NPASS Compound

Structure

CID169328 OpenBabel06191715542D 46 47 0 0 1 0 0 0 0 0999 V2000 1.7561 2.5718 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 0.9189 3.1187 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 4.9517 -2.2956 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 20 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 21 1 0 0 0 0 8 9 1 0 0 0 0 9 13 1 0 0 0 0 10 11 2 0 0 0 0 10 12 1 0 0 0 0 11 14 1 0 0 0 0 12 15 2 0 0 0 0 13 22 1 0 0 0 0 14 24 2 0 0 0 0 15 24 1 0 0 0 0 16 20 1 0 0 0 0 17 24 1 0 0 0 0 18 27 1 0 0 0 0 18 28 1 0 0 0 0 19 29 1 0 0 0 0 19 35 1 0 0 0 0 22 6 1 1 0 0 0 23 7 1 6 0 0 0 23 31 1 0 0 0 0 23 36 1 0 0 0 0 25 16 1 6 0 0 0 25 32 1 0 0 0 0 25 37 1 0 0 0 0 26 17 1 6 0 0 0 26 34 1 0 0 0 0 26 38 1 0 0 0 0 27 22 1 1 0 0 0 27 46 1 0 0 0 0 28 35 2 3 0 0 0 28 40 1 0 0 0 0 29 39 2 3 0 0 0 29 41 1 0 0 0 0 30 21 1 6 0 0 0 30 33 1 0 0 0 0 30 39 1 0 0 0 0 31 38 2 3 0 0 0 31 42 1 0 0 0 0 32 36 2 3 0 0 0 32 43 1 0 0 0 0 33 37 2 3 0 0 0 33 44 1 0 0 0 0 34 45 2 0 0 0 0 34 46 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	643.39
Volume:	672.294
LogP:	4.928
LogD:	4.282
LogS:	-4.215
# Rotatable Bonds:	9
TPSA:	171.8
# H-Bond Aceptor:	12
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.257
Synthetic Accessibility Score:	4.964
Fsp3:	0.647
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:	-5.467
MDCK Permeability:	8.816375338938087e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.854
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.912
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.041
Plasma Protein Binding (PPB):	79.10445404052734%
Volume Distribution (VD):	0.42
Pgp-substrate:	4.573761940002441%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.016
CYP2C19-inhibitor:	0.167
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.383
CYP2C9-substrate:	0.019
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.058
CYP3A4-inhibitor:	0.876
CYP3A4-substrate:	0.124

ADMET: Excretion

Clearance (CL):	6.532
Half-life (T1/2):	0.532

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.809
Drug-inuced Liver Injury (DILI):	0.607
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.121
Maximum Recommended Daily Dose:	0.789
Skin Sensitization:	0.21
Carcinogencity:	0.116
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.303

Download Data

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

Natural Product: NPC169328

Natural Product ID:	NPC169328
*Common Name:**	Arenamide B
IUPAC Name:	(3S,6S,9S,12S,19S)-3-benzyl-19-[(2S)-hexan-2-yl]-6-methyl-9-(2-methylpropyl)-12-propan-2-yl-1-oxa-4,7,10,13,16-pentazacyclononadecane-2,5,8,11,14,17-hexone
Synonyms:	Arenamide B
Standard InCHIKey:	HVPYLVISSBODEY-GAXORZTASA-N
Standard InCHI:	InChI=1S/C34H53N5O7/c1-8-9-13-22(6)27-18-28(40)35-19-29(41)39-30(21(4)5)33(44)37-25(16-20(2)3)32(43)36-23(7)31(42)38-26(34(45)46-27)17-24-14-11-10-12-15-24/h10-12,14-15,20-23,25-27,30H,8-9,13,16-19H2,1-7H3,(H,35,40)(H,36,43)(H,37,44)(H,38,42)(H,39,41)/t22-,23-,25-,26-,27-,30-/m0/s1
SMILES:	CCCC[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:	CHEMBL554587
PubChem CID:	42640845
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[549637]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	50.0	%	PMID[549637]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	19.2	ug.mL-1	PMID[549637]
NPT2	Others	Unspecified		IC50	=	1700.0	nM	PMID[549637]

☑ 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 NPC169328 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	91
0.1-0.2	463
0.2-0.3	2127
0.3-0.4	10374
0.4-0.5	23213
0.5-0.6	5170
0.6-0.7	904
0.7-0.8	278
0.8-0.85	48
0.85-0.9	18
0.9-0.95	4
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9909	High Similarity	NPC310467
0.9381	High Similarity	NPC237420
0.9052	High Similarity	NPC190663
0.9052	High Similarity	NPC478016
0.9052	High Similarity	NPC478015
0.9052	High Similarity	NPC477061
0.9052	High Similarity	NPC45777
0.9052	High Similarity	NPC478014
0.8898	High Similarity	NPC160493
0.8889	High Similarity	NPC80150
0.885	High Similarity	NPC474584
0.885	High Similarity	NPC273814
0.8833	High Similarity	NPC47667
0.8462	Intermediate Similarity	NPC197470
0.844	Intermediate Similarity	NPC12730
0.8403	Intermediate Similarity	NPC314992
0.8361	Intermediate Similarity	NPC35996
0.8321	Intermediate Similarity	NPC161069
0.8319	Intermediate Similarity	NPC327481
0.8304	Intermediate Similarity	NPC194390
0.8304	Intermediate Similarity	NPC224610
0.8304	Intermediate Similarity	NPC113326
0.8304	Intermediate Similarity	NPC88267
0.8258	Intermediate Similarity	NPC476978
0.8257	Intermediate Similarity	NPC473501
0.8257	Intermediate Similarity	NPC475439
0.8244	Intermediate Similarity	NPC263493
0.8244	Intermediate Similarity	NPC269398
0.8235	Intermediate Similarity	NPC2265
0.8226	Intermediate Similarity	NPC4974
0.8214	Intermediate Similarity	NPC164859
0.8195	Intermediate Similarity	NPC5620
0.819	Intermediate Similarity	NPC319579
0.8182	Intermediate Similarity	NPC139326
0.8168	Intermediate Similarity	NPC46098
0.8168	Intermediate Similarity	NPC307357
0.8168	Intermediate Similarity	NPC239762
0.8168	Intermediate Similarity	NPC268841
0.8168	Intermediate Similarity	NPC163392
0.8165	Intermediate Similarity	NPC25565
0.8154	Intermediate Similarity	NPC471264
0.8154	Intermediate Similarity	NPC68865
0.8154	Intermediate Similarity	NPC471265
0.8145	Intermediate Similarity	NPC476241
0.8145	Intermediate Similarity	NPC476260
0.812	Intermediate Similarity	NPC329011
0.8115	Intermediate Similarity	NPC476183
0.8092	Intermediate Similarity	NPC470884
0.8092	Intermediate Similarity	NPC98424
0.8092	Intermediate Similarity	NPC92784
0.8092	Intermediate Similarity	NPC178662
0.8092	Intermediate Similarity	NPC476133
0.808	Intermediate Similarity	NPC476179
0.808	Intermediate Similarity	NPC476125
0.8074	Intermediate Similarity	NPC138775
0.806	Intermediate Similarity	NPC209509
0.8049	Intermediate Similarity	NPC476281
0.8049	Intermediate Similarity	NPC476184
0.8045	Intermediate Similarity	NPC91953
0.8015	Intermediate Similarity	NPC127741
0.8015	Intermediate Similarity	NPC6570
0.7984	Intermediate Similarity	NPC246913
0.797	Intermediate Similarity	NPC197921
0.7956	Intermediate Similarity	NPC129666
0.7953	Intermediate Similarity	NPC210950
0.7953	Intermediate Similarity	NPC199738
0.7941	Intermediate Similarity	NPC135121
0.7941	Intermediate Similarity	NPC225648
0.7941	Intermediate Similarity	NPC329761
0.7926	Intermediate Similarity	NPC477217
0.7926	Intermediate Similarity	NPC201244
0.792	Intermediate Similarity	NPC476278
0.791	Intermediate Similarity	NPC197682
0.791	Intermediate Similarity	NPC469360
0.7909	Intermediate Similarity	NPC58674
0.7895	Intermediate Similarity	NPC471317
0.7891	Intermediate Similarity	NPC296712
0.7883	Intermediate Similarity	NPC105717
0.7874	Intermediate Similarity	NPC477937
0.7851	Intermediate Similarity	NPC188010
0.7846	Intermediate Similarity	NPC246079
0.7836	Intermediate Similarity	NPC469427
0.7836	Intermediate Similarity	NPC168113
0.7836	Intermediate Similarity	NPC469426
0.7826	Intermediate Similarity	NPC2501
0.7812	Intermediate Similarity	NPC319766
0.781	Intermediate Similarity	NPC145113
0.7805	Intermediate Similarity	NPC470546
0.7778	Intermediate Similarity	NPC46427
0.7778	Intermediate Similarity	NPC6975
0.7778	Intermediate Similarity	NPC176226
0.7737	Intermediate Similarity	NPC262077
0.7724	Intermediate Similarity	NPC470545
0.7721	Intermediate Similarity	NPC52748
0.7714	Intermediate Similarity	NPC162104
0.7698	Intermediate Similarity	NPC252878
0.7686	Intermediate Similarity	NPC276949
0.7686	Intermediate Similarity	NPC35850
0.768	Intermediate Similarity	NPC200964
0.7674	Intermediate Similarity	NPC152850
0.7674	Intermediate Similarity	NPC71933
0.7674	Intermediate Similarity	NPC89923
0.7674	Intermediate Similarity	NPC239990
0.7674	Intermediate Similarity	NPC105114
0.7669	Intermediate Similarity	NPC314835
0.766	Intermediate Similarity	NPC286551
0.766	Intermediate Similarity	NPC122590
0.7656	Intermediate Similarity	NPC101719
0.7642	Intermediate Similarity	NPC470544
0.763	Intermediate Similarity	NPC476259
0.7626	Intermediate Similarity	NPC471820
0.7626	Intermediate Similarity	NPC471821
0.7623	Intermediate Similarity	NPC33742
0.7619	Intermediate Similarity	NPC202521
0.7611	Intermediate Similarity	NPC122493
0.7611	Intermediate Similarity	NPC293628
0.7611	Intermediate Similarity	NPC10781
0.7597	Intermediate Similarity	NPC136453
0.7594	Intermediate Similarity	NPC248283
0.7589	Intermediate Similarity	NPC303045
0.7589	Intermediate Similarity	NPC161972
0.7581	Intermediate Similarity	NPC254088
0.7578	Intermediate Similarity	NPC222466
0.7569	Intermediate Similarity	NPC197743
0.7569	Intermediate Similarity	NPC297145
0.7544	Intermediate Similarity	NPC322598
0.754	Intermediate Similarity	NPC476990
0.7536	Intermediate Similarity	NPC316008
0.7536	Intermediate Similarity	NPC313867
0.7535	Intermediate Similarity	NPC473341
0.7523	Intermediate Similarity	NPC325441
0.7519	Intermediate Similarity	NPC470392
0.7519	Intermediate Similarity	NPC244866
0.7518	Intermediate Similarity	NPC7817
0.7518	Intermediate Similarity	NPC475168
0.75	Intermediate Similarity	NPC240848
0.75	Intermediate Similarity	NPC157311
0.75	Intermediate Similarity	NPC130309
0.7482	Intermediate Similarity	NPC314358
0.7481	Intermediate Similarity	NPC43755
0.7481	Intermediate Similarity	NPC473322
0.7465	Intermediate Similarity	NPC470274
0.7464	Intermediate Similarity	NPC314388
0.7464	Intermediate Similarity	NPC315283
0.746	Intermediate Similarity	NPC319950
0.7458	Intermediate Similarity	NPC67043
0.7456	Intermediate Similarity	NPC324569
0.7444	Intermediate Similarity	NPC326966
0.7444	Intermediate Similarity	NPC44805
0.7444	Intermediate Similarity	NPC8761
0.7436	Intermediate Similarity	NPC202613
0.7426	Intermediate Similarity	NPC132636
0.7424	Intermediate Similarity	NPC478147
0.7422	Intermediate Similarity	NPC291027
0.7422	Intermediate Similarity	NPC169485
0.7422	Intermediate Similarity	NPC213126
0.7422	Intermediate Similarity	NPC317474
0.7422	Intermediate Similarity	NPC84281
0.7422	Intermediate Similarity	NPC474862
0.7388	Intermediate Similarity	NPC287401
0.7387	Intermediate Similarity	NPC258627
0.7368	Intermediate Similarity	NPC255447
0.7365	Intermediate Similarity	NPC471053
0.7365	Intermediate Similarity	NPC471052
0.7365	Intermediate Similarity	NPC471051
0.7361	Intermediate Similarity	NPC470902
0.736	Intermediate Similarity	NPC239357
0.7357	Intermediate Similarity	NPC81026
0.7348	Intermediate Similarity	NPC472413
0.7348	Intermediate Similarity	NPC111428
0.7329	Intermediate Similarity	NPC56635
0.7324	Intermediate Similarity	NPC283783
0.7321	Intermediate Similarity	NPC226438
0.7321	Intermediate Similarity	NPC245259
0.7304	Intermediate Similarity	NPC311242
0.7293	Intermediate Similarity	NPC325651
0.7293	Intermediate Similarity	NPC69496
0.7287	Intermediate Similarity	NPC27581
0.7287	Intermediate Similarity	NPC142577
0.7286	Intermediate Similarity	NPC315266
0.7286	Intermediate Similarity	NPC266741
0.7279	Intermediate Similarity	NPC62104
0.7279	Intermediate Similarity	NPC1390
0.7273	Intermediate Similarity	NPC476353
0.7259	Intermediate Similarity	NPC233910
0.7259	Intermediate Similarity	NPC245836
0.7258	Intermediate Similarity	NPC1986
0.7258	Intermediate Similarity	NPC474544
0.7257	Intermediate Similarity	NPC323164
0.7252	Intermediate Similarity	NPC474847
0.725	Intermediate Similarity	NPC274089
0.725	Intermediate Similarity	NPC191215
0.7239	Intermediate Similarity	NPC183722
0.7234	Intermediate Similarity	NPC314114
0.7232	Intermediate Similarity	NPC159178
0.7232	Intermediate Similarity	NPC74936
0.7232	Intermediate Similarity	NPC209764
0.7232	Intermediate Similarity	NPC78041
0.7232	Intermediate Similarity	NPC141139
0.7232	Intermediate Similarity	NPC121872

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 NPC169328 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	83
0.1-0.2	305
0.2-0.3	738
0.3-0.4	2311
0.4-0.5	3430
0.5-0.6	1697
0.6-0.7	505
0.7-0.8	72
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.848	Intermediate Similarity	NPD4738	Phase 2
0.8462	Intermediate Similarity	NPD1348	Approved
0.8403	Intermediate Similarity	NPD2218	Phase 2
0.8403	Intermediate Similarity	NPD2217	Approved
0.8348	Intermediate Similarity	NPD3643	Approved
0.8348	Intermediate Similarity	NPD3642	Approved
0.8348	Intermediate Similarity	NPD3644	Approved
0.8182	Intermediate Similarity	NPD5981	Approved
0.8092	Intermediate Similarity	NPD6852	Discontinued
0.8065	Intermediate Similarity	NPD2584	Suspended
0.8015	Intermediate Similarity	NPD8173	Phase 2
0.8015	Intermediate Similarity	NPD8172	Phase 2
0.792	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD1040	Phase 2
0.7752	Intermediate Similarity	NPD7828	Discontinued
0.7742	Intermediate Similarity	NPD4209	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD8265	Approved
0.7681	Intermediate Similarity	NPD8323	Discontinued
0.7634	Intermediate Similarity	NPD3136	Phase 2
0.763	Intermediate Similarity	NPD6864	Phase 2
0.763	Intermediate Similarity	NPD6865	Phase 2
0.7611	Intermediate Similarity	NPD9566	Approved
0.7594	Intermediate Similarity	NPD8416	Discontinued
0.7565	Intermediate Similarity	NPD4760	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD2650	Approved
0.7541	Intermediate Similarity	NPD2652	Approved
0.7537	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1080	Approved
0.7462	Intermediate Similarity	NPD6302	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD7749	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD4125	Approved
0.7422	Intermediate Similarity	NPD4216	Approved
0.7422	Intermediate Similarity	NPD3132	Approved
0.7422	Intermediate Similarity	NPD2608	Approved
0.7422	Intermediate Similarity	NPD4217	Approved
0.7422	Intermediate Similarity	NPD2612	Approved
0.7422	Intermediate Similarity	NPD2609	Approved
0.7422	Intermediate Similarity	NPD4218	Approved
0.7422	Intermediate Similarity	NPD2611	Approved
0.7422	Intermediate Similarity	NPD3131	Approved
0.7422	Intermediate Similarity	NPD2610	Approved
0.7422	Intermediate Similarity	NPD4215	Approved
0.7411	Intermediate Similarity	NPD6690	Approved
0.7391	Intermediate Similarity	NPD7978	Discontinued
0.7385	Intermediate Similarity	NPD5367	Discontinued
0.7381	Intermediate Similarity	NPD4479	Discontinued
0.7345	Intermediate Similarity	NPD1066	Discontinued
0.7344	Intermediate Similarity	NPD2956	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD6390	Discontinued
0.7293	Intermediate Similarity	NPD2613	Approved
0.7287	Intermediate Similarity	NPD3603	Phase 3
0.7281	Intermediate Similarity	NPD4814	Discontinued
0.7279	Intermediate Similarity	NPD8643	Discontinued
0.7273	Intermediate Similarity	NPD3608	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD7342	Discontinued
0.7259	Intermediate Similarity	NPD2572	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD3089	Approved
0.7259	Intermediate Similarity	NPD2566	Approved
0.7259	Intermediate Similarity	NPD2570	Approved
0.7259	Intermediate Similarity	NPD4746	Phase 3
0.7259	Intermediate Similarity	NPD3090	Approved
0.7259	Intermediate Similarity	NPD2574	Discontinued
0.7259	Intermediate Similarity	NPD3616	Approved
0.7259	Intermediate Similarity	NPD3087	Approved
0.7259	Intermediate Similarity	NPD3614	Approved
0.7259	Intermediate Similarity	NPD2573	Approved
0.7259	Intermediate Similarity	NPD4745	Approved
0.7259	Intermediate Similarity	NPD3088	Approved
0.7259	Intermediate Similarity	NPD3615	Approved
0.7259	Intermediate Similarity	NPD2571	Approved
0.7257	Intermediate Similarity	NPD1814	Approved
0.7257	Intermediate Similarity	NPD1812	Approved
0.725	Intermediate Similarity	NPD467	Phase 1
0.7244	Intermediate Similarity	NPD2617	Discontinued
0.7244	Intermediate Similarity	NPD6093	Discontinued
0.7222	Intermediate Similarity	NPD4574	Approved
0.7222	Intermediate Similarity	NPD4576	Approved
0.7218	Intermediate Similarity	NPD3626	Phase 3
0.7218	Intermediate Similarity	NPD4177	Approved
0.7218	Intermediate Similarity	NPD4175	Approved
0.7214	Intermediate Similarity	NPD6119	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD2607	Approved
0.7167	Intermediate Similarity	NPD999	Phase 2
0.7165	Intermediate Similarity	NPD7522	Discontinued
0.7154	Intermediate Similarity	NPD5618	Discontinued
0.7153	Intermediate Similarity	NPD4686	Approved
0.7153	Intermediate Similarity	NPD4685	Phase 3
0.7153	Intermediate Similarity	NPD4684	Phase 3
0.7143	Intermediate Similarity	NPD7508	Discontinued
0.7121	Intermediate Similarity	NPD6325	Discontinued
0.7111	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5725	Approved
0.7101	Intermediate Similarity	NPD6073	Approved
0.7099	Intermediate Similarity	NPD6624	Discontinued
0.7094	Intermediate Similarity	NPD253	Approved
0.7092	Intermediate Similarity	NPD6681	Discovery
0.7083	Intermediate Similarity	NPD6088	Approved
0.708	Intermediate Similarity	NPD6623	Phase 3
0.708	Intermediate Similarity	NPD5323	Approved
0.7068	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD6901	Phase 3
0.7049	Intermediate Similarity	NPD6406	Approved
0.7037	Intermediate Similarity	NPD6359	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1067	Discontinued
0.7034	Intermediate Similarity	NPD7798	Approved
0.7031	Intermediate Similarity	NPD6065	Approved
0.7031	Intermediate Similarity	NPD1758	Phase 1
0.7027	Intermediate Similarity	NPD8417	Discontinued
0.7023	Intermediate Similarity	NPD4480	Approved
0.7023	Intermediate Similarity	NPD4806	Approved
0.7023	Intermediate Similarity	NPD4807	Approved
0.7021	Intermediate Similarity	NPD8076	Discontinued
0.7015	Intermediate Similarity	NPD3604	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD8118	Discontinued
0.7	Intermediate Similarity	NPD6647	Phase 2
0.7	Intermediate Similarity	NPD7972	Discontinued
0.6991	Remote Similarity	NPD5346	Phase 2
0.6991	Remote Similarity	NPD5347	Phase 2
0.6984	Remote Similarity	NPD1681	Approved
0.6984	Remote Similarity	NPD1682	Approved
0.6984	Remote Similarity	NPD1680	Approved
0.698	Remote Similarity	NPD6913	Approved
0.6977	Remote Similarity	NPD1759	Phase 1
0.6972	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD5705	Approved
0.6967	Remote Similarity	NPD5704	Approved
0.6967	Remote Similarity	NPD6685	Approved
0.6967	Remote Similarity	NPD5706	Approved
0.6957	Remote Similarity	NPD4153	Approved
0.6957	Remote Similarity	NPD5296	Approved
0.6953	Remote Similarity	NPD5291	Approved
0.6953	Remote Similarity	NPD3123	Discovery
0.6953	Remote Similarity	NPD5292	Approved
0.694	Remote Similarity	NPD2627	Approved
0.694	Remote Similarity	NPD2160	Approved
0.694	Remote Similarity	NPD2626	Approved
0.694	Remote Similarity	NPD2625	Approved
0.694	Remote Similarity	NPD2159	Approved
0.694	Remote Similarity	NPD2628	Approved
0.6935	Remote Similarity	NPD4233	Approved
0.6935	Remote Similarity	NPD4234	Approved
0.6934	Remote Similarity	NPD5299	Approved
0.6933	Remote Similarity	NPD8019	Approved
0.693	Remote Similarity	NPD3673	Approved
0.693	Remote Similarity	NPD3672	Approved
0.6929	Remote Similarity	NPD6295	Approved
0.6929	Remote Similarity	NPD6294	Approved
0.6923	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD4677	Discontinued
0.6912	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD8302	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD181	Approved
0.6901	Remote Similarity	NPD4152	Approved
0.6897	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD1018	Approved
0.6884	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD5747	Discontinued
0.6879	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7613	Discontinued
0.6867	Remote Similarity	NPD7105	Phase 1
0.685	Remote Similarity	NPD1373	Approved
0.685	Remote Similarity	NPD1371	Approved
0.685	Remote Similarity	NPD1374	Approved
0.685	Remote Similarity	NPD1370	Approved
0.6849	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3073	Approved
0.6842	Remote Similarity	NPD3071	Approved
0.6842	Remote Similarity	NPD3072	Approved
0.6838	Remote Similarity	NPD3664	Approved
0.6838	Remote Similarity	NPD3663	Approved
0.6838	Remote Similarity	NPD1081	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD3662	Phase 3
0.6838	Remote Similarity	NPD3661	Approved
0.6831	Remote Similarity	NPD7450	Phase 2
0.6824	Remote Similarity	NPD5982	Phase 2
0.6824	Remote Similarity	NPD7523	Phase 3
0.6821	Remote Similarity	NPD7495	Discontinued
0.6818	Remote Similarity	NPD4136	Approved
0.6818	Remote Similarity	NPD4106	Approved
0.6818	Remote Similarity	NPD4135	Approved
0.6814	Remote Similarity	NPD4793	Discontinued
0.6812	Remote Similarity	NPD4619	Approved
0.6812	Remote Similarity	NPD4621	Approved
0.6809	Remote Similarity	NPD4214	Discontinued
0.68	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1756	Approved
0.68	Remote Similarity	NPD1752	Approved
0.6797	Remote Similarity	NPD747	Discontinued
0.6788	Remote Similarity	NPD5201	Approved
0.6788	Remote Similarity	NPD4620	Approved
0.6788	Remote Similarity	NPD4617	Approved
0.6788	Remote Similarity	NPD5203	Approved
0.6774	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD6360	Discontinued
0.6767	Remote Similarity	NPD4762	Approved
0.6767	Remote Similarity	NPD4706	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