NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	215.11
Volume:	219.037
LogP:	1.021
LogD:	0.891
LogS:	-2.272
# Rotatable Bonds:	0
TPSA:	49.09
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.703
Synthetic Accessibility Score:	3.632
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.288
MDCK Permeability:	1.0212260349362623e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.887
Human Intestinal Absorption (HIA):	0.902
20% Bioavailability (F20%):	0.086
30% Bioavailability (F30%):	0.025

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.994
Plasma Protein Binding (PPB):	71.95574188232422%
Volume Distribution (VD):	1.49
Pgp-substrate:	26.162639617919922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.819
CYP1A2-substrate:	0.692
CYP2C19-inhibitor:	0.134
CYP2C19-substrate:	0.489
CYP2C9-inhibitor:	0.094
CYP2C9-substrate:	0.201
CYP2D6-inhibitor:	0.094
CYP2D6-substrate:	0.74
CYP3A4-inhibitor:	0.032
CYP3A4-substrate:	0.217

ADMET: Excretion

Clearance (CL):	2.945
Half-life (T1/2):	0.357

ADMET: Toxicity

hERG Blockers:	0.051
Human Hepatotoxicity (H-HT):	0.857
Drug-inuced Liver Injury (DILI):	0.533
AMES Toxicity:	0.97
Rat Oral Acute Toxicity:	0.18
Maximum Recommended Daily Dose:	0.798
Skin Sensitization:	0.396
Carcinogencity:	0.964
Eye Corrosion:	0.005
Eye Irritation:	0.038
Respiratory Toxicity:	0.428

Download Data

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

Natural Product: NPC473878

Natural Product ID:	NPC473878
*Common Name:**	Makaluvamine H
IUPAC Name:	n.a.
Synonyms:	Makaluvamine H
Standard InCHIKey:	RSEQSIHJWSQOOD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H13N3O.C2HF3O2/c1-14-4-3-7-6-15(2)11-10(7)9(14)5-8(13)12(11)16;3-2(4,5)1(6)7/h5-6,13H,3-4H2,1-2H3;(H,6,7)
SMILES:	CN1C=C2CC[N+](=C3C2=C1C(=O)C(=C3)N)C.C(=O)(C(F)(F)F)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454072
PubChem CID:	10520373
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives

*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]
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
IC50	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	5000.0	nM	PMID[488345]

☑ 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 NPC473878 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	272
0.1-0.2	2880
0.2-0.3	17220
0.3-0.4	15622
0.4-0.5	3185
0.5-0.6	2351
0.6-0.7	1036
0.7-0.8	119
0.8-0.85	4
0.85-0.9	4
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9514	High Similarity	NPC470679
0.9514	High Similarity	NPC217021
0.9441	High Similarity	NPC100726
0.9262	High Similarity	NPC470680
0.9262	High Similarity	NPC100104
0.9067	High Similarity	NPC474492
0.898	High Similarity	NPC102664
0.8919	High Similarity	NPC471655
0.86	High Similarity	NPC123906
0.8553	High Similarity	NPC251391
0.8526	High Similarity	NPC274981
0.8421	Intermediate Similarity	NPC313889
0.8366	Intermediate Similarity	NPC70406
0.8278	Intermediate Similarity	NPC467188
0.8217	Intermediate Similarity	NPC80681
0.8182	Intermediate Similarity	NPC182940
0.817	Intermediate Similarity	NPC105811
0.8148	Intermediate Similarity	NPC262338
0.7917	Intermediate Similarity	NPC191415
0.7911	Intermediate Similarity	NPC209362
0.7907	Intermediate Similarity	NPC268966
0.7898	Intermediate Similarity	NPC472260
0.7886	Intermediate Similarity	NPC292361
0.7857	Intermediate Similarity	NPC79777
0.7857	Intermediate Similarity	NPC234403
0.7857	Intermediate Similarity	NPC477042
0.7844	Intermediate Similarity	NPC157583
0.784	Intermediate Similarity	NPC265100
0.7821	Intermediate Similarity	NPC106757
0.7815	Intermediate Similarity	NPC65408
0.7805	Intermediate Similarity	NPC70949
0.7799	Intermediate Similarity	NPC229055
0.7751	Intermediate Similarity	NPC73994
0.775	Intermediate Similarity	NPC74357
0.7738	Intermediate Similarity	NPC237188
0.7738	Intermediate Similarity	NPC83774
0.7735	Intermediate Similarity	NPC88115
0.7733	Intermediate Similarity	NPC469359
0.7702	Intermediate Similarity	NPC213914
0.7682	Intermediate Similarity	NPC291517
0.7654	Intermediate Similarity	NPC474767
0.7647	Intermediate Similarity	NPC61011
0.7644	Intermediate Similarity	NPC103119
0.764	Intermediate Similarity	NPC473814
0.764	Intermediate Similarity	NPC78767
0.764	Intermediate Similarity	NPC167710
0.7633	Intermediate Similarity	NPC284775
0.7627	Intermediate Similarity	NPC93390
0.7616	Intermediate Similarity	NPC477003
0.76	Intermediate Similarity	NPC475874
0.7586	Intermediate Similarity	NPC474259
0.7586	Intermediate Similarity	NPC23476
0.7586	Intermediate Similarity	NPC477415
0.7584	Intermediate Similarity	NPC71236
0.7582	Intermediate Similarity	NPC472288
0.7576	Intermediate Similarity	NPC233380
0.7558	Intermediate Similarity	NPC102755
0.7543	Intermediate Similarity	NPC473628
0.753	Intermediate Similarity	NPC114637
0.7515	Intermediate Similarity	NPC469529
0.7514	Intermediate Similarity	NPC46895
0.7514	Intermediate Similarity	NPC216550
0.7472	Intermediate Similarity	NPC326422
0.7455	Intermediate Similarity	NPC242116
0.7443	Intermediate Similarity	NPC255909
0.7425	Intermediate Similarity	NPC56233
0.741	Intermediate Similarity	NPC478184
0.74	Intermediate Similarity	NPC313823
0.7397	Intermediate Similarity	NPC182570
0.7397	Intermediate Similarity	NPC265605
0.7397	Intermediate Similarity	NPC48564
0.7374	Intermediate Similarity	NPC221726
0.7374	Intermediate Similarity	NPC473821
0.7374	Intermediate Similarity	NPC477414
0.7374	Intermediate Similarity	NPC304203
0.7374	Intermediate Similarity	NPC225622
0.7365	Intermediate Similarity	NPC42372
0.7365	Intermediate Similarity	NPC115232
0.736	Intermediate Similarity	NPC476460
0.7348	Intermediate Similarity	NPC74153
0.733	Intermediate Similarity	NPC118084
0.731	Intermediate Similarity	NPC293216
0.7308	Intermediate Similarity	NPC476143
0.7308	Intermediate Similarity	NPC34837
0.7303	Intermediate Similarity	NPC469489
0.7273	Intermediate Similarity	NPC311282
0.7268	Intermediate Similarity	NPC81535
0.7268	Intermediate Similarity	NPC237414
0.7253	Intermediate Similarity	NPC106824
0.7248	Intermediate Similarity	NPC27740
0.7229	Intermediate Similarity	NPC293487
0.7226	Intermediate Similarity	NPC23215
0.7219	Intermediate Similarity	NPC41717
0.7213	Intermediate Similarity	NPC477044
0.7213	Intermediate Similarity	NPC477041
0.7209	Intermediate Similarity	NPC139763
0.7204	Intermediate Similarity	NPC317701
0.7202	Intermediate Similarity	NPC271797
0.7202	Intermediate Similarity	NPC21174
0.7202	Intermediate Similarity	NPC478182
0.7198	Intermediate Similarity	NPC128244
0.7195	Intermediate Similarity	NPC281094
0.7175	Intermediate Similarity	NPC133003
0.7174	Intermediate Similarity	NPC284338
0.7172	Intermediate Similarity	NPC476566
0.7168	Intermediate Similarity	NPC151635
0.7159	Intermediate Similarity	NPC159125
0.7152	Intermediate Similarity	NPC110126
0.7151	Intermediate Similarity	NPC252572
0.7128	Intermediate Similarity	NPC472065
0.7126	Intermediate Similarity	NPC14113
0.7126	Intermediate Similarity	NPC145885
0.7126	Intermediate Similarity	NPC84827
0.7125	Intermediate Similarity	NPC190296
0.7119	Intermediate Similarity	NPC467063
0.7112	Intermediate Similarity	NPC476252
0.711	Intermediate Similarity	NPC186068
0.7102	Intermediate Similarity	NPC470677
0.7097	Intermediate Similarity	NPC330326
0.7093	Intermediate Similarity	NPC302647
0.709	Intermediate Similarity	NPC469577
0.709	Intermediate Similarity	NPC475410
0.7086	Intermediate Similarity	NPC146373
0.7086	Intermediate Similarity	NPC166424
0.7086	Intermediate Similarity	NPC11126
0.7086	Intermediate Similarity	NPC245244
0.7086	Intermediate Similarity	NPC248462
0.7083	Intermediate Similarity	NPC477413
0.7081	Intermediate Similarity	NPC477004
0.7081	Intermediate Similarity	NPC123395
0.7081	Intermediate Similarity	NPC477045
0.7079	Intermediate Similarity	NPC295158
0.7074	Intermediate Similarity	NPC469563
0.7063	Intermediate Similarity	NPC101130
0.7063	Intermediate Similarity	NPC58268
0.7063	Intermediate Similarity	NPC114033
0.7063	Intermediate Similarity	NPC129412
0.7059	Intermediate Similarity	NPC71132
0.7059	Intermediate Similarity	NPC57398
0.7059	Intermediate Similarity	NPC471589
0.7059	Intermediate Similarity	NPC472069
0.7059	Intermediate Similarity	NPC472062
0.7059	Intermediate Similarity	NPC472063
0.7052	Intermediate Similarity	NPC477976
0.7049	Intermediate Similarity	NPC135950
0.7044	Intermediate Similarity	NPC73767
0.7041	Intermediate Similarity	NPC478185
0.7037	Intermediate Similarity	NPC472064
0.7037	Intermediate Similarity	NPC314372
0.7035	Intermediate Similarity	NPC91895
0.7033	Intermediate Similarity	NPC47190
0.7032	Intermediate Similarity	NPC256893
0.7025	Intermediate Similarity	NPC150259
0.7025	Intermediate Similarity	NPC105127
0.7025	Intermediate Similarity	NPC84911
0.7018	Intermediate Similarity	NPC478183
0.7017	Intermediate Similarity	NPC324091
0.7016	Intermediate Similarity	NPC61038
0.7007	Intermediate Similarity	NPC297486
0.7007	Intermediate Similarity	NPC240136
0.7007	Intermediate Similarity	NPC471402
0.7	Intermediate Similarity	NPC473946
0.6995	Remote Similarity	NPC472295
0.6995	Remote Similarity	NPC269886
0.6995	Remote Similarity	NPC81802
0.6995	Remote Similarity	NPC472210
0.6995	Remote Similarity	NPC247735
0.6989	Remote Similarity	NPC103361
0.6989	Remote Similarity	NPC126709
0.6989	Remote Similarity	NPC55772
0.6989	Remote Similarity	NPC248041
0.6984	Remote Similarity	NPC477043
0.6982	Remote Similarity	NPC473706
0.6973	Remote Similarity	NPC227582
0.6971	Remote Similarity	NPC267885
0.697	Remote Similarity	NPC40070
0.6968	Remote Similarity	NPC328596
0.6968	Remote Similarity	NPC328318
0.6964	Remote Similarity	NPC129721
0.6963	Remote Similarity	NPC116555
0.6963	Remote Similarity	NPC469578
0.6962	Remote Similarity	NPC96102
0.6962	Remote Similarity	NPC261195
0.6962	Remote Similarity	NPC29886
0.6961	Remote Similarity	NPC209917
0.6959	Remote Similarity	NPC91958
0.6952	Remote Similarity	NPC121327
0.6951	Remote Similarity	NPC179787
0.6951	Remote Similarity	NPC201380
0.6948	Remote Similarity	NPC89490
0.6941	Remote Similarity	NPC214106
0.6941	Remote Similarity	NPC194881
0.694	Remote Similarity	NPC472292
0.6936	Remote Similarity	NPC32534
0.6933	Remote Similarity	NPC159856
0.6933	Remote Similarity	NPC470440
0.6931	Remote Similarity	NPC138562
0.6928	Remote Similarity	NPC470233
0.6927	Remote Similarity	NPC228835
0.6927	Remote Similarity	NPC207851

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 NPC473878 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	519
0.2-0.3	1093
0.3-0.4	2013
0.4-0.5	2736
0.5-0.6	1972
0.6-0.7	611
0.7-0.8	45
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
0.8027	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD1270	Approved
0.7815	Intermediate Similarity	NPD200	Phase 2
0.7815	Intermediate Similarity	NPD201	Phase 2
0.7751	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1343	Approved
0.7665	Intermediate Similarity	NPD4524	Discontinued
0.7576	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD272	Approved
0.7439	Intermediate Similarity	NPD1630	Approved
0.7427	Intermediate Similarity	NPD2753	Discontinued
0.7417	Intermediate Similarity	NPD3475	Approved
0.7417	Intermediate Similarity	NPD3476	Approved
0.7397	Intermediate Similarity	NPD271	Approved
0.7397	Intermediate Similarity	NPD268	Approved
0.7397	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4988	Discontinued
0.7368	Intermediate Similarity	NPD3238	Discontinued
0.7333	Intermediate Similarity	NPD2213	Approved
0.7333	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2118	Approved
0.7333	Intermediate Similarity	NPD2119	Approved
0.7333	Intermediate Similarity	NPD991	Phase 2
0.7333	Intermediate Similarity	NPD2214	Approved
0.733	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD4643	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1631	Approved
0.7301	Intermediate Similarity	NPD180	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD4848	Phase 1
0.7289	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD460	Discontinued
0.7267	Intermediate Similarity	NPD9583	Approved
0.7261	Intermediate Similarity	NPD569	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD750	Phase 2
0.7241	Intermediate Similarity	NPD5473	Discontinued
0.7235	Intermediate Similarity	NPD1573	Approved
0.7235	Intermediate Similarity	NPD1575	Approved
0.7232	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7564	Discontinued
0.7215	Intermediate Similarity	NPD9599	Approved
0.72	Intermediate Similarity	NPD3178	Discontinued
0.7189	Intermediate Similarity	NPD5017	Discontinued
0.7176	Intermediate Similarity	NPD1292	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4030	Approved
0.7161	Intermediate Similarity	NPD4028	Approved
0.7161	Intermediate Similarity	NPD4029	Approved
0.7159	Intermediate Similarity	NPD7401	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD4924	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2481	Approved
0.7143	Intermediate Similarity	NPD2479	Phase 3
0.7143	Intermediate Similarity	NPD5400	Approved
0.7143	Intermediate Similarity	NPD175	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD9357	Approved
0.712	Intermediate Similarity	NPD7204	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD1905	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD9100	Approved
0.7063	Intermediate Similarity	NPD1722	Approved
0.7055	Intermediate Similarity	NPD4703	Approved
0.7055	Intermediate Similarity	NPD4702	Approved
0.7055	Intermediate Similarity	NPD4547	Phase 3
0.7051	Intermediate Similarity	NPD3942	Approved
0.7051	Intermediate Similarity	NPD3944	Approved
0.7045	Intermediate Similarity	NPD1643	Phase 3
0.7043	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6771	Discontinued
0.703	Intermediate Similarity	NPD9343	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6446	Discontinued
0.7011	Intermediate Similarity	NPD1586	Approved
0.7006	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3583	Phase 2
0.6989	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD2896	Discontinued
0.6978	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5020	Approved
0.6949	Remote Similarity	NPD3927	Phase 2
0.6948	Remote Similarity	NPD1031	Discontinued
0.6946	Remote Similarity	NPD2061	Approved
0.6943	Remote Similarity	NPD3385	Approved
0.694	Remote Similarity	NPD4922	Phase 2
0.6937	Remote Similarity	NPD786	Approved
0.6919	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD2290	Phase 3
0.6919	Remote Similarity	NPD2289	Phase 3
0.6914	Remote Similarity	NPD482	Approved
0.6911	Remote Similarity	NPD3905	Phase 3
0.691	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD1545	Discontinued
0.6895	Remote Similarity	NPD3947	Discontinued
0.6895	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD1587	Approved
0.6892	Remote Similarity	NPD9392	Approved
0.6892	Remote Similarity	NPD9396	Approved
0.6886	Remote Similarity	NPD2837	Discontinued
0.6885	Remote Similarity	NPD1658	Discontinued
0.6878	Remote Similarity	NPD2881	Approved
0.6878	Remote Similarity	NPD2879	Approved
0.6875	Remote Similarity	NPD6044	Discontinued
0.6872	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6787	Phase 2
0.6865	Remote Similarity	NPD7619	Phase 3
0.6865	Remote Similarity	NPD7618	Phase 3
0.6859	Remote Similarity	NPD2008	Discontinued
0.6859	Remote Similarity	NPD715	Phase 3
0.6855	Remote Similarity	NPD206	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD5809	Phase 3
0.6848	Remote Similarity	NPD1004	Phase 2
0.6848	Remote Similarity	NPD1005	Phase 2
0.6839	Remote Similarity	NPD1600	Suspended
0.6833	Remote Similarity	NPD1096	Discontinued
0.6832	Remote Similarity	NPD2069	Approved
0.6832	Remote Similarity	NPD2068	Approved
0.6832	Remote Similarity	NPD2071	Approved
0.6832	Remote Similarity	NPD2075	Approved
0.6832	Remote Similarity	NPD2074	Approved
0.6832	Remote Similarity	NPD768	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD2070	Approved
0.6832	Remote Similarity	NPD2072	Approved
0.6832	Remote Similarity	NPD2073	Approved
0.6831	Remote Similarity	NPD5686	Approved
0.6831	Remote Similarity	NPD5685	Approved
0.6813	Remote Similarity	NPD2770	Discontinued
0.681	Remote Similarity	NPD3717	Discontinued
0.681	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.681	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.681	Remote Similarity	NPD2006	Phase 2
0.6809	Remote Similarity	NPD6999	Discontinued
0.6809	Remote Similarity	NPD2405	Phase 3
0.6809	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD3100	Discontinued
0.6807	Remote Similarity	NPD2430	Phase 2
0.6806	Remote Similarity	NPD4299	Phase 1
0.6802	Remote Similarity	NPD5088	Discontinued
0.6795	Remote Similarity	NPD3654	Approved
0.6793	Remote Similarity	NPD2336	Approved
0.6788	Remote Similarity	NPD2509	Approved
0.6788	Remote Similarity	NPD7469	Discontinued
0.6788	Remote Similarity	NPD6459	Phase 2
0.6788	Remote Similarity	NPD2510	Approved
0.6786	Remote Similarity	NPD5888	Phase 2
0.6784	Remote Similarity	NPD2511	Approved
0.678	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.678	Remote Similarity	NPD4075	Phase 2
0.6776	Remote Similarity	NPD6068	Discontinued
0.6774	Remote Similarity	NPD1598	Discontinued
0.6774	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD6152	Phase 1
0.6769	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4326	Phase 2
0.6758	Remote Similarity	NPD7026	Phase 2
0.6757	Remote Similarity	NPD3431	Approved
0.6757	Remote Similarity	NPD269	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD3430	Approved
0.6757	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.674	Remote Similarity	NPD2091	Phase 2
0.674	Remote Similarity	NPD2096	Phase 2
0.6738	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD3839	Phase 2
0.6736	Remote Similarity	NPD3840	Phase 2
0.6736	Remote Similarity	NPD1506	Discontinued
0.6735	Remote Similarity	NPD2411	Approved
0.6726	Remote Similarity	NPD510	Phase 1
0.6723	Remote Similarity	NPD4883	Approved
0.6719	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD6987	Phase 1
0.6718	Remote Similarity	NPD4051	Discontinued
0.6717	Remote Similarity	NPD3394	Approved
0.6717	Remote Similarity	NPD3389	Approved
0.6717	Remote Similarity	NPD3393	Approved
0.6709	Remote Similarity	NPD803	Phase 1
0.6704	Remote Similarity	NPD3076	Approved
0.6704	Remote Similarity	NPD3077	Approved
0.6704	Remote Similarity	NPD3078	Approved
0.6704	Remote Similarity	NPD3079	Approved
0.6704	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD6664	Approved
0.6702	Remote Similarity	NPD1952	Discontinued
0.6701	Remote Similarity	NPD2443	Approved
0.6701	Remote Similarity	NPD2442	Approved
0.6686	Remote Similarity	NPD2012	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD3318	Approved
0.6685	Remote Similarity	NPD2094	Phase 2
0.6685	Remote Similarity	NPD3320	Approved
0.6685	Remote Similarity	NPD6471	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD2092	Phase 2
0.6685	Remote Similarity	NPD2095	Phase 2

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