NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	222.02
Volume:	203.37
LogP:	0.967
LogD:	0.701
LogS:	-2.525
# 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:	0.619
Synthetic Accessibility Score:	3.623
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:	-4.471
MDCK Permeability:	2.8080343327019364e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.888
Plasma Protein Binding (PPB):	77.03628540039062%
Volume Distribution (VD):	1.465
Pgp-substrate:	32.71015167236328%

ADMET: Metabolism

CYP1A2-inhibitor:	0.764
CYP1A2-substrate:	0.713
CYP2C19-inhibitor:	0.136
CYP2C19-substrate:	0.656
CYP2C9-inhibitor:	0.044
CYP2C9-substrate:	0.078
CYP2D6-inhibitor:	0.028
CYP2D6-substrate:	0.389
CYP3A4-inhibitor:	0.398
CYP3A4-substrate:	0.234

ADMET: Excretion

Clearance (CL):	1.687
Half-life (T1/2):	0.231

ADMET: Toxicity

hERG Blockers:	0.069
Human Hepatotoxicity (H-HT):	0.051
Drug-inuced Liver Injury (DILI):	0.962
AMES Toxicity:	0.514
Rat Oral Acute Toxicity:	0.834
Maximum Recommended Daily Dose:	0.392
Skin Sensitization:	0.877
Carcinogencity:	0.082
Eye Corrosion:	0.149
Eye Irritation:	0.838
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC229055

Natural Product ID:	NPC229055
*Common Name:**	Caulibugulone C
IUPAC Name:	6-chloro-7-(methylamino)isoquinoline-5,8-dione
Synonyms:	Caulibugulone C
Standard InCHIKey:	YIDGULDOJYFHGX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H7ClN2O2/c1-12-8-7(11)9(14)5-2-3-13-4-6(5)10(8)15/h2-4,12H,1H3
SMILES:	CNC1=C(C(=O)c2ccncc2C1=O)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL445969
PubChem CID:	2597
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	15

Activity Type	# Activity
Individual Protein	14
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	12589.3	nM	PMID[487752]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	22387.2	nM	PMID[487752]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	5623.4	nM	PMID[487752]
NPT583	Individual Protein	Inositol monophosphatase 1	Rattus norvegicus	Potency	=	11220.2	nM	PMID[487752]
NPT150	Individual Protein	Anthrax lethal factor	Bacillus anthracis	Potency	=	7943.3	nM	PMID[487752]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	2818.4	nM	PMID[487752]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	3981.1	nM	PMID[487752]
NPT277	Individual Protein	Caspase-1	Homo sapiens	Potency	=	2511.9	nM	PMID[487752]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	1584.9	nM	PMID[487752]
NPT58	Individual Protein	Bloom syndrome protein	Homo sapiens	Potency	=	17782.8	nM	PMID[487752]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	1584.9	nM	PMID[487752]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	19952.6	nM	PMID[487752]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.28	ug.mL-1	PMID[487751]
NPT2	Others	Unspecified		Potency	=	3981.1	nM	PMID[487752]
NPT93	Individual Protein	Survival motor neuron protein	Homo sapiens	Potency	=	10000.0	nM	PMID[487752]

☑ 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 NPC229055 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	434
0.1-0.2	9161
0.2-0.3	16687
0.3-0.4	10730
0.4-0.5	2740
0.5-0.6	2111
0.6-0.7	729
0.7-0.8	95
0.8-0.85	0
0.85-0.9	3
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9514	High Similarity	NPC105811
0.9241	High Similarity	NPC467188
0.9133	High Similarity	NPC74357
0.9	High Similarity	NPC251391
0.8947	High Similarity	NPC213914
0.894	High Similarity	NPC209362
0.8933	High Similarity	NPC70406
0.8926	High Similarity	NPC123906
0.8867	High Similarity	NPC313889
0.7901	Intermediate Similarity	NPC100104
0.7901	Intermediate Similarity	NPC470680
0.7879	Intermediate Similarity	NPC70949
0.7866	Intermediate Similarity	NPC233380
0.784	Intermediate Similarity	NPC474492
0.7838	Intermediate Similarity	NPC471589
0.7799	Intermediate Similarity	NPC473878
0.775	Intermediate Similarity	NPC217021
0.775	Intermediate Similarity	NPC470679
0.7736	Intermediate Similarity	NPC102664
0.7697	Intermediate Similarity	NPC265100
0.7688	Intermediate Similarity	NPC471655
0.7673	Intermediate Similarity	NPC100726
0.7622	Intermediate Similarity	NPC80681
0.7532	Intermediate Similarity	NPC291517
0.7527	Intermediate Similarity	NPC103361
0.7516	Intermediate Similarity	NPC330326
0.75	Intermediate Similarity	NPC284775
0.75	Intermediate Similarity	NPC83774
0.7486	Intermediate Similarity	NPC477003
0.7485	Intermediate Similarity	NPC274981
0.7472	Intermediate Similarity	NPC469489
0.7471	Intermediate Similarity	NPC191415
0.7414	Intermediate Similarity	NPC73994
0.7414	Intermediate Similarity	NPC61011
0.7403	Intermediate Similarity	NPC135950
0.7389	Intermediate Similarity	NPC216550
0.7375	Intermediate Similarity	NPC230085
0.7375	Intermediate Similarity	NPC159630
0.7368	Intermediate Similarity	NPC313823
0.7337	Intermediate Similarity	NPC42372
0.7333	Intermediate Similarity	NPC476460
0.7317	Intermediate Similarity	NPC472260
0.7299	Intermediate Similarity	NPC157583
0.7288	Intermediate Similarity	NPC46895
0.7273	Intermediate Similarity	NPC312860
0.7273	Intermediate Similarity	NPC470677
0.7253	Intermediate Similarity	NPC326422
0.7239	Intermediate Similarity	NPC112741
0.7235	Intermediate Similarity	NPC115232
0.7228	Intermediate Similarity	NPC167710
0.7222	Intermediate Similarity	NPC167400
0.7219	Intermediate Similarity	NPC242116
0.7216	Intermediate Similarity	NPC477042
0.7184	Intermediate Similarity	NPC293216
0.7184	Intermediate Similarity	NPC469529
0.7169	Intermediate Similarity	NPC107287
0.7168	Intermediate Similarity	NPC273532
0.7158	Intermediate Similarity	NPC304203
0.7151	Intermediate Similarity	NPC284338
0.7143	Intermediate Similarity	NPC476419
0.7143	Intermediate Similarity	NPC114974
0.7135	Intermediate Similarity	NPC102755
0.7127	Intermediate Similarity	NPC103119
0.7111	Intermediate Similarity	NPC118084
0.7107	Intermediate Similarity	NPC114310
0.7107	Intermediate Similarity	NPC65408
0.7102	Intermediate Similarity	NPC237188
0.7093	Intermediate Similarity	NPC114637
0.709	Intermediate Similarity	NPC317701
0.7089	Intermediate Similarity	NPC23215
0.707	Intermediate Similarity	NPC322488
0.7069	Intermediate Similarity	NPC262338
0.7069	Intermediate Similarity	NPC249614
0.7059	Intermediate Similarity	NPC166424
0.7059	Intermediate Similarity	NPC146373
0.7059	Intermediate Similarity	NPC245244
0.7043	Intermediate Similarity	NPC106824
0.7037	Intermediate Similarity	NPC472069
0.7037	Intermediate Similarity	NPC472063
0.7037	Intermediate Similarity	NPC472062
0.7037	Intermediate Similarity	NPC106757
0.7035	Intermediate Similarity	NPC2414
0.7024	Intermediate Similarity	NPC263455
0.7	Intermediate Similarity	NPC472288
0.7	Intermediate Similarity	NPC467063
0.6994	Remote Similarity	NPC41717
0.6993	Remote Similarity	NPC27740
0.6989	Remote Similarity	NPC109922
0.6987	Remote Similarity	NPC71236
0.6968	Remote Similarity	NPC477004
0.6966	Remote Similarity	NPC27802
0.6963	Remote Similarity	NPC88115
0.6949	Remote Similarity	NPC151635
0.694	Remote Similarity	NPC255909
0.6933	Remote Similarity	NPC476454
0.6927	Remote Similarity	NPC472064
0.6927	Remote Similarity	NPC472065
0.6923	Remote Similarity	NPC89490
0.6914	Remote Similarity	NPC315348
0.6914	Remote Similarity	NPC32002
0.6902	Remote Similarity	NPC324091
0.6902	Remote Similarity	NPC154339
0.6898	Remote Similarity	NPC128244
0.6882	Remote Similarity	NPC267343
0.6879	Remote Similarity	NPC329896
0.6879	Remote Similarity	NPC475090
0.6879	Remote Similarity	NPC475105
0.6878	Remote Similarity	NPC237414
0.6878	Remote Similarity	NPC474767
0.6875	Remote Similarity	NPC76540
0.6868	Remote Similarity	NPC133003
0.6857	Remote Similarity	NPC470894
0.6845	Remote Similarity	NPC202812
0.6845	Remote Similarity	NPC93390
0.6842	Remote Similarity	NPC121327
0.6835	Remote Similarity	NPC282398
0.6833	Remote Similarity	NPC79777
0.6833	Remote Similarity	NPC182940
0.6833	Remote Similarity	NPC471997
0.6828	Remote Similarity	NPC47190
0.6825	Remote Similarity	NPC34837
0.6821	Remote Similarity	NPC91958
0.6821	Remote Similarity	NPC143603
0.6821	Remote Similarity	NPC472070
0.6813	Remote Similarity	NPC110158
0.6809	Remote Similarity	NPC102592
0.6809	Remote Similarity	NPC79356
0.6802	Remote Similarity	NPC113812
0.6797	Remote Similarity	NPC265605
0.6797	Remote Similarity	NPC182570
0.6797	Remote Similarity	NPC48564
0.6793	Remote Similarity	NPC278434
0.6792	Remote Similarity	NPC471322
0.6792	Remote Similarity	NPC101165
0.6791	Remote Similarity	NPC473821
0.679	Remote Similarity	NPC471312
0.6789	Remote Similarity	NPC81535
0.6776	Remote Similarity	NPC311282
0.6774	Remote Similarity	NPC138370
0.6772	Remote Similarity	NPC78767
0.6772	Remote Similarity	NPC473814
0.6766	Remote Similarity	NPC302159
0.6742	Remote Similarity	NPC252572
0.674	Remote Similarity	NPC234403
0.6737	Remote Similarity	NPC248782
0.6724	Remote Similarity	NPC214106
0.672	Remote Similarity	NPC292361
0.672	Remote Similarity	NPC268966
0.671	Remote Similarity	NPC290094
0.671	Remote Similarity	NPC46358
0.6704	Remote Similarity	NPC139763
0.6687	Remote Similarity	NPC190296
0.6687	Remote Similarity	NPC256893
0.6686	Remote Similarity	NPC476464
0.6684	Remote Similarity	NPC74153
0.6684	Remote Similarity	NPC116555
0.6684	Remote Similarity	NPC143977
0.6667	Remote Similarity	NPC473706
0.6649	Remote Similarity	NPC272458
0.6649	Remote Similarity	NPC138562
0.6649	Remote Similarity	NPC477041
0.6649	Remote Similarity	NPC477044
0.6646	Remote Similarity	NPC471311
0.6646	Remote Similarity	NPC471313
0.6645	Remote Similarity	NPC240136
0.6645	Remote Similarity	NPC297486
0.6645	Remote Similarity	NPC471402
0.6644	Remote Similarity	NPC235843
0.6644	Remote Similarity	NPC231655
0.663	Remote Similarity	NPC207851
0.663	Remote Similarity	NPC14113
0.663	Remote Similarity	NPC145885
0.663	Remote Similarity	NPC84827
0.6629	Remote Similarity	NPC471943
0.6627	Remote Similarity	NPC477974
0.6613	Remote Similarity	NPC23476
0.6613	Remote Similarity	NPC474259
0.6613	Remote Similarity	NPC477415
0.6607	Remote Similarity	NPC314372
0.6597	Remote Similarity	NPC227582
0.6595	Remote Similarity	NPC282103
0.6593	Remote Similarity	NPC126709
0.6593	Remote Similarity	NPC55772
0.6593	Remote Similarity	NPC248041
0.6593	Remote Similarity	NPC11126
0.6591	Remote Similarity	NPC478184
0.659	Remote Similarity	NPC169586
0.6587	Remote Similarity	NPC136002
0.6585	Remote Similarity	NPC84911
0.6584	Remote Similarity	NPC324611
0.6582	Remote Similarity	NPC169625
0.6582	Remote Similarity	NPC202957
0.6579	Remote Similarity	NPC195239
0.6579	Remote Similarity	NPC157828
0.6578	Remote Similarity	NPC209917
0.6575	Remote Similarity	NPC267885
0.657	Remote Similarity	NPC281094
0.6561	Remote Similarity	NPC476322
0.6559	Remote Similarity	NPC469359
0.6546	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 NPC229055 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	232
0.1-0.2	765
0.2-0.3	1085
0.3-0.4	2085
0.4-0.5	2778
0.5-0.6	1747
0.6-0.7	419
0.7-0.8	38
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
0.8129	Intermediate Similarity	NPD1270	Approved
0.7881	Intermediate Similarity	NPD272	Approved
0.7867	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD2481	Approved
0.7824	Intermediate Similarity	NPD2479	Phase 3
0.764	Intermediate Similarity	NPD9343	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD9599	Approved
0.7572	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD4848	Phase 1
0.7547	Intermediate Similarity	NPD175	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD9100	Approved
0.7514	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD4304	Discovery
0.7427	Intermediate Similarity	NPD4524	Discontinued
0.7414	Intermediate Similarity	NPD3927	Phase 2
0.7405	Intermediate Similarity	NPD107	Approved
0.736	Intermediate Similarity	NPD2770	Discontinued
0.7333	Intermediate Similarity	NPD2061	Approved
0.7239	Intermediate Similarity	NPD9271	Approved
0.7234	Intermediate Similarity	NPD4299	Phase 1
0.7222	Intermediate Similarity	NPD9075	Approved
0.7222	Intermediate Similarity	NPD9074	Approved
0.7216	Intermediate Similarity	NPD1618	Phase 2
0.72	Intermediate Similarity	NPD2753	Discontinued
0.7192	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD4988	Discontinued
0.716	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD460	Discontinued
0.7151	Intermediate Similarity	NPD1343	Approved
0.7143	Intermediate Similarity	NPD3238	Discontinued
0.7125	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD201	Phase 2
0.7107	Intermediate Similarity	NPD200	Phase 2
0.7088	Intermediate Similarity	NPD1905	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD3583	Phase 2
0.7068	Intermediate Similarity	NPD4913	Phase 3
0.7066	Intermediate Similarity	NPD180	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD820	Phase 3
0.7019	Intermediate Similarity	NPD569	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1096	Discontinued
0.7	Intermediate Similarity	NPD4912	Phase 3
0.6993	Remote Similarity	NPD9357	Approved
0.6989	Remote Similarity	NPD4883	Approved
0.6989	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD991	Phase 2
0.6963	Remote Similarity	NPD944	Approved
0.6963	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2336	Approved
0.6954	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6787	Phase 2
0.6936	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD2074	Approved
0.6914	Remote Similarity	NPD2072	Approved
0.6914	Remote Similarity	NPD2073	Approved
0.6914	Remote Similarity	NPD2075	Approved
0.6906	Remote Similarity	NPD7564	Discontinued
0.6903	Remote Similarity	NPD9583	Approved
0.6897	Remote Similarity	NPD6446	Discontinued
0.6897	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD9392	Approved
0.6867	Remote Similarity	NPD9396	Approved
0.6859	Remote Similarity	NPD2119	Approved
0.6859	Remote Similarity	NPD2118	Approved
0.6852	Remote Similarity	NPD2896	Discontinued
0.6852	Remote Similarity	NPD1380	Discovery
0.6845	Remote Similarity	NPD5853	Phase 3
0.6845	Remote Similarity	NPD5855	Phase 3
0.6842	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD5400	Approved
0.6809	Remote Similarity	NPD2307	Discontinued
0.6798	Remote Similarity	NPD1586	Approved
0.6797	Remote Similarity	NPD270	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD271	Approved
0.6797	Remote Similarity	NPD268	Approved
0.6791	Remote Similarity	NPD1173	Approved
0.6782	Remote Similarity	NPD5088	Discontinued
0.6765	Remote Similarity	NPD3339	Approved
0.676	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.676	Remote Similarity	NPD6471	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD1598	Discontinued
0.6727	Remote Similarity	NPD1383	Phase 3
0.6727	Remote Similarity	NPD1382	Phase 2
0.6725	Remote Similarity	NPD2165	Phase 1
0.6724	Remote Similarity	NPD4384	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6771	Discontinued
0.6705	Remote Similarity	NPD1630	Approved
0.6705	Remote Similarity	NPD5611	Phase 2
0.6705	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD5854	Approved
0.6702	Remote Similarity	NPD7049	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4051	Discontinued
0.6687	Remote Similarity	NPD9726	Discontinued
0.6686	Remote Similarity	NPD3113	Approved
0.6686	Remote Similarity	NPD3112	Approved
0.6686	Remote Similarity	NPD3114	Approved
0.6686	Remote Similarity	NPD3115	Approved
0.6685	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD1587	Approved
0.6685	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD2509	Approved
0.6684	Remote Similarity	NPD2510	Approved
0.6684	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD2865	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD9098	Phase 3
0.6644	Remote Similarity	NPD9099	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6226	Phase 3
0.663	Remote Similarity	NPD3569	Discontinued
0.6627	Remote Similarity	NPD1722	Approved
0.6627	Remote Similarity	NPD4702	Approved
0.6627	Remote Similarity	NPD4703	Approved
0.6625	Remote Similarity	NPD3475	Approved
0.6625	Remote Similarity	NPD3476	Approved
0.6617	Remote Similarity	NPD3394	Approved
0.6617	Remote Similarity	NPD3389	Approved
0.6617	Remote Similarity	NPD3393	Approved
0.6617	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD2405	Phase 3
0.6615	Remote Similarity	NPD3947	Discontinued
0.6612	Remote Similarity	NPD3178	Discontinued
0.6611	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.661	Remote Similarity	NPD3929	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD2214	Approved
0.6609	Remote Similarity	NPD2213	Approved
0.6608	Remote Similarity	NPD510	Phase 1
0.6606	Remote Similarity	NPD945	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD3944	Approved
0.6605	Remote Similarity	NPD3942	Approved
0.6605	Remote Similarity	NPD4030	Approved
0.6605	Remote Similarity	NPD4029	Approved
0.6605	Remote Similarity	NPD4028	Approved
0.6592	Remote Similarity	NPD3116	Approved
0.6592	Remote Similarity	NPD3117	Approved
0.6591	Remote Similarity	NPD1631	Approved
0.6591	Remote Similarity	NPD1545	Discontinued
0.6587	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD803	Phase 1
0.6583	Remote Similarity	NPD6152	Phase 1
0.6582	Remote Similarity	NPD2008	Discontinued
0.6579	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD7175	Phase 1
0.6575	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD2511	Approved
0.6561	Remote Similarity	NPD4922	Phase 2
0.6556	Remote Similarity	NPD750	Phase 2
0.655	Remote Similarity	NPD6954	Phase 2
0.6546	Remote Similarity	NPD5017	Discontinued
0.6543	Remote Similarity	NPD5685	Approved
0.6543	Remote Similarity	NPD5686	Approved
0.6541	Remote Similarity	NPD721	Approved
0.6541	Remote Similarity	NPD9080	Approved
0.6536	Remote Similarity	NPD4973	Approved
0.6536	Remote Similarity	NPD1573	Approved
0.6536	Remote Similarity	NPD1575	Approved
0.6532	Remote Similarity	NPD2809	Approved
0.6531	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD206	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD3246	Discontinued
0.6522	Remote Similarity	NPD715	Phase 3
0.6519	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD482	Approved
0.6517	Remote Similarity	NPD5888	Phase 2
0.6517	Remote Similarity	NPD2823	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD4924	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD5415	Approved
0.6506	Remote Similarity	NPD786	Approved
0.6497	Remote Similarity	NPD7010	Phase 3
0.6486	Remote Similarity	NPD5213	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD5092	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6194	Discontinued
0.6484	Remote Similarity	NPD6044	Discontinued
0.6482	Remote Similarity	NPD1600	Suspended
0.6482	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD4376	Phase 3
0.6471	Remote Similarity	NPD7026	Phase 2
0.6468	Remote Similarity	NPD2411	Approved
0.6467	Remote Similarity	NPD5473	Discontinued
0.6467	Remote Similarity	NPD1643	Phase 3
0.6465	Remote Similarity	NPD1506	Discontinued
0.6459	Remote Similarity	NPD4845	Discontinued
0.6458	Remote Similarity	NPD2290	Phase 3
0.6458	Remote Similarity	NPD2289	Phase 3
0.6448	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD2831	Approved
0.6438	Remote Similarity	NPD9284	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