NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	265.97
Volume:	207.442
LogP:	1.045
LogD:	0.917
LogS:	-3.131
# Rotatable Bonds:	0
TPSA:	59.39
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.665
Synthetic Accessibility Score:	3.66
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.445
MDCK Permeability:	2.8987906262045726e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.933
Plasma Protein Binding (PPB):	72.2002182006836%
Volume Distribution (VD):	1.416
Pgp-substrate:	42.751060485839844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.804
CYP1A2-substrate:	0.653
CYP2C19-inhibitor:	0.25
CYP2C19-substrate:	0.348
CYP2C9-inhibitor:	0.383
CYP2C9-substrate:	0.096
CYP2D6-inhibitor:	0.033
CYP2D6-substrate:	0.412
CYP3A4-inhibitor:	0.733
CYP3A4-substrate:	0.338

ADMET: Excretion

Clearance (CL):	0.913
Half-life (T1/2):	0.187

ADMET: Toxicity

hERG Blockers:	0.157
Human Hepatotoxicity (H-HT):	0.198
Drug-inuced Liver Injury (DILI):	0.958
AMES Toxicity:	0.686
Rat Oral Acute Toxicity:	0.642
Maximum Recommended Daily Dose:	0.409
Skin Sensitization:	0.937
Carcinogencity:	0.135
Eye Corrosion:	0.568
Eye Irritation:	0.747
Respiratory Toxicity:	0.988

Download Data

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

Natural Product: NPC74357

Natural Product ID:	NPC74357
*Common Name:**	Caulibugulone B
IUPAC Name:	6-bromo-7-(methylamino)isoquinoline-5,8-dione
Synonyms:
Standard InCHIKey:	YZQJGPPACTZUKY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H7BrN2O2/c1-12-8-7(11)9(14)5-2-3-13-4-6(5)10(8)15/h2-4,12H,1H3
SMILES:	CNC1=C(Br)C(=O)c2c(C1=O)cncc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508779
PubChem CID:	2596
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002566] Isoquinolines and derivatives [CHEMONTID:0002567] Isoquinoline quinones

*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
NPO32967	caulibugula intermis	Species	Reduviidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738389]

☑ 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
Potency	19

Activity Type	# Activity
Individual Protein	18
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1226	Individual Protein	Caspase-7	Homo sapiens	Potency	=	3162.3	nM	PMID[519497]
NPT210	Individual Protein	Thyroid stimulating hormone receptor	Homo sapiens	Potency	=	39810.7	nM	PMID[519497]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	22387.2	nM	PMID[519497]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	5623.4	nM	PMID[519497]
NPT583	Individual Protein	Inositol monophosphatase 1	Rattus norvegicus	Potency	=	10000.0	nM	PMID[519497]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	39810.7	nM	PMID[519497]
NPT282	Individual Protein	MAP kinase ERK2	Homo sapiens	Potency	=	39810.7	nM	PMID[519497]
NPT150	Individual Protein	Anthrax lethal factor	Bacillus anthracis	Potency	=	19952.6	nM	PMID[519497]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	2238.7	nM	PMID[519497]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	794.3	nM	PMID[519497]
NPT277	Individual Protein	Caspase-1	Homo sapiens	Potency	=	1584.9	nM	PMID[519497]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	1995.3	nM	PMID[519497]
NPT58	Individual Protein	Bloom syndrome protein	Homo sapiens	Potency	=	14125.4	nM	PMID[519497]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	1258.9	nM	PMID[519497]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	17782.8	nM	PMID[519497]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.22	ug.mL-1	PMID[519496]
NPT2	Others	Unspecified		Potency	=	3981.1	nM	PMID[519497]
NPT93	Individual Protein	Survival motor neuron protein	Homo sapiens	Potency	=	10000.0	nM	PMID[519497]

☑ 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 NPC74357 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	459
0.1-0.2	9378
0.2-0.3	16921
0.3-0.4	10342
0.4-0.5	2679
0.5-0.6	2067
0.6-0.7	754
0.7-0.8	87
0.8-0.85	0
0.85-0.9	4
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9448	High Similarity	NPC105811
0.9178	High Similarity	NPC467188
0.9133	High Similarity	NPC229055
0.894	High Similarity	NPC251391
0.8889	High Similarity	NPC213914
0.8882	High Similarity	NPC209362
0.8874	High Similarity	NPC70406
0.8867	High Similarity	NPC123906
0.8684	High Similarity	NPC313889
0.8086	Intermediate Similarity	NPC274981
0.7853	Intermediate Similarity	NPC470680
0.7853	Intermediate Similarity	NPC100104
0.7831	Intermediate Similarity	NPC70949
0.7818	Intermediate Similarity	NPC233380
0.7791	Intermediate Similarity	NPC474492
0.7785	Intermediate Similarity	NPC471589
0.775	Intermediate Similarity	NPC473878
0.7702	Intermediate Similarity	NPC470679
0.7702	Intermediate Similarity	NPC217021
0.7651	Intermediate Similarity	NPC265100
0.764	Intermediate Similarity	NPC471655
0.7625	Intermediate Similarity	NPC100726
0.7576	Intermediate Similarity	NPC80681
0.7554	Intermediate Similarity	NPC106757
0.75	Intermediate Similarity	NPC476419
0.75	Intermediate Similarity	NPC2414
0.7486	Intermediate Similarity	NPC103361
0.7486	Intermediate Similarity	NPC477004
0.7484	Intermediate Similarity	NPC291517
0.7473	Intermediate Similarity	NPC88115
0.7468	Intermediate Similarity	NPC330326
0.7457	Intermediate Similarity	NPC83774
0.7457	Intermediate Similarity	NPC284775
0.7443	Intermediate Similarity	NPC477003
0.743	Intermediate Similarity	NPC469489
0.7429	Intermediate Similarity	NPC191415
0.7391	Intermediate Similarity	NPC237414
0.7371	Intermediate Similarity	NPC73994
0.7371	Intermediate Similarity	NPC182940
0.7371	Intermediate Similarity	NPC79777
0.7371	Intermediate Similarity	NPC61011
0.7363	Intermediate Similarity	NPC135950
0.7348	Intermediate Similarity	NPC216550
0.7345	Intermediate Similarity	NPC110158
0.7329	Intermediate Similarity	NPC159630
0.7329	Intermediate Similarity	NPC230085
0.732	Intermediate Similarity	NPC313823
0.7294	Intermediate Similarity	NPC42372
0.7293	Intermediate Similarity	NPC476460
0.7273	Intermediate Similarity	NPC472260
0.7273	Intermediate Similarity	NPC234403
0.7257	Intermediate Similarity	NPC157583
0.7247	Intermediate Similarity	NPC46895
0.7238	Intermediate Similarity	NPC268966
0.7229	Intermediate Similarity	NPC312860
0.7213	Intermediate Similarity	NPC326422
0.7195	Intermediate Similarity	NPC112741
0.7193	Intermediate Similarity	NPC115232
0.7189	Intermediate Similarity	NPC167710
0.7178	Intermediate Similarity	NPC167400
0.7176	Intermediate Similarity	NPC242116
0.7175	Intermediate Similarity	NPC477042
0.7152	Intermediate Similarity	NPC102664
0.7143	Intermediate Similarity	NPC469529
0.7143	Intermediate Similarity	NPC293216
0.7126	Intermediate Similarity	NPC273532
0.7126	Intermediate Similarity	NPC107287
0.712	Intermediate Similarity	NPC304203
0.7118	Intermediate Similarity	NPC473706
0.7112	Intermediate Similarity	NPC284338
0.7104	Intermediate Similarity	NPC114974
0.7095	Intermediate Similarity	NPC102755
0.7088	Intermediate Similarity	NPC103119
0.7072	Intermediate Similarity	NPC118084
0.7063	Intermediate Similarity	NPC114310
0.7063	Intermediate Similarity	NPC65408
0.7062	Intermediate Similarity	NPC237188
0.7053	Intermediate Similarity	NPC317701
0.7052	Intermediate Similarity	NPC114637
0.7044	Intermediate Similarity	NPC23215
0.7029	Intermediate Similarity	NPC249614
0.7029	Intermediate Similarity	NPC262338
0.7025	Intermediate Similarity	NPC322488
0.7013	Intermediate Similarity	NPC166424
0.7013	Intermediate Similarity	NPC146373
0.7013	Intermediate Similarity	NPC245244
0.7005	Intermediate Similarity	NPC106824
0.7	Intermediate Similarity	NPC472063
0.7	Intermediate Similarity	NPC472062
0.7	Intermediate Similarity	NPC472069
0.6982	Remote Similarity	NPC263455
0.6975	Remote Similarity	NPC316811
0.6961	Remote Similarity	NPC467063
0.6957	Remote Similarity	NPC475874
0.6957	Remote Similarity	NPC472288
0.6954	Remote Similarity	NPC41717
0.6952	Remote Similarity	NPC109922
0.6948	Remote Similarity	NPC27740
0.6944	Remote Similarity	NPC470677
0.6943	Remote Similarity	NPC71236
0.6939	Remote Similarity	NPC470702
0.6939	Remote Similarity	NPC473218
0.6918	Remote Similarity	NPC27802
0.691	Remote Similarity	NPC151635
0.6904	Remote Similarity	NPC470703
0.6902	Remote Similarity	NPC255909
0.6891	Remote Similarity	NPC472064
0.6891	Remote Similarity	NPC472065
0.6879	Remote Similarity	NPC89490
0.6865	Remote Similarity	NPC324091
0.6865	Remote Similarity	NPC154339
0.6862	Remote Similarity	NPC128244
0.6853	Remote Similarity	NPC477413
0.6845	Remote Similarity	NPC225622
0.6845	Remote Similarity	NPC267343
0.6845	Remote Similarity	NPC221726
0.6845	Remote Similarity	NPC477414
0.6842	Remote Similarity	NPC474767
0.6835	Remote Similarity	NPC475090
0.6835	Remote Similarity	NPC329896
0.6835	Remote Similarity	NPC475105
0.6831	Remote Similarity	NPC133003
0.6828	Remote Similarity	NPC76540
0.6818	Remote Similarity	NPC470894
0.6811	Remote Similarity	NPC473628
0.6809	Remote Similarity	NPC93390
0.6809	Remote Similarity	NPC202812
0.6806	Remote Similarity	NPC121327
0.6804	Remote Similarity	NPC82053
0.68	Remote Similarity	NPC474383
0.6796	Remote Similarity	NPC471997
0.6792	Remote Similarity	NPC282398
0.6791	Remote Similarity	NPC47190
0.6789	Remote Similarity	NPC34837
0.6786	Remote Similarity	NPC472070
0.6784	Remote Similarity	NPC474236
0.6776	Remote Similarity	NPC91958
0.6776	Remote Similarity	NPC143603
0.6772	Remote Similarity	NPC79356
0.6772	Remote Similarity	NPC102592
0.6763	Remote Similarity	NPC113812
0.676	Remote Similarity	NPC186068
0.6757	Remote Similarity	NPC278434
0.6755	Remote Similarity	NPC473821
0.6754	Remote Similarity	NPC81535
0.6753	Remote Similarity	NPC182570
0.6753	Remote Similarity	NPC48564
0.6753	Remote Similarity	NPC265605
0.675	Remote Similarity	NPC101165
0.675	Remote Similarity	NPC471322
0.6742	Remote Similarity	NPC54214
0.674	Remote Similarity	NPC233050
0.674	Remote Similarity	NPC276540
0.6739	Remote Similarity	NPC311282
0.6738	Remote Similarity	NPC138370
0.6737	Remote Similarity	NPC78767
0.6737	Remote Similarity	NPC473814
0.6726	Remote Similarity	NPC302159
0.6705	Remote Similarity	NPC27296
0.6704	Remote Similarity	NPC252572
0.6702	Remote Similarity	NPC248782
0.6686	Remote Similarity	NPC214106
0.6686	Remote Similarity	NPC75135
0.6684	Remote Similarity	NPC292361
0.6667	Remote Similarity	NPC260041
0.6667	Remote Similarity	NPC136957
0.6667	Remote Similarity	NPC290094
0.6667	Remote Similarity	NPC46358
0.6667	Remote Similarity	NPC139763
0.6667	Remote Similarity	NPC243381
0.6667	Remote Similarity	NPC275292
0.6667	Remote Similarity	NPC19696
0.665	Remote Similarity	NPC116555
0.6649	Remote Similarity	NPC476423
0.6649	Remote Similarity	NPC74153
0.6649	Remote Similarity	NPC143977
0.6649	Remote Similarity	NPC174281
0.6649	Remote Similarity	NPC475286
0.6647	Remote Similarity	NPC190296
0.6646	Remote Similarity	NPC256893
0.6628	Remote Similarity	NPC141926
0.6615	Remote Similarity	NPC138562
0.6615	Remote Similarity	NPC477041
0.6615	Remote Similarity	NPC477044
0.6614	Remote Similarity	NPC272458
0.6605	Remote Similarity	NPC20021
0.6604	Remote Similarity	NPC471311
0.6604	Remote Similarity	NPC471313
0.6601	Remote Similarity	NPC297486
0.6601	Remote Similarity	NPC471402
0.6601	Remote Similarity	NPC240136
0.66	Remote Similarity	NPC235843
0.6599	Remote Similarity	NPC231655
0.6597	Remote Similarity	NPC179701
0.6595	Remote Similarity	NPC207851
0.6593	Remote Similarity	NPC14113
0.6593	Remote Similarity	NPC84827
0.6593	Remote Similarity	NPC145885
0.6592	Remote Similarity	NPC471943
0.659	Remote Similarity	NPC34844

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 NPC74357 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	244
0.1-0.2	785
0.2-0.3	1112
0.3-0.4	2244
0.4-0.5	2762
0.5-0.6	1617
0.6-0.7	357
0.7-0.8	28
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8077	Intermediate Similarity	NPD1270	Approved
0.7829	Intermediate Similarity	NPD272	Approved
0.7815	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2481	Approved
0.7778	Intermediate Similarity	NPD2479	Phase 3
0.758	Intermediate Similarity	NPD9599	Approved
0.75	Intermediate Similarity	NPD175	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD9100	Approved
0.7358	Intermediate Similarity	NPD107	Approved
0.7289	Intermediate Similarity	NPD2061	Approved
0.7195	Intermediate Similarity	NPD9271	Approved
0.7178	Intermediate Similarity	NPD9075	Approved
0.7178	Intermediate Similarity	NPD9074	Approved
0.7175	Intermediate Similarity	NPD1618	Phase 2
0.7159	Intermediate Similarity	NPD2753	Discontinued
0.7158	Intermediate Similarity	NPD7098	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD4988	Discontinued
0.712	Intermediate Similarity	NPD460	Discontinued
0.7117	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD1343	Approved
0.7102	Intermediate Similarity	NPD3238	Discontinued
0.7066	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD9343	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD201	Phase 2
0.7063	Intermediate Similarity	NPD200	Phase 2
0.7043	Intermediate Similarity	NPD4848	Phase 1
0.7039	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD3583	Phase 2
0.7024	Intermediate Similarity	NPD180	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD820	Phase 3
0.6978	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD2071	Approved
0.6975	Remote Similarity	NPD2068	Approved
0.6975	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD2070	Approved
0.6975	Remote Similarity	NPD2069	Approved
0.6961	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD1096	Discontinued
0.6952	Remote Similarity	NPD2290	Phase 3
0.6952	Remote Similarity	NPD2289	Phase 3
0.6949	Remote Similarity	NPD4883	Approved
0.6948	Remote Similarity	NPD9357	Approved
0.6923	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD991	Phase 2
0.6919	Remote Similarity	NPD2336	Approved
0.6918	Remote Similarity	NPD1993	Approved
0.6918	Remote Similarity	NPD1994	Approved
0.6918	Remote Similarity	NPD1995	Approved
0.6914	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD4524	Discontinued
0.6891	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD3927	Phase 2
0.6875	Remote Similarity	NPD4304	Discovery
0.6868	Remote Similarity	NPD7564	Discontinued
0.6859	Remote Similarity	NPD9583	Approved
0.6857	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6446	Discontinued
0.6848	Remote Similarity	NPD2770	Discontinued
0.6839	Remote Similarity	NPD4299	Phase 1
0.6821	Remote Similarity	NPD9396	Approved
0.6821	Remote Similarity	NPD9392	Approved
0.6815	Remote Similarity	NPD2119	Approved
0.6815	Remote Similarity	NPD2118	Approved
0.681	Remote Similarity	NPD2896	Discontinued
0.6809	Remote Similarity	NPD5853	Phase 3
0.6809	Remote Similarity	NPD5855	Phase 3
0.6806	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD5400	Approved
0.6772	Remote Similarity	NPD2307	Discontinued
0.6755	Remote Similarity	NPD1173	Approved
0.6753	Remote Similarity	NPD268	Approved
0.6753	Remote Similarity	NPD271	Approved
0.6753	Remote Similarity	NPD270	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD1183	Approved
0.6743	Remote Similarity	NPD5088	Discontinued
0.6709	Remote Similarity	NPD1598	Discontinued
0.6686	Remote Similarity	NPD6771	Discontinued
0.6667	Remote Similarity	NPD5854	Approved
0.6667	Remote Similarity	NPD5611	Phase 2
0.6667	Remote Similarity	NPD4051	Discontinued
0.6667	Remote Similarity	NPD7049	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1630	Approved
0.665	Remote Similarity	NPD2510	Approved
0.665	Remote Similarity	NPD2509	Approved
0.6649	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD9726	Discontinued
0.6633	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD9099	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD4913	Phase 3
0.6599	Remote Similarity	NPD9098	Phase 3
0.6597	Remote Similarity	NPD6226	Phase 3
0.6596	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD3569	Discontinued
0.6588	Remote Similarity	NPD4702	Approved
0.6588	Remote Similarity	NPD4703	Approved
0.6587	Remote Similarity	NPD1722	Approved
0.6584	Remote Similarity	NPD3394	Approved
0.6584	Remote Similarity	NPD3476	Approved
0.6584	Remote Similarity	NPD3475	Approved
0.6584	Remote Similarity	NPD3393	Approved
0.6584	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD3389	Approved
0.6582	Remote Similarity	NPD3947	Discontinued
0.658	Remote Similarity	NPD2405	Phase 3
0.6576	Remote Similarity	NPD3178	Discontinued
0.6575	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD2213	Approved
0.6571	Remote Similarity	NPD2214	Approved
0.657	Remote Similarity	NPD510	Phase 1
0.6566	Remote Similarity	NPD768	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD3944	Approved
0.6564	Remote Similarity	NPD4030	Approved
0.6564	Remote Similarity	NPD3942	Approved
0.6564	Remote Similarity	NPD4029	Approved
0.6564	Remote Similarity	NPD4028	Approved
0.6554	Remote Similarity	NPD1545	Discontinued
0.6554	Remote Similarity	NPD1631	Approved
0.655	Remote Similarity	NPD6152	Phase 1
0.6548	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD2008	Discontinued
0.6545	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD803	Phase 1
0.6543	Remote Similarity	NPD7175	Phase 1
0.6538	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD7287	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD2511	Approved
0.6531	Remote Similarity	NPD4912	Phase 3
0.6526	Remote Similarity	NPD4922	Phase 2
0.6519	Remote Similarity	NPD750	Phase 2
0.6513	Remote Similarity	NPD5017	Discontinued
0.651	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD5686	Approved
0.6508	Remote Similarity	NPD5685	Approved
0.6505	Remote Similarity	NPD721	Approved
0.65	Remote Similarity	NPD1573	Approved
0.65	Remote Similarity	NPD9080	Approved
0.65	Remote Similarity	NPD1575	Approved
0.6497	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD944	Approved
0.6494	Remote Similarity	NPD2809	Approved
0.6489	Remote Similarity	NPD3246	Discontinued
0.6485	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD6787	Phase 2
0.6485	Remote Similarity	NPD206	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD5888	Phase 2
0.6484	Remote Similarity	NPD482	Approved
0.6484	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD715	Phase 3
0.648	Remote Similarity	NPD4924	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD786	Approved
0.6465	Remote Similarity	NPD7010	Phase 3
0.6456	Remote Similarity	NPD1996	Discontinued
0.6452	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.645	Remote Similarity	NPD1600	Suspended
0.6448	Remote Similarity	NPD6044	Discontinued
0.644	Remote Similarity	NPD4376	Phase 3
0.6436	Remote Similarity	NPD7026	Phase 2
0.6436	Remote Similarity	NPD2411	Approved
0.6432	Remote Similarity	NPD1506	Discontinued
0.6432	Remote Similarity	NPD1643	Phase 3
0.6432	Remote Similarity	NPD5473	Discontinued
0.6413	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD9284	Approved
0.6396	Remote Similarity	NPD7187	Phase 2
0.6391	Remote Similarity	NPD5020	Approved
0.6386	Remote Similarity	NPD792	Discontinued
0.6382	Remote Similarity	NPD3967	Approved
0.638	Remote Similarity	NPD9206	Approved
0.638	Remote Similarity	NPD9207	Approved
0.6374	Remote Similarity	NPD3347	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD8242	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD7618	Phase 3
0.6373	Remote Similarity	NPD7619	Phase 3
0.6369	Remote Similarity	NPD2073	Approved
0.6369	Remote Similarity	NPD2075	Approved
0.6369	Remote Similarity	NPD2074	Approved
0.6369	Remote Similarity	NPD2072	Approved
0.6359	Remote Similarity	NPD1982	Phase 1
0.6354	Remote Similarity	NPD981	Phase 2
0.6353	Remote Similarity	NPD1427	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD3717	Discontinued
0.635	Remote Similarity	NPD3371	Approved
0.635	Remote Similarity	NPD3905	Phase 3
0.634	Remote Similarity	NPD7027	Phase 3
0.6337	Remote Similarity	NPD7469	Discontinued

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