NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	224.07
Volume:	221.025
LogP:	1.221
LogD:	0.542
LogS:	-1.289
# Rotatable Bonds:	3
TPSA:	94.83
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.671
Synthetic Accessibility Score:	2.467
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:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.198
MDCK Permeability:	1.0145628948521335e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.023
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.031
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.034
Plasma Protein Binding (PPB):	92.3601303100586%
Volume Distribution (VD):	0.365
Pgp-substrate:	6.07280158996582%

ADMET: Metabolism

CYP1A2-inhibitor:	0.12
CYP1A2-substrate:	0.117
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.043
CYP2C9-substrate:	0.734
CYP2D6-inhibitor:	0.028
CYP2D6-substrate:	0.171
CYP3A4-inhibitor:	0.02
CYP3A4-substrate:	0.097

ADMET: Excretion

Clearance (CL):	9.019
Half-life (T1/2):	0.923

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.153
Drug-inuced Liver Injury (DILI):	0.927
AMES Toxicity:	0.255
Rat Oral Acute Toxicity:	0.056
Maximum Recommended Daily Dose:	0.024
Skin Sensitization:	0.809
Carcinogencity:	0.06
Eye Corrosion:	0.182
Eye Irritation:	0.888
Respiratory Toxicity:	0.381

Download Data

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

Natural Product: NPC48036

Natural Product ID:	NPC48036
*Common Name:**	6-Methylcurvulinic Acid
IUPAC Name:	2-(2-acetyl-3,5-dihydroxy-4-methylphenyl)acetic acid
Synonyms:
Standard InCHIKey:	RLDOSQILCSICAK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H12O5/c1-5-8(13)3-7(4-9(14)15)10(6(2)12)11(5)16/h3,13,16H,4H2,1-2H3,(H,14,15)
SMILES:	OC(=O)Cc1cc(O)c(c(c1C(=O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2385864
PubChem CID:	71725224
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730261]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15973055]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18656987]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21053938]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	Moroccan	n.a.	PMID[23713692]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26295595]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7766039]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	IC50	>	10000.0	nM	PMID[515748]

☑ 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 NPC48036 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	347
0.1-0.2	1642
0.2-0.3	3992
0.3-0.4	10605
0.4-0.5	8718
0.5-0.6	5355
0.6-0.7	6698
0.7-0.8	4542
0.8-0.85	562
0.85-0.9	182
0.9-0.95	49
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9603	High Similarity	NPC41263
0.9538	High Similarity	NPC278375
0.9535	High Similarity	NPC37299
0.9535	High Similarity	NPC180261
0.9462	High Similarity	NPC474519
0.9389	High Similarity	NPC290803
0.9365	High Similarity	NPC201728
0.9365	High Similarity	NPC262671
0.9318	High Similarity	NPC158481
0.9318	High Similarity	NPC118919
0.9259	High Similarity	NPC290550
0.9248	High Similarity	NPC471452
0.9237	High Similarity	NPC267205
0.9185	High Similarity	NPC99441
0.9167	High Similarity	NPC474394
0.9154	High Similarity	NPC247477
0.9154	High Similarity	NPC62219
0.9154	High Similarity	NPC17840
0.9118	High Similarity	NPC37530
0.9111	High Similarity	NPC162939
0.9104	High Similarity	NPC474771
0.9104	High Similarity	NPC65837
0.9104	High Similarity	NPC149372
0.9104	High Similarity	NPC474849
0.9104	High Similarity	NPC178467
0.9062	High Similarity	NPC477454
0.9048	High Similarity	NPC226275
0.9044	High Similarity	NPC165172
0.9037	High Similarity	NPC475974
0.903	High Similarity	NPC254847
0.903	High Similarity	NPC191976
0.8992	High Similarity	NPC473691
0.8971	High Similarity	NPC474655
0.8963	High Similarity	NPC471905
0.8963	High Similarity	NPC194579
0.8963	High Similarity	NPC53414
0.8963	High Similarity	NPC53206
0.8955	High Similarity	NPC161632
0.8939	High Similarity	NPC219892
0.8939	High Similarity	NPC189823
0.8913	High Similarity	NPC193555
0.8898	High Similarity	NPC215392
0.8897	High Similarity	NPC4214
0.8897	High Similarity	NPC472403
0.8897	High Similarity	NPC177307
0.8897	High Similarity	NPC9121
0.8889	High Similarity	NPC50455
0.8881	High Similarity	NPC282780
0.8881	High Similarity	NPC166480
0.8864	High Similarity	NPC296158
0.8855	High Similarity	NPC95537
0.8849	High Similarity	NPC159721
0.8841	High Similarity	NPC478217
0.8841	High Similarity	NPC313123
0.8832	High Similarity	NPC92655
0.8832	High Similarity	NPC143438
0.8832	High Similarity	NPC242994
0.8832	High Similarity	NPC138099
0.8828	High Similarity	NPC91105
0.8819	High Similarity	NPC146642
0.8806	High Similarity	NPC153783
0.8803	High Similarity	NPC471907
0.8788	High Similarity	NPC92624
0.8786	High Similarity	NPC151607
0.8786	High Similarity	NPC42540
0.8777	High Similarity	NPC73061
0.8769	High Similarity	NPC475733
0.8768	High Similarity	NPC169452
0.8768	High Similarity	NPC181560
0.8768	High Similarity	NPC183345
0.876	High Similarity	NPC65761
0.876	High Similarity	NPC472029
0.8759	High Similarity	NPC191835
0.875	High Similarity	NPC223836
0.8741	High Similarity	NPC44437
0.8741	High Similarity	NPC175943
0.874	High Similarity	NPC294037
0.873	High Similarity	NPC40649
0.873	High Similarity	NPC209486
0.8723	High Similarity	NPC473692
0.8723	High Similarity	NPC12402
0.8722	High Similarity	NPC259942
0.8714	High Similarity	NPC354984
0.8714	High Similarity	NPC471731
0.8714	High Similarity	NPC478202
0.8705	High Similarity	NPC305845
0.8705	High Similarity	NPC478201
0.8705	High Similarity	NPC472035
0.8705	High Similarity	NPC472603
0.8705	High Similarity	NPC110810
0.8705	High Similarity	NPC246638
0.8705	High Similarity	NPC204045
0.8702	High Similarity	NPC473751
0.8702	High Similarity	NPC160499
0.8696	High Similarity	NPC88269
0.8696	High Similarity	NPC275356
0.8696	High Similarity	NPC190457
0.8686	High Similarity	NPC71256
0.8686	High Similarity	NPC53001
0.8686	High Similarity	NPC70380
0.8682	High Similarity	NPC309765
0.8676	High Similarity	NPC180905
0.8676	High Similarity	NPC182496
0.8672	High Similarity	NPC149246
0.8662	High Similarity	NPC163846
0.8662	High Similarity	NPC225173
0.8643	High Similarity	NPC474961
0.8643	High Similarity	NPC94076
0.8643	High Similarity	NPC471733
0.8643	High Similarity	NPC182255
0.8643	High Similarity	NPC135524
0.8636	High Similarity	NPC209959
0.8633	High Similarity	NPC168471
0.8633	High Similarity	NPC472601
0.8633	High Similarity	NPC472600
0.8626	High Similarity	NPC10926
0.8623	High Similarity	NPC212693
0.8623	High Similarity	NPC87723
0.8623	High Similarity	NPC94248
0.8623	High Similarity	NPC33144
0.8623	High Similarity	NPC478200
0.8613	High Similarity	NPC86524
0.8613	High Similarity	NPC235115
0.8605	High Similarity	NPC303737
0.8603	High Similarity	NPC288089
0.8603	High Similarity	NPC12070
0.8603	High Similarity	NPC475645
0.8601	High Similarity	NPC166583
0.8601	High Similarity	NPC53362
0.8601	High Similarity	NPC125801
0.8593	High Similarity	NPC175738
0.8582	High Similarity	NPC293545
0.8582	High Similarity	NPC66593
0.8582	High Similarity	NPC313047
0.8582	High Similarity	NPC174905
0.8582	High Similarity	NPC474203
0.8582	High Similarity	NPC295712
0.8582	High Similarity	NPC147757
0.8582	High Similarity	NPC84266
0.8582	High Similarity	NPC451542
0.8571	High Similarity	NPC472605
0.8571	High Similarity	NPC472604
0.8571	High Similarity	NPC179898
0.8561	High Similarity	NPC8745
0.8561	High Similarity	NPC52358
0.8561	High Similarity	NPC105456
0.8561	High Similarity	NPC26924
0.8561	High Similarity	NPC268052
0.8561	High Similarity	NPC267846
0.8561	High Similarity	NPC139634
0.8552	High Similarity	NPC158866
0.8551	High Similarity	NPC135837
0.8551	High Similarity	NPC245058
0.855	High Similarity	NPC13238
0.8542	High Similarity	NPC37139
0.8542	High Similarity	NPC105415
0.854	High Similarity	NPC249272
0.8538	High Similarity	NPC283514
0.8529	High Similarity	NPC114183
0.8521	High Similarity	NPC126882
0.8521	High Similarity	NPC478203
0.8521	High Similarity	NPC193703
0.8521	High Similarity	NPC227841
0.8521	High Similarity	NPC471906
0.8521	High Similarity	NPC48762
0.8521	High Similarity	NPC21599
0.8521	High Similarity	NPC244691
0.8521	High Similarity	NPC210966
0.8516	High Similarity	NPC161617
0.8511	High Similarity	NPC322112
0.8511	High Similarity	NPC291078
0.8511	High Similarity	NPC82913
0.8507	High Similarity	NPC474998
0.8507	High Similarity	NPC109123
0.8504	High Similarity	NPC125252
0.85	High Similarity	NPC315578
0.8496	Intermediate Similarity	NPC169250
0.8496	Intermediate Similarity	NPC83572
0.8496	Intermediate Similarity	NPC116513
0.8496	Intermediate Similarity	NPC23126
0.8496	Intermediate Similarity	NPC266689
0.8496	Intermediate Similarity	NPC162612
0.8496	Intermediate Similarity	NPC190043
0.8496	Intermediate Similarity	NPC72158
0.8496	Intermediate Similarity	NPC105157
0.8496	Intermediate Similarity	NPC103356
0.8496	Intermediate Similarity	NPC100067
0.8496	Intermediate Similarity	NPC30501
0.8496	Intermediate Similarity	NPC98254
0.8493	Intermediate Similarity	NPC133856
0.8489	Intermediate Similarity	NPC13715
0.8489	Intermediate Similarity	NPC472602
0.8489	Intermediate Similarity	NPC123714
0.8489	Intermediate Similarity	NPC221104
0.8483	Intermediate Similarity	NPC291049
0.8483	Intermediate Similarity	NPC233267
0.8483	Intermediate Similarity	NPC198927
0.8478	Intermediate Similarity	NPC291454
0.8472	Intermediate Similarity	NPC471734
0.8472	Intermediate Similarity	NPC14098

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 NPC48036 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	321
0.1-0.2	1009
0.2-0.3	1770
0.3-0.4	2862
0.4-0.5	1849
0.5-0.6	923
0.6-0.7	319
0.7-0.8	86
0.8-0.85	9
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.903	High Similarity	NPD1509	Clinical (unspecified phase)
0.8521	High Similarity	NPD7390	Discontinued
0.8429	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD2532	Approved
0.8333	Intermediate Similarity	NPD2533	Approved
0.8333	Intermediate Similarity	NPD2534	Approved
0.8286	Intermediate Similarity	NPD5408	Approved
0.8286	Intermediate Similarity	NPD5406	Approved
0.8286	Intermediate Similarity	NPD5404	Approved
0.8286	Intermediate Similarity	NPD5405	Approved
0.8214	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD943	Approved
0.8182	Intermediate Similarity	NPD1201	Approved
0.8074	Intermediate Similarity	NPD1470	Approved
0.7943	Intermediate Similarity	NPD1607	Approved
0.7941	Intermediate Similarity	NPD1164	Approved
0.7895	Intermediate Similarity	NPD7819	Suspended
0.7885	Intermediate Similarity	NPD6232	Discontinued
0.7852	Intermediate Similarity	NPD9269	Phase 2
0.7848	Intermediate Similarity	NPD7473	Discontinued
0.782	Intermediate Similarity	NPD9268	Approved
0.7801	Intermediate Similarity	NPD1240	Approved
0.7748	Intermediate Similarity	NPD3226	Approved
0.7727	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD1510	Phase 2
0.7656	Intermediate Similarity	NPD74	Approved
0.7656	Intermediate Similarity	NPD9266	Approved
0.7655	Intermediate Similarity	NPD2935	Discontinued
0.7647	Intermediate Similarity	NPD7411	Suspended
0.7622	Intermediate Similarity	NPD230	Phase 1
0.76	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD6959	Discontinued
0.7594	Intermediate Similarity	NPD9493	Approved
0.7578	Intermediate Similarity	NPD9267	Approved
0.7578	Intermediate Similarity	NPD9264	Approved
0.7578	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD9263	Approved
0.7568	Intermediate Similarity	NPD3750	Approved
0.7556	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD5710	Approved
0.7547	Intermediate Similarity	NPD5711	Approved
0.75	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2800	Approved
0.75	Intermediate Similarity	NPD1243	Approved
0.7483	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2346	Discontinued
0.7453	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD1549	Phase 2
0.7417	Intermediate Similarity	NPD1511	Approved
0.7415	Intermediate Similarity	NPD1551	Phase 2
0.7405	Intermediate Similarity	NPD3749	Approved
0.7405	Intermediate Similarity	NPD7075	Discontinued
0.7368	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6599	Discontinued
0.7353	Intermediate Similarity	NPD9545	Approved
0.7333	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6651	Approved
0.7328	Intermediate Similarity	NPD4750	Phase 3
0.7325	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1512	Approved
0.7313	Intermediate Similarity	NPD9281	Approved
0.7292	Intermediate Similarity	NPD411	Approved
0.7267	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD9261	Approved
0.7261	Intermediate Similarity	NPD1934	Approved
0.7246	Intermediate Similarity	NPD4626	Approved
0.7244	Intermediate Similarity	NPD4380	Phase 2
0.7234	Intermediate Similarity	NPD1283	Approved
0.7233	Intermediate Similarity	NPD7768	Phase 2
0.723	Intermediate Similarity	NPD2799	Discontinued
0.723	Intermediate Similarity	NPD3748	Approved
0.7214	Intermediate Similarity	NPD9717	Approved
0.7212	Intermediate Similarity	NPD5844	Phase 1
0.719	Intermediate Similarity	NPD6799	Approved
0.7188	Intermediate Similarity	NPD846	Approved
0.7188	Intermediate Similarity	NPD940	Approved
0.7181	Intermediate Similarity	NPD6099	Approved
0.7181	Intermediate Similarity	NPD6100	Approved
0.7172	Intermediate Similarity	NPD3764	Approved
0.7161	Intermediate Similarity	NPD920	Approved
0.7152	Intermediate Similarity	NPD6801	Discontinued
0.7124	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD3300	Phase 2
0.7122	Intermediate Similarity	NPD3019	Approved
0.7122	Intermediate Similarity	NPD2932	Approved
0.7114	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1465	Phase 2
0.7107	Intermediate Similarity	NPD2801	Approved
0.7067	Intermediate Similarity	NPD2796	Approved
0.7063	Intermediate Similarity	NPD3817	Phase 2
0.7063	Intermediate Similarity	NPD1203	Approved
0.7037	Intermediate Similarity	NPD919	Approved
0.7032	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD447	Suspended
0.7021	Intermediate Similarity	NPD1281	Approved
0.7019	Intermediate Similarity	NPD3882	Suspended
0.7006	Intermediate Similarity	NPD6020	Phase 2
0.6993	Remote Similarity	NPD7003	Approved
0.6982	Remote Similarity	NPD6559	Discontinued
0.6939	Remote Similarity	NPD3268	Approved
0.6939	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD2313	Discontinued
0.6934	Remote Similarity	NPD5951	Approved
0.6929	Remote Similarity	NPD5691	Approved
0.6923	Remote Similarity	NPD5953	Discontinued
0.6914	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1471	Phase 3
0.6908	Remote Similarity	NPD2344	Approved
0.6901	Remote Similarity	NPD422	Phase 1
0.6883	Remote Similarity	NPD4628	Phase 3
0.6879	Remote Similarity	NPD8150	Discontinued
0.6875	Remote Similarity	NPD288	Approved
0.6871	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD7458	Discontinued
0.6855	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD1608	Approved
0.6848	Remote Similarity	NPD1247	Approved
0.6846	Remote Similarity	NPD1242	Phase 1
0.6826	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD6166	Phase 2
0.6826	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD2654	Approved
0.6809	Remote Similarity	NPD1651	Approved
0.6805	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD7286	Phase 2
0.6797	Remote Similarity	NPD844	Approved
0.6788	Remote Similarity	NPD5494	Approved
0.6781	Remote Similarity	NPD2798	Approved
0.6779	Remote Similarity	NPD520	Approved
0.6779	Remote Similarity	NPD6663	Approved
0.6776	Remote Similarity	NPD4308	Phase 3
0.6765	Remote Similarity	NPD7074	Phase 3
0.6757	Remote Similarity	NPD4625	Phase 3
0.6748	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD3818	Discontinued
0.6741	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5736	Approved
0.6731	Remote Similarity	NPD2309	Approved
0.673	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD37	Approved
0.6713	Remote Similarity	NPD3026	Approved
0.6713	Remote Similarity	NPD3023	Approved
0.6712	Remote Similarity	NPD3266	Approved
0.6712	Remote Similarity	NPD3267	Approved
0.6706	Remote Similarity	NPD7054	Approved
0.6705	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.669	Remote Similarity	NPD3025	Approved
0.669	Remote Similarity	NPD3024	Approved
0.6667	Remote Similarity	NPD2342	Discontinued
0.6667	Remote Similarity	NPD3400	Discontinued
0.6667	Remote Similarity	NPD7472	Approved
0.6667	Remote Similarity	NPD7635	Approved
0.6667	Remote Similarity	NPD8166	Discontinued
0.6667	Remote Similarity	NPD1809	Phase 2
0.6648	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD5402	Approved
0.6646	Remote Similarity	NPD4288	Approved
0.6643	Remote Similarity	NPD17	Approved
0.6643	Remote Similarity	NPD255	Approved
0.6643	Remote Similarity	NPD256	Approved
0.6643	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD8151	Discontinued
0.6628	Remote Similarity	NPD6797	Phase 2
0.6627	Remote Similarity	NPD6234	Discontinued
0.6625	Remote Similarity	NPD5403	Approved
0.6623	Remote Similarity	NPD2979	Phase 3
0.6621	Remote Similarity	NPD3972	Approved
0.662	Remote Similarity	NPD1759	Phase 1
0.6617	Remote Similarity	NPD1929	Approved
0.6617	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD1930	Approved
0.6609	Remote Similarity	NPD8313	Approved
0.6609	Remote Similarity	NPD8312	Approved
0.6607	Remote Similarity	NPD7229	Phase 3
0.6606	Remote Similarity	NPD4966	Approved
0.6606	Remote Similarity	NPD4965	Approved
0.6606	Remote Similarity	NPD4967	Phase 2
0.6604	Remote Similarity	NPD5401	Approved
0.6604	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.66	Remote Similarity	NPD1296	Phase 2
0.6599	Remote Similarity	NPD2797	Approved
0.6591	Remote Similarity	NPD289	Clinical (unspecified phase)
0.659	Remote Similarity	NPD7251	Discontinued
0.6579	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6832	Phase 2
0.6575	Remote Similarity	NPD4749	Approved
0.6575	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD1755	Approved
0.6556	Remote Similarity	NPD6534	Approved
0.6556	Remote Similarity	NPD6535	Approved
0.6554	Remote Similarity	NPD1019	Discontinued
0.6554	Remote Similarity	NPD257	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