NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	129.06
Volume:	144.922
LogP:	2.061
LogD:	2.058
LogS:	-1.481
# Rotatable Bonds:	0
TPSA:	12.89
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.531
Synthetic Accessibility Score:	1.542
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.141
MDCK Permeability:	3.6514928069664165e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.94
30% Bioavailability (F30%):	0.053

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.886
Plasma Protein Binding (PPB):	83.76776885986328%
Volume Distribution (VD):	2.287
Pgp-substrate:	17.612136840820312%

ADMET: Metabolism

CYP1A2-inhibitor:	0.986
CYP1A2-substrate:	0.582
CYP2C19-inhibitor:	0.854
CYP2C19-substrate:	0.439
CYP2C9-inhibitor:	0.273
CYP2C9-substrate:	0.556
CYP2D6-inhibitor:	0.736
CYP2D6-substrate:	0.618
CYP3A4-inhibitor:	0.584
CYP3A4-substrate:	0.346

ADMET: Excretion

Clearance (CL):	12.951
Half-life (T1/2):	0.67

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.093
Drug-inuced Liver Injury (DILI):	0.938
AMES Toxicity:	0.149
Rat Oral Acute Toxicity:	0.821
Maximum Recommended Daily Dose:	0.096
Skin Sensitization:	0.92
Carcinogencity:	0.323
Eye Corrosion:	0.377
Eye Irritation:	0.991
Respiratory Toxicity:	0.707

Download Data

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

Natural Product: NPC143603

Natural Product ID:	NPC143603
*Common Name:**	Isoquinoline
IUPAC Name:	isoquinoline
Synonyms:	2-Benzanine
Standard InCHIKey:	AWJUIBRHMBBTKR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H7N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-7H
SMILES:	c1ccc2c(c1)cncc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL12315
PubChem CID:	8405
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002566] Isoquinolines and derivatives

*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
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1002/elan.200403102]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2012.02.124]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[11077184]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[17328234]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[18321056]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower	n.a.	PMID[21804227]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	flower buds	Henan province, China	2005-MAY	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23265495]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[24279769]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
Ki	1
Others	21
Potency	7

Activity Type	# Activity
Individual Protein	4
Organism	1
Others	21
Protein Complex	1
Tissue	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	30637.9	nM	PubChem BioAssay data set
NPT1073	Individual Protein	Dopamine transporter	Rattus norvegicus	DA release	=	0.4	%	PMID[525644]
NPT1073	Individual Protein	Dopamine transporter	Rattus norvegicus	DA release	=	18.0	%	PMID[525644]
NPT592	Individual Protein	Rho-associated protein kinase 1	Homo sapiens	Activity	=	70.0	%	PMID[525650]
NPT2	Others	Unspecified		Potency	n.a.	1096.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	27306	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	30637.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61130.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54482.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	76958.8	nM	PubChem BioAssay data set
NPT35	Others	n.a.		pKa	=	5.4	n.a.	PMID[525642]
NPT805	Protein Complex	GABA-A receptor; anion channel	Rattus norvegicus	Ki	>	100000.0	nM	PMID[525643]
NPT35	Others	n.a.		Log PNalk	=	1.11	n.a.	PMID[525645]
NPT35	Others	n.a.		pKa	=	5.37	n.a.	PMID[525646]
NPT605	Organism	Homo sapiens	Homo sapiens	log Kp	=	-5.33	cm/s	PMID[525646]
NPT27	Others	Unspecified		Activity	=	44.5	%	PMID[525646]
NPT27	Others	Unspecified		log Pe	=	-4.05	cm/s	PMID[525646]
NPT27	Others	Unspecified		Activity	=	7.3	%	PMID[525646]
NPT35	Others	n.a.		LogP	=	2.08	n.a.	PMID[525647]
NPT615	Tissue	Skin	Homo sapiens	log Kp	=	-5.33	n.a.	PMID[525647]
NPT27	Others	Unspecified		log Pe	=	-4.05	n.a.	PMID[525647]
NPT615	Tissue	Skin	Homo sapiens	log Kp	=	-5.34	n.a.	PMID[525648]
NPT35	Others	n.a.		LogD	=	2.09	n.a.	PMID[525649]
NPT35	Others	n.a.		LogD	=	0.98	n.a.	PMID[525649]
NPT35	Others	n.a.		LogP	=	2.08	n.a.	PMID[525651]
NPT35	Others	n.a.		LogP	=	2.09	n.a.	PMID[525651]
NPT35	Others	n.a.		LogD7.4	n.a.	1.6	n.a.	PMID[525652]
NPT35	Others	n.a.		LogP	=	2.09	n.a.	PMID[525654]
NPT35	Others	n.a.		Solubility	=	5660.0	ug.mL-1	PMID[525654]

☑ 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 NPC143603 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	1478
0.1-0.2	13624
0.2-0.3	16611
0.3-0.4	5974
0.4-0.5	2533
0.5-0.6	1674
0.6-0.7	556
0.7-0.8	209
0.8-0.85	26
0.85-0.9	8
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9646	High Similarity	NPC91958
0.9076	High Similarity	NPC46358
0.9024	High Similarity	NPC282398
0.8938	High Similarity	NPC27802
0.8889	High Similarity	NPC240136
0.8889	High Similarity	NPC471402
0.8889	High Similarity	NPC297486
0.8839	High Similarity	NPC76540
0.8689	High Similarity	NPC476322
0.8595	High Similarity	NPC182570
0.8595	High Similarity	NPC265605
0.8595	High Similarity	NPC48564
0.8538	High Similarity	NPC169433
0.8504	High Similarity	NPC101165
0.8468	Intermediate Similarity	NPC146373
0.8468	Intermediate Similarity	NPC166424
0.8468	Intermediate Similarity	NPC83987
0.8468	Intermediate Similarity	NPC245244
0.8462	Intermediate Similarity	NPC235843
0.8455	Intermediate Similarity	NPC290094
0.8387	Intermediate Similarity	NPC27740
0.8374	Intermediate Similarity	NPC329825
0.8359	Intermediate Similarity	NPC256893
0.8346	Intermediate Similarity	NPC476131
0.8321	Intermediate Similarity	NPC314102
0.8321	Intermediate Similarity	NPC251722
0.8281	Intermediate Similarity	NPC69914
0.8254	Intermediate Similarity	NPC169625
0.8254	Intermediate Similarity	NPC202957
0.819	Intermediate Similarity	NPC231655
0.8162	Intermediate Similarity	NPC86288
0.8125	Intermediate Similarity	NPC89490
0.8077	Intermediate Similarity	NPC82295
0.8062	Intermediate Similarity	NPC329896
0.8062	Intermediate Similarity	NPC475090
0.8062	Intermediate Similarity	NPC475105
0.806	Intermediate Similarity	NPC315348
0.806	Intermediate Similarity	NPC316811
0.806	Intermediate Similarity	NPC32002
0.8047	Intermediate Similarity	NPC471313
0.8047	Intermediate Similarity	NPC471311
0.8033	Intermediate Similarity	NPC148140
0.797	Intermediate Similarity	NPC96102
0.797	Intermediate Similarity	NPC261195
0.797	Intermediate Similarity	NPC29886
0.7967	Intermediate Similarity	NPC81561
0.7939	Intermediate Similarity	NPC324611
0.791	Intermediate Similarity	NPC105127
0.791	Intermediate Similarity	NPC150259
0.791	Intermediate Similarity	NPC84911
0.7903	Intermediate Similarity	NPC162689
0.7903	Intermediate Similarity	NPC54102
0.7842	Intermediate Similarity	NPC63545
0.7817	Intermediate Similarity	NPC138842
0.7803	Intermediate Similarity	NPC471322
0.7794	Intermediate Similarity	NPC110126
0.7794	Intermediate Similarity	NPC73767
0.7786	Intermediate Similarity	NPC201380
0.7786	Intermediate Similarity	NPC470111
0.7786	Intermediate Similarity	NPC469811
0.7786	Intermediate Similarity	NPC179787
0.7778	Intermediate Similarity	NPC215519
0.7737	Intermediate Similarity	NPC230002
0.7737	Intermediate Similarity	NPC469768
0.7737	Intermediate Similarity	NPC469767
0.7737	Intermediate Similarity	NPC469783
0.7737	Intermediate Similarity	NPC469779
0.7737	Intermediate Similarity	NPC469761
0.7737	Intermediate Similarity	NPC469784
0.7737	Intermediate Similarity	NPC469780
0.7737	Intermediate Similarity	NPC279081
0.773	Intermediate Similarity	NPC321911
0.7681	Intermediate Similarity	NPC469766
0.7676	Intermediate Similarity	NPC40070
0.766	Intermediate Similarity	NPC477974
0.7655	Intermediate Similarity	NPC469897
0.7647	Intermediate Similarity	NPC65408
0.7642	Intermediate Similarity	NPC473901
0.7626	Intermediate Similarity	NPC190296
0.7622	Intermediate Similarity	NPC470233
0.7603	Intermediate Similarity	NPC80681
0.7603	Intermediate Similarity	NPC56765
0.7594	Intermediate Similarity	NPC315320
0.7589	Intermediate Similarity	NPC143872
0.7589	Intermediate Similarity	NPC288838
0.7569	Intermediate Similarity	NPC325903
0.7554	Intermediate Similarity	NPC476454
0.7551	Intermediate Similarity	NPC215584
0.7551	Intermediate Similarity	NPC44773
0.7538	Intermediate Similarity	NPC122718
0.752	Intermediate Similarity	NPC84268
0.7518	Intermediate Similarity	NPC314372
0.7518	Intermediate Similarity	NPC159856
0.7518	Intermediate Similarity	NPC285731
0.7518	Intermediate Similarity	NPC471312
0.75	Intermediate Similarity	NPC198988
0.75	Intermediate Similarity	NPC306397
0.75	Intermediate Similarity	NPC212125
0.75	Intermediate Similarity	NPC165370
0.7481	Intermediate Similarity	NPC322488
0.7466	Intermediate Similarity	NPC51054
0.746	Intermediate Similarity	NPC476566
0.745	Intermediate Similarity	NPC90723
0.745	Intermediate Similarity	NPC265100
0.7445	Intermediate Similarity	NPC325252
0.7444	Intermediate Similarity	NPC471589
0.7431	Intermediate Similarity	NPC53947
0.7424	Intermediate Similarity	NPC476140
0.7415	Intermediate Similarity	NPC129721
0.7415	Intermediate Similarity	NPC286427
0.7415	Intermediate Similarity	NPC236711
0.7413	Intermediate Similarity	NPC471957
0.741	Intermediate Similarity	NPC104483
0.7376	Intermediate Similarity	NPC20144
0.7376	Intermediate Similarity	NPC477977
0.7365	Intermediate Similarity	NPC318065
0.7365	Intermediate Similarity	NPC41257
0.7365	Intermediate Similarity	NPC293487
0.7365	Intermediate Similarity	NPC477591
0.7365	Intermediate Similarity	NPC206819
0.735	Intermediate Similarity	NPC213774
0.7347	Intermediate Similarity	NPC476464
0.7343	Intermediate Similarity	NPC316069
0.7333	Intermediate Similarity	NPC22079
0.7315	Intermediate Similarity	NPC122141
0.7315	Intermediate Similarity	NPC470204
0.731	Intermediate Similarity	NPC24678
0.731	Intermediate Similarity	NPC105818
0.7293	Intermediate Similarity	NPC135488
0.7293	Intermediate Similarity	NPC250361
0.7287	Intermediate Similarity	NPC11863
0.7286	Intermediate Similarity	NPC88097
0.7267	Intermediate Similarity	NPC478185
0.7267	Intermediate Similarity	NPC225018
0.7267	Intermediate Similarity	NPC470203
0.726	Intermediate Similarity	NPC216713
0.726	Intermediate Similarity	NPC470823
0.7252	Intermediate Similarity	NPC41174
0.7234	Intermediate Similarity	NPC2949
0.7234	Intermediate Similarity	NPC59084
0.7226	Intermediate Similarity	NPC330326
0.7219	Intermediate Similarity	NPC478184
0.7219	Intermediate Similarity	NPC97367
0.7219	Intermediate Similarity	NPC317105
0.7219	Intermediate Similarity	NPC478182
0.7211	Intermediate Similarity	NPC200214
0.7211	Intermediate Similarity	NPC73952
0.7211	Intermediate Similarity	NPC141926
0.7211	Intermediate Similarity	NPC469765
0.7211	Intermediate Similarity	NPC469763
0.7211	Intermediate Similarity	NPC25008
0.7211	Intermediate Similarity	NPC469760
0.7211	Intermediate Similarity	NPC259644
0.7211	Intermediate Similarity	NPC469786
0.7203	Intermediate Similarity	NPC471323
0.7194	Intermediate Similarity	NPC29702
0.719	Intermediate Similarity	NPC70949
0.7185	Intermediate Similarity	NPC473762
0.7183	Intermediate Similarity	NPC473868
0.7183	Intermediate Similarity	NPC63157
0.7181	Intermediate Similarity	NPC216643
0.7171	Intermediate Similarity	NPC274229
0.7162	Intermediate Similarity	NPC75540
0.7162	Intermediate Similarity	NPC80597
0.7162	Intermediate Similarity	NPC70922
0.7162	Intermediate Similarity	NPC211572
0.7162	Intermediate Similarity	NPC34844
0.7162	Intermediate Similarity	NPC212376
0.7153	Intermediate Similarity	NPC467188
0.7143	Intermediate Similarity	NPC116961
0.7143	Intermediate Similarity	NPC125746
0.7133	Intermediate Similarity	NPC92796
0.7133	Intermediate Similarity	NPC135141
0.7132	Intermediate Similarity	NPC473587
0.7124	Intermediate Similarity	NPC56233
0.7124	Intermediate Similarity	NPC478183
0.7121	Intermediate Similarity	NPC56856
0.7114	Intermediate Similarity	NPC469785
0.7113	Intermediate Similarity	NPC115611
0.7105	Intermediate Similarity	NPC473057
0.7097	Intermediate Similarity	NPC201634
0.7086	Intermediate Similarity	NPC279918
0.708	Intermediate Similarity	NPC475428
0.7075	Intermediate Similarity	NPC33421
0.7071	Intermediate Similarity	NPC218268
0.7067	Intermediate Similarity	NPC469762
0.7059	Intermediate Similarity	NPC477975
0.7055	Intermediate Similarity	NPC105811
0.7039	Intermediate Similarity	NPC471177
0.7039	Intermediate Similarity	NPC124542
0.7039	Intermediate Similarity	NPC282231
0.7039	Intermediate Similarity	NPC59779
0.7034	Intermediate Similarity	NPC470440
0.7034	Intermediate Similarity	NPC204141
0.7032	Intermediate Similarity	NPC91895
0.7032	Intermediate Similarity	NPC194411
0.7032	Intermediate Similarity	NPC97343
0.7032	Intermediate Similarity	NPC32534
0.7029	Intermediate Similarity	NPC179365
0.7029	Intermediate Similarity	NPC475450

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 NPC143603 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	587
0.1-0.2	913
0.2-0.3	925
0.3-0.4	2238
0.4-0.5	2461
0.5-0.6	1448
0.6-0.7	441
0.7-0.8	112
0.8-0.85	20
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.878	High Similarity	NPD2118	Approved
0.878	High Similarity	NPD2119	Approved
0.8661	High Similarity	NPD3944	Approved
0.8661	High Similarity	NPD3942	Approved
0.8661	High Similarity	NPD4028	Approved
0.8661	High Similarity	NPD4030	Approved
0.8661	High Similarity	NPD4029	Approved
0.8629	High Similarity	NPD992	Clinical (unspecified phase)
0.8629	High Similarity	NPD991	Phase 2
0.8629	High Similarity	NPD1598	Discontinued
0.8595	High Similarity	NPD270	Clinical (unspecified phase)
0.8595	High Similarity	NPD268	Approved
0.8595	High Similarity	NPD271	Approved
0.8425	Intermediate Similarity	NPD3475	Approved
0.8425	Intermediate Similarity	NPD3476	Approved
0.8403	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.8305	Intermediate Similarity	NPD4823	Approved
0.8305	Intermediate Similarity	NPD4824	Approved
0.8295	Intermediate Similarity	NPD1994	Approved
0.8295	Intermediate Similarity	NPD1993	Approved
0.8295	Intermediate Similarity	NPD1995	Approved
0.8254	Intermediate Similarity	NPD9583	Approved
0.824	Intermediate Similarity	NPD9357	Approved
0.8222	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.819	Intermediate Similarity	NPD9099	Clinical (unspecified phase)
0.819	Intermediate Similarity	NPD9098	Phase 3
0.814	Intermediate Similarity	NPD715	Phase 3
0.8074	Intermediate Similarity	NPD1722	Approved
0.806	Intermediate Similarity	NPD2071	Approved
0.806	Intermediate Similarity	NPD2072	Approved
0.806	Intermediate Similarity	NPD2070	Approved
0.806	Intermediate Similarity	NPD2075	Approved
0.806	Intermediate Similarity	NPD2074	Approved
0.806	Intermediate Similarity	NPD2073	Approved
0.806	Intermediate Similarity	NPD2068	Approved
0.806	Intermediate Similarity	NPD2069	Approved
0.803	Intermediate Similarity	NPD2141	Approved
0.803	Intermediate Similarity	NPD2140	Approved
0.803	Intermediate Similarity	NPD2142	Approved
0.8015	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7985	Intermediate Similarity	NPD2896	Discontinued
0.7971	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.797	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.797	Intermediate Similarity	NPD792	Discontinued
0.7937	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.7883	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7883	Intermediate Similarity	NPD2006	Phase 2
0.7883	Intermediate Similarity	NPD4510	Discontinued
0.7823	Intermediate Similarity	NPD9392	Approved
0.7823	Intermediate Similarity	NPD9396	Approved
0.7801	Intermediate Similarity	NPD2466	Phase 3
0.7801	Intermediate Similarity	NPD2465	Approved
0.7801	Intermediate Similarity	NPD2462	Phase 3
0.7794	Intermediate Similarity	NPD786	Approved
0.7794	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD4547	Phase 3
0.7762	Intermediate Similarity	NPD1328	Approved
0.773	Intermediate Similarity	NPD2430	Phase 2
0.7708	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD3813	Approved
0.7692	Intermediate Similarity	NPD3339	Approved
0.7687	Intermediate Similarity	NPD3385	Approved
0.766	Intermediate Similarity	NPD1661	Suspended
0.766	Intermediate Similarity	NPD4702	Approved
0.766	Intermediate Similarity	NPD4703	Approved
0.7647	Intermediate Similarity	NPD201	Phase 2
0.7647	Intermediate Similarity	NPD200	Phase 2
0.7639	Intermediate Similarity	NPD977	Approved
0.7639	Intermediate Similarity	NPD975	Approved
0.7639	Intermediate Similarity	NPD976	Approved
0.7622	Intermediate Similarity	NPD4641	Discontinued
0.7622	Intermediate Similarity	NPD3262	Approved
0.7594	Intermediate Similarity	NPD9206	Approved
0.7594	Intermediate Similarity	NPD9207	Approved
0.7589	Intermediate Similarity	NPD7469	Discontinued
0.7569	Intermediate Similarity	NPD2837	Discontinued
0.7536	Intermediate Similarity	NPD945	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD1270	Approved
0.7534	Intermediate Similarity	NPD6497	Approved
0.752	Intermediate Similarity	NPD60	Approved
0.7519	Intermediate Similarity	NPD3654	Approved
0.75	Intermediate Similarity	NPD9284	Approved
0.75	Intermediate Similarity	NPD9080	Approved
0.75	Intermediate Similarity	NPD5315	Discontinued
0.75	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1183	Approved
0.7483	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD3100	Discontinued
0.745	Intermediate Similarity	NPD3323	Discontinued
0.745	Intermediate Similarity	NPD3583	Phase 2
0.7447	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD2110	Approved
0.7407	Intermediate Similarity	NPD803	Phase 1
0.7407	Intermediate Similarity	NPD9726	Discontinued
0.7402	Intermediate Similarity	NPD8840	Approved
0.7397	Intermediate Similarity	NPD2165	Phase 1
0.7383	Intermediate Similarity	NPD4384	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD5400	Approved
0.7347	Intermediate Similarity	NPD3112	Approved
0.7347	Intermediate Similarity	NPD3114	Approved
0.7347	Intermediate Similarity	NPD2580	Discontinued
0.7347	Intermediate Similarity	NPD6026	Approved
0.7347	Intermediate Similarity	NPD3115	Approved
0.7347	Intermediate Similarity	NPD3113	Approved
0.7329	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD1253	Approved
0.7319	Intermediate Similarity	NPD1255	Approved
0.7319	Intermediate Similarity	NPD1254	Approved
0.7319	Intermediate Similarity	NPD1256	Approved
0.7313	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD2172	Phase 1
0.7308	Intermediate Similarity	NPD9598	Discontinued
0.7303	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD2581	Approved
0.7297	Intermediate Similarity	NPD2145	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD5541	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD2582	Approved
0.7279	Intermediate Similarity	NPD2809	Approved
0.7267	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD6554	Approved
0.7266	Intermediate Similarity	NPD45	Approved
0.726	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD947	Approved
0.7254	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD1561	Phase 2
0.7248	Intermediate Similarity	NPD1679	Approved
0.7248	Intermediate Similarity	NPD5255	Approved
0.7246	Intermediate Similarity	NPD272	Approved
0.7237	Intermediate Similarity	NPD3929	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD6446	Discontinued
0.7234	Intermediate Similarity	NPD1649	Discontinued
0.7234	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD9100	Approved
0.7214	Intermediate Similarity	NPD1380	Discovery
0.7211	Intermediate Similarity	NPD1917	Discontinued
0.7208	Intermediate Similarity	NPD3609	Approved
0.7208	Intermediate Similarity	NPD3610	Approved
0.72	Intermediate Similarity	NPD9705	Discontinued
0.72	Intermediate Similarity	NPD2511	Approved
0.72	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD112	Approved
0.7194	Intermediate Similarity	NPD206	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2720	Phase 1
0.7162	Intermediate Similarity	NPD2061	Approved
0.7153	Intermediate Similarity	NPD1251	Discontinued
0.7152	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4973	Approved
0.7143	Intermediate Similarity	NPD9506	Approved
0.7133	Intermediate Similarity	NPD5418	Discontinued
0.7133	Intermediate Similarity	NPD3717	Discontinued
0.7124	Intermediate Similarity	NPD5636	Discontinued
0.7113	Intermediate Similarity	NPD1395	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6635	Approved
0.7103	Intermediate Similarity	NPD1683	Approved
0.7092	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5254	Discontinued
0.7083	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1988	Phase 1
0.7078	Intermediate Similarity	NPD4639	Approved
0.7078	Intermediate Similarity	NPD4640	Approved
0.7078	Intermediate Similarity	NPD4638	Approved
0.7078	Intermediate Similarity	NPD5862	Discovery
0.7078	Intermediate Similarity	NPD2640	Approved
0.7078	Intermediate Similarity	NPD2641	Approved
0.707	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD5100	Phase 3
0.7063	Intermediate Similarity	NPD1382	Phase 2
0.7063	Intermediate Similarity	NPD1383	Phase 3
0.7059	Intermediate Similarity	NPD2780	Approved
0.7059	Intermediate Similarity	NPD2782	Approved
0.7055	Intermediate Similarity	NPD2089	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD8026	Phase 1
0.7039	Intermediate Similarity	NPD6771	Discontinued
0.7032	Intermediate Similarity	NPD5436	Phase 1
0.7029	Intermediate Similarity	NPD809	Discontinued
0.7025	Intermediate Similarity	NPD4181	Approved
0.7014	Intermediate Similarity	NPD1427	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2150	Discontinued
0.6993	Remote Similarity	NPD9599	Approved
0.6992	Remote Similarity	NPD5787	Discontinued
0.6974	Remote Similarity	NPD1404	Approved
0.6974	Remote Similarity	NPD1403	Approved
0.6972	Remote Similarity	NPD2323	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4811	Discontinued
0.6968	Remote Similarity	NPD2333	Discontinued
0.6968	Remote Similarity	NPD7287	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2781	Approved
0.6968	Remote Similarity	NPD2390	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD649	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4509	Discontinued
0.6966	Remote Similarity	NPD5671	Approved
0.6962	Remote Similarity	NPD6471	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD3238	Discontinued
0.695	Remote Similarity	NPD490	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD925	Approved
0.6948	Remote Similarity	NPD926	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