NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	252.09
Volume:	260.809
LogP:	2.55
LogD:	2.343
LogS:	-3.829
# Rotatable Bonds:	3
TPSA:	54.98
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.562
Synthetic Accessibility Score:	2.72
Fsp3:	0.067
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:	-4.976
MDCK Permeability:	2.2432035621022806e-05
Pgp-inhibitor:	0.019
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.032
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.903
Plasma Protein Binding (PPB):	72.07038116455078%
Volume Distribution (VD):	1.128
Pgp-substrate:	31.007850646972656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.991
CYP1A2-substrate:	0.373
CYP2C19-inhibitor:	0.431
CYP2C19-substrate:	0.205
CYP2C9-inhibitor:	0.701
CYP2C9-substrate:	0.716
CYP2D6-inhibitor:	0.721
CYP2D6-substrate:	0.806
CYP3A4-inhibitor:	0.621
CYP3A4-substrate:	0.424

ADMET: Excretion

Clearance (CL):	2.575
Half-life (T1/2):	0.472

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.275
Drug-inuced Liver Injury (DILI):	0.966
AMES Toxicity:	0.187
Rat Oral Acute Toxicity:	0.99
Maximum Recommended Daily Dose:	0.275
Skin Sensitization:	0.942
Carcinogencity:	0.652
Eye Corrosion:	0.12
Eye Irritation:	0.974
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC476287

Natural Product ID:	NPC476287
*Common Name:**	8-Acetoxy-1-Vinyl-Beta-Carboline
IUPAC Name:	(1-ethenyl-9H-pyrido[3,4-b]indol-8-yl) acetate
Synonyms:
Standard InCHIKey:	XORWASCXQLBVOH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H12N2O2/c1-3-12-14-11(7-8-16-12)10-5-4-6-13(15(10)17-14)19-9(2)18/h3-8,17H,1H2,2H3
SMILES:	C=Cc1nccc2c1[nH]c1c2cccc1OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL562170
PubChem CID:	45268886
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001140] Harmala 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
NPO25419	Pterocella vesiculosa	Species	n.a.	n.a.	n.a.	New Zealand	n.a.	PMID[18052329]
NPO25419	Pterocella vesiculosa	Species	n.a.	n.a.	n.a.	Alderman Islands off the North Island of New Zealand	n.a.	PMID[18052329]
NPO25419	Pterocella vesiculosa	Species	n.a.	n.a.	n.a.	New Zealand	n.a.	PMID[19220033]
NPO25419	Pterocella vesiculosa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19220033]
NPO25419	Pterocella vesiculosa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.65	ug.mL-1	PMID[542484]

☑ 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 NPC476287 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	532
0.1-0.2	4116
0.2-0.3	13245
0.3-0.4	9919
0.4-0.5	10251
0.5-0.6	2378
0.6-0.7	1845
0.7-0.8	369
0.8-0.85	29
0.85-0.9	8
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9421	High Similarity	NPC245816
0.9421	High Similarity	NPC476138
0.9082	High Similarity	NPC185782
0.8945	High Similarity	NPC26679
0.8866	High Similarity	NPC19872
0.8812	High Similarity	NPC470799
0.8812	High Similarity	NPC8022
0.8769	High Similarity	NPC176538
0.8718	High Similarity	NPC476167
0.8683	High Similarity	NPC292958
0.8667	High Similarity	NPC192315
0.8653	High Similarity	NPC475190
0.8535	High Similarity	NPC232727
0.852	High Similarity	NPC267928
0.8411	Intermediate Similarity	NPC469554
0.8411	Intermediate Similarity	NPC101543
0.8364	Intermediate Similarity	NPC260434
0.8333	Intermediate Similarity	NPC60621
0.8311	Intermediate Similarity	NPC148889
0.8284	Intermediate Similarity	NPC287208
0.8238	Intermediate Similarity	NPC284678
0.8204	Intermediate Similarity	NPC167860
0.8204	Intermediate Similarity	NPC123976
0.8195	Intermediate Similarity	NPC82548
0.8177	Intermediate Similarity	NPC475774
0.8163	Intermediate Similarity	NPC242928
0.8163	Intermediate Similarity	NPC296527
0.8135	Intermediate Similarity	NPC474798
0.8122	Intermediate Similarity	NPC76748
0.8102	Intermediate Similarity	NPC314954
0.809	Intermediate Similarity	NPC307963
0.8081	Intermediate Similarity	NPC92111
0.8053	Intermediate Similarity	NPC26543
0.8038	Intermediate Similarity	NPC118940
0.801	Intermediate Similarity	NPC251090
0.8	Intermediate Similarity	NPC122436
0.7981	Intermediate Similarity	NPC174758
0.7981	Intermediate Similarity	NPC193267
0.7981	Intermediate Similarity	NPC213530
0.7961	Intermediate Similarity	NPC285558
0.7952	Intermediate Similarity	NPC94157
0.7943	Intermediate Similarity	NPC5145
0.7943	Intermediate Similarity	NPC123839
0.7933	Intermediate Similarity	NPC266249
0.7919	Intermediate Similarity	NPC182222
0.791	Intermediate Similarity	NPC198673
0.7907	Intermediate Similarity	NPC310118
0.7905	Intermediate Similarity	NPC208284
0.7902	Intermediate Similarity	NPC470586
0.7895	Intermediate Similarity	NPC174672
0.7892	Intermediate Similarity	NPC128823
0.7879	Intermediate Similarity	NPC53534
0.7874	Intermediate Similarity	NPC475070
0.783	Intermediate Similarity	NPC39500
0.7826	Intermediate Similarity	NPC223427
0.7817	Intermediate Similarity	NPC176127
0.7789	Intermediate Similarity	NPC118511
0.7788	Intermediate Similarity	NPC470500
0.7772	Intermediate Similarity	NPC324149
0.7767	Intermediate Similarity	NPC315957
0.7767	Intermediate Similarity	NPC121772
0.7757	Intermediate Similarity	NPC274982
0.7756	Intermediate Similarity	NPC168911
0.7756	Intermediate Similarity	NPC239954
0.7745	Intermediate Similarity	NPC13880
0.7734	Intermediate Similarity	NPC84853
0.7727	Intermediate Similarity	NPC48938
0.7727	Intermediate Similarity	NPC110151
0.7713	Intermediate Similarity	NPC180504
0.7703	Intermediate Similarity	NPC470930
0.7696	Intermediate Similarity	NPC132642
0.7692	Intermediate Similarity	NPC258048
0.7689	Intermediate Similarity	NPC199667
0.7685	Intermediate Similarity	NPC184408
0.7679	Intermediate Similarity	NPC152620
0.7674	Intermediate Similarity	NPC288349
0.7653	Intermediate Similarity	NPC187501
0.765	Intermediate Similarity	NPC314002
0.7644	Intermediate Similarity	NPC295228
0.7642	Intermediate Similarity	NPC473181
0.7623	Intermediate Similarity	NPC476451
0.7623	Intermediate Similarity	NPC475253
0.7621	Intermediate Similarity	NPC156704
0.7617	Intermediate Similarity	NPC473180
0.7611	Intermediate Similarity	NPC235685
0.7608	Intermediate Similarity	NPC211813
0.76	Intermediate Similarity	NPC84478
0.76	Intermediate Similarity	NPC204717
0.7596	Intermediate Similarity	NPC45459
0.7596	Intermediate Similarity	NPC234197
0.7596	Intermediate Similarity	NPC315491
0.7581	Intermediate Similarity	NPC162530
0.7581	Intermediate Similarity	NPC266931
0.7577	Intermediate Similarity	NPC30540
0.7577	Intermediate Similarity	NPC101350
0.7576	Intermediate Similarity	NPC471891
0.7571	Intermediate Similarity	NPC476098
0.7563	Intermediate Similarity	NPC224764
0.755	Intermediate Similarity	NPC220765
0.7548	Intermediate Similarity	NPC187558
0.7545	Intermediate Similarity	NPC144452
0.7538	Intermediate Similarity	NPC314940
0.7538	Intermediate Similarity	NPC473764
0.7525	Intermediate Similarity	NPC171171
0.7512	Intermediate Similarity	NPC329793
0.7512	Intermediate Similarity	NPC476465
0.7512	Intermediate Similarity	NPC99666
0.7512	Intermediate Similarity	NPC170114
0.7512	Intermediate Similarity	NPC213308
0.7511	Intermediate Similarity	NPC196718
0.7511	Intermediate Similarity	NPC473186
0.7511	Intermediate Similarity	NPC102593
0.75	Intermediate Similarity	NPC161887
0.75	Intermediate Similarity	NPC212213
0.7489	Intermediate Similarity	NPC17565
0.7489	Intermediate Similarity	NPC473185
0.7489	Intermediate Similarity	NPC288987
0.7487	Intermediate Similarity	NPC42979
0.7478	Intermediate Similarity	NPC141053
0.7478	Intermediate Similarity	NPC473312
0.7477	Intermediate Similarity	NPC304926
0.7477	Intermediate Similarity	NPC209769
0.7477	Intermediate Similarity	NPC476041
0.7475	Intermediate Similarity	NPC20249
0.7475	Intermediate Similarity	NPC42591
0.7467	Intermediate Similarity	NPC474688
0.7465	Intermediate Similarity	NPC470549
0.7464	Intermediate Similarity	NPC18487
0.7464	Intermediate Similarity	NPC287437
0.7456	Intermediate Similarity	NPC15801
0.7455	Intermediate Similarity	NPC472099
0.7454	Intermediate Similarity	NPC472098
0.7454	Intermediate Similarity	NPC316981
0.7453	Intermediate Similarity	NPC132539
0.7445	Intermediate Similarity	NPC39370
0.7444	Intermediate Similarity	NPC470018
0.7443	Intermediate Similarity	NPC96321
0.7442	Intermediate Similarity	NPC471304
0.7438	Intermediate Similarity	NPC62749
0.7434	Intermediate Similarity	NPC49547
0.7432	Intermediate Similarity	NPC65277
0.7431	Intermediate Similarity	NPC152768
0.7431	Intermediate Similarity	NPC148183
0.7418	Intermediate Similarity	NPC300156
0.7414	Intermediate Similarity	NPC472434
0.7411	Intermediate Similarity	NPC74575
0.7409	Intermediate Similarity	NPC473179
0.7409	Intermediate Similarity	NPC208084
0.7406	Intermediate Similarity	NPC53144
0.7402	Intermediate Similarity	NPC46580
0.7385	Intermediate Similarity	NPC477979
0.7385	Intermediate Similarity	NPC118228
0.7384	Intermediate Similarity	NPC472435
0.7383	Intermediate Similarity	NPC193238
0.7378	Intermediate Similarity	NPC274640
0.7376	Intermediate Similarity	NPC225279
0.7368	Intermediate Similarity	NPC77555
0.7366	Intermediate Similarity	NPC24370
0.7366	Intermediate Similarity	NPC319232
0.7362	Intermediate Similarity	NPC165964
0.7361	Intermediate Similarity	NPC11464
0.736	Intermediate Similarity	NPC476518
0.7358	Intermediate Similarity	NPC57398
0.7356	Intermediate Similarity	NPC131017
0.735	Intermediate Similarity	NPC184964
0.7349	Intermediate Similarity	NPC477111
0.7346	Intermediate Similarity	NPC329747
0.7346	Intermediate Similarity	NPC477019
0.7343	Intermediate Similarity	NPC133140
0.7343	Intermediate Similarity	NPC195268
0.7339	Intermediate Similarity	NPC469592
0.7339	Intermediate Similarity	NPC471080
0.7336	Intermediate Similarity	NPC470164
0.7336	Intermediate Similarity	NPC323345
0.7333	Intermediate Similarity	NPC6215
0.7333	Intermediate Similarity	NPC72211
0.7333	Intermediate Similarity	NPC257851
0.7328	Intermediate Similarity	NPC171393
0.7328	Intermediate Similarity	NPC295452
0.7327	Intermediate Similarity	NPC118776
0.7327	Intermediate Similarity	NPC266551
0.7327	Intermediate Similarity	NPC219963
0.7325	Intermediate Similarity	NPC329631
0.7324	Intermediate Similarity	NPC162484
0.7324	Intermediate Similarity	NPC200836
0.7323	Intermediate Similarity	NPC252590
0.7323	Intermediate Similarity	NPC121658
0.7323	Intermediate Similarity	NPC14651
0.7321	Intermediate Similarity	NPC70259
0.7319	Intermediate Similarity	NPC91868
0.7319	Intermediate Similarity	NPC63971
0.7302	Intermediate Similarity	NPC321428
0.7302	Intermediate Similarity	NPC88008
0.7292	Intermediate Similarity	NPC472436
0.729	Intermediate Similarity	NPC47059
0.729	Intermediate Similarity	NPC165349
0.729	Intermediate Similarity	NPC329708
0.729	Intermediate Similarity	NPC264166
0.729	Intermediate Similarity	NPC274291
0.729	Intermediate Similarity	NPC118832

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 NPC476287 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	270
0.1-0.2	739
0.2-0.3	790
0.3-0.4	1480
0.4-0.5	2565
0.5-0.6	2154
0.6-0.7	991
0.7-0.8	154
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8364	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.8349	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.809	Intermediate Similarity	NPD1038	Approved
0.809	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.8053	Intermediate Similarity	NPD5482	Discontinued
0.8018	Intermediate Similarity	NPD5559	Phase 2
0.798	Intermediate Similarity	NPD3825	Phase 3
0.7964	Intermediate Similarity	NPD4454	Phase 2
0.796	Intermediate Similarity	NPD4418	Discontinued
0.7919	Intermediate Similarity	NPD4889	Approved
0.7883	Intermediate Similarity	NPD3006	Discontinued
0.784	Intermediate Similarity	NPD5612	Discontinued
0.7804	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD4795	Phase 2
0.7783	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD9705	Discontinued
0.7778	Intermediate Similarity	NPD112	Approved
0.7767	Intermediate Similarity	NPD1739	Approved
0.7767	Intermediate Similarity	NPD1740	Approved
0.7736	Intermediate Similarity	NPD5067	Phase 2
0.7736	Intermediate Similarity	NPD5066	Phase 2
0.7725	Intermediate Similarity	NPD6961	Discontinued
0.7714	Intermediate Similarity	NPD1392	Approved
0.771	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD4429	Discontinued
0.7685	Intermediate Similarity	NPD4372	Phase 1
0.7659	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7659	Intermediate Similarity	NPD3477	Phase 2
0.7647	Intermediate Similarity	NPD5450	Discontinued
0.7633	Intermediate Similarity	NPD4548	Discontinued
0.7626	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD1856	Discontinued
0.7603	Intermediate Similarity	NPD5018	Phase 3
0.7602	Intermediate Similarity	NPD7603	Discontinued
0.7598	Intermediate Similarity	NPD4440	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD484	Approved
0.7594	Intermediate Similarity	NPD5658	Approved
0.7593	Intermediate Similarity	NPD6643	Discontinued
0.758	Intermediate Similarity	NPD4881	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD5022	Discontinued
0.7569	Intermediate Similarity	NPD3402	Phase 1
0.7548	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD7222	Phase 2
0.7534	Intermediate Similarity	NPD6242	Discontinued
0.7525	Intermediate Similarity	NPD5256	Discontinued
0.7512	Intermediate Similarity	NPD6569	Phase 2
0.7512	Intermediate Similarity	NPD2189	Approved
0.7512	Intermediate Similarity	NPD2187	Approved
0.75	Intermediate Similarity	NPD3003	Approved
0.75	Intermediate Similarity	NPD5601	Phase 2
0.7489	Intermediate Similarity	NPD3514	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD1034	Phase 3
0.7488	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD3939	Suspended
0.7478	Intermediate Similarity	NPD7558	Phase 2
0.7469	Intermediate Similarity	NPD4442	Phase 2
0.7457	Intermediate Similarity	NPD8100	Phase 3
0.7449	Intermediate Similarity	NPD565	Phase 2
0.7445	Intermediate Similarity	NPD2951	Discontinued
0.7443	Intermediate Similarity	NPD5632	Approved
0.7427	Intermediate Similarity	NPD3343	Phase 3
0.7426	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD4204	Approved
0.7413	Intermediate Similarity	NPD4203	Approved
0.7407	Intermediate Similarity	NPD4131	Phase 3
0.7404	Intermediate Similarity	NPD5512	Phase 3
0.7404	Intermediate Similarity	NPD6550	Discontinued
0.7391	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD7453	Approved
0.7383	Intermediate Similarity	NPD7452	Approved
0.7381	Intermediate Similarity	NPD1768	Approved
0.7373	Intermediate Similarity	NPD7069	Discontinued
0.7362	Intermediate Similarity	NPD8101	Phase 3
0.7345	Intermediate Similarity	NPD8052	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD3924	Approved
0.7343	Intermediate Similarity	NPD3923	Approved
0.7343	Intermediate Similarity	NPD3922	Approved
0.7343	Intermediate Similarity	NPD3921	Approved
0.7339	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD9690	Approved
0.7336	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD4502	Phase 2
0.7325	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD6223	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD5903	Approved
0.7306	Intermediate Similarity	NPD5902	Approved
0.7299	Intermediate Similarity	NPD5999	Phase 2
0.729	Intermediate Similarity	NPD32	Approved
0.729	Intermediate Similarity	NPD4038	Approved
0.729	Intermediate Similarity	NPD4034	Approved
0.729	Intermediate Similarity	NPD4122	Approved
0.729	Intermediate Similarity	NPD4037	Approved
0.729	Intermediate Similarity	NPD4033	Approved
0.729	Intermediate Similarity	NPD3397	Phase 2
0.729	Intermediate Similarity	NPD4039	Approved
0.729	Intermediate Similarity	NPD4036	Approved
0.729	Intermediate Similarity	NPD4035	Approved
0.729	Intermediate Similarity	NPD31	Approved
0.7286	Intermediate Similarity	NPD7948	Phase 1
0.7285	Intermediate Similarity	NPD3354	Phase 2
0.7277	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD5479	Discontinued
0.7264	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD1032	Phase 2
0.7252	Intermediate Similarity	NPD7194	Discontinued
0.7246	Intermediate Similarity	NPD4558	Phase 2
0.7244	Intermediate Similarity	NPD1258	Discontinued
0.7238	Intermediate Similarity	NPD8442	Discontinued
0.7233	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD802	Phase 2
0.7222	Intermediate Similarity	NPD7067	Approved
0.7222	Intermediate Similarity	NPD5429	Discontinued
0.7222	Intermediate Similarity	NPD7068	Approved
0.7212	Intermediate Similarity	NPD1273	Discontinued
0.7208	Intermediate Similarity	NPD8049	Phase 2
0.7207	Intermediate Similarity	NPD6568	Discontinued
0.7204	Intermediate Similarity	NPD6988	Phase 1
0.7193	Intermediate Similarity	NPD6968	Phase 2
0.7193	Intermediate Similarity	NPD6969	Phase 2
0.7193	Intermediate Similarity	NPD8512	Phase 3
0.719	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD4919	Phase 3
0.7184	Intermediate Similarity	NPD4921	Phase 3
0.7184	Intermediate Similarity	NPD4920	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6473	Phase 1
0.7178	Intermediate Similarity	NPD4071	Approved
0.7178	Intermediate Similarity	NPD4072	Approved
0.7176	Intermediate Similarity	NPD8403	Phase 1
0.7156	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD4343	Phase 1
0.7155	Intermediate Similarity	NPD4344	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5930	Phase 3
0.7137	Intermediate Similarity	NPD7426	Phase 1
0.7136	Intermediate Similarity	NPD3815	Phase 1
0.7136	Intermediate Similarity	NPD3816	Phase 1
0.7136	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5948	Phase 2
0.713	Intermediate Similarity	NPD4885	Approved
0.7128	Intermediate Similarity	NPD2582	Approved
0.7128	Intermediate Similarity	NPD2581	Approved
0.7123	Intermediate Similarity	NPD5003	Discontinued
0.7118	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6147	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD5528	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD2509	Approved
0.711	Intermediate Similarity	NPD2510	Approved
0.711	Intermediate Similarity	NPD5529	Phase 1
0.7109	Intermediate Similarity	NPD3396	Approved
0.7109	Intermediate Similarity	NPD3395	Approved
0.7109	Intermediate Similarity	NPD6590	Discontinued
0.7104	Intermediate Similarity	NPD2314	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD2772	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD6494	Phase 2
0.7097	Intermediate Similarity	NPD5530	Phase 1
0.7091	Intermediate Similarity	NPD949	Phase 1
0.7091	Intermediate Similarity	NPD7470	Discontinued
0.7085	Intermediate Similarity	NPD424	Approved
0.7085	Intermediate Similarity	NPD425	Approved
0.7079	Intermediate Similarity	NPD5065	Approved
0.7073	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD9695	Approved
0.7062	Intermediate Similarity	NPD4551	Phase 2
0.7061	Intermediate Similarity	NPD7050	Clinical (unspecified phase)
0.7061	Intermediate Similarity	NPD7051	Phase 3
0.7059	Intermediate Similarity	NPD3330	Phase 1
0.7059	Intermediate Similarity	NPD6202	Discontinued
0.7056	Intermediate Similarity	NPD2175	Phase 3
0.7056	Intermediate Similarity	NPD1418	Phase 2
0.7056	Intermediate Similarity	NPD2177	Approved
0.7056	Intermediate Similarity	NPD2176	Approved
0.7054	Intermediate Similarity	NPD7395	Discontinued
0.7054	Intermediate Similarity	NPD6985	Discontinued
0.7048	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5913	Phase 3
0.7048	Intermediate Similarity	NPD2334	Discontinued
0.7044	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD2952	Discontinued
0.704	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD7467	Discontinued
0.7031	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD5644	Phase 1
0.7025	Intermediate Similarity	NPD8246	Approved
0.7025	Intermediate Similarity	NPD8247	Approved
0.7014	Intermediate Similarity	NPD6220	Phase 3
0.7014	Intermediate Similarity	NPD5416	Discontinued
0.7012	Intermediate Similarity	NPD7659	Discontinued
0.7	Intermediate Similarity	NPD2565	Phase 2
0.7	Intermediate Similarity	NPD2564	Approved
0.6996	Remote Similarity	NPD6964	Approved
0.6996	Remote Similarity	NPD6963	Approved
0.6995	Remote Similarity	NPD482	Approved
0.6987	Remote Similarity	NPD7676	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