NPASS Compound

Structure

NPC53744 OpenBabel07101718182D 33 37 0 0 1 0 0 0 0 0999 V2000 -0.9980 -3.6096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5860 -3.2937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 -0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 -0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8598 2.7906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2162 0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3729 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 -2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8861 2.7906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -1.4605 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5297 1.4605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6865 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2162 1.4605 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8432 0.4868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6865 -2.9211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 -0.9737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5297 0.4868 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3729 1.9474 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8432 0.4868 0.0000 C 0 0 1 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 3.3729 3.6338 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0594 1.9474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 1.4605 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 6 29 1 0 0 0 0 8 9 1 0 0 0 0 8 19 2 0 0 0 0 9 22 1 0 0 0 0 10 13 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 27 1 0 0 0 0 13 29 1 0 0 0 0 14 15 1 0 0 0 0 14 25 1 0 0 0 0 15 26 1 0 0 0 0 16 20 1 0 0 0 0 16 25 1 0 0 0 0 17 24 1 0 0 0 0 17 26 1 0 0 0 0 18 28 1 0 0 0 0 18 31 1 0 0 0 0 19 20 1 0 0 0 0 19 30 1 0 0 0 0 20 26 1 6 0 0 0 21 27 1 1 0 0 0 21 28 1 0 0 0 0 22 27 1 1 0 0 0 22 29 1 0 0 0 0 23 28 1 1 0 0 0 23 32 1 0 0 0 0 24 30 1 6 0 0 0 24 33 1 0 0 0 0 26 3 1 1 0 0 0 27 4 1 1 0 0 0 28 5 1 6 0 0 0 29 30 1 6 0 0 0 30 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	458.38
Volume:	508.388
LogP:	5.451
LogD:	4.394
LogS:	-4.727
# Rotatable Bonds:	1
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.415
Synthetic Accessibility Score:	4.994
Fsp3:	0.933
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:	-5.033
MDCK Permeability:	1.2241680451552384e-05
Pgp-inhibitor:	0.367
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.892
30% Bioavailability (F30%):	0.804

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.355
Plasma Protein Binding (PPB):	96.3610610961914%
Volume Distribution (VD):	1.151
Pgp-substrate:	2.4930548667907715%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.223
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.909
CYP2C9-inhibitor:	0.134
CYP2C9-substrate:	0.277
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.258
CYP3A4-inhibitor:	0.677
CYP3A4-substrate:	0.306

ADMET: Excretion

Clearance (CL):	6.87
Half-life (T1/2):	0.179

ADMET: Toxicity

hERG Blockers:	0.063
Human Hepatotoxicity (H-HT):	0.236
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.628
Maximum Recommended Daily Dose:	0.936
Skin Sensitization:	0.388
Carcinogencity:	0.078
Eye Corrosion:	0.01
Eye Irritation:	0.028
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC53744

Natural Product ID:	NPC53744
*Common Name:**	Olean-12-En-3Bea,15Alpha,24-Triol
IUPAC Name:	(3S,4S,4aR,6aR,6bS,7S,8aR,12aR,14aR,14bR)-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,7-diol
Synonyms:
Standard InCHIKey:	DMUKCLRLPXYUKD-LICRDSFHSA-N
Standard InCHI:	InChI=1S/C30H50O3/c1-25(2)14-15-26(3)17-24(33)30(7)19(20(26)16-25)8-9-22-27(4)12-11-23(32)28(5,18-31)21(27)10-13-29(22,30)6/h8,20-24,31-33H,9-18H2,1-7H3/t20-,21+,22+,23-,24-,26+,27-,28+,29+,30-/m0/s1
SMILES:	OC[C@@]1(C)[C@@H](O)CC[C@]2([C@H]1CC[C@@]1([C@@H]2CC=C2[C@@]1(C)[C@@H](O)C[C@@]1([C@H]2CC(CC1)(C)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL489552
PubChem CID:	14167260
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
NPO18290	Phyllanthus flexuosus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754608]
NPO18290	Phyllanthus flexuosus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18290	Phyllanthus flexuosus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18290	Phyllanthus flexuosus	Species	Phyllanthaceae	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
NPT1044	Individual Protein	DNA topoisomerase II alpha	Homo sapiens	IC50	=	38700.0	nM	PMID[485017]

☑ 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 NPC53744 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	208
0.1-0.2	1716
0.2-0.3	6688
0.3-0.4	16615
0.4-0.5	7357
0.5-0.6	4860
0.6-0.7	3607
0.7-0.8	1238
0.8-0.85	269
0.85-0.9	97
0.9-0.95	16
0.95-1	26

Similarity Score	Similarity Level	Natural Product ID
0.9863	High Similarity	NPC22955
0.9863	High Similarity	NPC196753
0.9863	High Similarity	NPC470396
0.9863	High Similarity	NPC99168
0.9863	High Similarity	NPC158662
0.9863	High Similarity	NPC253807
0.9863	High Similarity	NPC230295
0.9863	High Similarity	NPC98386
0.9863	High Similarity	NPC474989
0.973	High Similarity	NPC291379
0.9726	High Similarity	NPC101475
0.9726	High Similarity	NPC40394
0.9726	High Similarity	NPC157996
0.9726	High Similarity	NPC34177
0.9595	High Similarity	NPC300499
0.9589	High Similarity	NPC122418
0.9589	High Similarity	NPC265328
0.9589	High Similarity	NPC106364
0.9589	High Similarity	NPC120098
0.9589	High Similarity	NPC30590
0.9589	High Similarity	NPC290598
0.9589	High Similarity	NPC27765
0.9474	High Similarity	NPC242350
0.9452	High Similarity	NPC138374
0.9452	High Similarity	NPC34700
0.9359	High Similarity	NPC238992
0.9351	High Similarity	NPC47763
0.9342	High Similarity	NPC295131
0.9315	High Similarity	NPC100334
0.9231	High Similarity	NPC159168
0.9231	High Similarity	NPC253402
0.9231	High Similarity	NPC237795
0.9231	High Similarity	NPC82538
0.9221	High Similarity	NPC116202
0.92	High Similarity	NPC472805
0.92	High Similarity	NPC90979
0.9125	High Similarity	NPC237344
0.9103	High Similarity	NPC304285
0.9079	High Similarity	NPC72507
0.9054	High Similarity	NPC477138
0.9054	High Similarity	NPC91858
0.9054	High Similarity	NPC243342
0.9054	High Similarity	NPC471797
0.8947	High Similarity	NPC471798
0.8947	High Similarity	NPC477924
0.8933	High Similarity	NPC66566
0.8933	High Similarity	NPC477923
0.8933	High Similarity	NPC291503
0.8919	High Similarity	NPC211009
0.8919	High Similarity	NPC182717
0.8919	High Similarity	NPC471799
0.8889	High Similarity	NPC213412
0.8861	High Similarity	NPC248886
0.8784	High Similarity	NPC167706
0.8784	High Similarity	NPC242001
0.8784	High Similarity	NPC301226
0.878	High Similarity	NPC73064
0.8765	High Similarity	NPC133954
0.8765	High Similarity	NPC191965
0.8718	High Similarity	NPC472463
0.8701	High Similarity	NPC470711
0.8701	High Similarity	NPC470758
0.8701	High Similarity	NPC91594
0.869	High Similarity	NPC470589
0.869	High Similarity	NPC126369
0.869	High Similarity	NPC111110
0.8684	High Similarity	NPC144075
0.8675	High Similarity	NPC474512
0.8675	High Similarity	NPC181225
0.8675	High Similarity	NPC17733
0.8675	High Similarity	NPC473242
0.8675	High Similarity	NPC470629
0.8675	High Similarity	NPC290690
0.8659	High Similarity	NPC74363
0.8659	High Similarity	NPC84121
0.8659	High Similarity	NPC477579
0.8659	High Similarity	NPC235341
0.8659	High Similarity	NPC137306
0.8659	High Similarity	NPC475862
0.8659	High Similarity	NPC95594
0.8649	High Similarity	NPC145498
0.8649	High Similarity	NPC92801
0.8642	High Similarity	NPC180834
0.8642	High Similarity	NPC209802
0.863	High Similarity	NPC208999
0.859	High Similarity	NPC148977
0.859	High Similarity	NPC285761
0.859	High Similarity	NPC167037
0.859	High Similarity	NPC244385
0.859	High Similarity	NPC138621
0.859	High Similarity	NPC6978
0.859	High Similarity	NPC275910
0.8571	High Similarity	NPC321016
0.8571	High Similarity	NPC121798
0.8571	High Similarity	NPC240604
0.8571	High Similarity	NPC78067
0.8571	High Similarity	NPC237460
0.8571	High Similarity	NPC187785
0.8571	High Similarity	NPC274330
0.8571	High Similarity	NPC470588
0.8571	High Similarity	NPC265588
0.8571	High Similarity	NPC130520
0.8571	High Similarity	NPC263393
0.8571	High Similarity	NPC470749
0.8571	High Similarity	NPC293048
0.8571	High Similarity	NPC127689
0.8571	High Similarity	NPC198664
0.8571	High Similarity	NPC274079
0.8571	High Similarity	NPC234346
0.8571	High Similarity	NPC321381
0.8571	High Similarity	NPC106432
0.8571	High Similarity	NPC61543
0.8571	High Similarity	NPC259875
0.8571	High Similarity	NPC93662
0.8571	High Similarity	NPC225585
0.8571	High Similarity	NPC270768
0.8571	High Similarity	NPC477925
0.8571	High Similarity	NPC107059
0.8571	High Similarity	NPC189883
0.8571	High Similarity	NPC59263
0.8571	High Similarity	NPC143232
0.8571	High Similarity	NPC278091
0.8571	High Similarity	NPC300324
0.8554	High Similarity	NPC242468
0.8554	High Similarity	NPC171203
0.8554	High Similarity	NPC142415
0.8554	High Similarity	NPC88716
0.8554	High Similarity	NPC293564
0.8554	High Similarity	NPC307426
0.8554	High Similarity	NPC102683
0.8554	High Similarity	NPC68160
0.8554	High Similarity	NPC18064
0.8554	High Similarity	NPC98442
0.8554	High Similarity	NPC51700
0.8554	High Similarity	NPC130577
0.8537	High Similarity	NPC477578
0.8533	High Similarity	NPC110799
0.85	High Similarity	NPC476646
0.85	High Similarity	NPC474531
0.85	High Similarity	NPC470383
0.8488	Intermediate Similarity	NPC229281
0.8481	Intermediate Similarity	NPC1319
0.8481	Intermediate Similarity	NPC273410
0.8481	Intermediate Similarity	NPC80530
0.8471	Intermediate Similarity	NPC130278
0.8471	Intermediate Similarity	NPC471432
0.8471	Intermediate Similarity	NPC86372
0.8471	Intermediate Similarity	NPC172361
0.8471	Intermediate Similarity	NPC471433
0.8462	Intermediate Similarity	NPC198968
0.8462	Intermediate Similarity	NPC130136
0.8462	Intermediate Similarity	NPC318495
0.8462	Intermediate Similarity	NPC214570
0.8462	Intermediate Similarity	NPC155986
0.8452	Intermediate Similarity	NPC40552
0.8452	Intermediate Similarity	NPC246708
0.8452	Intermediate Similarity	NPC52169
0.8452	Intermediate Similarity	NPC182797
0.8442	Intermediate Similarity	NPC231256
0.8442	Intermediate Similarity	NPC22105
0.8442	Intermediate Similarity	NPC136188
0.8442	Intermediate Similarity	NPC134847
0.8442	Intermediate Similarity	NPC471723
0.8442	Intermediate Similarity	NPC240235
0.8442	Intermediate Similarity	NPC257347
0.8442	Intermediate Similarity	NPC28657
0.8442	Intermediate Similarity	NPC178383
0.8442	Intermediate Similarity	NPC230301
0.8442	Intermediate Similarity	NPC304309
0.8442	Intermediate Similarity	NPC285893
0.8442	Intermediate Similarity	NPC162742
0.8442	Intermediate Similarity	NPC288035
0.8442	Intermediate Similarity	NPC212879
0.8442	Intermediate Similarity	NPC141071
0.8442	Intermediate Similarity	NPC104387
0.8434	Intermediate Similarity	NPC72638
0.8434	Intermediate Similarity	NPC24277
0.8395	Intermediate Similarity	NPC310989
0.8395	Intermediate Similarity	NPC101462
0.8395	Intermediate Similarity	NPC30166
0.8391	Intermediate Similarity	NPC6818
0.8391	Intermediate Similarity	NPC191412
0.8391	Intermediate Similarity	NPC114159
0.8391	Intermediate Similarity	NPC159365
0.8378	Intermediate Similarity	NPC94192
0.8375	Intermediate Similarity	NPC322313
0.8375	Intermediate Similarity	NPC236237
0.8375	Intermediate Similarity	NPC102253
0.8375	Intermediate Similarity	NPC13554
0.8375	Intermediate Similarity	NPC236112
0.8375	Intermediate Similarity	NPC287749
0.8375	Intermediate Similarity	NPC96362
0.8372	Intermediate Similarity	NPC228784
0.8372	Intermediate Similarity	NPC282616
0.8372	Intermediate Similarity	NPC324341
0.8372	Intermediate Similarity	NPC155120
0.8372	Intermediate Similarity	NPC187722
0.8372	Intermediate Similarity	NPC966
0.8372	Intermediate Similarity	NPC288833
0.8354	Intermediate Similarity	NPC83351

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 NPC53744 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	1977
0.2-0.3	4177
0.3-0.4	1987
0.4-0.5	445
0.5-0.6	185
0.6-0.7	163
0.7-0.8	15
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.973	High Similarity	NPD7645	Phase 2
0.8442	Intermediate Similarity	NPD6942	Approved
0.8442	Intermediate Similarity	NPD7339	Approved
0.8375	Intermediate Similarity	NPD7525	Registered
0.8333	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD7515	Phase 2
0.7778	Intermediate Similarity	NPD7748	Approved
0.7765	Intermediate Similarity	NPD4786	Approved
0.7738	Intermediate Similarity	NPD3667	Approved
0.7625	Intermediate Similarity	NPD6926	Approved
0.7625	Intermediate Similarity	NPD6924	Approved
0.7586	Intermediate Similarity	NPD3618	Phase 1
0.7531	Intermediate Similarity	NPD8264	Approved
0.7528	Intermediate Similarity	NPD5328	Approved
0.7527	Intermediate Similarity	NPD7902	Approved
0.7471	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6933	Approved
0.7407	Intermediate Similarity	NPD4785	Approved
0.7407	Intermediate Similarity	NPD4784	Approved
0.7381	Intermediate Similarity	NPD6929	Approved
0.7375	Intermediate Similarity	NPD4243	Approved
0.7375	Intermediate Similarity	NPD7150	Approved
0.7375	Intermediate Similarity	NPD7152	Approved
0.7375	Intermediate Similarity	NPD7151	Approved
0.7363	Intermediate Similarity	NPD6079	Approved
0.7342	Intermediate Similarity	NPD6923	Approved
0.7342	Intermediate Similarity	NPD6922	Approved
0.7303	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD4748	Discontinued
0.7294	Intermediate Similarity	NPD6930	Phase 2
0.7294	Intermediate Similarity	NPD6931	Approved
0.7294	Intermediate Similarity	NPD7509	Discontinued
0.725	Intermediate Similarity	NPD7143	Approved
0.725	Intermediate Similarity	NPD7144	Approved
0.7204	Intermediate Similarity	NPD7900	Approved
0.7204	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD3666	Approved
0.7159	Intermediate Similarity	NPD3133	Approved
0.7159	Intermediate Similarity	NPD3665	Phase 1
0.7143	Intermediate Similarity	NPD6932	Approved
0.7143	Intermediate Similarity	NPD6925	Approved
0.7143	Intermediate Similarity	NPD5776	Phase 2
0.7097	Intermediate Similarity	NPD4202	Approved
0.7059	Intermediate Similarity	NPD7145	Approved
0.7045	Intermediate Similarity	NPD6695	Phase 3
0.6979	Remote Similarity	NPD4755	Approved
0.6977	Remote Similarity	NPD6683	Phase 2
0.6966	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD3668	Phase 3
0.6915	Remote Similarity	NPD6399	Phase 3
0.6914	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD7638	Approved
0.6905	Remote Similarity	NPD4190	Phase 3
0.6905	Remote Similarity	NPD5275	Approved
0.6897	Remote Similarity	NPD7332	Phase 2
0.6897	Remote Similarity	NPD7514	Phase 3
0.6889	Remote Similarity	NPD6893	Approved
0.6875	Remote Similarity	NPD5222	Approved
0.6875	Remote Similarity	NPD4697	Phase 3
0.6875	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5221	Approved
0.686	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7639	Approved
0.6837	Remote Similarity	NPD7640	Approved
0.6837	Remote Similarity	NPD4700	Approved
0.6837	Remote Similarity	NPD5286	Approved
0.6837	Remote Similarity	NPD5285	Approved
0.6837	Remote Similarity	NPD4696	Approved
0.6818	Remote Similarity	NPD6898	Phase 1
0.6818	Remote Similarity	NPD6902	Approved
0.6809	Remote Similarity	NPD8034	Phase 2
0.6809	Remote Similarity	NPD8035	Phase 2
0.6804	Remote Similarity	NPD5173	Approved
0.6782	Remote Similarity	NPD4195	Approved
0.6774	Remote Similarity	NPD4753	Phase 2
0.6774	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7524	Approved
0.6739	Remote Similarity	NPD7750	Discontinued
0.6735	Remote Similarity	NPD5290	Discontinued
0.6705	Remote Similarity	NPD4695	Discontinued
0.67	Remote Similarity	NPD5225	Approved
0.67	Remote Similarity	NPD5226	Approved
0.67	Remote Similarity	NPD5224	Approved
0.67	Remote Similarity	NPD4633	Approved
0.67	Remote Similarity	NPD5211	Phase 2
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7128	Approved
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD368	Approved
0.6667	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD6402	Approved
0.6634	Remote Similarity	NPD5174	Approved
0.6634	Remote Similarity	NPD5175	Approved
0.6632	Remote Similarity	NPD6411	Approved
0.663	Remote Similarity	NPD5279	Phase 3
0.66	Remote Similarity	NPD5223	Approved
0.6569	Remote Similarity	NPD5141	Approved
0.6566	Remote Similarity	NPD4225	Approved
0.6556	Remote Similarity	NPD4221	Approved
0.6556	Remote Similarity	NPD4223	Phase 3
0.6538	Remote Similarity	NPD6899	Approved
0.6538	Remote Similarity	NPD7320	Approved
0.6538	Remote Similarity	NPD6881	Approved
0.6522	Remote Similarity	NPD5329	Approved
0.6505	Remote Similarity	NPD4767	Approved
0.6505	Remote Similarity	NPD4768	Approved
0.6484	Remote Similarity	NPD4788	Approved
0.6476	Remote Similarity	NPD6372	Approved
0.6476	Remote Similarity	NPD6373	Approved
0.6471	Remote Similarity	NPD4754	Approved
0.6465	Remote Similarity	NPD6083	Phase 2
0.6465	Remote Similarity	NPD6084	Phase 2
0.6458	Remote Similarity	NPD7087	Discontinued
0.6452	Remote Similarity	NPD6409	Approved
0.6452	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5330	Approved
0.6452	Remote Similarity	NPD6684	Approved
0.6452	Remote Similarity	NPD7146	Approved
0.6452	Remote Similarity	NPD7521	Approved
0.6452	Remote Similarity	NPD7334	Approved
0.6442	Remote Similarity	NPD5697	Approved
0.6442	Remote Similarity	NPD5701	Approved
0.6436	Remote Similarity	NPD4159	Approved
0.6429	Remote Similarity	NPD4787	Phase 1
0.6429	Remote Similarity	NPD5210	Approved
0.6429	Remote Similarity	NPD4629	Approved
0.6421	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD6101	Approved
0.6415	Remote Similarity	NPD7290	Approved
0.6415	Remote Similarity	NPD6883	Approved
0.6415	Remote Similarity	NPD7102	Approved
0.6413	Remote Similarity	NPD4197	Approved
0.6383	Remote Similarity	NPD3573	Approved
0.6381	Remote Similarity	NPD5128	Approved
0.6381	Remote Similarity	NPD4729	Approved
0.6381	Remote Similarity	NPD4730	Approved
0.6364	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7115	Discovery
0.6355	Remote Similarity	NPD6847	Approved
0.6355	Remote Similarity	NPD6869	Approved
0.6355	Remote Similarity	NPD6649	Approved
0.6355	Remote Similarity	NPD6617	Approved
0.6355	Remote Similarity	NPD6650	Approved
0.6355	Remote Similarity	NPD8130	Phase 1
0.6353	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD6014	Approved
0.6321	Remote Similarity	NPD6013	Approved
0.6321	Remote Similarity	NPD6012	Approved
0.6316	Remote Similarity	NPD342	Phase 1
0.6316	Remote Similarity	NPD8328	Phase 3
0.6316	Remote Similarity	NPD6903	Approved
0.631	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.631	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6882	Approved
0.6296	Remote Similarity	NPD8297	Approved
0.6292	Remote Similarity	NPD3617	Approved
0.6286	Remote Similarity	NPD6412	Phase 2
0.6283	Remote Similarity	NPD8033	Approved
0.6277	Remote Similarity	NPD4690	Approved
0.6277	Remote Similarity	NPD5205	Approved
0.6277	Remote Similarity	NPD4138	Approved
0.6277	Remote Similarity	NPD4693	Phase 3
0.6277	Remote Similarity	NPD4688	Approved
0.6277	Remote Similarity	NPD4519	Discontinued
0.6277	Remote Similarity	NPD4623	Approved
0.6277	Remote Similarity	NPD4689	Approved
0.6262	Remote Similarity	NPD5248	Approved
0.6262	Remote Similarity	NPD5250	Approved
0.6262	Remote Similarity	NPD4634	Approved
0.6262	Remote Similarity	NPD5247	Approved
0.6262	Remote Similarity	NPD5251	Approved
0.6262	Remote Similarity	NPD5249	Phase 3
0.625	Remote Similarity	NPD6117	Approved
0.625	Remote Similarity	NPD6051	Approved
0.6226	Remote Similarity	NPD6011	Approved
0.6226	Remote Similarity	NPD5168	Approved
0.6214	Remote Similarity	NPD7632	Discontinued
0.6207	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD5215	Approved
0.6204	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD5217	Approved
0.6204	Remote Similarity	NPD5216	Approved
0.62	Remote Similarity	NPD7614	Phase 1
0.6195	Remote Similarity	NPD8377	Approved
0.6195	Remote Similarity	NPD8294	Approved
0.6186	Remote Similarity	NPD7136	Phase 2
0.618	Remote Similarity	NPD6116	Phase 1
0.6161	Remote Similarity	NPD7328	Approved
0.6161	Remote Similarity	NPD7327	Approved
0.6146	Remote Similarity	NPD5737	Approved
0.6146	Remote Similarity	NPD4722	Approved
0.6146	Remote Similarity	NPD4723	Approved
0.6146	Remote Similarity	NPD6672	Approved
0.614	Remote Similarity	NPD8296	Approved
0.614	Remote Similarity	NPD8335	Approved
0.614	Remote Similarity	NPD8378	Approved
0.614	Remote Similarity	NPD8380	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