NPASS Compound

Structure

NPC474058 OpenBabel07101719152D 25 29 0 0 1 0 0 0 0 0999 V2000 1.0901 -4.6205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5093 -4.0889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5093 -3.0889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6433 -4.5889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6433 -2.5889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3375 -5.0108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5537 -5.0108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5815 -2.8807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6407 -1.4229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 -1.8968 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7773 -4.0889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8262 -4.3980 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.7773 -3.0889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2395 -3.6338 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5602 -1.8160 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2384 -3.5889 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0650 -4.3980 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.8262 -2.7799 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.3133 -1.1580 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 0.2788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 14 2 0 0 0 0 5 16 2 0 0 0 0 6 8 1 0 0 0 0 6 15 1 0 0 0 0 7 9 1 0 0 0 0 7 13 2 0 0 0 0 8 21 1 0 0 0 0 9 25 1 0 0 0 0 10 12 1 0 0 0 0 11 12 1 0 0 0 0 11 18 1 0 0 0 0 12 13 1 1 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 19 1 0 0 0 0 16 22 1 0 0 0 0 17 10 1 1 0 0 0 17 19 1 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 18 23 1 6 0 0 0 19 22 1 0 0 0 0 20 24 2 0 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.18
Volume:	346.876
LogP:	2.407
LogD:	2.289
LogS:	-2.852
# Rotatable Bonds:	1
TPSA:	60.08
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.836
Synthetic Accessibility Score:	4.497
Fsp3:	0.5
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:	-5.094
MDCK Permeability:	9.592296919436194e-06
Pgp-inhibitor:	0.007
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.289
20% Bioavailability (F20%):	0.132
30% Bioavailability (F30%):	0.034

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.995
Plasma Protein Binding (PPB):	89.9271240234375%
Volume Distribution (VD):	4.169
Pgp-substrate:	11.935554504394531%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.094
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.898
CYP2C9-inhibitor:	0.062
CYP2C9-substrate:	0.923
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.743
CYP3A4-inhibitor:	0.055
CYP3A4-substrate:	0.855

ADMET: Excretion

Clearance (CL):	13.465
Half-life (T1/2):	0.433

ADMET: Toxicity

hERG Blockers:	0.756
Human Hepatotoxicity (H-HT):	0.742
Drug-inuced Liver Injury (DILI):	0.753
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.948
Maximum Recommended Daily Dose:	0.98
Skin Sensitization:	0.102
Carcinogencity:	0.791
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.922

Download Data

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

Natural Product: NPC474058

Natural Product ID:	NPC474058
*Common Name:**	Akagerine Lactone
IUPAC Name:	n.a.
Synonyms:	Akagerine Lactone
Standard InCHIKey:	ZKIUNXNZAGMWLK-CXKFYANOSA-N
Standard InCHI:	InChI=1S/C20H24N2O3/c1-21-8-6-15-14-4-2-3-5-16(14)22-18(23)11-12(10-17(21)19(15)22)13-7-9-25-20(13)24/h2-5,7,12,15,17-19,23H,6,8-11H2,1H3/t12-,15?,17+,18+,19?/m1/s1
SMILES:	CN1CCC2C3[C@@H]1C[C@H](C[C@@H](N3c1c2cccc1)O)C1=CCOC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459421
PubChem CID:	44559926
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
NPO15372	Strychnos johnsonii	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398531]
NPO15372	Strychnos johnsonii	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	3
Others	3

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	17000.0	nM	PMID[469118]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	25900.0	nM	PMID[469118]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	27500.0	nM	PMID[469118]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	53300.0	nM	PMID[469118]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	55200.0	nM	PMID[469118]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	60700.0	nM	PMID[469118]

☑ 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 NPC474058 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	190
0.1-0.2	883
0.2-0.3	3927
0.3-0.4	12395
0.4-0.5	19191
0.5-0.6	5291
0.6-0.7	700
0.7-0.8	112
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8323	Intermediate Similarity	NPC99043
0.8323	Intermediate Similarity	NPC218594
0.8086	Intermediate Similarity	NPC63210
0.8086	Intermediate Similarity	NPC97380
0.8086	Intermediate Similarity	NPC148468
0.8086	Intermediate Similarity	NPC193410
0.8086	Intermediate Similarity	NPC243673
0.8086	Intermediate Similarity	NPC263709
0.8086	Intermediate Similarity	NPC310403
0.8037	Intermediate Similarity	NPC248117
0.8025	Intermediate Similarity	NPC61013
0.7988	Intermediate Similarity	NPC203202
0.7988	Intermediate Similarity	NPC264482
0.7976	Intermediate Similarity	NPC210415
0.7976	Intermediate Similarity	NPC298851
0.7976	Intermediate Similarity	NPC293255
0.7976	Intermediate Similarity	NPC181138
0.7976	Intermediate Similarity	NPC21752
0.7976	Intermediate Similarity	NPC276993
0.7975	Intermediate Similarity	NPC36495
0.7914	Intermediate Similarity	NPC211525
0.7914	Intermediate Similarity	NPC153694
0.7904	Intermediate Similarity	NPC223595
0.7904	Intermediate Similarity	NPC224970
0.7904	Intermediate Similarity	NPC167724
0.7901	Intermediate Similarity	NPC161827
0.7895	Intermediate Similarity	NPC6974
0.7892	Intermediate Similarity	NPC470069
0.7892	Intermediate Similarity	NPC52059
0.7844	Intermediate Similarity	NPC472114
0.7844	Intermediate Similarity	NPC472115
0.784	Intermediate Similarity	NPC478076
0.7816	Intermediate Similarity	NPC97584
0.7805	Intermediate Similarity	NPC123241
0.7759	Intermediate Similarity	NPC159963
0.7733	Intermediate Similarity	NPC186669
0.7701	Intermediate Similarity	NPC113626
0.7674	Intermediate Similarity	NPC476441
0.7665	Intermediate Similarity	NPC293458
0.7584	Intermediate Similarity	NPC14994
0.7574	Intermediate Similarity	NPC472106
0.756	Intermediate Similarity	NPC472101
0.756	Intermediate Similarity	NPC472120
0.7556	Intermediate Similarity	NPC25401
0.7544	Intermediate Similarity	NPC472118
0.7529	Intermediate Similarity	NPC234987
0.7514	Intermediate Similarity	NPC469726
0.7514	Intermediate Similarity	NPC329338
0.7485	Intermediate Similarity	NPC113946
0.7457	Intermediate Similarity	NPC476425
0.7456	Intermediate Similarity	NPC472117
0.7396	Intermediate Similarity	NPC472102
0.7396	Intermediate Similarity	NPC225319
0.7396	Intermediate Similarity	NPC309531
0.7391	Intermediate Similarity	NPC245916
0.7356	Intermediate Similarity	NPC251212
0.7356	Intermediate Similarity	NPC96901
0.7356	Intermediate Similarity	NPC214626
0.7356	Intermediate Similarity	NPC139085
0.7353	Intermediate Similarity	NPC99632
0.7353	Intermediate Similarity	NPC282339
0.7353	Intermediate Similarity	NPC472121
0.7351	Intermediate Similarity	NPC90967
0.7326	Intermediate Similarity	NPC279527
0.7326	Intermediate Similarity	NPC214960
0.7321	Intermediate Similarity	NPC29285
0.7308	Intermediate Similarity	NPC22689
0.7308	Intermediate Similarity	NPC105055
0.7303	Intermediate Similarity	NPC476428
0.7303	Intermediate Similarity	NPC475962
0.7293	Intermediate Similarity	NPC181928
0.7253	Intermediate Similarity	NPC196251
0.7253	Intermediate Similarity	NPC102338
0.7253	Intermediate Similarity	NPC63199
0.7253	Intermediate Similarity	NPC111602
0.7249	Intermediate Similarity	NPC1464
0.7243	Intermediate Similarity	NPC220151
0.7243	Intermediate Similarity	NPC19692
0.7229	Intermediate Similarity	NPC473329
0.7225	Intermediate Similarity	NPC278887
0.7213	Intermediate Similarity	NPC473298
0.7198	Intermediate Similarity	NPC472323
0.7158	Intermediate Similarity	NPC175474
0.7151	Intermediate Similarity	NPC15840
0.7151	Intermediate Similarity	NPC11149
0.7143	Intermediate Similarity	NPC312870
0.7143	Intermediate Similarity	NPC199851
0.7143	Intermediate Similarity	NPC254240
0.7143	Intermediate Similarity	NPC294909
0.7143	Intermediate Similarity	NPC128265
0.7135	Intermediate Similarity	NPC476326
0.7135	Intermediate Similarity	NPC246140
0.7135	Intermediate Similarity	NPC195787
0.7135	Intermediate Similarity	NPC260075
0.7134	Intermediate Similarity	NPC314098
0.7134	Intermediate Similarity	NPC190945
0.7127	Intermediate Similarity	NPC472119
0.712	Intermediate Similarity	NPC5630
0.711	Intermediate Similarity	NPC313757
0.7104	Intermediate Similarity	NPC21425
0.7093	Intermediate Similarity	NPC315368
0.7088	Intermediate Similarity	NPC322621
0.7088	Intermediate Similarity	NPC52262
0.7083	Intermediate Similarity	NPC243756
0.7083	Intermediate Similarity	NPC87714
0.7081	Intermediate Similarity	NPC203628
0.7071	Intermediate Similarity	NPC234772
0.7062	Intermediate Similarity	NPC285622
0.7059	Intermediate Similarity	NPC473297
0.7059	Intermediate Similarity	NPC34717
0.7052	Intermediate Similarity	NPC286871
0.7049	Intermediate Similarity	NPC282092
0.7048	Intermediate Similarity	NPC472100
0.7048	Intermediate Similarity	NPC478039
0.7045	Intermediate Similarity	NPC469915
0.7037	Intermediate Similarity	NPC265642
0.7037	Intermediate Similarity	NPC138615
0.7037	Intermediate Similarity	NPC218733
0.7037	Intermediate Similarity	NPC132874
0.7032	Intermediate Similarity	NPC470343
0.7032	Intermediate Similarity	NPC472244
0.7022	Intermediate Similarity	NPC13367
0.701	Intermediate Similarity	NPC53344
0.7006	Intermediate Similarity	NPC318183
0.7	Intermediate Similarity	NPC321211
0.6994	Remote Similarity	NPC315051
0.6994	Remote Similarity	NPC143457
0.6989	Remote Similarity	NPC470971
0.6984	Remote Similarity	NPC475559
0.6984	Remote Similarity	NPC302548
0.6983	Remote Similarity	NPC129624
0.6982	Remote Similarity	NPC154602
0.6982	Remote Similarity	NPC314223
0.6965	Remote Similarity	NPC52254
0.6957	Remote Similarity	NPC66210
0.6954	Remote Similarity	NPC85651
0.6954	Remote Similarity	NPC176983
0.6946	Remote Similarity	NPC264589
0.694	Remote Similarity	NPC245741
0.694	Remote Similarity	NPC258480
0.6936	Remote Similarity	NPC471122
0.6935	Remote Similarity	NPC189661
0.6933	Remote Similarity	NPC319645
0.6933	Remote Similarity	NPC469560
0.6931	Remote Similarity	NPC303214
0.6919	Remote Similarity	NPC36836
0.6919	Remote Similarity	NPC63370
0.6915	Remote Similarity	NPC82070
0.6907	Remote Similarity	NPC329833
0.6902	Remote Similarity	NPC472209
0.6898	Remote Similarity	NPC28510
0.6898	Remote Similarity	NPC472097
0.6897	Remote Similarity	NPC201424
0.689	Remote Similarity	NPC243162
0.6885	Remote Similarity	NPC143533
0.6885	Remote Similarity	NPC477159
0.6882	Remote Similarity	NPC316405
0.6882	Remote Similarity	NPC284706
0.6881	Remote Similarity	NPC475609
0.6875	Remote Similarity	NPC475489
0.6872	Remote Similarity	NPC238457
0.6871	Remote Similarity	NPC281104
0.6867	Remote Similarity	NPC308197
0.6864	Remote Similarity	NPC242000
0.6859	Remote Similarity	NPC52557
0.6857	Remote Similarity	NPC35510
0.6857	Remote Similarity	NPC253667
0.6848	Remote Similarity	NPC470301
0.6848	Remote Similarity	NPC22082
0.6848	Remote Similarity	NPC186284
0.6842	Remote Similarity	NPC122106
0.6839	Remote Similarity	NPC471512
0.6839	Remote Similarity	NPC232600
0.6839	Remote Similarity	NPC469732
0.6826	Remote Similarity	NPC472103
0.6826	Remote Similarity	NPC314186
0.6824	Remote Similarity	NPC318086
0.6816	Remote Similarity	NPC292265
0.6811	Remote Similarity	NPC469460
0.6811	Remote Similarity	NPC79062
0.6811	Remote Similarity	NPC472107
0.681	Remote Similarity	NPC471123
0.6809	Remote Similarity	NPC22476
0.6804	Remote Similarity	NPC474077
0.6798	Remote Similarity	NPC469462
0.6793	Remote Similarity	NPC159125
0.6789	Remote Similarity	NPC221687
0.6788	Remote Similarity	NPC195461
0.6788	Remote Similarity	NPC81654
0.6788	Remote Similarity	NPC313985
0.6788	Remote Similarity	NPC49196
0.6788	Remote Similarity	NPC249150
0.6788	Remote Similarity	NPC79129
0.6784	Remote Similarity	NPC475763
0.678	Remote Similarity	NPC471124
0.6778	Remote Similarity	NPC177261
0.6772	Remote Similarity	NPC204970
0.6772	Remote Similarity	NPC472113
0.6772	Remote Similarity	NPC55493
0.6771	Remote Similarity	NPC100863

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 NPC474058 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	139
0.1-0.2	454
0.2-0.3	796
0.3-0.4	1226
0.4-0.5	3493
0.5-0.6	2595
0.6-0.7	428
0.7-0.8	19
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
0.7605	Intermediate Similarity	NPD7600	Phase 2
0.7516	Intermediate Similarity	NPD2670	Approved
0.744	Intermediate Similarity	NPD7599	Phase 2
0.7273	Intermediate Similarity	NPD5941	Approved
0.7273	Intermediate Similarity	NPD5942	Approved
0.7256	Intermediate Similarity	NPD4041	Approved
0.7212	Intermediate Similarity	NPD1802	Approved
0.7212	Intermediate Similarity	NPD1801	Approved
0.7178	Intermediate Similarity	NPD2820	Phase 3
0.716	Intermediate Similarity	NPD3625	Discontinued
0.7143	Intermediate Similarity	NPD4500	Approved
0.7143	Intermediate Similarity	NPD3170	Approved
0.7143	Intermediate Similarity	NPD3376	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4501	Approved
0.7135	Intermediate Similarity	NPD7114	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2435	Approved
0.7117	Intermediate Similarity	NPD2365	Approved
0.7104	Intermediate Similarity	NPD8103	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD4121	Phase 3
0.7101	Intermediate Similarity	NPD4120	Approved
0.7093	Intermediate Similarity	NPD2506	Approved
0.7073	Intermediate Similarity	NPD5024	Approved
0.7066	Intermediate Similarity	NPD7528	Approved
0.7059	Intermediate Similarity	NPD5742	Approved
0.7059	Intermediate Similarity	NPD5741	Approved
0.7059	Intermediate Similarity	NPD5743	Approved
0.7041	Intermediate Similarity	NPD3399	Approved
0.6978	Remote Similarity	NPD8281	Discontinued
0.6963	Remote Similarity	NPD6805	Discontinued
0.6947	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD2427	Approved
0.6933	Remote Similarity	NPD1110	Approved
0.6933	Remote Similarity	NPD1109	Approved
0.6927	Remote Similarity	NPD7940	Phase 3
0.6919	Remote Similarity	NPD6570	Approved
0.6919	Remote Similarity	NPD6891	Phase 2
0.6919	Remote Similarity	NPD6571	Approved
0.691	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD2994	Approved
0.6893	Remote Similarity	NPD2037	Approved
0.6875	Remote Similarity	NPD7036	Phase 3
0.6875	Remote Similarity	NPD7035	Approved
0.6871	Remote Similarity	NPD2567	Approved
0.6871	Remote Similarity	NPD2569	Approved
0.6868	Remote Similarity	NPD4330	Approved
0.6868	Remote Similarity	NPD4329	Approved
0.6864	Remote Similarity	NPD4432	Discontinued
0.6856	Remote Similarity	NPD7205	Discontinued
0.6842	Remote Similarity	NPD2117	Pre-registration
0.6842	Remote Similarity	NPD2115	Approved
0.6842	Remote Similarity	NPD2116	Approved
0.6833	Remote Similarity	NPD3423	Phase 2
0.6833	Remote Similarity	NPD3422	Phase 3
0.6833	Remote Similarity	NPD5466	Approved
0.6826	Remote Similarity	NPD2387	Approved
0.6821	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD2432	Approved
0.6816	Remote Similarity	NPD2431	Approved
0.681	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6659	Phase 2
0.6807	Remote Similarity	NPD2923	Approved
0.6805	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7244	Discontinued
0.6798	Remote Similarity	NPD2404	Discontinued
0.6798	Remote Similarity	NPD2454	Approved
0.6798	Remote Similarity	NPD2455	Approved
0.679	Remote Similarity	NPD5185	Approved
0.679	Remote Similarity	NPD5182	Approved
0.679	Remote Similarity	NPD5184	Approved
0.6788	Remote Similarity	NPD4600	Approved
0.6788	Remote Similarity	NPD4601	Approved
0.6786	Remote Similarity	NPD6017	Discontinued
0.6786	Remote Similarity	NPD5931	Phase 3
0.6786	Remote Similarity	NPD5932	Phase 3
0.6786	Remote Similarity	NPD5933	Phase 3
0.6782	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD3377	Discontinued
0.6778	Remote Similarity	NPD5997	Discontinued
0.6774	Remote Similarity	NPD2946	Phase 2
0.6758	Remote Similarity	NPD3792	Approved
0.6753	Remote Similarity	NPD3031	Approved
0.6753	Remote Similarity	NPD3030	Approved
0.6753	Remote Similarity	NPD6238	Discontinued
0.6753	Remote Similarity	NPD3032	Approved
0.6744	Remote Similarity	NPD2948	Discontinued
0.6742	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD3470	Approved
0.6739	Remote Similarity	NPD3471	Approved
0.6731	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD2608	Approved
0.6731	Remote Similarity	NPD2609	Approved
0.6731	Remote Similarity	NPD2611	Approved
0.6731	Remote Similarity	NPD4215	Approved
0.6731	Remote Similarity	NPD4216	Approved
0.6731	Remote Similarity	NPD3131	Approved
0.6731	Remote Similarity	NPD2610	Approved
0.6731	Remote Similarity	NPD4217	Approved
0.6731	Remote Similarity	NPD4218	Approved
0.6731	Remote Similarity	NPD2612	Approved
0.6731	Remote Similarity	NPD3132	Approved
0.6721	Remote Similarity	NPD3782	Discontinued
0.672	Remote Similarity	NPD5504	Discontinued
0.6703	Remote Similarity	NPD2083	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4602	Approved
0.6702	Remote Similarity	NPD4334	Discontinued
0.6688	Remote Similarity	NPD1360	Approved
0.6686	Remote Similarity	NPD6185	Discontinued
0.6686	Remote Similarity	NPD6622	Phase 1
0.6685	Remote Similarity	NPD5430	Discontinued
0.6684	Remote Similarity	NPD7569	Approved
0.6684	Remote Similarity	NPD7570	Approved
0.6667	Remote Similarity	NPD5186	Approved
0.6667	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5183	Approved
0.6667	Remote Similarity	NPD4682	Phase 2
0.6649	Remote Similarity	NPD6874	Approved
0.6649	Remote Similarity	NPD3435	Discontinued
0.6647	Remote Similarity	NPD4607	Approved
0.6647	Remote Similarity	NPD6416	Phase 2
0.6646	Remote Similarity	NPD2613	Approved
0.6633	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD3828	Approved
0.663	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD3790	Phase 2
0.6628	Remote Similarity	NPD5748	Phase 2
0.6627	Remote Similarity	NPD7487	Discontinued
0.6626	Remote Similarity	NPD1527	Phase 2
0.6626	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD2844	Phase 3
0.6609	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD6758	Approved
0.6608	Remote Similarity	NPD3352	Approved
0.6607	Remote Similarity	NPD6768	Approved
0.6606	Remote Similarity	NPD6073	Approved
0.6605	Remote Similarity	NPD1069	Approved
0.6605	Remote Similarity	NPD1070	Approved
0.6595	Remote Similarity	NPD6878	Phase 2
0.6595	Remote Similarity	NPD6879	Phase 2
0.6592	Remote Similarity	NPD2915	Discontinued
0.659	Remote Similarity	NPD5982	Phase 2
0.6588	Remote Similarity	NPD7295	Approved
0.6587	Remote Similarity	NPD989	Approved
0.6583	Remote Similarity	NPD6518	Discontinued
0.6579	Remote Similarity	NPD4499	Approved
0.6579	Remote Similarity	NPD2914	Approved
0.6579	Remote Similarity	NPD2913	Approved
0.6578	Remote Similarity	NPD3436	Approved
0.6576	Remote Similarity	NPD8006	Clinical (unspecified phase)
0.657	Remote Similarity	NPD4161	Discontinued
0.6566	Remote Similarity	NPD6342	Discontinued
0.6562	Remote Similarity	NPD553	Approved
0.6562	Remote Similarity	NPD9567	Approved
0.6562	Remote Similarity	NPD552	Approved
0.6558	Remote Similarity	NPD6069	Approved
0.6558	Remote Similarity	NPD6070	Approved
0.6557	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD4370	Phase 3
0.6536	Remote Similarity	NPD8008	Approved
0.6536	Remote Similarity	NPD8007	Approved
0.6534	Remote Similarity	NPD2836	Approved
0.6533	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD4513	Discontinued
0.6532	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD2574	Discontinued
0.6524	Remote Similarity	NPD3614	Approved
0.6524	Remote Similarity	NPD3615	Approved
0.6524	Remote Similarity	NPD3616	Approved
0.6524	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD4746	Phase 3
0.6524	Remote Similarity	NPD2570	Approved
0.6524	Remote Similarity	NPD4745	Approved
0.6524	Remote Similarity	NPD3088	Approved
0.6524	Remote Similarity	NPD2573	Approved
0.6524	Remote Similarity	NPD2566	Approved
0.6524	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD2949	Approved
0.6524	Remote Similarity	NPD2571	Approved
0.6524	Remote Similarity	NPD3090	Approved
0.6524	Remote Similarity	NPD3087	Approved
0.6524	Remote Similarity	NPD3089	Approved
0.6524	Remote Similarity	NPD2950	Approved
0.6522	Remote Similarity	NPD3978	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5104	Approved
0.6519	Remote Similarity	NPD3468	Approved
0.651	Remote Similarity	NPD4315	Phase 2
0.6509	Remote Similarity	NPD6566	Discontinued
0.6506	Remote Similarity	NPD5725	Approved
0.6505	Remote Similarity	NPD5899	Approved
0.6505	Remote Similarity	NPD5898	Approved
0.6505	Remote Similarity	NPD5897	Approved
0.6497	Remote Similarity	NPD6321	Discontinued
0.6494	Remote Similarity	NPD7606	Phase 3
0.6485	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.648	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.648	Remote Similarity	NPD6999	Discontinued
0.6478	Remote Similarity	NPD3622	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