NPASS Compound

Structure

NPC121333 OpenBabel07101718332D 31 35 0 0 1 0 0 0 0 0999 V2000 -5.6369 -1.1340 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 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.1910 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 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6369 -2.8660 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 -5.1369 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -2.0000 0.0000 C 0 0 2 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 2.5981 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 2 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 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6369 -2.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 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 -3.5491 -2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -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 27 1 0 0 0 0 3 28 1 0 0 0 0 4 5 2 0 0 0 0 4 12 1 0 0 0 0 5 15 1 0 0 0 0 6 13 1 0 0 0 0 6 16 1 0 0 0 0 7 14 2 0 0 0 0 7 18 1 0 0 0 0 8 17 2 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 9 24 1 0 0 0 0 10 20 1 0 0 0 0 10 29 1 0 0 0 0 12 21 2 0 0 0 0 12 22 1 0 0 0 0 13 15 2 0 0 0 0 13 21 1 0 0 0 0 14 17 1 0 0 0 0 14 23 1 0 0 0 0 15 30 1 0 0 0 0 16 11 1 1 0 0 0 16 30 1 0 0 0 0 17 29 1 0 0 0 0 18 19 2 0 0 0 0 18 27 1 0 0 0 0 19 28 1 0 0 0 0 20 23 1 6 0 0 0 20 31 1 0 0 0 0 21 31 1 0 0 0 0 22 23 1 0 0 0 0 22 25 2 0 0 0 0 23 26 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.13
Volume:	412.812
LogP:	2.408
LogD:	2.579
LogS:	-4.098
# Rotatable Bonds:	4
TPSA:	103.68
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.714
Synthetic Accessibility Score:	4.179
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:	-5.198
MDCK Permeability:	1.4740537153556943e-05
Pgp-inhibitor:	0.063
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.791
Plasma Protein Binding (PPB):	82.06990814208984%
Volume Distribution (VD):	1.147
Pgp-substrate:	12.81286334991455%

ADMET: Metabolism

CYP1A2-inhibitor:	0.077
CYP1A2-substrate:	0.562
CYP2C19-inhibitor:	0.331
CYP2C19-substrate:	0.789
CYP2C9-inhibitor:	0.282
CYP2C9-substrate:	0.411
CYP2D6-inhibitor:	0.046
CYP2D6-substrate:	0.748
CYP3A4-inhibitor:	0.576
CYP3A4-substrate:	0.774

ADMET: Excretion

Clearance (CL):	5.044
Half-life (T1/2):	0.547

ADMET: Toxicity

hERG Blockers:	0.055
Human Hepatotoxicity (H-HT):	0.671
Drug-inuced Liver Injury (DILI):	0.894
AMES Toxicity:	0.939
Rat Oral Acute Toxicity:	0.76
Maximum Recommended Daily Dose:	0.95
Skin Sensitization:	0.616
Carcinogencity:	0.804
Eye Corrosion:	0.003
Eye Irritation:	0.042
Respiratory Toxicity:	0.725

Download Data

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

Natural Product: NPC121333

Natural Product ID:	NPC121333
*Common Name:**	Dabinol
IUPAC Name:	n.a.
Synonyms:	12A-Hydroxyamorphigenin; 12Abeta-Hydroxyamorphigenin; Dabinol
Standard InCHIKey:	MYQAATJJIDGOMQ-AYPBNUJASA-N
Standard InCHI:	InChI=1S/C23H22O8/c1-11(9-24)16-6-13-15(30-16)5-4-12-21(13)31-20-10-29-17-8-19(28-3)18(27-2)7-14(17)23(20,26)22(12)25/h4-5,7-8,16,20,24,26H,1,6,9-10H2,2-3H3/t16-,20-,23-/m1/s1
SMILES:	C=C(CO)[C@H]1Cc2c(ccc3c2O[C@@H]2COc4cc(c(cc4[C@@]2(C3=O)O)OC)OC)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465761
PubChem CID:	44593485
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
NPO401	Berchemia discolor	Species	Rhamnaceae	Eukaryota	n.a.	Tanzanian	n.a.	PMID[17125241]
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]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO401	Berchemia discolor	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16886	Amorpha fruticosa	Species	Fabaceae	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
ED50	9
IC50	2
Others	8

Activity Type	# Activity
Cell Line	14
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT180	Cell Line	HCT-8	Homo sapiens	ED50	<	0.001	ug ml-1	PMID[489906]
NPT1091	Cell Line	RPMI-7951	Homo sapiens	ED50	<	0.001	ug ml-1	PMID[489906]
NPT91	Cell Line	KB	Homo sapiens	ED50	<	0.001	ug ml-1	PMID[489906]
NPT168	Cell Line	P388	Mus musculus	ED50	<	0.001	ug ml-1	PMID[489906]
NPT81	Cell Line	A549	Homo sapiens	ED50	<	0.001	ug ml-1	PMID[489906]
NPT672	Cell Line	TE-671	Homo sapiens	ED50	<	0.001	ug ml-1	PMID[489906]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	80.0	%	PMID[489907]
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	3.1	ug ml-1	PMID[489908]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	5.4	ug ml-1	PMID[489908]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	13.1	ug ml-1	PMID[489908]
NPT1864	Cell Line	L5178Y	Mus musculus	IC50	=	200.0	nM	PMID[489909]
NPT2	Others	Unspecified		Activity	=	100.0	%	PMID[489907]
NPT2	Others	Unspecified		Activity	=	89.7	%	PMID[489907]
NPT2	Others	Unspecified		Activity	=	24.2	%	PMID[489907]
NPT2	Others	Unspecified		IC50	=	3810.0	nM	PMID[489910]

☑ 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 NPC121333 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	435
0.1-0.2	1594
0.2-0.3	3626
0.3-0.4	8968
0.4-0.5	9254
0.5-0.6	3866
0.6-0.7	4922
0.7-0.8	5537
0.8-0.85	2711
0.85-0.9	1539
0.9-0.95	234
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9875	High Similarity	NPC242395
0.9875	High Similarity	NPC152477
0.9691	High Similarity	NPC74559
0.9627	High Similarity	NPC128293
0.9627	High Similarity	NPC173292
0.9576	High Similarity	NPC156635
0.9571	High Similarity	NPC103307
0.9568	High Similarity	NPC8965
0.9565	High Similarity	NPC234052
0.9509	High Similarity	NPC177480
0.9509	High Similarity	NPC326877
0.9448	High Similarity	NPC150131
0.9444	High Similarity	NPC62261
0.9444	High Similarity	NPC224280
0.9401	High Similarity	NPC67302
0.9387	High Similarity	NPC119589
0.9387	High Similarity	NPC471213
0.9383	High Similarity	NPC124038
0.9383	High Similarity	NPC273959
0.9383	High Similarity	NPC41301
0.9333	High Similarity	NPC279209
0.9333	High Similarity	NPC472276
0.9333	High Similarity	NPC102277
0.9329	High Similarity	NPC477154
0.9329	High Similarity	NPC6588
0.9329	High Similarity	NPC117854
0.9321	High Similarity	NPC474033
0.9321	High Similarity	NPC474034
0.9321	High Similarity	NPC472635
0.9321	High Similarity	NPC220912
0.9317	High Similarity	NPC298093
0.9317	High Similarity	NPC471976
0.9273	High Similarity	NPC288813
0.9268	High Similarity	NPC120593
0.9268	High Similarity	NPC170245
0.9264	High Similarity	NPC472625
0.9259	High Similarity	NPC228383
0.9259	High Similarity	NPC3629
0.9259	High Similarity	NPC472632
0.9259	High Similarity	NPC173137
0.9259	High Similarity	NPC471499
0.9259	High Similarity	NPC308992
0.9259	High Similarity	NPC134783
0.9255	High Similarity	NPC152904
0.9255	High Similarity	NPC473990
0.925	High Similarity	NPC303255
0.9235	High Similarity	NPC473883
0.9222	High Similarity	NPC310794
0.9212	High Similarity	NPC14662
0.9212	High Similarity	NPC158761
0.9207	High Similarity	NPC472277
0.9207	High Similarity	NPC326520
0.9207	High Similarity	NPC50960
0.9207	High Similarity	NPC300053
0.9207	High Similarity	NPC108433
0.9207	High Similarity	NPC470457
0.9202	High Similarity	NPC83922
0.9202	High Similarity	NPC81679
0.9202	High Similarity	NPC472448
0.9198	High Similarity	NPC263449
0.9198	High Similarity	NPC174953
0.9198	High Similarity	NPC282009
0.9198	High Similarity	NPC472624
0.9198	High Similarity	NPC475784
0.9198	High Similarity	NPC470326
0.9198	High Similarity	NPC287328
0.9167	High Similarity	NPC108202
0.9157	High Similarity	NPC165456
0.9152	High Similarity	NPC235610
0.9152	High Similarity	NPC477517
0.9152	High Similarity	NPC113093
0.9146	High Similarity	NPC18100
0.9146	High Similarity	NPC473313
0.9146	High Similarity	NPC470459
0.9146	High Similarity	NPC329669
0.9146	High Similarity	NPC472278
0.9146	High Similarity	NPC475985
0.9146	High Similarity	NPC236521
0.9146	High Similarity	NPC472281
0.9146	High Similarity	NPC152659
0.9146	High Similarity	NPC205265
0.9146	High Similarity	NPC248638
0.9141	High Similarity	NPC474038
0.9141	High Similarity	NPC167678
0.9141	High Similarity	NPC266314
0.9141	High Similarity	NPC289771
0.9141	High Similarity	NPC471212
0.9141	High Similarity	NPC472634
0.9141	High Similarity	NPC471210
0.9141	High Similarity	NPC165549
0.9141	High Similarity	NPC471211
0.9141	High Similarity	NPC26326
0.9141	High Similarity	NPC29876
0.9136	High Similarity	NPC95936
0.9136	High Similarity	NPC22192
0.9136	High Similarity	NPC55738
0.9136	High Similarity	NPC250214
0.9136	High Similarity	NPC187792
0.9102	High Similarity	NPC44558
0.9096	High Similarity	NPC470456
0.9096	High Similarity	NPC295082
0.9096	High Similarity	NPC247973
0.9096	High Similarity	NPC474024
0.9096	High Similarity	NPC260266
0.9096	High Similarity	NPC243877
0.9091	High Similarity	NPC293319
0.9091	High Similarity	NPC275780
0.9091	High Similarity	NPC72787
0.9091	High Similarity	NPC36
0.9091	High Similarity	NPC36916
0.9091	High Similarity	NPC7688
0.9091	High Similarity	NPC472450
0.9091	High Similarity	NPC125039
0.9091	High Similarity	NPC239752
0.9091	High Similarity	NPC58223
0.9091	High Similarity	NPC7154
0.9085	High Similarity	NPC476247
0.9085	High Similarity	NPC474150
0.9085	High Similarity	NPC474162
0.9085	High Similarity	NPC261470
0.9085	High Similarity	NPC25152
0.9085	High Similarity	NPC472402
0.9085	High Similarity	NPC229632
0.908	High Similarity	NPC118256
0.908	High Similarity	NPC119209
0.908	High Similarity	NPC472962
0.908	High Similarity	NPC472961
0.908	High Similarity	NPC472631
0.908	High Similarity	NPC204290
0.908	High Similarity	NPC476980
0.908	High Similarity	NPC470183
0.908	High Similarity	NPC328102
0.908	High Similarity	NPC192686
0.908	High Similarity	NPC472630
0.9074	High Similarity	NPC284820
0.9074	High Similarity	NPC19097
0.9074	High Similarity	NPC473272
0.9074	High Similarity	NPC162869
0.9074	High Similarity	NPC27337
0.9074	High Similarity	NPC210084
0.9074	High Similarity	NPC474055
0.9074	High Similarity	NPC474208
0.9074	High Similarity	NPC262286
0.9074	High Similarity	NPC476981
0.9074	High Similarity	NPC223787
0.9074	High Similarity	NPC78225
0.9074	High Similarity	NPC78071
0.9074	High Similarity	NPC36852
0.9074	High Similarity	NPC474836
0.9074	High Similarity	NPC67876
0.9074	High Similarity	NPC471209
0.9074	High Similarity	NPC48208
0.9074	High Similarity	NPC475267
0.9074	High Similarity	NPC99597
0.9074	High Similarity	NPC52530
0.9074	High Similarity	NPC156057
0.9074	High Similarity	NPC181960
0.9074	High Similarity	NPC291508
0.9074	High Similarity	NPC472598
0.9068	High Similarity	NPC37392
0.9059	High Similarity	NPC168584
0.9053	High Similarity	NPC472607
0.9048	High Similarity	NPC212038
0.9048	High Similarity	NPC81332
0.9048	High Similarity	NPC262580
0.9048	High Similarity	NPC475825
0.9048	High Similarity	NPC223375
0.9048	High Similarity	NPC257667
0.9048	High Similarity	NPC289396
0.9048	High Similarity	NPC271848
0.9048	High Similarity	NPC186847
0.9048	High Similarity	NPC472454
0.9042	High Similarity	NPC472383
0.9042	High Similarity	NPC472381
0.9036	High Similarity	NPC277480
0.9036	High Similarity	NPC39091
0.9036	High Similarity	NPC470462
0.9036	High Similarity	NPC472449
0.903	High Similarity	NPC474240
0.903	High Similarity	NPC7483
0.903	High Similarity	NPC306321
0.903	High Similarity	NPC189473
0.903	High Similarity	NPC303460
0.903	High Similarity	NPC186686
0.903	High Similarity	NPC472582
0.903	High Similarity	NPC23298
0.9024	High Similarity	NPC474239
0.9024	High Similarity	NPC474186
0.9024	High Similarity	NPC61010
0.9024	High Similarity	NPC198829
0.9024	High Similarity	NPC474187
0.9024	High Similarity	NPC142252
0.9024	High Similarity	NPC259456
0.9018	High Similarity	NPC53545
0.9018	High Similarity	NPC117418
0.9018	High Similarity	NPC204879
0.9018	High Similarity	NPC195832
0.9012	High Similarity	NPC291878
0.9012	High Similarity	NPC250922
0.9012	High Similarity	NPC35038

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 NPC121333 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	370
0.1-0.2	923
0.2-0.3	1798
0.3-0.4	2619
0.4-0.5	1833
0.5-0.6	969
0.6-0.7	440
0.7-0.8	145
0.8-0.85	37
0.85-0.9	12
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9317	High Similarity	NPD5494	Approved
0.9091	High Similarity	NPD6167	Clinical (unspecified phase)
0.9091	High Similarity	NPD6168	Clinical (unspecified phase)
0.9091	High Similarity	NPD6166	Phase 2
0.8896	High Similarity	NPD3882	Suspended
0.8889	High Similarity	NPD2393	Clinical (unspecified phase)
0.8827	High Similarity	NPD1934	Approved
0.8773	High Similarity	NPD2801	Approved
0.8757	High Similarity	NPD3818	Discontinued
0.8721	High Similarity	NPD4338	Clinical (unspecified phase)
0.8704	High Similarity	NPD4380	Phase 2
0.8655	High Similarity	NPD7074	Phase 3
0.8614	High Similarity	NPD7075	Discontinued
0.8613	High Similarity	NPD7808	Phase 3
0.8606	High Similarity	NPD3817	Phase 2
0.8605	High Similarity	NPD6797	Phase 2
0.8596	High Similarity	NPD7054	Approved
0.8596	High Similarity	NPD5844	Phase 1
0.8555	High Similarity	NPD7251	Discontinued
0.8547	High Similarity	NPD7472	Approved
0.8545	High Similarity	NPD7096	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD5402	Approved
0.8488	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8485	Intermediate Similarity	NPD6801	Discontinued
0.8462	Intermediate Similarity	NPD1247	Approved
0.8443	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8393	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8391	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1512	Approved
0.8323	Intermediate Similarity	NPD7819	Suspended
0.8274	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD3926	Phase 2
0.8246	Intermediate Similarity	NPD6959	Discontinued
0.8239	Intermediate Similarity	NPD6559	Discontinued
0.8221	Intermediate Similarity	NPD1511	Approved
0.8204	Intermediate Similarity	NPD7411	Suspended
0.8198	Intermediate Similarity	NPD6232	Discontinued
0.8171	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD7473	Discontinued
0.8137	Intermediate Similarity	NPD1549	Phase 2
0.8132	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD919	Approved
0.811	Intermediate Similarity	NPD6799	Approved
0.8107	Intermediate Similarity	NPD1465	Phase 2
0.8075	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD5403	Approved
0.8056	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD6599	Discontinued
0.8012	Intermediate Similarity	NPD2796	Approved
0.8011	Intermediate Similarity	NPD3751	Discontinued
0.7952	Intermediate Similarity	NPD5401	Approved
0.7912	Intermediate Similarity	NPD8434	Phase 2
0.7898	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD3787	Discontinued
0.7861	Intermediate Similarity	NPD3749	Approved
0.784	Intermediate Similarity	NPD1510	Phase 2
0.7831	Intermediate Similarity	NPD6781	Approved
0.7831	Intermediate Similarity	NPD6778	Approved
0.7831	Intermediate Similarity	NPD6782	Approved
0.7831	Intermediate Similarity	NPD6776	Approved
0.7831	Intermediate Similarity	NPD6777	Approved
0.7831	Intermediate Similarity	NPD6780	Approved
0.7831	Intermediate Similarity	NPD6779	Approved
0.7826	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD2800	Approved
0.7751	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD2533	Approved
0.7738	Intermediate Similarity	NPD2532	Approved
0.7738	Intermediate Similarity	NPD2534	Approved
0.7733	Intermediate Similarity	NPD37	Approved
0.7727	Intermediate Similarity	NPD7199	Phase 2
0.7717	Intermediate Similarity	NPD8150	Discontinued
0.7709	Intermediate Similarity	NPD7228	Approved
0.7708	Intermediate Similarity	NPD7435	Discontinued
0.7708	Intermediate Similarity	NPD7696	Phase 3
0.7708	Intermediate Similarity	NPD7697	Approved
0.7708	Intermediate Similarity	NPD7698	Approved
0.7702	Intermediate Similarity	NPD1240	Approved
0.7701	Intermediate Similarity	NPD4966	Approved
0.7701	Intermediate Similarity	NPD4967	Phase 2
0.7701	Intermediate Similarity	NPD4965	Approved
0.7701	Intermediate Similarity	NPD7768	Phase 2
0.7683	Intermediate Similarity	NPD2935	Discontinued
0.7665	Intermediate Similarity	NPD6190	Approved
0.765	Intermediate Similarity	NPD8313	Approved
0.765	Intermediate Similarity	NPD8312	Approved
0.7647	Intermediate Similarity	NPD920	Approved
0.7644	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7641	Intermediate Similarity	NPD7701	Phase 2
0.7614	Intermediate Similarity	NPD6234	Discontinued
0.7607	Intermediate Similarity	NPD1607	Approved
0.7605	Intermediate Similarity	NPD4628	Phase 3
0.7593	Intermediate Similarity	NPD943	Approved
0.7593	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD1613	Approved
0.7577	Intermediate Similarity	NPD7871	Phase 2
0.7577	Intermediate Similarity	NPD7870	Phase 2
0.7566	Intermediate Similarity	NPD6535	Approved
0.7566	Intermediate Similarity	NPD6534	Approved
0.7558	Intermediate Similarity	NPD3226	Approved
0.7545	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD7685	Pre-registration
0.7539	Intermediate Similarity	NPD7699	Phase 2
0.7539	Intermediate Similarity	NPD7700	Phase 2
0.7529	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3750	Approved
0.75	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1653	Approved
0.7487	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD7874	Approved
0.7446	Intermediate Similarity	NPD7240	Approved
0.744	Intermediate Similarity	NPD1243	Approved
0.7439	Intermediate Similarity	NPD447	Suspended
0.7437	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7437	Intermediate Similarity	NPD7801	Approved
0.7437	Intermediate Similarity	NPD7783	Phase 2
0.7425	Intermediate Similarity	NPD2344	Approved
0.7425	Intermediate Similarity	NPD2346	Discontinued
0.7424	Intermediate Similarity	NPD8151	Discontinued
0.7412	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD2799	Discontinued
0.7407	Intermediate Similarity	NPD3027	Phase 3
0.7391	Intermediate Similarity	NPD5953	Discontinued
0.7385	Intermediate Similarity	NPD6823	Phase 2
0.7381	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD230	Phase 1
0.733	Intermediate Similarity	NPD6844	Discontinued
0.7326	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7584	Approved
0.7308	Intermediate Similarity	NPD2403	Approved
0.7305	Intermediate Similarity	NPD3748	Approved
0.7305	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD5710	Approved
0.7293	Intermediate Similarity	NPD5711	Approved
0.7292	Intermediate Similarity	NPD4360	Phase 2
0.7292	Intermediate Similarity	NPD4363	Phase 3
0.7288	Intermediate Similarity	NPD8455	Phase 2
0.7284	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7286	Phase 2
0.7282	Intermediate Similarity	NPD7907	Approved
0.7278	Intermediate Similarity	NPD2424	Discontinued
0.7268	Intermediate Similarity	NPD4111	Phase 1
0.7268	Intermediate Similarity	NPD4665	Approved
0.7267	Intermediate Similarity	NPD7390	Discontinued
0.7262	Intermediate Similarity	NPD1551	Phase 2
0.7262	Intermediate Similarity	NPD6100	Approved
0.7262	Intermediate Similarity	NPD6099	Approved
0.7257	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD2313	Discontinued
0.7256	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD2309	Approved
0.7238	Intermediate Similarity	NPD8127	Discontinued
0.7229	Intermediate Similarity	NPD1933	Approved
0.7222	Intermediate Similarity	NPD8319	Approved
0.7222	Intermediate Similarity	NPD8320	Phase 1
0.7202	Intermediate Similarity	NPD7033	Discontinued
0.7198	Intermediate Similarity	NPD7229	Phase 3
0.7193	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD5760	Phase 2
0.7191	Intermediate Similarity	NPD5761	Phase 2
0.7186	Intermediate Similarity	NPD6651	Approved
0.7158	Intermediate Similarity	NPD5242	Approved
0.7157	Intermediate Similarity	NPD2493	Approved
0.7157	Intermediate Similarity	NPD2494	Approved
0.7135	Intermediate Similarity	NPD2163	Approved
0.7134	Intermediate Similarity	NPD4908	Phase 1
0.7128	Intermediate Similarity	NPD2973	Approved
0.7128	Intermediate Similarity	NPD2975	Approved
0.7128	Intermediate Similarity	NPD7549	Discontinued
0.7128	Intermediate Similarity	NPD2974	Approved
0.7126	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5124	Phase 1
0.7126	Intermediate Similarity	NPD6355	Discontinued
0.7125	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD1471	Phase 3
0.7115	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6233	Phase 2
0.7079	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD4361	Phase 2
0.7073	Intermediate Similarity	NPD2861	Phase 2
0.7073	Intermediate Similarity	NPD9494	Approved
0.7071	Intermediate Similarity	NPD3450	Approved
0.7071	Intermediate Similarity	NPD3452	Approved
0.7062	Intermediate Similarity	NPD6213	Phase 3
0.7062	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7458	Discontinued
0.7062	Intermediate Similarity	NPD6212	Phase 3
0.7056	Intermediate Similarity	NPD5353	Approved
0.705	Intermediate Similarity	NPD4582	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