NPASS Compound

Structure

CID76458 OpenBabel06191715412D 41 44 0 0 0 0 0 0 0 0999 V2000 -5.6843 4.1092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8183 3.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8183 2.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9523 2.1092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9523 1.1092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0863 0.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0863 -0.3908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2202 -0.8908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2202 -1.8908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3542 -2.3908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4882 -1.8908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3778 -2.3908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2439 -1.8908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1099 -2.3908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9759 -1.8908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8419 -2.3908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3060 -0.3908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3060 0.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7080 -1.8908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4400 2.1092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6691 2.4752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5740 2.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 2.4752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4400 -0.8908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5740 0.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7569 0.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4400 1.1092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7080 1.1092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7080 2.1092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7080 -0.8908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8419 -0.3908 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5740 -0.3908 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 1.4013 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7569 2.4182 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 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 1 0 0 0 0 8 9 1 0 0 0 0 9 10 2 0 0 0 0 10 11 1 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 19 1 0 0 0 0 17 18 1 0 0 0 0 17 24 1 0 0 0 0 18 29 1 0 0 0 0 19 36 1 0 0 0 0 20 22 2 0 0 0 0 20 29 1 0 0 0 0 21 23 2 0 0 0 0 21 30 1 0 0 0 0 22 32 1 0 0 0 0 23 33 1 0 0 0 0 24 38 1 0 0 0 0 25 29 2 0 0 0 0 25 31 1 0 0 0 0 26 30 2 0 0 0 0 26 35 1 0 0 0 0 27 31 1 0 0 0 0 27 34 2 0 0 0 0 28 39 1 0 0 0 0 28 40 1 0 0 0 0 30 34 1 0 0 0 0 31 32 2 0 0 0 0 32 41 1 0 0 0 0 33 35 2 0 0 0 0 33 39 1 0 0 0 0 34 41 1 0 0 0 0 35 40 1 0 0 0 0 36 37 2 0 0 0 0 36 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	560.35
Volume:	617.209
LogP:	9.798
LogD:	5.686
LogS:	-5.145
# Rotatable Bonds:	21
TPSA:	57.9
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.078
Synthetic Accessibility Score:	2.744
Fsp3:	0.528
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:	-5.003
MDCK Permeability:	2.362153827561997e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.025
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.981
30% Bioavailability (F30%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	102.40532684326172%
Volume Distribution (VD):	4.365
Pgp-substrate:	0.5820503234863281%

ADMET: Metabolism

CYP1A2-inhibitor:	0.569
CYP1A2-substrate:	0.143
CYP2C19-inhibitor:	0.582
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.111
CYP2C9-substrate:	0.946
CYP2D6-inhibitor:	0.887
CYP2D6-substrate:	0.923
CYP3A4-inhibitor:	0.898
CYP3A4-substrate:	0.081

ADMET: Excretion

Clearance (CL):	7.859
Half-life (T1/2):	0.123

ADMET: Toxicity

hERG Blockers:	0.455
Human Hepatotoxicity (H-HT):	0.157
Drug-inuced Liver Injury (DILI):	0.897
AMES Toxicity:	0.09
Rat Oral Acute Toxicity:	0.409
Maximum Recommended Daily Dose:	0.704
Skin Sensitization:	0.97
Carcinogencity:	0.126
Eye Corrosion:	0.003
Eye Irritation:	0.097
Respiratory Toxicity:	0.614

Download Data

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

Natural Product: NPC76458

Natural Product ID:	NPC76458
*Common Name:**	7-Demethoxyegonol Oleate
IUPAC Name:	3-[2-(1,3-benzodioxol-5-yl)-1-benzofuran-5-yl]propyl (Z)-octadec-9-enoate
Synonyms:	7-Demethoxyegonol Oleate
Standard InCHIKey:	GIGIGVBVJACSBJ-KTKRTIGZSA-N
Standard InCHI:	InChI=1S/C36H48O5/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-19-36(37)38-24-17-18-29-20-22-32-31(25-29)27-34(41-32)30-21-23-33-35(26-30)40-28-39-33/h9-10,20-23,25-27H,2-8,11-19,24,28H2,1H3/b10-9-
SMILES:	CCCCCCCC/C=CCCCCCCCC(=O)OCCCc1ccc2c(c1)cc(o2)c1ccc2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1834809
PubChem CID:	56600473
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

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	IC50	=	2200.0	nM	PMID[518285]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	=	3100.0	nM	PMID[518285]

☑ 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 NPC76458 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	420
0.1-0.2	1608
0.2-0.3	3687
0.3-0.4	9103
0.4-0.5	9615
0.5-0.6	3733
0.6-0.7	6686
0.7-0.8	7382
0.8-0.85	413
0.85-0.9	38
0.9-0.95	5
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC82733
0.9803	High Similarity	NPC296540
0.9803	High Similarity	NPC309335
0.98	High Similarity	NPC261484
0.9671	High Similarity	NPC15764
0.9608	High Similarity	NPC139876
0.9484	High Similarity	NPC19948
0.9474	High Similarity	NPC3273
0.9412	High Similarity	NPC261090
0.9295	High Similarity	NPC99968
0.9172	High Similarity	NPC109238
0.8902	High Similarity	NPC72455
0.8896	High Similarity	NPC135370
0.8846	High Similarity	NPC60211
0.8834	High Similarity	NPC41853
0.8824	High Similarity	NPC24257
0.8824	High Similarity	NPC153620
0.8797	High Similarity	NPC115123
0.8797	High Similarity	NPC239113
0.8782	High Similarity	NPC118332
0.8773	High Similarity	NPC475453
0.8773	High Similarity	NPC473531
0.8773	High Similarity	NPC167479
0.8727	High Similarity	NPC157522
0.8727	High Similarity	NPC475964
0.8726	High Similarity	NPC308555
0.872	High Similarity	NPC211309
0.8712	High Similarity	NPC471923
0.8675	High Similarity	NPC62640
0.8671	High Similarity	NPC54179
0.865	High Similarity	NPC187923
0.8634	High Similarity	NPC78944
0.8625	High Similarity	NPC19600
0.8623	High Similarity	NPC66804
0.8616	High Similarity	NPC268008
0.8616	High Similarity	NPC254163
0.8614	High Similarity	NPC473697
0.859	High Similarity	NPC127827
0.8571	High Similarity	NPC125713
0.8563	High Similarity	NPC316539
0.8562	High Similarity	NPC155063
0.8562	High Similarity	NPC109765
0.8544	High Similarity	NPC104353
0.8537	High Similarity	NPC477884
0.8535	High Similarity	NPC475722
0.8528	High Similarity	NPC116838
0.8528	High Similarity	NPC22130
0.8519	High Similarity	NPC65784
0.8509	High Similarity	NPC202495
0.8509	High Similarity	NPC310206
0.8491	Intermediate Similarity	NPC68882
0.8476	Intermediate Similarity	NPC110257
0.8466	Intermediate Similarity	NPC34376
0.8466	Intermediate Similarity	NPC15212
0.8457	Intermediate Similarity	NPC474043
0.8457	Intermediate Similarity	NPC113055
0.8457	Intermediate Similarity	NPC250076
0.8457	Intermediate Similarity	NPC325122
0.8452	Intermediate Similarity	NPC213900
0.8442	Intermediate Similarity	NPC27220
0.8418	Intermediate Similarity	NPC474305
0.8415	Intermediate Similarity	NPC18284
0.8415	Intermediate Similarity	NPC61141
0.8415	Intermediate Similarity	NPC273021
0.8412	Intermediate Similarity	NPC267549
0.8405	Intermediate Similarity	NPC474770
0.8402	Intermediate Similarity	NPC290304
0.8402	Intermediate Similarity	NPC236327
0.8395	Intermediate Similarity	NPC258644
0.8395	Intermediate Similarity	NPC477885
0.8393	Intermediate Similarity	NPC471921
0.8393	Intermediate Similarity	NPC474075
0.8393	Intermediate Similarity	NPC292712
0.8393	Intermediate Similarity	NPC20114
0.8393	Intermediate Similarity	NPC312006
0.8393	Intermediate Similarity	NPC471922
0.8393	Intermediate Similarity	NPC471920
0.8393	Intermediate Similarity	NPC129930
0.8393	Intermediate Similarity	NPC114550
0.8385	Intermediate Similarity	NPC234730
0.8385	Intermediate Similarity	NPC478238
0.8385	Intermediate Similarity	NPC80489
0.8375	Intermediate Similarity	NPC137813
0.8375	Intermediate Similarity	NPC144162
0.8373	Intermediate Similarity	NPC67450
0.8373	Intermediate Similarity	NPC155264
0.8373	Intermediate Similarity	NPC193881
0.8373	Intermediate Similarity	NPC210460
0.8365	Intermediate Similarity	NPC474975
0.8364	Intermediate Similarity	NPC100425
0.8364	Intermediate Similarity	NPC65846
0.8363	Intermediate Similarity	NPC161609
0.8363	Intermediate Similarity	NPC275690
0.8354	Intermediate Similarity	NPC475848
0.8354	Intermediate Similarity	NPC24193
0.8354	Intermediate Similarity	NPC319749
0.8354	Intermediate Similarity	NPC258322
0.8354	Intermediate Similarity	NPC216092
0.8354	Intermediate Similarity	NPC191352
0.8354	Intermediate Similarity	NPC474306
0.8353	Intermediate Similarity	NPC79736
0.8353	Intermediate Similarity	NPC67629
0.8344	Intermediate Similarity	NPC68619
0.8343	Intermediate Similarity	NPC184624
0.8333	Intermediate Similarity	NPC477380
0.8323	Intermediate Similarity	NPC478213
0.8323	Intermediate Similarity	NPC244371
0.8313	Intermediate Similarity	NPC220577
0.8304	Intermediate Similarity	NPC35266
0.8303	Intermediate Similarity	NPC198796
0.8303	Intermediate Similarity	NPC125991
0.8303	Intermediate Similarity	NPC302741
0.8302	Intermediate Similarity	NPC300983
0.8294	Intermediate Similarity	NPC193377
0.8293	Intermediate Similarity	NPC43971
0.8293	Intermediate Similarity	NPC239818
0.8293	Intermediate Similarity	NPC218471
0.8293	Intermediate Similarity	NPC243509
0.8293	Intermediate Similarity	NPC74749
0.8293	Intermediate Similarity	NPC19554
0.8291	Intermediate Similarity	NPC181464
0.8289	Intermediate Similarity	NPC102260
0.8289	Intermediate Similarity	NPC230968
0.8282	Intermediate Similarity	NPC474990
0.828	Intermediate Similarity	NPC224687
0.828	Intermediate Similarity	NPC296575
0.8274	Intermediate Similarity	NPC477165
0.8272	Intermediate Similarity	NPC284353
0.8272	Intermediate Similarity	NPC222185
0.8272	Intermediate Similarity	NPC10205
0.8269	Intermediate Similarity	NPC473090
0.8263	Intermediate Similarity	NPC174734
0.8263	Intermediate Similarity	NPC474042
0.8261	Intermediate Similarity	NPC153008
0.8261	Intermediate Similarity	NPC131121
0.8261	Intermediate Similarity	NPC148497
0.8261	Intermediate Similarity	NPC292460
0.8253	Intermediate Similarity	NPC179464
0.8253	Intermediate Similarity	NPC45943
0.8246	Intermediate Similarity	NPC196771
0.8242	Intermediate Similarity	NPC239890
0.8242	Intermediate Similarity	NPC469889
0.8242	Intermediate Similarity	NPC209411
0.8242	Intermediate Similarity	NPC94155
0.8235	Intermediate Similarity	NPC477881
0.8232	Intermediate Similarity	NPC50430
0.8232	Intermediate Similarity	NPC33320
0.8225	Intermediate Similarity	NPC52598
0.8221	Intermediate Similarity	NPC473900
0.8221	Intermediate Similarity	NPC301897
0.8221	Intermediate Similarity	NPC471405
0.8218	Intermediate Similarity	NPC167045
0.8218	Intermediate Similarity	NPC114120
0.8217	Intermediate Similarity	NPC474158
0.8217	Intermediate Similarity	NPC327052
0.8214	Intermediate Similarity	NPC247973
0.8214	Intermediate Similarity	NPC186392
0.8212	Intermediate Similarity	NPC205915
0.821	Intermediate Similarity	NPC178195
0.821	Intermediate Similarity	NPC348849
0.821	Intermediate Similarity	NPC57211
0.821	Intermediate Similarity	NPC279930
0.821	Intermediate Similarity	NPC186507
0.8205	Intermediate Similarity	NPC137920
0.8205	Intermediate Similarity	NPC125134
0.8205	Intermediate Similarity	NPC86455
0.8204	Intermediate Similarity	NPC279768
0.8199	Intermediate Similarity	NPC279061
0.8199	Intermediate Similarity	NPC134905
0.8199	Intermediate Similarity	NPC36130
0.8193	Intermediate Similarity	NPC478199
0.8193	Intermediate Similarity	NPC78612
0.8193	Intermediate Similarity	NPC414831
0.8193	Intermediate Similarity	NPC234536
0.8182	Intermediate Similarity	NPC304839
0.8182	Intermediate Similarity	NPC220582
0.8182	Intermediate Similarity	NPC477164
0.8182	Intermediate Similarity	NPC131557
0.8176	Intermediate Similarity	NPC247964
0.8171	Intermediate Similarity	NPC226759
0.8171	Intermediate Similarity	NPC19097
0.8166	Intermediate Similarity	NPC117911
0.8165	Intermediate Similarity	NPC87295
0.816	Intermediate Similarity	NPC180901
0.816	Intermediate Similarity	NPC300757
0.8158	Intermediate Similarity	NPC90083
0.8158	Intermediate Similarity	NPC170779
0.8155	Intermediate Similarity	NPC53640
0.8153	Intermediate Similarity	NPC50954
0.8153	Intermediate Similarity	NPC475000
0.8153	Intermediate Similarity	NPC15743
0.8148	Intermediate Similarity	NPC52623
0.8144	Intermediate Similarity	NPC132054
0.8144	Intermediate Similarity	NPC475865
0.8144	Intermediate Similarity	NPC100420
0.8144	Intermediate Similarity	NPC89131
0.8144	Intermediate Similarity	NPC91288
0.8141	Intermediate Similarity	NPC210354
0.8141	Intermediate Similarity	NPC176586
0.8137	Intermediate Similarity	NPC191104

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 NPC76458 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	356
0.1-0.2	929
0.2-0.3	1654
0.3-0.4	2634
0.4-0.5	1954
0.5-0.6	1009
0.6-0.7	455
0.7-0.8	152
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
0.8408	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD919	Approved
0.8072	Intermediate Similarity	NPD5494	Approved
0.8024	Intermediate Similarity	NPD1247	Approved
0.8	Intermediate Similarity	NPD3818	Discontinued
0.7962	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD920	Approved
0.7929	Intermediate Similarity	NPD3926	Phase 2
0.7919	Intermediate Similarity	NPD6559	Discontinued
0.7849	Intermediate Similarity	NPD5844	Phase 1
0.7834	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD3817	Phase 2
0.7826	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD7199	Phase 2
0.7809	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD3882	Suspended
0.7771	Intermediate Similarity	NPD7819	Suspended
0.7758	Intermediate Similarity	NPD6385	Approved
0.7758	Intermediate Similarity	NPD6386	Approved
0.774	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD1243	Approved
0.7733	Intermediate Similarity	NPD7473	Discontinued
0.7719	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD7074	Phase 3
0.7679	Intermediate Similarity	NPD4966	Approved
0.7679	Intermediate Similarity	NPD4967	Phase 2
0.7679	Intermediate Similarity	NPD4965	Approved
0.7665	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD6232	Discontinued
0.7644	Intermediate Similarity	NPD7054	Approved
0.7636	Intermediate Similarity	NPD7458	Discontinued
0.7628	Intermediate Similarity	NPD1933	Approved
0.7605	Intermediate Similarity	NPD1934	Approved
0.76	Intermediate Similarity	NPD7472	Approved
0.7588	Intermediate Similarity	NPD6234	Discontinued
0.7578	Intermediate Similarity	NPD4628	Phase 3
0.7571	Intermediate Similarity	NPD7808	Phase 3
0.7571	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD2801	Approved
0.756	Intermediate Similarity	NPD8455	Phase 2
0.7546	Intermediate Similarity	NPD6799	Approved
0.7529	Intermediate Similarity	NPD7075	Discontinued
0.7514	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD37	Approved
0.7484	Intermediate Similarity	NPD2799	Discontinued
0.7458	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7411	Suspended
0.7438	Intermediate Similarity	NPD2796	Approved
0.743	Intermediate Similarity	NPD8312	Approved
0.743	Intermediate Similarity	NPD8313	Approved
0.7427	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD7251	Discontinued
0.7396	Intermediate Similarity	NPD6801	Discontinued
0.7386	Intermediate Similarity	NPD7228	Approved
0.7381	Intermediate Similarity	NPD6599	Discontinued
0.7371	Intermediate Similarity	NPD6166	Phase 2
0.7371	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7768	Phase 2
0.736	Intermediate Similarity	NPD6797	Phase 2
0.7353	Intermediate Similarity	NPD1465	Phase 2
0.7329	Intermediate Similarity	NPD2935	Discontinued
0.7326	Intermediate Similarity	NPD3749	Approved
0.7325	Intermediate Similarity	NPD2313	Discontinued
0.7325	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD3226	Approved
0.7317	Intermediate Similarity	NPD2309	Approved
0.7314	Intermediate Similarity	NPD5242	Approved
0.7308	Intermediate Similarity	NPD6832	Phase 2
0.7308	Intermediate Similarity	NPD8434	Phase 2
0.7303	Intermediate Similarity	NPD3705	Approved
0.7299	Intermediate Similarity	NPD8127	Discontinued
0.7296	Intermediate Similarity	NPD447	Suspended
0.7289	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD17	Approved
0.7284	Intermediate Similarity	NPD2346	Discontinued
0.7273	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3748	Approved
0.7257	Intermediate Similarity	NPD7229	Phase 3
0.7257	Intermediate Similarity	NPD6808	Phase 2
0.7243	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD1511	Approved
0.7222	Intermediate Similarity	NPD7240	Approved
0.7212	Intermediate Similarity	NPD3887	Approved
0.7209	Intermediate Similarity	NPD5353	Approved
0.7209	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5536	Phase 2
0.7193	Intermediate Similarity	NPD6280	Approved
0.7193	Intermediate Similarity	NPD6279	Approved
0.7191	Intermediate Similarity	NPD2163	Approved
0.7188	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6355	Discontinued
0.7186	Intermediate Similarity	NPD2533	Approved
0.7186	Intermediate Similarity	NPD2534	Approved
0.7186	Intermediate Similarity	NPD2532	Approved
0.7178	Intermediate Similarity	NPD1471	Phase 3
0.7176	Intermediate Similarity	NPD4380	Phase 2
0.7143	Intermediate Similarity	NPD4420	Approved
0.7143	Intermediate Similarity	NPD1512	Approved
0.7143	Intermediate Similarity	NPD1608	Approved
0.7135	Intermediate Similarity	NPD6873	Phase 2
0.7125	Intermediate Similarity	NPD2979	Phase 3
0.711	Intermediate Similarity	NPD5402	Approved
0.7107	Intermediate Similarity	NPD6798	Discontinued
0.7083	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3146	Approved
0.7081	Intermediate Similarity	NPD230	Phase 1
0.7076	Intermediate Similarity	NPD7028	Phase 2
0.7073	Intermediate Similarity	NPD2353	Approved
0.7073	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD3750	Approved
0.7048	Intermediate Similarity	NPD4110	Phase 3
0.7048	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD3972	Approved
0.703	Intermediate Similarity	NPD1549	Phase 2
0.7025	Intermediate Similarity	NPD9494	Approved
0.7018	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD2438	Suspended
0.7006	Intermediate Similarity	NPD6959	Discontinued
0.7	Intermediate Similarity	NPD7177	Discontinued
0.7	Intermediate Similarity	NPD3764	Approved
0.6995	Remote Similarity	NPD5006	Approved
0.6995	Remote Similarity	NPD5005	Approved
0.697	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7266	Discontinued
0.697	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD1281	Approved
0.6968	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD2798	Approved
0.6961	Remote Similarity	NPD7286	Phase 2
0.6959	Remote Similarity	NPD1653	Approved
0.6957	Remote Similarity	NPD8032	Phase 2
0.6954	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD8151	Discontinued
0.6951	Remote Similarity	NPD1510	Phase 2
0.6946	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7003	Approved
0.6941	Remote Similarity	NPD5049	Phase 3
0.6941	Remote Similarity	NPD6273	Approved
0.694	Remote Similarity	NPD7038	Approved
0.694	Remote Similarity	NPD7039	Approved
0.6933	Remote Similarity	NPD1241	Discontinued
0.6919	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4307	Phase 2
0.6914	Remote Similarity	NPD1240	Approved
0.6914	Remote Similarity	NPD4060	Phase 1
0.6906	Remote Similarity	NPD3751	Discontinued
0.6905	Remote Similarity	NPD2354	Approved
0.6905	Remote Similarity	NPD6190	Approved
0.6901	Remote Similarity	NPD5403	Approved
0.6899	Remote Similarity	NPD3267	Approved
0.6899	Remote Similarity	NPD3266	Approved
0.6893	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD4107	Approved
0.689	Remote Similarity	NPD7097	Phase 1
0.6889	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6674	Discontinued
0.6886	Remote Similarity	NPD2800	Approved
0.6885	Remote Similarity	NPD5953	Discontinued
0.6884	Remote Similarity	NPD7783	Phase 2
0.6884	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD1651	Approved
0.6883	Remote Similarity	NPD5691	Approved
0.6882	Remote Similarity	NPD5401	Approved
0.6879	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD3787	Discontinued
0.6872	Remote Similarity	NPD7680	Approved
0.6867	Remote Similarity	NPD6004	Phase 3
0.6867	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6002	Phase 3
0.6867	Remote Similarity	NPD6005	Phase 3
0.6862	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6233	Phase 2
0.6848	Remote Similarity	NPD6765	Approved
0.6848	Remote Similarity	NPD6764	Approved
0.6848	Remote Similarity	NPD7033	Discontinued
0.6835	Remote Similarity	NPD1283	Approved
0.6835	Remote Similarity	NPD1876	Approved
0.6829	Remote Similarity	NPD1607	Approved
0.6826	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD5283	Phase 1
0.6818	Remote Similarity	NPD2296	Approved
0.6818	Remote Similarity	NPD9545	Approved
0.6818	Remote Similarity	NPD5977	Approved
0.6818	Remote Similarity	NPD5978	Approved
0.6807	Remote Similarity	NPD2531	Phase 2
0.6807	Remote Similarity	NPD1551	Phase 2
0.6807	Remote Similarity	NPD4477	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