NPASS Compound

Structure

NPC93390 OpenBabel07101718202D 24 27 0 0 0 0 0 0 0 0999 V2000 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7124 0.7796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0079 -0.8027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6259 0.3729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9215 -1.2094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9898 0.5986 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 4.1808 0.0108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6034 -0.9703 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 5.9034 0.1918 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 7.7305 -0.6216 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 2.4583 -0.1703 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 0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7422 0.2151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -2.5827 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.2673 0.4175 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 8.6440 -1.0284 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7871 1.2140 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 2 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:	319.13
Volume:	329.797
LogP:	3.247
LogD:	3.167
LogS:	-3.858
# Rotatable Bonds:	3
TPSA:	70.11
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.721
Synthetic Accessibility Score:	3.515
Fsp3:	0.158
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.008
MDCK Permeability:	1.8354092389927246e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.894
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.766
Plasma Protein Binding (PPB):	94.85071563720703%
Volume Distribution (VD):	0.885
Pgp-substrate:	5.472158908843994%

ADMET: Metabolism

CYP1A2-inhibitor:	0.978
CYP1A2-substrate:	0.83
CYP2C19-inhibitor:	0.274
CYP2C19-substrate:	0.149
CYP2C9-inhibitor:	0.23
CYP2C9-substrate:	0.817
CYP2D6-inhibitor:	0.879
CYP2D6-substrate:	0.928
CYP3A4-inhibitor:	0.224
CYP3A4-substrate:	0.359

ADMET: Excretion

Clearance (CL):	5.908
Half-life (T1/2):	0.766

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.546
Drug-inuced Liver Injury (DILI):	0.948
AMES Toxicity:	0.741
Rat Oral Acute Toxicity:	0.468
Maximum Recommended Daily Dose:	0.865
Skin Sensitization:	0.936
Carcinogencity:	0.958
Eye Corrosion:	0.003
Eye Irritation:	0.677
Respiratory Toxicity:	0.878

Download Data

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

Natural Product: NPC93390

Natural Product ID:	NPC93390
*Common Name:**	Makaluvamine E
IUPAC Name:	n.a.
Synonyms:	Makaluvamine E
Standard InCHIKey:	SRIGKAHCWXJXIV-SOFGYWHQSA-N
Standard InCHI:	InChI=1S/C19H17N3O2/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/h2-6,8,10-11,21,23H,7,9H2,1H3/b8-6+
SMILES:	Oc1ccc(cc1)/C=C/NC1=CC2=NCCc3c2c(C1=O)n(C)c3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509186
PubChem CID:	9973231
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	2

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.6	ug ml-1	PMID[492123]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	170.0	nM	PMID[492124]
NPT6399	Cell Line	XRS6	Cricetulus griseus	IC50	=	80.0	nM	PMID[492124]

☑ 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 NPC93390 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	331
0.1-0.2	3043
0.2-0.3	13465
0.3-0.4	5694
0.4-0.5	14622
0.5-0.6	3199
0.6-0.7	2087
0.7-0.8	241
0.8-0.85	5
0.85-0.9	4
0.9-0.95	1
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9885	High Similarity	NPC78767
0.9885	High Similarity	NPC473814
0.96	High Similarity	NPC473821
0.9548	High Similarity	NPC74153
0.8789	High Similarity	NPC61038
0.8632	High Similarity	NPC175602
0.8608	High Similarity	NPC207866
0.8564	High Similarity	NPC295158
0.8274	Intermediate Similarity	NPC110182
0.8168	Intermediate Similarity	NPC14686
0.8119	Intermediate Similarity	NPC269270
0.8023	Intermediate Similarity	NPC100726
0.7968	Intermediate Similarity	NPC241025
0.7931	Intermediate Similarity	NPC27041
0.7877	Intermediate Similarity	NPC475635
0.7829	Intermediate Similarity	NPC471655
0.7754	Intermediate Similarity	NPC271792
0.7707	Intermediate Similarity	NPC322064
0.7704	Intermediate Similarity	NPC472284
0.7627	Intermediate Similarity	NPC473878
0.7574	Intermediate Similarity	NPC183777
0.7571	Intermediate Similarity	NPC102664
0.7562	Intermediate Similarity	NPC472259
0.7538	Intermediate Similarity	NPC56170
0.7527	Intermediate Similarity	NPC302647
0.7525	Intermediate Similarity	NPC472286
0.7525	Intermediate Similarity	NPC472287
0.7486	Intermediate Similarity	NPC473804
0.7476	Intermediate Similarity	NPC276657
0.7454	Intermediate Similarity	NPC200553
0.7454	Intermediate Similarity	NPC279189
0.745	Intermediate Similarity	NPC315491
0.745	Intermediate Similarity	NPC45459
0.7449	Intermediate Similarity	NPC99666
0.7443	Intermediate Similarity	NPC119569
0.7433	Intermediate Similarity	NPC262338
0.7432	Intermediate Similarity	NPC470680
0.7432	Intermediate Similarity	NPC100104
0.7431	Intermediate Similarity	NPC477549
0.7429	Intermediate Similarity	NPC168209
0.7426	Intermediate Similarity	NPC53144
0.7404	Intermediate Similarity	NPC237740
0.7393	Intermediate Similarity	NPC54066
0.7391	Intermediate Similarity	NPC219087
0.7389	Intermediate Similarity	NPC470679
0.7389	Intermediate Similarity	NPC217021
0.7382	Intermediate Similarity	NPC182940
0.7381	Intermediate Similarity	NPC264285
0.7376	Intermediate Similarity	NPC470678
0.7373	Intermediate Similarity	NPC207686
0.7371	Intermediate Similarity	NPC171171
0.7366	Intermediate Similarity	NPC171787
0.7366	Intermediate Similarity	NPC41717
0.7363	Intermediate Similarity	NPC213308
0.736	Intermediate Similarity	NPC324149
0.736	Intermediate Similarity	NPC471448
0.7352	Intermediate Similarity	NPC162002
0.7348	Intermediate Similarity	NPC251391
0.7347	Intermediate Similarity	NPC268966
0.7347	Intermediate Similarity	NPC475874
0.7333	Intermediate Similarity	NPC46580
0.7333	Intermediate Similarity	NPC469727
0.7324	Intermediate Similarity	NPC175150
0.7324	Intermediate Similarity	NPC243633
0.732	Intermediate Similarity	NPC314002
0.7317	Intermediate Similarity	NPC270918
0.7312	Intermediate Similarity	NPC471178
0.7306	Intermediate Similarity	NPC174489
0.73	Intermediate Similarity	NPC156704
0.7297	Intermediate Similarity	NPC59779
0.7297	Intermediate Similarity	NPC124542
0.7297	Intermediate Similarity	NPC471177
0.7291	Intermediate Similarity	NPC57398
0.7291	Intermediate Similarity	NPC211813
0.7286	Intermediate Similarity	NPC202812
0.7283	Intermediate Similarity	NPC474492
0.7278	Intermediate Similarity	NPC123906
0.7277	Intermediate Similarity	NPC96890
0.7268	Intermediate Similarity	NPC204717
0.7264	Intermediate Similarity	NPC477041
0.7264	Intermediate Similarity	NPC477044
0.7264	Intermediate Similarity	NPC306376
0.7255	Intermediate Similarity	NPC200836
0.7251	Intermediate Similarity	NPC472285
0.7245	Intermediate Similarity	NPC206186
0.7245	Intermediate Similarity	NPC278434
0.7241	Intermediate Similarity	NPC471944
0.724	Intermediate Similarity	NPC15801
0.724	Intermediate Similarity	NPC26641
0.7236	Intermediate Similarity	NPC45850
0.7231	Intermediate Similarity	NPC311282
0.722	Intermediate Similarity	NPC477043
0.722	Intermediate Similarity	NPC88115
0.7216	Intermediate Similarity	NPC220765
0.7214	Intermediate Similarity	NPC227582
0.7213	Intermediate Similarity	NPC209362
0.7212	Intermediate Similarity	NPC124086
0.7212	Intermediate Similarity	NPC309845
0.7212	Intermediate Similarity	NPC85273
0.7208	Intermediate Similarity	NPC473628
0.7208	Intermediate Similarity	NPC209917
0.7207	Intermediate Similarity	NPC467188
0.7206	Intermediate Similarity	NPC106757
0.7202	Intermediate Similarity	NPC79777
0.7202	Intermediate Similarity	NPC477042
0.72	Intermediate Similarity	NPC146724
0.7196	Intermediate Similarity	NPC473317
0.719	Intermediate Similarity	NPC236668
0.7186	Intermediate Similarity	NPC47190
0.7183	Intermediate Similarity	NPC74360
0.7179	Intermediate Similarity	NPC207851
0.7178	Intermediate Similarity	NPC474916
0.7175	Intermediate Similarity	NPC37152
0.7172	Intermediate Similarity	NPC83111
0.717	Intermediate Similarity	NPC246658
0.7163	Intermediate Similarity	NPC16352
0.7163	Intermediate Similarity	NPC220851
0.7156	Intermediate Similarity	NPC194740
0.7156	Intermediate Similarity	NPC146976
0.715	Intermediate Similarity	NPC323969
0.7143	Intermediate Similarity	NPC24370
0.7143	Intermediate Similarity	NPC477045
0.7143	Intermediate Similarity	NPC319232
0.7143	Intermediate Similarity	NPC103361
0.7143	Intermediate Similarity	NPC474767
0.713	Intermediate Similarity	NPC122436
0.713	Intermediate Similarity	NPC101350
0.7129	Intermediate Similarity	NPC77555
0.7129	Intermediate Similarity	NPC90229
0.7127	Intermediate Similarity	NPC105811
0.7123	Intermediate Similarity	NPC326363
0.7122	Intermediate Similarity	NPC472063
0.7122	Intermediate Similarity	NPC472069
0.7122	Intermediate Similarity	NPC328318
0.7122	Intermediate Similarity	NPC328596
0.7122	Intermediate Similarity	NPC472062
0.7121	Intermediate Similarity	NPC183805
0.7113	Intermediate Similarity	NPC234403
0.7113	Intermediate Similarity	NPC73994
0.7108	Intermediate Similarity	NPC252338
0.7104	Intermediate Similarity	NPC70406
0.7103	Intermediate Similarity	NPC313804
0.7103	Intermediate Similarity	NPC315804
0.7101	Intermediate Similarity	NPC472064
0.7098	Intermediate Similarity	NPC184964
0.7097	Intermediate Similarity	NPC125597
0.7095	Intermediate Similarity	NPC82370
0.7092	Intermediate Similarity	NPC477003
0.7092	Intermediate Similarity	NPC228835
0.7085	Intermediate Similarity	NPC235685
0.7085	Intermediate Similarity	NPC184225
0.7079	Intermediate Similarity	NPC242209
0.7075	Intermediate Similarity	NPC239763
0.7075	Intermediate Similarity	NPC190401
0.7068	Intermediate Similarity	NPC253810
0.7067	Intermediate Similarity	NPC53344
0.7067	Intermediate Similarity	NPC88008
0.7062	Intermediate Similarity	NPC67659
0.7062	Intermediate Similarity	NPC72980
0.7062	Intermediate Similarity	NPC164340
0.7059	Intermediate Similarity	NPC284338
0.7059	Intermediate Similarity	NPC81535
0.7059	Intermediate Similarity	NPC123395
0.7053	Intermediate Similarity	NPC475070
0.7051	Intermediate Similarity	NPC229893
0.7049	Intermediate Similarity	NPC313889
0.7044	Intermediate Similarity	NPC167710
0.7042	Intermediate Similarity	NPC330009
0.7042	Intermediate Similarity	NPC476161
0.7037	Intermediate Similarity	NPC121069
0.7035	Intermediate Similarity	NPC75544
0.7033	Intermediate Similarity	NPC143075
0.7031	Intermediate Similarity	NPC63971
0.7031	Intermediate Similarity	NPC471294
0.7031	Intermediate Similarity	NPC91868
0.703	Intermediate Similarity	NPC135950
0.703	Intermediate Similarity	NPC276517
0.7027	Intermediate Similarity	NPC33229
0.7026	Intermediate Similarity	NPC61011
0.7023	Intermediate Similarity	NPC48317
0.702	Intermediate Similarity	NPC118084
0.7019	Intermediate Similarity	NPC317373
0.7018	Intermediate Similarity	NPC178858
0.7015	Intermediate Similarity	NPC216550
0.7014	Intermediate Similarity	NPC23294
0.7014	Intermediate Similarity	NPC477112
0.701	Intermediate Similarity	NPC284775
0.701	Intermediate Similarity	NPC157583
0.7009	Intermediate Similarity	NPC303384
0.7009	Intermediate Similarity	NPC298840
0.7009	Intermediate Similarity	NPC268393
0.7009	Intermediate Similarity	NPC191088
0.7009	Intermediate Similarity	NPC13599
0.7009	Intermediate Similarity	NPC3214
0.7005	Intermediate Similarity	NPC46895
0.7005	Intermediate Similarity	NPC476098
0.7005	Intermediate Similarity	NPC80681
0.7005	Intermediate Similarity	NPC98715
0.7005	Intermediate Similarity	NPC134848
0.7	Intermediate Similarity	NPC469489

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 NPC93390 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	573
0.2-0.3	916
0.3-0.4	921
0.4-0.5	2717
0.5-0.6	2657
0.6-0.7	1110
0.7-0.8	60
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
0.7762	Intermediate Similarity	NPD4845	Discontinued
0.7619	Intermediate Similarity	NPD3178	Discontinued
0.7562	Intermediate Similarity	NPD5901	Discontinued
0.7537	Intermediate Similarity	NPD6376	Discontinued
0.75	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD6242	Discontinued
0.7464	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD484	Approved
0.7405	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD7948	Phase 1
0.7346	Intermediate Similarity	NPD7203	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3326	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1643	Phase 3
0.7268	Intermediate Similarity	NPD1096	Discontinued
0.7263	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD3779	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD1631	Approved
0.7228	Intermediate Similarity	NPD6137	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD5866	Approved
0.722	Intermediate Similarity	NPD3947	Discontinued
0.7176	Intermediate Similarity	NPD7586	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD5065	Approved
0.7171	Intermediate Similarity	NPD5513	Phase 2
0.7143	Intermediate Similarity	NPD7603	Discontinued
0.713	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD6975	Discontinued
0.7116	Intermediate Similarity	NPD4923	Phase 1
0.7108	Intermediate Similarity	NPD5497	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD3315	Phase 3
0.7105	Intermediate Similarity	NPD1575	Approved
0.7105	Intermediate Similarity	NPD1573	Approved
0.7097	Intermediate Similarity	NPD1630	Approved
0.7083	Intermediate Similarity	NPD8356	Approved
0.7079	Intermediate Similarity	NPD4848	Phase 1
0.7073	Intermediate Similarity	NPD5017	Discontinued
0.7073	Intermediate Similarity	NPD4511	Phase 1
0.7071	Intermediate Similarity	NPD4948	Discontinued
0.7056	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD2781	Approved
0.7037	Intermediate Similarity	NPD2780	Approved
0.7037	Intermediate Similarity	NPD2782	Approved
0.7031	Intermediate Similarity	NPD750	Phase 2
0.703	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD5255	Approved
0.6986	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4429	Discontinued
0.6976	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD3814	Phase 1
0.6976	Remote Similarity	NPD6999	Discontinued
0.6974	Remote Similarity	NPD3959	Phase 2
0.6974	Remote Similarity	NPD3962	Phase 2
0.6972	Remote Similarity	NPD6173	Approved
0.6965	Remote Similarity	NPD2336	Approved
0.6963	Remote Similarity	NPD3393	Approved
0.6963	Remote Similarity	NPD3389	Approved
0.6963	Remote Similarity	NPD3394	Approved
0.6955	Remote Similarity	NPD7994	Phase 2
0.6955	Remote Similarity	NPD8430	Approved
0.6952	Remote Similarity	NPD2510	Approved
0.6952	Remote Similarity	NPD2509	Approved
0.6946	Remote Similarity	NPD3017	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD9510	Approved
0.6939	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6710	Phase 3
0.693	Remote Similarity	NPD4989	Phase 2
0.6923	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD6790	Phase 1
0.6904	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.69	Remote Similarity	NPD4988	Discontinued
0.6897	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD802	Phase 2
0.6897	Remote Similarity	NPD1038	Approved
0.6895	Remote Similarity	NPD5088	Discontinued
0.6892	Remote Similarity	NPD1659	Phase 1
0.689	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6987	Phase 1
0.6888	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD1587	Approved
0.6884	Remote Similarity	NPD2412	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD4889	Approved
0.6884	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD9398	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD2916	Discontinued
0.6866	Remote Similarity	NPD4021	Phase 2
0.6864	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6389	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD926	Approved
0.6859	Remote Similarity	NPD925	Approved
0.6848	Remote Similarity	NPD4702	Approved
0.6848	Remote Similarity	NPD4703	Approved
0.6847	Remote Similarity	NPD6569	Phase 2
0.6847	Remote Similarity	NPD6665	Discontinued
0.6847	Remote Similarity	NPD5937	Approved
0.6845	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD8479	Phase 2
0.6835	Remote Similarity	NPD7180	Phase 3
0.6833	Remote Similarity	NPD3263	Phase 3
0.6832	Remote Similarity	NPD3871	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD3870	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD3321	Discontinued
0.683	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.683	Remote Similarity	NPD7031	Phase 1
0.6829	Remote Similarity	NPD2307	Discontinued
0.6822	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD3918	Approved
0.6822	Remote Similarity	NPD3917	Approved
0.6821	Remote Similarity	NPD4883	Approved
0.6821	Remote Similarity	NPD482	Approved
0.6818	Remote Similarity	NPD6752	Phase 1
0.6818	Remote Similarity	NPD6753	Phase 1
0.6818	Remote Similarity	NPD2803	Discontinued
0.6818	Remote Similarity	NPD3386	Phase 2
0.6816	Remote Similarity	NPD5022	Discontinued
0.6814	Remote Similarity	NPD7853	Phase 2
0.681	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6808	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD3931	Approved
0.6794	Remote Similarity	NPD3928	Approved
0.6792	Remote Similarity	NPD7665	Phase 2
0.6792	Remote Similarity	NPD7467	Discontinued
0.6792	Remote Similarity	NPD7666	Phase 3
0.6791	Remote Similarity	NPD3243	Approved
0.6791	Remote Similarity	NPD3945	Discontinued
0.6787	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD2092	Phase 2
0.6784	Remote Similarity	NPD2094	Phase 2
0.6784	Remote Similarity	NPD2095	Phase 2
0.6784	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.678	Remote Similarity	NPD3396	Approved
0.678	Remote Similarity	NPD3395	Approved
0.6777	Remote Similarity	NPD7001	Phase 3
0.6776	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD3915	Approved
0.6774	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD2813	Phase 3
0.6774	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD6209	Approved
0.6769	Remote Similarity	NPD4524	Discontinued
0.6768	Remote Similarity	NPD5445	Approved
0.6766	Remote Similarity	NPD4375	Approved
0.6766	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4376	Phase 3
0.6759	Remote Similarity	NPD5149	Phase 2
0.6759	Remote Similarity	NPD5148	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5293	Phase 2
0.6758	Remote Similarity	NPD5850	Phase 3
0.6757	Remote Similarity	NPD5640	Discontinued
0.6757	Remote Similarity	NPD8289	Discontinued
0.6754	Remote Similarity	NPD4314	Approved
0.6754	Remote Similarity	NPD1685	Approved
0.6754	Remote Similarity	NPD1684	Approved
0.6754	Remote Similarity	NPD4313	Approved
0.675	Remote Similarity	NPD2091	Phase 2
0.675	Remote Similarity	NPD2096	Phase 2
0.675	Remote Similarity	NPD3569	Discontinued
0.6744	Remote Similarity	NPD8093	Discontinued
0.6738	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD4558	Phase 2
0.6736	Remote Similarity	NPD425	Approved
0.6736	Remote Similarity	NPD424	Approved
0.6735	Remote Similarity	NPD1586	Approved
0.6734	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD9364	Phase 2
0.6733	Remote Similarity	NPD9363	Approved
0.6731	Remote Similarity	NPD4548	Discontinued
0.6728	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD5612	Discontinued
0.6726	Remote Similarity	NPD3259	Approved
0.6725	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.672	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD8094	Discontinued
0.6702	Remote Similarity	NPD2511	Approved
0.6699	Remote Similarity	NPD4491	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD7010	Phase 3
0.6698	Remote Similarity	NPD3570	Phase 2
0.6698	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5475	Discontinued
0.6698	Remote Similarity	NPD7470	Discontinued
0.6696	Remote Similarity	NPD2951	Discontinued
0.6685	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD3813	Approved
0.6685	Remote Similarity	NPD2896	Discontinued
0.6683	Remote Similarity	NPD5820	Clinical (unspecified phase)

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