NPASS Compound

Structure

NPC133470 OpenBabel07101719252D 46 49 0 0 1 0 0 0 0 0999 V2000 -3.6676 -1.2476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0181 -2.8158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6546 4.7627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5966 -0.7775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9806 3.1678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2342 2.2212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0340 3.4215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8460 5.4440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5828 4.7978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5413 1.5282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3410 2.7285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0820 5.1290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3916 3.8366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0410 0.7368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1923 2.2068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8897 1.2268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0410 2.6968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9848 -1.4692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9017 1.0889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4949 0.2468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8902 -1.8442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0580 3.9853 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5946 1.7819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1923 1.2268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8897 2.2068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2732 4.1678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4636 3.5216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9551 1.3426 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8568 -0.4975 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6462 0.7368 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7042 3.2485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2012 4.4828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5216 0.4636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9612 1.6648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8789 -0.4334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1791 4.4187 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8971 2.6427 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.0192 2.3205 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.7848 -0.1825 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 5.7384 2.6968 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5529 3.7385 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0732 5.4544 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2991 -0.1330 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9328 1.5369 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6253 -1.3801 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 4 40 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 10 1 0 0 0 0 7 11 2 0 0 0 0 8 9 2 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 10 23 2 0 0 0 0 11 23 1 0 0 0 0 12 26 2 0 0 0 0 13 27 2 0 0 0 0 14 16 1 0 0 0 0 14 24 2 0 0 0 0 15 17 2 0 0 0 0 15 24 1 0 0 0 0 16 25 2 0 0 0 0 17 25 1 0 0 0 0 18 21 1 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 22 3 1 6 0 0 0 22 31 1 0 0 0 0 22 36 1 0 0 0 0 25 41 1 0 0 0 0 26 27 1 0 0 0 0 26 32 1 0 0 0 0 27 37 1 0 0 0 0 28 19 1 6 0 0 0 28 33 1 0 0 0 0 28 38 1 0 0 0 0 29 18 1 6 0 0 0 29 35 1 0 0 0 0 29 39 1 0 0 0 0 30 20 1 6 0 0 0 30 34 1 0 0 0 0 30 40 1 0 0 0 0 31 38 2 3 0 0 0 31 42 1 0 0 0 0 32 36 2 3 0 0 0 32 43 1 0 0 0 0 33 39 2 3 0 0 0 33 44 1 0 0 0 0 34 37 2 3 0 0 0 34 45 1 0 0 0 0 35 40 1 0 0 0 0 35 46 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	627.31
Volume:	650.505
LogP:	4.022
LogD:	3.758
LogS:	-5.305
# Rotatable Bonds:	6
TPSA:	156.94
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.283
Synthetic Accessibility Score:	4.438
Fsp3:	0.343
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:	-6.115
MDCK Permeability:	5.189637158764526e-05
Pgp-inhibitor:	0.886
Pgp-substrate:	0.978
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.429
30% Bioavailability (F30%):	0.676

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	92.28303527832031%
Volume Distribution (VD):	0.426
Pgp-substrate:	4.824648857116699%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.04
CYP2C19-inhibitor:	0.427
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.905
CYP2C9-substrate:	0.772
CYP2D6-inhibitor:	0.066
CYP2D6-substrate:	0.303
CYP3A4-inhibitor:	0.949
CYP3A4-substrate:	0.23

ADMET: Excretion

Clearance (CL):	3.824
Half-life (T1/2):	0.496

ADMET: Toxicity

hERG Blockers:	0.15
Human Hepatotoxicity (H-HT):	0.946
Drug-inuced Liver Injury (DILI):	0.956
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.823
Maximum Recommended Daily Dose:	0.9
Skin Sensitization:	0.153
Carcinogencity:	0.058
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.154

Download Data

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

Natural Product: NPC133470

Natural Product ID:	NPC133470
*Common Name:**	Cycloaspeptide C
IUPAC Name:	(4S,7S,10S,13S)-7-benzyl-13-[(4-hydroxyphenyl)methyl]-4,12-dimethyl-10-(2-methylpropyl)-3,6,9,12,15-pentazabicyclo[14.4.0]icosa-1(20),16,18-triene-2,5,8,11,14-pentone
Synonyms:	cycloaspeptide C
Standard InCHIKey:	WBLLMCDBMQQWEY-BJPINVTDSA-N
Standard InCHI:	InChI=1S/C35H41N5O6/c1-21(2)18-29-35(46)40(4)30(20-24-14-16-25(41)17-15-24)34(45)37-27-13-9-8-12-26(27)32(43)36-22(3)31(42)38-28(33(44)39-29)19-23-10-6-5-7-11-23/h5-17,21-22,28-30,41H,18-20H2,1-4H3,(H,36,43)(H,37,45)(H,38,42)(H,39,44)/t22-,28-,29-,30-/m0/s1
SMILES:	CC(C)C[C@H]1C(=O)N(C)[C@@H](Cc2ccc(cc2)O)C(=Nc2ccccc2C(=N[C@@H](C)C(=N[C@@H](Cc2ccccc2)C(=N1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL553487
PubChem CID:	45273572
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
NPO10809	Isaria farinosa	Species	Cordycipitaceae	Eukaryota	Cordyceps-colonizing isolate of Isaria farinosa	n.a.	n.a.	PMID[19572613]
NPO10809	Isaria farinosa	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21158423]
NPO10809	Isaria farinosa	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21495659]
NPO10809	Isaria farinosa	Species	Cordycipitaceae	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
GI50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	GI50	>	63400.0	nM	PMID[520332]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	31900.0	nM	PMID[520332]

☑ 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 NPC133470 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	250
0.1-0.2	1730
0.2-0.3	11352
0.3-0.4	6358
0.4-0.5	14712
0.5-0.6	6701
0.6-0.7	1369
0.7-0.8	205
0.8-0.85	9
0.85-0.9	5
0.9-0.95	1
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC191863
1.0	High Similarity	NPC289776
0.9257	High Similarity	NPC254798
0.8397	Intermediate Similarity	NPC233702
0.8258	Intermediate Similarity	NPC16188
0.817	Intermediate Similarity	NPC476989
0.8167	Intermediate Similarity	NPC311357
0.8012	Intermediate Similarity	NPC39822
0.8	Intermediate Similarity	NPC202198
0.7988	Intermediate Similarity	NPC158277
0.7987	Intermediate Similarity	NPC473491
0.7904	Intermediate Similarity	NPC328649
0.7892	Intermediate Similarity	NPC189116
0.7892	Intermediate Similarity	NPC223207
0.7844	Intermediate Similarity	NPC471771
0.7844	Intermediate Similarity	NPC290755
0.7844	Intermediate Similarity	NPC304074
0.7798	Intermediate Similarity	NPC141957
0.7778	Intermediate Similarity	NPC56685
0.7778	Intermediate Similarity	NPC279871
0.7771	Intermediate Similarity	NPC241794
0.773	Intermediate Similarity	NPC473460
0.7719	Intermediate Similarity	NPC248670
0.7712	Intermediate Similarity	NPC257390
0.7711	Intermediate Similarity	NPC469243
0.7683	Intermediate Similarity	NPC476268
0.7674	Intermediate Similarity	NPC136797
0.767	Intermediate Similarity	NPC294951
0.7669	Intermediate Similarity	NPC262166
0.7669	Intermediate Similarity	NPC5194
0.7669	Intermediate Similarity	NPC261934
0.7662	Intermediate Similarity	NPC244866
0.7661	Intermediate Similarity	NPC230611
0.7651	Intermediate Similarity	NPC244336
0.7644	Intermediate Similarity	NPC269750
0.7644	Intermediate Similarity	NPC194671
0.764	Intermediate Similarity	NPC9373
0.7633	Intermediate Similarity	NPC61004
0.7625	Intermediate Similarity	NPC81026
0.7605	Intermediate Similarity	NPC475544
0.7602	Intermediate Similarity	NPC40234
0.7588	Intermediate Similarity	NPC294516
0.7588	Intermediate Similarity	NPC107938
0.758	Intermediate Similarity	NPC242159
0.758	Intermediate Similarity	NPC313694
0.7572	Intermediate Similarity	NPC155506
0.7572	Intermediate Similarity	NPC165285
0.7572	Intermediate Similarity	NPC159767
0.7572	Intermediate Similarity	NPC473402
0.7562	Intermediate Similarity	NPC266741
0.7558	Intermediate Similarity	NPC89831
0.7545	Intermediate Similarity	NPC287757
0.7545	Intermediate Similarity	NPC319320
0.7529	Intermediate Similarity	NPC254700
0.7529	Intermediate Similarity	NPC196243
0.7526	Intermediate Similarity	NPC471561
0.7514	Intermediate Similarity	NPC475532
0.75	Intermediate Similarity	NPC473422
0.7485	Intermediate Similarity	NPC302597
0.7484	Intermediate Similarity	NPC326966
0.7471	Intermediate Similarity	NPC63931
0.7471	Intermediate Similarity	NPC476227
0.747	Intermediate Similarity	NPC473580
0.747	Intermediate Similarity	NPC244509
0.7459	Intermediate Similarity	NPC473305
0.7459	Intermediate Similarity	NPC163961
0.7443	Intermediate Similarity	NPC119652
0.7443	Intermediate Similarity	NPC97526
0.7443	Intermediate Similarity	NPC45037
0.7432	Intermediate Similarity	NPC470546
0.7429	Intermediate Similarity	NPC50016
0.7414	Intermediate Similarity	NPC306804
0.7414	Intermediate Similarity	NPC137627
0.7414	Intermediate Similarity	NPC273755
0.741	Intermediate Similarity	NPC39431
0.7399	Intermediate Similarity	NPC274198
0.7399	Intermediate Similarity	NPC198254
0.7381	Intermediate Similarity	NPC326349
0.7381	Intermediate Similarity	NPC323336
0.7374	Intermediate Similarity	NPC471050
0.7374	Intermediate Similarity	NPC471048
0.7374	Intermediate Similarity	NPC471049
0.7371	Intermediate Similarity	NPC473354
0.7371	Intermediate Similarity	NPC471165
0.7365	Intermediate Similarity	NPC470545
0.7341	Intermediate Similarity	NPC129486
0.7318	Intermediate Similarity	NPC471526
0.7303	Intermediate Similarity	NPC32064
0.7299	Intermediate Similarity	NPC276506
0.7299	Intermediate Similarity	NPC475204
0.7299	Intermediate Similarity	NPC475123
0.7297	Intermediate Similarity	NPC470544
0.7296	Intermediate Similarity	NPC471531
0.7294	Intermediate Similarity	NPC103250
0.7291	Intermediate Similarity	NPC326363
0.729	Intermediate Similarity	NPC473322
0.7278	Intermediate Similarity	NPC184437
0.7273	Intermediate Similarity	NPC26108
0.7273	Intermediate Similarity	NPC17698
0.7273	Intermediate Similarity	NPC164608
0.7268	Intermediate Similarity	NPC471532
0.7253	Intermediate Similarity	NPC94862
0.7241	Intermediate Similarity	NPC280022
0.7238	Intermediate Similarity	NPC315542
0.723	Intermediate Similarity	NPC317254
0.7229	Intermediate Similarity	NPC324081
0.7228	Intermediate Similarity	NPC24370
0.7228	Intermediate Similarity	NPC214142
0.7228	Intermediate Similarity	NPC92803
0.7228	Intermediate Similarity	NPC319232
0.72	Intermediate Similarity	NPC46009
0.7198	Intermediate Similarity	NPC276120
0.7197	Intermediate Similarity	NPC255447
0.7197	Intermediate Similarity	NPC120251
0.7192	Intermediate Similarity	NPC118559
0.7192	Intermediate Similarity	NPC304307
0.7192	Intermediate Similarity	NPC124920
0.7192	Intermediate Similarity	NPC261251
0.7192	Intermediate Similarity	NPC34580
0.7179	Intermediate Similarity	NPC111428
0.7174	Intermediate Similarity	NPC174629
0.7169	Intermediate Similarity	NPC245974
0.7167	Intermediate Similarity	NPC476321
0.7157	Intermediate Similarity	NPC100547
0.7152	Intermediate Similarity	NPC247298
0.715	Intermediate Similarity	NPC325976
0.7143	Intermediate Similarity	NPC138083
0.7143	Intermediate Similarity	NPC315388
0.7134	Intermediate Similarity	NPC325651
0.7133	Intermediate Similarity	NPC38458
0.7133	Intermediate Similarity	NPC311737
0.7125	Intermediate Similarity	NPC473360
0.7122	Intermediate Similarity	NPC95240
0.7122	Intermediate Similarity	NPC322135
0.7122	Intermediate Similarity	NPC223409
0.712	Intermediate Similarity	NPC18890
0.711	Intermediate Similarity	NPC476231
0.7097	Intermediate Similarity	NPC204970
0.7087	Intermediate Similarity	NPC14288
0.7086	Intermediate Similarity	NPC209463
0.7086	Intermediate Similarity	NPC473502
0.7083	Intermediate Similarity	NPC144691
0.7081	Intermediate Similarity	NPC471195
0.7081	Intermediate Similarity	NPC471196
0.707	Intermediate Similarity	NPC296712
0.7069	Intermediate Similarity	NPC472923
0.7067	Intermediate Similarity	NPC82963
0.7062	Intermediate Similarity	NPC328494
0.7053	Intermediate Similarity	NPC321592
0.7053	Intermediate Similarity	NPC54803
0.7045	Intermediate Similarity	NPC186617
0.7043	Intermediate Similarity	NPC473407
0.7043	Intermediate Similarity	NPC473378
0.7039	Intermediate Similarity	NPC283760
0.7029	Intermediate Similarity	NPC471130
0.7027	Intermediate Similarity	NPC234069
0.7019	Intermediate Similarity	NPC323752
0.7019	Intermediate Similarity	NPC323198
0.7019	Intermediate Similarity	NPC284888
0.7017	Intermediate Similarity	NPC153554
0.7013	Intermediate Similarity	NPC474862
0.7006	Intermediate Similarity	NPC473693
0.7006	Intermediate Similarity	NPC471568
0.7	Intermediate Similarity	NPC28945
0.7	Intermediate Similarity	NPC285343
0.6989	Remote Similarity	NPC61332
0.6989	Remote Similarity	NPC174122
0.6989	Remote Similarity	NPC29531
0.6989	Remote Similarity	NPC240130
0.6989	Remote Similarity	NPC64140
0.6988	Remote Similarity	NPC473804
0.6986	Remote Similarity	NPC245055
0.6986	Remote Similarity	NPC33064
0.6975	Remote Similarity	NPC6570
0.6974	Remote Similarity	NPC220698
0.6968	Remote Similarity	NPC328763
0.6962	Remote Similarity	NPC469666
0.6959	Remote Similarity	NPC471132
0.6951	Remote Similarity	NPC150712
0.6948	Remote Similarity	NPC71684
0.6947	Remote Similarity	NPC471592
0.6946	Remote Similarity	NPC119569
0.6938	Remote Similarity	NPC220852
0.6937	Remote Similarity	NPC45191
0.6936	Remote Similarity	NPC104345
0.6933	Remote Similarity	NPC118202
0.6928	Remote Similarity	NPC319950
0.6923	Remote Similarity	NPC475564
0.6923	Remote Similarity	NPC170302
0.6923	Remote Similarity	NPC475409
0.6923	Remote Similarity	NPC271792
0.6918	Remote Similarity	NPC478147
0.6914	Remote Similarity	NPC88970
0.691	Remote Similarity	NPC196091
0.6909	Remote Similarity	NPC91953
0.6909	Remote Similarity	NPC212850
0.6909	Remote Similarity	NPC83289
0.6909	Remote Similarity	NPC314113
0.6909	Remote Similarity	NPC189724
0.6891	Remote Similarity	NPC472329

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 NPC133470 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	159
0.1-0.2	488
0.2-0.3	947
0.3-0.4	853
0.4-0.5	2367
0.5-0.6	3481
0.6-0.7	822
0.7-0.8	33
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7866	Intermediate Similarity	NPD7735	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD7450	Phase 2
0.7701	Intermediate Similarity	NPD5445	Approved
0.7654	Intermediate Similarity	NPD7617	Discontinued
0.7598	Intermediate Similarity	NPD8025	Phase 2
0.7577	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7131	Phase 3
0.75	Intermediate Similarity	NPD7303	Discontinued
0.7384	Intermediate Similarity	NPD5823	Approved
0.7381	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7449	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD8103	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD6060	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD7695	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2791	Discontinued
0.7226	Intermediate Similarity	NPD7451	Discontinued
0.7225	Intermediate Similarity	NPD8303	Discontinued
0.7195	Intermediate Similarity	NPD5481	Discontinued
0.7193	Intermediate Similarity	NPD4485	Approved
0.7143	Intermediate Similarity	NPD2888	Approved
0.7143	Intermediate Similarity	NPD2889	Approved
0.7143	Intermediate Similarity	NPD2017	Approved
0.7143	Intermediate Similarity	NPD2890	Approved
0.7135	Intermediate Similarity	NPD8022	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4430	Phase 2
0.7126	Intermediate Similarity	NPD4432	Discontinued
0.7126	Intermediate Similarity	NPD5556	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6884	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD4652	Approved
0.7091	Intermediate Similarity	NPD7066	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6533	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD2098	Approved
0.7063	Intermediate Similarity	NPD6346	Approved
0.7035	Intermediate Similarity	NPD8019	Approved
0.7027	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6359	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6809	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6707	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7599	Phase 2
0.6994	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6283	Phase 2
0.6988	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD3136	Phase 2
0.6976	Remote Similarity	NPD7603	Discontinued
0.6954	Remote Similarity	NPD5599	Discontinued
0.6954	Remote Similarity	NPD7600	Phase 2
0.6954	Remote Similarity	NPD2097	Approved
0.6949	Remote Similarity	NPD7485	Phase 3
0.6949	Remote Similarity	NPD7484	Phase 3
0.694	Remote Similarity	NPD7883	Discontinued
0.6932	Remote Similarity	NPD3363	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6878	Phase 2
0.6923	Remote Similarity	NPD6879	Phase 2
0.6906	Remote Similarity	NPD6159	Phase 2
0.6882	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD4083	Discontinued
0.6866	Remote Similarity	NPD8149	Discontinued
0.6865	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5811	Approved
0.686	Remote Similarity	NPD3229	Phase 2
0.6859	Remote Similarity	NPD7948	Phase 1
0.6857	Remote Similarity	NPD6063	Approved
0.6857	Remote Similarity	NPD3558	Approved
0.6857	Remote Similarity	NPD3557	Approved
0.6857	Remote Similarity	NPD3556	Approved
0.6857	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3560	Approved
0.6845	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7602	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6519	Phase 2
0.6839	Remote Similarity	NPD7495	Discontinued
0.6837	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5078	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD8356	Approved
0.6826	Remote Similarity	NPD6301	Phase 2
0.6826	Remote Similarity	NPD5024	Approved
0.6825	Remote Similarity	NPD7569	Approved
0.6825	Remote Similarity	NPD7570	Approved
0.6821	Remote Similarity	NPD5631	Phase 3
0.6816	Remote Similarity	NPD7608	Discontinued
0.6816	Remote Similarity	NPD7968	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD4659	Approved
0.6807	Remote Similarity	NPD7978	Discontinued
0.6805	Remote Similarity	NPD3141	Discontinued
0.6804	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD2882	Phase 1
0.6802	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD6767	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD4515	Suspended
0.6788	Remote Similarity	NPD7810	Phase 3
0.6788	Remote Similarity	NPD7811	Phase 3
0.6788	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5819	Phase 2
0.6782	Remote Similarity	NPD2789	Approved
0.6779	Remote Similarity	NPD8430	Approved
0.6774	Remote Similarity	NPD6557	Phase 2
0.6774	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD3125	Approved
0.6762	Remote Similarity	NPD8106	Phase 2
0.6761	Remote Similarity	NPD5967	Approved
0.6758	Remote Similarity	NPD6645	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD5558	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD7686	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6522	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD3391	Approved
0.6746	Remote Similarity	NPD8323	Discontinued
0.6746	Remote Similarity	NPD5595	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD3277	Phase 3
0.6744	Remote Similarity	NPD7523	Phase 3
0.674	Remote Similarity	NPD3951	Phase 3
0.674	Remote Similarity	NPD3952	Approved
0.674	Remote Similarity	NPD3953	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6833	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD3802	Phase 3
0.6731	Remote Similarity	NPD3421	Phase 3
0.673	Remote Similarity	NPD4103	Phase 2
0.673	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD5186	Approved
0.6722	Remote Similarity	NPD5183	Approved
0.6721	Remote Similarity	NPD3965	Phase 1
0.672	Remote Similarity	NPD5923	Phase 1
0.6717	Remote Similarity	NPD7263	Phase 2
0.6707	Remote Similarity	NPD7720	Phase 2
0.6706	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4335	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD8315	Phase 1
0.6703	Remote Similarity	NPD5200	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4539	Phase 1
0.6686	Remote Similarity	NPD1968	Approved
0.6686	Remote Similarity	NPD2468	Approved
0.6686	Remote Similarity	NPD2469	Approved
0.6686	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD1967	Approved
0.6685	Remote Similarity	NPD7479	Phase 2
0.6684	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD5849	Approved
0.6684	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD2916	Discontinued
0.6667	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7944	Discontinued
0.6667	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2821	Approved
0.6667	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6457	Approved
0.6667	Remote Similarity	NPD5639	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD5937	Approved
0.6649	Remote Similarity	NPD4372	Phase 1
0.6648	Remote Similarity	NPD7011	Discontinued
0.6647	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7740	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD2228	Approved
0.6645	Remote Similarity	NPD2234	Approved
0.6645	Remote Similarity	NPD2229	Approved
0.6634	Remote Similarity	NPD7225	Discontinued
0.6633	Remote Similarity	NPD7817	Phase 1
0.6632	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.663	Remote Similarity	NPD3793	Phase 3
0.6628	Remote Similarity	NPD5941	Approved
0.6628	Remote Similarity	NPD5942	Approved
0.6627	Remote Similarity	NPD6636	Phase 3
0.6627	Remote Similarity	NPD3555	Approved
0.6627	Remote Similarity	NPD3554	Approved
0.6627	Remote Similarity	NPD3553	Approved
0.6627	Remote Similarity	NPD3552	Approved
0.6623	Remote Similarity	NPD3123	Discovery
0.662	Remote Similarity	NPD8016	Phase 3
0.662	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD8114	Approved
0.6616	Remote Similarity	NPD8115	Approved
0.6615	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD6874	Approved
0.6614	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD4003	Phase 3
0.6608	Remote Similarity	NPD5839	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD4093	Discontinued
0.66	Remote Similarity	NPD6376	Discontinued
0.6598	Remote Similarity	NPD4423	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD5641	Discontinued
0.6595	Remote Similarity	NPD7771	Discontinued
0.6591	Remote Similarity	NPD7105	Phase 1
0.6591	Remote Similarity	NPD6395	Phase 2
0.6591	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.659	Remote Similarity	NPD5748	Phase 2
0.6588	Remote Similarity	NPD6676	Phase 2
0.6587	Remote Similarity	NPD8311	Discontinued
0.6587	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD4986	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