NPASS Compound

Structure

CID177480 OpenBabel06191715552D 31 35 0 0 1 0 0 0 0 0999 V2000 0.2588 1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7934 0.3912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -3.0000 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 -5.1962 -3.0000 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 -6.9282 -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 -1.7321 0.0000 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 -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 -6.0622 -1.5000 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 -6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 2 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 -2.5981 -0.5000 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 -4.3301 -1.5000 0.0000 C 0 0 1 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 -4.3301 -2.5000 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 -7.7942 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 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 22 1 0 0 0 0 2 22 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 6 22 1 0 0 0 0 7 12 2 0 0 0 0 7 16 1 0 0 0 0 8 13 2 0 0 0 0 8 14 1 0 0 0 0 9 15 2 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 10 29 1 0 0 0 0 11 14 2 0 0 0 0 11 20 1 0 0 0 0 12 15 1 0 0 0 0 12 23 1 0 0 0 0 13 19 1 0 0 0 0 13 24 1 0 0 0 0 14 31 1 0 0 0 0 15 29 1 0 0 0 0 16 17 2 0 0 0 0 16 27 1 0 0 0 0 17 28 1 0 0 0 0 18 23 1 1 0 0 0 18 30 1 0 0 0 0 19 20 2 0 0 0 0 19 21 1 0 0 0 0 20 30 1 0 0 0 0 21 23 1 0 0 0 0 21 25 2 0 0 0 0 22 31 1 0 0 0 0 23 26 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.13
Volume:	412.812
LogP:	3.971
LogD:	3.699
LogS:	-4.247
# Rotatable Bonds:	2
TPSA:	103.68
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.756
Synthetic Accessibility Score:	3.966
Fsp3:	0.348
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.785
MDCK Permeability:	1.852954301284626e-05
Pgp-inhibitor:	0.874
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.03
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039
Plasma Protein Binding (PPB):	93.0734634399414%
Volume Distribution (VD):	0.771
Pgp-substrate:	8.470269203186035%

ADMET: Metabolism

CYP1A2-inhibitor:	0.205
CYP1A2-substrate:	0.823
CYP2C19-inhibitor:	0.46
CYP2C19-substrate:	0.8
CYP2C9-inhibitor:	0.673
CYP2C9-substrate:	0.725
CYP2D6-inhibitor:	0.63
CYP2D6-substrate:	0.418
CYP3A4-inhibitor:	0.848
CYP3A4-substrate:	0.806

ADMET: Excretion

Clearance (CL):	2.918
Half-life (T1/2):	0.245

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.894
Drug-inuced Liver Injury (DILI):	0.676
AMES Toxicity:	0.138
Rat Oral Acute Toxicity:	0.784
Maximum Recommended Daily Dose:	0.9
Skin Sensitization:	0.46
Carcinogencity:	0.82
Eye Corrosion:	0.003
Eye Irritation:	0.063
Respiratory Toxicity:	0.536

Download Data

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

Natural Product: NPC177480

Natural Product ID:	NPC177480
*Common Name:**	OFLCPNIRDVOOEZ-WZONZLPQSA-N
IUPAC Name:	n.a.
Synonyms:	11-Hydroxytephrosin
Standard InCHIKey:	OFLCPNIRDVOOEZ-WZONZLPQSA-N
Standard InCHI:	InChI=1S/C23H22O8/c1-22(2)6-5-11-14(31-22)8-13(24)19-20(11)30-18-10-29-15-9-17(28-4)16(27-3)7-12(15)23(18,26)21(19)25/h5-9,18,24,26H,10H2,1-4H3/t18-,23-/m1/s1
SMILES:	COc1cc2OC[C@@H]3[C@@](c2cc1OC)(O)C(=O)c1c(O3)c2C=CC(Oc2cc1O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL419669
PubChem CID:	155725
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001607] Rotenoids [CHEMONTID:0003528] Rotenones

*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
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18841906]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[28075580]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8326318]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8350086]
NPO6147	Eupatorium riparium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3890	Scopolia japonica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5753	Glycosmis montana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3890	Scopolia japonica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5753	Glycosmis montana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6147	Eupatorium riparium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6147	Eupatorium riparium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3890	Scopolia japonica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3890	Scopolia japonica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5368	Achillea cretica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2671	Pedicularis semitorta	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12750	Cordia americana	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6147	Eupatorium riparium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3890	Scopolia japonica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5753	Glycosmis montana	Species	Rutaceae	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	3
Others	2

Activity Type	# Activity
Individual Protein	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	>	23.0	uM	PMID[466484]
NPT2	Others	Unspecified		IC50	=	190.0	nM	PMID[466483]
NPT2	Others	Unspecified		IC50	=	4210.0	nM	PMID[466483]
NPT27	Others	Unspecified		IC50	>	47000.0	nM	PMID[466484]
NPT2	Others	Unspecified		Inhibition	=	60.0	%	PMID[466484]

☑ 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 NPC177480 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	437
0.1-0.2	1726
0.2-0.3	4144
0.3-0.4	10169
0.4-0.5	7945
0.5-0.6	3690
0.6-0.7	4922
0.7-0.8	5372
0.8-0.85	2630
0.85-0.9	1395
0.9-0.95	257
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9811	High Similarity	NPC8965
0.975	High Similarity	NPC326877
0.9689	High Similarity	NPC74559
0.9627	High Similarity	NPC242395
0.9625	High Similarity	NPC120593
0.9563	High Similarity	NPC234052
0.9563	High Similarity	NPC224280
0.9563	High Similarity	NPC62261
0.9509	High Similarity	NPC121333
0.9506	High Similarity	NPC152477
0.95	High Similarity	NPC41301
0.9448	High Similarity	NPC103307
0.9398	High Similarity	NPC67302
0.9383	High Similarity	NPC472449
0.9383	High Similarity	NPC471213
0.9379	High Similarity	NPC472625
0.9375	High Similarity	NPC173137
0.9375	High Similarity	NPC40037
0.9371	High Similarity	NPC152904
0.9329	High Similarity	NPC472276
0.9325	High Similarity	NPC477154
0.9325	High Similarity	NPC117854
0.9325	High Similarity	NPC6588
0.9325	High Similarity	NPC295082
0.9325	High Similarity	NPC158761
0.9321	High Similarity	NPC239752
0.9321	High Similarity	NPC275780
0.9321	High Similarity	NPC472450
0.9321	High Similarity	NPC470457
0.9321	High Similarity	NPC50960
0.9317	High Similarity	NPC474162
0.9317	High Similarity	NPC472448
0.9317	High Similarity	NPC261470
0.9317	High Similarity	NPC83922
0.9317	High Similarity	NPC220912
0.9317	High Similarity	NPC229632
0.9317	High Similarity	NPC474150
0.9317	High Similarity	NPC52204
0.9313	High Similarity	NPC119209
0.9313	High Similarity	NPC475784
0.9313	High Similarity	NPC118256
0.9313	High Similarity	NPC192686
0.9313	High Similarity	NPC204290
0.9308	High Similarity	NPC284820
0.9308	High Similarity	NPC473272
0.9277	High Similarity	NPC108202
0.9264	High Similarity	NPC173292
0.9264	High Similarity	NPC39091
0.9259	High Similarity	NPC236521
0.9259	High Similarity	NPC189473
0.9259	High Similarity	NPC273959
0.9259	High Similarity	NPC303460
0.9259	High Similarity	NPC306321
0.9259	High Similarity	NPC186686
0.9259	High Similarity	NPC248638
0.9259	High Similarity	NPC23298
0.9259	High Similarity	NPC152659
0.9259	High Similarity	NPC470459
0.9259	High Similarity	NPC146134
0.9255	High Similarity	NPC228383
0.9255	High Similarity	NPC266314
0.9255	High Similarity	NPC471210
0.9255	High Similarity	NPC167678
0.9255	High Similarity	NPC165549
0.9255	High Similarity	NPC472632
0.9255	High Similarity	NPC471212
0.9255	High Similarity	NPC471499
0.9255	High Similarity	NPC471211
0.9255	High Similarity	NPC29876
0.9255	High Similarity	NPC134783
0.9255	High Similarity	NPC289771
0.9255	High Similarity	NPC474038
0.9255	High Similarity	NPC26326
0.925	High Similarity	NPC473990
0.925	High Similarity	NPC250214
0.925	High Similarity	NPC95936
0.9245	High Similarity	NPC303255
0.9245	High Similarity	NPC146636
0.9226	High Similarity	NPC324742
0.9222	High Similarity	NPC156635
0.9207	High Similarity	NPC470456
0.9207	High Similarity	NPC14662
0.9207	High Similarity	NPC243877
0.9207	High Similarity	NPC260266
0.9202	High Similarity	NPC7154
0.9202	High Similarity	NPC36916
0.9202	High Similarity	NPC293319
0.9202	High Similarity	NPC125039
0.9202	High Similarity	NPC36
0.9202	High Similarity	NPC7688
0.9202	High Similarity	NPC58223
0.9202	High Similarity	NPC72787
0.9198	High Similarity	NPC474034
0.9198	High Similarity	NPC472402
0.9198	High Similarity	NPC474033
0.9198	High Similarity	NPC194427
0.9198	High Similarity	NPC25152
0.9193	High Similarity	NPC263449
0.9193	High Similarity	NPC287328
0.9193	High Similarity	NPC470326
0.9193	High Similarity	NPC174953
0.9193	High Similarity	NPC476980
0.9193	High Similarity	NPC246478
0.9193	High Similarity	NPC282009
0.9193	High Similarity	NPC471976
0.9187	High Similarity	NPC475267
0.9187	High Similarity	NPC27337
0.9187	High Similarity	NPC224137
0.9187	High Similarity	NPC471209
0.9187	High Similarity	NPC78225
0.9187	High Similarity	NPC189179
0.9187	High Similarity	NPC474836
0.9187	High Similarity	NPC476981
0.9187	High Similarity	NPC223787
0.9187	High Similarity	NPC474208
0.9187	High Similarity	NPC227192
0.9187	High Similarity	NPC156057
0.9187	High Similarity	NPC48208
0.9187	High Similarity	NPC162869
0.9187	High Similarity	NPC93376
0.9187	High Similarity	NPC75215
0.9182	High Similarity	NPC476169
0.9182	High Similarity	NPC37392
0.9176	High Similarity	NPC148710
0.9167	High Similarity	NPC168584
0.9157	High Similarity	NPC186847
0.9157	High Similarity	NPC472454
0.9157	High Similarity	NPC257667
0.9152	High Similarity	NPC107627
0.9152	High Similarity	NPC288813
0.9152	High Similarity	NPC165456
0.9146	High Similarity	NPC477517
0.9146	High Similarity	NPC37870
0.9146	High Similarity	NPC170245
0.9146	High Similarity	NPC43319
0.9146	High Similarity	NPC470462
0.9146	High Similarity	NPC128293
0.9146	High Similarity	NPC272502
0.9136	High Similarity	NPC474186
0.9136	High Similarity	NPC57715
0.9136	High Similarity	NPC308992
0.9136	High Similarity	NPC472634
0.9136	High Similarity	NPC198829
0.9136	High Similarity	NPC474187
0.9136	High Similarity	NPC3629
0.9136	High Similarity	NPC61010
0.9136	High Similarity	NPC259456
0.913	High Similarity	NPC4481
0.913	High Similarity	NPC261004
0.913	High Similarity	NPC288669
0.913	High Similarity	NPC253634
0.913	High Similarity	NPC105242
0.913	High Similarity	NPC193842
0.913	High Similarity	NPC143828
0.913	High Similarity	NPC18772
0.913	High Similarity	NPC204854
0.913	High Similarity	NPC19687
0.913	High Similarity	NPC300943
0.913	High Similarity	NPC204879
0.913	High Similarity	NPC176300
0.913	High Similarity	NPC115798
0.913	High Similarity	NPC117418
0.913	High Similarity	NPC18607
0.913	High Similarity	NPC53545
0.913	High Similarity	NPC55738
0.913	High Similarity	NPC7846
0.913	High Similarity	NPC22192
0.913	High Similarity	NPC130894
0.913	High Similarity	NPC152166
0.913	High Similarity	NPC191459
0.913	High Similarity	NPC9609
0.913	High Similarity	NPC25495
0.913	High Similarity	NPC22472
0.9125	High Similarity	NPC278778
0.9125	High Similarity	NPC291878
0.9125	High Similarity	NPC68093
0.9125	High Similarity	NPC474520
0.9125	High Similarity	NPC49824
0.9125	High Similarity	NPC255106
0.9125	High Similarity	NPC235165
0.9125	High Similarity	NPC195796
0.9125	High Similarity	NPC247017
0.9125	High Similarity	NPC178854
0.9125	High Similarity	NPC191146
0.9125	High Similarity	NPC268161
0.9125	High Similarity	NPC470600
0.9125	High Similarity	NPC98661
0.9125	High Similarity	NPC35038
0.9119	High Similarity	NPC86485
0.9107	High Similarity	NPC169733
0.9102	High Similarity	NPC310794
0.9096	High Similarity	NPC102277
0.9096	High Similarity	NPC279209
0.9091	High Similarity	NPC93099
0.9091	High Similarity	NPC218226
0.9091	High Similarity	NPC150131
0.9091	High Similarity	NPC474024
0.9085	High Similarity	NPC326520
0.908	High Similarity	NPC78332
0.908	High Similarity	NPC81679

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 NPC177480 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	969
0.2-0.3	1959
0.3-0.4	2574
0.4-0.5	1730
0.5-0.6	940
0.6-0.7	413
0.7-0.8	129
0.8-0.85	37
0.85-0.9	7
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9202	High Similarity	NPD6166	Phase 2
0.9202	High Similarity	NPD6168	Clinical (unspecified phase)
0.9202	High Similarity	NPD6167	Clinical (unspecified phase)
0.9	High Similarity	NPD2393	Clinical (unspecified phase)
0.9	High Similarity	NPD2801	Approved
0.8957	High Similarity	NPD5494	Approved
0.8938	High Similarity	NPD1934	Approved
0.8824	High Similarity	NPD7808	Phase 3
0.8824	High Similarity	NPD4338	Clinical (unspecified phase)
0.8817	High Similarity	NPD6797	Phase 2
0.881	High Similarity	NPD7054	Approved
0.8765	High Similarity	NPD7251	Discontinued
0.8757	High Similarity	NPD7074	Phase 3
0.8757	High Similarity	NPD7472	Approved
0.8712	High Similarity	NPD3817	Phase 2
0.8698	High Similarity	NPD7804	Clinical (unspecified phase)
0.8696	High Similarity	NPD4380	Phase 2
0.8659	High Similarity	NPD3882	Suspended
0.8616	High Similarity	NPD4378	Clinical (unspecified phase)
0.8606	High Similarity	NPD7075	Discontinued
0.8563	High Similarity	NPD6959	Discontinued
0.8562	High Similarity	NPD1512	Approved
0.8529	High Similarity	NPD3818	Discontinued
0.8476	Intermediate Similarity	NPD6801	Discontinued
0.8438	Intermediate Similarity	NPD1511	Approved
0.8434	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD5402	Approved
0.8372	Intermediate Similarity	NPD5844	Phase 1
0.8294	Intermediate Similarity	NPD6232	Discontinued
0.8272	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD7473	Discontinued
0.8235	Intermediate Similarity	NPD1247	Approved
0.8204	Intermediate Similarity	NPD7819	Suspended
0.8204	Intermediate Similarity	NPD1465	Phase 2
0.8176	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD1549	Phase 2
0.8122	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD7411	Suspended
0.8	Intermediate Similarity	NPD2796	Approved
0.7989	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD6799	Approved
0.7952	Intermediate Similarity	NPD5403	Approved
0.7937	Intermediate Similarity	NPD1510	Phase 2
0.7931	Intermediate Similarity	NPD3926	Phase 2
0.7921	Intermediate Similarity	NPD6559	Discontinued
0.7917	Intermediate Similarity	NPD6599	Discontinued
0.7912	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD919	Approved
0.7898	Intermediate Similarity	NPD3751	Discontinued
0.7874	Intermediate Similarity	NPD3787	Discontinued
0.7845	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD5401	Approved
0.7819	Intermediate Similarity	NPD6780	Approved
0.7819	Intermediate Similarity	NPD6776	Approved
0.7819	Intermediate Similarity	NPD6777	Approved
0.7819	Intermediate Similarity	NPD6779	Approved
0.7819	Intermediate Similarity	NPD6781	Approved
0.7819	Intermediate Similarity	NPD6778	Approved
0.7819	Intermediate Similarity	NPD6782	Approved
0.7744	Intermediate Similarity	NPD2800	Approved
0.7705	Intermediate Similarity	NPD8150	Discontinued
0.7696	Intermediate Similarity	NPD7698	Approved
0.7696	Intermediate Similarity	NPD7696	Phase 3
0.7696	Intermediate Similarity	NPD7435	Discontinued
0.7696	Intermediate Similarity	NPD7697	Approved
0.7688	Intermediate Similarity	NPD7768	Phase 2
0.7688	Intermediate Similarity	NPD1240	Approved
0.7669	Intermediate Similarity	NPD2935	Discontinued
0.7644	Intermediate Similarity	NPD3749	Approved
0.7637	Intermediate Similarity	NPD8313	Approved
0.7637	Intermediate Similarity	NPD8312	Approved
0.7632	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD7701	Phase 2
0.7619	Intermediate Similarity	NPD2534	Approved
0.7619	Intermediate Similarity	NPD2532	Approved
0.7619	Intermediate Similarity	NPD2533	Approved
0.7598	Intermediate Similarity	NPD7228	Approved
0.7593	Intermediate Similarity	NPD1607	Approved
0.759	Intermediate Similarity	NPD3750	Approved
0.7578	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD943	Approved
0.7578	Intermediate Similarity	NPD1613	Approved
0.7576	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD7870	Phase 2
0.7565	Intermediate Similarity	NPD7871	Phase 2
0.7553	Intermediate Similarity	NPD6535	Approved
0.7553	Intermediate Similarity	NPD6534	Approved
0.7545	Intermediate Similarity	NPD6190	Approved
0.7529	Intermediate Similarity	NPD920	Approved
0.7528	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD7699	Phase 2
0.7526	Intermediate Similarity	NPD7700	Phase 2
0.7514	Intermediate Similarity	NPD8434	Phase 2
0.7513	Intermediate Similarity	NPD7783	Phase 2
0.7513	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6234	Discontinued
0.7485	Intermediate Similarity	NPD1653	Approved
0.7474	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD7874	Approved
0.7462	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7390	Discontinued
0.7442	Intermediate Similarity	NPD3226	Approved
0.7438	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD7685	Pre-registration
0.7427	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD7801	Approved
0.7416	Intermediate Similarity	NPD7199	Phase 2
0.7414	Intermediate Similarity	NPD37	Approved
0.7411	Intermediate Similarity	NPD8151	Discontinued
0.7394	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD3027	Phase 3
0.7386	Intermediate Similarity	NPD4966	Approved
0.7386	Intermediate Similarity	NPD4967	Phase 2
0.7386	Intermediate Similarity	NPD4965	Approved
0.7381	Intermediate Similarity	NPD4628	Phase 3
0.7378	Intermediate Similarity	NPD6651	Approved
0.7377	Intermediate Similarity	NPD5953	Discontinued
0.7375	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD6823	Phase 2
0.7368	Intermediate Similarity	NPD4363	Phase 3
0.7368	Intermediate Similarity	NPD4360	Phase 2
0.7363	Intermediate Similarity	NPD7286	Phase 2
0.7349	Intermediate Similarity	NPD6100	Approved
0.7349	Intermediate Similarity	NPD6099	Approved
0.7346	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD447	Suspended
0.7317	Intermediate Similarity	NPD230	Phase 1
0.731	Intermediate Similarity	NPD7584	Approved
0.731	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD2346	Discontinued
0.7289	Intermediate Similarity	NPD2799	Discontinued
0.7289	Intermediate Similarity	NPD3748	Approved
0.7289	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8455	Phase 2
0.7246	Intermediate Similarity	NPD1551	Phase 2
0.7243	Intermediate Similarity	NPD7240	Approved
0.7239	Intermediate Similarity	NPD2313	Discontinued
0.7239	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4908	Phase 1
0.7219	Intermediate Similarity	NPD1243	Approved
0.7216	Intermediate Similarity	NPD6844	Discontinued
0.7209	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD8320	Phase 1
0.7208	Intermediate Similarity	NPD8319	Approved
0.7204	Intermediate Similarity	NPD7549	Discontinued
0.7202	Intermediate Similarity	NPD2344	Approved
0.7198	Intermediate Similarity	NPD2403	Approved
0.7193	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD5711	Approved
0.7182	Intermediate Similarity	NPD5710	Approved
0.7176	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD5124	Phase 1
0.7108	Intermediate Similarity	NPD1933	Approved
0.7108	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7907	Approved
0.7091	Intermediate Similarity	NPD6233	Phase 2
0.7085	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7033	Discontinued
0.7073	Intermediate Similarity	NPD4625	Phase 3
0.7062	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2424	Discontinued
0.7056	Intermediate Similarity	NPD2494	Approved
0.7056	Intermediate Similarity	NPD2493	Approved
0.7055	Intermediate Similarity	NPD2861	Phase 2
0.7055	Intermediate Similarity	NPD9494	Approved
0.7049	Intermediate Similarity	NPD5242	Approved
0.7048	Intermediate Similarity	NPD4060	Phase 1
0.7047	Intermediate Similarity	NPD6213	Phase 3
0.7047	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6212	Phase 3
0.7045	Intermediate Similarity	NPD7458	Discontinued
0.7045	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD2309	Approved
0.703	Intermediate Similarity	NPD6798	Discontinued
0.7011	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6355	Discontinued
0.7005	Intermediate Similarity	NPD4111	Phase 1
0.7005	Intermediate Similarity	NPD4665	Approved
0.7	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1610	Phase 2
0.6995	Remote Similarity	NPD7229	Phase 3
0.6974	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4361	Phase 2
0.697	Remote Similarity	NPD3450	Approved
0.697	Remote Similarity	NPD3452	Approved
0.6954	Remote Similarity	NPD8285	Discontinued
0.695	Remote Similarity	NPD4583	Approved
0.695	Remote Similarity	NPD4582	Approved
0.6944	Remote Similarity	NPD5353	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