NPASS Compound

Structure

CID275055 OpenBabel06191716082D 21 23 0 0 0 0 0 0 0 0999 V2000 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 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 4.3301 0.5000 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 -2.5981 0.5000 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 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 1.5000 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 -1.7321 -0.0000 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 O 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 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 1 9 2 0 0 0 0 2 4 2 0 0 0 0 2 9 1 0 0 0 0 3 11 2 0 0 0 0 4 11 1 0 0 0 0 5 9 1 0 0 0 0 5 10 2 0 0 0 0 6 12 2 0 0 0 0 6 13 1 0 0 0 0 7 12 1 0 0 0 0 7 14 2 0 0 0 0 8 10 1 0 0 0 0 8 21 1 0 0 0 0 10 16 1 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 13 15 2 0 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 14 21 1 0 0 0 0 15 16 1 0 0 0 0 16 20 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.24
Volume:	416.92
LogP:	2.792
LogD:	2.825
LogS:	-4.03
# Rotatable Bonds:	1
TPSA:	90.9
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.671
Synthetic Accessibility Score:	4.584
Fsp3:	0.792
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:	-4.909
MDCK Permeability:	1.3610644600703381e-05
Pgp-inhibitor:	0.022
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.954
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.329
Plasma Protein Binding (PPB):	89.33837127685547%
Volume Distribution (VD):	0.696
Pgp-substrate:	10.070667266845703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.759
CYP2C19-inhibitor:	0.049
CYP2C19-substrate:	0.673
CYP2C9-inhibitor:	0.107
CYP2C9-substrate:	0.088
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.172
CYP3A4-inhibitor:	0.891
CYP3A4-substrate:	0.306

ADMET: Excretion

Clearance (CL):	12.138
Half-life (T1/2):	0.251

ADMET: Toxicity

hERG Blockers:	0.279
Human Hepatotoxicity (H-HT):	0.437
Drug-inuced Liver Injury (DILI):	0.044
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.721
Maximum Recommended Daily Dose:	0.925
Skin Sensitization:	0.764
Carcinogencity:	0.677
Eye Corrosion:	0.029
Eye Irritation:	0.038
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC275055

Natural Product ID:	NPC275055
*Common Name:**	Demethyleucomin
IUPAC Name:	(3E)-5,7-dihydroxy-3-[(4-hydroxyphenyl)methylidene]chromen-4-one
Synonyms:
Standard InCHIKey:	PKCWSPYCHMNVKB-BJMVGYQFSA-N
Standard InCHI:	InChI=1S/C16H12O5/c17-11-3-1-9(2-4-11)5-10-8-21-14-7-12(18)6-13(19)15(14)16(10)20/h1-7,17-19H,8H2/b10-5+
SMILES:	c1cc(ccc1/C=C/1COc2cc(cc(c2C1=O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077616
PubChem CID:	15484393
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002507] Homoisoflavonoids

*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
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19757853]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21370894]
NPO33045	bellevalia eigii	Species	Hyacinthaceae	Eukaryota	Bulbs	Irbid, Jordan	n.a.	PMID[26147490]
NPO40241	Hyacinthaceae	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[30951308]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[8482946]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	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
GI50	4
IC50	6
Others	6

Activity Type	# Activity
Cell Line	4
CELL-LINE	1
Individual Protein	8
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT520	Cell Line	3T3-L1	Mus musculus	IC50	>	100000.0	nM	PMID[543681]
NPT582	Individual Protein	Monoamine oxidase B	Homo sapiens	IC50	=	8.61	nM	PMID[543682]
NPT261	Individual Protein	Monoamine oxidase A	Homo sapiens	IC50	=	11460.0	nM	PMID[543682]
NPT261	Individual Protein	Monoamine oxidase A	Homo sapiens	Inhibition	=	68.26	%	PMID[543682]
NPT261	Individual Protein	Monoamine oxidase A	Homo sapiens	Inhibition	=	61.76	%	PMID[543682]
NPT582	Individual Protein	Monoamine oxidase B	Homo sapiens	Inhibition	=	48.66	%	PMID[543682]
NPT582	Individual Protein	Monoamine oxidase B	Homo sapiens	Inhibition	=	36.22	%	PMID[543682]
NPT582	Individual Protein	Monoamine oxidase B	Homo sapiens	Activity	=	-1.68	%	PMID[543683]
NPT582	Individual Protein	Monoamine oxidase B	Homo sapiens	IC50	=	8709.64	nM	PMID[543683]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	>	20000.0	nM	PMID[543684]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	20000.0	nM	PMID[543684]
NPT5265	Cell Line	Y79	Homo sapiens	GI50	>	100000.0	nM	PMID[543685]
NPT2	Others	Unspecified		Ratio IC50	=	1331.0	n.a.	PMID[543682]
NPT2	Others	Unspecified		GI50	=	60000.0	nM	PMID[543685]
NPT2	Others	Unspecified		GI50	>	100000.0	nM	PMID[543685]
NPT21798	CELL-LINE	ARPE-19	Homo sapiens	GI50	>	100000.0	nM	PMID[543685]

☑ 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 NPC275055 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	364
0.1-0.2	1678
0.2-0.3	4651
0.3-0.4	11221
0.4-0.5	6336
0.5-0.6	3826
0.6-0.7	5695
0.7-0.8	5169
0.8-0.85	2146
0.85-0.9	1021
0.9-0.95	492
0.95-1	98

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC290291
0.9924	High Similarity	NPC188947
0.9924	High Similarity	NPC99333
0.9924	High Similarity	NPC280284
0.985	High Similarity	NPC261234
0.9774	High Similarity	NPC472460
0.9774	High Similarity	NPC118813
0.9774	High Similarity	NPC147686
0.9774	High Similarity	NPC329225
0.9704	High Similarity	NPC3188
0.9701	High Similarity	NPC150648
0.9701	High Similarity	NPC329203
0.9701	High Similarity	NPC274784
0.9701	High Similarity	NPC222342
0.9701	High Similarity	NPC225153
0.9701	High Similarity	NPC265871
0.9701	High Similarity	NPC20709
0.9701	High Similarity	NPC310135
0.9699	High Similarity	NPC287246
0.9699	High Similarity	NPC296490
0.9699	High Similarity	NPC79943
0.9699	High Similarity	NPC476480
0.9699	High Similarity	NPC266597
0.9699	High Similarity	NPC13768
0.9699	High Similarity	NPC188879
0.9699	High Similarity	NPC32441
0.9699	High Similarity	NPC84585
0.9699	High Similarity	NPC250266
0.9699	High Similarity	NPC107586
0.9699	High Similarity	NPC12296
0.9699	High Similarity	NPC243083
0.9699	High Similarity	NPC295261
0.9697	High Similarity	NPC9985
0.9697	High Similarity	NPC239495
0.9632	High Similarity	NPC202981
0.963	High Similarity	NPC6407
0.963	High Similarity	NPC284550
0.963	High Similarity	NPC76445
0.963	High Similarity	NPC188243
0.963	High Similarity	NPC129853
0.963	High Similarity	NPC110228
0.9627	High Similarity	NPC124269
0.9624	High Similarity	NPC124784
0.9624	High Similarity	NPC240593
0.9624	High Similarity	NPC231772
0.9624	High Similarity	NPC29353
0.9624	High Similarity	NPC194281
0.9624	High Similarity	NPC234133
0.9624	High Similarity	NPC47815
0.9624	High Similarity	NPC127447
0.9624	High Similarity	NPC473887
0.9621	High Similarity	NPC172262
0.9562	High Similarity	NPC143896
0.9562	High Similarity	NPC221432
0.9562	High Similarity	NPC164980
0.9562	High Similarity	NPC75049
0.9562	High Similarity	NPC149026
0.9562	High Similarity	NPC310130
0.9562	High Similarity	NPC169591
0.9562	High Similarity	NPC175504
0.9562	High Similarity	NPC91560
0.9562	High Similarity	NPC68104
0.9562	High Similarity	NPC39329
0.9562	High Similarity	NPC257097
0.9562	High Similarity	NPC150408
0.9559	High Similarity	NPC324386
0.9559	High Similarity	NPC4743
0.9559	High Similarity	NPC312391
0.9559	High Similarity	NPC213322
0.9556	High Similarity	NPC316480
0.9556	High Similarity	NPC140890
0.9545	High Similarity	NPC274121
0.9545	High Similarity	NPC57601
0.9545	High Similarity	NPC78540
0.9545	High Similarity	NPC50898
0.9545	High Similarity	NPC213216
0.9493	High Similarity	NPC473015
0.9493	High Similarity	NPC303185
0.9493	High Similarity	NPC209040
0.9493	High Similarity	NPC184649
0.9493	High Similarity	NPC236766
0.9493	High Similarity	NPC473013
0.9493	High Similarity	NPC197252
0.9489	High Similarity	NPC1089
0.9489	High Similarity	NPC125855
0.9489	High Similarity	NPC182852
0.9489	High Similarity	NPC324134
0.9489	High Similarity	NPC306829
0.9489	High Similarity	NPC32739
0.9489	High Similarity	NPC161506
0.9489	High Similarity	NPC37496
0.9489	High Similarity	NPC76372
0.9489	High Similarity	NPC167624
0.9489	High Similarity	NPC64915
0.9489	High Similarity	NPC220998
0.9489	High Similarity	NPC76338
0.9489	High Similarity	NPC78
0.9489	High Similarity	NPC107572
0.9489	High Similarity	NPC227579
0.9489	High Similarity	NPC324436
0.9489	High Similarity	NPC166482
0.9489	High Similarity	NPC194432
0.9489	High Similarity	NPC223500
0.9489	High Similarity	NPC10937
0.9489	High Similarity	NPC265040
0.9489	High Similarity	NPC177354
0.9489	High Similarity	NPC166934
0.9489	High Similarity	NPC228504
0.9489	High Similarity	NPC296917
0.9489	High Similarity	NPC328164
0.9489	High Similarity	NPC148757
0.9489	High Similarity	NPC66515
0.9489	High Similarity	NPC40833
0.9485	High Similarity	NPC269652
0.9485	High Similarity	NPC69769
0.9485	High Similarity	NPC281207
0.9478	High Similarity	NPC13408
0.9474	High Similarity	NPC125269
0.947	High Similarity	NPC257756
0.947	High Similarity	NPC205468
0.947	High Similarity	NPC87231
0.947	High Similarity	NPC212631
0.947	High Similarity	NPC129132
0.9424	High Similarity	NPC299011
0.9424	High Similarity	NPC229190
0.942	High Similarity	NPC81697
0.942	High Similarity	NPC166138
0.942	High Similarity	NPC113770
0.942	High Similarity	NPC107177
0.942	High Similarity	NPC106985
0.942	High Similarity	NPC223812
0.942	High Similarity	NPC316816
0.942	High Similarity	NPC125894
0.942	High Similarity	NPC278249
0.942	High Similarity	NPC214166
0.942	High Similarity	NPC77794
0.942	High Similarity	NPC185276
0.942	High Similarity	NPC85162
0.942	High Similarity	NPC478086
0.942	High Similarity	NPC18585
0.9416	High Similarity	NPC96408
0.9416	High Similarity	NPC279650
0.9416	High Similarity	NPC248372
0.9416	High Similarity	NPC166689
0.9416	High Similarity	NPC110038
0.9416	High Similarity	NPC110969
0.9416	High Similarity	NPC17170
0.9416	High Similarity	NPC136840
0.9416	High Similarity	NPC156190
0.9416	High Similarity	NPC258630
0.9412	High Similarity	NPC18260
0.9412	High Similarity	NPC143799
0.9412	High Similarity	NPC152042
0.9412	High Similarity	NPC241838
0.9412	High Similarity	NPC78913
0.9407	High Similarity	NPC303644
0.9407	High Similarity	NPC294409
0.9407	High Similarity	NPC116632
0.9407	High Similarity	NPC181124
0.9407	High Similarity	NPC228661
0.9407	High Similarity	NPC209560
0.9407	High Similarity	NPC162680
0.9407	High Similarity	NPC7013
0.9407	High Similarity	NPC299379
0.9403	High Similarity	NPC234560
0.9403	High Similarity	NPC39426
0.9398	High Similarity	NPC192304
0.9398	High Similarity	NPC337373
0.9398	High Similarity	NPC139813
0.9398	High Similarity	NPC188646
0.9398	High Similarity	NPC56031
0.9398	High Similarity	NPC175098
0.9398	High Similarity	NPC263670
0.9398	High Similarity	NPC472365
0.9398	High Similarity	NPC242294
0.9398	High Similarity	NPC312318
0.9394	High Similarity	NPC113006
0.9394	High Similarity	NPC64359
0.9394	High Similarity	NPC262359
0.9394	High Similarity	NPC308037
0.9357	High Similarity	NPC23728
0.9357	High Similarity	NPC95864
0.9357	High Similarity	NPC110303
0.9353	High Similarity	NPC470135
0.9353	High Similarity	NPC473014
0.9353	High Similarity	NPC131579
0.9353	High Similarity	NPC39045
0.9353	High Similarity	NPC470136
0.9353	High Similarity	NPC235217
0.9353	High Similarity	NPC131568
0.9353	High Similarity	NPC311144
0.9353	High Similarity	NPC271288
0.9348	High Similarity	NPC147145
0.9348	High Similarity	NPC144499
0.9348	High Similarity	NPC226636
0.9348	High Similarity	NPC73028
0.9348	High Similarity	NPC11561
0.9343	High Similarity	NPC184536
0.9343	High Similarity	NPC182421
0.9343	High Similarity	NPC270883

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 NPC275055 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	337
0.1-0.2	956
0.2-0.3	1571
0.3-0.4	2622
0.4-0.5	1819
0.5-0.6	1213
0.6-0.7	419
0.7-0.8	147
0.8-0.85	41
0.85-0.9	18
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9774	High Similarity	NPD1549	Phase 2
0.9699	High Similarity	NPD1550	Clinical (unspecified phase)
0.9699	High Similarity	NPD1552	Clinical (unspecified phase)
0.9403	High Similarity	NPD1510	Phase 2
0.9248	High Similarity	NPD1240	Approved
0.9111	High Similarity	NPD1607	Approved
0.9078	High Similarity	NPD4378	Clinical (unspecified phase)
0.9051	High Similarity	NPD2796	Approved
0.8966	High Similarity	NPD7411	Suspended
0.8944	High Similarity	NPD7410	Clinical (unspecified phase)
0.8904	High Similarity	NPD1934	Approved
0.8897	High Similarity	NPD4380	Phase 2
0.8873	High Similarity	NPD1511	Approved
0.8873	High Similarity	NPD6799	Approved
0.8844	High Similarity	NPD2393	Clinical (unspecified phase)
0.8792	High Similarity	NPD4381	Clinical (unspecified phase)
0.8792	High Similarity	NPD7075	Discontinued
0.8784	High Similarity	NPD8443	Clinical (unspecified phase)
0.8777	High Similarity	NPD1551	Phase 2
0.875	High Similarity	NPD1512	Approved
0.8716	High Similarity	NPD7096	Clinical (unspecified phase)
0.8716	High Similarity	NPD7819	Suspended
0.8662	High Similarity	NPD3750	Approved
0.86	High Similarity	NPD3882	Suspended
0.8591	High Similarity	NPD2801	Approved
0.8543	High Similarity	NPD3749	Approved
0.854	High Similarity	NPD6859	Clinical (unspecified phase)
0.8523	High Similarity	NPD6801	Discontinued
0.8514	High Similarity	NPD6599	Discontinued
0.8462	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8444	Intermediate Similarity	NPD1203	Approved
0.8435	Intermediate Similarity	NPD5403	Approved
0.8425	Intermediate Similarity	NPD5401	Approved
0.8421	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8392	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD7768	Phase 2
0.8333	Intermediate Similarity	NPD6166	Phase 2
0.8333	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD3748	Approved
0.8289	Intermediate Similarity	NPD3817	Phase 2
0.8276	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD6959	Discontinued
0.8258	Intermediate Similarity	NPD1548	Phase 1
0.8235	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD3818	Discontinued
0.8207	Intermediate Similarity	NPD2800	Approved
0.8194	Intermediate Similarity	NPD2344	Approved
0.8176	Intermediate Similarity	NPD7054	Approved
0.8176	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD1610	Phase 2
0.8129	Intermediate Similarity	NPD6832	Phase 2
0.8125	Intermediate Similarity	NPD7074	Phase 3
0.8125	Intermediate Similarity	NPD7472	Approved
0.8088	Intermediate Similarity	NPD9717	Approved
0.8082	Intermediate Similarity	NPD1243	Approved
0.8077	Intermediate Similarity	NPD5494	Approved
0.8075	Intermediate Similarity	NPD6797	Phase 2
0.8067	Intermediate Similarity	NPD920	Approved
0.8054	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD5402	Approved
0.8042	Intermediate Similarity	NPD6651	Approved
0.8028	Intermediate Similarity	NPD943	Approved
0.8025	Intermediate Similarity	NPD7251	Discontinued
0.8014	Intermediate Similarity	NPD2313	Discontinued
0.8	Intermediate Similarity	NPD2935	Discontinued
0.8	Intermediate Similarity	NPD4908	Phase 1
0.7975	Intermediate Similarity	NPD7808	Phase 3
0.7975	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD2309	Approved
0.7963	Intermediate Similarity	NPD5953	Discontinued
0.795	Intermediate Similarity	NPD7286	Phase 2
0.7931	Intermediate Similarity	NPD2799	Discontinued
0.7914	Intermediate Similarity	NPD6559	Discontinued
0.7905	Intermediate Similarity	NPD4628	Phase 3
0.7887	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7883	Intermediate Similarity	NPD422	Phase 1
0.7877	Intermediate Similarity	NPD6100	Approved
0.7877	Intermediate Similarity	NPD6099	Approved
0.7866	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD9545	Approved
0.7847	Intermediate Similarity	NPD1933	Approved
0.7842	Intermediate Similarity	NPD3225	Approved
0.7815	Intermediate Similarity	NPD2533	Approved
0.7815	Intermediate Similarity	NPD2532	Approved
0.7815	Intermediate Similarity	NPD2534	Approved
0.7808	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD7033	Discontinued
0.7762	Intermediate Similarity	NPD3268	Approved
0.7756	Intermediate Similarity	NPD1465	Phase 2
0.775	Intermediate Similarity	NPD6232	Discontinued
0.7744	Intermediate Similarity	NPD1241	Discontinued
0.7744	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD5844	Phase 1
0.773	Intermediate Similarity	NPD2798	Approved
0.7727	Intermediate Similarity	NPD3226	Approved
0.7724	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD2654	Approved
0.7716	Intermediate Similarity	NPD7473	Discontinued
0.7704	Intermediate Similarity	NPD9493	Approved
0.7703	Intermediate Similarity	NPD2346	Discontinued
0.7687	Intermediate Similarity	NPD4308	Phase 3
0.7673	Intermediate Similarity	NPD919	Approved
0.7667	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD2797	Approved
0.7655	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD1613	Approved
0.7622	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD1019	Discontinued
0.7603	Intermediate Similarity	NPD230	Phase 1
0.7595	Intermediate Similarity	NPD4288	Approved
0.7593	Intermediate Similarity	NPD3926	Phase 2
0.7582	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD1247	Approved
0.7571	Intermediate Similarity	NPD3972	Approved
0.7561	Intermediate Similarity	NPD3751	Discontinued
0.7552	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD3266	Approved
0.7535	Intermediate Similarity	NPD3267	Approved
0.7517	Intermediate Similarity	NPD1296	Phase 2
0.7517	Intermediate Similarity	NPD3764	Approved
0.7517	Intermediate Similarity	NPD411	Approved
0.7516	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4363	Phase 3
0.7514	Intermediate Similarity	NPD4360	Phase 2
0.7485	Intermediate Similarity	NPD4287	Approved
0.7485	Intermediate Similarity	NPD6104	Discontinued
0.7484	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD447	Suspended
0.7483	Intermediate Similarity	NPD5124	Phase 1
0.7483	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD1729	Discontinued
0.7464	Intermediate Similarity	NPD1894	Discontinued
0.745	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD1608	Approved
0.7447	Intermediate Similarity	NPD1481	Phase 2
0.7429	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD4307	Phase 2
0.7415	Intermediate Similarity	NPD3142	Approved
0.7415	Intermediate Similarity	NPD3140	Approved
0.7413	Intermediate Similarity	NPD1470	Approved
0.7403	Intermediate Similarity	NPD7390	Discontinued
0.7397	Intermediate Similarity	NPD6798	Discontinued
0.7389	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD1201	Approved
0.7376	Intermediate Similarity	NPD1535	Discovery
0.7375	Intermediate Similarity	NPD2296	Approved
0.7371	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD4361	Phase 2
0.7358	Intermediate Similarity	NPD6844	Discontinued
0.7338	Intermediate Similarity	NPD7440	Discontinued
0.7333	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4625	Phase 3
0.7317	Intermediate Similarity	NPD3787	Discontinued
0.7317	Intermediate Similarity	NPD5711	Approved
0.7317	Intermediate Similarity	NPD5710	Approved
0.731	Intermediate Similarity	NPD2861	Phase 2
0.7303	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD5889	Approved
0.7296	Intermediate Similarity	NPD5890	Approved
0.7292	Intermediate Similarity	NPD1164	Approved
0.7278	Intermediate Similarity	NPD7458	Discontinued
0.7273	Intermediate Similarity	NPD2354	Approved
0.7273	Intermediate Similarity	NPD4749	Approved
0.7255	Intermediate Similarity	NPD1652	Phase 2
0.725	Intermediate Similarity	NPD7577	Discontinued
0.7244	Intermediate Similarity	NPD4661	Approved
0.7244	Intermediate Similarity	NPD4662	Approved
0.7239	Intermediate Similarity	NPD9266	Approved
0.7239	Intermediate Similarity	NPD74	Approved
0.7237	Intermediate Similarity	NPD1471	Phase 3
0.7237	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD17	Approved
0.723	Intermediate Similarity	NPD6233	Phase 2
0.7222	Intermediate Similarity	NPD1876	Approved
0.72	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD8313	Approved
0.7193	Intermediate Similarity	NPD8312	Approved
0.7192	Intermediate Similarity	NPD9494	Approved
0.7179	Intermediate Similarity	NPD7212	Phase 2
0.7179	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7213	Phase 3
0.7178	Intermediate Similarity	NPD6971	Discontinued
0.7171	Intermediate Similarity	NPD5408	Approved
0.7171	Intermediate Similarity	NPD5406	Approved
0.7171	Intermediate Similarity	NPD5404	Approved
0.7171	Intermediate Similarity	NPD5405	Approved
0.7164	Intermediate Similarity	NPD9267	Approved
0.7164	Intermediate Similarity	NPD9264	Approved
0.7164	Intermediate Similarity	NPD9263	Approved
0.7164	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD3887	Approved
0.7158	Intermediate Similarity	NPD7584	Approved
0.7152	Intermediate Similarity	NPD7199	Phase 2
0.7143	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6280	Approved
0.7143	Intermediate Similarity	NPD6279	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