NPASS Compound

Structure

NPC52634 OpenBabel07101719152D 40 44 0 0 1 0 0 0 0 0999 V2000 1.9501 -5.4575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2372 -4.2985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5899 -3.7633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2298 -2.0691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 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 2.2591 -4.5064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8990 -2.8122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -1.1180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4899 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8771 -2.6043 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2989 -1.3968 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9641 3.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4899 0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 5 30 1 0 0 0 0 8 9 1 0 0 0 0 8 20 2 0 0 0 0 9 23 1 0 0 0 0 10 11 1 0 0 0 0 10 25 1 0 0 0 0 11 29 1 0 0 0 0 12 16 2 0 0 0 0 12 18 1 0 0 0 0 13 18 1 0 0 0 0 14 21 1 0 0 0 0 14 24 1 0 0 0 0 15 30 1 0 0 0 0 17 33 2 0 0 0 0 17 39 1 0 0 0 0 18 34 2 0 0 0 0 19 13 1 6 0 0 0 19 26 1 0 0 0 0 19 27 1 0 0 0 0 20 21 1 0 0 0 0 20 30 1 0 0 0 0 21 29 1 6 0 0 0 22 15 1 6 0 0 0 22 26 1 0 0 0 0 22 40 1 0 0 0 0 23 29 1 6 0 0 0 23 31 1 0 0 0 0 24 32 1 1 0 0 0 24 35 1 0 0 0 0 25 31 1 1 0 0 0 25 39 1 0 0 0 0 26 32 1 1 0 0 0 27 36 2 0 0 0 0 27 40 1 0 0 0 0 28 31 1 0 0 0 0 28 37 2 0 0 0 0 28 38 1 0 0 0 0 29 4 1 6 0 0 0 30 32 1 6 0 0 0 31 6 1 6 0 0 0 32 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	556.3
Volume:	573.749
LogP:	3.717
LogD:	2.415
LogS:	-3.724
# Rotatable Bonds:	7
TPSA:	134.27
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.325
Synthetic Accessibility Score:	5.31
Fsp3:	0.719
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.584
MDCK Permeability:	1.870457526820246e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.835
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.264
30% Bioavailability (F30%):	0.116

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.964
Plasma Protein Binding (PPB):	91.30926513671875%
Volume Distribution (VD):	0.354
Pgp-substrate:	10.33280086517334%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.117
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.639
CYP2C9-inhibitor:	0.222
CYP2C9-substrate:	0.937
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.103
CYP3A4-inhibitor:	0.141
CYP3A4-substrate:	0.18

ADMET: Excretion

Clearance (CL):	2.953
Half-life (T1/2):	0.886

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.412
Drug-inuced Liver Injury (DILI):	0.845
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.939
Maximum Recommended Daily Dose:	0.936
Skin Sensitization:	0.466
Carcinogencity:	0.206
Eye Corrosion:	0.003
Eye Irritation:	0.061
Respiratory Toxicity:	0.946

Download Data

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

Natural Product: NPC52634

Natural Product ID:	NPC52634
*Common Name:**	PGGDNFLHYMDIRS-QYWQWFLASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PGGDNFLHYMDIRS-QYWQWFLASA-N
Standard InCHI:	InChI=1S/C32H44O8/c1-16(2)12-18(34)13-19-26-22(40-27(19)36)15-30(5)20-8-9-23-29(4,21(20)14-24(35)32(26,30)7)11-10-25(39-17(3)33)31(23,6)28(37)38/h8,12,19,21-26,35H,9-11,13-15H2,1-7H3,(H,37,38)/t19-,21+,22+,23-,24+,25-,26-,29-,30-,31+,32+/m1/s1
SMILES:	CC(=CC(=O)C[C@@H]1[C@@H]2[C@H](C[C@]3(C)C4=CC[C@@H]5[C@](C)(CC[C@H]([C@@]5(C)C(=O)O)OC(=O)C)[C@H]4C[C@@H]([C@@]23C)O)OC1=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL499564
PubChem CID:	10602877
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[10869197]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1812212]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	leaves	n.a.	n.a.	PMID[9834145]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1859	Lantana camara	Species	Verbenaceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT670	Individual Protein	Thrombin	Homo sapiens	IC50	=	90.0	nM	PMID[546269]

☑ 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 NPC52634 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	236
0.1-0.2	1424
0.2-0.3	5065
0.3-0.4	8818
0.4-0.5	11955
0.5-0.6	6146
0.6-0.7	5874
0.7-0.8	2899
0.8-0.85	246
0.85-0.9	31
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9423	High Similarity	NPC220974
0.9135	High Similarity	NPC140723
0.9043	High Similarity	NPC174367
0.9043	High Similarity	NPC47113
0.8919	High Similarity	NPC266728
0.8919	High Similarity	NPC49492
0.8857	High Similarity	NPC22388
0.8807	High Similarity	NPC197428
0.8785	High Similarity	NPC231530
0.8785	High Similarity	NPC278628
0.8785	High Similarity	NPC196528
0.8774	High Similarity	NPC36321
0.875	High Similarity	NPC270958
0.8739	High Similarity	NPC962
0.8739	High Similarity	NPC202889
0.8692	High Similarity	NPC96268
0.8649	High Similarity	NPC280782
0.8649	High Similarity	NPC71348
0.8624	High Similarity	NPC94529
0.8621	High Similarity	NPC222688
0.8609	High Similarity	NPC109973
0.8598	High Similarity	NPC159442
0.8596	High Similarity	NPC118638
0.8571	High Similarity	NPC250109
0.8545	High Similarity	NPC304495
0.8534	High Similarity	NPC470921
0.8532	High Similarity	NPC59530
0.8519	High Similarity	NPC471293
0.8519	High Similarity	NPC29705
0.8509	High Similarity	NPC239273
0.8505	High Similarity	NPC275990
0.8496	Intermediate Similarity	NPC326542
0.8491	Intermediate Similarity	NPC108371
0.8491	Intermediate Similarity	NPC218383
0.8482	Intermediate Similarity	NPC170487
0.8482	Intermediate Similarity	NPC207251
0.8475	Intermediate Similarity	NPC473255
0.8462	Intermediate Similarity	NPC269642
0.8455	Intermediate Similarity	NPC258323
0.844	Intermediate Similarity	NPC102352
0.844	Intermediate Similarity	NPC295366
0.844	Intermediate Similarity	NPC96377
0.8426	Intermediate Similarity	NPC312900
0.8426	Intermediate Similarity	NPC87927
0.8421	Intermediate Similarity	NPC207217
0.8421	Intermediate Similarity	NPC72772
0.8421	Intermediate Similarity	NPC469794
0.8411	Intermediate Similarity	NPC52899
0.8411	Intermediate Similarity	NPC39683
0.8411	Intermediate Similarity	NPC289148
0.8411	Intermediate Similarity	NPC236585
0.8411	Intermediate Similarity	NPC163963
0.8411	Intermediate Similarity	NPC46848
0.8407	Intermediate Similarity	NPC472926
0.8396	Intermediate Similarity	NPC271387
0.8396	Intermediate Similarity	NPC471038
0.8396	Intermediate Similarity	NPC474793
0.8396	Intermediate Similarity	NPC153792
0.8393	Intermediate Similarity	NPC470281
0.8393	Intermediate Similarity	NPC118860
0.8393	Intermediate Similarity	NPC231589
0.8393	Intermediate Similarity	NPC43775
0.8393	Intermediate Similarity	NPC214797
0.8378	Intermediate Similarity	NPC241927
0.8378	Intermediate Similarity	NPC258543
0.8365	Intermediate Similarity	NPC111015
0.8364	Intermediate Similarity	NPC44063
0.8364	Intermediate Similarity	NPC201908
0.8364	Intermediate Similarity	NPC176949
0.8362	Intermediate Similarity	NPC473203
0.8362	Intermediate Similarity	NPC472933
0.8349	Intermediate Similarity	NPC255309
0.8349	Intermediate Similarity	NPC28656
0.8349	Intermediate Similarity	NPC98603
0.8348	Intermediate Similarity	NPC472927
0.8348	Intermediate Similarity	NPC472934
0.8347	Intermediate Similarity	NPC231529
0.8333	Intermediate Similarity	NPC271980
0.8333	Intermediate Similarity	NPC124544
0.8333	Intermediate Similarity	NPC88203
0.8333	Intermediate Similarity	NPC42399
0.8333	Intermediate Similarity	NPC473265
0.8333	Intermediate Similarity	NPC148628
0.8333	Intermediate Similarity	NPC214946
0.8333	Intermediate Similarity	NPC473788
0.8333	Intermediate Similarity	NPC470882
0.8333	Intermediate Similarity	NPC471398
0.8333	Intermediate Similarity	NPC76866
0.8333	Intermediate Similarity	NPC246736
0.8333	Intermediate Similarity	NPC243354
0.8333	Intermediate Similarity	NPC304832
0.8333	Intermediate Similarity	NPC286519
0.8333	Intermediate Similarity	NPC193934
0.8333	Intermediate Similarity	NPC475558
0.8333	Intermediate Similarity	NPC473928
0.8318	Intermediate Similarity	NPC267921
0.8318	Intermediate Similarity	NPC293866
0.8318	Intermediate Similarity	NPC287676
0.8304	Intermediate Similarity	NPC42776
0.8304	Intermediate Similarity	NPC179642
0.8304	Intermediate Similarity	NPC5284
0.8302	Intermediate Similarity	NPC253586
0.8288	Intermediate Similarity	NPC469845
0.8288	Intermediate Similarity	NPC211224
0.8288	Intermediate Similarity	NPC154608
0.8288	Intermediate Similarity	NPC192813
0.8288	Intermediate Similarity	NPC19412
0.8288	Intermediate Similarity	NPC277017
0.8286	Intermediate Similarity	NPC69548
0.8286	Intermediate Similarity	NPC184848
0.8286	Intermediate Similarity	NPC469599
0.8279	Intermediate Similarity	NPC241935
0.8279	Intermediate Similarity	NPC279478
0.8273	Intermediate Similarity	NPC200957
0.8273	Intermediate Similarity	NPC138908
0.8273	Intermediate Similarity	NPC37600
0.8273	Intermediate Similarity	NPC475571
0.8269	Intermediate Similarity	NPC470224
0.8269	Intermediate Similarity	NPC470375
0.8269	Intermediate Similarity	NPC470376
0.8264	Intermediate Similarity	NPC311534
0.8261	Intermediate Similarity	NPC148458
0.8257	Intermediate Similarity	NPC117185
0.8257	Intermediate Similarity	NPC216114
0.8257	Intermediate Similarity	NPC96217
0.8257	Intermediate Similarity	NPC236390
0.8257	Intermediate Similarity	NPC55872
0.8257	Intermediate Similarity	NPC122811
0.8257	Intermediate Similarity	NPC470310
0.8257	Intermediate Similarity	NPC282233
0.8257	Intermediate Similarity	NPC95585
0.8246	Intermediate Similarity	NPC9848
0.8246	Intermediate Similarity	NPC317210
0.8246	Intermediate Similarity	NPC260665
0.8246	Intermediate Similarity	NPC194100
0.8246	Intermediate Similarity	NPC312017
0.8246	Intermediate Similarity	NPC178981
0.8241	Intermediate Similarity	NPC121218
0.8241	Intermediate Similarity	NPC473514
0.8241	Intermediate Similarity	NPC253886
0.823	Intermediate Similarity	NPC471251
0.8224	Intermediate Similarity	NPC477813
0.8224	Intermediate Similarity	NPC78427
0.8224	Intermediate Similarity	NPC119036
0.8224	Intermediate Similarity	NPC114274
0.8224	Intermediate Similarity	NPC477854
0.8224	Intermediate Similarity	NPC89099
0.8224	Intermediate Similarity	NPC38296
0.8224	Intermediate Similarity	NPC38471
0.8224	Intermediate Similarity	NPC16911
0.8224	Intermediate Similarity	NPC98837
0.8224	Intermediate Similarity	NPC162459
0.8224	Intermediate Similarity	NPC20479
0.8224	Intermediate Similarity	NPC28864
0.8214	Intermediate Similarity	NPC2766
0.8214	Intermediate Similarity	NPC475941
0.8214	Intermediate Similarity	NPC474901
0.8211	Intermediate Similarity	NPC34963
0.8208	Intermediate Similarity	NPC42042
0.8208	Intermediate Similarity	NPC200054
0.8208	Intermediate Similarity	NPC173272
0.8208	Intermediate Similarity	NPC95565
0.8208	Intermediate Similarity	NPC329910
0.8208	Intermediate Similarity	NPC29410
0.8205	Intermediate Similarity	NPC475041
0.8205	Intermediate Similarity	NPC476960
0.8205	Intermediate Similarity	NPC319570
0.8198	Intermediate Similarity	NPC96333
0.8198	Intermediate Similarity	NPC144854
0.8198	Intermediate Similarity	NPC166993
0.8198	Intermediate Similarity	NPC88833
0.8198	Intermediate Similarity	NPC3316
0.8198	Intermediate Similarity	NPC83744
0.8198	Intermediate Similarity	NPC473037
0.8197	Intermediate Similarity	NPC470880
0.819	Intermediate Similarity	NPC287343
0.819	Intermediate Similarity	NPC97908
0.819	Intermediate Similarity	NPC122033
0.819	Intermediate Similarity	NPC159410
0.819	Intermediate Similarity	NPC470854
0.819	Intermediate Similarity	NPC471854
0.819	Intermediate Similarity	NPC474654
0.8182	Intermediate Similarity	NPC305496
0.8182	Intermediate Similarity	NPC228669
0.8182	Intermediate Similarity	NPC473253
0.8182	Intermediate Similarity	NPC13149
0.8182	Intermediate Similarity	NPC47281
0.8182	Intermediate Similarity	NPC287423
0.8182	Intermediate Similarity	NPC164835
0.8182	Intermediate Similarity	NPC84928
0.8182	Intermediate Similarity	NPC472228
0.8182	Intermediate Similarity	NPC472227
0.8174	Intermediate Similarity	NPC470953
0.8174	Intermediate Similarity	NPC117712
0.8174	Intermediate Similarity	NPC123117
0.8174	Intermediate Similarity	NPC473798
0.8173	Intermediate Similarity	NPC154101
0.8167	Intermediate Similarity	NPC8369
0.8167	Intermediate Similarity	NPC473505
0.8165	Intermediate Similarity	NPC136289

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 NPC52634 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	204
0.1-0.2	1725
0.2-0.3	4036
0.3-0.4	2097
0.4-0.5	594
0.5-0.6	194
0.6-0.7	140
0.7-0.8	118
0.8-0.85	32
0.85-0.9	10
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8889	High Similarity	NPD6372	Approved
0.8889	High Similarity	NPD6373	Approved
0.8727	High Similarity	NPD6649	Approved
0.8727	High Similarity	NPD6650	Approved
0.8624	High Similarity	NPD7320	Approved
0.8611	High Similarity	NPD6008	Approved
0.8611	High Similarity	NPD6402	Approved
0.8611	High Similarity	NPD5739	Approved
0.8611	High Similarity	NPD6675	Approved
0.8611	High Similarity	NPD7128	Approved
0.8487	Intermediate Similarity	NPD8293	Discontinued
0.8482	Intermediate Similarity	NPD8297	Approved
0.8475	Intermediate Similarity	NPD7492	Approved
0.8455	Intermediate Similarity	NPD6899	Approved
0.8455	Intermediate Similarity	NPD6881	Approved
0.8448	Intermediate Similarity	NPD6319	Approved
0.8448	Intermediate Similarity	NPD6054	Approved
0.8448	Intermediate Similarity	NPD6059	Approved
0.8417	Intermediate Similarity	NPD7736	Approved
0.8403	Intermediate Similarity	NPD6616	Approved
0.8393	Intermediate Similarity	NPD8130	Phase 1
0.8364	Intermediate Similarity	NPD5697	Approved
0.8364	Intermediate Similarity	NPD5701	Approved
0.8333	Intermediate Similarity	NPD7078	Approved
0.8319	Intermediate Similarity	NPD6882	Approved
0.8305	Intermediate Similarity	NPD6370	Approved
0.8304	Intermediate Similarity	NPD6883	Approved
0.8304	Intermediate Similarity	NPD7102	Approved
0.8304	Intermediate Similarity	NPD7290	Approved
0.823	Intermediate Similarity	NPD6869	Approved
0.823	Intermediate Similarity	NPD6617	Approved
0.823	Intermediate Similarity	NPD6847	Approved
0.822	Intermediate Similarity	NPD6015	Approved
0.822	Intermediate Similarity	NPD6016	Approved
0.8214	Intermediate Similarity	NPD6012	Approved
0.8214	Intermediate Similarity	NPD6014	Approved
0.8214	Intermediate Similarity	NPD6013	Approved
0.8151	Intermediate Similarity	NPD5988	Approved
0.8131	Intermediate Similarity	NPD4755	Approved
0.8125	Intermediate Similarity	NPD6011	Approved
0.8095	Intermediate Similarity	NPD6399	Phase 3
0.8087	Intermediate Similarity	NPD4632	Approved
0.807	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7982	Intermediate Similarity	NPD5286	Approved
0.7982	Intermediate Similarity	NPD4634	Approved
0.7982	Intermediate Similarity	NPD5285	Approved
0.7982	Intermediate Similarity	NPD4700	Approved
0.7982	Intermediate Similarity	NPD4696	Approved
0.7981	Intermediate Similarity	NPD5328	Approved
0.7963	Intermediate Similarity	NPD6083	Phase 2
0.7963	Intermediate Similarity	NPD6084	Phase 2
0.7963	Intermediate Similarity	NPD7902	Approved
0.7944	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7903	Intermediate Similarity	NPD7319	Approved
0.789	Intermediate Similarity	NPD7638	Approved
0.7881	Intermediate Similarity	NPD6009	Approved
0.787	Intermediate Similarity	NPD4697	Phase 3
0.7838	Intermediate Similarity	NPD5225	Approved
0.7838	Intermediate Similarity	NPD5226	Approved
0.7838	Intermediate Similarity	NPD4633	Approved
0.7838	Intermediate Similarity	NPD5211	Phase 2
0.7838	Intermediate Similarity	NPD5224	Approved
0.783	Intermediate Similarity	NPD6079	Approved
0.7823	Intermediate Similarity	NPD6033	Approved
0.7818	Intermediate Similarity	NPD7640	Approved
0.7818	Intermediate Similarity	NPD7639	Approved
0.7805	Intermediate Similarity	NPD7507	Approved
0.7797	Intermediate Similarity	NPD6274	Approved
0.7788	Intermediate Similarity	NPD4767	Approved
0.7788	Intermediate Similarity	NPD4768	Approved
0.7787	Intermediate Similarity	NPD8328	Phase 3
0.7787	Intermediate Similarity	NPD7604	Phase 2
0.7769	Intermediate Similarity	NPD5983	Phase 2
0.7769	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7768	Intermediate Similarity	NPD5174	Approved
0.7768	Intermediate Similarity	NPD5175	Approved
0.7757	Intermediate Similarity	NPD4202	Approved
0.775	Intermediate Similarity	NPD7101	Approved
0.775	Intermediate Similarity	NPD7100	Approved
0.7748	Intermediate Similarity	NPD5223	Approved
0.7727	Intermediate Similarity	NPD5696	Approved
0.7719	Intermediate Similarity	NPD6412	Phase 2
0.7714	Intermediate Similarity	NPD6903	Approved
0.7699	Intermediate Similarity	NPD5141	Approved
0.7692	Intermediate Similarity	NPD3618	Phase 1
0.7692	Intermediate Similarity	NPD5330	Approved
0.7692	Intermediate Similarity	NPD6684	Approved
0.7692	Intermediate Similarity	NPD7146	Approved
0.7692	Intermediate Similarity	NPD6409	Approved
0.7692	Intermediate Similarity	NPD7521	Approved
0.7692	Intermediate Similarity	NPD7334	Approved
0.7685	Intermediate Similarity	NPD7748	Approved
0.7685	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD7900	Approved
0.7667	Intermediate Similarity	NPD6335	Approved
0.7664	Intermediate Similarity	NPD8034	Phase 2
0.7664	Intermediate Similarity	NPD8035	Phase 2
0.7661	Intermediate Similarity	NPD6336	Discontinued
0.7652	Intermediate Similarity	NPD4730	Approved
0.7652	Intermediate Similarity	NPD4729	Approved
0.7623	Intermediate Similarity	NPD6909	Approved
0.7623	Intermediate Similarity	NPD6908	Approved
0.7615	Intermediate Similarity	NPD5695	Phase 3
0.7611	Intermediate Similarity	NPD4754	Approved
0.7583	Intermediate Similarity	NPD7115	Discovery
0.7583	Intermediate Similarity	NPD6317	Approved
0.7547	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD5222	Approved
0.7545	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD5221	Approved
0.7542	Intermediate Similarity	NPD6053	Discontinued
0.7523	Intermediate Similarity	NPD6001	Approved
0.7521	Intermediate Similarity	NPD6313	Approved
0.7521	Intermediate Similarity	NPD5249	Phase 3
0.7521	Intermediate Similarity	NPD5251	Approved
0.7521	Intermediate Similarity	NPD5247	Approved
0.7521	Intermediate Similarity	NPD5248	Approved
0.7521	Intermediate Similarity	NPD6314	Approved
0.7521	Intermediate Similarity	NPD5250	Approved
0.75	Intermediate Similarity	NPD7515	Phase 2
0.75	Intermediate Similarity	NPD3665	Phase 1
0.75	Intermediate Similarity	NPD3133	Approved
0.75	Intermediate Similarity	NPD3666	Approved
0.75	Intermediate Similarity	NPD5128	Approved
0.7477	Intermediate Similarity	NPD5173	Approved
0.7477	Intermediate Similarity	NPD4753	Phase 2
0.7436	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD5737	Approved
0.7383	Intermediate Similarity	NPD6672	Approved
0.736	Intermediate Similarity	NPD6067	Discontinued
0.7358	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6868	Approved
0.7339	Intermediate Similarity	NPD5284	Approved
0.7339	Intermediate Similarity	NPD5281	Approved
0.7333	Intermediate Similarity	NPD4786	Approved
0.7315	Intermediate Similarity	NPD6904	Approved
0.7315	Intermediate Similarity	NPD6080	Approved
0.7315	Intermediate Similarity	NPD6673	Approved
0.7311	Intermediate Similarity	NPD5215	Approved
0.7311	Intermediate Similarity	NPD5216	Approved
0.7311	Intermediate Similarity	NPD5217	Approved
0.7297	Intermediate Similarity	NPD4629	Approved
0.7297	Intermediate Similarity	NPD5210	Approved
0.7295	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD6333	Approved
0.7293	Intermediate Similarity	NPD6334	Approved
0.7258	Intermediate Similarity	NPD8294	Approved
0.7258	Intermediate Similarity	NPD8377	Approved
0.7248	Intermediate Similarity	NPD5207	Approved
0.7236	Intermediate Similarity	NPD7327	Approved
0.7236	Intermediate Similarity	NPD7328	Approved
0.7227	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD5169	Approved
0.7227	Intermediate Similarity	NPD5135	Approved
0.7227	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD7632	Discontinued
0.7203	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD8033	Approved
0.72	Intermediate Similarity	NPD8380	Approved
0.72	Intermediate Similarity	NPD8379	Approved
0.72	Intermediate Similarity	NPD8335	Approved
0.72	Intermediate Similarity	NPD8378	Approved
0.72	Intermediate Similarity	NPD8296	Approved
0.7182	Intermediate Similarity	NPD6411	Approved
0.7177	Intermediate Similarity	NPD7516	Approved
0.7167	Intermediate Similarity	NPD5127	Approved
0.7143	Intermediate Similarity	NPD3667	Approved
0.7143	Intermediate Similarity	NPD4223	Phase 3
0.7143	Intermediate Similarity	NPD4221	Approved
0.7105	Intermediate Similarity	NPD4225	Approved
0.7103	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD5329	Approved
0.7064	Intermediate Similarity	NPD5208	Approved
0.7059	Intermediate Similarity	NPD6686	Approved
0.7037	Intermediate Similarity	NPD6098	Approved
0.7027	Intermediate Similarity	NPD5693	Phase 1
0.7027	Intermediate Similarity	NPD6050	Approved
0.7023	Intermediate Similarity	NPD5956	Approved
0.7009	Intermediate Similarity	NPD4197	Approved
0.7009	Intermediate Similarity	NPD6052	Approved
0.7	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6101	Approved
0.7	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD5167	Approved
0.6991	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6435	Approved
0.6975	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD3573	Approved
0.6964	Remote Similarity	NPD5778	Approved
0.6964	Remote Similarity	NPD5779	Approved
0.6949	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5692	Phase 3
0.6929	Remote Similarity	NPD7503	Approved
0.6917	Remote Similarity	NPD5168	Approved
0.6911	Remote Similarity	NPD8133	Approved
0.6903	Remote Similarity	NPD5282	Discontinued
0.6881	Remote Similarity	NPD4689	Approved
0.6881	Remote Similarity	NPD4693	Phase 3
0.6881	Remote Similarity	NPD5279	Phase 3

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