NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.14
Volume:	263.658
LogP:	1.329
LogD:	1.156
LogS:	-4.368
# Rotatable Bonds:	0
TPSA:	59.06
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.668
Synthetic Accessibility Score:	5.955
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.869
MDCK Permeability:	1.903560769278556e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.069
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.869
Plasma Protein Binding (PPB):	24.691394805908203%
Volume Distribution (VD):	1.235
Pgp-substrate:	61.10475158691406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.667
CYP2C19-inhibitor:	0.053
CYP2C19-substrate:	0.855
CYP2C9-inhibitor:	0.028
CYP2C9-substrate:	0.07
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.2
CYP3A4-inhibitor:	0.076
CYP3A4-substrate:	0.409

ADMET: Excretion

Clearance (CL):	8.373
Half-life (T1/2):	0.611

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.533
Drug-inuced Liver Injury (DILI):	0.084
AMES Toxicity:	0.059
Rat Oral Acute Toxicity:	0.459
Maximum Recommended Daily Dose:	0.912
Skin Sensitization:	0.918
Carcinogencity:	0.897
Eye Corrosion:	0.03
Eye Irritation:	0.454
Respiratory Toxicity:	0.896

Download Data

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

Natural Product: NPC123505

Natural Product ID:	NPC123505
*Common Name:**	Trichothecolone
IUPAC Name:	n.a.
Synonyms:	Trichothecolone
Standard InCHIKey:	BURHPZJXARNGQY-LACSLYJWSA-N
Standard InCHI:	InChI=1S/C15H20O4/c1-8-4-11-13(2,6-9(8)16)14(3)10(17)5-12(19-11)15(14)7-18-15/h4,10-12,17H,5-7H2,1-3H3/t10-,11-,12-,13+,14-,15+/m1/s1
SMILES:	CC1=C[C@@H]2[C@](C)(CC1=O)[C@@]1(C)[C@@H](C[C@H]([C@]31CO3)O2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481642
PubChem CID:	12444504
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0001789] Trichothecenes

*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
NPO12483	Holarrhena floribunda	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10650079]
NPO12483	Holarrhena floribunda	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16441070]
NPO12483	Holarrhena floribunda	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO28075	Crataegus sanguinea	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12483	Holarrhena floribunda	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20735	Aconitum balfourii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12483	Holarrhena floribunda	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28075	Crataegus sanguinea	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20735	Aconitum balfourii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28355	Pseudocyphellaria crocata	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28075	Crataegus sanguinea	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12483	Holarrhena floribunda	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28249	Macaranga pleiostemon	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27977	Crotalaria verrucosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20735	Aconitum balfourii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28692	Pteris undulata	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28673	Cucumaria echinata	Species	Cucumariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28547	Arthrocnemum glaucum	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28285	Taxus harringtonia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28657	Incarvillea mairei	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29355	Asaemia axillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24825	Colchicum bulbocodium	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28237	Miconia langsdorffii	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23154	Paysonia grandiflora	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27920	Piper kwashoense	Species	Piperaceae	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
EC50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	EC50	=	10.6	ug.mL-1	PMID[468679]
NPT2359	Cell Line	SK-MEL-30	Homo sapiens	EC50	=	8.6	ug.mL-1	PMID[468679]
NPT81	Cell Line	A549	Homo sapiens	EC50	=	7.1	ug.mL-1	PMID[468679]
NPT83	Cell Line	MCF7	Homo sapiens	EC50	=	10.6	ug.mL-1	PMID[468679]

☑ 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 NPC123505 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	209
0.1-0.2	1287
0.2-0.3	4793
0.3-0.4	8668
0.4-0.5	13889
0.5-0.6	7624
0.6-0.7	5170
0.7-0.8	988
0.8-0.85	55
0.85-0.9	9
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.95	High Similarity	NPC77089
0.9406	High Similarity	NPC41551
0.9406	High Similarity	NPC50223
0.91	High Similarity	NPC169843
0.875	High Similarity	NPC187876
0.8654	High Similarity	NPC10150
0.8585	High Similarity	NPC474750
0.8515	High Similarity	NPC79631
0.8447	Intermediate Similarity	NPC474783
0.8447	Intermediate Similarity	NPC260809
0.835	Intermediate Similarity	NPC252242
0.835	Intermediate Similarity	NPC475956
0.8349	Intermediate Similarity	NPC305044
0.8349	Intermediate Similarity	NPC265290
0.8333	Intermediate Similarity	NPC98038
0.8333	Intermediate Similarity	NPC313921
0.83	Intermediate Similarity	NPC240838
0.8265	Intermediate Similarity	NPC197107
0.8257	Intermediate Similarity	NPC101400
0.8257	Intermediate Similarity	NPC101965
0.8252	Intermediate Similarity	NPC26557
0.8235	Intermediate Similarity	NPC212465
0.8235	Intermediate Similarity	NPC177232
0.8235	Intermediate Similarity	NPC474957
0.8235	Intermediate Similarity	NPC79449
0.8173	Intermediate Similarity	NPC214714
0.8173	Intermediate Similarity	NPC475986
0.8173	Intermediate Similarity	NPC200672
0.8137	Intermediate Similarity	NPC476057
0.8137	Intermediate Similarity	NPC182811
0.8137	Intermediate Similarity	NPC347923
0.8125	Intermediate Similarity	NPC474286
0.8125	Intermediate Similarity	NPC475130
0.8113	Intermediate Similarity	NPC93026
0.8113	Intermediate Similarity	NPC265502
0.8113	Intermediate Similarity	NPC469960
0.8113	Intermediate Similarity	NPC29389
0.8095	Intermediate Similarity	NPC232515
0.8091	Intermediate Similarity	NPC317210
0.8058	Intermediate Similarity	NPC274458
0.8037	Intermediate Similarity	NPC108682
0.8037	Intermediate Similarity	NPC469959
0.8037	Intermediate Similarity	NPC472263
0.8037	Intermediate Similarity	NPC469957
0.8036	Intermediate Similarity	NPC475305
0.7982	Intermediate Similarity	NPC79579
0.7965	Intermediate Similarity	NPC475401
0.7944	Intermediate Similarity	NPC54737
0.7925	Intermediate Similarity	NPC473624
0.7905	Intermediate Similarity	NPC471401
0.7895	Intermediate Similarity	NPC477092
0.7857	Intermediate Similarity	NPC326542
0.7857	Intermediate Similarity	NPC238667
0.7838	Intermediate Similarity	NPC126691
0.7822	Intermediate Similarity	NPC475441
0.7818	Intermediate Similarity	NPC76084
0.781	Intermediate Similarity	NPC13743
0.781	Intermediate Similarity	NPC98813
0.7807	Intermediate Similarity	NPC153440
0.7759	Intermediate Similarity	NPC310511
0.7748	Intermediate Similarity	NPC475495
0.7739	Intermediate Similarity	NPC5292
0.7731	Intermediate Similarity	NPC287423
0.7727	Intermediate Similarity	NPC139838
0.7727	Intermediate Similarity	NPC59489
0.7719	Intermediate Similarity	NPC474518
0.7714	Intermediate Similarity	NPC222303
0.7714	Intermediate Similarity	NPC65700
0.7706	Intermediate Similarity	NPC144459
0.7692	Intermediate Similarity	NPC107493
0.7679	Intermediate Similarity	NPC473522
0.7679	Intermediate Similarity	NPC475277
0.7679	Intermediate Similarity	NPC477093
0.7679	Intermediate Similarity	NPC207251
0.7672	Intermediate Similarity	NPC474585
0.7664	Intermediate Similarity	NPC70369
0.7658	Intermediate Similarity	NPC5103
0.7658	Intermediate Similarity	NPC206595
0.7642	Intermediate Similarity	NPC471381
0.7642	Intermediate Similarity	NPC280963
0.7636	Intermediate Similarity	NPC329417
0.7636	Intermediate Similarity	NPC177064
0.7636	Intermediate Similarity	NPC472825
0.7632	Intermediate Similarity	NPC190286
0.7632	Intermediate Similarity	NPC298278
0.7627	Intermediate Similarity	NPC469789
0.7619	Intermediate Similarity	NPC91695
0.7619	Intermediate Similarity	NPC70145
0.7615	Intermediate Similarity	NPC243998
0.7615	Intermediate Similarity	NPC60681
0.7611	Intermediate Similarity	NPC287075
0.7607	Intermediate Similarity	NPC46570
0.7607	Intermediate Similarity	NPC472000
0.7607	Intermediate Similarity	NPC472001
0.7607	Intermediate Similarity	NPC471999
0.7596	Intermediate Similarity	NPC270013
0.7596	Intermediate Similarity	NPC37408
0.7596	Intermediate Similarity	NPC316215
0.7596	Intermediate Similarity	NPC14961
0.7593	Intermediate Similarity	NPC474775
0.7586	Intermediate Similarity	NPC472667
0.7586	Intermediate Similarity	NPC475041
0.7586	Intermediate Similarity	NPC270850
0.7586	Intermediate Similarity	NPC305260
0.7573	Intermediate Similarity	NPC212486
0.7573	Intermediate Similarity	NPC125180
0.757	Intermediate Similarity	NPC207885
0.757	Intermediate Similarity	NPC171759
0.757	Intermediate Similarity	NPC150923
0.757	Intermediate Similarity	NPC477950
0.7568	Intermediate Similarity	NPC471400
0.7568	Intermediate Similarity	NPC470257
0.7563	Intermediate Similarity	NPC81736
0.7563	Intermediate Similarity	NPC172154
0.7547	Intermediate Similarity	NPC109556
0.7547	Intermediate Similarity	NPC221615
0.7547	Intermediate Similarity	NPC473326
0.7547	Intermediate Similarity	NPC23364
0.7545	Intermediate Similarity	NPC83744
0.7545	Intermediate Similarity	NPC470192
0.7544	Intermediate Similarity	NPC178289
0.7544	Intermediate Similarity	NPC474181
0.7524	Intermediate Similarity	NPC18019
0.7524	Intermediate Similarity	NPC476315
0.7524	Intermediate Similarity	NPC24956
0.7523	Intermediate Similarity	NPC296950
0.7523	Intermediate Similarity	NPC258532
0.7522	Intermediate Similarity	NPC236217
0.7521	Intermediate Similarity	NPC143755
0.75	Intermediate Similarity	NPC185530
0.75	Intermediate Similarity	NPC193741
0.75	Intermediate Similarity	NPC81386
0.75	Intermediate Similarity	NPC57405
0.75	Intermediate Similarity	NPC253906
0.75	Intermediate Similarity	NPC474035
0.75	Intermediate Similarity	NPC118405
0.75	Intermediate Similarity	NPC293112
0.75	Intermediate Similarity	NPC303942
0.7479	Intermediate Similarity	NPC204812
0.7479	Intermediate Similarity	NPC11895
0.7478	Intermediate Similarity	NPC106228
0.7478	Intermediate Similarity	NPC138372
0.7478	Intermediate Similarity	NPC148458
0.7477	Intermediate Similarity	NPC65941
0.7477	Intermediate Similarity	NPC288876
0.7477	Intermediate Similarity	NPC186861
0.7477	Intermediate Similarity	NPC474720
0.7476	Intermediate Similarity	NPC221282
0.7476	Intermediate Similarity	NPC476705
0.7476	Intermediate Similarity	NPC472705
0.7459	Intermediate Similarity	NPC470880
0.7458	Intermediate Similarity	NPC67569
0.7456	Intermediate Similarity	NPC962
0.7456	Intermediate Similarity	NPC469496
0.7456	Intermediate Similarity	NPC194100
0.7456	Intermediate Similarity	NPC469463
0.7456	Intermediate Similarity	NPC469454
0.7456	Intermediate Similarity	NPC250109
0.7455	Intermediate Similarity	NPC150531
0.7455	Intermediate Similarity	NPC97202
0.7455	Intermediate Similarity	NPC49958
0.7455	Intermediate Similarity	NPC314244
0.7455	Intermediate Similarity	NPC260268
0.7455	Intermediate Similarity	NPC476027
0.7455	Intermediate Similarity	NPC214264
0.7455	Intermediate Similarity	NPC302607
0.7455	Intermediate Similarity	NPC319077
0.7455	Intermediate Similarity	NPC50692
0.7455	Intermediate Similarity	NPC48733
0.7455	Intermediate Similarity	NPC296945
0.7455	Intermediate Similarity	NPC171137
0.7455	Intermediate Similarity	NPC152695
0.7455	Intermediate Similarity	NPC223450
0.7455	Intermediate Similarity	NPC202167
0.7455	Intermediate Similarity	NPC85829
0.7453	Intermediate Similarity	NPC471150
0.7453	Intermediate Similarity	NPC161493
0.7438	Intermediate Similarity	NPC473253
0.7436	Intermediate Similarity	NPC476960
0.7436	Intermediate Similarity	NPC61520
0.7436	Intermediate Similarity	NPC473203
0.7434	Intermediate Similarity	NPC71680
0.7434	Intermediate Similarity	NPC474846
0.7434	Intermediate Similarity	NPC469655
0.7434	Intermediate Similarity	NPC304180
0.7434	Intermediate Similarity	NPC317107
0.7434	Intermediate Similarity	NPC469656
0.7434	Intermediate Similarity	NPC179798
0.7431	Intermediate Similarity	NPC26478
0.7431	Intermediate Similarity	NPC110989
0.7429	Intermediate Similarity	NPC213698
0.7429	Intermediate Similarity	NPC214694
0.7429	Intermediate Similarity	NPC170120
0.7429	Intermediate Similarity	NPC52044
0.7417	Intermediate Similarity	NPC241456
0.7417	Intermediate Similarity	NPC8369
0.7417	Intermediate Similarity	NPC32868
0.7417	Intermediate Similarity	NPC8374
0.7414	Intermediate Similarity	NPC218970
0.7414	Intermediate Similarity	NPC239273

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 NPC123505 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	1602
0.2-0.3	4038
0.3-0.4	2292
0.4-0.5	604
0.5-0.6	222
0.6-0.7	207
0.7-0.8	13
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
0.7387	Intermediate Similarity	NPD6412	Phase 2
0.7368	Intermediate Similarity	NPD6053	Discontinued
0.7345	Intermediate Similarity	NPD6371	Approved
0.7227	Intermediate Similarity	NPD6319	Approved
0.7227	Intermediate Similarity	NPD6054	Approved
0.7212	Intermediate Similarity	NPD6698	Approved
0.7212	Intermediate Similarity	NPD46	Approved
0.7193	Intermediate Similarity	NPD4634	Approved
0.7182	Intermediate Similarity	NPD5211	Phase 2
0.7167	Intermediate Similarity	NPD6015	Approved
0.7167	Intermediate Similarity	NPD6016	Approved
0.7156	Intermediate Similarity	NPD5286	Approved
0.7156	Intermediate Similarity	NPD5285	Approved
0.7156	Intermediate Similarity	NPD4696	Approved
0.7155	Intermediate Similarity	NPD4632	Approved
0.7143	Intermediate Similarity	NPD6008	Approved
0.713	Intermediate Similarity	NPD4755	Approved
0.7119	Intermediate Similarity	NPD7115	Discovery
0.7107	Intermediate Similarity	NPD6370	Approved
0.7107	Intermediate Similarity	NPD5988	Approved
0.7083	Intermediate Similarity	NPD6059	Approved
0.708	Intermediate Similarity	NPD5697	Approved
0.7073	Intermediate Similarity	NPD7507	Approved
0.7069	Intermediate Similarity	NPD8297	Approved
0.7054	Intermediate Similarity	NPD5141	Approved
0.7027	Intermediate Similarity	NPD5226	Approved
0.7027	Intermediate Similarity	NPD4633	Approved
0.7027	Intermediate Similarity	NPD5224	Approved
0.7027	Intermediate Similarity	NPD5225	Approved
0.7018	Intermediate Similarity	NPD6881	Approved
0.7018	Intermediate Similarity	NPD6899	Approved
0.7018	Intermediate Similarity	NPD6686	Approved
0.7	Intermediate Similarity	NPD4700	Approved
0.6992	Remote Similarity	NPD7492	Approved
0.6991	Remote Similarity	NPD7128	Approved
0.6991	Remote Similarity	NPD6675	Approved
0.6991	Remote Similarity	NPD6402	Approved
0.6991	Remote Similarity	NPD5739	Approved
0.6983	Remote Similarity	NPD6649	Approved
0.6983	Remote Similarity	NPD6650	Approved
0.6975	Remote Similarity	NPD6009	Approved
0.6964	Remote Similarity	NPD5174	Approved
0.6964	Remote Similarity	NPD5175	Approved
0.6961	Remote Similarity	NPD3665	Phase 1
0.6961	Remote Similarity	NPD3133	Approved
0.6961	Remote Similarity	NPD3666	Approved
0.6957	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6012	Approved
0.6957	Remote Similarity	NPD6013	Approved
0.6957	Remote Similarity	NPD6373	Approved
0.6957	Remote Similarity	NPD6372	Approved
0.6957	Remote Similarity	NPD6014	Approved
0.6952	Remote Similarity	NPD4753	Phase 2
0.6944	Remote Similarity	NPD4629	Approved
0.6944	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5210	Approved
0.6937	Remote Similarity	NPD5223	Approved
0.6935	Remote Similarity	NPD6616	Approved
0.693	Remote Similarity	NPD5701	Approved
0.693	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD7604	Phase 2
0.6909	Remote Similarity	NPD7638	Approved
0.6905	Remote Similarity	NPD7319	Approved
0.6897	Remote Similarity	NPD7102	Approved
0.6897	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6883	Approved
0.6897	Remote Similarity	NPD7290	Approved
0.6893	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5785	Approved
0.6885	Remote Similarity	NPD5983	Phase 2
0.688	Remote Similarity	NPD7078	Approved
0.687	Remote Similarity	NPD6011	Approved
0.687	Remote Similarity	NPD7320	Approved
0.6852	Remote Similarity	NPD5282	Discontinued
0.6847	Remote Similarity	NPD7639	Approved
0.6847	Remote Similarity	NPD7640	Approved
0.6838	Remote Similarity	NPD6847	Approved
0.6838	Remote Similarity	NPD6617	Approved
0.6838	Remote Similarity	NPD6869	Approved
0.6838	Remote Similarity	NPD8130	Phase 1
0.6825	Remote Similarity	NPD7736	Approved
0.6818	Remote Similarity	NPD6084	Phase 2
0.6818	Remote Similarity	NPD6083	Phase 2
0.6792	Remote Similarity	NPD1695	Approved
0.6789	Remote Similarity	NPD5695	Phase 3
0.678	Remote Similarity	NPD6882	Approved
0.6765	Remote Similarity	NPD6435	Approved
0.6759	Remote Similarity	NPD4202	Approved
0.6757	Remote Similarity	NPD5696	Approved
0.6746	Remote Similarity	NPD8293	Discontinued
0.6731	Remote Similarity	NPD1694	Approved
0.6724	Remote Similarity	NPD4729	Approved
0.6724	Remote Similarity	NPD4730	Approved
0.6724	Remote Similarity	NPD5128	Approved
0.6696	Remote Similarity	NPD4767	Approved
0.6696	Remote Similarity	NPD4768	Approved
0.6667	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD7260	Phase 2
0.6667	Remote Similarity	NPD3618	Phase 1
0.6667	Remote Similarity	NPD6079	Approved
0.6638	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5328	Approved
0.6613	Remote Similarity	NPD7503	Approved
0.6612	Remote Similarity	NPD6274	Approved
0.661	Remote Similarity	NPD5248	Approved
0.661	Remote Similarity	NPD5249	Phase 3
0.661	Remote Similarity	NPD5247	Approved
0.661	Remote Similarity	NPD5251	Approved
0.661	Remote Similarity	NPD5250	Approved
0.6602	Remote Similarity	NPD4223	Phase 3
0.6602	Remote Similarity	NPD4221	Approved
0.6577	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD4697	Phase 3
0.6577	Remote Similarity	NPD5222	Approved
0.6577	Remote Similarity	NPD5221	Approved
0.6574	Remote Similarity	NPD7838	Discovery
0.6569	Remote Similarity	NPD5368	Approved
0.6562	Remote Similarity	NPD6033	Approved
0.6555	Remote Similarity	NPD5217	Approved
0.6555	Remote Similarity	NPD5216	Approved
0.6555	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD5215	Approved
0.6518	Remote Similarity	NPD5173	Approved
0.6514	Remote Similarity	NPD5281	Approved
0.6514	Remote Similarity	NPD5284	Approved
0.6514	Remote Similarity	NPD5693	Phase 1
0.6509	Remote Similarity	NPD6409	Approved
0.6509	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6684	Approved
0.6509	Remote Similarity	NPD5330	Approved
0.6509	Remote Similarity	NPD7146	Approved
0.6509	Remote Similarity	NPD7521	Approved
0.6509	Remote Similarity	NPD5690	Phase 2
0.6509	Remote Similarity	NPD7334	Approved
0.6504	Remote Similarity	NPD7327	Approved
0.6504	Remote Similarity	NPD7328	Approved
0.648	Remote Similarity	NPD8033	Approved
0.6476	Remote Similarity	NPD4197	Approved
0.6471	Remote Similarity	NPD5169	Approved
0.6471	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5135	Approved
0.6462	Remote Similarity	NPD5956	Approved
0.646	Remote Similarity	NPD4225	Approved
0.646	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6399	Phase 3
0.6452	Remote Similarity	NPD7516	Approved
0.6452	Remote Similarity	NPD4522	Approved
0.6452	Remote Similarity	NPD7101	Approved
0.6452	Remote Similarity	NPD7100	Approved
0.6442	Remote Similarity	NPD3667	Approved
0.6441	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD6317	Approved
0.6417	Remote Similarity	NPD5127	Approved
0.6415	Remote Similarity	NPD5329	Approved
0.6415	Remote Similarity	NPD5363	Approved
0.64	Remote Similarity	NPD8294	Approved
0.64	Remote Similarity	NPD8377	Approved
0.6389	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6903	Approved
0.6378	Remote Similarity	NPD6067	Discontinued
0.6371	Remote Similarity	NPD6313	Approved
0.6371	Remote Similarity	NPD6314	Approved
0.6371	Remote Similarity	NPD6335	Approved
0.6364	Remote Similarity	NPD6845	Suspended
0.6355	Remote Similarity	NPD5279	Phase 3
0.6355	Remote Similarity	NPD4689	Approved
0.6355	Remote Similarity	NPD4138	Approved
0.6355	Remote Similarity	NPD4694	Approved
0.6355	Remote Similarity	NPD4688	Approved
0.6355	Remote Similarity	NPD4249	Approved
0.6355	Remote Similarity	NPD5280	Approved
0.6355	Remote Similarity	NPD5786	Approved
0.6355	Remote Similarity	NPD5205	Approved
0.6355	Remote Similarity	NPD4693	Phase 3
0.6355	Remote Similarity	NPD4690	Approved
0.6349	Remote Similarity	NPD8380	Approved
0.6349	Remote Similarity	NPD8513	Phase 3
0.6349	Remote Similarity	NPD8515	Approved
0.6349	Remote Similarity	NPD8516	Approved
0.6349	Remote Similarity	NPD8517	Approved
0.6349	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD8296	Approved
0.6349	Remote Similarity	NPD8379	Approved
0.6349	Remote Similarity	NPD8335	Approved
0.6349	Remote Similarity	NPD8378	Approved
0.6348	Remote Similarity	NPD5344	Discontinued
0.6339	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD4786	Approved
0.6306	Remote Similarity	NPD5778	Approved
0.6306	Remote Similarity	NPD5779	Approved
0.6296	Remote Similarity	NPD4251	Approved
0.6296	Remote Similarity	NPD4250	Approved
0.6293	Remote Similarity	NPD7632	Discontinued
0.6286	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD1696	Phase 3
0.6262	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.626	Remote Similarity	NPD5167	Approved
0.625	Remote Similarity	NPD4822	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