NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.21
Volume:	303.703
LogP:	6.563
LogD:	4.711
LogS:	-4.129
# Rotatable Bonds:	9
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.619
Synthetic Accessibility Score:	2.137
Fsp3:	0.647
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.858
MDCK Permeability:	1.4934855244064238e-05
Pgp-inhibitor:	0.438
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.139
Plasma Protein Binding (PPB):	98.27618408203125%
Volume Distribution (VD):	3.06
Pgp-substrate:	1.122397780418396%

ADMET: Metabolism

CYP1A2-inhibitor:	0.93
CYP1A2-substrate:	0.592
CYP2C19-inhibitor:	0.843
CYP2C19-substrate:	0.135
CYP2C9-inhibitor:	0.364
CYP2C9-substrate:	0.957
CYP2D6-inhibitor:	0.867
CYP2D6-substrate:	0.813
CYP3A4-inhibitor:	0.269
CYP3A4-substrate:	0.106

ADMET: Excretion

Clearance (CL):	7.827
Half-life (T1/2):	0.538

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.046
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.127
Rat Oral Acute Toxicity:	0.092
Maximum Recommended Daily Dose:	0.13
Skin Sensitization:	0.948
Carcinogencity:	0.03
Eye Corrosion:	0.656
Eye Irritation:	0.965
Respiratory Toxicity:	0.643

Download Data

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

Natural Product: NPC37802

Natural Product ID:	NPC37802
*Common Name:**	Resorstatin
IUPAC Name:	2-hexyl-5-pentylbenzene-1,3-diol
Synonyms:	resorstatin
Standard InCHIKey:	GAZJVWPMPITOLB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H28O2/c1-3-5-7-9-11-15-16(18)12-14(13-17(15)19)10-8-6-4-2/h12-13,18-19H,3-11H2,1-2H3
SMILES:	CCCCCCc1c(O)cc(cc1O)CCCCC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL496838
PubChem CID:	198749
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000137] Resorcinols

*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
NPO8493	Capraria biflora	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11087595]
NPO33648	Pseudomonas sp. Ki19	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16643045]
NPO25696	Hyptis brevipes	Species	Lamiaceae	Eukaryota	Whole Plant	Tawangmangu village, Karanganyar, Central Java, Indonesia	2003-FEB	PMID[19422206]
NPO25696	Hyptis brevipes	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[19422206]
NPO8881	Centipeda minima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23189738]
NPO25696	Hyptis brevipes	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23282042]
NPO17878	Ips paraconfusus	Species	Curculionidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24318848]
NPO25696	Hyptis brevipes	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28099005]
NPO5119.1	Pseudomonas chlororaphis subsp. aurantiaca	Subspecies	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31999458]
NPO8881	Centipeda minima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11075	Aglaia tomentosa	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18407	Pteris fauriei	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8881	Centipeda minima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21339	Upuna borneensis	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8881	Centipeda minima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12468	Asarum heterotropoides	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12468	Asarum heterotropoides	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8881	Centipeda minima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18407	Pteris fauriei	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10032	Backhousia citriodora	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1807	Senecio macrocephalus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25696	Hyptis brevipes	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5119.1	Pseudomonas chlororaphis subsp. aurantiaca	Subspecies	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO19816	Crotalaria novae-hollandiae	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21339	Upuna borneensis	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8881	Centipeda minima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11075	Aglaia tomentosa	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12468	Asarum heterotropoides	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8239	Mentha timija	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8493	Capraria biflora	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14138	Centaurea aspera	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18446	Paradendryphiella salina	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18405	Trichoderma avellaneum	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17878	Ips paraconfusus	Species	Curculionidae	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
MIC	12

Activity Type	# Activity
Organism	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	=	50.0	ug.mL-1	PMID[545057]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	50.0	ug.mL-1	PMID[545057]
NPT2647	Organism	Drechslera	Drechslera	MIC	=	50.0	ug.mL-1	PMID[545057]
NPT1278	Organism	Fusarium culmorum	Fusarium culmorum	MIC	=	50.0	ug.mL-1	PMID[545057]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	7.0	ug.mL-1	PMID[545057]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	6.0	ug.mL-1	PMID[545057]
NPT2714	Organism	Pseudomonas savastanoi pv. savastanoi	Pseudomonas savastanoi pv. savastanoi	MIC	=	50.0	ug.mL-1	PMID[545057]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	4.2	ug.mL-1	PMID[545058]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	4.2	ug.mL-1	PMID[545058]
NPT3721	Organism	Enterococcus hirae	Enterococcus hirae	MIC	=	4.2	ug.mL-1	PMID[545058]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MIC	=	4.2	ug.mL-1	PMID[545058]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	8.4	ug.mL-1	PMID[545058]

☑ 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 NPC37802 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	279
0.1-0.2	1669
0.2-0.3	5210
0.3-0.4	14302
0.4-0.5	5052
0.5-0.6	8538
0.6-0.7	5794
0.7-0.8	1531
0.8-0.85	167
0.85-0.9	89
0.9-0.95	48
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
0.9898	High Similarity	NPC99836
0.9898	High Similarity	NPC12640
0.9898	High Similarity	NPC201662
0.9897	High Similarity	NPC244513
0.9897	High Similarity	NPC227458
0.9897	High Similarity	NPC218879
0.9798	High Similarity	NPC204901
0.9798	High Similarity	NPC158253
0.9798	High Similarity	NPC232523
0.9604	High Similarity	NPC186385
0.9604	High Similarity	NPC33728
0.9604	High Similarity	NPC19808
0.9604	High Similarity	NPC299568
0.9505	High Similarity	NPC174981
0.949	High Similarity	NPC147310
0.949	High Similarity	NPC166313
0.949	High Similarity	NPC137415
0.949	High Similarity	NPC11280
0.949	High Similarity	NPC24407
0.949	High Similarity	NPC294186
0.949	High Similarity	NPC192032
0.9417	High Similarity	NPC224527
0.9394	High Similarity	NPC94351
0.9394	High Similarity	NPC85479
0.9394	High Similarity	NPC106396
0.9394	High Similarity	NPC168303
0.9394	High Similarity	NPC71002
0.9394	High Similarity	NPC302219
0.9394	High Similarity	NPC222522
0.9394	High Similarity	NPC53051
0.9394	High Similarity	NPC24404
0.9394	High Similarity	NPC242342
0.9394	High Similarity	NPC146798
0.9394	High Similarity	NPC313030
0.9394	High Similarity	NPC249828
0.9388	High Similarity	NPC10588
0.9388	High Similarity	NPC166761
0.9327	High Similarity	NPC166995
0.9293	High Similarity	NPC72947
0.9293	High Similarity	NPC284011
0.9238	High Similarity	NPC23804
0.9238	High Similarity	NPC117846
0.9238	High Similarity	NPC263753
0.9238	High Similarity	NPC319803
0.9135	High Similarity	NPC224870
0.9109	High Similarity	NPC241891
0.9109	High Similarity	NPC102216
0.9065	High Similarity	NPC246760
0.9065	High Similarity	NPC84999
0.9057	High Similarity	NPC261343
0.9048	High Similarity	NPC476632
0.9048	High Similarity	NPC165770
0.9048	High Similarity	NPC4493
0.9048	High Similarity	NPC225679
0.9029	High Similarity	NPC61033
0.9029	High Similarity	NPC305603
0.902	High Similarity	NPC246056
0.902	High Similarity	NPC134829
0.8969	High Similarity	NPC295295
0.8962	High Similarity	NPC43525
0.8932	High Similarity	NPC118286
0.8932	High Similarity	NPC302681
0.8932	High Similarity	NPC470700
0.8932	High Similarity	NPC39097
0.8932	High Similarity	NPC39664
0.8932	High Similarity	NPC109691
0.8911	High Similarity	NPC477685
0.8911	High Similarity	NPC100340
0.8911	High Similarity	NPC143659
0.89	High Similarity	NPC80027
0.8846	High Similarity	NPC54844
0.8835	High Similarity	NPC474839
0.8818	High Similarity	NPC9592
0.8818	High Similarity	NPC48781
0.8818	High Similarity	NPC206
0.8818	High Similarity	NPC144343
0.8818	High Similarity	NPC190514
0.8812	High Similarity	NPC72729
0.8807	High Similarity	NPC115808
0.88	High Similarity	NPC6597
0.88	High Similarity	NPC79241
0.8796	High Similarity	NPC107240
0.8785	High Similarity	NPC473521
0.8762	High Similarity	NPC63698
0.8762	High Similarity	NPC61885
0.8739	High Similarity	NPC191866
0.8739	High Similarity	NPC184302
0.8738	High Similarity	NPC30506
0.8738	High Similarity	NPC119860
0.8727	High Similarity	NPC470760
0.8725	High Similarity	NPC252105
0.8713	High Similarity	NPC33675
0.8713	High Similarity	NPC299762
0.87	High Similarity	NPC259512
0.87	High Similarity	NPC312132
0.8673	High Similarity	NPC231150
0.8667	High Similarity	NPC66834
0.8654	High Similarity	NPC47284
0.8654	High Similarity	NPC292452
0.8641	High Similarity	NPC471228
0.8641	High Similarity	NPC235762
0.8627	High Similarity	NPC174911
0.8627	High Similarity	NPC248396
0.8627	High Similarity	NPC48730
0.8627	High Similarity	NPC129373
0.8614	High Similarity	NPC291789
0.8614	High Similarity	NPC152097
0.8598	High Similarity	NPC168657
0.8586	High Similarity	NPC147284
0.8586	High Similarity	NPC306884
0.8586	High Similarity	NPC3358
0.8586	High Similarity	NPC210497
0.8586	High Similarity	NPC162314
0.8586	High Similarity	NPC94139
0.8585	High Similarity	NPC306295
0.8584	High Similarity	NPC218753
0.8584	High Similarity	NPC24125
0.8571	High Similarity	NPC53740
0.8571	High Similarity	NPC248904
0.8571	High Similarity	NPC469913
0.8571	High Similarity	NPC192
0.8559	High Similarity	NPC277588
0.8559	High Similarity	NPC33270
0.8559	High Similarity	NPC69261
0.8558	High Similarity	NPC475225
0.8545	High Similarity	NPC808
0.8544	High Similarity	NPC80800
0.8532	High Similarity	NPC62546
0.8532	High Similarity	NPC162113
0.8529	High Similarity	NPC260775
0.8519	High Similarity	NPC469912
0.8509	High Similarity	NPC39029
0.8505	High Similarity	NPC202647
0.8496	Intermediate Similarity	NPC69006
0.8476	Intermediate Similarity	NPC471350
0.8476	Intermediate Similarity	NPC117115
0.8468	Intermediate Similarity	NPC150624
0.8462	Intermediate Similarity	NPC315022
0.8462	Intermediate Similarity	NPC108497
0.8455	Intermediate Similarity	NPC249270
0.8447	Intermediate Similarity	NPC248573
0.8447	Intermediate Similarity	NPC161571
0.8447	Intermediate Similarity	NPC275053
0.8447	Intermediate Similarity	NPC70677
0.8447	Intermediate Similarity	NPC130756
0.8447	Intermediate Similarity	NPC12931
0.844	Intermediate Similarity	NPC228452
0.844	Intermediate Similarity	NPC302371
0.8435	Intermediate Similarity	NPC122175
0.8435	Intermediate Similarity	NPC18128
0.8435	Intermediate Similarity	NPC77789
0.8431	Intermediate Similarity	NPC475078
0.8426	Intermediate Similarity	NPC475018
0.8407	Intermediate Similarity	NPC137294
0.8407	Intermediate Similarity	NPC85895
0.8396	Intermediate Similarity	NPC310456
0.8393	Intermediate Similarity	NPC320864
0.8381	Intermediate Similarity	NPC315936
0.8381	Intermediate Similarity	NPC272029
0.8378	Intermediate Similarity	NPC53906
0.8378	Intermediate Similarity	NPC232165
0.8367	Intermediate Similarity	NPC27974
0.8362	Intermediate Similarity	NPC96940
0.8349	Intermediate Similarity	NPC151537
0.8349	Intermediate Similarity	NPC54373
0.8333	Intermediate Similarity	NPC223451
0.8318	Intermediate Similarity	NPC151477
0.8317	Intermediate Similarity	NPC76938
0.8317	Intermediate Similarity	NPC152415
0.8317	Intermediate Similarity	NPC245187
0.8304	Intermediate Similarity	NPC123559
0.8304	Intermediate Similarity	NPC114064
0.8291	Intermediate Similarity	NPC224342
0.8291	Intermediate Similarity	NPC139774
0.8291	Intermediate Similarity	NPC174729
0.8288	Intermediate Similarity	NPC276737
0.8288	Intermediate Similarity	NPC22610
0.8286	Intermediate Similarity	NPC168393
0.8286	Intermediate Similarity	NPC269212
0.8269	Intermediate Similarity	NPC130103
0.8265	Intermediate Similarity	NPC407
0.8265	Intermediate Similarity	NPC307235
0.8257	Intermediate Similarity	NPC242178
0.8257	Intermediate Similarity	NPC132720
0.8252	Intermediate Similarity	NPC474073
0.8246	Intermediate Similarity	NPC121866
0.8246	Intermediate Similarity	NPC217174
0.8235	Intermediate Similarity	NPC222146
0.8235	Intermediate Similarity	NPC32714
0.823	Intermediate Similarity	NPC474933
0.823	Intermediate Similarity	NPC221549
0.823	Intermediate Similarity	NPC127894
0.823	Intermediate Similarity	NPC15860
0.823	Intermediate Similarity	NPC50521
0.823	Intermediate Similarity	NPC219070
0.823	Intermediate Similarity	NPC470759
0.823	Intermediate Similarity	NPC244816
0.8224	Intermediate Similarity	NPC155072
0.8224	Intermediate Similarity	NPC21594
0.8224	Intermediate Similarity	NPC164576

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 NPC37802 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	269
0.1-0.2	1053
0.2-0.3	1644
0.3-0.4	2996
0.4-0.5	1724
0.5-0.6	1076
0.6-0.7	336
0.7-0.8	44
0.8-0.85	4
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9604	High Similarity	NPD4750	Phase 3
0.91	High Similarity	NPD846	Approved
0.91	High Similarity	NPD940	Approved
0.898	High Similarity	NPD844	Approved
0.87	High Similarity	NPD288	Approved
0.8447	Intermediate Similarity	NPD1242	Phase 1
0.8362	Intermediate Similarity	NPD4749	Approved
0.8269	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD2859	Approved
0.8058	Intermediate Similarity	NPD2860	Approved
0.8039	Intermediate Similarity	NPD845	Approved
0.8	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3020	Approved
0.7961	Intermediate Similarity	NPD2933	Approved
0.7961	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD2934	Approved
0.7951	Intermediate Similarity	NPD4625	Phase 3
0.7946	Intermediate Similarity	NPD7635	Approved
0.7886	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD1809	Phase 2
0.7818	Intermediate Similarity	NPD2342	Discontinued
0.7732	Intermediate Similarity	NPD9093	Approved
0.7679	Intermediate Similarity	NPD3021	Approved
0.7679	Intermediate Similarity	NPD3022	Approved
0.7653	Intermediate Similarity	NPD9089	Approved
0.76	Intermediate Similarity	NPD111	Approved
0.7586	Intermediate Similarity	NPD6671	Approved
0.7568	Intermediate Similarity	NPD1445	Approved
0.7568	Intermediate Similarity	NPD1444	Approved
0.7462	Intermediate Similarity	NPD6099	Approved
0.7462	Intermediate Similarity	NPD6100	Approved
0.744	Intermediate Similarity	NPD4908	Phase 1
0.7438	Intermediate Similarity	NPD1610	Phase 2
0.7407	Intermediate Similarity	NPD9273	Approved
0.7398	Intermediate Similarity	NPD6696	Suspended
0.7395	Intermediate Similarity	NPD1548	Phase 1
0.7381	Intermediate Similarity	NPD3027	Phase 3
0.7368	Intermediate Similarity	NPD1792	Phase 2
0.736	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD9500	Approved
0.7295	Intermediate Similarity	NPD422	Phase 1
0.728	Intermediate Similarity	NPD599	Approved
0.728	Intermediate Similarity	NPD859	Approved
0.728	Intermediate Similarity	NPD858	Approved
0.728	Intermediate Similarity	NPD602	Approved
0.7273	Intermediate Similarity	NPD4626	Approved
0.7252	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD3091	Approved
0.7241	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD9094	Approved
0.7154	Intermediate Similarity	NPD3092	Approved
0.7154	Intermediate Similarity	NPD1201	Approved
0.7131	Intermediate Similarity	NPD2932	Approved
0.7131	Intermediate Similarity	NPD4059	Approved
0.7131	Intermediate Similarity	NPD3019	Approved
0.7119	Intermediate Similarity	NPD2228	Approved
0.7119	Intermediate Similarity	NPD2234	Approved
0.7119	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD2229	Approved
0.7107	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD228	Approved
0.7083	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD7390	Discontinued
0.7077	Intermediate Similarity	NPD1613	Approved
0.7077	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD943	Approved
0.7063	Intermediate Similarity	NPD3094	Phase 2
0.7059	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1793	Approved
0.7059	Intermediate Similarity	NPD497	Approved
0.7059	Intermediate Similarity	NPD1791	Approved
0.704	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD1778	Approved
0.6992	Remote Similarity	NPD2286	Discontinued
0.6975	Remote Similarity	NPD495	Approved
0.6975	Remote Similarity	NPD496	Approved
0.6975	Remote Similarity	NPD1398	Phase 1
0.6975	Remote Similarity	NPD498	Approved
0.697	Remote Similarity	NPD2568	Approved
0.697	Remote Similarity	NPD1607	Approved
0.6964	Remote Similarity	NPD3028	Approved
0.6953	Remote Similarity	NPD3018	Phase 2
0.6953	Remote Similarity	NPD2861	Phase 2
0.6942	Remote Similarity	NPD7340	Approved
0.6935	Remote Similarity	NPD1980	Approved
0.6935	Remote Similarity	NPD1983	Approved
0.6935	Remote Similarity	NPD1981	Approved
0.693	Remote Similarity	NPD9608	Approved
0.693	Remote Similarity	NPD9610	Approved
0.6929	Remote Similarity	NPD1135	Approved
0.6929	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD1129	Approved
0.6929	Remote Similarity	NPD1134	Approved
0.6929	Remote Similarity	NPD1470	Approved
0.6929	Remote Similarity	NPD1133	Approved
0.6929	Remote Similarity	NPD1131	Approved
0.6923	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD9618	Approved
0.6917	Remote Similarity	NPD9614	Approved
0.6911	Remote Similarity	NPD4093	Discontinued
0.6911	Remote Similarity	NPD5691	Approved
0.6897	Remote Similarity	NPD290	Approved
0.6891	Remote Similarity	NPD9379	Approved
0.6891	Remote Similarity	NPD9377	Approved
0.688	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.688	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD3095	Discontinued
0.6855	Remote Similarity	NPD4589	Approved
0.6855	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1751	Approved
0.6842	Remote Similarity	NPD4097	Suspended
0.6838	Remote Similarity	NPD74	Approved
0.6838	Remote Similarity	NPD9266	Approved
0.6838	Remote Similarity	NPD2684	Approved
0.6837	Remote Similarity	NPD9087	Approved
0.6829	Remote Similarity	NPD5303	Approved
0.6829	Remote Similarity	NPD1759	Phase 1
0.6829	Remote Similarity	NPD5304	Approved
0.6829	Remote Similarity	NPD7330	Discontinued
0.6825	Remote Similarity	NPD9269	Phase 2
0.6825	Remote Similarity	NPD2230	Approved
0.6825	Remote Similarity	NPD2233	Approved
0.6825	Remote Similarity	NPD2232	Approved
0.6818	Remote Similarity	NPD2238	Phase 2
0.6818	Remote Similarity	NPD1240	Approved
0.6815	Remote Similarity	NPD5408	Approved
0.6815	Remote Similarity	NPD5405	Approved
0.6815	Remote Similarity	NPD5404	Approved
0.6815	Remote Similarity	NPD5406	Approved
0.6803	Remote Similarity	NPD9493	Approved
0.6803	Remote Similarity	NPD405	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3496	Discontinued
0.6794	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD9268	Approved
0.6774	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD2982	Phase 2
0.6772	Remote Similarity	NPD2983	Phase 2
0.6752	Remote Similarity	NPD9263	Approved
0.6752	Remote Similarity	NPD9267	Approved
0.6752	Remote Similarity	NPD9264	Approved
0.6748	Remote Similarity	NPD16	Approved
0.6748	Remote Similarity	NPD1758	Phase 1
0.6748	Remote Similarity	NPD9613	Approved
0.6748	Remote Similarity	NPD856	Approved
0.6748	Remote Similarity	NPD9615	Approved
0.6748	Remote Similarity	NPD9616	Approved
0.6742	Remote Similarity	NPD6407	Approved
0.6742	Remote Similarity	NPD6405	Approved
0.6741	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD9088	Approved
0.6721	Remote Similarity	NPD709	Approved
0.672	Remote Similarity	NPD9381	Approved
0.672	Remote Similarity	NPD9384	Approved
0.6715	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD5283	Phase 1
0.6694	Remote Similarity	NPD316	Approved
0.6693	Remote Similarity	NPD2981	Phase 2
0.6692	Remote Similarity	NPD5736	Approved
0.6692	Remote Similarity	NPD1555	Discontinued
0.6667	Remote Similarity	NPD2532	Approved
0.6667	Remote Similarity	NPD2533	Approved
0.6667	Remote Similarity	NPD2534	Approved
0.6667	Remote Similarity	NPD2797	Approved
0.6667	Remote Similarity	NPD968	Approved
0.6667	Remote Similarity	NPD7636	Approved
0.6667	Remote Similarity	NPD3143	Discontinued
0.6642	Remote Similarity	NPD230	Phase 1
0.6641	Remote Similarity	NPD4659	Approved
0.6641	Remote Similarity	NPD9622	Approved
0.6641	Remote Similarity	NPD596	Approved
0.6641	Remote Similarity	NPD1755	Approved
0.6641	Remote Similarity	NPD600	Approved
0.6634	Remote Similarity	NPD9294	Approved
0.6619	Remote Similarity	NPD3892	Phase 2
0.6618	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD1510	Phase 2
0.6615	Remote Similarity	NPD2195	Approved
0.6615	Remote Similarity	NPD6584	Phase 3
0.6615	Remote Similarity	NPD2194	Approved
0.6614	Remote Similarity	NPD1091	Approved
0.6613	Remote Similarity	NPD317	Approved
0.6613	Remote Similarity	NPD318	Approved
0.6612	Remote Similarity	NPD7843	Approved
0.661	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD256	Approved
0.6585	Remote Similarity	NPD7157	Approved
0.6585	Remote Similarity	NPD255	Approved
0.6569	Remote Similarity	NPD2935	Discontinued
0.6569	Remote Similarity	NPD1551	Phase 2
0.6567	Remote Similarity	NPD4060	Phase 1
0.6567	Remote Similarity	NPD468	Phase 1
0.6565	Remote Similarity	NPD3635	Approved
0.6565	Remote Similarity	NPD3637	Approved
0.6565	Remote Similarity	NPD3636	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