0 0 0 0 2 15 1 0 0 0 0 5 6 1 0 0 0 0 5 20 1 0 0 0 0 6 21 1 0 0 0 0 7 10 1 0 0 0 0 7 18 1 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 9 24 1 0 0 0 0 11 17 1 0 0 0 0 12 16 1 0 0 0 0 12 26 1 0 0 0 0 13 25 1 0 0 0 0 13 32 1 0 0 0 0 14 16 1 0 0 0 0 14 23 1 0 0 0 0 15 28 2 0 0 0 0 15 33 1 0 0 0 0 16 11 1 6 0 0 0 17 22 1 0 0 0 0 17 29 1 1 0 0 0 18 24 1 6 0 0 0 18 25 1 0 0 0 0 19 25 1 1 0 0 0 19 33 1 0 0 0 0 20 27 2 0 0 0 0 20 30 1 0 0 0 0 21 27 1 0 0 0 0 21 32 1 1 0 0 0 22 24 1 6 0 0 0 22 26 1 0 0 0 0 23 26 1 0 0 0 0 23 31 2 0 0 0 0 24 3 1 6 0 0 0 25 4 1 1 0 0 0 26 10 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	459.26
Volume:	468.662
LogP:	1.77
LogD:	2.164
LogS:	-3.767
# Rotatable Bonds:	5
TPSA:	101.93
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.495
Synthetic Accessibility Score:	6.239
Fsp3:	0.808
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:	-4.912
MDCK Permeability:	3.5308534279465675e-05
Pgp-inhibitor:	0.977
Pgp-substrate:	0.922
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.111
30% Bioavailability (F30%):	0.573

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.656
Plasma Protein Binding (PPB):	36.36471176147461%
Volume Distribution (VD):	0.553
Pgp-substrate:	59.00514602661133%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.119
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.36
CYP2C9-inhibitor:	0.021
CYP2C9-substrate:	0.033
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.105
CYP3A4-inhibitor:	0.592
CYP3A4-substrate:	0.249

ADMET: Excretion

Clearance (CL):	2.965
Half-life (T1/2):	0.363

ADMET: Toxicity

hERG Blockers:	0.487
Human Hepatotoxicity (H-HT):	0.098
Drug-inuced Liver Injury (DILI):	0.223
AMES Toxicity:	0.589
Rat Oral Acute Toxicity:	0.331
Maximum Recommended Daily Dose:	0.954
Skin Sensitization:	0.914
Carcinogencity:	0.712
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC106479

Natural Product ID:	NPC106479
*Common Name:**	Excisusin F
IUPAC Name:	n.a.
Synonyms:	Excisusin F
Standard InCHIKey:	UDIMVRVKHIXRQH-TYORKGSASA-N
Standard InCHI:	InChI=1S/C26H37NO6/c1-14-16-11-17(29)22-24(3)9-8-19(33-15(2)28)25(4,13-32-21-6-5-20(30)27-21)18(24)7-10-26(22,12-16)23(14)31/h16-19,21-22,29H,1,5-13H2,2-4H3,(H,27,30)/t16-,17+,18+,19+,21-,22+,24-,25+,26-/m1/s1
SMILES:	CC(=O)O[C@H]1CC[C@@]2([C@@H]([C@]1(C)CO[C@@H]1CCC(=N1)O)CC[C@]13[C@H]2[C@@H](O)C[C@H](C1)C(=C)C3=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1668468
PubChem CID:	53323644
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
NPO26913	Isodon excisus	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[10896056]
NPO26913	Isodon excisus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374970]
NPO26913	Isodon excisus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17338565]
NPO26913	Isodon excisus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21273070]
NPO26913	Isodon excisus	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[22066578]
NPO26913	Isodon excisus	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	10400.0	nM	PMID[492899]

☑ 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 NPC106479 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	100
0.1-0.2	902
0.2-0.3	5106
0.3-0.4	17051
0.4-0.5	8159
0.5-0.6	7241
0.6-0.7	3755
0.7-0.8	366
0.8-0.85	16
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8269	Intermediate Similarity	NPC294263
0.8113	Intermediate Similarity	NPC98639
0.8056	Intermediate Similarity	NPC20479
0.8056	Intermediate Similarity	NPC28864
0.8056	Intermediate Similarity	NPC38296
0.8056	Intermediate Similarity	NPC38471
0.8056	Intermediate Similarity	NPC98837
0.8056	Intermediate Similarity	NPC162459
0.8037	Intermediate Similarity	NPC200054
0.8037	Intermediate Similarity	NPC29410
0.7982	Intermediate Similarity	NPC293866
0.7963	Intermediate Similarity	NPC10864
0.7909	Intermediate Similarity	NPC46848
0.789	Intermediate Similarity	NPC471038
0.789	Intermediate Similarity	NPC89099
0.787	Intermediate Similarity	NPC13949
0.7863	Intermediate Similarity	NPC470540
0.7838	Intermediate Similarity	NPC275990
0.783	Intermediate Similarity	NPC250753
0.7778	Intermediate Similarity	NPC210214
0.7768	Intermediate Similarity	NPC87927
0.7748	Intermediate Similarity	NPC52899
0.7748	Intermediate Similarity	NPC252614
0.7748	Intermediate Similarity	NPC289148
0.7748	Intermediate Similarity	NPC163963
0.7727	Intermediate Similarity	NPC474793
0.7706	Intermediate Similarity	NPC329910
0.7706	Intermediate Similarity	NPC104568
0.7699	Intermediate Similarity	NPC301787
0.7692	Intermediate Similarity	NPC471042
0.7685	Intermediate Similarity	NPC272635
0.7685	Intermediate Similarity	NPC169751
0.7679	Intermediate Similarity	NPC88203
0.7679	Intermediate Similarity	NPC246736
0.7679	Intermediate Similarity	NPC304832
0.7679	Intermediate Similarity	NPC76866
0.7679	Intermediate Similarity	NPC286519
0.7679	Intermediate Similarity	NPC214946
0.7679	Intermediate Similarity	NPC148628
0.7667	Intermediate Similarity	NPC470276
0.7658	Intermediate Similarity	NPC287676
0.7632	Intermediate Similarity	NPC200957
0.7632	Intermediate Similarity	NPC138908
0.7632	Intermediate Similarity	NPC222833
0.7619	Intermediate Similarity	NPC174619
0.7615	Intermediate Similarity	NPC470229
0.7615	Intermediate Similarity	NPC470232
0.7611	Intermediate Similarity	NPC139347
0.7611	Intermediate Similarity	NPC209298
0.7611	Intermediate Similarity	NPC470310
0.7611	Intermediate Similarity	NPC122811
0.7611	Intermediate Similarity	NPC277074
0.7589	Intermediate Similarity	NPC121218
0.7589	Intermediate Similarity	NPC236585
0.7589	Intermediate Similarity	NPC253886
0.7589	Intermediate Similarity	NPC148279
0.7568	Intermediate Similarity	NPC78427
0.7568	Intermediate Similarity	NPC16911
0.7565	Intermediate Similarity	NPC176949
0.7565	Intermediate Similarity	NPC166993
0.7565	Intermediate Similarity	NPC201908
0.7544	Intermediate Similarity	NPC98603
0.7523	Intermediate Similarity	NPC47853
0.7523	Intermediate Similarity	NPC475118
0.7523	Intermediate Similarity	NPC470386
0.7523	Intermediate Similarity	NPC470385
0.7523	Intermediate Similarity	NPC303863
0.7522	Intermediate Similarity	NPC170615
0.7522	Intermediate Similarity	NPC136289
0.75	Intermediate Similarity	NPC146683
0.75	Intermediate Similarity	NPC211403
0.75	Intermediate Similarity	NPC198242
0.75	Intermediate Similarity	NPC273155
0.75	Intermediate Similarity	NPC267921
0.75	Intermediate Similarity	NPC112895
0.75	Intermediate Similarity	NPC470388
0.75	Intermediate Similarity	NPC218123
0.75	Intermediate Similarity	NPC231278
0.7478	Intermediate Similarity	NPC265127
0.7456	Intermediate Similarity	NPC216114
0.7456	Intermediate Similarity	NPC96217
0.7453	Intermediate Similarity	NPC153604
0.7434	Intermediate Similarity	NPC81530
0.7431	Intermediate Similarity	NPC244356
0.7431	Intermediate Similarity	NPC224060
0.7431	Intermediate Similarity	NPC59170
0.7414	Intermediate Similarity	NPC96333
0.7414	Intermediate Similarity	NPC88833
0.7411	Intermediate Similarity	NPC26270
0.7407	Intermediate Similarity	NPC180849
0.7404	Intermediate Similarity	NPC118800
0.7404	Intermediate Similarity	NPC471037
0.7391	Intermediate Similarity	NPC119329
0.7391	Intermediate Similarity	NPC84928
0.7391	Intermediate Similarity	NPC13149
0.7391	Intermediate Similarity	NPC47281
0.7391	Intermediate Similarity	NPC101842
0.7387	Intermediate Similarity	NPC219353
0.7387	Intermediate Similarity	NPC470387
0.7383	Intermediate Similarity	NPC474719
0.7377	Intermediate Similarity	NPC476956
0.735	Intermediate Similarity	NPC63841
0.735	Intermediate Similarity	NPC211224
0.7345	Intermediate Similarity	NPC293890
0.7339	Intermediate Similarity	NPC160506
0.7339	Intermediate Similarity	NPC470230
0.7328	Intermediate Similarity	NPC295366
0.7328	Intermediate Similarity	NPC37600
0.7328	Intermediate Similarity	NPC50535
0.7328	Intermediate Similarity	NPC28791
0.7321	Intermediate Similarity	NPC253586
0.7311	Intermediate Similarity	NPC329953
0.7304	Intermediate Similarity	NPC112009
0.7297	Intermediate Similarity	NPC231060
0.7297	Intermediate Similarity	NPC266431
0.7297	Intermediate Similarity	NPC205173
0.7297	Intermediate Similarity	NPC138245
0.7297	Intermediate Similarity	NPC84018
0.7297	Intermediate Similarity	NPC29112
0.7295	Intermediate Similarity	NPC470275
0.729	Intermediate Similarity	NPC33768
0.729	Intermediate Similarity	NPC264005
0.729	Intermediate Similarity	NPC269360
0.7288	Intermediate Similarity	NPC218602
0.7281	Intermediate Similarity	NPC295276
0.7281	Intermediate Similarity	NPC71706
0.7281	Intermediate Similarity	NPC471790
0.7281	Intermediate Similarity	NPC14634
0.7273	Intermediate Similarity	NPC181594
0.7273	Intermediate Similarity	NPC471902
0.7273	Intermediate Similarity	NPC59350
0.7273	Intermediate Similarity	NPC144739
0.7273	Intermediate Similarity	NPC473690
0.7273	Intermediate Similarity	NPC287118
0.7266	Intermediate Similarity	NPC476957
0.7265	Intermediate Similarity	NPC470952
0.7265	Intermediate Similarity	NPC61071
0.7265	Intermediate Similarity	NPC186054
0.7265	Intermediate Similarity	NPC251824
0.7265	Intermediate Similarity	NPC86852
0.7257	Intermediate Similarity	NPC288
0.7257	Intermediate Similarity	NPC109059
0.7248	Intermediate Similarity	NPC80401
0.7241	Intermediate Similarity	NPC96268
0.7241	Intermediate Similarity	NPC474558
0.7241	Intermediate Similarity	NPC202793
0.7227	Intermediate Similarity	NPC328052
0.7227	Intermediate Similarity	NPC471093
0.7227	Intermediate Similarity	NPC474786
0.7227	Intermediate Similarity	NPC320383
0.7227	Intermediate Similarity	NPC137104
0.7227	Intermediate Similarity	NPC49730
0.7227	Intermediate Similarity	NPC98069
0.7222	Intermediate Similarity	NPC4309
0.7222	Intermediate Similarity	NPC56413
0.7217	Intermediate Similarity	NPC309388
0.7217	Intermediate Similarity	NPC15396
0.7217	Intermediate Similarity	NPC475803
0.7217	Intermediate Similarity	NPC124544
0.7207	Intermediate Similarity	NPC302008
0.7207	Intermediate Similarity	NPC289539
0.7207	Intermediate Similarity	NPC261333
0.7207	Intermediate Similarity	NPC191094
0.7207	Intermediate Similarity	NPC91772
0.7207	Intermediate Similarity	NPC215271
0.7207	Intermediate Similarity	NPC292374
0.7207	Intermediate Similarity	NPC153775
0.7207	Intermediate Similarity	NPC129004
0.7207	Intermediate Similarity	NPC104371
0.7207	Intermediate Similarity	NPC111524
0.7207	Intermediate Similarity	NPC101233
0.7207	Intermediate Similarity	NPC29247
0.7203	Intermediate Similarity	NPC473410
0.7203	Intermediate Similarity	NPC232133
0.7203	Intermediate Similarity	NPC469984
0.7203	Intermediate Similarity	NPC471094
0.7196	Intermediate Similarity	NPC2783
0.7196	Intermediate Similarity	NPC12774
0.7193	Intermediate Similarity	NPC94906
0.7193	Intermediate Similarity	NPC476274
0.7193	Intermediate Similarity	NPC108371
0.7193	Intermediate Similarity	NPC201406
0.719	Intermediate Similarity	NPC471252
0.7182	Intermediate Similarity	NPC471901
0.7182	Intermediate Similarity	NPC476168
0.7182	Intermediate Similarity	NPC299185
0.7182	Intermediate Similarity	NPC475416
0.7182	Intermediate Similarity	NPC278106
0.7179	Intermediate Similarity	NPC164600
0.7179	Intermediate Similarity	NPC103172
0.7179	Intermediate Similarity	NPC4115
0.7167	Intermediate Similarity	NPC470281
0.7167	Intermediate Similarity	NPC29505
0.7156	Intermediate Similarity	NPC57954
0.7156	Intermediate Similarity	NPC471043
0.7156	Intermediate Similarity	NPC213832
0.7155	Intermediate Similarity	NPC180204
0.7155	Intermediate Similarity	NPC159442
0.7155	Intermediate Similarity	NPC140723
0.7155	Intermediate Similarity	NPC469985

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 NPC106479 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	89
0.1-0.2	775
0.2-0.3	3697
0.3-0.4	3383
0.4-0.5	768
0.5-0.6	252
0.6-0.7	160
0.7-0.8	26
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
0.7339	Intermediate Similarity	NPD8035	Phase 2
0.7339	Intermediate Similarity	NPD8034	Phase 2
0.7203	Intermediate Similarity	NPD7320	Approved
0.7203	Intermediate Similarity	NPD6881	Approved
0.7203	Intermediate Similarity	NPD6899	Approved
0.72	Intermediate Similarity	NPD6909	Approved
0.72	Intermediate Similarity	NPD6908	Approved
0.7179	Intermediate Similarity	NPD7128	Approved
0.7179	Intermediate Similarity	NPD6675	Approved
0.7179	Intermediate Similarity	NPD5739	Approved
0.7179	Intermediate Similarity	NPD6402	Approved
0.7167	Intermediate Similarity	NPD6650	Approved
0.7167	Intermediate Similarity	NPD6649	Approved
0.7164	Intermediate Similarity	NPD6334	Approved
0.7164	Intermediate Similarity	NPD6333	Approved
0.7143	Intermediate Similarity	NPD6373	Approved
0.7143	Intermediate Similarity	NPD6372	Approved
0.7119	Intermediate Similarity	NPD5697	Approved
0.7103	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7102	Approved
0.7083	Intermediate Similarity	NPD6883	Approved
0.7083	Intermediate Similarity	NPD7290	Approved
0.7043	Intermediate Similarity	NPD8418	Phase 2
0.7025	Intermediate Similarity	NPD6617	Approved
0.7025	Intermediate Similarity	NPD6847	Approved
0.7025	Intermediate Similarity	NPD8130	Phase 1
0.7025	Intermediate Similarity	NPD6869	Approved
0.7	Intermediate Similarity	NPD6014	Approved
0.7	Intermediate Similarity	NPD6013	Approved
0.7	Intermediate Similarity	NPD6012	Approved
0.6975	Remote Similarity	NPD5701	Approved
0.6967	Remote Similarity	NPD8297	Approved
0.6967	Remote Similarity	NPD6882	Approved
0.6964	Remote Similarity	NPD6399	Phase 3
0.6917	Remote Similarity	NPD6011	Approved
0.6875	Remote Similarity	NPD6079	Approved
0.687	Remote Similarity	NPD7902	Approved
0.6847	Remote Similarity	NPD5328	Approved
0.6754	Remote Similarity	NPD7748	Approved
0.6752	Remote Similarity	NPD5286	Approved
0.6752	Remote Similarity	NPD4696	Approved
0.6752	Remote Similarity	NPD5285	Approved
0.6748	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7515	Phase 2
0.6724	Remote Similarity	NPD4755	Approved
0.6692	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD6116	Phase 1
0.6641	Remote Similarity	NPD7101	Approved
0.6641	Remote Similarity	NPD7100	Approved
0.664	Remote Similarity	NPD8298	Phase 2
0.6639	Remote Similarity	NPD5226	Approved
0.6639	Remote Similarity	NPD5211	Phase 2
0.6639	Remote Similarity	NPD5224	Approved
0.6639	Remote Similarity	NPD5225	Approved
0.6639	Remote Similarity	NPD4633	Approved
0.6638	Remote Similarity	NPD5221	Approved
0.6638	Remote Similarity	NPD5222	Approved
0.6638	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD4697	Phase 3
0.6612	Remote Similarity	NPD6008	Approved
0.661	Remote Similarity	NPD4700	Approved
0.6609	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7900	Approved
0.6606	Remote Similarity	NPD4788	Approved
0.6583	Remote Similarity	NPD5175	Approved
0.6583	Remote Similarity	NPD5174	Approved
0.6581	Remote Similarity	NPD6083	Phase 2
0.6581	Remote Similarity	NPD5173	Approved
0.6581	Remote Similarity	NPD6084	Phase 2
0.6577	Remote Similarity	NPD3618	Phase 1
0.6571	Remote Similarity	NPD6117	Approved
0.6562	Remote Similarity	NPD6335	Approved
0.6555	Remote Similarity	NPD5223	Approved
0.6538	Remote Similarity	NPD6921	Approved
0.6538	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6868	Approved
0.6532	Remote Similarity	NPD6420	Discontinued
0.6529	Remote Similarity	NPD5141	Approved
0.6525	Remote Similarity	NPD7638	Approved
0.6522	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD7492	Approved
0.6508	Remote Similarity	NPD4632	Approved
0.6493	Remote Similarity	NPD7736	Approved
0.6484	Remote Similarity	NPD6317	Approved
0.6484	Remote Similarity	NPD7115	Discovery
0.6471	Remote Similarity	NPD7639	Approved
0.6471	Remote Similarity	NPD6404	Discontinued
0.6471	Remote Similarity	NPD7640	Approved
0.6466	Remote Similarity	NPD6616	Approved
0.6466	Remote Similarity	NPD7507	Approved
0.6462	Remote Similarity	NPD6319	Approved
0.6462	Remote Similarity	NPD6054	Approved
0.6449	Remote Similarity	NPD6114	Approved
0.6449	Remote Similarity	NPD6118	Approved
0.6449	Remote Similarity	NPD6115	Approved
0.6449	Remote Similarity	NPD6697	Approved
0.6434	Remote Similarity	NPD6314	Approved
0.6434	Remote Similarity	NPD6313	Approved
0.6418	Remote Similarity	NPD7078	Approved
0.641	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD6914	Discontinued
0.6396	Remote Similarity	NPD4786	Approved
0.6387	Remote Similarity	NPD5696	Approved
0.6385	Remote Similarity	NPD7518	Approved
0.6385	Remote Similarity	NPD7517	Approved
0.6385	Remote Similarity	NPD7519	Approved
0.6381	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD4202	Approved
0.6371	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD5128	Approved
0.6371	Remote Similarity	NPD4730	Approved
0.6371	Remote Similarity	NPD4729	Approved
0.6364	Remote Similarity	NPD6370	Approved
0.6357	Remote Similarity	NPD6009	Approved
0.6341	Remote Similarity	NPD4767	Approved
0.6341	Remote Similarity	NPD4768	Approved
0.6336	Remote Similarity	NPD6059	Approved
0.6324	Remote Similarity	NPD7319	Approved
0.6316	Remote Similarity	NPD6903	Approved
0.6316	Remote Similarity	NPD5737	Approved
0.6316	Remote Similarity	NPD6672	Approved
0.6316	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4754	Approved
0.6296	Remote Similarity	NPD8293	Discontinued
0.6288	Remote Similarity	NPD6015	Approved
0.6288	Remote Similarity	NPD6016	Approved
0.6288	Remote Similarity	NPD5983	Phase 2
0.6283	Remote Similarity	NPD7334	Approved
0.6283	Remote Similarity	NPD5330	Approved
0.6283	Remote Similarity	NPD6409	Approved
0.6283	Remote Similarity	NPD6684	Approved
0.6283	Remote Similarity	NPD7146	Approved
0.6283	Remote Similarity	NPD7521	Approved
0.6271	Remote Similarity	NPD5695	Phase 3
0.627	Remote Similarity	NPD5250	Approved
0.627	Remote Similarity	NPD4634	Approved
0.627	Remote Similarity	NPD5248	Approved
0.627	Remote Similarity	NPD5249	Phase 3
0.627	Remote Similarity	NPD5247	Approved
0.627	Remote Similarity	NPD5251	Approved
0.625	Remote Similarity	NPD8133	Approved
0.6241	Remote Similarity	NPD5988	Approved
0.6228	Remote Similarity	NPD3573	Approved
0.6222	Remote Similarity	NPD6336	Discontinued
0.622	Remote Similarity	NPD5216	Approved
0.622	Remote Similarity	NPD5215	Approved
0.622	Remote Similarity	NPD5217	Approved
0.6216	Remote Similarity	NPD3667	Approved
0.6212	Remote Similarity	NPD7148	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD7147	Phase 3
0.6194	Remote Similarity	NPD8328	Phase 3
0.619	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6187	Remote Similarity	NPD6845	Suspended
0.6182	Remote Similarity	NPD7525	Registered
0.6168	Remote Similarity	NPD3703	Phase 2
0.6154	Remote Similarity	NPD6411	Approved
0.6142	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD5135	Approved
0.6142	Remote Similarity	NPD5169	Approved
0.6134	Remote Similarity	NPD5210	Approved
0.6134	Remote Similarity	NPD4629	Approved
0.6126	Remote Similarity	NPD1448	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD4753	Phase 2
0.6116	Remote Similarity	NPD4225	Approved
0.6115	Remote Similarity	NPD7260	Phase 2
0.6111	Remote Similarity	NPD5168	Approved
0.6111	Remote Similarity	NPD6686	Approved
0.6106	Remote Similarity	NPD3666	Approved
0.6106	Remote Similarity	NPD3133	Approved
0.6106	Remote Similarity	NPD3665	Phase 1
0.6098	Remote Similarity	NPD7632	Discontinued
0.6094	Remote Similarity	NPD5127	Approved
0.6083	Remote Similarity	NPD7614	Phase 1
0.6083	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6074	Remote Similarity	NPD7122	Discontinued
0.6063	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.605	Remote Similarity	NPD6001	Approved
0.6032	Remote Similarity	NPD6412	Phase 2
0.6017	Remote Similarity	NPD5284	Approved
0.6017	Remote Similarity	NPD5281	Approved
0.6016	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5985	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD6101	Approved
0.5983	Remote Similarity	NPD6080	Approved
0.5983	Remote Similarity	NPD6904	Approved
0.5983	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD6673	Approved
0.5954	Remote Similarity	NPD5167	Approved
0.5952	Remote Similarity	NPD6920	Discontinued
0.595	Remote Similarity	NPD7732	Phase 3
0.594	Remote Similarity	NPD7328	Approved
0.594	Remote Similarity	NPD7327	Approved
0.5932	Remote Similarity	NPD6701	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data