NPASS Compound

Structure

CID180011 OpenBabel06191715552D 25 27 0 0 0 0 0 0 0 0999 V2000 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 5 2 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 4 24 1 0 0 0 0 5 19 1 0 0 0 0 6 7 2 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 8 11 2 0 0 0 0 8 12 1 0 0 0 0 9 15 1 0 0 0 0 9 16 2 0 0 0 0 10 17 2 0 0 0 0 10 20 1 0 0 0 0 11 13 1 0 0 0 0 11 21 1 0 0 0 0 12 14 2 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 13 18 2 0 0 0 0 14 18 1 0 0 0 0 14 19 1 0 0 0 0 15 23 2 0 0 0 0 16 17 1 0 0 0 0 16 25 1 0 0 0 0 17 24 1 0 0 0 0 18 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.11
Volume:	343.16
LogP:	3.932
LogD:	2.888
LogS:	-4.03
# Rotatable Bonds:	3
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.497
Synthetic Accessibility Score:	3.08
Fsp3:	0.211
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.901
MDCK Permeability:	1.5096205970621668e-05
Pgp-inhibitor:	0.113
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.086
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	91.95221710205078%
Volume Distribution (VD):	0.962
Pgp-substrate:	13.594463348388672%

ADMET: Metabolism

CYP1A2-inhibitor:	0.938
CYP1A2-substrate:	0.817
CYP2C19-inhibitor:	0.302
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.734
CYP2C9-substrate:	0.894
CYP2D6-inhibitor:	0.265
CYP2D6-substrate:	0.249
CYP3A4-inhibitor:	0.28
CYP3A4-substrate:	0.153

ADMET: Excretion

Clearance (CL):	1.522
Half-life (T1/2):	0.68

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.081
Drug-inuced Liver Injury (DILI):	0.97
AMES Toxicity:	0.731
Rat Oral Acute Toxicity:	0.457
Maximum Recommended Daily Dose:	0.238
Skin Sensitization:	0.784
Carcinogencity:	0.417
Eye Corrosion:	0.011
Eye Irritation:	0.9
Respiratory Toxicity:	0.475

Download Data

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

Natural Product: NPC180011

Natural Product ID:	NPC180011
*Common Name:**	ZEOKDWPZNMUQNT-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZEOKDWPZNMUQNT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H18O6/c1-5-19(2,3)14-12(22)8-11(21)13-15(23)9-6-7-10(20)17(24-4)16(9)25-18(13)14/h5-8,20-22H,1H2,2-4H3
SMILES:	COc1c(O)ccc2c1oc1c(c2=O)c(O)cc(c1C(C=C)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3327041
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO9520	Cratoxylum sumatranum	Species	Hypericaceae	Eukaryota	n.a.	twig	n.a.	PMID[11908969]
NPO9520	Cratoxylum sumatranum	Species	Hypericaceae	Eukaryota	n.a.	stem	n.a.	PMID[11908969]
NPO9520	Cratoxylum sumatranum	Species	Hypericaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11908969]
NPO16745	Scorzonera judaica	Species	Asteraceae	Eukaryota	roots	Daba desert reserve (50 km South of Amman), Jordan	2009-APR	PMID[21650157]
NPO16745	Scorzonera judaica	Species	Asteraceae	Eukaryota	n.a.	tuberous root	n.a.	PMID[21650157]
NPO8797	Cudrania tricuspidata	Species	Moraceae	Eukaryota	Root barks	n.a.	n.a.	PMID[25051453]
NPO8797	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27420919]
NPO19227	Hippoglossus hippoglossus	Species	Pleuronectidae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16038	Ribes rubrum	Species	Grossulariaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16038	Ribes rubrum	Species	Grossulariaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO16038	Ribes rubrum	Species	Grossulariaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO19227	Hippoglossus hippoglossus	Species	Pleuronectidae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO16038	Ribes rubrum	Species	Grossulariaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO8797	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19227	Hippoglossus hippoglossus	Species	Pleuronectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17438	Polygala virgata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19560	Populus italica	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18657	Galanthus gracilis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18005	Artemisia leucodes	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19359	Parmotrema delicatulum	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19501	Pseudosuberites hyalinus	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13263	Verbena brasiliensis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11770	Amphicome emodi	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16038	Ribes rubrum	Species	Grossulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14950	Ardisia polycephala	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6106	Hymeniacidon perlevis	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9520	Cratoxylum sumatranum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16745	Scorzonera judaica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18995	Gaultheria itoana	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8797	Cudrania tricuspidata	Species	Moraceae	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
EC50	1
Others	1

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Ratio EC50	=	7.0	n.a.	PMID[462970]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	700.0	nM	PMID[462970]

☑ 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 NPC180011 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	449
0.1-0.2	2004
0.2-0.3	4524
0.3-0.4	11071
0.4-0.5	6751
0.5-0.6	3854
0.6-0.7	5316
0.7-0.8	4864
0.8-0.85	2138
0.85-0.9	1145
0.9-0.95	534
0.95-1	47

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC219867
0.9933	High Similarity	NPC115853
0.9867	High Similarity	NPC161960
0.9867	High Similarity	NPC187745
0.9867	High Similarity	NPC304008
0.9803	High Similarity	NPC57715
0.9737	High Similarity	NPC188433
0.9733	High Similarity	NPC117992
0.9733	High Similarity	NPC256925
0.9733	High Similarity	NPC168247
0.9733	High Similarity	NPC230149
0.9733	High Similarity	NPC152951
0.9733	High Similarity	NPC57674
0.9675	High Similarity	NPC205265
0.9675	High Similarity	NPC472281
0.9673	High Similarity	NPC234644
0.9671	High Similarity	NPC235448
0.9667	High Similarity	NPC49402
0.9667	High Similarity	NPC227337
0.9667	High Similarity	NPC273462
0.9667	High Similarity	NPC70433
0.9667	High Similarity	NPC33051
0.9613	High Similarity	NPC472277
0.9605	High Similarity	NPC79053
0.9548	High Similarity	NPC319200
0.9548	High Similarity	NPC303460
0.9548	High Similarity	NPC187491
0.9548	High Similarity	NPC306321
0.9548	High Similarity	NPC220313
0.9548	High Similarity	NPC18100
0.9545	High Similarity	NPC472275
0.9542	High Similarity	NPC172770
0.9542	High Similarity	NPC185258
0.9542	High Similarity	NPC204879
0.9539	High Similarity	NPC470600
0.9539	High Similarity	NPC472455
0.9477	High Similarity	NPC36852
0.9477	High Similarity	NPC136674
0.9477	High Similarity	NPC78225
0.9477	High Similarity	NPC129684
0.9477	High Similarity	NPC291508
0.9477	High Similarity	NPC262286
0.9477	High Similarity	NPC299520
0.9477	High Similarity	NPC474681
0.9477	High Similarity	NPC218313
0.9474	High Similarity	NPC234255
0.9474	High Similarity	NPC472280
0.9474	High Similarity	NPC200246
0.947	High Similarity	NPC477231
0.947	High Similarity	NPC257648
0.9467	High Similarity	NPC29231
0.943	High Similarity	NPC288813
0.9419	High Similarity	NPC32694
0.9412	High Similarity	NPC133970
0.9412	High Similarity	NPC138243
0.9412	High Similarity	NPC6633
0.9412	High Similarity	NPC191146
0.9412	High Similarity	NPC195796
0.9412	High Similarity	NPC5322
0.9412	High Similarity	NPC291878
0.9412	High Similarity	NPC68093
0.9412	High Similarity	NPC278778
0.9412	High Similarity	NPC35038
0.9408	High Similarity	NPC469550
0.9404	High Similarity	NPC31363
0.9396	High Similarity	NPC77378
0.9371	High Similarity	NPC472276
0.9359	High Similarity	NPC474162
0.9359	High Similarity	NPC472448
0.9359	High Similarity	NPC83922
0.9359	High Similarity	NPC474150
0.9355	High Similarity	NPC45146
0.9355	High Similarity	NPC476980
0.9355	High Similarity	NPC80375
0.9355	High Similarity	NPC228785
0.9355	High Similarity	NPC14353
0.9355	High Similarity	NPC36217
0.9355	High Similarity	NPC56085
0.9355	High Similarity	NPC235018
0.9355	High Similarity	NPC471973
0.9351	High Similarity	NPC474055
0.9351	High Similarity	NPC52889
0.9351	High Similarity	NPC27337
0.9351	High Similarity	NPC472598
0.9351	High Similarity	NPC472963
0.9346	High Similarity	NPC113906
0.9346	High Similarity	NPC477503
0.9346	High Similarity	NPC255807
0.9346	High Similarity	NPC31018
0.9346	High Similarity	NPC470327
0.9346	High Similarity	NPC45849
0.9346	High Similarity	NPC200761
0.9342	High Similarity	NPC260979
0.9342	High Similarity	NPC161277
0.9342	High Similarity	NPC471982
0.9342	High Similarity	NPC39732
0.9342	High Similarity	NPC60972
0.9342	High Similarity	NPC237994
0.9342	High Similarity	NPC472912
0.9342	High Similarity	NPC39007
0.9338	High Similarity	NPC472279
0.9333	High Similarity	NPC196277
0.9333	High Similarity	NPC43669
0.9333	High Similarity	NPC272721
0.9304	High Similarity	NPC235610
0.9299	High Similarity	NPC473313
0.9299	High Similarity	NPC472278
0.9299	High Similarity	NPC329669
0.9299	High Similarity	NPC124038
0.9295	High Similarity	NPC167678
0.9295	High Similarity	NPC258331
0.9295	High Similarity	NPC61010
0.9295	High Similarity	NPC278052
0.9295	High Similarity	NPC29876
0.9295	High Similarity	NPC472906
0.9295	High Similarity	NPC40491
0.9295	High Similarity	NPC266314
0.9295	High Similarity	NPC134783
0.929	High Similarity	NPC55738
0.929	High Similarity	NPC100123
0.929	High Similarity	NPC184755
0.929	High Similarity	NPC95936
0.929	High Similarity	NPC74178
0.929	High Similarity	NPC250214
0.9286	High Similarity	NPC209614
0.9286	High Similarity	NPC472626
0.9286	High Similarity	NPC472916
0.9286	High Similarity	NPC3980
0.9286	High Similarity	NPC470328
0.9286	High Similarity	NPC472907
0.9281	High Similarity	NPC167091
0.9281	High Similarity	NPC292214
0.9281	High Similarity	NPC88645
0.9281	High Similarity	NPC472905
0.9281	High Similarity	NPC271779
0.9281	High Similarity	NPC206238
0.9281	High Similarity	NPC18727
0.9281	High Similarity	NPC213896
0.9281	High Similarity	NPC192083
0.9276	High Similarity	NPC154345
0.9276	High Similarity	NPC256406
0.9276	High Similarity	NPC171010
0.9241	High Similarity	NPC62261
0.9241	High Similarity	NPC239752
0.9241	High Similarity	NPC300053
0.9241	High Similarity	NPC275780
0.9241	High Similarity	NPC472450
0.9241	High Similarity	NPC108433
0.9236	High Similarity	NPC476247
0.9236	High Similarity	NPC78332
0.9236	High Similarity	NPC261470
0.9236	High Similarity	NPC474034
0.9236	High Similarity	NPC470694
0.9236	High Similarity	NPC474033
0.9236	High Similarity	NPC201800
0.9231	High Similarity	NPC282009
0.9231	High Similarity	NPC472624
0.9231	High Similarity	NPC204290
0.9231	High Similarity	NPC119209
0.9231	High Similarity	NPC297212
0.9231	High Similarity	NPC320359
0.9231	High Similarity	NPC474960
0.9231	High Similarity	NPC476283
0.9231	High Similarity	NPC287328
0.9231	High Similarity	NPC192686
0.9231	High Similarity	NPC28241
0.9231	High Similarity	NPC118256
0.9226	High Similarity	NPC472911
0.9226	High Similarity	NPC156057
0.9226	High Similarity	NPC474208
0.9226	High Similarity	NPC300727
0.9226	High Similarity	NPC241904
0.9226	High Similarity	NPC162869
0.9226	High Similarity	NPC96167
0.9226	High Similarity	NPC469584
0.9226	High Similarity	NPC165977
0.9226	High Similarity	NPC217677
0.9226	High Similarity	NPC472914
0.9226	High Similarity	NPC472913
0.9226	High Similarity	NPC99597
0.9226	High Similarity	NPC111969
0.9226	High Similarity	NPC210084
0.9226	High Similarity	NPC475267
0.9226	High Similarity	NPC222814
0.9226	High Similarity	NPC476981
0.9226	High Similarity	NPC223787
0.9226	High Similarity	NPC474836
0.9226	High Similarity	NPC472910
0.9226	High Similarity	NPC245758
0.9226	High Similarity	NPC67876
0.9226	High Similarity	NPC48208
0.9226	High Similarity	NPC181960
0.9221	High Similarity	NPC226025
0.9221	High Similarity	NPC321779
0.9221	High Similarity	NPC2928
0.9221	High Similarity	NPC256612
0.9221	High Similarity	NPC20830
0.9216	High Similarity	NPC101996
0.9216	High Similarity	NPC236637
0.9216	High Similarity	NPC120537

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 NPC180011 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	418
0.1-0.2	1028
0.2-0.3	1844
0.3-0.4	2669
0.4-0.5	1740
0.5-0.6	949
0.6-0.7	350
0.7-0.8	102
0.8-0.85	34
0.85-0.9	10
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9281	High Similarity	NPD2393	Clinical (unspecified phase)
0.9216	High Similarity	NPD1934	Approved
0.9156	High Similarity	NPD2801	Approved
0.9038	High Similarity	NPD3882	Suspended
0.8816	High Similarity	NPD1511	Approved
0.8765	High Similarity	NPD6166	Phase 2
0.8765	High Similarity	NPD6168	Clinical (unspecified phase)
0.8765	High Similarity	NPD6167	Clinical (unspecified phase)
0.875	High Similarity	NPD5494	Approved
0.8701	High Similarity	NPD1512	Approved
0.8659	High Similarity	NPD3818	Discontinued
0.8636	High Similarity	NPD4378	Clinical (unspecified phase)
0.8625	High Similarity	NPD7075	Discontinued
0.8599	High Similarity	NPD4380	Phase 2
0.8562	High Similarity	NPD4868	Clinical (unspecified phase)
0.8554	High Similarity	NPD7074	Phase 3
0.8553	High Similarity	NPD7819	Suspended
0.8553	High Similarity	NPD7096	Clinical (unspecified phase)
0.8528	High Similarity	NPD6232	Discontinued
0.85	High Similarity	NPD3817	Phase 2
0.8494	Intermediate Similarity	NPD7054	Approved
0.8487	Intermediate Similarity	NPD1549	Phase 2
0.8485	Intermediate Similarity	NPD7473	Discontinued
0.8443	Intermediate Similarity	NPD7472	Approved
0.8438	Intermediate Similarity	NPD1465	Phase 2
0.8421	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD6801	Discontinued
0.8365	Intermediate Similarity	NPD6599	Discontinued
0.8313	Intermediate Similarity	NPD7411	Suspended
0.8312	Intermediate Similarity	NPD2800	Approved
0.8294	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD1510	Phase 2
0.8284	Intermediate Similarity	NPD6797	Phase 2
0.8282	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD5844	Phase 1
0.8267	Intermediate Similarity	NPD1240	Approved
0.8267	Intermediate Similarity	NPD943	Approved
0.8242	Intermediate Similarity	NPD6959	Discontinued
0.8235	Intermediate Similarity	NPD7251	Discontinued
0.8235	Intermediate Similarity	NPD2796	Approved
0.8217	Intermediate Similarity	NPD6799	Approved
0.8187	Intermediate Similarity	NPD7808	Phase 3
0.8158	Intermediate Similarity	NPD1607	Approved
0.8144	Intermediate Similarity	NPD3926	Phase 2
0.8095	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD1247	Approved
0.8023	Intermediate Similarity	NPD6559	Discontinued
0.8012	Intermediate Similarity	NPD919	Approved
0.8	Intermediate Similarity	NPD7768	Phase 2
0.7952	Intermediate Similarity	NPD3749	Approved
0.7922	Intermediate Similarity	NPD6651	Approved
0.7912	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD4628	Phase 3
0.7911	Intermediate Similarity	NPD3750	Approved
0.7898	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD2935	Discontinued
0.7885	Intermediate Similarity	NPD6099	Approved
0.7885	Intermediate Similarity	NPD6100	Approved
0.7881	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD5402	Approved
0.7826	Intermediate Similarity	NPD2533	Approved
0.7826	Intermediate Similarity	NPD2532	Approved
0.7826	Intermediate Similarity	NPD2534	Approved
0.7821	Intermediate Similarity	NPD2799	Discontinued
0.7821	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD1613	Approved
0.7744	Intermediate Similarity	NPD3226	Approved
0.7742	Intermediate Similarity	NPD230	Phase 1
0.7742	Intermediate Similarity	NPD447	Suspended
0.773	Intermediate Similarity	NPD920	Approved
0.773	Intermediate Similarity	NPD5403	Approved
0.7722	Intermediate Similarity	NPD2344	Approved
0.7722	Intermediate Similarity	NPD2346	Discontinued
0.7709	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD1551	Phase 2
0.7657	Intermediate Similarity	NPD5953	Discontinued
0.7644	Intermediate Similarity	NPD7286	Phase 2
0.7628	Intermediate Similarity	NPD1933	Approved
0.7625	Intermediate Similarity	NPD1243	Approved
0.7607	Intermediate Similarity	NPD5401	Approved
0.7602	Intermediate Similarity	NPD7199	Phase 2
0.7597	Intermediate Similarity	NPD3027	Phase 3
0.7595	Intermediate Similarity	NPD3748	Approved
0.7588	Intermediate Similarity	NPD6234	Discontinued
0.7582	Intermediate Similarity	NPD9494	Approved
0.7571	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD2313	Discontinued
0.7546	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD2309	Approved
0.7527	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD3751	Discontinued
0.7485	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD7390	Discontinued
0.743	Intermediate Similarity	NPD8312	Approved
0.743	Intermediate Similarity	NPD8313	Approved
0.7425	Intermediate Similarity	NPD7458	Discontinued
0.7419	Intermediate Similarity	NPD4908	Phase 1
0.7403	Intermediate Similarity	NPD8434	Phase 2
0.7396	Intermediate Similarity	NPD37	Approved
0.7394	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7228	Approved
0.7372	Intermediate Similarity	NPD4625	Phase 3
0.7368	Intermediate Similarity	NPD4967	Phase 2
0.7368	Intermediate Similarity	NPD4965	Approved
0.7368	Intermediate Similarity	NPD4966	Approved
0.7365	Intermediate Similarity	NPD1653	Approved
0.7356	Intermediate Similarity	NPD5711	Approved
0.7356	Intermediate Similarity	NPD5710	Approved
0.7356	Intermediate Similarity	NPD3787	Discontinued
0.7338	Intermediate Similarity	NPD1203	Approved
0.7318	Intermediate Similarity	NPD7685	Pre-registration
0.7317	Intermediate Similarity	NPD6190	Approved
0.7314	Intermediate Similarity	NPD5242	Approved
0.7303	Intermediate Similarity	NPD1610	Phase 2
0.7303	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD2798	Approved
0.7289	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD4360	Phase 2
0.7258	Intermediate Similarity	NPD4363	Phase 3
0.7255	Intermediate Similarity	NPD3972	Approved
0.7249	Intermediate Similarity	NPD6776	Approved
0.7249	Intermediate Similarity	NPD6782	Approved
0.7249	Intermediate Similarity	NPD6778	Approved
0.7249	Intermediate Similarity	NPD6777	Approved
0.7249	Intermediate Similarity	NPD6781	Approved
0.7249	Intermediate Similarity	NPD6779	Approved
0.7249	Intermediate Similarity	NPD6780	Approved
0.7226	Intermediate Similarity	NPD1470	Approved
0.7219	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD8151	Discontinued
0.7215	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD3268	Approved
0.7213	Intermediate Similarity	NPD8150	Discontinued
0.7197	Intermediate Similarity	NPD6832	Phase 2
0.7175	Intermediate Similarity	NPD2403	Approved
0.7159	Intermediate Similarity	NPD7229	Phase 3
0.7152	Intermediate Similarity	NPD8166	Discontinued
0.7152	Intermediate Similarity	NPD7003	Approved
0.7143	Intermediate Similarity	NPD1608	Approved
0.7143	Intermediate Similarity	NPD9717	Approved
0.7143	Intermediate Similarity	NPD9269	Phase 2
0.7135	Intermediate Similarity	NPD7435	Discontinued
0.7135	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD4361	Phase 2
0.7128	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD6104	Discontinued
0.7126	Intermediate Similarity	NPD4357	Discontinued
0.7125	Intermediate Similarity	NPD4060	Phase 1
0.7117	Intermediate Similarity	NPD5404	Approved
0.7117	Intermediate Similarity	NPD5406	Approved
0.7117	Intermediate Similarity	NPD5405	Approved
0.7117	Intermediate Similarity	NPD5408	Approved
0.7115	Intermediate Similarity	NPD2797	Approved
0.7113	Intermediate Similarity	NPD7584	Approved
0.7111	Intermediate Similarity	NPD1729	Discontinued
0.711	Intermediate Similarity	NPD5353	Approved
0.7102	Intermediate Similarity	NPD8127	Discontinued
0.7097	Intermediate Similarity	NPD4749	Approved
0.7086	Intermediate Similarity	NPD5536	Phase 2
0.7081	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1201	Approved
0.7073	Intermediate Similarity	NPD1471	Phase 3
0.7055	Intermediate Similarity	NPD7033	Discontinued
0.7055	Intermediate Similarity	NPD4308	Phase 3
0.7052	Intermediate Similarity	NPD5761	Phase 2
0.7052	Intermediate Similarity	NPD5760	Phase 2
0.7049	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD4110	Phase 3
0.7048	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7696	Phase 3
0.7047	Intermediate Similarity	NPD7698	Approved
0.7047	Intermediate Similarity	NPD7697	Approved
0.7044	Intermediate Similarity	NPD7095	Approved
0.7043	Intermediate Similarity	NPD4287	Approved
0.7041	Intermediate Similarity	NPD6273	Approved
0.7039	Intermediate Similarity	NPD1548	Phase 1
0.7035	Intermediate Similarity	NPD6386	Approved
0.7035	Intermediate Similarity	NPD6385	Approved
0.7033	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD2494	Approved
0.7031	Intermediate Similarity	NPD2493	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