NPASS Compound

Structure

NPC475874 OpenBabel07101719142D 25 29 0 0 1 0 0 0 0 0999 V2000 -0.4683 -3.9916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4084 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4097 -3.6543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7042 0.4066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4084 -1.8131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2744 -0.3131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2855 -3.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2946 -3.3450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2744 -2.3131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1404 -0.8131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1160 -2.3611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7042 -1.2197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8254 -2.0237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9966 -1.8872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.8131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1404 -1.8131 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.7569 -1.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4084 -0.8131 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.2744 -3.3131 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -4.0065 -0.3131 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -1.5882 -2.6703 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 1.7194 -2.5783 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.0065 -2.3131 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4900 -0.4300 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 1 8 1 0 0 0 0 2 4 2 0 0 0 0 2 18 1 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 9 2 0 0 0 0 5 18 1 0 0 0 0 6 10 2 0 0 0 0 6 18 1 0 0 0 0 7 8 2 0 0 0 0 7 23 1 0 0 0 0 8 11 1 0 0 0 0 9 16 1 0 0 0 0 9 19 1 0 0 0 0 10 16 1 0 0 0 0 10 20 1 0 0 0 0 11 13 1 0 0 0 0 11 14 2 0 0 0 0 12 13 1 0 0 0 0 12 15 2 0 0 0 0 12 18 1 0 0 0 0 13 21 2 0 0 0 0 14 17 1 0 0 0 0 14 23 1 0 0 0 0 15 17 1 0 0 0 0 15 22 1 0 0 0 0 16 24 1 0 0 0 0 17 25 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.94
Volume:	345.148
LogP:	4.016
LogD:	3.162
LogS:	-3.642
# Rotatable Bonds:	0
TPSA:	80.97
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.542
Synthetic Accessibility Score:	5.019
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.002
MDCK Permeability:	1.4741814993612934e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.618
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.488
Plasma Protein Binding (PPB):	95.73932647705078%
Volume Distribution (VD):	1.285
Pgp-substrate:	1.7265276908874512%

ADMET: Metabolism

CYP1A2-inhibitor:	0.371
CYP1A2-substrate:	0.426
CYP2C19-inhibitor:	0.534
CYP2C19-substrate:	0.182
CYP2C9-inhibitor:	0.643
CYP2C9-substrate:	0.937
CYP2D6-inhibitor:	0.917
CYP2D6-substrate:	0.873
CYP3A4-inhibitor:	0.378
CYP3A4-substrate:	0.242

ADMET: Excretion

Clearance (CL):	1.456
Half-life (T1/2):	0.699

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.235
Drug-inuced Liver Injury (DILI):	0.947
AMES Toxicity:	0.457
Rat Oral Acute Toxicity:	0.994
Maximum Recommended Daily Dose:	0.195
Skin Sensitization:	0.537
Carcinogencity:	0.94
Eye Corrosion:	0.003
Eye Irritation:	0.076
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC475874

Natural Product ID:	NPC475874
*Common Name:**	RZRKLCBSFPOTIQ-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RZRKLCBSFPOTIQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H13Br2N3O2/c19-9-5-18(6-10(20)16(9)24)2-4-22-15-12(18)13-11-8(1-3-21-13)7-23-14(11)17(15)25/h2,4-7,16,22-24H,1,3H2
SMILES:	BrC1=CC2(C=CNC3=C2C2=NCCc4c2c(C3=O)[nH]c4)C=C(C1O)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517755
PubChem CID:	11248264
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
NPO32524	latrunculid sponges	Species	n.a.	n.a.	n.a.	South African	n.a.	PMID[15332840]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	197.0	nM	PMID[543918]

☑ 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 NPC475874 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	300
0.1-0.2	2482
0.2-0.3	14606
0.3-0.4	18487
0.4-0.5	3343
0.5-0.6	2386
0.6-0.7	995
0.7-0.8	76
0.8-0.85	13
0.85-0.9	3
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9822	High Similarity	NPC473628
0.9306	High Similarity	NPC473946
0.9181	High Similarity	NPC234403
0.9181	High Similarity	NPC79777
0.908	High Similarity	NPC474258
0.8941	High Similarity	NPC262338
0.8851	High Similarity	NPC182940
0.8824	High Similarity	NPC143075
0.8564	High Similarity	NPC268966
0.8525	High Similarity	NPC477414
0.8525	High Similarity	NPC221726
0.8525	High Similarity	NPC225622
0.8409	Intermediate Similarity	NPC186068
0.8352	Intermediate Similarity	NPC23476
0.8352	Intermediate Similarity	NPC477415
0.8352	Intermediate Similarity	NPC474259
0.8118	Intermediate Similarity	NPC471655
0.8114	Intermediate Similarity	NPC274981
0.8071	Intermediate Similarity	NPC477413
0.8046	Intermediate Similarity	NPC474492
0.8	Intermediate Similarity	NPC470680
0.8	Intermediate Similarity	NPC100104
0.7887	Intermediate Similarity	NPC106757
0.7806	Intermediate Similarity	NPC88115
0.7806	Intermediate Similarity	NPC469563
0.7688	Intermediate Similarity	NPC100726
0.7656	Intermediate Similarity	NPC473821
0.7634	Intermediate Similarity	NPC477042
0.7629	Intermediate Similarity	NPC74153
0.7619	Intermediate Similarity	NPC469359
0.7612	Intermediate Similarity	NPC469562
0.7612	Intermediate Similarity	NPC220594
0.76	Intermediate Similarity	NPC473878
0.759	Intermediate Similarity	NPC477044
0.759	Intermediate Similarity	NPC477041
0.7557	Intermediate Similarity	NPC217021
0.7557	Intermediate Similarity	NPC470679
0.75	Intermediate Similarity	NPC175602
0.7462	Intermediate Similarity	NPC477045
0.7443	Intermediate Similarity	NPC102664
0.7426	Intermediate Similarity	NPC469578
0.7411	Intermediate Similarity	NPC476143
0.7389	Intermediate Similarity	NPC61038
0.7363	Intermediate Similarity	NPC477043
0.736	Intermediate Similarity	NPC78767
0.736	Intermediate Similarity	NPC473814
0.736	Intermediate Similarity	NPC167710
0.7347	Intermediate Similarity	NPC93390
0.7333	Intermediate Similarity	NPC47190
0.7268	Intermediate Similarity	NPC209917
0.7246	Intermediate Similarity	NPC207866
0.7222	Intermediate Similarity	NPC292361
0.7219	Intermediate Similarity	NPC302647
0.7206	Intermediate Similarity	NPC469577
0.7206	Intermediate Similarity	NPC475410
0.7182	Intermediate Similarity	NPC209362
0.7158	Intermediate Similarity	NPC157583
0.7158	Intermediate Similarity	NPC284775
0.715	Intermediate Similarity	NPC477003
0.7143	Intermediate Similarity	NPC98715
0.7143	Intermediate Similarity	NPC476252
0.7143	Intermediate Similarity	NPC477416
0.7129	Intermediate Similarity	NPC300183
0.7114	Intermediate Similarity	NPC477004
0.7097	Intermediate Similarity	NPC71132
0.7056	Intermediate Similarity	NPC123906
0.7039	Intermediate Similarity	NPC46225
0.7039	Intermediate Similarity	NPC225821
0.7037	Intermediate Similarity	NPC6982
0.7033	Intermediate Similarity	NPC469544
0.7033	Intermediate Similarity	NPC110182
0.7033	Intermediate Similarity	NPC251391
0.7011	Intermediate Similarity	NPC213914
0.701	Intermediate Similarity	NPC328596
0.701	Intermediate Similarity	NPC328318
0.7005	Intermediate Similarity	NPC127677
0.7005	Intermediate Similarity	NPC258062
0.7	Intermediate Similarity	NPC202812
0.6985	Remote Similarity	NPC216550
0.6959	Remote Similarity	NPC191415
0.6957	Remote Similarity	NPC74357
0.695	Remote Similarity	NPC304203
0.6946	Remote Similarity	NPC237414
0.6935	Remote Similarity	NPC476460
0.6923	Remote Similarity	NPC102755
0.6916	Remote Similarity	NPC269270
0.6915	Remote Similarity	NPC233380
0.6915	Remote Similarity	NPC42372
0.689	Remote Similarity	NPC271862
0.6889	Remote Similarity	NPC467188
0.6888	Remote Similarity	NPC110158
0.6885	Remote Similarity	NPC70406
0.6884	Remote Similarity	NPC154339
0.6884	Remote Similarity	NPC14686
0.6872	Remote Similarity	NPC87856
0.6872	Remote Similarity	NPC151976
0.6866	Remote Similarity	NPC267343
0.6866	Remote Similarity	NPC326422
0.686	Remote Similarity	NPC327592
0.6859	Remote Similarity	NPC470498
0.6857	Remote Similarity	NPC291517
0.6856	Remote Similarity	NPC215795
0.6856	Remote Similarity	NPC11126
0.6856	Remote Similarity	NPC176199
0.6842	Remote Similarity	NPC70949
0.684	Remote Similarity	NPC267965
0.6834	Remote Similarity	NPC103119
0.6834	Remote Similarity	NPC255909
0.6832	Remote Similarity	NPC195239
0.6832	Remote Similarity	NPC157828
0.6829	Remote Similarity	NPC252338
0.6827	Remote Similarity	NPC317373
0.6825	Remote Similarity	NPC115232
0.6822	Remote Similarity	NPC472285
0.6821	Remote Similarity	NPC73994
0.6816	Remote Similarity	NPC475635
0.6813	Remote Similarity	NPC105811
0.6804	Remote Similarity	NPC237188
0.6802	Remote Similarity	NPC228835
0.68	Remote Similarity	NPC83111
0.6798	Remote Similarity	NPC11445
0.6796	Remote Similarity	NPC159856
0.6792	Remote Similarity	NPC471194
0.6792	Remote Similarity	NPC471193
0.6791	Remote Similarity	NPC80681
0.6788	Remote Similarity	NPC293216
0.678	Remote Similarity	NPC474767
0.6776	Remote Similarity	NPC471192
0.6776	Remote Similarity	NPC132211
0.6769	Remote Similarity	NPC213468
0.6768	Remote Similarity	NPC311282
0.6765	Remote Similarity	NPC227582
0.6761	Remote Similarity	NPC23215
0.6749	Remote Similarity	NPC294693
0.6748	Remote Similarity	NPC269203
0.6748	Remote Similarity	NPC13456
0.6748	Remote Similarity	NPC166209
0.6748	Remote Similarity	NPC77241
0.6739	Remote Similarity	NPC24678
0.6739	Remote Similarity	NPC313889
0.6739	Remote Similarity	NPC105818
0.6731	Remote Similarity	NPC317701
0.672	Remote Similarity	NPC75135
0.6718	Remote Similarity	NPC68354
0.6718	Remote Similarity	NPC151939
0.6718	Remote Similarity	NPC83774
0.6717	Remote Similarity	NPC207851
0.6701	Remote Similarity	NPC275305
0.6701	Remote Similarity	NPC37423
0.6701	Remote Similarity	NPC149155
0.6701	Remote Similarity	NPC203468
0.6701	Remote Similarity	NPC110500
0.67	Remote Similarity	NPC17059
0.67	Remote Similarity	NPC278434
0.6699	Remote Similarity	NPC220797
0.6699	Remote Similarity	NPC474318
0.6699	Remote Similarity	NPC201266
0.6699	Remote Similarity	NPC268744
0.6699	Remote Similarity	NPC475914
0.6699	Remote Similarity	NPC153123
0.6698	Remote Similarity	NPC203614
0.6698	Remote Similarity	NPC204491
0.6684	Remote Similarity	NPC248041
0.6684	Remote Similarity	NPC55772
0.6684	Remote Similarity	NPC283219
0.6684	Remote Similarity	NPC126709
0.6683	Remote Similarity	NPC260900
0.6683	Remote Similarity	NPC308931
0.6683	Remote Similarity	NPC99939
0.6683	Remote Similarity	NPC295158
0.6682	Remote Similarity	NPC470703
0.6667	Remote Similarity	NPC72956
0.6667	Remote Similarity	NPC82370
0.6667	Remote Similarity	NPC267885
0.6667	Remote Similarity	NPC78020
0.6667	Remote Similarity	NPC473706
0.665	Remote Similarity	NPC34837
0.665	Remote Similarity	NPC131887
0.665	Remote Similarity	NPC472292
0.665	Remote Similarity	NPC315555
0.665	Remote Similarity	NPC61011
0.6649	Remote Similarity	NPC469762
0.6636	Remote Similarity	NPC473218
0.6636	Remote Similarity	NPC153980
0.6636	Remote Similarity	NPC318299
0.6636	Remote Similarity	NPC470702
0.6636	Remote Similarity	NPC6865
0.6636	Remote Similarity	NPC207020
0.6635	Remote Similarity	NPC471944
0.6634	Remote Similarity	NPC77061
0.6634	Remote Similarity	NPC179701
0.6631	Remote Similarity	NPC470507
0.663	Remote Similarity	NPC58268
0.663	Remote Similarity	NPC101130
0.663	Remote Similarity	NPC114033
0.663	Remote Similarity	NPC129412
0.6623	Remote Similarity	NPC477420
0.6623	Remote Similarity	NPC477418
0.6621	Remote Similarity	NPC2395
0.6618	Remote Similarity	NPC474177

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 NPC475874 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	613
0.2-0.3	925
0.3-0.4	2378
0.4-0.5	2936
0.5-0.6	1812
0.6-0.7	306
0.7-0.8	2
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
0.7135	Intermediate Similarity	NPD3178	Discontinued
0.7062	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5901	Discontinued
0.6869	Remote Similarity	NPD3961	Discontinued
0.6821	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5473	Discontinued
0.6728	Remote Similarity	NPD1996	Discontinued
0.6718	Remote Similarity	NPD2753	Discontinued
0.6718	Remote Similarity	NPD3506	Approved
0.6718	Remote Similarity	NPD3505	Approved
0.6716	Remote Similarity	NPD4848	Phase 1
0.6702	Remote Similarity	NPD2213	Approved
0.6702	Remote Similarity	NPD2214	Approved
0.6701	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD482	Approved
0.67	Remote Similarity	NPD4988	Discontinued
0.6698	Remote Similarity	NPD3389	Approved
0.6698	Remote Similarity	NPD3393	Approved
0.6698	Remote Similarity	NPD3394	Approved
0.6684	Remote Similarity	NPD4076	Approved
0.6684	Remote Similarity	NPD4079	Approved
0.6667	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3238	Discontinued
0.6667	Remote Similarity	NPD7618	Phase 3
0.6667	Remote Similarity	NPD7619	Phase 3
0.665	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.665	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD2095	Phase 2
0.6583	Remote Similarity	NPD2092	Phase 2
0.6583	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD2094	Phase 2
0.6582	Remote Similarity	NPD4075	Phase 2
0.6569	Remote Similarity	NPD4922	Phase 2
0.655	Remote Similarity	NPD2091	Phase 2
0.655	Remote Similarity	NPD2096	Phase 2
0.6542	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD1270	Approved
0.6537	Remote Similarity	NPD460	Discontinued
0.6533	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD2510	Approved
0.6526	Remote Similarity	NPD6376	Discontinued
0.6526	Remote Similarity	NPD2509	Approved
0.6524	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6664	Approved
0.6507	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD3100	Discontinued
0.65	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6482	Remote Similarity	NPD1643	Phase 3
0.6482	Remote Similarity	NPD2481	Approved
0.6482	Remote Similarity	NPD2479	Phase 3
0.6477	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD1096	Discontinued
0.6468	Remote Similarity	NPD7564	Discontinued
0.6465	Remote Similarity	NPD4051	Discontinued
0.6447	Remote Similarity	NPD4883	Approved
0.6447	Remote Similarity	NPD5065	Approved
0.6443	Remote Similarity	NPD6446	Discontinued
0.6435	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD1600	Suspended
0.6417	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.641	Remote Similarity	NPD1343	Approved
0.6408	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD750	Phase 2
0.6394	Remote Similarity	NPD2289	Phase 3
0.6394	Remote Similarity	NPD2290	Phase 3
0.6385	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD3947	Discontinued
0.6383	Remote Similarity	NPD2172	Phase 1
0.6381	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5400	Approved
0.6372	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD4924	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4128	Approved
0.6359	Remote Similarity	NPD2336	Approved
0.6354	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD6242	Discontinued
0.6351	Remote Similarity	NPD484	Approved
0.6347	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD7234	Approved
0.6341	Remote Similarity	NPD7233	Approved
0.634	Remote Similarity	NPD1631	Approved
0.634	Remote Similarity	NPD5088	Discontinued
0.633	Remote Similarity	NPD3918	Approved
0.633	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.633	Remote Similarity	NPD3917	Approved
0.6327	Remote Similarity	NPD4640	Approved
0.6327	Remote Similarity	NPD4638	Approved
0.6327	Remote Similarity	NPD4639	Approved
0.6313	Remote Similarity	NPD4524	Discontinued
0.6313	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4499	Approved
0.6308	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD6987	Phase 1
0.63	Remote Similarity	NPD2144	Approved
0.6296	Remote Similarity	NPD4463	Approved
0.6296	Remote Similarity	NPD4462	Approved
0.6294	Remote Similarity	NPD1575	Approved
0.6294	Remote Similarity	NPD1573	Approved
0.6291	Remote Similarity	NPD7187	Phase 2
0.629	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD3915	Approved
0.6281	Remote Similarity	NPD2928	Phase 2
0.6279	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD7010	Phase 3
0.6276	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.627	Remote Similarity	NPD1722	Approved
0.6269	Remote Similarity	NPD1630	Approved
0.6256	Remote Similarity	NPD7455	Approved
0.6256	Remote Similarity	NPD3583	Phase 2
0.6256	Remote Similarity	NPD8093	Discontinued
0.6256	Remote Similarity	NPD7454	Approved
0.6256	Remote Similarity	NPD4845	Discontinued
0.625	Remote Similarity	NPD786	Approved
0.6244	Remote Similarity	NPD5809	Phase 3
0.6244	Remote Similarity	NPD7026	Phase 2
0.6238	Remote Similarity	NPD2307	Discontinued
0.6233	Remote Similarity	NPD5426	Phase 3
0.6232	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.623	Remote Similarity	NPD200	Phase 2
0.623	Remote Similarity	NPD201	Phase 2
0.623	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6227	Remote Similarity	NPD3795	Approved
0.6227	Remote Similarity	NPD3794	Approved
0.6227	Remote Similarity	NPD5888	Phase 2
0.6227	Remote Similarity	NPD8094	Discontinued
0.6219	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.621	Remote Similarity	NPD7470	Discontinued
0.6207	Remote Similarity	NPD3038	Discontinued
0.6204	Remote Similarity	NPD7957	Phase 1
0.6204	Remote Similarity	NPD7001	Phase 3
0.6204	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD2008	Discontinued
0.6202	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7944	Discontinued
0.6186	Remote Similarity	NPD6176	Phase 1
0.6184	Remote Similarity	NPD6068	Discontinued
0.6183	Remote Similarity	NPD5020	Approved
0.6182	Remote Similarity	NPD2411	Approved
0.6176	Remote Similarity	NPD3319	Phase 1
0.6176	Remote Similarity	NPD3318	Approved
0.6176	Remote Similarity	NPD3320	Approved
0.6175	Remote Similarity	NPD1506	Discontinued
0.6173	Remote Similarity	NPD3323	Discontinued
0.6168	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5017	Discontinued
0.6166	Remote Similarity	NPD6026	Approved
0.6162	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD6595	Phase 3
0.6157	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.6157	Remote Similarity	NPD4299	Phase 1
0.6154	Remote Similarity	NPD2511	Approved
0.615	Remote Similarity	NPD6248	Phase 2
0.615	Remote Similarity	NPD6999	Discontinued
0.615	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.615	Remote Similarity	NPD6249	Phase 2
0.6146	Remote Similarity	NPD2837	Discontinued
0.6143	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD2720	Phase 1
0.614	Remote Similarity	NPD8289	Discontinued
0.614	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD4181	Approved
0.6138	Remote Similarity	NPD7469	Discontinued
0.6136	Remote Similarity	NPD6152	Phase 1
0.6136	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6135	Remote Similarity	NPD2770	Discontinued
0.6135	Remote Similarity	NPD4948	Discontinued
0.6135	Remote Similarity	NPD3246	Discontinued
0.6131	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6123	Remote Similarity	NPD6753	Phase 1
0.6123	Remote Similarity	NPD6752	Phase 1
0.6122	Remote Similarity	NPD6771	Discontinued
0.6121	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD4601	Approved
0.6121	Remote Similarity	NPD6479	Discontinued
0.6121	Remote Similarity	NPD4600	Approved
0.6117	Remote Similarity	NPD6017	Discontinued
0.6117	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD6164	Phase 2
0.6114	Remote Similarity	NPD2809	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