NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	251.14
Volume:	268.238
LogP:	2.264
LogD:	2.584
LogS:	-1.682
# Rotatable Bonds:	0
TPSA:	29.85
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.665
Synthetic Accessibility Score:	3.232
Fsp3:	0.312
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.952
MDCK Permeability:	1.7975742593989708e-05
Pgp-inhibitor:	0.549
Pgp-substrate:	0.841
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.064
30% Bioavailability (F30%):	0.545

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.905
Plasma Protein Binding (PPB):	76.54447174072266%
Volume Distribution (VD):	2.041
Pgp-substrate:	23.04616928100586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.978
CYP1A2-substrate:	0.891
CYP2C19-inhibitor:	0.168
CYP2C19-substrate:	0.802
CYP2C9-inhibitor:	0.054
CYP2C9-substrate:	0.408
CYP2D6-inhibitor:	0.554
CYP2D6-substrate:	0.87
CYP3A4-inhibitor:	0.118
CYP3A4-substrate:	0.638

ADMET: Excretion

Clearance (CL):	7.12
Half-life (T1/2):	0.4

ADMET: Toxicity

hERG Blockers:	0.728
Human Hepatotoxicity (H-HT):	0.914
Drug-inuced Liver Injury (DILI):	0.1
AMES Toxicity:	0.84
Rat Oral Acute Toxicity:	0.799
Maximum Recommended Daily Dose:	0.948
Skin Sensitization:	0.042
Carcinogencity:	0.11
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.9

Download Data

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

Natural Product: NPC476219

Natural Product ID:	NPC476219
*Common Name:**	Tabernine A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VBMLQDYYOPHOCB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H17N3/c1-10-9-13-12-5-3-4-6-14(12)18-16(13)15-7-8-17-11(2)19(10)15/h3-6,9,11,17H,7-8H2,1-2H3
SMILES:	CC1NCCc2n1c(C)cc1c2nc2c1cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL555046
PubChem CID:	44179503
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001213] Pyridoindoles [CHEMONTID:0001914] Beta carbolines

*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
NPO32684	tabernaemontana elegans	Species	Apocynaceae	Eukaryota	leaves	n.a.	n.a.	PMID[19473031]
NPO32684	tabernaemontana elegans	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27704811]

☑ 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	6

Activity Type	# Activity
Cell Line	2
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	ID50	=	45.9	uM	PMID[497254]
NPT1864	Cell Line	L5178Y	Mus musculus	ID50	=	37.5	uM	PMID[497254]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Flu intensity	=	18.5	n.a.	PMID[497254]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio	=	1.73	n.a.	PMID[497254]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Flu intensity	=	7.7	n.a.	PMID[497254]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio	=	0.72	n.a.	PMID[497254]

☑ 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 NPC476219 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	1098
0.1-0.2	14396
0.2-0.3	17351
0.3-0.4	4319
0.4-0.5	2407
0.5-0.6	1874
0.6-0.7	955
0.7-0.8	249
0.8-0.85	45
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9589	High Similarity	NPC476297
0.8836	High Similarity	NPC115611
0.8639	High Similarity	NPC88097
0.8553	High Similarity	NPC321911
0.8535	High Similarity	NPC470203
0.8506	High Similarity	NPC325903
0.8497	Intermediate Similarity	NPC40070
0.8493	Intermediate Similarity	NPC198988
0.8487	Intermediate Similarity	NPC179787
0.8487	Intermediate Similarity	NPC469811
0.8487	Intermediate Similarity	NPC201380
0.8471	Intermediate Similarity	NPC470204
0.8467	Intermediate Similarity	NPC20144
0.8435	Intermediate Similarity	NPC325252
0.8428	Intermediate Similarity	NPC2165
0.8428	Intermediate Similarity	NPC195507
0.8421	Intermediate Similarity	NPC63545
0.8366	Intermediate Similarity	NPC21605
0.8355	Intermediate Similarity	NPC204141
0.8354	Intermediate Similarity	NPC122141
0.8333	Intermediate Similarity	NPC59084
0.8333	Intermediate Similarity	NPC284635
0.8291	Intermediate Similarity	NPC221786
0.8291	Intermediate Similarity	NPC475990
0.8291	Intermediate Similarity	NPC474880
0.8278	Intermediate Similarity	NPC473868
0.8278	Intermediate Similarity	NPC63157
0.825	Intermediate Similarity	NPC317105
0.8239	Intermediate Similarity	NPC229173
0.8212	Intermediate Similarity	NPC2949
0.8205	Intermediate Similarity	NPC470233
0.8187	Intermediate Similarity	NPC225018
0.8182	Intermediate Similarity	NPC280852
0.8129	Intermediate Similarity	NPC470111
0.8113	Intermediate Similarity	NPC236711
0.8067	Intermediate Similarity	NPC218268
0.8026	Intermediate Similarity	NPC73767
0.8026	Intermediate Similarity	NPC104483
0.8026	Intermediate Similarity	NPC110126
0.8025	Intermediate Similarity	NPC478182
0.8025	Intermediate Similarity	NPC478184
0.8	Intermediate Similarity	NPC82331
0.8	Intermediate Similarity	NPC470440
0.7974	Intermediate Similarity	NPC469768
0.7974	Intermediate Similarity	NPC469767
0.7974	Intermediate Similarity	NPC469779
0.7974	Intermediate Similarity	NPC469784
0.7974	Intermediate Similarity	NPC469783
0.7974	Intermediate Similarity	NPC469761
0.7974	Intermediate Similarity	NPC469780
0.7973	Intermediate Similarity	NPC22079
0.7964	Intermediate Similarity	NPC474958
0.7949	Intermediate Similarity	NPC478186
0.7939	Intermediate Similarity	NPC474897
0.7922	Intermediate Similarity	NPC469766
0.7919	Intermediate Similarity	NPC475450
0.7914	Intermediate Similarity	NPC271797
0.7914	Intermediate Similarity	NPC21174
0.7911	Intermediate Similarity	NPC53947
0.7911	Intermediate Similarity	NPC33421
0.7907	Intermediate Similarity	NPC141612
0.7907	Intermediate Similarity	NPC17273
0.7907	Intermediate Similarity	NPC135601
0.7904	Intermediate Similarity	NPC471579
0.7904	Intermediate Similarity	NPC317054
0.7895	Intermediate Similarity	NPC251722
0.7895	Intermediate Similarity	NPC314102
0.7895	Intermediate Similarity	NPC84911
0.7895	Intermediate Similarity	NPC105127
0.7882	Intermediate Similarity	NPC307191
0.784	Intermediate Similarity	NPC56765
0.784	Intermediate Similarity	NPC477591
0.784	Intermediate Similarity	NPC293487
0.7834	Intermediate Similarity	NPC288838
0.7829	Intermediate Similarity	NPC261195
0.7829	Intermediate Similarity	NPC96102
0.7829	Intermediate Similarity	NPC29886
0.7823	Intermediate Similarity	NPC250361
0.7818	Intermediate Similarity	NPC56233
0.7791	Intermediate Similarity	NPC255229
0.7791	Intermediate Similarity	NPC108011
0.7791	Intermediate Similarity	NPC81229
0.7785	Intermediate Similarity	NPC473587
0.7778	Intermediate Similarity	NPC150259
0.7778	Intermediate Similarity	NPC125746
0.7771	Intermediate Similarity	NPC231536
0.7758	Intermediate Similarity	NPC274229
0.7748	Intermediate Similarity	NPC473930
0.7733	Intermediate Similarity	NPC475428
0.7722	Intermediate Similarity	NPC143872
0.7718	Intermediate Similarity	NPC473762
0.7711	Intermediate Similarity	NPC478183
0.7697	Intermediate Similarity	NPC247987
0.7692	Intermediate Similarity	NPC81561
0.7683	Intermediate Similarity	NPC215584
0.7683	Intermediate Similarity	NPC44773
0.7682	Intermediate Similarity	NPC179365
0.7671	Intermediate Similarity	NPC41174
0.7669	Intermediate Similarity	NPC216643
0.7665	Intermediate Similarity	NPC317430
0.7658	Intermediate Similarity	NPC314372
0.7643	Intermediate Similarity	NPC190296
0.7639	Intermediate Similarity	NPC162689
0.7639	Intermediate Similarity	NPC54102
0.7636	Intermediate Similarity	NPC478185
0.7636	Intermediate Similarity	NPC194881
0.7633	Intermediate Similarity	NPC472123
0.7633	Intermediate Similarity	NPC161861
0.763	Intermediate Similarity	NPC472109
0.763	Intermediate Similarity	NPC472110
0.7628	Intermediate Similarity	NPC279081
0.7622	Intermediate Similarity	NPC206819
0.7622	Intermediate Similarity	NPC318065
0.7622	Intermediate Similarity	NPC148140
0.7619	Intermediate Similarity	NPC91895
0.7619	Intermediate Similarity	NPC97343
0.759	Intermediate Similarity	NPC90723
0.7578	Intermediate Similarity	NPC105818
0.7578	Intermediate Similarity	NPC24678
0.7568	Intermediate Similarity	NPC122718
0.7566	Intermediate Similarity	NPC82295
0.7561	Intermediate Similarity	NPC286427
0.7516	Intermediate Similarity	NPC230002
0.7516	Intermediate Similarity	NPC2272
0.7515	Intermediate Similarity	NPC135141
0.7515	Intermediate Similarity	NPC32534
0.7515	Intermediate Similarity	NPC92796
0.7515	Intermediate Similarity	NPC41257
0.75	Intermediate Similarity	NPC476566
0.7486	Intermediate Similarity	NPC472294
0.7485	Intermediate Similarity	NPC469760
0.7485	Intermediate Similarity	NPC200214
0.7485	Intermediate Similarity	NPC469763
0.7485	Intermediate Similarity	NPC73952
0.7485	Intermediate Similarity	NPC469765
0.7485	Intermediate Similarity	NPC469786
0.7485	Intermediate Similarity	NPC25008
0.7485	Intermediate Similarity	NPC259644
0.7473	Intermediate Similarity	NPC265576
0.7453	Intermediate Similarity	NPC114209
0.7453	Intermediate Similarity	NPC471957
0.7452	Intermediate Similarity	NPC312092
0.7439	Intermediate Similarity	NPC212376
0.7439	Intermediate Similarity	NPC211572
0.7439	Intermediate Similarity	NPC80597
0.7439	Intermediate Similarity	NPC70922
0.7439	Intermediate Similarity	NPC75540
0.7438	Intermediate Similarity	NPC86288
0.7438	Intermediate Similarity	NPC469525
0.7438	Intermediate Similarity	NPC159856
0.7415	Intermediate Similarity	NPC215519
0.7414	Intermediate Similarity	NPC16659
0.7407	Intermediate Similarity	NPC37548
0.74	Intermediate Similarity	NPC146373
0.74	Intermediate Similarity	NPC166424
0.74	Intermediate Similarity	NPC245244
0.7394	Intermediate Similarity	NPC476464
0.7383	Intermediate Similarity	NPC46358
0.7375	Intermediate Similarity	NPC242556
0.7374	Intermediate Similarity	NPC324091
0.7371	Intermediate Similarity	NPC191415
0.7368	Intermediate Similarity	NPC201634
0.7356	Intermediate Similarity	NPC265710
0.7356	Intermediate Similarity	NPC12649
0.7346	Intermediate Similarity	NPC477134
0.7345	Intermediate Similarity	NPC133003
0.7341	Intermediate Similarity	NPC472122
0.7341	Intermediate Similarity	NPC24594
0.7333	Intermediate Similarity	NPC34844
0.7333	Intermediate Similarity	NPC27740
0.733	Intermediate Similarity	NPC139291
0.733	Intermediate Similarity	NPC472108
0.7317	Intermediate Similarity	NPC470823
0.731	Intermediate Similarity	NPC194411
0.7305	Intermediate Similarity	NPC300238
0.7299	Intermediate Similarity	NPC326575
0.7299	Intermediate Similarity	NPC240088
0.7299	Intermediate Similarity	NPC473380
0.7294	Intermediate Similarity	NPC49217
0.7289	Intermediate Similarity	NPC469785
0.7288	Intermediate Similarity	NPC284678
0.7283	Intermediate Similarity	NPC329688
0.7283	Intermediate Similarity	NPC189812
0.7283	Intermediate Similarity	NPC297034
0.7278	Intermediate Similarity	NPC169433
0.7273	Intermediate Similarity	NPC69914
0.7273	Intermediate Similarity	NPC141926
0.7273	Intermediate Similarity	NPC281094
0.7257	Intermediate Similarity	NPC133261
0.7256	Intermediate Similarity	NPC148592
0.7251	Intermediate Similarity	NPC63751
0.7246	Intermediate Similarity	NPC469762
0.7246	Intermediate Similarity	NPC129721
0.7232	Intermediate Similarity	NPC470205
0.7232	Intermediate Similarity	NPC48938
0.7232	Intermediate Similarity	NPC102755
0.7229	Intermediate Similarity	NPC470507
0.7229	Intermediate Similarity	NPC38736
0.7226	Intermediate Similarity	NPC101165
0.7225	Intermediate Similarity	NPC477611

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 NPC476219 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	378
0.1-0.2	964
0.2-0.3	931
0.3-0.4	1906
0.4-0.5	2204
0.5-0.6	1890
0.6-0.7	732
0.7-0.8	137
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9103	High Similarity	NPD4637	Clinical (unspecified phase)
0.8681	High Similarity	NPD3385	Approved
0.8543	High Similarity	NPD1683	Approved
0.8528	High Similarity	NPD3341	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD2150	Discontinued
0.8397	Intermediate Similarity	NPD2927	Phase 3
0.8387	Intermediate Similarity	NPD2837	Discontinued
0.8366	Intermediate Similarity	NPD4547	Phase 3
0.8276	Intermediate Similarity	NPD3654	Approved
0.8225	Intermediate Similarity	NPD3378	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD1313	Approved
0.8133	Intermediate Similarity	NPD6554	Approved
0.8133	Intermediate Similarity	NPD45	Approved
0.8092	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD509	Phase 3
0.8067	Intermediate Similarity	NPD1256	Approved
0.8067	Intermediate Similarity	NPD1254	Approved
0.8067	Intermediate Similarity	NPD1255	Approved
0.8067	Intermediate Similarity	NPD1253	Approved
0.8049	Intermediate Similarity	NPD2875	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD1722	Approved
0.8024	Intermediate Similarity	NPD7111	Discontinued
0.8	Intermediate Similarity	NPD6828	Phase 2
0.8	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD5254	Discontinued
0.7929	Intermediate Similarity	NPD5962	Phase 2
0.7908	Intermediate Similarity	NPD786	Approved
0.7886	Intermediate Similarity	NPD4615	Phase 2
0.7882	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD4047	Discontinued
0.787	Intermediate Similarity	NPD2930	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD7394	Phase 2
0.7853	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD715	Phase 3
0.7848	Intermediate Similarity	NPD3100	Discontinued
0.7848	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD5671	Approved
0.7818	Intermediate Similarity	NPD6794	Approved
0.7805	Intermediate Similarity	NPD3323	Discontinued
0.7778	Intermediate Similarity	NPD1895	Discontinued
0.7771	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD2333	Discontinued
0.7765	Intermediate Similarity	NPD6469	Phase 3
0.7765	Intermediate Similarity	NPD6468	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD977	Approved
0.7764	Intermediate Similarity	NPD975	Approved
0.7764	Intermediate Similarity	NPD976	Approved
0.7758	Intermediate Similarity	NPD1333	Phase 3
0.7756	Intermediate Similarity	NPD2006	Phase 2
0.7751	Intermediate Similarity	NPD2406	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD1016	Phase 2
0.7744	Intermediate Similarity	NPD1015	Phase 2
0.774	Intermediate Similarity	NPD3485	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD5538	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD2430	Phase 2
0.7719	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD1215	Discontinued
0.7709	Intermediate Similarity	NPD2880	Discontinued
0.7709	Intermediate Similarity	NPD5462	Discontinued
0.7701	Intermediate Similarity	NPD2591	Phase 2
0.7692	Intermediate Similarity	NPD7006	Approved
0.7688	Intermediate Similarity	NPD4463	Approved
0.7688	Intermediate Similarity	NPD4462	Approved
0.7679	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD4326	Phase 2
0.7667	Intermediate Similarity	NPD947	Approved
0.7665	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD6285	Phase 2
0.7651	Intermediate Similarity	NPD1002	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD3475	Approved
0.7616	Intermediate Similarity	NPD3476	Approved
0.7602	Intermediate Similarity	NPD4181	Approved
0.76	Intermediate Similarity	NPD4902	Discontinued
0.7595	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD3799	Suspended
0.7584	Intermediate Similarity	NPD7722	Suspended
0.7582	Intermediate Similarity	NPD3942	Approved
0.7582	Intermediate Similarity	NPD3944	Approved
0.7582	Intermediate Similarity	NPD6816	Phase 3
0.7578	Intermediate Similarity	NPD2172	Phase 1
0.7576	Intermediate Similarity	NPD6074	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD5021	Discontinued
0.7558	Intermediate Similarity	NPD40	Phase 2
0.7558	Intermediate Similarity	NPD5730	Phase 2
0.7548	Intermediate Similarity	NPD1262	Discovery
0.7545	Intermediate Similarity	NPD3889	Approved
0.7533	Intermediate Similarity	NPD2119	Approved
0.7533	Intermediate Similarity	NPD991	Phase 2
0.7533	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD2118	Approved
0.753	Intermediate Similarity	NPD2149	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD6761	Discontinued
0.7528	Intermediate Similarity	NPD3419	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD5436	Phase 1
0.7514	Intermediate Similarity	NPD3830	Phase 1
0.75	Intermediate Similarity	NPD2478	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2580	Discontinued
0.7487	Intermediate Similarity	NPD2443	Approved
0.7487	Intermediate Similarity	NPD2442	Approved
0.7485	Intermediate Similarity	NPD4128	Approved
0.7485	Intermediate Similarity	NPD5065	Approved
0.7484	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD4023	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD6271	Approved
0.7471	Intermediate Similarity	NPD3610	Approved
0.7471	Intermediate Similarity	NPD5806	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD3609	Approved
0.7459	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7023	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD2640	Approved
0.7456	Intermediate Similarity	NPD2641	Approved
0.7455	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD803	Phase 1
0.744	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD2165	Phase 1
0.7432	Intermediate Similarity	NPD5787	Discontinued
0.7429	Intermediate Similarity	NPD4441	Phase 2
0.7427	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD2480	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD2524	Discontinued
0.7414	Intermediate Similarity	NPD1873	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD702	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD5418	Discontinued
0.7401	Intermediate Similarity	NPD6721	Phase 1
0.7401	Intermediate Similarity	NPD2793	Discontinued
0.7394	Intermediate Similarity	NPD3112	Approved
0.7394	Intermediate Similarity	NPD3115	Approved
0.7394	Intermediate Similarity	NPD3113	Approved
0.7394	Intermediate Similarity	NPD3114	Approved
0.7386	Intermediate Similarity	NPD5463	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD4509	Discontinued
0.7363	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD2465	Approved
0.7362	Intermediate Similarity	NPD2462	Phase 3
0.7362	Intermediate Similarity	NPD2466	Phase 3
0.736	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD4029	Approved
0.7355	Intermediate Similarity	NPD4030	Approved
0.7355	Intermediate Similarity	NPD4028	Approved
0.7349	Intermediate Similarity	NPD5300	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD4298	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD3348	Phase 2
0.7338	Intermediate Similarity	NPD1251	Discontinued
0.7337	Intermediate Similarity	NPD2915	Discontinued
0.733	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD5315	Discontinued
0.7321	Intermediate Similarity	NPD6771	Discontinued
0.7317	Intermediate Similarity	NPD2882	Phase 1
0.7315	Intermediate Similarity	NPD1561	Phase 2
0.7303	Intermediate Similarity	NPD2409	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4811	Discontinued
0.7293	Intermediate Similarity	NPD3431	Approved
0.7293	Intermediate Similarity	NPD3430	Approved
0.7289	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7469	Discontinued
0.7278	Intermediate Similarity	NPD2818	Discontinued
0.7273	Intermediate Similarity	NPD1707	Approved
0.7273	Intermediate Similarity	NPD1708	Approved
0.7263	Intermediate Similarity	NPD2408	Discontinued
0.7262	Intermediate Similarity	NPD1404	Approved
0.7262	Intermediate Similarity	NPD1403	Approved
0.7257	Intermediate Similarity	NPD3409	Phase 1
0.7251	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD2868	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4075	Phase 2
0.7241	Intermediate Similarity	NPD5104	Approved
0.7241	Intermediate Similarity	NPD2751	Phase 1
0.7232	Intermediate Similarity	NPD3512	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD5996	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6192	Phase 3
0.7222	Intermediate Similarity	NPD3630	Approved
0.7222	Intermediate Similarity	NPD3629	Approved
0.7213	Intermediate Similarity	NPD4999	Phase 3
0.7213	Intermediate Similarity	NPD4998	Phase 3
0.7212	Intermediate Similarity	NPD2128	Phase 1
0.72	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD6577	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD2142	Approved
0.7197	Intermediate Similarity	NPD2140	Approved
0.7197	Intermediate Similarity	NPD2141	Approved
0.7196	Intermediate Similarity	NPD2008	Discontinued
0.7193	Intermediate Similarity	NPD2639	Approved
0.7193	Intermediate Similarity	NPD2392	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD2642	Approved
0.7193	Intermediate Similarity	NPD3361	Phase 1
0.7191	Intermediate Similarity	NPD7564	Discontinued
0.7178	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7867	Phase 1
0.7169	Intermediate Similarity	NPD3339	Approved
0.7168	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD1893	Phase 2
0.7159	Intermediate Similarity	NPD1892	Phase 2

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