NPASS Compound

Structure

CID30570 OpenBabel06191715362D 38 43 0 0 1 0 0 0 0 0999 V2000 -2.6412 2.1867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1071 1.3403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7442 -2.4378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1022 0.0054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3764 2.7422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8877 1.8959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9485 -2.4378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7948 -1.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3339 -0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4875 0.0054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9485 0.4940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7948 0.9826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8877 3.5886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4446 1.0495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4218 2.7422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6412 -1.4606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1298 1.3403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1022 -1.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9105 1.8959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4218 1.0495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9559 0.2032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7948 -0.9719 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3339 -1.4606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4446 -0.6432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7906 -1.3694 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4218 -0.6432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9485 -0.4833 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6412 -0.4833 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6412 0.4940 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1022 -0.9719 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9105 3.5886 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.1802 -1.9492 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1970 -3.2812 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9105 -1.4895 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6185 0.4940 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4875 -1.9492 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9105 0.2032 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 17 2 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 27 1 0 0 0 0 5 6 2 0 0 0 0 5 13 1 0 0 0 0 6 19 1 0 0 0 0 7 8 1 0 0 0 0 7 18 2 0 0 0 0 8 22 1 0 0 0 0 9 10 1 0 0 0 0 9 23 1 0 0 0 0 10 28 1 0 0 0 0 11 12 1 0 0 0 0 11 27 1 0 0 0 0 12 29 1 0 0 0 0 13 31 2 0 0 0 0 14 20 2 0 0 0 0 14 21 1 0 0 0 0 15 19 2 0 0 0 0 15 31 1 0 0 0 0 16 28 1 0 0 0 0 16 36 1 0 0 0 0 17 29 1 0 0 0 0 19 20 1 0 0 0 0 20 37 1 0 0 0 0 21 24 2 0 0 0 0 21 38 1 0 0 0 0 22 27 1 6 0 0 0 22 28 1 0 0 0 0 23 32 2 0 0 0 0 23 36 1 0 0 0 0 24 25 1 0 0 0 0 24 26 1 0 0 0 0 25 30 1 6 0 0 0 25 33 1 0 0 0 0 26 34 2 0 0 0 0 26 37 1 0 0 0 0 27 30 1 1 0 0 0 28 29 1 6 0 0 0 29 35 1 1 0 0 0 30 18 1 1 0 0 0 30 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	519.23
Volume:	524.897
LogP:	2.697
LogD:	2.566
LogS:	-4.216
# Rotatable Bonds:	2
TPSA:	119.09
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.446
Synthetic Accessibility Score:	5.738
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
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:	-4.887
MDCK Permeability:	2.002545261348132e-05
Pgp-inhibitor:	0.112
Pgp-substrate:	0.505
Human Intestinal Absorption (HIA):	0.079
20% Bioavailability (F20%):	0.283
30% Bioavailability (F30%):	0.919

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.868
Plasma Protein Binding (PPB):	76.01636505126953%
Volume Distribution (VD):	1.507
Pgp-substrate:	20.19173812866211%

ADMET: Metabolism

CYP1A2-inhibitor:	0.139
CYP1A2-substrate:	0.833
CYP2C19-inhibitor:	0.346
CYP2C19-substrate:	0.593
CYP2C9-inhibitor:	0.323
CYP2C9-substrate:	0.061
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.925
CYP3A4-substrate:	0.639

ADMET: Excretion

Clearance (CL):	5.927
Half-life (T1/2):	0.428

ADMET: Toxicity

hERG Blockers:	0.587
Human Hepatotoxicity (H-HT):	0.787
Drug-inuced Liver Injury (DILI):	0.807
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.902
Maximum Recommended Daily Dose:	0.974
Skin Sensitization:	0.217
Carcinogencity:	0.581
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.929

Download Data

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

Natural Product: NPC30570

Natural Product ID:	NPC30570
*Common Name:**	Oxalicine B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GADSICAILMLRQB-GVRUMSNVSA-N
Standard InCHI:	InChI=1S/C30H33NO7/c1-17(2)29(35)12-11-27(4)22(28(29)10-9-23(32)36-16-28)8-7-18(3)30(27)25(33)24-21(38-30)14-20(37-26(24)34)19-6-5-13-31-15-19/h5-7,13-15,22,25,33,35H,1,8-12,16H2,2-4H3/t22-,25-,27+,28-,29+,30+/m0/s1
SMILES:	O=C1CC[C@]2(CO1)[C@H]1CC=C([C@@]3([C@]1(C)CC[C@@]2(O)C(=C)C)Oc1c([C@@H]3O)c(=O)oc(c1)c1cccnc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL474673
PubChem CID:	21593946
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
NPO302	Penicillium thiersii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787428]
NPO3117	Aconitum legendrei	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15125.2	Taxus wallichiana var. wallichiana	Varieties	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3117	Aconitum legendrei	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3117	Aconitum legendrei	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9566	Abies canadensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10069	Chaptalia nutans	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15125.2	Taxus wallichiana var. wallichiana	Varieties	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10990	Myristica surinamensis	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9135	Ligularia fauriei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3117	Aconitum legendrei	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2803	Lyonetia clerkella	Species	Lyonetiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO302	Penicillium thiersii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11104	Diadema antillarum	Species	Diadematidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9915	Pieris brassicae	Species	Pieridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2010	Viburnum ichangense	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8958	Centella erecta	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6764	Dianthus japonicus	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8763	Erythrina herbacea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16983	Persea obovatifolia	Species	Lauraceae	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
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	62.0	%	PMID[492487]
NPT352	Organism	Frankliniella occidentalis	Frankliniella occidentalis	mortality	=	32.0	%	PMID[492488]
NPT348	Organism	Myzus persicae	Myzus persicae	mortality	=	82.0	%	PMID[492488]
NPT348	Organism	Myzus persicae	Myzus persicae	mortality	=	87.0	%	PMID[492488]

☑ 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 NPC30570 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	409
0.1-0.2	1751
0.2-0.3	4292
0.3-0.4	10674
0.4-0.5	9807
0.5-0.6	12953
0.6-0.7	2477
0.7-0.8	219
0.8-0.85	95
0.85-0.9	15
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9843	High Similarity	NPC292517
0.9742	High Similarity	NPC162812
0.9278	High Similarity	NPC475835
0.9029	High Similarity	NPC124029
0.8937	High Similarity	NPC211920
0.8932	High Similarity	NPC477902
0.89	High Similarity	NPC477906
0.878	High Similarity	NPC216428
0.8768	High Similarity	NPC264674
0.8756	High Similarity	NPC103230
0.8732	High Similarity	NPC62367
0.8725	High Similarity	NPC477907
0.8725	High Similarity	NPC42678
0.8725	High Similarity	NPC477909
0.8725	High Similarity	NPC477910
0.8706	High Similarity	NPC472550
0.8706	High Similarity	NPC48042
0.8706	High Similarity	NPC304179
0.8696	High Similarity	NPC477912
0.867	High Similarity	NPC472553
0.866	High Similarity	NPC26881
0.8657	High Similarity	NPC63041
0.8647	High Similarity	NPC477901
0.8632	High Similarity	NPC150698
0.8632	High Similarity	NPC96801
0.8619	High Similarity	NPC148860
0.8606	High Similarity	NPC477903
0.8599	High Similarity	NPC472555
0.8592	High Similarity	NPC206343
0.8592	High Similarity	NPC477908
0.8578	High Similarity	NPC475601
0.8565	High Similarity	NPC477911
0.8565	High Similarity	NPC235364
0.8524	High Similarity	NPC471980
0.851	High Similarity	NPC84815
0.851	High Similarity	NPC301368
0.8505	High Similarity	NPC469748
0.8502	High Similarity	NPC475408
0.8502	High Similarity	NPC471014
0.8502	High Similarity	NPC471016
0.8498	Intermediate Similarity	NPC91125
0.8495	Intermediate Similarity	NPC228331
0.8495	Intermediate Similarity	NPC319128
0.8483	Intermediate Similarity	NPC477900
0.8483	Intermediate Similarity	NPC328154
0.8483	Intermediate Similarity	NPC477899
0.8476	Intermediate Similarity	NPC127026
0.8476	Intermediate Similarity	NPC127720
0.8462	Intermediate Similarity	NPC144779
0.8462	Intermediate Similarity	NPC294579
0.8454	Intermediate Similarity	NPC470306
0.8413	Intermediate Similarity	NPC6981
0.8341	Intermediate Similarity	NPC35208
0.8317	Intermediate Similarity	NPC4421
0.831	Intermediate Similarity	NPC475137
0.831	Intermediate Similarity	NPC473850
0.831	Intermediate Similarity	NPC475498
0.8295	Intermediate Similarity	NPC238278
0.8286	Intermediate Similarity	NPC158020
0.8286	Intermediate Similarity	NPC6576
0.8286	Intermediate Similarity	NPC473115
0.8286	Intermediate Similarity	NPC212768
0.8286	Intermediate Similarity	NPC473089
0.8286	Intermediate Similarity	NPC75600
0.8279	Intermediate Similarity	NPC471977
0.8279	Intermediate Similarity	NPC471190
0.8279	Intermediate Similarity	NPC475644
0.8279	Intermediate Similarity	NPC470486
0.8273	Intermediate Similarity	NPC253482
0.8263	Intermediate Similarity	NPC250807
0.8263	Intermediate Similarity	NPC76565
0.8263	Intermediate Similarity	NPC57797
0.8257	Intermediate Similarity	NPC475426
0.8252	Intermediate Similarity	NPC472752
0.8249	Intermediate Similarity	NPC30456
0.8243	Intermediate Similarity	NPC475648
0.8233	Intermediate Similarity	NPC328186
0.8233	Intermediate Similarity	NPC122968
0.8233	Intermediate Similarity	NPC475631
0.8233	Intermediate Similarity	NPC228377
0.8233	Intermediate Similarity	NPC475600
0.8233	Intermediate Similarity	NPC476110
0.8233	Intermediate Similarity	NPC477787
0.8233	Intermediate Similarity	NPC87152
0.8203	Intermediate Similarity	NPC475303
0.8203	Intermediate Similarity	NPC475596
0.8203	Intermediate Similarity	NPC316841
0.8194	Intermediate Similarity	NPC475362
0.8186	Intermediate Similarity	NPC473506
0.8174	Intermediate Similarity	NPC170751
0.8174	Intermediate Similarity	NPC327769
0.8148	Intermediate Similarity	NPC285411
0.8148	Intermediate Similarity	NPC146824
0.8148	Intermediate Similarity	NPC14116
0.8146	Intermediate Similarity	NPC289086
0.8134	Intermediate Similarity	NPC476467
0.8128	Intermediate Similarity	NPC237702
0.8119	Intermediate Similarity	NPC292416
0.8119	Intermediate Similarity	NPC473689
0.8111	Intermediate Similarity	NPC311196
0.8111	Intermediate Similarity	NPC134384
0.8091	Intermediate Similarity	NPC475406
0.8082	Intermediate Similarity	NPC320324
0.8082	Intermediate Similarity	NPC213143
0.8082	Intermediate Similarity	NPC244839
0.8082	Intermediate Similarity	NPC319880
0.8056	Intermediate Similarity	NPC233727
0.8054	Intermediate Similarity	NPC38959
0.8054	Intermediate Similarity	NPC327904
0.8047	Intermediate Similarity	NPC477788
0.8019	Intermediate Similarity	NPC62844
0.8019	Intermediate Similarity	NPC193361
0.7957	Intermediate Similarity	NPC471015
0.7944	Intermediate Similarity	NPC187494
0.7885	Intermediate Similarity	NPC148896
0.7885	Intermediate Similarity	NPC471013
0.7885	Intermediate Similarity	NPC180668
0.7877	Intermediate Similarity	NPC280473
0.7877	Intermediate Similarity	NPC323551
0.7864	Intermediate Similarity	NPC470279
0.784	Intermediate Similarity	NPC51008
0.784	Intermediate Similarity	NPC41724
0.7834	Intermediate Similarity	NPC253314
0.783	Intermediate Similarity	NPC40919
0.783	Intermediate Similarity	NPC470189
0.7817	Intermediate Similarity	NPC475315
0.7817	Intermediate Similarity	NPC324619
0.7787	Intermediate Similarity	NPC473833
0.7778	Intermediate Similarity	NPC319556
0.7773	Intermediate Similarity	NPC475533
0.7773	Intermediate Similarity	NPC470190
0.7758	Intermediate Similarity	NPC471004
0.7749	Intermediate Similarity	NPC476516
0.7749	Intermediate Similarity	NPC10904
0.7729	Intermediate Similarity	NPC160127
0.7729	Intermediate Similarity	NPC50997
0.7729	Intermediate Similarity	NPC476090
0.771	Intermediate Similarity	NPC111732
0.7685	Intermediate Similarity	NPC207531
0.7681	Intermediate Similarity	NPC324245
0.7681	Intermediate Similarity	NPC320748
0.7674	Intermediate Similarity	NPC165837
0.7673	Intermediate Similarity	NPC325775
0.7673	Intermediate Similarity	NPC328798
0.7656	Intermediate Similarity	NPC32451
0.7656	Intermediate Similarity	NPC328559
0.7647	Intermediate Similarity	NPC471978
0.7633	Intermediate Similarity	NPC329024
0.7617	Intermediate Similarity	NPC326930
0.7617	Intermediate Similarity	NPC53255
0.7617	Intermediate Similarity	NPC85879
0.7617	Intermediate Similarity	NPC475301
0.7608	Intermediate Similarity	NPC79223
0.7594	Intermediate Similarity	NPC309498
0.7585	Intermediate Similarity	NPC13603
0.7573	Intermediate Similarity	NPC328928
0.7562	Intermediate Similarity	NPC327373
0.7559	Intermediate Similarity	NPC156044
0.7512	Intermediate Similarity	NPC59033
0.7512	Intermediate Similarity	NPC317672
0.75	Intermediate Similarity	NPC476517
0.7488	Intermediate Similarity	NPC289786
0.7479	Intermediate Similarity	NPC471979
0.7476	Intermediate Similarity	NPC127647
0.7475	Intermediate Similarity	NPC325093
0.7475	Intermediate Similarity	NPC322043
0.7465	Intermediate Similarity	NPC25442
0.7465	Intermediate Similarity	NPC12944
0.7463	Intermediate Similarity	NPC471997
0.7406	Intermediate Similarity	NPC155792
0.7402	Intermediate Similarity	NPC318020
0.7379	Intermediate Similarity	NPC182814
0.7345	Intermediate Similarity	NPC57690
0.7333	Intermediate Similarity	NPC141428
0.7333	Intermediate Similarity	NPC235885
0.7297	Intermediate Similarity	NPC314270
0.7277	Intermediate Similarity	NPC2395
0.7251	Intermediate Similarity	NPC473053
0.7246	Intermediate Similarity	NPC107123
0.7212	Intermediate Similarity	NPC44354
0.7207	Intermediate Similarity	NPC204491
0.7204	Intermediate Similarity	NPC20593
0.7204	Intermediate Similarity	NPC146724
0.7195	Intermediate Similarity	NPC317752
0.7183	Intermediate Similarity	NPC102008
0.7178	Intermediate Similarity	NPC478045
0.715	Intermediate Similarity	NPC123395
0.7149	Intermediate Similarity	NPC151976
0.7149	Intermediate Similarity	NPC37473
0.7149	Intermediate Similarity	NPC267926
0.7149	Intermediate Similarity	NPC318299
0.7137	Intermediate Similarity	NPC266192
0.7136	Intermediate Similarity	NPC477975
0.711	Intermediate Similarity	NPC238457
0.711	Intermediate Similarity	NPC18661
0.7105	Intermediate Similarity	NPC473449
0.7101	Intermediate Similarity	NPC207851
0.7089	Intermediate Similarity	NPC15406
0.7089	Intermediate Similarity	NPC109922
0.7085	Intermediate Similarity	NPC474217

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 NPC30570 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	262
0.1-0.2	610
0.2-0.3	870
0.3-0.4	1993
0.4-0.5	2764
0.5-0.6	2076
0.6-0.7	546
0.7-0.8	29
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7696	Intermediate Similarity	NPD8468	Phase 2
0.7569	Intermediate Similarity	NPD8326	Phase 3
0.7569	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD8325	Phase 3
0.75	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6635	Approved
0.7385	Intermediate Similarity	NPD7069	Discontinued
0.7363	Intermediate Similarity	NPD6641	Approved
0.7363	Intermediate Similarity	NPD6642	Approved
0.7363	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5088	Discontinued
0.7339	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD6529	Discontinued
0.7222	Intermediate Similarity	NPD7396	Approved
0.7191	Intermediate Similarity	NPD1483	Discontinued
0.7183	Intermediate Similarity	NPD7777	Approved
0.7183	Intermediate Similarity	NPD7778	Approved
0.7183	Intermediate Similarity	NPD53	Approved
0.7179	Intermediate Similarity	NPD6026	Approved
0.7156	Intermediate Similarity	NPD6361	Phase 2
0.713	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD7234	Approved
0.7129	Intermediate Similarity	NPD7233	Approved
0.7123	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7106	Intermediate Similarity	NPD7885	Phase 2
0.7106	Intermediate Similarity	NPD7886	Phase 2
0.7094	Intermediate Similarity	NPD8409	Suspended
0.7083	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD4086	Phase 1
0.704	Intermediate Similarity	NPD3795	Approved
0.704	Intermediate Similarity	NPD3794	Approved
0.7032	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD8063	Discontinued
0.6985	Remote Similarity	NPD2511	Approved
0.6955	Remote Similarity	NPD7010	Phase 3
0.6947	Remote Similarity	NPD4989	Phase 2
0.6933	Remote Similarity	NPD7707	Approved
0.693	Remote Similarity	NPD8479	Phase 2
0.6912	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.691	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5147	Discontinued
0.69	Remote Similarity	NPD6298	Discontinued
0.6884	Remote Similarity	NPD820	Phase 3
0.6884	Remote Similarity	NPD4427	Phase 2
0.6881	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.688	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD4375	Approved
0.6855	Remote Similarity	NPD7708	Approved
0.6852	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD7562	Approved
0.6842	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.684	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD4889	Approved
0.682	Remote Similarity	NPD8485	Approved
0.6815	Remote Similarity	NPD7955	Approved
0.6815	Remote Similarity	NPD7956	Approved
0.6813	Remote Similarity	NPD7803	Approved
0.6789	Remote Similarity	NPD8370	Discontinued
0.6784	Remote Similarity	NPD4897	Phase 2
0.6781	Remote Similarity	NPD7426	Phase 1
0.6776	Remote Similarity	NPD3321	Discontinued
0.6765	Remote Similarity	NPD5891	Approved
0.6759	Remote Similarity	NPD4529	Approved
0.6759	Remote Similarity	NPD4528	Approved
0.6759	Remote Similarity	NPD4526	Approved
0.6759	Remote Similarity	NPD4551	Phase 2
0.6757	Remote Similarity	NPD4122	Approved
0.6757	Remote Similarity	NPD4035	Approved
0.6757	Remote Similarity	NPD4033	Approved
0.6757	Remote Similarity	NPD4038	Approved
0.6757	Remote Similarity	NPD32	Approved
0.6757	Remote Similarity	NPD31	Approved
0.6757	Remote Similarity	NPD4034	Approved
0.6757	Remote Similarity	NPD4036	Approved
0.6757	Remote Similarity	NPD4039	Approved
0.6757	Remote Similarity	NPD4037	Approved
0.6756	Remote Similarity	NPD6262	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD5506	Approved
0.6753	Remote Similarity	NPD5507	Approved
0.6748	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD6206	Phase 1
0.6734	Remote Similarity	NPD8373	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD4021	Phase 2
0.6727	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD4500	Approved
0.6727	Remote Similarity	NPD4601	Approved
0.6727	Remote Similarity	NPD4600	Approved
0.6727	Remote Similarity	NPD4501	Approved
0.6726	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD6276	Discontinued
0.6719	Remote Similarity	NPD2896	Discontinued
0.6713	Remote Similarity	NPD6665	Discontinued
0.671	Remote Similarity	NPD3280	Approved
0.6709	Remote Similarity	NPD7796	Approved
0.6709	Remote Similarity	NPD7797	Approved
0.6696	Remote Similarity	NPD7878	Phase 2
0.6694	Remote Similarity	NPD8412	Phase 1
0.6682	Remote Similarity	NPD8020	Approved
0.6682	Remote Similarity	NPD8021	Approved
0.6682	Remote Similarity	NPD3386	Phase 2
0.6681	Remote Similarity	NPD3393	Approved
0.6681	Remote Similarity	NPD3394	Approved
0.6681	Remote Similarity	NPD3389	Approved
0.6667	Remote Similarity	NPD2336	Approved
0.6667	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5003	Discontinued
0.6652	Remote Similarity	NPD4417	Approved
0.6651	Remote Similarity	NPD4334	Discontinued
0.6639	Remote Similarity	NPD7967	Discontinued
0.6638	Remote Similarity	NPD5640	Discontinued
0.6636	Remote Similarity	NPD3924	Approved
0.6636	Remote Similarity	NPD3921	Approved
0.6636	Remote Similarity	NPD3922	Approved
0.6636	Remote Similarity	NPD6569	Phase 2
0.6636	Remote Similarity	NPD3923	Approved
0.6635	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD5899	Approved
0.6635	Remote Similarity	NPD43	Approved
0.6635	Remote Similarity	NPD6182	Approved
0.6635	Remote Similarity	NPD5898	Approved
0.6635	Remote Similarity	NPD5897	Approved
0.6634	Remote Similarity	NPD2582	Approved
0.6634	Remote Similarity	NPD2581	Approved
0.6624	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD7395	Discontinued
0.662	Remote Similarity	NPD8360	Approved
0.662	Remote Similarity	NPD8361	Approved
0.662	Remote Similarity	NPD2544	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD2510	Approved
0.6593	Remote Similarity	NPD2509	Approved
0.6583	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.658	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7470	Discontinued
0.6578	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD7957	Phase 1
0.6578	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6479	Discontinued
0.6574	Remote Similarity	NPD8091	Phase 3
0.6571	Remote Similarity	NPD5100	Phase 3
0.6568	Remote Similarity	NPD8289	Discontinued
0.6565	Remote Similarity	NPD5148	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD5149	Phase 2
0.6564	Remote Similarity	NPD4437	Phase 3
0.6562	Remote Similarity	NPD5513	Phase 2
0.6562	Remote Similarity	NPD5487	Phase 1
0.6561	Remote Similarity	NPD6261	Phase 3
0.656	Remote Similarity	NPD4376	Phase 3
0.6559	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6568	Discontinued
0.6552	Remote Similarity	NPD1926	Approved
0.655	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.655	Remote Similarity	NPD3816	Phase 1
0.655	Remote Similarity	NPD3815	Phase 1
0.6549	Remote Similarity	NPD5429	Discontinued
0.6548	Remote Similarity	NPD3813	Approved
0.6548	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD2307	Discontinued
0.6544	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD6281	Approved
0.6544	Remote Similarity	NPD8435	Approved
0.6544	Remote Similarity	NPD2564	Approved
0.6544	Remote Similarity	NPD2565	Phase 2
0.6543	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD6494	Phase 2
0.6542	Remote Similarity	NPD7558	Phase 2
0.654	Remote Similarity	NPD1032	Phase 2
0.654	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD2809	Approved
0.6533	Remote Similarity	NPD2831	Approved
0.6533	Remote Similarity	NPD9271	Approved
0.6532	Remote Similarity	NPD6248	Phase 2
0.6532	Remote Similarity	NPD6874	Approved
0.6532	Remote Similarity	NPD8101	Phase 3
0.6532	Remote Similarity	NPD6249	Phase 2
0.6528	Remote Similarity	NPD6791	Phase 2
0.6525	Remote Similarity	NPD3925	Approved
0.6522	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.652	Remote Similarity	NPD5255	Approved
0.6518	Remote Similarity	NPD7187	Phase 2
0.6516	Remote Similarity	NPD7417	Discontinued
0.6516	Remote Similarity	NPD7576	Discontinued
0.6513	Remote Similarity	NPD8465	Approved
0.6513	Remote Similarity	NPD8466	Approved
0.6513	Remote Similarity	NPD8467	Approved
0.6511	Remote Similarity	NPD8356	Approved
0.6508	Remote Similarity	NPD7169	Suspended
0.6507	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD6219	Discontinued
0.65	Remote Similarity	NPD3396	Approved
0.65	Remote Similarity	NPD5015	Clinical (unspecified phase)
0.65	Remote Similarity	NPD3395	Approved
0.6494	Remote Similarity	NPD8112	Clinical (unspecified phase)

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