NPASS Compound

Structure

CID292415 OpenBabel06191716102D 30 32 0 0 1 0 0 0 0 0999 V2000 4.8296 -3.7083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2779 -2.0353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3052 -0.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4836 -4.6049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3461 -1.5176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2247 -3.6390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2588 -3.3801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6049 -2.4836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5731 -0.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4392 -1.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5708 -2.7424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4392 -0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4495 -4.8637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7071 -0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9319 -2.9319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5731 -2.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.4142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8978 -3.1907 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7071 -1.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7071 -1.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6730 -1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 -0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7083 -5.8296 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5731 -3.2071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6310 -0.3244 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3801 -1.2588 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 3.1566 -4.1566 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -2.4142 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 27 1 0 0 0 0 6 7 2 0 0 0 0 6 16 1 0 0 0 0 7 18 1 0 0 0 0 8 12 1 0 0 0 0 9 13 2 0 0 0 0 9 15 1 0 0 0 0 10 13 1 0 0 0 0 10 17 2 0 0 0 0 11 15 1 0 0 0 0 11 28 1 0 0 0 0 14 24 2 0 0 0 0 14 29 1 0 0 0 0 15 21 2 0 0 0 0 16 19 1 0 0 0 0 16 22 2 0 0 0 0 17 21 1 0 0 0 0 17 25 1 0 0 0 0 18 20 2 0 0 0 0 18 30 1 0 0 0 0 19 8 1 6 0 0 0 19 29 1 0 0 0 0 20 22 1 0 0 0 0 20 23 1 0 0 0 0 21 30 1 0 0 0 0 22 27 1 0 0 0 0 23 26 2 0 0 0 0 23 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	414.17
Volume:	421.135
LogP:	4.445
LogD:	3.563
LogS:	-4.443
# Rotatable Bonds:	6
TPSA:	91.29
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.701
Synthetic Accessibility Score:	3.408
Fsp3:	0.391
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:	-4.869
MDCK Permeability:	2.1342490072129294e-05
Pgp-inhibitor:	0.412
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.159
Plasma Protein Binding (PPB):	97.86035919189453%
Volume Distribution (VD):	0.693
Pgp-substrate:	6.473630905151367%

ADMET: Metabolism

CYP1A2-inhibitor:	0.559
CYP1A2-substrate:	0.553
CYP2C19-inhibitor:	0.934
CYP2C19-substrate:	0.46
CYP2C9-inhibitor:	0.871
CYP2C9-substrate:	0.915
CYP2D6-inhibitor:	0.413
CYP2D6-substrate:	0.486
CYP3A4-inhibitor:	0.482
CYP3A4-substrate:	0.569

ADMET: Excretion

Clearance (CL):	7.642
Half-life (T1/2):	0.429

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.07
Drug-inuced Liver Injury (DILI):	0.659
AMES Toxicity:	0.517
Rat Oral Acute Toxicity:	0.836
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.345
Carcinogencity:	0.873
Eye Corrosion:	0.003
Eye Irritation:	0.763
Respiratory Toxicity:	0.666

Download Data

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

Natural Product: NPC292415

Natural Product ID:	NPC292415
*Common Name:**	Purpactin A
IUPAC Name:	[(1S)-1-(6-hydroxy-1-methoxy-8-methyl-12-oxo-10H-benzo[b][1,5]benzodioxocin-2-yl)-3-methylbutyl] acetate
Synonyms:
Standard InCHIKey:	NUYFKDBCHFKOBT-IBGZPJMESA-N
Standard InCHI:	InChI=1S/C23H26O7/c1-12(2)8-19(29-14(4)24)16-6-7-18-20(22(16)27-5)23(26)28-11-15-9-13(3)10-17(25)21(15)30-18/h6-7,9-10,12,19,25H,8,11H2,1-5H3/t19-/m0/s1
SMILES:	COc1c(ccc2c1C(=O)OCc1c(O2)c(O)cc(c1)C)[C@@H](OC(=O)C)CC(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL116226
PubChem CID:	10341722
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000254] Ethers [CHEMONTID:0002463] Diarylethers

*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
NPO29948	Penicillium purpurogenum	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2010354]
NPO29948	Penicillium purpurogenum	Species	Trichocomaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21879714]
NPO33444	penicillium pinophilum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22264170]
NPO33444	penicillium pinophilum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26291474]
NPO40759	Okeania sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26539973]
NPO40759	Okeania sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27359053]
NPO40759	Okeania sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[28294609]
NPO40759	Okeania sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[28541699]
NPO40759	Okeania sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29019684]
NPO40759	Okeania sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29667822]
NPO40759	Okeania sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[32040324]
NPO40759	Okeania sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[32173199]
NPO40759	Okeania sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[32267694]
NPO29948	Penicillium purpurogenum	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32293887]

☑ 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
EC50	1
IC50	6
Others	1

Activity Type	# Activity
Individual Protein	2
Organism	2
SINGLE PROTEIN	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4191	Individual Protein	Oxytocin receptor	Rattus norvegicus	IC50	=	8400.0	nM	PMID[466013]
NPT4192	Individual Protein	Vasopressin V2 receptor	Sus scrofa	IC50	>	100000.0	nM	PMID[466013]
NPT2540	Organism	Balanus amphitrite	Balanus amphitrite	EC50	=	10.0	ug.mL-1	PMID[466014]
NPT2540	Organism	Balanus amphitrite	Balanus amphitrite	Ratio CC50/EC50	>	50.0	n.a.	PMID[466014]
NPT24667	SINGLE PROTEIN	Sterol O-acyltransferase 1	Chlorocebus aethiops	IC50	=	2500.0	nM	PMID[466015]
NPT24668	SINGLE PROTEIN	Sterol O-acyltransferase 2	Chlorocebus aethiops	IC50	=	1500.0	nM	PMID[466015]
NPT24667	SINGLE PROTEIN	Sterol O-acyltransferase 1	Chlorocebus aethiops	IC50	=	900.0	nM	PMID[466015]
NPT24668	SINGLE PROTEIN	Sterol O-acyltransferase 2	Chlorocebus aethiops	IC50	=	1800.0	nM	PMID[466015]

☑ 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 NPC292415 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	368
0.1-0.2	1486
0.2-0.3	3857
0.3-0.4	8703
0.4-0.5	9541
0.5-0.6	3418
0.6-0.7	4693
0.7-0.8	5859
0.8-0.85	3273
0.85-0.9	1261
0.9-0.95	218
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC473106
0.9934	High Similarity	NPC103201
0.9804	High Similarity	NPC349525
0.9669	High Similarity	NPC298802
0.9605	High Similarity	NPC286052
0.9603	High Similarity	NPC199773
0.9416	High Similarity	NPC195796
0.9416	High Similarity	NPC291878
0.9416	High Similarity	NPC35038
0.9416	High Similarity	NPC278778
0.9355	High Similarity	NPC27337
0.9355	High Similarity	NPC108456
0.9355	High Similarity	NPC474055
0.9355	High Similarity	NPC291508
0.9355	High Similarity	NPC472598
0.9351	High Similarity	NPC477503
0.9351	High Similarity	NPC45849
0.9351	High Similarity	NPC470327
0.9351	High Similarity	NPC200761
0.9295	High Similarity	NPC83763
0.9295	High Similarity	NPC168616
0.929	High Similarity	NPC470328
0.929	High Similarity	NPC209614
0.929	High Similarity	NPC472626
0.9286	High Similarity	NPC18727
0.9286	High Similarity	NPC213896
0.9286	High Similarity	NPC192083
0.9236	High Similarity	NPC119209
0.9236	High Similarity	NPC282009
0.9236	High Similarity	NPC472624
0.9236	High Similarity	NPC118256
0.9236	High Similarity	NPC36217
0.9236	High Similarity	NPC192686
0.9236	High Similarity	NPC287328
0.9231	High Similarity	NPC223787
0.9226	High Similarity	NPC226025
0.9226	High Similarity	NPC321779
0.9221	High Similarity	NPC302950
0.9221	High Similarity	NPC106976
0.9221	High Similarity	NPC472912
0.9221	High Similarity	NPC219582
0.9221	High Similarity	NPC236637
0.9221	High Similarity	NPC289968
0.9221	High Similarity	NPC471982
0.9187	High Similarity	NPC207575
0.9187	High Similarity	NPC472452
0.9187	High Similarity	NPC13481
0.9182	High Similarity	NPC234004
0.9177	High Similarity	NPC471210
0.9177	High Similarity	NPC26326
0.9177	High Similarity	NPC471499
0.9177	High Similarity	NPC112418
0.9177	High Similarity	NPC266314
0.9177	High Similarity	NPC474038
0.9177	High Similarity	NPC472632
0.9177	High Similarity	NPC472634
0.9172	High Similarity	NPC95936
0.9172	High Similarity	NPC22192
0.9172	High Similarity	NPC250214
0.9167	High Similarity	NPC227062
0.9167	High Similarity	NPC472456
0.9161	High Similarity	NPC74924
0.9161	High Similarity	NPC298692
0.9161	High Similarity	NPC475895
0.9119	High Similarity	NPC474034
0.9119	High Similarity	NPC8300
0.9119	High Similarity	NPC472635
0.9119	High Similarity	NPC474162
0.9119	High Similarity	NPC474150
0.9119	High Similarity	NPC474033
0.9119	High Similarity	NPC471745
0.9119	High Similarity	NPC476247
0.9119	High Similarity	NPC201800
0.9114	High Similarity	NPC472630
0.9114	High Similarity	NPC470326
0.9114	High Similarity	NPC174953
0.9114	High Similarity	NPC475784
0.9114	High Similarity	NPC472631
0.9114	High Similarity	NPC328102
0.9114	High Similarity	NPC471744
0.9108	High Similarity	NPC472910
0.9108	High Similarity	NPC471515
0.9108	High Similarity	NPC471479
0.9108	High Similarity	NPC78225
0.9108	High Similarity	NPC299520
0.9108	High Similarity	NPC284820
0.9108	High Similarity	NPC473272
0.9108	High Similarity	NPC474208
0.9108	High Similarity	NPC471209
0.9108	High Similarity	NPC222689
0.9108	High Similarity	NPC474836
0.9108	High Similarity	NPC472914
0.9108	High Similarity	NPC96167
0.9108	High Similarity	NPC472913
0.9108	High Similarity	NPC129684
0.9108	High Similarity	NPC35598
0.9108	High Similarity	NPC156057
0.9108	High Similarity	NPC245758
0.9108	High Similarity	NPC48208
0.9108	High Similarity	NPC162869
0.9108	High Similarity	NPC472911
0.9108	High Similarity	NPC475267
0.9108	High Similarity	NPC222814
0.9103	High Similarity	NPC234255
0.9103	High Similarity	NPC168247
0.9103	High Similarity	NPC117992
0.9103	High Similarity	NPC230149
0.9103	High Similarity	NPC152951
0.9103	High Similarity	NPC57674
0.9097	High Similarity	NPC260979
0.9091	High Similarity	NPC88804
0.9091	High Similarity	NPC338131
0.9091	High Similarity	NPC3825
0.9091	High Similarity	NPC472279
0.9062	High Similarity	NPC472625
0.9062	High Similarity	NPC186686
0.9062	High Similarity	NPC124038
0.9057	High Similarity	NPC134783
0.9057	High Similarity	NPC471212
0.9057	High Similarity	NPC471211
0.9057	High Similarity	NPC142252
0.9051	High Similarity	NPC53545
0.9051	High Similarity	NPC74178
0.9051	High Similarity	NPC473990
0.9051	High Similarity	NPC117418
0.9051	High Similarity	NPC210459
0.9051	High Similarity	NPC184755
0.9045	High Similarity	NPC471985
0.9045	High Similarity	NPC68093
0.9045	High Similarity	NPC13858
0.9045	High Similarity	NPC320825
0.9045	High Similarity	NPC317383
0.9045	High Similarity	NPC235165
0.9045	High Similarity	NPC54928
0.9045	High Similarity	NPC326037
0.9045	High Similarity	NPC472455
0.9045	High Similarity	NPC191146
0.9045	High Similarity	NPC255106
0.9045	High Similarity	NPC471500
0.9038	High Similarity	NPC70433
0.9038	High Similarity	NPC33051
0.9038	High Similarity	NPC469550
0.9038	High Similarity	NPC227337
0.9038	High Similarity	NPC273462
0.9038	High Similarity	NPC49402
0.9032	High Similarity	NPC256406
0.9032	High Similarity	NPC75695
0.9026	High Similarity	NPC52005
0.9026	High Similarity	NPC137062
0.9026	High Similarity	NPC48479
0.9026	High Similarity	NPC177298
0.9026	High Similarity	NPC287101
0.9026	High Similarity	NPC223579
0.9026	High Similarity	NPC183950
0.9006	High Similarity	NPC472277
0.9006	High Similarity	NPC130920
0.9006	High Similarity	NPC471788
0.9006	High Similarity	NPC85057
0.9006	High Similarity	NPC62261
0.9006	High Similarity	NPC293319
0.9006	High Similarity	NPC300053
0.9006	High Similarity	NPC108433
0.9	High Similarity	NPC81679
0.8994	High Similarity	NPC476980
0.8994	High Similarity	NPC476283
0.8994	High Similarity	NPC53889
0.8994	High Similarity	NPC321399
0.8994	High Similarity	NPC299436
0.8987	High Similarity	NPC262286
0.8987	High Similarity	NPC470402
0.8987	High Similarity	NPC52889
0.8987	High Similarity	NPC36852
0.8987	High Similarity	NPC469584
0.8987	High Similarity	NPC52530
0.8987	High Similarity	NPC67876
0.8987	High Similarity	NPC210084
0.8987	High Similarity	NPC99597
0.8981	High Similarity	NPC472280
0.8981	High Similarity	NPC37392
0.8981	High Similarity	NPC16082
0.8981	High Similarity	NPC256925
0.8981	High Similarity	NPC82592
0.8981	High Similarity	NPC31018
0.8981	High Similarity	NPC133392
0.8981	High Similarity	NPC67396
0.8981	High Similarity	NPC213622
0.8981	High Similarity	NPC255807
0.8981	High Similarity	NPC472909
0.8974	High Similarity	NPC39732
0.8974	High Similarity	NPC237994
0.8974	High Similarity	NPC63187
0.8974	High Similarity	NPC477231
0.8974	High Similarity	NPC295646
0.8974	High Similarity	NPC323626
0.8974	High Similarity	NPC60972
0.8974	High Similarity	NPC157784
0.8974	High Similarity	NPC257648
0.8974	High Similarity	NPC37684
0.8974	High Similarity	NPC324233
0.8961	High Similarity	NPC294852

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 NPC292415 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	325
0.1-0.2	898
0.2-0.3	1846
0.3-0.4	2551
0.4-0.5	1768
0.5-0.6	1036
0.6-0.7	518
0.7-0.8	151
0.8-0.85	40
0.85-0.9	15
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9286	High Similarity	NPD2393	Clinical (unspecified phase)
0.9221	High Similarity	NPD1934	Approved
0.8917	High Similarity	NPD2801	Approved
0.8861	High Similarity	NPD3817	Phase 2
0.8805	High Similarity	NPD4868	Clinical (unspecified phase)
0.8805	High Similarity	NPD3882	Suspended
0.8773	High Similarity	NPD6168	Clinical (unspecified phase)
0.8773	High Similarity	NPD6166	Phase 2
0.8773	High Similarity	NPD6167	Clinical (unspecified phase)
0.875	High Similarity	NPD7075	Discontinued
0.8701	High Similarity	NPD1511	Approved
0.8679	High Similarity	NPD7096	Clinical (unspecified phase)
0.8675	High Similarity	NPD7074	Phase 3
0.8667	High Similarity	NPD3818	Discontinued
0.865	High Similarity	NPD6232	Discontinued
0.8614	High Similarity	NPD7054	Approved
0.8606	High Similarity	NPD7473	Discontinued
0.859	High Similarity	NPD1512	Approved
0.8563	High Similarity	NPD7472	Approved
0.8528	High Similarity	NPD5494	Approved
0.8526	High Similarity	NPD4378	Clinical (unspecified phase)
0.8521	High Similarity	NPD4338	Clinical (unspecified phase)
0.8503	High Similarity	NPD5844	Phase 1
0.85	High Similarity	NPD6801	Discontinued
0.8491	Intermediate Similarity	NPD4380	Phase 2
0.8462	Intermediate Similarity	NPD6799	Approved
0.8447	Intermediate Similarity	NPD7819	Suspended
0.8402	Intermediate Similarity	NPD6797	Phase 2
0.8353	Intermediate Similarity	NPD7251	Discontinued
0.8323	Intermediate Similarity	NPD7411	Suspended
0.8312	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD7808	Phase 3
0.8293	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD6599	Discontinued
0.8258	Intermediate Similarity	NPD1549	Phase 2
0.8258	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD2935	Discontinued
0.8242	Intermediate Similarity	NPD919	Approved
0.8221	Intermediate Similarity	NPD1465	Phase 2
0.8187	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD2534	Approved
0.8176	Intermediate Similarity	NPD2533	Approved
0.8176	Intermediate Similarity	NPD2532	Approved
0.8176	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD6559	Discontinued
0.8129	Intermediate Similarity	NPD2796	Approved
0.8121	Intermediate Similarity	NPD7768	Phase 2
0.8105	Intermediate Similarity	NPD230	Phase 1
0.8065	Intermediate Similarity	NPD1510	Phase 2
0.8063	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD5402	Approved
0.8039	Intermediate Similarity	NPD1240	Approved
0.8038	Intermediate Similarity	NPD4628	Phase 3
0.8036	Intermediate Similarity	NPD6959	Discontinued
0.8026	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD6234	Discontinued
0.8013	Intermediate Similarity	NPD1551	Phase 2
0.8	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD447	Suspended
0.7975	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD5403	Approved
0.7961	Intermediate Similarity	NPD3027	Phase 3
0.7935	Intermediate Similarity	NPD1607	Approved
0.7929	Intermediate Similarity	NPD1247	Approved
0.7929	Intermediate Similarity	NPD7199	Phase 2
0.7922	Intermediate Similarity	NPD943	Approved
0.7922	Intermediate Similarity	NPD1613	Approved
0.7922	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD920	Approved
0.7853	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD5401	Approved
0.7836	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD2799	Discontinued
0.7831	Intermediate Similarity	NPD37	Approved
0.7821	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD3750	Approved
0.7798	Intermediate Similarity	NPD4966	Approved
0.7798	Intermediate Similarity	NPD4965	Approved
0.7798	Intermediate Similarity	NPD4967	Phase 2
0.7778	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD5953	Discontinued
0.7759	Intermediate Similarity	NPD7286	Phase 2
0.775	Intermediate Similarity	NPD2800	Approved
0.775	Intermediate Similarity	NPD1243	Approved
0.7733	Intermediate Similarity	NPD3926	Phase 2
0.773	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD7228	Approved
0.7697	Intermediate Similarity	NPD1653	Approved
0.7654	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD6190	Approved
0.7651	Intermediate Similarity	NPD3226	Approved
0.7647	Intermediate Similarity	NPD3749	Approved
0.7643	Intermediate Similarity	NPD1933	Approved
0.7595	Intermediate Similarity	NPD6651	Approved
0.7593	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD1203	Approved
0.758	Intermediate Similarity	NPD4060	Phase 1
0.7572	Intermediate Similarity	NPD5710	Approved
0.7572	Intermediate Similarity	NPD5711	Approved
0.7564	Intermediate Similarity	NPD2313	Discontinued
0.756	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6832	Phase 2
0.7542	Intermediate Similarity	NPD8312	Approved
0.7542	Intermediate Similarity	NPD8313	Approved
0.7541	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6355	Discontinued
0.7532	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD5353	Approved
0.7529	Intermediate Similarity	NPD5242	Approved
0.7528	Intermediate Similarity	NPD7685	Pre-registration
0.7516	Intermediate Similarity	NPD2346	Discontinued
0.7515	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8434	Phase 2
0.75	Intermediate Similarity	NPD3748	Approved
0.75	Intermediate Similarity	NPD1608	Approved
0.75	Intermediate Similarity	NPD7033	Discontinued
0.7486	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD9494	Approved
0.7473	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7229	Phase 3
0.7452	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6798	Discontinued
0.7447	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD5124	Phase 1
0.7421	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD9269	Phase 2
0.7386	Intermediate Similarity	NPD9717	Approved
0.7378	Intermediate Similarity	NPD4110	Phase 3
0.7378	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2797	Approved
0.7353	Intermediate Similarity	NPD6385	Approved
0.7353	Intermediate Similarity	NPD6386	Approved
0.7346	Intermediate Similarity	NPD6099	Approved
0.7346	Intermediate Similarity	NPD6100	Approved
0.7342	Intermediate Similarity	NPD3268	Approved
0.7338	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7458	Discontinued
0.7325	Intermediate Similarity	NPD4908	Phase 1
0.7322	Intermediate Similarity	NPD8150	Discontinued
0.732	Intermediate Similarity	NPD422	Phase 1
0.7314	Intermediate Similarity	NPD8127	Discontinued
0.7305	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD3751	Discontinued
0.7303	Intermediate Similarity	NPD17	Approved
0.7301	Intermediate Similarity	NPD2344	Approved
0.7296	Intermediate Similarity	NPD6233	Phase 2
0.7284	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3787	Discontinued
0.7273	Intermediate Similarity	NPD4363	Phase 3
0.7273	Intermediate Similarity	NPD4360	Phase 2
0.7267	Intermediate Similarity	NPD8455	Phase 2
0.7246	Intermediate Similarity	NPD7390	Discontinued
0.7238	Intermediate Similarity	NPD7240	Approved
0.7233	Intermediate Similarity	NPD411	Approved
0.7231	Intermediate Similarity	NPD8151	Discontinued
0.7212	Intermediate Similarity	NPD1652	Phase 2
0.7208	Intermediate Similarity	NPD1610	Phase 2
0.7195	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7266	Discontinued
0.7195	Intermediate Similarity	NPD6002	Phase 3
0.7195	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6005	Phase 3
0.7195	Intermediate Similarity	NPD6004	Phase 3
0.7178	Intermediate Similarity	NPD4308	Phase 3
0.7171	Intermediate Similarity	NPD9545	Approved
0.716	Intermediate Similarity	NPD6273	Approved
0.7157	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7783	Phase 2
0.715	Intermediate Similarity	NPD7435	Discontinued
0.7143	Intermediate Similarity	NPD7038	Approved
0.7143	Intermediate Similarity	NPD7039	Approved
0.7135	Intermediate Similarity	NPD3455	Phase 2
0.7134	Intermediate Similarity	NPD5408	Approved
0.7134	Intermediate Similarity	NPD2438	Suspended
0.7134	Intermediate Similarity	NPD5404	Approved
0.7134	Intermediate Similarity	NPD5406	Approved
0.7134	Intermediate Similarity	NPD5405	Approved
0.7128	Intermediate Similarity	NPD7584	Approved
0.7126	Intermediate Similarity	NPD2309	Approved
0.7124	Intermediate Similarity	NPD9268	Approved
0.712	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD7549	Discontinued
0.7097	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2798	Approved
0.7089	Intermediate Similarity	NPD1019	Discontinued
0.7083	Intermediate Similarity	NPD6776	Approved
0.7083	Intermediate Similarity	NPD6780	Approved
0.7083	Intermediate Similarity	NPD6781	Approved
0.7083	Intermediate Similarity	NPD6777	Approved
0.7083	Intermediate Similarity	NPD6778	Approved
0.7083	Intermediate Similarity	NPD6779	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