NPASS Compound

Structure

NPC111428 OpenBabel07101719252D 52 55 0 0 1 0 0 0 0 0999 V2000 4.1920 4.9959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6202 -0.7392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2928 -3.0623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3702 2.0702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7984 2.1865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4572 -3.5447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2928 -2.0974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5346 1.5877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3702 3.0351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9628 2.6690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7984 1.2216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6215 -3.0623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4572 -1.6149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6989 2.0702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5346 3.5175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1271 2.1865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9628 0.7392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7859 5.8716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6215 6.3541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7859 -1.6149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0277 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4559 0.2567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6202 3.5175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1920 0.7392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6215 -2.0974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6989 3.0351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1271 1.2216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7859 4.9067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7859 -0.6500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1920 3.5175 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6202 0.7392 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6215 7.3190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.2567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5718 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5220 2.6108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9503 1.6459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7361 4.7391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8356 -0.4825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7859 7.8014 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.9503 2.6108 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.5220 1.6459 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8356 4.7391 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.7361 -0.4825 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.5718 4.2567 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4572 7.8014 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6202 4.9959 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1920 -0.7392 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4723 2.7784 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9005 1.4783 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0662 5.6459 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5056 -1.3892 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 44 1 0 0 0 0 2 45 1 0 0 0 0 3 6 2 0 0 0 0 3 7 1 0 0 0 0 4 8 2 0 0 0 0 4 9 1 0 0 0 0 5 10 2 0 0 0 0 5 11 1 0 0 0 0 6 12 1 0 0 0 0 7 13 2 0 0 0 0 8 14 1 0 0 0 0 9 15 2 0 0 0 0 10 16 1 0 0 0 0 11 17 2 0 0 0 0 12 25 2 0 0 0 0 13 25 1 0 0 0 0 14 26 2 0 0 0 0 15 26 1 0 0 0 0 16 27 2 0 0 0 0 17 27 1 0 0 0 0 18 19 1 0 0 0 0 19 32 1 0 0 0 0 20 25 1 0 0 0 0 21 26 1 0 0 0 0 22 27 1 0 0 0 0 23 33 1 0 0 0 0 23 40 1 0 0 0 0 24 34 1 0 0 0 0 24 41 1 0 0 0 0 28 18 1 1 0 0 0 28 37 1 0 0 0 0 28 42 1 0 0 0 0 29 20 1 1 0 0 0 29 38 1 0 0 0 0 29 43 1 0 0 0 0 30 21 1 1 0 0 0 30 35 1 0 0 0 0 30 44 1 0 0 0 0 31 22 1 1 0 0 0 31 36 1 0 0 0 0 31 45 1 0 0 0 0 32 39 2 0 0 0 0 32 46 1 0 0 0 0 33 42 2 3 0 0 0 33 47 1 0 0 0 0 34 43 2 3 0 0 0 34 48 1 0 0 0 0 35 41 2 3 0 0 0 35 49 1 0 0 0 0 36 40 2 3 0 0 0 36 50 1 0 0 0 0 37 44 1 0 0 0 0 37 51 2 0 0 0 0 38 45 1 0 0 0 0 38 52 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	711.34
Volume:	727.904
LogP:	0.665
LogD:	1.115
LogS:	-3.082
# Rotatable Bonds:	9
TPSA:	200.11
# H-Bond Aceptor:	14
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.203
Synthetic Accessibility Score:	4.622
Fsp3:	0.342
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.058
MDCK Permeability:	0.00015582186460960656
Pgp-inhibitor:	0.996
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.828
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.05
Plasma Protein Binding (PPB):	75.27088928222656%
Volume Distribution (VD):	0.3
Pgp-substrate:	27.463821411132812%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.02
CYP2C19-inhibitor:	0.136
CYP2C19-substrate:	0.046
CYP2C9-inhibitor:	0.466
CYP2C9-substrate:	0.033
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.096
CYP3A4-inhibitor:	0.923
CYP3A4-substrate:	0.066

ADMET: Excretion

Clearance (CL):	2.847
Half-life (T1/2):	0.57

ADMET: Toxicity

hERG Blockers:	0.084
Human Hepatotoxicity (H-HT):	0.28
Drug-inuced Liver Injury (DILI):	0.585
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.854
Maximum Recommended Daily Dose:	0.888
Skin Sensitization:	0.343
Carcinogencity:	0.013
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.127

Download Data

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

Natural Product: NPC111428

Natural Product ID:	NPC111428
*Common Name:**	Scleramide
IUPAC Name:	3-[(2S,5S,11S,14S)-5,11,14-tribenzyl-4,13-dimethyl-3,6,9,12,15,18-hexaoxo-1,4,7,10,13,16-hexazacyclooctadec-2-yl]propanamide
Synonyms:	Scleramide
Standard InCHIKey:	UTVCBQCZOQNCAY-ORYMTKCHSA-N
Standard InCHI:	InChI=1S/C38H45N7O7/c1-44-30(21-26-14-8-4-9-15-26)35(49)41-24-34(48)43-29(20-25-12-6-3-7-13-25)38(52)45(2)31(22-27-16-10-5-11-17-27)36(50)40-23-33(47)42-28(37(44)51)18-19-32(39)46/h3-17,28-31H,18-24H2,1-2H3,(H2,39,46)(H,40,50)(H,41,49)(H,42,47)(H,43,48)/t28-,29-,30-,31-/m0/s1
SMILES:	OC(=N)CC[C@@H]1N=C(O)CN=C(O)[C@H](Cc2ccccc2)N(C)C(=O)[C@@H](N=C(CN=C([C@@H](N(C1=O)C)Cc1ccccc1)O)O)Cc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509938
PubChem CID:	10818573
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000064] Macrolactams

*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
NPO7803	Aspergillus sclerotiorum	Species	Aspergillaceae	Eukaryota	sclerotia	n.a.	n.a.	PMID[10924188]
NPO7803	Aspergillus sclerotiorum	Species	Aspergillaceae	Eukaryota	Sclerotia	n.a.	n.a.	PMID[8946752]

☑ 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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	27.0	%	PMID[553490]

☑ 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 NPC111428 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	145
0.1-0.2	1066
0.2-0.3	6878
0.3-0.4	16849
0.4-0.5	14274
0.5-0.6	2596
0.6-0.7	550
0.7-0.8	297
0.8-0.85	29
0.85-0.9	11
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9206	High Similarity	NPC255447
0.9048	High Similarity	NPC473322
0.9008	High Similarity	NPC470546
0.8926	High Similarity	NPC470545
0.8843	High Similarity	NPC470544
0.871	High Similarity	NPC200964
0.8661	High Similarity	NPC101719
0.864	High Similarity	NPC71684
0.8583	High Similarity	NPC222466
0.8538	High Similarity	NPC200589
0.8525	High Similarity	NPC33742
0.837	Intermediate Similarity	NPC132636
0.8359	Intermediate Similarity	NPC6975
0.8293	Intermediate Similarity	NPC35850
0.8293	Intermediate Similarity	NPC276949
0.824	Intermediate Similarity	NPC285926
0.824	Intermediate Similarity	NPC315276
0.824	Intermediate Similarity	NPC14672
0.8203	Intermediate Similarity	NPC202521
0.8154	Intermediate Similarity	NPC22746
0.8125	Intermediate Similarity	NPC476990
0.8095	Intermediate Similarity	NPC239357
0.8077	Intermediate Similarity	NPC46427
0.8071	Intermediate Similarity	NPC209509
0.806	Intermediate Similarity	NPC130309
0.8056	Intermediate Similarity	NPC122590
0.8043	Intermediate Similarity	NPC163392
0.8043	Intermediate Similarity	NPC239762
0.8015	Intermediate Similarity	NPC248283
0.8	Intermediate Similarity	NPC252878
0.7985	Intermediate Similarity	NPC300315
0.7973	Intermediate Similarity	NPC473003
0.7958	Intermediate Similarity	NPC16188
0.7929	Intermediate Similarity	NPC161069
0.7872	Intermediate Similarity	NPC52748
0.7862	Intermediate Similarity	NPC233702
0.7847	Intermediate Similarity	NPC2501
0.7836	Intermediate Similarity	NPC319766
0.7829	Intermediate Similarity	NPC220698
0.7829	Intermediate Similarity	NPC328649
0.7823	Intermediate Similarity	NPC469903
0.781	Intermediate Similarity	NPC287401
0.7808	Intermediate Similarity	NPC473341
0.7803	Intermediate Similarity	NPC474082
0.7803	Intermediate Similarity	NPC175726
0.7778	Intermediate Similarity	NPC474584
0.777	Intermediate Similarity	NPC127741
0.777	Intermediate Similarity	NPC471264
0.777	Intermediate Similarity	NPC471265
0.7762	Intermediate Similarity	NPC262077
0.7761	Intermediate Similarity	NPC477937
0.776	Intermediate Similarity	NPC319579
0.7754	Intermediate Similarity	NPC141050
0.7746	Intermediate Similarity	NPC476978
0.7733	Intermediate Similarity	NPC471527
0.7724	Intermediate Similarity	NPC254798
0.7714	Intermediate Similarity	NPC98424
0.7714	Intermediate Similarity	NPC92784
0.7714	Intermediate Similarity	NPC470884
0.7714	Intermediate Similarity	NPC178662
0.7714	Intermediate Similarity	NPC476133
0.7708	Intermediate Similarity	NPC138775
0.7692	Intermediate Similarity	NPC5620
0.7687	Intermediate Similarity	NPC202198
0.7662	Intermediate Similarity	NPC469904
0.7655	Intermediate Similarity	NPC471820
0.7655	Intermediate Similarity	NPC471821
0.7655	Intermediate Similarity	NPC105717
0.7642	Intermediate Similarity	NPC473418
0.7635	Intermediate Similarity	NPC473002
0.7632	Intermediate Similarity	NPC471053
0.7632	Intermediate Similarity	NPC471052
0.7632	Intermediate Similarity	NPC471051
0.763	Intermediate Similarity	NPC136453
0.7616	Intermediate Similarity	NPC469902
0.7606	Intermediate Similarity	NPC269398
0.7606	Intermediate Similarity	NPC263493
0.7606	Intermediate Similarity	NPC476989
0.7582	Intermediate Similarity	NPC223207
0.7574	Intermediate Similarity	NPC239990
0.7574	Intermediate Similarity	NPC152850
0.7574	Intermediate Similarity	NPC105114
0.7574	Intermediate Similarity	NPC71933
0.7574	Intermediate Similarity	NPC89923
0.7569	Intermediate Similarity	NPC315266
0.7566	Intermediate Similarity	NPC241794
0.7552	Intermediate Similarity	NPC139326
0.7552	Intermediate Similarity	NPC77905
0.7535	Intermediate Similarity	NPC476259
0.7532	Intermediate Similarity	NPC471771
0.7532	Intermediate Similarity	NPC290755
0.7532	Intermediate Similarity	NPC304074
0.7517	Intermediate Similarity	NPC314114
0.7516	Intermediate Similarity	NPC306804
0.75	Intermediate Similarity	NPC314388
0.75	Intermediate Similarity	NPC315283
0.7484	Intermediate Similarity	NPC141957
0.7483	Intermediate Similarity	NPC297145
0.7483	Intermediate Similarity	NPC197743
0.7483	Intermediate Similarity	NPC129666
0.7468	Intermediate Similarity	NPC155506
0.7468	Intermediate Similarity	NPC159767
0.7465	Intermediate Similarity	NPC89489
0.745	Intermediate Similarity	NPC286551
0.745	Intermediate Similarity	NPC56685
0.7448	Intermediate Similarity	NPC313867
0.7448	Intermediate Similarity	NPC316008
0.7448	Intermediate Similarity	NPC322878
0.744	Intermediate Similarity	NPC45033
0.7434	Intermediate Similarity	NPC287757
0.7434	Intermediate Similarity	NPC1390
0.7434	Intermediate Similarity	NPC62104
0.7434	Intermediate Similarity	NPC319320
0.7431	Intermediate Similarity	NPC197682
0.7431	Intermediate Similarity	NPC176226
0.7421	Intermediate Similarity	NPC196243
0.7419	Intermediate Similarity	NPC61004
0.7413	Intermediate Similarity	NPC307357
0.7413	Intermediate Similarity	NPC268841
0.7413	Intermediate Similarity	NPC46098
0.741	Intermediate Similarity	NPC157311
0.7397	Intermediate Similarity	NPC314358
0.7394	Intermediate Similarity	NPC68865
0.7391	Intermediate Similarity	NPC469666
0.7386	Intermediate Similarity	NPC469243
0.7383	Intermediate Similarity	NPC162104
0.7375	Intermediate Similarity	NPC473001
0.7368	Intermediate Similarity	NPC324850
0.7361	Intermediate Similarity	NPC168113
0.7357	Intermediate Similarity	NPC44805
0.7357	Intermediate Similarity	NPC8761
0.7355	Intermediate Similarity	NPC473501
0.7355	Intermediate Similarity	NPC475439
0.7348	Intermediate Similarity	NPC169328
0.7347	Intermediate Similarity	NPC311658
0.7343	Intermediate Similarity	NPC242159
0.7343	Intermediate Similarity	NPC313694
0.7342	Intermediate Similarity	NPC230611
0.7339	Intermediate Similarity	NPC164859
0.7329	Intermediate Similarity	NPC269750
0.7329	Intermediate Similarity	NPC471680
0.7329	Intermediate Similarity	NPC45037
0.7329	Intermediate Similarity	NPC194671
0.732	Intermediate Similarity	NPC244336
0.7317	Intermediate Similarity	NPC138083
0.7315	Intermediate Similarity	NPC473491
0.7315	Intermediate Similarity	NPC7817
0.7315	Intermediate Similarity	NPC475168
0.7302	Intermediate Similarity	NPC327481
0.7299	Intermediate Similarity	NPC47667
0.7299	Intermediate Similarity	NPC4974
0.7296	Intermediate Similarity	NPC273755
0.7296	Intermediate Similarity	NPC137627
0.7293	Intermediate Similarity	NPC310467
0.7287	Intermediate Similarity	NPC329011
0.7279	Intermediate Similarity	NPC35996
0.7278	Intermediate Similarity	NPC198254
0.7278	Intermediate Similarity	NPC274198
0.7273	Intermediate Similarity	NPC25565
0.7273	Intermediate Similarity	NPC475544
0.7261	Intermediate Similarity	NPC107938
0.7261	Intermediate Similarity	NPC294516
0.725	Intermediate Similarity	NPC477462
0.725	Intermediate Similarity	NPC164608
0.725	Intermediate Similarity	NPC473402
0.725	Intermediate Similarity	NPC279871
0.725	Intermediate Similarity	NPC136797
0.7248	Intermediate Similarity	NPC283783
0.7244	Intermediate Similarity	NPC210377
0.7244	Intermediate Similarity	NPC217804
0.7244	Intermediate Similarity	NPC5719
0.7244	Intermediate Similarity	NPC22883
0.7241	Intermediate Similarity	NPC469426
0.7241	Intermediate Similarity	NPC469427
0.7236	Intermediate Similarity	NPC12730
0.7234	Intermediate Similarity	NPC257390
0.7234	Intermediate Similarity	NPC246079
0.7233	Intermediate Similarity	NPC89831
0.723	Intermediate Similarity	NPC225648
0.723	Intermediate Similarity	NPC329761
0.723	Intermediate Similarity	NPC135121
0.7213	Intermediate Similarity	NPC311242
0.7211	Intermediate Similarity	NPC477217
0.7211	Intermediate Similarity	NPC201244
0.7205	Intermediate Similarity	NPC50016
0.7203	Intermediate Similarity	NPC314835
0.72	Intermediate Similarity	NPC471317
0.7197	Intermediate Similarity	NPC15068
0.7197	Intermediate Similarity	NPC197470
0.7185	Intermediate Similarity	NPC478015
0.7185	Intermediate Similarity	NPC478014
0.7185	Intermediate Similarity	NPC27833
0.7185	Intermediate Similarity	NPC478016
0.7183	Intermediate Similarity	NPC244866
0.7181	Intermediate Similarity	NPC240848
0.7179	Intermediate Similarity	NPC191863
0.7179	Intermediate Similarity	NPC133470
0.7179	Intermediate Similarity	NPC289776
0.7171	Intermediate Similarity	NPC470902
0.717	Intermediate Similarity	NPC40234

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 NPC111428 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	112
0.1-0.2	363
0.2-0.3	758
0.3-0.4	1743
0.4-0.5	3592
0.5-0.6	2026
0.6-0.7	462
0.7-0.8	90
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8527	High Similarity	NPD5339	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD7720	Phase 2
0.8214	Intermediate Similarity	NPD8323	Discontinued
0.8175	Intermediate Similarity	NPD7728	Clinical (unspecified phase)
0.8162	Intermediate Similarity	NPD8172	Phase 2
0.8162	Intermediate Similarity	NPD8173	Phase 2
0.8085	Intermediate Similarity	NPD7602	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD8290	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD4677	Discontinued
0.7842	Intermediate Similarity	NPD6901	Phase 3
0.7826	Intermediate Similarity	NPD8643	Discontinued
0.7803	Intermediate Similarity	NPD3073	Approved
0.7803	Intermediate Similarity	NPD2584	Suspended
0.7803	Intermediate Similarity	NPD3072	Approved
0.7803	Intermediate Similarity	NPD3071	Approved
0.7801	Intermediate Similarity	NPD8076	Discontinued
0.777	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD5341	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD5581	Approved
0.7727	Intermediate Similarity	NPD4762	Approved
0.7727	Intermediate Similarity	NPD4761	Approved
0.7721	Intermediate Similarity	NPD5263	Approved
0.7721	Intermediate Similarity	NPD4125	Approved
0.7704	Intermediate Similarity	NPD3608	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD4706	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD7979	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD3125	Approved
0.7535	Intermediate Similarity	NPD5301	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD6073	Approved
0.7518	Intermediate Similarity	NPD4175	Approved
0.7518	Intermediate Similarity	NPD4177	Approved
0.7517	Intermediate Similarity	NPD8315	Phase 1
0.75	Intermediate Similarity	NPD8416	Discontinued
0.75	Intermediate Similarity	NPD7613	Discontinued
0.75	Intermediate Similarity	NPD999	Phase 2
0.75	Intermediate Similarity	NPD6623	Phase 3
0.7483	Intermediate Similarity	NPD7450	Phase 2
0.7482	Intermediate Similarity	NPD3632	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD6552	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD6295	Approved
0.7465	Intermediate Similarity	NPD6294	Approved
0.7464	Intermediate Similarity	NPD4676	Approved
0.7447	Intermediate Similarity	NPD3908	Approved
0.7445	Intermediate Similarity	NPD4151	Approved
0.7391	Intermediate Similarity	NPD7828	Discontinued
0.7376	Intermediate Similarity	NPD8265	Approved
0.7365	Intermediate Similarity	NPD6088	Approved
0.7357	Intermediate Similarity	NPD1330	Phase 2
0.7357	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD3644	Approved
0.7344	Intermediate Similarity	NPD3642	Approved
0.7344	Intermediate Similarity	NPD3643	Approved
0.7319	Intermediate Similarity	NPD3604	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD3561	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD7130	Phase 3
0.7299	Intermediate Similarity	NPD5577	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD5578	Approved
0.7299	Intermediate Similarity	NPD6792	Phase 3
0.7299	Intermediate Similarity	NPD5367	Discontinued
0.7273	Intermediate Similarity	NPD5725	Approved
0.7266	Intermediate Similarity	NPD3626	Phase 3
0.7266	Intermediate Similarity	NPD3040	Approved
0.7259	Intermediate Similarity	NPD2956	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD5296	Approved
0.7248	Intermediate Similarity	NPD6631	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD7892	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6897	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1040	Phase 2
0.7222	Intermediate Similarity	NPD6852	Discontinued
0.7222	Intermediate Similarity	NPD5717	Approved
0.7197	Intermediate Similarity	NPD1348	Approved
0.7183	Intermediate Similarity	NPD941	Approved
0.7179	Intermediate Similarity	NPD8351	Phase 2
0.7162	Intermediate Similarity	NPD1968	Approved
0.7162	Intermediate Similarity	NPD1967	Approved
0.7153	Intermediate Similarity	NPD6817	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5759	Approved
0.7143	Intermediate Similarity	NPD7679	Phase 2
0.7133	Intermediate Similarity	NPD8165	Discontinued
0.7133	Intermediate Similarity	NPD5323	Approved
0.7122	Intermediate Similarity	NPD6302	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7080	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD6038	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD4126	Approved
0.7097	Intermediate Similarity	NPD7011	Discontinued
0.7092	Intermediate Similarity	NPD6359	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD4432	Discontinued
0.7078	Intermediate Similarity	NPD7267	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD2088	Approved
0.7075	Intermediate Similarity	NPD2087	Approved
0.7063	Intermediate Similarity	NPD7634	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5747	Discontinued
0.7055	Intermediate Similarity	NPD8362	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7303	Discontinued
0.7039	Intermediate Similarity	NPD6078	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD8125	Discontinued
0.7029	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6681	Discovery
0.7014	Intermediate Similarity	NPD4153	Approved
0.6993	Remote Similarity	NPD2078	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD5299	Approved
0.6993	Remote Similarity	NPD7131	Phase 3
0.6987	Remote Similarity	NPD8019	Approved
0.6985	Remote Similarity	NPD5981	Approved
0.6984	Remote Similarity	NPD4119	Approved
0.6984	Remote Similarity	NPD5716	Approved
0.698	Remote Similarity	NPD5024	Approved
0.697	Remote Similarity	NPD480	Approved
0.6968	Remote Similarity	NPD8417	Discontinued
0.6966	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7522	Discontinued
0.6959	Remote Similarity	NPD2022	Approved
0.6953	Remote Similarity	NPD1018	Approved
0.6948	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7508	Discontinued
0.6939	Remote Similarity	NPD6864	Phase 2
0.6939	Remote Similarity	NPD6865	Phase 2
0.6934	Remote Similarity	NPD7342	Discontinued
0.6928	Remote Similarity	NPD5748	Phase 2
0.6923	Remote Similarity	NPD2047	Approved
0.6923	Remote Similarity	NPD2044	Approved
0.6923	Remote Similarity	NPD2043	Approved
0.6923	Remote Similarity	NPD2051	Approved
0.6923	Remote Similarity	NPD2045	Approved
0.6923	Remote Similarity	NPD21	Approved
0.6923	Remote Similarity	NPD2049	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2050	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2048	Approved
0.6923	Remote Similarity	NPD2046	Approved
0.6923	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD3598	Phase 3
0.6912	Remote Similarity	NPD6343	Approved
0.6912	Remote Similarity	NPD6345	Approved
0.6912	Remote Similarity	NPD2218	Phase 2
0.6912	Remote Similarity	NPD2217	Approved
0.6909	Remote Similarity	NPD7771	Discontinued
0.6906	Remote Similarity	NPD5335	Discontinued
0.6899	Remote Similarity	NPD7600	Phase 2
0.6894	Remote Similarity	NPD7485	Phase 3
0.6894	Remote Similarity	NPD7484	Phase 3
0.689	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD3123	Discovery
0.6885	Remote Similarity	NPD1814	Approved
0.6885	Remote Similarity	NPD1812	Approved
0.6875	Remote Similarity	NPD8303	Discontinued
0.6875	Remote Similarity	NPD2846	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4214	Discontinued
0.6871	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5265	Approved
0.6867	Remote Similarity	NPD5264	Approved
0.6866	Remote Similarity	NPD3551	Approved
0.6855	Remote Similarity	NPD4564	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD4565	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD4152	Approved
0.6838	Remote Similarity	NPD3806	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7599	Phase 2
0.6828	Remote Similarity	NPD8118	Discontinued
0.6824	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD4733	Approved
0.6809	Remote Similarity	NPD6325	Discontinued
0.6809	Remote Similarity	NPD2031	Discontinued
0.6806	Remote Similarity	NPD4794	Discontinued
0.6802	Remote Similarity	NPD8240	Discontinued
0.68	Remote Similarity	NPD2437	Approved
0.68	Remote Similarity	NPD9566	Approved
0.68	Remote Similarity	NPD2436	Approved
0.6797	Remote Similarity	NPD5613	Approved
0.6797	Remote Similarity	NPD2014	Approved
0.6797	Remote Similarity	NPD5614	Approved
0.6797	Remote Similarity	NPD2016	Approved
0.6797	Remote Similarity	NPD2013	Approved
0.6788	Remote Similarity	NPD998	Approved
0.6779	Remote Similarity	NPD7512	Approved
0.6779	Remote Similarity	NPD7511	Approved
0.6772	Remote Similarity	NPD4760	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5162	Approved
0.6763	Remote Similarity	NPD3881	Discontinued
0.6757	Remote Similarity	NPD8154	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD5942	Approved
0.6753	Remote Similarity	NPD5941	Approved
0.6753	Remote Similarity	NPD4682	Phase 2
0.6748	Remote Similarity	NPD7968	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7608	Discontinued
0.6748	Remote Similarity	NPD6690	Approved
0.6746	Remote Similarity	NPD4117	Approved
0.6739	Remote Similarity	NPD6994	Approved
0.6739	Remote Similarity	NPD6993	Approved
0.6732	Remote Similarity	NPD3519	Discontinued
0.6732	Remote Similarity	NPD5308	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD4803	Discontinued
0.6713	Remote Similarity	NPD7451	Discontinued
0.6712	Remote Similarity	NPD7086	Phase 2
0.6711	Remote Similarity	NPD6655	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