NPASS Compound

Structure

NPC297212 OpenBabel07101719252D 32 35 0 0 1 0 0 0 0 0999 V2000 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7321 -0.0000 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 3.4641 -0.0000 0.0000 C 0 0 0 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 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 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 -4.3301 -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 -1.7321 -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 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 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 2 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 -0.8660 -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 -0.8660 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 -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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 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 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 2 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 4 31 1 0 0 0 0 5 6 1 0 0 0 0 5 9 1 0 0 0 0 6 14 1 0 0 0 0 7 8 2 0 0 0 0 7 15 1 0 0 0 0 8 18 1 0 0 0 0 9 26 1 0 0 0 0 10 15 2 0 0 0 0 10 19 1 0 0 0 0 11 16 1 0 0 0 0 12 20 1 0 0 0 0 12 21 2 0 0 0 0 13 22 2 0 0 0 0 13 23 1 0 0 0 0 14 17 1 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 16 25 2 0 0 0 0 17 11 1 6 0 0 0 17 26 1 0 0 0 0 18 19 2 0 0 0 0 18 27 1 0 0 0 0 19 28 1 0 0 0 0 20 24 1 0 0 0 0 20 29 2 0 0 0 0 21 32 1 0 0 0 0 22 31 1 0 0 0 0 23 24 2 0 0 0 0 23 32 1 0 0 0 0 24 25 1 0 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	436.19
Volume:	453.039
LogP:	5.969
LogD:	3.463
LogS:	-3.623
# Rotatable Bonds:	4
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.368
Synthetic Accessibility Score:	3.523
Fsp3:	0.346
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:	-4.768
MDCK Permeability:	1.4376710169017315e-05
Pgp-inhibitor:	0.502
Pgp-substrate:	0.869
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.761
30% Bioavailability (F30%):	0.793

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	95.33914184570312%
Volume Distribution (VD):	0.625
Pgp-substrate:	4.8516716957092285%

ADMET: Metabolism

CYP1A2-inhibitor:	0.632
CYP1A2-substrate:	0.893
CYP2C19-inhibitor:	0.635
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.779
CYP2C9-substrate:	0.907
CYP2D6-inhibitor:	0.469
CYP2D6-substrate:	0.892
CYP3A4-inhibitor:	0.233
CYP3A4-substrate:	0.177

ADMET: Excretion

Clearance (CL):	5.283
Half-life (T1/2):	0.222

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.09
Drug-inuced Liver Injury (DILI):	0.546
AMES Toxicity:	0.396
Rat Oral Acute Toxicity:	0.62
Maximum Recommended Daily Dose:	0.94
Skin Sensitization:	0.923
Carcinogencity:	0.104
Eye Corrosion:	0.003
Eye Irritation:	0.899
Respiratory Toxicity:	0.94

Download Data

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

Natural Product: NPC297212

Natural Product ID:	NPC297212
*Common Name:**	Ugonin K
IUPAC Name:	2-(3,4-dihydroxyphenyl)-6-[[(1S)-2,2-dimethyl-6-methylidenecyclohexyl]methyl]-5-hydroxy-7-methoxychromen-4-one
Synonyms:	Ugonin K
Standard InCHIKey:	ROCKAKPPZWGROR-QGZVFWFLSA-N
Standard InCHI:	InChI=1S/C26H28O6/c1-14-6-5-9-26(2,3)17(14)11-16-22(31-4)13-23-24(25(16)30)20(29)12-21(32-23)15-7-8-18(27)19(28)10-15/h7-8,10,12-13,17,27-28,30H,1,5-6,9,11H2,2-4H3/t17-/m1/s1
SMILES:	C=C1CCCC(C)(C)[C@@H]1Cc1c(cc2c(c(=O)cc(c3ccc(c(c3)O)O)o2)c1O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL563689
PubChem CID:	12114698
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003503] 6-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
NPO11959	Helminthostachys zeylanica	Species	Ophioglossaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19583252]
NPO11959	Helminthostachys zeylanica	Species	Ophioglossaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[28169537]
NPO11959	Helminthostachys zeylanica	Species	Ophioglossaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11959	Helminthostachys zeylanica	Species	Ophioglossaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11959	Helminthostachys zeylanica	Species	Ophioglossaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[514265]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[514265]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[514265]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2000.0	nM	PMID[514265]

☑ 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 NPC297212 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	445
0.1-0.2	1703
0.2-0.3	3448
0.3-0.4	8895
0.4-0.5	9632
0.5-0.6	3868
0.6-0.7	5075
0.7-0.8	5326
0.8-0.85	2677
0.85-0.9	1393
0.9-0.95	222
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC46736
0.9868	High Similarity	NPC476280
0.9805	High Similarity	NPC476295
0.9805	High Similarity	NPC12461
0.9803	High Similarity	NPC197856
0.974	High Similarity	NPC206605
0.9542	High Similarity	NPC3980
0.9484	High Similarity	NPC476283
0.947	High Similarity	NPC88804
0.947	High Similarity	NPC3825
0.9423	High Similarity	NPC32694
0.9423	High Similarity	NPC472275
0.9412	High Similarity	NPC170492
0.9371	High Similarity	NPC476306
0.9363	High Similarity	NPC474150
0.9363	High Similarity	NPC474162
0.9363	High Similarity	NPC78332
0.9359	High Similarity	NPC235018
0.9359	High Similarity	NPC45146
0.9359	High Similarity	NPC28241
0.9355	High Similarity	NPC273843
0.9351	High Similarity	NPC133392
0.9346	High Similarity	NPC157784
0.9346	High Similarity	NPC471982
0.9346	High Similarity	NPC63187
0.9346	High Similarity	NPC37684
0.9304	High Similarity	NPC220313
0.9304	High Similarity	NPC186686
0.9299	High Similarity	NPC187354
0.9299	High Similarity	NPC234644
0.9299	High Similarity	NPC278427
0.9299	High Similarity	NPC57715
0.9299	High Similarity	NPC472906
0.9295	High Similarity	NPC172770
0.9295	High Similarity	NPC235448
0.9295	High Similarity	NPC210459
0.9295	High Similarity	NPC185258
0.929	High Similarity	NPC471985
0.929	High Similarity	NPC170026
0.929	High Similarity	NPC276444
0.929	High Similarity	NPC475799
0.929	High Similarity	NPC282307
0.929	High Similarity	NPC13779
0.9286	High Similarity	NPC213896
0.9286	High Similarity	NPC192083
0.9281	High Similarity	NPC154345
0.9281	High Similarity	NPC59162
0.9281	High Similarity	NPC205046
0.9281	High Similarity	NPC304295
0.9272	High Similarity	NPC108406
0.9245	High Similarity	NPC239752
0.9245	High Similarity	NPC156432
0.9245	High Similarity	NPC275780
0.9245	High Similarity	NPC472450
0.9241	High Similarity	NPC329760
0.9236	High Similarity	NPC119209
0.9236	High Similarity	NPC471973
0.9236	High Similarity	NPC80375
0.9236	High Similarity	NPC36217
0.9236	High Similarity	NPC192686
0.9236	High Similarity	NPC118256
0.9236	High Similarity	NPC321399
0.9236	High Similarity	NPC188433
0.9231	High Similarity	NPC219867
0.9231	High Similarity	NPC161960
0.9231	High Similarity	NPC218871
0.9231	High Similarity	NPC471209
0.9231	High Similarity	NPC237418
0.9231	High Similarity	NPC187745
0.9231	High Similarity	NPC476630
0.9231	High Similarity	NPC304008
0.9231	High Similarity	NPC180011
0.9231	High Similarity	NPC79053
0.9226	High Similarity	NPC321779
0.9226	High Similarity	NPC67396
0.9226	High Similarity	NPC56786
0.9226	High Similarity	NPC80534
0.9226	High Similarity	NPC234255
0.9221	High Similarity	NPC249570
0.9221	High Similarity	NPC106976
0.9193	High Similarity	NPC165456
0.9193	High Similarity	NPC300307
0.9193	High Similarity	NPC288813
0.9193	High Similarity	NPC188079
0.9187	High Similarity	NPC43319
0.9187	High Similarity	NPC171985
0.9187	High Similarity	NPC320741
0.9187	High Similarity	NPC39091
0.9182	High Similarity	NPC207690
0.9182	High Similarity	NPC23298
0.9182	High Similarity	NPC306321
0.9182	High Similarity	NPC303460
0.9182	High Similarity	NPC189473
0.9177	High Similarity	NPC142252
0.9177	High Similarity	NPC26326
0.9177	High Similarity	NPC474038
0.9177	High Similarity	NPC198829
0.9172	High Similarity	NPC53545
0.9172	High Similarity	NPC204879
0.9172	High Similarity	NPC85121
0.9172	High Similarity	NPC74178
0.9172	High Similarity	NPC469658
0.9172	High Similarity	NPC184755
0.9172	High Similarity	NPC117418
0.9167	High Similarity	NPC278778
0.9167	High Similarity	NPC24640
0.9167	High Similarity	NPC291878
0.9167	High Similarity	NPC142339
0.9167	High Similarity	NPC115853
0.9167	High Similarity	NPC195796
0.9167	High Similarity	NPC472455
0.9167	High Similarity	NPC35038
0.9161	High Similarity	NPC74924
0.9161	High Similarity	NPC298692
0.9161	High Similarity	NPC476631
0.9156	High Similarity	NPC305965
0.915	High Similarity	NPC52005
0.915	High Similarity	NPC87125
0.915	High Similarity	NPC171916
0.915	High Similarity	NPC137062
0.915	High Similarity	NPC177298
0.915	High Similarity	NPC270465
0.915	High Similarity	NPC223579
0.915	High Similarity	NPC38545
0.915	High Similarity	NPC48479
0.915	High Similarity	NPC287101
0.915	High Similarity	NPC183950
0.913	High Similarity	NPC218226
0.9125	High Similarity	NPC303174
0.9125	High Similarity	NPC473286
0.9125	High Similarity	NPC293319
0.9125	High Similarity	NPC472277
0.9119	High Similarity	NPC83922
0.9119	High Similarity	NPC470694
0.9119	High Similarity	NPC194427
0.9119	High Similarity	NPC472448
0.9119	High Similarity	NPC476247
0.9119	High Similarity	NPC229632
0.9119	High Similarity	NPC201800
0.9114	High Similarity	NPC228785
0.9114	High Similarity	NPC475784
0.9114	High Similarity	NPC474960
0.9114	High Similarity	NPC328102
0.9114	High Similarity	NPC14353
0.9114	High Similarity	NPC204290
0.9114	High Similarity	NPC476980
0.9114	High Similarity	NPC56085
0.9108	High Similarity	NPC78225
0.9108	High Similarity	NPC218313
0.9108	High Similarity	NPC136674
0.9108	High Similarity	NPC299520
0.9108	High Similarity	NPC284820
0.9108	High Similarity	NPC473272
0.9108	High Similarity	NPC236796
0.9108	High Similarity	NPC474055
0.9108	High Similarity	NPC291508
0.9108	High Similarity	NPC129684
0.9108	High Similarity	NPC472598
0.9108	High Similarity	NPC27337
0.9108	High Similarity	NPC474681
0.9108	High Similarity	NPC52889
0.9103	High Similarity	NPC168247
0.9103	High Similarity	NPC117992
0.9103	High Similarity	NPC470327
0.9103	High Similarity	NPC113906
0.9103	High Similarity	NPC230149
0.9103	High Similarity	NPC45849
0.9103	High Similarity	NPC200761
0.9103	High Similarity	NPC472280
0.9103	High Similarity	NPC152951
0.9103	High Similarity	NPC57674
0.9103	High Similarity	NPC477503
0.9097	High Similarity	NPC237994
0.9097	High Similarity	NPC60972
0.9097	High Similarity	NPC39732
0.9097	High Similarity	NPC260979
0.9097	High Similarity	NPC472912
0.9097	High Similarity	NPC324233
0.9097	High Similarity	NPC323626
0.9091	High Similarity	NPC184136
0.9091	High Similarity	NPC149127
0.9091	High Similarity	NPC286342
0.9091	High Similarity	NPC188871
0.9091	High Similarity	NPC85131
0.9085	High Similarity	NPC119059
0.9085	High Similarity	NPC166036
0.9085	High Similarity	NPC120464
0.9085	High Similarity	NPC238279
0.9085	High Similarity	NPC3036
0.9085	High Similarity	NPC203077
0.9085	High Similarity	NPC195202
0.908	High Similarity	NPC4200
0.9074	High Similarity	NPC476637
0.9074	High Similarity	NPC107627
0.9073	High Similarity	NPC279121
0.9073	High Similarity	NPC11700
0.9068	High Similarity	NPC224851
0.9068	High Similarity	NPC472449
0.9068	High Similarity	NPC37870
0.9062	High Similarity	NPC270837

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 NPC297212 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	388
0.1-0.2	942
0.2-0.3	1636
0.3-0.4	2681
0.4-0.5	1946
0.5-0.6	963
0.6-0.7	410
0.7-0.8	136
0.8-0.85	36
0.85-0.9	12
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9286	High Similarity	NPD2393	Clinical (unspecified phase)
0.9073	High Similarity	NPD1511	Approved
0.9038	High Similarity	NPD2801	Approved
0.8974	High Similarity	NPD1934	Approved
0.8954	High Similarity	NPD1512	Approved
0.8889	High Similarity	NPD4378	Clinical (unspecified phase)
0.8773	High Similarity	NPD6168	Clinical (unspecified phase)
0.8773	High Similarity	NPD6166	Phase 2
0.8773	High Similarity	NPD6167	Clinical (unspecified phase)
0.8645	High Similarity	NPD7410	Clinical (unspecified phase)
0.8625	High Similarity	NPD8443	Clinical (unspecified phase)
0.8608	High Similarity	NPD4380	Phase 2
0.8606	High Similarity	NPD7473	Discontinued
0.8571	High Similarity	NPD3882	Suspended
0.8537	High Similarity	NPD6232	Discontinued
0.8528	High Similarity	NPD5494	Approved
0.8509	High Similarity	NPD3817	Phase 2
0.8503	High Similarity	NPD7054	Approved
0.8476	Intermediate Similarity	NPD6959	Discontinued
0.8457	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD7074	Phase 3
0.8452	Intermediate Similarity	NPD7472	Approved
0.8447	Intermediate Similarity	NPD7819	Suspended
0.8443	Intermediate Similarity	NPD3818	Discontinued
0.8402	Intermediate Similarity	NPD6797	Phase 2
0.8353	Intermediate Similarity	NPD7251	Discontinued
0.8323	Intermediate Similarity	NPD7411	Suspended
0.8312	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD1510	Phase 2
0.8293	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD7075	Discontinued
0.8284	Intermediate Similarity	NPD5844	Phase 1
0.8258	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD1549	Phase 2
0.8247	Intermediate Similarity	NPD2796	Approved
0.8221	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD2800	Approved
0.8198	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8198	Intermediate Similarity	NPD7808	Phase 3
0.8176	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD6801	Discontinued
0.8158	Intermediate Similarity	NPD1240	Approved
0.8153	Intermediate Similarity	NPD3750	Approved
0.8148	Intermediate Similarity	NPD6599	Discontinued
0.8121	Intermediate Similarity	NPD7768	Phase 2
0.811	Intermediate Similarity	NPD1465	Phase 2
0.8107	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD1607	Approved
0.8039	Intermediate Similarity	NPD943	Approved
0.8013	Intermediate Similarity	NPD6099	Approved
0.8013	Intermediate Similarity	NPD6100	Approved
0.8	Intermediate Similarity	NPD6799	Approved
0.7977	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD3749	Approved
0.795	Intermediate Similarity	NPD2532	Approved
0.795	Intermediate Similarity	NPD2534	Approved
0.795	Intermediate Similarity	NPD2533	Approved
0.7935	Intermediate Similarity	NPD6651	Approved
0.7898	Intermediate Similarity	NPD2935	Discontinued
0.7888	Intermediate Similarity	NPD7390	Discontinued
0.7866	Intermediate Similarity	NPD3226	Approved
0.7862	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD5402	Approved
0.7834	Intermediate Similarity	NPD3748	Approved
0.7834	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD6559	Discontinued
0.7824	Intermediate Similarity	NPD1247	Approved
0.7811	Intermediate Similarity	NPD919	Approved
0.7792	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD5403	Approved
0.7733	Intermediate Similarity	NPD3926	Phase 2
0.773	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD2799	Discontinued
0.7722	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7199	Phase 2
0.7712	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD6234	Discontinued
0.7702	Intermediate Similarity	NPD4628	Phase 3
0.7702	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1613	Approved
0.7692	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD4908	Phase 1
0.7643	Intermediate Similarity	NPD230	Phase 1
0.764	Intermediate Similarity	NPD1243	Approved
0.7636	Intermediate Similarity	NPD920	Approved
0.7636	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD2346	Discontinued
0.7622	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD5401	Approved
0.7564	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD2313	Discontinued
0.7562	Intermediate Similarity	NPD1551	Phase 2
0.7556	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD4360	Phase 2
0.7554	Intermediate Similarity	NPD4363	Phase 3
0.7545	Intermediate Similarity	NPD7458	Discontinued
0.7542	Intermediate Similarity	NPD8312	Approved
0.7542	Intermediate Similarity	NPD8313	Approved
0.7541	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2344	Approved
0.7515	Intermediate Similarity	NPD37	Approved
0.7515	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3027	Phase 3
0.75	Intermediate Similarity	NPD7228	Approved
0.75	Intermediate Similarity	NPD3751	Discontinued
0.75	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7003	Approved
0.7485	Intermediate Similarity	NPD4965	Approved
0.7485	Intermediate Similarity	NPD4966	Approved
0.7485	Intermediate Similarity	NPD8166	Discontinued
0.7485	Intermediate Similarity	NPD4967	Phase 2
0.7472	Intermediate Similarity	NPD5953	Discontinued
0.7471	Intermediate Similarity	NPD7229	Phase 3
0.7471	Intermediate Similarity	NPD3787	Discontinued
0.7458	Intermediate Similarity	NPD7286	Phase 2
0.7455	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD3268	Approved
0.744	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD447	Suspended
0.7419	Intermediate Similarity	NPD2798	Approved
0.7418	Intermediate Similarity	NPD8434	Phase 2
0.7389	Intermediate Similarity	NPD4625	Phase 3
0.738	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD5710	Approved
0.7371	Intermediate Similarity	NPD5711	Approved
0.7365	Intermediate Similarity	NPD6273	Approved
0.7355	Intermediate Similarity	NPD2797	Approved
0.7346	Intermediate Similarity	NPD5404	Approved
0.7346	Intermediate Similarity	NPD5405	Approved
0.7346	Intermediate Similarity	NPD5406	Approved
0.7346	Intermediate Similarity	NPD5408	Approved
0.7333	Intermediate Similarity	NPD2309	Approved
0.7326	Intermediate Similarity	NPD4361	Phase 2
0.7326	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD8150	Discontinued
0.732	Intermediate Similarity	NPD1610	Phase 2
0.732	Intermediate Similarity	NPD1201	Approved
0.7314	Intermediate Similarity	NPD8127	Discontinued
0.7273	Intermediate Similarity	NPD1608	Approved
0.7267	Intermediate Similarity	NPD5761	Phase 2
0.7267	Intermediate Similarity	NPD5760	Phase 2
0.7263	Intermediate Similarity	NPD6781	Approved
0.7263	Intermediate Similarity	NPD6779	Approved
0.7263	Intermediate Similarity	NPD6777	Approved
0.7263	Intermediate Similarity	NPD6776	Approved
0.7263	Intermediate Similarity	NPD6778	Approved
0.7263	Intermediate Similarity	NPD6780	Approved
0.7263	Intermediate Similarity	NPD6782	Approved
0.725	Intermediate Similarity	NPD4060	Phase 1
0.7244	Intermediate Similarity	NPD1470	Approved
0.7244	Intermediate Similarity	NPD1203	Approved
0.7238	Intermediate Similarity	NPD7685	Pre-registration
0.7233	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD8151	Discontinued
0.7229	Intermediate Similarity	NPD6190	Approved
0.7226	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD4288	Approved
0.7205	Intermediate Similarity	NPD5124	Phase 1
0.7205	Intermediate Similarity	NPD1933	Approved
0.7205	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7033	Discontinued
0.7176	Intermediate Similarity	NPD1653	Approved
0.7171	Intermediate Similarity	NPD1548	Phase 1
0.7161	Intermediate Similarity	NPD3972	Approved
0.7152	Intermediate Similarity	NPD9494	Approved
0.7151	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7435	Discontinued
0.7134	Intermediate Similarity	NPD3266	Approved
0.7134	Intermediate Similarity	NPD3267	Approved
0.7128	Intermediate Similarity	NPD7584	Approved
0.7115	Intermediate Similarity	NPD4749	Approved
0.7111	Intermediate Similarity	NPD7177	Discontinued
0.7107	Intermediate Similarity	NPD6832	Phase 2
0.7099	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD422	Phase 1
0.7097	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD2403	Approved
0.7083	Intermediate Similarity	NPD3300	Phase 2
0.7078	Intermediate Similarity	NPD17	Approved
0.7073	Intermediate Similarity	NPD4308	Phase 3
0.7071	Intermediate Similarity	NPD7783	Phase 2
0.7071	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD3225	Approved
0.7069	Intermediate Similarity	NPD8455	Phase 2
0.7063	Intermediate Similarity	NPD7095	Approved
0.7062	Intermediate Similarity	NPD7697	Approved
0.7062	Intermediate Similarity	NPD7696	Phase 3
0.7062	Intermediate Similarity	NPD7698	Approved
0.7059	Intermediate Similarity	NPD4287	Approved
0.7051	Intermediate Similarity	NPD9717	Approved
0.7051	Intermediate Similarity	NPD9269	Phase 2
0.7049	Intermediate Similarity	NPD7240	Approved
0.7047	Intermediate Similarity	NPD2493	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