NPASS Compound

Structure

NPC155670 OpenBabel07101719122D 72 72 0 0 1 0 0 0 0 0999 V2000 7.8892 6.1532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3600 -7.4358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6295 -7.3633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8816 -2.8622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5704 -3.9939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8650 -6.4165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5592 -6.0564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9071 -2.6703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8956 -1.2480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5857 -8.0601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2681 6.9369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2788 6.7908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9107 5.8611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9214 5.7150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5533 4.7852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5640 4.6391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1959 3.7093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2066 3.5632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8385 2.6335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8492 2.4874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4811 1.5576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5082 1.4115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2776 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2721 0.7045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5575 -5.9009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2459 -2.2926 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4003 -4.7693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1696 -1.1031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8449 0.7304 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0588 -7.5997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5157 -6.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8993 -3.0495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6082 -5.7474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9908 -1.6738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3370 -7.0915 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8763 0.4818 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6898 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7132 -5.3651 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2636 -2.4799 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4492 -4.4602 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4230 -6.7234 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2648 -1.5289 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8449 0.7304 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6788 -0.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4593 -8.4550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3449 -7.2168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4187 -0.6845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0758 -6.1356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3264 -3.4780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6366 -3.4780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3860 -6.1356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7290 -0.6845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2668 -6.7234 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.8135 0.4818 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.3528 -7.0915 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.9546 -1.5289 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.1390 -4.4602 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.0234 -5.3651 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.5738 -2.4799 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.9702 1.7226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6733 -0.3136 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0910 -1.0181 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4591 -8.4341 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0225 -9.3313 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3449 -8.2168 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1893 -0.0471 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7603 -6.8646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3244 -3.5407 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6346 -3.5407 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0706 -6.8646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4995 -0.0471 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 31 1 0 0 0 0 3 31 1 0 0 0 0 4 32 1 0 0 0 0 5 32 1 0 0 0 0 6 33 1 0 0 0 0 7 33 1 0 0 0 0 8 34 1 0 0 0 0 9 34 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 23 24 1 0 0 0 0 24 44 1 0 0 0 0 25 31 1 0 0 0 0 26 32 1 0 0 0 0 27 33 1 0 0 0 0 28 34 1 0 0 0 0 29 36 1 0 0 0 0 29 43 1 0 0 0 0 30 45 1 0 0 0 0 35 10 1 6 0 0 0 35 46 1 0 0 0 0 35 53 1 0 0 0 0 36 22 1 1 0 0 0 36 72 1 0 0 0 0 37 23 1 6 0 0 0 37 47 1 0 0 0 0 37 54 1 0 0 0 0 38 25 1 6 0 0 0 38 48 1 0 0 0 0 38 57 1 0 0 0 0 39 26 1 6 0 0 0 39 49 1 0 0 0 0 39 56 1 0 0 0 0 40 27 1 6 0 0 0 40 50 1 0 0 0 0 40 58 1 0 0 0 0 41 30 1 6 0 0 0 41 51 1 0 0 0 0 41 55 1 0 0 0 0 42 28 1 6 0 0 0 42 52 1 0 0 0 0 42 59 1 0 0 0 0 43 54 2 3 0 0 0 43 60 1 0 0 0 0 44 61 2 0 0 0 0 44 62 1 0 0 0 0 45 63 2 0 0 0 0 45 64 1 0 0 0 0 46 55 2 3 0 0 0 46 65 1 0 0 0 0 47 56 2 3 0 0 0 47 66 1 0 0 0 0 48 53 2 3 0 0 0 48 67 1 0 0 0 0 49 57 2 3 0 0 0 49 68 1 0 0 0 0 50 59 2 3 0 0 0 50 69 1 0 0 0 0 51 58 2 3 0 0 0 51 70 1 0 0 0 0 52 71 2 0 0 0 0 52 72 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1021.67
Volume:	1064.277
LogP:	8.23
LogD:	3.98
LogS:	-3.1
# Rotatable Bonds:	25
TPSA:	315.07
# H-Bond Aceptor:	20
# H-Bond Donor:	9
# Rings:	1
# Heavy Atoms:	20

MedChem Properties

QED Drug-Likeness Score:	0.032
Synthetic Accessibility Score:	6.317
Fsp3:	0.808
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.531
MDCK Permeability:	8.08433469501324e-05
Pgp-inhibitor:	0.098
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.338
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.963

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.087
Plasma Protein Binding (PPB):	72.8358383178711%
Volume Distribution (VD):	0.719
Pgp-substrate:	5.16489315032959%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.036
CYP2C9-inhibitor:	0.076
CYP2C9-substrate:	0.999
CYP2D6-inhibitor:	0.083
CYP2D6-substrate:	0.031
CYP3A4-inhibitor:	0.109
CYP3A4-substrate:	0.003

ADMET: Excretion

Clearance (CL):	1.271
Half-life (T1/2):	0.787

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.999
Drug-inuced Liver Injury (DILI):	0.878
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.979
Skin Sensitization:	0.438
Carcinogencity:	0.287
Eye Corrosion:	0.005
Eye Irritation:	0.009
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC155670

Natural Product ID:	NPC155670
*Common Name:**	3-((3S,6S,9S,12S,15S,18S,21S,25R)-9-(Carboxymethyl)-3,6,15,18-Tetraisobutyl-12-Methyl-2,5,8,11,14,17,20,23-Octaoxo-25-Tridecyl-1-Oxa-4,7,10,13,16,19,22-Heptaazacyclopentacosan-21-Yl)Propanoic Acid
IUPAC Name:	3-[(3S,6S,9S,12S,15S,18S,21S,25R)-9-(carboxymethyl)-12-methyl-3,6,15,18-tetrakis(2-methylpropyl)-2,5,8,11,14,17,20,23-octaoxo-25-tridecyl-1-oxa-4,7,10,13,16,19,22-heptazacyclopentacos-21-yl]propanoic acid
Synonyms:
Standard InCHIKey:	DBWQOVCXXYQRNR-PPIUSPOOSA-N
Standard InCHI:	InChI=1S/C52H91N7O13/c1-11-12-13-14-15-16-17-18-19-20-21-22-36-29-43(60)54-37(23-24-44(61)62)47(66)56-39(26-32(4)5)49(68)57-38(25-31(2)3)48(67)53-35(10)46(65)55-41(30-45(63)64)51(70)58-40(27-33(6)7)50(69)59-42(28-34(8)9)52(71)72-36/h31-42H,11-30H2,1-10H3,(H,53,67)(H,54,60)(H,55,65)(H,56,66)(H,57,68)(H,58,70)(H,59,69)(H,61,62)(H,63,64)/t35-,36+,37-,38-,39-,40-,41-,42-/m0/s1
SMILES:	CCCCCCCCCCCCC[C@@H]1CC(=N[C@@H](CCC(=O)O)C(=N[C@@H](CC(C)C)C(=N[C@@H](CC(C)C)C(=N[C@H](C(=N[C@H](C(=N[C@H](C(=N[C@H](C(=O)O1)CC(C)C)O)CC(C)C)O)CC(=O)O)O)C)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689219
PubChem CID:	51039600
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
NPO33144	bacillus amyloliquefaciens strain bo7	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[21235220]

☑ 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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT610	Others	Molecular identity unknown		Activity	=	29.0	%	PMID[511501]

☑ 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 NPC155670 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	3119
0.2-0.3	21849
0.3-0.4	13793
0.4-0.5	3136
0.5-0.6	471
0.6-0.7	114
0.7-0.8	37
0.8-0.85	5
0.85-0.9	17
0.9-0.95	7
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC145748
1.0	High Similarity	NPC95478
0.9872	High Similarity	NPC227051
0.9048	High Similarity	NPC477729
0.8354	Intermediate Similarity	NPC86064
0.8228	Intermediate Similarity	NPC43219
0.8077	Intermediate Similarity	NPC478256
0.8046	Intermediate Similarity	NPC477728
0.7952	Intermediate Similarity	NPC478017
0.7952	Intermediate Similarity	NPC315535
0.7952	Intermediate Similarity	NPC315131
0.7831	Intermediate Similarity	NPC316242
0.7791	Intermediate Similarity	NPC477730
0.7738	Intermediate Similarity	NPC473984
0.75	Intermediate Similarity	NPC474298
0.75	Intermediate Similarity	NPC28348
0.75	Intermediate Similarity	NPC474299
0.75	Intermediate Similarity	NPC475808
0.75	Intermediate Similarity	NPC473985
0.7419	Intermediate Similarity	NPC270005
0.7419	Intermediate Similarity	NPC208537
0.7375	Intermediate Similarity	NPC470110
0.7356	Intermediate Similarity	NPC314466
0.7349	Intermediate Similarity	NPC138435
0.725	Intermediate Similarity	NPC470109
0.7229	Intermediate Similarity	NPC141325
0.7179	Intermediate Similarity	NPC327252
0.7176	Intermediate Similarity	NPC476130
0.7176	Intermediate Similarity	NPC476324
0.7125	Intermediate Similarity	NPC470108
0.7111	Intermediate Similarity	NPC320936
0.7073	Intermediate Similarity	NPC193280
0.7073	Intermediate Similarity	NPC314273
0.7024	Intermediate Similarity	NPC320865
0.7024	Intermediate Similarity	NPC477641
0.7024	Intermediate Similarity	NPC477643
0.7	Intermediate Similarity	NPC47135
0.6988	Remote Similarity	NPC477642
0.6988	Remote Similarity	NPC476285
0.697	Remote Similarity	NPC220234
0.6897	Remote Similarity	NPC472594
0.6835	Remote Similarity	NPC477644
0.6824	Remote Similarity	NPC474403
0.68	Remote Similarity	NPC475440
0.6786	Remote Similarity	NPC476291
0.6757	Remote Similarity	NPC477237
0.6747	Remote Similarity	NPC195165
0.6735	Remote Similarity	NPC470283
0.6667	Remote Similarity	NPC472595
0.6667	Remote Similarity	NPC476523
0.6667	Remote Similarity	NPC159369
0.6667	Remote Similarity	NPC472579
0.6667	Remote Similarity	NPC39290
0.6637	Remote Similarity	NPC477238
0.6602	Remote Similarity	NPC301148
0.6602	Remote Similarity	NPC5864
0.6602	Remote Similarity	NPC124554
0.6571	Remote Similarity	NPC475918
0.6562	Remote Similarity	NPC292345
0.6562	Remote Similarity	NPC193386
0.6552	Remote Similarity	NPC476248
0.6545	Remote Similarity	NPC471645
0.6538	Remote Similarity	NPC198344
0.6512	Remote Similarity	NPC477200
0.6495	Remote Similarity	NPC474593
0.6495	Remote Similarity	NPC475801
0.6476	Remote Similarity	NPC124549
0.6463	Remote Similarity	NPC145658
0.6452	Remote Similarity	NPC474312
0.6429	Remote Similarity	NPC474576
0.6392	Remote Similarity	NPC470284
0.6375	Remote Similarity	NPC473599
0.6364	Remote Similarity	NPC62263
0.6364	Remote Similarity	NPC315237
0.6364	Remote Similarity	NPC471098
0.6364	Remote Similarity	NPC173763
0.6341	Remote Similarity	NPC145627
0.6321	Remote Similarity	NPC74035
0.63	Remote Similarity	NPC226513
0.6296	Remote Similarity	NPC67009
0.6296	Remote Similarity	NPC171734
0.6264	Remote Similarity	NPC37681
0.625	Remote Similarity	NPC472578
0.6196	Remote Similarity	NPC474833
0.619	Remote Similarity	NPC188453
0.619	Remote Similarity	NPC42320
0.6173	Remote Similarity	NPC321468
0.6173	Remote Similarity	NPC321536
0.6173	Remote Similarity	NPC327748
0.617	Remote Similarity	NPC246005
0.617	Remote Similarity	NPC84128
0.617	Remote Similarity	NPC53858
0.6168	Remote Similarity	NPC323720
0.6167	Remote Similarity	NPC477793
0.6167	Remote Similarity	NPC329919
0.6161	Remote Similarity	NPC471202
0.6161	Remote Similarity	NPC63191
0.6132	Remote Similarity	NPC227622
0.6126	Remote Similarity	NPC476875
0.6125	Remote Similarity	NPC317147
0.6118	Remote Similarity	NPC326651
0.6118	Remote Similarity	NPC325117
0.6118	Remote Similarity	NPC322319
0.6111	Remote Similarity	NPC475637
0.6104	Remote Similarity	NPC322946
0.6098	Remote Similarity	NPC143722
0.6098	Remote Similarity	NPC327170
0.6098	Remote Similarity	NPC329564
0.6092	Remote Similarity	NPC126779
0.6092	Remote Similarity	NPC474812
0.6076	Remote Similarity	NPC322573
0.6026	Remote Similarity	NPC263065
0.6026	Remote Similarity	NPC189178
0.6019	Remote Similarity	NPC128303
0.6	Remote Similarity	NPC263281
0.6	Remote Similarity	NPC15413
0.5976	Remote Similarity	NPC316826
0.5976	Remote Similarity	NPC317143
0.5974	Remote Similarity	NPC319110
0.5974	Remote Similarity	NPC329181
0.5963	Remote Similarity	NPC241394
0.5962	Remote Similarity	NPC160066
0.5949	Remote Similarity	NPC270041
0.593	Remote Similarity	NPC474402
0.5926	Remote Similarity	NPC318260
0.5918	Remote Similarity	NPC83839
0.5914	Remote Similarity	NPC477145
0.5914	Remote Similarity	NPC473741
0.5904	Remote Similarity	NPC471129
0.59	Remote Similarity	NPC322966
0.5882	Remote Similarity	NPC273185
0.5872	Remote Similarity	NPC14537
0.5862	Remote Similarity	NPC201968
0.5862	Remote Similarity	NPC209734
0.5856	Remote Similarity	NPC70235
0.5849	Remote Similarity	NPC474952
0.5844	Remote Similarity	NPC80350
0.5824	Remote Similarity	NPC178919
0.5818	Remote Similarity	NPC473252
0.5816	Remote Similarity	NPC253975
0.5816	Remote Similarity	NPC192025
0.5816	Remote Similarity	NPC125253
0.581	Remote Similarity	NPC313821
0.581	Remote Similarity	NPC134504
0.581	Remote Similarity	NPC473597
0.581	Remote Similarity	NPC47076
0.5804	Remote Similarity	NPC329305
0.5802	Remote Similarity	NPC38463
0.5802	Remote Similarity	NPC325985
0.5798	Remote Similarity	NPC315188
0.5795	Remote Similarity	NPC306696
0.5784	Remote Similarity	NPC477538
0.5783	Remote Similarity	NPC320598
0.5783	Remote Similarity	NPC254541
0.578	Remote Similarity	NPC215988
0.578	Remote Similarity	NPC476877
0.5776	Remote Similarity	NPC222481
0.5776	Remote Similarity	NPC470621
0.5766	Remote Similarity	NPC137453
0.5763	Remote Similarity	NPC169328
0.5743	Remote Similarity	NPC203170
0.5714	Remote Similarity	NPC470652
0.5714	Remote Similarity	NPC55274
0.5714	Remote Similarity	NPC315897
0.5714	Remote Similarity	NPC470363
0.5714	Remote Similarity	NPC475150
0.5714	Remote Similarity	NPC310467
0.5701	Remote Similarity	NPC234542
0.5701	Remote Similarity	NPC475758
0.569	Remote Similarity	NPC259586
0.569	Remote Similarity	NPC103391
0.569	Remote Similarity	NPC50694
0.569	Remote Similarity	NPC472536
0.5688	Remote Similarity	NPC477198
0.5688	Remote Similarity	NPC475149
0.5688	Remote Similarity	NPC471097
0.5684	Remote Similarity	NPC316807
0.5682	Remote Similarity	NPC118524
0.568	Remote Similarity	NPC313657
0.5676	Remote Similarity	NPC471844
0.5676	Remote Similarity	NPC476876
0.5673	Remote Similarity	NPC469998
0.5664	Remote Similarity	NPC473578
0.5663	Remote Similarity	NPC190385
0.5663	Remote Similarity	NPC189301
0.5663	Remote Similarity	NPC328447
0.5663	Remote Similarity	NPC176164
0.566	Remote Similarity	NPC189629
0.566	Remote Similarity	NPC123141
0.5657	Remote Similarity	NPC477199
0.5656	Remote Similarity	NPC470653
0.5656	Remote Similarity	NPC470654
0.5656	Remote Similarity	NPC470650
0.5648	Remote Similarity	NPC13175
0.5648	Remote Similarity	NPC475791
0.5648	Remote Similarity	NPC473224
0.5645	Remote Similarity	NPC47667
0.5644	Remote Similarity	NPC470282
0.5638	Remote Similarity	NPC330017
0.5632	Remote Similarity	NPC325597

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 NPC155670 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	82
0.1-0.2	2224
0.2-0.3	4648
0.3-0.4	1604
0.4-0.5	431
0.5-0.6	133
0.6-0.7	20
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
0.7952	Intermediate Similarity	NPD7918	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD7917	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD8394	Approved
0.7284	Intermediate Similarity	NPD3724	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD3160	Suspended
0.7179	Intermediate Similarity	NPD575	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD574	Approved
0.7037	Intermediate Similarity	NPD1429	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD2256	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6944	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD3716	Discontinued
0.7	Intermediate Similarity	NPD7345	Approved
0.6889	Remote Similarity	NPD1448	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD2263	Discontinued
0.6813	Remote Similarity	NPD7643	Phase 1
0.6705	Remote Similarity	NPD2689	Clinical (unspecified phase)
0.66	Remote Similarity	NPD6428	Approved
0.6596	Remote Similarity	NPD619	Phase 3
0.6591	Remote Similarity	NPD1453	Phase 1
0.6562	Remote Similarity	NPD618	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD8305	Approved
0.6389	Remote Similarity	NPD8306	Approved
0.6337	Remote Similarity	NPD7844	Discontinued
0.63	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD4759	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3187	Discontinued
0.6239	Remote Similarity	NPD6941	Approved
0.6226	Remote Similarity	NPD8275	Approved
0.6226	Remote Similarity	NPD8276	Approved
0.6224	Remote Similarity	NPD4264	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6699	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD6421	Discontinued
0.6132	Remote Similarity	NPD8083	Approved
0.6132	Remote Similarity	NPD8138	Approved
0.6132	Remote Similarity	NPD8084	Approved
0.6132	Remote Similarity	NPD8085	Approved
0.6132	Remote Similarity	NPD8139	Approved
0.6132	Remote Similarity	NPD8082	Approved
0.6132	Remote Similarity	NPD8086	Approved
0.6111	Remote Similarity	NPD8393	Approved
0.6106	Remote Similarity	NPD7915	Approved
0.6106	Remote Similarity	NPD7916	Approved
0.6105	Remote Similarity	NPD4829	Discontinued
0.6104	Remote Similarity	NPD9441	Phase 2
0.6092	Remote Similarity	NPD4242	Approved
0.6067	Remote Similarity	NPD1147	Phase 2
0.6058	Remote Similarity	NPD8038	Phase 2
0.6055	Remote Similarity	NPD8307	Discontinued
0.6055	Remote Similarity	NPD8140	Approved
0.6049	Remote Similarity	NPD9433	Approved
0.6044	Remote Similarity	NPD2257	Approved
0.6026	Remote Similarity	NPD9205	Approved
0.6026	Remote Similarity	NPD9204	Approved
0.6019	Remote Similarity	NPD8081	Approved
0.6018	Remote Similarity	NPD8298	Phase 2
0.5981	Remote Similarity	NPD7141	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD7140	Approved
0.5981	Remote Similarity	NPD7139	Approved
0.598	Remote Similarity	NPD1447	Phase 3
0.598	Remote Similarity	NPD1446	Phase 3
0.5977	Remote Similarity	NPD4241	Registered
0.5962	Remote Similarity	NPD4228	Discovery
0.5955	Remote Similarity	NPD9446	Approved
0.5949	Remote Similarity	NPD9419	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD8045	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD7760	Phase 2
0.5918	Remote Similarity	NPD7759	Phase 2
0.5909	Remote Similarity	NPD8175	Discontinued
0.5893	Remote Similarity	NPD8087	Discontinued
0.5889	Remote Similarity	NPD6704	Discontinued
0.5876	Remote Similarity	NPD3733	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD2255	Approved
0.5843	Remote Similarity	NPD2696	Approved
0.5843	Remote Similarity	NPD2697	Approved
0.5843	Remote Similarity	NPD2694	Approved
0.5843	Remote Similarity	NPD2695	Approved
0.581	Remote Similarity	NPD3189	Approved
0.581	Remote Similarity	NPD3191	Approved
0.581	Remote Similarity	NPD3190	Approved
0.5804	Remote Similarity	NPD6413	Approved
0.5784	Remote Similarity	NPD4261	Phase 1
0.578	Remote Similarity	NPD6122	Discontinued
0.5778	Remote Similarity	NPD2262	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD882	Phase 2
0.5773	Remote Similarity	NPD883	Phase 2
0.5769	Remote Similarity	NPD573	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD3723	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD1825	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7841	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8174	Phase 2
0.5699	Remote Similarity	NPD11	Approved
0.5699	Remote Similarity	NPD376	Approved
0.5688	Remote Similarity	NPD8301	Approved
0.5688	Remote Similarity	NPD8300	Approved
0.5682	Remote Similarity	NPD9421	Phase 1
0.5682	Remote Similarity	NPD886	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD8277	Approved
0.5663	Remote Similarity	NPD9023	Clinical (unspecified phase)
0.5663	Remote Similarity	NPD9661	Approved
0.5648	Remote Similarity	NPD8418	Phase 2
0.5632	Remote Similarity	NPD7909	Approved
0.5632	Remote Similarity	NPD348	Approved
0.5632	Remote Similarity	NPD1831	Phase 3
0.5618	Remote Similarity	NPD337	Discontinued

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