NPASS Compound

Structure

NPC472890 OpenBabel07101719162D 30 32 0 0 1 0 0 0 0 0999 V2000 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 3 4 2 0 0 0 0 3 13 1 0 0 0 0 4 17 1 0 0 0 0 5 10 2 0 0 0 0 5 12 1 0 0 0 0 6 11 1 0 0 0 0 6 13 2 0 0 0 0 7 11 2 0 0 0 0 7 16 1 0 0 0 0 8 12 2 0 0 0 0 8 15 1 0 0 0 0 9 29 1 0 0 0 0 10 18 1 0 0 0 0 11 14 1 0 0 0 0 12 22 1 0 0 0 0 13 29 1 0 0 0 0 14 9 1 6 0 0 0 14 19 1 0 0 0 0 15 18 2 0 0 0 0 15 23 1 0 0 0 0 16 21 1 0 0 0 0 16 24 2 0 0 0 0 17 25 2 0 0 0 0 17 26 1 0 0 0 0 18 20 1 0 0 0 0 19 21 1 1 0 0 0 19 30 1 0 0 0 0 20 27 2 0 0 0 0 20 30 1 0 0 0 0 21 2 1 1 0 0 0 21 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.11
Volume:	401.487
LogP:	1.909
LogD:	1.45
LogS:	-3.416
# Rotatable Bonds:	5
TPSA:	150.59
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.423
Synthetic Accessibility Score:	4.362
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.511
MDCK Permeability:	1.3643351849168539e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.987
Human Intestinal Absorption (HIA):	0.086
20% Bioavailability (F20%):	0.867
30% Bioavailability (F30%):	0.843

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.079
Plasma Protein Binding (PPB):	78.25737762451172%
Volume Distribution (VD):	0.392
Pgp-substrate:	9.751542091369629%

ADMET: Metabolism

CYP1A2-inhibitor:	0.556
CYP1A2-substrate:	0.093
CYP2C19-inhibitor:	0.05
CYP2C19-substrate:	0.046
CYP2C9-inhibitor:	0.28
CYP2C9-substrate:	0.688
CYP2D6-inhibitor:	0.324
CYP2D6-substrate:	0.096
CYP3A4-inhibitor:	0.524
CYP3A4-substrate:	0.16

ADMET: Excretion

Clearance (CL):	4.479
Half-life (T1/2):	0.909

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.896
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.443
Rat Oral Acute Toxicity:	0.369
Maximum Recommended Daily Dose:	0.964
Skin Sensitization:	0.947
Carcinogencity:	0.617
Eye Corrosion:	0.375
Eye Irritation:	0.925
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC472890

Natural Product ID:	NPC472890
*Common Name:**	ZDFHVFVPRFCIRZ-SMGAZDJTSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZDFHVFVPRFCIRZ-SMGAZDJTSA-N
Standard InCHI:	InChI=1S/C21H20O9/c1-10-5-12(22)8-15(23)18(10)20(27)30-19-14-9-29-13(3-4-17(25)26)6-11(14)7-16(24)21(19,2)28/h3-8,14,19,22-23,28H,9H2,1-2H3,(H,25,26)/b4-3+/t14-,19+,21+/m1/s1
SMILES:	CC1=CC(=CC(=C1C(=O)OC2C3COC(=CC3=CC(=O)C2(C)O)C=CC(=O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3593565
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001350] Benzoic acid esters [CHEMONTID:0004701] p-Hydroxybenzoic acid esters [CHEMONTID:0004702] p-Hydroxybenzoic acid alkyl 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
NPO33336	Penicillium sp. HN29-3B1	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26230970]
NPO33693	Talaromyces aculeatus DS-62013	Species	Trichocomaceae	Eukaryota	n.a.	saline-alkali soil, Shandong Province, China	2013-APR	PMID[28749670]

☑ 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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT60	Individual Protein	Lysosomal alpha-glucosidase	Homo sapiens	IC50	=	28000.0	nM	PMID[450474]

☑ 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 NPC472890 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	357
0.1-0.2	1374
0.2-0.3	3327
0.3-0.4	7302
0.4-0.5	10259
0.5-0.6	4971
0.6-0.7	6070
0.7-0.8	7581
0.8-0.85	1253
0.85-0.9	168
0.9-0.95	20
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9866	High Similarity	NPC478225
0.9865	High Similarity	NPC69043
0.9865	High Similarity	NPC478230
0.9865	High Similarity	NPC478221
0.9864	High Similarity	NPC76041
0.9864	High Similarity	NPC184284
0.9797	High Similarity	NPC137301
0.9797	High Similarity	NPC478231
0.9733	High Similarity	NPC472889
0.9732	High Similarity	NPC208173
0.9732	High Similarity	NPC170189
0.973	High Similarity	NPC478224
0.973	High Similarity	NPC115249
0.9728	High Similarity	NPC472891
0.9603	High Similarity	NPC478226
0.96	High Similarity	NPC317585
0.9463	High Similarity	NPC164762
0.94	High Similarity	NPC91809
0.9396	High Similarity	NPC84142
0.9346	High Similarity	NPC246466
0.929	High Similarity	NPC317544
0.9236	High Similarity	NPC191930
0.9172	High Similarity	NPC249181
0.9119	High Similarity	NPC283041
0.9079	High Similarity	NPC56204
0.9073	High Similarity	NPC73411
0.9073	High Similarity	NPC215711
0.9057	High Similarity	NPC20237
0.9032	High Similarity	NPC472050
0.9026	High Similarity	NPC471695
0.9007	High Similarity	NPC210320
0.8986	High Similarity	NPC158634
0.8981	High Similarity	NPC472055
0.8968	High Similarity	NPC99381
0.8944	High Similarity	NPC328321
0.8919	High Similarity	NPC158472
0.8917	High Similarity	NPC470339
0.8912	High Similarity	NPC478200
0.8912	High Similarity	NPC33144
0.8896	High Similarity	NPC70016
0.8896	High Similarity	NPC215921
0.8889	High Similarity	NPC237440
0.8889	High Similarity	NPC270160
0.8867	High Similarity	NPC478202
0.8859	High Similarity	NPC244923
0.8859	High Similarity	NPC472035
0.8859	High Similarity	NPC478201
0.8851	High Similarity	NPC247409
0.8851	High Similarity	NPC32360
0.8851	High Similarity	NPC52358
0.8851	High Similarity	NPC268052
0.8839	High Similarity	NPC470340
0.8824	High Similarity	NPC94781
0.8808	High Similarity	NPC210966
0.8808	High Similarity	NPC126882
0.8808	High Similarity	NPC478203
0.8808	High Similarity	NPC210425
0.8808	High Similarity	NPC280404
0.8808	High Similarity	NPC277426
0.8808	High Similarity	NPC86373
0.8805	High Similarity	NPC117985
0.8784	High Similarity	NPC191835
0.8782	High Similarity	NPC155686
0.8774	High Similarity	NPC200773
0.8774	High Similarity	NPC240768
0.8766	High Similarity	NPC280753
0.8766	High Similarity	NPC44378
0.8766	High Similarity	NPC4423
0.8766	High Similarity	NPC77325
0.8758	High Similarity	NPC81835
0.8758	High Similarity	NPC472036
0.875	High Similarity	NPC472034
0.875	High Similarity	NPC257558
0.875	High Similarity	NPC83272
0.8733	High Similarity	NPC478217
0.8733	High Similarity	NPC313123
0.8733	High Similarity	NPC53649
0.8726	High Similarity	NPC471456
0.8725	High Similarity	NPC92655
0.8718	High Similarity	NPC167903
0.8716	High Similarity	NPC70380
0.871	High Similarity	NPC469619
0.871	High Similarity	NPC469670
0.8693	High Similarity	NPC472033
0.8693	High Similarity	NPC202112
0.8693	High Similarity	NPC51513
0.8693	High Similarity	NPC473023
0.8684	High Similarity	NPC151607
0.8684	High Similarity	NPC103910
0.8684	High Similarity	NPC42540
0.8675	High Similarity	NPC474385
0.8675	High Similarity	NPC82913
0.8671	High Similarity	NPC478027
0.8667	High Similarity	NPC156872
0.8662	High Similarity	NPC281703
0.8662	High Similarity	NPC125487
0.8658	High Similarity	NPC9121
0.8658	High Similarity	NPC94248
0.8658	High Similarity	NPC472403
0.8658	High Similarity	NPC472602
0.8658	High Similarity	NPC212693
0.8658	High Similarity	NPC177307
0.8654	High Similarity	NPC46882
0.8654	High Similarity	NPC132990
0.865	High Similarity	NPC473094
0.8649	High Similarity	NPC235115
0.8642	High Similarity	NPC472049
0.8642	High Similarity	NPC294722
0.8639	High Similarity	NPC175943
0.8618	High Similarity	NPC159721
0.8618	High Similarity	NPC51106
0.8618	High Similarity	NPC472006
0.8614	High Similarity	NPC294149
0.8609	High Similarity	NPC67650
0.8609	High Similarity	NPC1704
0.8609	High Similarity	NPC472603
0.8609	High Similarity	NPC130485
0.8609	High Similarity	NPC475730
0.8608	High Similarity	NPC68727
0.8608	High Similarity	NPC473241
0.8606	High Similarity	NPC472620
0.8599	High Similarity	NPC51824
0.8599	High Similarity	NPC113608
0.8599	High Similarity	NPC470337
0.8599	High Similarity	NPC470338
0.8599	High Similarity	NPC268992
0.8599	High Similarity	NPC180944
0.8599	High Similarity	NPC256141
0.8598	High Similarity	NPC472619
0.8598	High Similarity	NPC473096
0.8598	High Similarity	NPC473095
0.8591	High Similarity	NPC71256
0.859	High Similarity	NPC158866
0.859	High Similarity	NPC180351
0.859	High Similarity	NPC295036
0.8589	High Similarity	NPC165460
0.8581	High Similarity	NPC471641
0.8581	High Similarity	NPC240253
0.8581	High Similarity	NPC240622
0.8581	High Similarity	NPC471642
0.8571	High Similarity	NPC92589
0.8571	High Similarity	NPC153783
0.8571	High Similarity	NPC107625
0.8571	High Similarity	NPC112418
0.8562	High Similarity	NPC475201
0.8562	High Similarity	NPC257025
0.8553	High Similarity	NPC227062
0.8553	High Similarity	NPC322112
0.8544	High Similarity	NPC192189
0.8544	High Similarity	NPC472799
0.8543	High Similarity	NPC472601
0.8543	High Similarity	NPC472600
0.8543	High Similarity	NPC155205
0.8535	High Similarity	NPC205918
0.8535	High Similarity	NPC471229
0.8535	High Similarity	NPC295650
0.8533	High Similarity	NPC126739
0.8533	High Similarity	NPC197666
0.8528	High Similarity	NPC211592
0.8528	High Similarity	NPC475979
0.8526	High Similarity	NPC476684
0.8526	High Similarity	NPC120171
0.8519	High Similarity	NPC473022
0.8519	High Similarity	NPC471745
0.8516	High Similarity	NPC166583
0.8516	High Similarity	NPC52106
0.8516	High Similarity	NPC53362
0.8516	High Similarity	NPC476463
0.8516	High Similarity	NPC259632
0.8509	High Similarity	NPC243701
0.8509	High Similarity	NPC471744
0.8506	High Similarity	NPC312789
0.85	High Similarity	NPC473395
0.85	High Similarity	NPC257309
0.85	High Similarity	NPC263483
0.8497	Intermediate Similarity	NPC21873
0.8497	Intermediate Similarity	NPC354984
0.8497	Intermediate Similarity	NPC471731
0.8497	Intermediate Similarity	NPC469542
0.8494	Intermediate Similarity	NPC473113
0.8491	Intermediate Similarity	NPC16082
0.8491	Intermediate Similarity	NPC80534
0.8491	Intermediate Similarity	NPC82592
0.8491	Intermediate Similarity	NPC237560
0.8491	Intermediate Similarity	NPC79998
0.8491	Intermediate Similarity	NPC56786
0.8487	Intermediate Similarity	NPC472605
0.8487	Intermediate Similarity	NPC472604
0.8481	Intermediate Similarity	NPC161159
0.8477	Intermediate Similarity	NPC295339
0.8477	Intermediate Similarity	NPC88269
0.8477	Intermediate Similarity	NPC105456
0.8477	Intermediate Similarity	NPC139634
0.8471	Intermediate Similarity	NPC150928
0.8471	Intermediate Similarity	NPC267117
0.8471	Intermediate Similarity	NPC225854
0.8471	Intermediate Similarity	NPC179178
0.8471	Intermediate Similarity	NPC85131
0.8467	Intermediate Similarity	NPC135837
0.8467	Intermediate Similarity	NPC178467

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 NPC472890 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	302
0.1-0.2	868
0.2-0.3	1817
0.3-0.4	2631
0.4-0.5	1914
0.5-0.6	1062
0.6-0.7	391
0.7-0.8	146
0.8-0.85	18
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.86	High Similarity	NPD970	Clinical (unspecified phase)
0.85	High Similarity	NPD7075	Discontinued
0.8491	Intermediate Similarity	NPD3817	Phase 2
0.8365	Intermediate Similarity	NPD6801	Discontinued
0.8354	Intermediate Similarity	NPD4380	Phase 2
0.8323	Intermediate Similarity	NPD6799	Approved
0.8313	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD7819	Suspended
0.8261	Intermediate Similarity	NPD5402	Approved
0.8253	Intermediate Similarity	NPD7473	Discontinued
0.8239	Intermediate Similarity	NPD6599	Discontinued
0.8182	Intermediate Similarity	NPD6232	Discontinued
0.8165	Intermediate Similarity	NPD5403	Approved
0.816	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD2532	Approved
0.8153	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD2533	Approved
0.8153	Intermediate Similarity	NPD2534	Approved
0.8137	Intermediate Similarity	NPD1934	Approved
0.8101	Intermediate Similarity	NPD1512	Approved
0.8098	Intermediate Similarity	NPD3882	Suspended
0.8092	Intermediate Similarity	NPD8150	Discontinued
0.8086	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD2801	Approved
0.8084	Intermediate Similarity	NPD6166	Phase 2
0.8084	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD6797	Phase 2
0.8039	Intermediate Similarity	NPD1510	Phase 2
0.8038	Intermediate Similarity	NPD5401	Approved
0.8013	Intermediate Similarity	NPD3750	Approved
0.8012	Intermediate Similarity	NPD7251	Discontinued
0.8011	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD3818	Discontinued
0.7988	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1511	Approved
0.7965	Intermediate Similarity	NPD7808	Phase 3
0.7961	Intermediate Similarity	NPD230	Phase 1
0.7941	Intermediate Similarity	NPD7054	Approved
0.7941	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD6959	Discontinued
0.7895	Intermediate Similarity	NPD7472	Approved
0.7885	Intermediate Similarity	NPD1549	Phase 2
0.7871	Intermediate Similarity	NPD2796	Approved
0.7853	Intermediate Similarity	NPD7411	Suspended
0.7848	Intermediate Similarity	NPD6190	Approved
0.7836	Intermediate Similarity	NPD5844	Phase 1
0.7821	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD6559	Discontinued
0.7792	Intermediate Similarity	NPD1607	Approved
0.7791	Intermediate Similarity	NPD7074	Phase 3
0.7785	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1240	Approved
0.7746	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD3749	Approved
0.7692	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3748	Approved
0.7684	Intermediate Similarity	NPD8434	Phase 2
0.7674	Intermediate Similarity	NPD3751	Discontinued
0.7673	Intermediate Similarity	NPD4628	Phase 3
0.7673	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1465	Phase 2
0.7643	Intermediate Similarity	NPD2935	Discontinued
0.7643	Intermediate Similarity	NPD1551	Phase 2
0.764	Intermediate Similarity	NPD7390	Discontinued
0.7633	Intermediate Similarity	NPD5494	Approved
0.7627	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD3226	Approved
0.7598	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD7435	Discontinued
0.7574	Intermediate Similarity	NPD6234	Discontinued
0.7574	Intermediate Similarity	NPD919	Approved
0.756	Intermediate Similarity	NPD7768	Phase 2
0.7548	Intermediate Similarity	NPD943	Approved
0.7544	Intermediate Similarity	NPD5710	Approved
0.7544	Intermediate Similarity	NPD5711	Approved
0.754	Intermediate Similarity	NPD8319	Approved
0.754	Intermediate Similarity	NPD8320	Phase 1
0.7527	Intermediate Similarity	NPD6534	Approved
0.7527	Intermediate Similarity	NPD6535	Approved
0.7514	Intermediate Similarity	NPD6782	Approved
0.7514	Intermediate Similarity	NPD6780	Approved
0.7514	Intermediate Similarity	NPD6777	Approved
0.7514	Intermediate Similarity	NPD6776	Approved
0.7514	Intermediate Similarity	NPD8313	Approved
0.7514	Intermediate Similarity	NPD6779	Approved
0.7514	Intermediate Similarity	NPD6778	Approved
0.7514	Intermediate Similarity	NPD8312	Approved
0.7514	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD37	Approved
0.7483	Intermediate Similarity	NPD9545	Approved
0.7456	Intermediate Similarity	NPD4967	Phase 2
0.7456	Intermediate Similarity	NPD4966	Approved
0.7456	Intermediate Similarity	NPD4965	Approved
0.7452	Intermediate Similarity	NPD6651	Approved
0.7442	Intermediate Similarity	NPD3787	Discontinued
0.7421	Intermediate Similarity	NPD6100	Approved
0.7421	Intermediate Similarity	NPD5406	Approved
0.7421	Intermediate Similarity	NPD6099	Approved
0.7421	Intermediate Similarity	NPD5408	Approved
0.7421	Intermediate Similarity	NPD5404	Approved
0.7421	Intermediate Similarity	NPD5405	Approved
0.7419	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD3764	Approved
0.7405	Intermediate Similarity	NPD7700	Phase 2
0.7405	Intermediate Similarity	NPD7699	Phase 2
0.7394	Intermediate Similarity	NPD920	Approved
0.7394	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2800	Approved
0.7391	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD7199	Phase 2
0.7375	Intermediate Similarity	NPD2346	Discontinued
0.7362	Intermediate Similarity	NPD3300	Phase 2
0.7351	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD9493	Approved
0.7344	Intermediate Similarity	NPD7874	Approved
0.7344	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD7685	Pre-registration
0.7302	Intermediate Similarity	NPD7696	Phase 3
0.7302	Intermediate Similarity	NPD7698	Approved
0.7302	Intermediate Similarity	NPD7697	Approved
0.7299	Intermediate Similarity	NPD3926	Phase 2
0.7292	Intermediate Similarity	NPD8151	Discontinued
0.7284	Intermediate Similarity	NPD1243	Approved
0.7283	Intermediate Similarity	NPD1247	Approved
0.7278	Intermediate Similarity	NPD447	Suspended
0.7273	Intermediate Similarity	NPD7228	Approved
0.7273	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7871	Phase 2
0.7263	Intermediate Similarity	NPD7870	Phase 2
0.7256	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2799	Discontinued
0.7247	Intermediate Similarity	NPD5953	Discontinued
0.7246	Intermediate Similarity	NPD1653	Approved
0.724	Intermediate Similarity	NPD7701	Phase 2
0.7239	Intermediate Similarity	NPD8166	Discontinued
0.7237	Intermediate Similarity	NPD9269	Phase 2
0.7216	Intermediate Similarity	NPD7801	Approved
0.7215	Intermediate Similarity	NPD4060	Phase 1
0.7208	Intermediate Similarity	NPD1470	Approved
0.7202	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7458	Discontinued
0.7179	Intermediate Similarity	NPD6832	Phase 2
0.7171	Intermediate Similarity	NPD1201	Approved
0.717	Intermediate Similarity	NPD6355	Discontinued
0.7169	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD2798	Approved
0.7159	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7236	Approved
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7135	Intermediate Similarity	NPD7286	Phase 2
0.7124	Intermediate Similarity	NPD9717	Approved
0.7114	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD8368	Discontinued
0.7097	Intermediate Similarity	NPD1203	Approved
0.7093	Intermediate Similarity	NPD4288	Approved
0.7093	Intermediate Similarity	NPD5353	Approved
0.7089	Intermediate Similarity	NPD3268	Approved
0.7089	Intermediate Similarity	NPD411	Approved
0.7089	Intermediate Similarity	NPD2313	Discontinued
0.7089	Intermediate Similarity	NPD6798	Discontinued
0.7086	Intermediate Similarity	NPD9268	Approved
0.7079	Intermediate Similarity	NPD7799	Discontinued
0.7073	Intermediate Similarity	NPD1652	Phase 2
0.7072	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD6823	Phase 2
0.7063	Intermediate Similarity	NPD5124	Phase 1
0.7063	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD2403	Approved
0.7059	Intermediate Similarity	NPD422	Phase 1
0.7055	Intermediate Similarity	NPD7266	Discontinued
0.7047	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7229	Phase 3
0.7044	Intermediate Similarity	NPD6233	Phase 2
0.7041	Intermediate Similarity	NPD7783	Phase 2
0.7041	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7239	Suspended
0.7037	Intermediate Similarity	NPD4308	Phase 3
0.703	Intermediate Similarity	NPD7003	Approved
0.7024	Intermediate Similarity	NPD6273	Approved
0.7006	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6213	Phase 3
0.7005	Intermediate Similarity	NPD6212	Phase 3
0.6995	Remote Similarity	NPD8407	Phase 2
0.6994	Remote Similarity	NPD2438	Suspended
0.6987	Remote Similarity	NPD2797	Approved
0.698	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4749	Approved
0.6963	Remote Similarity	NPD7501	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