NPASS Compound

Structure

NPC471985 OpenBabel07101718292D 31 34 0 0 0 0 0 0 0 0999 V2000 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 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 -0.5000 -1.8660 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 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 1.7321 2.0000 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 3.4641 3.0000 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 -0.0000 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 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 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 4.3301 3.5000 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 3.4641 2.0000 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 0.8660 0.5000 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 -0.0000 -1.0000 0.0000 C 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 6.0622 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 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 4.3301 1.5000 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 13 1 0 0 0 0 2 13 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 6 1 0 0 0 0 5 13 2 0 0 0 0 6 16 1 0 0 0 0 7 8 2 0 0 0 0 7 14 1 0 0 0 0 8 25 1 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 15 2 0 0 0 0 10 20 1 0 0 0 0 11 17 2 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 12 21 2 0 0 0 0 14 23 1 0 0 0 0 15 21 1 0 0 0 0 16 17 1 0 0 0 0 16 24 2 0 0 0 0 17 26 1 0 0 0 0 18 22 2 0 0 0 0 18 27 1 0 0 0 0 19 22 1 0 0 0 0 19 28 2 0 0 0 0 20 23 2 0 0 0 0 20 29 1 0 0 0 0 21 30 1 0 0 0 0 22 24 1 0 0 0 0 23 31 1 0 0 0 0 24 30 1 0 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	420.16
Volume:	433.107
LogP:	6.331
LogD:	3.744
LogS:	-2.407
# Rotatable Bonds:	3
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.499
Synthetic Accessibility Score:	3.295
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:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.963
MDCK Permeability:	1.4818752788414713e-05
Pgp-inhibitor:	0.764
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.227
20% Bioavailability (F20%):	0.632
30% Bioavailability (F30%):	0.787

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	95.52554321289062%
Volume Distribution (VD):	0.719
Pgp-substrate:	5.813541412353516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.881
CYP1A2-substrate:	0.268
CYP2C19-inhibitor:	0.824
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.86
CYP2C9-substrate:	0.874
CYP2D6-inhibitor:	0.8
CYP2D6-substrate:	0.198
CYP3A4-inhibitor:	0.419
CYP3A4-substrate:	0.113

ADMET: Excretion

Clearance (CL):	4.772
Half-life (T1/2):	0.271

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.883
Drug-inuced Liver Injury (DILI):	0.888
AMES Toxicity:	0.208
Rat Oral Acute Toxicity:	0.344
Maximum Recommended Daily Dose:	0.897
Skin Sensitization:	0.885
Carcinogencity:	0.548
Eye Corrosion:	0.003
Eye Irritation:	0.339
Respiratory Toxicity:	0.859

Download Data

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

Natural Product: NPC471985

Natural Product ID:	NPC471985
*Common Name:**	LJVOUFXVBIKXNV-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LJVOUFXVBIKXNV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H24O6/c1-13(2)5-6-16-17(26)11-18(27)22-19(28)12-21(30-24(16)22)15-9-14-7-8-25(3,4)31-23(14)20(29)10-15/h5,7-12,26-27,29H,6H2,1-4H3
SMILES:	CC(=CCC1=C2C(=C(C=C1O)O)C(=O)C=C(O2)C3=CC4=C(C(=C3)O)OC(C=C4)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3314710
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003504] 8-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
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12081149]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	root	n.a.	PMID[22051934]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	aerial parts	herbal garden of Chungbuk National University, Cheongju, Korea	2012-Oct	PMID[24963714]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	aerial part	n.a.	Database[Article]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23024	Epimedium koreanum	Species	Berberidaceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[508246]

☑ 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 NPC471985 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	447
0.1-0.2	1845
0.2-0.3	4582
0.3-0.4	11024
0.4-0.5	6717
0.5-0.6	3611
0.6-0.7	5090
0.7-0.8	4720
0.8-0.85	2348
0.85-0.9	1454
0.9-0.95	769
0.95-1	90

Similarity Score	Similarity Level	Natural Product ID
0.9865	High Similarity	NPC170492
0.9737	High Similarity	NPC259456
0.9735	High Similarity	NPC74178
0.9735	High Similarity	NPC184755
0.9733	High Similarity	NPC276444
0.9673	High Similarity	NPC78332
0.9671	High Similarity	NPC118256
0.9671	High Similarity	NPC204290
0.9671	High Similarity	NPC119209
0.9671	High Similarity	NPC192686
0.9669	High Similarity	NPC218313
0.9669	High Similarity	NPC476630
0.9669	High Similarity	NPC237418
0.9669	High Similarity	NPC218871
0.9669	High Similarity	NPC474681
0.9667	High Similarity	NPC234255
0.9667	High Similarity	NPC472280
0.9664	High Similarity	NPC471982
0.9664	High Similarity	NPC237994
0.9662	High Similarity	NPC3825
0.9662	High Similarity	NPC88804
0.9608	High Similarity	NPC167678
0.9608	High Similarity	NPC29876
0.9608	High Similarity	NPC474038
0.9605	High Similarity	NPC204879
0.9603	High Similarity	NPC133970
0.9603	High Similarity	NPC472455
0.9603	High Similarity	NPC282307
0.9603	High Similarity	NPC170026
0.9603	High Similarity	NPC5322
0.9603	High Similarity	NPC6633
0.9597	High Similarity	NPC154345
0.9545	High Similarity	NPC472448
0.9545	High Similarity	NPC474150
0.9545	High Similarity	NPC83922
0.9545	High Similarity	NPC474162
0.9545	High Similarity	NPC261470
0.9542	High Similarity	NPC475784
0.9542	High Similarity	NPC471973
0.9542	High Similarity	NPC476980
0.9539	High Similarity	NPC27337
0.9539	High Similarity	NPC473272
0.9539	High Similarity	NPC52889
0.9539	High Similarity	NPC284820
0.9536	High Similarity	NPC200246
0.9533	High Similarity	NPC157784
0.9533	High Similarity	NPC63187
0.9533	High Similarity	NPC37684
0.9484	High Similarity	NPC189473
0.9484	High Similarity	NPC23298
0.9484	High Similarity	NPC472625
0.9484	High Similarity	NPC186686
0.9481	High Similarity	NPC471210
0.9481	High Similarity	NPC26326
0.9481	High Similarity	NPC198829
0.9481	High Similarity	NPC234644
0.9481	High Similarity	NPC472632
0.9477	High Similarity	NPC280680
0.9474	High Similarity	NPC278778
0.9474	High Similarity	NPC195796
0.9474	High Similarity	NPC470600
0.9474	High Similarity	NPC191146
0.9474	High Similarity	NPC291878
0.9474	High Similarity	NPC35038
0.9474	High Similarity	NPC68093
0.947	High Similarity	NPC49402
0.947	High Similarity	NPC33051
0.947	High Similarity	NPC273462
0.947	High Similarity	NPC227337
0.947	High Similarity	NPC70433
0.9467	High Similarity	NPC304295
0.9467	High Similarity	NPC205046
0.9467	High Similarity	NPC59162
0.9463	High Similarity	NPC183950
0.9463	High Similarity	NPC52005
0.9463	High Similarity	NPC48479
0.9463	High Similarity	NPC177298
0.9463	High Similarity	NPC137062
0.9463	High Similarity	NPC223579
0.9463	High Similarity	NPC287101
0.9423	High Similarity	NPC130920
0.9423	High Similarity	NPC303174
0.9423	High Similarity	NPC85057
0.9423	High Similarity	NPC239752
0.9423	High Similarity	NPC50960
0.9423	High Similarity	NPC472450
0.9423	High Similarity	NPC275780
0.9419	High Similarity	NPC194427
0.9419	High Similarity	NPC474033
0.9419	High Similarity	NPC474034
0.9416	High Similarity	NPC188433
0.9416	High Similarity	NPC28241
0.9416	High Similarity	NPC328102
0.9416	High Similarity	NPC472624
0.9416	High Similarity	NPC174953
0.9416	High Similarity	NPC476280
0.9412	High Similarity	NPC78225
0.9412	High Similarity	NPC474055
0.9412	High Similarity	NPC136674
0.9412	High Similarity	NPC291508
0.9412	High Similarity	NPC471209
0.9412	High Similarity	NPC476981
0.9412	High Similarity	NPC472598
0.9412	High Similarity	NPC78071
0.9408	High Similarity	NPC45849
0.9408	High Similarity	NPC200761
0.9408	High Similarity	NPC168247
0.9408	High Similarity	NPC256925
0.9408	High Similarity	NPC470327
0.9408	High Similarity	NPC57674
0.9408	High Similarity	NPC133392
0.9408	High Similarity	NPC152951
0.9408	High Similarity	NPC477503
0.9408	High Similarity	NPC117992
0.9408	High Similarity	NPC230149
0.9404	High Similarity	NPC60972
0.9404	High Similarity	NPC249570
0.9404	High Similarity	NPC39732
0.9396	High Similarity	NPC195202
0.9396	High Similarity	NPC120464
0.9367	High Similarity	NPC165456
0.9367	High Similarity	NPC476637
0.9363	High Similarity	NPC37870
0.9363	High Similarity	NPC472449
0.9363	High Similarity	NPC43319
0.9363	High Similarity	NPC39091
0.9359	High Similarity	NPC303460
0.9359	High Similarity	NPC306321
0.9355	High Similarity	NPC258331
0.9355	High Similarity	NPC471212
0.9355	High Similarity	NPC472634
0.9355	High Similarity	NPC57715
0.9355	High Similarity	NPC40037
0.9355	High Similarity	NPC471211
0.9355	High Similarity	NPC134783
0.9351	High Similarity	NPC53545
0.9351	High Similarity	NPC46736
0.9351	High Similarity	NPC197856
0.9351	High Similarity	NPC187792
0.9351	High Similarity	NPC473990
0.9351	High Similarity	NPC469658
0.9351	High Similarity	NPC117418
0.9346	High Similarity	NPC470328
0.9346	High Similarity	NPC472626
0.9346	High Similarity	NPC3980
0.9346	High Similarity	NPC138243
0.9346	High Similarity	NPC209614
0.9342	High Similarity	NPC78326
0.9342	High Similarity	NPC176775
0.9342	High Similarity	NPC476631
0.9342	High Similarity	NPC74924
0.9342	High Similarity	NPC47781
0.9342	High Similarity	NPC22519
0.9342	High Similarity	NPC18727
0.9342	High Similarity	NPC69394
0.9342	High Similarity	NPC145379
0.9342	High Similarity	NPC213896
0.9342	High Similarity	NPC274327
0.9342	High Similarity	NPC160951
0.9342	High Similarity	NPC192083
0.9342	High Similarity	NPC255350
0.9342	High Similarity	NPC183878
0.9342	High Similarity	NPC231018
0.9342	High Similarity	NPC236223
0.9342	High Similarity	NPC270620
0.9342	High Similarity	NPC179126
0.9338	High Similarity	NPC125062
0.9338	High Similarity	NPC54394
0.9338	High Similarity	NPC256406
0.9338	High Similarity	NPC252933
0.9338	High Similarity	NPC200740
0.9329	High Similarity	NPC12200
0.9329	High Similarity	NPC108406
0.9329	High Similarity	NPC62536
0.9329	High Similarity	NPC33265
0.9308	High Similarity	NPC101107
0.9304	High Similarity	NPC218226
0.9299	High Similarity	NPC62261
0.9299	High Similarity	NPC470773
0.9299	High Similarity	NPC156432
0.9299	High Similarity	NPC293319
0.9295	High Similarity	NPC329760
0.9295	High Similarity	NPC476247
0.9295	High Similarity	NPC472635
0.9295	High Similarity	NPC206605
0.9295	High Similarity	NPC25152
0.9295	High Similarity	NPC229632
0.9295	High Similarity	NPC8300
0.929	High Similarity	NPC474960
0.929	High Similarity	NPC282009
0.929	High Similarity	NPC36217
0.929	High Similarity	NPC287328
0.929	High Similarity	NPC472631
0.929	High Similarity	NPC139036
0.929	High Similarity	NPC297212
0.929	High Similarity	NPC246478
0.929	High Similarity	NPC472630
0.9286	High Similarity	NPC187745
0.9286	High Similarity	NPC273843
0.9286	High Similarity	NPC223787

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 NPC471985 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	401
0.1-0.2	977
0.2-0.3	1738
0.3-0.4	2718
0.4-0.5	1775
0.5-0.6	981
0.6-0.7	387
0.7-0.8	112
0.8-0.85	37
0.85-0.9	16
0.9-0.95	8
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9342	High Similarity	NPD2393	Clinical (unspecified phase)
0.9342	High Similarity	NPD2801	Approved
0.9276	High Similarity	NPD1934	Approved
0.9257	High Similarity	NPD1511	Approved
0.9133	High Similarity	NPD1512	Approved
0.894	High Similarity	NPD4378	Clinical (unspecified phase)
0.8938	High Similarity	NPD6166	Phase 2
0.8938	High Similarity	NPD6167	Clinical (unspecified phase)
0.8938	High Similarity	NPD6168	Clinical (unspecified phase)
0.8854	High Similarity	NPD3882	Suspended
0.8816	High Similarity	NPD7410	Clinical (unspecified phase)
0.879	High Similarity	NPD3817	Phase 2
0.8774	High Similarity	NPD4380	Phase 2
0.8773	High Similarity	NPD7054	Approved
0.872	High Similarity	NPD7472	Approved
0.872	High Similarity	NPD7074	Phase 3
0.8712	High Similarity	NPD3818	Discontinued
0.8571	High Similarity	NPD5494	Approved
0.8554	High Similarity	NPD6797	Phase 2
0.8503	High Similarity	NPD7251	Discontinued
0.85	High Similarity	NPD4868	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD6232	Discontinued
0.8452	Intermediate Similarity	NPD7808	Phase 3
0.8452	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD7075	Discontinued
0.8424	Intermediate Similarity	NPD7473	Discontinued
0.8375	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1510	Phase 2
0.8323	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD6801	Discontinued
0.8301	Intermediate Similarity	NPD1549	Phase 2
0.8289	Intermediate Similarity	NPD2796	Approved
0.8261	Intermediate Similarity	NPD1465	Phase 2
0.8261	Intermediate Similarity	NPD7819	Suspended
0.825	Intermediate Similarity	NPD7411	Suspended
0.8214	Intermediate Similarity	NPD5844	Phase 1
0.82	Intermediate Similarity	NPD943	Approved
0.82	Intermediate Similarity	NPD1240	Approved
0.8182	Intermediate Similarity	NPD6959	Discontinued
0.8153	Intermediate Similarity	NPD6799	Approved
0.8098	Intermediate Similarity	NPD5402	Approved
0.8092	Intermediate Similarity	NPD1607	Approved
0.8077	Intermediate Similarity	NPD3750	Approved
0.8072	Intermediate Similarity	NPD1247	Approved
0.8061	Intermediate Similarity	NPD919	Approved
0.8054	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD2800	Approved
0.8012	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5403	Approved
0.7987	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD6559	Discontinued
0.7963	Intermediate Similarity	NPD6599	Discontinued
0.7949	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD7768	Phase 2
0.7935	Intermediate Similarity	NPD2935	Discontinued
0.7929	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD3749	Approved
0.7875	Intermediate Similarity	NPD5401	Approved
0.787	Intermediate Similarity	NPD3926	Phase 2
0.7843	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD1613	Approved
0.7792	Intermediate Similarity	NPD447	Suspended
0.7785	Intermediate Similarity	NPD1243	Approved
0.7785	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD2534	Approved
0.7764	Intermediate Similarity	NPD2532	Approved
0.7764	Intermediate Similarity	NPD2533	Approved
0.7763	Intermediate Similarity	NPD3027	Phase 3
0.7756	Intermediate Similarity	NPD3748	Approved
0.7712	Intermediate Similarity	NPD2313	Discontinued
0.7707	Intermediate Similarity	NPD6100	Approved
0.7707	Intermediate Similarity	NPD6099	Approved
0.7702	Intermediate Similarity	NPD7390	Discontinued
0.7683	Intermediate Similarity	NPD3226	Approved
0.7677	Intermediate Similarity	NPD230	Phase 1
0.7669	Intermediate Similarity	NPD920	Approved
0.7654	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD2799	Discontinued
0.7643	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD6651	Approved
0.7614	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD1551	Phase 2
0.7593	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD2346	Discontinued
0.7547	Intermediate Similarity	NPD2344	Approved
0.7546	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD7199	Phase 2
0.7531	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6234	Discontinued
0.7516	Intermediate Similarity	NPD4628	Phase 3
0.7516	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5953	Discontinued
0.7486	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7286	Phase 2
0.7484	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD1933	Approved
0.7429	Intermediate Similarity	NPD3751	Discontinued
0.7419	Intermediate Similarity	NPD4625	Phase 3
0.741	Intermediate Similarity	NPD1653	Approved
0.7407	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD9494	Approved
0.7399	Intermediate Similarity	NPD3787	Discontinued
0.7391	Intermediate Similarity	NPD4360	Phase 2
0.7391	Intermediate Similarity	NPD4363	Phase 3
0.7386	Intermediate Similarity	NPD1203	Approved
0.7372	Intermediate Similarity	NPD3268	Approved
0.7362	Intermediate Similarity	NPD6190	Approved
0.7362	Intermediate Similarity	NPD2309	Approved
0.736	Intermediate Similarity	NPD7685	Pre-registration
0.7355	Intermediate Similarity	NPD4908	Phase 1
0.7342	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD5124	Phase 1
0.7338	Intermediate Similarity	NPD2798	Approved
0.7337	Intermediate Similarity	NPD37	Approved
0.7333	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7584	Approved
0.733	Intermediate Similarity	NPD7228	Approved
0.732	Intermediate Similarity	NPD3225	Approved
0.7312	Intermediate Similarity	NPD4308	Phase 3
0.7312	Intermediate Similarity	NPD7033	Discontinued
0.731	Intermediate Similarity	NPD4966	Approved
0.731	Intermediate Similarity	NPD4967	Phase 2
0.731	Intermediate Similarity	NPD4965	Approved
0.7278	Intermediate Similarity	NPD8312	Approved
0.7278	Intermediate Similarity	NPD8313	Approved
0.7273	Intermediate Similarity	NPD2797	Approved
0.7237	Intermediate Similarity	NPD422	Phase 1
0.72	Intermediate Similarity	NPD5710	Approved
0.72	Intermediate Similarity	NPD5711	Approved
0.72	Intermediate Similarity	NPD1548	Phase 1
0.7196	Intermediate Similarity	NPD6778	Approved
0.7196	Intermediate Similarity	NPD6779	Approved
0.7196	Intermediate Similarity	NPD6776	Approved
0.7196	Intermediate Similarity	NPD6777	Approved
0.7196	Intermediate Similarity	NPD6782	Approved
0.7196	Intermediate Similarity	NPD6780	Approved
0.7196	Intermediate Similarity	NPD6781	Approved
0.719	Intermediate Similarity	NPD9717	Approved
0.719	Intermediate Similarity	NPD9269	Phase 2
0.719	Intermediate Similarity	NPD1608	Approved
0.7166	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD4361	Phase 2
0.716	Intermediate Similarity	NPD7458	Discontinued
0.716	Intermediate Similarity	NPD5405	Approved
0.716	Intermediate Similarity	NPD5406	Approved
0.716	Intermediate Similarity	NPD5408	Approved
0.716	Intermediate Similarity	NPD5404	Approved
0.7159	Intermediate Similarity	NPD5242	Approved
0.7158	Intermediate Similarity	NPD8150	Discontinued
0.7158	Intermediate Similarity	NPD8434	Phase 2
0.7151	Intermediate Similarity	NPD4288	Approved
0.7143	Intermediate Similarity	NPD4749	Approved
0.7134	Intermediate Similarity	NPD6832	Phase 2
0.7126	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1201	Approved
0.7124	Intermediate Similarity	NPD1610	Phase 2
0.7124	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD2403	Approved
0.7102	Intermediate Similarity	NPD7229	Phase 3
0.7083	Intermediate Similarity	NPD5049	Phase 3
0.7083	Intermediate Similarity	NPD7435	Discontinued
0.7077	Intermediate Similarity	NPD8151	Discontinued
0.7076	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD2424	Discontinued
0.707	Intermediate Similarity	NPD3018	Phase 2
0.7063	Intermediate Similarity	NPD4307	Phase 2
0.7063	Intermediate Similarity	NPD4060	Phase 1
0.7059	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3267	Approved
0.7051	Intermediate Similarity	NPD1470	Approved
0.7051	Intermediate Similarity	NPD3266	Approved
0.7048	Intermediate Similarity	NPD2354	Approved
0.7044	Intermediate Similarity	NPD6798	Discontinued
0.7044	Intermediate Similarity	NPD411	Approved
0.7035	Intermediate Similarity	NPD6844	Discontinued
0.7033	Intermediate Similarity	NPD7549	Discontinued
0.703	Intermediate Similarity	NPD2654	Approved
0.7022	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD5536	Phase 2
0.7018	Intermediate Similarity	NPD6585	Discontinued
0.7006	Intermediate Similarity	NPD3300	Phase 2
0.7005	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7783	Phase 2
0.6995	Remote Similarity	NPD7697	Approved
0.6995	Remote Similarity	NPD7696	Phase 3
0.6995	Remote Similarity	NPD7698	Approved
0.6994	Remote Similarity	NPD8455	Phase 2

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