NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	266.08
Volume:	255.85
LogP:	3.967
LogD:	1.15
LogS:	-3.187
# Rotatable Bonds:	1
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.669
Synthetic Accessibility Score:	3.684
Fsp3:	0.385
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.743
MDCK Permeability:	6.584422408195678e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.023

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056
Plasma Protein Binding (PPB):	97.84354400634766%
Volume Distribution (VD):	0.425
Pgp-substrate:	2.3412649631500244%

ADMET: Metabolism

CYP1A2-inhibitor:	0.119
CYP1A2-substrate:	0.436
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.281
CYP2C9-substrate:	0.109
CYP2D6-inhibitor:	0.083
CYP2D6-substrate:	0.102
CYP3A4-inhibitor:	0.062
CYP3A4-substrate:	0.056

ADMET: Excretion

Clearance (CL):	1.16
Half-life (T1/2):	0.745

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.273
Drug-inuced Liver Injury (DILI):	0.97
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.07
Maximum Recommended Daily Dose:	0.022
Skin Sensitization:	0.111
Carcinogencity:	0.085
Eye Corrosion:	0.003
Eye Irritation:	0.409
Respiratory Toxicity:	0.347

Download Data

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

Natural Product: NPC245058

Natural Product ID:	NPC245058
*Common Name:**	Dihydrocitrinone
IUPAC Name:	(3R,4S)-6,8-dihydroxy-3,4,5-trimethyl-1-oxo-3,4-dihydroisochromene-7-carboxylic acid
Synonyms:	Dihydrocitrinone
Standard InCHIKey:	VVVMDYGNIVXIIG-INEUFUBQSA-N
Standard InCHI:	InChI=1S/C13H14O6/c1-4-6(3)19-13(18)8-7(4)5(2)10(14)9(11(8)15)12(16)17/h4,6,14-15H,1-3H3,(H,16,17)/t4-,6-/m1/s1
SMILES:	C[C@H]1OC(=O)c2c([C@@H]1C)c(C)c(c(c2O)C(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465858
PubChem CID:	163095
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001105] Phthalic acid and derivatives [CHEMONTID:0004009] Phthalate esters [CHEMONTID:0004010] m-Phthalate esters

*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]
NPO32513	Penicillium citrinum	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18281952]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18656987]
NPO19812	Pimelea simplex	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21049973]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21053938]
NPO20842	Beauveria felina	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21438588]
NPO33186	penicillium citrinum hgy1-5	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21761866]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	Moroccan	n.a.	PMID[23713692]
NPO20842	Beauveria felina	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23822585]
NPO20842	Beauveria felina	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26295595]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26295595]
NPO41450	Penicillium citrinum + Aspergillus sydowii	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[31953204]
NPO12352	Magnolia baillonii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3437284]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7766039]
NPO19551	Cocculus pendulus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19812	Pimelea simplex	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19812	Pimelea simplex	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19551	Cocculus pendulus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11741	Glycosmis parviflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20842	Beauveria felina	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18651	Piper lolot	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18223	Dictyostelium brefeldianum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19551	Cocculus pendulus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19146	Cosmos bipinnatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19681	Hypoxis filiformis	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14131	Phyllanthus maderaspatensis	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18898	Madhuca utilis	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17984	Aplysia angasi	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10921	Cercospora ligustri	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12352	Magnolia baillonii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19611	Ipomoea tuberosa	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19812	Pimelea simplex	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13189	Carex folliculata	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16902	Dendroctonus brevicomis	Species	Curculionidae	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	4

Activity Type	# Activity
Cell Line	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[460792]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	10000.0	nM	PMID[460792]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	10000.0	nM	PMID[460792]
NPT1	Others	Radical scavenging activity		IC50	>	1000000.0	nM	PMID[460791]

☑ 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 NPC245058 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	323
0.1-0.2	1590
0.2-0.3	3676
0.3-0.4	8515
0.4-0.5	10906
0.5-0.6	4835
0.6-0.7	7489
0.7-0.8	4831
0.8-0.85	404
0.85-0.9	105
0.9-0.95	20
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9771	High Similarity	NPC156967
0.9621	High Similarity	NPC472599
0.947	High Similarity	NPC475645
0.9462	High Similarity	NPC296158
0.9407	High Similarity	NPC88269
0.9275	High Similarity	NPC159721
0.9209	High Similarity	NPC151607
0.9209	High Similarity	NPC42540
0.9197	High Similarity	NPC472601
0.9197	High Similarity	NPC472600
0.9137	High Similarity	NPC471731
0.913	High Similarity	NPC472604
0.913	High Similarity	NPC472603
0.913	High Similarity	NPC472605
0.913	High Similarity	NPC37530
0.9065	High Similarity	NPC471733
0.9058	High Similarity	NPC99441
0.9051	High Similarity	NPC221104
0.9044	High Similarity	NPC158481
0.9044	High Similarity	NPC235115
0.9007	High Similarity	NPC473692
0.9	High Similarity	NPC472610
0.8913	High Similarity	NPC472602
0.8905	High Similarity	NPC50455
0.8905	High Similarity	NPC291454
0.8881	High Similarity	NPC471734
0.8857	High Similarity	NPC470842
0.8857	High Similarity	NPC53649
0.8849	High Similarity	NPC275356
0.8841	High Similarity	NPC70380
0.8824	High Similarity	NPC153783
0.8811	High Similarity	NPC471735
0.8811	High Similarity	NPC473023
0.8794	High Similarity	NPC82913
0.8786	High Similarity	NPC187690
0.8786	High Similarity	NPC165172
0.8786	High Similarity	NPC155205
0.8777	High Similarity	NPC94248
0.8777	High Similarity	NPC212693
0.8777	High Similarity	NPC191835
0.875	High Similarity	NPC53362
0.875	High Similarity	NPC8817
0.875	High Similarity	NPC166583
0.8741	High Similarity	NPC75694
0.8732	High Similarity	NPC478202
0.8732	High Similarity	NPC469542
0.8723	High Similarity	NPC313123
0.8723	High Similarity	NPC478217
0.8714	High Similarity	NPC32360
0.8714	High Similarity	NPC105456
0.8714	High Similarity	NPC139634
0.8714	High Similarity	NPC268052
0.8705	High Similarity	NPC194579
0.8696	High Similarity	NPC278375
0.869	High Similarity	NPC470359
0.8681	High Similarity	NPC470357
0.8676	High Similarity	NPC219892
0.8676	High Similarity	NPC189823
0.8662	High Similarity	NPC322112
0.8652	High Similarity	NPC168471
0.8649	High Similarity	NPC472799
0.8649	High Similarity	NPC471695
0.8643	High Similarity	NPC33144
0.8643	High Similarity	NPC478200
0.8623	High Similarity	NPC474394
0.8623	High Similarity	NPC175943
0.8621	High Similarity	NPC137296
0.8592	High Similarity	NPC478201
0.8592	High Similarity	NPC1704
0.8592	High Similarity	NPC472035
0.8592	High Similarity	NPC158634
0.8592	High Similarity	NPC67650
0.8592	High Similarity	NPC149533
0.8582	High Similarity	NPC92655
0.8571	High Similarity	NPC474849
0.8571	High Similarity	NPC474771
0.8571	High Similarity	NPC135837
0.8571	High Similarity	NPC149372
0.8571	High Similarity	NPC150928
0.8571	High Similarity	NPC261292
0.8571	High Similarity	NPC301915
0.8571	High Similarity	NPC119929
0.8571	High Similarity	NPC65837
0.8571	High Similarity	NPC71256
0.8571	High Similarity	NPC178467
0.8561	High Similarity	NPC27407
0.8561	High Similarity	NPC290803
0.8561	High Similarity	NPC142027
0.8552	High Similarity	NPC163846
0.8552	High Similarity	NPC260946
0.8552	High Similarity	NPC225173
0.8551	High Similarity	NPC48036
0.8551	High Similarity	NPC470988
0.854	High Similarity	NPC214702
0.854	High Similarity	NPC470831
0.8531	High Similarity	NPC469579
0.8521	High Similarity	NPC64664
0.8521	High Similarity	NPC158472
0.8514	High Similarity	NPC477672
0.8514	High Similarity	NPC133856
0.8514	High Similarity	NPC477673
0.8511	High Similarity	NPC472403
0.8511	High Similarity	NPC475974
0.8503	High Similarity	NPC233267
0.8503	High Similarity	NPC291049
0.85	High Similarity	NPC471690
0.8493	Intermediate Similarity	NPC125801
0.8489	Intermediate Similarity	NPC470984
0.8483	Intermediate Similarity	NPC471689
0.8478	Intermediate Similarity	NPC476389
0.8472	Intermediate Similarity	NPC472006
0.8472	Intermediate Similarity	NPC51106
0.8467	Intermediate Similarity	NPC477687
0.8467	Intermediate Similarity	NPC149618
0.8467	Intermediate Similarity	NPC477671
0.8467	Intermediate Similarity	NPC89625
0.8462	Intermediate Similarity	NPC244923
0.8456	Intermediate Similarity	NPC87708
0.8456	Intermediate Similarity	NPC273483
0.8456	Intermediate Similarity	NPC271681
0.8451	Intermediate Similarity	NPC474655
0.8451	Intermediate Similarity	NPC247409
0.8451	Intermediate Similarity	NPC52358
0.8446	Intermediate Similarity	NPC158866
0.8435	Intermediate Similarity	NPC105415
0.8435	Intermediate Similarity	NPC37139
0.8429	Intermediate Similarity	NPC180905
0.8429	Intermediate Similarity	NPC182496
0.8425	Intermediate Similarity	NPC470570
0.8417	Intermediate Similarity	NPC180261
0.8417	Intermediate Similarity	NPC37299
0.8414	Intermediate Similarity	NPC126882
0.8414	Intermediate Similarity	NPC478203
0.8414	Intermediate Similarity	NPC210966
0.8414	Intermediate Similarity	NPC48762
0.8411	Intermediate Similarity	NPC477674
0.8411	Intermediate Similarity	NPC477675
0.8403	Intermediate Similarity	NPC157497
0.8403	Intermediate Similarity	NPC81337
0.8403	Intermediate Similarity	NPC94076
0.8403	Intermediate Similarity	NPC285659
0.8403	Intermediate Similarity	NPC182255
0.8403	Intermediate Similarity	NPC474385
0.84	Intermediate Similarity	NPC470102
0.84	Intermediate Similarity	NPC192189
0.84	Intermediate Similarity	NPC477669
0.8389	Intermediate Similarity	NPC72958
0.8389	Intermediate Similarity	NPC232645
0.838	Intermediate Similarity	NPC177307
0.838	Intermediate Similarity	NPC9121
0.8378	Intermediate Similarity	NPC237440
0.8378	Intermediate Similarity	NPC270160
0.8378	Intermediate Similarity	NPC4423
0.8378	Intermediate Similarity	NPC77325
0.8369	Intermediate Similarity	NPC118919
0.8367	Intermediate Similarity	NPC476463
0.8367	Intermediate Similarity	NPC474108
0.8367	Intermediate Similarity	NPC177995
0.8367	Intermediate Similarity	NPC304351
0.8367	Intermediate Similarity	NPC245757
0.8366	Intermediate Similarity	NPC470358
0.8357	Intermediate Similarity	NPC474519
0.8356	Intermediate Similarity	NPC83272
0.8356	Intermediate Similarity	NPC472034
0.8356	Intermediate Similarity	NPC257558
0.8356	Intermediate Similarity	NPC34482
0.8345	Intermediate Similarity	NPC185624
0.8345	Intermediate Similarity	NPC472344
0.8345	Intermediate Similarity	NPC84266
0.8345	Intermediate Similarity	NPC470556
0.8333	Intermediate Similarity	NPC217447
0.8333	Intermediate Similarity	NPC470987
0.8333	Intermediate Similarity	NPC90411
0.8333	Intermediate Similarity	NPC167903
0.8333	Intermediate Similarity	NPC469818
0.8333	Intermediate Similarity	NPC21378
0.8333	Intermediate Similarity	NPC175978
0.8333	Intermediate Similarity	NPC62219
0.8333	Intermediate Similarity	NPC475730
0.8322	Intermediate Similarity	NPC179178
0.8322	Intermediate Similarity	NPC202595
0.8322	Intermediate Similarity	NPC325983
0.8311	Intermediate Similarity	NPC240622
0.8311	Intermediate Similarity	NPC240253
0.8311	Intermediate Similarity	NPC471642
0.8311	Intermediate Similarity	NPC221352
0.8311	Intermediate Similarity	NPC471641
0.8311	Intermediate Similarity	NPC153417
0.831	Intermediate Similarity	NPC470989
0.831	Intermediate Similarity	NPC470985
0.831	Intermediate Similarity	NPC470983
0.831	Intermediate Similarity	NPC470982
0.8299	Intermediate Similarity	NPC107625
0.8299	Intermediate Similarity	NPC267509
0.8299	Intermediate Similarity	NPC472033
0.8298	Intermediate Similarity	NPC470844
0.8289	Intermediate Similarity	NPC4547
0.8288	Intermediate Similarity	NPC210425
0.8288	Intermediate Similarity	NPC474939
0.8288	Intermediate Similarity	NPC307895

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 NPC245058 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	283
0.1-0.2	1094
0.2-0.3	2067
0.3-0.4	2712
0.4-0.5	1729
0.5-0.6	918
0.6-0.7	268
0.7-0.8	74
0.8-0.85	2
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8741	High Similarity	NPD2533	Approved
0.8741	High Similarity	NPD2534	Approved
0.8741	High Similarity	NPD2532	Approved
0.8582	High Similarity	NPD970	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD5710	Approved
0.8141	Intermediate Similarity	NPD5711	Approved
0.8039	Intermediate Similarity	NPD7819	Suspended
0.7986	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD6651	Approved
0.7962	Intermediate Similarity	NPD6959	Discontinued
0.7799	Intermediate Similarity	NPD6232	Discontinued
0.777	Intermediate Similarity	NPD2800	Approved
0.7764	Intermediate Similarity	NPD7473	Discontinued
0.7756	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD1607	Approved
0.7703	Intermediate Similarity	NPD1549	Phase 2
0.7692	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD7411	Suspended
0.7658	Intermediate Similarity	NPD7075	Discontinued
0.7655	Intermediate Similarity	NPD230	Phase 1
0.7619	Intermediate Similarity	NPD1510	Phase 2
0.7586	Intermediate Similarity	NPD1240	Approved
0.758	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD5404	Approved
0.7568	Intermediate Similarity	NPD5408	Approved
0.7568	Intermediate Similarity	NPD5406	Approved
0.7568	Intermediate Similarity	NPD5405	Approved
0.7568	Intermediate Similarity	NPD1551	Phase 2
0.7566	Intermediate Similarity	NPD7390	Discontinued
0.7561	Intermediate Similarity	NPD5844	Phase 1
0.7516	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1934	Approved
0.75	Intermediate Similarity	NPD4380	Phase 2
0.7485	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD2935	Discontinued
0.7436	Intermediate Similarity	NPD3226	Approved
0.7405	Intermediate Similarity	NPD6801	Discontinued
0.74	Intermediate Similarity	NPD2346	Discontinued
0.7391	Intermediate Similarity	NPD9545	Approved
0.7389	Intermediate Similarity	NPD6599	Discontinued
0.7375	Intermediate Similarity	NPD7768	Phase 2
0.7368	Intermediate Similarity	NPD3750	Approved
0.7329	Intermediate Similarity	NPD3749	Approved
0.7308	Intermediate Similarity	NPD920	Approved
0.7303	Intermediate Similarity	NPD1243	Approved
0.729	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD1465	Phase 2
0.7246	Intermediate Similarity	NPD9493	Approved
0.723	Intermediate Similarity	NPD943	Approved
0.7226	Intermediate Similarity	NPD1511	Approved
0.7226	Intermediate Similarity	NPD6799	Approved
0.7219	Intermediate Similarity	NPD6559	Discontinued
0.7219	Intermediate Similarity	NPD6099	Approved
0.7219	Intermediate Similarity	NPD2796	Approved
0.7219	Intermediate Similarity	NPD6100	Approved
0.7215	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD8150	Discontinued
0.719	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD1201	Approved
0.7181	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD5124	Phase 1
0.7161	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1283	Approved
0.7152	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4628	Phase 3
0.7134	Intermediate Similarity	NPD5494	Approved
0.7134	Intermediate Similarity	NPD1512	Approved
0.7117	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1470	Approved
0.7103	Intermediate Similarity	NPD1164	Approved
0.7099	Intermediate Similarity	NPD3817	Phase 2
0.7095	Intermediate Similarity	NPD3764	Approved
0.7095	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD919	Approved
0.707	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6166	Phase 2
0.7066	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3882	Suspended
0.7041	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3748	Approved
0.7039	Intermediate Similarity	NPD2799	Discontinued
0.7037	Intermediate Similarity	NPD2801	Approved
0.7	Intermediate Similarity	NPD7074	Phase 3
0.698	Remote Similarity	NPD411	Approved
0.6975	Remote Similarity	NPD37	Approved
0.697	Remote Similarity	NPD6234	Discontinued
0.6959	Remote Similarity	NPD5953	Discontinued
0.6951	Remote Similarity	NPD4966	Approved
0.6951	Remote Similarity	NPD4965	Approved
0.6951	Remote Similarity	NPD4967	Phase 2
0.6944	Remote Similarity	NPD1281	Approved
0.6941	Remote Similarity	NPD7054	Approved
0.6941	Remote Similarity	NPD7286	Phase 2
0.6936	Remote Similarity	NPD8313	Approved
0.6936	Remote Similarity	NPD8312	Approved
0.6923	Remote Similarity	NPD4626	Approved
0.6923	Remote Similarity	NPD7003	Approved
0.6901	Remote Similarity	NPD7472	Approved
0.6897	Remote Similarity	NPD9717	Approved
0.6897	Remote Similarity	NPD9269	Phase 2
0.6897	Remote Similarity	NPD1608	Approved
0.6882	Remote Similarity	NPD3818	Discontinued
0.6879	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6535	Approved
0.6872	Remote Similarity	NPD6534	Approved
0.6871	Remote Similarity	NPD1203	Approved
0.686	Remote Similarity	NPD6797	Phase 2
0.6853	Remote Similarity	NPD9268	Approved
0.6853	Remote Similarity	NPD5691	Approved
0.6845	Remote Similarity	NPD8151	Discontinued
0.6845	Remote Similarity	NPD7229	Phase 3
0.6836	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD422	Phase 1
0.6821	Remote Similarity	NPD7251	Discontinued
0.6811	Remote Similarity	NPD8320	Phase 1
0.6811	Remote Similarity	NPD8319	Approved
0.68	Remote Similarity	NPD4625	Phase 3
0.679	Remote Similarity	NPD7458	Discontinued
0.6788	Remote Similarity	NPD5402	Approved
0.6786	Remote Similarity	NPD1247	Approved
0.6784	Remote Similarity	NPD7228	Approved
0.6782	Remote Similarity	NPD7808	Phase 3
0.6782	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD2979	Phase 3
0.6774	Remote Similarity	NPD2438	Suspended
0.677	Remote Similarity	NPD5403	Approved
0.6766	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD7700	Phase 2
0.6758	Remote Similarity	NPD7699	Phase 2
0.6757	Remote Similarity	NPD7435	Discontinued
0.6755	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD2313	Discontinued
0.6755	Remote Similarity	NPD7985	Registered
0.675	Remote Similarity	NPD5401	Approved
0.6735	Remote Similarity	NPD4749	Approved
0.6732	Remote Similarity	NPD447	Suspended
0.6712	Remote Similarity	NPD1610	Phase 2
0.6711	Remote Similarity	NPD6663	Approved
0.6711	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD6273	Approved
0.6707	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.669	Remote Similarity	NPD17	Approved
0.6686	Remote Similarity	NPD7199	Phase 2
0.6686	Remote Similarity	NPD7177	Discontinued
0.6685	Remote Similarity	NPD6781	Approved
0.6685	Remote Similarity	NPD6780	Approved
0.6685	Remote Similarity	NPD6776	Approved
0.6685	Remote Similarity	NPD6777	Approved
0.6685	Remote Similarity	NPD6778	Approved
0.6685	Remote Similarity	NPD6782	Approved
0.6685	Remote Similarity	NPD6779	Approved
0.6667	Remote Similarity	NPD4060	Phase 1
0.6667	Remote Similarity	NPD5736	Approved
0.6667	Remote Similarity	NPD74	Approved
0.6667	Remote Similarity	NPD1398	Phase 1
0.6667	Remote Similarity	NPD9266	Approved
0.6645	Remote Similarity	NPD3268	Approved
0.6643	Remote Similarity	NPD7340	Approved
0.663	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.663	Remote Similarity	NPD6213	Phase 3
0.663	Remote Similarity	NPD6212	Phase 3
0.6624	Remote Similarity	NPD6002	Phase 3
0.6624	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD6005	Phase 3
0.6624	Remote Similarity	NPD6004	Phase 3
0.6624	Remote Similarity	NPD2344	Approved
0.6623	Remote Similarity	NPD4908	Phase 1
0.6623	Remote Similarity	NPD6832	Phase 2
0.6623	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD4750	Phase 3
0.6608	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD8166	Discontinued
0.6604	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD7033	Discontinued
0.6603	Remote Similarity	NPD4308	Phase 3
0.6601	Remote Similarity	NPD520	Approved
0.6597	Remote Similarity	NPD7644	Approved
0.6597	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD7783	Phase 2
0.6595	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD9264	Approved
0.6594	Remote Similarity	NPD9267	Approved
0.6594	Remote Similarity	NPD9263	Approved
0.6593	Remote Similarity	NPD4360	Phase 2

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