NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	194.07
Volume:	184.926
LogP:	-0.508
LogD:	-0.241
LogS:	-1.358
# Rotatable Bonds:	1
TPSA:	78.25
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.552
Synthetic Accessibility Score:	3.227
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.928
MDCK Permeability:	1.0390190254838672e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.03
Human Intestinal Absorption (HIA):	0.135
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.224

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.756
Plasma Protein Binding (PPB):	21.12126350402832%
Volume Distribution (VD):	1.301
Pgp-substrate:	75.89861297607422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.058
CYP1A2-substrate:	0.916
CYP2C19-inhibitor:	0.054
CYP2C19-substrate:	0.302
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.639
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.258
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.117

ADMET: Excretion

Clearance (CL):	2.655
Half-life (T1/2):	0.856

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.428
Drug-inuced Liver Injury (DILI):	0.054
AMES Toxicity:	0.18
Rat Oral Acute Toxicity:	0.227
Maximum Recommended Daily Dose:	0.621
Skin Sensitization:	0.137
Carcinogencity:	0.551
Eye Corrosion:	0.003
Eye Irritation:	0.175
Respiratory Toxicity:	0.377

Download Data

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

Natural Product: NPC311282

Natural Product ID:	NPC311282
*Common Name:**	Makaluvic Acid A
IUPAC Name:	5-methyl-4-oxo-6,7-dihydro-2H-pyrrolo[3,4-c]pyridine-3-carboxylic acid
Synonyms:
Standard InCHIKey:	PTBJVLGXDFOMFM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H10N2O3/c1-11-3-2-5-4-10-7(9(13)14)6(5)8(11)12/h4,10H,2-3H2,1H3,(H,13,14)
SMILES:	CN1CCc2c(C1=O)c([nH]c2)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463010
PubChem CID:	10726460
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000213] Pyrrolopyridines

*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
NPO32524	latrunculid sponges	Species	n.a.	n.a.	n.a.	South African	n.a.	PMID[15332840]
NPO32467	zyzzya fuliginosus	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[8946754]

☑ 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
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	28399.0	nM	PMID[496935]

☑ 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 NPC311282 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	320
0.1-0.2	4404
0.2-0.3	15367
0.3-0.4	15757
0.4-0.5	3202
0.5-0.6	2631
0.6-0.7	927
0.7-0.8	85
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8929	High Similarity	NPC302647
0.7966	Intermediate Similarity	NPC273532
0.7771	Intermediate Similarity	NPC470680
0.7771	Intermediate Similarity	NPC100104
0.7746	Intermediate Similarity	NPC33229
0.7701	Intermediate Similarity	NPC75544
0.7697	Intermediate Similarity	NPC41717
0.7647	Intermediate Similarity	NPC278434
0.7614	Intermediate Similarity	NPC474492
0.7526	Intermediate Similarity	NPC103361
0.7474	Intermediate Similarity	NPC469489
0.7444	Intermediate Similarity	NPC233380
0.7409	Intermediate Similarity	NPC135950
0.7404	Intermediate Similarity	NPC229893
0.7399	Intermediate Similarity	NPC302159
0.7389	Intermediate Similarity	NPC274981
0.7379	Intermediate Similarity	NPC269270
0.7371	Intermediate Similarity	NPC77061
0.736	Intermediate Similarity	NPC471944
0.7358	Intermediate Similarity	NPC473821
0.7344	Intermediate Similarity	NPC138370
0.7343	Intermediate Similarity	NPC14686
0.733	Intermediate Similarity	NPC470679
0.733	Intermediate Similarity	NPC217021
0.7323	Intermediate Similarity	NPC57398
0.7314	Intermediate Similarity	NPC123906
0.7313	Intermediate Similarity	NPC266249
0.7291	Intermediate Similarity	NPC82370
0.7288	Intermediate Similarity	NPC251391
0.7288	Intermediate Similarity	NPC312860
0.7273	Intermediate Similarity	NPC473878
0.7273	Intermediate Similarity	NPC471655
0.7255	Intermediate Similarity	NPC110182
0.7245	Intermediate Similarity	NPC74153
0.7241	Intermediate Similarity	NPC123839
0.7231	Intermediate Similarity	NPC93390
0.7211	Intermediate Similarity	NPC207851
0.7202	Intermediate Similarity	NPC83111
0.7194	Intermediate Similarity	NPC109922
0.7194	Intermediate Similarity	NPC292361
0.7189	Intermediate Similarity	NPC249614
0.7181	Intermediate Similarity	NPC126709
0.7181	Intermediate Similarity	NPC248041
0.7166	Intermediate Similarity	NPC476419
0.7165	Intermediate Similarity	NPC114974
0.7157	Intermediate Similarity	NPC473814
0.7157	Intermediate Similarity	NPC78767
0.7151	Intermediate Similarity	NPC263455
0.715	Intermediate Similarity	NPC221873
0.7143	Intermediate Similarity	NPC202812
0.7143	Intermediate Similarity	NPC167400
0.7143	Intermediate Similarity	NPC52831
0.7143	Intermediate Similarity	NPC325705
0.7128	Intermediate Similarity	NPC111275
0.712	Intermediate Similarity	NPC477003
0.709	Intermediate Similarity	NPC283219
0.7087	Intermediate Similarity	NPC118940
0.7085	Intermediate Similarity	NPC293917
0.7074	Intermediate Similarity	NPC267885
0.7072	Intermediate Similarity	NPC213914
0.7071	Intermediate Similarity	NPC141454
0.7062	Intermediate Similarity	NPC100726
0.7062	Intermediate Similarity	NPC105811
0.7056	Intermediate Similarity	NPC209362
0.7037	Intermediate Similarity	NPC84827
0.7037	Intermediate Similarity	NPC14113
0.7037	Intermediate Similarity	NPC145885
0.7033	Intermediate Similarity	NPC472285
0.7026	Intermediate Similarity	NPC154339
0.7024	Intermediate Similarity	NPC61038
0.7022	Intermediate Similarity	NPC102664
0.7021	Intermediate Similarity	NPC203468
0.7021	Intermediate Similarity	NPC110500
0.7021	Intermediate Similarity	NPC149155
0.7005	Intermediate Similarity	NPC267343
0.6989	Remote Similarity	NPC159630
0.6989	Remote Similarity	NPC230085
0.6983	Remote Similarity	NPC313889
0.6978	Remote Similarity	NPC475870
0.6978	Remote Similarity	NPC212742
0.6977	Remote Similarity	NPC328029
0.6965	Remote Similarity	NPC45459
0.6965	Remote Similarity	NPC315491
0.6963	Remote Similarity	NPC317010
0.6961	Remote Similarity	NPC175602
0.695	Remote Similarity	NPC131887
0.695	Remote Similarity	NPC474916
0.6949	Remote Similarity	NPC467188
0.6944	Remote Similarity	NPC472260
0.6944	Remote Similarity	NPC70406
0.6943	Remote Similarity	NPC228835
0.6941	Remote Similarity	NPC182222
0.6936	Remote Similarity	NPC114310
0.6927	Remote Similarity	NPC270918
0.6923	Remote Similarity	NPC471193
0.6923	Remote Similarity	NPC36498
0.6923	Remote Similarity	NPC471194
0.6919	Remote Similarity	NPC469717
0.6915	Remote Similarity	NPC123395
0.6912	Remote Similarity	NPC472259
0.6911	Remote Similarity	NPC11126
0.6907	Remote Similarity	NPC282103
0.6905	Remote Similarity	NPC36405
0.6902	Remote Similarity	NPC63338
0.6902	Remote Similarity	NPC324203
0.6902	Remote Similarity	NPC322976
0.6898	Remote Similarity	NPC78020
0.689	Remote Similarity	NPC207866
0.6887	Remote Similarity	NPC74360
0.6881	Remote Similarity	NPC213308
0.6878	Remote Similarity	NPC82053
0.6872	Remote Similarity	NPC94752
0.6866	Remote Similarity	NPC248782
0.6863	Remote Similarity	NPC165599
0.6857	Remote Similarity	NPC477979
0.6847	Remote Similarity	NPC98864
0.6845	Remote Similarity	NPC316403
0.6842	Remote Similarity	NPC6865
0.6842	Remote Similarity	NPC153980
0.6837	Remote Similarity	NPC17059
0.6833	Remote Similarity	NPC477549
0.6833	Remote Similarity	NPC13432
0.6828	Remote Similarity	NPC162268
0.6825	Remote Similarity	NPC322064
0.6825	Remote Similarity	NPC253810
0.6825	Remote Similarity	NPC262338
0.6823	Remote Similarity	NPC164340
0.6823	Remote Similarity	NPC55772
0.6821	Remote Similarity	NPC133003
0.6818	Remote Similarity	NPC476460
0.6813	Remote Similarity	NPC107287
0.6812	Remote Similarity	NPC476524
0.6812	Remote Similarity	NPC171787
0.6811	Remote Similarity	NPC131718
0.6808	Remote Similarity	NPC315804
0.6808	Remote Similarity	NPC313804
0.6802	Remote Similarity	NPC473628
0.6802	Remote Similarity	NPC209917
0.6802	Remote Similarity	NPC322488
0.6794	Remote Similarity	NPC72956
0.6792	Remote Similarity	NPC27041
0.6786	Remote Similarity	NPC235684
0.6786	Remote Similarity	NPC62749
0.6782	Remote Similarity	NPC29702
0.6778	Remote Similarity	NPC112741
0.6776	Remote Similarity	NPC229055
0.6768	Remote Similarity	NPC475874
0.6766	Remote Similarity	NPC179701
0.6763	Remote Similarity	NPC183777
0.6763	Remote Similarity	NPC244741
0.6762	Remote Similarity	NPC219087
0.6757	Remote Similarity	NPC113812
0.6755	Remote Similarity	NPC474696
0.6753	Remote Similarity	NPC191415
0.6749	Remote Similarity	NPC474767
0.6748	Remote Similarity	NPC132539
0.6748	Remote Similarity	NPC473376
0.6746	Remote Similarity	NPC309845
0.6745	Remote Similarity	NPC471192
0.6739	Remote Similarity	NPC74357
0.6736	Remote Similarity	NPC219336
0.6735	Remote Similarity	NPC295158
0.6735	Remote Similarity	NPC476423
0.6734	Remote Similarity	NPC210123
0.6733	Remote Similarity	NPC156704
0.6733	Remote Similarity	NPC262898
0.6727	Remote Similarity	NPC260434
0.6726	Remote Similarity	NPC15801
0.672	Remote Similarity	NPC473706
0.672	Remote Similarity	NPC322644
0.6717	Remote Similarity	NPC213629
0.6717	Remote Similarity	NPC44354
0.6702	Remote Similarity	NPC474383
0.6702	Remote Similarity	NPC2414
0.6701	Remote Similarity	NPC315555
0.67	Remote Similarity	NPC171317
0.67	Remote Similarity	NPC67288
0.6699	Remote Similarity	NPC138562
0.6699	Remote Similarity	NPC317701
0.6699	Remote Similarity	NPC476098
0.6698	Remote Similarity	NPC276657
0.6697	Remote Similarity	NPC207686
0.6697	Remote Similarity	NPC196718
0.6697	Remote Similarity	NPC102593
0.6697	Remote Similarity	NPC319232
0.6697	Remote Similarity	NPC24370
0.6685	Remote Similarity	NPC63562
0.6684	Remote Similarity	NPC165495
0.6684	Remote Similarity	NPC183662
0.6684	Remote Similarity	NPC256828
0.6684	Remote Similarity	NPC15573
0.6684	Remote Similarity	NPC217372
0.6683	Remote Similarity	NPC102592
0.6683	Remote Similarity	NPC79356
0.6683	Remote Similarity	NPC300183
0.6682	Remote Similarity	NPC281049
0.6667	Remote Similarity	NPC477004
0.6667	Remote Similarity	NPC12944
0.6667	Remote Similarity	NPC37268
0.6667	Remote Similarity	NPC469563

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 NPC311282 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	586
0.2-0.3	1020
0.3-0.4	2225
0.4-0.5	2884
0.5-0.6	1833
0.6-0.7	403
0.7-0.8	17
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8156	Intermediate Similarity	NPD3178	Discontinued
0.7772	Intermediate Similarity	NPD1096	Discontinued
0.7701	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7663	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD485	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD1996	Discontinued
0.7326	Intermediate Similarity	NPD1643	Phase 3
0.7306	Intermediate Similarity	NPD6665	Discontinued
0.7171	Intermediate Similarity	NPD3917	Approved
0.7171	Intermediate Similarity	NPD3918	Approved
0.7171	Intermediate Similarity	NPD3916	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9074	Approved
0.7143	Intermediate Similarity	NPD9075	Approved
0.7143	Intermediate Similarity	NPD9510	Approved
0.7143	Intermediate Similarity	NPD2509	Approved
0.7143	Intermediate Similarity	NPD2510	Approved
0.7122	Intermediate Similarity	NPD3915	Approved
0.7085	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD3947	Discontinued
0.7079	Intermediate Similarity	NPD5901	Discontinued
0.7075	Intermediate Similarity	NPD6173	Approved
0.7074	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD482	Approved
0.701	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD3389	Approved
0.6986	Remote Similarity	NPD3393	Approved
0.6986	Remote Similarity	NPD3394	Approved
0.6965	Remote Similarity	NPD484	Approved
0.6957	Remote Similarity	NPD7470	Discontinued
0.6943	Remote Similarity	NPD2096	Phase 2
0.6943	Remote Similarity	NPD2091	Phase 2
0.6923	Remote Similarity	NPD9364	Phase 2
0.6923	Remote Similarity	NPD9363	Approved
0.6914	Remote Similarity	NPD107	Approved
0.6902	Remote Similarity	NPD9398	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD2095	Phase 2
0.6891	Remote Similarity	NPD2094	Phase 2
0.6891	Remote Similarity	NPD2092	Phase 2
0.6884	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD4559	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD750	Phase 2
0.6847	Remote Similarity	NPD5017	Discontinued
0.6842	Remote Similarity	NPD8097	Phase 3
0.6842	Remote Similarity	NPD8096	Phase 3
0.684	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD9362	Approved
0.6837	Remote Similarity	NPD4948	Discontinued
0.6837	Remote Similarity	NPD6752	Phase 1
0.6837	Remote Similarity	NPD6753	Phase 1
0.6821	Remote Similarity	NPD272	Approved
0.6812	Remote Similarity	NPD6376	Discontinued
0.6804	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD9271	Approved
0.6772	Remote Similarity	NPD1573	Approved
0.6772	Remote Similarity	NPD1575	Approved
0.6762	Remote Similarity	NPD8093	Discontinued
0.6755	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD5065	Approved
0.6754	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.675	Remote Similarity	NPD1173	Approved
0.6738	Remote Similarity	NPD1631	Approved
0.6729	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7619	Phase 3
0.6716	Remote Similarity	NPD7618	Phase 3
0.6713	Remote Similarity	NPD8356	Approved
0.6703	Remote Similarity	NPD820	Phase 3
0.67	Remote Similarity	NPD4922	Phase 2
0.6699	Remote Similarity	NPD3968	Approved
0.6698	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD3006	Discontinued
0.6682	Remote Similarity	NPD1623	Approved
0.6667	Remote Similarity	NPD6999	Discontinued
0.6667	Remote Similarity	NPD2213	Approved
0.6667	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5426	Phase 3
0.6667	Remote Similarity	NPD3353	Approved
0.6667	Remote Similarity	NPD2214	Approved
0.6648	Remote Similarity	NPD201	Phase 2
0.6648	Remote Similarity	NPD200	Phase 2
0.6635	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD5475	Discontinued
0.6632	Remote Similarity	NPD2844	Phase 3
0.6621	Remote Similarity	NPD7603	Discontinued
0.6618	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD706	Phase 1
0.6614	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD9382	Approved
0.6613	Remote Similarity	NPD9383	Approved
0.6605	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD3410	Approved
0.6603	Remote Similarity	NPD3411	Phase 2
0.6601	Remote Similarity	NPD2289	Phase 3
0.6601	Remote Similarity	NPD2290	Phase 3
0.6595	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD4845	Discontinued
0.6591	Remote Similarity	NPD8430	Approved
0.6587	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD460	Discontinued
0.6578	Remote Similarity	NPD1630	Approved
0.6578	Remote Similarity	NPD5255	Approved
0.6576	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD510	Phase 1
0.6575	Remote Similarity	NPD175	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD8094	Discontinued
0.6567	Remote Similarity	NPD2336	Approved
0.6558	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD3967	Approved
0.6553	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD8289	Discontinued
0.6542	Remote Similarity	NPD7970	Approved
0.6542	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5317	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD1659	Phase 1
0.6531	Remote Similarity	NPD1618	Phase 2
0.6528	Remote Similarity	NPD7878	Phase 2
0.6526	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD3321	Discontinued
0.6516	Remote Similarity	NPD6165	Phase 2
0.6516	Remote Similarity	NPD6164	Phase 2
0.6507	Remote Similarity	NPD4903	Approved
0.6507	Remote Similarity	NPD944	Approved
0.6507	Remote Similarity	NPD8098	Approved
0.6507	Remote Similarity	NPD4905	Approved
0.6507	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD6987	Phase 1
0.6507	Remote Similarity	NPD4906	Approved
0.65	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD6369	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD7666	Phase 3
0.6493	Remote Similarity	NPD7665	Phase 2
0.6486	Remote Similarity	NPD1571	Phase 2
0.6485	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.648	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.648	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD4904	Approved
0.6476	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD7001	Phase 3
0.6476	Remote Similarity	NPD7010	Phase 3
0.6476	Remote Similarity	NPD3507	Phase 2
0.6471	Remote Similarity	NPD7711	Discontinued
0.6455	Remote Similarity	NPD2511	Approved
0.6453	Remote Similarity	NPD4376	Phase 3
0.6453	Remote Similarity	NPD5505	Discontinued
0.6452	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6445	Remote Similarity	NPD1506	Discontinued
0.6439	Remote Similarity	NPD2307	Discontinued
0.6436	Remote Similarity	NPD2564	Approved
0.6436	Remote Similarity	NPD2565	Phase 2
0.6429	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD3243	Approved
0.641	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6664	Approved
0.6407	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD1591	Approved
0.6402	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD704	Clinical (unspecified phase)
0.64	Remote Similarity	NPD1572	Phase 2
0.64	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD1587	Approved
0.6389	Remote Similarity	NPD5293	Phase 2
0.6386	Remote Similarity	NPD6068	Discontinued
0.6385	Remote Similarity	NPD5510	Approved
0.6381	Remote Similarity	NPD6176	Phase 1
0.6368	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD5809	Phase 3
0.6368	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.635	Remote Similarity	NPD721	Approved
0.6347	Remote Similarity	NPD6770	Approved
0.6343	Remote Similarity	NPD3795	Approved
0.6343	Remote Similarity	NPD3794	Approved
0.6338	Remote Similarity	NPD1997	Phase 2
0.6337	Remote Similarity	NPD4988	Discontinued
0.6335	Remote Similarity	NPD6209	Approved
0.6333	Remote Similarity	NPD2896	Discontinued
0.633	Remote Similarity	NPD6710	Phase 3
0.633	Remote Similarity	NPD2813	Phase 3
0.633	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD4883	Approved
0.6324	Remote Similarity	NPD4703	Approved
0.6324	Remote Similarity	NPD1270	Approved
0.6324	Remote Similarity	NPD4702	Approved
0.6323	Remote Similarity	NPD3263	Phase 3
0.6322	Remote Similarity	NPD9284	Approved

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