NPASS Compound

Structure

NPC473772 OpenBabel07101718242D 44 43 0 0 1 0 0 0 0 0999 V2000 8.6603 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 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 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 2 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 2 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 17 2 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 18 20 2 0 0 0 0 19 21 1 0 0 0 0 20 22 1 0 0 0 0 21 23 1 0 0 0 0 22 24 1 0 0 0 0 23 25 1 0 0 0 0 24 26 1 0 0 0 0 25 27 1 0 0 0 0 26 28 1 0 0 0 0 27 29 1 0 0 0 0 28 30 1 0 0 0 0 29 31 1 0 0 0 0 30 32 1 0 0 0 0 31 33 1 0 0 0 0 32 34 1 0 0 0 0 33 38 1 0 0 0 0 34 39 1 0 0 0 0 35 37 1 0 0 0 0 35 43 1 0 0 0 0 36 37 1 0 0 0 0 36 44 1 0 0 0 0 37 40 1 0 0 0 0 38 41 2 0 0 0 0 38 43 1 0 0 0 0 39 42 2 0 0 0 0 39 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	612.48
Volume:	705.959
LogP:	6.874
LogD:	5.583
LogS:	-2.304
# Rotatable Bonds:	32
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	0
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.038
Synthetic Accessibility Score:	3.742
Fsp3:	0.641
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
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:	-5.073
MDCK Permeability:	0.00011265195644227788
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.117
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	100.8936996459961%
Volume Distribution (VD):	1.994
Pgp-substrate:	0.46468111872673035%

ADMET: Metabolism

CYP1A2-inhibitor:	0.117
CYP1A2-substrate:	0.181
CYP2C19-inhibitor:	0.188
CYP2C19-substrate:	0.072
CYP2C9-inhibitor:	0.218
CYP2C9-substrate:	0.953
CYP2D6-inhibitor:	0.912
CYP2D6-substrate:	0.923
CYP3A4-inhibitor:	0.982
CYP3A4-substrate:	0.155

ADMET: Excretion

Clearance (CL):	4.298
Half-life (T1/2):	0.941

ADMET: Toxicity

hERG Blockers:	0.41
Human Hepatotoxicity (H-HT):	0.223
Drug-inuced Liver Injury (DILI):	0.014
AMES Toxicity:	0.839
Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.887
Skin Sensitization:	0.984
Carcinogencity:	0.215
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.678

Download Data

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

Natural Product: NPC473772

Natural Product ID:	NPC473772
*Common Name:**	1,3-Dilinolenin
IUPAC Name:	[2-hydroxy-3-[(10Z,13Z,15E)-octadeca-10,13,15-trienoyl]oxypropyl] (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
Synonyms:	1,3-Dilinolenin
Standard InCHIKey:	BNJWNDPSWUOBCU-PRQTYVEHSA-N
Standard InCHI:	InChI=1S/C39H64O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(41)43-35-37(40)36-44-39(42)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h5-9,11-12,14-15,17-18,20,37,40H,3-4,10,13,16,19,21-36H2,1-2H3/b7-5+,8-6-,11-9-,14-12-,17-15-,20-18-
SMILES:	CC/C=CC/C=CC/C=CCCCCCCCC(=O)OCC(COC(=O)CCCCCCCC/C=CC/C=CC=CCC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451416
PubChem CID:	44575262
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000504] Lineolic acids and derivatives

*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
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	roots	purchased from Kiu Shun Trading Ltd., Vancouver, Canada	2000	PMID[16643021]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25538068]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27400088]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15462	Angelica sinensis	Species	Apiaceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1785	Individual Protein	Serotonin 7 (5-HT7) receptor	Homo sapiens	Inhibition	=	0.0	%	PMID[456004]

☑ 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 NPC473772 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	177
0.1-0.2	1689
0.2-0.3	7151
0.3-0.4	17802
0.4-0.5	9547
0.5-0.6	5076
0.6-0.7	1026
0.7-0.8	187
0.8-0.85	15
0.85-0.9	4
0.9-0.95	13
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9846	High Similarity	NPC476660
0.9688	High Similarity	NPC475443
0.9688	High Similarity	NPC473829
0.9538	High Similarity	NPC473559
0.9538	High Similarity	NPC48218
0.9538	High Similarity	NPC324981
0.9538	High Similarity	NPC141481
0.9385	High Similarity	NPC104537
0.9385	High Similarity	NPC330426
0.9385	High Similarity	NPC271921
0.9385	High Similarity	NPC148192
0.9385	High Similarity	NPC127091
0.9385	High Similarity	NPC22101
0.9231	High Similarity	NPC476656
0.9231	High Similarity	NPC476659
0.913	High Similarity	NPC474321
0.9077	High Similarity	NPC476655
0.9077	High Similarity	NPC476657
0.9077	High Similarity	NPC476654
0.9062	High Similarity	NPC54925
0.8923	High Similarity	NPC476658
0.8696	High Similarity	NPC42526
0.8462	Intermediate Similarity	NPC81896
0.8462	Intermediate Similarity	NPC321919
0.8333	Intermediate Similarity	NPC321838
0.8333	Intermediate Similarity	NPC201939
0.8261	Intermediate Similarity	NPC99619
0.8261	Intermediate Similarity	NPC26500
0.8235	Intermediate Similarity	NPC245947
0.8235	Intermediate Similarity	NPC136164
0.8235	Intermediate Similarity	NPC326268
0.8235	Intermediate Similarity	NPC255863
0.8235	Intermediate Similarity	NPC318420
0.8182	Intermediate Similarity	NPC243532
0.8143	Intermediate Similarity	NPC209327
0.8143	Intermediate Similarity	NPC273508
0.8088	Intermediate Similarity	NPC68343
0.8088	Intermediate Similarity	NPC328089
0.8052	Intermediate Similarity	NPC21693
0.8052	Intermediate Similarity	NPC236649
0.8026	Intermediate Similarity	NPC263574
0.8026	Intermediate Similarity	NPC469747
0.7971	Intermediate Similarity	NPC296436
0.7971	Intermediate Similarity	NPC176215
0.7969	Intermediate Similarity	NPC10316
0.7969	Intermediate Similarity	NPC228473
0.7969	Intermediate Similarity	NPC28779
0.7969	Intermediate Similarity	NPC223677
0.7969	Intermediate Similarity	NPC200845
0.7969	Intermediate Similarity	NPC128061
0.7945	Intermediate Similarity	NPC325627
0.7895	Intermediate Similarity	NPC11796
0.7895	Intermediate Similarity	NPC218817
0.7867	Intermediate Similarity	NPC190400
0.7867	Intermediate Similarity	NPC49392
0.7857	Intermediate Similarity	NPC83965
0.7848	Intermediate Similarity	NPC470313
0.7848	Intermediate Similarity	NPC473500
0.7848	Intermediate Similarity	NPC38295
0.7848	Intermediate Similarity	NPC156089
0.7846	Intermediate Similarity	NPC18951
0.7808	Intermediate Similarity	NPC320119
0.7794	Intermediate Similarity	NPC320305
0.7794	Intermediate Similarity	NPC328776
0.7778	Intermediate Similarity	NPC143396
0.7746	Intermediate Similarity	NPC193029
0.7746	Intermediate Similarity	NPC25298
0.7746	Intermediate Similarity	NPC473357
0.7727	Intermediate Similarity	NPC323436
0.7703	Intermediate Similarity	NPC470435
0.7703	Intermediate Similarity	NPC326024
0.7656	Intermediate Similarity	NPC39633
0.7656	Intermediate Similarity	NPC309606
0.7656	Intermediate Similarity	NPC71761
0.7656	Intermediate Similarity	NPC139545
0.7647	Intermediate Similarity	NPC328311
0.7647	Intermediate Similarity	NPC327112
0.7647	Intermediate Similarity	NPC143857
0.7647	Intermediate Similarity	NPC229252
0.7625	Intermediate Similarity	NPC196102
0.7625	Intermediate Similarity	NPC178758
0.7625	Intermediate Similarity	NPC253801
0.7619	Intermediate Similarity	NPC313670
0.76	Intermediate Similarity	NPC227396
0.7576	Intermediate Similarity	NPC477201
0.7571	Intermediate Similarity	NPC470320
0.7538	Intermediate Similarity	NPC25417
0.7538	Intermediate Similarity	NPC23155
0.7538	Intermediate Similarity	NPC469937
0.7538	Intermediate Similarity	NPC320588
0.7538	Intermediate Similarity	NPC261831
0.7538	Intermediate Similarity	NPC53463
0.7538	Intermediate Similarity	NPC290563
0.7538	Intermediate Similarity	NPC424
0.7538	Intermediate Similarity	NPC32467
0.7538	Intermediate Similarity	NPC281972
0.7538	Intermediate Similarity	NPC88966
0.7538	Intermediate Similarity	NPC6095
0.7538	Intermediate Similarity	NPC154245
0.7538	Intermediate Similarity	NPC87564
0.7538	Intermediate Similarity	NPC85813
0.7536	Intermediate Similarity	NPC40082
0.7534	Intermediate Similarity	NPC130618
0.7534	Intermediate Similarity	NPC470436
0.7534	Intermediate Similarity	NPC317583
0.7532	Intermediate Similarity	NPC110813
0.7531	Intermediate Similarity	NPC163093
0.75	Intermediate Similarity	NPC73310
0.75	Intermediate Similarity	NPC473780
0.75	Intermediate Similarity	NPC145914
0.75	Intermediate Similarity	NPC473712
0.75	Intermediate Similarity	NPC131002
0.75	Intermediate Similarity	NPC473529
0.75	Intermediate Similarity	NPC475159
0.75	Intermediate Similarity	NPC478100
0.75	Intermediate Similarity	NPC180363
0.75	Intermediate Similarity	NPC94875
0.75	Intermediate Similarity	NPC329829
0.75	Intermediate Similarity	NPC65930
0.75	Intermediate Similarity	NPC11332
0.7468	Intermediate Similarity	NPC469920
0.7468	Intermediate Similarity	NPC200446
0.7468	Intermediate Similarity	NPC103634
0.7463	Intermediate Similarity	NPC225929
0.7442	Intermediate Similarity	NPC478037
0.7442	Intermediate Similarity	NPC478036
0.7439	Intermediate Similarity	NPC477014
0.7439	Intermediate Similarity	NPC477013
0.7439	Intermediate Similarity	NPC471567
0.7439	Intermediate Similarity	NPC475206
0.7439	Intermediate Similarity	NPC120398
0.7439	Intermediate Similarity	NPC322529
0.7436	Intermediate Similarity	NPC133377
0.7424	Intermediate Similarity	NPC52264
0.7407	Intermediate Similarity	NPC144415
0.7403	Intermediate Similarity	NPC470899
0.7391	Intermediate Similarity	NPC251042
0.7391	Intermediate Similarity	NPC122521
0.7391	Intermediate Similarity	NPC174447
0.7385	Intermediate Similarity	NPC36061
0.7385	Intermediate Similarity	NPC321062
0.7385	Intermediate Similarity	NPC294548
0.7385	Intermediate Similarity	NPC70387
0.7385	Intermediate Similarity	NPC1813
0.7385	Intermediate Similarity	NPC139029
0.7381	Intermediate Similarity	NPC201046
0.7361	Intermediate Similarity	NPC478101
0.7353	Intermediate Similarity	NPC469373
0.7349	Intermediate Similarity	NPC279267
0.7349	Intermediate Similarity	NPC69082
0.7349	Intermediate Similarity	NPC309211
0.7349	Intermediate Similarity	NPC477015
0.7344	Intermediate Similarity	NPC262968
0.7342	Intermediate Similarity	NPC209995
0.7342	Intermediate Similarity	NPC1180
0.7324	Intermediate Similarity	NPC226592
0.7317	Intermediate Similarity	NPC156804
0.7294	Intermediate Similarity	NPC159369
0.7294	Intermediate Similarity	NPC39290
0.7286	Intermediate Similarity	NPC113293
0.7286	Intermediate Similarity	NPC325929
0.7286	Intermediate Similarity	NPC66460
0.7286	Intermediate Similarity	NPC271282
0.7284	Intermediate Similarity	NPC474252
0.7273	Intermediate Similarity	NPC260396
0.7273	Intermediate Similarity	NPC137538
0.7262	Intermediate Similarity	NPC477959
0.7262	Intermediate Similarity	NPC86005
0.7262	Intermediate Similarity	NPC178215
0.726	Intermediate Similarity	NPC49863
0.726	Intermediate Similarity	NPC478097
0.7246	Intermediate Similarity	NPC322186
0.7246	Intermediate Similarity	NPC106851
0.7246	Intermediate Similarity	NPC274927
0.7246	Intermediate Similarity	NPC329249
0.7237	Intermediate Similarity	NPC329890
0.7237	Intermediate Similarity	NPC329914
0.7231	Intermediate Similarity	NPC281245
0.7231	Intermediate Similarity	NPC92114
0.7229	Intermediate Similarity	NPC283085
0.7229	Intermediate Similarity	NPC470400
0.7229	Intermediate Similarity	NPC231009
0.7229	Intermediate Similarity	NPC235809
0.7229	Intermediate Similarity	NPC39167
0.7229	Intermediate Similarity	NPC292809
0.7229	Intermediate Similarity	NPC329838
0.7229	Intermediate Similarity	NPC473478
0.7229	Intermediate Similarity	NPC66346
0.7229	Intermediate Similarity	NPC132496
0.7229	Intermediate Similarity	NPC473156
0.7229	Intermediate Similarity	NPC329615
0.7229	Intermediate Similarity	NPC25764
0.7229	Intermediate Similarity	NPC103284
0.7229	Intermediate Similarity	NPC477018
0.7229	Intermediate Similarity	NPC286338
0.7229	Intermediate Similarity	NPC1083
0.7229	Intermediate Similarity	NPC77871
0.7229	Intermediate Similarity	NPC475268
0.7229	Intermediate Similarity	NPC223871
0.7229	Intermediate Similarity	NPC39279

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 NPC473772 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	146
0.1-0.2	2409
0.2-0.3	3872
0.3-0.4	1899
0.4-0.5	632
0.5-0.6	142
0.6-0.7	34
0.7-0.8	15
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
0.8358	Intermediate Similarity	NPD3197	Phase 1
0.7647	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD4266	Approved
0.7538	Intermediate Similarity	NPD3730	Approved
0.7538	Intermediate Similarity	NPD3728	Approved
0.7538	Intermediate Similarity	NPD3195	Phase 2
0.7538	Intermediate Similarity	NPD3194	Approved
0.7538	Intermediate Similarity	NPD3196	Approved
0.7529	Intermediate Similarity	NPD7983	Approved
0.7385	Intermediate Similarity	NPD3172	Approved
0.7353	Intermediate Similarity	NPD6109	Phase 1
0.7344	Intermediate Similarity	NPD29	Approved
0.7344	Intermediate Similarity	NPD28	Approved
0.726	Intermediate Similarity	NPD4247	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6435	Approved
0.6988	Remote Similarity	NPD7154	Phase 3
0.6897	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6101	Approved
0.6875	Remote Similarity	NPD5343	Approved
0.6875	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD8039	Approved
0.6829	Remote Similarity	NPD5368	Approved
0.6829	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7838	Discovery
0.6818	Remote Similarity	NPD46	Approved
0.6818	Remote Similarity	NPD6698	Approved
0.6769	Remote Similarity	NPD3173	Approved
0.6747	Remote Similarity	NPD5369	Approved
0.6742	Remote Similarity	NPD6411	Approved
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.663	Remote Similarity	NPD7839	Suspended
0.6615	Remote Similarity	NPD622	Approved
0.6588	Remote Similarity	NPD5362	Discontinued
0.6585	Remote Similarity	NPD4268	Approved
0.6585	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4271	Approved
0.6562	Remote Similarity	NPD3174	Discontinued
0.6471	Remote Similarity	NPD4270	Approved
0.6471	Remote Similarity	NPD4269	Approved
0.6463	Remote Similarity	NPD4756	Discovery
0.6429	Remote Similarity	NPD4822	Approved
0.6429	Remote Similarity	NPD4820	Approved
0.6429	Remote Similarity	NPD4819	Approved
0.6429	Remote Similarity	NPD4252	Approved
0.6429	Remote Similarity	NPD4821	Approved
0.6406	Remote Similarity	NPD2699	Approved
0.6406	Remote Similarity	NPD6097	Approved
0.6406	Remote Similarity	NPD6096	Approved
0.6386	Remote Similarity	NPD3732	Approved
0.6364	Remote Similarity	NPD5786	Approved
0.6308	Remote Similarity	NPD39	Approved
0.6308	Remote Similarity	NPD4222	Approved
0.6292	Remote Similarity	NPD4251	Approved
0.6292	Remote Similarity	NPD4250	Approved
0.625	Remote Similarity	NPD5363	Approved
0.618	Remote Similarity	NPD6422	Discontinued
0.618	Remote Similarity	NPD4249	Approved
0.6146	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD5785	Approved
0.6082	Remote Similarity	NPD7798	Approved
0.6056	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD3704	Approved
0.6023	Remote Similarity	NPD5331	Approved
0.6023	Remote Similarity	NPD5332	Approved
0.6022	Remote Similarity	NPD7637	Suspended
0.6	Remote Similarity	NPD5326	Phase 3
0.5978	Remote Similarity	NPD5370	Suspended
0.5977	Remote Similarity	NPD4790	Discontinued
0.5974	Remote Similarity	NPD7909	Approved
0.5962	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD819	Approved
0.5952	Remote Similarity	NPD818	Approved
0.5909	Remote Similarity	NPD5209	Approved
0.5895	Remote Similarity	NPD7748	Approved
0.5889	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5857	Remote Similarity	NPD6927	Phase 3
0.5851	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5844	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD6686	Approved
0.5823	Remote Similarity	NPD7331	Phase 2
0.5802	Remote Similarity	NPD8277	Approved
0.5789	Remote Similarity	NPD6399	Phase 3
0.578	Remote Similarity	NPD7641	Discontinued
0.5766	Remote Similarity	NPD8513	Phase 3
0.5766	Remote Similarity	NPD8516	Approved
0.5766	Remote Similarity	NPD8517	Approved
0.5766	Remote Similarity	NPD8515	Approved
0.5766	Remote Similarity	NPD8444	Approved
0.5755	Remote Similarity	NPD8297	Approved
0.5733	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6371	Approved
0.5714	Remote Similarity	NPD6083	Phase 2
0.5714	Remote Similarity	NPD6421	Discontinued
0.5714	Remote Similarity	NPD6084	Phase 2
0.5714	Remote Similarity	NPD7902	Approved
0.5696	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5692	Remote Similarity	NPD2270	Approved
0.5684	Remote Similarity	NPD7515	Phase 2
0.5679	Remote Similarity	NPD8278	Approved
0.5664	Remote Similarity	NPD7829	Approved
0.5664	Remote Similarity	NPD7830	Approved
0.5657	Remote Similarity	NPD4225	Approved
0.5652	Remote Similarity	NPD6409	Approved
0.5652	Remote Similarity	NPD6684	Approved
0.5652	Remote Similarity	NPD7146	Approved
0.5652	Remote Similarity	NPD5330	Approved
0.5652	Remote Similarity	NPD7521	Approved
0.5652	Remote Similarity	NPD7334	Approved
0.5625	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD8299	Approved
0.5614	Remote Similarity	NPD8342	Approved
0.5614	Remote Similarity	NPD8341	Approved
0.5614	Remote Similarity	NPD8340	Approved
0.5612	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.56	Remote Similarity	NPD6648	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