NPASS Compound

Structure

NPC74153 OpenBabel07101718242D 23 26 0 0 0 0 0 0 0 0999 V2000 -4.7359 -3.8410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7178 -2.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5449 -3.2532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5268 -1.8520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0133 -4.0220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0997 -3.6153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4614 -2.7398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8223 -3.4343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4403 -2.2587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0817 -2.2140 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0574 -1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -3.0827 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.9952 -2.6208 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.2494 -1.6709 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9449 -0.9406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 1 11 2 0 0 0 0 2 4 2 0 0 0 0 2 11 1 0 0 0 0 3 13 2 0 0 0 0 4 13 1 0 0 0 0 5 7 1 0 0 0 0 5 11 1 0 0 0 0 6 8 1 0 0 0 0 6 12 1 0 0 0 0 7 20 1 0 0 0 0 8 19 1 0 0 0 0 9 14 1 0 0 0 0 9 15 2 0 0 0 0 10 12 2 0 0 0 0 10 21 1 0 0 0 0 12 16 1 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 14 19 2 0 0 0 0 15 18 1 0 0 0 0 15 20 1 0 0 0 0 16 17 2 0 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 23 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	307.13
Volume:	315.137
LogP:	3.312
LogD:	2.831
LogS:	-4.236
# Rotatable Bonds:	4
TPSA:	80.64
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.557
Synthetic Accessibility Score:	3.087
Fsp3:	0.167
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:	-5.119
MDCK Permeability:	5.809868980577448e-06
Pgp-inhibitor:	0.009
Pgp-substrate:	0.977
Human Intestinal Absorption (HIA):	0.037
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031
Plasma Protein Binding (PPB):	97.39938354492188%
Volume Distribution (VD):	0.511
Pgp-substrate:	2.5445473194122314%

ADMET: Metabolism

CYP1A2-inhibitor:	0.98
CYP1A2-substrate:	0.642
CYP2C19-inhibitor:	0.774
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.718
CYP2C9-substrate:	0.909
CYP2D6-inhibitor:	0.939
CYP2D6-substrate:	0.913
CYP3A4-inhibitor:	0.336
CYP3A4-substrate:	0.181

ADMET: Excretion

Clearance (CL):	7.613
Half-life (T1/2):	0.889

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.659
Drug-inuced Liver Injury (DILI):	0.947
AMES Toxicity:	0.915
Rat Oral Acute Toxicity:	0.657
Maximum Recommended Daily Dose:	0.911
Skin Sensitization:	0.952
Carcinogencity:	0.738
Eye Corrosion:	0.003
Eye Irritation:	0.23
Respiratory Toxicity:	0.78

Download Data

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

Natural Product: NPC74153

Natural Product ID:	NPC74153
*Common Name:**	Makaluvamine D
IUPAC Name:	n.a.
Synonyms:	Makaluvamine D
Standard InCHIKey:	BBIQXQHDNKDTQK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H17N3O2/c22-13-3-1-11(2-4-13)5-7-20-15-9-14-16-12(6-8-19-14)10-21-17(16)18(15)23/h1-4,9-10,20-22H,5-8H2
SMILES:	c1cc(ccc1CCNC1=CC2=NCCc3c[nH]c(c23)C1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453817
PubChem CID:	n.a.
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]
NPO33184	sceptrella sp.	Species	Latrunculiidae	Eukaryota	n.a.	Korean	n.a.	PMID[20055495]
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	4
MIC	6

Activity Type	# Activity
Cell Line	3
Individual Protein	1
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1821	Individual Protein	Sortase	Staphylococcus aureus	IC50	=	148500.0	nM	PMID[483323]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	24600.0	nM	PMID[483323]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	170.0	nM	PMID[483324]
NPT6399	Cell Line	XRS6	Cricetulus griseus	IC50	=	80.0	nM	PMID[483324]
NPT1190	Organism	Salmonella enterica	Salmonella enterica	MIC	=	100.0	ug.mL-1	PMID[483323]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[483323]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[483323]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[483323]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	50.0	ug.mL-1	PMID[483323]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	25.0	ug.mL-1	PMID[483323]

☑ 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 NPC74153 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	358
0.1-0.2	3188
0.2-0.3	13505
0.3-0.4	6123
0.4-0.5	14210
0.5-0.6	2856
0.6-0.7	2101
0.7-0.8	341
0.8-0.85	5
0.85-0.9	4
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9828	High Similarity	NPC473821
0.9661	High Similarity	NPC78767
0.9661	High Similarity	NPC473814
0.9548	High Similarity	NPC93390
0.8936	High Similarity	NPC175602
0.8796	High Similarity	NPC61038
0.8615	High Similarity	NPC207866
0.8564	High Similarity	NPC110182
0.837	Intermediate Similarity	NPC295158
0.83	Intermediate Similarity	NPC27041
0.823	Intermediate Similarity	NPC475635
0.8218	Intermediate Similarity	NPC269270
0.8177	Intermediate Similarity	NPC14686
0.8046	Intermediate Similarity	NPC471655
0.798	Intermediate Similarity	NPC322064
0.794	Intermediate Similarity	NPC183777
0.7826	Intermediate Similarity	NPC262338
0.7826	Intermediate Similarity	NPC276657
0.7824	Intermediate Similarity	NPC99666
0.7817	Intermediate Similarity	NPC45459
0.7817	Intermediate Similarity	NPC315491
0.7793	Intermediate Similarity	NPC200553
0.7793	Intermediate Similarity	NPC279189
0.7789	Intermediate Similarity	NPC241025
0.7745	Intermediate Similarity	NPC219087
0.7732	Intermediate Similarity	NPC324149
0.773	Intermediate Similarity	NPC302647
0.7729	Intermediate Similarity	NPC264285
0.7727	Intermediate Similarity	NPC213308
0.7723	Intermediate Similarity	NPC171787
0.771	Intermediate Similarity	NPC207686
0.7708	Intermediate Similarity	NPC46580
0.7685	Intermediate Similarity	NPC162002
0.768	Intermediate Similarity	NPC474492
0.7673	Intermediate Similarity	NPC270918
0.7665	Intermediate Similarity	NPC156704
0.766	Intermediate Similarity	NPC96890
0.7653	Intermediate Similarity	NPC202812
0.7639	Intermediate Similarity	NPC174489
0.7629	Intermediate Similarity	NPC475874
0.7627	Intermediate Similarity	NPC100726
0.7617	Intermediate Similarity	NPC278434
0.7608	Intermediate Similarity	NPC168209
0.7604	Intermediate Similarity	NPC477549
0.7604	Intermediate Similarity	NPC314002
0.7592	Intermediate Similarity	NPC220765
0.7579	Intermediate Similarity	NPC79777
0.7579	Intermediate Similarity	NPC271792
0.7577	Intermediate Similarity	NPC473628
0.7569	Intermediate Similarity	NPC26641
0.7565	Intermediate Similarity	NPC171171
0.7552	Intermediate Similarity	NPC204717
0.7541	Intermediate Similarity	NPC470680
0.7541	Intermediate Similarity	NPC100104
0.7538	Intermediate Similarity	NPC472284
0.7538	Intermediate Similarity	NPC83111
0.7538	Intermediate Similarity	NPC306376
0.7538	Intermediate Similarity	NPC477044
0.7538	Intermediate Similarity	NPC477041
0.7512	Intermediate Similarity	NPC471944
0.75	Intermediate Similarity	NPC175150
0.75	Intermediate Similarity	NPC16352
0.75	Intermediate Similarity	NPC243633
0.75	Intermediate Similarity	NPC37152
0.7489	Intermediate Similarity	NPC15801
0.7488	Intermediate Similarity	NPC477043
0.7487	Intermediate Similarity	NPC77555
0.7487	Intermediate Similarity	NPC227582
0.7487	Intermediate Similarity	NPC209917
0.7487	Intermediate Similarity	NPC234403
0.7487	Intermediate Similarity	NPC477042
0.7474	Intermediate Similarity	NPC184964
0.7462	Intermediate Similarity	NPC56170
0.7462	Intermediate Similarity	NPC47190
0.7461	Intermediate Similarity	NPC477003
0.7453	Intermediate Similarity	NPC473317
0.7441	Intermediate Similarity	NPC74360
0.744	Intermediate Similarity	NPC82370
0.7437	Intermediate Similarity	NPC242209
0.7429	Intermediate Similarity	NPC469727
0.7429	Intermediate Similarity	NPC472285
0.7418	Intermediate Similarity	NPC220851
0.7416	Intermediate Similarity	NPC237740
0.7415	Intermediate Similarity	NPC88008
0.7413	Intermediate Similarity	NPC477045
0.7406	Intermediate Similarity	NPC323969
0.74	Intermediate Similarity	NPC167710
0.7387	Intermediate Similarity	NPC276517
0.7383	Intermediate Similarity	NPC229893
0.7383	Intermediate Similarity	NPC122436
0.7382	Intermediate Similarity	NPC284775
0.7379	Intermediate Similarity	NPC143075
0.7376	Intermediate Similarity	NPC252338
0.7376	Intermediate Similarity	NPC101350
0.736	Intermediate Similarity	NPC119569
0.736	Intermediate Similarity	NPC154339
0.7351	Intermediate Similarity	NPC131718
0.7349	Intermediate Similarity	NPC125597
0.7348	Intermediate Similarity	NPC473878
0.7347	Intermediate Similarity	NPC477415
0.7347	Intermediate Similarity	NPC23476
0.7347	Intermediate Similarity	NPC474259
0.7344	Intermediate Similarity	NPC72980
0.7333	Intermediate Similarity	NPC178858
0.733	Intermediate Similarity	NPC235685
0.7327	Intermediate Similarity	NPC194740
0.7322	Intermediate Similarity	NPC33229
0.7317	Intermediate Similarity	NPC472259
0.7317	Intermediate Similarity	NPC470500
0.7315	Intermediate Similarity	NPC24370
0.7315	Intermediate Similarity	NPC319232
0.7308	Intermediate Similarity	NPC309845
0.7303	Intermediate Similarity	NPC473804
0.7294	Intermediate Similarity	NPC326363
0.7287	Intermediate Similarity	NPC41717
0.7282	Intermediate Similarity	NPC228835
0.7282	Intermediate Similarity	NPC472286
0.7282	Intermediate Similarity	NPC472287
0.7277	Intermediate Similarity	NPC48317
0.7277	Intermediate Similarity	NPC131887
0.7273	Intermediate Similarity	NPC23294
0.7273	Intermediate Similarity	NPC274981
0.7269	Intermediate Similarity	NPC91868
0.7269	Intermediate Similarity	NPC63971
0.7268	Intermediate Similarity	NPC98715
0.7268	Intermediate Similarity	NPC53144
0.7268	Intermediate Similarity	NPC134848
0.7268	Intermediate Similarity	NPC476098
0.7252	Intermediate Similarity	NPC184225
0.725	Intermediate Similarity	NPC267343
0.725	Intermediate Similarity	NPC45850
0.725	Intermediate Similarity	NPC304203
0.7245	Intermediate Similarity	NPC311282
0.724	Intermediate Similarity	NPC182222
0.724	Intermediate Similarity	NPC97902
0.7236	Intermediate Similarity	NPC476460
0.7236	Intermediate Similarity	NPC138370
0.7234	Intermediate Similarity	NPC471178
0.7233	Intermediate Similarity	NPC475070
0.7225	Intermediate Similarity	NPC303951
0.7222	Intermediate Similarity	NPC221873
0.7219	Intermediate Similarity	NPC471177
0.7219	Intermediate Similarity	NPC124542
0.7219	Intermediate Similarity	NPC59779
0.7217	Intermediate Similarity	NPC330009
0.7216	Intermediate Similarity	NPC182940
0.7214	Intermediate Similarity	NPC146724
0.7214	Intermediate Similarity	NPC195239
0.7214	Intermediate Similarity	NPC326634
0.7214	Intermediate Similarity	NPC157828
0.7212	Intermediate Similarity	NPC39679
0.7212	Intermediate Similarity	NPC210828
0.7212	Intermediate Similarity	NPC86834
0.7202	Intermediate Similarity	NPC111275
0.72	Intermediate Similarity	NPC471448
0.7198	Intermediate Similarity	NPC102664
0.7198	Intermediate Similarity	NPC63109
0.7194	Intermediate Similarity	NPC207851
0.7189	Intermediate Similarity	NPC476818
0.7188	Intermediate Similarity	NPC110500
0.7188	Intermediate Similarity	NPC149155
0.7188	Intermediate Similarity	NPC203468
0.7181	Intermediate Similarity	NPC102423
0.7178	Intermediate Similarity	NPC11445
0.7174	Intermediate Similarity	NPC251391
0.7172	Intermediate Similarity	NPC206186
0.7172	Intermediate Similarity	NPC17059
0.7171	Intermediate Similarity	NPC300183
0.717	Intermediate Similarity	NPC50562
0.7165	Intermediate Similarity	NPC55772
0.7165	Intermediate Similarity	NPC248041
0.7165	Intermediate Similarity	NPC283219
0.7165	Intermediate Similarity	NPC126709
0.7165	Intermediate Similarity	NPC42979
0.7165	Intermediate Similarity	NPC11126
0.7164	Intermediate Similarity	NPC307963
0.7163	Intermediate Similarity	NPC225821
0.7163	Intermediate Similarity	NPC54066
0.7163	Intermediate Similarity	NPC46225
0.7162	Intermediate Similarity	NPC325976
0.7158	Intermediate Similarity	NPC63751
0.7158	Intermediate Similarity	NPC78020
0.7157	Intermediate Similarity	NPC74413
0.715	Intermediate Similarity	NPC224764
0.715	Intermediate Similarity	NPC267885
0.7149	Intermediate Similarity	NPC196718
0.7143	Intermediate Similarity	NPC90229
0.7136	Intermediate Similarity	NPC211813
0.7136	Intermediate Similarity	NPC67658
0.7136	Intermediate Similarity	NPC32771
0.7136	Intermediate Similarity	NPC470678
0.7129	Intermediate Similarity	NPC258062
0.7129	Intermediate Similarity	NPC127677
0.7123	Intermediate Similarity	NPC236668
0.7123	Intermediate Similarity	NPC266931
0.7121	Intermediate Similarity	NPC235684
0.712	Intermediate Similarity	NPC470679
0.712	Intermediate Similarity	NPC217021
0.7117	Intermediate Similarity	NPC323752
0.7115	Intermediate Similarity	NPC472064

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 NPC74153 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	212
0.1-0.2	599
0.2-0.3	896
0.3-0.4	1002
0.4-0.5	2796
0.5-0.6	2570
0.6-0.7	1018
0.7-0.8	57
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
0.7914	Intermediate Similarity	NPD3178	Discontinued
0.7839	Intermediate Similarity	NPD5901	Discontinued
0.7817	Intermediate Similarity	NPD484	Approved
0.7784	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD7948	Phase 1
0.7723	Intermediate Similarity	NPD6376	Discontinued
0.7656	Intermediate Similarity	NPD6242	Discontinued
0.7644	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD4845	Discontinued
0.746	Intermediate Similarity	NPD5065	Approved
0.7352	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD7603	Discontinued
0.7268	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD3326	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD4511	Phase 1
0.7241	Intermediate Similarity	NPD3814	Phase 1
0.7217	Intermediate Similarity	NPD3389	Approved
0.7217	Intermediate Similarity	NPD3394	Approved
0.7217	Intermediate Similarity	NPD3393	Approved
0.7196	Intermediate Similarity	NPD7203	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD1096	Discontinued
0.7194	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD482	Approved
0.7184	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD1038	Approved
0.7164	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD3918	Approved
0.7156	Intermediate Similarity	NPD3916	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD3917	Approved
0.715	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2092	Phase 2
0.7143	Intermediate Similarity	NPD2095	Phase 2
0.7143	Intermediate Similarity	NPD2094	Phase 2
0.7143	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD2510	Approved
0.7129	Intermediate Similarity	NPD2509	Approved
0.7122	Intermediate Similarity	NPD5497	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7586	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD3779	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD3915	Approved
0.7107	Intermediate Similarity	NPD2091	Phase 2
0.7107	Intermediate Similarity	NPD2096	Phase 2
0.7101	Intermediate Similarity	NPD5513	Phase 2
0.7098	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD802	Phase 2
0.7073	Intermediate Similarity	NPD6137	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD2781	Approved
0.7067	Intermediate Similarity	NPD3947	Discontinued
0.7065	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD5612	Discontinued
0.7053	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD2780	Approved
0.7053	Intermediate Similarity	NPD2782	Approved
0.7021	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1631	Approved
0.6995	Remote Similarity	NPD5866	Approved
0.6991	Remote Similarity	NPD4429	Discontinued
0.6982	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD4923	Phase 1
0.6961	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD3017	Clinical (unspecified phase)
0.696	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1643	Phase 3
0.6954	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.695	Remote Similarity	NPD3315	Phase 3
0.695	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1573	Approved
0.6943	Remote Similarity	NPD1575	Approved
0.6941	Remote Similarity	NPD8356	Approved
0.6927	Remote Similarity	NPD4848	Phase 1
0.6916	Remote Similarity	NPD8093	Discontinued
0.6915	Remote Similarity	NPD4948	Discontinued
0.6913	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6753	Phase 1
0.6909	Remote Similarity	NPD6173	Approved
0.6909	Remote Similarity	NPD6752	Phase 1
0.6908	Remote Similarity	NPD3825	Phase 3
0.6897	Remote Similarity	NPD4558	Phase 2
0.6892	Remote Similarity	NPD7994	Phase 2
0.6891	Remote Similarity	NPD2844	Phase 3
0.689	Remote Similarity	NPD6975	Discontinued
0.6884	Remote Similarity	NPD8094	Discontinued
0.6884	Remote Similarity	NPD3243	Approved
0.6881	Remote Similarity	NPD4021	Phase 2
0.6875	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD750	Phase 2
0.6869	Remote Similarity	NPD5445	Approved
0.6869	Remote Similarity	NPD7470	Discontinued
0.6866	Remote Similarity	NPD4989	Phase 2
0.6863	Remote Similarity	NPD5937	Approved
0.6863	Remote Similarity	NPD6665	Discontinued
0.6849	Remote Similarity	NPD6530	Approved
0.6849	Remote Similarity	NPD6531	Approved
0.6845	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1630	Approved
0.6842	Remote Similarity	NPD5255	Approved
0.684	Remote Similarity	NPD3962	Phase 2
0.684	Remote Similarity	NPD3959	Phase 2
0.6837	Remote Similarity	NPD3330	Phase 1
0.6837	Remote Similarity	NPD4883	Approved
0.6834	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD2803	Discontinued
0.683	Remote Similarity	NPD1659	Phase 1
0.683	Remote Similarity	NPD5022	Discontinued
0.6828	Remote Similarity	NPD7853	Phase 2
0.6825	Remote Similarity	NPD5426	Phase 3
0.6823	Remote Similarity	NPD5140	Approved
0.6823	Remote Similarity	NPD5138	Approved
0.6823	Remote Similarity	NPD5088	Discontinued
0.6818	Remote Similarity	NPD4079	Approved
0.6818	Remote Similarity	NPD4076	Approved
0.6816	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD4889	Approved
0.6816	Remote Similarity	NPD8430	Approved
0.6814	Remote Similarity	NPD2336	Approved
0.6808	Remote Similarity	NPD2916	Discontinued
0.6806	Remote Similarity	NPD3945	Discontinued
0.6804	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD7618	Phase 3
0.6796	Remote Similarity	NPD7619	Phase 3
0.6795	Remote Similarity	NPD5482	Discontinued
0.6791	Remote Similarity	NPD5067	Phase 2
0.6791	Remote Similarity	NPD5066	Phase 2
0.6784	Remote Similarity	NPD9510	Approved
0.6784	Remote Similarity	NPD5473	Discontinued
0.6782	Remote Similarity	NPD706	Phase 1
0.678	Remote Similarity	NPD4376	Phase 3
0.678	Remote Similarity	NPD6569	Phase 2
0.6773	Remote Similarity	NPD1996	Discontinued
0.6771	Remote Similarity	NPD1685	Approved
0.6771	Remote Similarity	NPD1684	Approved
0.6771	Remote Similarity	NPD3263	Phase 3
0.6769	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD3506	Approved
0.6768	Remote Similarity	NPD3505	Approved
0.6768	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD5017	Discontinued
0.6758	Remote Similarity	NPD5632	Approved
0.6755	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD424	Approved
0.6753	Remote Similarity	NPD425	Approved
0.675	Remote Similarity	NPD3386	Phase 2
0.6749	Remote Similarity	NPD4988	Discontinued
0.6749	Remote Similarity	NPD3961	Discontinued
0.6746	Remote Similarity	NPD4548	Discontinued
0.6746	Remote Similarity	NPD6999	Discontinued
0.6746	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.673	Remote Similarity	NPD3928	Approved
0.673	Remote Similarity	NPD3931	Approved
0.6729	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD3795	Approved
0.6728	Remote Similarity	NPD3794	Approved
0.6719	Remote Similarity	NPD9398	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD4075	Phase 2
0.6715	Remote Similarity	NPD3396	Approved
0.6715	Remote Similarity	NPD3395	Approved
0.6714	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD6389	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD7010	Phase 3
0.6713	Remote Similarity	NPD5475	Discontinued
0.6713	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD6710	Phase 3
0.671	Remote Similarity	NPD6790	Phase 1
0.6703	Remote Similarity	NPD3813	Approved
0.6703	Remote Similarity	NPD2896	Discontinued
0.6701	Remote Similarity	NPD926	Approved
0.6701	Remote Similarity	NPD925	Approved
0.67	Remote Similarity	NPD2481	Approved
0.67	Remote Similarity	NPD2479	Phase 3
0.6699	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD3404	Approved
0.6697	Remote Similarity	NPD5850	Phase 3
0.6696	Remote Similarity	NPD4314	Approved
0.6696	Remote Similarity	NPD8289	Discontinued
0.6696	Remote Similarity	NPD4313	Approved
0.6684	Remote Similarity	NPD4703	Approved
0.6684	Remote Similarity	NPD1325	Approved
0.6684	Remote Similarity	NPD4702	Approved
0.6684	Remote Similarity	NPD1326	Approved
0.6684	Remote Similarity	NPD2061	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data