NPASS Compound

Structure

NPC80956 OpenBabel07101719142D 56 61 0 0 1 0 0 0 0 0999 V2000 -7.9376 0.5252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0993 1.9772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9011 2.7806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3350 1.1612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5856 2.8154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7461 -0.9267 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7047 0.5252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0993 1.0092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6505 1.8456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5856 1.8475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9079 -0.4428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7758 1.0092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9376 2.4611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8360 3.0312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2700 1.4117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4239 3.2994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5844 -0.4428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7047 -0.4428 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4239 1.3635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9079 0.5252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7758 1.9772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5205 2.3467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2622 2.8154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2207 -1.2811 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2622 1.8475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7461 1.0092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0604 -1.0604 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5844 0.5252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6176 -1.7650 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2610 0.5252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2194 1.3446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6176 1.8475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4239 -1.2811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7855 -0.2749 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.6141 0.5252 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9376 3.4291 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0866 3.9661 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9544 0.7273 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4239 4.2674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4227 -0.9267 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6141 2.4611 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4555 2.5972 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1004 3.2994 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9051 -1.9655 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1004 1.3635 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7461 1.9772 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0223 -1.1688 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2610 -0.4428 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5884 2.7135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3671 2.7825 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1083 -1.9655 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2207 1.3635 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 -5.4227 1.0092 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5856 -1.7650 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4700 0.4096 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 2 0 0 0 0 1 12 1 0 0 0 0 2 8 1 0 0 0 0 2 13 2 0 0 0 0 3 9 2 0 0 0 0 3 14 1 0 0 0 0 4 9 1 0 0 0 0 4 15 2 0 0 0 0 5 10 2 0 0 0 0 5 16 1 0 0 0 0 6 11 2 0 0 0 0 6 17 1 0 0 0 0 7 52 1 0 0 0 0 8 30 1 0 0 0 0 9 31 1 0 0 0 0 10 19 1 0 0 0 0 10 32 1 0 0 0 0 11 20 1 0 0 0 0 11 33 1 0 0 0 0 12 21 2 0 0 0 0 12 35 1 0 0 0 0 13 21 1 0 0 0 0 13 36 1 0 0 0 0 14 22 2 0 0 0 0 14 37 1 0 0 0 0 15 22 1 0 0 0 0 15 38 1 0 0 0 0 16 23 2 0 0 0 0 16 39 1 0 0 0 0 17 28 2 0 0 0 0 17 40 1 0 0 0 0 18 7 1 6 0 0 0 18 24 1 0 0 0 0 18 53 1 0 0 0 0 19 20 1 0 0 0 0 19 25 2 0 0 0 0 20 26 2 0 0 0 0 21 41 1 0 0 0 0 22 42 1 0 0 0 0 23 25 1 0 0 0 0 23 43 1 0 0 0 0 24 29 1 0 0 0 0 24 44 1 1 0 0 0 25 45 1 0 0 0 0 26 28 1 0 0 0 0 26 46 1 0 0 0 0 27 29 1 0 0 0 0 27 34 1 0 0 0 0 27 47 1 1 0 0 0 28 54 1 0 0 0 0 29 55 1 6 0 0 0 30 48 2 0 0 0 0 30 54 1 0 0 0 0 31 49 2 0 0 0 0 31 56 1 0 0 0 0 32 50 2 0 0 0 0 32 52 1 0 0 0 0 33 51 2 0 0 0 0 33 55 1 0 0 0 0 34 53 1 0 0 0 0 34 56 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	786.09
Volume:	696.483
LogP:	1.479
LogD:	1.001
LogS:	-3.538
# Rotatable Bonds:	6
TPSA:	377.42
# H-Bond Aceptor:	22
# H-Bond Donor:	13
# Rings:	6
# Heavy Atoms:	22

MedChem Properties

QED Drug-Likeness Score:	0.057
Synthetic Accessibility Score:	6.145
Fsp3:	0.176
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-7.08
MDCK Permeability:	1.053610958479112e-05
Pgp-inhibitor:	0.429
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.976
20% Bioavailability (F20%):	0.95
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	88.85518646240234%
Volume Distribution (VD):	0.477
Pgp-substrate:	28.61349868774414%

ADMET: Metabolism

CYP1A2-inhibitor:	0.268
CYP1A2-substrate:	0.004
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.02
CYP2C9-inhibitor:	0.465
CYP2C9-substrate:	0.023
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.068
CYP3A4-inhibitor:	0.014
CYP3A4-substrate:	0.001

ADMET: Excretion

Clearance (CL):	7.217
Half-life (T1/2):	0.966

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.193
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.096
Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.012
Skin Sensitization:	0.958
Carcinogencity:	0.005
Eye Corrosion:	0.003
Eye Irritation:	0.925
Respiratory Toxicity:	0.004

Download Data

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

Natural Product: NPC80956

Natural Product ID:	NPC80956
*Common Name:**	Mallorepanin
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QLLMARJXKLXEEY-LXPSXXTQSA-N
Standard InCHI:	InChI=1S/C34H26O22/c35-12-1-8(2-13(36)21(12)41)30(48)54-28-17(40)6-11-20(26(28)46)19-10(5-16(39)23(43)25(19)45)32(50)52-7-18-24(44)29(55-33(11)51)27(47)34(53-18)56-31(49)9-3-14(37)22(42)15(38)4-9/h1-6,18,24,27,29,34-47H,7H2/t18-,24-,27-,29+,34+/m1/s1
SMILES:	c1c(cc(c(c1O)O)O)C(=O)Oc1c(cc2c(-c3c(cc(c(c3O)O)O)C(=O)OC[C@@H]3[C@H]([C@@H]([C@H]([C@@H](O3)OC(=O)c3cc(c(c(c3)O)O)O)O)OC2=O)O)c1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2289445
PubChem CID:	11479809
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO27007	Cunonia macrophylla	Species	Cunoniaceae	Eukaryota	n.a.	New Caledonia	n.a.	PMID[15652581]
NPO27007	Cunonia macrophylla	Species	Cunoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27007	Cunonia macrophylla	Species	Cunoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27007	Cunonia macrophylla	Species	Cunoniaceae	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	1
Others	4

Activity Type	# Activity
Organism	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[551705]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	10.0	mm	PMID[551705]
NPT1285	Organism	Corynebacterium accolens	Corynebacterium accolens	IZ	=	10.0	mm	PMID[551705]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	10.0	mm	PMID[551705]
NPT1286	Organism	Pectobacterium carotovorum	Pectobacterium carotovorum	IZ	=	15.0	mm	PMID[551705]

☑ 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 NPC80956 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	434
0.1-0.2	1792
0.2-0.3	4012
0.3-0.4	9046
0.4-0.5	8779
0.5-0.6	4542
0.6-0.7	5681
0.7-0.8	6408
0.8-0.85	1261
0.85-0.9	602
0.9-0.95	115
0.95-1	25

Similarity Score	Similarity Level	Natural Product ID
0.9759	High Similarity	NPC297574
0.9759	High Similarity	NPC472723
0.9649	High Similarity	NPC173872
0.9649	High Similarity	NPC119094
0.9647	High Similarity	NPC111490
0.9647	High Similarity	NPC261623
0.9645	High Similarity	NPC129533
0.9645	High Similarity	NPC123259
0.9588	High Similarity	NPC231254
0.9586	High Similarity	NPC8940
0.9535	High Similarity	NPC269046
0.9535	High Similarity	NPC7839
0.9535	High Similarity	NPC477083
0.9535	High Similarity	NPC477081
0.9535	High Similarity	NPC142291
0.9532	High Similarity	NPC469650
0.9515	High Similarity	NPC470271
0.9515	High Similarity	NPC311389
0.948	High Similarity	NPC31208
0.948	High Similarity	NPC160543
0.948	High Similarity	NPC472720
0.948	High Similarity	NPC469652
0.948	High Similarity	NPC93065
0.948	High Similarity	NPC472724
0.948	High Similarity	NPC472721
0.9477	High Similarity	NPC65489
0.9477	High Similarity	NPC469649
0.9477	High Similarity	NPC260521
0.9477	High Similarity	NPC237202
0.9455	High Similarity	NPC175793
0.9422	High Similarity	NPC158214
0.9422	High Similarity	NPC290289
0.9422	High Similarity	NPC240200
0.9422	High Similarity	NPC223534
0.9405	High Similarity	NPC263119
0.9405	High Similarity	NPC473550
0.9405	High Similarity	NPC34436
0.9405	High Similarity	NPC166674
0.9405	High Similarity	NPC46640
0.9405	High Similarity	NPC219600
0.9401	High Similarity	NPC470272
0.9401	High Similarity	NPC181778
0.9398	High Similarity	NPC261411
0.9398	High Similarity	NPC43918
0.9398	High Similarity	NPC473818
0.9398	High Similarity	NPC190204
0.9368	High Similarity	NPC187632
0.9368	High Similarity	NPC201814
0.9357	High Similarity	NPC208797
0.9357	High Similarity	NPC53680
0.9341	High Similarity	NPC149300
0.9318	High Similarity	NPC476358
0.9318	High Similarity	NPC477082
0.9314	High Similarity	NPC264302
0.9314	High Similarity	NPC97924
0.9314	High Similarity	NPC40078
0.9314	High Similarity	NPC471091
0.9294	High Similarity	NPC79736
0.9294	High Similarity	NPC67629
0.9286	High Similarity	NPC47521
0.9281	High Similarity	NPC31034
0.9273	High Similarity	NPC291957
0.9273	High Similarity	NPC14030
0.9244	High Similarity	NPC125352
0.924	High Similarity	NPC267549
0.9226	High Similarity	NPC198125
0.9226	High Similarity	NPC95421
0.9217	High Similarity	NPC470898
0.9181	High Similarity	NPC473713
0.9118	High Similarity	NPC65333
0.9118	High Similarity	NPC38438
0.9112	High Similarity	NPC197708
0.9112	High Similarity	NPC658
0.9106	High Similarity	NPC189312
0.9106	High Similarity	NPC3474
0.9102	High Similarity	NPC121290
0.908	High Similarity	NPC297503
0.908	High Similarity	NPC97119
0.908	High Similarity	NPC135831
0.9075	High Similarity	NPC471030
0.9064	High Similarity	NPC88560
0.9064	High Similarity	NPC175230
0.9064	High Similarity	NPC172033
0.9059	High Similarity	NPC149011
0.9059	High Similarity	NPC204937
0.9042	High Similarity	NPC285108
0.9042	High Similarity	NPC33298
0.9036	High Similarity	NPC289346
0.9036	High Similarity	NPC24164
0.9034	High Similarity	NPC105591
0.9034	High Similarity	NPC179947
0.903	High Similarity	NPC238419
0.903	High Similarity	NPC172419
0.9023	High Similarity	NPC170203
0.9017	High Similarity	NPC476623
0.9017	High Similarity	NPC476619
0.9017	High Similarity	NPC476622
0.9017	High Similarity	NPC476620
0.9017	High Similarity	NPC476621
0.9017	High Similarity	NPC476618
0.9006	High Similarity	NPC102851
0.9006	High Similarity	NPC100251
0.9006	High Similarity	NPC174140
0.9006	High Similarity	NPC5786
0.9006	High Similarity	NPC47140
0.9006	High Similarity	NPC67134
0.8983	High Similarity	NPC473618
0.8977	High Similarity	NPC104910
0.8977	High Similarity	NPC474093
0.8976	High Similarity	NPC87317
0.8971	High Similarity	NPC132111
0.897	High Similarity	NPC88803
0.897	High Similarity	NPC300845
0.897	High Similarity	NPC104983
0.897	High Similarity	NPC247629
0.897	High Similarity	NPC250436
0.897	High Similarity	NPC291948
0.897	High Similarity	NPC239019
0.897	High Similarity	NPC318432
0.8966	High Similarity	NPC472725
0.8966	High Similarity	NPC472726
0.896	High Similarity	NPC472991
0.896	High Similarity	NPC472992
0.8953	High Similarity	NPC472993
0.8953	High Similarity	NPC98583
0.8953	High Similarity	NPC163165
0.8941	High Similarity	NPC217781
0.8935	High Similarity	NPC162169
0.8935	High Similarity	NPC166851
0.8929	High Similarity	NPC476372
0.8929	High Similarity	NPC90905
0.8929	High Similarity	NPC4013
0.8929	High Similarity	NPC476371
0.8927	High Similarity	NPC269625
0.8927	High Similarity	NPC475179
0.8922	High Similarity	NPC203020
0.8922	High Similarity	NPC24627
0.8922	High Similarity	NPC53889
0.8922	High Similarity	NPC239966
0.892	High Similarity	NPC49690
0.8916	High Similarity	NPC114179
0.8916	High Similarity	NPC160512
0.8916	High Similarity	NPC156818
0.8916	High Similarity	NPC68324
0.8916	High Similarity	NPC289322
0.8916	High Similarity	NPC38779
0.8916	High Similarity	NPC1913
0.8914	High Similarity	NPC117668
0.8914	High Similarity	NPC469371
0.8908	High Similarity	NPC472387
0.8908	High Similarity	NPC253521
0.8908	High Similarity	NPC196127
0.8908	High Similarity	NPC293626
0.8908	High Similarity	NPC217387
0.8908	High Similarity	NPC267680
0.8908	High Similarity	NPC258044
0.8908	High Similarity	NPC37668
0.8908	High Similarity	NPC113836
0.8882	High Similarity	NPC142707
0.8882	High Similarity	NPC49983
0.8882	High Similarity	NPC26536
0.8882	High Similarity	NPC317671
0.8876	High Similarity	NPC67959
0.8864	High Similarity	NPC199172
0.8864	High Similarity	NPC470718
0.8864	High Similarity	NPC35924
0.8862	High Similarity	NPC114791
0.8862	High Similarity	NPC37502
0.8862	High Similarity	NPC318826
0.8862	High Similarity	NPC40702
0.8862	High Similarity	NPC210501
0.8862	High Similarity	NPC141331
0.8862	High Similarity	NPC267627
0.8862	High Similarity	NPC104222
0.8862	High Similarity	NPC160780
0.8862	High Similarity	NPC289811
0.8857	High Similarity	NPC198902
0.8857	High Similarity	NPC212290
0.8851	High Similarity	NPC144097
0.8851	High Similarity	NPC61904
0.8844	High Similarity	NPC316539
0.8837	High Similarity	NPC52598
0.8837	High Similarity	NPC476365
0.883	High Similarity	NPC116745
0.883	High Similarity	NPC249977
0.883	High Similarity	NPC45400
0.883	High Similarity	NPC298847
0.8824	High Similarity	NPC7752
0.8824	High Similarity	NPC165720
0.8824	High Similarity	NPC142614
0.882	High Similarity	NPC97817
0.882	High Similarity	NPC72554
0.882	High Similarity	NPC30011
0.8814	High Similarity	NPC470713
0.8814	High Similarity	NPC470720
0.8814	High Similarity	NPC470416
0.8814	High Similarity	NPC470717
0.8814	High Similarity	NPC25946
0.8814	High Similarity	NPC460984
0.8814	High Similarity	NPC318119

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 NPC80956 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	384
0.1-0.2	963
0.2-0.3	1964
0.3-0.4	2668
0.4-0.5	1796
0.5-0.6	873
0.6-0.7	355
0.7-0.8	117
0.8-0.85	22
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9006	High Similarity	NPD7993	Clinical (unspecified phase)
0.897	High Similarity	NPD4868	Clinical (unspecified phase)
0.8735	High Similarity	NPD1465	Phase 2
0.8671	High Similarity	NPD5844	Phase 1
0.8621	High Similarity	NPD7074	Phase 3
0.8621	High Similarity	NPD7472	Approved
0.8613	High Similarity	NPD3818	Discontinued
0.858	High Similarity	NPD4338	Clinical (unspecified phase)
0.8563	High Similarity	NPD7054	Approved
0.8475	Intermediate Similarity	NPD7808	Phase 3
0.8466	Intermediate Similarity	NPD6797	Phase 2
0.8427	Intermediate Similarity	NPD8313	Approved
0.8427	Intermediate Similarity	NPD8312	Approved
0.8418	Intermediate Similarity	NPD7251	Discontinued
0.84	Intermediate Similarity	NPD7228	Approved
0.8398	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8391	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8391	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8391	Intermediate Similarity	NPD6166	Phase 2
0.8363	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD8455	Phase 2
0.8218	Intermediate Similarity	NPD7199	Phase 2
0.8208	Intermediate Similarity	NPD6234	Discontinued
0.8171	Intermediate Similarity	NPD6232	Discontinued
0.8135	Intermediate Similarity	NPD8151	Discontinued
0.8129	Intermediate Similarity	NPD1934	Approved
0.8129	Intermediate Similarity	NPD37	Approved
0.8114	Intermediate Similarity	NPD6959	Discontinued
0.8108	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD1653	Approved
0.8092	Intermediate Similarity	NPD4965	Approved
0.8092	Intermediate Similarity	NPD4966	Approved
0.8092	Intermediate Similarity	NPD4967	Phase 2
0.8045	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8034	Intermediate Similarity	NPD7473	Discontinued
0.8023	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD7240	Approved
0.8011	Intermediate Similarity	NPD6559	Discontinued
0.8011	Intermediate Similarity	NPD7685	Pre-registration
0.7978	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7977	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD3749	Approved
0.7941	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD3751	Discontinued
0.7874	Intermediate Similarity	NPD7819	Suspended
0.7874	Intermediate Similarity	NPD2801	Approved
0.7865	Intermediate Similarity	NPD3787	Discontinued
0.7829	Intermediate Similarity	NPD3817	Phase 2
0.7803	Intermediate Similarity	NPD4380	Phase 2
0.7784	Intermediate Similarity	NPD7768	Phase 2
0.7784	Intermediate Similarity	NPD3882	Suspended
0.7778	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7783	Phase 2
0.774	Intermediate Similarity	NPD7075	Discontinued
0.7692	Intermediate Similarity	NPD3750	Approved
0.7661	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD1511	Approved
0.7657	Intermediate Similarity	NPD7411	Suspended
0.7654	Intermediate Similarity	NPD5494	Approved
0.7627	Intermediate Similarity	NPD5402	Approved
0.7627	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD7680	Approved
0.7602	Intermediate Similarity	NPD7435	Discontinued
0.7577	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD1512	Approved
0.7571	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD6190	Approved
0.7543	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD6780	Approved
0.7538	Intermediate Similarity	NPD6776	Approved
0.7538	Intermediate Similarity	NPD6781	Approved
0.7538	Intermediate Similarity	NPD6782	Approved
0.7538	Intermediate Similarity	NPD6777	Approved
0.7538	Intermediate Similarity	NPD6779	Approved
0.7538	Intermediate Similarity	NPD6778	Approved
0.753	Intermediate Similarity	NPD230	Phase 1
0.7515	Intermediate Similarity	NPD7266	Discontinued
0.7514	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6801	Discontinued
0.7485	Intermediate Similarity	NPD4628	Phase 3
0.7475	Intermediate Similarity	NPD7871	Phase 2
0.7475	Intermediate Similarity	NPD7870	Phase 2
0.7471	Intermediate Similarity	NPD1549	Phase 2
0.747	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD1613	Approved
0.7463	Intermediate Similarity	NPD7874	Approved
0.7463	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5403	Approved
0.7424	Intermediate Similarity	NPD7698	Approved
0.7424	Intermediate Similarity	NPD7697	Approved
0.7424	Intermediate Similarity	NPD7696	Phase 3
0.7418	Intermediate Similarity	NPD8127	Discontinued
0.7412	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD3748	Approved
0.7368	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD7701	Phase 2
0.7356	Intermediate Similarity	NPD6799	Approved
0.7345	Intermediate Similarity	NPD7458	Discontinued
0.7326	Intermediate Similarity	NPD6674	Discontinued
0.7326	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD2533	Approved
0.7314	Intermediate Similarity	NPD2534	Approved
0.7314	Intermediate Similarity	NPD5401	Approved
0.7314	Intermediate Similarity	NPD2532	Approved
0.7314	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6599	Discontinued
0.73	Intermediate Similarity	NPD8319	Approved
0.73	Intermediate Similarity	NPD8320	Phase 1
0.7286	Intermediate Similarity	NPD6823	Phase 2
0.7282	Intermediate Similarity	NPD6534	Approved
0.7282	Intermediate Similarity	NPD6535	Approved
0.7273	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD7699	Phase 2
0.7259	Intermediate Similarity	NPD7700	Phase 2
0.7257	Intermediate Similarity	NPD7390	Discontinued
0.7255	Intermediate Similarity	NPD7801	Approved
0.7247	Intermediate Similarity	NPD3226	Approved
0.7243	Intermediate Similarity	NPD3926	Phase 2
0.724	Intermediate Similarity	NPD8150	Discontinued
0.7229	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD919	Approved
0.7193	Intermediate Similarity	NPD1510	Phase 2
0.7192	Intermediate Similarity	NPD7585	Approved
0.719	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD7229	Phase 3
0.7186	Intermediate Similarity	NPD3027	Phase 3
0.7175	Intermediate Similarity	NPD6273	Approved
0.7151	Intermediate Similarity	NPD2796	Approved
0.715	Intermediate Similarity	NPD8434	Phase 2
0.7143	Intermediate Similarity	NPD7583	Approved
0.7143	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7177	Discontinued
0.712	Intermediate Similarity	NPD7549	Discontinued
0.7118	Intermediate Similarity	NPD1933	Approved
0.7118	Intermediate Similarity	NPD447	Suspended
0.7086	Intermediate Similarity	NPD7003	Approved
0.7086	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD4287	Approved
0.7059	Intermediate Similarity	NPD943	Approved
0.7059	Intermediate Similarity	NPD5242	Approved
0.7056	Intermediate Similarity	NPD6213	Phase 3
0.7056	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6212	Phase 3
0.7052	Intermediate Similarity	NPD5406	Approved
0.7052	Intermediate Similarity	NPD5404	Approved
0.7052	Intermediate Similarity	NPD5408	Approved
0.7052	Intermediate Similarity	NPD1551	Phase 2
0.7052	Intermediate Similarity	NPD5405	Approved
0.7049	Intermediate Similarity	NPD5353	Approved
0.7042	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD3764	Approved
0.7035	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD4908	Phase 1
0.7015	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD8166	Discontinued
0.6979	Remote Similarity	NPD7038	Approved
0.6979	Remote Similarity	NPD7039	Approved
0.6976	Remote Similarity	NPD7584	Approved
0.697	Remote Similarity	NPD9269	Phase 2
0.6959	Remote Similarity	NPD1240	Approved
0.6957	Remote Similarity	NPD4288	Approved
0.6954	Remote Similarity	NPD6099	Approved
0.6954	Remote Similarity	NPD6100	Approved
0.6954	Remote Similarity	NPD2935	Discontinued
0.6952	Remote Similarity	NPD1247	Approved
0.6944	Remote Similarity	NPD920	Approved
0.6941	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6798	Discontinued
0.6939	Remote Similarity	NPD6841	Approved
0.6939	Remote Similarity	NPD6843	Phase 3
0.6939	Remote Similarity	NPD6842	Approved
0.6936	Remote Similarity	NPD7097	Phase 1
0.6927	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD5710	Approved
0.6915	Remote Similarity	NPD5711	Approved
0.6914	Remote Similarity	NPD2346	Discontinued
0.6905	Remote Similarity	NPD7930	Approved
0.69	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1607	Approved
0.6864	Remote Similarity	NPD9494	Approved
0.6863	Remote Similarity	NPD5006	Approved
0.6863	Remote Similarity	NPD5005	Approved
0.6839	Remote Similarity	NPD5953	Discontinued
0.6836	Remote Similarity	NPD1243	Approved
0.6836	Remote Similarity	NPD1652	Phase 2
0.6821	Remote Similarity	NPD5124	Phase 1
0.6821	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD1091	Approved
0.6802	Remote Similarity	NPD6233	Phase 2
0.68	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD6386	Approved
0.6793	Remote Similarity	NPD7615	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data