NPASS Compound

Structure

NPC208069 OpenBabel07101718242D 45 49 0 0 1 0 0 0 0 0999 V2000 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -5.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -4.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 1.9019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2942 -3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -5.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -0.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -0.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -6.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -4.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 0.4019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -4.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -1.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -1.7321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8301 -1.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -1.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -4.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4282 -1.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -1.7321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5000 -2.5981 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8301 -7.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -4.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -4.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -3.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2942 -1.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -3.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 1.4019 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4282 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -1.5981 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 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 5 42 1 0 0 0 0 6 43 1 0 0 0 0 7 8 1 0 0 0 0 7 14 2 0 0 0 0 9 15 1 0 0 0 0 9 18 1 0 0 0 0 10 17 2 0 0 0 0 10 20 1 0 0 0 0 11 17 1 0 0 0 0 11 22 2 0 0 0 0 12 19 1 0 0 0 0 12 23 1 0 0 0 0 13 21 1 0 0 0 0 13 32 1 0 0 0 0 15 34 2 0 0 0 0 16 18 2 0 0 0 0 16 19 1 0 0 0 0 17 42 1 0 0 0 0 18 26 1 0 0 0 0 19 28 2 0 0 0 0 20 24 2 0 0 0 0 20 30 1 0 0 0 0 21 29 1 0 0 0 0 21 35 1 6 0 0 0 22 24 1 0 0 0 0 22 44 1 0 0 0 0 23 32 1 0 0 0 0 23 36 2 0 0 0 0 24 27 1 0 0 0 0 25 26 2 0 0 0 0 25 27 1 0 0 0 0 25 28 1 0 0 0 0 26 37 1 0 0 0 0 27 38 2 0 0 0 0 28 44 1 0 0 0 0 29 33 1 1 0 0 0 29 45 1 0 0 0 0 30 39 2 0 0 0 0 30 43 1 0 0 0 0 31 32 1 6 0 0 0 31 33 1 0 0 0 0 31 40 1 0 0 0 0 32 41 1 6 0 0 0 33 8 1 1 0 0 0 33 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	120.06
Volume:	136.612
LogP:	1.155
LogD:	1.296
LogS:	-1.009
# Rotatable Bonds:	2
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.539
Synthetic Accessibility Score:	1.706
Fsp3:	0.125
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.291
MDCK Permeability:	3.267739521106705e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.056
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.933
Plasma Protein Binding (PPB):	36.94427490234375%
Volume Distribution (VD):	1.575
Pgp-substrate:	67.031982421875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.699
CYP1A2-substrate:	0.448
CYP2C19-inhibitor:	0.225
CYP2C19-substrate:	0.3
CYP2C9-inhibitor:	0.024
CYP2C9-substrate:	0.115
CYP2D6-inhibitor:	0.157
CYP2D6-substrate:	0.479
CYP3A4-inhibitor:	0.018
CYP3A4-substrate:	0.251

ADMET: Excretion

Clearance (CL):	9.592
Half-life (T1/2):	0.784

ADMET: Toxicity

hERG Blockers:	0.097
Human Hepatotoxicity (H-HT):	0.059
Drug-inuced Liver Injury (DILI):	0.313
AMES Toxicity:	0.395
Rat Oral Acute Toxicity:	0.019
Maximum Recommended Daily Dose:	0.03
Skin Sensitization:	0.957
Carcinogencity:	0.319
Eye Corrosion:	0.973
Eye Irritation:	0.992
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC208069

Natural Product ID:	NPC208069
*Common Name:**	Pestalofone E
IUPAC Name:	methyl 8-hydroxy-3-methoxy-6-methyl-9-oxo-7-(2-oxopropyl)-5-[2-oxo-2-[(1S,2S,4R,5R,6R)-2,4,5-trihydroxy-6-(3-methylbut-2-enyl)-7-oxabicyclo[4.1.0]heptan-4-yl]ethyl]xanthene-1-carboxylate
Synonyms:	Pestalofone E
Standard InCHIKey:	FYULFHVQQBWSCF-JRLFQTPXSA-N
Standard InCHI:	InChI=1S/C33H36O12/c1-14(2)7-8-33-29(45-33)21(35)13-32(41,31(33)40)23(36)12-19-16(4)18(9-15(3)34)26(37)25-27(38)24-20(30(39)43-6)10-17(42-5)11-22(24)44-28(19)25/h7,10-11,21,29,31,35,37,40-41H,8-9,12-13H2,1-6H3/t21-,29-,31+,32-,33-/m0/s1
SMILES:	COC(=O)c1cc(OC)cc2c1c(=O)c1c(o2)c(CC(=O)[C@@]2(O)C[C@H](O)[C@H]3[C@]([C@@H]2O)(CC=C(C)C)O3)c(c(c1O)CC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL443191
PubChem CID:	42609855
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones [CHEMONTID:0003518] 4-prenylated xanthones

*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
NPO22690	Pestalotiopsis fici	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18468908]
NPO22690	Pestalotiopsis fici	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19101157]
NPO22690	Pestalotiopsis fici	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19618920]
NPO22690	Pestalotiopsis fici	Species	Sporocadaceae	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
EC50	1
IC50	1
MIC	1
Others	1

Activity Type	# Activity
Cell Line	1
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1452	Cell Line	C8166	Homo sapiens	CC50	>	200000.0	nM	PMID[525559]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	93700.0	nM	PMID[525559]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	IC50	=	900.0	nM	PMID[525559]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	=	31200.0	nM	PMID[525559]

☑ 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 NPC208069 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	1687
0.2-0.3	3556
0.3-0.4	8332
0.4-0.5	9767
0.5-0.6	5104
0.6-0.7	5472
0.7-0.8	5534
0.8-0.85	2582
0.85-0.9	224
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9222	High Similarity	NPC472049
0.9205	High Similarity	NPC314672
0.9186	High Similarity	NPC477683
0.9186	High Similarity	NPC477682
0.9181	High Similarity	NPC68381
0.9138	High Similarity	NPC475148
0.9138	High Similarity	NPC475656
0.9112	High Similarity	NPC76647
0.908	High Similarity	NPC475161
0.908	High Similarity	NPC477860
0.9064	High Similarity	NPC473113
0.9064	High Similarity	NPC111536
0.9064	High Similarity	NPC271385
0.9064	High Similarity	NPC5029
0.9064	High Similarity	NPC30432
0.9064	High Similarity	NPC76128
0.9029	High Similarity	NPC313452
0.9017	High Similarity	NPC46958
0.9017	High Similarity	NPC475233
0.9012	High Similarity	NPC472054
0.9012	High Similarity	NPC476311
0.9006	High Similarity	NPC298778
0.9	High Similarity	NPC225419
0.9	High Similarity	NPC473094
0.8982	High Similarity	NPC472055
0.8971	High Similarity	NPC315221
0.896	High Similarity	NPC294149
0.8953	High Similarity	NPC158226
0.8947	High Similarity	NPC473096
0.8947	High Similarity	NPC473095
0.8947	High Similarity	NPC99613
0.8947	High Similarity	NPC49487
0.8944	High Similarity	NPC314020
0.8935	High Similarity	NPC474240
0.8927	High Similarity	NPC197972
0.8922	High Similarity	NPC470339
0.8914	High Similarity	NPC212290
0.8908	High Similarity	NPC469345
0.8908	High Similarity	NPC312630
0.8908	High Similarity	NPC324220
0.8908	High Similarity	NPC475246
0.8902	High Similarity	NPC154986
0.8902	High Similarity	NPC98776
0.8895	High Similarity	NPC241874
0.8889	High Similarity	NPC472622
0.8889	High Similarity	NPC474024
0.8882	High Similarity	NPC475888
0.8876	High Similarity	NPC105591
0.8876	High Similarity	NPC211107
0.8869	High Similarity	NPC470810
0.8857	High Similarity	NPC207467
0.8857	High Similarity	NPC476210
0.8857	High Similarity	NPC476199
0.8851	High Similarity	NPC474345
0.8851	High Similarity	NPC3718
0.8851	High Similarity	NPC232412
0.8851	High Similarity	NPC199533
0.8851	High Similarity	NPC86809
0.8851	High Similarity	NPC98667
0.8851	High Similarity	NPC470454
0.8851	High Similarity	NPC146803
0.8844	High Similarity	NPC472620
0.8844	High Similarity	NPC477836
0.8837	High Similarity	NPC102810
0.8837	High Similarity	NPC222455
0.8837	High Similarity	NPC163130
0.8837	High Similarity	NPC165979
0.8833	High Similarity	NPC48474
0.883	High Similarity	NPC207575
0.883	High Similarity	NPC29160
0.883	High Similarity	NPC125465
0.883	High Similarity	NPC13481
0.883	High Similarity	NPC472621
0.882	High Similarity	NPC112380
0.882	High Similarity	NPC87583
0.8817	High Similarity	NPC117985
0.8817	High Similarity	NPC3629
0.8817	High Similarity	NPC474239
0.8814	High Similarity	NPC475662
0.8814	High Similarity	NPC473717
0.8814	High Similarity	NPC473631
0.8814	High Similarity	NPC293227
0.8807	High Similarity	NPC473785
0.8807	High Similarity	NPC473729
0.8807	High Similarity	NPC277710
0.8807	High Similarity	NPC114257
0.8807	High Similarity	NPC84494
0.8807	High Similarity	NPC153578
0.8807	High Similarity	NPC245059
0.8807	High Similarity	NPC299149
0.8802	High Similarity	NPC164427
0.8793	High Similarity	NPC469393
0.8791	High Similarity	NPC314687
0.8791	High Similarity	NPC470198
0.8791	High Similarity	NPC470193
0.8791	High Similarity	NPC470196
0.8791	High Similarity	NPC470194
0.8791	High Similarity	NPC470197
0.8791	High Similarity	NPC470200
0.8791	High Similarity	NPC316274
0.8791	High Similarity	NPC470195
0.8791	High Similarity	NPC282474
0.8786	High Similarity	NPC251144
0.8786	High Similarity	NPC313717
0.8786	High Similarity	NPC241387
0.8786	High Similarity	NPC315306
0.8786	High Similarity	NPC313304
0.8779	High Similarity	NPC218226
0.8779	High Similarity	NPC324522
0.8779	High Similarity	NPC470341
0.8779	High Similarity	NPC150131
0.8779	High Similarity	NPC6588
0.8779	High Similarity	NPC234331
0.8779	High Similarity	NPC477154
0.8779	High Similarity	NPC472058
0.8779	High Similarity	NPC107009
0.8779	High Similarity	NPC105414
0.8779	High Similarity	NPC234497
0.8779	High Similarity	NPC117854
0.8772	High Similarity	NPC471788
0.8765	High Similarity	NPC478229
0.8765	High Similarity	NPC473961
0.8757	High Similarity	NPC470448
0.8757	High Similarity	NPC470452
0.8757	High Similarity	NPC284495
0.8757	High Similarity	NPC471976
0.8757	High Similarity	NPC470453
0.8757	High Similarity	NPC164047
0.875	High Similarity	NPC131405
0.875	High Similarity	NPC281137
0.875	High Similarity	NPC282390
0.8743	High Similarity	NPC175192
0.8743	High Similarity	NPC162248
0.8743	High Similarity	NPC99381
0.8743	High Similarity	NPC68727
0.8743	High Similarity	NPC245975
0.8743	High Similarity	NPC326910
0.8743	High Similarity	NPC63105
0.8736	High Similarity	NPC271848
0.8736	High Similarity	NPC81332
0.8736	High Similarity	NPC262580
0.8736	High Similarity	NPC212038
0.8736	High Similarity	NPC289396
0.8736	High Similarity	NPC121333
0.8735	High Similarity	NPC154683
0.8735	High Similarity	NPC40356
0.8735	High Similarity	NPC321363
0.8735	High Similarity	NPC253904
0.8728	High Similarity	NPC326877
0.8728	High Similarity	NPC472619
0.8728	High Similarity	NPC259905
0.8721	High Similarity	NPC471823
0.8721	High Similarity	NPC178173
0.8721	High Similarity	NPC477835
0.8721	High Similarity	NPC178851
0.8721	High Similarity	NPC471213
0.8721	High Similarity	NPC43319
0.8715	High Similarity	NPC229817
0.8715	High Similarity	NPC475352
0.8715	High Similarity	NPC221140
0.8715	High Similarity	NPC473686
0.8715	High Similarity	NPC475220
0.8713	High Similarity	NPC474350
0.8713	High Similarity	NPC236132
0.8713	High Similarity	NPC7483
0.8713	High Similarity	NPC41301
0.8713	High Similarity	NPC197168
0.8706	High Similarity	NPC474186
0.8706	High Similarity	NPC474351
0.8706	High Similarity	NPC475883
0.8706	High Similarity	NPC478222
0.8701	High Similarity	NPC473607
0.8701	High Similarity	NPC113446
0.8698	High Similarity	NPC85121
0.869	High Similarity	NPC215917
0.869	High Similarity	NPC208152
0.869	High Similarity	NPC471787
0.869	High Similarity	NPC472050
0.869	High Similarity	NPC20530
0.869	High Similarity	NPC10754
0.869	High Similarity	NPC78492
0.869	High Similarity	NPC146211
0.8686	High Similarity	NPC476374
0.8686	High Similarity	NPC199357
0.8686	High Similarity	NPC213052
0.8683	High Similarity	NPC293286
0.8683	High Similarity	NPC100134
0.8683	High Similarity	NPC469405
0.8683	High Similarity	NPC209760
0.8681	High Similarity	NPC314459
0.8681	High Similarity	NPC470199
0.8678	High Similarity	NPC193698
0.8678	High Similarity	NPC74559
0.8678	High Similarity	NPC124470
0.8678	High Similarity	NPC109827
0.8675	High Similarity	NPC470569
0.8675	High Similarity	NPC478148
0.8674	High Similarity	NPC295436
0.8671	High Similarity	NPC158761
0.8671	High Similarity	NPC249977

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 NPC208069 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	379
0.1-0.2	985
0.2-0.3	1920
0.3-0.4	2617
0.4-0.5	1892
0.5-0.6	871
0.6-0.7	315
0.7-0.8	132
0.8-0.85	35
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8876	High Similarity	NPD7879	Clinical (unspecified phase)
0.875	High Similarity	NPD7075	Discontinued
0.8683	High Similarity	NPD7819	Suspended
0.8621	High Similarity	NPD5844	Phase 1
0.8613	High Similarity	NPD7473	Discontinued
0.8571	High Similarity	NPD7096	Clinical (unspecified phase)
0.8547	High Similarity	NPD6232	Discontinued
0.8488	Intermediate Similarity	NPD6959	Discontinued
0.8471	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8448	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8448	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8448	Intermediate Similarity	NPD6166	Phase 2
0.8444	Intermediate Similarity	NPD8150	Discontinued
0.8418	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8409	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8402	Intermediate Similarity	NPD6801	Discontinued
0.8393	Intermediate Similarity	NPD4380	Phase 2
0.8353	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8352	Intermediate Similarity	NPD3751	Discontinued
0.8324	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8307	Intermediate Similarity	NPD7435	Discontinued
0.8304	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD5402	Approved
0.8278	Intermediate Similarity	NPD8312	Approved
0.8278	Intermediate Similarity	NPD8313	Approved
0.8235	Intermediate Similarity	NPD7411	Suspended
0.8222	Intermediate Similarity	NPD7808	Phase 3
0.8208	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8198	Intermediate Similarity	NPD3817	Phase 2
0.8187	Intermediate Similarity	NPD1934	Approved
0.8187	Intermediate Similarity	NPD8151	Discontinued
0.8176	Intermediate Similarity	NPD6599	Discontinued
0.8167	Intermediate Similarity	NPD7251	Discontinued
0.8167	Intermediate Similarity	NPD6559	Discontinued
0.8156	Intermediate Similarity	NPD7074	Phase 3
0.8152	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD6779	Approved
0.8148	Intermediate Similarity	NPD6776	Approved
0.8148	Intermediate Similarity	NPD6778	Approved
0.8148	Intermediate Similarity	NPD6780	Approved
0.8148	Intermediate Similarity	NPD6777	Approved
0.8148	Intermediate Similarity	NPD6781	Approved
0.8148	Intermediate Similarity	NPD6782	Approved
0.8144	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD7874	Approved
0.8142	Intermediate Similarity	NPD8434	Phase 2
0.8136	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD3787	Discontinued
0.8118	Intermediate Similarity	NPD3226	Approved
0.8115	Intermediate Similarity	NPD7698	Approved
0.8115	Intermediate Similarity	NPD7697	Approved
0.8115	Intermediate Similarity	NPD7696	Phase 3
0.8114	Intermediate Similarity	NPD5494	Approved
0.8111	Intermediate Similarity	NPD6797	Phase 2
0.8101	Intermediate Similarity	NPD7054	Approved
0.8095	Intermediate Similarity	NPD2534	Approved
0.8095	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD2533	Approved
0.8095	Intermediate Similarity	NPD2532	Approved
0.8087	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8073	Intermediate Similarity	NPD7871	Phase 2
0.8073	Intermediate Similarity	NPD7870	Phase 2
0.8056	Intermediate Similarity	NPD7472	Approved
0.8046	Intermediate Similarity	NPD3882	Suspended
0.8046	Intermediate Similarity	NPD7768	Phase 2
0.8045	Intermediate Similarity	NPD3818	Discontinued
0.8041	Intermediate Similarity	NPD7701	Phase 2
0.8036	Intermediate Similarity	NPD6799	Approved
0.8035	Intermediate Similarity	NPD2801	Approved
0.8035	Intermediate Similarity	NPD1465	Phase 2
0.8	Intermediate Similarity	NPD5403	Approved
0.8	Intermediate Similarity	NPD3749	Approved
0.7988	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD7699	Phase 2
0.7947	Intermediate Similarity	NPD7700	Phase 2
0.7919	Intermediate Similarity	NPD7783	Phase 2
0.7919	Intermediate Similarity	NPD7801	Approved
0.7919	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD8320	Phase 1
0.7887	Intermediate Similarity	NPD8319	Approved
0.7884	Intermediate Similarity	NPD6535	Approved
0.7884	Intermediate Similarity	NPD6534	Approved
0.7882	Intermediate Similarity	NPD5401	Approved
0.7844	Intermediate Similarity	NPD1549	Phase 2
0.7836	Intermediate Similarity	NPD1512	Approved
0.7801	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD2346	Discontinued
0.7784	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD4628	Phase 3
0.7751	Intermediate Similarity	NPD3750	Approved
0.7747	Intermediate Similarity	NPD7228	Approved
0.7745	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.772	Intermediate Similarity	NPD8285	Discontinued
0.7719	Intermediate Similarity	NPD1511	Approved
0.7701	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6823	Phase 2
0.767	Intermediate Similarity	NPD37	Approved
0.7654	Intermediate Similarity	NPD6234	Discontinued
0.7647	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD4967	Phase 2
0.764	Intermediate Similarity	NPD4965	Approved
0.764	Intermediate Similarity	NPD4966	Approved
0.7624	Intermediate Similarity	NPD5710	Approved
0.7624	Intermediate Similarity	NPD5711	Approved
0.7619	Intermediate Similarity	NPD2935	Discontinued
0.7619	Intermediate Similarity	NPD2796	Approved
0.7616	Intermediate Similarity	NPD7390	Discontinued
0.7602	Intermediate Similarity	NPD6190	Approved
0.7588	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD7685	Pre-registration
0.756	Intermediate Similarity	NPD1510	Phase 2
0.7556	Intermediate Similarity	NPD919	Approved
0.7545	Intermediate Similarity	NPD1607	Approved
0.7527	Intermediate Similarity	NPD5953	Discontinued
0.7515	Intermediate Similarity	NPD6099	Approved
0.7515	Intermediate Similarity	NPD1551	Phase 2
0.7515	Intermediate Similarity	NPD6100	Approved
0.7487	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD3926	Phase 2
0.7486	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7199	Phase 2
0.7473	Intermediate Similarity	NPD1247	Approved
0.7471	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD3748	Approved
0.743	Intermediate Similarity	NPD8455	Phase 2
0.7425	Intermediate Similarity	NPD1240	Approved
0.7419	Intermediate Similarity	NPD7286	Phase 2
0.7411	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7458	Discontinued
0.7394	Intermediate Similarity	NPD7240	Approved
0.7386	Intermediate Similarity	NPD920	Approved
0.7384	Intermediate Similarity	NPD2800	Approved
0.7371	Intermediate Similarity	NPD6212	Phase 3
0.7371	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD6213	Phase 3
0.7353	Intermediate Similarity	NPD2799	Discontinued
0.7341	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7229	Phase 3
0.731	Intermediate Similarity	NPD5408	Approved
0.731	Intermediate Similarity	NPD5404	Approved
0.731	Intermediate Similarity	NPD5405	Approved
0.731	Intermediate Similarity	NPD5406	Approved
0.7305	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD8127	Discontinued
0.7283	Intermediate Similarity	NPD1243	Approved
0.7278	Intermediate Similarity	NPD230	Phase 1
0.7277	Intermediate Similarity	NPD7584	Approved
0.7273	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD6273	Approved
0.723	Intermediate Similarity	NPD8059	Phase 3
0.723	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4060	Phase 1
0.7202	Intermediate Similarity	NPD2313	Discontinued
0.7198	Intermediate Similarity	NPD7930	Approved
0.7181	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD7177	Discontinued
0.7174	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD8366	Approved
0.7151	Intermediate Similarity	NPD1653	Approved
0.7151	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4625	Phase 3
0.7143	Intermediate Similarity	NPD7003	Approved
0.7135	Intermediate Similarity	NPD6651	Approved
0.7129	Intermediate Similarity	NPD8404	Phase 2
0.7128	Intermediate Similarity	NPD4287	Approved
0.7118	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD1613	Approved
0.7118	Intermediate Similarity	NPD943	Approved
0.7101	Intermediate Similarity	NPD6798	Discontinued
0.7101	Intermediate Similarity	NPD7985	Registered
0.7101	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6674	Discontinued
0.7083	Intermediate Similarity	NPD6832	Phase 2
0.7083	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD447	Suspended
0.7076	Intermediate Similarity	NPD6355	Discontinued
0.7076	Intermediate Similarity	NPD5124	Phase 1
0.7075	Intermediate Similarity	NPD7907	Approved
0.7073	Intermediate Similarity	NPD7585	Approved
0.7071	Intermediate Similarity	NPD4363	Phase 3
0.7071	Intermediate Similarity	NPD4360	Phase 2
0.7069	Intermediate Similarity	NPD2344	Approved
0.7059	Intermediate Similarity	NPD6233	Phase 2
0.7052	Intermediate Similarity	NPD7033	Discontinued
0.7051	Intermediate Similarity	NPD8067	Phase 3
0.7049	Intermediate Similarity	NPD5761	Phase 2
0.7049	Intermediate Similarity	NPD5760	Phase 2
0.7045	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD8360	Approved
0.7041	Intermediate Similarity	NPD8361	Approved
0.7024	Intermediate Similarity	NPD7583	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