NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	188.06
Volume:	188.159
LogP:	0.477
LogD:	0.46
LogS:	-1.743
# Rotatable Bonds:	0
TPSA:	59.39
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.608
Synthetic Accessibility Score:	2.969
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.462
MDCK Permeability:	2.6928491934086196e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.916
Plasma Protein Binding (PPB):	57.779109954833984%
Volume Distribution (VD):	1.512
Pgp-substrate:	64.30013275146484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.847
CYP1A2-substrate:	0.609
CYP2C19-inhibitor:	0.2
CYP2C19-substrate:	0.169
CYP2C9-inhibitor:	0.086
CYP2C9-substrate:	0.109
CYP2D6-inhibitor:	0.089
CYP2D6-substrate:	0.41
CYP3A4-inhibitor:	0.353
CYP3A4-substrate:	0.216

ADMET: Excretion

Clearance (CL):	4.323
Half-life (T1/2):	0.291

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.153
Drug-inuced Liver Injury (DILI):	0.958
AMES Toxicity:	0.655
Rat Oral Acute Toxicity:	0.753
Maximum Recommended Daily Dose:	0.122
Skin Sensitization:	0.871
Carcinogencity:	0.118
Eye Corrosion:	0.017
Eye Irritation:	0.869
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC105811

Natural Product ID:	NPC105811
*Common Name:**	Caulibugulone A
IUPAC Name:	7-(methylamino)isoquinoline-5,8-dione
Synonyms:
Standard InCHIKey:	PETJKYHAQBWMDY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H8N2O2/c1-11-8-4-9(13)6-2-3-12-5-7(6)10(8)14/h2-5,11H,1H3
SMILES:	CNC1=CC(=O)c2ccncc2C1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL480286
PubChem CID:	2595
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

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.34	ug.mL-1	PMID[531314]

☑ 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 NPC105811 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	392
0.1-0.2	7992
0.2-0.3	15572
0.3-0.4	12611
0.4-0.5	2949
0.5-0.6	2048
0.6-0.7	953
0.7-0.8	162
0.8-0.85	8
0.85-0.9	0
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9712	High Similarity	NPC467188
0.9514	High Similarity	NPC229055
0.9448	High Similarity	NPC74357
0.9444	High Similarity	NPC251391
0.9384	High Similarity	NPC213914
0.9379	High Similarity	NPC209362
0.9375	High Similarity	NPC70406
0.9371	High Similarity	NPC123906
0.9041	High Similarity	NPC313889
0.8269	Intermediate Similarity	NPC100104
0.8269	Intermediate Similarity	NPC470680
0.8239	Intermediate Similarity	NPC70949
0.8228	Intermediate Similarity	NPC233380
0.8205	Intermediate Similarity	NPC474492
0.817	Intermediate Similarity	NPC473878
0.8117	Intermediate Similarity	NPC217021
0.8117	Intermediate Similarity	NPC470679
0.8112	Intermediate Similarity	NPC471589
0.8052	Intermediate Similarity	NPC471655
0.805	Intermediate Similarity	NPC265100
0.8039	Intermediate Similarity	NPC100726
0.7975	Intermediate Similarity	NPC80681
0.7841	Intermediate Similarity	NPC103361
0.7831	Intermediate Similarity	NPC83774
0.7831	Intermediate Similarity	NPC284775
0.7811	Intermediate Similarity	NPC477003
0.7798	Intermediate Similarity	NPC191415
0.7791	Intermediate Similarity	NPC469489
0.7785	Intermediate Similarity	NPC291517
0.777	Intermediate Similarity	NPC330326
0.7738	Intermediate Similarity	NPC73994
0.7738	Intermediate Similarity	NPC61011
0.7716	Intermediate Similarity	NPC274981
0.7714	Intermediate Similarity	NPC135950
0.7701	Intermediate Similarity	NPC216550
0.7658	Intermediate Similarity	NPC472260
0.7644	Intermediate Similarity	NPC476460
0.7619	Intermediate Similarity	NPC157583
0.7619	Intermediate Similarity	NPC313823
0.7613	Intermediate Similarity	NPC230085
0.7613	Intermediate Similarity	NPC159630
0.7602	Intermediate Similarity	NPC46895
0.7561	Intermediate Similarity	NPC42372
0.7561	Intermediate Similarity	NPC115232
0.7557	Intermediate Similarity	NPC326422
0.7546	Intermediate Similarity	NPC242116
0.7532	Intermediate Similarity	NPC102664
0.7529	Intermediate Similarity	NPC477042
0.7528	Intermediate Similarity	NPC167710
0.75	Intermediate Similarity	NPC312860
0.75	Intermediate Similarity	NPC107287
0.75	Intermediate Similarity	NPC293216
0.75	Intermediate Similarity	NPC469529
0.7468	Intermediate Similarity	NPC112741
0.7458	Intermediate Similarity	NPC304203
0.7456	Intermediate Similarity	NPC476419
0.7452	Intermediate Similarity	NPC167400
0.7451	Intermediate Similarity	NPC65408
0.7444	Intermediate Similarity	NPC284338
0.7443	Intermediate Similarity	NPC114974
0.7442	Intermediate Similarity	NPC102755
0.7429	Intermediate Similarity	NPC103119
0.7415	Intermediate Similarity	NPC245244
0.7415	Intermediate Similarity	NPC166424
0.7415	Intermediate Similarity	NPC146373
0.7414	Intermediate Similarity	NPC118084
0.7412	Intermediate Similarity	NPC237188
0.741	Intermediate Similarity	NPC114637
0.7381	Intermediate Similarity	NPC273532
0.7381	Intermediate Similarity	NPC262338
0.7381	Intermediate Similarity	NPC249614
0.7377	Intermediate Similarity	NPC317701
0.7347	Intermediate Similarity	NPC27740
0.7346	Intermediate Similarity	NPC263455
0.7338	Intermediate Similarity	NPC27802
0.7338	Intermediate Similarity	NPC114310
0.7338	Intermediate Similarity	NPC472288
0.7333	Intermediate Similarity	NPC106824
0.7322	Intermediate Similarity	NPC106757
0.7322	Intermediate Similarity	NPC472069
0.7322	Intermediate Similarity	NPC472062
0.7322	Intermediate Similarity	NPC472063
0.732	Intermediate Similarity	NPC23215
0.7305	Intermediate Similarity	NPC41717
0.7303	Intermediate Similarity	NPC322488
0.7299	Intermediate Similarity	NPC467063
0.7283	Intermediate Similarity	NPC470677
0.7278	Intermediate Similarity	NPC109922
0.7267	Intermediate Similarity	NPC89490
0.7253	Intermediate Similarity	NPC477004
0.7251	Intermediate Similarity	NPC151635
0.7246	Intermediate Similarity	NPC2414
0.7243	Intermediate Similarity	NPC88115
0.7232	Intermediate Similarity	NPC255909
0.7219	Intermediate Similarity	NPC475090
0.7219	Intermediate Similarity	NPC329896
0.7219	Intermediate Similarity	NPC475105
0.7219	Intermediate Similarity	NPC71236
0.7204	Intermediate Similarity	NPC472065
0.7204	Intermediate Similarity	NPC472064
0.7191	Intermediate Similarity	NPC324091
0.7191	Intermediate Similarity	NPC154339
0.7182	Intermediate Similarity	NPC128244
0.7172	Intermediate Similarity	NPC91958
0.7171	Intermediate Similarity	NPC282398
0.7167	Intermediate Similarity	NPC267343
0.7159	Intermediate Similarity	NPC133003
0.7158	Intermediate Similarity	NPC474767
0.7158	Intermediate Similarity	NPC237414
0.7143	Intermediate Similarity	NPC182570
0.7143	Intermediate Similarity	NPC48564
0.7143	Intermediate Similarity	NPC265605
0.7127	Intermediate Similarity	NPC93390
0.7127	Intermediate Similarity	NPC202812
0.7126	Intermediate Similarity	NPC182940
0.7126	Intermediate Similarity	NPC79777
0.7126	Intermediate Similarity	NPC471997
0.7124	Intermediate Similarity	NPC471322
0.7124	Intermediate Similarity	NPC101165
0.7122	Intermediate Similarity	NPC76540
0.712	Intermediate Similarity	NPC121327
0.7111	Intermediate Similarity	NPC47190
0.7104	Intermediate Similarity	NPC34837
0.709	Intermediate Similarity	NPC472070
0.7088	Intermediate Similarity	NPC79356
0.7088	Intermediate Similarity	NPC102592
0.7072	Intermediate Similarity	NPC473821
0.7065	Intermediate Similarity	NPC81535
0.7062	Intermediate Similarity	NPC311282
0.7059	Intermediate Similarity	NPC470894
0.7056	Intermediate Similarity	NPC138370
0.7055	Intermediate Similarity	NPC143603
0.7049	Intermediate Similarity	NPC473814
0.7049	Intermediate Similarity	NPC78767
0.7047	Intermediate Similarity	NPC290094
0.7035	Intermediate Similarity	NPC252572
0.7029	Intermediate Similarity	NPC234403
0.7024	Intermediate Similarity	NPC214106
0.7013	Intermediate Similarity	NPC256893
0.7006	Intermediate Similarity	NPC113812
0.7006	Intermediate Similarity	NPC110158
0.7	Intermediate Similarity	NPC190296
0.7	Intermediate Similarity	NPC268966
0.6995	Remote Similarity	NPC292361
0.6994	Remote Similarity	NPC139763
0.6986	Remote Similarity	NPC240136
0.6986	Remote Similarity	NPC297486
0.6986	Remote Similarity	NPC471402
0.6983	Remote Similarity	NPC278434
0.6975	Remote Similarity	NPC302159
0.6974	Remote Similarity	NPC471311
0.6974	Remote Similarity	NPC471313
0.6957	Remote Similarity	NPC74153
0.6952	Remote Similarity	NPC143977
0.6947	Remote Similarity	NPC116555
0.6933	Remote Similarity	NPC477974
0.6933	Remote Similarity	NPC46358
0.6923	Remote Similarity	NPC272458
0.6919	Remote Similarity	NPC477041
0.6919	Remote Similarity	NPC248782
0.6919	Remote Similarity	NPC477044
0.6919	Remote Similarity	NPC471943
0.6915	Remote Similarity	NPC138562
0.6914	Remote Similarity	NPC84827
0.6914	Remote Similarity	NPC145885
0.6914	Remote Similarity	NPC314372
0.6914	Remote Similarity	NPC14113
0.691	Remote Similarity	NPC207851
0.6908	Remote Similarity	NPC202957
0.6908	Remote Similarity	NPC169625
0.6903	Remote Similarity	NPC324611
0.6899	Remote Similarity	NPC84911
0.6894	Remote Similarity	NPC136002
0.6889	Remote Similarity	NPC474259
0.6889	Remote Similarity	NPC477415
0.6889	Remote Similarity	NPC23476
0.6887	Remote Similarity	NPC476322
0.6882	Remote Similarity	NPC478184
0.6879	Remote Similarity	NPC231655
0.6875	Remote Similarity	NPC11126
0.6875	Remote Similarity	NPC55772
0.6875	Remote Similarity	NPC235843
0.6875	Remote Similarity	NPC248041
0.6875	Remote Similarity	NPC126709
0.6872	Remote Similarity	NPC282103
0.6867	Remote Similarity	NPC281094
0.6865	Remote Similarity	NPC227582
0.6864	Remote Similarity	NPC473706
0.6857	Remote Similarity	NPC267885
0.6851	Remote Similarity	NPC209917
0.6848	Remote Similarity	NPC157828
0.6848	Remote Similarity	NPC195239
0.6835	Remote Similarity	NPC29702
0.6835	Remote Similarity	NPC261195
0.6835	Remote Similarity	NPC29886
0.6835	Remote Similarity	NPC96102
0.6833	Remote Similarity	NPC469359
0.6816	Remote Similarity	NPC285923
0.6813	Remote Similarity	NPC110126
0.6813	Remote Similarity	NPC475874

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 NPC105811 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	214
0.1-0.2	713
0.2-0.3	1099
0.3-0.4	1961
0.4-0.5	2773
0.5-0.6	1792
0.6-0.7	533
0.7-0.8	61
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8523	High Similarity	NPD1270	Approved
0.8276	Intermediate Similarity	NPD272	Approved
0.8264	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD2481	Approved
0.8171	Intermediate Similarity	NPD2479	Phase 3
0.8	Intermediate Similarity	NPD9599	Approved
0.7908	Intermediate Similarity	NPD175	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD9100	Approved
0.7673	Intermediate Similarity	NPD2061	Approved
0.7647	Intermediate Similarity	NPD107	Approved
0.7571	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD1618	Phase 2
0.7515	Intermediate Similarity	NPD2753	Discontinued
0.75	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD4988	Discontinued
0.747	Intermediate Similarity	NPD1343	Approved
0.7468	Intermediate Similarity	NPD9271	Approved
0.7458	Intermediate Similarity	NPD460	Discontinued
0.7456	Intermediate Similarity	NPD3238	Discontinued
0.7452	Intermediate Similarity	NPD9075	Approved
0.7452	Intermediate Similarity	NPD9074	Approved
0.7451	Intermediate Similarity	NPD200	Phase 2
0.7451	Intermediate Similarity	NPD201	Phase 2
0.7438	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD9343	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3583	Phase 2
0.7391	Intermediate Similarity	NPD180	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD4848	Phase 1
0.7362	Intermediate Similarity	NPD820	Phase 3
0.7355	Intermediate Similarity	NPD569	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD9357	Approved
0.7315	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD991	Phase 2
0.7314	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD1096	Discontinued
0.7294	Intermediate Similarity	NPD4883	Approved
0.7262	Intermediate Similarity	NPD1292	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD9583	Approved
0.7247	Intermediate Similarity	NPD2336	Approved
0.7246	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD4524	Discontinued
0.7225	Intermediate Similarity	NPD3927	Phase 2
0.7222	Intermediate Similarity	NPD9392	Approved
0.7222	Intermediate Similarity	NPD9396	Approved
0.7204	Intermediate Similarity	NPD7289	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD4643	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6446	Discontinued
0.72	Intermediate Similarity	NPD2118	Approved
0.72	Intermediate Similarity	NPD7564	Discontinued
0.72	Intermediate Similarity	NPD2119	Approved
0.7189	Intermediate Similarity	NPD4304	Discovery
0.7179	Intermediate Similarity	NPD2896	Discontinued
0.7175	Intermediate Similarity	NPD2770	Discontinued
0.7151	Intermediate Similarity	NPD4299	Phase 1
0.7143	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD271	Approved
0.7143	Intermediate Similarity	NPD268	Approved
0.7127	Intermediate Similarity	NPD5853	Phase 3
0.7127	Intermediate Similarity	NPD5855	Phase 3
0.7126	Intermediate Similarity	NPD5400	Approved
0.712	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD2307	Discontinued
0.7086	Intermediate Similarity	NPD1598	Discontinued
0.7083	Intermediate Similarity	NPD5088	Discontinued
0.7072	Intermediate Similarity	NPD1173	Approved
0.7024	Intermediate Similarity	NPD6771	Discontinued
0.7013	Intermediate Similarity	NPD9726	Discontinued
0.7006	Intermediate Similarity	NPD1630	Approved
0.7	Intermediate Similarity	NPD5611	Phase 2
0.7	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD5854	Approved
0.6973	Remote Similarity	NPD7049	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD4051	Discontinued
0.6962	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD3475	Approved
0.6948	Remote Similarity	NPD3476	Approved
0.6947	Remote Similarity	NPD2509	Approved
0.6947	Remote Similarity	NPD2510	Approved
0.6937	Remote Similarity	NPD1722	Approved
0.6933	Remote Similarity	NPD4702	Approved
0.6933	Remote Similarity	NPD4703	Approved
0.6927	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4028	Approved
0.6923	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3944	Approved
0.6923	Remote Similarity	NPD4029	Approved
0.6923	Remote Similarity	NPD4030	Approved
0.6923	Remote Similarity	NPD3942	Approved
0.6918	Remote Similarity	NPD768	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.691	Remote Similarity	NPD3569	Discontinued
0.6909	Remote Similarity	NPD510	Phase 1
0.6906	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2213	Approved
0.6905	Remote Similarity	NPD2214	Approved
0.6903	Remote Similarity	NPD803	Phase 1
0.6902	Remote Similarity	NPD6226	Phase 3
0.6897	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD4913	Phase 3
0.6894	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD3178	Discontinued
0.6882	Remote Similarity	NPD1545	Discontinued
0.6882	Remote Similarity	NPD2405	Phase 3
0.6882	Remote Similarity	NPD1631	Approved
0.6879	Remote Similarity	NPD9098	Phase 3
0.6879	Remote Similarity	NPD9099	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD3947	Discontinued
0.6872	Remote Similarity	NPD3394	Approved
0.6872	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD3389	Approved
0.6872	Remote Similarity	NPD3393	Approved
0.6864	Remote Similarity	NPD2511	Approved
0.6857	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD7175	Phase 1
0.6848	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2008	Discontinued
0.6839	Remote Similarity	NPD750	Phase 2
0.6839	Remote Similarity	NPD715	Phase 3
0.6839	Remote Similarity	NPD6152	Phase 1
0.6835	Remote Similarity	NPD206	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD4922	Phase 2
0.6826	Remote Similarity	NPD2809	Approved
0.6825	Remote Similarity	NPD4912	Phase 3
0.6821	Remote Similarity	NPD1575	Approved
0.6821	Remote Similarity	NPD1573	Approved
0.6816	Remote Similarity	NPD721	Approved
0.6813	Remote Similarity	NPD786	Approved
0.6813	Remote Similarity	NPD5685	Approved
0.6813	Remote Similarity	NPD5686	Approved
0.6811	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5017	Discontinued
0.68	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.68	Remote Similarity	NPD482	Approved
0.6796	Remote Similarity	NPD3246	Discontinued
0.6789	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD944	Approved
0.6772	Remote Similarity	NPD4924	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD6787	Phase 2
0.6769	Remote Similarity	NPD5888	Phase 2
0.6761	Remote Similarity	NPD6044	Discontinued
0.676	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD7010	Phase 3
0.6753	Remote Similarity	NPD9284	Approved
0.6753	Remote Similarity	NPD9080	Approved
0.6742	Remote Similarity	NPD5473	Discontinued
0.6742	Remote Similarity	NPD1643	Phase 3
0.674	Remote Similarity	NPD7026	Phase 2
0.6739	Remote Similarity	NPD4376	Phase 3
0.6736	Remote Similarity	NPD1600	Suspended
0.6731	Remote Similarity	NPD9206	Approved
0.6731	Remote Similarity	NPD9207	Approved
0.673	Remote Similarity	NPD792	Discontinued
0.6728	Remote Similarity	NPD5020	Approved
0.6723	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.672	Remote Similarity	NPD2290	Phase 3
0.672	Remote Similarity	NPD2289	Phase 3
0.6719	Remote Similarity	NPD1506	Discontinued
0.6718	Remote Similarity	NPD2411	Approved
0.6708	Remote Similarity	NPD2074	Approved
0.6708	Remote Similarity	NPD2069	Approved
0.6708	Remote Similarity	NPD2075	Approved
0.6708	Remote Similarity	NPD2071	Approved
0.6708	Remote Similarity	NPD2073	Approved
0.6708	Remote Similarity	NPD2068	Approved
0.6708	Remote Similarity	NPD2070	Approved
0.6708	Remote Similarity	NPD2072	Approved
0.6689	Remote Similarity	NPD9598	Discontinued
0.6687	Remote Similarity	NPD1427	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD3717	Discontinued
0.6686	Remote Similarity	NPD3347	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7187	Phase 2
0.6667	Remote Similarity	NPD1649	Discontinued
0.6667	Remote Similarity	NPD7618	Phase 3
0.6667	Remote Similarity	NPD3967	Approved
0.6667	Remote Similarity	NPD7469	Discontinued
0.6667	Remote Similarity	NPD1395	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7619	Phase 3
0.665	Remote Similarity	NPD8242	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD981	Phase 2
0.6649	Remote Similarity	NPD1982	Phase 1
0.6646	Remote Similarity	NPD1994	Approved
0.6646	Remote Similarity	NPD1993	Approved
0.6646	Remote Similarity	NPD1380	Discovery
0.6646	Remote Similarity	NPD1995	Approved
0.6645	Remote Similarity	NPD748	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD4823	Approved
0.6644	Remote Similarity	NPD4824	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