NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	201.09
Volume:	201.741
LogP:	0.715
LogD:	1.41
LogS:	-2.589
# Rotatable Bonds:	0
TPSA:	63.54
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.503
Synthetic Accessibility Score:	3.657
Fsp3:	0.182
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:	-4.899
MDCK Permeability:	8.660327694087755e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.956
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.992
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.619
Plasma Protein Binding (PPB):	79.37791442871094%
Volume Distribution (VD):	1.678
Pgp-substrate:	27.075984954833984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.975
CYP1A2-substrate:	0.834
CYP2C19-inhibitor:	0.062
CYP2C19-substrate:	0.316
CYP2C9-inhibitor:	0.106
CYP2C9-substrate:	0.444
CYP2D6-inhibitor:	0.313
CYP2D6-substrate:	0.859
CYP3A4-inhibitor:	0.065
CYP3A4-substrate:	0.15

ADMET: Excretion

Clearance (CL):	8.346
Half-life (T1/2):	0.6

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.406
Drug-inuced Liver Injury (DILI):	0.856
AMES Toxicity:	0.916
Rat Oral Acute Toxicity:	0.23
Maximum Recommended Daily Dose:	0.509
Skin Sensitization:	0.801
Carcinogencity:	0.945
Eye Corrosion:	0.004
Eye Irritation:	0.461
Respiratory Toxicity:	0.917

Download Data

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

Natural Product: NPC100726

Natural Product ID:	NPC100726
*Common Name:**	Makaluvamine A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RUIRYCQUTHWLMZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H11N3O/c1-14-5-6-2-3-13-8-4-7(12)11(15)10(14)9(6)8/h4-5H,2-3,12H2,1H3
SMILES:	Cn1cc2CCN=C3C=C(C(=O)c1c23)N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449905
PubChem CID:	4002
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001734] Pyrroloquinolines [CHEMONTID:0002829] Pyrrolo[4,3,2-de]quinolines

*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
NPO32549	zyzzya fuliginosa	Species	n.a.	Eukaryota	n.a.	indopacific	n.a.	PMID[12027767]
NPO32549	zyzzya fuliginosa	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[16180829]
NPO32549	zyzzya fuliginosa	Species	n.a.	Eukaryota	n.a.	pohnpeian	n.a.	PMID[8691207]
NPO32467	zyzzya fuliginosus	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[8946754]
NPO32549	zyzzya fuliginosa	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[9134749]

☑ 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
ED50	1
IC50	3
Others	1

Activity Type	# Activity
Cell Line	3
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.4	ug ml-1	PMID[514008]
NPT1044	Individual Protein	DNA topoisomerase II alpha	Homo sapiens	IC90	=	41000.0	nM	PMID[514010]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	170.0	nM	PMID[514010]
NPT6399	Cell Line	XRS6	Cricetulus griseus	IC50	=	80.0	nM	PMID[514010]
NPT2	Others	Unspecified		IC50	=	5000.0	nM	PMID[514009]

☑ 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 NPC100726 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	455
0.1-0.2	5850
0.2-0.3	18766
0.3-0.4	11607
0.4-0.5	2721
0.5-0.6	2116
0.6-0.7	1009
0.7-0.8	145
0.8-0.85	19
0.85-0.9	6
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9441	High Similarity	NPC471655
0.9441	High Similarity	NPC473878
0.9371	High Similarity	NPC102664
0.898	High Similarity	NPC470679
0.898	High Similarity	NPC217021
0.875	High Similarity	NPC470680
0.875	High Similarity	NPC100104
0.8562	High Similarity	NPC474492
0.8467	Intermediate Similarity	NPC123906
0.8421	Intermediate Similarity	NPC251391
0.8395	Intermediate Similarity	NPC182940
0.8365	Intermediate Similarity	NPC262338
0.8289	Intermediate Similarity	NPC313889
0.8267	Intermediate Similarity	NPC467188
0.8235	Intermediate Similarity	NPC70406
0.8107	Intermediate Similarity	NPC268966
0.8061	Intermediate Similarity	NPC79777
0.8061	Intermediate Similarity	NPC234403
0.805	Intermediate Similarity	NPC274981
0.8039	Intermediate Similarity	NPC105811
0.8023	Intermediate Similarity	NPC93390
0.7975	Intermediate Similarity	NPC80681
0.7931	Intermediate Similarity	NPC473814
0.7931	Intermediate Similarity	NPC78767
0.7905	Intermediate Similarity	NPC291517
0.7898	Intermediate Similarity	NPC209362
0.7885	Intermediate Similarity	NPC472260
0.7844	Intermediate Similarity	NPC477042
0.7818	Intermediate Similarity	NPC469529
0.7808	Intermediate Similarity	NPC71236
0.78	Intermediate Similarity	NPC472288
0.7778	Intermediate Similarity	NPC477415
0.7778	Intermediate Similarity	NPC23476
0.7778	Intermediate Similarity	NPC474259
0.7759	Intermediate Similarity	NPC473821
0.7709	Intermediate Similarity	NPC106757
0.7688	Intermediate Similarity	NPC475874
0.7673	Intermediate Similarity	NPC229055
0.7669	Intermediate Similarity	NPC233380
0.7633	Intermediate Similarity	NPC73994
0.763	Intermediate Similarity	NPC473628
0.7627	Intermediate Similarity	NPC74153
0.7625	Intermediate Similarity	NPC74357
0.7624	Intermediate Similarity	NPC88115
0.7619	Intermediate Similarity	NPC284775
0.7619	Intermediate Similarity	NPC83774
0.7588	Intermediate Similarity	NPC191415
0.7578	Intermediate Similarity	NPC213914
0.7576	Intermediate Similarity	NPC70949
0.7557	Intermediate Similarity	NPC225622
0.7557	Intermediate Similarity	NPC477414
0.7557	Intermediate Similarity	NPC221726
0.7542	Intermediate Similarity	NPC474767
0.7529	Intermediate Similarity	NPC61011
0.7514	Intermediate Similarity	NPC469359
0.75	Intermediate Similarity	NPC477003
0.75	Intermediate Similarity	NPC265100
0.7472	Intermediate Similarity	NPC292361
0.7451	Intermediate Similarity	NPC65408
0.7434	Intermediate Similarity	NPC23215
0.743	Intermediate Similarity	NPC167710
0.7412	Intermediate Similarity	NPC157583
0.7412	Intermediate Similarity	NPC237188
0.741	Intermediate Similarity	NPC114637
0.7401	Intermediate Similarity	NPC216550
0.7399	Intermediate Similarity	NPC46895
0.7383	Intermediate Similarity	NPC313823
0.7381	Intermediate Similarity	NPC302647
0.7333	Intermediate Similarity	NPC242116
0.7294	Intermediate Similarity	NPC186068
0.7289	Intermediate Similarity	NPC478184
0.7284	Intermediate Similarity	NPC281094
0.7263	Intermediate Similarity	NPC304203
0.7253	Intermediate Similarity	NPC81535
0.7247	Intermediate Similarity	NPC476460
0.7246	Intermediate Similarity	NPC42372
0.7246	Intermediate Similarity	NPC115232
0.7241	Intermediate Similarity	NPC102755
0.7232	Intermediate Similarity	NPC103119
0.7216	Intermediate Similarity	NPC118084
0.7212	Intermediate Similarity	NPC293487
0.7198	Intermediate Similarity	NPC477041
0.7198	Intermediate Similarity	NPC477044
0.7193	Intermediate Similarity	NPC293216
0.7191	Intermediate Similarity	NPC469489
0.7186	Intermediate Similarity	NPC478182
0.7168	Intermediate Similarity	NPC11126
0.7167	Intermediate Similarity	NPC326422
0.7159	Intermediate Similarity	NPC295158
0.7143	Intermediate Similarity	NPC106824
0.7143	Intermediate Similarity	NPC182570
0.7143	Intermediate Similarity	NPC265605
0.7143	Intermediate Similarity	NPC48564
0.7104	Intermediate Similarity	NPC476143
0.7101	Intermediate Similarity	NPC41717
0.709	Intermediate Similarity	NPC61038
0.7079	Intermediate Similarity	NPC473946
0.7068	Intermediate Similarity	NPC477413
0.7065	Intermediate Similarity	NPC477045
0.7065	Intermediate Similarity	NPC284338
0.7062	Intermediate Similarity	NPC311282
0.7044	Intermediate Similarity	NPC58268
0.7044	Intermediate Similarity	NPC129412
0.7044	Intermediate Similarity	NPC114033
0.7044	Intermediate Similarity	NPC101130
0.7041	Intermediate Similarity	NPC71132
0.7039	Intermediate Similarity	NPC471589
0.7039	Intermediate Similarity	NPC255909
0.7033	Intermediate Similarity	NPC202812
0.7025	Intermediate Similarity	NPC110126
0.7024	Intermediate Similarity	NPC478185
0.7018	Intermediate Similarity	NPC471943
0.7017	Intermediate Similarity	NPC47190
0.7017	Intermediate Similarity	NPC472292
0.7011	Intermediate Similarity	NPC14113
0.7011	Intermediate Similarity	NPC145885
0.7011	Intermediate Similarity	NPC84827
0.7006	Intermediate Similarity	NPC228835
0.7005	Intermediate Similarity	NPC317701
0.7005	Intermediate Similarity	NPC138562
0.7	Intermediate Similarity	NPC190296
0.7	Intermediate Similarity	NPC27740
0.7	Intermediate Similarity	NPC56233
0.7	Intermediate Similarity	NPC136002
0.7	Intermediate Similarity	NPC478183
0.6995	Remote Similarity	NPC472293
0.6989	Remote Similarity	NPC470677
0.6981	Remote Similarity	NPC238499
0.6973	Remote Similarity	NPC477004
0.6973	Remote Similarity	NPC237414
0.6968	Remote Similarity	NPC477043
0.6968	Remote Similarity	NPC330326
0.6966	Remote Similarity	NPC133003
0.6966	Remote Similarity	NPC474258
0.6964	Remote Similarity	NPC473706
0.6954	Remote Similarity	NPC151635
0.6952	Remote Similarity	NPC472062
0.6952	Remote Similarity	NPC472063
0.6952	Remote Similarity	NPC472069
0.6949	Remote Similarity	NPC159125
0.6947	Remote Similarity	NPC143075
0.6944	Remote Similarity	NPC75544
0.6944	Remote Similarity	NPC209917
0.6943	Remote Similarity	NPC195704
0.6943	Remote Similarity	NPC14448
0.6943	Remote Similarity	NPC167200
0.6943	Remote Similarity	NPC200397
0.6943	Remote Similarity	NPC138596
0.6943	Remote Similarity	NPC64661
0.6943	Remote Similarity	NPC292434
0.6943	Remote Similarity	NPC207866
0.6943	Remote Similarity	NPC98156
0.694	Remote Similarity	NPC135950
0.6936	Remote Similarity	NPC252572
0.6931	Remote Similarity	NPC175602
0.6919	Remote Similarity	NPC91895
0.6919	Remote Similarity	NPC34837
0.6919	Remote Similarity	NPC32534
0.6918	Remote Similarity	NPC291389
0.6918	Remote Similarity	NPC471574
0.6918	Remote Similarity	NPC73767
0.6915	Remote Similarity	NPC476252
0.6914	Remote Similarity	NPC314372
0.691	Remote Similarity	NPC467063
0.6902	Remote Similarity	NPC128244
0.6899	Remote Similarity	NPC105127
0.6899	Remote Similarity	NPC150259
0.6899	Remote Similarity	NPC84911
0.6895	Remote Similarity	NPC469577
0.6895	Remote Similarity	NPC475410
0.6882	Remote Similarity	NPC103361
0.6882	Remote Similarity	NPC123395
0.6882	Remote Similarity	NPC472296
0.6882	Remote Similarity	NPC472297
0.6879	Remote Similarity	NPC249614
0.6878	Remote Similarity	NPC469563
0.6875	Remote Similarity	NPC12649
0.6875	Remote Similarity	NPC248041
0.6875	Remote Similarity	NPC126709
0.6872	Remote Similarity	NPC99939
0.6872	Remote Similarity	NPC308931
0.6862	Remote Similarity	NPC57398
0.6857	Remote Similarity	NPC267885
0.6845	Remote Similarity	NPC121327
0.6842	Remote Similarity	NPC2414
0.6842	Remote Similarity	NPC472065
0.6842	Remote Similarity	NPC472064
0.6835	Remote Similarity	NPC261195
0.6835	Remote Similarity	NPC29886
0.6835	Remote Similarity	NPC96102
0.6821	Remote Similarity	NPC65080
0.6818	Remote Similarity	NPC473380
0.6818	Remote Similarity	NPC240088
0.6813	Remote Similarity	NPC324091
0.6813	Remote Similarity	NPC154339
0.681	Remote Similarity	NPC159856
0.6803	Remote Similarity	NPC476566
0.68	Remote Similarity	NPC139763
0.68	Remote Similarity	NPC149155
0.68	Remote Similarity	NPC110500

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 NPC100726 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	241
0.1-0.2	621
0.2-0.3	1138
0.3-0.4	2066
0.4-0.5	2621
0.5-0.6	1848
0.6-0.7	563
0.7-0.8	52
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
0.7738	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD1270	Approved
0.75	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD200	Phase 2
0.7451	Intermediate Similarity	NPD201	Phase 2
0.7434	Intermediate Similarity	NPD272	Approved
0.7423	Intermediate Similarity	NPD1630	Approved
0.7374	Intermediate Similarity	NPD4848	Phase 1
0.7371	Intermediate Similarity	NPD4988	Discontinued
0.7365	Intermediate Similarity	NPD1343	Approved
0.7355	Intermediate Similarity	NPD569	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD4524	Discontinued
0.7294	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD1631	Approved
0.7283	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD5400	Approved
0.7209	Intermediate Similarity	NPD2753	Discontinued
0.7184	Intermediate Similarity	NPD3178	Discontinued
0.7174	Intermediate Similarity	NPD5017	Discontinued
0.7151	Intermediate Similarity	NPD3238	Discontinued
0.7143	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD271	Approved
0.7143	Intermediate Similarity	NPD268	Approved
0.7135	Intermediate Similarity	NPD750	Phase 2
0.7126	Intermediate Similarity	NPD1643	Phase 3
0.7125	Intermediate Similarity	NPD175	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD1573	Approved
0.7118	Intermediate Similarity	NPD1575	Approved
0.7089	Intermediate Similarity	NPD9599	Approved
0.7073	Intermediate Similarity	NPD180	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3475	Approved
0.7059	Intermediate Similarity	NPD3476	Approved
0.7059	Intermediate Similarity	NPD1292	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7401	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD9343	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7564	Discontinued
0.7	Intermediate Similarity	NPD9357	Approved
0.7	Intermediate Similarity	NPD5686	Approved
0.7	Intermediate Similarity	NPD4643	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5685	Approved
0.6994	Remote Similarity	NPD1586	Approved
0.6988	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD460	Discontinued
0.6974	Remote Similarity	NPD2118	Approved
0.6974	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD991	Phase 2
0.6974	Remote Similarity	NPD2119	Approved
0.6968	Remote Similarity	NPD9100	Approved
0.6935	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1004	Phase 2
0.6933	Remote Similarity	NPD1005	Phase 2
0.6932	Remote Similarity	NPD3927	Phase 2
0.6932	Remote Similarity	NPD5473	Discontinued
0.6928	Remote Similarity	NPD1031	Discontinued
0.6927	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD9583	Approved
0.6906	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2214	Approved
0.6905	Remote Similarity	NPD2213	Approved
0.6902	Remote Similarity	NPD2289	Phase 3
0.6902	Remote Similarity	NPD2290	Phase 3
0.6893	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.689	Remote Similarity	NPD3100	Discontinued
0.6882	Remote Similarity	NPD1545	Discontinued
0.6878	Remote Similarity	NPD3947	Discontinued
0.6878	Remote Similarity	NPD4299	Phase 1
0.6875	Remote Similarity	NPD1587	Approved
0.6867	Remote Similarity	NPD748	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD4924	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4075	Phase 2
0.6857	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD2479	Phase 3
0.6836	Remote Similarity	NPD2481	Approved
0.6835	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD2061	Approved
0.6823	Remote Similarity	NPD1600	Suspended
0.6816	Remote Similarity	NPD1096	Discontinued
0.6815	Remote Similarity	NPD4028	Approved
0.6815	Remote Similarity	NPD4030	Approved
0.6815	Remote Similarity	NPD4029	Approved
0.6813	Remote Similarity	NPD786	Approved
0.6802	Remote Similarity	NPD6446	Discontinued
0.6802	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.68	Remote Similarity	NPD482	Approved
0.6796	Remote Similarity	NPD2770	Discontinued
0.6789	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD3583	Phase 2
0.6782	Remote Similarity	NPD3347	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD2336	Approved
0.6774	Remote Similarity	NPD1952	Discontinued
0.6757	Remote Similarity	NPD9396	Approved
0.6757	Remote Similarity	NPD9392	Approved
0.6754	Remote Similarity	NPD2008	Discontinued
0.6739	Remote Similarity	NPD4922	Phase 2
0.6736	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.673	Remote Similarity	NPD206	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD1722	Approved
0.6728	Remote Similarity	NPD5020	Approved
0.6727	Remote Similarity	NPD4702	Approved
0.6727	Remote Similarity	NPD4703	Approved
0.6727	Remote Similarity	NPD4547	Phase 3
0.6725	Remote Similarity	NPD6771	Discontinued
0.672	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD3942	Approved
0.6709	Remote Similarity	NPD3944	Approved
0.6705	Remote Similarity	NPD4883	Approved
0.6702	Remote Similarity	NPD5901	Discontinued
0.6702	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD1658	Discontinued
0.6684	Remote Similarity	NPD2881	Approved
0.6684	Remote Similarity	NPD2879	Approved
0.6667	Remote Similarity	NPD3654	Approved
0.6648	Remote Similarity	NPD5809	Phase 3
0.6647	Remote Similarity	NPD2915	Discontinued
0.6646	Remote Similarity	NPD2896	Discontinued
0.6633	Remote Similarity	NPD2411	Approved
0.6632	Remote Similarity	NPD3839	Phase 2
0.6632	Remote Similarity	NPD3840	Phase 2
0.6632	Remote Similarity	NPD1506	Discontinued
0.6631	Remote Similarity	NPD2307	Discontinued
0.663	Remote Similarity	NPD3871	Clinical (unspecified phase)
0.663	Remote Similarity	NPD3870	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD269	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD6987	Phase 1
0.6614	Remote Similarity	NPD2405	Phase 3
0.6613	Remote Similarity	NPD4348	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD3246	Discontinued
0.6612	Remote Similarity	NPD3961	Discontinued
0.6604	Remote Similarity	NPD3385	Approved
0.6599	Remote Similarity	NPD6787	Phase 2
0.6598	Remote Similarity	NPD6459	Phase 2
0.659	Remote Similarity	NPD5088	Discontinued
0.6585	Remote Similarity	NPD2006	Phase 2
0.6582	Remote Similarity	NPD803	Phase 1
0.6582	Remote Similarity	NPD6152	Phase 1
0.658	Remote Similarity	NPD3967	Approved
0.6578	Remote Similarity	NPD7618	Phase 3
0.6578	Remote Similarity	NPD7619	Phase 3
0.6575	Remote Similarity	NPD2095	Phase 2
0.6575	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD2092	Phase 2
0.6575	Remote Similarity	NPD3318	Approved
0.6575	Remote Similarity	NPD3319	Phase 1
0.6575	Remote Similarity	NPD2094	Phase 2
0.6575	Remote Similarity	NPD3320	Approved
0.6573	Remote Similarity	NPD6044	Discontinued
0.6573	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD7402	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4638	Approved
0.6571	Remote Similarity	NPD4639	Approved
0.6571	Remote Similarity	NPD4640	Approved
0.6568	Remote Similarity	NPD2837	Discontinued
0.6564	Remote Similarity	NPD107	Approved
0.6557	Remote Similarity	NPD4940	Approved
0.6546	Remote Similarity	NPD3905	Phase 3
0.6543	Remote Similarity	NPD7027	Phase 3
0.6538	Remote Similarity	NPD1598	Discontinued
0.6538	Remote Similarity	NPD2096	Phase 2
0.6538	Remote Similarity	NPD721	Approved
0.6538	Remote Similarity	NPD2091	Phase 2
0.6536	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD2412	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD715	Phase 3
0.6515	Remote Similarity	NPD5888	Phase 2
0.6513	Remote Similarity	NPD2509	Approved
0.6513	Remote Similarity	NPD2510	Approved
0.6509	Remote Similarity	NPD510	Phase 1
0.6503	Remote Similarity	NPD2073	Approved
0.6503	Remote Similarity	NPD4336	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD2070	Approved
0.6503	Remote Similarity	NPD2072	Approved
0.6503	Remote Similarity	NPD768	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD2071	Approved
0.6503	Remote Similarity	NPD2069	Approved
0.6503	Remote Similarity	NPD2074	Approved
0.6503	Remote Similarity	NPD2075	Approved
0.6503	Remote Similarity	NPD2068	Approved
0.6497	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD2580	Discontinued
0.6489	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD2430	Phase 2
0.6486	Remote Similarity	NPD7175	Phase 1
0.6486	Remote Similarity	NPD6068	Discontinued
0.6485	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD3717	Discontinued

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