NPASS Compound

Structure

NPC59239 OpenBabel07101719522D 24 27 0 0 1 0 0 0 0 0999 V2000 2.7352 -1.5285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8527 -3.1077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7569 -1.1560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3453 -0.2931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0292 -2.0887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6914 -1.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4067 0.4675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2488 0.9219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0740 -0.5947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8381 -2.0634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9372 0.9735 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9264 -1.5539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8825 -1.5792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -2.1140 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7060 -0.5602 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8971 -0.5348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9117 -0.5095 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3038 -0.2150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8089 -0.0253 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3187 1.9458 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8089 0.0253 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0146 1.0443 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0610 -1.5243 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 12 2 0 0 0 0 5 13 1 0 0 0 0 6 15 1 0 0 0 0 7 11 1 0 0 0 0 7 19 1 0 0 0 0 8 11 1 0 0 0 0 9 20 1 0 0 0 0 9 24 1 0 0 0 0 10 12 1 0 0 0 0 11 21 1 6 0 0 0 12 17 1 0 0 0 0 13 14 1 0 0 0 0 13 16 2 0 0 0 0 14 6 1 6 0 0 0 14 24 1 0 0 0 0 15 19 1 0 0 0 0 15 20 1 1 0 0 0 16 18 1 0 0 0 0 16 20 1 0 0 0 0 17 18 2 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 20 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.2
Volume:	347.502
LogP:	3.57
LogD:	2.735
LogS:	-3.693
# Rotatable Bonds:	1
TPSA:	69.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.685
Synthetic Accessibility Score:	5.619
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.741
MDCK Permeability:	1.2480992154451087e-05
Pgp-inhibitor:	0.255
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.947
30% Bioavailability (F30%):	0.181

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.656
Plasma Protein Binding (PPB):	96.2953109741211%
Volume Distribution (VD):	3.09
Pgp-substrate:	5.4995341300964355%

ADMET: Metabolism

CYP1A2-inhibitor:	0.065
CYP1A2-substrate:	0.702
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.825
CYP2C9-inhibitor:	0.147
CYP2C9-substrate:	0.485
CYP2D6-inhibitor:	0.066
CYP2D6-substrate:	0.262
CYP3A4-inhibitor:	0.201
CYP3A4-substrate:	0.317

ADMET: Excretion

Clearance (CL):	11.252
Half-life (T1/2):	0.542

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.425
Drug-inuced Liver Injury (DILI):	0.048
AMES Toxicity:	0.142
Rat Oral Acute Toxicity:	0.779
Maximum Recommended Daily Dose:	0.988
Skin Sensitization:	0.947
Carcinogencity:	0.617
Eye Corrosion:	0.004
Eye Irritation:	0.682
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: NPC59239

Natural Product ID:	NPC59239
*Common Name:**	KRVFRLOLTQRXBW-MRQYSOIQSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KRVFRLOLTQRXBW-MRQYSOIQSA-N
Standard InCHI:	InChI=1S/C20H28O4/c1-10(2)12-5-13-14-6-15-19(3,4)7-11(21)8-20(15,9-24-14)16(13)18(23)17(12)22/h5,10-11,14-15,21-23H,6-9H2,1-4H3/t11-,14-,15-,20+/m0/s1
SMILES:	O[C@H]1CC(C)(C)[C@H]2[C@@]3(C1)CO[C@@H](C2)c1c3c(O)c(c(c1)C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581362
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] 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
NPO1371	Teucrium viscidum	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[23337296]
NPO1371	Teucrium viscidum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24484201]
NPO1371	Teucrium viscidum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25739048]
NPO1371	Teucrium viscidum	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	6

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[508088]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	10000.0	nM	PMID[508088]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	10000.0	nM	PMID[508088]
NPT2	Others	Unspecified		IC50	>	1000000.0	nM	PMID[508088]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[508088]

☑ 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 NPC59239 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	416
0.1-0.2	1435
0.2-0.3	3264
0.3-0.4	7524
0.4-0.5	10424
0.5-0.6	7266
0.6-0.7	9572
0.7-0.8	2611
0.8-0.85	157
0.85-0.9	21
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.984	High Similarity	NPC99795
0.9453	High Similarity	NPC78575
0.9453	High Similarity	NPC312341
0.9098	High Similarity	NPC68292
0.8992	High Similarity	NPC471077
0.8929	High Similarity	NPC127046
0.8921	High Similarity	NPC84786
0.8872	High Similarity	NPC227719
0.8857	High Similarity	NPC474991
0.8837	High Similarity	NPC124030
0.875	High Similarity	NPC471794
0.8702	High Similarity	NPC186889
0.8672	High Similarity	NPC474115
0.8671	High Similarity	NPC183380
0.8657	High Similarity	NPC321086
0.8643	High Similarity	NPC473845
0.8626	High Similarity	NPC470724
0.8621	High Similarity	NPC475227
0.8621	High Similarity	NPC200645
0.8621	High Similarity	NPC106669
0.8594	High Similarity	NPC470414
0.8592	High Similarity	NPC474397
0.8583	High Similarity	NPC469644
0.8582	High Similarity	NPC472457
0.8561	High Similarity	NPC265075
0.8561	High Similarity	NPC476536
0.8531	High Similarity	NPC473876
0.8511	High Similarity	NPC164183
0.8511	High Similarity	NPC473108
0.8507	High Similarity	NPC470727
0.8504	High Similarity	NPC471671
0.8496	Intermediate Similarity	NPC201069
0.8496	Intermediate Similarity	NPC223912
0.8485	Intermediate Similarity	NPC321822
0.8485	Intermediate Similarity	NPC325294
0.8483	Intermediate Similarity	NPC2745
0.8462	Intermediate Similarity	NPC191899
0.8462	Intermediate Similarity	NPC246229
0.8451	Intermediate Similarity	NPC90645
0.8425	Intermediate Similarity	NPC157783
0.8425	Intermediate Similarity	NPC172219
0.8425	Intermediate Similarity	NPC325860
0.8425	Intermediate Similarity	NPC304510
0.8417	Intermediate Similarity	NPC32630
0.8414	Intermediate Similarity	NPC158784
0.8414	Intermediate Similarity	NPC195561
0.8409	Intermediate Similarity	NPC470726
0.8409	Intermediate Similarity	NPC476653
0.8406	Intermediate Similarity	NPC470733
0.8397	Intermediate Similarity	NPC473451
0.8394	Intermediate Similarity	NPC311256
0.8394	Intermediate Similarity	NPC471942
0.8392	Intermediate Similarity	NPC233980
0.8382	Intermediate Similarity	NPC228843
0.838	Intermediate Similarity	NPC133251
0.8372	Intermediate Similarity	NPC135467
0.8372	Intermediate Similarity	NPC260832
0.837	Intermediate Similarity	NPC196193
0.837	Intermediate Similarity	NPC143483
0.8359	Intermediate Similarity	NPC154030
0.8359	Intermediate Similarity	NPC469609
0.8358	Intermediate Similarity	NPC472968
0.8356	Intermediate Similarity	NPC302915
0.8346	Intermediate Similarity	NPC38893
0.8346	Intermediate Similarity	NPC43000
0.8346	Intermediate Similarity	NPC92
0.8346	Intermediate Similarity	NPC308311
0.8346	Intermediate Similarity	NPC477137
0.8346	Intermediate Similarity	NPC100414
0.8346	Intermediate Similarity	NPC469663
0.8322	Intermediate Similarity	NPC126707
0.8321	Intermediate Similarity	NPC474453
0.832	Intermediate Similarity	NPC471179
0.8298	Intermediate Similarity	NPC35216
0.8296	Intermediate Similarity	NPC470747
0.8286	Intermediate Similarity	NPC230124
0.8286	Intermediate Similarity	NPC6300
0.8286	Intermediate Similarity	NPC475757
0.8286	Intermediate Similarity	NPC184613
0.8286	Intermediate Similarity	NPC474640
0.8286	Intermediate Similarity	NPC114171
0.8284	Intermediate Similarity	NPC108164
0.8281	Intermediate Similarity	NPC477136
0.8281	Intermediate Similarity	NPC16030
0.8276	Intermediate Similarity	NPC303013
0.8276	Intermediate Similarity	NPC212142
0.8276	Intermediate Similarity	NPC474940
0.8276	Intermediate Similarity	NPC179809
0.8276	Intermediate Similarity	NPC159697
0.8276	Intermediate Similarity	NPC474795
0.8276	Intermediate Similarity	NPC130959
0.8273	Intermediate Similarity	NPC472800
0.8273	Intermediate Similarity	NPC29799
0.8273	Intermediate Similarity	NPC209985
0.8273	Intermediate Similarity	NPC263367
0.8273	Intermediate Similarity	NPC477939
0.8273	Intermediate Similarity	NPC177160
0.8273	Intermediate Similarity	NPC10737
0.8273	Intermediate Similarity	NPC234952
0.8273	Intermediate Similarity	NPC54743
0.8273	Intermediate Similarity	NPC470802
0.8273	Intermediate Similarity	NPC156502
0.8268	Intermediate Similarity	NPC35797
0.8268	Intermediate Similarity	NPC192948
0.8261	Intermediate Similarity	NPC478085
0.8261	Intermediate Similarity	NPC49603
0.8261	Intermediate Similarity	NPC193026
0.8261	Intermediate Similarity	NPC187616
0.8254	Intermediate Similarity	NPC317869
0.8248	Intermediate Similarity	NPC303144
0.8248	Intermediate Similarity	NPC165612
0.8239	Intermediate Similarity	NPC186033
0.8222	Intermediate Similarity	NPC245826
0.8222	Intermediate Similarity	NPC307050
0.8222	Intermediate Similarity	NPC148366
0.8222	Intermediate Similarity	NPC277458
0.8222	Intermediate Similarity	NPC474178
0.8222	Intermediate Similarity	NPC311293
0.8222	Intermediate Similarity	NPC252307
0.8219	Intermediate Similarity	NPC220006
0.8219	Intermediate Similarity	NPC181452
0.8207	Intermediate Similarity	NPC101376
0.8203	Intermediate Similarity	NPC219112
0.8203	Intermediate Similarity	NPC308828
0.8201	Intermediate Similarity	NPC473413
0.8195	Intermediate Similarity	NPC257682
0.8195	Intermediate Similarity	NPC131747
0.8195	Intermediate Similarity	NPC146355
0.8194	Intermediate Similarity	NPC272619
0.8194	Intermediate Similarity	NPC286245
0.8182	Intermediate Similarity	NPC472451
0.8182	Intermediate Similarity	NPC321402
0.8182	Intermediate Similarity	NPC152946
0.8176	Intermediate Similarity	NPC160196
0.8169	Intermediate Similarity	NPC71046
0.8163	Intermediate Similarity	NPC260781
0.8163	Intermediate Similarity	NPC145979
0.8163	Intermediate Similarity	NPC214326
0.8163	Intermediate Similarity	NPC218041
0.8163	Intermediate Similarity	NPC225815
0.8163	Intermediate Similarity	NPC185955
0.8163	Intermediate Similarity	NPC182368
0.8163	Intermediate Similarity	NPC9933
0.8163	Intermediate Similarity	NPC469706
0.8163	Intermediate Similarity	NPC469707
0.8156	Intermediate Similarity	NPC70682
0.8156	Intermediate Similarity	NPC260741
0.8151	Intermediate Similarity	NPC291326
0.8151	Intermediate Similarity	NPC474856
0.8151	Intermediate Similarity	NPC290902
0.8151	Intermediate Similarity	NPC117788
0.8151	Intermediate Similarity	NPC474834
0.8148	Intermediate Similarity	NPC118533
0.8148	Intermediate Similarity	NPC165045
0.8148	Intermediate Similarity	NPC21563
0.8138	Intermediate Similarity	NPC274454
0.8138	Intermediate Similarity	NPC96576
0.8138	Intermediate Similarity	NPC471608
0.8138	Intermediate Similarity	NPC215678
0.8134	Intermediate Similarity	NPC4286
0.8134	Intermediate Similarity	NPC76119
0.8134	Intermediate Similarity	NPC148627
0.8129	Intermediate Similarity	NPC473107
0.8129	Intermediate Similarity	NPC209199
0.8125	Intermediate Similarity	NPC469795
0.8125	Intermediate Similarity	NPC253015
0.8125	Intermediate Similarity	NPC471065
0.8125	Intermediate Similarity	NPC147179
0.8125	Intermediate Similarity	NPC50250
0.8117	Intermediate Similarity	NPC25889
0.8116	Intermediate Similarity	NPC321502
0.8116	Intermediate Similarity	NPC254275
0.8116	Intermediate Similarity	NPC18842
0.8112	Intermediate Similarity	NPC59841
0.8112	Intermediate Similarity	NPC475891
0.8112	Intermediate Similarity	NPC204347
0.8112	Intermediate Similarity	NPC2613
0.8102	Intermediate Similarity	NPC153739
0.8102	Intermediate Similarity	NPC77040
0.8102	Intermediate Similarity	NPC242807
0.8102	Intermediate Similarity	NPC64201
0.8102	Intermediate Similarity	NPC92164
0.8102	Intermediate Similarity	NPC257582
0.8102	Intermediate Similarity	NPC241522
0.8102	Intermediate Similarity	NPC42300
0.8102	Intermediate Similarity	NPC145305
0.8102	Intermediate Similarity	NPC187998
0.8102	Intermediate Similarity	NPC174495
0.8099	Intermediate Similarity	NPC308768
0.8099	Intermediate Similarity	NPC259519
0.8099	Intermediate Similarity	NPC12668
0.8095	Intermediate Similarity	NPC44452
0.8095	Intermediate Similarity	NPC211561
0.8095	Intermediate Similarity	NPC474893
0.8095	Intermediate Similarity	NPC475940
0.8092	Intermediate Similarity	NPC3239
0.8092	Intermediate Similarity	NPC282255
0.8092	Intermediate Similarity	NPC475245
0.8088	Intermediate Similarity	NPC45774
0.8088	Intermediate Similarity	NPC129570

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 NPC59239 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	337
0.1-0.2	821
0.2-0.3	1684
0.3-0.4	2866
0.4-0.5	1872
0.5-0.6	1035
0.6-0.7	474
0.7-0.8	61
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
0.8169	Intermediate Similarity	NPD6674	Discontinued
0.8138	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.8116	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8116	Intermediate Similarity	NPD3620	Phase 2
0.7917	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD3094	Phase 2
0.7857	Intermediate Similarity	NPD1613	Approved
0.7857	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD3092	Approved
0.777	Intermediate Similarity	NPD3027	Phase 3
0.7714	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD3091	Approved
0.7656	Intermediate Similarity	NPD3021	Approved
0.7656	Intermediate Similarity	NPD3022	Approved
0.7655	Intermediate Similarity	NPD7266	Discontinued
0.7626	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD2861	Phase 2
0.7589	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD5126	Approved
0.7556	Intermediate Similarity	NPD5125	Phase 3
0.7554	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD5735	Approved
0.7536	Intermediate Similarity	NPD6696	Suspended
0.7533	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD4625	Phase 3
0.75	Intermediate Similarity	NPD8166	Discontinued
0.7483	Intermediate Similarity	NPD4060	Phase 1
0.7481	Intermediate Similarity	NPD7635	Approved
0.7464	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD4908	Phase 1
0.7426	Intermediate Similarity	NPD3095	Discontinued
0.741	Intermediate Similarity	NPD8651	Approved
0.7407	Intermediate Similarity	NPD7228	Approved
0.7391	Intermediate Similarity	NPD27	Approved
0.7391	Intermediate Similarity	NPD2489	Approved
0.7338	Intermediate Similarity	NPD4749	Approved
0.7329	Intermediate Similarity	NPD2969	Approved
0.7329	Intermediate Similarity	NPD2970	Approved
0.7296	Intermediate Similarity	NPD6234	Discontinued
0.7293	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD7741	Discontinued
0.7267	Intermediate Similarity	NPD3051	Approved
0.7261	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD4097	Suspended
0.7259	Intermediate Similarity	NPD7340	Approved
0.7254	Intermediate Similarity	NPD5736	Approved
0.7241	Intermediate Similarity	NPD4140	Approved
0.7231	Intermediate Similarity	NPD2342	Discontinued
0.7214	Intermediate Similarity	NPD5327	Phase 3
0.7197	Intermediate Similarity	NPD37	Approved
0.7194	Intermediate Similarity	NPD3705	Approved
0.7194	Intermediate Similarity	NPD1610	Phase 2
0.7192	Intermediate Similarity	NPD3657	Discovery
0.7181	Intermediate Similarity	NPD5763	Approved
0.7181	Intermediate Similarity	NPD5762	Approved
0.7174	Intermediate Similarity	NPD4626	Approved
0.717	Intermediate Similarity	NPD4966	Approved
0.717	Intermediate Similarity	NPD4965	Approved
0.717	Intermediate Similarity	NPD4967	Phase 2
0.7164	Intermediate Similarity	NPD1398	Phase 1
0.7164	Intermediate Similarity	NPD5283	Phase 1
0.7152	Intermediate Similarity	NPD5844	Phase 1
0.7143	Intermediate Similarity	NPD7313	Approved
0.7143	Intermediate Similarity	NPD7311	Approved
0.7143	Intermediate Similarity	NPD228	Approved
0.7143	Intermediate Similarity	NPD7312	Approved
0.7143	Intermediate Similarity	NPD7310	Approved
0.7121	Intermediate Similarity	NPD4750	Phase 3
0.712	Intermediate Similarity	NPD1809	Phase 2
0.7118	Intermediate Similarity	NPD4663	Approved
0.7114	Intermediate Similarity	NPD6100	Approved
0.7114	Intermediate Similarity	NPD6099	Approved
0.7101	Intermediate Similarity	NPD5691	Approved
0.7101	Intermediate Similarity	NPD7309	Approved
0.7078	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4624	Approved
0.7059	Intermediate Similarity	NPD7157	Approved
0.7055	Intermediate Similarity	NPD6663	Approved
0.705	Intermediate Similarity	NPD3019	Approved
0.705	Intermediate Similarity	NPD2932	Approved
0.705	Intermediate Similarity	NPD4059	Approved
0.7041	Intermediate Similarity	NPD4578	Approved
0.7041	Intermediate Similarity	NPD4577	Approved
0.7037	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6353	Approved
0.7015	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD7041	Phase 2
0.6994	Remote Similarity	NPD6959	Discontinued
0.6994	Remote Similarity	NPD8127	Discontinued
0.6993	Remote Similarity	NPD2677	Approved
0.6981	Remote Similarity	NPD1934	Approved
0.698	Remote Similarity	NPD4536	Approved
0.698	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4538	Approved
0.6977	Remote Similarity	NPD7906	Approved
0.697	Remote Similarity	NPD6166	Phase 2
0.697	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD3645	Discontinued
0.6959	Remote Similarity	NPD5124	Phase 1
0.6959	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD3020	Approved
0.6934	Remote Similarity	NPD6671	Approved
0.6929	Remote Similarity	NPD288	Approved
0.6928	Remote Similarity	NPD4628	Phase 3
0.6928	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7240	Approved
0.6899	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD2238	Phase 2
0.6883	Remote Similarity	NPD6190	Approved
0.6871	Remote Similarity	NPD7985	Registered
0.6857	Remote Similarity	NPD1357	Approved
0.6855	Remote Similarity	NPD4380	Phase 2
0.6853	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.685	Remote Similarity	NPD844	Approved
0.6848	Remote Similarity	NPD6232	Discontinued
0.6839	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1653	Approved
0.6832	Remote Similarity	NPD5929	Approved
0.6831	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD1091	Approved
0.6831	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD4666	Phase 3
0.6826	Remote Similarity	NPD7473	Discontinued
0.6825	Remote Similarity	NPD845	Approved
0.6821	Remote Similarity	NPD5960	Phase 3
0.6821	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD5588	Approved
0.6821	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7003	Approved
0.6818	Remote Similarity	NPD4110	Phase 3
0.6818	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD4198	Discontinued
0.6809	Remote Similarity	NPD9381	Approved
0.6809	Remote Similarity	NPD9384	Approved
0.6806	Remote Similarity	NPD1283	Approved
0.6805	Remote Similarity	NPD7074	Phase 3
0.6795	Remote Similarity	NPD2421	Approved
0.6795	Remote Similarity	NPD2420	Approved
0.6794	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD2684	Approved
0.679	Remote Similarity	NPD2560	Approved
0.679	Remote Similarity	NPD2563	Approved
0.6786	Remote Similarity	NPD1548	Phase 1
0.6779	Remote Similarity	NPD2979	Phase 3
0.6779	Remote Similarity	NPD3059	Approved
0.6779	Remote Similarity	NPD3061	Approved
0.6779	Remote Similarity	NPD3062	Approved
0.6772	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5709	Phase 3
0.6766	Remote Similarity	NPD4481	Phase 3
0.6763	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD5177	Phase 3
0.6752	Remote Similarity	NPD2533	Approved
0.6752	Remote Similarity	NPD2532	Approved
0.6752	Remote Similarity	NPD2534	Approved
0.6747	Remote Similarity	NPD6071	Discontinued
0.6746	Remote Similarity	NPD7054	Approved
0.6744	Remote Similarity	NPD8312	Approved
0.6744	Remote Similarity	NPD8313	Approved
0.6738	Remote Similarity	NPD1651	Approved
0.6736	Remote Similarity	NPD9622	Approved
0.6735	Remote Similarity	NPD2605	Approved
0.6735	Remote Similarity	NPD2606	Approved
0.6733	Remote Similarity	NPD230	Phase 1
0.6731	Remote Similarity	NPD5058	Phase 3
0.6728	Remote Similarity	NPD8455	Phase 2
0.6728	Remote Similarity	NPD1465	Phase 2
0.6727	Remote Similarity	NPD5494	Approved
0.6724	Remote Similarity	NPD8150	Discontinued
0.6719	Remote Similarity	NPD2859	Approved
0.6719	Remote Similarity	NPD2860	Approved
0.6715	Remote Similarity	NPD7843	Approved
0.6713	Remote Similarity	NPD1611	Approved
0.6711	Remote Similarity	NPD7743	Approved
0.6711	Remote Similarity	NPD4108	Discontinued
0.6711	Remote Similarity	NPD7742	Approved
0.6711	Remote Similarity	NPD1753	Discontinued
0.671	Remote Similarity	NPD6331	Phase 2
0.6709	Remote Similarity	NPD6090	Discontinued
0.6709	Remote Similarity	NPD6273	Approved
0.6707	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7833	Phase 2
0.6707	Remote Similarity	NPD7831	Phase 2
0.6706	Remote Similarity	NPD7472	Approved
0.6705	Remote Similarity	NPD2490	Approved
0.6705	Remote Similarity	NPD2488	Approved
0.669	Remote Similarity	NPD2286	Discontinued
0.669	Remote Similarity	NPD1778	Approved
0.669	Remote Similarity	NPD1751	Approved
0.669	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD7095	Approved
0.6689	Remote Similarity	NPD5156	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