NPASS Compound

Structure

NPC106757 OpenBabel07101718282D 27 31 0 0 1 0 0 0 0 0999 V2000 0.9839 0.1786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2618 -0.7349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1877 -1.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1278 2.5783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1290 -1.0760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4236 2.9848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9938 0.2651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9938 2.2651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4339 -0.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4248 -0.7667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8598 1.7651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8598 0.7651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1278 0.7651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6034 0.2172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4236 1.3586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5448 0.5545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7194 1.7651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7228 0.6911 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9625 1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1278 1.7651 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7259 2.2651 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -3.3076 -0.0921 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7194 2.5783 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 -5.7259 0.2651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2294 2.1482 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2618 0.2651 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 27 1 0 0 0 0 3 5 2 0 0 0 0 3 10 1 0 0 0 0 4 6 2 0 0 0 0 5 22 1 0 0 0 0 6 23 1 0 0 0 0 7 12 1 0 0 0 0 7 13 2 0 0 0 0 8 11 2 0 0 0 0 8 20 1 0 0 0 0 9 10 2 0 0 0 0 9 24 1 0 0 0 0 10 14 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 25 2 0 0 0 0 13 20 1 0 0 0 0 13 27 1 0 0 0 0 14 16 1 0 0 0 0 14 18 2 0 0 0 0 15 16 1 0 0 0 0 15 17 2 0 0 0 0 15 20 1 0 0 0 0 16 22 2 0 0 0 0 17 19 1 0 0 0 0 17 23 1 0 0 0 0 18 19 1 0 0 0 0 18 24 1 0 0 0 0 19 26 2 0 0 0 0 20 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	439.0
Volume:	373.693
LogP:	2.997
LogD:	2.823
LogS:	-4.715
# Rotatable Bonds:	1
TPSA:	64.32
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.675
Synthetic Accessibility Score:	5.309
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.962
MDCK Permeability:	2.767211481113918e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.084
20% Bioavailability (F20%):	0.897
30% Bioavailability (F30%):	0.038

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.337
Plasma Protein Binding (PPB):	93.7308120727539%
Volume Distribution (VD):	0.632
Pgp-substrate:	4.530073642730713%

ADMET: Metabolism

CYP1A2-inhibitor:	0.961
CYP1A2-substrate:	0.172
CYP2C19-inhibitor:	0.945
CYP2C19-substrate:	0.278
CYP2C9-inhibitor:	0.959
CYP2C9-substrate:	0.105
CYP2D6-inhibitor:	0.88
CYP2D6-substrate:	0.108
CYP3A4-inhibitor:	0.891
CYP3A4-substrate:	0.492

ADMET: Excretion

Clearance (CL):	0.612
Half-life (T1/2):	0.216

ADMET: Toxicity

hERG Blockers:	0.219
Human Hepatotoxicity (H-HT):	0.887
Drug-inuced Liver Injury (DILI):	0.632
AMES Toxicity:	0.879
Rat Oral Acute Toxicity:	0.91
Maximum Recommended Daily Dose:	0.934
Skin Sensitization:	0.848
Carcinogencity:	0.852
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC106757

Natural Product ID:	NPC106757
*Common Name:**	Discorhabdin T
IUPAC Name:	n.a.
Synonyms:	Discorhabdin T
Standard InCHIKey:	WNBYWMPTAIULLI-HXUWFJFHSA-N
Standard InCHI:	InChI=1S/C20H14BrN3O2S/c1-24-9-10-3-5-22-16-14(10)18(24)19(26)17-15(16)20(4-6-23-17)8-11(21)12(25)7-13(20)27-2/h3-9,23H,1-2H3/t20-/m1/s1
SMILES:	CSC1=CC(=O)C(=C[C@@]21C=CNc1c2c2nccc3c2c(c1=O)n(c3)C)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516799
PubChem CID:	21777407
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001626] Phenanthrolines

*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
NPO31291	Batzella	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[10.1021/jo00110a021]
NPO31291	Batzella	n.a.	n.a.	n.a.	n.a.	Caribbean	n.a.	PMID[14695808]
NPO31291	Batzella	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9917313]

☑ 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

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	IC50	>	5000.0	nM	PMID[572486]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	5000.0	nM	PMID[572486]
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	=	700.0	nM	PMID[572486]

☑ 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 NPC106757 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	543
0.1-0.2	4483
0.2-0.3	17855
0.3-0.4	13946
0.4-0.5	2471
0.5-0.6	2218
0.6-0.7	1056
0.7-0.8	111
0.8-0.85	10
0.85-0.9	1
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.989	High Similarity	NPC88115
0.9066	High Similarity	NPC268966
0.8525	High Similarity	NPC182940
0.8421	Intermediate Similarity	NPC477414
0.8421	Intermediate Similarity	NPC221726
0.8421	Intermediate Similarity	NPC225622
0.8404	Intermediate Similarity	NPC103119
0.8324	Intermediate Similarity	NPC79777
0.8259	Intermediate Similarity	NPC477413
0.8226	Intermediate Similarity	NPC234403
0.8211	Intermediate Similarity	NPC255909
0.8158	Intermediate Similarity	NPC477415
0.8158	Intermediate Similarity	NPC23476
0.8158	Intermediate Similarity	NPC474259
0.801	Intermediate Similarity	NPC469359
0.8	Intermediate Similarity	NPC262338
0.7926	Intermediate Similarity	NPC157583
0.7919	Intermediate Similarity	NPC167710
0.7897	Intermediate Similarity	NPC216550
0.7887	Intermediate Similarity	NPC475874
0.7821	Intermediate Similarity	NPC473878
0.7744	Intermediate Similarity	NPC473628
0.7737	Intermediate Similarity	NPC237188
0.773	Intermediate Similarity	NPC274981
0.7717	Intermediate Similarity	NPC470680
0.7717	Intermediate Similarity	NPC100104
0.7709	Intermediate Similarity	NPC100726
0.7707	Intermediate Similarity	NPC143075
0.768	Intermediate Similarity	NPC217021
0.768	Intermediate Similarity	NPC470679
0.7612	Intermediate Similarity	NPC476143
0.7568	Intermediate Similarity	NPC474492
0.7554	Intermediate Similarity	NPC74357
0.7539	Intermediate Similarity	NPC186068
0.7527	Intermediate Similarity	NPC471655
0.7525	Intermediate Similarity	NPC34837
0.7474	Intermediate Similarity	NPC477042
0.7446	Intermediate Similarity	NPC251391
0.7421	Intermediate Similarity	NPC70949
0.7404	Intermediate Similarity	NPC469577
0.7404	Intermediate Similarity	NPC475410
0.7391	Intermediate Similarity	NPC70406
0.7391	Intermediate Similarity	NPC469563
0.7385	Intermediate Similarity	NPC73994
0.738	Intermediate Similarity	NPC80681
0.7363	Intermediate Similarity	NPC47190
0.736	Intermediate Similarity	NPC467063
0.736	Intermediate Similarity	NPC477003
0.7347	Intermediate Similarity	NPC191415
0.7343	Intermediate Similarity	NPC476252
0.7337	Intermediate Similarity	NPC473946
0.7327	Intermediate Similarity	NPC326422
0.7322	Intermediate Similarity	NPC105811
0.7317	Intermediate Similarity	NPC477004
0.7317	Intermediate Similarity	NPC237414
0.7308	Intermediate Similarity	NPC467188
0.7292	Intermediate Similarity	NPC91895
0.7286	Intermediate Similarity	NPC469578
0.7283	Intermediate Similarity	NPC123906
0.7283	Intermediate Similarity	NPC102664
0.7282	Intermediate Similarity	NPC284775
0.7241	Intermediate Similarity	NPC304203
0.7233	Intermediate Similarity	NPC474767
0.7228	Intermediate Similarity	NPC476460
0.722	Intermediate Similarity	NPC473814
0.722	Intermediate Similarity	NPC78767
0.7217	Intermediate Similarity	NPC469562
0.7217	Intermediate Similarity	NPC220594
0.7206	Intermediate Similarity	NPC93390
0.7194	Intermediate Similarity	NPC83774
0.719	Intermediate Similarity	NPC472065
0.7177	Intermediate Similarity	NPC317701
0.7171	Intermediate Similarity	NPC128244
0.7151	Intermediate Similarity	NPC313889
0.715	Intermediate Similarity	NPC81535
0.715	Intermediate Similarity	NPC474258
0.7135	Intermediate Similarity	NPC115232
0.7129	Intermediate Similarity	NPC328318
0.7129	Intermediate Similarity	NPC328596
0.7128	Intermediate Similarity	NPC209362
0.7122	Intermediate Similarity	NPC294693
0.7121	Intermediate Similarity	NPC61011
0.7109	Intermediate Similarity	NPC472064
0.7098	Intermediate Similarity	NPC478183
0.7092	Intermediate Similarity	NPC469529
0.7089	Intermediate Similarity	NPC61038
0.7083	Intermediate Similarity	NPC265100
0.7067	Intermediate Similarity	NPC284338
0.7065	Intermediate Similarity	NPC133003
0.7062	Intermediate Similarity	NPC327592
0.705	Intermediate Similarity	NPC102755
0.7048	Intermediate Similarity	NPC472069
0.7048	Intermediate Similarity	NPC472063
0.7048	Intermediate Similarity	NPC472062
0.7047	Intermediate Similarity	NPC71132
0.7037	Intermediate Similarity	NPC229055
0.703	Intermediate Similarity	NPC118084
0.7028	Intermediate Similarity	NPC317373
0.7021	Intermediate Similarity	NPC472260
0.7018	Intermediate Similarity	NPC477416
0.7015	Intermediate Similarity	NPC46895
0.701	Intermediate Similarity	NPC324091
0.701	Intermediate Similarity	NPC114637
0.6995	Remote Similarity	NPC478184
0.6995	Remote Similarity	NPC478182
0.699	Remote Similarity	NPC473821
0.6971	Remote Similarity	NPC74153
0.6971	Remote Similarity	NPC106824
0.6965	Remote Similarity	NPC159125
0.6963	Remote Similarity	NPC213914
0.6959	Remote Similarity	NPC42372
0.6959	Remote Similarity	NPC207866
0.6957	Remote Similarity	NPC195239
0.6957	Remote Similarity	NPC157828
0.6954	Remote Similarity	NPC252572
0.6952	Remote Similarity	NPC252338
0.6948	Remote Similarity	NPC175602
0.6943	Remote Similarity	NPC242116
0.6938	Remote Similarity	NPC477041
0.6938	Remote Similarity	NPC477044
0.6934	Remote Similarity	NPC138562
0.6931	Remote Similarity	NPC110158
0.6927	Remote Similarity	NPC293487
0.6923	Remote Similarity	NPC56233
0.6923	Remote Similarity	NPC11445
0.6919	Remote Similarity	NPC293216
0.6912	Remote Similarity	NPC470702
0.6912	Remote Similarity	NPC473218
0.6905	Remote Similarity	NPC475914
0.6905	Remote Similarity	NPC268744
0.6905	Remote Similarity	NPC153123
0.6905	Remote Similarity	NPC220797
0.6905	Remote Similarity	NPC474318
0.6905	Remote Similarity	NPC201266
0.69	Remote Similarity	NPC11126
0.6897	Remote Similarity	NPC308931
0.6897	Remote Similarity	NPC99939
0.689	Remote Similarity	NPC227582
0.6887	Remote Similarity	NPC260900
0.6884	Remote Similarity	NPC151635
0.6881	Remote Similarity	NPC470703
0.6872	Remote Similarity	NPC269203
0.6872	Remote Similarity	NPC77241
0.6872	Remote Similarity	NPC166209
0.6872	Remote Similarity	NPC13456
0.6872	Remote Similarity	NPC121327
0.686	Remote Similarity	NPC272458
0.6852	Remote Similarity	NPC472070
0.6847	Remote Similarity	NPC228835
0.6842	Remote Similarity	NPC102592
0.6842	Remote Similarity	NPC79356
0.6835	Remote Similarity	NPC318299
0.6825	Remote Similarity	NPC74413
0.6825	Remote Similarity	NPC477045
0.6821	Remote Similarity	NPC21174
0.6821	Remote Similarity	NPC271797
0.6816	Remote Similarity	NPC248462
0.6809	Remote Similarity	NPC477418
0.6809	Remote Similarity	NPC477420
0.6808	Remote Similarity	NPC143977
0.6806	Remote Similarity	NPC281094
0.6804	Remote Similarity	NPC317752
0.6786	Remote Similarity	NPC233380
0.6783	Remote Similarity	NPC475635
0.6779	Remote Similarity	NPC472292
0.6769	Remote Similarity	NPC194881
0.6769	Remote Similarity	NPC478185
0.6768	Remote Similarity	NPC32534
0.6768	Remote Similarity	NPC471943
0.6766	Remote Similarity	NPC145885
0.6766	Remote Similarity	NPC14113
0.6766	Remote Similarity	NPC84827
0.6766	Remote Similarity	NPC248454
0.6765	Remote Similarity	NPC21429
0.6762	Remote Similarity	NPC472293
0.6762	Remote Similarity	NPC292361
0.6754	Remote Similarity	NPC216713
0.6749	Remote Similarity	NPC470677
0.6744	Remote Similarity	NPC477043
0.6739	Remote Similarity	NPC65408
0.6734	Remote Similarity	NPC6982
0.6733	Remote Similarity	NPC213468
0.6733	Remote Similarity	NPC12649
0.6729	Remote Similarity	NPC57398
0.6728	Remote Similarity	NPC116555
0.6726	Remote Similarity	NPC19170
0.6721	Remote Similarity	NPC291517
0.6719	Remote Similarity	NPC200214
0.6716	Remote Similarity	NPC470205
0.6698	Remote Similarity	NPC98715
0.6697	Remote Similarity	NPC237740
0.6684	Remote Similarity	NPC214106
0.6684	Remote Similarity	NPC471957
0.6683	Remote Similarity	NPC154339
0.6682	Remote Similarity	NPC471193
0.6682	Remote Similarity	NPC472116
0.6682	Remote Similarity	NPC179701
0.6682	Remote Similarity	NPC110182
0.6682	Remote Similarity	NPC471194
0.6682	Remote Similarity	NPC98864

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 NPC106757 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	279
0.1-0.2	628
0.2-0.3	1030
0.3-0.4	2300
0.4-0.5	2485
0.5-0.6	1866
0.6-0.7	539
0.7-0.8	23
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
0.7565	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD4988	Discontinued
0.736	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD4848	Phase 1
0.7233	Intermediate Similarity	NPD6137	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD1270	Approved
0.7212	Intermediate Similarity	NPD4924	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD5473	Discontinued
0.7194	Intermediate Similarity	NPD2753	Discontinued
0.7188	Intermediate Similarity	NPD4643	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7564	Discontinued
0.7183	Intermediate Similarity	NPD6152	Phase 1
0.7143	Intermediate Similarity	NPD3238	Discontinued
0.7143	Intermediate Similarity	NPD6044	Discontinued
0.7114	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD1343	Approved
0.7059	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4851	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD2481	Approved
0.7035	Intermediate Similarity	NPD2479	Phase 3
0.7033	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4051	Discontinued
0.6965	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6446	Discontinued
0.6923	Remote Similarity	NPD7027	Phase 3
0.6904	Remote Similarity	NPD3610	Approved
0.6904	Remote Similarity	NPD3609	Approved
0.6901	Remote Similarity	NPD4299	Phase 1
0.6881	Remote Similarity	NPD5888	Phase 2
0.6875	Remote Similarity	NPD7618	Phase 3
0.6875	Remote Similarity	NPD7619	Phase 3
0.6875	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD4524	Discontinued
0.6869	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD5400	Approved
0.6856	Remote Similarity	NPD5315	Discontinued
0.685	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7195	Clinical (unspecified phase)
0.683	Remote Similarity	NPD6173	Approved
0.683	Remote Similarity	NPD7661	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5901	Discontinued
0.6822	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6987	Phase 1
0.6806	Remote Similarity	NPD6459	Phase 2
0.6804	Remote Similarity	NPD6787	Phase 2
0.6802	Remote Similarity	NPD2641	Approved
0.6802	Remote Similarity	NPD2640	Approved
0.68	Remote Similarity	NPD4075	Phase 2
0.6786	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD750	Phase 2
0.678	Remote Similarity	NPD5809	Phase 3
0.6779	Remote Similarity	NPD4922	Phase 2
0.6777	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD4547	Phase 3
0.6763	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD2290	Phase 3
0.6762	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD2289	Phase 3
0.6761	Remote Similarity	NPD5017	Discontinued
0.6759	Remote Similarity	NPD3905	Phase 3
0.6753	Remote Similarity	NPD1630	Approved
0.675	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD3961	Discontinued
0.6748	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD460	Discontinued
0.6745	Remote Similarity	NPD2405	Phase 3
0.6742	Remote Similarity	NPD3393	Approved
0.6742	Remote Similarity	NPD3394	Approved
0.6742	Remote Similarity	NPD3389	Approved
0.6739	Remote Similarity	NPD201	Phase 2
0.6739	Remote Similarity	NPD200	Phase 2
0.6737	Remote Similarity	NPD3100	Discontinued
0.6735	Remote Similarity	NPD3583	Phase 2
0.6731	Remote Similarity	NPD2336	Approved
0.673	Remote Similarity	NPD6664	Approved
0.6726	Remote Similarity	NPD5198	Approved
0.6726	Remote Similarity	NPD5199	Approved
0.6713	Remote Similarity	NPD2008	Discontinued
0.6713	Remote Similarity	NPD6156	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD2720	Phase 1
0.6699	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD7026	Phase 2
0.6697	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD5685	Approved
0.6683	Remote Similarity	NPD5686	Approved
0.6682	Remote Similarity	NPD2411	Approved
0.6667	Remote Similarity	NPD5636	Discontinued
0.6667	Remote Similarity	NPD3947	Discontinued
0.6667	Remote Similarity	NPD2548	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD2881	Approved
0.6651	Remote Similarity	NPD2509	Approved
0.6651	Remote Similarity	NPD2879	Approved
0.6651	Remote Similarity	NPD2510	Approved
0.665	Remote Similarity	NPD4336	Clinical (unspecified phase)
0.665	Remote Similarity	NPD3079	Approved
0.665	Remote Similarity	NPD3077	Approved
0.665	Remote Similarity	NPD1631	Approved
0.665	Remote Similarity	NPD3078	Approved
0.665	Remote Similarity	NPD1545	Discontinued
0.665	Remote Similarity	NPD3076	Approved
0.6635	Remote Similarity	NPD7175	Phase 1
0.6634	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD1403	Approved
0.6633	Remote Similarity	NPD1404	Approved
0.6633	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD1996	Discontinued
0.662	Remote Similarity	NPD4304	Discovery
0.662	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.662	Remote Similarity	NPD1982	Phase 1
0.6618	Remote Similarity	NPD3927	Phase 2
0.6606	Remote Similarity	NPD7455	Approved
0.6606	Remote Similarity	NPD7454	Approved
0.6606	Remote Similarity	NPD1506	Discontinued
0.6605	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD2307	Discontinued
0.6603	Remote Similarity	NPD4499	Approved
0.66	Remote Similarity	NPD1573	Approved
0.66	Remote Similarity	NPD1575	Approved
0.6599	Remote Similarity	NPD2385	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD6771	Discontinued
0.6597	Remote Similarity	NPD1004	Phase 2
0.6597	Remote Similarity	NPD1005	Phase 2
0.659	Remote Similarity	NPD7207	Approved
0.659	Remote Similarity	NPD7208	Approved
0.659	Remote Similarity	NPD7209	Approved
0.659	Remote Similarity	NPD5426	Phase 3
0.6589	Remote Similarity	NPD7308	Discontinued
0.6589	Remote Similarity	NPD6999	Discontinued
0.6589	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD2770	Discontinued
0.6585	Remote Similarity	NPD3178	Discontinued
0.6584	Remote Similarity	NPD482	Approved
0.6583	Remote Similarity	NPD2639	Approved
0.6583	Remote Similarity	NPD2642	Approved
0.658	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD7187	Phase 2
0.6569	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD3323	Discontinued
0.6562	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD5853	Phase 3
0.6557	Remote Similarity	NPD5855	Phase 3
0.6553	Remote Similarity	NPD5106	Approved
0.6553	Remote Similarity	NPD5105	Approved
0.6552	Remote Similarity	NPD5104	Approved
0.655	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD2837	Discontinued
0.6546	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD1600	Suspended
0.6542	Remote Similarity	NPD4364	Phase 1
0.654	Remote Similarity	NPD5505	Discontinued
0.6533	Remote Similarity	NPD2915	Discontinued
0.6532	Remote Similarity	NPD6954	Phase 2
0.653	Remote Similarity	NPD4913	Phase 3
0.6528	Remote Similarity	NPD3890	Phase 2
0.6528	Remote Similarity	NPD2172	Phase 1
0.6528	Remote Similarity	NPD3891	Phase 2
0.6522	Remote Similarity	NPD2091	Phase 2
0.6522	Remote Similarity	NPD2096	Phase 2
0.652	Remote Similarity	NPD3505	Approved
0.652	Remote Similarity	NPD3506	Approved
0.6516	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD1722	Approved
0.6505	Remote Similarity	NPD206	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD3475	Approved
0.6503	Remote Similarity	NPD3476	Approved
0.65	Remote Similarity	NPD7665	Phase 2
0.65	Remote Similarity	NPD2443	Approved
0.65	Remote Similarity	NPD7666	Phase 3
0.65	Remote Similarity	NPD2442	Approved
0.6497	Remote Similarity	NPD2213	Approved
0.6497	Remote Similarity	NPD2214	Approved
0.6495	Remote Similarity	NPD5446	Phase 2
0.6493	Remote Similarity	NPD1658	Discontinued
0.6489	Remote Similarity	NPD2069	Approved
0.6489	Remote Similarity	NPD2068	Approved
0.6489	Remote Similarity	NPD2071	Approved
0.6489	Remote Similarity	NPD2070	Approved
0.6488	Remote Similarity	NPD4076	Approved
0.6488	Remote Similarity	NPD4079	Approved
0.6486	Remote Similarity	NPD5475	Discontinued
0.6484	Remote Similarity	NPD7010	Phase 3
0.6484	Remote Similarity	NPD3967	Approved
0.6477	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD2430	Phase 2
0.6476	Remote Similarity	NPD6242	Discontinued
0.6474	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD2006	Phase 2
0.6473	Remote Similarity	NPD3318	Approved
0.6473	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