NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	482.23
Volume:	487.218
LogP:	3.896
LogD:	2.851
LogS:	-4.942
# Rotatable Bonds:	3
TPSA:	95.34
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.45
Synthetic Accessibility Score:	5.569
Fsp3:	0.679
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:	-5.358
MDCK Permeability:	1.4370871213031933e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.947
30% Bioavailability (F30%):	0.913

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.157
Plasma Protein Binding (PPB):	86.9317398071289%
Volume Distribution (VD):	2.569
Pgp-substrate:	12.012991905212402%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.126
CYP2C19-inhibitor:	0.205
CYP2C19-substrate:	0.627
CYP2C9-inhibitor:	0.753
CYP2C9-substrate:	0.027
CYP2D6-inhibitor:	0.097
CYP2D6-substrate:	0.07
CYP3A4-inhibitor:	0.765
CYP3A4-substrate:	0.722

ADMET: Excretion

Clearance (CL):	4.313
Half-life (T1/2):	0.348

ADMET: Toxicity

hERG Blockers:	0.113
Human Hepatotoxicity (H-HT):	0.563
Drug-inuced Liver Injury (DILI):	0.323
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.946
Maximum Recommended Daily Dose:	0.925
Skin Sensitization:	0.222
Carcinogencity:	0.155
Eye Corrosion:	0.103
Eye Irritation:	0.133
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC209362

Natural Product ID:	NPC209362
*Common Name:**	Caulibugulone F
IUPAC Name:	n.a.
Synonyms:	Caulibugulone F
Standard InCHIKey:	MUUKBLUCRRGACD-XNTDXEJSSA-N
Standard InCHI:	InChI=1S/C12H13N3O2/c1-13-11-6-10(15-4-5-16)8-2-3-14-7-9(8)12(11)17/h2-3,6-7,13,16H,4-5H2,1H3/b15-10+
SMILES:	CNC1=C/C(=NCCO)/c2ccncc2C1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL525254
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004707] Organic nitrogen compounds [CHEMONTID:0000278] Organonitrogen compounds [CHEMONTID:0002892] Quinonimines [CHEMONTID:0002895] P-quinonimines

*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	=	0.1	ug.mL-1	PMID[575366]

☑ 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 NPC209362 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	207
0.1-0.2	4493
0.2-0.3	16157
0.3-0.4	15155
0.4-0.5	3082
0.5-0.6	2202
0.6-0.7	1218
0.7-0.8	172
0.8-0.85	1
0.85-0.9	6
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9592	High Similarity	NPC213914
0.951	High Similarity	NPC467188
0.9379	High Similarity	NPC105811
0.9	High Similarity	NPC251391
0.894	High Similarity	NPC229055
0.8933	High Similarity	NPC70406
0.8926	High Similarity	NPC123906
0.8882	High Similarity	NPC74357
0.8618	High Similarity	NPC313889
0.8082	Intermediate Similarity	NPC471589
0.8012	Intermediate Similarity	NPC100104
0.8012	Intermediate Similarity	NPC470680
0.7988	Intermediate Similarity	NPC70949
0.795	Intermediate Similarity	NPC474492
0.7911	Intermediate Similarity	NPC473878
0.7911	Intermediate Similarity	NPC471655
0.7898	Intermediate Similarity	NPC100726
0.7866	Intermediate Similarity	NPC233380
0.7862	Intermediate Similarity	NPC470679
0.7862	Intermediate Similarity	NPC217021
0.784	Intermediate Similarity	NPC80681
0.7821	Intermediate Similarity	NPC103361
0.7805	Intermediate Similarity	NPC265100
0.7764	Intermediate Similarity	NPC263455
0.7727	Intermediate Similarity	NPC114974
0.7718	Intermediate Similarity	NPC313823
0.7706	Intermediate Similarity	NPC284775
0.7706	Intermediate Similarity	NPC83774
0.7697	Intermediate Similarity	NPC135950
0.7674	Intermediate Similarity	NPC191415
0.767	Intermediate Similarity	NPC469489
0.7662	Intermediate Similarity	NPC472288
0.7647	Intermediate Similarity	NPC291517
0.7616	Intermediate Similarity	NPC73994
0.7616	Intermediate Similarity	NPC61011
0.7602	Intermediate Similarity	NPC157583
0.7593	Intermediate Similarity	NPC312860
0.7586	Intermediate Similarity	NPC477003
0.7545	Intermediate Similarity	NPC42372
0.7531	Intermediate Similarity	NPC472260
0.753	Intermediate Similarity	NPC242116
0.7529	Intermediate Similarity	NPC102755
0.7527	Intermediate Similarity	NPC474767
0.75	Intermediate Similarity	NPC41717
0.7486	Intermediate Similarity	NPC46895
0.7486	Intermediate Similarity	NPC216550
0.7485	Intermediate Similarity	NPC293216
0.7485	Intermediate Similarity	NPC274981
0.7485	Intermediate Similarity	NPC107287
0.7472	Intermediate Similarity	NPC154339
0.7471	Intermediate Similarity	NPC273532
0.7471	Intermediate Similarity	NPC249614
0.7459	Intermediate Similarity	NPC109922
0.7451	Intermediate Similarity	NPC256893
0.7444	Intermediate Similarity	NPC267343
0.7442	Intermediate Similarity	NPC476419
0.7438	Intermediate Similarity	NPC167400
0.743	Intermediate Similarity	NPC476460
0.7419	Intermediate Similarity	NPC23215
0.7414	Intermediate Similarity	NPC477042
0.7407	Intermediate Similarity	NPC102664
0.7403	Intermediate Similarity	NPC330326
0.7396	Intermediate Similarity	NPC114637
0.7386	Intermediate Similarity	NPC207851
0.7384	Intermediate Similarity	NPC469529
0.7375	Intermediate Similarity	NPC159630
0.7375	Intermediate Similarity	NPC230085
0.7365	Intermediate Similarity	NPC473706
0.7363	Intermediate Similarity	NPC292361
0.7348	Intermediate Similarity	NPC326422
0.7346	Intermediate Similarity	NPC112741
0.7337	Intermediate Similarity	NPC284338
0.7322	Intermediate Similarity	NPC167710
0.732	Intermediate Similarity	NPC71236
0.7314	Intermediate Similarity	NPC471997
0.7303	Intermediate Similarity	NPC118084
0.7283	Intermediate Similarity	NPC477041
0.7283	Intermediate Similarity	NPC477044
0.7273	Intermediate Similarity	NPC470677
0.7273	Intermediate Similarity	NPC317701
0.7267	Intermediate Similarity	NPC262338
0.7253	Intermediate Similarity	NPC304203
0.7235	Intermediate Similarity	NPC115232
0.7228	Intermediate Similarity	NPC106824
0.7222	Intermediate Similarity	NPC255909
0.7222	Intermediate Similarity	NPC103119
0.7222	Intermediate Similarity	NPC209917
0.7219	Intermediate Similarity	NPC472063
0.7219	Intermediate Similarity	NPC472062
0.7219	Intermediate Similarity	NPC472069
0.7215	Intermediate Similarity	NPC114310
0.7213	Intermediate Similarity	NPC202812
0.7213	Intermediate Similarity	NPC93390
0.72	Intermediate Similarity	NPC237188
0.7198	Intermediate Similarity	NPC47190
0.7182	Intermediate Similarity	NPC475874
0.7179	Intermediate Similarity	NPC322488
0.7178	Intermediate Similarity	NPC302159
0.7171	Intermediate Similarity	NPC245244
0.7171	Intermediate Similarity	NPC146373
0.7171	Intermediate Similarity	NPC166424
0.7158	Intermediate Similarity	NPC473821
0.7151	Intermediate Similarity	NPC295158
0.7151	Intermediate Similarity	NPC477045
0.7143	Intermediate Similarity	NPC151635
0.7143	Intermediate Similarity	NPC89490
0.7135	Intermediate Similarity	NPC78767
0.7135	Intermediate Similarity	NPC473814
0.7128	Intermediate Similarity	NPC106757
0.7128	Intermediate Similarity	NPC328318
0.7128	Intermediate Similarity	NPC328596
0.7119	Intermediate Similarity	NPC317010
0.7115	Intermediate Similarity	NPC471322
0.7107	Intermediate Similarity	NPC65408
0.7105	Intermediate Similarity	NPC472064
0.7105	Intermediate Similarity	NPC27740
0.7105	Intermediate Similarity	NPC472065
0.7099	Intermediate Similarity	NPC190296
0.7097	Intermediate Similarity	NPC475105
0.7097	Intermediate Similarity	NPC329896
0.7097	Intermediate Similarity	NPC475090
0.7095	Intermediate Similarity	NPC467063
0.7088	Intermediate Similarity	NPC324091
0.7083	Intermediate Similarity	NPC27802
0.7083	Intermediate Similarity	NPC472070
0.7081	Intermediate Similarity	NPC79356
0.7081	Intermediate Similarity	NPC102592
0.7062	Intermediate Similarity	NPC11126
0.7062	Intermediate Similarity	NPC248041
0.7062	Intermediate Similarity	NPC126709
0.7059	Intermediate Similarity	NPC237414
0.7059	Intermediate Similarity	NPC81535
0.7059	Intermediate Similarity	NPC477004
0.7056	Intermediate Similarity	NPC133003
0.7056	Intermediate Similarity	NPC311282
0.7053	Intermediate Similarity	NPC88115
0.7053	Intermediate Similarity	NPC477043
0.7052	Intermediate Similarity	NPC470894
0.7045	Intermediate Similarity	NPC267885
0.7043	Intermediate Similarity	NPC74153
0.7033	Intermediate Similarity	NPC473628
0.7022	Intermediate Similarity	NPC182940
0.7022	Intermediate Similarity	NPC79777
0.7012	Intermediate Similarity	NPC314372
0.7005	Intermediate Similarity	NPC248782
0.7	Intermediate Similarity	NPC113812
0.7	Intermediate Similarity	NPC110158
0.6989	Remote Similarity	NPC203468
0.6989	Remote Similarity	NPC128244
0.6989	Remote Similarity	NPC149155
0.6989	Remote Similarity	NPC139763
0.6989	Remote Similarity	NPC110500
0.6978	Remote Similarity	NPC278434
0.6977	Remote Similarity	NPC469813
0.6977	Remote Similarity	NPC476446
0.6977	Remote Similarity	NPC78375
0.6971	Remote Similarity	NPC470498
0.6968	Remote Similarity	NPC471313
0.6968	Remote Similarity	NPC123395
0.6968	Remote Similarity	NPC471311
0.6966	Remote Similarity	NPC283219
0.6963	Remote Similarity	NPC327592
0.6957	Remote Similarity	NPC138370
0.6944	Remote Similarity	NPC159125
0.6943	Remote Similarity	NPC282398
0.6941	Remote Similarity	NPC469762
0.6937	Remote Similarity	NPC29702
0.6936	Remote Similarity	NPC2414
0.6933	Remote Similarity	NPC91958
0.6932	Remote Similarity	NPC252572
0.6931	Remote Similarity	NPC121327
0.6928	Remote Similarity	NPC290094
0.6927	Remote Similarity	NPC234403
0.6927	Remote Similarity	NPC317373
0.6923	Remote Similarity	NPC474236
0.6923	Remote Similarity	NPC33229
0.6915	Remote Similarity	NPC34837
0.6911	Remote Similarity	NPC138562
0.691	Remote Similarity	NPC14113
0.691	Remote Similarity	NPC84827
0.691	Remote Similarity	NPC145885
0.6909	Remote Similarity	NPC159856
0.6908	Remote Similarity	NPC48564
0.6908	Remote Similarity	NPC182570
0.6908	Remote Similarity	NPC265605
0.6906	Remote Similarity	NPC228835
0.6906	Remote Similarity	NPC285923
0.6902	Remote Similarity	NPC268966
0.6899	Remote Similarity	NPC324611
0.6899	Remote Similarity	NPC101165
0.6897	Remote Similarity	NPC54988
0.6895	Remote Similarity	NPC98864
0.6882	Remote Similarity	NPC469785
0.6879	Remote Similarity	NPC40779
0.6879	Remote Similarity	NPC311276
0.6875	Remote Similarity	NPC302647
0.6875	Remote Similarity	NPC76540
0.6872	Remote Similarity	NPC55772
0.6872	Remote Similarity	NPC123839
0.6862	Remote Similarity	NPC227582

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 NPC209362 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	592
0.2-0.3	1097
0.3-0.4	1816
0.4-0.5	2717
0.5-0.6	2029
0.6-0.7	681
0.7-0.8	64
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
0.8	Intermediate Similarity	NPD272	Approved
0.7987	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD1618	Phase 2
0.7719	Intermediate Similarity	NPD2479	Phase 3
0.7719	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD2481	Approved
0.7688	Intermediate Similarity	NPD1096	Discontinued
0.7674	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD175	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD9599	Approved
0.7564	Intermediate Similarity	NPD569	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD2061	Approved
0.7484	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD460	Discontinued
0.7438	Intermediate Similarity	NPD9074	Approved
0.7438	Intermediate Similarity	NPD9075	Approved
0.7423	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD107	Approved
0.7403	Intermediate Similarity	NPD9100	Approved
0.7399	Intermediate Similarity	NPD2753	Discontinued
0.7378	Intermediate Similarity	NPD180	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD1343	Approved
0.7349	Intermediate Similarity	NPD820	Phase 3
0.7346	Intermediate Similarity	NPD9271	Approved
0.7341	Intermediate Similarity	NPD3238	Discontinued
0.7337	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD9343	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD4051	Discontinued
0.731	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD7289	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD4883	Approved
0.7277	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD4988	Discontinued
0.7238	Intermediate Similarity	NPD2336	Approved
0.7219	Intermediate Similarity	NPD9357	Approved
0.7191	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD991	Phase 2
0.719	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD5088	Discontinued
0.7176	Intermediate Similarity	NPD3583	Phase 2
0.7175	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD4848	Phase 1
0.717	Intermediate Similarity	NPD2896	Discontinued
0.716	Intermediate Similarity	NPD2511	Approved
0.7126	Intermediate Similarity	NPD2809	Approved
0.7124	Intermediate Similarity	NPD9583	Approved
0.7119	Intermediate Similarity	NPD3927	Phase 2
0.7115	Intermediate Similarity	NPD9726	Discontinued
0.7112	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD201	Phase 2
0.7107	Intermediate Similarity	NPD200	Phase 2
0.7099	Intermediate Similarity	NPD1427	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD9392	Approved
0.7095	Intermediate Similarity	NPD7564	Discontinued
0.7095	Intermediate Similarity	NPD9396	Approved
0.7093	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD2307	Discontinued
0.7079	Intermediate Similarity	NPD3178	Discontinued
0.7078	Intermediate Similarity	NPD2118	Approved
0.7078	Intermediate Similarity	NPD2119	Approved
0.7069	Intermediate Similarity	NPD485	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD1173	Approved
0.7063	Intermediate Similarity	NPD1380	Discovery
0.7052	Intermediate Similarity	NPD1292	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD4702	Approved
0.703	Intermediate Similarity	NPD4703	Approved
0.7029	Intermediate Similarity	NPD750	Phase 2
0.7029	Intermediate Similarity	NPD4524	Discontinued
0.7018	Intermediate Similarity	NPD5400	Approved
0.7017	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7098	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2213	Approved
0.7	Intermediate Similarity	NPD2214	Approved
0.6994	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6446	Discontinued
0.6994	Remote Similarity	NPD5611	Phase 2
0.6989	Remote Similarity	NPD482	Approved
0.6984	Remote Similarity	NPD5017	Discontinued
0.6978	Remote Similarity	NPD2770	Discontinued
0.6977	Remote Similarity	NPD1631	Approved
0.6968	Remote Similarity	NPD7049	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD4299	Phase 1
0.6944	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD2509	Approved
0.6943	Remote Similarity	NPD2510	Approved
0.6935	Remote Similarity	NPD5853	Phase 3
0.6935	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD5855	Phase 3
0.6933	Remote Similarity	NPD1383	Phase 3
0.6933	Remote Similarity	NPD1382	Phase 2
0.6927	Remote Similarity	NPD1643	Phase 3
0.6919	Remote Similarity	NPD6771	Discontinued
0.6919	Remote Similarity	NPD4376	Phase 3
0.6911	Remote Similarity	NPD4304	Discovery
0.6908	Remote Similarity	NPD268	Approved
0.6908	Remote Similarity	NPD270	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD271	Approved
0.6906	Remote Similarity	NPD3569	Discontinued
0.6906	Remote Similarity	NPD721	Approved
0.6905	Remote Similarity	NPD510	Phase 1
0.6901	Remote Similarity	NPD1630	Approved
0.6893	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3117	Approved
0.6875	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3947	Discontinued
0.6875	Remote Similarity	NPD3116	Approved
0.6872	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD3394	Approved
0.6869	Remote Similarity	NPD3393	Approved
0.6869	Remote Similarity	NPD3389	Approved
0.6859	Remote Similarity	NPD1598	Discontinued
0.6857	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD5888	Phase 2
0.6852	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7618	Phase 3
0.6845	Remote Similarity	NPD7619	Phase 3
0.6835	Remote Similarity	NPD3475	Approved
0.6835	Remote Similarity	NPD3476	Approved
0.6831	Remote Similarity	NPD7026	Phase 2
0.6829	Remote Similarity	NPD5020	Approved
0.6829	Remote Similarity	NPD4805	Approved
0.6829	Remote Similarity	NPD1722	Approved
0.6821	Remote Similarity	NPD1600	Suspended
0.6818	Remote Similarity	NPD1575	Approved
0.6818	Remote Similarity	NPD1573	Approved
0.6813	Remote Similarity	NPD3944	Approved
0.6813	Remote Similarity	NPD4028	Approved
0.6813	Remote Similarity	NPD3942	Approved
0.6813	Remote Similarity	NPD4029	Approved
0.6813	Remote Similarity	NPD4030	Approved
0.6811	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6226	Phase 3
0.6809	Remote Similarity	NPD2290	Phase 3
0.6809	Remote Similarity	NPD2289	Phase 3
0.68	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD3246	Discontinued
0.679	Remote Similarity	NPD9506	Approved
0.6789	Remote Similarity	NPD5854	Approved
0.6789	Remote Similarity	NPD2405	Phase 3
0.6788	Remote Similarity	NPD3717	Discontinued
0.6788	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD944	Approved
0.6771	Remote Similarity	NPD7187	Phase 2
0.6768	Remote Similarity	NPD3795	Approved
0.6768	Remote Similarity	NPD3794	Approved
0.6768	Remote Similarity	NPD1395	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7469	Discontinued
0.6759	Remote Similarity	NPD9098	Phase 3
0.6759	Remote Similarity	NPD9099	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD2092	Phase 2
0.6758	Remote Similarity	NPD2094	Phase 2
0.6758	Remote Similarity	NPD2095	Phase 2
0.6753	Remote Similarity	NPD7010	Phase 3
0.6752	Remote Similarity	NPD9284	Approved
0.6752	Remote Similarity	NPD9080	Approved
0.6751	Remote Similarity	NPD6152	Phase 1
0.6744	Remote Similarity	NPD2582	Approved
0.6744	Remote Similarity	NPD2581	Approved
0.674	Remote Similarity	NPD9510	Approved
0.6738	Remote Similarity	NPD4922	Phase 2
0.6734	Remote Similarity	NPD8242	Clinical (unspecified phase)
0.673	Remote Similarity	NPD9206	Approved
0.673	Remote Similarity	NPD9207	Approved
0.673	Remote Similarity	NPD715	Phase 3
0.6728	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD1661	Suspended
0.6724	Remote Similarity	NPD8026	Phase 1
0.6722	Remote Similarity	NPD3505	Approved
0.6722	Remote Similarity	NPD3506	Approved
0.6721	Remote Similarity	NPD2096	Phase 2
0.6721	Remote Similarity	NPD2091	Phase 2
0.672	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.672	Remote Similarity	NPD5685	Approved
0.672	Remote Similarity	NPD5686	Approved
0.6719	Remote Similarity	NPD7817	Phase 1
0.6719	Remote Similarity	NPD7727	Phase 2
0.6718	Remote Similarity	NPD3371	Approved
0.6716	Remote Similarity	NPD6173	Approved
0.6707	Remote Similarity	NPD768	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD786	Approved
0.6707	Remote Similarity	NPD4804	Approved
0.6705	Remote Similarity	NPD5255	Approved
0.6701	Remote Similarity	NPD8115	Approved
0.6701	Remote Similarity	NPD8114	Approved
0.6701	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.67	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD803	Phase 1
0.6686	Remote Similarity	NPD6026	Approved
0.6686	Remote Similarity	NPD1183	Approved
0.6686	Remote Similarity	NPD1545	Discontinued
0.6685	Remote Similarity	NPD4076	Approved
0.6685	Remote Similarity	NPD4079	Approved
0.6684	Remote Similarity	NPD6180	Clinical (unspecified phase)

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