NPASS Compound

Structure

CID19097 OpenBabel06191715342D 29 33 0 0 1 0 0 0 0 0999 V2000 -3.9049 -1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9049 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -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 -1.8171 -1.1910 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4049 -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 0.5000 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 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -2.0000 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 4.3301 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 0.5000 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 1.7321 -1.0000 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 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -2.8090 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 11 2 0 0 0 0 2 11 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 6 2 0 0 0 0 5 12 1 0 0 0 0 6 15 1 0 0 0 0 7 13 2 0 0 0 0 7 18 1 0 0 0 0 8 14 1 0 0 0 0 8 16 1 0 0 0 0 9 17 2 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 10 27 1 0 0 0 0 12 22 1 0 0 0 0 12 23 2 0 0 0 0 13 17 1 0 0 0 0 13 21 1 0 0 0 0 14 15 2 0 0 0 0 14 23 1 0 0 0 0 15 28 1 0 0 0 0 16 11 1 1 0 0 0 16 28 1 0 0 0 0 17 27 1 0 0 0 0 18 19 2 0 0 0 0 18 25 1 0 0 0 0 19 26 1 0 0 0 0 20 21 2 0 0 0 0 20 29 1 0 0 0 0 21 22 1 0 0 0 0 22 24 2 0 0 0 0 23 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.13
Volume:	392.595
LogP:	3.974
LogD:	2.973
LogS:	-6.238
# Rotatable Bonds:	3
TPSA:	67.13
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.621
Synthetic Accessibility Score:	3.461
Fsp3:	0.261
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.776
MDCK Permeability:	2.3963011699379422e-05
Pgp-inhibitor:	0.608
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038
Plasma Protein Binding (PPB):	87.54994201660156%
Volume Distribution (VD):	0.688
Pgp-substrate:	7.677676677703857%

ADMET: Metabolism

CYP1A2-inhibitor:	0.209
CYP1A2-substrate:	0.978
CYP2C19-inhibitor:	0.461
CYP2C19-substrate:	0.495
CYP2C9-inhibitor:	0.793
CYP2C9-substrate:	0.924
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.927
CYP3A4-inhibitor:	0.294
CYP3A4-substrate:	0.547

ADMET: Excretion

Clearance (CL):	3.361
Half-life (T1/2):	0.21

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.998
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.916
Rat Oral Acute Toxicity:	0.61
Maximum Recommended Daily Dose:	0.904
Skin Sensitization:	0.062
Carcinogencity:	0.368
Eye Corrosion:	0.003
Eye Irritation:	0.042
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC19097

Natural Product ID:	NPC19097
*Common Name:**	Dehydrorotenone
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GFERNZCCTZEIET-MRXNPFEDSA-N
Standard InCHI:	InChI=1S/C23H20O6/c1-11(2)16-8-14-15(28-16)6-5-12-22(24)21-13-7-18(25-3)19(26-4)9-17(13)27-10-20(21)29-23(12)14/h5-7,9,16H,1,8,10H2,2-4H3/t16-/m1/s1
SMILES:	C=C(C)[C@H]1Cc2c(ccc3c(=O)c4-c5cc(c(cc5OCc4oc23)OC)OC)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL7940
PubChem CID:	99190
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
NPO32669	derris malaccensis plain	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975515]
NPO5753	Glycosmis montana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
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]
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]
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]
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	2
MIC	1
Others	6

Activity Type	# Activity
Cell Line	2
Individual Protein	2
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[536613]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[536613]
NPT938	Organism	Cavia porcellus	Cavia porcellus	Inhibition	=	0.0	%	PMID[536611]
NPT938	Organism	Cavia porcellus	Cavia porcellus	Collapse time	=	216.0	s	PMID[536611]
NPT938	Organism	Cavia porcellus	Cavia porcellus	Collapse time	=	248.0	s	PMID[536611]
NPT451	Organism	Helicobacter pylori	Helicobacter pylori	MIC	=	9.8	ug.mL-1	PMID[536612]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	113.51	%	PMID[536614]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	92.82	%	PMID[536614]

☑ 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 NPC19097 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	518
0.1-0.2	1903
0.2-0.3	4695
0.3-0.4	11215
0.4-0.5	6817
0.5-0.6	3964
0.6-0.7	5864
0.7-0.8	4818
0.8-0.85	1977
0.85-0.9	849
0.9-0.95	75
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9667	High Similarity	NPC472408
0.9667	High Similarity	NPC128961
0.9608	High Similarity	NPC298093
0.9539	High Similarity	NPC180340
0.9484	High Similarity	NPC18284
0.9484	High Similarity	NPC273021
0.947	High Similarity	NPC166201
0.947	High Similarity	NPC40033
0.9467	High Similarity	NPC5840
0.9467	High Similarity	NPC189270
0.9419	High Similarity	NPC165549
0.9396	High Similarity	NPC205522
0.9359	High Similarity	NPC81679
0.9333	High Similarity	NPC63256
0.9333	High Similarity	NPC476342
0.9333	High Similarity	NPC10304
0.9329	High Similarity	NPC216314
0.9329	High Similarity	NPC106461
0.9329	High Similarity	NPC14958
0.9329	High Similarity	NPC120924
0.9329	High Similarity	NPC110639
0.9329	High Similarity	NPC40818
0.9329	High Similarity	NPC195919
0.9329	High Similarity	NPC215932
0.9304	High Similarity	NPC128293
0.9304	High Similarity	NPC173292
0.9299	High Similarity	NPC65846
0.9295	High Similarity	NPC34376
0.929	High Similarity	NPC113055
0.9281	High Similarity	NPC186507
0.9272	High Similarity	NPC238366
0.9267	High Similarity	NPC85233
0.9262	High Similarity	NPC471590
0.9262	High Similarity	NPC136278
0.9236	High Similarity	NPC261470
0.9226	High Similarity	NPC476981
0.9226	High Similarity	NPC78071
0.9221	High Similarity	NPC478238
0.92	High Similarity	NPC283002
0.92	High Similarity	NPC302408
0.92	High Similarity	NPC231013
0.9195	High Similarity	NPC182842
0.9195	High Similarity	NPC23955
0.9195	High Similarity	NPC113089
0.9187	High Similarity	NPC152477
0.9177	High Similarity	NPC273959
0.9172	High Similarity	NPC259456
0.9172	High Similarity	NPC40037
0.9167	High Similarity	NPC187792
0.9161	High Similarity	NPC155063
0.9161	High Similarity	NPC248299
0.9156	High Similarity	NPC280937
0.9156	High Similarity	NPC478213
0.9145	High Similarity	NPC69752
0.9133	High Similarity	NPC165512
0.913	High Similarity	NPC472276
0.913	High Similarity	NPC190351
0.9128	High Similarity	NPC476054
0.9128	High Similarity	NPC9966
0.9128	High Similarity	NPC70853
0.9119	High Similarity	NPC50960
0.9119	High Similarity	NPC475369
0.9114	High Similarity	NPC83922
0.9114	High Similarity	NPC478199
0.9114	High Similarity	NPC472448
0.9114	High Similarity	NPC302741
0.9108	High Similarity	NPC476980
0.9108	High Similarity	NPC328102
0.9103	High Similarity	NPC473272
0.9103	High Similarity	NPC258644
0.9103	High Similarity	NPC284820
0.9103	High Similarity	NPC310206
0.9097	High Similarity	NPC37392
0.9091	High Similarity	NPC68882
0.9091	High Similarity	NPC153008
0.9091	High Similarity	NPC148497
0.9091	High Similarity	NPC292460
0.9085	High Similarity	NPC201547
0.9085	High Similarity	NPC259058
0.9074	High Similarity	NPC121333
0.9068	High Similarity	NPC288813
0.9068	High Similarity	NPC242395
0.9067	High Similarity	NPC293201
0.9062	High Similarity	NPC120593
0.906	High Similarity	NPC29536
0.906	High Similarity	NPC124467
0.906	High Similarity	NPC185607
0.906	High Similarity	NPC214919
0.9057	High Similarity	NPC124038
0.9051	High Similarity	NPC167678
0.9051	High Similarity	NPC29876
0.9051	High Similarity	NPC258331
0.9045	High Similarity	NPC184755
0.9045	High Similarity	NPC469658
0.9045	High Similarity	NPC95936
0.9045	High Similarity	NPC74178
0.9045	High Similarity	NPC250214
0.9032	High Similarity	NPC57211
0.9032	High Similarity	NPC472915
0.9032	High Similarity	NPC244371
0.9026	High Similarity	NPC279061
0.9026	High Similarity	NPC262623
0.9026	High Similarity	NPC308451
0.9026	High Similarity	NPC226973
0.9026	High Similarity	NPC208043
0.902	High Similarity	NPC181250
0.9018	High Similarity	NPC310794
0.9013	High Similarity	NPC117463
0.9013	High Similarity	NPC470511
0.9013	High Similarity	NPC299923
0.9006	High Similarity	NPC8965
0.9	High Similarity	NPC472277
0.9	High Similarity	NPC300053
0.9	High Similarity	NPC326520
0.9	High Similarity	NPC108433
0.8994	High Similarity	NPC229632
0.8994	High Similarity	NPC194427
0.8993	High Similarity	NPC58229
0.8987	High Similarity	NPC119209
0.8987	High Similarity	NPC118256
0.8987	High Similarity	NPC472624
0.8987	High Similarity	NPC475784
0.8987	High Similarity	NPC204290
0.8987	High Similarity	NPC192686
0.8987	High Similarity	NPC477164
0.8981	High Similarity	NPC223787
0.8981	High Similarity	NPC210084
0.8981	High Similarity	NPC474836
0.8981	High Similarity	NPC99597
0.8981	High Similarity	NPC262286
0.8981	High Similarity	NPC470402
0.8981	High Similarity	NPC474208
0.8981	High Similarity	NPC475267
0.8981	High Similarity	NPC156057
0.8981	High Similarity	NPC36852
0.8981	High Similarity	NPC291508
0.8981	High Similarity	NPC78225
0.8981	High Similarity	NPC181960
0.8981	High Similarity	NPC162869
0.8981	High Similarity	NPC48208
0.8974	High Similarity	NPC226025
0.8974	High Similarity	NPC256612
0.8974	High Similarity	NPC134287
0.8974	High Similarity	NPC472909
0.8974	High Similarity	NPC213622
0.8974	High Similarity	NPC20830
0.8974	High Similarity	NPC130589
0.8974	High Similarity	NPC39184
0.8968	High Similarity	NPC134677
0.8968	High Similarity	NPC52623
0.8961	High Similarity	NPC239363
0.8961	High Similarity	NPC156953
0.8961	High Similarity	NPC306821
0.8957	High Similarity	NPC475825
0.8957	High Similarity	NPC223375
0.8951	High Similarity	NPC165456
0.8951	High Similarity	NPC471287
0.8947	High Similarity	NPC310259
0.8944	High Similarity	NPC155264
0.8944	High Similarity	NPC67450
0.8944	High Similarity	NPC170245
0.8944	High Similarity	NPC119589
0.8944	High Similarity	NPC210460
0.8944	High Similarity	NPC193881
0.8938	High Similarity	NPC18100
0.8938	High Similarity	NPC329669
0.8938	High Similarity	NPC472278
0.8938	High Similarity	NPC472281
0.8938	High Similarity	NPC205265
0.8938	High Similarity	NPC473313
0.8931	High Similarity	NPC266314
0.8931	High Similarity	NPC474187
0.8931	High Similarity	NPC474186
0.8931	High Similarity	NPC134783
0.8931	High Similarity	NPC198829
0.8931	High Similarity	NPC264293
0.8931	High Similarity	NPC26326
0.8931	High Similarity	NPC474038
0.8924	High Similarity	NPC238405
0.8924	High Similarity	NPC204879
0.8924	High Similarity	NPC257914
0.8924	High Similarity	NPC104459
0.8917	High Similarity	NPC138243
0.8917	High Similarity	NPC68093
0.8917	High Similarity	NPC303255
0.8917	High Similarity	NPC282307
0.8917	High Similarity	NPC278778
0.8917	High Similarity	NPC235165
0.8917	High Similarity	NPC472916
0.8917	High Similarity	NPC276444
0.8917	High Similarity	NPC170026
0.8917	High Similarity	NPC191146
0.8917	High Similarity	NPC35038
0.8917	High Similarity	NPC195796
0.8917	High Similarity	NPC291878
0.8917	High Similarity	NPC255106
0.8917	High Similarity	NPC472455
0.8917	High Similarity	NPC471985
0.891	High Similarity	NPC274327
0.891	High Similarity	NPC176775

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 NPC19097 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	427
0.1-0.2	1009
0.2-0.3	1821
0.3-0.4	2688
0.4-0.5	1832
0.5-0.6	895
0.6-0.7	336
0.7-0.8	109
0.8-0.85	27
0.85-0.9	5
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9608	High Similarity	NPD5494	Approved
0.8931	High Similarity	NPD1247	Approved
0.891	High Similarity	NPD2801	Approved
0.879	High Similarity	NPD2393	Clinical (unspecified phase)
0.8726	High Similarity	NPD1934	Approved
0.8725	High Similarity	NPD2796	Approved
0.8679	High Similarity	NPD3882	Suspended
0.8659	High Similarity	NPD3818	Discontinued
0.8616	High Similarity	NPD3817	Phase 2
0.8571	High Similarity	NPD919	Approved
0.8481	Intermediate Similarity	NPD4380	Phase 2
0.8424	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD6166	Phase 2
0.8424	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD5402	Approved
0.8383	Intermediate Similarity	NPD5844	Phase 1
0.8364	Intermediate Similarity	NPD3926	Phase 2
0.8333	Intermediate Similarity	NPD1511	Approved
0.8323	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD920	Approved
0.8274	Intermediate Similarity	NPD7054	Approved
0.8261	Intermediate Similarity	NPD6801	Discontinued
0.8228	Intermediate Similarity	NPD1512	Approved
0.8225	Intermediate Similarity	NPD7472	Approved
0.8225	Intermediate Similarity	NPD7074	Phase 3
0.8221	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD7819	Suspended
0.8176	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD7075	Discontinued
0.8165	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD1549	Phase 2
0.8101	Intermediate Similarity	NPD6799	Approved
0.8086	Intermediate Similarity	NPD7411	Suspended
0.8084	Intermediate Similarity	NPD6232	Discontinued
0.8081	Intermediate Similarity	NPD7808	Phase 3
0.8077	Intermediate Similarity	NPD1243	Approved
0.807	Intermediate Similarity	NPD6797	Phase 2
0.8065	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD1510	Phase 2
0.8049	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD7473	Discontinued
0.8038	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD7251	Discontinued
0.7953	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD5403	Approved
0.7937	Intermediate Similarity	NPD5401	Approved
0.7919	Intermediate Similarity	NPD6559	Discontinued
0.7917	Intermediate Similarity	NPD6959	Discontinued
0.7914	Intermediate Similarity	NPD6599	Discontinued
0.7821	Intermediate Similarity	NPD3748	Approved
0.7792	Intermediate Similarity	NPD1240	Approved
0.7771	Intermediate Similarity	NPD2935	Discontinued
0.7759	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD2800	Approved
0.7716	Intermediate Similarity	NPD2534	Approved
0.7716	Intermediate Similarity	NPD2533	Approved
0.7716	Intermediate Similarity	NPD2532	Approved
0.7692	Intermediate Similarity	NPD1607	Approved
0.7679	Intermediate Similarity	NPD7768	Phase 2
0.7674	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD1465	Phase 2
0.7633	Intermediate Similarity	NPD3749	Approved
0.7628	Intermediate Similarity	NPD1933	Approved
0.7625	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD3750	Approved
0.7564	Intermediate Similarity	NPD943	Approved
0.7548	Intermediate Similarity	NPD2313	Discontinued
0.7533	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD447	Suspended
0.7514	Intermediate Similarity	NPD5242	Approved
0.75	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD37	Approved
0.7484	Intermediate Similarity	NPD2799	Discontinued
0.7472	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD4965	Approved
0.7471	Intermediate Similarity	NPD4967	Phase 2
0.7471	Intermediate Similarity	NPD4966	Approved
0.7453	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD3226	Approved
0.7419	Intermediate Similarity	NPD6832	Phase 2
0.7414	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD5353	Approved
0.7405	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6844	Discontinued
0.7391	Intermediate Similarity	NPD2344	Approved
0.7391	Intermediate Similarity	NPD2346	Discontinued
0.7386	Intermediate Similarity	NPD3751	Discontinued
0.7384	Intermediate Similarity	NPD6234	Discontinued
0.7371	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD2403	Approved
0.7362	Intermediate Similarity	NPD4628	Phase 3
0.736	Intermediate Similarity	NPD5953	Discontinued
0.7356	Intermediate Similarity	NPD3787	Discontinued
0.7345	Intermediate Similarity	NPD7286	Phase 2
0.7342	Intermediate Similarity	NPD1613	Approved
0.7342	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD6385	Approved
0.7337	Intermediate Similarity	NPD6386	Approved
0.7329	Intermediate Similarity	NPD1551	Phase 2
0.7308	Intermediate Similarity	NPD8434	Phase 2
0.7301	Intermediate Similarity	NPD2654	Approved
0.7296	Intermediate Similarity	NPD230	Phase 1
0.7288	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD1471	Phase 3
0.7267	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD1653	Approved
0.7261	Intermediate Similarity	NPD3027	Phase 3
0.7257	Intermediate Similarity	NPD7229	Phase 3
0.7256	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD2309	Approved
0.72	Intermediate Similarity	NPD5536	Phase 2
0.7197	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7228	Approved
0.7181	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2798	Approved
0.7166	Intermediate Similarity	NPD4363	Phase 3
0.7166	Intermediate Similarity	NPD4360	Phase 2
0.716	Intermediate Similarity	NPD7033	Discontinued
0.7159	Intermediate Similarity	NPD5710	Approved
0.7159	Intermediate Similarity	NPD5711	Approved
0.7158	Intermediate Similarity	NPD6780	Approved
0.7158	Intermediate Similarity	NPD6778	Approved
0.7158	Intermediate Similarity	NPD6781	Approved
0.7158	Intermediate Similarity	NPD6776	Approved
0.7158	Intermediate Similarity	NPD6782	Approved
0.7158	Intermediate Similarity	NPD6779	Approved
0.7158	Intermediate Similarity	NPD6777	Approved
0.7143	Intermediate Similarity	NPD8313	Approved
0.7143	Intermediate Similarity	NPD8312	Approved
0.7143	Intermediate Similarity	NPD6651	Approved
0.7135	Intermediate Similarity	NPD5890	Approved
0.7135	Intermediate Similarity	NPD5889	Approved
0.7134	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD7685	Pre-registration
0.7126	Intermediate Similarity	NPD7390	Discontinued
0.7108	Intermediate Similarity	NPD6190	Approved
0.7107	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD8127	Discontinued
0.7093	Intermediate Similarity	NPD6279	Approved
0.7093	Intermediate Similarity	NPD6280	Approved
0.7083	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5005	Approved
0.7083	Intermediate Similarity	NPD5006	Approved
0.7081	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5124	Phase 1
0.7073	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD6808	Phase 2
0.7055	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7697	Approved
0.7047	Intermediate Similarity	NPD7696	Phase 3
0.7047	Intermediate Similarity	NPD7698	Approved
0.7047	Intermediate Similarity	NPD7435	Discontinued
0.7037	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4361	Phase 2
0.7035	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD7240	Approved
0.7032	Intermediate Similarity	NPD3972	Approved
0.703	Intermediate Similarity	NPD2424	Discontinued
0.7027	Intermediate Similarity	NPD8150	Discontinued
0.7026	Intermediate Similarity	NPD7584	Approved
0.7025	Intermediate Similarity	NPD3018	Phase 2
0.7025	Intermediate Similarity	NPD9494	Approved
0.7019	Intermediate Similarity	NPD4307	Phase 2
0.7018	Intermediate Similarity	NPD7458	Discontinued
0.7018	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD8285	Discontinued
0.7012	Intermediate Similarity	NPD6099	Approved
0.7012	Intermediate Similarity	NPD6100	Approved
0.701	Intermediate Similarity	NPD7870	Phase 2
0.701	Intermediate Similarity	NPD7871	Phase 2
0.7006	Intermediate Similarity	NPD3266	Approved
0.7006	Intermediate Similarity	NPD3267	Approved
0.7006	Intermediate Similarity	NPD3887	Approved
0.7	Intermediate Similarity	NPD2163	Approved
0.6995	Remote Similarity	NPD7549	Discontinued
0.6989	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4908	Phase 1
0.6977	Remote Similarity	NPD6585	Discontinued
0.6963	Remote Similarity	NPD4420	Approved
0.6962	Remote Similarity	NPD1019	Discontinued
0.6957	Remote Similarity	NPD6233	Phase 2
0.6954	Remote Similarity	NPD5761	Phase 2
0.6954	Remote Similarity	NPD8151	Discontinued
0.6954	Remote Similarity	NPD5760	Phase 2
0.6948	Remote Similarity	NPD17	Approved
0.6946	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6273	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