NPASS Compound

Structure

NPC202112 OpenBabel07101719132D 23 25 0 0 1 0 0 0 0 0999 V2000 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -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 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 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 -1.7321 -2.0000 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 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 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 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 4 1 0 0 0 0 2 9 2 0 0 0 0 3 5 2 0 0 0 0 3 9 1 0 0 0 0 4 10 2 0 0 0 0 5 10 1 0 0 0 0 6 11 2 0 0 0 0 6 12 1 0 0 0 0 7 11 1 0 0 0 0 7 13 2 0 0 0 0 8 18 2 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 15 2 0 0 0 0 12 17 1 0 0 0 0 13 15 1 0 0 0 0 13 21 1 0 0 0 0 14 9 1 6 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 16 8 1 6 0 0 0 16 23 1 0 0 0 0 17 22 2 0 0 0 0 17 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.08
Volume:	308.569
LogP:	2.054
LogD:	1.76
LogS:	-3.312
# Rotatable Bonds:	2
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.733
Synthetic Accessibility Score:	3.473
Fsp3:	0.176
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:	-4.874
MDCK Permeability:	8.788802006165497e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.956
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.029
Plasma Protein Binding (PPB):	95.75458526611328%
Volume Distribution (VD):	0.49
Pgp-substrate:	3.867116928100586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.232
CYP1A2-substrate:	0.526
CYP2C19-inhibitor:	0.529
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.805
CYP2C9-substrate:	0.977
CYP2D6-inhibitor:	0.627
CYP2D6-substrate:	0.661
CYP3A4-inhibitor:	0.611
CYP3A4-substrate:	0.232

ADMET: Excretion

Clearance (CL):	18.147
Half-life (T1/2):	0.889

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.225
Drug-inuced Liver Injury (DILI):	0.806
AMES Toxicity:	0.059
Rat Oral Acute Toxicity:	0.304
Maximum Recommended Daily Dose:	0.541
Skin Sensitization:	0.794
Carcinogencity:	0.104
Eye Corrosion:	0.009
Eye Irritation:	0.897
Respiratory Toxicity:	0.136

Download Data

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

Natural Product: NPC202112

Natural Product ID:	NPC202112
*Common Name:**	Phayomphenol A1
IUPAC Name:	(3R,4S)-3-acetyl-5,7-dihydroxy-4-(4-hydroxyphenyl)-3,4-dihydroisochromen-1-one
Synonyms:	Phayomphenol A1
Standard InCHIKey:	ULVDXYXKRNQCCO-HOCLYGCPSA-N
Standard InCHI:	InChI=1S/C17H14O6/c1-8(18)16-14(9-2-4-10(19)5-3-9)15-12(17(22)23-16)6-11(20)7-13(15)21/h2-7,14,16,19-21H,1H3/t14-,16-/m0/s1
SMILES:	Oc1ccc(cc1)[C@@H]1[C@@H](OC(=O)c2c1c(O)cc(c2)O)C(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1939274
PubChem CID:	57391943
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003411] 2-benzopyrans

*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
NPO26194	Shorea roxburghii	Species	Dipterocarpaceae	Eukaryota	Barks	n.a.	n.a.	PMID[22209731]
NPO26194	Shorea roxburghii	Species	Dipterocarpaceae	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	3
Others	8

Activity Type	# Activity
Individual Protein	5
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT462	Individual Protein	Sucrase-isomaltase	Rattus norvegicus	IC50	>	400000.0	nM	PMID[506675]
NPT462	Individual Protein	Sucrase-isomaltase	Rattus norvegicus	Inhibition	=	6.4	%	PMID[506675]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	189.3	%	PMID[506675]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	199.5	%	PMID[506675]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	159.2	%	PMID[506675]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	184.1	%	PMID[506675]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	178.1	%	PMID[506675]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	166.2	%	PMID[506675]
NPT671	Individual Protein	Acidic alpha-glucosidase	Rattus norvegicus	IC50	>	400000.0	nM	PMID[506675]
NPT671	Individual Protein	Acidic alpha-glucosidase	Rattus norvegicus	Inhibition	=	4.0	%	PMID[506675]
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	=	39800.0	nM	PMID[506675]

☑ 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 NPC202112 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	325
0.1-0.2	1385
0.2-0.3	3157
0.3-0.4	6973
0.4-0.5	11051
0.5-0.6	4369
0.6-0.7	6021
0.7-0.8	8070
0.8-0.85	1236
0.85-0.9	103
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC51513
0.9521	High Similarity	NPC125487
0.9521	High Similarity	NPC281703
0.9375	High Similarity	NPC81835
0.9021	High Similarity	NPC155205
0.8951	High Similarity	NPC52358
0.8828	High Similarity	NPC53649
0.8828	High Similarity	NPC244923
0.8811	High Similarity	NPC301915
0.8811	High Similarity	NPC261292
0.88	High Similarity	NPC56204
0.88	High Similarity	NPC470107
0.875	High Similarity	NPC478200
0.875	High Similarity	NPC191835
0.875	High Similarity	NPC472602
0.875	High Similarity	NPC33144
0.8742	High Similarity	NPC230848
0.8741	High Similarity	NPC235115
0.8733	High Similarity	NPC77325
0.8733	High Similarity	NPC84142
0.8733	High Similarity	NPC4423
0.8725	High Similarity	NPC476463
0.8723	High Similarity	NPC476389
0.8716	High Similarity	NPC131766
0.8707	High Similarity	NPC478202
0.8699	High Similarity	NPC478217
0.8699	High Similarity	NPC313123
0.8699	High Similarity	NPC472035
0.8699	High Similarity	NPC472603
0.8699	High Similarity	NPC478201
0.8693	High Similarity	NPC208173
0.8693	High Similarity	NPC170189
0.8693	High Similarity	NPC472890
0.8693	High Similarity	NPC478221
0.869	High Similarity	NPC88269
0.8684	High Similarity	NPC76041
0.8684	High Similarity	NPC184284
0.8681	High Similarity	NPC71256
0.8681	High Similarity	NPC70380
0.8675	High Similarity	NPC164762
0.8675	High Similarity	NPC295036
0.8658	High Similarity	NPC470570
0.8649	High Similarity	NPC478203
0.8649	High Similarity	NPC42540
0.8649	High Similarity	NPC126882
0.8649	High Similarity	NPC151607
0.8649	High Similarity	NPC193703
0.8649	High Similarity	NPC21599
0.8649	High Similarity	NPC48762
0.8649	High Similarity	NPC210966
0.863	High Similarity	NPC472601
0.863	High Similarity	NPC472600
0.8627	High Similarity	NPC478231
0.8621	High Similarity	NPC212693
0.8621	High Similarity	NPC94248
0.8618	High Similarity	NPC295650
0.8618	High Similarity	NPC91809
0.8609	High Similarity	NPC477941
0.8609	High Similarity	NPC80370
0.8591	High Similarity	NPC184649
0.8591	High Similarity	NPC257558
0.8591	High Similarity	NPC303185
0.8591	High Similarity	NPC34482
0.8591	High Similarity	NPC83272
0.8581	High Similarity	NPC472006
0.8581	High Similarity	NPC472889
0.8581	High Similarity	NPC159721
0.8581	High Similarity	NPC478225
0.8581	High Similarity	NPC354984
0.8571	High Similarity	NPC158634
0.8571	High Similarity	NPC472605
0.8571	High Similarity	NPC317585
0.8571	High Similarity	NPC472604
0.8571	High Similarity	NPC69043
0.8571	High Similarity	NPC478230
0.8571	High Similarity	NPC99381
0.8562	High Similarity	NPC268052
0.8562	High Similarity	NPC474843
0.8562	High Similarity	NPC161159
0.8562	High Similarity	NPC115249
0.8553	High Similarity	NPC472891
0.8543	High Similarity	NPC215711
0.8543	High Similarity	NPC94781
0.8543	High Similarity	NPC172329
0.8543	High Similarity	NPC73411
0.8543	High Similarity	NPC221352
0.8543	High Similarity	NPC2569
0.8542	High Similarity	NPC27407
0.8533	High Similarity	NPC472033
0.8533	High Similarity	NPC268366
0.8533	High Similarity	NPC107625
0.8533	High Similarity	NPC299011
0.8531	High Similarity	NPC153783
0.8523	High Similarity	NPC113770
0.8523	High Similarity	NPC471906
0.8521	High Similarity	NPC198249
0.8516	High Similarity	NPC227062
0.8514	High Similarity	NPC49108
0.8514	High Similarity	NPC250755
0.8514	High Similarity	NPC137649
0.8506	High Similarity	NPC137301
0.8503	High Similarity	NPC158472
0.8497	Intermediate Similarity	NPC92747
0.8497	Intermediate Similarity	NPC215921
0.8497	Intermediate Similarity	NPC265862
0.8497	Intermediate Similarity	NPC39819
0.8497	Intermediate Similarity	NPC70016
0.8493	Intermediate Similarity	NPC472403
0.8493	Intermediate Similarity	NPC9121
0.8493	Intermediate Similarity	NPC177307
0.8493	Intermediate Similarity	NPC221104
0.8487	Intermediate Similarity	NPC120171
0.8483	Intermediate Similarity	NPC291454
0.8477	Intermediate Similarity	NPC259632
0.8477	Intermediate Similarity	NPC77903
0.8477	Intermediate Similarity	NPC210320
0.8477	Intermediate Similarity	NPC17101
0.8477	Intermediate Similarity	NPC472036
0.8471	Intermediate Similarity	NPC24627
0.8471	Intermediate Similarity	NPC471744
0.8467	Intermediate Similarity	NPC472034
0.8467	Intermediate Similarity	NPC311144
0.8466	Intermediate Similarity	NPC171706
0.8462	Intermediate Similarity	NPC478190
0.8456	Intermediate Similarity	NPC202981
0.8456	Intermediate Similarity	NPC51106
0.8456	Intermediate Similarity	NPC471731
0.8456	Intermediate Similarity	NPC472610
0.8456	Intermediate Similarity	NPC73028
0.8456	Intermediate Similarity	NPC469542
0.8456	Intermediate Similarity	NPC310340
0.8446	Intermediate Similarity	NPC1704
0.8446	Intermediate Similarity	NPC470842
0.8446	Intermediate Similarity	NPC67650
0.8442	Intermediate Similarity	NPC167903
0.8442	Intermediate Similarity	NPC478224
0.8438	Intermediate Similarity	NPC477517
0.8435	Intermediate Similarity	NPC32360
0.8435	Intermediate Similarity	NPC92655
0.8435	Intermediate Similarity	NPC105456
0.8435	Intermediate Similarity	NPC275356
0.8435	Intermediate Similarity	NPC86744
0.8435	Intermediate Similarity	NPC19622
0.8435	Intermediate Similarity	NPC139634
0.8435	Intermediate Similarity	NPC112789
0.8431	Intermediate Similarity	NPC267117
0.8431	Intermediate Similarity	NPC225854
0.8425	Intermediate Similarity	NPC65837
0.8425	Intermediate Similarity	NPC178467
0.8425	Intermediate Similarity	NPC474771
0.8425	Intermediate Similarity	NPC149372
0.8425	Intermediate Similarity	NPC474849
0.8421	Intermediate Similarity	NPC153417
0.8421	Intermediate Similarity	NPC39195
0.8418	Intermediate Similarity	NPC112418
0.8414	Intermediate Similarity	NPC142027
0.8411	Intermediate Similarity	NPC473023
0.8411	Intermediate Similarity	NPC267509
0.8408	Intermediate Similarity	NPC470339
0.8403	Intermediate Similarity	NPC472591
0.84	Intermediate Similarity	NPC184702
0.84	Intermediate Similarity	NPC470216
0.84	Intermediate Similarity	NPC470932
0.8392	Intermediate Similarity	NPC219892
0.8392	Intermediate Similarity	NPC189823
0.8392	Intermediate Similarity	NPC214702
0.8392	Intermediate Similarity	NPC470831
0.8389	Intermediate Similarity	NPC471733
0.8389	Intermediate Similarity	NPC18714
0.8389	Intermediate Similarity	NPC474385
0.8389	Intermediate Similarity	NPC297985
0.8389	Intermediate Similarity	NPC103752
0.8389	Intermediate Similarity	NPC469579
0.8387	Intermediate Similarity	NPC203080
0.8378	Intermediate Similarity	NPC254994
0.8378	Intermediate Similarity	NPC275903
0.8377	Intermediate Similarity	NPC221249
0.8377	Intermediate Similarity	NPC205918
0.8377	Intermediate Similarity	NPC471229
0.8369	Intermediate Similarity	NPC209959
0.8367	Intermediate Similarity	NPC475974
0.8367	Intermediate Similarity	NPC197666
0.8367	Intermediate Similarity	NPC126739
0.8366	Intermediate Similarity	NPC306343
0.8366	Intermediate Similarity	NPC44378
0.8366	Intermediate Similarity	NPC280753
0.8366	Intermediate Similarity	NPC476684
0.8366	Intermediate Similarity	NPC270160
0.8366	Intermediate Similarity	NPC277032
0.8366	Intermediate Similarity	NPC9099
0.8366	Intermediate Similarity	NPC247219
0.8366	Intermediate Similarity	NPC237440
0.8365	Intermediate Similarity	NPC471745
0.8355	Intermediate Similarity	NPC142863
0.8355	Intermediate Similarity	NPC308200
0.8355	Intermediate Similarity	NPC52106
0.8355	Intermediate Similarity	NPC119767
0.8355	Intermediate Similarity	NPC5568
0.8354	Intermediate Similarity	NPC472055
0.8354	Intermediate Similarity	NPC155101

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 NPC202112 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	293
0.1-0.2	894
0.2-0.3	1507
0.3-0.4	2514
0.4-0.5	2066
0.5-0.6	1210
0.6-0.7	471
0.7-0.8	177
0.8-0.85	18
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8387	Intermediate Similarity	NPD7819	Suspended
0.8344	Intermediate Similarity	NPD7075	Discontinued
0.8322	Intermediate Similarity	NPD3750	Approved
0.8311	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD1549	Phase 2
0.8165	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD230	Phase 1
0.8121	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD1510	Phase 2
0.8105	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD1934	Approved
0.8069	Intermediate Similarity	NPD3764	Approved
0.8039	Intermediate Similarity	NPD6799	Approved
0.8038	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5844	Phase 1
0.8	Intermediate Similarity	NPD3749	Approved
0.7988	Intermediate Similarity	NPD7473	Discontinued
0.7987	Intermediate Similarity	NPD2533	Approved
0.7987	Intermediate Similarity	NPD2534	Approved
0.7987	Intermediate Similarity	NPD3748	Approved
0.7987	Intermediate Similarity	NPD2532	Approved
0.7987	Intermediate Similarity	NPD3817	Phase 2
0.7975	Intermediate Similarity	NPD6801	Discontinued
0.7962	Intermediate Similarity	NPD4380	Phase 2
0.7962	Intermediate Similarity	NPD6599	Discontinued
0.7959	Intermediate Similarity	NPD1240	Approved
0.7937	Intermediate Similarity	NPD3882	Suspended
0.7925	Intermediate Similarity	NPD1465	Phase 2
0.7914	Intermediate Similarity	NPD6232	Discontinued
0.7911	Intermediate Similarity	NPD7411	Suspended
0.7908	Intermediate Similarity	NPD6190	Approved
0.7904	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD5402	Approved
0.7875	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD6959	Discontinued
0.7852	Intermediate Similarity	NPD1607	Approved
0.7838	Intermediate Similarity	NPD943	Approved
0.7821	Intermediate Similarity	NPD1512	Approved
0.7818	Intermediate Similarity	NPD6166	Phase 2
0.7818	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD2935	Discontinued
0.7815	Intermediate Similarity	NPD2796	Approved
0.7811	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD9545	Approved
0.7778	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD2346	Discontinued
0.7759	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD8150	Discontinued
0.7711	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD2801	Approved
0.7692	Intermediate Similarity	NPD7390	Discontinued
0.7692	Intermediate Similarity	NPD1511	Approved
0.7692	Intermediate Similarity	NPD6797	Phase 2
0.7683	Intermediate Similarity	NPD5494	Approved
0.7679	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD3226	Approved
0.7673	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD5403	Approved
0.7647	Intermediate Similarity	NPD7251	Discontinued
0.7643	Intermediate Similarity	NPD5401	Approved
0.7619	Intermediate Similarity	NPD3818	Discontinued
0.7619	Intermediate Similarity	NPD3751	Discontinued
0.7613	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD4628	Phase 3
0.7607	Intermediate Similarity	NPD7768	Phase 2
0.7603	Intermediate Similarity	NPD1470	Approved
0.7602	Intermediate Similarity	NPD7808	Phase 3
0.7582	Intermediate Similarity	NPD1551	Phase 2
0.7582	Intermediate Similarity	NPD5404	Approved
0.7582	Intermediate Similarity	NPD5406	Approved
0.7582	Intermediate Similarity	NPD5405	Approved
0.7582	Intermediate Similarity	NPD6100	Approved
0.7582	Intermediate Similarity	NPD6099	Approved
0.7582	Intermediate Similarity	NPD5408	Approved
0.7572	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD37	Approved
0.7529	Intermediate Similarity	NPD7074	Phase 3
0.7517	Intermediate Similarity	NPD9269	Phase 2
0.7516	Intermediate Similarity	NPD2799	Discontinued
0.7515	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD4966	Approved
0.75	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD4967	Phase 2
0.7485	Intermediate Similarity	NPD5711	Approved
0.7485	Intermediate Similarity	NPD5710	Approved
0.7485	Intermediate Similarity	NPD7229	Phase 3
0.7483	Intermediate Similarity	NPD4060	Phase 1
0.7483	Intermediate Similarity	NPD9268	Approved
0.7471	Intermediate Similarity	NPD7054	Approved
0.7467	Intermediate Similarity	NPD3268	Approved
0.7448	Intermediate Similarity	NPD1201	Approved
0.7442	Intermediate Similarity	NPD6559	Discontinued
0.7438	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD920	Approved
0.7434	Intermediate Similarity	NPD6355	Discontinued
0.7427	Intermediate Similarity	NPD7472	Approved
0.741	Intermediate Similarity	NPD919	Approved
0.7405	Intermediate Similarity	NPD7236	Approved
0.7397	Intermediate Similarity	NPD1608	Approved
0.7394	Intermediate Similarity	NPD9493	Approved
0.7391	Intermediate Similarity	NPD8319	Approved
0.7391	Intermediate Similarity	NPD8320	Phase 1
0.7389	Intermediate Similarity	NPD7003	Approved
0.7381	Intermediate Similarity	NPD3787	Discontinued
0.7375	Intermediate Similarity	NPD6273	Approved
0.7365	Intermediate Similarity	NPD2797	Approved
0.7362	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD6798	Discontinued
0.7351	Intermediate Similarity	NPD2313	Discontinued
0.7346	Intermediate Similarity	NPD7458	Discontinued
0.7337	Intermediate Similarity	NPD7435	Discontinued
0.7333	Intermediate Similarity	NPD4288	Approved
0.7333	Intermediate Similarity	NPD4908	Phase 1
0.7329	Intermediate Similarity	NPD1610	Phase 2
0.7325	Intermediate Similarity	NPD2800	Approved
0.7321	Intermediate Similarity	NPD7199	Phase 2
0.7312	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7228	Approved
0.7308	Intermediate Similarity	NPD2344	Approved
0.7308	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1283	Approved
0.729	Intermediate Similarity	NPD4308	Phase 3
0.7283	Intermediate Similarity	NPD5953	Discontinued
0.7278	Intermediate Similarity	NPD6535	Approved
0.7278	Intermediate Similarity	NPD6534	Approved
0.7278	Intermediate Similarity	NPD8166	Discontinued
0.7267	Intermediate Similarity	NPD7286	Phase 2
0.7257	Intermediate Similarity	NPD8313	Approved
0.7257	Intermediate Similarity	NPD8312	Approved
0.7248	Intermediate Similarity	NPD3267	Approved
0.7248	Intermediate Similarity	NPD1164	Approved
0.7248	Intermediate Similarity	NPD3266	Approved
0.7248	Intermediate Similarity	NPD1203	Approved
0.7237	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD8434	Phase 2
0.7219	Intermediate Similarity	NPD1247	Approved
0.7215	Intermediate Similarity	NPD1243	Approved
0.7208	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2798	Approved
0.7192	Intermediate Similarity	NPD17	Approved
0.719	Intermediate Similarity	NPD6663	Approved
0.719	Intermediate Similarity	NPD6233	Phase 2
0.7188	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD1876	Approved
0.7178	Intermediate Similarity	NPD7239	Suspended
0.7174	Intermediate Similarity	NPD6782	Approved
0.7174	Intermediate Similarity	NPD6779	Approved
0.7174	Intermediate Similarity	NPD6777	Approved
0.7174	Intermediate Similarity	NPD6776	Approved
0.7174	Intermediate Similarity	NPD6778	Approved
0.7174	Intermediate Similarity	NPD6781	Approved
0.7174	Intermediate Similarity	NPD6780	Approved
0.7158	Intermediate Similarity	NPD7699	Phase 2
0.7158	Intermediate Similarity	NPD7700	Phase 2
0.7153	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5736	Approved
0.7151	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1613	Approved
0.7143	Intermediate Similarity	NPD2979	Phase 3
0.7143	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7685	Pre-registration
0.7135	Intermediate Similarity	NPD3926	Phase 2
0.7135	Intermediate Similarity	NPD5242	Approved
0.7126	Intermediate Similarity	NPD5353	Approved
0.7125	Intermediate Similarity	NPD3887	Approved
0.7125	Intermediate Similarity	NPD2309	Approved
0.7125	Intermediate Similarity	NPD2354	Approved
0.7122	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6832	Phase 2
0.7105	Intermediate Similarity	NPD7874	Approved
0.7105	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5124	Phase 1
0.7097	Intermediate Similarity	NPD447	Suspended
0.7097	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD422	Phase 1
0.7095	Intermediate Similarity	NPD1281	Approved
0.7095	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7266	Discontinued
0.7089	Intermediate Similarity	NPD1471	Phase 3
0.707	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD7033	Discontinued
0.7059	Intermediate Similarity	NPD7698	Approved
0.7059	Intermediate Similarity	NPD7696	Phase 3
0.7059	Intermediate Similarity	NPD7697	Approved
0.7059	Intermediate Similarity	NPD4625	Phase 3
0.7056	Intermediate Similarity	NPD4287	Approved
0.7053	Intermediate Similarity	NPD8151	Discontinued

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