NPASS Compound

Structure

NPC263753 OpenBabel07101718182D 24 24 0 0 0 0 0 0 0 0999 V2000 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 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 0.8660 3.5000 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 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 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 -0.0000 3.0000 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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 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 1 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 18 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 15 2 0 0 0 0 9 17 1 0 0 0 0 10 12 1 0 0 0 0 10 16 2 0 0 0 0 11 13 1 0 0 0 0 11 17 2 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 14 18 2 0 0 0 0 14 21 1 0 0 0 0 18 19 1 0 0 0 0 19 22 2 0 0 0 0 20 21 2 0 0 0 0 20 22 1 0 0 0 0 21 23 1 0 0 0 0 22 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.24
Volume:	382.273
LogP:	7.157
LogD:	4.839
LogS:	-4.251
# Rotatable Bonds:	7
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.589
Synthetic Accessibility Score:	2.987
Fsp3:	0.455
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:	-4.788
MDCK Permeability:	1.9339431673870422e-05
Pgp-inhibitor:	0.168
Pgp-substrate:	0.09
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.989
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.066
Plasma Protein Binding (PPB):	98.08515930175781%
Volume Distribution (VD):	6.826
Pgp-substrate:	3.210789442062378%

ADMET: Metabolism

CYP1A2-inhibitor:	0.812
CYP1A2-substrate:	0.242
CYP2C19-inhibitor:	0.707
CYP2C19-substrate:	0.269
CYP2C9-inhibitor:	0.664
CYP2C9-substrate:	0.966
CYP2D6-inhibitor:	0.766
CYP2D6-substrate:	0.734
CYP3A4-inhibitor:	0.289
CYP3A4-substrate:	0.158

ADMET: Excretion

Clearance (CL):	12.16
Half-life (T1/2):	0.349

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.87
Drug-inuced Liver Injury (DILI):	0.012
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.054
Skin Sensitization:	0.935
Carcinogencity:	0.042
Eye Corrosion:	0.003
Eye Irritation:	0.691
Respiratory Toxicity:	0.285

Download Data

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

Natural Product: NPC263753

Natural Product ID:	NPC263753
*Common Name:**	Piperogalin
IUPAC Name:	2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-methyl-4-(3-methylbut-2-enyl)benzene-1,3-diol
Synonyms:	Piperogalin
Standard InCHIKey:	XGLWDZCGSBTQLD-GZTJUZNOSA-N
Standard InCHI:	InChI=1S/C22H32O2/c1-15(2)8-7-9-17(5)11-13-20-21(23)14-18(6)19(22(20)24)12-10-16(3)4/h8,10-11,14,23-24H,7,9,12-13H2,1-6H3/b17-11+
SMILES:	CC(=CCC/C(=C/Cc1c(cc(C)c(CC=C(C)C)c1O)O)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL470032
PubChem CID:	10336642
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0000051] Aromatic monoterpenoids

*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
NPO17403	Peperomia galioides	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7769398]
NPO17403	Peperomia galioides	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8759169]
NPO17403	Peperomia galioides	Species	Piperaceae	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
Others	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	42.0	%	PMID[485532]
NPT1208	Organism	Leishmania braziliensis	Leishmania braziliensis	Activity	>	90.0	%	PMID[485532]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Activity	>	90.0	%	PMID[485532]
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	Activity	>	90.0	%	PMID[485532]

☑ 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 NPC263753 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	331
0.1-0.2	1741
0.2-0.3	4628
0.3-0.4	13711
0.4-0.5	5848
0.5-0.6	7719
0.6-0.7	6546
0.7-0.8	1861
0.8-0.85	191
0.85-0.9	93
0.9-0.95	25
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9714	High Similarity	NPC224870
0.9358	High Similarity	NPC107240
0.9333	High Similarity	NPC99836
0.9333	High Similarity	NPC12640
0.9333	High Similarity	NPC201662
0.9266	High Similarity	NPC117846
0.9245	High Similarity	NPC204901
0.9245	High Similarity	NPC232523
0.9245	High Similarity	NPC158253
0.9238	High Similarity	NPC37802
0.9189	High Similarity	NPC115808
0.9174	High Similarity	NPC166995
0.9143	High Similarity	NPC218879
0.9143	High Similarity	NPC227458
0.9143	High Similarity	NPC244513
0.9107	High Similarity	NPC470760
0.9083	High Similarity	NPC476632
0.9083	High Similarity	NPC165770
0.9083	High Similarity	NPC225679
0.9083	High Similarity	NPC4493
0.9074	High Similarity	NPC186385
0.9074	High Similarity	NPC299568
0.9027	High Similarity	NPC206
0.9	High Similarity	NPC473521
0.9	High Similarity	NPC43525
0.8952	High Similarity	NPC192032
0.8952	High Similarity	NPC11280
0.8952	High Similarity	NPC294186
0.8952	High Similarity	NPC166313
0.8952	High Similarity	NPC147310
0.8952	High Similarity	NPC24407
0.8952	High Similarity	NPC137415
0.8929	High Similarity	NPC246760
0.8929	High Similarity	NPC84999
0.8919	High Similarity	NPC23804
0.8909	High Similarity	NPC151537
0.8909	High Similarity	NPC224527
0.8909	High Similarity	NPC469912
0.8899	High Similarity	NPC33728
0.8899	High Similarity	NPC19808
0.8889	High Similarity	NPC151477
0.8879	High Similarity	NPC237667
0.8879	High Similarity	NPC39029
0.8868	High Similarity	NPC242342
0.8868	High Similarity	NPC24404
0.8868	High Similarity	NPC53051
0.8868	High Similarity	NPC249828
0.8868	High Similarity	NPC313030
0.8868	High Similarity	NPC168303
0.8868	High Similarity	NPC71002
0.8868	High Similarity	NPC106396
0.8868	High Similarity	NPC302219
0.8868	High Similarity	NPC222522
0.8868	High Similarity	NPC85479
0.8868	High Similarity	NPC146798
0.8868	High Similarity	NPC94351
0.8814	High Similarity	NPC224342
0.8807	High Similarity	NPC174981
0.8807	High Similarity	NPC63698
0.8807	High Similarity	NPC61885
0.8796	High Similarity	NPC21594
0.8793	High Similarity	NPC24125
0.8783	High Similarity	NPC191866
0.8774	High Similarity	NPC72947
0.8774	High Similarity	NPC284011
0.875	High Similarity	NPC319803
0.8739	High Similarity	NPC105031
0.8729	High Similarity	NPC53567
0.8727	High Similarity	NPC202647
0.8707	High Similarity	NPC282255
0.8704	High Similarity	NPC117115
0.8679	High Similarity	NPC10588
0.8679	High Similarity	NPC166761
0.8673	High Similarity	NPC249270
0.8661	High Similarity	NPC302371
0.8661	High Similarity	NPC46940
0.8621	High Similarity	NPC151197
0.8621	High Similarity	NPC217174
0.8611	High Similarity	NPC272029
0.8609	High Similarity	NPC304510
0.8609	High Similarity	NPC172219
0.8609	High Similarity	NPC277588
0.8596	High Similarity	NPC474486
0.8585	High Similarity	NPC80027
0.8583	High Similarity	NPC293801
0.8571	High Similarity	NPC260323
0.8571	High Similarity	NPC95716
0.8571	High Similarity	NPC176279
0.8559	High Similarity	NPC58865
0.8547	High Similarity	NPC3239
0.8545	High Similarity	NPC305603
0.8545	High Similarity	NPC61033
0.8534	High Similarity	NPC9592
0.8534	High Similarity	NPC48781
0.8534	High Similarity	NPC154030
0.8534	High Similarity	NPC471671
0.8534	High Similarity	NPC144343
0.8532	High Similarity	NPC134829
0.8532	High Similarity	NPC246056
0.8532	High Similarity	NPC474839
0.8522	High Similarity	NPC471668
0.8512	High Similarity	NPC82299
0.8505	High Similarity	NPC211885
0.8496	Intermediate Similarity	NPC250323
0.8482	Intermediate Similarity	NPC132720
0.8462	Intermediate Similarity	NPC469644
0.8455	Intermediate Similarity	NPC470700
0.8455	Intermediate Similarity	NPC109691
0.8455	Intermediate Similarity	NPC302681
0.8455	Intermediate Similarity	NPC248904
0.8455	Intermediate Similarity	NPC39097
0.8455	Intermediate Similarity	NPC469913
0.8455	Intermediate Similarity	NPC39664
0.8455	Intermediate Similarity	NPC118286
0.8443	Intermediate Similarity	NPC473221
0.844	Intermediate Similarity	NPC241891
0.844	Intermediate Similarity	NPC119860
0.844	Intermediate Similarity	NPC102216
0.844	Intermediate Similarity	NPC30506
0.8435	Intermediate Similarity	NPC35797
0.8435	Intermediate Similarity	NPC192948
0.8426	Intermediate Similarity	NPC252105
0.8426	Intermediate Similarity	NPC477685
0.8421	Intermediate Similarity	NPC715
0.8421	Intermediate Similarity	NPC261343
0.839	Intermediate Similarity	NPC223451
0.839	Intermediate Similarity	NPC69006
0.8378	Intermediate Similarity	NPC54844
0.8374	Intermediate Similarity	NPC215300
0.8374	Intermediate Similarity	NPC24869
0.8364	Intermediate Similarity	NPC99557
0.8364	Intermediate Similarity	NPC219286
0.8364	Intermediate Similarity	NPC292452
0.8364	Intermediate Similarity	NPC471350
0.8362	Intermediate Similarity	NPC38893
0.8362	Intermediate Similarity	NPC477137
0.8362	Intermediate Similarity	NPC308311
0.8361	Intermediate Similarity	NPC170485
0.8348	Intermediate Similarity	NPC195922
0.8333	Intermediate Similarity	NPC57199
0.8333	Intermediate Similarity	NPC72729
0.8333	Intermediate Similarity	NPC225506
0.8333	Intermediate Similarity	NPC180261
0.8333	Intermediate Similarity	NPC37299
0.8333	Intermediate Similarity	NPC471179
0.832	Intermediate Similarity	NPC160623
0.8319	Intermediate Similarity	NPC13482
0.8319	Intermediate Similarity	NPC102639
0.8319	Intermediate Similarity	NPC141782
0.8318	Intermediate Similarity	NPC79241
0.8318	Intermediate Similarity	NPC6597
0.8318	Intermediate Similarity	NPC77492
0.8305	Intermediate Similarity	NPC93071
0.8305	Intermediate Similarity	NPC126002
0.8304	Intermediate Similarity	NPC11554
0.8293	Intermediate Similarity	NPC53781
0.8291	Intermediate Similarity	NPC477136
0.8286	Intermediate Similarity	NPC295295
0.8276	Intermediate Similarity	NPC472893
0.8273	Intermediate Similarity	NPC238696
0.8257	Intermediate Similarity	NPC143659
0.8257	Intermediate Similarity	NPC100340
0.825	Intermediate Similarity	NPC476633
0.8241	Intermediate Similarity	NPC252821
0.8241	Intermediate Similarity	NPC299762
0.8241	Intermediate Similarity	NPC33675
0.8241	Intermediate Similarity	NPC122005
0.823	Intermediate Similarity	NPC314187
0.8226	Intermediate Similarity	NPC38017
0.8224	Intermediate Similarity	NPC259512
0.8224	Intermediate Similarity	NPC312132
0.822	Intermediate Similarity	NPC469609
0.822	Intermediate Similarity	NPC190514
0.8214	Intermediate Similarity	NPC66834
0.8211	Intermediate Similarity	NPC145659
0.8211	Intermediate Similarity	NPC473691
0.8211	Intermediate Similarity	NPC9292
0.8208	Intermediate Similarity	NPC245187
0.8205	Intermediate Similarity	NPC261973
0.8205	Intermediate Similarity	NPC141001
0.8205	Intermediate Similarity	NPC219112
0.8198	Intermediate Similarity	NPC47284
0.8198	Intermediate Similarity	NPC138942
0.8197	Intermediate Similarity	NPC228503
0.8197	Intermediate Similarity	NPC138248
0.819	Intermediate Similarity	NPC268160
0.8182	Intermediate Similarity	NPC122175
0.8182	Intermediate Similarity	NPC168393
0.8182	Intermediate Similarity	NPC269212
0.8182	Intermediate Similarity	NPC108497
0.8182	Intermediate Similarity	NPC168829
0.8182	Intermediate Similarity	NPC71094
0.8182	Intermediate Similarity	NPC120172
0.8182	Intermediate Similarity	NPC74137
0.8175	Intermediate Similarity	NPC282508
0.8175	Intermediate Similarity	NPC8899
0.8175	Intermediate Similarity	NPC15543
0.8174	Intermediate Similarity	NPC228425
0.8165	Intermediate Similarity	NPC129373
0.8165	Intermediate Similarity	NPC248573

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 NPC263753 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	330
0.1-0.2	1039
0.2-0.3	1698
0.3-0.4	3031
0.4-0.5	1648
0.5-0.6	1002
0.6-0.7	336
0.7-0.8	58
0.8-0.85	6
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9074	High Similarity	NPD4750	Phase 3
0.8774	High Similarity	NPD940	Approved
0.8774	High Similarity	NPD846	Approved
0.8333	Intermediate Similarity	NPD7635	Approved
0.8302	Intermediate Similarity	NPD844	Approved
0.8224	Intermediate Similarity	NPD288	Approved
0.8165	Intermediate Similarity	NPD1242	Phase 1
0.816	Intermediate Similarity	NPD4625	Phase 3
0.8131	Intermediate Similarity	NPD1809	Phase 2
0.8065	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.8053	Intermediate Similarity	NPD2342	Discontinued
0.7967	Intermediate Similarity	NPD4749	Approved
0.7944	Intermediate Similarity	NPD845	Approved
0.7909	Intermediate Similarity	NPD3020	Approved
0.787	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD2859	Approved
0.7798	Intermediate Similarity	NPD2860	Approved
0.7787	Intermediate Similarity	NPD4626	Approved
0.776	Intermediate Similarity	NPD6696	Suspended
0.7727	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD2933	Approved
0.7706	Intermediate Similarity	NPD2934	Approved
0.7627	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD3091	Approved
0.7607	Intermediate Similarity	NPD3021	Approved
0.7607	Intermediate Similarity	NPD3022	Approved
0.754	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD7390	Discontinued
0.752	Intermediate Similarity	NPD3092	Approved
0.75	Intermediate Similarity	NPD3019	Approved
0.75	Intermediate Similarity	NPD4059	Approved
0.75	Intermediate Similarity	NPD2932	Approved
0.75	Intermediate Similarity	NPD2286	Discontinued
0.75	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD3094	Phase 2
0.7419	Intermediate Similarity	NPD5691	Approved
0.7407	Intermediate Similarity	NPD6099	Approved
0.7407	Intermediate Similarity	NPD6100	Approved
0.7385	Intermediate Similarity	NPD4908	Phase 1
0.7381	Intermediate Similarity	NPD1610	Phase 2
0.7358	Intermediate Similarity	NPD111	Approved
0.7317	Intermediate Similarity	NPD7340	Approved
0.7313	Intermediate Similarity	NPD4097	Suspended
0.7295	Intermediate Similarity	NPD497	Approved
0.728	Intermediate Similarity	NPD4093	Discontinued
0.7279	Intermediate Similarity	NPD5406	Approved
0.7279	Intermediate Similarity	NPD5404	Approved
0.7279	Intermediate Similarity	NPD5405	Approved
0.7279	Intermediate Similarity	NPD5408	Approved
0.7244	Intermediate Similarity	NPD1201	Approved
0.7236	Intermediate Similarity	NPD6671	Approved
0.7222	Intermediate Similarity	NPD3095	Discontinued
0.7222	Intermediate Similarity	NPD1751	Approved
0.7213	Intermediate Similarity	NPD498	Approved
0.7213	Intermediate Similarity	NPD1398	Phase 1
0.7213	Intermediate Similarity	NPD495	Approved
0.7213	Intermediate Similarity	NPD496	Approved
0.7203	Intermediate Similarity	NPD1445	Approved
0.7203	Intermediate Similarity	NPD1444	Approved
0.72	Intermediate Similarity	NPD1548	Phase 1
0.7197	Intermediate Similarity	NPD3027	Phase 3
0.7194	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD5736	Approved
0.7167	Intermediate Similarity	NPD1792	Phase 2
0.7154	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9093	Approved
0.7121	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD2532	Approved
0.7113	Intermediate Similarity	NPD2534	Approved
0.7113	Intermediate Similarity	NPD2533	Approved
0.7109	Intermediate Similarity	NPD422	Phase 1
0.7094	Intermediate Similarity	NPD9500	Approved
0.7087	Intermediate Similarity	NPD4589	Approved
0.7075	Intermediate Similarity	NPD9089	Approved
0.7073	Intermediate Similarity	NPD2229	Approved
0.7073	Intermediate Similarity	NPD2228	Approved
0.7073	Intermediate Similarity	NPD2234	Approved
0.7063	Intermediate Similarity	NPD5304	Approved
0.7063	Intermediate Similarity	NPD5303	Approved
0.7063	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4060	Phase 1
0.7023	Intermediate Similarity	NPD1133	Approved
0.7023	Intermediate Similarity	NPD1131	Approved
0.7023	Intermediate Similarity	NPD1135	Approved
0.7023	Intermediate Similarity	NPD1129	Approved
0.7023	Intermediate Similarity	NPD1470	Approved
0.7023	Intermediate Similarity	NPD1134	Approved
0.7008	Intermediate Similarity	NPD1651	Approved
0.7008	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.697	Remote Similarity	NPD2195	Approved
0.697	Remote Similarity	NPD2194	Approved
0.6963	Remote Similarity	NPD6405	Approved
0.6963	Remote Similarity	NPD6663	Approved
0.6963	Remote Similarity	NPD6407	Approved
0.6957	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD1283	Approved
0.6929	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD7330	Discontinued
0.6917	Remote Similarity	NPD3636	Approved
0.6917	Remote Similarity	NPD2861	Phase 2
0.6917	Remote Similarity	NPD3637	Approved
0.6917	Remote Similarity	NPD3635	Approved
0.6912	Remote Similarity	NPD1613	Approved
0.6912	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD943	Approved
0.6911	Remote Similarity	NPD228	Approved
0.6899	Remote Similarity	NPD3143	Discontinued
0.6899	Remote Similarity	NPD3023	Approved
0.6899	Remote Similarity	NPD3026	Approved
0.6897	Remote Similarity	NPD9273	Approved
0.6875	Remote Similarity	NPD3025	Approved
0.6875	Remote Similarity	NPD3024	Approved
0.6866	Remote Similarity	NPD2606	Approved
0.6866	Remote Similarity	NPD2605	Approved
0.6842	Remote Similarity	NPD858	Approved
0.6842	Remote Similarity	NPD599	Approved
0.6842	Remote Similarity	NPD859	Approved
0.6842	Remote Similarity	NPD602	Approved
0.6842	Remote Similarity	NPD4624	Approved
0.6835	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD5156	Approved
0.6815	Remote Similarity	NPD5155	Approved
0.6812	Remote Similarity	NPD1607	Approved
0.6812	Remote Similarity	NPD2568	Approved
0.68	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD3070	Discontinued
0.6791	Remote Similarity	NPD3018	Phase 2
0.6788	Remote Similarity	NPD3620	Phase 2
0.6788	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD2238	Phase 2
0.6788	Remote Similarity	NPD1555	Discontinued
0.678	Remote Similarity	NPD3028	Approved
0.6772	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7636	Approved
0.6769	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD1164	Approved
0.6765	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6232	Discontinued
0.675	Remote Similarity	NPD9608	Approved
0.675	Remote Similarity	NPD9610	Approved
0.6748	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD1793	Approved
0.6746	Remote Similarity	NPD1791	Approved
0.6746	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD1669	Approved
0.6742	Remote Similarity	NPD5327	Phase 3
0.6741	Remote Similarity	NPD3594	Approved
0.6741	Remote Similarity	NPD3595	Approved
0.6739	Remote Similarity	NPD5735	Approved
0.6738	Remote Similarity	NPD4721	Approved
0.6738	Remote Similarity	NPD4725	Approved
0.6738	Remote Similarity	NPD4726	Approved
0.6733	Remote Similarity	NPD7819	Suspended
0.6731	Remote Similarity	NPD7473	Discontinued
0.672	Remote Similarity	NPD9379	Approved
0.672	Remote Similarity	NPD9377	Approved
0.6718	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD1611	Approved
0.6718	Remote Similarity	NPD1281	Approved
0.6714	Remote Similarity	NPD7742	Approved
0.6714	Remote Similarity	NPD7743	Approved
0.6713	Remote Similarity	NPD3750	Approved
0.6696	Remote Similarity	NPD9094	Approved
0.6694	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD7157	Approved
0.6693	Remote Similarity	NPD709	Approved
0.6692	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD8651	Approved
0.6691	Remote Similarity	NPD2157	Approved
0.669	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.669	Remote Similarity	NPD7041	Phase 2
0.6688	Remote Similarity	NPD6959	Discontinued
0.6667	Remote Similarity	NPD2230	Approved
0.6667	Remote Similarity	NPD2935	Discontinued
0.6667	Remote Similarity	NPD2232	Approved
0.6667	Remote Similarity	NPD1240	Approved
0.6667	Remote Similarity	NPD9269	Phase 2
0.6667	Remote Similarity	NPD37	Approved
0.6667	Remote Similarity	NPD2684	Approved
0.6667	Remote Similarity	NPD5283	Phase 1
0.6667	Remote Similarity	NPD2233	Approved
0.6644	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD3553	Approved
0.6643	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD2209	Approved
0.6643	Remote Similarity	NPD6674	Discontinued
0.6643	Remote Similarity	NPD3554	Approved
0.6643	Remote Similarity	NPD2211	Approved
0.6643	Remote Similarity	NPD3552	Approved
0.6643	Remote Similarity	NPD3555	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