NPASS Compound

Structure

NPC475964 OpenBabel07101718312D 26 29 0 0 0 0 0 0 0 0999 V2000 -6.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 -5.0878 -1.6750 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 -2.5411 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 -4.5878 -0.8090 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 10 1 0 0 0 0 2 22 1 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 5 11 2 0 0 0 0 5 15 1 0 0 0 0 6 13 2 0 0 0 0 6 17 1 0 0 0 0 7 16 2 0 0 0 0 7 18 1 0 0 0 0 8 14 1 0 0 0 0 8 20 2 0 0 0 0 9 23 1 0 0 0 0 9 24 1 0 0 0 0 10 21 2 0 0 0 0 10 25 1 0 0 0 0 11 25 1 0 0 0 0 12 15 2 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 13 16 1 0 0 0 0 14 19 2 0 0 0 0 15 22 1 0 0 0 0 16 26 1 0 0 0 0 17 18 2 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.07
Volume:	340.758
LogP:	3.453
LogD:	2.902
LogS:	-6.093
# Rotatable Bonds:	5
TPSA:	84.2
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.402
Synthetic Accessibility Score:	2.653
Fsp3:	0.158
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:	-4.811
MDCK Permeability:	6.783015123801306e-05
Pgp-inhibitor:	0.198
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.245
Plasma Protein Binding (PPB):	92.5466537475586%
Volume Distribution (VD):	1.162
Pgp-substrate:	9.037806510925293%

ADMET: Metabolism

CYP1A2-inhibitor:	0.974
CYP1A2-substrate:	0.35
CYP2C19-inhibitor:	0.942
CYP2C19-substrate:	0.107
CYP2C9-inhibitor:	0.697
CYP2C9-substrate:	0.909
CYP2D6-inhibitor:	0.912
CYP2D6-substrate:	0.851
CYP3A4-inhibitor:	0.905
CYP3A4-substrate:	0.153

ADMET: Excretion

Clearance (CL):	9.481
Half-life (T1/2):	0.174

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.151
Drug-inuced Liver Injury (DILI):	0.939
AMES Toxicity:	0.818
Rat Oral Acute Toxicity:	0.068
Maximum Recommended Daily Dose:	0.883
Skin Sensitization:	0.464
Carcinogencity:	0.957
Eye Corrosion:	0.009
Eye Irritation:	0.304
Respiratory Toxicity:	0.643

Download Data

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

Natural Product: NPC475964

Natural Product ID:	NPC475964
*Common Name:**	Spinosan A Acetate
IUPAC Name:	[4-(7-formylfuro[2,3-f][1,3]benzodioxol-6-yl)-3-methoxyphenyl] acetate
Synonyms:	Spinosan A Acetate
Standard InCHIKey:	GPYDUSJZIYFWHD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H14O7/c1-10(21)25-11-3-4-12(15(5-11)22-2)19-14(8-20)13-6-17-18(24-9-23-17)7-16(13)26-19/h3-8H,9H2,1-2H3
SMILES:	COc1cc(ccc1c1oc2c(c1C=O)cc1c(c2)OCO1)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519793
PubChem CID:	11530466
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	1

Activity Type	# Activity
Individual Protein	1
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	=	62.0	n.a.	PMID[569898]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	140000.0	nM	PMID[569898]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	140000.0	nM	PMID[569898]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	140000.0	nM	PMID[569898]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	>	140000.0	nM	PMID[569898]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	140000.0	nM	PMID[569898]
NPT3006	Organism	Enterococcus faecalis V583	Enterococcus faecalis V583	MIC	>	140000.0	nM	PMID[569898]

☑ 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 NPC475964 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	492
0.1-0.2	2043
0.2-0.3	4993
0.3-0.4	10703
0.4-0.5	7201
0.5-0.6	4012
0.6-0.7	5911
0.7-0.8	5561
0.8-0.85	1540
0.85-0.9	211
0.9-0.95	29
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9573	High Similarity	NPC72455
0.9515	High Similarity	NPC236327
0.9515	High Similarity	NPC290304
0.9325	High Similarity	NPC187923
0.9281	High Similarity	NPC66804
0.9157	High Similarity	NPC41853
0.9096	High Similarity	NPC167479
0.9048	High Similarity	NPC157522
0.903	High Similarity	NPC110257
0.8994	High Similarity	NPC62640
0.8929	High Similarity	NPC211309
0.8922	High Similarity	NPC155264
0.8922	High Similarity	NPC67450
0.8922	High Similarity	NPC193881
0.8922	High Similarity	NPC210460
0.8916	High Similarity	NPC179464
0.8889	High Similarity	NPC244371
0.8855	High Similarity	NPC78612
0.8855	High Similarity	NPC234536
0.8855	High Similarity	NPC478199
0.8841	High Similarity	NPC258644
0.8827	High Similarity	NPC153008
0.8827	High Similarity	NPC148497
0.8827	High Similarity	NPC292460
0.882	High Similarity	NPC474975
0.8802	High Similarity	NPC65846
0.878	High Similarity	NPC261484
0.8773	High Similarity	NPC186507
0.8773	High Similarity	NPC478213
0.8757	High Similarity	NPC86477
0.875	High Similarity	NPC291110
0.8743	High Similarity	NPC61141
0.8735	High Similarity	NPC131557
0.8735	High Similarity	NPC243509
0.8727	High Similarity	NPC82733
0.8727	High Similarity	NPC76458
0.8713	High Similarity	NPC292794
0.8712	High Similarity	NPC68882
0.8683	High Similarity	NPC188486
0.8683	High Similarity	NPC216092
0.8683	High Similarity	NPC109238
0.8675	High Similarity	NPC33320
0.8675	High Similarity	NPC15764
0.8667	High Similarity	NPC45131
0.8667	High Similarity	NPC301897
0.8663	High Similarity	NPC261471
0.8663	High Similarity	NPC233956
0.8659	High Similarity	NPC57211
0.8655	High Similarity	NPC190351
0.8655	High Similarity	NPC144288
0.865	High Similarity	NPC279061
0.8647	High Similarity	NPC320789
0.8639	High Similarity	NPC29411
0.8631	High Similarity	NPC18284
0.8631	High Similarity	NPC469575
0.8631	High Similarity	NPC312056
0.8631	High Similarity	NPC273021
0.8631	High Similarity	NPC84515
0.8629	High Similarity	NPC97523
0.8625	High Similarity	NPC224687
0.8623	High Similarity	NPC139876
0.8614	High Similarity	NPC310206
0.8606	High Similarity	NPC478238
0.8598	High Similarity	NPC308555
0.8598	High Similarity	NPC52623
0.8571	High Similarity	NPC309335
0.8571	High Similarity	NPC296540
0.8571	High Similarity	NPC264293
0.8571	High Similarity	NPC183843
0.8563	High Similarity	NPC104459
0.8563	High Similarity	NPC196879
0.8563	High Similarity	NPC257914
0.8563	High Similarity	NPC107244
0.8563	High Similarity	NPC238405
0.8563	High Similarity	NPC62518
0.8563	High Similarity	NPC16935
0.8563	High Similarity	NPC215375
0.8554	High Similarity	NPC155063
0.8547	High Similarity	NPC218533
0.8547	High Similarity	NPC281835
0.8547	High Similarity	NPC78830
0.8545	High Similarity	NPC279930
0.8538	High Similarity	NPC247973
0.8537	High Similarity	NPC474663
0.8537	High Similarity	NPC198615
0.8537	High Similarity	NPC104353
0.8529	High Similarity	NPC173149
0.8529	High Similarity	NPC179015
0.8528	High Similarity	NPC88445
0.8521	High Similarity	NPC19948
0.8509	High Similarity	NPC296575
0.8506	High Similarity	NPC224165
0.8506	High Similarity	NPC53917
0.8503	High Similarity	NPC167595
0.8503	High Similarity	NPC474990
0.8494	Intermediate Similarity	NPC254163
0.8494	Intermediate Similarity	NPC233776
0.8494	Intermediate Similarity	NPC284353
0.8494	Intermediate Similarity	NPC3273
0.8485	Intermediate Similarity	NPC67654
0.848	Intermediate Similarity	NPC113093
0.848	Intermediate Similarity	NPC472895
0.8476	Intermediate Similarity	NPC191104
0.8476	Intermediate Similarity	NPC29056
0.8471	Intermediate Similarity	NPC133065
0.8471	Intermediate Similarity	NPC1706
0.8471	Intermediate Similarity	NPC39305
0.8471	Intermediate Similarity	NPC59295
0.8471	Intermediate Similarity	NPC263092
0.8471	Intermediate Similarity	NPC1755
0.8471	Intermediate Similarity	NPC470178
0.8466	Intermediate Similarity	NPC63256
0.8466	Intermediate Similarity	NPC10304
0.8462	Intermediate Similarity	NPC34376
0.8462	Intermediate Similarity	NPC162668
0.8462	Intermediate Similarity	NPC209411
0.8462	Intermediate Similarity	NPC239890
0.8462	Intermediate Similarity	NPC295009
0.8462	Intermediate Similarity	NPC260640
0.8457	Intermediate Similarity	NPC231013
0.8457	Intermediate Similarity	NPC24258
0.8457	Intermediate Similarity	NPC164384
0.8452	Intermediate Similarity	NPC113055
0.8452	Intermediate Similarity	NPC250076
0.8452	Intermediate Similarity	NPC325122
0.8448	Intermediate Similarity	NPC37606
0.8443	Intermediate Similarity	NPC13879
0.8443	Intermediate Similarity	NPC261090
0.8439	Intermediate Similarity	NPC131866
0.8439	Intermediate Similarity	NPC120220
0.8436	Intermediate Similarity	NPC73703
0.8424	Intermediate Similarity	NPC473732
0.8424	Intermediate Similarity	NPC156244
0.8421	Intermediate Similarity	NPC39306
0.8421	Intermediate Similarity	NPC36320
0.8421	Intermediate Similarity	NPC45449
0.8415	Intermediate Similarity	NPC238366
0.8415	Intermediate Similarity	NPC474648
0.8412	Intermediate Similarity	NPC76687
0.8412	Intermediate Similarity	NPC238995
0.8412	Intermediate Similarity	NPC108767
0.8409	Intermediate Similarity	NPC297807
0.8409	Intermediate Similarity	NPC98546
0.8405	Intermediate Similarity	NPC74539
0.8405	Intermediate Similarity	NPC205522
0.8405	Intermediate Similarity	NPC304443
0.8402	Intermediate Similarity	NPC74749
0.8402	Intermediate Similarity	NPC43971
0.8402	Intermediate Similarity	NPC298093
0.8402	Intermediate Similarity	NPC78944
0.8402	Intermediate Similarity	NPC285973
0.8402	Intermediate Similarity	NPC474770
0.8402	Intermediate Similarity	NPC225624
0.8402	Intermediate Similarity	NPC19554
0.8393	Intermediate Similarity	NPC19097
0.8391	Intermediate Similarity	NPC475825
0.8391	Intermediate Similarity	NPC174700
0.8391	Intermediate Similarity	NPC178737
0.8391	Intermediate Similarity	NPC472584
0.8391	Intermediate Similarity	NPC223375
0.8383	Intermediate Similarity	NPC122623
0.8383	Intermediate Similarity	NPC276059
0.8383	Intermediate Similarity	NPC295608
0.8383	Intermediate Similarity	NPC34725
0.8383	Intermediate Similarity	NPC241774
0.8383	Intermediate Similarity	NPC250769
0.8383	Intermediate Similarity	NPC278010
0.8373	Intermediate Similarity	NPC130015
0.8373	Intermediate Similarity	NPC475116
0.8373	Intermediate Similarity	NPC38361
0.8372	Intermediate Similarity	NPC277480
0.8363	Intermediate Similarity	NPC300984
0.8363	Intermediate Similarity	NPC89131
0.8362	Intermediate Similarity	NPC329161
0.8362	Intermediate Similarity	NPC470091
0.8362	Intermediate Similarity	NPC240887
0.8354	Intermediate Similarity	NPC183236
0.8353	Intermediate Similarity	NPC258322
0.8353	Intermediate Similarity	NPC15212
0.8353	Intermediate Similarity	NPC99968
0.8353	Intermediate Similarity	NPC303565
0.8353	Intermediate Similarity	NPC191352
0.8352	Intermediate Similarity	NPC156635
0.8344	Intermediate Similarity	NPC24257
0.8344	Intermediate Similarity	NPC14958
0.8344	Intermediate Similarity	NPC153620
0.8344	Intermediate Similarity	NPC216314
0.8344	Intermediate Similarity	NPC195919
0.8344	Intermediate Similarity	NPC215932
0.8344	Intermediate Similarity	NPC40818
0.8344	Intermediate Similarity	NPC120924
0.8344	Intermediate Similarity	NPC106461
0.8344	Intermediate Similarity	NPC110639
0.8343	Intermediate Similarity	NPC473834
0.8343	Intermediate Similarity	NPC474568
0.8343	Intermediate Similarity	NPC50430
0.8343	Intermediate Similarity	NPC125713
0.8343	Intermediate Similarity	NPC310794
0.8333	Intermediate Similarity	NPC474983
0.8333	Intermediate Similarity	NPC257277

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 NPC475964 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	411
0.1-0.2	1013
0.2-0.3	2015
0.3-0.4	2721
0.4-0.5	1731
0.5-0.6	825
0.6-0.7	299
0.7-0.8	114
0.8-0.85	15
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8675	High Similarity	NPD919	Approved
0.8571	High Similarity	NPD1247	Approved
0.8471	Intermediate Similarity	NPD3926	Phase 2
0.8405	Intermediate Similarity	NPD920	Approved
0.8402	Intermediate Similarity	NPD5494	Approved
0.8293	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8218	Intermediate Similarity	NPD3818	Discontinued
0.816	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8136	Intermediate Similarity	NPD6559	Discontinued
0.8059	Intermediate Similarity	NPD3817	Phase 2
0.8012	Intermediate Similarity	NPD3882	Suspended
0.8	Intermediate Similarity	NPD2801	Approved
0.7989	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1243	Approved
0.7966	Intermediate Similarity	NPD5844	Phase 1
0.7941	Intermediate Similarity	NPD1934	Approved
0.7886	Intermediate Similarity	NPD6232	Discontinued
0.7861	Intermediate Similarity	NPD3749	Approved
0.7853	Intermediate Similarity	NPD7473	Discontinued
0.7829	Intermediate Similarity	NPD7199	Phase 2
0.7821	Intermediate Similarity	NPD7074	Phase 3
0.7784	Intermediate Similarity	NPD6799	Approved
0.7765	Intermediate Similarity	NPD7054	Approved
0.774	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD7472	Approved
0.7719	Intermediate Similarity	NPD6599	Discontinued
0.7701	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7819	Suspended
0.7683	Intermediate Similarity	NPD2796	Approved
0.7679	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD1933	Approved
0.7636	Intermediate Similarity	NPD2344	Approved
0.76	Intermediate Similarity	NPD4966	Approved
0.76	Intermediate Similarity	NPD4965	Approved
0.76	Intermediate Similarity	NPD4967	Phase 2
0.7598	Intermediate Similarity	NPD6166	Phase 2
0.7598	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD7808	Phase 3
0.7586	Intermediate Similarity	NPD1465	Phase 2
0.7586	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD6797	Phase 2
0.7574	Intermediate Similarity	NPD1511	Approved
0.7543	Intermediate Similarity	NPD5402	Approved
0.7541	Intermediate Similarity	NPD7251	Discontinued
0.754	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6234	Discontinued
0.7485	Intermediate Similarity	NPD1512	Approved
0.7471	Intermediate Similarity	NPD7411	Suspended
0.7458	Intermediate Similarity	NPD7075	Discontinued
0.7456	Intermediate Similarity	NPD2309	Approved
0.7439	Intermediate Similarity	NPD447	Suspended
0.7429	Intermediate Similarity	NPD6801	Discontinued
0.7429	Intermediate Similarity	NPD37	Approved
0.7418	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD3748	Approved
0.7396	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6808	Phase 2
0.7381	Intermediate Similarity	NPD1549	Phase 2
0.7365	Intermediate Similarity	NPD1551	Phase 2
0.7348	Intermediate Similarity	NPD5242	Approved
0.734	Intermediate Similarity	NPD8434	Phase 2
0.7333	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD2533	Approved
0.7326	Intermediate Similarity	NPD2532	Approved
0.7326	Intermediate Similarity	NPD2534	Approved
0.7322	Intermediate Similarity	NPD3751	Discontinued
0.7321	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1510	Phase 2
0.7303	Intermediate Similarity	NPD7768	Phase 2
0.7297	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD5006	Approved
0.7296	Intermediate Similarity	NPD5005	Approved
0.7287	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1240	Approved
0.7262	Intermediate Similarity	NPD2935	Discontinued
0.7257	Intermediate Similarity	NPD3226	Approved
0.7239	Intermediate Similarity	NPD6832	Phase 2
0.7235	Intermediate Similarity	NPD2800	Approved
0.7232	Intermediate Similarity	NPD6280	Approved
0.7232	Intermediate Similarity	NPD6279	Approved
0.7228	Intermediate Similarity	NPD7228	Approved
0.7225	Intermediate Similarity	NPD5401	Approved
0.7222	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1471	Phase 3
0.7216	Intermediate Similarity	NPD4380	Phase 2
0.72	Intermediate Similarity	NPD1653	Approved
0.7193	Intermediate Similarity	NPD3750	Approved
0.7186	Intermediate Similarity	NPD1607	Approved
0.7179	Intermediate Similarity	NPD4420	Approved
0.7152	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5403	Approved
0.7143	Intermediate Similarity	NPD6959	Discontinued
0.7135	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD230	Phase 1
0.7104	Intermediate Similarity	NPD3787	Discontinued
0.7101	Intermediate Similarity	NPD2799	Discontinued
0.7093	Intermediate Similarity	NPD4628	Phase 3
0.7086	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6386	Approved
0.7079	Intermediate Similarity	NPD6385	Approved
0.7074	Intermediate Similarity	NPD7240	Approved
0.7066	Intermediate Similarity	NPD943	Approved
0.7056	Intermediate Similarity	NPD5353	Approved
0.7021	Intermediate Similarity	NPD5953	Discontinued
0.7018	Intermediate Similarity	NPD2346	Discontinued
0.7011	Intermediate Similarity	NPD7229	Phase 3
0.7	Intermediate Similarity	NPD8312	Approved
0.7	Intermediate Similarity	NPD8313	Approved
0.6995	Remote Similarity	NPD8151	Discontinued
0.6995	Remote Similarity	NPD4287	Approved
0.6984	Remote Similarity	NPD7685	Pre-registration
0.6961	Remote Similarity	NPD2296	Approved
0.6946	Remote Similarity	NPD2313	Discontinued
0.6935	Remote Similarity	NPD2403	Approved
0.6927	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7783	Phase 2
0.6915	Remote Similarity	NPD7286	Phase 2
0.6915	Remote Similarity	NPD7435	Discontinued
0.6909	Remote Similarity	NPD1019	Discontinued
0.6894	Remote Similarity	NPD17	Approved
0.6872	Remote Similarity	NPD7458	Discontinued
0.685	Remote Similarity	NPD6777	Approved
0.685	Remote Similarity	NPD6782	Approved
0.685	Remote Similarity	NPD6779	Approved
0.685	Remote Similarity	NPD6780	Approved
0.685	Remote Similarity	NPD6778	Approved
0.685	Remote Similarity	NPD6781	Approved
0.685	Remote Similarity	NPD6776	Approved
0.6849	Remote Similarity	NPD4846	Phase 2
0.6848	Remote Similarity	NPD1203	Approved
0.6848	Remote Similarity	NPD3266	Approved
0.6848	Remote Similarity	NPD3267	Approved
0.6836	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD5711	Approved
0.6828	Remote Similarity	NPD5710	Approved
0.6813	Remote Similarity	NPD8455	Phase 2
0.681	Remote Similarity	NPD3705	Approved
0.681	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD2798	Approved
0.6798	Remote Similarity	NPD7870	Phase 2
0.6798	Remote Similarity	NPD7871	Phase 2
0.6788	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD7549	Discontinued
0.6768	Remote Similarity	NPD1608	Approved
0.6768	Remote Similarity	NPD9717	Approved
0.6766	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD9494	Approved
0.6765	Remote Similarity	NPD4307	Phase 2
0.6749	Remote Similarity	NPD7697	Approved
0.6749	Remote Similarity	NPD7698	Approved
0.6749	Remote Similarity	NPD7696	Phase 3
0.6746	Remote Similarity	NPD1296	Phase 2
0.6743	Remote Similarity	NPD2654	Approved
0.6721	Remote Similarity	NPD5760	Phase 2
0.6721	Remote Similarity	NPD5761	Phase 2
0.6715	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD7874	Approved
0.6708	Remote Similarity	NPD5536	Phase 2
0.6705	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD1876	Approved
0.6684	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD2163	Approved
0.6684	Remote Similarity	NPD8127	Discontinued
0.6667	Remote Similarity	NPD1613	Approved
0.6667	Remote Similarity	NPD3972	Approved
0.6667	Remote Similarity	NPD3887	Approved
0.6667	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7680	Approved
0.6667	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6190	Approved
0.6649	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD3268	Approved
0.6647	Remote Similarity	NPD411	Approved
0.6647	Remote Similarity	NPD3764	Approved
0.6629	Remote Similarity	NPD2353	Approved
0.6629	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD6355	Discontinued
0.6627	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD7701	Phase 2
0.661	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.661	Remote Similarity	NPD4110	Phase 3
0.661	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7033	Discontinued
0.6609	Remote Similarity	NPD4308	Phase 3
0.6608	Remote Similarity	NPD6233	Phase 2
0.6604	Remote Similarity	NPD8404	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