NPASS Compound

Structure

CID5130 OpenBabel06191715322D 24 26 0 0 1 0 0 0 0 0999 V2000 4.7135 0.7791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0949 -3.0871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3213 -2.7180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5533 2.2680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3158 1.5581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4000 1.2605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7976 -0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7976 0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3158 -2.5211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7553 -1.9389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2316 1.2605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2316 -1.2605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3158 -1.5581 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4000 -1.2605 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8340 -0.4815 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4000 -2.8186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 0.4815 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1470 -1.0592 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1024 -3.7345 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4060 2.9193 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7976 -2.0396 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 -2.0396 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 3.7976 2.0396 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 2 0 0 0 0 2 9 2 0 0 0 0 3 10 1 0 0 0 0 5 6 1 0 0 0 0 5 11 1 0 0 0 0 6 17 1 0 0 0 0 7 8 1 0 0 0 0 7 12 1 0 0 0 0 8 11 1 0 0 0 0 9 16 1 0 0 0 0 10 18 2 0 0 0 0 10 21 1 0 0 0 0 11 24 1 1 0 0 0 12 13 1 0 0 0 0 12 21 1 1 0 0 0 13 9 1 1 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 14 22 1 6 0 0 0 15 17 1 1 0 0 0 15 23 1 0 0 0 0 16 19 2 0 0 0 0 16 22 1 0 0 0 0 17 4 1 1 0 0 0 17 23 1 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	818.29
Volume:	828.389
LogP:	6.543
LogD:	3.805
LogS:	-3.487
# Rotatable Bonds:	17
TPSA:	167.03
# H-Bond Aceptor:	13
# H-Bond Donor:	0
# Rings:	7
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.118
Synthetic Accessibility Score:	6.034
Fsp3:	0.362
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.372
MDCK Permeability:	4.143276237300597e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.093
20% Bioavailability (F20%):	0.978
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	102.88282012939453%
Volume Distribution (VD):	1.806
Pgp-substrate:	4.4073710441589355%

ADMET: Metabolism

CYP1A2-inhibitor:	0.063
CYP1A2-substrate:	0.015
CYP2C19-inhibitor:	0.463
CYP2C19-substrate:	0.045
CYP2C9-inhibitor:	0.302
CYP2C9-substrate:	0.042
CYP2D6-inhibitor:	0.341
CYP2D6-substrate:	0.02
CYP3A4-inhibitor:	0.429
CYP3A4-substrate:	0.212

ADMET: Excretion

Clearance (CL):	5.856
Half-life (T1/2):	0.582

ADMET: Toxicity

hERG Blockers:	0.722
Human Hepatotoxicity (H-HT):	0.948
Drug-inuced Liver Injury (DILI):	0.993
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.006
Skin Sensitization:	0.134
Carcinogencity:	0.109
Eye Corrosion:	0.003
Eye Irritation:	0.319
Respiratory Toxicity:	0.067

Download Data

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

Natural Product: NPC5130

Natural Product ID:	NPC5130
*Common Name:**	Peroxyferolide
IUPAC Name:	n.a.
Synonyms:	Peroxyferolide
Standard InCHIKey:	IHYLMNWQQGXGJT-TYVJZBCKSA-N
Standard InCHI:	InChI=1S/C17H22O7/c1-8-7-12(21-10(3)18)13-9(2)16(19)22-14(13)15-17(4,23-15)6-5-11(8)24-20/h11-15,20H,1-2,5-7H2,3-4H3/t11-,12-,13-,14+,15-,17-/m1/s1
SMILES:	OO[C@@H]1CC[C@@]2(C)O[C@@H]2[C@@H]2[C@@H]([C@@H](CC1=C)OC(=O)C)C(=C)C(=O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518136
PubChem CID:	442290
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	roots	n.a.	n.a.	PMID[16989524]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[22863942]
NPO12721	Liriodendron tulipifera	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[24042007]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12721	Liriodendron tulipifera	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12721	Liriodendron tulipifera	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12721	Liriodendron tulipifera	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12721	Liriodendron tulipifera	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.29	ug ml-1	PMID[453541]

☑ 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 NPC5130 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	257
0.1-0.2	2112
0.2-0.3	6913
0.3-0.4	15043
0.4-0.5	10326
0.5-0.6	5650
0.6-0.7	1947
0.7-0.8	353
0.8-0.85	65
0.85-0.9	30
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9157	High Similarity	NPC138647
0.9157	High Similarity	NPC470238
0.908	High Similarity	NPC475881
0.908	High Similarity	NPC70251
0.907	High Similarity	NPC151770
0.8837	High Similarity	NPC231889
0.8824	High Similarity	NPC304509
0.8824	High Similarity	NPC149725
0.8824	High Similarity	NPC47958
0.881	High Similarity	NPC257358
0.881	High Similarity	NPC474472
0.8764	High Similarity	NPC212486
0.875	High Similarity	NPC475748
0.8696	High Similarity	NPC474213
0.8667	High Similarity	NPC473330
0.8667	High Similarity	NPC473316
0.8667	High Similarity	NPC190294
0.8636	High Similarity	NPC166919
0.8621	High Similarity	NPC186148
0.8605	High Similarity	NPC50362
0.8605	High Similarity	NPC38468
0.8605	High Similarity	NPC319795
0.8588	High Similarity	NPC128429
0.8588	High Similarity	NPC272814
0.8571	High Similarity	NPC475659
0.8571	High Similarity	NPC14961
0.8571	High Similarity	NPC270013
0.8523	High Similarity	NPC177629
0.8523	High Similarity	NPC58219
0.8511	High Similarity	NPC201718
0.8506	High Similarity	NPC470242
0.8506	High Similarity	NPC50637
0.8478	Intermediate Similarity	NPC76862
0.8478	Intermediate Similarity	NPC470883
0.8478	Intermediate Similarity	NPC31645
0.8478	Intermediate Similarity	NPC39859
0.8478	Intermediate Similarity	NPC476315
0.8478	Intermediate Similarity	NPC473859
0.8478	Intermediate Similarity	NPC158416
0.8462	Intermediate Similarity	NPC303942
0.8462	Intermediate Similarity	NPC57405
0.8462	Intermediate Similarity	NPC471147
0.8462	Intermediate Similarity	NPC81386
0.8462	Intermediate Similarity	NPC474035
0.8452	Intermediate Similarity	NPC474981
0.8444	Intermediate Similarity	NPC184463
0.8427	Intermediate Similarity	NPC307411
0.8427	Intermediate Similarity	NPC92974
0.8404	Intermediate Similarity	NPC288876
0.8387	Intermediate Similarity	NPC323421
0.8387	Intermediate Similarity	NPC328562
0.8352	Intermediate Similarity	NPC475912
0.8352	Intermediate Similarity	NPC476300
0.8333	Intermediate Similarity	NPC49342
0.8333	Intermediate Similarity	NPC251385
0.8333	Intermediate Similarity	NPC51004
0.8315	Intermediate Similarity	NPC202672
0.8298	Intermediate Similarity	NPC279561
0.8298	Intermediate Similarity	NPC473326
0.8295	Intermediate Similarity	NPC474949
0.8295	Intermediate Similarity	NPC475019
0.8295	Intermediate Similarity	NPC474762
0.8295	Intermediate Similarity	NPC476015
0.828	Intermediate Similarity	NPC279621
0.8276	Intermediate Similarity	NPC474780
0.8261	Intermediate Similarity	NPC140543
0.8242	Intermediate Similarity	NPC12172
0.8242	Intermediate Similarity	NPC208886
0.8242	Intermediate Similarity	NPC30515
0.8211	Intermediate Similarity	NPC186861
0.8202	Intermediate Similarity	NPC475703
0.8202	Intermediate Similarity	NPC190753
0.8182	Intermediate Similarity	NPC329749
0.8172	Intermediate Similarity	NPC475900
0.8172	Intermediate Similarity	NPC474947
0.8172	Intermediate Similarity	NPC36954
0.8172	Intermediate Similarity	NPC476053
0.8152	Intermediate Similarity	NPC81419
0.8152	Intermediate Similarity	NPC179746
0.8152	Intermediate Similarity	NPC228451
0.8152	Intermediate Similarity	NPC125674
0.8152	Intermediate Similarity	NPC475838
0.814	Intermediate Similarity	NPC141810
0.8132	Intermediate Similarity	NPC206614
0.8132	Intermediate Similarity	NPC474323
0.8132	Intermediate Similarity	NPC329857
0.8132	Intermediate Similarity	NPC469718
0.8132	Intermediate Similarity	NPC312042
0.8125	Intermediate Similarity	NPC15993
0.8125	Intermediate Similarity	NPC264477
0.8125	Intermediate Similarity	NPC476270
0.8125	Intermediate Similarity	NPC477511
0.8118	Intermediate Similarity	NPC617
0.8105	Intermediate Similarity	NPC208233
0.809	Intermediate Similarity	NPC284902
0.809	Intermediate Similarity	NPC162071
0.8085	Intermediate Similarity	NPC17585
0.8085	Intermediate Similarity	NPC476009
0.8085	Intermediate Similarity	NPC35498
0.8068	Intermediate Similarity	NPC475963
0.8068	Intermediate Similarity	NPC3464
0.8068	Intermediate Similarity	NPC151176
0.8065	Intermediate Similarity	NPC476267
0.8065	Intermediate Similarity	NPC474247
0.8043	Intermediate Similarity	NPC20713
0.8041	Intermediate Similarity	NPC320019
0.8041	Intermediate Similarity	NPC324017
0.8022	Intermediate Similarity	NPC474032
0.8022	Intermediate Similarity	NPC474951
0.8022	Intermediate Similarity	NPC472872
0.8022	Intermediate Similarity	NPC173926
0.8021	Intermediate Similarity	NPC471381
0.8	Intermediate Similarity	NPC471140
0.8	Intermediate Similarity	NPC118601
0.8	Intermediate Similarity	NPC471150
0.8	Intermediate Similarity	NPC270270
0.7979	Intermediate Similarity	NPC471141
0.7955	Intermediate Similarity	NPC170286
0.7938	Intermediate Similarity	NPC474339
0.7938	Intermediate Similarity	NPC47880
0.7938	Intermediate Similarity	NPC164598
0.7938	Intermediate Similarity	NPC473332
0.7935	Intermediate Similarity	NPC476004
0.7935	Intermediate Similarity	NPC473619
0.7935	Intermediate Similarity	NPC62815
0.7935	Intermediate Similarity	NPC474761
0.7931	Intermediate Similarity	NPC207188
0.7912	Intermediate Similarity	NPC178875
0.7912	Intermediate Similarity	NPC281516
0.79	Intermediate Similarity	NPC477513
0.7895	Intermediate Similarity	NPC230800
0.7889	Intermediate Similarity	NPC469626
0.7889	Intermediate Similarity	NPC204048
0.7889	Intermediate Similarity	NPC475491
0.7879	Intermediate Similarity	NPC474741
0.7879	Intermediate Similarity	NPC477510
0.7879	Intermediate Similarity	NPC471143
0.7872	Intermediate Similarity	NPC66581
0.7857	Intermediate Similarity	NPC149371
0.7857	Intermediate Similarity	NPC471148
0.7849	Intermediate Similarity	NPC470373
0.7849	Intermediate Similarity	NPC155215
0.7849	Intermediate Similarity	NPC470379
0.7849	Intermediate Similarity	NPC473321
0.7841	Intermediate Similarity	NPC246076
0.7835	Intermediate Similarity	NPC475949
0.7835	Intermediate Similarity	NPC477512
0.7812	Intermediate Similarity	NPC474921
0.78	Intermediate Similarity	NPC243998
0.78	Intermediate Similarity	NPC223450
0.78	Intermediate Similarity	NPC54737
0.7789	Intermediate Similarity	NPC163228
0.7789	Intermediate Similarity	NPC471142
0.7778	Intermediate Similarity	NPC215364
0.7778	Intermediate Similarity	NPC474547
0.7766	Intermediate Similarity	NPC472874
0.7766	Intermediate Similarity	NPC273579
0.7766	Intermediate Similarity	NPC258216
0.7766	Intermediate Similarity	NPC295204
0.7766	Intermediate Similarity	NPC288240
0.7766	Intermediate Similarity	NPC162205
0.7742	Intermediate Similarity	NPC65359
0.7742	Intermediate Similarity	NPC179394
0.7742	Intermediate Similarity	NPC144133
0.7742	Intermediate Similarity	NPC475855
0.7742	Intermediate Similarity	NPC80875
0.7732	Intermediate Similarity	NPC45125
0.7732	Intermediate Similarity	NPC471144
0.7727	Intermediate Similarity	NPC47635
0.7717	Intermediate Similarity	NPC217983
0.7717	Intermediate Similarity	NPC79549
0.7717	Intermediate Similarity	NPC473715
0.7717	Intermediate Similarity	NPC224652
0.7717	Intermediate Similarity	NPC207114
0.7708	Intermediate Similarity	NPC476275
0.7701	Intermediate Similarity	NPC80999
0.7701	Intermediate Similarity	NPC19841
0.7692	Intermediate Similarity	NPC304558
0.7684	Intermediate Similarity	NPC71589
0.7677	Intermediate Similarity	NPC474747
0.7667	Intermediate Similarity	NPC72464
0.766	Intermediate Similarity	NPC469627
0.766	Intermediate Similarity	NPC191339
0.766	Intermediate Similarity	NPC158061
0.766	Intermediate Similarity	NPC329952
0.766	Intermediate Similarity	NPC184063
0.766	Intermediate Similarity	NPC165180
0.766	Intermediate Similarity	NPC286341
0.766	Intermediate Similarity	NPC133698
0.7634	Intermediate Similarity	NPC4986
0.7634	Intermediate Similarity	NPC215556
0.7634	Intermediate Similarity	NPC295312
0.7629	Intermediate Similarity	NPC474313
0.7609	Intermediate Similarity	NPC266957
0.7609	Intermediate Similarity	NPC24728
0.7609	Intermediate Similarity	NPC248602
0.7604	Intermediate Similarity	NPC477922
0.7604	Intermediate Similarity	NPC472873
0.7604	Intermediate Similarity	NPC107476
0.7604	Intermediate Similarity	NPC56369

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 NPC5130 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	297
0.1-0.2	2876
0.2-0.3	3719
0.3-0.4	1564
0.4-0.5	508
0.5-0.6	173
0.6-0.7	11
0.7-0.8	1
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8605	High Similarity	NPD1733	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD1695	Approved
0.7368	Intermediate Similarity	NPD6698	Approved
0.7368	Intermediate Similarity	NPD46	Approved
0.7048	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7838	Discovery
0.69	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6371	Approved
0.6768	Remote Similarity	NPD7983	Approved
0.6486	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD6008	Approved
0.6476	Remote Similarity	NPD6648	Approved
0.6422	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5344	Discontinued
0.6396	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6686	Approved
0.6311	Remote Similarity	NPD5282	Discontinued
0.6306	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD6053	Discontinued
0.6226	Remote Similarity	NPD4225	Approved
0.6216	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD5778	Approved
0.6214	Remote Similarity	NPD5779	Approved
0.6207	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6435	Approved
0.6186	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD1694	Approved
0.6134	Remote Similarity	NPD8517	Approved
0.6134	Remote Similarity	NPD8515	Approved
0.6134	Remote Similarity	NPD8516	Approved
0.6134	Remote Similarity	NPD8513	Phase 3
0.6122	Remote Similarity	NPD7154	Phase 3
0.61	Remote Similarity	NPD4249	Approved
0.6068	Remote Similarity	NPD7115	Discovery
0.604	Remote Similarity	NPD4250	Approved
0.604	Remote Similarity	NPD4251	Approved
0.6033	Remote Similarity	NPD7642	Approved
0.6019	Remote Similarity	NPD5785	Approved
0.5979	Remote Similarity	NPD5368	Approved
0.5948	Remote Similarity	NPD8133	Approved
0.5941	Remote Similarity	NPD5786	Approved
0.5922	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD6101	Approved
0.5918	Remote Similarity	NPD5369	Approved
0.5902	Remote Similarity	NPD7830	Approved
0.5902	Remote Similarity	NPD7829	Approved
0.5888	Remote Similarity	NPD7839	Suspended
0.5887	Remote Similarity	NPD8074	Phase 3
0.5868	Remote Similarity	NPD8269	Approved
0.5868	Remote Similarity	NPD8267	Approved
0.5868	Remote Similarity	NPD8266	Approved
0.5868	Remote Similarity	NPD8268	Approved
0.5859	Remote Similarity	NPD5209	Approved
0.5842	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD5363	Approved
0.5816	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD4822	Approved
0.5816	Remote Similarity	NPD4821	Approved
0.5816	Remote Similarity	NPD4820	Approved
0.5816	Remote Similarity	NPD4819	Approved
0.5812	Remote Similarity	NPD4632	Approved
0.581	Remote Similarity	NPD6411	Approved
0.5806	Remote Similarity	NPD7507	Approved
0.58	Remote Similarity	NPD5362	Discontinued
0.5785	Remote Similarity	NPD6319	Approved
0.578	Remote Similarity	NPD7638	Approved
0.5755	Remote Similarity	NPD6399	Phase 3
0.575	Remote Similarity	NPD7641	Discontinued
0.5727	Remote Similarity	NPD7639	Approved
0.5727	Remote Similarity	NPD7640	Approved
0.5726	Remote Similarity	NPD8297	Approved
0.5726	Remote Similarity	NPD7492	Approved
0.5725	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5703	Remote Similarity	NPD7260	Phase 2
0.5702	Remote Similarity	NPD5697	Approved
0.57	Remote Similarity	NPD4269	Approved
0.57	Remote Similarity	NPD4270	Approved
0.568	Remote Similarity	NPD8451	Approved
0.568	Remote Similarity	NPD6616	Approved
0.568	Remote Similarity	NPD8273	Phase 1
0.5676	Remote Similarity	NPD1700	Approved
0.5669	Remote Similarity	NPD7319	Approved
0.5667	Remote Similarity	NPD6009	Approved
0.566	Remote Similarity	NPD8034	Phase 2
0.566	Remote Similarity	NPD8035	Phase 2
0.5659	Remote Similarity	NPD6845	Suspended
0.5656	Remote Similarity	NPD6054	Approved
0.5652	Remote Similarity	NPD6899	Approved
0.5652	Remote Similarity	NPD6881	Approved
0.5645	Remote Similarity	NPD7604	Phase 2
0.5641	Remote Similarity	NPD6649	Approved
0.5641	Remote Similarity	NPD6650	Approved
0.5635	Remote Similarity	NPD8448	Approved
0.5635	Remote Similarity	NPD7078	Approved
0.5631	Remote Similarity	NPD6422	Discontinued
0.5625	Remote Similarity	NPD8039	Approved
0.5614	Remote Similarity	NPD5739	Approved
0.5614	Remote Similarity	NPD6402	Approved
0.5614	Remote Similarity	NPD7128	Approved
0.5614	Remote Similarity	NPD6675	Approved
0.5612	Remote Similarity	NPD4271	Approved
0.5612	Remote Similarity	NPD4268	Approved
0.561	Remote Similarity	NPD5983	Phase 2
0.561	Remote Similarity	NPD6921	Approved
0.561	Remote Similarity	NPD6015	Approved
0.561	Remote Similarity	NPD6016	Approved
0.5603	Remote Similarity	NPD6014	Approved
0.5603	Remote Similarity	NPD6372	Approved
0.5603	Remote Similarity	NPD6012	Approved
0.5603	Remote Similarity	NPD6373	Approved
0.5603	Remote Similarity	NPD6013	Approved
0.56	Remote Similarity	NPD1779	Approved
0.56	Remote Similarity	NPD1780	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