NPASS Compound

Structure

NPC290304 OpenBabel07101719242D 23 26 0 0 0 0 0 0 0 0999 V2000 2.0878 -3.4071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2219 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3601 -3.3122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -2.5411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6342 -1.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6342 0.0000 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 20 1 0 0 0 0 2 3 2 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 4 9 2 0 0 0 0 4 13 1 0 0 0 0 5 11 2 0 0 0 0 5 15 1 0 0 0 0 6 14 2 0 0 0 0 6 16 1 0 0 0 0 7 12 1 0 0 0 0 7 18 2 0 0 0 0 8 21 1 0 0 0 0 8 22 1 0 0 0 0 9 19 1 0 0 0 0 10 13 2 0 0 0 0 10 17 1 0 0 0 0 11 12 1 0 0 0 0 11 14 1 0 0 0 0 12 17 2 0 0 0 0 13 20 1 0 0 0 0 14 23 1 0 0 0 0 15 16 2 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	312.06
Volume:	300.012
LogP:	3.406
LogD:	3.244
LogS:	-4.833
# Rotatable Bonds:	3
TPSA:	78.13
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.747
Synthetic Accessibility Score:	2.655
Fsp3:	0.118
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.75
MDCK Permeability:	2.8561466024257243e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.033

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.037
Plasma Protein Binding (PPB):	96.28978729248047%
Volume Distribution (VD):	0.981
Pgp-substrate:	3.3112258911132812%

ADMET: Metabolism

CYP1A2-inhibitor:	0.987
CYP1A2-substrate:	0.477
CYP2C19-inhibitor:	0.938
CYP2C19-substrate:	0.099
CYP2C9-inhibitor:	0.583
CYP2C9-substrate:	0.914
CYP2D6-inhibitor:	0.972
CYP2D6-substrate:	0.902
CYP3A4-inhibitor:	0.923
CYP3A4-substrate:	0.128

ADMET: Excretion

Clearance (CL):	13.976
Half-life (T1/2):	0.293

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.169
Drug-inuced Liver Injury (DILI):	0.951
AMES Toxicity:	0.737
Rat Oral Acute Toxicity:	0.032
Maximum Recommended Daily Dose:	0.85
Skin Sensitization:	0.181
Carcinogencity:	0.942
Eye Corrosion:	0.025
Eye Irritation:	0.739
Respiratory Toxicity:	0.584

Download Data

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

Natural Product: NPC290304

Natural Product ID:	NPC290304
*Common Name:**	Spinosan A
IUPAC Name:	6-(4-hydroxy-2-methoxyphenyl)furo[2,3-f][1,3]benzodioxole-7-carbaldehyde
Synonyms:
Standard InCHIKey:	DIWHINIZDYGBCS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H12O6/c1-20-13-4-9(19)2-3-10(13)17-12(7-18)11-5-15-16(22-8-21-15)6-14(11)23-17/h2-7,19H,8H2,1H3
SMILES:	COc1cc(O)ccc1c1oc2c(c1C=O)cc1c(c2)OCO1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517523
PubChem CID:	11529700
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO32589	dalea spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499327]

☑ 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
MIC	6
Others	2

Activity Type	# Activity
Individual Protein	2
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2794	Individual Protein	Quinolone resistance protein norA	Staphylococcus aureus	FC	=	15.0	n.a.	PMID[534127]
NPT2794	Individual Protein	Quinolone resistance protein norA	Staphylococcus aureus	FC	=	8.0	n.a.	PMID[534127]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	140000.0	nM	PMID[534127]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	140000.0	nM	PMID[534127]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	140000.0	nM	PMID[534127]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	>	140000.0	nM	PMID[534127]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	140000.0	nM	PMID[534127]
NPT3006	Organism	Enterococcus faecalis V583	Enterococcus faecalis V583	MIC	>	140000.0	nM	PMID[534127]

☑ 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 NPC290304 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	458
0.1-0.2	1972
0.2-0.3	4801
0.3-0.4	10913
0.4-0.5	6863
0.5-0.6	3983
0.6-0.7	5458
0.7-0.8	5397
0.8-0.85	2008
0.85-0.9	770
0.9-0.95	67
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC236327
0.9515	High Similarity	NPC475964
0.9506	High Similarity	NPC110257
0.9398	High Similarity	NPC157522
0.9394	High Similarity	NPC211309
0.9212	High Similarity	NPC187923
0.9212	High Similarity	NPC291110
0.9172	High Similarity	NPC66804
0.9167	High Similarity	NPC292794
0.9146	High Similarity	NPC188486
0.9136	High Similarity	NPC45131
0.9112	High Similarity	NPC72455
0.9091	High Similarity	NPC469575
0.9091	High Similarity	NPC312056
0.9091	High Similarity	NPC84515
0.9048	High Similarity	NPC41853
0.9024	High Similarity	NPC196879
0.9024	High Similarity	NPC62518
0.9024	High Similarity	NPC16935
0.9024	High Similarity	NPC215375
0.9012	High Similarity	NPC183843
0.8988	High Similarity	NPC247973
0.8988	High Similarity	NPC167479
0.8963	High Similarity	NPC474990
0.8963	High Similarity	NPC167595
0.8951	High Similarity	NPC67654
0.8922	High Similarity	NPC1706
0.8922	High Similarity	NPC59295
0.8922	High Similarity	NPC1755
0.8922	High Similarity	NPC133065
0.8922	High Similarity	NPC470178
0.8922	High Similarity	NPC263092
0.8922	High Similarity	NPC39305
0.8916	High Similarity	NPC295009
0.8916	High Similarity	NPC162668
0.8916	High Similarity	NPC260640
0.8889	High Similarity	NPC156244
0.8889	High Similarity	NPC62640
0.8882	High Similarity	NPC131866
0.8876	High Similarity	NPC86477
0.8869	High Similarity	NPC45449
0.8869	High Similarity	NPC29411
0.8869	High Similarity	NPC39306
0.8869	High Similarity	NPC36320
0.8862	High Similarity	NPC238995
0.8855	High Similarity	NPC285973
0.8855	High Similarity	NPC225624
0.883	High Similarity	NPC223375
0.883	High Similarity	NPC475825
0.883	High Similarity	NPC174700
0.8817	High Similarity	NPC277480
0.8788	High Similarity	NPC160015
0.8788	High Similarity	NPC247677
0.878	High Similarity	NPC244371
0.8779	High Similarity	NPC473834
0.8779	High Similarity	NPC261471
0.8779	High Similarity	NPC233956
0.8779	High Similarity	NPC310794
0.8772	High Similarity	NPC476641
0.8765	High Similarity	NPC50394
0.8765	High Similarity	NPC320789
0.8765	High Similarity	NPC42892
0.8757	High Similarity	NPC37183
0.875	High Similarity	NPC272722
0.875	High Similarity	NPC478199
0.8743	High Similarity	NPC269906
0.8743	High Similarity	NPC97523
0.8735	High Similarity	NPC258644
0.8735	High Similarity	NPC260902
0.8735	High Similarity	NPC181960
0.8735	High Similarity	NPC296957
0.8728	High Similarity	NPC287243
0.8727	High Similarity	NPC18954
0.8721	High Similarity	NPC54098
0.8721	High Similarity	NPC260263
0.8721	High Similarity	NPC230619
0.872	High Similarity	NPC125300
0.872	High Similarity	NPC292460
0.872	High Similarity	NPC148497
0.872	High Similarity	NPC35544
0.872	High Similarity	NPC104728
0.872	High Similarity	NPC153008
0.8712	High Similarity	NPC234152
0.8706	High Similarity	NPC113093
0.8698	High Similarity	NPC65846
0.869	High Similarity	NPC94155
0.869	High Similarity	NPC304387
0.8683	High Similarity	NPC472877
0.8683	High Similarity	NPC476349
0.8683	High Similarity	NPC476350
0.8678	High Similarity	NPC24258
0.8678	High Similarity	NPC156635
0.8675	High Similarity	NPC472461
0.8675	High Similarity	NPC261090
0.8671	High Similarity	NPC476640
0.8671	High Similarity	NPC277510
0.8671	High Similarity	NPC65885
0.8671	High Similarity	NPC82217
0.8671	High Similarity	NPC216842
0.8667	High Similarity	NPC478213
0.8667	High Similarity	NPC472915
0.8667	High Similarity	NPC280937
0.8663	High Similarity	NPC212748
0.8663	High Similarity	NPC105511
0.8663	High Similarity	NPC281835
0.8663	High Similarity	NPC218533
0.8663	High Similarity	NPC44558
0.8663	High Similarity	NPC78830
0.8659	High Similarity	NPC149614
0.8659	High Similarity	NPC117579
0.8659	High Similarity	NPC115324
0.8655	High Similarity	NPC470704
0.8655	High Similarity	NPC186392
0.8655	High Similarity	NPC76482
0.8647	High Similarity	NPC38914
0.8642	High Similarity	NPC17816
0.8639	High Similarity	NPC125991
0.8639	High Similarity	NPC76687
0.8631	High Similarity	NPC131557
0.8631	High Similarity	NPC304839
0.8631	High Similarity	NPC220582
0.8623	High Similarity	NPC99597
0.8623	High Similarity	NPC210084
0.8614	High Similarity	NPC31018
0.8614	High Similarity	NPC472909
0.8614	High Similarity	NPC2928
0.8614	High Similarity	NPC37392
0.8614	High Similarity	NPC255807
0.8613	High Similarity	NPC178737
0.8613	High Similarity	NPC48773
0.8613	High Similarity	NPC307286
0.8613	High Similarity	NPC205076
0.8613	High Similarity	NPC307518
0.8611	High Similarity	NPC60848
0.8606	High Similarity	NPC68882
0.8606	High Similarity	NPC207624
0.8605	High Similarity	NPC472381
0.8605	High Similarity	NPC247136
0.8605	High Similarity	NPC471287
0.8605	High Similarity	NPC202470
0.8605	High Similarity	NPC472383
0.8598	High Similarity	NPC306821
0.8598	High Similarity	NPC179183
0.8598	High Similarity	NPC156953
0.8596	High Similarity	NPC53640
0.8588	High Similarity	NPC89131
0.858	High Similarity	NPC99968
0.858	High Similarity	NPC470756
0.858	High Similarity	NPC109238
0.8571	High Similarity	NPC8127
0.8571	High Similarity	NPC49667
0.8571	High Similarity	NPC164384
0.8571	High Similarity	NPC471841
0.8571	High Similarity	NPC195832
0.8571	High Similarity	NPC107244
0.8563	High Similarity	NPC472916
0.8563	High Similarity	NPC13879
0.8563	High Similarity	NPC235165
0.8563	High Similarity	NPC255106
0.8563	High Similarity	NPC37606
0.8555	High Similarity	NPC28042
0.8555	High Similarity	NPC120220
0.8555	High Similarity	NPC474434
0.8555	High Similarity	NPC22195
0.8555	High Similarity	NPC34287
0.8555	High Similarity	NPC21190
0.8555	High Similarity	NPC224462
0.8555	High Similarity	NPC471416
0.8555	High Similarity	NPC183357
0.8555	High Similarity	NPC190351
0.8554	High Similarity	NPC57211
0.8554	High Similarity	NPC206238
0.8554	High Similarity	NPC167091
0.8554	High Similarity	NPC271779
0.8554	High Similarity	NPC88645
0.8554	High Similarity	NPC292214
0.8547	High Similarity	NPC241820
0.8547	High Similarity	NPC73703
0.8547	High Similarity	NPC73929
0.8547	High Similarity	NPC93099
0.8547	High Similarity	NPC47905
0.8547	High Similarity	NPC135345
0.8547	High Similarity	NPC139683
0.8547	High Similarity	NPC471288
0.8545	High Similarity	NPC58668
0.8545	High Similarity	NPC308451
0.8545	High Similarity	NPC193976
0.8545	High Similarity	NPC262623
0.8545	High Similarity	NPC208043
0.8545	High Similarity	NPC288316
0.8545	High Similarity	NPC106372
0.8545	High Similarity	NPC23668
0.8545	High Similarity	NPC170169
0.8545	High Similarity	NPC279061
0.8545	High Similarity	NPC226973
0.8538	High Similarity	NPC300053
0.8538	High Similarity	NPC165720
0.8529	High Similarity	NPC81679
0.8529	High Similarity	NPC18284
0.8529	High Similarity	NPC273021

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 NPC290304 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	414
0.1-0.2	987
0.2-0.3	1972
0.3-0.4	2755
0.4-0.5	1713
0.5-0.6	871
0.6-0.7	290
0.7-0.8	109
0.8-0.85	35
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8655	High Similarity	NPD3818	Discontinued
0.8471	Intermediate Similarity	NPD1247	Approved
0.8457	Intermediate Similarity	NPD6559	Discontinued
0.8452	Intermediate Similarity	NPD3882	Suspended
0.8443	Intermediate Similarity	NPD2801	Approved
0.8383	Intermediate Similarity	NPD1934	Approved
0.8372	Intermediate Similarity	NPD3926	Phase 2
0.8304	Intermediate Similarity	NPD5494	Approved
0.8246	Intermediate Similarity	NPD919	Approved
0.8239	Intermediate Similarity	NPD7074	Phase 3
0.8202	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7054	Approved
0.8136	Intermediate Similarity	NPD7472	Approved
0.8118	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD6232	Discontinued
0.8086	Intermediate Similarity	NPD2344	Approved
0.8081	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD7473	Discontinued
0.8012	Intermediate Similarity	NPD1511	Approved
0.8011	Intermediate Similarity	NPD6166	Phase 2
0.8011	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7808	Phase 3
0.7989	Intermediate Similarity	NPD6797	Phase 2
0.7978	Intermediate Similarity	NPD5844	Phase 1
0.7977	Intermediate Similarity	NPD3749	Approved
0.7976	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD920	Approved
0.7965	Intermediate Similarity	NPD3817	Phase 2
0.7944	Intermediate Similarity	NPD7251	Discontinued
0.7919	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD1512	Approved
0.7892	Intermediate Similarity	NPD2309	Approved
0.7857	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD7199	Phase 2
0.7818	Intermediate Similarity	NPD1549	Phase 2
0.7798	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD1510	Phase 2
0.7738	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6234	Discontinued
0.7716	Intermediate Similarity	NPD1240	Approved
0.7714	Intermediate Similarity	NPD4966	Approved
0.7714	Intermediate Similarity	NPD4967	Phase 2
0.7714	Intermediate Similarity	NPD4965	Approved
0.7701	Intermediate Similarity	NPD1465	Phase 2
0.7701	Intermediate Similarity	NPD7819	Suspended
0.7692	Intermediate Similarity	NPD6799	Approved
0.768	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD7075	Discontinued
0.7665	Intermediate Similarity	NPD2800	Approved
0.7647	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD6599	Discontinued
0.763	Intermediate Similarity	NPD4380	Phase 2
0.7624	Intermediate Similarity	NPD3751	Discontinued
0.7622	Intermediate Similarity	NPD1607	Approved
0.7619	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD1551	Phase 2
0.759	Intermediate Similarity	NPD2796	Approved
0.7586	Intermediate Similarity	NPD7411	Suspended
0.756	Intermediate Similarity	NPD1243	Approved
0.7557	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD5402	Approved
0.7545	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD2534	Approved
0.7544	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD2532	Approved
0.7544	Intermediate Similarity	NPD2533	Approved
0.7543	Intermediate Similarity	NPD37	Approved
0.7542	Intermediate Similarity	NPD6959	Discontinued
0.7514	Intermediate Similarity	NPD7768	Phase 2
0.7514	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD943	Approved
0.7487	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD2935	Discontinued
0.7474	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD447	Suspended
0.7447	Intermediate Similarity	NPD8434	Phase 2
0.7443	Intermediate Similarity	NPD6801	Discontinued
0.7432	Intermediate Similarity	NPD7228	Approved
0.7412	Intermediate Similarity	NPD3750	Approved
0.736	Intermediate Similarity	NPD2296	Approved
0.7349	Intermediate Similarity	NPD230	Phase 1
0.7349	Intermediate Similarity	NPD1933	Approved
0.7314	Intermediate Similarity	NPD1653	Approved
0.7308	Intermediate Similarity	NPD3787	Discontinued
0.7273	Intermediate Similarity	NPD3226	Approved
0.7251	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5953	Discontinued
0.7209	Intermediate Similarity	NPD4628	Phase 3
0.7208	Intermediate Similarity	NPD6776	Approved
0.7208	Intermediate Similarity	NPD6781	Approved
0.7208	Intermediate Similarity	NPD6778	Approved
0.7208	Intermediate Similarity	NPD6777	Approved
0.7208	Intermediate Similarity	NPD6780	Approved
0.7208	Intermediate Similarity	NPD6782	Approved
0.7208	Intermediate Similarity	NPD6779	Approved
0.7196	Intermediate Similarity	NPD8312	Approved
0.7196	Intermediate Similarity	NPD8313	Approved
0.7195	Intermediate Similarity	NPD9494	Approved
0.7181	Intermediate Similarity	NPD7685	Pre-registration
0.7178	Intermediate Similarity	NPD8151	Discontinued
0.7169	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD5403	Approved
0.7151	Intermediate Similarity	NPD6280	Approved
0.7151	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6279	Approved
0.715	Intermediate Similarity	NPD7871	Phase 2
0.715	Intermediate Similarity	NPD7870	Phase 2
0.7143	Intermediate Similarity	NPD5401	Approved
0.7135	Intermediate Similarity	NPD1471	Phase 3
0.7121	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6808	Phase 2
0.7118	Intermediate Similarity	NPD2799	Discontinued
0.7118	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD3748	Approved
0.7112	Intermediate Similarity	NPD7286	Phase 2
0.71	Intermediate Similarity	NPD7698	Approved
0.71	Intermediate Similarity	NPD7696	Phase 3
0.71	Intermediate Similarity	NPD7697	Approved
0.71	Intermediate Similarity	NPD7435	Discontinued
0.7098	Intermediate Similarity	NPD4287	Approved
0.709	Intermediate Similarity	NPD7240	Approved
0.7083	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1613	Approved
0.7081	Intermediate Similarity	NPD5242	Approved
0.7053	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD5006	Approved
0.705	Intermediate Similarity	NPD5005	Approved
0.7048	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD2346	Discontinued
0.7027	Intermediate Similarity	NPD7229	Phase 3
0.7027	Intermediate Similarity	NPD5710	Approved
0.7027	Intermediate Similarity	NPD5711	Approved
0.7024	Intermediate Similarity	NPD7783	Phase 2
0.7024	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD5760	Phase 2
0.7017	Intermediate Similarity	NPD5761	Phase 2
0.7006	Intermediate Similarity	NPD3027	Phase 3
0.6988	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7458	Discontinued
0.6979	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1203	Approved
0.6964	Remote Similarity	NPD2313	Discontinued
0.6961	Remote Similarity	NPD7701	Phase 2
0.6957	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6534	Approved
0.6954	Remote Similarity	NPD6535	Approved
0.6949	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD4420	Approved
0.6928	Remote Similarity	NPD2798	Approved
0.6901	Remote Similarity	NPD6651	Approved
0.6893	Remote Similarity	NPD7874	Approved
0.6893	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7390	Discontinued
0.6881	Remote Similarity	NPD6823	Phase 2
0.6879	Remote Similarity	NPD6100	Approved
0.6879	Remote Similarity	NPD6099	Approved
0.6875	Remote Similarity	NPD6190	Approved
0.6864	Remote Similarity	NPD3764	Approved
0.6862	Remote Similarity	NPD2403	Approved
0.686	Remote Similarity	NPD7801	Approved
0.6854	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.685	Remote Similarity	NPD7700	Phase 2
0.685	Remote Similarity	NPD7699	Phase 2
0.6848	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD7680	Approved
0.6845	Remote Similarity	NPD6832	Phase 2
0.6845	Remote Similarity	NPD4908	Phase 1
0.6831	Remote Similarity	NPD8455	Phase 2
0.6829	Remote Similarity	NPD7584	Approved
0.6818	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6386	Approved
0.6813	Remote Similarity	NPD6385	Approved
0.6793	Remote Similarity	NPD5353	Approved
0.6789	Remote Similarity	NPD2163	Approved
0.6788	Remote Similarity	NPD7549	Discontinued
0.6788	Remote Similarity	NPD1608	Approved
0.6788	Remote Similarity	NPD9717	Approved
0.6787	Remote Similarity	NPD4846	Phase 2
0.6772	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD7028	Phase 2
0.6744	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD6212	Phase 3
0.6734	Remote Similarity	NPD6213	Phase 3
0.6734	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD7907	Approved
0.6727	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD3705	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