NPASS Compound

Structure

CID187923 OpenBabel06191715572D 22 25 0 0 0 0 0 0 0 0999 V2000 5.6514 -3.7286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2133 -3.8007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0828 -3.0577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7706 -0.6496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9294 -0.1639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7706 -1.6215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3950 0.8874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0877 -0.6497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9295 -2.1073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4048 -0.6498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0878 -1.6216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5631 -0.1641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -1.6217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5632 -2.1075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7220 -1.6218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7219 -0.6499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9295 -3.0787 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5633 -3.0789 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1192 -2.1076 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3610 0.7860 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 3.2466 -2.1074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 8 1 0 0 0 0 6 9 2 0 0 0 0 7 20 1 0 0 0 0 7 21 1 0 0 0 0 8 10 1 0 0 0 0 8 11 2 0 0 0 0 9 11 1 0 0 0 0 9 17 1 0 0 0 0 10 12 2 0 0 0 0 10 13 1 0 0 0 0 11 22 1 0 0 0 0 12 16 1 0 0 0 0 12 20 1 0 0 0 0 13 14 2 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 14 18 1 0 0 0 0 15 16 2 0 0 0 0 15 19 1 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.08
Volume:	287.989
LogP:	3.116
LogD:	3.302
LogS:	-4.687
# Rotatable Bonds:	3
TPSA:	59.29
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.739
Synthetic Accessibility Score:	2.679
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.597
MDCK Permeability:	3.627488695201464e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.166
Plasma Protein Binding (PPB):	79.26033020019531%
Volume Distribution (VD):	0.95
Pgp-substrate:	15.333146095275879%

ADMET: Metabolism

CYP1A2-inhibitor:	0.946
CYP1A2-substrate:	0.952
CYP2C19-inhibitor:	0.958
CYP2C19-substrate:	0.872
CYP2C9-inhibitor:	0.722
CYP2C9-substrate:	0.922
CYP2D6-inhibitor:	0.146
CYP2D6-substrate:	0.911
CYP3A4-inhibitor:	0.815
CYP3A4-substrate:	0.488

ADMET: Excretion

Clearance (CL):	11.129
Half-life (T1/2):	0.315

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.303
Drug-inuced Liver Injury (DILI):	0.981
AMES Toxicity:	0.566
Rat Oral Acute Toxicity:	0.086
Maximum Recommended Daily Dose:	0.027
Skin Sensitization:	0.632
Carcinogencity:	0.947
Eye Corrosion:	0.005
Eye Irritation:	0.224
Respiratory Toxicity:	0.571

Download Data

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

Natural Product: NPC187923

Natural Product ID:	NPC187923
*Common Name:**	1,2-Methylenedioxy-3,4,6-Trimethoxydibenzofuran
IUPAC Name:	4,5,7-trimethoxy-[1]benzofuro[2,3-g][1,3]benzodioxole
Synonyms:
Standard InCHIKey:	SUYTZNXJVBRFQQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H14O6/c1-17-9-6-4-5-8-10-12-16(21-7-20-12)15(19-3)14(18-2)13(10)22-11(8)9/h4-6H,7H2,1-3H3
SMILES:	COc1cccc2c3c4c(c(c(c3oc12)OC)OC)OCO4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1270046
PubChem CID:	49831389
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans [CHEMONTID:0000015] Dibenzofurans

*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
NPO5061.1	Rhaphiolepis indica var. tashiroi	Varieties	Rosaceae	Eukaryota	n.a.	root	n.a.	DOI[10.1021/np100200s]
NPO5061.1	Rhaphiolepis indica var. tashiroi	Varieties	Rosaceae	Eukaryota	Roots	Wutai, Pingtung County, Taiwan	2007-SEP	PMID[20839880]

☑ 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
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[492983]

☑ 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 NPC187923 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	520
0.1-0.2	2080
0.2-0.3	5078
0.3-0.4	11192
0.4-0.5	6427
0.5-0.6	3999
0.6-0.7	5939
0.7-0.8	5385
0.8-0.85	1569
0.85-0.9	451
0.9-0.95	52
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9367	High Similarity	NPC131557
0.9325	High Similarity	NPC475964
0.9313	High Similarity	NPC110257
0.9268	High Similarity	NPC62640
0.9212	High Similarity	NPC236327
0.9212	High Similarity	NPC290304
0.9212	High Similarity	NPC66804
0.9202	High Similarity	NPC211309
0.9182	High Similarity	NPC257914
0.9182	High Similarity	NPC238405
0.9182	High Similarity	NPC104459
0.9172	High Similarity	NPC279930
0.9172	High Similarity	NPC244371
0.9152	High Similarity	NPC72455
0.9114	High Similarity	NPC3273
0.9114	High Similarity	NPC284353
0.9108	High Similarity	NPC292460
0.9085	High Similarity	NPC41853
0.9074	High Similarity	NPC39305
0.9074	High Similarity	NPC59295
0.9074	High Similarity	NPC1706
0.9074	High Similarity	NPC263092
0.9074	High Similarity	NPC1755
0.9024	High Similarity	NPC167479
0.9018	High Similarity	NPC45449
0.9018	High Similarity	NPC36320
0.9012	High Similarity	NPC238995
0.9012	High Similarity	NPC478199
0.9	High Similarity	NPC258644
0.8987	High Similarity	NPC153008
0.8987	High Similarity	NPC148497
0.8976	High Similarity	NPC157522
0.8951	High Similarity	NPC188486
0.8951	High Similarity	NPC109238
0.8944	High Similarity	NPC15764
0.8938	High Similarity	NPC45131
0.8931	High Similarity	NPC478213
0.8916	High Similarity	NPC476641
0.891	High Similarity	NPC117463
0.8903	High Similarity	NPC224687
0.8896	High Similarity	NPC84515
0.8896	High Similarity	NPC302741
0.8896	High Similarity	NPC312056
0.8896	High Similarity	NPC272722
0.8889	High Similarity	NPC269906
0.8889	High Similarity	NPC139876
0.8868	High Similarity	NPC68882
0.8862	High Similarity	NPC54098
0.8862	High Similarity	NPC230619
0.8848	High Similarity	NPC155264
0.8848	High Similarity	NPC193881
0.8848	High Similarity	NPC113093
0.8848	High Similarity	NPC67450
0.8848	High Similarity	NPC210460
0.8841	High Similarity	NPC179464
0.8834	High Similarity	NPC99968
0.8834	High Similarity	NPC296540
0.8834	High Similarity	NPC309335
0.8834	High Similarity	NPC264293
0.8827	High Similarity	NPC16935
0.8827	High Similarity	NPC196879
0.8812	High Similarity	NPC57211
0.881	High Similarity	NPC216842
0.881	High Similarity	NPC476640
0.881	High Similarity	NPC82217
0.881	High Similarity	NPC65885
0.8805	High Similarity	NPC279061
0.8797	High Similarity	NPC69752
0.8795	High Similarity	NPC76482
0.8782	High Similarity	NPC296575
0.878	High Similarity	NPC273021
0.878	High Similarity	NPC18284
0.878	High Similarity	NPC234536
0.878	High Similarity	NPC19948
0.878	High Similarity	NPC469575
0.878	High Similarity	NPC78612
0.8765	High Similarity	NPC310206
0.8765	High Similarity	NPC474990
0.8758	High Similarity	NPC478238
0.8757	High Similarity	NPC287243
0.875	High Similarity	NPC52623
0.8743	High Similarity	NPC247136
0.8742	High Similarity	NPC474975
0.8742	High Similarity	NPC259058
0.8742	High Similarity	NPC201547
0.8734	High Similarity	NPC10304
0.8734	High Similarity	NPC63256
0.8727	High Similarity	NPC133065
0.8727	High Similarity	NPC65846
0.8726	High Similarity	NPC231013
0.872	High Similarity	NPC162668
0.8712	High Similarity	NPC62518
0.8712	High Similarity	NPC250076
0.8712	High Similarity	NPC215375
0.8712	High Similarity	NPC195832
0.8706	High Similarity	NPC8127
0.8706	High Similarity	NPC24258
0.8706	High Similarity	NPC156635
0.8706	High Similarity	NPC49667
0.8704	High Similarity	NPC155063
0.8704	High Similarity	NPC472461
0.8704	High Similarity	NPC261484
0.8683	High Similarity	NPC247973
0.8683	High Similarity	NPC470704
0.8683	High Similarity	NPC42892
0.8679	High Similarity	NPC181250
0.8675	High Similarity	NPC39306
0.8671	High Similarity	NPC205522
0.8671	High Similarity	NPC299923
0.8659	High Similarity	NPC243509
0.8655	High Similarity	NPC98546
0.865	High Similarity	NPC76458
0.865	High Similarity	NPC167595
0.865	High Similarity	NPC82733
0.8642	High Similarity	NPC241774
0.8642	High Similarity	NPC122623
0.8642	High Similarity	NPC34725
0.8642	High Similarity	NPC276059
0.8614	High Similarity	NPC470178
0.8608	High Similarity	NPC106461
0.8608	High Similarity	NPC310259
0.8608	High Similarity	NPC215932
0.8608	High Similarity	NPC40818
0.8608	High Similarity	NPC110639
0.8608	High Similarity	NPC14958
0.8606	High Similarity	NPC295009
0.8606	High Similarity	NPC216092
0.8606	High Similarity	NPC34376
0.8606	High Similarity	NPC260640
0.8605	High Similarity	NPC183843
0.8598	High Similarity	NPC33320
0.8598	High Similarity	NPC113055
0.8589	High Similarity	NPC301897
0.8589	High Similarity	NPC261090
0.8589	High Similarity	NPC257277
0.8588	High Similarity	NPC474568
0.858	High Similarity	NPC186507
0.858	High Similarity	NPC190351
0.858	High Similarity	NPC135370
0.858	High Similarity	NPC144288
0.8571	High Similarity	NPC220577
0.8571	High Similarity	NPC104353
0.8562	High Similarity	NPC238366
0.8554	High Similarity	NPC61141
0.8553	High Similarity	NPC85233
0.8547	High Similarity	NPC297807
0.8547	High Similarity	NPC67302
0.8545	High Similarity	NPC65784
0.8545	High Similarity	NPC225624
0.8545	High Similarity	NPC298093
0.8545	High Similarity	NPC285973
0.8544	High Similarity	NPC136278
0.8537	High Similarity	NPC19097
0.8529	High Similarity	NPC475825
0.8529	High Similarity	NPC174700
0.8529	High Similarity	NPC223375
0.8528	High Similarity	NPC18954
0.8528	High Similarity	NPC189960
0.8528	High Similarity	NPC32557
0.8526	High Similarity	NPC58229
0.8521	High Similarity	NPC202470
0.8519	High Similarity	NPC134677
0.8519	High Similarity	NPC304954
0.8519	High Similarity	NPC125300
0.8519	High Similarity	NPC301123
0.8512	High Similarity	NPC277480
0.8509	High Similarity	NPC234152
0.8494	Intermediate Similarity	NPC94155
0.8491	Intermediate Similarity	NPC216314
0.8491	Intermediate Similarity	NPC283002
0.8491	Intermediate Similarity	NPC302408
0.8491	Intermediate Similarity	NPC120924
0.8491	Intermediate Similarity	NPC195919
0.8488	Intermediate Similarity	NPC471841
0.8488	Intermediate Similarity	NPC107244
0.8481	Intermediate Similarity	NPC113089
0.8481	Intermediate Similarity	NPC23955
0.848	Intermediate Similarity	NPC310794
0.848	Intermediate Similarity	NPC233956
0.848	Intermediate Similarity	NPC473834
0.8476	Intermediate Similarity	NPC266960
0.8476	Intermediate Similarity	NPC178854
0.8476	Intermediate Similarity	NPC245546
0.8476	Intermediate Similarity	NPC303255
0.8476	Intermediate Similarity	NPC43243
0.8471	Intermediate Similarity	NPC28042
0.8471	Intermediate Similarity	NPC72249
0.8466	Intermediate Similarity	NPC86485
0.8466	Intermediate Similarity	NPC472408
0.8466	Intermediate Similarity	NPC476289
0.8462	Intermediate Similarity	NPC474948
0.8462	Intermediate Similarity	NPC42230
0.8462	Intermediate Similarity	NPC135345
0.8462	Intermediate Similarity	NPC50394
0.8462	Intermediate Similarity	NPC86477
0.8457	Intermediate Similarity	NPC98028
0.8457	Intermediate Similarity	NPC115324
0.8457	Intermediate Similarity	NPC198615
0.8457	Intermediate Similarity	NPC474170
0.8457	Intermediate Similarity	NPC472535

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 NPC187923 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	436
0.1-0.2	1008
0.2-0.3	1909
0.3-0.4	2764
0.4-0.5	1737
0.5-0.6	845
0.6-0.7	310
0.7-0.8	114
0.8-0.85	21
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8834	High Similarity	NPD1247	Approved
0.8727	High Similarity	NPD3926	Phase 2
0.8598	High Similarity	NPD919	Approved
0.8545	High Similarity	NPD5494	Approved
0.8476	Intermediate Similarity	NPD3882	Suspended
0.8353	Intermediate Similarity	NPD3818	Discontinued
0.8323	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD3817	Phase 2
0.8242	Intermediate Similarity	NPD2801	Approved
0.8218	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD1934	Approved
0.8025	Intermediate Similarity	NPD6799	Approved
0.8011	Intermediate Similarity	NPD7808	Phase 3
0.8	Intermediate Similarity	NPD6797	Phase 2
0.7988	Intermediate Similarity	NPD920	Approved
0.7965	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD7251	Discontinued
0.7955	Intermediate Similarity	NPD6559	Discontinued
0.7952	Intermediate Similarity	NPD6599	Discontinued
0.7943	Intermediate Similarity	NPD7074	Phase 3
0.7927	Intermediate Similarity	NPD1512	Approved
0.7919	Intermediate Similarity	NPD6166	Phase 2
0.7919	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD1243	Approved
0.7886	Intermediate Similarity	NPD7054	Approved
0.7866	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD7472	Approved
0.7812	Intermediate Similarity	NPD2796	Approved
0.7811	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD1511	Approved
0.7803	Intermediate Similarity	NPD6232	Discontinued
0.7784	Intermediate Similarity	NPD5844	Phase 1
0.7778	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3749	Approved
0.7771	Intermediate Similarity	NPD7473	Discontinued
0.7765	Intermediate Similarity	NPD5402	Approved
0.7758	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7199	Phase 2
0.7744	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7075	Discontinued
0.7673	Intermediate Similarity	NPD1933	Approved
0.7654	Intermediate Similarity	NPD2344	Approved
0.7647	Intermediate Similarity	NPD6801	Discontinued
0.7627	Intermediate Similarity	NPD3751	Discontinued
0.7616	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD7819	Suspended
0.7546	Intermediate Similarity	NPD1471	Phase 3
0.7514	Intermediate Similarity	NPD4967	Phase 2
0.7514	Intermediate Similarity	NPD4966	Approved
0.7514	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD1240	Approved
0.75	Intermediate Similarity	NPD3787	Discontinued
0.75	Intermediate Similarity	NPD1549	Phase 2
0.75	Intermediate Similarity	NPD1465	Phase 2
0.747	Intermediate Similarity	NPD2309	Approved
0.744	Intermediate Similarity	NPD5401	Approved
0.7439	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6234	Discontinued
0.7423	Intermediate Similarity	NPD1510	Phase 2
0.7423	Intermediate Similarity	NPD3748	Approved
0.7416	Intermediate Similarity	NPD2403	Approved
0.7407	Intermediate Similarity	NPD1607	Approved
0.7403	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD7411	Suspended
0.738	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5403	Approved
0.7349	Intermediate Similarity	NPD2800	Approved
0.7346	Intermediate Similarity	NPD447	Suspended
0.7341	Intermediate Similarity	NPD37	Approved
0.7337	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD4380	Phase 2
0.7289	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD943	Approved
0.7273	Intermediate Similarity	NPD2935	Discontinued
0.7263	Intermediate Similarity	NPD5242	Approved
0.7257	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD6959	Discontinued
0.7235	Intermediate Similarity	NPD2532	Approved
0.7235	Intermediate Similarity	NPD2534	Approved
0.7235	Intermediate Similarity	NPD2533	Approved
0.7222	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7768	Phase 2
0.7216	Intermediate Similarity	NPD5006	Approved
0.7216	Intermediate Similarity	NPD5005	Approved
0.7202	Intermediate Similarity	NPD3750	Approved
0.7202	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD8434	Phase 2
0.7143	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6280	Approved
0.7143	Intermediate Similarity	NPD7228	Approved
0.7143	Intermediate Similarity	NPD6279	Approved
0.7134	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6808	Phase 2
0.7108	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD2799	Discontinued
0.7098	Intermediate Similarity	NPD4420	Approved
0.7069	Intermediate Similarity	NPD3226	Approved
0.7066	Intermediate Similarity	NPD1551	Phase 2
0.7055	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD2163	Approved
0.7041	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6832	Phase 2
0.703	Intermediate Similarity	NPD230	Phase 1
0.7026	Intermediate Similarity	NPD6782	Approved
0.7026	Intermediate Similarity	NPD6781	Approved
0.7026	Intermediate Similarity	NPD6780	Approved
0.7026	Intermediate Similarity	NPD6778	Approved
0.7026	Intermediate Similarity	NPD6777	Approved
0.7026	Intermediate Similarity	NPD6779	Approved
0.7026	Intermediate Similarity	NPD6776	Approved
0.7024	Intermediate Similarity	NPD2346	Discontinued
0.7019	Intermediate Similarity	NPD2798	Approved
0.7011	Intermediate Similarity	NPD1653	Approved
0.7005	Intermediate Similarity	NPD7435	Discontinued
0.7	Intermediate Similarity	NPD4628	Phase 3
0.6994	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6385	Approved
0.6989	Remote Similarity	NPD7240	Approved
0.6989	Remote Similarity	NPD6386	Approved
0.697	Remote Similarity	NPD7870	Phase 2
0.697	Remote Similarity	NPD7871	Phase 2
0.6966	Remote Similarity	NPD2296	Approved
0.6966	Remote Similarity	NPD5353	Approved
0.6951	Remote Similarity	NPD2313	Discontinued
0.6941	Remote Similarity	NPD2654	Approved
0.693	Remote Similarity	NPD4846	Phase 2
0.6923	Remote Similarity	NPD2353	Approved
0.6923	Remote Similarity	NPD7229	Phase 3
0.6923	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7698	Approved
0.6919	Remote Similarity	NPD7697	Approved
0.6919	Remote Similarity	NPD7696	Phase 3
0.6918	Remote Similarity	NPD3705	Approved
0.6918	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD8313	Approved
0.6915	Remote Similarity	NPD8312	Approved
0.6911	Remote Similarity	NPD4287	Approved
0.6899	Remote Similarity	NPD17	Approved
0.6898	Remote Similarity	NPD7685	Pre-registration
0.686	Remote Similarity	NPD3887	Approved
0.686	Remote Similarity	NPD6190	Approved
0.6853	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD5953	Discontinued
0.6832	Remote Similarity	NPD8151	Discontinued
0.6829	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7286	Phase 2
0.6826	Remote Similarity	NPD6355	Discontinued
0.6815	Remote Similarity	NPD5536	Phase 2
0.6807	Remote Similarity	NPD6233	Phase 2
0.6805	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD7874	Approved
0.6782	Remote Similarity	NPD7701	Phase 2
0.678	Remote Similarity	NPD7458	Discontinued
0.6772	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.677	Remote Similarity	NPD1608	Approved
0.677	Remote Similarity	NPD3972	Approved
0.6769	Remote Similarity	NPD6534	Approved
0.6769	Remote Similarity	NPD6535	Approved
0.6768	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD1613	Approved
0.6765	Remote Similarity	NPD7783	Phase 2
0.6765	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD2354	Approved
0.6757	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD3266	Approved
0.6748	Remote Similarity	NPD1203	Approved
0.6748	Remote Similarity	NPD3267	Approved
0.6747	Remote Similarity	NPD6798	Discontinued
0.6743	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD3146	Approved
0.6743	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD7028	Phase 2
0.674	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD5711	Approved
0.6739	Remote Similarity	NPD5710	Approved
0.6722	Remote Similarity	NPD8455	Phase 2
0.6707	Remote Similarity	NPD1019	Discontinued
0.6702	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD3027	Phase 3
0.6687	Remote Similarity	NPD1876	Approved
0.6686	Remote Similarity	NPD7390	Discontinued
0.6683	Remote Similarity	NPD7801	Approved
0.6667	Remote Similarity	NPD9717	Approved
0.6667	Remote Similarity	NPD6099	Approved
0.6667	Remote Similarity	NPD4307	Phase 2
0.6667	Remote Similarity	NPD3018	Phase 2
0.6667	Remote Similarity	NPD7699	Phase 2

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