NPASS Compound

Structure

NPC19432 OpenBabel07101718232D 22 25 0 0 1 0 0 0 0 0999 V2000 -3.8764 -1.1957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1767 1.0879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0398 2.0879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 -0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6802 0.7331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2407 -1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2435 -1.5593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5889 1.8969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9209 -0.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1767 1.0879 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9058 1.5879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6379 1.5879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6802 -0.7331 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7718 0.0879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9058 0.5879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6379 0.5879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 0.2225 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5889 0.2788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7718 2.0879 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 -4.8979 -0.6722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7718 3.0879 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 2 0 0 0 0 3 11 1 0 0 0 0 4 20 1 0 0 0 0 5 20 1 0 0 0 0 6 7 1 0 0 0 0 6 9 1 0 0 0 0 8 10 1 0 0 0 0 8 12 1 0 0 0 0 9 14 1 0 0 0 0 10 2 1 1 0 0 0 10 18 1 0 0 0 0 11 15 1 0 0 0 0 11 19 2 0 0 0 0 12 16 2 0 0 0 0 12 19 1 0 0 0 0 13 7 1 6 0 0 0 13 17 1 0 0 0 0 13 20 1 0 0 0 0 14 15 2 0 0 0 0 14 16 1 0 0 0 0 16 18 1 0 0 0 0 17 15 1 6 0 0 0 17 20 1 0 0 0 0 18 21 2 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	296.18
Volume:	324.648
LogP:	5.307
LogD:	4.067
LogS:	-5.869
# Rotatable Bonds:	0
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.758
Synthetic Accessibility Score:	4.266
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.795
MDCK Permeability:	1.791015893104486e-05
Pgp-inhibitor:	0.971
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.739
30% Bioavailability (F30%):	0.764

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.147
Plasma Protein Binding (PPB):	99.16312408447266%
Volume Distribution (VD):	2.974
Pgp-substrate:	1.2625657320022583%

ADMET: Metabolism

CYP1A2-inhibitor:	0.319
CYP1A2-substrate:	0.921
CYP2C19-inhibitor:	0.47
CYP2C19-substrate:	0.845
CYP2C9-inhibitor:	0.586
CYP2C9-substrate:	0.937
CYP2D6-inhibitor:	0.097
CYP2D6-substrate:	0.84
CYP3A4-inhibitor:	0.365
CYP3A4-substrate:	0.599

ADMET: Excretion

Clearance (CL):	5.888
Half-life (T1/2):	0.033

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.381
Drug-inuced Liver Injury (DILI):	0.138
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.636
Maximum Recommended Daily Dose:	0.914
Skin Sensitization:	0.805
Carcinogencity:	0.022
Eye Corrosion:	0.003
Eye Irritation:	0.108
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC19432

Natural Product ID:	NPC19432
*Common Name:**	Jatropholone A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BMHPRIPRPDSKRK-MNRXQERYSA-N
Standard InCHI:	InChI=1S/C20H24O2/c1-9-6-7-13-17(20(13,4)5)15-11(3)19(22)12-8-10(2)18(21)16(12)14(9)15/h10,13,17,22H,1,6-8H2,2-5H3/t10-,13+,17+/m0/s1
SMILES:	C=C1CC[C@@H]2[C@H](c3c(C)c(c4C[C@H](C)C(=O)c4c13)O)C2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1088068
PubChem CID:	46881274
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000027] Indanes [CHEMONTID:0001151] Indanones

*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
NPO19811	Jatropha integerrima	Species	Euphorbiaceae	Eukaryota	latex	n.a.	n.a.	PMID[17067157]
NPO19811	Jatropha integerrima	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19943622]
NPO19811	Jatropha integerrima	Species	Euphorbiaceae	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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	5.4	ug.mL-1	PMID[462998]

☑ 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 NPC19432 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	332
0.1-0.2	1670
0.2-0.3	3575
0.3-0.4	10227
0.4-0.5	10850
0.5-0.6	9714
0.6-0.7	5436
0.7-0.8	854
0.8-0.85	32
0.85-0.9	4
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9449	High Similarity	NPC52368
0.9449	High Similarity	NPC218854
0.896	High Similarity	NPC12818
0.864	High Similarity	NPC190971
0.8605	High Similarity	NPC176130
0.8605	High Similarity	NPC78364
0.8605	High Similarity	NPC84672
0.8605	High Similarity	NPC69424
0.8605	High Similarity	NPC72667
0.855	High Similarity	NPC108129
0.8527	High Similarity	NPC254492
0.8516	High Similarity	NPC199273
0.8504	High Similarity	NPC282577
0.8473	Intermediate Similarity	NPC276238
0.8473	Intermediate Similarity	NPC171460
0.8397	Intermediate Similarity	NPC3009
0.8358	Intermediate Similarity	NPC138472
0.8358	Intermediate Similarity	NPC111845
0.8346	Intermediate Similarity	NPC471851
0.8333	Intermediate Similarity	NPC303910
0.8308	Intermediate Similarity	NPC123506
0.8296	Intermediate Similarity	NPC202225
0.8281	Intermediate Similarity	NPC154696
0.8258	Intermediate Similarity	NPC96024
0.8235	Intermediate Similarity	NPC153088
0.8222	Intermediate Similarity	NPC477139
0.8222	Intermediate Similarity	NPC78307
0.8175	Intermediate Similarity	NPC299734
0.8154	Intermediate Similarity	NPC273683
0.8116	Intermediate Similarity	NPC36868
0.8116	Intermediate Similarity	NPC475957
0.8102	Intermediate Similarity	NPC477596
0.8062	Intermediate Similarity	NPC32322
0.8062	Intermediate Similarity	NPC259703
0.8058	Intermediate Similarity	NPC230811
0.8047	Intermediate Similarity	NPC258366
0.8047	Intermediate Similarity	NPC31296
0.8047	Intermediate Similarity	NPC79933
0.8047	Intermediate Similarity	NPC473974
0.803	Intermediate Similarity	NPC137750
0.8029	Intermediate Similarity	NPC477594
0.8015	Intermediate Similarity	NPC275145
0.7986	Intermediate Similarity	NPC147691
0.7984	Intermediate Similarity	NPC318552
0.7984	Intermediate Similarity	NPC190501
0.7971	Intermediate Similarity	NPC244640
0.7971	Intermediate Similarity	NPC279291
0.797	Intermediate Similarity	NPC15837
0.7958	Intermediate Similarity	NPC477209
0.7955	Intermediate Similarity	NPC181334
0.7943	Intermediate Similarity	NPC471853
0.7941	Intermediate Similarity	NPC476847
0.7939	Intermediate Similarity	NPC176208
0.7923	Intermediate Similarity	NPC472046
0.7923	Intermediate Similarity	NPC241001
0.7923	Intermediate Similarity	NPC474175
0.7891	Intermediate Similarity	NPC174087
0.7887	Intermediate Similarity	NPC477275
0.7883	Intermediate Similarity	NPC474109
0.7879	Intermediate Similarity	NPC471187
0.7868	Intermediate Similarity	NPC253488
0.7863	Intermediate Similarity	NPC249340
0.7863	Intermediate Similarity	NPC162935
0.7862	Intermediate Similarity	NPC477208
0.7857	Intermediate Similarity	NPC49911
0.7857	Intermediate Similarity	NPC53001
0.7857	Intermediate Similarity	NPC242136
0.7857	Intermediate Similarity	NPC277559
0.7857	Intermediate Similarity	NPC477592
0.7836	Intermediate Similarity	NPC269598
0.7832	Intermediate Similarity	NPC248068
0.7826	Intermediate Similarity	NPC59459
0.7826	Intermediate Similarity	NPC263817
0.7826	Intermediate Similarity	NPC114183
0.7812	Intermediate Similarity	NPC477453
0.781	Intermediate Similarity	NPC17083
0.781	Intermediate Similarity	NPC291001
0.781	Intermediate Similarity	NPC41847
0.7803	Intermediate Similarity	NPC307174
0.7803	Intermediate Similarity	NPC121168
0.7803	Intermediate Similarity	NPC11250
0.7801	Intermediate Similarity	NPC87723
0.7801	Intermediate Similarity	NPC477593
0.7795	Intermediate Similarity	NPC274839
0.7794	Intermediate Similarity	NPC117899
0.7793	Intermediate Similarity	NPC225351
0.7786	Intermediate Similarity	NPC471670
0.7786	Intermediate Similarity	NPC474311
0.7786	Intermediate Similarity	NPC472308
0.7778	Intermediate Similarity	NPC231717
0.777	Intermediate Similarity	NPC50924
0.777	Intermediate Similarity	NPC270899
0.777	Intermediate Similarity	NPC12070
0.7761	Intermediate Similarity	NPC477454
0.7761	Intermediate Similarity	NPC131799
0.773	Intermediate Similarity	NPC119542
0.7727	Intermediate Similarity	NPC120545
0.7724	Intermediate Similarity	NPC309169
0.7724	Intermediate Similarity	NPC196941
0.7724	Intermediate Similarity	NPC160839
0.7721	Intermediate Similarity	NPC229894
0.7721	Intermediate Similarity	NPC48248
0.7721	Intermediate Similarity	NPC193203
0.7714	Intermediate Similarity	NPC290803
0.7714	Intermediate Similarity	NPC474076
0.7714	Intermediate Similarity	NPC249272
0.771	Intermediate Similarity	NPC478121
0.7708	Intermediate Similarity	NPC308572
0.7704	Intermediate Similarity	NPC473691
0.7704	Intermediate Similarity	NPC227741
0.7704	Intermediate Similarity	NPC472047
0.7704	Intermediate Similarity	NPC136342
0.7704	Intermediate Similarity	NPC160499
0.7704	Intermediate Similarity	NPC295202
0.7704	Intermediate Similarity	NPC49647
0.7704	Intermediate Similarity	NPC71610
0.7698	Intermediate Similarity	NPC37299
0.7698	Intermediate Similarity	NPC180261
0.7692	Intermediate Similarity	NPC169452
0.7692	Intermediate Similarity	NPC181560
0.7687	Intermediate Similarity	NPC5568
0.7687	Intermediate Similarity	NPC152525
0.7687	Intermediate Similarity	NPC142956
0.7687	Intermediate Similarity	NPC15127
0.7687	Intermediate Similarity	NPC68756
0.7681	Intermediate Similarity	NPC93015
0.7681	Intermediate Similarity	NPC18798
0.7681	Intermediate Similarity	NPC164295
0.7681	Intermediate Similarity	NPC239134
0.7674	Intermediate Similarity	NPC83718
0.7669	Intermediate Similarity	NPC297057
0.7669	Intermediate Similarity	NPC91478
0.766	Intermediate Similarity	NPC86524
0.766	Intermediate Similarity	NPC193358
0.766	Intermediate Similarity	NPC191976
0.7655	Intermediate Similarity	NPC100242
0.7647	Intermediate Similarity	NPC471530
0.7647	Intermediate Similarity	NPC30491
0.7647	Intermediate Similarity	NPC262936
0.7643	Intermediate Similarity	NPC293454
0.7643	Intermediate Similarity	NPC166480
0.7643	Intermediate Similarity	NPC282780
0.7639	Intermediate Similarity	NPC92079
0.7639	Intermediate Similarity	NPC477595
0.7634	Intermediate Similarity	NPC473767
0.763	Intermediate Similarity	NPC87985
0.7626	Intermediate Similarity	NPC165612
0.7626	Intermediate Similarity	NPC312560
0.7626	Intermediate Similarity	NPC58685
0.7622	Intermediate Similarity	NPC138099
0.7622	Intermediate Similarity	NPC242994
0.7622	Intermediate Similarity	NPC162939
0.7619	Intermediate Similarity	NPC143685
0.7615	Intermediate Similarity	NPC160199
0.7612	Intermediate Similarity	NPC174991
0.7612	Intermediate Similarity	NPC198014
0.7609	Intermediate Similarity	NPC62219
0.7606	Intermediate Similarity	NPC471905
0.7606	Intermediate Similarity	NPC471452
0.76	Intermediate Similarity	NPC64586
0.7597	Intermediate Similarity	NPC469719
0.7597	Intermediate Similarity	NPC322197
0.7597	Intermediate Similarity	NPC161304
0.7594	Intermediate Similarity	NPC253627
0.7589	Intermediate Similarity	NPC80035
0.7589	Intermediate Similarity	NPC283088
0.7589	Intermediate Similarity	NPC258502
0.7586	Intermediate Similarity	NPC184935
0.7586	Intermediate Similarity	NPC193555
0.7584	Intermediate Similarity	NPC142654
0.7576	Intermediate Similarity	NPC285829
0.7576	Intermediate Similarity	NPC206778
0.7574	Intermediate Similarity	NPC306765
0.7574	Intermediate Similarity	NPC474737
0.7571	Intermediate Similarity	NPC53896
0.7571	Intermediate Similarity	NPC49742
0.7571	Intermediate Similarity	NPC225051
0.7571	Intermediate Similarity	NPC474715
0.7571	Intermediate Similarity	NPC4170
0.7571	Intermediate Similarity	NPC115458
0.7571	Intermediate Similarity	NPC48036
0.7571	Intermediate Similarity	NPC52407
0.7571	Intermediate Similarity	NPC267205
0.7569	Intermediate Similarity	NPC96421
0.7569	Intermediate Similarity	NPC476534
0.7569	Intermediate Similarity	NPC473527
0.7568	Intermediate Similarity	NPC52692
0.7557	Intermediate Similarity	NPC273282
0.7557	Intermediate Similarity	NPC474890
0.7557	Intermediate Similarity	NPC161943
0.7556	Intermediate Similarity	NPC234890
0.7556	Intermediate Similarity	NPC173978
0.7556	Intermediate Similarity	NPC74507
0.7554	Intermediate Similarity	NPC474517
0.7554	Intermediate Similarity	NPC244699
0.7554	Intermediate Similarity	NPC85342
0.7554	Intermediate Similarity	NPC72669
0.7552	Intermediate Similarity	NPC123714
0.7552	Intermediate Similarity	NPC4214
0.7552	Intermediate Similarity	NPC13715

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 NPC19432 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	345
0.1-0.2	1055
0.2-0.3	1778
0.3-0.4	3008
0.4-0.5	1930
0.5-0.6	846
0.6-0.7	175
0.7-0.8	13
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
0.8047	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD3019	Approved
0.7984	Intermediate Similarity	NPD2932	Approved
0.7535	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD3026	Approved
0.7388	Intermediate Similarity	NPD3023	Approved
0.7368	Intermediate Similarity	NPD3025	Approved
0.7368	Intermediate Similarity	NPD3024	Approved
0.7333	Intermediate Similarity	NPD1201	Approved
0.7315	Intermediate Similarity	NPD2534	Approved
0.7315	Intermediate Similarity	NPD2533	Approved
0.7315	Intermediate Similarity	NPD2532	Approved
0.7273	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD7390	Discontinued
0.7246	Intermediate Similarity	NPD1470	Approved
0.7183	Intermediate Similarity	NPD6663	Approved
0.7143	Intermediate Similarity	NPD5736	Approved
0.7123	Intermediate Similarity	NPD5405	Approved
0.7123	Intermediate Similarity	NPD5406	Approved
0.7123	Intermediate Similarity	NPD5404	Approved
0.7123	Intermediate Similarity	NPD5408	Approved
0.7086	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4059	Approved
0.7047	Intermediate Similarity	NPD7003	Approved
0.7037	Intermediate Similarity	NPD3091	Approved
0.6992	Remote Similarity	NPD5951	Approved
0.6992	Remote Similarity	NPD1809	Phase 2
0.698	Remote Similarity	NPD2800	Approved
0.697	Remote Similarity	NPD7635	Approved
0.6939	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD4626	Approved
0.6934	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD1876	Approved
0.6918	Remote Similarity	NPD6651	Approved
0.6906	Remote Similarity	NPD3972	Approved
0.6846	Remote Similarity	NPD2346	Discontinued
0.6838	Remote Similarity	NPD7610	Discontinued
0.6835	Remote Similarity	NPD3092	Approved
0.6824	Remote Similarity	NPD2799	Discontinued
0.6824	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6273	Approved
0.6809	Remote Similarity	NPD1283	Approved
0.68	Remote Similarity	NPD288	Approved
0.6795	Remote Similarity	NPD7458	Discontinued
0.6781	Remote Similarity	NPD943	Approved
0.6779	Remote Similarity	NPD6100	Approved
0.6779	Remote Similarity	NPD6099	Approved
0.6761	Remote Similarity	NPD1164	Approved
0.6739	Remote Similarity	NPD1651	Approved
0.6738	Remote Similarity	NPD1755	Approved
0.6733	Remote Similarity	NPD2344	Approved
0.6732	Remote Similarity	NPD3300	Phase 2
0.672	Remote Similarity	NPD844	Approved
0.6718	Remote Similarity	NPD2342	Discontinued
0.6718	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD8032	Phase 2
0.6694	Remote Similarity	NPD845	Approved
0.6691	Remote Similarity	NPD3095	Discontinued
0.6691	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2935	Discontinued
0.6667	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD5711	Approved
0.6646	Remote Similarity	NPD5710	Approved
0.6644	Remote Similarity	NPD3764	Approved
0.6643	Remote Similarity	NPD3094	Phase 2
0.6641	Remote Similarity	NPD289	Clinical (unspecified phase)
0.664	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7473	Discontinued
0.6619	Remote Similarity	NPD5691	Approved
0.6617	Remote Similarity	NPD4750	Phase 3
0.6601	Remote Similarity	NPD8166	Discontinued
0.6596	Remote Similarity	NPD1281	Approved
0.6582	Remote Similarity	NPD3226	Approved
0.6577	Remote Similarity	NPD1607	Approved
0.6562	Remote Similarity	NPD3020	Approved
0.6558	Remote Similarity	NPD2309	Approved
0.6552	Remote Similarity	NPD4208	Discontinued
0.6547	Remote Similarity	NPD7009	Phase 2
0.6547	Remote Similarity	NPD9545	Approved
0.6545	Remote Similarity	NPD6232	Discontinued
0.6522	Remote Similarity	NPD7340	Approved
0.6519	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD7236	Approved
0.6507	Remote Similarity	NPD4207	Discontinued
0.6494	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD4628	Phase 3
0.6485	Remote Similarity	NPD6959	Discontinued
0.6483	Remote Similarity	NPD4624	Approved
0.6483	Remote Similarity	NPD2798	Approved
0.6463	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD6696	Suspended
0.6454	Remote Similarity	NPD1751	Approved
0.6444	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD1240	Approved
0.6438	Remote Similarity	NPD7028	Phase 2
0.6438	Remote Similarity	NPD9494	Approved
0.6434	Remote Similarity	NPD4878	Approved
0.6434	Remote Similarity	NPD9269	Phase 2
0.6433	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD1398	Phase 1
0.642	Remote Similarity	NPD7819	Suspended
0.6418	Remote Similarity	NPD74	Approved
0.6418	Remote Similarity	NPD9266	Approved
0.6415	Remote Similarity	NPD7239	Suspended
0.6412	Remote Similarity	NPD1929	Approved
0.6412	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD1930	Approved
0.6405	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6403	Remote Similarity	NPD9493	Approved
0.6397	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD9268	Approved
0.6378	Remote Similarity	NPD1693	Approved
0.6375	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.637	Remote Similarity	NPD3021	Approved
0.637	Remote Similarity	NPD3022	Approved
0.6358	Remote Similarity	NPD4097	Suspended
0.6351	Remote Similarity	NPD7008	Discontinued
0.6343	Remote Similarity	NPD9267	Approved
0.6343	Remote Similarity	NPD9264	Approved
0.6343	Remote Similarity	NPD9263	Approved
0.6333	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD3620	Phase 2
0.6333	Remote Similarity	NPD4140	Approved
0.6333	Remote Similarity	NPD2979	Phase 3
0.6329	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD2859	Approved
0.6328	Remote Similarity	NPD2860	Approved
0.6327	Remote Similarity	NPD4212	Discontinued
0.6319	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5190	Phase 2
0.6309	Remote Similarity	NPD2313	Discontinued
0.6309	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD2066	Phase 3
0.6299	Remote Similarity	NPD1471	Phase 3
0.6294	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD230	Phase 1
0.6286	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD3750	Approved
0.628	Remote Similarity	NPD5978	Approved
0.628	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.628	Remote Similarity	NPD5977	Approved
0.6279	Remote Similarity	NPD3495	Discontinued
0.6275	Remote Similarity	NPD1510	Phase 2
0.6268	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD7961	Discontinued
0.6257	Remote Similarity	NPD4603	Phase 2
0.6257	Remote Similarity	NPD6020	Phase 2
0.625	Remote Similarity	NPD2934	Approved
0.625	Remote Similarity	NPD2933	Approved
0.6234	Remote Similarity	NPD4477	Approved
0.6234	Remote Similarity	NPD4476	Approved
0.6225	Remote Similarity	NPD4060	Phase 1
0.6224	Remote Similarity	NPD2286	Discontinued
0.6224	Remote Similarity	NPD1778	Approved
0.622	Remote Similarity	NPD1088	Approved
0.6212	Remote Similarity	NPD940	Approved
0.6212	Remote Similarity	NPD846	Approved
0.6207	Remote Similarity	NPD1608	Approved
0.6204	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.62	Remote Similarity	NPD3268	Approved
0.619	Remote Similarity	NPD2797	Approved
0.6181	Remote Similarity	NPD3143	Discontinued
0.6169	Remote Similarity	NPD7742	Approved
0.6169	Remote Similarity	NPD7743	Approved
0.6164	Remote Similarity	NPD5327	Phase 3
0.6163	Remote Similarity	NPD5844	Phase 1
0.6154	Remote Similarity	NPD4093	Discontinued
0.6149	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD2195	Approved
0.6149	Remote Similarity	NPD2194	Approved
0.6149	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD3882	Suspended
0.6144	Remote Similarity	NPD2157	Approved
0.6144	Remote Similarity	NPD6353	Approved
0.6143	Remote Similarity	NPD2629	Approved
0.6135	Remote Similarity	NPD4380	Phase 2
0.6135	Remote Similarity	NPD6599	Discontinued
0.6129	Remote Similarity	NPD2438	Suspended
0.6129	Remote Similarity	NPD2531	Phase 2
0.6127	Remote Similarity	NPD7644	Approved
0.6121	Remote Similarity	NPD5761	Phase 2
0.6121	Remote Similarity	NPD5760	Phase 2
0.6121	Remote Similarity	NPD2801	Approved
0.6119	Remote Similarity	NPD1237	Approved
0.6111	Remote Similarity	NPD4589	Approved
0.6108	Remote Similarity	NPD3749	Approved
0.6107	Remote Similarity	NPD3636	Approved
0.6107	Remote Similarity	NPD3637	Approved
0.6107	Remote Similarity	NPD3635	Approved
0.6099	Remote Similarity	NPD3317	Approved
0.6099	Remote Similarity	NPD256	Approved
0.6099	Remote Similarity	NPD255	Approved
0.6096	Remote Similarity	NPD3070	Discontinued

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