NPASS Compound

Structure

NPC470276 OpenBabel07101718192D 39 43 0 0 1 0 0 0 0 0999 V2000 -3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5628 -0.3864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9885 -2.7044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1261 0.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1859 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7375 -2.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6065 -0.8023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2757 -1.5454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6284 -1.0102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9345 -3.0827 0.0000 C 0 0 0 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 1.9400 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9229 -2.0806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2538 -1.3375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3194 -1.9612 0.0000 C 0 0 2 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 3.3412 -2.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4049 -1.0000 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 1.7321 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.9011 -1.8727 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4049 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 22 1 0 0 0 0 4 24 2 0 0 0 0 5 31 1 0 0 0 0 7 8 1 0 0 0 0 8 18 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 22 2 0 0 0 0 11 23 1 0 0 0 0 12 14 1 0 0 0 0 12 25 1 0 0 0 0 13 15 1 0 0 0 0 13 28 1 0 0 0 0 14 32 1 0 0 0 0 16 17 1 0 0 0 0 16 31 1 0 0 0 0 17 33 1 0 0 0 0 18 35 1 0 0 0 0 19 27 1 0 0 0 0 20 22 1 0 0 0 0 20 36 2 0 0 0 0 21 33 1 0 0 0 0 21 34 1 0 0 0 0 23 3 1 1 0 0 0 23 25 1 0 0 0 0 24 29 1 0 0 0 0 24 30 1 0 0 0 0 25 31 1 1 0 0 0 26 19 1 1 0 0 0 26 29 1 0 0 0 0 26 39 1 0 0 0 0 27 32 1 6 0 0 0 27 33 1 0 0 0 0 28 35 2 3 0 0 0 28 37 1 0 0 0 0 29 34 1 1 0 0 0 30 38 2 0 0 0 0 30 39 1 0 0 0 0 31 32 1 1 0 0 0 32 6 1 6 0 0 0 33 34 1 6 0 0 0 34 15 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	537.38
Volume:	586.813
LogP:	5.358
LogD:	4.677
LogS:	-4.535
# Rotatable Bonds:	12
TPSA:	72.47
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.134
Synthetic Accessibility Score:	5.63
Fsp3:	0.794
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	3
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.144
MDCK Permeability:	2.4523402316845022e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.142
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	99.71048736572266%
Volume Distribution (VD):	0.836
Pgp-substrate:	2.3397693634033203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.345
CYP2C19-inhibitor:	0.658
CYP2C19-substrate:	0.84
CYP2C9-inhibitor:	0.464
CYP2C9-substrate:	0.175
CYP2D6-inhibitor:	0.674
CYP2D6-substrate:	0.321
CYP3A4-inhibitor:	0.95
CYP3A4-substrate:	0.411

ADMET: Excretion

Clearance (CL):	4.491
Half-life (T1/2):	0.303

ADMET: Toxicity

hERG Blockers:	0.837
Human Hepatotoxicity (H-HT):	0.346
Drug-inuced Liver Injury (DILI):	0.446
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.273
Maximum Recommended Daily Dose:	0.882
Skin Sensitization:	0.956
Carcinogencity:	0.264
Eye Corrosion:	0.006
Eye Irritation:	0.025
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC470276

Natural Product ID:	NPC470276
*Common Name:**	ONVBEKYLAHOXOC-FKBWSEEPSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ONVBEKYLAHOXOC-FKBWSEEPSA-N
Standard InCHI:	InChI=1S/C34H51NO4/c1-7-8-18-35-28(37)13-15-34-21-33(34)17-16-31(5)25(23(3)11-9-10-22(2)20-36)12-14-32(31,6)27(33)19-26-29(34)24(4)30(38)39-26/h10,20,23,25-27,29H,4,7-9,11-19,21H2,1-3,5-6H3,(H,35,37)/b22-10+/t23-,25-,26-,27+,29-,31-,32+,33+,34-/m1/s1
SMILES:	CCCCNC(=O)CCC12CC13CCC4(C(CCC4(C3CC5C2C(=C)C(=O)O5)C)C(C)CCC=C(C)C=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1939896
PubChem CID:	57394680
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
NPO33315	gardenia spp.	Species	Rubiaceae	Eukaryota	n.a.	Thai	n.a.	PMID[22142538]

☑ 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
Others	1

Activity Type	# Activity
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT177	Tissue	Aorta	Rattus norvegicus	Inhibition	=	10.0	%	PMID[538221]

☑ 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 NPC470276 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	106
0.1-0.2	724
0.2-0.3	3239
0.3-0.4	16541
0.4-0.5	9338
0.5-0.6	8925
0.6-0.7	3604
0.7-0.8	210
0.8-0.85	4
0.85-0.9	4
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9545	High Similarity	NPC470275
0.8796	High Similarity	NPC176883
0.8519	High Similarity	NPC476303
0.8519	High Similarity	NPC470906
0.8288	Intermediate Similarity	NPC476237
0.8257	Intermediate Similarity	NPC252295
0.8241	Intermediate Similarity	NPC307164
0.8099	Intermediate Similarity	NPC470277
0.7928	Intermediate Similarity	NPC473155
0.7895	Intermediate Similarity	NPC119329
0.7851	Intermediate Similarity	NPC9714
0.7807	Intermediate Similarity	NPC180204
0.777	Intermediate Similarity	NPC470274
0.7768	Intermediate Similarity	NPC98868
0.7699	Intermediate Similarity	NPC201406
0.7667	Intermediate Similarity	NPC106479
0.7658	Intermediate Similarity	NPC293052
0.7652	Intermediate Similarity	NPC112009
0.7583	Intermediate Similarity	NPC69291
0.7565	Intermediate Similarity	NPC155332
0.7565	Intermediate Similarity	NPC32577
0.7565	Intermediate Similarity	NPC114540
0.7545	Intermediate Similarity	NPC476187
0.7545	Intermediate Similarity	NPC470113
0.7523	Intermediate Similarity	NPC288699
0.7519	Intermediate Similarity	NPC246209
0.75	Intermediate Similarity	NPC183012
0.75	Intermediate Similarity	NPC36688
0.75	Intermediate Similarity	NPC120321
0.75	Intermediate Similarity	NPC33473
0.7478	Intermediate Similarity	NPC303559
0.7478	Intermediate Similarity	NPC118174
0.7477	Intermediate Similarity	NPC474185
0.7477	Intermediate Similarity	NPC470224
0.7463	Intermediate Similarity	NPC476558
0.7456	Intermediate Similarity	NPC57079
0.7456	Intermediate Similarity	NPC108368
0.7455	Intermediate Similarity	NPC471896
0.7442	Intermediate Similarity	NPC476957
0.7434	Intermediate Similarity	NPC327788
0.7419	Intermediate Similarity	NPC476956
0.7417	Intermediate Similarity	NPC328052
0.7391	Intermediate Similarity	NPC35751
0.7391	Intermediate Similarity	NPC266955
0.7387	Intermediate Similarity	NPC233345
0.7387	Intermediate Similarity	NPC26888
0.7387	Intermediate Similarity	NPC186363
0.7387	Intermediate Similarity	NPC72845
0.7377	Intermediate Similarity	NPC122056
0.7373	Intermediate Similarity	NPC173172
0.7373	Intermediate Similarity	NPC475414
0.7368	Intermediate Similarity	NPC474343
0.7368	Intermediate Similarity	NPC291634
0.7368	Intermediate Similarity	NPC253826
0.7368	Intermediate Similarity	NPC110937
0.7364	Intermediate Similarity	NPC204556
0.7364	Intermediate Similarity	NPC128496
0.735	Intermediate Similarity	NPC297617
0.7339	Intermediate Similarity	NPC470012
0.7339	Intermediate Similarity	NPC167877
0.7333	Intermediate Similarity	NPC218602
0.7328	Intermediate Similarity	NPC115899
0.7321	Intermediate Similarity	NPC38232
0.7321	Intermediate Similarity	NPC139692
0.7321	Intermediate Similarity	NPC472871
0.7317	Intermediate Similarity	NPC470540
0.7311	Intermediate Similarity	NPC475294
0.7311	Intermediate Similarity	NPC220974
0.7311	Intermediate Similarity	NPC131665
0.7311	Intermediate Similarity	NPC255387
0.7311	Intermediate Similarity	NPC475176
0.7304	Intermediate Similarity	NPC194196
0.7297	Intermediate Similarity	NPC175628
0.7297	Intermediate Similarity	NPC111585
0.7297	Intermediate Similarity	NPC148414
0.7295	Intermediate Similarity	NPC71348
0.7295	Intermediate Similarity	NPC470063
0.7288	Intermediate Similarity	NPC189616
0.7288	Intermediate Similarity	NPC472868
0.7281	Intermediate Similarity	NPC471039
0.7273	Intermediate Similarity	NPC179642
0.7273	Intermediate Similarity	NPC470496
0.7273	Intermediate Similarity	NPC16270
0.7273	Intermediate Similarity	NPC473229
0.7265	Intermediate Similarity	NPC136289
0.7265	Intermediate Similarity	NPC476081
0.7258	Intermediate Similarity	NPC196931
0.7257	Intermediate Similarity	NPC57117
0.7257	Intermediate Similarity	NPC476186
0.7257	Intermediate Similarity	NPC159410
0.7257	Intermediate Similarity	NPC471720
0.7257	Intermediate Similarity	NPC471040
0.725	Intermediate Similarity	NPC475418
0.725	Intermediate Similarity	NPC306265
0.725	Intermediate Similarity	NPC275539
0.725	Intermediate Similarity	NPC318363
0.725	Intermediate Similarity	NPC189075
0.725	Intermediate Similarity	NPC473482
0.7248	Intermediate Similarity	NPC477920
0.7241	Intermediate Similarity	NPC47024
0.7241	Intermediate Similarity	NPC476274
0.7241	Intermediate Similarity	NPC470074
0.7241	Intermediate Similarity	NPC471413
0.7227	Intermediate Similarity	NPC266570
0.7222	Intermediate Similarity	NPC470011
0.7217	Intermediate Similarity	NPC292133
0.7217	Intermediate Similarity	NPC108078
0.7217	Intermediate Similarity	NPC73911
0.7217	Intermediate Similarity	NPC126815
0.7213	Intermediate Similarity	NPC474315
0.7207	Intermediate Similarity	NPC474396
0.7207	Intermediate Similarity	NPC73995
0.7207	Intermediate Similarity	NPC474889
0.7207	Intermediate Similarity	NPC66344
0.7207	Intermediate Similarity	NPC50488
0.7203	Intermediate Similarity	NPC475526
0.7203	Intermediate Similarity	NPC329345
0.7203	Intermediate Similarity	NPC473283
0.7203	Intermediate Similarity	NPC72151
0.72	Intermediate Similarity	NPC284068
0.72	Intermediate Similarity	NPC167606
0.72	Intermediate Similarity	NPC20302
0.72	Intermediate Similarity	NPC473656
0.72	Intermediate Similarity	NPC140055
0.72	Intermediate Similarity	NPC286528
0.7193	Intermediate Similarity	NPC84383
0.7193	Intermediate Similarity	NPC476174
0.7193	Intermediate Similarity	NPC279974
0.719	Intermediate Similarity	NPC474901
0.719	Intermediate Similarity	NPC475065
0.719	Intermediate Similarity	NPC475941
0.7182	Intermediate Similarity	NPC305029
0.7182	Intermediate Similarity	NPC181103
0.7179	Intermediate Similarity	NPC471412
0.7179	Intermediate Similarity	NPC476223
0.7179	Intermediate Similarity	NPC310981
0.7179	Intermediate Similarity	NPC473514
0.7179	Intermediate Similarity	NPC81530
0.7179	Intermediate Similarity	NPC168319
0.7179	Intermediate Similarity	NPC476240
0.7179	Intermediate Similarity	NPC194028
0.7179	Intermediate Similarity	NPC224720
0.7177	Intermediate Similarity	NPC147912
0.7177	Intermediate Similarity	NPC67259
0.7177	Intermediate Similarity	NPC123117
0.7168	Intermediate Similarity	NPC476304
0.7167	Intermediate Similarity	NPC302788
0.7167	Intermediate Similarity	NPC179380
0.7167	Intermediate Similarity	NPC110496
0.7155	Intermediate Similarity	NPC473154
0.7155	Intermediate Similarity	NPC216478
0.7155	Intermediate Similarity	NPC471966
0.7155	Intermediate Similarity	NPC176845
0.7155	Intermediate Similarity	NPC478056
0.7154	Intermediate Similarity	NPC285956
0.7154	Intermediate Similarity	NPC15095
0.7154	Intermediate Similarity	NPC264634
0.7154	Intermediate Similarity	NPC475524
0.7154	Intermediate Similarity	NPC100267
0.7143	Intermediate Similarity	NPC50774
0.7143	Intermediate Similarity	NPC257457
0.7143	Intermediate Similarity	NPC474842
0.7143	Intermediate Similarity	NPC475965
0.7143	Intermediate Similarity	NPC311554
0.7143	Intermediate Similarity	NPC475372
0.7143	Intermediate Similarity	NPC152467
0.7143	Intermediate Similarity	NPC709
0.7131	Intermediate Similarity	NPC475563
0.7131	Intermediate Similarity	NPC475134
0.713	Intermediate Similarity	NPC151725
0.713	Intermediate Similarity	NPC78473
0.713	Intermediate Similarity	NPC106425
0.713	Intermediate Similarity	NPC234993
0.713	Intermediate Similarity	NPC242848
0.713	Intermediate Similarity	NPC301534
0.713	Intermediate Similarity	NPC134072
0.713	Intermediate Similarity	NPC122324
0.713	Intermediate Similarity	NPC250757
0.712	Intermediate Similarity	NPC298278
0.712	Intermediate Similarity	NPC270958
0.712	Intermediate Similarity	NPC72772
0.712	Intermediate Similarity	NPC469794
0.7119	Intermediate Similarity	NPC162973
0.7119	Intermediate Similarity	NPC475320
0.7119	Intermediate Similarity	NPC320447
0.7117	Intermediate Similarity	NPC215831
0.7117	Intermediate Similarity	NPC117122
0.7117	Intermediate Similarity	NPC277771
0.7117	Intermediate Similarity	NPC226863
0.7107	Intermediate Similarity	NPC476802
0.7107	Intermediate Similarity	NPC469844
0.7107	Intermediate Similarity	NPC89171
0.7107	Intermediate Similarity	NPC177064
0.7105	Intermediate Similarity	NPC477130
0.7105	Intermediate Similarity	NPC294266
0.7105	Intermediate Similarity	NPC477129
0.7105	Intermediate Similarity	NPC124207
0.7097	Intermediate Similarity	NPC202889
0.7097	Intermediate Similarity	NPC73050
0.7094	Intermediate Similarity	NPC476299

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 NPC470276 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	93
0.1-0.2	625
0.2-0.3	3035
0.3-0.4	3883
0.4-0.5	1008
0.5-0.6	352
0.6-0.7	151
0.7-0.8	3
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.72	Intermediate Similarity	NPD7115	Discovery
0.7193	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6399	Phase 3
0.7155	Intermediate Similarity	NPD7638	Approved
0.7094	Intermediate Similarity	NPD7639	Approved
0.7094	Intermediate Similarity	NPD6404	Discontinued
0.7094	Intermediate Similarity	NPD7640	Approved
0.7009	Intermediate Similarity	NPD4225	Approved
0.6957	Remote Similarity	NPD7748	Approved
0.6942	Remote Similarity	NPD6008	Approved
0.693	Remote Similarity	NPD8034	Phase 2
0.693	Remote Similarity	NPD8035	Phase 2
0.6923	Remote Similarity	NPD7902	Approved
0.687	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD6908	Approved
0.6846	Remote Similarity	NPD6909	Approved
0.6838	Remote Similarity	NPD4697	Phase 3
0.6829	Remote Similarity	NPD6899	Approved
0.6829	Remote Similarity	NPD6881	Approved
0.6829	Remote Similarity	NPD7320	Approved
0.681	Remote Similarity	NPD6001	Approved
0.6803	Remote Similarity	NPD5739	Approved
0.6803	Remote Similarity	NPD6402	Approved
0.6803	Remote Similarity	NPD6675	Approved
0.6803	Remote Similarity	NPD7128	Approved
0.68	Remote Similarity	NPD6649	Approved
0.68	Remote Similarity	NPD8130	Phase 1
0.68	Remote Similarity	NPD6650	Approved
0.6786	Remote Similarity	NPD3618	Phase 1
0.6783	Remote Similarity	NPD6079	Approved
0.6774	Remote Similarity	NPD6372	Approved
0.6774	Remote Similarity	NPD6373	Approved
0.6754	Remote Similarity	NPD5328	Approved
0.6748	Remote Similarity	NPD5697	Approved
0.6746	Remote Similarity	NPD8297	Approved
0.6742	Remote Similarity	NPD7604	Phase 2
0.6727	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6883	Approved
0.672	Remote Similarity	NPD7290	Approved
0.672	Remote Similarity	NPD6420	Discontinued
0.672	Remote Similarity	NPD7102	Approved
0.6696	Remote Similarity	NPD1694	Approved
0.6694	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD6903	Approved
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD8418	Phase 2
0.6667	Remote Similarity	NPD6617	Approved
0.6667	Remote Similarity	NPD5737	Approved
0.6667	Remote Similarity	NPD6672	Approved
0.6667	Remote Similarity	NPD6869	Approved
0.6642	Remote Similarity	NPD7507	Approved
0.664	Remote Similarity	NPD6013	Approved
0.664	Remote Similarity	NPD6012	Approved
0.664	Remote Similarity	NPD6014	Approved
0.6639	Remote Similarity	NPD6084	Phase 2
0.6639	Remote Similarity	NPD6083	Phase 2
0.6638	Remote Similarity	NPD7515	Phase 2
0.6637	Remote Similarity	NPD5330	Approved
0.6637	Remote Similarity	NPD6684	Approved
0.6637	Remote Similarity	NPD7146	Approved
0.6637	Remote Similarity	NPD7334	Approved
0.6637	Remote Similarity	NPD6409	Approved
0.6637	Remote Similarity	NPD7521	Approved
0.6617	Remote Similarity	NPD7122	Discontinued
0.6614	Remote Similarity	NPD6882	Approved
0.6613	Remote Similarity	NPD5701	Approved
0.6607	Remote Similarity	NPD4786	Approved
0.6596	Remote Similarity	NPD6333	Approved
0.6596	Remote Similarity	NPD6334	Approved
0.6594	Remote Similarity	NPD6845	Suspended
0.6583	Remote Similarity	NPD5696	Approved
0.6557	Remote Similarity	NPD7632	Discontinued
0.6555	Remote Similarity	NPD5222	Approved
0.6555	Remote Similarity	NPD5221	Approved
0.6555	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7260	Phase 2
0.6522	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5173	Approved
0.6496	Remote Similarity	NPD7319	Approved
0.6496	Remote Similarity	NPD5693	Phase 1
0.6471	Remote Similarity	NPD5695	Phase 3
0.6466	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD6868	Approved
0.6441	Remote Similarity	NPD4202	Approved
0.6429	Remote Similarity	NPD3667	Approved
0.6423	Remote Similarity	NPD5211	Phase 2
0.6417	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5785	Approved
0.6393	Remote Similarity	NPD5285	Approved
0.6393	Remote Similarity	NPD4696	Approved
0.6393	Remote Similarity	NPD5286	Approved
0.6364	Remote Similarity	NPD4755	Approved
0.6364	Remote Similarity	NPD6335	Approved
0.6348	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD5223	Approved
0.6336	Remote Similarity	NPD6274	Approved
0.6333	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD6673	Approved
0.6325	Remote Similarity	NPD6904	Approved
0.6325	Remote Similarity	NPD6080	Approved
0.6324	Remote Similarity	NPD7492	Approved
0.632	Remote Similarity	NPD5141	Approved
0.6316	Remote Similarity	NPD7101	Approved
0.6316	Remote Similarity	NPD3666	Approved
0.6316	Remote Similarity	NPD7100	Approved
0.6316	Remote Similarity	NPD3133	Approved
0.6316	Remote Similarity	NPD3665	Phase 1
0.6308	Remote Similarity	NPD4632	Approved
0.6304	Remote Similarity	NPD7736	Approved
0.6299	Remote Similarity	NPD6686	Approved
0.629	Remote Similarity	NPD5225	Approved
0.629	Remote Similarity	NPD5224	Approved
0.629	Remote Similarity	NPD4633	Approved
0.629	Remote Similarity	NPD5226	Approved
0.6288	Remote Similarity	NPD6317	Approved
0.6277	Remote Similarity	NPD6616	Approved
0.6271	Remote Similarity	NPD5207	Approved
0.6269	Remote Similarity	NPD6054	Approved
0.626	Remote Similarity	NPD4700	Approved
0.625	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD6314	Approved
0.6241	Remote Similarity	NPD6313	Approved
0.624	Remote Similarity	NPD5174	Approved
0.624	Remote Similarity	NPD5175	Approved
0.6232	Remote Similarity	NPD8293	Discontinued
0.6232	Remote Similarity	NPD7078	Approved
0.6231	Remote Similarity	NPD6053	Discontinued
0.6222	Remote Similarity	NPD8033	Approved
0.6218	Remote Similarity	NPD5281	Approved
0.6218	Remote Similarity	NPD5284	Approved
0.6198	Remote Similarity	NPD5210	Approved
0.6198	Remote Similarity	NPD4629	Approved
0.6186	Remote Similarity	NPD6051	Approved
0.6186	Remote Similarity	NPD4753	Phase 2
0.6176	Remote Similarity	NPD6370	Approved
0.6174	Remote Similarity	NPD3668	Phase 3
0.6165	Remote Similarity	NPD6009	Approved
0.6154	Remote Similarity	NPD3573	Approved
0.6148	Remote Similarity	NPD8294	Approved
0.6148	Remote Similarity	NPD6319	Approved
0.6148	Remote Similarity	NPD6059	Approved
0.6148	Remote Similarity	NPD8377	Approved
0.6142	Remote Similarity	NPD6640	Phase 3
0.614	Remote Similarity	NPD4223	Phase 3
0.614	Remote Similarity	NPD4221	Approved
0.6121	Remote Similarity	NPD5329	Approved
0.6119	Remote Similarity	NPD7328	Approved
0.6119	Remote Similarity	NPD7327	Approved
0.6115	Remote Similarity	NPD8074	Phase 3
0.6111	Remote Similarity	NPD4754	Approved
0.6111	Remote Similarity	NPD6052	Approved
0.6106	Remote Similarity	NPD7525	Registered
0.6103	Remote Similarity	NPD8296	Approved
0.6103	Remote Similarity	NPD5983	Phase 2
0.6103	Remote Similarity	NPD6016	Approved
0.6103	Remote Similarity	NPD8380	Approved
0.6103	Remote Similarity	NPD8335	Approved
0.6103	Remote Similarity	NPD8379	Approved
0.6103	Remote Similarity	NPD8378	Approved
0.6103	Remote Similarity	NPD6015	Approved
0.6102	Remote Similarity	NPD5208	Approved
0.6099	Remote Similarity	NPD6914	Discontinued
0.6094	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD5362	Discontinued
0.6083	Remote Similarity	NPD7637	Suspended
0.6083	Remote Similarity	NPD6050	Approved
0.6077	Remote Similarity	NPD6371	Approved
0.6074	Remote Similarity	NPD7517	Approved
0.6074	Remote Similarity	NPD7516	Approved
0.6074	Remote Similarity	NPD7519	Approved
0.6074	Remote Similarity	NPD7518	Approved
0.6068	Remote Similarity	NPD6098	Approved
0.6068	Remote Similarity	NPD5279	Phase 3
0.6061	Remote Similarity	NPD8298	Phase 2
0.6058	Remote Similarity	NPD5988	Approved
0.605	Remote Similarity	NPD1695	Approved
0.6047	Remote Similarity	NPD5168	Approved
0.6047	Remote Similarity	NPD4729	Approved
0.6047	Remote Similarity	NPD4730	Approved
0.6047	Remote Similarity	NPD5128	Approved
0.6043	Remote Similarity	NPD6336	Discontinued
0.6036	Remote Similarity	NPD6117	Approved
0.6034	Remote Similarity	NPD4197	Approved
0.6026	Remote Similarity	NPD7625	Phase 1
0.6016	Remote Similarity	NPD7614	Phase 1
0.6016	Remote Similarity	NPD4767	Approved
0.6016	Remote Similarity	NPD7333	Discontinued
0.6016	Remote Similarity	NPD7732	Phase 3
0.6016	Remote Similarity	NPD4768	Approved
0.6	Remote Similarity	NPD5692	Phase 3
0.5985	Remote Similarity	NPD6921	Approved
0.5984	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD5707	Approved
0.5983	Remote Similarity	NPD6082	Clinical (unspecified phase)

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