NPASS Compound

Structure

CID309335 OpenBabel06191716122D 43 46 0 0 0 0 0 0 0 0999 V2000 4.2451 1.6910 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 5.1111 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1111 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9771 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9771 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8432 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8432 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9771 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9771 -4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1111 -4.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2451 -4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3791 -4.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5130 -4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6470 -4.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7810 -4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0850 -4.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -2.8090 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 -0.9511 -4.3090 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 -2.6831 -3.3090 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 -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 -3.3090 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 -0.0850 -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 -1.8171 -2.8090 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 3 1 0 0 0 0 2 39 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 2 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 20 1 0 0 0 0 18 19 1 0 0 0 0 18 23 1 0 0 0 0 19 29 1 0 0 0 0 20 36 1 0 0 0 0 21 22 2 0 0 0 0 21 30 1 0 0 0 0 22 32 1 0 0 0 0 23 40 1 0 0 0 0 24 29 2 0 0 0 0 24 31 1 0 0 0 0 25 29 1 0 0 0 0 25 35 2 0 0 0 0 26 30 2 0 0 0 0 26 34 1 0 0 0 0 27 31 1 0 0 0 0 27 33 2 0 0 0 0 28 41 1 0 0 0 0 28 42 1 0 0 0 0 30 33 1 0 0 0 0 31 37 2 0 0 0 0 32 34 2 0 0 0 0 32 41 1 0 0 0 0 33 43 1 0 0 0 0 34 42 1 0 0 0 0 35 37 1 0 0 0 0 35 39 1 0 0 0 0 36 38 2 0 0 0 0 36 40 1 0 0 0 0 37 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	588.35
Volume:	640.659
LogP:	8.391
LogD:	5.833
LogS:	-3.504
# Rotatable Bonds:	21
TPSA:	67.13
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.074
Synthetic Accessibility Score:	2.984
Fsp3:	0.486
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.954
MDCK Permeability:	5.067835809313692e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.163
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.061
Plasma Protein Binding (PPB):	102.29823303222656%
Volume Distribution (VD):	5.196
Pgp-substrate:	0.6612423062324524%

ADMET: Metabolism

CYP1A2-inhibitor:	0.648
CYP1A2-substrate:	0.18
CYP2C19-inhibitor:	0.871
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.422
CYP2C9-substrate:	0.954
CYP2D6-inhibitor:	0.931
CYP2D6-substrate:	0.951
CYP3A4-inhibitor:	0.971
CYP3A4-substrate:	0.083

ADMET: Excretion

Clearance (CL):	7.828
Half-life (T1/2):	0.566

ADMET: Toxicity

hERG Blockers:	0.206
Human Hepatotoxicity (H-HT):	0.375
Drug-inuced Liver Injury (DILI):	0.917
AMES Toxicity:	0.226
Rat Oral Acute Toxicity:	0.168
Maximum Recommended Daily Dose:	0.881
Skin Sensitization:	0.961
Carcinogencity:	0.225
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.866

Download Data

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

Natural Product: NPC309335

Natural Product ID:	NPC309335
*Common Name:**	Egonol-9(Z),12(Z)Linoleate
IUPAC Name:	3-[2-(1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propyl (9Z,12Z)-octadeca-9,12-dienoate
Synonyms:	Egonol-9(Z),12(Z)-Linoleate
Standard InCHIKey:	NHCDDUNWYVJRPS-NQLNTKRDSA-N
Standard InCHI:	InChI=1S/C37H48O6/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20-36(38)40-23-18-19-29-24-31-27-33(43-37(31)35(25-29)39-2)30-21-22-32-34(26-30)42-28-41-32/h7-8,10-11,21-22,24-27H,3-6,9,12-20,23,28H2,1-2H3/b8-7-,11-10-
SMILES:	CCCCC/C=CC/C=CCCCCCCCC(=O)OCCCc1cc2cc(c3ccc4c(c3)OCO4)oc2c(c1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1834806
PubChem CID:	56598866
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
IC50	2
Others	1

Activity Type	# Activity
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	IC50	=	1400.0	nM	PMID[475950]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	=	1700.0	nM	PMID[475950]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	Inhibition	=	77.6	%	PMID[475950]

☑ 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 NPC309335 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	434
0.1-0.2	1636
0.2-0.3	3949
0.3-0.4	9226
0.4-0.5	9364
0.5-0.6	3892
0.6-0.7	7036
0.7-0.8	6755
0.8-0.85	364
0.85-0.9	28
0.9-0.95	4
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC296540
0.9868	High Similarity	NPC15764
0.9804	High Similarity	NPC139876
0.9803	High Similarity	NPC76458
0.9803	High Similarity	NPC82733
0.9677	High Similarity	NPC19948
0.9671	High Similarity	NPC3273
0.9608	High Similarity	NPC261484
0.9487	High Similarity	NPC99968
0.9363	High Similarity	NPC109238
0.9231	High Similarity	NPC261090
0.908	High Similarity	NPC135370
0.9038	High Similarity	NPC60211
0.8855	High Similarity	NPC62640
0.8834	High Similarity	NPC187923
0.8805	High Similarity	NPC268008
0.8743	High Similarity	NPC72455
0.8704	High Similarity	NPC65784
0.8675	High Similarity	NPC41853
0.8654	High Similarity	NPC153620
0.8654	High Similarity	NPC24257
0.8642	High Similarity	NPC250076
0.8636	High Similarity	NPC27220
0.8634	High Similarity	NPC239113
0.8634	High Similarity	NPC115123
0.8616	High Similarity	NPC118332
0.8614	High Similarity	NPC473531
0.8614	High Similarity	NPC167479
0.8614	High Similarity	NPC475453
0.8571	High Similarity	NPC157522
0.8571	High Similarity	NPC475964
0.8563	High Similarity	NPC211309
0.8562	High Similarity	NPC308555
0.8554	High Similarity	NPC193881
0.8554	High Similarity	NPC155264
0.8554	High Similarity	NPC471923
0.8554	High Similarity	NPC210460
0.8554	High Similarity	NPC67450
0.8537	High Similarity	NPC216092
0.8509	High Similarity	NPC54179
0.8485	Intermediate Similarity	NPC302741
0.8476	Intermediate Similarity	NPC243509
0.8476	Intermediate Similarity	NPC78944
0.8471	Intermediate Similarity	NPC66804
0.8466	Intermediate Similarity	NPC19600
0.8462	Intermediate Similarity	NPC473697
0.8457	Intermediate Similarity	NPC254163
0.8457	Intermediate Similarity	NPC80489
0.8457	Intermediate Similarity	NPC284353
0.8434	Intermediate Similarity	NPC179464
0.8428	Intermediate Similarity	NPC127827
0.8415	Intermediate Similarity	NPC68619
0.8415	Intermediate Similarity	NPC125713
0.8415	Intermediate Similarity	NPC33320
0.8412	Intermediate Similarity	NPC316539
0.8405	Intermediate Similarity	NPC155063
0.8405	Intermediate Similarity	NPC109765
0.8395	Intermediate Similarity	NPC279930
0.8393	Intermediate Similarity	NPC186392
0.8385	Intermediate Similarity	NPC104353
0.8383	Intermediate Similarity	NPC279768
0.8383	Intermediate Similarity	NPC477884
0.8375	Intermediate Similarity	NPC475722
0.8373	Intermediate Similarity	NPC22130
0.8373	Intermediate Similarity	NPC234536
0.8373	Intermediate Similarity	NPC78612
0.8373	Intermediate Similarity	NPC116838
0.8364	Intermediate Similarity	NPC131557
0.8354	Intermediate Similarity	NPC202495
0.8354	Intermediate Similarity	NPC310206
0.8333	Intermediate Similarity	NPC68882
0.8323	Intermediate Similarity	NPC110257
0.8323	Intermediate Similarity	NPC132054
0.8313	Intermediate Similarity	NPC15212
0.8313	Intermediate Similarity	NPC34376
0.8304	Intermediate Similarity	NPC474568
0.8303	Intermediate Similarity	NPC257914
0.8303	Intermediate Similarity	NPC238405
0.8303	Intermediate Similarity	NPC104459
0.8303	Intermediate Similarity	NPC325122
0.8303	Intermediate Similarity	NPC113055
0.8303	Intermediate Similarity	NPC474043
0.8294	Intermediate Similarity	NPC144288
0.8291	Intermediate Similarity	NPC213900
0.8274	Intermediate Similarity	NPC173149
0.8274	Intermediate Similarity	NPC179015
0.8266	Intermediate Similarity	NPC267549
0.8263	Intermediate Similarity	NPC272722
0.8263	Intermediate Similarity	NPC61141
0.8263	Intermediate Similarity	NPC18284
0.8263	Intermediate Similarity	NPC273021
0.8261	Intermediate Similarity	NPC474305
0.8256	Intermediate Similarity	NPC290304
0.8256	Intermediate Similarity	NPC236327
0.8253	Intermediate Similarity	NPC474770
0.825	Intermediate Similarity	NPC117463
0.8246	Intermediate Similarity	NPC312006
0.8246	Intermediate Similarity	NPC471920
0.8246	Intermediate Similarity	NPC20114
0.8246	Intermediate Similarity	NPC129930
0.8246	Intermediate Similarity	NPC114550
0.8246	Intermediate Similarity	NPC292712
0.8246	Intermediate Similarity	NPC471922
0.8246	Intermediate Similarity	NPC471921
0.8246	Intermediate Similarity	NPC474075
0.8242	Intermediate Similarity	NPC258644
0.8242	Intermediate Similarity	NPC477885
0.8232	Intermediate Similarity	NPC478238
0.8232	Intermediate Similarity	NPC234730
0.8225	Intermediate Similarity	NPC475214
0.8225	Intermediate Similarity	NPC298071
0.8221	Intermediate Similarity	NPC137813
0.8221	Intermediate Similarity	NPC144162
0.8218	Intermediate Similarity	NPC161609
0.8218	Intermediate Similarity	NPC275690
0.8214	Intermediate Similarity	NPC100425
0.8214	Intermediate Similarity	NPC65846
0.821	Intermediate Similarity	NPC474975
0.8208	Intermediate Similarity	NPC67629
0.8208	Intermediate Similarity	NPC107244
0.8208	Intermediate Similarity	NPC79736
0.8204	Intermediate Similarity	NPC264293
0.8204	Intermediate Similarity	NPC191352
0.8204	Intermediate Similarity	NPC319749
0.8204	Intermediate Similarity	NPC258322
0.8199	Intermediate Similarity	NPC474306
0.8199	Intermediate Similarity	NPC475848
0.8199	Intermediate Similarity	NPC24193
0.8198	Intermediate Similarity	NPC184624
0.8187	Intermediate Similarity	NPC51404
0.8182	Intermediate Similarity	NPC477380
0.8176	Intermediate Similarity	NPC42230
0.8176	Intermediate Similarity	NPC474948
0.8171	Intermediate Similarity	NPC478213
0.8171	Intermediate Similarity	NPC244371
0.8171	Intermediate Similarity	NPC475996
0.8166	Intermediate Similarity	NPC36320
0.8166	Intermediate Similarity	NPC474647
0.8166	Intermediate Similarity	NPC475953
0.8165	Intermediate Similarity	NPC28326
0.8161	Intermediate Similarity	NPC35266
0.816	Intermediate Similarity	NPC98028
0.816	Intermediate Similarity	NPC220577
0.8155	Intermediate Similarity	NPC125991
0.8155	Intermediate Similarity	NPC198796
0.8155	Intermediate Similarity	NPC475144
0.815	Intermediate Similarity	NPC224165
0.815	Intermediate Similarity	NPC193377
0.815	Intermediate Similarity	NPC53917
0.8148	Intermediate Similarity	NPC300983
0.8144	Intermediate Similarity	NPC239818
0.8144	Intermediate Similarity	NPC74749
0.8144	Intermediate Similarity	NPC218471
0.8144	Intermediate Similarity	NPC43971
0.8144	Intermediate Similarity	NPC19554
0.8144	Intermediate Similarity	NPC472961
0.8144	Intermediate Similarity	NPC269906
0.8144	Intermediate Similarity	NPC472962
0.8137	Intermediate Similarity	NPC181464
0.8133	Intermediate Similarity	NPC474990
0.8129	Intermediate Similarity	NPC476180
0.8129	Intermediate Similarity	NPC230968
0.8129	Intermediate Similarity	NPC102260
0.8129	Intermediate Similarity	NPC477165
0.8125	Intermediate Similarity	NPC224687
0.8125	Intermediate Similarity	NPC296575
0.8121	Intermediate Similarity	NPC10205
0.8121	Intermediate Similarity	NPC222185
0.8121	Intermediate Similarity	NPC471746
0.8118	Intermediate Similarity	NPC113093
0.8118	Intermediate Similarity	NPC474042
0.8118	Intermediate Similarity	NPC174734
0.8113	Intermediate Similarity	NPC473090
0.811	Intermediate Similarity	NPC131121
0.811	Intermediate Similarity	NPC148497
0.811	Intermediate Similarity	NPC292460
0.811	Intermediate Similarity	NPC153008
0.8107	Intermediate Similarity	NPC472582
0.8107	Intermediate Similarity	NPC45943
0.8103	Intermediate Similarity	NPC196771
0.8103	Intermediate Similarity	NPC156635
0.8095	Intermediate Similarity	NPC209411
0.8095	Intermediate Similarity	NPC239890
0.8095	Intermediate Similarity	NPC469889
0.8095	Intermediate Similarity	NPC94155
0.8092	Intermediate Similarity	NPC65885
0.8092	Intermediate Similarity	NPC477881
0.8092	Intermediate Similarity	NPC233956
0.8084	Intermediate Similarity	NPC228501
0.8084	Intermediate Similarity	NPC50430
0.8081	Intermediate Similarity	NPC475434
0.8081	Intermediate Similarity	NPC52598
0.8079	Intermediate Similarity	NPC167045
0.8079	Intermediate Similarity	NPC114120
0.8075	Intermediate Similarity	NPC25496
0.8072	Intermediate Similarity	NPC301897
0.8072	Intermediate Similarity	NPC473900
0.8072	Intermediate Similarity	NPC471405
0.8072	Intermediate Similarity	NPC257277
0.807	Intermediate Similarity	NPC247973

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 NPC309335 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	369
0.1-0.2	933
0.2-0.3	1721
0.3-0.4	2641
0.4-0.5	1936
0.5-0.6	987
0.6-0.7	427
0.7-0.8	129
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8415	Intermediate Similarity	NPD919	Approved
0.825	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD1247	Approved
0.8176	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD3817	Phase 2
0.8	Intermediate Similarity	NPD3926	Phase 2
0.7964	Intermediate Similarity	NPD3882	Suspended
0.7929	Intermediate Similarity	NPD5494	Approved
0.7895	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD3818	Discontinued
0.7844	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD920	Approved
0.7784	Intermediate Similarity	NPD6559	Discontinued
0.774	Intermediate Similarity	NPD7808	Phase 3
0.774	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD6799	Approved
0.7714	Intermediate Similarity	NPD5844	Phase 1
0.7706	Intermediate Similarity	NPD7075	Discontinued
0.7688	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7199	Phase 2
0.7657	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD7819	Suspended
0.7619	Intermediate Similarity	NPD6385	Approved
0.7619	Intermediate Similarity	NPD6386	Approved
0.7614	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7473	Discontinued
0.7593	Intermediate Similarity	NPD1243	Approved
0.7584	Intermediate Similarity	NPD7251	Discontinued
0.7574	Intermediate Similarity	NPD6801	Discontinued
0.7571	Intermediate Similarity	NPD7074	Phase 3
0.7561	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD6599	Discontinued
0.7544	Intermediate Similarity	NPD4965	Approved
0.7544	Intermediate Similarity	NPD4966	Approved
0.7544	Intermediate Similarity	NPD4967	Phase 2
0.7529	Intermediate Similarity	NPD6232	Discontinued
0.7529	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD6797	Phase 2
0.7528	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7054	Approved
0.75	Intermediate Similarity	NPD7458	Discontinued
0.7484	Intermediate Similarity	NPD1933	Approved
0.7472	Intermediate Similarity	NPD7472	Approved
0.7471	Intermediate Similarity	NPD1934	Approved
0.7457	Intermediate Similarity	NPD6234	Discontinued
0.7443	Intermediate Similarity	NPD6166	Phase 2
0.7443	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD4628	Phase 3
0.7427	Intermediate Similarity	NPD2801	Approved
0.7427	Intermediate Similarity	NPD8455	Phase 2
0.7405	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3887	Approved
0.7389	Intermediate Similarity	NPD7685	Pre-registration
0.7377	Intermediate Similarity	NPD8434	Phase 2
0.7375	Intermediate Similarity	NPD6355	Discontinued
0.7368	Intermediate Similarity	NPD37	Approved
0.7365	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD2344	Approved
0.7362	Intermediate Similarity	NPD1471	Phase 3
0.736	Intermediate Similarity	NPD2163	Approved
0.7346	Intermediate Similarity	NPD2799	Discontinued
0.731	Intermediate Similarity	NPD7411	Suspended
0.7308	Intermediate Similarity	NPD8312	Approved
0.7308	Intermediate Similarity	NPD8313	Approved
0.7301	Intermediate Similarity	NPD2796	Approved
0.7299	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6798	Discontinued
0.7283	Intermediate Similarity	NPD5402	Approved
0.7263	Intermediate Similarity	NPD7228	Approved
0.7262	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD3146	Approved
0.7256	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD2353	Approved
0.7241	Intermediate Similarity	NPD7768	Phase 2
0.7225	Intermediate Similarity	NPD1465	Phase 2
0.7219	Intermediate Similarity	NPD1512	Approved
0.72	Intermediate Similarity	NPD3749	Approved
0.7195	Intermediate Similarity	NPD2935	Discontinued
0.7193	Intermediate Similarity	NPD3226	Approved
0.7191	Intermediate Similarity	NPD5242	Approved
0.7188	Intermediate Similarity	NPD2313	Discontinued
0.7188	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD2309	Approved
0.7175	Intermediate Similarity	NPD8127	Discontinued
0.717	Intermediate Similarity	NPD6832	Phase 2
0.7161	Intermediate Similarity	NPD3705	Approved
0.716	Intermediate Similarity	NPD447	Suspended
0.7152	Intermediate Similarity	NPD2346	Discontinued
0.7151	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD17	Approved
0.7135	Intermediate Similarity	NPD6808	Phase 2
0.7135	Intermediate Similarity	NPD7229	Phase 3
0.7134	Intermediate Similarity	NPD3748	Approved
0.7118	Intermediate Similarity	NPD5049	Phase 3
0.7104	Intermediate Similarity	NPD7240	Approved
0.7101	Intermediate Similarity	NPD1511	Approved
0.7099	Intermediate Similarity	NPD4060	Phase 1
0.7086	Intermediate Similarity	NPD5353	Approved
0.7086	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2354	Approved
0.7083	Intermediate Similarity	NPD6190	Approved
0.7076	Intermediate Similarity	NPD5403	Approved
0.7072	Intermediate Similarity	NPD3751	Discontinued
0.7069	Intermediate Similarity	NPD6280	Approved
0.7069	Intermediate Similarity	NPD6279	Approved
0.7062	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5401	Approved
0.7059	Intermediate Similarity	NPD5536	Phase 2
0.7059	Intermediate Similarity	NPD2532	Approved
0.7059	Intermediate Similarity	NPD2534	Approved
0.7059	Intermediate Similarity	NPD2533	Approved
0.7055	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD4380	Phase 2
0.7047	Intermediate Similarity	NPD4107	Approved
0.7039	Intermediate Similarity	NPD3787	Discontinued
0.7037	Intermediate Similarity	NPD6233	Phase 2
0.7031	Intermediate Similarity	NPD4420	Approved
0.7011	Intermediate Similarity	NPD6764	Approved
0.7011	Intermediate Similarity	NPD6873	Phase 2
0.7011	Intermediate Similarity	NPD6765	Approved
0.7006	Intermediate Similarity	NPD1608	Approved
0.6994	Remote Similarity	NPD2979	Phase 3
0.6961	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7028	Phase 2
0.6951	Remote Similarity	NPD230	Phase 1
0.6939	Remote Similarity	NPD7435	Discontinued
0.6923	Remote Similarity	NPD4482	Phase 3
0.6923	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3750	Approved
0.6923	Remote Similarity	NPD4110	Phase 3
0.6914	Remote Similarity	NPD7095	Approved
0.6905	Remote Similarity	NPD1549	Phase 2
0.6899	Remote Similarity	NPD3972	Approved
0.6897	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD9494	Approved
0.6889	Remote Similarity	NPD6959	Discontinued
0.6888	Remote Similarity	NPD5005	Approved
0.6888	Remote Similarity	NPD5006	Approved
0.6886	Remote Similarity	NPD2438	Suspended
0.6885	Remote Similarity	NPD7177	Discontinued
0.6875	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD3764	Approved
0.6862	Remote Similarity	NPD6784	Approved
0.6862	Remote Similarity	NPD6785	Approved
0.685	Remote Similarity	NPD8151	Discontinued
0.6848	Remote Similarity	NPD7286	Phase 2
0.6845	Remote Similarity	NPD7266	Discontinued
0.6845	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD5763	Approved
0.6845	Remote Similarity	NPD5762	Approved
0.6839	Remote Similarity	NPD1653	Approved
0.6836	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1281	Approved
0.6835	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD2798	Approved
0.6829	Remote Similarity	NPD8032	Phase 2
0.6829	Remote Similarity	NPD4062	Phase 3
0.6828	Remote Similarity	NPD7038	Approved
0.6828	Remote Similarity	NPD7039	Approved
0.6826	Remote Similarity	NPD1510	Phase 2
0.6824	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7003	Approved
0.6821	Remote Similarity	NPD6273	Approved
0.6818	Remote Similarity	NPD7870	Phase 2
0.6818	Remote Similarity	NPD7871	Phase 2
0.6816	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7874	Approved
0.6809	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD2897	Discontinued
0.6804	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD1241	Discontinued
0.6788	Remote Similarity	NPD4307	Phase 2
0.6788	Remote Similarity	NPD1240	Approved
0.6782	Remote Similarity	NPD7783	Phase 2
0.6782	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD2403	Approved
0.6774	Remote Similarity	NPD5953	Discontinued
0.677	Remote Similarity	NPD3267	Approved
0.677	Remote Similarity	NPD3266	Approved
0.6768	Remote Similarity	NPD7698	Approved
0.6768	Remote Similarity	NPD7697	Approved
0.6768	Remote Similarity	NPD7696	Phase 3
0.6768	Remote Similarity	NPD7680	Approved
0.6766	Remote Similarity	NPD7097	Phase 1
0.6765	Remote Similarity	NPD6674	Discontinued
0.6765	Remote Similarity	NPD2800	Approved
0.676	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD1651	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