NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	218.07
Volume:	214.245
LogP:	-0.112
LogD:	-0.165
LogS:	-0.912
# Rotatable Bonds:	2
TPSA:	79.62
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.773
Synthetic Accessibility Score:	3.052
Fsp3:	0.273
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.492
MDCK Permeability:	1.380530829919735e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.042
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.043

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.579
Plasma Protein Binding (PPB):	49.892921447753906%
Volume Distribution (VD):	1.447
Pgp-substrate:	64.27130126953125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.455
CYP1A2-substrate:	0.48
CYP2C19-inhibitor:	0.049
CYP2C19-substrate:	0.075
CYP2C9-inhibitor:	0.039
CYP2C9-substrate:	0.157
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.185
CYP3A4-inhibitor:	0.12
CYP3A4-substrate:	0.227

ADMET: Excretion

Clearance (CL):	3.501
Half-life (T1/2):	0.432

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.144
Drug-inuced Liver Injury (DILI):	0.958
AMES Toxicity:	0.502
Rat Oral Acute Toxicity:	0.169
Maximum Recommended Daily Dose:	0.024
Skin Sensitization:	0.866
Carcinogencity:	0.151
Eye Corrosion:	0.011
Eye Irritation:	0.669
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC213914

Natural Product ID:	NPC213914
*Common Name:**	Caulibugulone D
IUPAC Name:	7-(2-hydroxyethylamino)isoquinoline-5,8-dione
Synonyms:	Caulibugulone D
Standard InCHIKey:	JPUNXFPVVKDHNP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H10N2O3/c14-4-3-13-9-5-10(15)7-1-2-12-6-8(7)11(9)16/h1-2,5-6,13-14H,3-4H2
SMILES:	c1cncc2c1C(=O)C=C(C2=O)NCCO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL447876
PubChem CID:	2598
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
NPT1226	Individual Protein	Caspase-7	Homo sapiens	Potency	=	12589.3	nM	PMID[478277]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	39810.7	nM	PMID[478277]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	6309.6	nM	PMID[478277]
NPT150	Individual Protein	Anthrax lethal factor	Bacillus anthracis	Potency	=	25118.9	nM	PMID[478277]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	3548.1	nM	PMID[478277]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	3162.3	nM	PMID[478277]
NPT277	Individual Protein	Caspase-1	Homo sapiens	Potency	=	3162.3	nM	PMID[478277]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	3981.1	nM	PMID[478277]
NPT58	Individual Protein	Bloom syndrome protein	Homo sapiens	Potency	=	28183.8	nM	PMID[478277]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	7943.3	nM	PMID[478277]
NPT1139	Individual Protein	Arachidonate 15-lipoxygenase, type II	Homo sapiens	Potency	n.a.	15848.9	nM	PMID[478277]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	15848.9	nM	PMID[478277]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1.67	ug.mL-1	PMID[478276]
NPT2	Others	Unspecified		Potency	=	1995.3	nM	PMID[478277]
NPT93	Individual Protein	Survival motor neuron protein	Homo sapiens	Potency	=	5011.9	nM	PMID[478277]

☑ 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 NPC213914 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	236
0.1-0.2	5242
0.2-0.3	16290
0.3-0.4	14434
0.4-0.5	3109
0.5-0.6	2268
0.6-0.7	989
0.7-0.8	119
0.8-0.85	0
0.85-0.9	7
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9592	High Similarity	NPC209362
0.9384	High Similarity	NPC105811
0.9116	High Similarity	NPC467188
0.8947	High Similarity	NPC229055
0.8889	High Similarity	NPC74357
0.8882	High Similarity	NPC251391
0.8816	High Similarity	NPC70406
0.8808	High Similarity	NPC123906
0.8506	High Similarity	NPC313889
0.7988	Intermediate Similarity	NPC233380
0.7973	Intermediate Similarity	NPC471589
0.7963	Intermediate Similarity	NPC474492
0.7833	Intermediate Similarity	NPC103361
0.7805	Intermediate Similarity	NPC100104
0.7805	Intermediate Similarity	NPC470680
0.7784	Intermediate Similarity	NPC70949
0.7778	Intermediate Similarity	NPC263455
0.774	Intermediate Similarity	NPC114974
0.7709	Intermediate Similarity	NPC135950
0.7702	Intermediate Similarity	NPC473878
0.7702	Intermediate Similarity	NPC471655
0.7684	Intermediate Similarity	NPC469489
0.7654	Intermediate Similarity	NPC470679
0.7654	Intermediate Similarity	NPC217021
0.7616	Intermediate Similarity	NPC284775
0.7607	Intermediate Similarity	NPC312860
0.7605	Intermediate Similarity	NPC265100
0.76	Intermediate Similarity	NPC477003
0.7578	Intermediate Similarity	NPC100726
0.756	Intermediate Similarity	NPC42372
0.7541	Intermediate Similarity	NPC474767
0.753	Intermediate Similarity	NPC80681
0.7514	Intermediate Similarity	NPC83774
0.75	Intermediate Similarity	NPC313823
0.75	Intermediate Similarity	NPC274981
0.7486	Intermediate Similarity	NPC191415
0.7486	Intermediate Similarity	NPC154339
0.7485	Intermediate Similarity	NPC273532
0.7473	Intermediate Similarity	NPC109922
0.7473	Intermediate Similarity	NPC292361
0.7457	Intermediate Similarity	NPC476419
0.7444	Intermediate Similarity	NPC476460
0.7443	Intermediate Similarity	NPC102755
0.7436	Intermediate Similarity	NPC291517
0.7429	Intermediate Similarity	NPC73994
0.7429	Intermediate Similarity	NPC61011
0.7419	Intermediate Similarity	NPC330326
0.7414	Intermediate Similarity	NPC157583
0.7403	Intermediate Similarity	NPC216550
0.7399	Intermediate Similarity	NPC293216
0.7381	Intermediate Similarity	NPC473706
0.7363	Intermediate Similarity	NPC326422
0.7363	Intermediate Similarity	NPC267343
0.7346	Intermediate Similarity	NPC167400
0.7342	Intermediate Similarity	NPC472288
0.7337	Intermediate Similarity	NPC167710
0.7337	Intermediate Similarity	NPC242116
0.7325	Intermediate Similarity	NPC23215
0.731	Intermediate Similarity	NPC41717
0.7303	Intermediate Similarity	NPC46895
0.7303	Intermediate Similarity	NPC207851
0.7289	Intermediate Similarity	NPC107287
0.7268	Intermediate Similarity	NPC304203
0.7258	Intermediate Similarity	NPC284338
0.7251	Intermediate Similarity	NPC115232
0.7244	Intermediate Similarity	NPC256893
0.7233	Intermediate Similarity	NPC114310
0.7232	Intermediate Similarity	NPC477042
0.7232	Intermediate Similarity	NPC471997
0.7229	Intermediate Similarity	NPC472260
0.7209	Intermediate Similarity	NPC114637
0.7197	Intermediate Similarity	NPC322488
0.7191	Intermediate Similarity	NPC470677
0.719	Intermediate Similarity	NPC166424
0.719	Intermediate Similarity	NPC146373
0.719	Intermediate Similarity	NPC245244
0.7184	Intermediate Similarity	NPC249614
0.7184	Intermediate Similarity	NPC262338
0.7178	Intermediate Similarity	NPC230085
0.7178	Intermediate Similarity	NPC159630
0.7152	Intermediate Similarity	NPC112741
0.7151	Intermediate Similarity	NPC106824
0.7143	Intermediate Similarity	NPC103119
0.7143	Intermediate Similarity	NPC472062
0.7143	Intermediate Similarity	NPC472063
0.7143	Intermediate Similarity	NPC472069
0.7135	Intermediate Similarity	NPC202812
0.7135	Intermediate Similarity	NPC317010
0.7127	Intermediate Similarity	NPC118084
0.7124	Intermediate Similarity	NPC27740
0.7119	Intermediate Similarity	NPC237188
0.7112	Intermediate Similarity	NPC477044
0.7112	Intermediate Similarity	NPC477041
0.7111	Intermediate Similarity	NPC467063
0.7108	Intermediate Similarity	NPC102664
0.7105	Intermediate Similarity	NPC317701
0.7102	Intermediate Similarity	NPC469529
0.7091	Intermediate Similarity	NPC302159
0.7074	Intermediate Similarity	NPC477004
0.7072	Intermediate Similarity	NPC311282
0.7052	Intermediate Similarity	NPC2414
0.7051	Intermediate Similarity	NPC89490
0.7049	Intermediate Similarity	NPC209917
0.7049	Intermediate Similarity	NPC255909
0.7031	Intermediate Similarity	NPC472064
0.7031	Intermediate Similarity	NPC472065
0.7027	Intermediate Similarity	NPC47190
0.7021	Intermediate Similarity	NPC248782
0.7019	Intermediate Similarity	NPC65408
0.7017	Intermediate Similarity	NPC110158
0.7011	Intermediate Similarity	NPC475874
0.701	Intermediate Similarity	NPC472070
0.7006	Intermediate Similarity	NPC329896
0.7006	Intermediate Similarity	NPC475090
0.7006	Intermediate Similarity	NPC71236
0.7006	Intermediate Similarity	NPC475105
0.7	Intermediate Similarity	NPC98864
0.6995	Remote Similarity	NPC278434
0.6989	Remote Similarity	NPC473821
0.6984	Remote Similarity	NPC477045
0.6983	Remote Similarity	NPC126709
0.6983	Remote Similarity	NPC248041
0.6983	Remote Similarity	NPC11126
0.6983	Remote Similarity	NPC283219
0.6979	Remote Similarity	NPC88115
0.6978	Remote Similarity	NPC295158
0.6971	Remote Similarity	NPC470894
0.6968	Remote Similarity	NPC473814
0.6968	Remote Similarity	NPC74153
0.6968	Remote Similarity	NPC78767
0.6966	Remote Similarity	NPC151635
0.6963	Remote Similarity	NPC328596
0.6963	Remote Similarity	NPC106757
0.6963	Remote Similarity	NPC328318
0.6962	Remote Similarity	NPC282398
0.6957	Remote Similarity	NPC473628
0.6952	Remote Similarity	NPC93390
0.6944	Remote Similarity	NPC79777
0.6941	Remote Similarity	NPC33229
0.6941	Remote Similarity	NPC474236
0.6927	Remote Similarity	NPC138562
0.6919	Remote Similarity	NPC324091
0.6919	Remote Similarity	NPC113812
0.6918	Remote Similarity	NPC471322
0.6915	Remote Similarity	NPC79356
0.6915	Remote Similarity	NPC102592
0.6915	Remote Similarity	NPC128244
0.691	Remote Similarity	NPC110500
0.691	Remote Similarity	NPC203468
0.691	Remote Similarity	NPC149155
0.6909	Remote Similarity	NPC190296
0.6897	Remote Similarity	NPC229893
0.6897	Remote Similarity	NPC469813
0.6897	Remote Similarity	NPC78375
0.6897	Remote Similarity	NPC476446
0.6895	Remote Similarity	NPC237414
0.6891	Remote Similarity	NPC477043
0.6889	Remote Similarity	NPC55772
0.6885	Remote Similarity	NPC133003
0.6882	Remote Similarity	NPC138370
0.6872	Remote Similarity	NPC267885
0.6871	Remote Similarity	NPC27802
0.686	Remote Similarity	NPC469762
0.6859	Remote Similarity	NPC121327
0.6854	Remote Similarity	NPC252572
0.6852	Remote Similarity	NPC29702
0.6851	Remote Similarity	NPC182940
0.6851	Remote Similarity	NPC234403
0.6842	Remote Similarity	NPC34837
0.6842	Remote Similarity	NPC91958
0.6833	Remote Similarity	NPC14113
0.6833	Remote Similarity	NPC145885
0.6833	Remote Similarity	NPC84827
0.6831	Remote Similarity	NPC228835
0.6826	Remote Similarity	NPC159856
0.6826	Remote Similarity	NPC314372
0.6818	Remote Similarity	NPC54988
0.6816	Remote Similarity	NPC139763
0.6813	Remote Similarity	NPC101165
0.6813	Remote Similarity	NPC324611
0.6806	Remote Similarity	NPC81535
0.6806	Remote Similarity	NPC123395
0.6804	Remote Similarity	NPC473239
0.6804	Remote Similarity	NPC327592
0.6802	Remote Similarity	NPC469785
0.6802	Remote Similarity	NPC123839
0.6798	Remote Similarity	NPC302647
0.6798	Remote Similarity	NPC470498
0.6793	Remote Similarity	NPC318020
0.6789	Remote Similarity	NPC227582
0.6786	Remote Similarity	NPC266249
0.6786	Remote Similarity	NPC116555
0.678	Remote Similarity	NPC78020
0.6774	Remote Similarity	NPC182814
0.6772	Remote Similarity	NPC294693
0.6772	Remote Similarity	NPC195239
0.6772	Remote Similarity	NPC471311
0.6772	Remote Similarity	NPC471313
0.6772	Remote Similarity	NPC157828
0.6772	Remote Similarity	NPC20593

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 NPC213914 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	620
0.2-0.3	1079
0.3-0.4	1935
0.4-0.5	2881
0.5-0.6	1888
0.6-0.7	538
0.7-0.8	41
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8047	Intermediate Similarity	NPD1618	Phase 2
0.8025	Intermediate Similarity	NPD1270	Approved
0.7941	Intermediate Similarity	NPD2479	Phase 3
0.7941	Intermediate Similarity	NPD2481	Approved
0.7778	Intermediate Similarity	NPD272	Approved
0.7763	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD2061	Approved
0.7643	Intermediate Similarity	NPD9599	Approved
0.76	Intermediate Similarity	NPD1096	Discontinued
0.7529	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD175	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD9100	Approved
0.7358	Intermediate Similarity	NPD569	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD9075	Approved
0.7346	Intermediate Similarity	NPD9074	Approved
0.7333	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD4051	Discontinued
0.7312	Intermediate Similarity	NPD107	Approved
0.7302	Intermediate Similarity	NPD7289	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD4883	Approved
0.7292	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD460	Discontinued
0.7229	Intermediate Similarity	NPD9343	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD180	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD820	Phase 3
0.7152	Intermediate Similarity	NPD9271	Approved
0.7119	Intermediate Similarity	NPD2753	Discontinued
0.7117	Intermediate Similarity	NPD1427	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD991	Phase 2
0.7097	Intermediate Similarity	NPD4848	Phase 1
0.7095	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD3583	Phase 2
0.7088	Intermediate Similarity	NPD4988	Discontinued
0.7081	Intermediate Similarity	NPD1380	Discovery
0.7081	Intermediate Similarity	NPD2896	Discontinued
0.7081	Intermediate Similarity	NPD1173	Approved
0.7069	Intermediate Similarity	NPD1343	Approved
0.7065	Intermediate Similarity	NPD2336	Approved
0.7062	Intermediate Similarity	NPD3238	Discontinued
0.7052	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD9726	Discontinued
0.7024	Intermediate Similarity	NPD510	Phase 1
0.7019	Intermediate Similarity	NPD200	Phase 2
0.7019	Intermediate Similarity	NPD201	Phase 2
0.7018	Intermediate Similarity	NPD2213	Approved
0.7018	Intermediate Similarity	NPD2214	Approved
0.7017	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD4304	Discovery
0.7011	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3178	Discontinued
0.6994	Remote Similarity	NPD5088	Discontinued
0.6977	Remote Similarity	NPD2511	Approved
0.6971	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD5855	Phase 3
0.6952	Remote Similarity	NPD5853	Phase 3
0.6951	Remote Similarity	NPD1382	Phase 2
0.6951	Remote Similarity	NPD1383	Phase 3
0.6941	Remote Similarity	NPD2809	Approved
0.694	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD4376	Phase 3
0.6923	Remote Similarity	NPD7564	Discontinued
0.6923	Remote Similarity	NPD3569	Discontinued
0.6915	Remote Similarity	NPD2307	Discontinued
0.6914	Remote Similarity	NPD6446	Discontinued
0.6914	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5611	Phase 2
0.691	Remote Similarity	NPD482	Approved
0.691	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD9357	Approved
0.6902	Remote Similarity	NPD2770	Discontinued
0.6895	Remote Similarity	NPD7049	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD4299	Phase 1
0.6887	Remote Similarity	NPD9396	Approved
0.6887	Remote Similarity	NPD9392	Approved
0.6884	Remote Similarity	NPD3394	Approved
0.6884	Remote Similarity	NPD3393	Approved
0.6884	Remote Similarity	NPD3389	Approved
0.6875	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD2509	Approved
0.6872	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD2510	Approved
0.6871	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5888	Phase 2
0.6868	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4524	Discontinued
0.6854	Remote Similarity	NPD750	Phase 2
0.6851	Remote Similarity	NPD1643	Phase 3
0.6851	Remote Similarity	NPD3927	Phase 2
0.6848	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5400	Approved
0.6823	Remote Similarity	NPD5017	Discontinued
0.6821	Remote Similarity	NPD3371	Approved
0.6816	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD9583	Approved
0.6811	Remote Similarity	NPD3246	Discontinued
0.6804	Remote Similarity	NPD3947	Discontinued
0.6798	Remote Similarity	NPD3117	Approved
0.6798	Remote Similarity	NPD3116	Approved
0.6796	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD2118	Approved
0.6772	Remote Similarity	NPD1598	Discontinued
0.6772	Remote Similarity	NPD2119	Approved
0.6755	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD1722	Approved
0.6747	Remote Similarity	NPD4805	Approved
0.6746	Remote Similarity	NPD4702	Approved
0.6746	Remote Similarity	NPD4703	Approved
0.6742	Remote Similarity	NPD1573	Approved
0.6742	Remote Similarity	NPD1575	Approved
0.6739	Remote Similarity	NPD2091	Phase 2
0.6739	Remote Similarity	NPD2096	Phase 2
0.6737	Remote Similarity	NPD6226	Phase 3
0.6735	Remote Similarity	NPD3411	Phase 2
0.6735	Remote Similarity	NPD3410	Approved
0.6727	Remote Similarity	NPD768	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD5854	Approved
0.6718	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD944	Approved
0.6717	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.671	Remote Similarity	NPD271	Approved
0.671	Remote Similarity	NPD268	Approved
0.671	Remote Similarity	NPD270	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD803	Phase 1
0.6707	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD9506	Approved
0.6705	Remote Similarity	NPD1631	Approved
0.67	Remote Similarity	NPD3794	Approved
0.67	Remote Similarity	NPD3795	Approved
0.6687	Remote Similarity	NPD1395	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD2095	Phase 2
0.6685	Remote Similarity	NPD2094	Phase 2
0.6685	Remote Similarity	NPD2092	Phase 2
0.6684	Remote Similarity	NPD7618	Phase 3
0.6684	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7619	Phase 3
0.6684	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6068	Discontinued
0.6684	Remote Similarity	NPD7010	Phase 3
0.6667	Remote Similarity	NPD8242	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9080	Approved
0.6667	Remote Similarity	NPD6665	Discontinued
0.6667	Remote Similarity	NPD9510	Approved
0.6667	Remote Similarity	NPD3968	Approved
0.6667	Remote Similarity	NPD7026	Phase 2
0.665	Remote Similarity	NPD6173	Approved
0.665	Remote Similarity	NPD4913	Phase 3
0.6649	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD2290	Phase 3
0.6649	Remote Similarity	NPD7817	Phase 1
0.6649	Remote Similarity	NPD7727	Phase 2
0.6649	Remote Similarity	NPD2289	Phase 3
0.6649	Remote Similarity	NPD721	Approved
0.6648	Remote Similarity	NPD6771	Discontinued
0.6648	Remote Similarity	NPD8026	Phase 1
0.6646	Remote Similarity	NPD9206	Approved
0.6646	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD9207	Approved
0.6634	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD8115	Approved
0.6633	Remote Similarity	NPD8114	Approved
0.6632	Remote Similarity	NPD2405	Phase 3
0.6629	Remote Similarity	NPD1630	Approved
0.6627	Remote Similarity	NPD4804	Approved
0.6615	Remote Similarity	NPD7187	Phase 2
0.6609	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD2748	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD1527	Phase 2
0.66	Remote Similarity	NPD5475	Discontinued
0.6599	Remote Similarity	NPD2008	Discontinued
0.6599	Remote Similarity	NPD3967	Approved
0.6596	Remote Similarity	NPD7175	Phase 1
0.6595	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD5510	Approved
0.6583	Remote Similarity	NPD1600	Suspended
0.6579	Remote Similarity	NPD4922	Phase 2
0.6576	Remote Similarity	NPD5473	Discontinued
0.6571	Remote Similarity	NPD2582	Approved
0.6571	Remote Similarity	NPD2581	Approved
0.6566	Remote Similarity	NPD3840	Phase 2
0.6566	Remote Similarity	NPD3839	Phase 2
0.6564	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD9284	Approved
0.6561	Remote Similarity	NPD5686	Approved
0.6561	Remote Similarity	NPD5685	Approved
0.6559	Remote Similarity	NPD6178	Phase 3
0.6557	Remote Similarity	NPD3506	Approved
0.6557	Remote Similarity	NPD3505	Approved
0.655	Remote Similarity	NPD7998	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