NPASS Compound

Structure

NPC471051 OpenBabel07101718272D 71 74 0 0 1 0 0 0 0 0999 V2000 3.9040 -5.6857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.8853 -9.0670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5053 -0.6832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8510 -5.6857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3139 -8.9180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4978 -6.1189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.6727 -6.7134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9040 -0.6271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3908 -4.8426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9485 -9.3319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0657 -1.5518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.6777 -6.8830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.1169 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.3871 -7.8121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.0184 -6.1668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.7358 -2.2119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.1567 -1.6207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.4372 -8.0250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.0684 -6.3797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.3944 -3.1236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.8153 -2.5324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9791 -2.8762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.2945 -3.6706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.8779 -7.7346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.0928 -4.1956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9305 -2.3133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3643 -4.8426 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 11.2507 -8.6531 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 9.4186 -5.8028 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 16.7778 -7.3088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.4342 -3.2839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5981 -2.3668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.4036 -2.1343 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 14.2186 -7.0183 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 15.1326 -4.3558 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.9040 -2.3133 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 14.1122 -3.9193 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.8510 -3.9995 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 11.4897 -7.7094 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 9.2583 -4.8426 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 11.4897 -1.9758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.4036 -7.5508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3908 -3.1564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8245 -3.9995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4186 -3.8823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.2186 -2.6668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.1326 -5.3293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5981 -7.3183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8819 -3.0262 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 12.4598 -1.8954 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.3643 -3.1564 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 12.4598 -7.7898 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.3113 -4.8426 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 14.8165 -6.2501 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 14.8165 -3.4350 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 14.2611 -4.8813 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.2507 -1.0320 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 13.7946 -8.4423 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9040 -3.9995 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3113 -3.1564 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4978 -3.5662 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 14.8779 -1.9506 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 16.0928 -5.4896 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0657 -8.1333 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4702 -0.4967 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4967 -1.4702 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4702 -2.4437 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3908 -1.4702 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4437 -1.4702 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8819 -6.6590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4702 -1.4702 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 27 1 0 0 0 0 5 28 1 0 0 0 0 6 29 1 0 0 0 0 7 54 1 0 0 0 0 8 68 1 0 0 0 0 9 27 1 0 0 0 0 10 28 1 0 0 0 0 11 32 2 0 0 0 0 12 14 2 0 0 0 0 12 15 1 0 0 0 0 13 16 2 0 0 0 0 13 17 1 0 0 0 0 14 18 1 0 0 0 0 15 19 2 0 0 0 0 16 20 1 0 0 0 0 17 21 2 0 0 0 0 18 30 2 0 0 0 0 19 30 1 0 0 0 0 20 31 2 0 0 0 0 21 31 1 0 0 0 0 22 23 1 0 0 0 0 22 33 1 0 0 0 0 23 37 1 0 0 0 0 24 30 1 0 0 0 0 24 34 1 0 0 0 0 25 31 1 0 0 0 0 25 35 1 0 0 0 0 26 36 1 0 0 0 0 26 69 1 0 0 0 0 27 38 1 0 0 0 0 28 39 1 0 0 0 0 29 40 1 0 0 0 0 29 70 1 0 0 0 0 32 41 1 0 0 0 0 32 49 1 0 0 0 0 33 46 1 0 0 0 0 33 50 1 0 0 0 0 34 42 1 0 0 0 0 34 54 1 0 0 0 0 35 47 1 0 0 0 0 35 55 1 0 0 0 0 36 43 1 0 0 0 0 36 68 1 0 0 0 0 37 55 1 0 0 0 0 37 56 1 0 0 0 0 38 44 1 0 0 0 0 38 51 1 0 0 0 0 39 48 1 0 0 0 0 39 52 1 0 0 0 0 40 45 1 0 0 0 0 40 53 1 0 0 0 0 41 50 2 0 0 0 0 41 57 1 0 0 0 0 42 52 2 0 0 0 0 42 58 1 0 0 0 0 43 51 2 0 0 0 0 43 59 1 0 0 0 0 44 53 2 0 0 0 0 44 60 1 0 0 0 0 45 49 2 0 0 0 0 45 61 1 0 0 0 0 46 55 1 0 0 0 0 46 62 2 0 0 0 0 47 54 1 0 0 0 0 47 63 2 0 0 0 0 48 64 2 0 0 0 0 48 70 1 0 0 0 0 65 71 1 0 0 0 0 66 71 2 0 0 0 0 67 71 2 0 0 0 0 69 71 1 0 0 0 0 M CHG 1 57 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	1012.43
Volume:	991.013
LogP:	0.378
LogD:	0.204
LogS:	-0.87
# Rotatable Bonds:	18
TPSA:	311.8
# H-Bond Aceptor:	22
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	23

MedChem Properties

QED Drug-Likeness Score:	0.096
Synthetic Accessibility Score:	7.16
Fsp3:	0.542
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:	-6.197
MDCK Permeability:	5.091528146294877e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.911
20% Bioavailability (F20%):	0.933
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	90.48164367675781%
Volume Distribution (VD):	0.996
Pgp-substrate:	2.714456558227539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.011
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.028
CYP2C9-substrate:	0.028
CYP2D6-inhibitor:	0.105
CYP2D6-substrate:	0.045
CYP3A4-inhibitor:	0.023
CYP3A4-substrate:	0.076

ADMET: Excretion

Clearance (CL):	2.372
Half-life (T1/2):	0.489

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.983
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.532
Maximum Recommended Daily Dose:	0.958
Skin Sensitization:	0.379
Carcinogencity:	0.298
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.905

Download Data

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

Natural Product: NPC471051

Natural Product ID:	NPC471051
*Common Name:**	Symplostatin 7
IUPAC Name:	sodium;[(2R)-3-[[(2S,3S)-1-[[(2S,5S,8S,11R,12S,15Z,18S,21R)-2,5-dibenzyl-8-[(2R)-butan-2-yl]-15-ethylidene-21-hydroxy-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-2-methoxy-3-oxopropyl] sulfate
Synonyms:	symplostatin 7
Standard InCHIKey:	PQKKBRUUQQKZIM-OFYOIGKZSA-M
Standard InCHI:	InChI=1S/C48H67N7O15S.Na/c1-9-27(4)38(51-43(59)36(68-8)26-69-71(65,66)67)44(60)53-40-29(6)70-48(64)39(28(5)10-2)52-42(58)34(24-30-18-14-12-15-19-30)54(7)47(63)35(25-31-20-16-13-17-21-31)55-37(56)23-22-33(46(55)62)50-41(57)32(11-3)49-45(40)61;/h11-21,27-29,33-40,56H,9-10,22-26H2,1-8H3,(H,49,61)(H,50,57)(H,51,59)(H,52,58)(H,53,60)(H,65,66,67);/q;+1/p-1/b32-11-;/t27-,28+,29+,33-,34-,35-,36+,37+,38-,39-,40-;/m0./s1
SMILES:	CC[C@H]([C@@H]1N=C(O)[C@H](Cc2ccccc2)N(C)C(=O)[C@H](Cc2ccccc2)N2[C@H](O)CC[C@@H](C2=O)N=C(/C(=C/C)/N=C([C@H]([C@H](OC1=O)C)N=C([C@H]([C@H](CC)C)N=C([C@@H](COS(=O)(=O)O)OC)O)O)O)[O-])C.[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2338552
PubChem CID:	71717727
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides

*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
NPO33098	cyanobacteria	Phylum	n.a.	Bacteria	n.a.	n.a.	n.a.	PMID[19715320]
NPO33098	cyanobacteria	Phylum	n.a.	Bacteria	n.a.	n.a.	n.a.	PMID[23350733]

☑ 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	4
Others	1

Activity Type	# Activity
Individual Protein	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT279	Individual Protein	Leukocyte elastase	Homo sapiens	IC50	=	195.0	nM	PMID[543923]
NPT2	Others	Unspecified		Activity	=	70.7	%	PMID[543923]
NPT2	Others	Unspecified		IC50	>	10000.0	nM	PMID[543923]
NPT2	Others	Unspecified		IC50	=	515.0	nM	PMID[543923]
NPT2	Others	Unspecified		IC50	=	77.0	nM	PMID[543923]

☑ 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 NPC471051 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	167
0.1-0.2	859
0.2-0.3	3292
0.3-0.4	15605
0.4-0.5	18445
0.5-0.6	3473
0.6-0.7	608
0.7-0.8	197
0.8-0.85	40
0.85-0.9	4
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471052
1.0	High Similarity	NPC471053
0.9091	High Similarity	NPC471527
0.908	High Similarity	NPC471049
0.908	High Similarity	NPC471048
0.908	High Similarity	NPC471050
0.8716	High Similarity	NPC239762
0.8716	High Similarity	NPC163392
0.8698	High Similarity	NPC163961
0.8698	High Similarity	NPC473305
0.8537	High Similarity	NPC279871
0.8512	High Similarity	NPC294951
0.8503	High Similarity	NPC476321
0.8462	Intermediate Similarity	NPC473341
0.8462	Intermediate Similarity	NPC122590
0.8452	Intermediate Similarity	NPC471526
0.8447	Intermediate Similarity	NPC210377
0.8447	Intermediate Similarity	NPC217804
0.8447	Intermediate Similarity	NPC5719
0.8447	Intermediate Similarity	NPC22883
0.8383	Intermediate Similarity	NPC269750
0.8383	Intermediate Similarity	NPC194671
0.8344	Intermediate Similarity	NPC63040
0.8333	Intermediate Similarity	NPC127741
0.8313	Intermediate Similarity	NPC477462
0.8313	Intermediate Similarity	NPC473354
0.8312	Intermediate Similarity	NPC262077
0.8282	Intermediate Similarity	NPC15068
0.8269	Intermediate Similarity	NPC2501
0.8258	Intermediate Similarity	NPC135121
0.8253	Intermediate Similarity	NPC273755
0.8247	Intermediate Similarity	NPC201244
0.8247	Intermediate Similarity	NPC477217
0.8199	Intermediate Similarity	NPC62104
0.8199	Intermediate Similarity	NPC1390
0.8182	Intermediate Similarity	NPC52748
0.8155	Intermediate Similarity	NPC50016
0.8144	Intermediate Similarity	NPC137627
0.8144	Intermediate Similarity	NPC306804
0.8137	Intermediate Similarity	NPC197743
0.8137	Intermediate Similarity	NPC297145
0.8125	Intermediate Similarity	NPC302715
0.8121	Intermediate Similarity	NPC107938
0.8121	Intermediate Similarity	NPC294516
0.8117	Intermediate Similarity	NPC161069
0.8114	Intermediate Similarity	NPC473378
0.8114	Intermediate Similarity	NPC473407
0.8105	Intermediate Similarity	NPC268841
0.8105	Intermediate Similarity	NPC307357
0.8105	Intermediate Similarity	NPC46098
0.8095	Intermediate Similarity	NPC155506
0.8095	Intermediate Similarity	NPC26108
0.8095	Intermediate Similarity	NPC159767
0.8092	Intermediate Similarity	NPC68865
0.8089	Intermediate Similarity	NPC471820
0.8089	Intermediate Similarity	NPC471821
0.8059	Intermediate Similarity	NPC45037
0.8024	Intermediate Similarity	NPC40234
0.8013	Intermediate Similarity	NPC209509
0.7988	Intermediate Similarity	NPC476227
0.7987	Intermediate Similarity	NPC475168
0.7987	Intermediate Similarity	NPC7817
0.7976	Intermediate Similarity	NPC230611
0.7949	Intermediate Similarity	NPC476978
0.7911	Intermediate Similarity	NPC138775
0.7898	Intermediate Similarity	NPC5620
0.7885	Intermediate Similarity	NPC197682
0.7885	Intermediate Similarity	NPC176226
0.7882	Intermediate Similarity	NPC473402
0.7848	Intermediate Similarity	NPC314358
0.784	Intermediate Similarity	NPC470902
0.7826	Intermediate Similarity	NPC162104
0.7821	Intermediate Similarity	NPC168113
0.7797	Intermediate Similarity	NPC102959
0.7785	Intermediate Similarity	NPC316008
0.7785	Intermediate Similarity	NPC313867
0.7756	Intermediate Similarity	NPC476259
0.7753	Intermediate Similarity	NPC60516
0.775	Intermediate Similarity	NPC105717
0.7722	Intermediate Similarity	NPC315283
0.7722	Intermediate Similarity	NPC314388
0.7719	Intermediate Similarity	NPC248670
0.7707	Intermediate Similarity	NPC263493
0.7707	Intermediate Similarity	NPC269398
0.7706	Intermediate Similarity	NPC475123
0.7706	Intermediate Similarity	NPC475204
0.7706	Intermediate Similarity	NPC46009
0.7702	Intermediate Similarity	NPC129666
0.7692	Intermediate Similarity	NPC92784
0.7692	Intermediate Similarity	NPC98424
0.7692	Intermediate Similarity	NPC476133
0.7692	Intermediate Similarity	NPC470884
0.7692	Intermediate Similarity	NPC178662
0.7688	Intermediate Similarity	NPC145113
0.7669	Intermediate Similarity	NPC286551
0.7658	Intermediate Similarity	NPC139326
0.7632	Intermediate Similarity	NPC111428
0.7628	Intermediate Similarity	NPC471265
0.7628	Intermediate Similarity	NPC471264
0.7578	Intermediate Similarity	NPC225648
0.7578	Intermediate Similarity	NPC329761
0.7572	Intermediate Similarity	NPC471165
0.7562	Intermediate Similarity	NPC315266
0.7556	Intermediate Similarity	NPC240130
0.7556	Intermediate Similarity	NPC61332
0.7532	Intermediate Similarity	NPC130309
0.7532	Intermediate Similarity	NPC255447
0.7527	Intermediate Similarity	NPC65714
0.7516	Intermediate Similarity	NPC473322
0.7471	Intermediate Similarity	NPC63931
0.7457	Intermediate Similarity	NPC89831
0.7451	Intermediate Similarity	NPC105114
0.7451	Intermediate Similarity	NPC239990
0.7451	Intermediate Similarity	NPC71933
0.7451	Intermediate Similarity	NPC319766
0.7451	Intermediate Similarity	NPC89923
0.7451	Intermediate Similarity	NPC152850
0.7446	Intermediate Similarity	NPC473371
0.7432	Intermediate Similarity	NPC470546
0.7432	Intermediate Similarity	NPC237420
0.7423	Intermediate Similarity	NPC240848
0.7417	Intermediate Similarity	NPC6975
0.7417	Intermediate Similarity	NPC46427
0.7405	Intermediate Similarity	NPC471592
0.7399	Intermediate Similarity	NPC196091
0.7386	Intermediate Similarity	NPC136453
0.7375	Intermediate Similarity	NPC469427
0.7375	Intermediate Similarity	NPC469426
0.7372	Intermediate Similarity	NPC246079
0.7371	Intermediate Similarity	NPC158277
0.7365	Intermediate Similarity	NPC169328
0.7365	Intermediate Similarity	NPC470545
0.736	Intermediate Similarity	NPC473404
0.7358	Intermediate Similarity	NPC132636
0.7351	Intermediate Similarity	NPC252878
0.7333	Intermediate Similarity	NPC45777
0.7333	Intermediate Similarity	NPC477061
0.7315	Intermediate Similarity	NPC310467
0.7308	Intermediate Similarity	NPC157311
0.7297	Intermediate Similarity	NPC470544
0.7285	Intermediate Similarity	NPC202521
0.7273	Intermediate Similarity	NPC317362
0.7273	Intermediate Similarity	NPC323662
0.7273	Intermediate Similarity	NPC318930
0.7262	Intermediate Similarity	NPC469903
0.7261	Intermediate Similarity	NPC8761
0.7261	Intermediate Similarity	NPC44805
0.7238	Intermediate Similarity	NPC315542
0.7219	Intermediate Similarity	NPC476990
0.7219	Intermediate Similarity	NPC200964
0.7219	Intermediate Similarity	NPC190663
0.7215	Intermediate Similarity	NPC287401
0.7208	Intermediate Similarity	NPC47667
0.7193	Intermediate Similarity	NPC114806
0.7193	Intermediate Similarity	NPC469901
0.7193	Intermediate Similarity	NPC469902
0.7179	Intermediate Similarity	NPC469666
0.7175	Intermediate Similarity	NPC326407
0.7175	Intermediate Similarity	NPC317725
0.717	Intermediate Similarity	NPC248283
0.7169	Intermediate Similarity	NPC283783
0.7158	Intermediate Similarity	NPC94862
0.7151	Intermediate Similarity	NPC73655
0.7151	Intermediate Similarity	NPC328763
0.715	Intermediate Similarity	NPC220060
0.7143	Intermediate Similarity	NPC473000
0.7135	Intermediate Similarity	NPC24617
0.7134	Intermediate Similarity	NPC200589
0.7124	Intermediate Similarity	NPC160493
0.7105	Intermediate Similarity	NPC477551
0.7105	Intermediate Similarity	NPC478014
0.7105	Intermediate Similarity	NPC478015
0.7105	Intermediate Similarity	NPC478016
0.7102	Intermediate Similarity	NPC473693
0.7102	Intermediate Similarity	NPC471568
0.7097	Intermediate Similarity	NPC101719
0.709	Intermediate Similarity	NPC477550
0.709	Intermediate Similarity	NPC477552
0.7086	Intermediate Similarity	NPC220698
0.7083	Intermediate Similarity	NPC233702
0.7081	Intermediate Similarity	NPC43755
0.7081	Intermediate Similarity	NPC64140
0.7081	Intermediate Similarity	NPC174122
0.7078	Intermediate Similarity	NPC35996
0.7069	Intermediate Similarity	NPC472923
0.7059	Intermediate Similarity	NPC71684
0.7056	Intermediate Similarity	NPC475421
0.7048	Intermediate Similarity	NPC16188
0.7045	Intermediate Similarity	NPC469904
0.7045	Intermediate Similarity	NPC186617
0.7043	Intermediate Similarity	NPC248822
0.7041	Intermediate Similarity	NPC262166
0.7039	Intermediate Similarity	NPC469900
0.7032	Intermediate Similarity	NPC222466
0.703	Intermediate Similarity	NPC322878
0.7029	Intermediate Similarity	NPC254700
0.7027	Intermediate Similarity	NPC234069
0.7026	Intermediate Similarity	NPC469444
0.7016	Intermediate Similarity	NPC469443
0.7005	Intermediate Similarity	NPC277306

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 NPC471051 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	108
0.1-0.2	349
0.2-0.3	675
0.3-0.4	1912
0.4-0.5	3863
0.5-0.6	1938
0.6-0.7	297
0.7-0.8	8
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
0.7911	Intermediate Similarity	NPD8323	Discontinued
0.7628	Intermediate Similarity	NPD8173	Phase 2
0.7628	Intermediate Similarity	NPD8172	Phase 2
0.753	Intermediate Similarity	NPD8417	Discontinued
0.7381	Intermediate Similarity	NPD7749	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD2584	Suspended
0.725	Intermediate Similarity	NPD6852	Discontinued
0.7239	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6073	Approved
0.7143	Intermediate Similarity	NPD6294	Approved
0.7143	Intermediate Similarity	NPD6295	Approved
0.7125	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD7608	Discontinued
0.707	Intermediate Similarity	NPD4175	Approved
0.707	Intermediate Similarity	NPD4177	Approved
0.7066	Intermediate Similarity	NPD6088	Approved
0.7065	Intermediate Similarity	NPD8103	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD8416	Discontinued
0.7063	Intermediate Similarity	NPD5296	Approved
0.7063	Intermediate Similarity	NPD8265	Approved
0.7051	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4677	Discontinued
0.7019	Intermediate Similarity	NPD8643	Discontinued
0.7006	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8315	Phase 1
0.6987	Remote Similarity	NPD3125	Approved
0.6982	Remote Similarity	NPD7613	Discontinued
0.6975	Remote Similarity	NPD5725	Approved
0.697	Remote Similarity	NPD6681	Discovery
0.6962	Remote Similarity	NPD3626	Phase 3
0.6957	Remote Similarity	NPD6623	Phase 3
0.6954	Remote Similarity	NPD7600	Phase 2
0.6946	Remote Similarity	NPD6552	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4620	Approved
0.6918	Remote Similarity	NPD5201	Approved
0.6918	Remote Similarity	NPD4125	Approved
0.6918	Remote Similarity	NPD5203	Approved
0.6918	Remote Similarity	NPD4617	Approved
0.6918	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD8076	Discontinued
0.6899	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7599	Phase 2
0.6894	Remote Similarity	NPD5747	Discontinued
0.6879	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4738	Phase 2
0.6852	Remote Similarity	NPD5120	Approved
0.6852	Remote Similarity	NPD5121	Approved
0.6852	Remote Similarity	NPD5119	Approved
0.6832	Remote Similarity	NPD5581	Approved
0.6813	Remote Similarity	NPD5263	Approved
0.6795	Remote Similarity	NPD4706	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD7683	Discontinued
0.679	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.679	Remote Similarity	NPD3561	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD2218	Phase 2
0.6753	Remote Similarity	NPD2217	Approved
0.6752	Remote Similarity	NPD3073	Approved
0.6752	Remote Similarity	NPD3072	Approved
0.6752	Remote Similarity	NPD3071	Approved
0.6747	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD7131	Phase 3
0.6732	Remote Similarity	NPD4576	Approved
0.6732	Remote Similarity	NPD4574	Approved
0.6728	Remote Similarity	NPD4619	Approved
0.6728	Remote Similarity	NPD4621	Approved
0.6728	Remote Similarity	NPD1330	Phase 2
0.6728	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6901	Phase 3
0.6725	Remote Similarity	NPD4432	Discontinued
0.6725	Remote Similarity	NPD4682	Phase 2
0.6724	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD8351	Phase 2
0.671	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7720	Phase 2
0.6688	Remote Similarity	NPD4761	Approved
0.6688	Remote Similarity	NPD4762	Approved
0.6688	Remote Similarity	NPD7522	Discontinued
0.6687	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD4151	Approved
0.6686	Remote Similarity	NPD7105	Phase 1
0.6686	Remote Similarity	NPD6676	Phase 2
0.6667	Remote Similarity	NPD7485	Phase 3
0.6667	Remote Similarity	NPD5723	Approved
0.6667	Remote Similarity	NPD7484	Phase 3
0.6667	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7511	Approved
0.6647	Remote Similarity	NPD7512	Approved
0.6628	Remote Similarity	NPD5941	Approved
0.6628	Remote Similarity	NPD5942	Approved
0.6628	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD5264	Approved
0.6627	Remote Similarity	NPD5265	Approved
0.6626	Remote Similarity	NPD7908	Discontinued
0.6625	Remote Similarity	NPD2625	Approved
0.6625	Remote Similarity	NPD2160	Approved
0.6625	Remote Similarity	NPD2628	Approved
0.6625	Remote Similarity	NPD2627	Approved
0.6625	Remote Similarity	NPD2159	Approved
0.6625	Remote Similarity	NPD2626	Approved
0.6615	Remote Similarity	NPD7811	Phase 3
0.6615	Remote Similarity	NPD7810	Phase 3
0.661	Remote Similarity	NPD4557	Approved
0.6609	Remote Similarity	NPD7836	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD4676	Approved
0.6603	Remote Similarity	NPD5981	Approved
0.6596	Remote Similarity	NPD6851	Approved
0.6596	Remote Similarity	NPD6853	Approved
0.6588	Remote Similarity	NPD1968	Approved
0.6588	Remote Similarity	NPD1967	Approved
0.6584	Remote Similarity	NPD3604	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7965	Phase 2
0.6557	Remote Similarity	NPD7964	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD4172	Approved
0.6548	Remote Similarity	NPD4173	Approved
0.6545	Remote Similarity	NPD4153	Approved
0.6543	Remote Similarity	NPD7828	Discontinued
0.6543	Remote Similarity	NPD5759	Approved
0.6541	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD2891	Approved
0.6509	Remote Similarity	NPD4152	Approved
0.6508	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD8356	Approved
0.6503	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD2613	Approved
0.6491	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD2575	Approved
0.6489	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD6865	Phase 2
0.6488	Remote Similarity	NPD6864	Phase 2
0.6485	Remote Similarity	NPD3090	Approved
0.6485	Remote Similarity	NPD4746	Phase 3
0.6485	Remote Similarity	NPD2574	Discontinued
0.6485	Remote Similarity	NPD7714	Approved
0.6485	Remote Similarity	NPD3615	Approved
0.6485	Remote Similarity	NPD2571	Approved
0.6485	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD7715	Approved
0.6485	Remote Similarity	NPD2566	Approved
0.6485	Remote Similarity	NPD2570	Approved
0.6485	Remote Similarity	NPD4745	Approved
0.6485	Remote Similarity	NPD3614	Approved
0.6485	Remote Similarity	NPD3087	Approved
0.6485	Remote Similarity	NPD3088	Approved
0.6485	Remote Similarity	NPD3616	Approved
0.6485	Remote Similarity	NPD3089	Approved
0.6485	Remote Similarity	NPD2573	Approved
0.6478	Remote Similarity	NPD4806	Approved
0.6478	Remote Similarity	NPD4807	Approved
0.6478	Remote Similarity	NPD4215	Approved
0.6478	Remote Similarity	NPD2610	Approved
0.6478	Remote Similarity	NPD3132	Approved
0.6478	Remote Similarity	NPD2611	Approved
0.6478	Remote Similarity	NPD4217	Approved
0.6478	Remote Similarity	NPD4218	Approved
0.6478	Remote Similarity	NPD2608	Approved
0.6478	Remote Similarity	NPD2609	Approved
0.6478	Remote Similarity	NPD2612	Approved
0.6478	Remote Similarity	NPD3131	Approved
0.6478	Remote Similarity	NPD4216	Approved
0.6474	Remote Similarity	NPD6631	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD7510	Approved
0.6467	Remote Similarity	NPD8124	Phase 3
0.6467	Remote Similarity	NPD8126	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD8303	Discontinued
0.6463	Remote Similarity	NPD6039	Approved
0.6461	Remote Similarity	NPD7011	Discontinued
0.6461	Remote Similarity	NPD8019	Approved
0.646	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.646	Remote Similarity	NPD5578	Approved
0.646	Remote Similarity	NPD6792	Phase 3
0.6453	Remote Similarity	NPD7602	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD7968	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD3644	Approved
0.6447	Remote Similarity	NPD3642	Approved
0.6447	Remote Similarity	NPD3643	Approved
0.6446	Remote Similarity	NPD6309	Approved
0.6446	Remote Similarity	NPD6311	Approved
0.6446	Remote Similarity	NPD6310	Approved
0.6446	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD5204	Approved
0.6441	Remote Similarity	NPD7463	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD6345	Approved
0.6433	Remote Similarity	NPD6343	Approved
0.642	Remote Similarity	NPD7745	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD4106	Approved
0.6415	Remote Similarity	NPD4136	Approved
0.6415	Remote Similarity	NPD4135	Approved
0.6407	Remote Similarity	NPD4684	Phase 3
0.6407	Remote Similarity	NPD3908	Approved
0.6407	Remote Similarity	NPD4686	Approved
0.6407	Remote Similarity	NPD4685	Phase 3
0.6404	Remote Similarity	NPD3067	Approved
0.6402	Remote Similarity	NPD7979	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