NPASS Compound

Structure

CID310467 OpenBabel06191716122D 48 49 0 0 1 0 0 0 0 0999 V2000 2.7034 4.0218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4205 -7.0183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3947 -8.4139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1965 -5.0307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0954 -6.3677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7579 1.7641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4596 -4.6377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8662 4.5687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9740 4.1172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9189 3.1187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9517 -2.2956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0266 2.6672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0857 -2.7956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9517 -1.2956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0285 1.6687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2197 -2.2956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0857 -0.7956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6990 -6.8277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3537 -0.7956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9697 0.1087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0424 -1.9077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5047 -7.4200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2600 -5.3814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9207 1.2172 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5673 -4.1861 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2197 -1.2956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -5.8338 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4876 -1.2956 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9758 0.2187 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8741 -0.3181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1798 -2.8982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4880 -4.7457 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8658 -3.2317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1533 -5.5617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7339 -5.4024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8519 -0.5237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5909 -1.0154 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9751 -4.9919 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.8074 -5.7787 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.8383 -2.2321 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.9880 -3.8796 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4439 0.5037 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1794 -2.9257 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8564 -3.3691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5801 -6.4661 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2576 -6.2543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5087 0.2304 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 8 1 0 0 0 0 2 22 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 23 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 12 1 0 0 0 0 11 13 2 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 13 16 1 0 0 0 0 14 17 2 0 0 0 0 15 24 1 0 0 0 0 16 26 2 0 0 0 0 17 26 1 0 0 0 0 18 22 1 0 0 0 0 19 26 1 0 0 0 0 20 29 1 0 0 0 0 20 30 1 0 0 0 0 21 31 1 0 0 0 0 21 37 1 0 0 0 0 24 6 1 1 0 0 0 25 7 1 6 0 0 0 25 33 1 0 0 0 0 25 38 1 0 0 0 0 27 18 1 6 0 0 0 27 34 1 0 0 0 0 27 39 1 0 0 0 0 28 19 1 6 0 0 0 28 36 1 0 0 0 0 28 40 1 0 0 0 0 29 24 1 1 0 0 0 29 48 1 0 0 0 0 30 37 2 3 0 0 0 30 42 1 0 0 0 0 31 41 2 3 0 0 0 31 43 1 0 0 0 0 32 23 1 6 0 0 0 32 35 1 0 0 0 0 32 41 1 0 0 0 0 33 40 2 3 0 0 0 33 44 1 0 0 0 0 34 38 2 3 0 0 0 34 45 1 0 0 0 0 35 39 2 3 0 0 0 35 46 1 0 0 0 0 36 47 2 0 0 0 0 36 48 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	671.43
Volume:	706.886
LogP:	5.763
LogD:	4.651
LogS:	-4.334
# Rotatable Bonds:	11
TPSA:	171.8
# H-Bond Aceptor:	12
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.178
Synthetic Accessibility Score:	4.99
Fsp3:	0.667
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:	-5.379
MDCK Permeability:	5.513500582310371e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.86
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.984
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031
Plasma Protein Binding (PPB):	87.81892395019531%
Volume Distribution (VD):	0.449
Pgp-substrate:	2.6806511878967285%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.018
CYP2C19-inhibitor:	0.254
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.483
CYP2C9-substrate:	0.022
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.056
CYP3A4-inhibitor:	0.915
CYP3A4-substrate:	0.136

ADMET: Excretion

Clearance (CL):	5.938
Half-life (T1/2):	0.399

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.841
Drug-inuced Liver Injury (DILI):	0.59
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.136
Maximum Recommended Daily Dose:	0.843
Skin Sensitization:	0.217
Carcinogencity:	0.12
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.326

Download Data

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

Natural Product: NPC310467

Natural Product ID:	NPC310467
*Common Name:**	Arenamide A
IUPAC Name:	(3S,6S,9S,12S,19S)-3-benzyl-6-methyl-9-(2-methylpropyl)-19-[(2S)-octan-2-yl]-12-propan-2-yl-1-oxa-4,7,10,13,16-pentazacyclononadecane-2,5,8,11,14,17-hexone
Synonyms:	Arenamide A
Standard InCHIKey:	HQEBGENSMXBRMP-GZMZQGJJSA-N
Standard InCHI:	InChI=1S/C36H57N5O7/c1-8-9-10-12-15-24(6)29-20-30(42)37-21-31(43)41-32(23(4)5)35(46)39-27(18-22(2)3)34(45)38-25(7)33(44)40-28(36(47)48-29)19-26-16-13-11-14-17-26/h11,13-14,16-17,22-25,27-29,32H,8-10,12,15,18-21H2,1-7H3,(H,37,42)(H,38,45)(H,39,46)(H,40,44)(H,41,43)/t24-,25-,27-,28-,29-,32-/m0/s1
SMILES:	CCCCCC[C@H](C)[C@@H]1CC(=NCC(=N[C@@H](C(C)C)C(=N[C@@H](CC(C)C)C(=N[C@@H](C)C(=N[C@@H](Cc2ccccc2)C(=O)O1)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL552496
PubChem CID:	42640846
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
NPO15076	Salinispora arenicola	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15916417]
NPO15076	Salinispora arenicola	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17253854]
NPO15076	Salinispora arenicola	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17323993]
NPO15076	Salinispora arenicola	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19117399]
NPO15076	Salinispora arenicola	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31313922]
NPO15076	Salinispora arenicola	Species	Micromonosporaceae	Bacteria	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
IC50	2
Others	2

Activity Type	# Activity
Cell Line	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	35.0	%	PMID[558905]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	50.0	%	PMID[558905]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	13.2	ug.mL-1	PMID[558905]
NPT2	Others	Unspecified		IC50	=	3700.0	nM	PMID[558905]

☑ 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 NPC310467 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	93
0.1-0.2	469
0.2-0.3	1982
0.3-0.4	9483
0.4-0.5	23727
0.5-0.6	5670
0.6-0.7	913
0.7-0.8	281
0.8-0.85	51
0.85-0.9	14
0.9-0.95	9
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9909	High Similarity	NPC169328
0.9298	High Similarity	NPC237420
0.9138	High Similarity	NPC478016
0.9138	High Similarity	NPC190663
0.9138	High Similarity	NPC478015
0.9138	High Similarity	NPC478014
0.8983	High Similarity	NPC160493
0.8974	High Similarity	NPC477061
0.8974	High Similarity	NPC80150
0.8974	High Similarity	NPC45777
0.8772	High Similarity	NPC273814
0.8772	High Similarity	NPC474584
0.876	High Similarity	NPC47667
0.8397	Intermediate Similarity	NPC161069
0.839	Intermediate Similarity	NPC197470
0.8364	Intermediate Similarity	NPC12730
0.8333	Intermediate Similarity	NPC314992
0.8333	Intermediate Similarity	NPC476978
0.8321	Intermediate Similarity	NPC263493
0.8321	Intermediate Similarity	NPC269398
0.8293	Intermediate Similarity	NPC35996
0.8271	Intermediate Similarity	NPC5620
0.8258	Intermediate Similarity	NPC139326
0.8246	Intermediate Similarity	NPC327481
0.823	Intermediate Similarity	NPC224610
0.823	Intermediate Similarity	NPC194390
0.823	Intermediate Similarity	NPC113326
0.823	Intermediate Similarity	NPC88267
0.8182	Intermediate Similarity	NPC475439
0.8182	Intermediate Similarity	NPC473501
0.8167	Intermediate Similarity	NPC2265
0.816	Intermediate Similarity	NPC4974
0.8148	Intermediate Similarity	NPC138775
0.8142	Intermediate Similarity	NPC164859
0.812	Intermediate Similarity	NPC319579
0.812	Intermediate Similarity	NPC91953
0.8106	Intermediate Similarity	NPC268841
0.8106	Intermediate Similarity	NPC239762
0.8106	Intermediate Similarity	NPC163392
0.8106	Intermediate Similarity	NPC46098
0.8106	Intermediate Similarity	NPC307357
0.8092	Intermediate Similarity	NPC471265
0.8092	Intermediate Similarity	NPC471264
0.8092	Intermediate Similarity	NPC68865
0.8091	Intermediate Similarity	NPC25565
0.808	Intermediate Similarity	NPC476241
0.808	Intermediate Similarity	NPC476260
0.8062	Intermediate Similarity	NPC246913
0.8051	Intermediate Similarity	NPC329011
0.8049	Intermediate Similarity	NPC476183
0.8045	Intermediate Similarity	NPC197921
0.803	Intermediate Similarity	NPC92784
0.803	Intermediate Similarity	NPC178662
0.803	Intermediate Similarity	NPC470884
0.803	Intermediate Similarity	NPC98424
0.803	Intermediate Similarity	NPC476133
0.8029	Intermediate Similarity	NPC129666
0.8016	Intermediate Similarity	NPC476179
0.8016	Intermediate Similarity	NPC476125
0.8015	Intermediate Similarity	NPC225648
0.8015	Intermediate Similarity	NPC329761
0.8015	Intermediate Similarity	NPC135121
0.8	Intermediate Similarity	NPC209509
0.7984	Intermediate Similarity	NPC476184
0.7984	Intermediate Similarity	NPC476281
0.7969	Intermediate Similarity	NPC296712
0.7955	Intermediate Similarity	NPC127741
0.7955	Intermediate Similarity	NPC6570
0.7934	Intermediate Similarity	NPC188010
0.7899	Intermediate Similarity	NPC2501
0.7891	Intermediate Similarity	NPC210950
0.7891	Intermediate Similarity	NPC199738
0.7868	Intermediate Similarity	NPC477217
0.7868	Intermediate Similarity	NPC201244
0.7857	Intermediate Similarity	NPC476278
0.7852	Intermediate Similarity	NPC469360
0.7852	Intermediate Similarity	NPC197682
0.7838	Intermediate Similarity	NPC58674
0.7826	Intermediate Similarity	NPC471317
0.7826	Intermediate Similarity	NPC105717
0.7812	Intermediate Similarity	NPC477937
0.7786	Intermediate Similarity	NPC246079
0.7786	Intermediate Similarity	NPC162104
0.7778	Intermediate Similarity	NPC469427
0.7778	Intermediate Similarity	NPC168113
0.7778	Intermediate Similarity	NPC469426
0.7754	Intermediate Similarity	NPC145113
0.7752	Intermediate Similarity	NPC319766
0.7742	Intermediate Similarity	NPC470546
0.7734	Intermediate Similarity	NPC101719
0.773	Intermediate Similarity	NPC122590
0.7721	Intermediate Similarity	NPC176226
0.7717	Intermediate Similarity	NPC6975
0.7717	Intermediate Similarity	NPC46427
0.7681	Intermediate Similarity	NPC262077
0.7664	Intermediate Similarity	NPC52748
0.7661	Intermediate Similarity	NPC470545
0.7656	Intermediate Similarity	NPC222466
0.7639	Intermediate Similarity	NPC297145
0.7639	Intermediate Similarity	NPC197743
0.7638	Intermediate Similarity	NPC252878
0.7623	Intermediate Similarity	NPC276949
0.7623	Intermediate Similarity	NPC35850
0.7619	Intermediate Similarity	NPC200964
0.7615	Intermediate Similarity	NPC239990
0.7615	Intermediate Similarity	NPC152850
0.7615	Intermediate Similarity	NPC71933
0.7615	Intermediate Similarity	NPC89923
0.7615	Intermediate Similarity	NPC105114
0.7612	Intermediate Similarity	NPC314835
0.7606	Intermediate Similarity	NPC286551
0.7581	Intermediate Similarity	NPC470544
0.7574	Intermediate Similarity	NPC476259
0.7571	Intermediate Similarity	NPC471821
0.7571	Intermediate Similarity	NPC240848
0.7571	Intermediate Similarity	NPC471820
0.7561	Intermediate Similarity	NPC33742
0.7559	Intermediate Similarity	NPC202521
0.7544	Intermediate Similarity	NPC293628
0.7544	Intermediate Similarity	NPC10781
0.7544	Intermediate Similarity	NPC122493
0.7538	Intermediate Similarity	NPC136453
0.7537	Intermediate Similarity	NPC248283
0.7535	Intermediate Similarity	NPC470274
0.7522	Intermediate Similarity	NPC303045
0.7522	Intermediate Similarity	NPC161972
0.752	Intermediate Similarity	NPC254088
0.75	Intermediate Similarity	NPC84281
0.75	Intermediate Similarity	NPC169485
0.75	Intermediate Similarity	NPC291027
0.75	Intermediate Similarity	NPC213126
0.75	Intermediate Similarity	NPC317474
0.7483	Intermediate Similarity	NPC473341
0.7482	Intermediate Similarity	NPC316008
0.7482	Intermediate Similarity	NPC313867
0.748	Intermediate Similarity	NPC476990
0.7478	Intermediate Similarity	NPC322598
0.7465	Intermediate Similarity	NPC7817
0.7465	Intermediate Similarity	NPC475168
0.7463	Intermediate Similarity	NPC470392
0.7463	Intermediate Similarity	NPC244866
0.7455	Intermediate Similarity	NPC325441
0.7444	Intermediate Similarity	NPC130309
0.7444	Intermediate Similarity	NPC157311
0.7429	Intermediate Similarity	NPC314358
0.7426	Intermediate Similarity	NPC43755
0.7424	Intermediate Similarity	NPC473322
0.7424	Intermediate Similarity	NPC472413
0.741	Intermediate Similarity	NPC315283
0.741	Intermediate Similarity	NPC314388
0.7402	Intermediate Similarity	NPC319950
0.7395	Intermediate Similarity	NPC67043
0.7391	Intermediate Similarity	NPC324569
0.7388	Intermediate Similarity	NPC44805
0.7388	Intermediate Similarity	NPC326966
0.7388	Intermediate Similarity	NPC8761
0.7373	Intermediate Similarity	NPC202613
0.7372	Intermediate Similarity	NPC132636
0.7368	Intermediate Similarity	NPC478147
0.7368	Intermediate Similarity	NPC69496
0.7364	Intermediate Similarity	NPC474862
0.7348	Intermediate Similarity	NPC476353
0.7333	Intermediate Similarity	NPC245836
0.7333	Intermediate Similarity	NPC287401
0.7333	Intermediate Similarity	NPC191215
0.7333	Intermediate Similarity	NPC233910
0.7333	Intermediate Similarity	NPC274089
0.7321	Intermediate Similarity	NPC258627
0.7315	Intermediate Similarity	NPC471053
0.7315	Intermediate Similarity	NPC471051
0.7315	Intermediate Similarity	NPC471052
0.7313	Intermediate Similarity	NPC183722
0.7313	Intermediate Similarity	NPC255447
0.7311	Intermediate Similarity	NPC19136
0.731	Intermediate Similarity	NPC470902
0.7308	Intermediate Similarity	NPC472415
0.7305	Intermediate Similarity	NPC81026
0.7302	Intermediate Similarity	NPC239357
0.7293	Intermediate Similarity	NPC111428
0.7279	Intermediate Similarity	NPC56635
0.7273	Intermediate Similarity	NPC283783
0.7257	Intermediate Similarity	NPC226438
0.7257	Intermediate Similarity	NPC245259
0.7241	Intermediate Similarity	NPC311242
0.7239	Intermediate Similarity	NPC325651
0.7236	Intermediate Similarity	NPC323007
0.7234	Intermediate Similarity	NPC315266
0.7234	Intermediate Similarity	NPC266741
0.7231	Intermediate Similarity	NPC142577
0.7231	Intermediate Similarity	NPC27581
0.723	Intermediate Similarity	NPC1390
0.723	Intermediate Similarity	NPC62104
0.72	Intermediate Similarity	NPC474544
0.72	Intermediate Similarity	NPC1986
0.7197	Intermediate Similarity	NPC474847
0.7197	Intermediate Similarity	NPC472414
0.7193	Intermediate Similarity	NPC323164
0.7192	Intermediate Similarity	NPC39431
0.7183	Intermediate Similarity	NPC314114
0.7181	Intermediate Similarity	NPC471527

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 NPC310467 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	84
0.1-0.2	310
0.2-0.3	746
0.3-0.4	2233
0.4-0.5	3410
0.5-0.6	1760
0.6-0.7	516
0.7-0.8	83
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8435	Intermediate Similarity	NPD3644	Approved
0.8435	Intermediate Similarity	NPD3642	Approved
0.8435	Intermediate Similarity	NPD3643	Approved
0.8413	Intermediate Similarity	NPD4738	Phase 2
0.839	Intermediate Similarity	NPD1348	Approved
0.8333	Intermediate Similarity	NPD2217	Approved
0.8333	Intermediate Similarity	NPD2218	Phase 2
0.8264	Intermediate Similarity	NPD5981	Approved
0.8092	Intermediate Similarity	NPD8173	Phase 2
0.8092	Intermediate Similarity	NPD8172	Phase 2
0.803	Intermediate Similarity	NPD6852	Discontinued
0.8	Intermediate Similarity	NPD2584	Suspended
0.7857	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD4209	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD8265	Approved
0.7754	Intermediate Similarity	NPD8323	Discontinued
0.7692	Intermediate Similarity	NPD7828	Discontinued
0.7692	Intermediate Similarity	NPD1040	Phase 2
0.768	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD4760	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD2652	Approved
0.7623	Intermediate Similarity	NPD2650	Approved
0.7576	Intermediate Similarity	NPD3136	Phase 2
0.7574	Intermediate Similarity	NPD6865	Phase 2
0.7574	Intermediate Similarity	NPD6864	Phase 2
0.7544	Intermediate Similarity	NPD9566	Approved
0.7538	Intermediate Similarity	NPD6302	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD8416	Discontinued
0.7517	Intermediate Similarity	NPD7749	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3131	Approved
0.75	Intermediate Similarity	NPD2612	Approved
0.75	Intermediate Similarity	NPD2611	Approved
0.75	Intermediate Similarity	NPD4218	Approved
0.75	Intermediate Similarity	NPD4215	Approved
0.75	Intermediate Similarity	NPD2608	Approved
0.75	Intermediate Similarity	NPD2609	Approved
0.75	Intermediate Similarity	NPD2610	Approved
0.75	Intermediate Similarity	NPD3132	Approved
0.75	Intermediate Similarity	NPD4217	Approved
0.75	Intermediate Similarity	NPD4216	Approved
0.7481	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD4479	Discontinued
0.7434	Intermediate Similarity	NPD1080	Approved
0.7422	Intermediate Similarity	NPD2956	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4125	Approved
0.7368	Intermediate Similarity	NPD2613	Approved
0.7368	Intermediate Similarity	NPD4814	Discontinued
0.7364	Intermediate Similarity	NPD3603	Phase 3
0.7353	Intermediate Similarity	NPD8643	Discontinued
0.7348	Intermediate Similarity	NPD3608	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD6690	Approved
0.7338	Intermediate Similarity	NPD7978	Discontinued
0.7333	Intermediate Similarity	NPD2574	Discontinued
0.7333	Intermediate Similarity	NPD2573	Approved
0.7333	Intermediate Similarity	NPD3615	Approved
0.7333	Intermediate Similarity	NPD2570	Approved
0.7333	Intermediate Similarity	NPD2571	Approved
0.7333	Intermediate Similarity	NPD3614	Approved
0.7333	Intermediate Similarity	NPD3616	Approved
0.7333	Intermediate Similarity	NPD3087	Approved
0.7333	Intermediate Similarity	NPD4745	Approved
0.7333	Intermediate Similarity	NPD4746	Phase 3
0.7333	Intermediate Similarity	NPD2572	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3089	Approved
0.7333	Intermediate Similarity	NPD467	Phase 1
0.7333	Intermediate Similarity	NPD3090	Approved
0.7333	Intermediate Similarity	NPD2566	Approved
0.7333	Intermediate Similarity	NPD3088	Approved
0.7328	Intermediate Similarity	NPD5367	Discontinued
0.7323	Intermediate Similarity	NPD2617	Discontinued
0.7323	Intermediate Similarity	NPD6093	Discontinued
0.7302	Intermediate Similarity	NPD4576	Approved
0.7302	Intermediate Similarity	NPD4574	Approved
0.7292	Intermediate Similarity	NPD6390	Discontinued
0.7281	Intermediate Similarity	NPD1066	Discontinued
0.7258	Intermediate Similarity	NPD2607	Approved
0.7244	Intermediate Similarity	NPD7522	Discontinued
0.7231	Intermediate Similarity	NPD5618	Discontinued
0.7226	Intermediate Similarity	NPD4685	Phase 3
0.7226	Intermediate Similarity	NPD4684	Phase 3
0.7226	Intermediate Similarity	NPD4686	Approved
0.7209	Intermediate Similarity	NPD7342	Discontinued
0.7197	Intermediate Similarity	NPD6325	Discontinued
0.7193	Intermediate Similarity	NPD1814	Approved
0.7193	Intermediate Similarity	NPD1812	Approved
0.7185	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD253	Approved
0.7164	Intermediate Similarity	NPD4175	Approved
0.7164	Intermediate Similarity	NPD4177	Approved
0.7164	Intermediate Similarity	NPD3626	Phase 3
0.7163	Intermediate Similarity	NPD6119	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD1067	Discontinued
0.7109	Intermediate Similarity	NPD6065	Approved
0.7107	Intermediate Similarity	NPD999	Phase 2
0.7099	Intermediate Similarity	NPD4806	Approved
0.7099	Intermediate Similarity	NPD4480	Approved
0.7099	Intermediate Similarity	NPD4807	Approved
0.7095	Intermediate Similarity	NPD8417	Discontinued
0.7087	Intermediate Similarity	NPD7508	Discontinued
0.708	Intermediate Similarity	NPD8118	Discontinued
0.708	Intermediate Similarity	NPD5346	Phase 2
0.708	Intermediate Similarity	NPD5347	Phase 2
0.7063	Intermediate Similarity	NPD1681	Approved
0.7063	Intermediate Similarity	NPD1680	Approved
0.7063	Intermediate Similarity	NPD1682	Approved
0.705	Intermediate Similarity	NPD5725	Approved
0.705	Intermediate Similarity	NPD6073	Approved
0.7049	Intermediate Similarity	NPD5705	Approved
0.7049	Intermediate Similarity	NPD5704	Approved
0.7049	Intermediate Similarity	NPD6685	Approved
0.7049	Intermediate Similarity	NPD5706	Approved
0.7045	Intermediate Similarity	NPD6624	Discontinued
0.7042	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD6681	Discovery
0.7034	Intermediate Similarity	NPD6088	Approved
0.7031	Intermediate Similarity	NPD3123	Discovery
0.7029	Intermediate Similarity	NPD6623	Phase 3
0.7029	Intermediate Similarity	NPD5323	Approved
0.7018	Intermediate Similarity	NPD3673	Approved
0.7018	Intermediate Similarity	NPD3672	Approved
0.7016	Intermediate Similarity	NPD4234	Approved
0.7016	Intermediate Similarity	NPD4233	Approved
0.7015	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6901	Phase 3
0.6992	Remote Similarity	NPD6406	Approved
0.6985	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD8302	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD1758	Phase 1
0.6975	Remote Similarity	NPD7798	Approved
0.6972	Remote Similarity	NPD8076	Discontinued
0.6972	Remote Similarity	NPD4152	Approved
0.6967	Remote Similarity	NPD1018	Approved
0.6963	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD3604	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7972	Discontinued
0.6942	Remote Similarity	NPD6647	Phase 2
0.6933	Remote Similarity	NPD6913	Approved
0.6929	Remote Similarity	NPD1373	Approved
0.6929	Remote Similarity	NPD1371	Approved
0.6929	Remote Similarity	NPD1370	Approved
0.6929	Remote Similarity	NPD1374	Approved
0.6923	Remote Similarity	NPD1759	Phase 1
0.6912	Remote Similarity	NPD3662	Phase 3
0.6912	Remote Similarity	NPD3661	Approved
0.6912	Remote Similarity	NPD3664	Approved
0.6912	Remote Similarity	NPD3663	Approved
0.6906	Remote Similarity	NPD5296	Approved
0.6906	Remote Similarity	NPD4153	Approved
0.6903	Remote Similarity	NPD4793	Discontinued
0.6899	Remote Similarity	NPD5292	Approved
0.6899	Remote Similarity	NPD5291	Approved
0.6894	Remote Similarity	NPD4135	Approved
0.6894	Remote Similarity	NPD4136	Approved
0.6894	Remote Similarity	NPD4106	Approved
0.6889	Remote Similarity	NPD2625	Approved
0.6889	Remote Similarity	NPD2627	Approved
0.6889	Remote Similarity	NPD2628	Approved
0.6889	Remote Similarity	NPD2160	Approved
0.6889	Remote Similarity	NPD2159	Approved
0.6889	Remote Similarity	NPD2626	Approved
0.6887	Remote Similarity	NPD8019	Approved
0.6884	Remote Similarity	NPD4619	Approved
0.6884	Remote Similarity	NPD4621	Approved
0.6884	Remote Similarity	NPD5299	Approved
0.688	Remote Similarity	NPD1756	Approved
0.688	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.688	Remote Similarity	NPD1752	Approved
0.6879	Remote Similarity	NPD6295	Approved
0.6879	Remote Similarity	NPD6294	Approved
0.6875	Remote Similarity	NPD747	Discontinued
0.6875	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD4677	Discontinued
0.6861	Remote Similarity	NPD4620	Approved
0.6861	Remote Similarity	NPD5201	Approved
0.6861	Remote Similarity	NPD5203	Approved
0.6861	Remote Similarity	NPD4617	Approved
0.6855	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.685	Remote Similarity	NPD181	Approved
0.6835	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD5747	Discontinued
0.6831	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD3648	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD3400	Discontinued
0.6824	Remote Similarity	NPD7613	Discontinued
0.6821	Remote Similarity	NPD7105	Phase 1
0.6818	Remote Similarity	NPD5306	Approved
0.6818	Remote Similarity	NPD5305	Approved
0.6803	Remote Similarity	NPD5765	Approved
0.6803	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD3072	Approved
0.6791	Remote Similarity	NPD3073	Approved
0.6791	Remote Similarity	NPD3071	Approved
0.6788	Remote Similarity	NPD5204	Approved
0.6786	Remote Similarity	NPD5120	Approved
0.6786	Remote Similarity	NPD5121	Approved
0.6786	Remote Similarity	NPD5119	Approved

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