NPASS Compound

Structure

CID198829 OpenBabel06191715582D 33 36 0 0 0 0 0 0 0 0999 V2000 6.0622 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 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 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 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 0.5000 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 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 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 3.4641 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 4 5 1 0 0 0 0 4 12 2 0 0 0 0 5 14 1 0 0 0 0 6 7 2 0 0 0 0 6 13 1 0 0 0 0 7 25 1 0 0 0 0 8 15 2 0 0 0 0 8 17 1 0 0 0 0 9 16 2 0 0 0 0 9 18 1 0 0 0 0 10 19 2 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 26 1 0 0 0 0 13 20 2 0 0 0 0 13 24 1 0 0 0 0 14 22 1 0 0 0 0 14 23 2 0 0 0 0 15 16 1 0 0 0 0 15 23 1 0 0 0 0 16 27 1 0 0 0 0 17 18 2 0 0 0 0 17 28 1 0 0 0 0 18 29 1 0 0 0 0 19 21 1 0 0 0 0 19 30 1 0 0 0 0 20 33 1 0 0 0 0 21 22 1 0 0 0 0 21 24 2 0 0 0 0 22 31 2 0 0 0 0 23 32 1 0 0 0 0 24 32 1 0 0 0 0 25 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	452.15
Volume:	450.687
LogP:	4.423
LogD:	2.964
LogS:	-3.323
# Rotatable Bonds:	4
TPSA:	140.59
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.228
Synthetic Accessibility Score:	3.497
Fsp3:	0.24
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.913
MDCK Permeability:	1.3250926713226363e-05
Pgp-inhibitor:	0.037
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.11
20% Bioavailability (F20%):	0.643
30% Bioavailability (F30%):	0.88

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	94.7603530883789%
Volume Distribution (VD):	0.625
Pgp-substrate:	7.283335208892822%

ADMET: Metabolism

CYP1A2-inhibitor:	0.77
CYP1A2-substrate:	0.142
CYP2C19-inhibitor:	0.1
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.786
CYP2C9-substrate:	0.483
CYP2D6-inhibitor:	0.381
CYP2D6-substrate:	0.197
CYP3A4-inhibitor:	0.23
CYP3A4-substrate:	0.085

ADMET: Excretion

Clearance (CL):	5.92
Half-life (T1/2):	0.807

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.864
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.68
Rat Oral Acute Toxicity:	0.555
Maximum Recommended Daily Dose:	0.897
Skin Sensitization:	0.45
Carcinogencity:	0.731
Eye Corrosion:	0.003
Eye Irritation:	0.74
Respiratory Toxicity:	0.36

Download Data

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

Natural Product: NPC198829

Natural Product ID:	NPC198829
*Common Name:**	5-Hydroxy-3-[(Z)-4-Hydroxy-3-Methylbut-2-Enyl]-8,8-Dimethyl-2-(2,4,5-Trihydroxyphenyl)Pyrano[2,3-H]Chromen-4-One
IUPAC Name:	5-hydroxy-3-[(Z)-4-hydroxy-3-methylbut-2-enyl]-8,8-dimethyl-2-(2,4,5-trihydroxyphenyl)pyrano[2,3-h]chromen-4-one
Synonyms:
Standard InCHIKey:	UTYRRYOOGHLXNT-QCDXTXTGSA-N
Standard InCHI:	InChI=1S/C25H24O8/c1-12(11-26)4-5-14-22(31)21-19(30)10-20-13(6-7-25(2,3)33-20)24(21)32-23(14)15-8-17(28)18(29)9-16(15)27/h4,6-10,26-30H,5,11H2,1-3H3/b12-4-
SMILES:	OC/C(=CCc1c(oc2c(c1=O)c(O)cc1c2C=CC(O1)(C)C)c1cc(O)c(cc1O)O)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689345
PubChem CID:	53321447
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003501] 3-prenylated flavones

*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
NPO8211	Artocarpus odoratissimus	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21275386]
NPO8211	Artocarpus odoratissimus	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1422	Individual Protein	ATP-binding cassette sub-family G member 2	Homo sapiens	IC50	=	6500.0	nM	PMID[496685]

☑ 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 NPC198829 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	432
0.1-0.2	1703
0.2-0.3	4190
0.3-0.4	10411
0.4-0.5	7774
0.5-0.6	3657
0.6-0.7	5120
0.7-0.8	4759
0.8-0.85	2302
0.85-0.9	1593
0.9-0.95	731
0.95-1	25

Similarity Score	Similarity Level	Natural Product ID
0.9737	High Similarity	NPC276444
0.9679	High Similarity	NPC50960
0.9677	High Similarity	NPC194427
0.9673	High Similarity	NPC476630
0.9673	High Similarity	NPC218871
0.961	High Similarity	NPC469658
0.9608	High Similarity	NPC282307
0.9608	High Similarity	NPC170026
0.9605	High Similarity	NPC170492
0.9551	High Similarity	NPC261470
0.9487	High Similarity	NPC26326
0.9487	High Similarity	NPC474038
0.9487	High Similarity	NPC259456
0.9484	High Similarity	NPC117418
0.9484	High Similarity	NPC74178
0.9484	High Similarity	NPC53545
0.9484	High Similarity	NPC184755
0.9481	High Similarity	NPC471985
0.9427	High Similarity	NPC83922
0.9427	High Similarity	NPC472448
0.9423	High Similarity	NPC119209
0.9423	High Similarity	NPC118256
0.9423	High Similarity	NPC476980
0.9423	High Similarity	NPC204290
0.9423	High Similarity	NPC28241
0.9423	High Similarity	NPC475784
0.9423	High Similarity	NPC192686
0.9419	High Similarity	NPC237418
0.9419	High Similarity	NPC471209
0.9416	High Similarity	NPC321779
0.9412	High Similarity	NPC249570
0.9408	High Similarity	NPC88804
0.9408	High Similarity	NPC3825
0.9367	High Similarity	NPC470459
0.9367	High Similarity	NPC472625
0.9363	High Similarity	NPC142252
0.9363	High Similarity	NPC266314
0.9363	High Similarity	NPC289771
0.9363	High Similarity	NPC40037
0.9363	High Similarity	NPC29876
0.9363	High Similarity	NPC167678
0.9363	High Similarity	NPC472632
0.9363	High Similarity	NPC472634
0.9359	High Similarity	NPC187792
0.9351	High Similarity	NPC192083
0.9351	High Similarity	NPC476631
0.9351	High Similarity	NPC74924
0.9351	High Similarity	NPC213896
0.9346	High Similarity	NPC154345
0.9313	High Similarity	NPC471288
0.9313	High Similarity	NPC158761
0.9308	High Similarity	NPC156432
0.9308	High Similarity	NPC239752
0.9308	High Similarity	NPC275780
0.9308	High Similarity	NPC470457
0.9308	High Similarity	NPC472450
0.9304	High Similarity	NPC474034
0.9304	High Similarity	NPC474033
0.9304	High Similarity	NPC474150
0.9304	High Similarity	NPC329760
0.9304	High Similarity	NPC474162
0.9304	High Similarity	NPC472635
0.9304	High Similarity	NPC220912
0.9299	High Similarity	NPC472631
0.9299	High Similarity	NPC328102
0.9299	High Similarity	NPC472630
0.9299	High Similarity	NPC174953
0.9295	High Similarity	NPC470402
0.9295	High Similarity	NPC476981
0.9295	High Similarity	NPC78103
0.9295	High Similarity	NPC223787
0.9295	High Similarity	NPC52889
0.9295	High Similarity	NPC474055
0.9295	High Similarity	NPC284820
0.9295	High Similarity	NPC27337
0.9295	High Similarity	NPC473272
0.9295	High Similarity	NPC78225
0.9295	High Similarity	NPC78071
0.9295	High Similarity	NPC472598
0.929	High Similarity	NPC92659
0.929	High Similarity	NPC146165
0.929	High Similarity	NPC227325
0.929	High Similarity	NPC4455
0.929	High Similarity	NPC280339
0.929	High Similarity	NPC234255
0.929	High Similarity	NPC133392
0.929	High Similarity	NPC128863
0.929	High Similarity	NPC470681
0.929	High Similarity	NPC2476
0.929	High Similarity	NPC196439
0.929	High Similarity	NPC138360
0.929	High Similarity	NPC201136
0.929	High Similarity	NPC213622
0.929	High Similarity	NPC50715
0.929	High Similarity	NPC163780
0.929	High Similarity	NPC183597
0.929	High Similarity	NPC113906
0.929	High Similarity	NPC167815
0.9286	High Similarity	NPC323626
0.9286	High Similarity	NPC157784
0.9286	High Similarity	NPC106976
0.9286	High Similarity	NPC37684
0.9286	High Similarity	NPC471982
0.9286	High Similarity	NPC324233
0.9286	High Similarity	NPC63187
0.9281	High Similarity	NPC37348
0.9281	High Similarity	NPC184136
0.9276	High Similarity	NPC119059
0.9255	High Similarity	NPC471287
0.925	High Similarity	NPC471213
0.925	High Similarity	NPC39091
0.925	High Similarity	NPC470462
0.9245	High Similarity	NPC189473
0.9245	High Similarity	NPC186686
0.9245	High Similarity	NPC207690
0.9245	High Similarity	NPC476295
0.9245	High Similarity	NPC41301
0.9245	High Similarity	NPC23298
0.9241	High Similarity	NPC471499
0.9241	High Similarity	NPC471211
0.9241	High Similarity	NPC228383
0.9241	High Similarity	NPC258331
0.9241	High Similarity	NPC471210
0.9241	High Similarity	NPC471212
0.9236	High Similarity	NPC284127
0.9236	High Similarity	NPC473990
0.9236	High Similarity	NPC250214
0.9236	High Similarity	NPC476410
0.9236	High Similarity	NPC95936
0.9236	High Similarity	NPC22192
0.9236	High Similarity	NPC172202
0.9236	High Similarity	NPC204879
0.9231	High Similarity	NPC472455
0.9231	High Similarity	NPC68093
0.9231	High Similarity	NPC278778
0.9231	High Similarity	NPC35038
0.9231	High Similarity	NPC291878
0.9231	High Similarity	NPC195796
0.9231	High Similarity	NPC191146
0.9226	High Similarity	NPC183878
0.9226	High Similarity	NPC75279
0.9226	High Similarity	NPC160951
0.9226	High Similarity	NPC255350
0.9226	High Similarity	NPC176775
0.9226	High Similarity	NPC69394
0.9226	High Similarity	NPC47781
0.9226	High Similarity	NPC145379
0.9226	High Similarity	NPC22519
0.9226	High Similarity	NPC276409
0.9226	High Similarity	NPC231018
0.9226	High Similarity	NPC274327
0.9226	High Similarity	NPC298692
0.9226	High Similarity	NPC250822
0.9221	High Similarity	NPC205046
0.9221	High Similarity	NPC59162
0.9221	High Similarity	NPC304295
0.9216	High Similarity	NPC5173
0.9216	High Similarity	NPC38545
0.9216	High Similarity	NPC171916
0.9211	High Similarity	NPC108406
0.9193	High Similarity	NPC117854
0.9193	High Similarity	NPC470456
0.9193	High Similarity	NPC243877
0.9193	High Similarity	NPC477154
0.9193	High Similarity	NPC6588
0.9187	High Similarity	NPC303174
0.9187	High Similarity	NPC259757
0.9187	High Similarity	NPC85057
0.9187	High Similarity	NPC130920
0.9182	High Similarity	NPC476247
0.9182	High Similarity	NPC229632
0.9182	High Similarity	NPC81679
0.9182	High Similarity	NPC78332
0.9177	High Similarity	NPC470326
0.9177	High Similarity	NPC282009
0.9177	High Similarity	NPC297212
0.9177	High Similarity	NPC321399
0.9177	High Similarity	NPC471976
0.9177	High Similarity	NPC246478
0.9177	High Similarity	NPC472624
0.9177	High Similarity	NPC476280
0.9177	High Similarity	NPC476283
0.9177	High Similarity	NPC287328
0.9172	High Similarity	NPC227192
0.9172	High Similarity	NPC472914
0.9172	High Similarity	NPC63454
0.9172	High Similarity	NPC472911
0.9172	High Similarity	NPC162869
0.9172	High Similarity	NPC48208
0.9172	High Similarity	NPC222814
0.9172	High Similarity	NPC245758
0.9172	High Similarity	NPC475267
0.9172	High Similarity	NPC75215
0.9172	High Similarity	NPC262286
0.9172	High Similarity	NPC36852
0.9172	High Similarity	NPC472910
0.9172	High Similarity	NPC183851
0.9172	High Similarity	NPC93376
0.9172	High Similarity	NPC474681
0.9172	High Similarity	NPC224137

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 NPC198829 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	386
0.1-0.2	946
0.2-0.3	1780
0.3-0.4	2657
0.4-0.5	1842
0.5-0.6	973
0.6-0.7	378
0.7-0.8	131
0.8-0.85	35
0.85-0.9	18
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9351	High Similarity	NPD2393	Clinical (unspecified phase)
0.9226	High Similarity	NPD2801	Approved
0.9038	High Similarity	NPD1934	Approved
0.9013	High Similarity	NPD1511	Approved
0.8951	High Similarity	NPD6168	Clinical (unspecified phase)
0.8951	High Similarity	NPD6167	Clinical (unspecified phase)
0.8951	High Similarity	NPD6166	Phase 2
0.891	High Similarity	NPD4380	Phase 2
0.8896	High Similarity	NPD1512	Approved
0.8831	High Similarity	NPD4378	Clinical (unspecified phase)
0.8788	High Similarity	NPD7054	Approved
0.8735	High Similarity	NPD7074	Phase 3
0.8735	High Similarity	NPD7472	Approved
0.8727	High Similarity	NPD3818	Discontinued
0.871	High Similarity	NPD7410	Clinical (unspecified phase)
0.869	High Similarity	NPD4338	Clinical (unspecified phase)
0.8688	High Similarity	NPD3817	Phase 2
0.8683	High Similarity	NPD6797	Phase 2
0.8634	High Similarity	NPD3882	Suspended
0.8631	High Similarity	NPD7251	Discontinued
0.8589	High Similarity	NPD5494	Approved
0.858	High Similarity	NPD4381	Clinical (unspecified phase)
0.8519	High Similarity	NPD4868	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD7808	Phase 3
0.8466	Intermediate Similarity	NPD7075	Discontinued
0.8457	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8457	Intermediate Similarity	NPD5402	Approved
0.8452	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD6801	Discontinued
0.8395	Intermediate Similarity	NPD7819	Suspended
0.8385	Intermediate Similarity	NPD7411	Suspended
0.8377	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD1510	Phase 2
0.8343	Intermediate Similarity	NPD5844	Phase 1
0.8323	Intermediate Similarity	NPD1549	Phase 2
0.8313	Intermediate Similarity	NPD6959	Discontinued
0.8312	Intermediate Similarity	NPD2796	Approved
0.8282	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD6232	Discontinued
0.8225	Intermediate Similarity	NPD7473	Discontinued
0.814	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD5403	Approved
0.8105	Intermediate Similarity	NPD1240	Approved
0.8095	Intermediate Similarity	NPD1247	Approved
0.8092	Intermediate Similarity	NPD6559	Discontinued
0.8077	Intermediate Similarity	NPD2935	Discontinued
0.8063	Intermediate Similarity	NPD6799	Approved
0.8059	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD5401	Approved
0.8	Intermediate Similarity	NPD1607	Approved
0.7987	Intermediate Similarity	NPD943	Approved
0.7964	Intermediate Similarity	NPD7768	Phase 2
0.7952	Intermediate Similarity	NPD1465	Phase 2
0.7879	Intermediate Similarity	NPD6599	Discontinued
0.7875	Intermediate Similarity	NPD3750	Approved
0.7871	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD1613	Approved
0.787	Intermediate Similarity	NPD919	Approved
0.7862	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD2800	Approved
0.7791	Intermediate Similarity	NPD2533	Approved
0.7791	Intermediate Similarity	NPD2534	Approved
0.7791	Intermediate Similarity	NPD2532	Approved
0.779	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD230	Phase 1
0.7706	Intermediate Similarity	NPD3749	Approved
0.7697	Intermediate Similarity	NPD920	Approved
0.7688	Intermediate Similarity	NPD3926	Phase 2
0.7677	Intermediate Similarity	NPD3027	Phase 3
0.7662	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD6651	Approved
0.7651	Intermediate Similarity	NPD1653	Approved
0.7628	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD5953	Discontinued
0.7625	Intermediate Similarity	NPD1551	Phase 2
0.7622	Intermediate Similarity	NPD7390	Discontinued
0.7607	Intermediate Similarity	NPD6190	Approved
0.7605	Intermediate Similarity	NPD3226	Approved
0.7593	Intermediate Similarity	NPD1243	Approved
0.759	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD7199	Phase 2
0.7562	Intermediate Similarity	NPD3748	Approved
0.7561	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD3751	Discontinued
0.7546	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD4628	Phase 3
0.7529	Intermediate Similarity	NPD3787	Discontinued
0.7527	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6099	Approved
0.7516	Intermediate Similarity	NPD6100	Approved
0.7516	Intermediate Similarity	NPD2313	Discontinued
0.7516	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4363	Phase 3
0.7514	Intermediate Similarity	NPD4360	Phase 2
0.7514	Intermediate Similarity	NPD7286	Phase 2
0.7514	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6777	Approved
0.75	Intermediate Similarity	NPD6779	Approved
0.75	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD6780	Approved
0.75	Intermediate Similarity	NPD6778	Approved
0.75	Intermediate Similarity	NPD6782	Approved
0.75	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6776	Approved
0.7484	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD5124	Phase 1
0.747	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD6234	Discontinued
0.7453	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD7033	Discontinued
0.7453	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2799	Discontinued
0.7448	Intermediate Similarity	NPD7584	Approved
0.7403	Intermediate Similarity	NPD8312	Approved
0.7403	Intermediate Similarity	NPD8313	Approved
0.7389	Intermediate Similarity	NPD7685	Pre-registration
0.7389	Intermediate Similarity	NPD4908	Phase 1
0.7386	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD7435	Discontinued
0.7377	Intermediate Similarity	NPD8150	Discontinued
0.7377	Intermediate Similarity	NPD8434	Phase 2
0.7375	Intermediate Similarity	NPD447	Suspended
0.7368	Intermediate Similarity	NPD6844	Discontinued
0.7368	Intermediate Similarity	NPD37	Approved
0.7362	Intermediate Similarity	NPD2346	Discontinued
0.7362	Intermediate Similarity	NPD2344	Approved
0.736	Intermediate Similarity	NPD7228	Approved
0.7341	Intermediate Similarity	NPD4965	Approved
0.7341	Intermediate Similarity	NPD4967	Phase 2
0.7341	Intermediate Similarity	NPD4966	Approved
0.7333	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7783	Phase 2
0.7296	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7696	Phase 3
0.7292	Intermediate Similarity	NPD7697	Approved
0.7292	Intermediate Similarity	NPD7698	Approved
0.7287	Intermediate Similarity	NPD4361	Phase 2
0.7287	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6832	Phase 2
0.7262	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD7870	Phase 2
0.7254	Intermediate Similarity	NPD7871	Phase 2
0.724	Intermediate Similarity	NPD6823	Phase 2
0.7237	Intermediate Similarity	NPD1548	Phase 1
0.7234	Intermediate Similarity	NPD6535	Approved
0.7234	Intermediate Similarity	NPD6534	Approved
0.7233	Intermediate Similarity	NPD4625	Phase 3
0.7232	Intermediate Similarity	NPD5710	Approved
0.7232	Intermediate Similarity	NPD5711	Approved
0.7231	Intermediate Similarity	NPD7701	Phase 2
0.7215	Intermediate Similarity	NPD9494	Approved
0.7197	Intermediate Similarity	NPD1203	Approved
0.7194	Intermediate Similarity	NPD8151	Discontinued
0.7193	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD3268	Approved
0.7186	Intermediate Similarity	NPD2309	Approved
0.7179	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1610	Phase 2
0.7161	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1933	Approved
0.716	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7874	Approved
0.7152	Intermediate Similarity	NPD2798	Approved
0.7135	Intermediate Similarity	NPD7229	Phase 3
0.7134	Intermediate Similarity	NPD4308	Phase 3
0.7134	Intermediate Similarity	NPD3225	Approved
0.7126	Intermediate Similarity	NPD8455	Phase 2
0.7121	Intermediate Similarity	NPD7801	Approved
0.712	Intermediate Similarity	NPD7700	Phase 2
0.712	Intermediate Similarity	NPD7699	Phase 2
0.711	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD2424	Discontinued
0.7107	Intermediate Similarity	NPD2861	Phase 2
0.7093	Intermediate Similarity	NPD7458	Discontinued
0.7089	Intermediate Similarity	NPD2797	Approved
0.7081	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7549	Discontinued
0.7056	Intermediate Similarity	NPD7585	Approved
0.7056	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD422	Phase 1
0.7048	Intermediate Similarity	NPD7266	Discontinued
0.7037	Intermediate Similarity	NPD6233	Phase 2
0.7006	Intermediate Similarity	NPD9269	Phase 2
0.7006	Intermediate Similarity	NPD1608	Approved
0.7006	Intermediate Similarity	NPD9717	Approved
0.7005	Intermediate Similarity	NPD7583	Approved
0.7	Intermediate Similarity	NPD5242	Approved
0.6995	Remote Similarity	NPD1729	Discontinued
0.6994	Remote Similarity	NPD4060	Phase 1
0.6989	Remote Similarity	NPD4288	Approved
0.6988	Remote Similarity	NPD5406	Approved
0.6988	Remote Similarity	NPD5404	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