NPASS Compound

Structure

NPC473561 OpenBabel07101718202D 43 45 0 0 1 0 0 0 0 0999 V2000 26.1397 -1.9233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0933 -1.7796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 25.2387 -2.3572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 24.4125 -1.7939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 23.5115 -2.2278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 22.6853 -1.6645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 21.7843 -2.0983 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 20.9581 -1.5350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 20.0571 -1.9689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 19.2308 -1.4056 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7769 -0.3740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9678 0.2138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6904 0.0327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.3299 -1.8395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0543 -0.1930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4994 -0.5551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.5036 -1.2761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2453 0.3948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4130 -0.1483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.6027 -1.7100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1026 -0.2622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0221 -0.6553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.6969 -2.5645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.7060 -2.6988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5227 0.5759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7014 -2.4731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3317 -0.0119 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.2220 -0.7361 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 15.7764 -1.1467 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 14.8755 -1.5806 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 12.2881 -1.6192 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 13.2721 -1.7978 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2272 -1.0064 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 15.8512 -0.1495 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6386 1.6637 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0434 -1.7200 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.7004 -2.4282 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 13.9949 -1.1067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 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 14 1 0 0 0 0 11 12 1 0 0 0 0 11 13 1 0 0 0 0 12 15 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 16 19 1 0 0 0 0 17 20 1 0 0 0 0 18 30 1 0 0 0 0 20 32 1 0 0 0 0 21 22 1 0 0 0 0 21 31 1 0 0 0 0 23 24 1 0 0 0 0 23 33 1 0 0 0 0 25 28 1 0 0 0 0 25 29 2 0 0 0 0 26 29 1 0 0 0 0 26 30 1 0 0 0 0 27 40 1 0 0 0 0 27 41 1 0 0 0 0 28 2 1 6 0 0 0 28 42 1 0 0 0 0 29 36 1 0 0 0 0 30 37 1 1 0 0 0 31 19 1 6 0 0 0 31 40 1 0 0 0 0 32 38 1 6 0 0 0 33 32 1 1 0 0 0 33 43 1 0 0 0 0 34 22 1 6 0 0 0 34 35 1 0 0 0 0 34 41 1 0 0 0 0 35 24 1 6 0 0 0 35 43 1 0 0 0 0 36 39 2 0 0 0 0 36 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	608.47
Volume:	661.801
LogP:	9.355
LogD:	5.086
LogS:	-7.152
# Rotatable Bonds:	23
TPSA:	101.52
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.107
Synthetic Accessibility Score:	4.564
Fsp3:	0.889
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:	-5.126
MDCK Permeability:	2.266064620926045e-05
Pgp-inhibitor:	0.034
Pgp-substrate:	0.935
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.989
30% Bioavailability (F30%):	0.3

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	98.5701675415039%
Volume Distribution (VD):	0.491
Pgp-substrate:	2.5954344272613525%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.328
CYP2C19-inhibitor:	0.07
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.05
CYP2C9-substrate:	0.916
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.069
CYP3A4-inhibitor:	0.157
CYP3A4-substrate:	0.034

ADMET: Excretion

Clearance (CL):	3.889
Half-life (T1/2):	0.041

ADMET: Toxicity

hERG Blockers:	0.147
Human Hepatotoxicity (H-HT):	0.501
Drug-inuced Liver Injury (DILI):	0.371
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.163
Maximum Recommended Daily Dose:	0.893
Skin Sensitization:	0.974
Carcinogencity:	0.038
Eye Corrosion:	0.003
Eye Irritation:	0.032
Respiratory Toxicity:	0.105

Download Data

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

Natural Product: NPC473561

Natural Product ID:	NPC473561
*Common Name:**	Javoricin Formal
IUPAC Name:	(2S)-4-[(2R)-2-hydroxy-9-[(4R,7R)-7-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]-1,3-dioxepan-4-yl]nonyl]-2-methyl-2H-furan-5-one
Synonyms:	Javoricin Formal
Standard InCHIKey:	LAAZBSDOLUOJBG-SNBOQNFJSA-N
Standard InCHI:	InChI=1S/C36H64O7/c1-3-4-5-6-7-8-9-10-14-17-20-32(38)33-23-24-35(43-33)34-22-21-31(40-27-41-34)19-16-13-11-12-15-18-30(37)26-29-25-28(2)42-36(29)39/h25,28,30-35,37-38H,3-24,26-27H2,1-2H3/t28-,30+,31+,32+,33+,34+,35+/m0/s1
SMILES:	CCCCCCCCCCCCC(C1CCC(O1)C2CCC(OCO2)CCCCCCCC(CC3=CC(OC3=O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL445720
PubChem CID:	10603759
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
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473425]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975482]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17401878]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	stem	n.a.	PMID[17401878]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	root	n.a.	PMID[17401878]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7494150]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7673926]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7673935]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7673936]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	leaves	n.a.	n.a.	PMID[8946744]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[8991944]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[9584396]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26234	Annona muricata	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
IC50	3
Others	1

Activity Type	# Activity
Cell Line	3
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	0.02	ug.mL-1	PMID[558976]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	2.9	ug.mL-1	PMID[558976]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	5.6	ug.mL-1	PMID[558976]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	Inhibition	=	31.0	%	PMID[558976]

☑ 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 NPC473561 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	215
0.1-0.2	1707
0.2-0.3	6058
0.3-0.4	14396
0.4-0.5	10878
0.5-0.6	6685
0.6-0.7	2239
0.7-0.8	346
0.8-0.85	46
0.85-0.9	107
0.9-0.95	16
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475173
1.0	High Similarity	NPC473663
1.0	High Similarity	NPC473723
0.9545	High Similarity	NPC473520
0.9432	High Similarity	NPC473707
0.9318	High Similarity	NPC473904
0.9302	High Similarity	NPC240695
0.9302	High Similarity	NPC232555
0.9302	High Similarity	NPC171174
0.9302	High Similarity	NPC62118
0.9302	High Similarity	NPC114694
0.9302	High Similarity	NPC142117
0.9302	High Similarity	NPC107717
0.9302	High Similarity	NPC475581
0.9302	High Similarity	NPC231096
0.9205	High Similarity	NPC139418
0.9186	High Similarity	NPC286338
0.9186	High Similarity	NPC223871
0.9186	High Similarity	NPC231009
0.9186	High Similarity	NPC283085
0.9186	High Similarity	NPC473669
0.9186	High Similarity	NPC66346
0.9186	High Similarity	NPC473478
0.9186	High Similarity	NPC82795
0.9186	High Similarity	NPC132496
0.9186	High Similarity	NPC107986
0.9186	High Similarity	NPC103284
0.9186	High Similarity	NPC1083
0.9186	High Similarity	NPC110710
0.9186	High Similarity	NPC473651
0.9091	High Similarity	NPC48338
0.9091	High Similarity	NPC233551
0.9091	High Similarity	NPC40376
0.9091	High Similarity	NPC261952
0.9091	High Similarity	NPC81045
0.9091	High Similarity	NPC21208
0.9091	High Similarity	NPC133730
0.9091	High Similarity	NPC287164
0.9091	High Similarity	NPC151403
0.9091	High Similarity	NPC61257
0.9091	High Similarity	NPC20339
0.9091	High Similarity	NPC171135
0.9091	High Similarity	NPC242364
0.9091	High Similarity	NPC320569
0.9091	High Similarity	NPC172821
0.9091	High Similarity	NPC191929
0.9091	High Similarity	NPC274446
0.9091	High Similarity	NPC39754
0.9091	High Similarity	NPC234077
0.9091	High Similarity	NPC169511
0.9091	High Similarity	NPC280621
0.9091	High Similarity	NPC100454
0.908	High Similarity	NPC134885
0.908	High Similarity	NPC103523
0.908	High Similarity	NPC473687
0.908	High Similarity	NPC69082
0.908	High Similarity	NPC134807
0.908	High Similarity	NPC134865
0.908	High Similarity	NPC279267
0.908	High Similarity	NPC210218
0.908	High Similarity	NPC204686
0.908	High Similarity	NPC219498
0.908	High Similarity	NPC308412
0.907	High Similarity	NPC156804
0.8989	High Similarity	NPC473504
0.8989	High Similarity	NPC42598
0.8989	High Similarity	NPC93794
0.8989	High Similarity	NPC477011
0.8989	High Similarity	NPC91067
0.8989	High Similarity	NPC318963
0.8989	High Similarity	NPC40066
0.8989	High Similarity	NPC81778
0.8989	High Similarity	NPC20621
0.8977	High Similarity	NPC178215
0.8966	High Similarity	NPC329615
0.8966	High Similarity	NPC471567
0.8966	High Similarity	NPC322529
0.8966	High Similarity	NPC120398
0.8966	High Similarity	NPC329838
0.8901	High Similarity	NPC11456
0.8889	High Similarity	NPC239517
0.8864	High Similarity	NPC241360
0.8864	High Similarity	NPC47937
0.8864	High Similarity	NPC293136
0.8864	High Similarity	NPC112685
0.8864	High Similarity	NPC132940
0.8851	High Similarity	NPC163093
0.8837	High Similarity	NPC94875
0.8837	High Similarity	NPC131002
0.8837	High Similarity	NPC473712
0.8837	High Similarity	NPC65930
0.8837	High Similarity	NPC145914
0.8837	High Similarity	NPC73310
0.8837	High Similarity	NPC473529
0.8837	High Similarity	NPC180363
0.8837	High Similarity	NPC475159
0.8837	High Similarity	NPC329829
0.8837	High Similarity	NPC11332
0.8837	High Similarity	NPC473780
0.8778	High Similarity	NPC14901
0.8778	High Similarity	NPC130359
0.8764	High Similarity	NPC20533
0.8764	High Similarity	NPC476583
0.8764	High Similarity	NPC258068
0.875	High Similarity	NPC473156
0.875	High Similarity	NPC319036
0.875	High Similarity	NPC235809
0.875	High Similarity	NPC39167
0.875	High Similarity	NPC470400
0.875	High Similarity	NPC202055
0.875	High Similarity	NPC9678
0.875	High Similarity	NPC182383
0.875	High Similarity	NPC292809
0.875	High Similarity	NPC477014
0.875	High Similarity	NPC25764
0.875	High Similarity	NPC473671
0.875	High Similarity	NPC77871
0.875	High Similarity	NPC477018
0.875	High Similarity	NPC477013
0.875	High Similarity	NPC100921
0.875	High Similarity	NPC475268
0.875	High Similarity	NPC39279
0.8736	High Similarity	NPC144415
0.8736	High Similarity	NPC253801
0.8667	High Similarity	NPC473905
0.8667	High Similarity	NPC320458
0.8667	High Similarity	NPC89001
0.8652	High Similarity	NPC25703
0.8652	High Similarity	NPC473840
0.8652	High Similarity	NPC477010
0.8652	High Similarity	NPC282815
0.8652	High Similarity	NPC219652
0.8652	High Similarity	NPC477015
0.8652	High Similarity	NPC309211
0.8571	High Similarity	NPC477017
0.8571	High Similarity	NPC477016
0.8571	High Similarity	NPC280612
0.8556	High Similarity	NPC473649
0.8556	High Similarity	NPC159750
0.8556	High Similarity	NPC154097
0.8556	High Similarity	NPC470401
0.8556	High Similarity	NPC473995
0.8352	Intermediate Similarity	NPC477012
0.8111	Intermediate Similarity	NPC229799
0.8111	Intermediate Similarity	NPC286770
0.8111	Intermediate Similarity	NPC284472
0.8061	Intermediate Similarity	NPC187268
0.8041	Intermediate Similarity	NPC306041
0.8022	Intermediate Similarity	NPC288471
0.8022	Intermediate Similarity	NPC41856
0.8	Intermediate Similarity	NPC475046
0.8	Intermediate Similarity	NPC310450
0.8	Intermediate Similarity	NPC11383
0.8	Intermediate Similarity	NPC474959
0.8	Intermediate Similarity	NPC30515
0.7917	Intermediate Similarity	NPC81419
0.7917	Intermediate Similarity	NPC179746
0.7895	Intermediate Similarity	NPC80875
0.7895	Intermediate Similarity	NPC475995
0.7895	Intermediate Similarity	NPC474098
0.7895	Intermediate Similarity	NPC473619
0.7895	Intermediate Similarity	NPC51004
0.7895	Intermediate Similarity	NPC118078
0.7812	Intermediate Similarity	NPC184463
0.7812	Intermediate Similarity	NPC12172
0.7812	Intermediate Similarity	NPC208886
0.7812	Intermediate Similarity	NPC473321
0.7789	Intermediate Similarity	NPC307411
0.7789	Intermediate Similarity	NPC295312
0.7755	Intermediate Similarity	NPC36954
0.7755	Intermediate Similarity	NPC471141
0.7742	Intermediate Similarity	NPC21469
0.7732	Intermediate Similarity	NPC472196
0.7732	Intermediate Similarity	NPC472195
0.7732	Intermediate Similarity	NPC288240
0.7732	Intermediate Similarity	NPC320089
0.7732	Intermediate Similarity	NPC162205
0.7732	Intermediate Similarity	NPC475912
0.7732	Intermediate Similarity	NPC273579
0.7732	Intermediate Similarity	NPC476300
0.7732	Intermediate Similarity	NPC295204
0.7732	Intermediate Similarity	NPC238090
0.7723	Intermediate Similarity	NPC473332
0.7708	Intermediate Similarity	NPC476004
0.7708	Intermediate Similarity	NPC474761
0.77	Intermediate Similarity	NPC473326
0.77	Intermediate Similarity	NPC203627
0.7684	Intermediate Similarity	NPC202672
0.7677	Intermediate Similarity	NPC54731
0.7653	Intermediate Similarity	NPC159698
0.7653	Intermediate Similarity	NPC474035
0.7653	Intermediate Similarity	NPC81386
0.7653	Intermediate Similarity	NPC474338
0.7647	Intermediate Similarity	NPC86077
0.764	Intermediate Similarity	NPC475711
0.7629	Intermediate Similarity	NPC472197
0.7604	Intermediate Similarity	NPC474032
0.76	Intermediate Similarity	NPC266842
0.7579	Intermediate Similarity	NPC160138
0.7579	Intermediate Similarity	NPC248602

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 NPC473561 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	204
0.1-0.2	2414
0.2-0.3	3904
0.3-0.4	1847
0.4-0.5	572
0.5-0.6	178
0.6-0.7	29
0.7-0.8	2
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
0.7526	Intermediate Similarity	NPD46	Approved
0.7526	Intermediate Similarity	NPD6698	Approved
0.7524	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6686	Approved
0.7353	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7838	Discovery
0.7091	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6371	Approved
0.6931	Remote Similarity	NPD7983	Approved
0.6731	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD8515	Approved
0.6695	Remote Similarity	NPD8516	Approved
0.6695	Remote Similarity	NPD8517	Approved
0.6695	Remote Similarity	NPD8513	Phase 3
0.6667	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD1695	Approved
0.6535	Remote Similarity	NPD4250	Approved
0.6535	Remote Similarity	NPD4251	Approved
0.6505	Remote Similarity	NPD5785	Approved
0.6475	Remote Similarity	NPD7507	Approved
0.6446	Remote Similarity	NPD7829	Approved
0.6446	Remote Similarity	NPD7830	Approved
0.6436	Remote Similarity	NPD4249	Approved
0.6435	Remote Similarity	NPD6053	Discontinued
0.64	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD4225	Approved
0.6337	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD5363	Approved
0.632	Remote Similarity	NPD7319	Approved
0.6311	Remote Similarity	NPD7642	Approved
0.6303	Remote Similarity	NPD7641	Discontinued
0.63	Remote Similarity	NPD5362	Discontinued
0.63	Remote Similarity	NPD7154	Phase 3
0.6292	Remote Similarity	NPD3197	Phase 1
0.629	Remote Similarity	NPD8074	Phase 3
0.6283	Remote Similarity	NPD6412	Phase 2
0.6281	Remote Similarity	NPD8033	Approved
0.6273	Remote Similarity	NPD5344	Discontinued
0.6204	Remote Similarity	NPD7839	Suspended
0.6198	Remote Similarity	NPD8294	Approved
0.6198	Remote Similarity	NPD8377	Approved
0.6186	Remote Similarity	NPD4756	Discovery
0.6167	Remote Similarity	NPD7328	Approved
0.6167	Remote Similarity	NPD7327	Approved
0.6162	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD8380	Approved
0.6148	Remote Similarity	NPD8335	Approved
0.6148	Remote Similarity	NPD8379	Approved
0.6148	Remote Similarity	NPD8296	Approved
0.6148	Remote Similarity	NPD8444	Approved
0.6148	Remote Similarity	NPD8378	Approved
0.6116	Remote Similarity	NPD7516	Approved
0.6107	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD7638	Approved
0.6087	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.608	Remote Similarity	NPD8451	Approved
0.604	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.604	Remote Similarity	NPD4269	Approved
0.604	Remote Similarity	NPD4270	Approved
0.6036	Remote Similarity	NPD7640	Approved
0.6036	Remote Similarity	NPD7639	Approved
0.6034	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD8448	Approved
0.6019	Remote Similarity	NPD5282	Discontinued
0.6	Remote Similarity	NPD4252	Approved
0.5984	Remote Similarity	NPD7736	Approved
0.598	Remote Similarity	NPD6110	Phase 1
0.5966	Remote Similarity	NPD8133	Approved
0.5962	Remote Similarity	NPD5786	Approved
0.596	Remote Similarity	NPD4271	Approved
0.596	Remote Similarity	NPD4268	Approved
0.595	Remote Similarity	NPD7115	Discovery
0.5941	Remote Similarity	NPD5369	Approved
0.5926	Remote Similarity	NPD5778	Approved
0.5926	Remote Similarity	NPD5779	Approved
0.592	Remote Similarity	NPD8328	Phase 3
0.5906	Remote Similarity	NPD8293	Discontinued
0.5897	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD6648	Approved
0.5891	Remote Similarity	NPD8392	Approved
0.5891	Remote Similarity	NPD8390	Approved
0.5891	Remote Similarity	NPD8391	Approved
0.5887	Remote Similarity	NPD8266	Approved
0.5887	Remote Similarity	NPD8268	Approved
0.5887	Remote Similarity	NPD8267	Approved
0.5887	Remote Similarity	NPD8269	Approved
0.5887	Remote Similarity	NPD7503	Approved
0.5882	Remote Similarity	NPD6435	Approved
0.5873	Remote Similarity	NPD8340	Approved
0.5873	Remote Similarity	NPD7492	Approved
0.5873	Remote Similarity	NPD8299	Approved
0.5873	Remote Similarity	NPD8342	Approved
0.5873	Remote Similarity	NPD8341	Approved
0.5865	Remote Similarity	NPD1694	Approved
0.5847	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD4820	Approved
0.5842	Remote Similarity	NPD4819	Approved
0.5842	Remote Similarity	NPD4821	Approved
0.5842	Remote Similarity	NPD4822	Approved
0.584	Remote Similarity	NPD8080	Discontinued
0.584	Remote Similarity	NPD6370	Approved
0.5827	Remote Similarity	NPD6616	Approved
0.5825	Remote Similarity	NPD5332	Approved
0.5825	Remote Similarity	NPD5331	Approved
0.582	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.582	Remote Similarity	NPD7500	Approved
0.5816	Remote Similarity	NPD8039	Approved
0.5806	Remote Similarity	NPD6054	Approved
0.58	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD4790	Discontinued
0.5781	Remote Similarity	NPD7078	Approved
0.5778	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD5209	Approved
0.5714	Remote Similarity	NPD6421	Discontinued
0.5703	Remote Similarity	NPD8273	Phase 1
0.5699	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD6009	Approved
0.5691	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD5368	Approved
0.568	Remote Similarity	NPD6059	Approved
0.5669	Remote Similarity	NPD6067	Discontinued
0.5667	Remote Similarity	NPD2204	Approved
0.5652	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD5370	Suspended
0.5638	Remote Similarity	NPD3704	Approved
0.5636	Remote Similarity	NPD6399	Phase 3
0.5635	Remote Similarity	NPD6015	Approved
0.5635	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5635	Remote Similarity	NPD6016	Approved
0.5632	Remote Similarity	NPD3730	Approved
0.5632	Remote Similarity	NPD3728	Approved
0.5632	Remote Similarity	NPD3196	Approved
0.5632	Remote Similarity	NPD3195	Phase 2
0.5632	Remote Similarity	NPD3194	Approved
0.5632	Remote Similarity	NPD4266	Approved
0.5606	Remote Similarity	NPD7260	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