NPASS Compound

Structure

CID322878 OpenBabel06191716162D 54 56 0 0 1 0 0 0 0 0999 V2000 -1.7247 3.7583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3643 2.2922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5848 -5.2839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0760 1.5064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0370 -8.1173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9598 -1.6168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0194 2.8027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7466 -2.7690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8805 -2.2690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7466 -3.7690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5827 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0145 -2.7690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8805 -4.2690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 -0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9654 -1.7662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3993 -0.8653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1485 -4.2690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9738 -6.3978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3393 2.0696 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9047 -4.5509 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5127 0.6802 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0145 -3.7690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9682 -1.8410 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2824 -3.7690 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1229 -5.4089 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0429 -6.7631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6340 1.1141 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5282 -3.7690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6117 1.1141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7457 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1229 -5.4089 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3410 -4.5509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7225 -1.8410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7331 0.6802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2457 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.0784 -5.1142 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.8935 -2.8382 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.1673 -5.1142 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.6478 -2.8382 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.6229 1.2631 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 -0.2611 -6.1396 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3942 -4.2690 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9064 2.0696 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6766 -0.5007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2719 -6.3978 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3391 -5.2839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7197 -1.7662 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1697 1.5064 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8304 0.1104 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8939 -7.7519 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3965 -0.7905 0.0000 S 0 0 3 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 5 53 1 0 0 0 0 6 54 1 0 0 0 0 7 20 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 12 1 0 0 0 0 10 13 2 0 0 0 0 11 14 1 0 0 0 0 11 16 1 0 0 0 0 12 23 2 0 0 0 0 13 23 1 0 0 0 0 15 17 1 0 0 0 0 16 43 1 0 0 0 0 17 54 1 0 0 0 0 18 23 1 0 0 0 0 19 28 1 0 0 0 0 20 2 1 6 0 0 0 21 3 1 1 0 0 0 21 30 1 0 0 0 0 21 38 1 0 0 0 0 22 4 1 1 0 0 0 22 31 1 0 0 0 0 22 37 1 0 0 0 0 24 15 1 1 0 0 0 24 32 1 0 0 0 0 24 39 1 0 0 0 0 25 18 1 1 0 0 0 25 34 1 0 0 0 0 25 41 1 0 0 0 0 26 19 1 1 0 0 0 26 33 1 0 0 0 0 26 40 1 0 0 0 0 27 14 1 1 0 0 0 27 35 1 0 0 0 0 27 43 1 0 0 0 0 28 44 2 0 0 0 0 28 53 1 0 0 0 0 29 20 1 1 0 0 0 29 36 1 0 0 0 0 29 42 1 0 0 0 0 30 39 2 3 0 0 0 30 45 1 0 0 0 0 31 42 2 3 0 0 0 31 46 1 0 0 0 0 32 37 2 3 0 0 0 32 47 1 0 0 0 0 33 38 2 3 0 0 0 33 48 1 0 0 0 0 34 40 2 3 0 0 0 34 49 1 0 0 0 0 35 41 2 3 0 0 0 35 50 1 0 0 0 0 36 43 1 0 0 0 0 36 51 2 0 0 0 0 52 54 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	775.36
Volume:	759.93
LogP:	-0.077
LogD:	-0.238
LogS:	-1.802
# Rotatable Bonds:	10
TPSA:	251.25
# H-Bond Aceptor:	17
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.147
Synthetic Accessibility Score:	5.973
Fsp3:	0.611
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:	-5.958
MDCK Permeability:	0.00010670057963579893
Pgp-inhibitor:	0.918
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.812
20% Bioavailability (F20%):	0.837
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.044
Plasma Protein Binding (PPB):	15.662571907043457%
Volume Distribution (VD):	0.432
Pgp-substrate:	67.76065826416016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.006
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.04
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.051
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.067
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.007

ADMET: Excretion

Clearance (CL):	2.34
Half-life (T1/2):	0.824

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.994
Drug-inuced Liver Injury (DILI):	0.932
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.571
Skin Sensitization:	0.319
Carcinogencity:	0.352
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.944

Download Data

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

Natural Product: NPC322878

Natural Product ID:	NPC322878
*Common Name:**	Phakellistatin 14
IUPAC Name:	methyl 2-[(3S,6S,9S,12S,15S,18S,21S)-18-benzyl-3-[(2S)-butan-2-yl]-6,12-dimethyl-9-(2-methylsulfinylethyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazabicyclo[19.3.0]tetracosan-15-yl]acetate
Synonyms:	phakellistatin 14
Standard InCHIKey:	ZBIJFJOAXJXGTR-KLZQDHKKSA-N
Standard InCHI:	InChI=1S/C36H53N7O10S/c1-7-20(2)29-36(51)43-16-11-14-27(43)35(50)41-25(18-23-12-9-8-10-13-23)34(49)40-26(19-28(44)53-5)33(48)38-21(3)30(45)39-24(15-17-54(6)52)32(47)37-22(4)31(46)42-29/h8-10,12-13,20-22,24-27,29H,7,11,14-19H2,1-6H3,(H,37,47)(H,38,48)(H,39,45)(H,40,49)(H,41,50)(H,42,46)/t20-,21-,22-,24-,25-,26-,27-,29-,54?/m0/s1
SMILES:	COC(=O)C[C@@H]1N=C(O)[C@H](Cc2ccccc2)N=C(O)[C@@H]2CCCN2C(=O)[C@@H](N=C([C@@H](N=C([C@@H](N=C([C@@H](N=C1O)C)O)CCS(=O)C)O)C)O)[C@H](CC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL502751
PubChem CID:	11308763
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

*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
NPO30912	Phakellia	Genus	Bubaridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679318]

☑ 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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	5.0	ug ml-1	PMID[505155]

☑ 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 NPC322878 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	139
0.1-0.2	835
0.2-0.3	5373
0.3-0.4	24438
0.4-0.5	9642
0.5-0.6	1553
0.6-0.7	469
0.7-0.8	219
0.8-0.85	24
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8955	High Similarity	NPC300315
0.8571	High Similarity	NPC286551
0.844	Intermediate Similarity	NPC471265
0.844	Intermediate Similarity	NPC471264
0.8425	Intermediate Similarity	NPC105717
0.8252	Intermediate Similarity	NPC89489
0.8235	Intermediate Similarity	NPC6975
0.8148	Intermediate Similarity	NPC200964
0.8125	Intermediate Similarity	NPC178662
0.8125	Intermediate Similarity	NPC476133
0.8125	Intermediate Similarity	NPC470884
0.8125	Intermediate Similarity	NPC92784
0.8125	Intermediate Similarity	NPC98424
0.8095	Intermediate Similarity	NPC313867
0.8095	Intermediate Similarity	NPC209509
0.8095	Intermediate Similarity	NPC316008
0.8088	Intermediate Similarity	NPC202521
0.8085	Intermediate Similarity	NPC130309
0.8041	Intermediate Similarity	NPC314358
0.8027	Intermediate Similarity	NPC315283
0.8027	Intermediate Similarity	NPC314388
0.8027	Intermediate Similarity	NPC476978
0.8015	Intermediate Similarity	NPC476990
0.8014	Intermediate Similarity	NPC263493
0.8014	Intermediate Similarity	NPC269398
0.8	Intermediate Similarity	NPC283783
0.7973	Intermediate Similarity	NPC5620
0.7972	Intermediate Similarity	NPC287401
0.7971	Intermediate Similarity	NPC46427
0.7959	Intermediate Similarity	NPC468984
0.7958	Intermediate Similarity	NPC255447
0.7899	Intermediate Similarity	NPC252878
0.7868	Intermediate Similarity	NPC470546
0.7823	Intermediate Similarity	NPC163392
0.7823	Intermediate Similarity	NPC239762
0.7794	Intermediate Similarity	NPC470545
0.7785	Intermediate Similarity	NPC52748
0.777	Intermediate Similarity	NPC168113
0.7763	Intermediate Similarity	NPC2501
0.7763	Intermediate Similarity	NPC129666
0.7733	Intermediate Similarity	NPC315266
0.773	Intermediate Similarity	NPC326407
0.773	Intermediate Similarity	NPC317725
0.773	Intermediate Similarity	NPC317362
0.773	Intermediate Similarity	NPC318930
0.7721	Intermediate Similarity	NPC470544
0.7718	Intermediate Similarity	NPC161069
0.7718	Intermediate Similarity	NPC197682
0.7718	Intermediate Similarity	NPC139326
0.7718	Intermediate Similarity	NPC176226
0.7703	Intermediate Similarity	NPC476259
0.7697	Intermediate Similarity	NPC240848
0.7692	Intermediate Similarity	NPC473322
0.7671	Intermediate Similarity	NPC248283
0.7662	Intermediate Similarity	NPC162104
0.7643	Intermediate Similarity	NPC197743
0.7643	Intermediate Similarity	NPC297145
0.7639	Intermediate Similarity	NPC200589
0.7622	Intermediate Similarity	NPC319766
0.7613	Intermediate Similarity	NPC122590
0.7597	Intermediate Similarity	NPC475168
0.7597	Intermediate Similarity	NPC7817
0.7582	Intermediate Similarity	NPC471820
0.7582	Intermediate Similarity	NPC471821
0.7568	Intermediate Similarity	NPC68865
0.7568	Intermediate Similarity	NPC127741
0.7566	Intermediate Similarity	NPC262077
0.7536	Intermediate Similarity	NPC254088
0.7533	Intermediate Similarity	NPC469427
0.7533	Intermediate Similarity	NPC469426
0.7516	Intermediate Similarity	NPC329761
0.7516	Intermediate Similarity	NPC225648
0.7516	Intermediate Similarity	NPC138775
0.75	Intermediate Similarity	NPC471680
0.7483	Intermediate Similarity	NPC101719
0.7483	Intermediate Similarity	NPC77905
0.7465	Intermediate Similarity	NPC474082
0.7465	Intermediate Similarity	NPC175726
0.7464	Intermediate Similarity	NPC315276
0.7464	Intermediate Similarity	NPC14672
0.7464	Intermediate Similarity	NPC239357
0.7464	Intermediate Similarity	NPC285926
0.7452	Intermediate Similarity	NPC470902
0.7448	Intermediate Similarity	NPC111428
0.7432	Intermediate Similarity	NPC141050
0.7421	Intermediate Similarity	NPC323336
0.7421	Intermediate Similarity	NPC326349
0.7413	Intermediate Similarity	NPC222466
0.7403	Intermediate Similarity	NPC145113
0.74	Intermediate Similarity	NPC132636
0.7362	Intermediate Similarity	NPC61004
0.7351	Intermediate Similarity	NPC46098
0.7351	Intermediate Similarity	NPC268841
0.7351	Intermediate Similarity	NPC307357
0.7324	Intermediate Similarity	NPC71684
0.7319	Intermediate Similarity	NPC33742
0.7297	Intermediate Similarity	NPC246079
0.7296	Intermediate Similarity	NPC469903
0.7292	Intermediate Similarity	NPC22746
0.7278	Intermediate Similarity	NPC56685
0.7278	Intermediate Similarity	NPC473341
0.7246	Intermediate Similarity	NPC276949
0.7246	Intermediate Similarity	NPC35850
0.7241	Intermediate Similarity	NPC47667
0.7222	Intermediate Similarity	NPC469901
0.7215	Intermediate Similarity	NPC300443
0.7207	Intermediate Similarity	NPC477527
0.7205	Intermediate Similarity	NPC324850
0.7197	Intermediate Similarity	NPC13470
0.7184	Intermediate Similarity	NPC4910
0.7179	Intermediate Similarity	NPC135121
0.7179	Intermediate Similarity	NPC311658
0.7179	Intermediate Similarity	NPC16188
0.717	Intermediate Similarity	NPC262166
0.7169	Intermediate Similarity	NPC473000
0.7163	Intermediate Similarity	NPC169328
0.7161	Intermediate Similarity	NPC477217
0.7161	Intermediate Similarity	NPC201244
0.716	Intermediate Similarity	NPC469898
0.7152	Intermediate Similarity	NPC473491
0.7143	Intermediate Similarity	NPC197470
0.7126	Intermediate Similarity	NPC40234
0.7126	Intermediate Similarity	NPC475123
0.7126	Intermediate Similarity	NPC475204
0.7117	Intermediate Similarity	NPC469902
0.7117	Intermediate Similarity	NPC471527
0.7113	Intermediate Similarity	NPC310467
0.7113	Intermediate Similarity	NPC237420
0.7101	Intermediate Similarity	NPC471165
0.7101	Intermediate Similarity	NPC477462
0.7093	Intermediate Similarity	NPC477637
0.7086	Intermediate Similarity	NPC329731
0.7078	Intermediate Similarity	NPC476989
0.7063	Intermediate Similarity	NPC202198
0.7063	Intermediate Similarity	NPC261934
0.7063	Intermediate Similarity	NPC5194
0.7059	Intermediate Similarity	NPC469900
0.7055	Intermediate Similarity	NPC24617
0.7055	Intermediate Similarity	NPC1390
0.7055	Intermediate Similarity	NPC62104
0.705	Intermediate Similarity	NPC474584
0.7039	Intermediate Similarity	NPC59827
0.7039	Intermediate Similarity	NPC184933
0.703	Intermediate Similarity	NPC471053
0.703	Intermediate Similarity	NPC471051
0.703	Intermediate Similarity	NPC471052
0.7018	Intermediate Similarity	NPC473001
0.7012	Intermediate Similarity	NPC114806
0.7006	Intermediate Similarity	NPC329961
0.7006	Intermediate Similarity	NPC122427
0.6993	Remote Similarity	NPC43755
0.6988	Remote Similarity	NPC217804
0.6988	Remote Similarity	NPC472923
0.6988	Remote Similarity	NPC5719
0.6988	Remote Similarity	NPC210377
0.6988	Remote Similarity	NPC22883
0.6978	Remote Similarity	NPC329011
0.6975	Remote Similarity	NPC244509
0.697	Remote Similarity	NPC241794
0.6946	Remote Similarity	NPC15068
0.6941	Remote Similarity	NPC137627
0.6936	Remote Similarity	NPC153554
0.6927	Remote Similarity	NPC165538
0.6905	Remote Similarity	NPC63040
0.6901	Remote Similarity	NPC26108
0.6899	Remote Similarity	NPC81026
0.6897	Remote Similarity	NPC477061
0.6897	Remote Similarity	NPC45777
0.6897	Remote Similarity	NPC478016
0.6897	Remote Similarity	NPC478014
0.6897	Remote Similarity	NPC302169
0.6897	Remote Similarity	NPC478015
0.6894	Remote Similarity	NPC233702
0.6882	Remote Similarity	NPC89831
0.6867	Remote Similarity	NPC73655
0.6864	Remote Similarity	NPC469904
0.6861	Remote Similarity	NPC327481
0.6851	Remote Similarity	NPC477632
0.6851	Remote Similarity	NPC477638
0.6848	Remote Similarity	NPC244336
0.6835	Remote Similarity	NPC266741
0.6816	Remote Similarity	NPC477636
0.681	Remote Similarity	NPC39431
0.681	Remote Similarity	NPC473002
0.6807	Remote Similarity	NPC473003
0.6805	Remote Similarity	NPC107938
0.6805	Remote Similarity	NPC294516
0.6805	Remote Similarity	NPC328649
0.6802	Remote Similarity	NPC476227
0.68	Remote Similarity	NPC71933
0.68	Remote Similarity	NPC105114
0.68	Remote Similarity	NPC152850
0.68	Remote Similarity	NPC89923
0.68	Remote Similarity	NPC239990
0.6786	Remote Similarity	NPC63931
0.6778	Remote Similarity	NPC477526
0.6768	Remote Similarity	NPC476268
0.6767	Remote Similarity	NPC473501
0.6767	Remote Similarity	NPC475439
0.6765	Remote Similarity	NPC186617

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 NPC322878 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	101
0.1-0.2	343
0.2-0.3	730
0.3-0.4	2498
0.4-0.5	3967
0.5-0.6	1162
0.6-0.7	259
0.7-0.8	83
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8676	High Similarity	NPD4125	Approved
0.8493	Intermediate Similarity	NPD7892	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD2045	Approved
0.8085	Intermediate Similarity	NPD2044	Approved
0.8085	Intermediate Similarity	NPD2047	Approved
0.8085	Intermediate Similarity	NPD21	Approved
0.8085	Intermediate Similarity	NPD2043	Approved
0.8085	Intermediate Similarity	NPD2051	Approved
0.8085	Intermediate Similarity	NPD2049	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD2048	Approved
0.8085	Intermediate Similarity	NPD2050	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD2046	Approved
0.8082	Intermediate Similarity	NPD2022	Approved
0.8042	Intermediate Similarity	NPD8416	Discontinued
0.7959	Intermediate Similarity	NPD2087	Approved
0.7959	Intermediate Similarity	NPD8076	Discontinued
0.7959	Intermediate Similarity	NPD2088	Approved
0.7945	Intermediate Similarity	NPD3480	Approved
0.7931	Intermediate Similarity	NPD8172	Phase 2
0.7931	Intermediate Similarity	NPD8173	Phase 2
0.7917	Intermediate Similarity	NPD5323	Approved
0.7862	Intermediate Similarity	NPD8643	Discontinued
0.7857	Intermediate Similarity	NPD5367	Discontinued
0.7842	Intermediate Similarity	NPD2584	Suspended
0.7785	Intermediate Similarity	NPD2436	Approved
0.7785	Intermediate Similarity	NPD2437	Approved
0.7778	Intermediate Similarity	NPD8126	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD8124	Phase 3
0.7778	Intermediate Similarity	NPD5230	Approved
0.7778	Intermediate Similarity	NPD5229	Approved
0.7778	Intermediate Similarity	NPD5299	Approved
0.7763	Intermediate Similarity	NPD5613	Approved
0.7763	Intermediate Similarity	NPD3987	Approved
0.7763	Intermediate Similarity	NPD3988	Approved
0.7763	Intermediate Similarity	NPD5614	Approved
0.7746	Intermediate Similarity	NPD3608	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD3561	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD6304	Approved
0.7702	Intermediate Similarity	NPD6303	Approved
0.7692	Intermediate Similarity	NPD7828	Discontinued
0.7677	Intermediate Similarity	NPD4646	Approved
0.7677	Intermediate Similarity	NPD4647	Approved
0.7677	Intermediate Similarity	NPD4648	Approved
0.7669	Intermediate Similarity	NPD7964	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD7965	Phase 2
0.7658	Intermediate Similarity	NPD4567	Approved
0.7658	Intermediate Similarity	NPD4566	Approved
0.7635	Intermediate Similarity	NPD6901	Phase 3
0.7635	Intermediate Similarity	NPD4126	Approved
0.7619	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD5264	Approved
0.7616	Intermediate Similarity	NPD5265	Approved
0.755	Intermediate Similarity	NPD5341	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD7728	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD4557	Approved
0.7434	Intermediate Similarity	NPD6119	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD6552	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD3073	Approved
0.7343	Intermediate Similarity	NPD3072	Approved
0.7343	Intermediate Similarity	NPD3071	Approved
0.7333	Intermediate Similarity	NPD4652	Approved
0.7329	Intermediate Similarity	NPD4175	Approved
0.7329	Intermediate Similarity	NPD4177	Approved
0.7317	Intermediate Similarity	NPD4508	Discontinued
0.7284	Intermediate Similarity	NPD2097	Approved
0.7273	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4762	Approved
0.7273	Intermediate Similarity	NPD4761	Approved
0.723	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD5298	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5725	Approved
0.7219	Intermediate Similarity	NPD6073	Approved
0.72	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD2014	Approved
0.7197	Intermediate Similarity	NPD2016	Approved
0.7197	Intermediate Similarity	NPD2013	Approved
0.7195	Intermediate Similarity	NPD2098	Approved
0.7179	Intermediate Similarity	NPD8323	Discontinued
0.7162	Intermediate Similarity	NPD7979	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD5263	Approved
0.7162	Intermediate Similarity	NPD4676	Approved
0.7143	Intermediate Similarity	NPD1348	Approved
0.7143	Intermediate Similarity	NPD2891	Approved
0.7125	Intermediate Similarity	NPD8315	Phase 1
0.7107	Intermediate Similarity	NPD7613	Discontinued
0.7107	Intermediate Similarity	NPD7303	Discontinued
0.7105	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5004	Approved
0.7095	Intermediate Similarity	NPD3040	Approved
0.7086	Intermediate Similarity	NPD4153	Approved
0.7067	Intermediate Similarity	NPD1330	Phase 2
0.7067	Intermediate Similarity	NPD2078	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4209	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD8022	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD1713	Approved
0.7034	Intermediate Similarity	NPD4706	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD7634	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD5747	Discontinued
0.7019	Intermediate Similarity	NPD6670	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD3125	Approved
0.7	Intermediate Similarity	NPD5638	Approved
0.6994	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6093	Discontinued
0.6989	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6631	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD8303	Discontinued
0.6944	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3509	Approved
0.6918	Remote Similarity	NPD3510	Approved
0.6875	Remote Similarity	NPD1582	Approved
0.6875	Remote Similarity	NPD1581	Approved
0.6867	Remote Similarity	NPD5759	Approved
0.6854	Remote Similarity	NPD5851	Approved
0.6854	Remote Similarity	NPD5852	Approved
0.6842	Remote Similarity	NPD7908	Discontinued
0.6842	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6852	Discontinued
0.6832	Remote Similarity	NPD4432	Discontinued
0.6826	Remote Similarity	NPD8351	Phase 2
0.6824	Remote Similarity	NPD4677	Discontinued
0.6813	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD6864	Phase 2
0.6795	Remote Similarity	NPD6865	Phase 2
0.6759	Remote Similarity	NPD2218	Phase 2
0.6759	Remote Similarity	NPD2217	Approved
0.6758	Remote Similarity	NPD8339	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6623	Phase 3
0.6752	Remote Similarity	NPD7511	Approved
0.6752	Remote Similarity	NPD7512	Approved
0.673	Remote Similarity	NPD3508	Approved
0.671	Remote Similarity	NPD5780	Phase 2
0.6707	Remote Similarity	NPD7599	Phase 2
0.669	Remote Similarity	NPD6360	Discontinued
0.6687	Remote Similarity	NPD6679	Phase 3
0.6687	Remote Similarity	NPD6678	Phase 3
0.6687	Remote Similarity	NPD6680	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5485	Approved
0.6686	Remote Similarity	NPD5484	Approved
0.6667	Remote Similarity	NPD3643	Approved
0.6667	Remote Similarity	NPD2889	Approved
0.6667	Remote Similarity	NPD6681	Discovery
0.6667	Remote Similarity	NPD6088	Approved
0.6667	Remote Similarity	NPD4794	Discontinued
0.6667	Remote Similarity	NPD3644	Approved
0.6667	Remote Similarity	NPD2888	Approved
0.6667	Remote Similarity	NPD3642	Approved
0.6667	Remote Similarity	NPD2017	Approved
0.6667	Remote Similarity	NPD1067	Discontinued
0.6667	Remote Similarity	NPD2516	Approved
0.6667	Remote Similarity	NPD2890	Approved
0.6646	Remote Similarity	NPD7740	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD8265	Approved
0.6645	Remote Similarity	NPD3626	Phase 3
0.6645	Remote Similarity	NPD5296	Approved
0.6643	Remote Similarity	NPD3598	Phase 3
0.6628	Remote Similarity	NPD2517	Approved
0.6627	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD8417	Discontinued
0.6604	Remote Similarity	NPD7720	Phase 2
0.6599	Remote Similarity	NPD5981	Approved
0.6585	Remote Similarity	NPD6390	Discontinued
0.6585	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD1967	Approved
0.6584	Remote Similarity	NPD1968	Approved
0.6582	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD4158	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD3648	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD4151	Approved
0.6579	Remote Similarity	NPD3588	Discontinued
0.6575	Remote Similarity	NPD2117	Pre-registration
0.6575	Remote Similarity	NPD2116	Approved
0.6575	Remote Similarity	NPD2115	Approved
0.6568	Remote Similarity	NPD6646	Discontinued
0.6561	Remote Similarity	NPD7510	Approved
0.6556	Remote Similarity	NPD6325	Discontinued
0.6541	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD8362	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD6408	Phase 1
0.6533	Remote Similarity	NPD5702	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD2994	Approved
0.6519	Remote Similarity	NPD6294	Approved
0.6519	Remote Similarity	NPD4214	Discontinued
0.6519	Remote Similarity	NPD6295	Approved
0.6516	Remote Similarity	NPD5581	Approved
0.6513	Remote Similarity	NPD4100	Approved
0.6513	Remote Similarity	NPD4099	Approved
0.6513	Remote Similarity	NPD6302	Clinical (unspecified phase)
0.651	Remote Similarity	NPD5187	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD5077	Approved
0.6503	Remote Similarity	NPD5076	Approved
0.6497	Remote Similarity	NPD3908	Approved
0.6497	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD7695	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