NPASS Compound

Structure

NPC293458 OpenBabel07101718222D 29 33 0 0 1 0 0 0 0 0999 V2000 -2.5370 1.8762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6202 -1.4610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3611 5.1266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5853 2.1834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9856 0.4214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3922 1.1256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1725 0.4214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9856 1.8298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7319 0.0259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7169 1.0258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5461 0.4769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9463 -0.3232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8884 -1.4869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5692 2.2783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7618 -1.9739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8734 -0.4870 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2003 2.5411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7659 1.1256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1725 1.8298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8855 2.1033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3197 3.5339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0150 0.9999 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8435 1.5128 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9705 1.2946 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6284 2.4341 0.0000 N 0 0 0 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 -1.7767 -2.9738 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2392 3.9269 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4804 4.1337 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 15 1 0 0 0 0 3 29 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 18 2 0 0 0 0 8 19 2 0 0 0 0 9 10 2 0 0 0 0 9 16 1 0 0 0 0 10 23 1 0 0 0 0 11 12 1 0 0 0 0 12 26 1 0 0 0 0 13 15 1 0 0 0 0 13 16 1 0 0 0 0 14 17 1 0 0 0 0 14 23 1 0 0 0 0 15 27 2 0 0 0 0 16 26 1 6 0 0 0 17 20 2 0 0 0 0 17 21 1 0 0 0 0 18 19 1 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 20 24 1 0 0 0 0 20 25 1 0 0 0 0 21 28 2 0 0 0 0 21 29 1 0 0 0 0 22 23 1 1 0 0 0 22 24 1 0 0 0 0 22 26 1 0 0 0 0 23 4 1 6 0 0 0 24 11 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.21
Volume:	410.787
LogP:	1.981
LogD:	1.944
LogS:	-3.578
# Rotatable Bonds:	5
TPSA:	58.97
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.58
Synthetic Accessibility Score:	5.339
Fsp3:	0.542
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:	-4.876
MDCK Permeability:	2.8130827558925375e-05
Pgp-inhibitor:	0.975
Pgp-substrate:	0.149
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.03
30% Bioavailability (F30%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.991
Plasma Protein Binding (PPB):	42.450626373291016%
Volume Distribution (VD):	1.648
Pgp-substrate:	62.58323287963867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.04
CYP1A2-substrate:	0.54
CYP2C19-inhibitor:	0.229
CYP2C19-substrate:	0.938
CYP2C9-inhibitor:	0.385
CYP2C9-substrate:	0.184
CYP2D6-inhibitor:	0.873
CYP2D6-substrate:	0.872
CYP3A4-inhibitor:	0.93
CYP3A4-substrate:	0.907

ADMET: Excretion

Clearance (CL):	3.011
Half-life (T1/2):	0.351

ADMET: Toxicity

hERG Blockers:	0.12
Human Hepatotoxicity (H-HT):	0.936
Drug-inuced Liver Injury (DILI):	0.211
AMES Toxicity:	0.328
Rat Oral Acute Toxicity:	0.5
Maximum Recommended Daily Dose:	0.917
Skin Sensitization:	0.495
Carcinogencity:	0.342
Eye Corrosion:	0.004
Eye Irritation:	0.017
Respiratory Toxicity:	0.881

Download Data

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

Natural Product: NPC293458

Natural Product ID:	NPC293458
*Common Name:**	JRXQFQWABJSNMW-GRYKHCQJSA-N
IUPAC Name:	n.a.
Synonyms:	3-Alpha-Acetonyltabersonine
Standard InCHIKey:	JRXQFQWABJSNMW-GRYKHCQJSA-N
Standard InCHI:	InChI=1S/C24H28N2O3/c1-4-23-10-9-16(13-15(2)27)26-12-11-24(22(23)26)18-7-5-6-8-19(18)25-20(24)17(14-23)21(28)29-3/h5-10,16,22,25H,4,11-14H2,1-3H3/t16-,22-,23-,24-/m0/s1
SMILES:	COC(=O)C1=C2Nc3c([C@@]42[C@@H]2[C@@](C1)(CC)C=C[C@H](N2CC4)CC(=O)C)cccc3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2011515
PubChem CID:	14463025
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002672] Plumeran-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
NPO33137	melodinus suaveolens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22260257]
NPO33137	melodinus suaveolens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24274642]

☑ 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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	200.0	nM	PMID[531618]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	300.0	nM	PMID[531618]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	600.0	nM	PMID[531618]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	400.0	nM	PMID[531618]
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	500.0	nM	PMID[531618]

☑ 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 NPC293458 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	239
0.1-0.2	1050
0.2-0.3	5213
0.3-0.4	18858
0.4-0.5	12298
0.5-0.6	4124
0.6-0.7	757
0.7-0.8	128
0.8-0.85	10
0.85-0.9	7
0.9-0.95	11
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9797	High Similarity	NPC123241
0.9533	High Similarity	NPC61013
0.9408	High Similarity	NPC248117
0.9355	High Similarity	NPC223595
0.9355	High Similarity	NPC167724
0.9355	High Similarity	NPC224970
0.9342	High Similarity	NPC193410
0.9125	High Similarity	NPC186669
0.908	High Similarity	NPC97584
0.8944	High Similarity	NPC203202
0.8944	High Similarity	NPC264482
0.8882	High Similarity	NPC329338
0.8882	High Similarity	NPC469726
0.8846	High Similarity	NPC36495
0.872	High Similarity	NPC218594
0.872	High Similarity	NPC6974
0.872	High Similarity	NPC99043
0.869	High Similarity	NPC14994
0.8675	High Similarity	NPC159963
0.8588	High Similarity	NPC5630
0.8538	High Similarity	NPC22476
0.8538	High Similarity	NPC203628
0.85	High Similarity	NPC282339
0.85	High Similarity	NPC99632
0.8343	Intermediate Similarity	NPC303214
0.8324	Intermediate Similarity	NPC25401
0.8121	Intermediate Similarity	NPC214960
0.8121	Intermediate Similarity	NPC279527
0.8111	Intermediate Similarity	NPC232600
0.8098	Intermediate Similarity	NPC225319
0.8035	Intermediate Similarity	NPC52262
0.7978	Intermediate Similarity	NPC87714
0.7978	Intermediate Similarity	NPC475147
0.7888	Intermediate Similarity	NPC243756
0.7845	Intermediate Similarity	NPC138615
0.7845	Intermediate Similarity	NPC265642
0.7845	Intermediate Similarity	NPC132874
0.7845	Intermediate Similarity	NPC218733
0.784	Intermediate Similarity	NPC122106
0.7807	Intermediate Similarity	NPC475133
0.7758	Intermediate Similarity	NPC113946
0.7719	Intermediate Similarity	NPC139085
0.7719	Intermediate Similarity	NPC214626
0.7719	Intermediate Similarity	NPC251212
0.7716	Intermediate Similarity	NPC473329
0.7684	Intermediate Similarity	NPC119722
0.7683	Intermediate Similarity	NPC478076
0.7665	Intermediate Similarity	NPC474058
0.7602	Intermediate Similarity	NPC472118
0.7595	Intermediate Similarity	NPC130251
0.7586	Intermediate Similarity	NPC260075
0.756	Intermediate Similarity	NPC472102
0.756	Intermediate Similarity	NPC309531
0.7547	Intermediate Similarity	NPC301760
0.7515	Intermediate Similarity	NPC472117
0.7515	Intermediate Similarity	NPC469741
0.7487	Intermediate Similarity	NPC1464
0.7485	Intermediate Similarity	NPC469536
0.7459	Intermediate Similarity	NPC100863
0.7455	Intermediate Similarity	NPC154602
0.7444	Intermediate Similarity	NPC181928
0.7437	Intermediate Similarity	NPC115588
0.7436	Intermediate Similarity	NPC126556
0.7427	Intermediate Similarity	NPC470069
0.7427	Intermediate Similarity	NPC52059
0.7425	Intermediate Similarity	NPC161827
0.7423	Intermediate Similarity	NPC264589
0.7423	Intermediate Similarity	NPC189661
0.7414	Intermediate Similarity	NPC285622
0.741	Intermediate Similarity	NPC285381
0.7407	Intermediate Similarity	NPC190945
0.7396	Intermediate Similarity	NPC269449
0.7368	Intermediate Similarity	NPC246140
0.7368	Intermediate Similarity	NPC195787
0.7356	Intermediate Similarity	NPC292265
0.7349	Intermediate Similarity	NPC475763
0.734	Intermediate Similarity	NPC469732
0.7314	Intermediate Similarity	NPC96901
0.7312	Intermediate Similarity	NPC162440
0.731	Intermediate Similarity	NPC472120
0.731	Intermediate Similarity	NPC286871
0.731	Intermediate Similarity	NPC472121
0.731	Intermediate Similarity	NPC77777
0.731	Intermediate Similarity	NPC472101
0.7294	Intermediate Similarity	NPC310403
0.7294	Intermediate Similarity	NPC263709
0.7294	Intermediate Similarity	NPC148468
0.7294	Intermediate Similarity	NPC97380
0.7294	Intermediate Similarity	NPC63210
0.7294	Intermediate Similarity	NPC243673
0.7268	Intermediate Similarity	NPC473298
0.7258	Intermediate Similarity	NPC473375
0.7258	Intermediate Similarity	NPC97100
0.7239	Intermediate Similarity	NPC469537
0.7225	Intermediate Similarity	NPC472106
0.7222	Intermediate Similarity	NPC471164
0.7216	Intermediate Similarity	NPC21752
0.7216	Intermediate Similarity	NPC298851
0.7216	Intermediate Similarity	NPC276993
0.7216	Intermediate Similarity	NPC181138
0.7216	Intermediate Similarity	NPC476425
0.7216	Intermediate Similarity	NPC210415
0.7216	Intermediate Similarity	NPC293255
0.7204	Intermediate Similarity	NPC220151
0.7204	Intermediate Similarity	NPC34717
0.7204	Intermediate Similarity	NPC19692
0.7184	Intermediate Similarity	NPC472114
0.7184	Intermediate Similarity	NPC472115
0.7174	Intermediate Similarity	NPC105055
0.7174	Intermediate Similarity	NPC22689
0.7172	Intermediate Similarity	NPC195636
0.7168	Intermediate Similarity	NPC313757
0.716	Intermediate Similarity	NPC315051
0.7159	Intermediate Similarity	NPC318183
0.7158	Intermediate Similarity	NPC21425
0.7151	Intermediate Similarity	NPC201424
0.7151	Intermediate Similarity	NPC321211
0.7143	Intermediate Similarity	NPC322621
0.7135	Intermediate Similarity	NPC211525
0.7135	Intermediate Similarity	NPC476441
0.7135	Intermediate Similarity	NPC153694
0.7135	Intermediate Similarity	NPC329833
0.7128	Intermediate Similarity	NPC90967
0.7125	Intermediate Similarity	NPC173295
0.712	Intermediate Similarity	NPC137589
0.7113	Intermediate Similarity	NPC285192
0.7112	Intermediate Similarity	NPC221687
0.711	Intermediate Similarity	NPC176983
0.7083	Intermediate Similarity	NPC318086
0.7081	Intermediate Similarity	NPC314333
0.7076	Intermediate Similarity	NPC63370
0.7076	Intermediate Similarity	NPC36836
0.707	Intermediate Similarity	NPC209389
0.7065	Intermediate Similarity	NPC476069
0.7056	Intermediate Similarity	NPC127996
0.7052	Intermediate Similarity	NPC315368
0.7048	Intermediate Similarity	NPC151171
0.7041	Intermediate Similarity	NPC314223
0.703	Intermediate Similarity	NPC128476
0.703	Intermediate Similarity	NPC308197
0.7027	Intermediate Similarity	NPC63199
0.7027	Intermediate Similarity	NPC196251
0.7027	Intermediate Similarity	NPC111602
0.7027	Intermediate Similarity	NPC102338
0.7024	Intermediate Similarity	NPC242000
0.7022	Intermediate Similarity	NPC177261
0.7018	Intermediate Similarity	NPC473297
0.7012	Intermediate Similarity	NPC186284
0.7012	Intermediate Similarity	NPC22082
0.7	Intermediate Similarity	NPC476326
0.6994	Remote Similarity	NPC319645
0.6994	Remote Similarity	NPC471122
0.6993	Remote Similarity	NPC179605
0.6993	Remote Similarity	NPC279385
0.6989	Remote Similarity	NPC329858
0.6984	Remote Similarity	NPC245916
0.6977	Remote Similarity	NPC29285
0.6975	Remote Similarity	NPC471123
0.6957	Remote Similarity	NPC223242
0.6957	Remote Similarity	NPC49184
0.6954	Remote Similarity	NPC68650
0.6948	Remote Similarity	NPC103292
0.6928	Remote Similarity	NPC177684
0.6928	Remote Similarity	NPC291962
0.6927	Remote Similarity	NPC19175
0.6927	Remote Similarity	NPC67904
0.6927	Remote Similarity	NPC138830
0.6915	Remote Similarity	NPC471197
0.6893	Remote Similarity	NPC278887
0.6891	Remote Similarity	NPC471512
0.689	Remote Similarity	NPC139373
0.689	Remote Similarity	NPC469560
0.6889	Remote Similarity	NPC475097
0.6885	Remote Similarity	NPC476428
0.6883	Remote Similarity	NPC161956
0.6883	Remote Similarity	NPC112373
0.6883	Remote Similarity	NPC258531
0.6881	Remote Similarity	NPC471198
0.6879	Remote Similarity	NPC472244
0.6879	Remote Similarity	NPC470343
0.6872	Remote Similarity	NPC355
0.6865	Remote Similarity	NPC316141
0.6856	Remote Similarity	NPC162730
0.6854	Remote Similarity	NPC63047
0.6854	Remote Similarity	NPC475248
0.6848	Remote Similarity	NPC470317
0.6839	Remote Similarity	NPC254240
0.6839	Remote Similarity	NPC312870
0.6839	Remote Similarity	NPC199851
0.6839	Remote Similarity	NPC294909
0.6839	Remote Similarity	NPC128265
0.6839	Remote Similarity	NPC222029
0.6839	Remote Similarity	NPC257490
0.6836	Remote Similarity	NPC471124
0.6833	Remote Similarity	NPC473743
0.6831	Remote Similarity	NPC286994
0.6825	Remote Similarity	NPC472292
0.6825	Remote Similarity	NPC55493
0.6818	Remote Similarity	NPC476231
0.6813	Remote Similarity	NPC194562

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 NPC293458 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	482
0.2-0.3	808
0.3-0.4	1240
0.4-0.5	3674
0.5-0.6	2399
0.6-0.7	369
0.7-0.8	24
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
0.7602	Intermediate Similarity	NPD3376	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD2037	Approved
0.7407	Intermediate Similarity	NPD2435	Approved
0.7401	Intermediate Similarity	NPD4330	Approved
0.7401	Intermediate Similarity	NPD4329	Approved
0.7394	Intermediate Similarity	NPD2737	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD1802	Approved
0.7378	Intermediate Similarity	NPD1801	Approved
0.7356	Intermediate Similarity	NPD2431	Approved
0.7356	Intermediate Similarity	NPD2432	Approved
0.7345	Intermediate Similarity	NPD3782	Discontinued
0.7341	Intermediate Similarity	NPD2455	Approved
0.7341	Intermediate Similarity	NPD2454	Approved
0.7341	Intermediate Similarity	NPD2404	Discontinued
0.733	Intermediate Similarity	NPD3978	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD4041	Approved
0.7305	Intermediate Similarity	NPD3399	Approved
0.7288	Intermediate Similarity	NPD3792	Approved
0.7263	Intermediate Similarity	NPD3471	Approved
0.7263	Intermediate Similarity	NPD3470	Approved
0.7251	Intermediate Similarity	NPD2506	Approved
0.7229	Intermediate Similarity	NPD7528	Approved
0.7228	Intermediate Similarity	NPD5504	Discontinued
0.7205	Intermediate Similarity	NPD3170	Approved
0.7202	Intermediate Similarity	NPD2948	Discontinued
0.7143	Intermediate Similarity	NPD2670	Approved
0.7093	Intermediate Similarity	NPD2427	Approved
0.7091	Intermediate Similarity	NPD7487	Discontinued
0.7081	Intermediate Similarity	NPD4499	Approved
0.7079	Intermediate Similarity	NPD3423	Phase 2
0.7079	Intermediate Similarity	NPD3422	Phase 3
0.7076	Intermediate Similarity	NPD6571	Approved
0.7076	Intermediate Similarity	NPD6570	Approved
0.7063	Intermediate Similarity	NPD5185	Approved
0.7063	Intermediate Similarity	NPD5184	Approved
0.7063	Intermediate Similarity	NPD5182	Approved
0.7059	Intermediate Similarity	NPD2790	Discontinued
0.7056	Intermediate Similarity	NPD2869	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7244	Discontinued
0.7048	Intermediate Similarity	NPD6017	Discontinued
0.7045	Intermediate Similarity	NPD3468	Approved
0.7039	Intermediate Similarity	NPD2083	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3828	Approved
0.7022	Intermediate Similarity	NPD3377	Discontinued
0.6995	Remote Similarity	NPD4412	Phase 2
0.6994	Remote Similarity	NPD1109	Approved
0.6994	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD1110	Approved
0.6983	Remote Similarity	NPD5466	Approved
0.6974	Remote Similarity	NPD1668	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7478	Approved
0.6941	Remote Similarity	NPD7606	Phase 3
0.6932	Remote Similarity	NPD7036	Phase 3
0.6932	Remote Similarity	NPD7035	Approved
0.6919	Remote Similarity	NPD4493	Discontinued
0.6893	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8008	Approved
0.6875	Remote Similarity	NPD8007	Approved
0.6868	Remote Similarity	NPD7881	Approved
0.6867	Remote Similarity	NPD2923	Approved
0.6867	Remote Similarity	NPD6768	Approved
0.6865	Remote Similarity	NPD2397	Discontinued
0.6862	Remote Similarity	NPD3884	Discontinued
0.6862	Remote Similarity	NPD3304	Phase 2
0.6853	Remote Similarity	NPD4859	Phase 1
0.6851	Remote Similarity	NPD3948	Discontinued
0.6848	Remote Similarity	NPD8281	Discontinued
0.6845	Remote Similarity	NPD6185	Discontinued
0.6839	Remote Similarity	NPD4500	Approved
0.6839	Remote Similarity	NPD4501	Approved
0.6824	Remote Similarity	NPD4888	Discontinued
0.6816	Remote Similarity	NPD5186	Approved
0.6816	Remote Similarity	NPD5183	Approved
0.6813	Remote Similarity	NPD8006	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD3625	Discontinued
0.6805	Remote Similarity	NPD4607	Approved
0.6788	Remote Similarity	NPD1626	Approved
0.6786	Remote Similarity	NPD5918	Discontinued
0.6786	Remote Similarity	NPD3947	Discontinued
0.6768	Remote Similarity	NPD4082	Approved
0.6766	Remote Similarity	NPD4455	Discontinued
0.6765	Remote Similarity	NPD6758	Approved
0.6765	Remote Similarity	NPD3352	Approved
0.6761	Remote Similarity	NPD4311	Approved
0.6753	Remote Similarity	NPD6805	Discontinued
0.6746	Remote Similarity	NPD7295	Approved
0.6743	Remote Similarity	NPD8630	Approved
0.6742	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.674	Remote Similarity	NPD5997	Discontinued
0.6726	Remote Similarity	NPD7082	Approved
0.6726	Remote Similarity	NPD2820	Phase 3
0.6725	Remote Similarity	NPD5942	Approved
0.6725	Remote Similarity	NPD5941	Approved
0.6717	Remote Similarity	NPD4596	Phase 1
0.6716	Remote Similarity	NPD3888	Discontinued
0.6716	Remote Similarity	NPD4492	Approved
0.6716	Remote Similarity	NPD4494	Approved
0.6707	Remote Similarity	NPD2470	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD7940	Phase 3
0.67	Remote Similarity	NPD3893	Discontinued
0.6686	Remote Similarity	NPD4513	Discontinued
0.6686	Remote Similarity	NPD7259	Approved
0.6685	Remote Similarity	NPD7775	Approved
0.6684	Remote Similarity	NPD6557	Phase 2
0.6667	Remote Similarity	NPD1070	Approved
0.6667	Remote Similarity	NPD2365	Approved
0.6667	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD486	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1069	Approved
0.6667	Remote Similarity	NPD5086	Approved
0.6667	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.665	Remote Similarity	NPD7205	Discontinued
0.665	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD5937	Approved
0.6648	Remote Similarity	NPD5430	Discontinued
0.6647	Remote Similarity	NPD7670	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD2994	Approved
0.6633	Remote Similarity	NPD3314	Discontinued
0.6631	Remote Similarity	NPD3436	Approved
0.6629	Remote Similarity	NPD7220	Approved
0.6628	Remote Similarity	NPD4161	Discontinued
0.6627	Remote Similarity	NPD1625	Approved
0.6627	Remote Similarity	NPD4430	Phase 2
0.6627	Remote Similarity	NPD5024	Approved
0.6627	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD9567	Approved
0.6625	Remote Similarity	NPD552	Approved
0.6625	Remote Similarity	NPD553	Approved
0.6613	Remote Similarity	NPD3435	Discontinued
0.6606	Remote Similarity	NPD2791	Discontinued
0.6604	Remote Similarity	NPD1640	Clinical (unspecified phase)
0.66	Remote Similarity	NPD4022	Approved
0.66	Remote Similarity	NPD2510	Approved
0.66	Remote Similarity	NPD2509	Approved
0.66	Remote Similarity	NPD3472	Approved
0.6597	Remote Similarity	NPD4370	Phase 3
0.6596	Remote Similarity	NPD3413	Approved
0.6596	Remote Similarity	NPD3414	Approved
0.6593	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD3790	Phase 2
0.6585	Remote Similarity	NPD1527	Phase 2
0.6582	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD2117	Pre-registration
0.6581	Remote Similarity	NPD2115	Approved
0.6581	Remote Similarity	NPD2116	Approved
0.6575	Remote Similarity	NPD2844	Phase 3
0.6568	Remote Similarity	NPD6566	Discontinued
0.655	Remote Similarity	NPD5932	Phase 3
0.655	Remote Similarity	NPD5931	Phase 3
0.655	Remote Similarity	NPD5933	Phase 3
0.6543	Remote Similarity	NPD995	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD3372	Discontinued
0.6533	Remote Similarity	NPD5901	Discontinued
0.6533	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD6342	Discontinued
0.6526	Remote Similarity	NPD6891	Phase 2
0.6519	Remote Similarity	NPD2946	Phase 2
0.6517	Remote Similarity	NPD7599	Phase 2
0.6503	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD1165	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD3032	Approved
0.6497	Remote Similarity	NPD1663	Discontinued
0.6497	Remote Similarity	NPD3031	Approved
0.6497	Remote Similarity	NPD2836	Approved
0.6497	Remote Similarity	NPD4600	Approved
0.6497	Remote Similarity	NPD4601	Approved
0.6497	Remote Similarity	NPD3030	Approved
0.649	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6457	Approved
0.6482	Remote Similarity	NPD6176	Phase 1
0.6467	Remote Similarity	NPD7854	Phase 2
0.6465	Remote Similarity	NPD6238	Discontinued
0.6462	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD5928	Phase 1
0.6457	Remote Similarity	NPD5982	Phase 2
0.6453	Remote Similarity	NPD6622	Phase 1
0.6453	Remote Similarity	NPD5860	Discontinued
0.6452	Remote Similarity	NPD5600	Discontinued
0.645	Remote Similarity	NPD8282	Approved
0.645	Remote Similarity	NPD56	Approved
0.645	Remote Similarity	NPD8283	Approved
0.6441	Remote Similarity	NPD1093	Approved
0.6441	Remote Similarity	NPD4045	Phase 2
0.6441	Remote Similarity	NPD1092	Approved
0.6441	Remote Similarity	NPD4042	Phase 2
0.6438	Remote Similarity	NPD1360	Approved
0.6433	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD2567	Approved
0.6429	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD2569	Approved
0.6425	Remote Similarity	NPD4393	Approved
0.6425	Remote Similarity	NPD2336	Approved
0.6425	Remote Similarity	NPD5042	Phase 1

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