NPASS Compound

Structure

CID15764 OpenBabel06191715342D 27 30 0 0 0 0 0 0 0 0999 V2000 7.8793 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 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 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.8090 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 2.6831 0.3090 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 0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6705 2.0115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 1.8090 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 -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 -3.5878 0.8090 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 -3.0878 1.6750 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 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5659 1.0169 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7569 2.4182 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 13 1 0 0 0 0 2 23 1 0 0 0 0 3 4 1 0 0 0 0 3 7 1 0 0 0 0 4 14 1 0 0 0 0 5 6 2 0 0 0 0 5 15 1 0 0 0 0 6 17 1 0 0 0 0 7 24 1 0 0 0 0 8 14 2 0 0 0 0 8 16 1 0 0 0 0 9 14 1 0 0 0 0 9 20 2 0 0 0 0 10 15 2 0 0 0 0 10 19 1 0 0 0 0 11 16 1 0 0 0 0 11 18 2 0 0 0 0 12 25 1 0 0 0 0 12 26 1 0 0 0 0 13 22 2 0 0 0 0 13 24 1 0 0 0 0 15 18 1 0 0 0 0 16 21 2 0 0 0 0 17 19 2 0 0 0 0 17 25 1 0 0 0 0 18 27 1 0 0 0 0 19 26 1 0 0 0 0 20 21 1 0 0 0 0 20 23 1 0 0 0 0 21 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	368.13
Volume:	369.196
LogP:	4.751
LogD:	3.715
LogS:	-6.583
# Rotatable Bonds:	7
TPSA:	67.13
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.476
Synthetic Accessibility Score:	2.413
Fsp3:	0.286
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:	-4.823
MDCK Permeability:	4.550869925878942e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.119

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.285
Plasma Protein Binding (PPB):	98.42217254638672%
Volume Distribution (VD):	1.362
Pgp-substrate:	3.2645046710968018%

ADMET: Metabolism

CYP1A2-inhibitor:	0.993
CYP1A2-substrate:	0.238
CYP2C19-inhibitor:	0.97
CYP2C19-substrate:	0.069
CYP2C9-inhibitor:	0.886
CYP2C9-substrate:	0.919
CYP2D6-inhibitor:	0.971
CYP2D6-substrate:	0.915
CYP3A4-inhibitor:	0.954
CYP3A4-substrate:	0.241

ADMET: Excretion

Clearance (CL):	11.399
Half-life (T1/2):	0.252

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.256
Drug-inuced Liver Injury (DILI):	0.934
AMES Toxicity:	0.299
Rat Oral Acute Toxicity:	0.048
Maximum Recommended Daily Dose:	0.832
Skin Sensitization:	0.101
Carcinogencity:	0.895
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.459

Download Data

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

Natural Product: NPC15764

Natural Product ID:	NPC15764
*Common Name:**	Egonol Acetate
IUPAC Name:	3-[2-(1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propyl acetate
Synonyms:	Egonol Acetate
Standard InCHIKey:	KOUYRIXNPBTZIN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H20O6/c1-13(22)24-7-3-4-14-8-16-11-18(27-21(16)20(9-14)23-2)15-5-6-17-19(10-15)26-12-25-17/h5-6,8-11H,3-4,7,12H2,1-2H3
SMILES:	COc1cc(CCCOC(=O)C)cc2c1oc(c2)c1ccc2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1667984
PubChem CID:	14018770
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
NPO14098	Styrax agrestis	Species	Styracaceae	Eukaryota	fruits	Thua Thien, Hue district, Vietnam	n.a.	PMID[21939219]
NPO14098	Styrax agrestis	Species	Styracaceae	Eukaryota	n.a.	ripe fruit	n.a.	PMID[21939219]
NPO14098	Styrax agrestis	Species	Styracaceae	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
MIC	1
Others	1

Activity Type	# Activity
Individual Protein	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	Inhibition	=	64.6	%	PMID[465776]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	200.0	ug.mL-1	PMID[465775]

☑ 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 NPC15764 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	430
0.1-0.2	1848
0.2-0.3	4378
0.3-0.4	9740
0.4-0.5	8347
0.5-0.6	3881
0.6-0.7	7105
0.7-0.8	6453
0.8-0.85	462
0.85-0.9	40
0.9-0.95	2
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC139876
0.9868	High Similarity	NPC309335
0.9868	High Similarity	NPC296540
0.9804	High Similarity	NPC19948
0.98	High Similarity	NPC3273
0.9735	High Similarity	NPC261484
0.9671	High Similarity	NPC76458
0.9671	High Similarity	NPC82733
0.961	High Similarity	NPC99968
0.9484	High Similarity	NPC109238
0.9351	High Similarity	NPC261090
0.9193	High Similarity	NPC135370
0.9156	High Similarity	NPC60211
0.8963	High Similarity	NPC62640
0.8944	High Similarity	NPC187923
0.8917	High Similarity	NPC268008
0.8848	High Similarity	NPC72455
0.8812	High Similarity	NPC65784
0.878	High Similarity	NPC41853
0.8766	High Similarity	NPC153620
0.8766	High Similarity	NPC24257
0.875	High Similarity	NPC27220
0.875	High Similarity	NPC250076
0.8742	High Similarity	NPC115123
0.8742	High Similarity	NPC239113
0.8726	High Similarity	NPC118332
0.872	High Similarity	NPC167479
0.8675	High Similarity	NPC475964
0.8675	High Similarity	NPC157522
0.8671	High Similarity	NPC308555
0.8667	High Similarity	NPC211309
0.8659	High Similarity	NPC155264
0.8659	High Similarity	NPC67450
0.8659	High Similarity	NPC193881
0.8659	High Similarity	NPC210460
0.8642	High Similarity	NPC216092
0.8616	High Similarity	NPC54179
0.8589	High Similarity	NPC302741
0.858	High Similarity	NPC78944
0.858	High Similarity	NPC243509
0.8571	High Similarity	NPC19600
0.8571	High Similarity	NPC66804
0.8562	High Similarity	NPC254163
0.8562	High Similarity	NPC80489
0.8562	High Similarity	NPC284353
0.8545	High Similarity	NPC471923
0.8537	High Similarity	NPC179464
0.8535	High Similarity	NPC127827
0.8519	High Similarity	NPC68619
0.8519	High Similarity	NPC125713
0.8519	High Similarity	NPC33320
0.8509	High Similarity	NPC155063
0.8509	High Similarity	NPC109765
0.85	High Similarity	NPC279930
0.8494	Intermediate Similarity	NPC186392
0.8494	Intermediate Similarity	NPC475453
0.8494	Intermediate Similarity	NPC473531
0.8491	Intermediate Similarity	NPC104353
0.8485	Intermediate Similarity	NPC279768
0.8481	Intermediate Similarity	NPC475722
0.8476	Intermediate Similarity	NPC78612
0.8476	Intermediate Similarity	NPC116838
0.8476	Intermediate Similarity	NPC22130
0.8476	Intermediate Similarity	NPC234536
0.8466	Intermediate Similarity	NPC131557
0.8457	Intermediate Similarity	NPC310206
0.8457	Intermediate Similarity	NPC202495
0.8438	Intermediate Similarity	NPC68882
0.8424	Intermediate Similarity	NPC132054
0.8424	Intermediate Similarity	NPC110257
0.8415	Intermediate Similarity	NPC15212
0.8415	Intermediate Similarity	NPC34376
0.8405	Intermediate Similarity	NPC257914
0.8405	Intermediate Similarity	NPC325122
0.8405	Intermediate Similarity	NPC104459
0.8405	Intermediate Similarity	NPC474043
0.8405	Intermediate Similarity	NPC113055
0.8405	Intermediate Similarity	NPC238405
0.8402	Intermediate Similarity	NPC474568
0.8397	Intermediate Similarity	NPC213900
0.8393	Intermediate Similarity	NPC144288
0.8373	Intermediate Similarity	NPC179015
0.8373	Intermediate Similarity	NPC173149
0.8364	Intermediate Similarity	NPC18284
0.8364	Intermediate Similarity	NPC273021
0.8364	Intermediate Similarity	NPC272722
0.8364	Intermediate Similarity	NPC61141
0.8354	Intermediate Similarity	NPC474770
0.8354	Intermediate Similarity	NPC117463
0.8353	Intermediate Similarity	NPC290304
0.8353	Intermediate Similarity	NPC236327
0.8344	Intermediate Similarity	NPC258644
0.8343	Intermediate Similarity	NPC129930
0.8343	Intermediate Similarity	NPC471920
0.8343	Intermediate Similarity	NPC114550
0.8343	Intermediate Similarity	NPC292712
0.8343	Intermediate Similarity	NPC471921
0.8343	Intermediate Similarity	NPC473697
0.8343	Intermediate Similarity	NPC312006
0.8343	Intermediate Similarity	NPC20114
0.8343	Intermediate Similarity	NPC474075
0.8343	Intermediate Similarity	NPC471922
0.8333	Intermediate Similarity	NPC478238
0.8333	Intermediate Similarity	NPC234730
0.8323	Intermediate Similarity	NPC137813
0.8323	Intermediate Similarity	NPC298071
0.8323	Intermediate Similarity	NPC144162
0.8313	Intermediate Similarity	NPC474975
0.8313	Intermediate Similarity	NPC65846
0.8304	Intermediate Similarity	NPC107244
0.8303	Intermediate Similarity	NPC191352
0.8303	Intermediate Similarity	NPC258322
0.8303	Intermediate Similarity	NPC264293
0.8302	Intermediate Similarity	NPC24193
0.8294	Intermediate Similarity	NPC316539
0.8294	Intermediate Similarity	NPC184624
0.8284	Intermediate Similarity	NPC51404
0.8274	Intermediate Similarity	NPC42230
0.8274	Intermediate Similarity	NPC474948
0.8272	Intermediate Similarity	NPC244371
0.8272	Intermediate Similarity	NPC478213
0.8269	Intermediate Similarity	NPC28326
0.8266	Intermediate Similarity	NPC475996
0.8263	Intermediate Similarity	NPC36320
0.8263	Intermediate Similarity	NPC477884
0.8263	Intermediate Similarity	NPC475953
0.8261	Intermediate Similarity	NPC98028
0.8261	Intermediate Similarity	NPC220577
0.8253	Intermediate Similarity	NPC125991
0.8253	Intermediate Similarity	NPC198796
0.825	Intermediate Similarity	NPC474305
0.825	Intermediate Similarity	NPC300983
0.8246	Intermediate Similarity	NPC224165
0.8246	Intermediate Similarity	NPC53917
0.8246	Intermediate Similarity	NPC193377
0.8242	Intermediate Similarity	NPC472962
0.8242	Intermediate Similarity	NPC74749
0.8242	Intermediate Similarity	NPC269906
0.8242	Intermediate Similarity	NPC19554
0.8242	Intermediate Similarity	NPC239818
0.8242	Intermediate Similarity	NPC218471
0.8242	Intermediate Similarity	NPC43971
0.8242	Intermediate Similarity	NPC472961
0.8239	Intermediate Similarity	NPC181464
0.8235	Intermediate Similarity	NPC102260
0.8235	Intermediate Similarity	NPC230968
0.8232	Intermediate Similarity	NPC474990
0.8228	Intermediate Similarity	NPC224687
0.8228	Intermediate Similarity	NPC296575
0.8221	Intermediate Similarity	NPC471746
0.8221	Intermediate Similarity	NPC10205
0.8217	Intermediate Similarity	NPC473090
0.8214	Intermediate Similarity	NPC474042
0.8214	Intermediate Similarity	NPC113093
0.8214	Intermediate Similarity	NPC174734
0.821	Intermediate Similarity	NPC153008
0.821	Intermediate Similarity	NPC131121
0.821	Intermediate Similarity	NPC148497
0.821	Intermediate Similarity	NPC292460
0.8204	Intermediate Similarity	NPC472582
0.8198	Intermediate Similarity	NPC196771
0.8198	Intermediate Similarity	NPC156635
0.8193	Intermediate Similarity	NPC469889
0.8193	Intermediate Similarity	NPC209411
0.8193	Intermediate Similarity	NPC239890
0.8193	Intermediate Similarity	NPC94155
0.8187	Intermediate Similarity	NPC65885
0.8187	Intermediate Similarity	NPC233956
0.8187	Intermediate Similarity	NPC474306
0.8187	Intermediate Similarity	NPC475848
0.8182	Intermediate Similarity	NPC228501
0.8182	Intermediate Similarity	NPC50430
0.8176	Intermediate Similarity	NPC52598
0.8176	Intermediate Similarity	NPC25496
0.8171	Intermediate Similarity	NPC301897
0.8171	Intermediate Similarity	NPC471405
0.8171	Intermediate Similarity	NPC473900
0.8171	Intermediate Similarity	NPC477380
0.8166	Intermediate Similarity	NPC247973
0.8165	Intermediate Similarity	NPC474158
0.8165	Intermediate Similarity	NPC327052
0.816	Intermediate Similarity	NPC57211
0.816	Intermediate Similarity	NPC178195
0.816	Intermediate Similarity	NPC186507
0.816	Intermediate Similarity	NPC348849
0.8158	Intermediate Similarity	NPC205915
0.8155	Intermediate Similarity	NPC474647
0.8155	Intermediate Similarity	NPC45449
0.8153	Intermediate Similarity	NPC137920
0.8153	Intermediate Similarity	NPC86455
0.8153	Intermediate Similarity	NPC125134
0.815	Intermediate Similarity	NPC35266
0.815	Intermediate Similarity	NPC267549
0.815	Intermediate Similarity	NPC47191
0.8148	Intermediate Similarity	NPC474388
0.8148	Intermediate Similarity	NPC474170
0.8148	Intermediate Similarity	NPC36130
0.8148	Intermediate Similarity	NPC279061
0.8148	Intermediate Similarity	NPC472535
0.8148	Intermediate Similarity	NPC134905

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 NPC15764 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	378
0.1-0.2	963
0.2-0.3	1733
0.3-0.4	2653
0.4-0.5	1880
0.5-0.6	985
0.6-0.7	419
0.7-0.8	130
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8519	High Similarity	NPD919	Approved
0.8354	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD1247	Approved
0.828	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD3817	Phase 2
0.8095	Intermediate Similarity	NPD3926	Phase 2
0.8061	Intermediate Similarity	NPD3882	Suspended
0.8024	Intermediate Similarity	NPD5494	Approved
0.7988	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD3818	Discontinued
0.7911	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD920	Approved
0.7874	Intermediate Similarity	NPD6559	Discontinued
0.7831	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD6799	Approved
0.7803	Intermediate Similarity	NPD5844	Phase 1
0.7785	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7199	Phase 2
0.7738	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7075	Discontinued
0.7688	Intermediate Similarity	NPD1243	Approved
0.7665	Intermediate Similarity	NPD6801	Discontinued
0.7654	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD6599	Discontinued
0.7633	Intermediate Similarity	NPD4966	Approved
0.7633	Intermediate Similarity	NPD4965	Approved
0.7633	Intermediate Similarity	NPD4967	Phase 2
0.7627	Intermediate Similarity	NPD7808	Phase 3
0.7619	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6232	Discontinued
0.7614	Intermediate Similarity	NPD6797	Phase 2
0.7605	Intermediate Similarity	NPD6386	Approved
0.7605	Intermediate Similarity	NPD6385	Approved
0.7586	Intermediate Similarity	NPD7473	Discontinued
0.758	Intermediate Similarity	NPD1933	Approved
0.7571	Intermediate Similarity	NPD7251	Discontinued
0.7569	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD1934	Approved
0.7557	Intermediate Similarity	NPD7074	Phase 3
0.7544	Intermediate Similarity	NPD6234	Discontinued
0.7543	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD4628	Phase 3
0.7529	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6166	Phase 2
0.7529	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7819	Suspended
0.7515	Intermediate Similarity	NPD2801	Approved
0.7514	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7054	Approved
0.75	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3887	Approved
0.7485	Intermediate Similarity	NPD7458	Discontinued
0.7458	Intermediate Similarity	NPD7472	Approved
0.7456	Intermediate Similarity	NPD37	Approved
0.7455	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD1471	Phase 3
0.7453	Intermediate Similarity	NPD2344	Approved
0.7443	Intermediate Similarity	NPD2163	Approved
0.7438	Intermediate Similarity	NPD2799	Discontinued
0.7396	Intermediate Similarity	NPD7411	Suspended
0.7391	Intermediate Similarity	NPD2796	Approved
0.7389	Intermediate Similarity	NPD6798	Discontinued
0.7384	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5402	Approved
0.7358	Intermediate Similarity	NPD6355	Discontinued
0.7349	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD3146	Approved
0.7346	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD2353	Approved
0.731	Intermediate Similarity	NPD8455	Phase 2
0.731	Intermediate Similarity	NPD1465	Phase 2
0.7305	Intermediate Similarity	NPD1512	Approved
0.7297	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD2935	Discontinued
0.7283	Intermediate Similarity	NPD3749	Approved
0.7278	Intermediate Similarity	NPD3226	Approved
0.7278	Intermediate Similarity	NPD7685	Pre-registration
0.7278	Intermediate Similarity	NPD2313	Discontinued
0.7273	Intermediate Similarity	NPD5242	Approved
0.7273	Intermediate Similarity	NPD2309	Approved
0.7268	Intermediate Similarity	NPD8434	Phase 2
0.7255	Intermediate Similarity	NPD3705	Approved
0.725	Intermediate Similarity	NPD447	Suspended
0.7247	Intermediate Similarity	NPD7228	Approved
0.7239	Intermediate Similarity	NPD2346	Discontinued
0.7237	Intermediate Similarity	NPD17	Approved
0.7222	Intermediate Similarity	NPD3748	Approved
0.7216	Intermediate Similarity	NPD6808	Phase 2
0.7202	Intermediate Similarity	NPD5049	Phase 3
0.7198	Intermediate Similarity	NPD8312	Approved
0.7198	Intermediate Similarity	NPD8313	Approved
0.7188	Intermediate Similarity	NPD4060	Phase 1
0.7186	Intermediate Similarity	NPD1511	Approved
0.717	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2354	Approved
0.7169	Intermediate Similarity	NPD6190	Approved
0.716	Intermediate Similarity	NPD5403	Approved
0.7152	Intermediate Similarity	NPD6832	Phase 2
0.7152	Intermediate Similarity	NPD5536	Phase 2
0.7151	Intermediate Similarity	NPD6280	Approved
0.7151	Intermediate Similarity	NPD6279	Approved
0.7151	Intermediate Similarity	NPD3751	Discontinued
0.7143	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5401	Approved
0.7143	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2533	Approved
0.7143	Intermediate Similarity	NPD2534	Approved
0.7143	Intermediate Similarity	NPD2532	Approved
0.7135	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4380	Phase 2
0.7126	Intermediate Similarity	NPD7768	Phase 2
0.7125	Intermediate Similarity	NPD6233	Phase 2
0.712	Intermediate Similarity	NPD4107	Approved
0.7119	Intermediate Similarity	NPD3787	Discontinued
0.7119	Intermediate Similarity	NPD7229	Phase 3
0.7105	Intermediate Similarity	NPD4420	Approved
0.7097	Intermediate Similarity	NPD1608	Approved
0.7088	Intermediate Similarity	NPD7240	Approved
0.7088	Intermediate Similarity	NPD6764	Approved
0.7088	Intermediate Similarity	NPD6765	Approved
0.7081	Intermediate Similarity	NPD2979	Phase 3
0.7069	Intermediate Similarity	NPD5353	Approved
0.7062	Intermediate Similarity	NPD8127	Discontinued
0.7041	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD230	Phase 1
0.7035	Intermediate Similarity	NPD7028	Phase 2
0.7006	Intermediate Similarity	NPD4110	Phase 3
0.7006	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3750	Approved
0.6995	Remote Similarity	NPD4482	Phase 3
0.6994	Remote Similarity	NPD6873	Phase 2
0.6988	Remote Similarity	NPD1549	Phase 2
0.6987	Remote Similarity	NPD3972	Approved
0.6981	Remote Similarity	NPD9494	Approved
0.6977	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.697	Remote Similarity	NPD2438	Suspended
0.6966	Remote Similarity	NPD6959	Discontinued
0.6962	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7177	Discontinued
0.6959	Remote Similarity	NPD5006	Approved
0.6959	Remote Similarity	NPD5005	Approved
0.6957	Remote Similarity	NPD3764	Approved
0.6935	Remote Similarity	NPD6785	Approved
0.6935	Remote Similarity	NPD6784	Approved
0.6928	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7435	Discontinued
0.6923	Remote Similarity	NPD1281	Approved
0.6919	Remote Similarity	NPD1653	Approved
0.6918	Remote Similarity	NPD2798	Approved
0.6914	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4062	Phase 3
0.6909	Remote Similarity	NPD1510	Phase 2
0.6905	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7003	Approved
0.6902	Remote Similarity	NPD7039	Approved
0.6902	Remote Similarity	NPD7038	Approved
0.6901	Remote Similarity	NPD6273	Approved
0.6894	Remote Similarity	NPD7095	Approved
0.6887	Remote Similarity	NPD1241	Discontinued
0.6886	Remote Similarity	NPD2897	Discontinued
0.6875	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1240	Approved
0.6871	Remote Similarity	NPD4307	Phase 2
0.6855	Remote Similarity	NPD3267	Approved
0.6855	Remote Similarity	NPD3266	Approved
0.6851	Remote Similarity	NPD2403	Approved
0.6848	Remote Similarity	NPD5953	Discontinued
0.6845	Remote Similarity	NPD2800	Approved
0.6839	Remote Similarity	NPD1651	Approved
0.6839	Remote Similarity	NPD5691	Approved
0.6836	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD7286	Phase 2
0.6826	Remote Similarity	NPD5763	Approved
0.6826	Remote Similarity	NPD6005	Phase 3
0.6826	Remote Similarity	NPD5762	Approved
0.6826	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD6004	Phase 3
0.6826	Remote Similarity	NPD7266	Discontinued
0.6826	Remote Similarity	NPD6002	Phase 3
0.6826	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7033	Discontinued
0.6792	Remote Similarity	NPD1876	Approved
0.6792	Remote Similarity	NPD1283	Approved
0.6791	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD1607	Approved
0.6786	Remote Similarity	NPD970	Clinical (unspecified phase)
0.678	Remote Similarity	NPD5977	Approved
0.678	Remote Similarity	NPD5978	Approved
0.678	Remote Similarity	NPD2296	Approved
0.6776	Remote Similarity	NPD5283	Phase 1

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