NPASS Compound

Structure

NPC472276 OpenBabel07101718302D 29 33 0 0 1 0 0 0 0 0999 V2000 8.6010 -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 -1.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8053 -2.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7564 -2.4781 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 1.7321 -2.0000 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 7.6010 -1.0000 0.0000 C 0 0 1 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 0.8660 -1.5000 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 6.0622 -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 6.0622 -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 -2.0000 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 0.8660 -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 7.0132 -1.8090 0.0000 C 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 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -0.1910 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 2 22 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 23 1 0 0 0 0 6 7 2 0 0 0 0 6 11 1 0 0 0 0 7 22 1 0 0 0 0 8 12 2 0 0 0 0 8 13 1 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 1 1 1 0 0 0 10 23 1 0 0 0 0 10 27 1 0 0 0 0 11 20 2 0 0 0 0 11 21 1 0 0 0 0 12 18 1 0 0 0 0 12 20 1 0 0 0 0 13 21 2 0 0 0 0 13 24 1 0 0 0 0 14 16 1 0 0 0 0 14 28 1 0 0 0 0 15 17 2 0 0 0 0 15 27 1 0 0 0 0 16 18 1 0 0 0 0 16 19 2 0 0 0 0 17 19 1 0 0 0 0 17 23 1 0 0 0 0 18 25 2 0 0 0 0 19 26 1 0 0 0 0 20 28 1 0 0 0 0 21 29 1 0 0 0 0 22 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	394.14
Volume:	395.232
LogP:	5.528
LogD:	3.452
LogS:	-3.624
# Rotatable Bonds:	0
TPSA:	89.13
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.542
Synthetic Accessibility Score:	3.959
Fsp3:	0.348
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:	-4.814
MDCK Permeability:	2.1809080863022245e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.071
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	92.73925018310547%
Volume Distribution (VD):	0.829
Pgp-substrate:	10.642457008361816%

ADMET: Metabolism

CYP1A2-inhibitor:	0.586
CYP1A2-substrate:	0.595
CYP2C19-inhibitor:	0.599
CYP2C19-substrate:	0.167
CYP2C9-inhibitor:	0.857
CYP2C9-substrate:	0.866
CYP2D6-inhibitor:	0.54
CYP2D6-substrate:	0.27
CYP3A4-inhibitor:	0.325
CYP3A4-substrate:	0.255

ADMET: Excretion

Clearance (CL):	1.832
Half-life (T1/2):	0.18

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.887
Drug-inuced Liver Injury (DILI):	0.962
AMES Toxicity:	0.303
Rat Oral Acute Toxicity:	0.96
Maximum Recommended Daily Dose:	0.906
Skin Sensitization:	0.694
Carcinogencity:	0.908
Eye Corrosion:	0.003
Eye Irritation:	0.613
Respiratory Toxicity:	0.837

Download Data

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

Natural Product: NPC472276

Natural Product ID:	NPC472276
*Common Name:**	UNAGKSRBZSVESZ-JTQLQIEISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UNAGKSRBZSVESZ-JTQLQIEISA-N
Standard InCHI:	InChI=1S/C23H22O6/c1-10-23(4,5)17-15(27-10)9-14-16(19(17)26)18(25)12-8-13(24)21-11(20(12)28-14)6-7-22(2,3)29-21/h6-10,24,26H,1-5H3/t10-/m0/s1
SMILES:	Oc1cc2c(c3c1OC(C)(C)C=C3)oc1c(c2=O)c(O)c2c(c1)O[C@H](C2(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3357565
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones [CHEMONTID:0003521] Pyranoxanthones

*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
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[15787460]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787460]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16203143]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16919944]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	root bark	n.a.	n.a.	PMID[17608532]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17950599]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	fruits	n.a.	n.a.	PMID[19113968]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[19191562]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[19280148]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19285413]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19660948]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[25322455]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	root barks	purchased from the local herbal market, Chungbuk, Korea	2012-JUL	PMID[26227773]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	15900.0	nM	PMID[473873]

☑ 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 NPC472276 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	459
0.1-0.2	1811
0.2-0.3	3935
0.3-0.4	10311
0.4-0.5	8208
0.5-0.6	3777
0.6-0.7	5460
0.7-0.8	4977
0.8-0.85	2341
0.85-0.9	1161
0.9-0.95	244
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9812	High Similarity	NPC288813
0.9686	High Similarity	NPC472281
0.9686	High Similarity	NPC205265
0.9686	High Similarity	NPC303460
0.9686	High Similarity	NPC306321
0.9625	High Similarity	NPC472277
0.9563	High Similarity	NPC329669
0.9563	High Similarity	NPC473313
0.9563	High Similarity	NPC18100
0.9563	High Similarity	NPC472278
0.956	High Similarity	NPC57715
0.9512	High Similarity	NPC310794
0.95	High Similarity	NPC81679
0.95	High Similarity	NPC83922
0.95	High Similarity	NPC261470
0.95	High Similarity	NPC472448
0.9497	High Similarity	NPC188433
0.9448	High Similarity	NPC165456
0.9448	High Similarity	NPC152477
0.9448	High Similarity	NPC242395
0.9444	High Similarity	NPC170245
0.9444	High Similarity	NPC173292
0.9441	High Similarity	NPC124038
0.9437	High Similarity	NPC29876
0.9437	High Similarity	NPC167678
0.9437	High Similarity	NPC234644
0.9387	High Similarity	NPC8965
0.9383	High Similarity	NPC239752
0.9383	High Similarity	NPC50960
0.9383	High Similarity	NPC473286
0.9383	High Similarity	NPC326520
0.9383	High Similarity	NPC275780
0.9383	High Similarity	NPC108433
0.9383	High Similarity	NPC300053
0.9383	High Similarity	NPC472450
0.9379	High Similarity	NPC474162
0.9379	High Similarity	NPC474150
0.9379	High Similarity	NPC472402
0.9375	High Similarity	NPC204290
0.9375	High Similarity	NPC192686
0.9375	High Similarity	NPC118256
0.9375	High Similarity	NPC119209
0.9375	High Similarity	NPC476283
0.9375	High Similarity	NPC476980
0.9375	High Similarity	NPC472624
0.9375	High Similarity	NPC328102
0.9371	High Similarity	NPC180011
0.9371	High Similarity	NPC219867
0.9371	High Similarity	NPC79053
0.9333	High Similarity	NPC121333
0.9329	High Similarity	NPC177480
0.9325	High Similarity	NPC235610
0.9325	High Similarity	NPC39091
0.9325	High Similarity	NPC120593
0.9325	High Similarity	NPC128293
0.9321	High Similarity	NPC189473
0.9321	High Similarity	NPC220313
0.9321	High Similarity	NPC273959
0.9321	High Similarity	NPC475985
0.9321	High Similarity	NPC186686
0.9321	High Similarity	NPC23298
0.9317	High Similarity	NPC472275
0.9317	High Similarity	NPC134783
0.9317	High Similarity	NPC474038
0.9317	High Similarity	NPC259456
0.9313	High Similarity	NPC204879
0.9313	High Similarity	NPC172770
0.9313	High Similarity	NPC250214
0.9313	High Similarity	NPC95936
0.9313	High Similarity	NPC185258
0.9308	High Similarity	NPC115853
0.9268	High Similarity	NPC117854
0.9268	High Similarity	NPC6588
0.9268	High Similarity	NPC477154
0.9264	High Similarity	NPC234052
0.9264	High Similarity	NPC62261
0.9264	High Similarity	NPC224280
0.9259	High Similarity	NPC220912
0.9259	High Similarity	NPC329760
0.9259	High Similarity	NPC474034
0.9259	High Similarity	NPC472635
0.9259	High Similarity	NPC229632
0.9259	High Similarity	NPC474033
0.9255	High Similarity	NPC80375
0.9255	High Similarity	NPC475784
0.925	High Similarity	NPC36852
0.925	High Similarity	NPC475267
0.925	High Similarity	NPC291508
0.925	High Similarity	NPC476981
0.925	High Similarity	NPC210084
0.925	High Similarity	NPC27337
0.925	High Similarity	NPC52889
0.925	High Similarity	NPC156057
0.925	High Similarity	NPC474208
0.925	High Similarity	NPC474681
0.925	High Similarity	NPC284820
0.925	High Similarity	NPC474836
0.925	High Similarity	NPC48208
0.925	High Similarity	NPC473272
0.925	High Similarity	NPC161960
0.925	High Similarity	NPC78225
0.925	High Similarity	NPC162869
0.925	High Similarity	NPC304008
0.925	High Similarity	NPC196448
0.925	High Similarity	NPC262286
0.925	High Similarity	NPC218313
0.925	High Similarity	NPC99597
0.925	High Similarity	NPC223787
0.925	High Similarity	NPC187745
0.9245	High Similarity	NPC256925
0.9245	High Similarity	NPC200246
0.9226	High Similarity	NPC67302
0.9217	High Similarity	NPC475825
0.9217	High Similarity	NPC223375
0.9207	High Similarity	NPC472449
0.9207	High Similarity	NPC119589
0.9207	High Similarity	NPC43319
0.9207	High Similarity	NPC277480
0.9207	High Similarity	NPC37870
0.9202	High Similarity	NPC152659
0.9202	High Similarity	NPC41301
0.9202	High Similarity	NPC236521
0.9202	High Similarity	NPC248638
0.9202	High Similarity	NPC472625
0.9198	High Similarity	NPC187354
0.9198	High Similarity	NPC26326
0.9198	High Similarity	NPC61010
0.9198	High Similarity	NPC228383
0.9198	High Similarity	NPC266314
0.9198	High Similarity	NPC40037
0.9198	High Similarity	NPC32694
0.9198	High Similarity	NPC258331
0.9198	High Similarity	NPC471210
0.9198	High Similarity	NPC472632
0.9193	High Similarity	NPC184755
0.9193	High Similarity	NPC74178
0.9187	High Similarity	NPC133970
0.9187	High Similarity	NPC278778
0.9187	High Similarity	NPC255106
0.9187	High Similarity	NPC68093
0.9187	High Similarity	NPC6633
0.9187	High Similarity	NPC235165
0.9187	High Similarity	NPC291878
0.9187	High Similarity	NPC195796
0.9187	High Similarity	NPC35038
0.9187	High Similarity	NPC191146
0.9187	High Similarity	NPC138243
0.9187	High Similarity	NPC5322
0.9187	High Similarity	NPC470600
0.9187	High Similarity	NPC472455
0.9187	High Similarity	NPC472916
0.9167	High Similarity	NPC156635
0.9157	High Similarity	NPC74559
0.9157	High Similarity	NPC103307
0.9152	High Similarity	NPC218226
0.9152	High Similarity	NPC243877
0.9152	High Similarity	NPC247973
0.9152	High Similarity	NPC150131
0.9146	High Similarity	NPC37183
0.9146	High Similarity	NPC293319
0.9141	High Similarity	NPC476247
0.9141	High Similarity	NPC25152
0.9141	High Similarity	NPC78332
0.9141	High Similarity	NPC194427
0.9136	High Similarity	NPC174953
0.9136	High Similarity	NPC14353
0.9136	High Similarity	NPC298093
0.9136	High Similarity	NPC474960
0.9136	High Similarity	NPC471973
0.9136	High Similarity	NPC139036
0.9136	High Similarity	NPC471976
0.9136	High Similarity	NPC228785
0.9136	High Similarity	NPC28241
0.9136	High Similarity	NPC45146
0.9136	High Similarity	NPC235018
0.9136	High Similarity	NPC36217
0.9136	High Similarity	NPC56085
0.913	High Similarity	NPC129684
0.913	High Similarity	NPC96167
0.913	High Similarity	NPC222814
0.913	High Similarity	NPC181960
0.913	High Similarity	NPC245758
0.913	High Similarity	NPC472598
0.913	High Similarity	NPC472910
0.913	High Similarity	NPC472911
0.913	High Similarity	NPC471209
0.913	High Similarity	NPC474055
0.913	High Similarity	NPC470402
0.913	High Similarity	NPC472914
0.913	High Similarity	NPC19097
0.913	High Similarity	NPC469584
0.913	High Similarity	NPC472913
0.913	High Similarity	NPC299520
0.9125	High Similarity	NPC37392
0.9125	High Similarity	NPC2928
0.9125	High Similarity	NPC117992
0.9125	High Similarity	NPC256612
0.9125	High Similarity	NPC134287
0.9125	High Similarity	NPC470327
0.9125	High Similarity	NPC45849

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 NPC472276 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	393
0.1-0.2	958
0.2-0.3	1882
0.3-0.4	2686
0.4-0.5	1824
0.5-0.6	897
0.6-0.7	354
0.7-0.8	118
0.8-0.85	27
0.85-0.9	10
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9136	High Similarity	NPD5494	Approved
0.9062	High Similarity	NPD2801	Approved
0.9062	High Similarity	NPD2393	Clinical (unspecified phase)
0.9	High Similarity	NPD1934	Approved
0.8834	High Similarity	NPD3882	Suspended
0.881	High Similarity	NPD3818	Discontinued
0.869	High Similarity	NPD6166	Phase 2
0.869	High Similarity	NPD6167	Clinical (unspecified phase)
0.869	High Similarity	NPD6168	Clinical (unspecified phase)
0.8642	High Similarity	NPD4380	Phase 2
0.8555	High Similarity	NPD4338	Clinical (unspecified phase)
0.8538	High Similarity	NPD7054	Approved
0.85	High Similarity	NPD1511	Approved
0.8494	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8488	Intermediate Similarity	NPD7472	Approved
0.8488	Intermediate Similarity	NPD7074	Phase 3
0.843	Intermediate Similarity	NPD5844	Phase 1
0.8395	Intermediate Similarity	NPD1512	Approved
0.8333	Intermediate Similarity	NPD7075	Discontinued
0.8333	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6797	Phase 2
0.8323	Intermediate Similarity	NPD3817	Phase 2
0.8294	Intermediate Similarity	NPD1247	Approved
0.8286	Intermediate Similarity	NPD7251	Discontinued
0.8263	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD7808	Phase 3
0.8221	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD6801	Discontinued
0.8187	Intermediate Similarity	NPD1549	Phase 2
0.8187	Intermediate Similarity	NPD6959	Discontinued
0.8155	Intermediate Similarity	NPD1465	Phase 2
0.8155	Intermediate Similarity	NPD7819	Suspended
0.814	Intermediate Similarity	NPD6232	Discontinued
0.8137	Intermediate Similarity	NPD2800	Approved
0.8125	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8114	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD5402	Approved
0.8103	Intermediate Similarity	NPD7473	Discontinued
0.8079	Intermediate Similarity	NPD6559	Discontinued
0.8063	Intermediate Similarity	NPD2796	Approved
0.8036	Intermediate Similarity	NPD7411	Suspended
0.8023	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1510	Phase 2
0.7976	Intermediate Similarity	NPD6599	Discontinued
0.7965	Intermediate Similarity	NPD919	Approved
0.7907	Intermediate Similarity	NPD3749	Approved
0.7901	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD3926	Phase 2
0.7869	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD6799	Approved
0.7798	Intermediate Similarity	NPD920	Approved
0.7784	Intermediate Similarity	NPD2532	Approved
0.7784	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD2534	Approved
0.7784	Intermediate Similarity	NPD2533	Approved
0.775	Intermediate Similarity	NPD1240	Approved
0.775	Intermediate Similarity	NPD943	Approved
0.7746	Intermediate Similarity	NPD7768	Phase 2
0.773	Intermediate Similarity	NPD2935	Discontinued
0.7692	Intermediate Similarity	NPD5403	Approved
0.7663	Intermediate Similarity	NPD8434	Phase 2
0.7657	Intermediate Similarity	NPD6234	Discontinued
0.7654	Intermediate Similarity	NPD1607	Approved
0.7654	Intermediate Similarity	NPD3751	Discontinued
0.7651	Intermediate Similarity	NPD3750	Approved
0.7651	Intermediate Similarity	NPD4628	Phase 3
0.764	Intermediate Similarity	NPD1613	Approved
0.764	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7592	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD7685	Pre-registration
0.7574	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD5401	Approved
0.7556	Intermediate Similarity	NPD7228	Approved
0.7544	Intermediate Similarity	NPD1653	Approved
0.7541	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD3787	Discontinued
0.7515	Intermediate Similarity	NPD6099	Approved
0.7515	Intermediate Similarity	NPD6100	Approved
0.75	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6777	Approved
0.75	Intermediate Similarity	NPD6782	Approved
0.75	Intermediate Similarity	NPD6780	Approved
0.75	Intermediate Similarity	NPD6778	Approved
0.75	Intermediate Similarity	NPD6779	Approved
0.75	Intermediate Similarity	NPD6776	Approved
0.7485	Intermediate Similarity	NPD1243	Approved
0.7485	Intermediate Similarity	NPD230	Phase 1
0.7485	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD7199	Phase 2
0.7471	Intermediate Similarity	NPD37	Approved
0.747	Intermediate Similarity	NPD2344	Approved
0.7456	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD3027	Phase 3
0.7443	Intermediate Similarity	NPD4966	Approved
0.7443	Intermediate Similarity	NPD4965	Approved
0.7443	Intermediate Similarity	NPD4967	Phase 2
0.744	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6651	Approved
0.7438	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD7286	Phase 2
0.7405	Intermediate Similarity	NPD8312	Approved
0.7405	Intermediate Similarity	NPD8313	Approved
0.7399	Intermediate Similarity	NPD3226	Approved
0.7396	Intermediate Similarity	NPD6190	Approved
0.7389	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD7435	Discontinued
0.738	Intermediate Similarity	NPD8150	Discontinued
0.7378	Intermediate Similarity	NPD447	Suspended
0.7368	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2346	Discontinued
0.7349	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD3748	Approved
0.7349	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD2799	Discontinued
0.7337	Intermediate Similarity	NPD5953	Discontinued
0.7333	Intermediate Similarity	NPD5710	Approved
0.7333	Intermediate Similarity	NPD5711	Approved
0.733	Intermediate Similarity	NPD4360	Phase 2
0.733	Intermediate Similarity	NPD4363	Phase 3
0.7317	Intermediate Similarity	NPD7907	Approved
0.731	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1551	Phase 2
0.7304	Intermediate Similarity	NPD4665	Approved
0.7304	Intermediate Similarity	NPD4111	Phase 1
0.7301	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD2313	Discontinued
0.7296	Intermediate Similarity	NPD7696	Phase 3
0.7296	Intermediate Similarity	NPD7697	Approved
0.7296	Intermediate Similarity	NPD7698	Approved
0.7294	Intermediate Similarity	NPD2309	Approved
0.7282	Intermediate Similarity	NPD2494	Approved
0.7282	Intermediate Similarity	NPD2493	Approved
0.7273	Intermediate Similarity	NPD6844	Discontinued
0.7273	Intermediate Similarity	NPD7584	Approved
0.7259	Intermediate Similarity	NPD7870	Phase 2
0.7259	Intermediate Similarity	NPD7871	Phase 2
0.7254	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD6823	Phase 2
0.724	Intermediate Similarity	NPD6535	Approved
0.724	Intermediate Similarity	NPD6534	Approved
0.7236	Intermediate Similarity	NPD7701	Phase 2
0.7235	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD5761	Phase 2
0.7232	Intermediate Similarity	NPD5760	Phase 2
0.7222	Intermediate Similarity	NPD9494	Approved
0.7214	Intermediate Similarity	NPD7783	Phase 2
0.7214	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7390	Discontinued
0.72	Intermediate Similarity	NPD8151	Discontinued
0.72	Intermediate Similarity	NPD7458	Discontinued
0.7195	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD3450	Approved
0.7194	Intermediate Similarity	NPD3452	Approved
0.7182	Intermediate Similarity	NPD8127	Discontinued
0.7178	Intermediate Similarity	NPD4908	Phase 1
0.7172	Intermediate Similarity	NPD4583	Approved
0.7172	Intermediate Similarity	NPD4582	Approved
0.7169	Intermediate Similarity	NPD1933	Approved
0.7168	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD7549	Discontinued
0.7164	Intermediate Similarity	NPD7874	Approved
0.7164	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD2403	Approved
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD7229	Phase 3
0.7129	Intermediate Similarity	NPD7801	Approved
0.7128	Intermediate Similarity	NPD7700	Phase 2
0.7128	Intermediate Similarity	NPD7699	Phase 2
0.7121	Intermediate Similarity	NPD4002	Approved
0.7121	Intermediate Similarity	NPD4004	Approved
0.7118	Intermediate Similarity	NPD2424	Discontinued
0.7117	Intermediate Similarity	NPD2861	Phase 2
0.7113	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4361	Phase 2
0.7112	Intermediate Similarity	NPD7240	Approved
0.7104	Intermediate Similarity	NPD5242	Approved
0.7102	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD2975	Approved
0.7077	Intermediate Similarity	NPD2974	Approved
0.7077	Intermediate Similarity	NPD2973	Approved
0.7066	Intermediate Similarity	NPD5124	Phase 1
0.7066	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD4287	Approved
0.703	Intermediate Similarity	NPD4625	Phase 3
0.7029	Intermediate Similarity	NPD6273	Approved
0.7022	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD1729	Discontinued
0.7	Intermediate Similarity	NPD5353	Approved
0.6995	Remote Similarity	NPD2488	Approved
0.6995	Remote Similarity	NPD2490	Approved
0.6988	Remote Similarity	NPD6410	Clinical (unspecified phase)

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