NPASS Compound

Structure

NPC20144 OpenBabel07101719512D 21 25 0 0 1 0 0 0 0 0999 V2000 1.5699 -3.7299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6453 -3.4762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4797 -0.4967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4797 -1.4555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9362 -0.9109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6493 -0.0173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6493 -1.9349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5171 0.6755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5590 -1.5299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5994 -2.2651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6874 -0.2300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5636 0.7757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3768 -2.3233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8190 -0.4967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9071 -0.2004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8190 -1.4555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3435 -0.9761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3900 -0.8759 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1602 -1.6209 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 1.9071 -1.7518 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 3 4 2 0 0 0 0 3 6 1 0 0 0 0 4 7 1 0 0 0 0 5 9 1 0 0 0 0 5 11 1 0 0 0 0 6 14 2 0 0 0 0 7 16 2 0 0 0 0 8 12 1 0 0 0 0 8 15 1 0 0 0 0 9 19 1 0 0 0 0 10 13 2 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 17 2 0 0 0 0 16 21 1 0 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 19 1 6 0 0 0 18 20 1 0 0 0 0 19 2 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	278.18
Volume:	303.209
LogP:	4.301
LogD:	3.653
LogS:	-3.68
# Rotatable Bonds:	1
TPSA:	8.17
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.758
Synthetic Accessibility Score:	3.897
Fsp3:	0.474
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.887
MDCK Permeability:	2.2542326405528e-05
Pgp-inhibitor:	0.03
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.875
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.996
Plasma Protein Binding (PPB):	84.10796356201172%
Volume Distribution (VD):	2.327
Pgp-substrate:	11.598934173583984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.411
CYP1A2-substrate:	0.533
CYP2C19-inhibitor:	0.227
CYP2C19-substrate:	0.919
CYP2C9-inhibitor:	0.053
CYP2C9-substrate:	0.25
CYP2D6-inhibitor:	0.988
CYP2D6-substrate:	0.9
CYP3A4-inhibitor:	0.93
CYP3A4-substrate:	0.861

ADMET: Excretion

Clearance (CL):	10.286
Half-life (T1/2):	0.236

ADMET: Toxicity

hERG Blockers:	0.643
Human Hepatotoxicity (H-HT):	0.657
Drug-inuced Liver Injury (DILI):	0.104
AMES Toxicity:	0.283
Rat Oral Acute Toxicity:	0.485
Maximum Recommended Daily Dose:	0.982
Skin Sensitization:	0.355
Carcinogencity:	0.754
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.748

Download Data

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

Natural Product: NPC20144

Natural Product ID:	NPC20144
*Common Name:**	VKTOXAGUZWAECL-MOPGFXCFSA-N
IUPAC Name:	n.a.
Synonyms:	(-)-Eburnamenine
Standard InCHIKey:	VKTOXAGUZWAECL-MOPGFXCFSA-N
Standard InCHI:	InChI=1S/C19H22N2/c1-2-19-9-5-11-20-12-8-15-14-6-3-4-7-16(14)21(13-10-19)17(15)18(19)20/h3-4,6-7,10,13,18H,2,5,8-9,11-12H2,1H3/t18-,19+/m1/s1
SMILES:	CC[C@]12CCCN3CCc4c5ccccc5n(C=C1)c4[C@H]23
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1097688
PubChem CID:	15559073
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002671] Eburnan-type alkaloids

*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
NPO33278	melodinus henryi	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20041704]

☑ 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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[548148]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[548148]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[548148]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	>	40000.0	nM	PMID[548148]

☑ 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 NPC20144 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	899
0.1-0.2	6857
0.2-0.3	21390
0.3-0.4	7280
0.4-0.5	2593
0.5-0.6	2192
0.6-0.7	1020
0.7-0.8	370
0.8-0.85	65
0.85-0.9	26
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.8897	High Similarity	NPC40070
0.8794	High Similarity	NPC88097
0.8794	High Similarity	NPC104483
0.875	High Similarity	NPC469525
0.8733	High Similarity	NPC81229
0.8733	High Similarity	NPC255229
0.8553	High Similarity	NPC194881
0.8543	High Similarity	NPC475990
0.8511	High Similarity	NPC198988
0.8472	Intermediate Similarity	NPC2949
0.8467	Intermediate Similarity	NPC476219
0.8451	Intermediate Similarity	NPC325252
0.8392	Intermediate Similarity	NPC251722
0.8392	Intermediate Similarity	NPC150259
0.8392	Intermediate Similarity	NPC314102
0.8378	Intermediate Similarity	NPC21605
0.8323	Intermediate Similarity	NPC195507
0.8323	Intermediate Similarity	NPC2165
0.8301	Intermediate Similarity	NPC474880
0.8301	Intermediate Similarity	NPC221786
0.8288	Intermediate Similarity	NPC473868
0.8288	Intermediate Similarity	NPC63157
0.8267	Intermediate Similarity	NPC33421
0.8258	Intermediate Similarity	NPC478182
0.825	Intermediate Similarity	NPC326575
0.8247	Intermediate Similarity	NPC229173
0.8227	Intermediate Similarity	NPC22079
0.8219	Intermediate Similarity	NPC59084
0.8209	Intermediate Similarity	NPC81561
0.8141	Intermediate Similarity	NPC469541
0.8134	Intermediate Similarity	NPC148140
0.8133	Intermediate Similarity	NPC470111
0.8105	Intermediate Similarity	NPC476297
0.8092	Intermediate Similarity	NPC470233
0.8086	Intermediate Similarity	NPC133261
0.8069	Intermediate Similarity	NPC218268
0.8067	Intermediate Similarity	NPC478186
0.8065	Intermediate Similarity	NPC293487
0.8052	Intermediate Similarity	NPC51054
0.8039	Intermediate Similarity	NPC281094
0.8027	Intermediate Similarity	NPC73767
0.8025	Intermediate Similarity	NPC21174
0.8025	Intermediate Similarity	NPC271797
0.8015	Intermediate Similarity	NPC54102
0.8015	Intermediate Similarity	NPC162689
0.8013	Intermediate Similarity	NPC179787
0.8013	Intermediate Similarity	NPC201380
0.8	Intermediate Similarity	NPC476566
0.8	Intermediate Similarity	NPC129721
0.8	Intermediate Similarity	NPC204141
0.8	Intermediate Similarity	NPC470440
0.7986	Intermediate Similarity	NPC46358
0.7973	Intermediate Similarity	NPC469768
0.7973	Intermediate Similarity	NPC469767
0.7973	Intermediate Similarity	NPC469779
0.7973	Intermediate Similarity	NPC469784
0.7973	Intermediate Similarity	NPC469783
0.7973	Intermediate Similarity	NPC469761
0.7973	Intermediate Similarity	NPC469780
0.7973	Intermediate Similarity	NPC115611
0.7963	Intermediate Similarity	NPC24594
0.7963	Intermediate Similarity	NPC472122
0.7963	Intermediate Similarity	NPC280852
0.7961	Intermediate Similarity	NPC321911
0.7961	Intermediate Similarity	NPC37548
0.7949	Intermediate Similarity	NPC206819
0.7949	Intermediate Similarity	NPC318065
0.7949	Intermediate Similarity	NPC56765
0.7947	Intermediate Similarity	NPC63545
0.7937	Intermediate Similarity	NPC474897
0.7929	Intermediate Similarity	NPC122718
0.7925	Intermediate Similarity	NPC478183
0.7922	Intermediate Similarity	NPC325903
0.7919	Intermediate Similarity	NPC469766
0.7911	Intermediate Similarity	NPC478184
0.7905	Intermediate Similarity	NPC110126
0.7899	Intermediate Similarity	NPC215519
0.7895	Intermediate Similarity	NPC469811
0.7891	Intermediate Similarity	NPC84911
0.7852	Intermediate Similarity	NPC238499
0.7848	Intermediate Similarity	NPC478185
0.7843	Intermediate Similarity	NPC187951
0.784	Intermediate Similarity	NPC472123
0.7834	Intermediate Similarity	NPC41257
0.7834	Intermediate Similarity	NPC477591
0.7826	Intermediate Similarity	NPC91895
0.7823	Intermediate Similarity	NPC29886
0.7823	Intermediate Similarity	NPC96102
0.7823	Intermediate Similarity	NPC261195
0.7818	Intermediate Similarity	NPC187827
0.7818	Intermediate Similarity	NPC472105
0.7815	Intermediate Similarity	NPC242556
0.7812	Intermediate Similarity	NPC56233
0.7793	Intermediate Similarity	NPC475450
0.7785	Intermediate Similarity	NPC122141
0.7784	Intermediate Similarity	NPC258480
0.7771	Intermediate Similarity	NPC286427
0.777	Intermediate Similarity	NPC105127
0.777	Intermediate Similarity	NPC125746
0.7764	Intermediate Similarity	NPC317430
0.7756	Intermediate Similarity	NPC38736
0.7756	Intermediate Similarity	NPC470507
0.7736	Intermediate Similarity	NPC225018
0.773	Intermediate Similarity	NPC161861
0.7725	Intermediate Similarity	NPC143533
0.7725	Intermediate Similarity	NPC472109
0.7725	Intermediate Similarity	NPC472110
0.7725	Intermediate Similarity	NPC472104
0.7722	Intermediate Similarity	NPC6436
0.7718	Intermediate Similarity	NPC169433
0.7716	Intermediate Similarity	NPC32534
0.7714	Intermediate Similarity	NPC182570
0.7714	Intermediate Similarity	NPC48564
0.7714	Intermediate Similarity	NPC265605
0.7712	Intermediate Similarity	NPC143872
0.7711	Intermediate Similarity	NPC15840
0.7707	Intermediate Similarity	NPC285469
0.7692	Intermediate Similarity	NPC66210
0.7692	Intermediate Similarity	NPC250361
0.7679	Intermediate Similarity	NPC472294
0.7677	Intermediate Similarity	NPC53947
0.7676	Intermediate Similarity	NPC476322
0.766	Intermediate Similarity	NPC41174
0.7658	Intermediate Similarity	NPC236711
0.7655	Intermediate Similarity	NPC473587
0.7647	Intermediate Similarity	NPC86288
0.7647	Intermediate Similarity	NPC314372
0.7633	Intermediate Similarity	NPC79062
0.7633	Intermediate Similarity	NPC472107
0.7632	Intermediate Similarity	NPC190296
0.7626	Intermediate Similarity	NPC91958
0.7625	Intermediate Similarity	NPC470203
0.7619	Intermediate Similarity	NPC473930
0.7616	Intermediate Similarity	NPC279081
0.7616	Intermediate Similarity	NPC284635
0.7613	Intermediate Similarity	NPC124005
0.7613	Intermediate Similarity	NPC2272
0.7609	Intermediate Similarity	NPC192209
0.7607	Intermediate Similarity	NPC194411
0.7607	Intermediate Similarity	NPC65080
0.7603	Intermediate Similarity	NPC69914
0.7603	Intermediate Similarity	NPC475428
0.7597	Intermediate Similarity	NPC288838
0.7586	Intermediate Similarity	NPC473762
0.7578	Intermediate Similarity	NPC317105
0.7578	Intermediate Similarity	NPC90723
0.7574	Intermediate Similarity	NPC472119
0.7566	Intermediate Similarity	NPC277157
0.7564	Intermediate Similarity	NPC105818
0.7564	Intermediate Similarity	NPC24678
0.7562	Intermediate Similarity	NPC470204
0.7562	Intermediate Similarity	NPC215584
0.7562	Intermediate Similarity	NPC44773
0.7554	Intermediate Similarity	NPC297486
0.7554	Intermediate Similarity	NPC240136
0.7554	Intermediate Similarity	NPC471402
0.7551	Intermediate Similarity	NPC179365
0.7551	Intermediate Similarity	NPC82295
0.755	Intermediate Similarity	NPC315348
0.755	Intermediate Similarity	NPC316811
0.755	Intermediate Similarity	NPC32002
0.7548	Intermediate Similarity	NPC477134
0.7547	Intermediate Similarity	NPC299594
0.7545	Intermediate Similarity	NPC12649
0.7535	Intermediate Similarity	NPC329825
0.7534	Intermediate Similarity	NPC476131
0.7532	Intermediate Similarity	NPC285731
0.7532	Intermediate Similarity	NPC207726
0.753	Intermediate Similarity	NPC121903
0.7516	Intermediate Similarity	NPC16667
0.7515	Intermediate Similarity	NPC472108
0.7515	Intermediate Similarity	NPC139291
0.75	Intermediate Similarity	NPC230002
0.7485	Intermediate Similarity	NPC28848
0.7485	Intermediate Similarity	NPC474561
0.7485	Intermediate Similarity	NPC49954
0.7485	Intermediate Similarity	NPC234987
0.7485	Intermediate Similarity	NPC14325
0.7485	Intermediate Similarity	NPC478077
0.7484	Intermediate Similarity	NPC129042
0.7471	Intermediate Similarity	NPC471386
0.747	Intermediate Similarity	NPC275305
0.747	Intermediate Similarity	NPC37423
0.747	Intermediate Similarity	NPC471579
0.7468	Intermediate Similarity	NPC469763
0.7468	Intermediate Similarity	NPC469760
0.7468	Intermediate Similarity	NPC469786
0.7468	Intermediate Similarity	NPC73952
0.7468	Intermediate Similarity	NPC25008
0.7468	Intermediate Similarity	NPC259644
0.7468	Intermediate Similarity	NPC200743
0.7468	Intermediate Similarity	NPC469765
0.7468	Intermediate Similarity	NPC200214
0.7455	Intermediate Similarity	NPC82331
0.7455	Intermediate Similarity	NPC158129
0.7448	Intermediate Similarity	NPC476140
0.7445	Intermediate Similarity	NPC296163
0.7445	Intermediate Similarity	NPC187036
0.7442	Intermediate Similarity	NPC472323
0.7439	Intermediate Similarity	NPC63751

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 NPC20144 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	386
0.1-0.2	670
0.2-0.3	1049
0.3-0.4	1799
0.4-0.5	2319
0.5-0.6	1909
0.6-0.7	819
0.7-0.8	172
0.8-0.85	21
0.85-0.9	4
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8978	High Similarity	NPD3385	Approved
0.8873	High Similarity	NPD4637	Clinical (unspecified phase)
0.8686	High Similarity	NPD3654	Approved
0.863	High Similarity	NPD4547	Phase 3
0.8611	High Similarity	NPD4047	Discontinued
0.8562	High Similarity	NPD1683	Approved
0.8392	Intermediate Similarity	NPD6554	Approved
0.8392	Intermediate Similarity	NPD45	Approved
0.8302	Intermediate Similarity	NPD5104	Approved
0.8227	Intermediate Similarity	NPD3475	Approved
0.8227	Intermediate Similarity	NPD3476	Approved
0.8182	Intermediate Similarity	NPD3944	Approved
0.8182	Intermediate Similarity	NPD3942	Approved
0.8158	Intermediate Similarity	NPD2837	Discontinued
0.8143	Intermediate Similarity	NPD2119	Approved
0.8143	Intermediate Similarity	NPD2118	Approved
0.8089	Intermediate Similarity	NPD2915	Discontinued
0.8079	Intermediate Similarity	NPD3100	Discontinued
0.8041	Intermediate Similarity	NPD1722	Approved
0.8027	Intermediate Similarity	NPD786	Approved
0.7987	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD2006	Phase 2
0.7975	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD715	Phase 3
0.7962	Intermediate Similarity	NPD5315	Discontinued
0.7961	Intermediate Similarity	NPD2430	Phase 2
0.7961	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD5538	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD5075	Discontinued
0.7947	Intermediate Similarity	NPD7469	Discontinued
0.7945	Intermediate Similarity	NPD1256	Approved
0.7945	Intermediate Similarity	NPD1255	Approved
0.7945	Intermediate Similarity	NPD1254	Approved
0.7945	Intermediate Similarity	NPD1253	Approved
0.7935	Intermediate Similarity	NPD2580	Discontinued
0.7931	Intermediate Similarity	NPD4028	Approved
0.7931	Intermediate Similarity	NPD4029	Approved
0.7931	Intermediate Similarity	NPD4030	Approved
0.7914	Intermediate Similarity	NPD7111	Discontinued
0.7911	Intermediate Similarity	NPD3323	Discontinued
0.7885	Intermediate Similarity	NPD4326	Phase 2
0.7871	Intermediate Similarity	NPD6285	Phase 2
0.7823	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD2150	Discontinued
0.7815	Intermediate Similarity	NPD5254	Discontinued
0.7815	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD2172	Phase 1
0.7785	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD4640	Approved
0.7764	Intermediate Similarity	NPD4639	Approved
0.7764	Intermediate Similarity	NPD4638	Approved
0.775	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD5418	Discontinued
0.7714	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD268	Approved
0.7714	Intermediate Similarity	NPD271	Approved
0.7697	Intermediate Similarity	NPD5671	Approved
0.7697	Intermediate Similarity	NPD4509	Discontinued
0.7697	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD4128	Approved
0.7654	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7394	Phase 2
0.7639	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD991	Phase 2
0.7636	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD2882	Phase 1
0.7625	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD4181	Approved
0.7561	Intermediate Similarity	NPD6828	Phase 2
0.7561	Intermediate Similarity	NPD3609	Approved
0.7561	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD3610	Approved
0.755	Intermediate Similarity	NPD2071	Approved
0.755	Intermediate Similarity	NPD2075	Approved
0.755	Intermediate Similarity	NPD2072	Approved
0.755	Intermediate Similarity	NPD2069	Approved
0.755	Intermediate Similarity	NPD2068	Approved
0.755	Intermediate Similarity	NPD2073	Approved
0.755	Intermediate Similarity	NPD2070	Approved
0.755	Intermediate Similarity	NPD2074	Approved
0.7548	Intermediate Similarity	NPD4703	Approved
0.7548	Intermediate Similarity	NPD4702	Approved
0.7534	Intermediate Similarity	NPD947	Approved
0.7516	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6158	Phase 2
0.7484	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD2466	Phase 3
0.7452	Intermediate Similarity	NPD4463	Approved
0.7452	Intermediate Similarity	NPD2462	Phase 3
0.7452	Intermediate Similarity	NPD2465	Approved
0.7452	Intermediate Similarity	NPD4462	Approved
0.7451	Intermediate Similarity	NPD5020	Approved
0.744	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD2640	Approved
0.7439	Intermediate Similarity	NPD2641	Approved
0.7436	Intermediate Similarity	NPD1661	Suspended
0.7432	Intermediate Similarity	NPD1251	Discontinued
0.7425	Intermediate Similarity	NPD4075	Phase 2
0.7421	Intermediate Similarity	NPD977	Approved
0.7421	Intermediate Similarity	NPD975	Approved
0.7421	Intermediate Similarity	NPD976	Approved
0.7413	Intermediate Similarity	NPD5787	Discontinued
0.7407	Intermediate Similarity	NPD6771	Discontinued
0.7394	Intermediate Similarity	NPD2875	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4602	Approved
0.7381	Intermediate Similarity	NPD3506	Approved
0.7381	Intermediate Similarity	NPD3505	Approved
0.7378	Intermediate Similarity	NPD6794	Approved
0.7375	Intermediate Similarity	NPD3113	Approved
0.7375	Intermediate Similarity	NPD3112	Approved
0.7375	Intermediate Similarity	NPD3114	Approved
0.7375	Intermediate Similarity	NPD3115	Approved
0.7368	Intermediate Similarity	NPD4957	Phase 2
0.7365	Intermediate Similarity	NPD5065	Approved
0.7341	Intermediate Similarity	NPD3961	Discontinued
0.7337	Intermediate Similarity	NPD4079	Approved
0.7337	Intermediate Similarity	NPD4076	Approved
0.7333	Intermediate Similarity	NPD5021	Discontinued
0.7329	Intermediate Similarity	NPD9583	Approved
0.7329	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6497	Approved
0.7317	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD2720	Phase 1
0.7312	Intermediate Similarity	NPD2165	Phase 1
0.7305	Intermediate Similarity	NPD7217	Approved
0.7305	Intermediate Similarity	NPD7216	Approved
0.7303	Intermediate Similarity	NPD1262	Discovery
0.7292	Intermediate Similarity	NPD1561	Phase 2
0.7292	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD5255	Approved
0.7279	Intermediate Similarity	NPD4116	Approved
0.7273	Intermediate Similarity	NPD3929	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4811	Discontinued
0.7267	Intermediate Similarity	NPD1993	Approved
0.7267	Intermediate Similarity	NPD5892	Approved
0.7267	Intermediate Similarity	NPD1994	Approved
0.7267	Intermediate Similarity	NPD1995	Approved
0.7267	Intermediate Similarity	NPD2927	Phase 3
0.7262	Intermediate Similarity	NPD3859	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7006	Approved
0.7239	Intermediate Similarity	NPD1403	Approved
0.7239	Intermediate Similarity	NPD1404	Approved
0.7234	Intermediate Similarity	NPD7480	Approved
0.7234	Intermediate Similarity	NPD7481	Approved
0.7229	Intermediate Similarity	NPD2333	Discontinued
0.7229	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2406	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6044	Discontinued
0.7212	Intermediate Similarity	NPD1313	Approved
0.7212	Intermediate Similarity	NPD509	Phase 3
0.7208	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3630	Approved
0.7197	Intermediate Similarity	NPD3629	Approved
0.7195	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD9357	Approved
0.7191	Intermediate Similarity	NPD7619	Phase 3
0.7191	Intermediate Similarity	NPD7618	Phase 3
0.7186	Intermediate Similarity	NPD5436	Phase 1
0.7184	Intermediate Similarity	NPD3378	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5444	Phase 1
0.7179	Intermediate Similarity	NPD4510	Discontinued
0.7171	Intermediate Similarity	NPD2141	Approved
0.7171	Intermediate Similarity	NPD4880	Discontinued
0.7171	Intermediate Similarity	NPD2142	Approved
0.7171	Intermediate Similarity	NPD2140	Approved
0.7169	Intermediate Similarity	NPD2639	Approved
0.7169	Intermediate Similarity	NPD2642	Approved
0.7168	Intermediate Similarity	NPD7564	Discontinued
0.7159	Intermediate Similarity	NPD6281	Approved
0.7159	Intermediate Similarity	NPD4499	Approved
0.7143	Intermediate Similarity	NPD3339	Approved
0.7143	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6074	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5862	Discovery
0.7126	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD3348	Phase 2
0.7117	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD5473	Discontinued
0.7091	Intermediate Similarity	NPD2149	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4384	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD4902	Discontinued
0.7086	Intermediate Similarity	NPD803	Phase 1
0.7086	Intermediate Similarity	NPD6217	Discontinued
0.7083	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD1721	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD4615	Phase 2
0.7076	Intermediate Similarity	NPD4398	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4985	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD6469	Phase 3
0.7072	Intermediate Similarity	NPD6468	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