NPASS Compound

Structure

NPC473814 OpenBabel07101718222D 24 27 0 0 0 0 0 0 0 0999 V2000 6.8401 -0.4887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2297 -4.1314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1002 -2.6237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3592 -3.6288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2297 -2.1211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9707 -4.1314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6650 -2.6667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8412 -3.6288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7701 -3.6664 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2576 -4.0893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4361 -1.3019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1002 -3.6288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7467 -2.2579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3592 -2.6237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0386 -3.8484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5822 -3.6288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9335 -2.8487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1203 -2.2579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5212 -2.8138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9569 -4.2572 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.7117 -4.1314 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.4309 -1.3019 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.4887 -2.1211 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5855 -2.4466 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 4 1 0 0 0 0 2 12 2 0 0 0 0 3 5 2 0 0 0 0 3 12 1 0 0 0 0 4 14 2 0 0 0 0 5 14 1 0 0 0 0 6 8 1 0 0 0 0 6 12 1 0 0 0 0 7 9 1 0 0 0 0 7 13 1 0 0 0 0 8 21 1 0 0 0 0 9 20 1 0 0 0 0 10 15 1 0 0 0 0 10 16 2 0 0 0 0 11 13 2 0 0 0 0 11 22 1 0 0 0 0 13 17 1 0 0 0 0 14 23 1 0 0 0 0 15 17 1 0 0 0 0 15 20 2 0 0 0 0 16 19 1 0 0 0 0 16 21 1 0 0 0 0 17 18 2 0 0 0 0 18 19 1 0 0 0 0 18 22 1 0 0 0 0 19 24 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	321.15
Volume:	332.433
LogP:	3.338
LogD:	3.106
LogS:	-3.93
# Rotatable Bonds:	4
TPSA:	69.78
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.644
Synthetic Accessibility Score:	3.118
Fsp3:	0.211
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.001
MDCK Permeability:	1.0037058927991893e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.038
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.512
Plasma Protein Binding (PPB):	96.6004867553711%
Volume Distribution (VD):	0.859
Pgp-substrate:	3.129182815551758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.983
CYP1A2-substrate:	0.76
CYP2C19-inhibitor:	0.693
CYP2C19-substrate:	0.077
CYP2C9-inhibitor:	0.619
CYP2C9-substrate:	0.874
CYP2D6-inhibitor:	0.904
CYP2D6-substrate:	0.915
CYP3A4-inhibitor:	0.345
CYP3A4-substrate:	0.185

ADMET: Excretion

Clearance (CL):	8.573
Half-life (T1/2):	0.791

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.587
Drug-inuced Liver Injury (DILI):	0.834
AMES Toxicity:	0.905
Rat Oral Acute Toxicity:	0.31
Maximum Recommended Daily Dose:	0.908
Skin Sensitization:	0.934
Carcinogencity:	0.925
Eye Corrosion:	0.003
Eye Irritation:	0.309
Respiratory Toxicity:	0.758

Download Data

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

Natural Product: NPC473814

Natural Product ID:	NPC473814
*Common Name:**	Makaluvamine K Tfa Salt
IUPAC Name:	n.a.
Synonyms:	Makaluvamine K; Makaluvamines K Trifluroacetate
Standard InCHIKey:	QDEXEFRWSDXCCX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H19N3O2.C2HF3O2/c1-22-11-13-7-9-20-15-10-16(19(24)18(22)17(13)15)21-8-6-12-2-4-14(23)5-3-12;3-2(4,5)1(6)7/h2-5,10-11,21,23H,6-9H2,1H3;(H,6,7)
SMILES:	CN1C=C2CCN=C3C2=C1C(=O)C(=C3)NCCC4=CC=C(C=C4)O.C(=O)(C(F)(F)F)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452506
PubChem CID:	44559897
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]
NPO33461	zyzzya sp.	Species	n.a.	Eukaryota	n.a.	Australian	n.a.	PMID[22686608]
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	3
Others	2

Activity Type	# Activity
Cell Line	1
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	1100.0	nM	PMID[458278]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	396.0	nM	PMID[458278]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	300.0	nM	PMID[458278]
NPT2	Others	Unspecified		Ratio IC50	=	3.0	n.a.	PMID[458278]
NPT2	Others	Unspecified		Ratio IC50	=	4.0	n.a.	PMID[458278]

☑ 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 NPC473814 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	2767
0.2-0.3	13104
0.3-0.4	5960
0.4-0.5	15165
0.5-0.6	3193
0.6-0.7	2033
0.7-0.8	161
0.8-0.85	5
0.85-0.9	0
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC78767
0.9885	High Similarity	NPC93390
0.9661	High Similarity	NPC74153
0.9492	High Similarity	NPC473821
0.8796	High Similarity	NPC61038
0.8639	High Similarity	NPC175602
0.8615	High Similarity	NPC207866
0.8571	High Similarity	NPC295158
0.8376	Intermediate Similarity	NPC110182
0.8177	Intermediate Similarity	NPC14686
0.8128	Intermediate Similarity	NPC269270
0.803	Intermediate Similarity	NPC27041
0.7979	Intermediate Similarity	NPC241025
0.7972	Intermediate Similarity	NPC475635
0.7931	Intermediate Similarity	NPC100726
0.7805	Intermediate Similarity	NPC322064
0.7766	Intermediate Similarity	NPC271792
0.774	Intermediate Similarity	NPC471655
0.7716	Intermediate Similarity	NPC472284
0.7673	Intermediate Similarity	NPC183777
0.764	Intermediate Similarity	NPC473878
0.7574	Intermediate Similarity	NPC472259
0.7571	Intermediate Similarity	NPC276657
0.7557	Intermediate Similarity	NPC119569
0.7551	Intermediate Similarity	NPC99666
0.7551	Intermediate Similarity	NPC56170
0.755	Intermediate Similarity	NPC315491
0.755	Intermediate Similarity	NPC45459
0.7546	Intermediate Similarity	NPC279189
0.7546	Intermediate Similarity	NPC200553
0.754	Intermediate Similarity	NPC262338
0.7537	Intermediate Similarity	NPC472286
0.7537	Intermediate Similarity	NPC472287
0.7524	Intermediate Similarity	NPC168209
0.7523	Intermediate Similarity	NPC477549
0.75	Intermediate Similarity	NPC473804
0.7488	Intermediate Similarity	NPC219087
0.7487	Intermediate Similarity	NPC182940
0.7486	Intermediate Similarity	NPC102664
0.7476	Intermediate Similarity	NPC264285
0.7474	Intermediate Similarity	NPC171171
0.7465	Intermediate Similarity	NPC207686
0.7463	Intermediate Similarity	NPC171787
0.7463	Intermediate Similarity	NPC213308
0.7462	Intermediate Similarity	NPC324149
0.7447	Intermediate Similarity	NPC302647
0.7446	Intermediate Similarity	NPC470680
0.7446	Intermediate Similarity	NPC100104
0.7443	Intermediate Similarity	NPC162002
0.7438	Intermediate Similarity	NPC53144
0.7436	Intermediate Similarity	NPC46580
0.7429	Intermediate Similarity	NPC469727
0.7423	Intermediate Similarity	NPC314002
0.7418	Intermediate Similarity	NPC243633
0.7418	Intermediate Similarity	NPC175150
0.7416	Intermediate Similarity	NPC237740
0.7415	Intermediate Similarity	NPC270918
0.7406	Intermediate Similarity	NPC54066
0.7403	Intermediate Similarity	NPC470679
0.7403	Intermediate Similarity	NPC217021
0.74	Intermediate Similarity	NPC156704
0.7397	Intermediate Similarity	NPC174489
0.7391	Intermediate Similarity	NPC474492
0.7389	Intermediate Similarity	NPC470678
0.7387	Intermediate Similarity	NPC202812
0.7382	Intermediate Similarity	NPC96890
0.738	Intermediate Similarity	NPC41717
0.7374	Intermediate Similarity	NPC471448
0.7371	Intermediate Similarity	NPC204717
0.7363	Intermediate Similarity	NPC477041
0.7363	Intermediate Similarity	NPC306376
0.7363	Intermediate Similarity	NPC477044
0.736	Intermediate Similarity	NPC475874
0.736	Intermediate Similarity	NPC268966
0.7347	Intermediate Similarity	NPC278434
0.7346	Intermediate Similarity	NPC472285
0.734	Intermediate Similarity	NPC471944
0.7337	Intermediate Similarity	NPC45850
0.733	Intermediate Similarity	NPC15801
0.733	Intermediate Similarity	NPC26641
0.7326	Intermediate Similarity	NPC471178
0.732	Intermediate Similarity	NPC220765
0.7317	Intermediate Similarity	NPC477043
0.7317	Intermediate Similarity	NPC88115
0.7313	Intermediate Similarity	NPC227582
0.7312	Intermediate Similarity	NPC471177
0.7312	Intermediate Similarity	NPC59779
0.7312	Intermediate Similarity	NPC124542
0.731	Intermediate Similarity	NPC473628
0.731	Intermediate Similarity	NPC209917
0.7308	Intermediate Similarity	NPC309845
0.7306	Intermediate Similarity	NPC477042
0.7306	Intermediate Similarity	NPC79777
0.7304	Intermediate Similarity	NPC211813
0.7304	Intermediate Similarity	NPC57398
0.729	Intermediate Similarity	NPC473317
0.7286	Intermediate Similarity	NPC47190
0.7277	Intermediate Similarity	NPC74360
0.7273	Intermediate Similarity	NPC83111
0.7268	Intermediate Similarity	NPC200836
0.7268	Intermediate Similarity	NPC251391
0.7265	Intermediate Similarity	NPC37152
0.7259	Intermediate Similarity	NPC206186
0.7256	Intermediate Similarity	NPC220851
0.7256	Intermediate Similarity	NPC16352
0.7248	Intermediate Similarity	NPC194740
0.7243	Intermediate Similarity	NPC323969
0.7241	Intermediate Similarity	NPC477045
0.7235	Intermediate Similarity	NPC24370
0.7235	Intermediate Similarity	NPC319232
0.7228	Intermediate Similarity	NPC77555
0.7225	Intermediate Similarity	NPC85273
0.7225	Intermediate Similarity	NPC124086
0.7222	Intermediate Similarity	NPC122436
0.722	Intermediate Similarity	NPC101350
0.722	Intermediate Similarity	NPC106757
0.7216	Intermediate Similarity	NPC234403
0.7215	Intermediate Similarity	NPC326363
0.7214	Intermediate Similarity	NPC146724
0.7206	Intermediate Similarity	NPC252338
0.7204	Intermediate Similarity	NPC236668
0.7202	Intermediate Similarity	NPC184964
0.7198	Intermediate Similarity	NPC472064
0.7198	Intermediate Similarity	NPC123906
0.7194	Intermediate Similarity	NPC207851
0.7194	Intermediate Similarity	NPC228835
0.7194	Intermediate Similarity	NPC477003
0.7192	Intermediate Similarity	NPC474916
0.719	Intermediate Similarity	NPC82370
0.7189	Intermediate Similarity	NPC125597
0.7183	Intermediate Similarity	NPC246658
0.7178	Intermediate Similarity	NPC242209
0.7175	Intermediate Similarity	NPC184225
0.7175	Intermediate Similarity	NPC235685
0.717	Intermediate Similarity	NPC146976
0.7165	Intermediate Similarity	NPC72980
0.7163	Intermediate Similarity	NPC88008
0.7157	Intermediate Similarity	NPC311282
0.715	Intermediate Similarity	NPC475070
0.7143	Intermediate Similarity	NPC229893
0.7143	Intermediate Similarity	NPC90229
0.7143	Intermediate Similarity	NPC167710
0.7136	Intermediate Similarity	NPC472063
0.7136	Intermediate Similarity	NPC472069
0.7136	Intermediate Similarity	NPC476161
0.7136	Intermediate Similarity	NPC330009
0.7136	Intermediate Similarity	NPC328318
0.7136	Intermediate Similarity	NPC183805
0.7136	Intermediate Similarity	NPC472062
0.7136	Intermediate Similarity	NPC328596
0.7135	Intermediate Similarity	NPC209362
0.7129	Intermediate Similarity	NPC276517
0.7129	Intermediate Similarity	NPC143075
0.7128	Intermediate Similarity	NPC73994
0.7127	Intermediate Similarity	NPC467188
0.7118	Intermediate Similarity	NPC91868
0.7118	Intermediate Similarity	NPC63971
0.7116	Intermediate Similarity	NPC313804
0.7116	Intermediate Similarity	NPC315804
0.7113	Intermediate Similarity	NPC284775
0.7109	Intermediate Similarity	NPC23294
0.7105	Intermediate Similarity	NPC178858
0.7104	Intermediate Similarity	NPC477112
0.7101	Intermediate Similarity	NPC476098
0.7101	Intermediate Similarity	NPC134848
0.7101	Intermediate Similarity	NPC98715
0.71	Intermediate Similarity	NPC154339
0.7094	Intermediate Similarity	NPC292361
0.7089	Intermediate Similarity	NPC239763
0.7089	Intermediate Similarity	NPC190401
0.7089	Intermediate Similarity	NPC50562
0.7087	Intermediate Similarity	NPC300183
0.7085	Intermediate Similarity	NPC23476
0.7085	Intermediate Similarity	NPC97902
0.7085	Intermediate Similarity	NPC182222
0.7085	Intermediate Similarity	NPC474259
0.7085	Intermediate Similarity	NPC477415
0.7085	Intermediate Similarity	NPC325976
0.7081	Intermediate Similarity	NPC53344
0.7079	Intermediate Similarity	NPC267343
0.7077	Intermediate Similarity	NPC67659
0.7077	Intermediate Similarity	NPC11126
0.7077	Intermediate Similarity	NPC164340
0.7074	Intermediate Similarity	NPC131718
0.7073	Intermediate Similarity	NPC474767
0.7073	Intermediate Similarity	NPC284338
0.7073	Intermediate Similarity	NPC81535
0.7073	Intermediate Similarity	NPC123395
0.7073	Intermediate Similarity	NPC103361
0.7067	Intermediate Similarity	NPC470500
0.7065	Intermediate Similarity	NPC138370
0.7062	Intermediate Similarity	NPC303951
0.7056	Intermediate Similarity	NPC67658
0.7051	Intermediate Similarity	NPC121069
0.705	Intermediate Similarity	NPC32771
0.7049	Intermediate Similarity	NPC105811
0.7048	Intermediate Similarity	NPC39679
0.7047	Intermediate Similarity	NPC259545
0.7047	Intermediate Similarity	NPC471294
0.7044	Intermediate Similarity	NPC157828

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 NPC473814 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	587
0.2-0.3	862
0.3-0.4	1024
0.4-0.5	2740
0.5-0.6	2671
0.6-0.7	1028
0.7-0.8	64
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
0.7773	Intermediate Similarity	NPD4845	Discontinued
0.7725	Intermediate Similarity	NPD3178	Discontinued
0.7662	Intermediate Similarity	NPD5901	Discontinued
0.7635	Intermediate Similarity	NPD6376	Discontinued
0.7602	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD6242	Discontinued
0.756	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD484	Approved
0.7487	Intermediate Similarity	NPD7948	Phase 1
0.7368	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7203	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD3326	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD3947	Discontinued
0.7282	Intermediate Similarity	NPD1096	Discontinued
0.7277	Intermediate Similarity	NPD5065	Approved
0.7273	Intermediate Similarity	NPD1631	Approved
0.7241	Intermediate Similarity	NPD6137	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD5866	Approved
0.7235	Intermediate Similarity	NPD7603	Discontinued
0.7222	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD1643	Phase 3
0.7206	Intermediate Similarity	NPD5497	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD3779	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD7586	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5513	Phase 2
0.7171	Intermediate Similarity	NPD4511	Phase 1
0.7136	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD6975	Discontinued
0.7135	Intermediate Similarity	NPD750	Phase 2
0.713	Intermediate Similarity	NPD4923	Phase 1
0.7122	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD3315	Phase 3
0.712	Intermediate Similarity	NPD1573	Approved
0.712	Intermediate Similarity	NPD1575	Approved
0.7112	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD1630	Approved
0.7107	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD8356	Approved
0.7094	Intermediate Similarity	NPD4848	Phase 1
0.7085	Intermediate Similarity	NPD4948	Discontinued
0.7081	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3814	Phase 1
0.7071	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD4429	Discontinued
0.7068	Intermediate Similarity	NPD2781	Approved
0.7068	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD6173	Approved
0.7061	Intermediate Similarity	NPD3959	Phase 2
0.7061	Intermediate Similarity	NPD3962	Phase 2
0.7056	Intermediate Similarity	NPD3394	Approved
0.7056	Intermediate Similarity	NPD3389	Approved
0.7056	Intermediate Similarity	NPD3393	Approved
0.7053	Intermediate Similarity	NPD2780	Approved
0.7053	Intermediate Similarity	NPD2782	Approved
0.7048	Intermediate Similarity	NPD2510	Approved
0.7048	Intermediate Similarity	NPD2509	Approved
0.7045	Intermediate Similarity	NPD7994	Phase 2
0.7044	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD3017	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5255	Approved
0.7019	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD5017	Discontinued
0.6995	Remote Similarity	NPD802	Phase 2
0.6995	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD1038	Approved
0.699	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.699	Remote Similarity	NPD6999	Discontinued
0.698	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.698	Remote Similarity	NPD2336	Approved
0.6974	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD8430	Approved
0.6967	Remote Similarity	NPD2916	Discontinued
0.6955	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5937	Approved
0.6946	Remote Similarity	NPD6665	Discontinued
0.6944	Remote Similarity	NPD6710	Phase 3
0.6944	Remote Similarity	NPD4989	Phase 2
0.6935	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6790	Phase 1
0.6923	Remote Similarity	NPD482	Approved
0.692	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD3918	Approved
0.6916	Remote Similarity	NPD3917	Approved
0.6915	Remote Similarity	NPD4988	Discontinued
0.6911	Remote Similarity	NPD5088	Discontinued
0.6909	Remote Similarity	NPD2803	Discontinued
0.6909	Remote Similarity	NPD6753	Phase 1
0.6909	Remote Similarity	NPD6752	Phase 1
0.6906	Remote Similarity	NPD1659	Phase 1
0.6906	Remote Similarity	NPD5022	Discontinued
0.6905	Remote Similarity	NPD6987	Phase 1
0.6905	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD1587	Approved
0.6903	Remote Similarity	NPD7853	Phase 2
0.6901	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.69	Remote Similarity	NPD4889	Approved
0.6898	Remote Similarity	NPD2412	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.689	Remote Similarity	NPD3931	Approved
0.689	Remote Similarity	NPD3928	Approved
0.6884	Remote Similarity	NPD2095	Phase 2
0.6884	Remote Similarity	NPD2094	Phase 2
0.6884	Remote Similarity	NPD3243	Approved
0.6884	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD2092	Phase 2
0.6881	Remote Similarity	NPD4021	Phase 2
0.6875	Remote Similarity	NPD6389	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5445	Approved
0.6869	Remote Similarity	NPD3915	Approved
0.6869	Remote Similarity	NPD9510	Approved
0.6866	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD4703	Approved
0.6865	Remote Similarity	NPD4702	Approved
0.6863	Remote Similarity	NPD6569	Phase 2
0.686	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD1684	Approved
0.6859	Remote Similarity	NPD1685	Approved
0.6853	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5293	Phase 2
0.685	Remote Similarity	NPD2091	Phase 2
0.685	Remote Similarity	NPD2096	Phase 2
0.6849	Remote Similarity	NPD8479	Phase 2
0.6847	Remote Similarity	NPD3321	Discontinued
0.6847	Remote Similarity	NPD3871	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD3263	Phase 3
0.6847	Remote Similarity	NPD3870	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD8289	Discontinued
0.6845	Remote Similarity	NPD2307	Discontinued
0.6844	Remote Similarity	NPD7031	Phase 1
0.6837	Remote Similarity	NPD8093	Discontinued
0.6837	Remote Similarity	NPD4883	Approved
0.6834	Remote Similarity	NPD3386	Phase 2
0.6827	Remote Similarity	NPD4548	Discontinued
0.6825	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4558	Phase 2
0.682	Remote Similarity	NPD5612	Discontinued
0.682	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.682	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6808	Remote Similarity	NPD7665	Phase 2
0.6808	Remote Similarity	NPD7666	Phase 3
0.6806	Remote Similarity	NPD3945	Discontinued
0.6806	Remote Similarity	NPD9398	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD8094	Discontinued
0.6802	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD3395	Approved
0.6796	Remote Similarity	NPD3396	Approved
0.6792	Remote Similarity	NPD7001	Phase 3
0.6792	Remote Similarity	NPD7010	Phase 3
0.6792	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD7470	Discontinued
0.6791	Remote Similarity	NPD5475	Discontinued
0.6791	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD2813	Phase 3
0.6789	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD926	Approved
0.6788	Remote Similarity	NPD925	Approved
0.6786	Remote Similarity	NPD4524	Discontinued
0.678	Remote Similarity	NPD4376	Phase 3
0.6774	Remote Similarity	NPD5149	Phase 2
0.6774	Remote Similarity	NPD5148	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD7180	Phase 3
0.6773	Remote Similarity	NPD5850	Phase 3
0.6769	Remote Similarity	NPD4314	Approved
0.6769	Remote Similarity	NPD4313	Approved
0.6767	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7564	Discontinued
0.6766	Remote Similarity	NPD3569	Discontinued
0.6761	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD424	Approved
0.6753	Remote Similarity	NPD425	Approved
0.6751	Remote Similarity	NPD1586	Approved
0.675	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD5999	Phase 2
0.6745	Remote Similarity	NPD5426	Phase 3
0.6741	Remote Similarity	NPD3259	Approved
0.6737	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD5138	Approved
0.6736	Remote Similarity	NPD5140	Approved
0.6735	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD4079	Approved
0.6734	Remote Similarity	NPD4076	Approved
0.673	Remote Similarity	NPD7187	Phase 2
0.6729	Remote Similarity	NPD7467	Discontinued
0.6728	Remote Similarity	NPD3795	Approved
0.6728	Remote Similarity	NPD3794	Approved
0.6726	Remote Similarity	NPD8106	Phase 2
0.6726	Remote Similarity	NPD4890	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