NPASS Compound

Structure

CID36354 OpenBabel06191715362D 42 46 0 0 0 0 0 0 0 0999 V2000 -2.5428 -4.4043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0856 0.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5428 -3.4255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6952 -4.8936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0856 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2380 1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6952 -2.9362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 -4.4043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2380 -0.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3904 0.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5428 -1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3904 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6952 2.9362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5428 1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3904 -1.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2380 -0.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5428 3.4255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3904 1.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5428 -0.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 -3.4255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3904 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5428 -0.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6952 1.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2380 -1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3904 2.9362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6952 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6952 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6952 0.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 -0.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0856 -1.9574 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2380 3.4255 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 -1.4681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6952 0.9787 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5428 1.4681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 2.4468 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 -1.4681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 -0.4894 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 4 1 0 0 0 0 2 5 2 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 2 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 7 21 2 0 0 0 0 8 21 1 0 0 0 0 9 22 2 0 0 0 0 10 22 1 0 0 0 0 11 15 1 0 0 0 0 11 23 2 0 0 0 0 12 16 2 0 0 0 0 12 23 1 0 0 0 0 13 17 1 0 0 0 0 13 24 2 0 0 0 0 14 18 2 0 0 0 0 14 24 1 0 0 0 0 15 25 2 0 0 0 0 16 25 1 0 0 0 0 17 26 2 0 0 0 0 18 26 1 0 0 0 0 19 21 1 0 0 0 0 19 27 1 0 0 0 0 20 22 1 0 0 0 0 20 28 1 0 0 0 0 23 29 1 0 0 0 0 24 30 1 0 0 0 0 25 35 1 0 0 0 0 26 36 1 0 0 0 0 27 37 2 0 0 0 0 27 41 1 0 0 0 0 28 38 2 0 0 0 0 28 42 1 0 0 0 0 29 31 2 0 0 0 0 29 33 1 0 0 0 0 30 32 2 0 0 0 0 30 34 1 0 0 0 0 31 32 1 0 0 0 0 31 39 1 0 0 0 0 32 40 1 0 0 0 0 33 34 2 0 0 0 0 33 41 1 0 0 0 0 34 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	562.16
Volume:	579.34
LogP:	5.434
LogD:	3.711
LogS:	-3.51
# Rotatable Bonds:	10
TPSA:	133.52
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.101
Synthetic Accessibility Score:	2.511
Fsp3:	0.059
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.298
MDCK Permeability:	2.1080881197121926e-05
Pgp-inhibitor:	0.157
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.984
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	102.43348693847656%
Volume Distribution (VD):	0.227
Pgp-substrate:	0.6506995558738708%

ADMET: Metabolism

CYP1A2-inhibitor:	0.841
CYP1A2-substrate:	0.021
CYP2C19-inhibitor:	0.966
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.778
CYP2C9-substrate:	0.977
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.341
CYP3A4-inhibitor:	0.191
CYP3A4-substrate:	0.243

ADMET: Excretion

Clearance (CL):	6.359
Half-life (T1/2):	0.862

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.028
Drug-inuced Liver Injury (DILI):	0.975
AMES Toxicity:	0.131
Rat Oral Acute Toxicity:	0.867
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.613
Carcinogencity:	0.219
Eye Corrosion:	0.003
Eye Irritation:	0.856
Respiratory Toxicity:	0.03

Download Data

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

Natural Product: NPC36354

Natural Product ID:	NPC36354
*Common Name:**	Vialinin A
IUPAC Name:	[3,4-dihydroxy-2,5-bis(4-hydroxyphenyl)-6-(2-phenylacetyl)oxyphenyl] 2-phenylacetate
Synonyms:	Vialinin A
Standard InCHIKey:	NOJUKCRPSUMHQQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C34H26O8/c35-25-15-11-23(12-16-25)29-31(39)32(40)30(24-13-17-26(36)18-14-24)34(42-28(38)20-22-9-5-2-6-10-22)33(29)41-27(37)19-21-7-3-1-4-8-21/h1-18,35-36,39-40H,19-20H2
SMILES:	c1ccc(cc1)CC(=O)Oc1c(c2ccc(cc2)O)c(c(c(c2ccc(cc2)O)c1OC(=O)Cc1ccccc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2012938
PubChem CID:	11563133
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002042] Terphenyls [CHEMONTID:0002126] P-terphenyls

*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
NPO5475	Thelephora terrestris	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5475	Thelephora terrestris	Species	Thelephoraceae	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
EC50	1
IC50	11
Ki	4

Activity Type	# Activity
Cell Line	5
Individual Protein	9
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	IC50	=	0.09	nM	PMID[464113]
NPT2659	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 5	Homo sapiens	Ki	=	4000.0	nM	PMID[464114]
NPT2663	Individual Protein	Ubiquitin carboxyl-terminal hydrolase isozyme L1	Homo sapiens	IC50	=	22300.0	nM	PMID[464114]
NPT2664	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 4	Homo sapiens	IC50	=	1500.0	nM	PMID[464114]
NPT2659	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 5	Homo sapiens	Ki	=	12500.0	nM	PMID[464114]
NPT2659	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 5	Homo sapiens	IC50	=	5900.0	nM	PMID[464114]
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	IC50	=	0.09	nM	PMID[464114]
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	IC50	=	0.09	nM	PMID[464115]
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	IC50	=	0.25	nM	PMID[464115]
NPT5212	Individual Protein	Sentrin-specific protease 1	Homo sapiens	Ki	=	1070.0	nM	PMID[464116]
NPT5212	Individual Protein	Sentrin-specific protease 1	Homo sapiens	Ki	=	930.0	nM	PMID[464116]
NPT5212	Individual Protein	Sentrin-specific protease 1	Homo sapiens	IC50	=	1640.0	nM	PMID[464116]
NPT5212	Individual Protein	Sentrin-specific protease 1	Homo sapiens	IC50	=	1890.0	nM	PMID[464116]
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	IC50	=	0.09	nM	PMID[464116]
NPT1	Others	Radical scavenging activity		EC50	=	14000.0	nM	PMID[464113]
NPT2	Others	Unspecified		IC50	=	0.04	nM	PMID[464116]

☑ 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 NPC36354 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	405
0.1-0.2	1912
0.2-0.3	4775
0.3-0.4	11524
0.4-0.5	6264
0.5-0.6	4165
0.6-0.7	6051
0.7-0.8	6951
0.8-0.85	561
0.85-0.9	76
0.9-0.95	9
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9933	High Similarity	NPC36077
0.9669	High Similarity	NPC292385
0.9669	High Similarity	NPC125709
0.9423	High Similarity	NPC174311
0.9299	High Similarity	NPC55121
0.9272	High Similarity	NPC113790
0.9177	High Similarity	NPC476200
0.9177	High Similarity	NPC192258
0.9139	High Similarity	NPC97937
0.9139	High Similarity	NPC170239
0.9139	High Similarity	NPC275125
0.913	High Similarity	NPC476279
0.9007	High Similarity	NPC125617
0.8974	High Similarity	NPC7178
0.8974	High Similarity	NPC62903
0.8938	High Similarity	NPC140346
0.8929	High Similarity	NPC154527
0.8917	High Similarity	NPC155015
0.8917	High Similarity	NPC142479
0.8876	High Similarity	NPC226725
0.8824	High Similarity	NPC95652
0.8824	High Similarity	NPC150714
0.879	High Similarity	NPC476154
0.8773	High Similarity	NPC9309
0.8765	High Similarity	NPC67959
0.8667	High Similarity	NPC48956
0.8642	High Similarity	NPC109061
0.8642	High Similarity	NPC177100
0.8642	High Similarity	NPC155754
0.8642	High Similarity	NPC124747
0.8642	High Similarity	NPC139540
0.8634	High Similarity	NPC24339
0.8634	High Similarity	NPC98083
0.8634	High Similarity	NPC94220
0.8634	High Similarity	NPC166456
0.8634	High Similarity	NPC287458
0.8634	High Similarity	NPC7543
0.8606	High Similarity	NPC473818
0.8606	High Similarity	NPC167231
0.8606	High Similarity	NPC215802
0.8598	High Similarity	NPC142614
0.859	High Similarity	NPC139839
0.8589	High Similarity	NPC476372
0.8589	High Similarity	NPC476371
0.8588	High Similarity	NPC47883
0.8588	High Similarity	NPC8940
0.858	High Similarity	NPC98892
0.858	High Similarity	NPC297807
0.8562	High Similarity	NPC472335
0.8562	High Similarity	NPC476642
0.8562	High Similarity	NPC472332
0.8553	High Similarity	NPC61783
0.8553	High Similarity	NPC474656
0.8553	High Similarity	NPC20520
0.8545	High Similarity	NPC272560
0.8535	High Similarity	NPC476969
0.8528	High Similarity	NPC34089
0.8528	High Similarity	NPC196179
0.8521	High Similarity	NPC216307
0.8512	High Similarity	NPC98583
0.8509	High Similarity	NPC165483
0.8503	High Similarity	NPC180768
0.8503	High Similarity	NPC476365
0.8503	High Similarity	NPC17884
0.8503	High Similarity	NPC19273
0.8503	High Similarity	NPC91043
0.8491	Intermediate Similarity	NPC120774
0.8491	Intermediate Similarity	NPC264875
0.8491	Intermediate Similarity	NPC163598
0.8485	Intermediate Similarity	NPC259757
0.8471	Intermediate Similarity	NPC98546
0.8471	Intermediate Similarity	NPC281549
0.8467	Intermediate Similarity	NPC66840
0.8467	Intermediate Similarity	NPC256307
0.8466	Intermediate Similarity	NPC53889
0.8466	Intermediate Similarity	NPC476373
0.8466	Intermediate Similarity	NPC301089
0.8466	Intermediate Similarity	NPC24164
0.8462	Intermediate Similarity	NPC126291
0.8457	Intermediate Similarity	NPC185526
0.8457	Intermediate Similarity	NPC112954
0.8457	Intermediate Similarity	NPC289322
0.8457	Intermediate Similarity	NPC114179
0.8457	Intermediate Similarity	NPC38779
0.8457	Intermediate Similarity	NPC156818
0.8457	Intermediate Similarity	NPC160512
0.8457	Intermediate Similarity	NPC68324
0.8452	Intermediate Similarity	NPC100251
0.8452	Intermediate Similarity	NPC65333
0.8439	Intermediate Similarity	NPC469650
0.8424	Intermediate Similarity	NPC272064
0.8421	Intermediate Similarity	NPC201145
0.8421	Intermediate Similarity	NPC80956
0.8421	Intermediate Similarity	NPC6262
0.8421	Intermediate Similarity	NPC90615
0.8421	Intermediate Similarity	NPC25111
0.8421	Intermediate Similarity	NPC272157
0.8421	Intermediate Similarity	NPC73535
0.8415	Intermediate Similarity	NPC216916
0.8408	Intermediate Similarity	NPC262297
0.8405	Intermediate Similarity	NPC87317
0.8402	Intermediate Similarity	NPC149846
0.8395	Intermediate Similarity	NPC318432
0.8395	Intermediate Similarity	NPC104983
0.8395	Intermediate Similarity	NPC291948
0.8395	Intermediate Similarity	NPC250436
0.8395	Intermediate Similarity	NPC88803
0.8395	Intermediate Similarity	NPC300845
0.8391	Intermediate Similarity	NPC248315
0.8391	Intermediate Similarity	NPC269625
0.8391	Intermediate Similarity	NPC260521
0.8391	Intermediate Similarity	NPC469649
0.8387	Intermediate Similarity	NPC34245
0.8387	Intermediate Similarity	NPC256555
0.8387	Intermediate Similarity	NPC110067
0.8387	Intermediate Similarity	NPC7439
0.8387	Intermediate Similarity	NPC91492
0.8385	Intermediate Similarity	NPC8712
0.8373	Intermediate Similarity	NPC477840
0.8372	Intermediate Similarity	NPC125352
0.8364	Intermediate Similarity	NPC477841
0.8364	Intermediate Similarity	NPC219927
0.8364	Intermediate Similarity	NPC473445
0.8355	Intermediate Similarity	NPC476639
0.8355	Intermediate Similarity	NPC300846
0.8355	Intermediate Similarity	NPC114155
0.8354	Intermediate Similarity	NPC188967
0.8344	Intermediate Similarity	NPC40222
0.8344	Intermediate Similarity	NPC125495
0.8344	Intermediate Similarity	NPC268515
0.8344	Intermediate Similarity	NPC287275
0.8343	Intermediate Similarity	NPC223534
0.8343	Intermediate Similarity	NPC158226
0.8343	Intermediate Similarity	NPC477083
0.8343	Intermediate Similarity	NPC477081
0.8343	Intermediate Similarity	NPC174700
0.8343	Intermediate Similarity	NPC290289
0.8343	Intermediate Similarity	NPC158214
0.8343	Intermediate Similarity	NPC240200
0.8333	Intermediate Similarity	NPC67424
0.8333	Intermediate Similarity	NPC261623
0.8333	Intermediate Similarity	NPC474134
0.8333	Intermediate Similarity	NPC111490
0.8333	Intermediate Similarity	NPC171932
0.8333	Intermediate Similarity	NPC28440
0.8333	Intermediate Similarity	NPC131128
0.8333	Intermediate Similarity	NPC280493
0.8323	Intermediate Similarity	NPC472087
0.8323	Intermediate Similarity	NPC289968
0.8323	Intermediate Similarity	NPC472088
0.8323	Intermediate Similarity	NPC78809
0.8314	Intermediate Similarity	NPC324742
0.8313	Intermediate Similarity	NPC291977
0.8313	Intermediate Similarity	NPC121290
0.8313	Intermediate Similarity	NPC45943
0.8312	Intermediate Similarity	NPC165026
0.8312	Intermediate Similarity	NPC295719
0.8312	Intermediate Similarity	NPC262189
0.8312	Intermediate Similarity	NPC34431
0.8312	Intermediate Similarity	NPC73505
0.8312	Intermediate Similarity	NPC22317
0.8302	Intermediate Similarity	NPC318373
0.8302	Intermediate Similarity	NPC321657
0.8302	Intermediate Similarity	NPC30688
0.8302	Intermediate Similarity	NPC475250
0.8302	Intermediate Similarity	NPC176903
0.8301	Intermediate Similarity	NPC38874
0.8295	Intermediate Similarity	NPC93065
0.8295	Intermediate Similarity	NPC472721
0.8295	Intermediate Similarity	NPC187632
0.8295	Intermediate Similarity	NPC160543
0.8295	Intermediate Similarity	NPC469652
0.8295	Intermediate Similarity	NPC472720
0.8295	Intermediate Similarity	NPC472724
0.8295	Intermediate Similarity	NPC31208
0.8293	Intermediate Similarity	NPC40702
0.8293	Intermediate Similarity	NPC190487
0.8293	Intermediate Similarity	NPC37502
0.8293	Intermediate Similarity	NPC154304
0.8293	Intermediate Similarity	NPC328122
0.8293	Intermediate Similarity	NPC267627
0.8291	Intermediate Similarity	NPC208507
0.8291	Intermediate Similarity	NPC472333
0.8289	Intermediate Similarity	NPC252095
0.8289	Intermediate Similarity	NPC261873
0.8289	Intermediate Similarity	NPC111655
0.8289	Intermediate Similarity	NPC283009
0.8284	Intermediate Similarity	NPC265214
0.8284	Intermediate Similarity	NPC124470
0.8284	Intermediate Similarity	NPC109827
0.8274	Intermediate Similarity	NPC470704
0.8272	Intermediate Similarity	NPC178134
0.8272	Intermediate Similarity	NPC469888
0.8263	Intermediate Similarity	NPC130920
0.8263	Intermediate Similarity	NPC85057
0.8261	Intermediate Similarity	NPC476391
0.8261	Intermediate Similarity	NPC476434
0.8258	Intermediate Similarity	NPC19158
0.8258	Intermediate Similarity	NPC477082
0.8258	Intermediate Similarity	NPC472089

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 NPC36354 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	386
0.1-0.2	983
0.2-0.3	1869
0.3-0.4	2701
0.4-0.5	1720
0.5-0.6	937
0.6-0.7	431
0.7-0.8	114
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8443	Intermediate Similarity	NPD5844	Phase 1
0.8395	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD1465	Phase 2
0.8235	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD6232	Discontinued
0.8049	Intermediate Similarity	NPD2801	Approved
0.8047	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD6166	Phase 2
0.8	Intermediate Similarity	NPD7473	Discontinued
0.7964	Intermediate Similarity	NPD6234	Discontinued
0.7947	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD8455	Phase 2
0.7881	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD1934	Approved
0.787	Intermediate Similarity	NPD7199	Phase 2
0.7849	Intermediate Similarity	NPD7228	Approved
0.7844	Intermediate Similarity	NPD7768	Phase 2
0.7829	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD1511	Approved
0.7784	Intermediate Similarity	NPD3817	Phase 2
0.7778	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD37	Approved
0.7765	Intermediate Similarity	NPD6959	Discontinued
0.7759	Intermediate Similarity	NPD7074	Phase 3
0.775	Intermediate Similarity	NPD3750	Approved
0.7744	Intermediate Similarity	NPD1653	Approved
0.7742	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1613	Approved
0.7738	Intermediate Similarity	NPD4966	Approved
0.7738	Intermediate Similarity	NPD4965	Approved
0.7738	Intermediate Similarity	NPD4967	Phase 2
0.7733	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1512	Approved
0.7725	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD7054	Approved
0.7657	Intermediate Similarity	NPD7472	Approved
0.7644	Intermediate Similarity	NPD3818	Discontinued
0.7588	Intermediate Similarity	NPD3749	Approved
0.7584	Intermediate Similarity	NPD8312	Approved
0.7584	Intermediate Similarity	NPD8313	Approved
0.7574	Intermediate Similarity	NPD5402	Approved
0.7548	Intermediate Similarity	NPD3027	Phase 3
0.7531	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD3882	Suspended
0.7528	Intermediate Similarity	NPD7808	Phase 3
0.7514	Intermediate Similarity	NPD6797	Phase 2
0.75	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD4908	Phase 1
0.7472	Intermediate Similarity	NPD7251	Discontinued
0.7472	Intermediate Similarity	NPD6559	Discontinued
0.747	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD8127	Discontinued
0.7452	Intermediate Similarity	NPD6233	Phase 2
0.7438	Intermediate Similarity	NPD3748	Approved
0.743	Intermediate Similarity	NPD7549	Discontinued
0.7414	Intermediate Similarity	NPD3787	Discontinued
0.7412	Intermediate Similarity	NPD7819	Suspended
0.7399	Intermediate Similarity	NPD5494	Approved
0.7396	Intermediate Similarity	NPD7411	Suspended
0.7394	Intermediate Similarity	NPD7390	Discontinued
0.7391	Intermediate Similarity	NPD6100	Approved
0.7391	Intermediate Similarity	NPD6099	Approved
0.7389	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6798	Discontinued
0.7384	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD7075	Discontinued
0.7378	Intermediate Similarity	NPD6190	Approved
0.7374	Intermediate Similarity	NPD7240	Approved
0.7368	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD4380	Phase 2
0.7337	Intermediate Similarity	NPD6599	Discontinued
0.7325	Intermediate Similarity	NPD4625	Phase 3
0.7317	Intermediate Similarity	NPD7003	Approved
0.7317	Intermediate Similarity	NPD8166	Discontinued
0.7317	Intermediate Similarity	NPD4628	Phase 3
0.7305	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD2797	Approved
0.7284	Intermediate Similarity	NPD2935	Discontinued
0.7284	Intermediate Similarity	NPD1551	Phase 2
0.7284	Intermediate Similarity	NPD5408	Approved
0.7284	Intermediate Similarity	NPD5404	Approved
0.7284	Intermediate Similarity	NPD5405	Approved
0.7284	Intermediate Similarity	NPD5406	Approved
0.7278	Intermediate Similarity	NPD3226	Approved
0.7278	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD5403	Approved
0.725	Intermediate Similarity	NPD447	Suspended
0.7246	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7229	Phase 3
0.7215	Intermediate Similarity	NPD7095	Approved
0.7209	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1608	Approved
0.7208	Intermediate Similarity	NPD1481	Phase 2
0.7207	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6746	Phase 2
0.7188	Intermediate Similarity	NPD7680	Approved
0.7186	Intermediate Similarity	NPD6799	Approved
0.717	Intermediate Similarity	NPD3268	Approved
0.7161	Intermediate Similarity	NPD4749	Approved
0.7152	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6801	Discontinued
0.7151	Intermediate Similarity	NPD3751	Discontinued
0.7143	Intermediate Similarity	NPD1610	Phase 2
0.7143	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5401	Approved
0.7143	Intermediate Similarity	NPD422	Phase 1
0.7143	Intermediate Similarity	NPD6355	Discontinued
0.7143	Intermediate Similarity	NPD1535	Discovery
0.7143	Intermediate Similarity	NPD230	Phase 1
0.7134	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD4308	Phase 3
0.7115	Intermediate Similarity	NPD3225	Approved
0.7108	Intermediate Similarity	NPD4110	Phase 3
0.7108	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7783	Phase 2
0.7107	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD8151	Discontinued
0.7091	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD1549	Phase 2
0.7089	Intermediate Similarity	NPD2861	Phase 2
0.7081	Intermediate Similarity	NPD4060	Phase 1
0.7079	Intermediate Similarity	NPD3926	Phase 2
0.7076	Intermediate Similarity	NPD7458	Discontinued
0.7068	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD8053	Approved
0.7065	Intermediate Similarity	NPD8054	Approved
0.7065	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD919	Approved
0.7041	Intermediate Similarity	NPD2532	Approved
0.7041	Intermediate Similarity	NPD2534	Approved
0.7041	Intermediate Similarity	NPD2533	Approved
0.7032	Intermediate Similarity	NPD1611	Approved
0.7018	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD17	Approved
0.7012	Intermediate Similarity	NPD1510	Phase 2
0.7006	Intermediate Similarity	NPD1283	Approved
0.6995	Remote Similarity	NPD7039	Approved
0.6995	Remote Similarity	NPD7038	Approved
0.6995	Remote Similarity	NPD7685	Pre-registration
0.6994	Remote Similarity	NPD1607	Approved
0.6994	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1548	Phase 1
0.6981	Remote Similarity	NPD3018	Phase 2
0.6975	Remote Similarity	NPD943	Approved
0.6971	Remote Similarity	NPD4288	Approved
0.697	Remote Similarity	NPD2438	Suspended
0.6962	Remote Similarity	NPD1203	Approved
0.6961	Remote Similarity	NPD7177	Discontinued
0.6957	Remote Similarity	NPD3764	Approved
0.6957	Remote Similarity	NPD1296	Phase 2
0.6951	Remote Similarity	NPD7097	Phase 1
0.6946	Remote Similarity	NPD6674	Discontinued
0.6943	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD2346	Discontinued
0.6928	Remote Similarity	NPD7266	Discontinued
0.6914	Remote Similarity	NPD8032	Phase 2
0.6911	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6273	Approved
0.6893	Remote Similarity	NPD6971	Discontinued
0.6872	Remote Similarity	NPD1247	Approved
0.6871	Remote Similarity	NPD1240	Approved
0.6871	Remote Similarity	NPD2979	Phase 3
0.6871	Remote Similarity	NPD4307	Phase 2
0.6867	Remote Similarity	NPD2796	Approved
0.6855	Remote Similarity	NPD3267	Approved
0.6855	Remote Similarity	NPD3266	Approved
0.6852	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD1652	Phase 2
0.6837	Remote Similarity	NPD7435	Discontinued
0.6835	Remote Similarity	NPD2982	Phase 2
0.6835	Remote Similarity	NPD2983	Phase 2
0.6829	Remote Similarity	NPD5124	Phase 1
0.6829	Remote Similarity	NPD1933	Approved
0.6829	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD5535	Approved
0.6815	Remote Similarity	NPD1281	Approved
0.6809	Remote Similarity	NPD8150	Discontinued
0.6807	Remote Similarity	NPD7033	Discontinued
0.6807	Remote Similarity	NPD2799	Discontinued
0.6802	Remote Similarity	NPD7871	Phase 2
0.6802	Remote Similarity	NPD7870	Phase 2
0.6796	Remote Similarity	NPD5242	Approved
0.6795	Remote Similarity	NPD1778	Approved
0.6784	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD2981	Phase 2
0.6772	Remote Similarity	NPD9269	Phase 2
0.6769	Remote Similarity	NPD6776	Approved
0.6769	Remote Similarity	NPD6780	Approved
0.6769	Remote Similarity	NPD6778	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