NPASS Compound

Structure

CID178215 OpenBabel06191715552D 43 44 0 0 1 0 0 0 0 0999 V2000 6.1623 14.0828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2668 13.0883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1804 12.6816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2849 11.6870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1984 11.2803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3030 10.2858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2165 9.8790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3210 8.8845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2346 8.4778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3391 7.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2526 7.0765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5388 3.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5388 3.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5388 2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0388 3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0388 3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5388 2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0388 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3572 6.0820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.2413 4.1808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.0334 3.2026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5388 2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0388 3.0981 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.0388 1.3660 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 10.0388 3.0981 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 12.2707 5.6753 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.5388 2.2321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 12.3752 4.6808 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 12.0388 3.0981 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5388 3.9641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5388 2.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.5388 3.9641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.0797 6.2631 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.0388 1.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 -1.2601 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 11.6321 4.0116 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 26 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 20 1 0 0 0 0 13 14 1 0 0 0 0 13 16 1 0 0 0 0 14 17 1 0 0 0 0 15 18 1 0 0 0 0 15 19 1 0 0 0 0 16 28 1 0 0 0 0 17 30 1 0 0 0 0 18 28 1 0 0 0 0 19 29 1 0 0 0 0 20 31 1 0 0 0 0 21 22 1 0 0 0 0 21 33 1 0 0 0 0 22 34 1 0 0 0 0 23 26 1 0 0 0 0 23 27 2 0 0 0 0 24 27 1 0 0 0 0 24 29 1 0 0 0 0 25 30 1 0 0 0 0 25 32 1 0 0 0 0 26 42 1 0 0 0 0 27 35 1 0 0 0 0 28 36 1 0 0 0 0 29 37 1 0 0 0 0 30 38 1 0 0 0 0 31 39 1 6 0 0 0 32 40 1 1 0 0 0 33 31 1 6 0 0 0 33 43 1 0 0 0 0 34 32 1 1 0 0 0 34 43 1 0 0 0 0 35 41 2 0 0 0 0 35 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	612.46
Volume:	661.852
LogP:	6.446
LogD:	4.351
LogS:	-4.865
# Rotatable Bonds:	26
TPSA:	143.75
# H-Bond Aceptor:	8
# H-Bond Donor:	6
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.064
Synthetic Accessibility Score:	4.708
Fsp3:	0.886
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.359
MDCK Permeability:	1.4343474504130427e-05
Pgp-inhibitor:	0.104
Pgp-substrate:	0.889
Human Intestinal Absorption (HIA):	0.433
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	96.86714935302734%
Volume Distribution (VD):	1.06
Pgp-substrate:	3.442223072052002%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.712
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.092
CYP2C9-substrate:	0.948
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.042
CYP3A4-inhibitor:	0.086
CYP3A4-substrate:	0.025

ADMET: Excretion

Clearance (CL):	11.067
Half-life (T1/2):	0.217

ADMET: Toxicity

hERG Blockers:	0.075
Human Hepatotoxicity (H-HT):	0.379
Drug-inuced Liver Injury (DILI):	0.007
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.898
Skin Sensitization:	0.97
Carcinogencity:	0.077
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.787

Download Data

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

Natural Product: NPC178215

Natural Product ID:	NPC178215
*Common Name:**	Annomonicin
IUPAC Name:	2-methyl-4-[(13S)-2,6,11,13-tetrahydroxy-13-[(2S,5S)-5-[(1S)-1-hydroxytridecyl]oxolan-2-yl]tridecyl]-2H-furan-5-one
Synonyms:	Annomonicin
Standard InCHIKey:	XSUSTMTXAXHLDT-VMKMKWRQSA-N
Standard InCHI:	InChI=1S/C35H64O8/c1-3-4-5-6-7-8-9-10-11-12-20-31(39)33-21-22-34(43-33)32(40)25-30(38)17-14-13-16-28(36)18-15-19-29(37)24-27-23-26(2)42-35(27)41/h23,26,28-34,36-40H,3-22,24-25H2,1-2H3/t26?,28?,29?,30?,31-,32-,33-,34-/m0/s1
SMILES:	CCCCCCCCCCCC[C@@H]([C@@H]1CC[C@@H]([C@H](CC(CCCCC(CCCC(CC2=CC(C)OC2=O)O)O)O)O)O1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451655
PubChem CID:	21674082
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002518] Annonaceous acetogenins

*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
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1021/np50053a043]
NPO13370	Annona montana	Species	Annonaceae	Eukaryota	n.a.	trunk bark	n.a.	DOI[10.1039/P19820001205]
NPO13370	Annona montana	Species	Annonaceae	Eukaryota	n.a.	root	n.a.	DOI[10.1039/P19820001205]
NPO13370	Annona montana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568766]
NPO13370	Annona montana	Species	Annonaceae	Eukaryota	n.a.	seed	n.a.	PMID[18687006]
NPO13370	Annona montana	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[18687006]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8277309]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO13370	Annona montana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13370	Annona montana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13370	Annona montana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9632	Annona reticulata	Species	Annonaceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	2.4	10'-1 ug/ml	PMID[551659]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	1.73	ug ml-1	PMID[551659]

☑ 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 NPC178215 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	182
0.1-0.2	1397
0.2-0.3	5506
0.3-0.4	13064
0.4-0.5	11729
0.5-0.6	6935
0.6-0.7	3007
0.7-0.8	658
0.8-0.85	46
0.85-0.9	44
0.9-0.95	60
0.95-1	69

Similarity Score	Similarity Level	Natural Product ID
0.9878	High Similarity	NPC233551
0.9878	High Similarity	NPC48338
0.9878	High Similarity	NPC40376
0.9878	High Similarity	NPC280621
0.9878	High Similarity	NPC20339
0.9878	High Similarity	NPC21208
0.9877	High Similarity	NPC134865
0.9877	High Similarity	NPC103523
0.9753	High Similarity	NPC1083
0.9753	High Similarity	NPC66346
0.9753	High Similarity	NPC473669
0.9753	High Similarity	NPC103284
0.9753	High Similarity	NPC223871
0.9753	High Similarity	NPC283085
0.9753	High Similarity	NPC286338
0.9753	High Similarity	NPC82795
0.9753	High Similarity	NPC110710
0.9753	High Similarity	NPC132496
0.9753	High Similarity	NPC107986
0.9753	High Similarity	NPC473651
0.9753	High Similarity	NPC231009
0.9753	High Similarity	NPC477013
0.9753	High Similarity	NPC477014
0.9753	High Similarity	NPC473478
0.9643	High Similarity	NPC239517
0.9634	High Similarity	NPC308412
0.9634	High Similarity	NPC475581
0.9634	High Similarity	NPC477015
0.9634	High Similarity	NPC240695
0.9634	High Similarity	NPC279267
0.9634	High Similarity	NPC134807
0.9634	High Similarity	NPC171174
0.9634	High Similarity	NPC107717
0.9634	High Similarity	NPC231096
0.9634	High Similarity	NPC219498
0.9634	High Similarity	NPC473687
0.9634	High Similarity	NPC114694
0.9634	High Similarity	NPC62118
0.9634	High Similarity	NPC142117
0.9634	High Similarity	NPC134885
0.9634	High Similarity	NPC69082
0.9634	High Similarity	NPC210218
0.9634	High Similarity	NPC232555
0.9634	High Similarity	NPC204686
0.963	High Similarity	NPC163093
0.9524	High Similarity	NPC130359
0.9524	High Similarity	NPC139418
0.9524	High Similarity	NPC280612
0.9524	High Similarity	NPC40066
0.9524	High Similarity	NPC14901
0.9524	High Similarity	NPC42598
0.9524	High Similarity	NPC318963
0.9524	High Similarity	NPC20621
0.9524	High Similarity	NPC473504
0.9524	High Similarity	NPC81778
0.9524	High Similarity	NPC91067
0.9524	High Similarity	NPC93794
0.9524	High Similarity	NPC477011
0.9512	High Similarity	NPC329615
0.9512	High Similarity	NPC471567
0.9512	High Similarity	NPC120398
0.9512	High Similarity	NPC329838
0.9412	High Similarity	NPC473904
0.9405	High Similarity	NPC81045
0.9405	High Similarity	NPC151403
0.9405	High Similarity	NPC171135
0.9405	High Similarity	NPC191929
0.9405	High Similarity	NPC274446
0.9405	High Similarity	NPC169511
0.9405	High Similarity	NPC287164
0.9405	High Similarity	NPC242364
0.9405	High Similarity	NPC320569
0.9405	High Similarity	NPC172821
0.9405	High Similarity	NPC100454
0.9405	High Similarity	NPC261952
0.9405	High Similarity	NPC39754
0.9405	High Similarity	NPC234077
0.9405	High Similarity	NPC473905
0.9405	High Similarity	NPC320458
0.9405	High Similarity	NPC133730
0.9405	High Similarity	NPC89001
0.9405	High Similarity	NPC61257
0.9398	High Similarity	NPC112685
0.939	High Similarity	NPC156804
0.9383	High Similarity	NPC145914
0.9383	High Similarity	NPC73310
0.9383	High Similarity	NPC94875
0.9383	High Similarity	NPC131002
0.9383	High Similarity	NPC65930
0.9383	High Similarity	NPC473780
0.9383	High Similarity	NPC473529
0.9383	High Similarity	NPC329829
0.9383	High Similarity	NPC11332
0.9383	High Similarity	NPC180363
0.9383	High Similarity	NPC473712
0.9383	High Similarity	NPC475159
0.9294	High Similarity	NPC477017
0.9294	High Similarity	NPC477016
0.9286	High Similarity	NPC476583
0.9286	High Similarity	NPC258068
0.9286	High Similarity	NPC20533
0.9277	High Similarity	NPC322529
0.9277	High Similarity	NPC182383
0.9268	High Similarity	NPC144415
0.9268	High Similarity	NPC253801
0.9195	High Similarity	NPC11456
0.9167	High Similarity	NPC47937
0.9167	High Similarity	NPC132940
0.9167	High Similarity	NPC219652
0.9167	High Similarity	NPC473840
0.9167	High Similarity	NPC25703
0.9167	High Similarity	NPC282815
0.9167	High Similarity	NPC293136
0.9167	High Similarity	NPC241360
0.9059	High Similarity	NPC477012
0.9048	High Similarity	NPC473671
0.9048	High Similarity	NPC39279
0.9048	High Similarity	NPC235809
0.9048	High Similarity	NPC77871
0.9048	High Similarity	NPC470400
0.9048	High Similarity	NPC292809
0.9048	High Similarity	NPC319036
0.9048	High Similarity	NPC9678
0.9048	High Similarity	NPC475268
0.9048	High Similarity	NPC477018
0.9048	High Similarity	NPC100921
0.9048	High Similarity	NPC202055
0.9048	High Similarity	NPC25764
0.9048	High Similarity	NPC473156
0.9048	High Similarity	NPC39167
0.8977	High Similarity	NPC475173
0.8977	High Similarity	NPC473561
0.8977	High Similarity	NPC473723
0.8977	High Similarity	NPC473663
0.8941	High Similarity	NPC477010
0.8941	High Similarity	NPC309211
0.8864	High Similarity	NPC473707
0.8837	High Similarity	NPC473649
0.8837	High Similarity	NPC473995
0.8837	High Similarity	NPC154097
0.8837	High Similarity	NPC159750
0.8837	High Similarity	NPC470401
0.8556	High Similarity	NPC473520
0.837	Intermediate Similarity	NPC36954
0.8352	Intermediate Similarity	NPC162205
0.8352	Intermediate Similarity	NPC288240
0.8352	Intermediate Similarity	NPC295204
0.8352	Intermediate Similarity	NPC273579
0.8352	Intermediate Similarity	NPC476300
0.8333	Intermediate Similarity	NPC473619
0.8295	Intermediate Similarity	NPC469483
0.8242	Intermediate Similarity	NPC184463
0.8242	Intermediate Similarity	NPC30515
0.8242	Intermediate Similarity	NPC473321
0.8182	Intermediate Similarity	NPC21469
0.8161	Intermediate Similarity	NPC229799
0.8161	Intermediate Similarity	NPC286770
0.8161	Intermediate Similarity	NPC116543
0.8161	Intermediate Similarity	NPC284472
0.8152	Intermediate Similarity	NPC81419
0.8152	Intermediate Similarity	NPC179746
0.8152	Intermediate Similarity	NPC475912
0.8132	Intermediate Similarity	NPC474232
0.8132	Intermediate Similarity	NPC473448
0.8132	Intermediate Similarity	NPC51004
0.8105	Intermediate Similarity	NPC187268
0.8105	Intermediate Similarity	NPC473326
0.8085	Intermediate Similarity	NPC476315
0.8085	Intermediate Similarity	NPC279621
0.8046	Intermediate Similarity	NPC310450
0.8046	Intermediate Similarity	NPC475046
0.8046	Intermediate Similarity	NPC474959
0.8046	Intermediate Similarity	NPC11383
0.8043	Intermediate Similarity	NPC208886
0.8043	Intermediate Similarity	NPC12172
0.8023	Intermediate Similarity	NPC470147
0.8023	Intermediate Similarity	NPC133226
0.8023	Intermediate Similarity	NPC47653
0.8022	Intermediate Similarity	NPC295312
0.8022	Intermediate Similarity	NPC307411
0.8	Intermediate Similarity	NPC279214
0.8	Intermediate Similarity	NPC221095
0.7979	Intermediate Similarity	NPC471142
0.7979	Intermediate Similarity	NPC14961
0.7979	Intermediate Similarity	NPC270013
0.7979	Intermediate Similarity	NPC471141
0.7957	Intermediate Similarity	NPC212486
0.7955	Intermediate Similarity	NPC40746
0.7955	Intermediate Similarity	NPC169575
0.7955	Intermediate Similarity	NPC475947
0.7935	Intermediate Similarity	NPC476004
0.7935	Intermediate Similarity	NPC474761
0.7927	Intermediate Similarity	NPC84038
0.7917	Intermediate Similarity	NPC471144
0.7912	Intermediate Similarity	NPC473715
0.7912	Intermediate Similarity	NPC202672
0.7912	Intermediate Similarity	NPC475819
0.7907	Intermediate Similarity	NPC470149
0.7907	Intermediate Similarity	NPC470148
0.7907	Intermediate Similarity	NPC180725

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 NPC178215 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	2142
0.2-0.3	3825
0.3-0.4	2074
0.4-0.5	646
0.5-0.6	240
0.6-0.7	49
0.7-0.8	4
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
0.8132	Intermediate Similarity	NPD46	Approved
0.8132	Intermediate Similarity	NPD6698	Approved
0.79	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD7838	Discovery
0.7474	Intermediate Similarity	NPD7983	Approved
0.7308	Intermediate Similarity	NPD6686	Approved
0.72	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6371	Approved
0.7103	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4250	Approved
0.6875	Remote Similarity	NPD4251	Approved
0.6863	Remote Similarity	NPD4225	Approved
0.6837	Remote Similarity	NPD5785	Approved
0.6809	Remote Similarity	NPD7154	Phase 3
0.6771	Remote Similarity	NPD4249	Approved
0.6735	Remote Similarity	NPD1695	Approved
0.6667	Remote Similarity	NPD5363	Approved
0.6667	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3197	Phase 1
0.6667	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD5362	Discontinued
0.6571	Remote Similarity	NPD5344	Discontinued
0.6552	Remote Similarity	NPD8517	Approved
0.6552	Remote Similarity	NPD8515	Approved
0.6552	Remote Similarity	NPD8513	Phase 3
0.6552	Remote Similarity	NPD8516	Approved
0.6522	Remote Similarity	NPD4756	Discovery
0.6505	Remote Similarity	NPD7839	Suspended
0.6452	Remote Similarity	NPD4268	Approved
0.6452	Remote Similarity	NPD4271	Approved
0.6437	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6053	Discontinued
0.6392	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5778	Approved
0.6373	Remote Similarity	NPD5779	Approved
0.6354	Remote Similarity	NPD6435	Approved
0.6354	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD4269	Approved
0.6354	Remote Similarity	NPD4270	Approved
0.6348	Remote Similarity	NPD7115	Discovery
0.6333	Remote Similarity	NPD7507	Approved
0.6316	Remote Similarity	NPD4820	Approved
0.6316	Remote Similarity	NPD4822	Approved
0.6316	Remote Similarity	NPD4821	Approved
0.6316	Remote Similarity	NPD4819	Approved
0.6316	Remote Similarity	NPD4252	Approved
0.6311	Remote Similarity	NPD5282	Discontinued
0.6306	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7829	Approved
0.6303	Remote Similarity	NPD7830	Approved
0.6281	Remote Similarity	NPD8074	Phase 3
0.6263	Remote Similarity	NPD5786	Approved
0.625	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5369	Approved
0.6226	Remote Similarity	NPD7638	Approved
0.6179	Remote Similarity	NPD7319	Approved
0.6173	Remote Similarity	NPD3728	Approved
0.6173	Remote Similarity	NPD3730	Approved
0.6168	Remote Similarity	NPD7640	Approved
0.6168	Remote Similarity	NPD7639	Approved
0.6168	Remote Similarity	NPD6648	Approved
0.6167	Remote Similarity	NPD7642	Approved
0.6162	Remote Similarity	NPD1694	Approved
0.6154	Remote Similarity	NPD7641	Discontinued
0.6146	Remote Similarity	NPD5368	Approved
0.6134	Remote Similarity	NPD8033	Approved
0.6129	Remote Similarity	NPD8039	Approved
0.6122	Remote Similarity	NPD5332	Approved
0.6122	Remote Similarity	NPD5331	Approved
0.6122	Remote Similarity	NPD6110	Phase 1
0.6118	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD4790	Discontinued
0.6071	Remote Similarity	NPD9119	Approved
0.6071	Remote Similarity	NPD69	Approved
0.605	Remote Similarity	NPD8294	Approved
0.605	Remote Similarity	NPD8377	Approved
0.6023	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.602	Remote Similarity	NPD5209	Approved
0.6017	Remote Similarity	NPD7328	Approved
0.6017	Remote Similarity	NPD7327	Approved
0.6	Remote Similarity	NPD8296	Approved
0.6	Remote Similarity	NPD8444	Approved
0.6	Remote Similarity	NPD8378	Approved
0.6	Remote Similarity	NPD8379	Approved
0.6	Remote Similarity	NPD8335	Approved
0.6	Remote Similarity	NPD8380	Approved
0.6	Remote Similarity	NPD8297	Approved
0.5982	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD6412	Phase 2
0.5977	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD3195	Phase 2
0.5976	Remote Similarity	NPD4266	Approved
0.5976	Remote Similarity	NPD3196	Approved
0.5976	Remote Similarity	NPD3194	Approved
0.5966	Remote Similarity	NPD7516	Approved
0.5965	Remote Similarity	NPD6421	Discontinued
0.5962	Remote Similarity	NPD7637	Suspended
0.5955	Remote Similarity	NPD3704	Approved
0.5952	Remote Similarity	NPD9118	Approved
0.5935	Remote Similarity	NPD8451	Approved
0.5935	Remote Similarity	NPD8273	Phase 1
0.5932	Remote Similarity	NPD7505	Discontinued
0.5922	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD5370	Suspended
0.5922	Remote Similarity	NPD6101	Approved
0.5913	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD2204	Approved
0.5905	Remote Similarity	NPD6399	Phase 3
0.5887	Remote Similarity	NPD8448	Approved
0.5882	Remote Similarity	NPD6109	Phase 1
0.5854	Remote Similarity	NPD3172	Approved
0.5833	Remote Similarity	NPD7902	Approved
0.5827	Remote Similarity	NPD7260	Phase 2
0.5826	Remote Similarity	NPD2067	Discontinued
0.5812	Remote Similarity	NPD8133	Approved
0.581	Remote Similarity	NPD6411	Approved
0.581	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD6927	Phase 3
0.5798	Remote Similarity	NPD7500	Approved
0.5785	Remote Similarity	NPD6319	Approved
0.5781	Remote Similarity	NPD6845	Suspended
0.5778	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD6650	Approved
0.5776	Remote Similarity	NPD6649	Approved
0.5772	Remote Similarity	NPD8328	Phase 3
0.5748	Remote Similarity	NPD8391	Approved
0.5748	Remote Similarity	NPD8392	Approved
0.5748	Remote Similarity	NPD8390	Approved
0.5741	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD6372	Approved
0.5739	Remote Similarity	NPD6373	Approved
0.5738	Remote Similarity	NPD7503	Approved
0.5726	Remote Similarity	NPD8340	Approved
0.5726	Remote Similarity	NPD7492	Approved
0.5726	Remote Similarity	NPD8299	Approved
0.5726	Remote Similarity	NPD8341	Approved
0.5726	Remote Similarity	NPD8342	Approved
0.5714	Remote Similarity	NPD7736	Approved
0.5701	Remote Similarity	NPD7748	Approved
0.5691	Remote Similarity	NPD8080	Discontinued
0.5688	Remote Similarity	NPD6083	Phase 2
0.5688	Remote Similarity	NPD6084	Phase 2
0.568	Remote Similarity	NPD6616	Approved
0.5678	Remote Similarity	NPD4632	Approved
0.5667	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD6054	Approved
0.5652	Remote Similarity	NPD7320	Approved
0.5652	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD6899	Approved
0.5652	Remote Similarity	NPD6881	Approved
0.5641	Remote Similarity	NPD8130	Phase 1
0.5635	Remote Similarity	NPD8293	Discontinued
0.5635	Remote Similarity	NPD7078	Approved
0.5631	Remote Similarity	NPD6422	Discontinued
0.5625	Remote Similarity	NPD7632	Discontinued
0.5614	Remote Similarity	NPD5739	Approved
0.5614	Remote Similarity	NPD6402	Approved
0.5614	Remote Similarity	NPD6008	Approved
0.5614	Remote Similarity	NPD7128	Approved
0.5614	Remote Similarity	NPD6675	Approved
0.561	Remote Similarity	NPD8267	Approved
0.561	Remote Similarity	NPD8269	Approved
0.561	Remote Similarity	NPD29	Approved
0.561	Remote Similarity	NPD28	Approved
0.561	Remote Similarity	NPD8266	Approved
0.561	Remote Similarity	NPD8268	Approved
0.5604	Remote Similarity	NPD7331	Phase 2

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