NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	180.05
Volume:	167.63
LogP:	-1.103
LogD:	-0.422
LogS:	-1.679
# Rotatable Bonds:	1
TPSA:	89.11
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.46
Synthetic Accessibility Score:	3.317
Fsp3:	0.125
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:	-4.961
MDCK Permeability:	5.497059191839071e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.035
Human Intestinal Absorption (HIA):	0.673
20% Bioavailability (F20%):	0.112
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.783
Plasma Protein Binding (PPB):	17.0462589263916%
Volume Distribution (VD):	0.723
Pgp-substrate:	77.23899841308594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.641
CYP2C19-inhibitor:	0.073
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.7
CYP2D6-inhibitor:	0.028
CYP2D6-substrate:	0.204
CYP3A4-inhibitor:	0.008
CYP3A4-substrate:	0.032

ADMET: Excretion

Clearance (CL):	3.325
Half-life (T1/2):	0.926

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.181
Drug-inuced Liver Injury (DILI):	0.54
AMES Toxicity:	0.162
Rat Oral Acute Toxicity:	0.61
Maximum Recommended Daily Dose:	0.757
Skin Sensitization:	0.392
Carcinogencity:	0.305
Eye Corrosion:	0.003
Eye Irritation:	0.794
Respiratory Toxicity:	0.664

Download Data

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

Natural Product: NPC302647

Natural Product ID:	NPC302647
*Common Name:**	Makaluvic Acid C
IUPAC Name:	4-oxo-2,5,6,7-tetrahydropyrrolo[3,4-c]pyridine-3-carboxylic acid
Synonyms:	Makaluvic Acid C
Standard InCHIKey:	FZJIKBLWZILHGL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H8N2O3/c11-7-5-4(1-2-9-7)3-10-6(5)8(12)13/h3,10H,1-2H2,(H,9,11)(H,12,13)
SMILES:	C1CN=C(c2c1c[nH]c2C(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL507654
PubChem CID:	11401113
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
NPO9722	Strongylodesma aliwaliensis	n.a.	n.a.	n.a.	n.a.	South African	n.a.	PMID[15844938]
NPO9722	Strongylodesma aliwaliensis	n.a.	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
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	150000.0	nM	PMID[531240]

☑ 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 NPC302647 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	303
0.1-0.2	3886
0.2-0.3	14236
0.3-0.4	16847
0.4-0.5	3730
0.5-0.6	2598
0.6-0.7	964
0.7-0.8	124
0.8-0.85	7
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	NPC311282
0.8448	Intermediate Similarity	NPC75544
0.8221	Intermediate Similarity	NPC33229
0.8012	Intermediate Similarity	NPC273532
0.7857	Intermediate Similarity	NPC473821
0.7836	Intermediate Similarity	NPC41717
0.7818	Intermediate Similarity	NPC471655
0.7778	Intermediate Similarity	NPC278434
0.7772	Intermediate Similarity	NPC77061
0.773	Intermediate Similarity	NPC74153
0.7668	Intermediate Similarity	NPC82370
0.7636	Intermediate Similarity	NPC302159
0.7596	Intermediate Similarity	NPC83111
0.7527	Intermediate Similarity	NPC93390
0.7514	Intermediate Similarity	NPC207851
0.7486	Intermediate Similarity	NPC248041
0.7486	Intermediate Similarity	NPC283219
0.7486	Intermediate Similarity	NPC126709
0.7447	Intermediate Similarity	NPC78767
0.7447	Intermediate Similarity	NPC473814
0.7442	Intermediate Similarity	NPC474492
0.7433	Intermediate Similarity	NPC202812
0.743	Intermediate Similarity	NPC111275
0.7416	Intermediate Similarity	NPC149155
0.7416	Intermediate Similarity	NPC203468
0.7416	Intermediate Similarity	NPC110500
0.7409	Intermediate Similarity	NPC175602
0.7399	Intermediate Similarity	NPC100104
0.7399	Intermediate Similarity	NPC470680
0.7387	Intermediate Similarity	NPC472285
0.7384	Intermediate Similarity	NPC475870
0.7384	Intermediate Similarity	NPC212742
0.7381	Intermediate Similarity	NPC100726
0.7374	Intermediate Similarity	NPC267885
0.7366	Intermediate Similarity	NPC138370
0.7348	Intermediate Similarity	NPC325705
0.7348	Intermediate Similarity	NPC52831
0.7344	Intermediate Similarity	NPC57398
0.7337	Intermediate Similarity	NPC102664
0.733	Intermediate Similarity	NPC315491
0.733	Intermediate Similarity	NPC45459
0.7303	Intermediate Similarity	NPC262338
0.7299	Intermediate Similarity	NPC131718
0.7296	Intermediate Similarity	NPC61038
0.7292	Intermediate Similarity	NPC471944
0.7288	Intermediate Similarity	NPC78020
0.7258	Intermediate Similarity	NPC473628
0.7255	Intermediate Similarity	NPC229893
0.7245	Intermediate Similarity	NPC266249
0.7238	Intermediate Similarity	NPC14113
0.7238	Intermediate Similarity	NPC84827
0.7238	Intermediate Similarity	NPC145885
0.7235	Intermediate Similarity	NPC13432
0.7219	Intermediate Similarity	NPC475874
0.7216	Intermediate Similarity	NPC162268
0.7216	Intermediate Similarity	NPC274981
0.7209	Intermediate Similarity	NPC312860
0.72	Intermediate Similarity	NPC324203
0.72	Intermediate Similarity	NPC322976
0.72	Intermediate Similarity	NPC63338
0.7195	Intermediate Similarity	NPC328029
0.7188	Intermediate Similarity	NPC103361
0.7186	Intermediate Similarity	NPC118940
0.7173	Intermediate Similarity	NPC141454
0.7173	Intermediate Similarity	NPC156704
0.7172	Intermediate Similarity	NPC123839
0.7166	Intermediate Similarity	NPC221873
0.7164	Intermediate Similarity	NPC36405
0.716	Intermediate Similarity	NPC167400
0.715	Intermediate Similarity	NPC213308
0.715	Intermediate Similarity	NPC207866
0.7128	Intermediate Similarity	NPC469489
0.712	Intermediate Similarity	NPC292361
0.7119	Intermediate Similarity	NPC102423
0.7112	Intermediate Similarity	NPC36498
0.7111	Intermediate Similarity	NPC249614
0.7104	Intermediate Similarity	NPC55772
0.7097	Intermediate Similarity	NPC295158
0.7093	Intermediate Similarity	NPC473878
0.7091	Intermediate Similarity	NPC29702
0.7088	Intermediate Similarity	NPC476419
0.7074	Intermediate Similarity	NPC209917
0.7069	Intermediate Similarity	NPC263455
0.7068	Intermediate Similarity	NPC135950
0.7065	Intermediate Similarity	NPC234403
0.7065	Intermediate Similarity	NPC79777
0.7059	Intermediate Similarity	NPC315555
0.7059	Intermediate Similarity	NPC235684
0.7048	Intermediate Similarity	NPC114310
0.7047	Intermediate Similarity	NPC131887
0.7041	Intermediate Similarity	NPC165599
0.7037	Intermediate Similarity	NPC154339
0.7027	Intermediate Similarity	NPC71037
0.702	Intermediate Similarity	NPC244741
0.7017	Intermediate Similarity	NPC253810
0.7015	Intermediate Similarity	NPC110182
0.701	Intermediate Similarity	NPC123395
0.6994	Remote Similarity	NPC52110
0.6985	Remote Similarity	NPC143075
0.6984	Remote Similarity	NPC321708
0.6983	Remote Similarity	NPC233380
0.698	Remote Similarity	NPC229348
0.6973	Remote Similarity	NPC317010
0.6971	Remote Similarity	NPC63562
0.6963	Remote Similarity	NPC15801
0.6961	Remote Similarity	NPC256828
0.6959	Remote Similarity	NPC67288
0.6954	Remote Similarity	NPC217021
0.6954	Remote Similarity	NPC470679
0.6952	Remote Similarity	NPC228835
0.6943	Remote Similarity	NPC179701
0.6936	Remote Similarity	NPC123906
0.6932	Remote Similarity	NPC141353
0.6931	Remote Similarity	NPC17059
0.6928	Remote Similarity	NPC291517
0.6927	Remote Similarity	NPC267343
0.6919	Remote Similarity	NPC11126
0.6915	Remote Similarity	NPC282103
0.6915	Remote Similarity	NPC241025
0.6914	Remote Similarity	NPC251391
0.691	Remote Similarity	NPC279918
0.691	Remote Similarity	NPC322644
0.6909	Remote Similarity	NPC322488
0.6907	Remote Similarity	NPC262898
0.6893	Remote Similarity	NPC74360
0.6893	Remote Similarity	NPC132680
0.6893	Remote Similarity	NPC269919
0.6891	Remote Similarity	NPC276517
0.6885	Remote Similarity	NPC313791
0.6884	Remote Similarity	NPC82053
0.6878	Remote Similarity	NPC62749
0.6875	Remote Similarity	NPC209362
0.6872	Remote Similarity	NPC282231
0.6872	Remote Similarity	NPC248782
0.6872	Remote Similarity	NPC474916
0.6869	Remote Similarity	NPC182222
0.6865	Remote Similarity	NPC183662
0.6865	Remote Similarity	NPC217372
0.6865	Remote Similarity	NPC15573
0.6864	Remote Similarity	NPC85443
0.6856	Remote Similarity	NPC109922
0.685	Remote Similarity	NPC183777
0.685	Remote Similarity	NPC88008
0.6845	Remote Similarity	NPC469717
0.6842	Remote Similarity	NPC474259
0.6842	Remote Similarity	NPC477415
0.6842	Remote Similarity	NPC23476
0.6837	Remote Similarity	NPC474767
0.6834	Remote Similarity	NPC477043
0.6833	Remote Similarity	NPC194640
0.6828	Remote Similarity	NPC164340
0.6828	Remote Similarity	NPC213468
0.6828	Remote Similarity	NPC219336
0.6826	Remote Similarity	NPC23215
0.6825	Remote Similarity	NPC192712
0.6823	Remote Similarity	NPC114974
0.6816	Remote Similarity	NPC171787
0.6814	Remote Similarity	NPC89508
0.6812	Remote Similarity	NPC269270
0.6809	Remote Similarity	NPC48938
0.6802	Remote Similarity	NPC159630
0.6802	Remote Similarity	NPC230085
0.6798	Remote Similarity	NPC213914
0.6791	Remote Similarity	NPC477042
0.6791	Remote Similarity	NPC182940
0.6786	Remote Similarity	NPC477044
0.6786	Remote Similarity	NPC477041
0.6786	Remote Similarity	NPC306376
0.6784	Remote Similarity	NPC476098
0.6779	Remote Similarity	NPC14686
0.6772	Remote Similarity	NPC165495
0.6768	Remote Similarity	NPC98864
0.6766	Remote Similarity	NPC321428
0.6766	Remote Similarity	NPC270918
0.6765	Remote Similarity	NPC219087
0.6763	Remote Similarity	NPC467188
0.6763	Remote Similarity	NPC159856
0.6761	Remote Similarity	NPC109158
0.676	Remote Similarity	NPC230869
0.676	Remote Similarity	NPC113812
0.6758	Remote Similarity	NPC54988
0.6758	Remote Similarity	NPC49954
0.6758	Remote Similarity	NPC474561
0.6758	Remote Similarity	NPC474696
0.6754	Remote Similarity	NPC46580
0.6751	Remote Similarity	NPC477045
0.6751	Remote Similarity	NPC293917
0.675	Remote Similarity	NPC469563
0.6749	Remote Similarity	NPC309845
0.6749	Remote Similarity	NPC469562
0.6749	Remote Similarity	NPC220594
0.674	Remote Similarity	NPC263439
0.674	Remote Similarity	NPC211187
0.6737	Remote Similarity	NPC280290
0.6737	Remote Similarity	NPC314002
0.6733	Remote Similarity	NPC476524
0.6729	Remote Similarity	NPC267853
0.6729	Remote Similarity	NPC315062
0.6723	Remote Similarity	NPC107287
0.6721	Remote Similarity	NPC63751

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 NPC302647 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	553
0.2-0.3	1004
0.3-0.4	2111
0.4-0.5	3042
0.5-0.6	1862
0.6-0.7	372
0.7-0.8	27
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8529	High Similarity	NPD3178	Discontinued
0.8061	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7539	Intermediate Similarity	NPD5901	Discontinued
0.7514	Intermediate Similarity	NPD1096	Discontinued
0.75	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD482	Approved
0.7401	Intermediate Similarity	NPD485	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD3918	Approved
0.736	Intermediate Similarity	NPD3916	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD3917	Approved
0.7348	Intermediate Similarity	NPD9510	Approved
0.733	Intermediate Similarity	NPD484	Approved
0.731	Intermediate Similarity	NPD3915	Approved
0.7268	Intermediate Similarity	NPD2094	Phase 2
0.7268	Intermediate Similarity	NPD2092	Phase 2
0.7268	Intermediate Similarity	NPD2095	Phase 2
0.7228	Intermediate Similarity	NPD2091	Phase 2
0.7228	Intermediate Similarity	NPD2096	Phase 2
0.7216	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD9074	Approved
0.716	Intermediate Similarity	NPD9075	Approved
0.7158	Intermediate Similarity	NPD1643	Phase 3
0.7112	Intermediate Similarity	NPD9364	Phase 2
0.7112	Intermediate Similarity	NPD9363	Approved
0.7108	Intermediate Similarity	NPD1996	Discontinued
0.7108	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD750	Phase 2
0.7053	Intermediate Similarity	NPD6665	Discontinued
0.7027	Intermediate Similarity	NPD9362	Approved
0.6989	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD706	Phase 1
0.6961	Remote Similarity	NPD1575	Approved
0.6961	Remote Similarity	NPD1573	Approved
0.6931	Remote Similarity	NPD4948	Discontinued
0.6927	Remote Similarity	NPD1631	Approved
0.6923	Remote Similarity	NPD107	Approved
0.6919	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD2844	Phase 3
0.69	Remote Similarity	NPD2510	Approved
0.69	Remote Similarity	NPD2509	Approved
0.6893	Remote Similarity	NPD9382	Approved
0.6893	Remote Similarity	NPD9383	Approved
0.6884	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7470	Discontinued
0.6842	Remote Similarity	NPD6752	Phase 1
0.6842	Remote Similarity	NPD6753	Phase 1
0.6832	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3393	Approved
0.6829	Remote Similarity	NPD3389	Approved
0.6829	Remote Similarity	NPD3394	Approved
0.6804	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD8097	Phase 3
0.6765	Remote Similarity	NPD8096	Phase 3
0.676	Remote Similarity	NPD1630	Approved
0.6757	Remote Similarity	NPD5065	Approved
0.6753	Remote Similarity	NPD1173	Approved
0.6751	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5317	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD9271	Approved
0.6683	Remote Similarity	NPD8093	Discontinued
0.6682	Remote Similarity	NPD6173	Approved
0.6667	Remote Similarity	NPD8098	Approved
0.6622	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD820	Phase 3
0.6609	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD9080	Approved
0.6603	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD3353	Approved
0.6584	Remote Similarity	NPD3947	Discontinued
0.6582	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD5255	Approved
0.6573	Remote Similarity	NPD510	Phase 1
0.6564	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD1587	Approved
0.6557	Remote Similarity	NPD5138	Approved
0.6557	Remote Similarity	NPD5140	Approved
0.6553	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7970	Approved
0.6538	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD5017	Discontinued
0.6513	Remote Similarity	NPD5117	Phase 2
0.6513	Remote Similarity	NPD2565	Phase 2
0.6513	Remote Similarity	NPD2564	Approved
0.6512	Remote Similarity	NPD4845	Discontinued
0.6512	Remote Similarity	NPD2896	Discontinued
0.6506	Remote Similarity	NPD9284	Approved
0.6504	Remote Similarity	NPD5482	Discontinued
0.6502	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD5426	Phase 3
0.65	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.649	Remote Similarity	NPD8094	Discontinued
0.6488	Remote Similarity	NPD6376	Discontinued
0.6485	Remote Similarity	NPD8073	Approved
0.6484	Remote Similarity	NPD704	Clinical (unspecified phase)
0.648	Remote Similarity	NPD2336	Approved
0.6473	Remote Similarity	NPD5475	Discontinued
0.6471	Remote Similarity	NPD7001	Phase 3
0.6465	Remote Similarity	NPD7603	Discontinued
0.6462	Remote Similarity	NPD6242	Discontinued
0.6456	Remote Similarity	NPD6529	Discontinued
0.6455	Remote Similarity	NPD3006	Discontinued
0.6453	Remote Similarity	NPD9506	Approved
0.6453	Remote Similarity	NPD8072	Approved
0.6452	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD4376	Phase 3
0.6445	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD180	Clinical (unspecified phase)
0.644	Remote Similarity	NPD6452	Discontinued
0.6439	Remote Similarity	NPD3410	Approved
0.6439	Remote Similarity	NPD3411	Phase 2
0.6429	Remote Similarity	NPD3321	Discontinued
0.6429	Remote Similarity	NPD1213	Phase 3
0.6425	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD944	Approved
0.6418	Remote Similarity	NPD6999	Discontinued
0.6418	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4702	Approved
0.6404	Remote Similarity	NPD4703	Approved
0.6402	Remote Similarity	NPD1586	Approved
0.6402	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7948	Phase 1
0.64	Remote Similarity	NPD1592	Phase 3
0.6398	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.639	Remote Similarity	NPD4559	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD4076	Approved
0.6387	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD4079	Approved
0.6386	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD5088	Discontinued
0.6377	Remote Similarity	NPD3968	Approved
0.6372	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD981	Phase 2
0.6359	Remote Similarity	NPD4086	Phase 1
0.6355	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.635	Remote Similarity	NPD2307	Discontinued
0.6346	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD4499	Approved
0.6343	Remote Similarity	NPD1649	Discontinued
0.6341	Remote Similarity	NPD4903	Approved
0.6341	Remote Similarity	NPD6987	Phase 1
0.6341	Remote Similarity	NPD4905	Approved
0.6341	Remote Similarity	NPD4906	Approved
0.6335	Remote Similarity	NPD3506	Approved
0.6335	Remote Similarity	NPD3505	Approved
0.6332	Remote Similarity	NPD1038	Approved
0.6332	Remote Similarity	NPD460	Discontinued
0.6332	Remote Similarity	NPD4528	Approved
0.6332	Remote Similarity	NPD802	Phase 2
0.6332	Remote Similarity	NPD4529	Approved
0.6332	Remote Similarity	NPD4526	Approved
0.633	Remote Similarity	NPD1326	Approved
0.633	Remote Similarity	NPD1325	Approved
0.6329	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD3813	Approved
0.6328	Remote Similarity	NPD1352	Discontinued
0.6327	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6326	Remote Similarity	NPD8356	Approved
0.6321	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD2813	Phase 3
0.6318	Remote Similarity	NPD5003	Discontinued
0.6316	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD158	Discontinued
0.6313	Remote Similarity	NPD8289	Discontinued
0.6311	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD7957	Phase 1
0.6311	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4904	Approved
0.6304	Remote Similarity	NPD2214	Approved
0.6304	Remote Similarity	NPD604	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD2213	Approved
0.6301	Remote Similarity	NPD198	Clinical (unspecified phase)
0.63	Remote Similarity	NPD4427	Phase 2
0.6298	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD5510	Approved
0.6296	Remote Similarity	NPD2123	Phase 3
0.629	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD5596	Phase 2
0.6287	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD3717	Discontinued
0.6269	Remote Similarity	NPD6595	Phase 3
0.6269	Remote Similarity	NPD2290	Phase 3

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