NPASS Compound

Structure

NPC47667 OpenBabel07101718312D 59 60 0 0 1 0 0 0 0 0999 V2000 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9904 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9904 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -5.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.2583 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.3923 -6.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.6603 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -5.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -4.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -6.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 -7.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 22 1 0 0 0 0 7 9 2 0 0 0 0 7 10 1 0 0 0 0 8 11 2 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 10 14 2 0 0 0 0 11 15 1 0 0 0 0 12 16 2 0 0 0 0 13 25 2 0 0 0 0 14 25 1 0 0 0 0 15 26 2 0 0 0 0 16 26 1 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 18 29 1 0 0 0 0 19 31 1 0 0 0 0 20 30 1 0 0 0 0 20 41 1 0 0 0 0 22 34 1 0 0 0 0 23 5 1 6 0 0 0 23 35 1 0 0 0 0 23 42 1 0 0 0 0 24 6 1 1 0 0 0 24 36 1 0 0 0 0 24 43 1 0 0 0 0 27 19 1 1 0 0 0 27 37 1 0 0 0 0 27 44 1 0 0 0 0 28 17 1 1 0 0 0 28 40 1 0 0 0 0 28 45 1 0 0 0 0 29 46 2 3 0 0 0 29 48 1 0 0 0 0 30 42 2 3 0 0 0 30 49 1 0 0 0 0 31 50 2 0 0 0 0 31 51 1 0 0 0 0 32 21 1 6 0 0 0 32 39 1 0 0 0 0 32 46 1 0 0 0 0 33 34 1 0 0 0 0 33 38 1 6 0 0 0 33 47 1 0 0 0 0 34 52 1 6 0 0 0 35 45 2 3 0 0 0 35 53 1 0 0 0 0 36 47 2 3 0 0 0 36 54 1 0 0 0 0 37 43 2 3 0 0 0 37 55 1 0 0 0 0 38 41 2 3 0 0 0 38 56 1 0 0 0 0 39 44 2 3 0 0 0 39 57 1 0 0 0 0 40 58 2 0 0 0 0 40 59 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	825.39
Volume:	826.196
LogP:	0.859
LogD:	1.812
LogS:	-1.405
# Rotatable Bonds:	27
TPSA:	309.0
# H-Bond Aceptor:	19
# H-Bond Donor:	10
# Rings:	2
# Heavy Atoms:	19

MedChem Properties

QED Drug-Likeness Score:	0.056
Synthetic Accessibility Score:	5.146
Fsp3:	0.475
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:	-6.068
MDCK Permeability:	1.2041943591611926e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.797
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.025

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.106
Plasma Protein Binding (PPB):	42.79633331298828%
Volume Distribution (VD):	0.361
Pgp-substrate:	55.646217346191406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.028
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.335
CYP2D6-inhibitor:	0.058
CYP2D6-substrate:	0.036
CYP3A4-inhibitor:	0.053
CYP3A4-substrate:	0.008

ADMET: Excretion

Clearance (CL):	1.329
Half-life (T1/2):	0.925

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.949
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.02
Skin Sensitization:	0.53
Carcinogencity:	0.001
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC47667

Natural Product ID:	NPC47667
*Common Name:**	(2S,5R,11R,14S,17R)-2-Benzyl-11-((S)-1-Hydroxy-2-Methylpropyl)-5,14-Dimethyl-17-((S)-3-Methyl-2-(2-Phenylacetamido)Butanamido)-4,7,10,13,16-Pentaoxo-3,6,9,12,15-Pentaazanonadecane-1,19-Dioic Acid
IUPAC Name:	(3R)-4-[[(2S)-1-[[(2R,3S)-1-[[2-[[(2R)-1-[[(1S)-1-carboxy-2-phenylethyl]amino]-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-hydroxy-4-methyl-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-[[(2S)-3-methyl-2-[(2-phenylacetyl)amino]butanoyl]amino]-4-oxobutanoic acid
Synonyms:
Standard InCHIKey:	AYHQEXAHORNEMG-CGBMOQSMSA-N
Standard InCHI:	InChI=1S/C40H55N7O12/c1-21(2)32(46-29(48)18-26-15-11-8-12-16-26)39(57)44-27(19-31(50)51)37(55)43-24(6)36(54)47-33(34(52)22(3)4)38(56)41-20-30(49)42-23(5)35(53)45-28(40(58)59)17-25-13-9-7-10-14-25/h7-16,21-24,27-28,32-34,52H,17-20H2,1-6H3,(H,41,56)(H,42,49)(H,43,55)(H,44,57)(H,45,53)(H,46,48)(H,47,54)(H,50,51)(H,58,59)/t23-,24+,27-,28+,32+,33-,34+/m1/s1
SMILES:	OC(=O)C[C@H](C(=N[C@H](C(=N[C@H]([C@H](C(C)C)O)C(=NCC(=N[C@@H](C(=N[C@H](C(=O)O)Cc1ccccc1)O)C)O)O)O)C)O)N=C([C@H](C(C)C)N=C(Cc1ccccc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2010812
PubChem CID:	57331968
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32824	kibdelosporangium sp. ak-aa56	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22264203]

☑ 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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	IZ	=	7.1	mm	PMID[541956]

☑ 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 NPC47667 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	99
0.1-0.2	532
0.2-0.3	2098
0.3-0.4	9629
0.4-0.5	22346
0.5-0.6	6668
0.6-0.7	1024
0.7-0.8	256
0.8-0.85	30
0.85-0.9	14
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8833	High Similarity	NPC169328
0.877	High Similarity	NPC477061
0.877	High Similarity	NPC45777
0.877	High Similarity	NPC478014
0.877	High Similarity	NPC478015
0.877	High Similarity	NPC478016
0.876	High Similarity	NPC310467
0.856	High Similarity	NPC35996
0.832	Intermediate Similarity	NPC190663
0.8306	Intermediate Similarity	NPC237420
0.8264	Intermediate Similarity	NPC474584
0.8211	Intermediate Similarity	NPC197470
0.8205	Intermediate Similarity	NPC224610
0.8205	Intermediate Similarity	NPC194390
0.8205	Intermediate Similarity	NPC88267
0.8205	Intermediate Similarity	NPC113326
0.8189	Intermediate Similarity	NPC160493
0.8182	Intermediate Similarity	NPC329011
0.816	Intermediate Similarity	NPC314992
0.8099	Intermediate Similarity	NPC319579
0.8	Intermediate Similarity	NPC2265
0.8	Intermediate Similarity	NPC4974
0.7941	Intermediate Similarity	NPC127741
0.791	Intermediate Similarity	NPC246913
0.7891	Intermediate Similarity	NPC80150
0.7863	Intermediate Similarity	NPC12730
0.7857	Intermediate Similarity	NPC209509
0.7842	Intermediate Similarity	NPC161069
0.7823	Intermediate Similarity	NPC273814
0.7817	Intermediate Similarity	NPC105717
0.7803	Intermediate Similarity	NPC477937
0.7769	Intermediate Similarity	NPC327481
0.7744	Intermediate Similarity	NPC210950
0.7744	Intermediate Similarity	NPC199738
0.7744	Intermediate Similarity	NPC319766
0.7734	Intermediate Similarity	NPC470546
0.7721	Intermediate Similarity	NPC244866
0.7714	Intermediate Similarity	NPC91953
0.7714	Intermediate Similarity	NPC139326
0.7698	Intermediate Similarity	NPC239762
0.7698	Intermediate Similarity	NPC163392
0.7698	Intermediate Similarity	NPC476259
0.7692	Intermediate Similarity	NPC475439
0.7692	Intermediate Similarity	NPC473501
0.7667	Intermediate Similarity	NPC164859
0.766	Intermediate Similarity	NPC476978
0.7656	Intermediate Similarity	NPC470545
0.7652	Intermediate Similarity	NPC476241
0.7652	Intermediate Similarity	NPC476260
0.7647	Intermediate Similarity	NPC326966
0.7643	Intermediate Similarity	NPC263493
0.7643	Intermediate Similarity	NPC197921
0.7643	Intermediate Similarity	NPC269398
0.7622	Intermediate Similarity	NPC138775
0.7607	Intermediate Similarity	NPC25565
0.7603	Intermediate Similarity	NPC122590
0.7603	Intermediate Similarity	NPC286551
0.7594	Intermediate Similarity	NPC476179
0.7594	Intermediate Similarity	NPC476125
0.7589	Intermediate Similarity	NPC469360
0.7589	Intermediate Similarity	NPC197682
0.7578	Intermediate Similarity	NPC470544
0.7571	Intermediate Similarity	NPC268841
0.7571	Intermediate Similarity	NPC307357
0.7571	Intermediate Similarity	NPC46098
0.7554	Intermediate Similarity	NPC43755
0.7554	Intermediate Similarity	NPC471265
0.7554	Intermediate Similarity	NPC471264
0.7554	Intermediate Similarity	NPC6570
0.7519	Intermediate Similarity	NPC254088
0.7518	Intermediate Similarity	NPC168113
0.75	Intermediate Similarity	NPC188010
0.75	Intermediate Similarity	NPC135121
0.75	Intermediate Similarity	NPC225648
0.75	Intermediate Similarity	NPC329761
0.75	Intermediate Similarity	NPC92784
0.75	Intermediate Similarity	NPC476133
0.75	Intermediate Similarity	NPC178662
0.75	Intermediate Similarity	NPC98424
0.75	Intermediate Similarity	NPC470884
0.75	Intermediate Similarity	NPC132636
0.75	Intermediate Similarity	NPC325651
0.7483	Intermediate Similarity	NPC201244
0.7483	Intermediate Similarity	NPC477217
0.7483	Intermediate Similarity	NPC5620
0.7481	Intermediate Similarity	NPC476183
0.7465	Intermediate Similarity	NPC176226
0.7445	Intermediate Similarity	NPC255447
0.7444	Intermediate Similarity	NPC46427
0.7444	Intermediate Similarity	NPC6975
0.7429	Intermediate Similarity	NPC68865
0.7426	Intermediate Similarity	NPC473322
0.7426	Intermediate Similarity	NPC296712
0.7424	Intermediate Similarity	NPC476184
0.7424	Intermediate Similarity	NPC476281
0.7419	Intermediate Similarity	NPC40234
0.7415	Intermediate Similarity	NPC162104
0.74	Intermediate Similarity	NPC207675
0.74	Intermediate Similarity	NPC212699
0.7397	Intermediate Similarity	NPC132771
0.7397	Intermediate Similarity	NPC2501
0.7379	Intermediate Similarity	NPC145113
0.7377	Intermediate Similarity	NPC471317
0.7373	Intermediate Similarity	NPC58674
0.7372	Intermediate Similarity	NPC69496
0.7368	Intermediate Similarity	NPC84281
0.7368	Intermediate Similarity	NPC169485
0.7368	Intermediate Similarity	NPC213126
0.7368	Intermediate Similarity	NPC252878
0.7368	Intermediate Similarity	NPC317474
0.7368	Intermediate Similarity	NPC291027
0.7368	Intermediate Similarity	NPC474862
0.7364	Intermediate Similarity	NPC235421
0.7353	Intermediate Similarity	NPC239990
0.7353	Intermediate Similarity	NPC71933
0.7353	Intermediate Similarity	NPC89923
0.7353	Intermediate Similarity	NPC105114
0.7353	Intermediate Similarity	NPC152850
0.7338	Intermediate Similarity	NPC287401
0.7333	Intermediate Similarity	NPC474847
0.7319	Intermediate Similarity	NPC130309
0.7319	Intermediate Similarity	NPC183722
0.7313	Intermediate Similarity	NPC476278
0.731	Intermediate Similarity	NPC262077
0.731	Intermediate Similarity	NPC314114
0.7299	Intermediate Similarity	NPC472413
0.7299	Intermediate Similarity	NPC111428
0.7297	Intermediate Similarity	NPC300443
0.7293	Intermediate Similarity	NPC202521
0.7292	Intermediate Similarity	NPC52748
0.7287	Intermediate Similarity	NPC33742
0.7285	Intermediate Similarity	NPC197743
0.7285	Intermediate Similarity	NPC56635
0.7285	Intermediate Similarity	NPC297145
0.7279	Intermediate Similarity	NPC136453
0.7279	Intermediate Similarity	NPC129666
0.7278	Intermediate Similarity	NPC317362
0.7278	Intermediate Similarity	NPC318930
0.7273	Intermediate Similarity	NPC469426
0.7273	Intermediate Similarity	NPC469427
0.7273	Intermediate Similarity	NPC319950
0.7266	Intermediate Similarity	NPC45191
0.7258	Intermediate Similarity	NPC211551
0.725	Intermediate Similarity	NPC311242
0.7246	Intermediate Similarity	NPC478147
0.7241	Intermediate Similarity	NPC322878
0.7241	Intermediate Similarity	NPC314287
0.7234	Intermediate Similarity	NPC314835
0.7227	Intermediate Similarity	NPC303045
0.7227	Intermediate Similarity	NPC161972
0.7218	Intermediate Similarity	NPC476990
0.7218	Intermediate Similarity	NPC200964
0.7214	Intermediate Similarity	NPC233910
0.7214	Intermediate Similarity	NPC245836
0.7209	Intermediate Similarity	NPC35850
0.7209	Intermediate Similarity	NPC276949
0.7208	Intermediate Similarity	NPC471053
0.7208	Intermediate Similarity	NPC471052
0.7208	Intermediate Similarity	NPC471051
0.7206	Intermediate Similarity	NPC472414
0.7206	Intermediate Similarity	NPC101719
0.7194	Intermediate Similarity	NPC157311
0.7185	Intermediate Similarity	NPC175726
0.7185	Intermediate Similarity	NPC474082
0.7181	Intermediate Similarity	NPC470274
0.7179	Intermediate Similarity	NPC258627
0.7179	Intermediate Similarity	NPC172128
0.717	Intermediate Similarity	NPC476227
0.7164	Intermediate Similarity	NPC71684
0.7161	Intermediate Similarity	NPC63931
0.7143	Intermediate Similarity	NPC8761
0.7143	Intermediate Similarity	NPC44805
0.7143	Intermediate Similarity	NPC246079
0.7133	Intermediate Similarity	NPC473341
0.7132	Intermediate Similarity	NPC222466
0.7123	Intermediate Similarity	NPC315266
0.7122	Intermediate Similarity	NPC200589
0.7111	Intermediate Similarity	NPC27581
0.7107	Intermediate Similarity	NPC137627
0.7107	Intermediate Similarity	NPC248670
0.7107	Intermediate Similarity	NPC293628
0.7107	Intermediate Similarity	NPC10781
0.7107	Intermediate Similarity	NPC306804
0.7107	Intermediate Similarity	NPC122493
0.7103	Intermediate Similarity	NPC316202
0.7095	Intermediate Similarity	NPC471820
0.7095	Intermediate Similarity	NPC240848
0.7095	Intermediate Similarity	NPC471821
0.7092	Intermediate Similarity	NPC470392
0.7078	Intermediate Similarity	NPC471527
0.7077	Intermediate Similarity	NPC1986
0.7077	Intermediate Similarity	NPC474544
0.7075	Intermediate Similarity	NPC314358
0.707	Intermediate Similarity	NPC107938
0.707	Intermediate Similarity	NPC294516
0.7063	Intermediate Similarity	NPC471165
0.7063	Intermediate Similarity	NPC208725
0.7063	Intermediate Similarity	NPC326407
0.7063	Intermediate Similarity	NPC159767
0.7063	Intermediate Similarity	NPC26108

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 NPC47667 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	93
0.1-0.2	333
0.2-0.3	724
0.3-0.4	2074
0.4-0.5	3428
0.5-0.6	1905
0.6-0.7	517
0.7-0.8	72
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8211	Intermediate Similarity	NPD1348	Approved
0.816	Intermediate Similarity	NPD2217	Approved
0.816	Intermediate Similarity	NPD2218	Phase 2
0.8106	Intermediate Similarity	NPD4738	Phase 2
0.8099	Intermediate Similarity	NPD3644	Approved
0.8099	Intermediate Similarity	NPD3643	Approved
0.8099	Intermediate Similarity	NPD3642	Approved
0.8095	Intermediate Similarity	NPD5981	Approved
0.7984	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD6302	Clinical (unspecified phase)
0.7926	Intermediate Similarity	NPD8416	Discontinued
0.7883	Intermediate Similarity	NPD6852	Discontinued
0.7868	Intermediate Similarity	NPD8643	Discontinued
0.7852	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD7828	Discontinued
0.7714	Intermediate Similarity	NPD7978	Discontinued
0.7574	Intermediate Similarity	NPD3136	Phase 2
0.7541	Intermediate Similarity	NPD1040	Phase 2
0.75	Intermediate Similarity	NPD8323	Discontinued
0.7462	Intermediate Similarity	NPD4479	Discontinued
0.7447	Intermediate Similarity	NPD6864	Phase 2
0.7447	Intermediate Similarity	NPD6865	Phase 2
0.7429	Intermediate Similarity	NPD8173	Phase 2
0.7429	Intermediate Similarity	NPD8172	Phase 2
0.7415	Intermediate Similarity	NPD7613	Discontinued
0.741	Intermediate Similarity	NPD8265	Approved
0.7372	Intermediate Similarity	NPD2613	Approved
0.7368	Intermediate Similarity	NPD2611	Approved
0.7368	Intermediate Similarity	NPD4218	Approved
0.7368	Intermediate Similarity	NPD3131	Approved
0.7368	Intermediate Similarity	NPD4215	Approved
0.7368	Intermediate Similarity	NPD4216	Approved
0.7368	Intermediate Similarity	NPD2610	Approved
0.7368	Intermediate Similarity	NPD3132	Approved
0.7368	Intermediate Similarity	NPD2612	Approved
0.7368	Intermediate Similarity	NPD2609	Approved
0.7368	Intermediate Similarity	NPD4217	Approved
0.7368	Intermediate Similarity	NPD2608	Approved
0.7313	Intermediate Similarity	NPD6624	Discontinued
0.731	Intermediate Similarity	NPD3400	Discontinued
0.7293	Intermediate Similarity	NPD2956	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD7749	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD7523	Phase 3
0.7239	Intermediate Similarity	NPD5618	Discontinued
0.7222	Intermediate Similarity	NPD8076	Discontinued
0.7219	Intermediate Similarity	NPD8417	Discontinued
0.7214	Intermediate Similarity	NPD3089	Approved
0.7214	Intermediate Similarity	NPD2571	Approved
0.7214	Intermediate Similarity	NPD2572	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD2566	Approved
0.7214	Intermediate Similarity	NPD3614	Approved
0.7214	Intermediate Similarity	NPD3090	Approved
0.7214	Intermediate Similarity	NPD2574	Discontinued
0.7214	Intermediate Similarity	NPD3088	Approved
0.7214	Intermediate Similarity	NPD3616	Approved
0.7214	Intermediate Similarity	NPD2570	Approved
0.7214	Intermediate Similarity	NPD2573	Approved
0.7214	Intermediate Similarity	NPD3615	Approved
0.7214	Intermediate Similarity	NPD4746	Phase 3
0.7214	Intermediate Similarity	NPD4745	Approved
0.7214	Intermediate Similarity	NPD3087	Approved
0.7213	Intermediate Similarity	NPD4760	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD2584	Suspended
0.7133	Intermediate Similarity	NPD6901	Phase 3
0.7132	Intermediate Similarity	NPD2607	Approved
0.7121	Intermediate Similarity	NPD7522	Discontinued
0.712	Intermediate Similarity	NPD999	Phase 2
0.7113	Intermediate Similarity	NPD4685	Phase 3
0.7113	Intermediate Similarity	NPD4686	Approved
0.7113	Intermediate Similarity	NPD4684	Phase 3
0.7107	Intermediate Similarity	NPD9566	Approved
0.7099	Intermediate Similarity	NPD7508	Discontinued
0.7083	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6325	Discontinued
0.7047	Intermediate Similarity	NPD6682	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4574	Approved
0.7045	Intermediate Similarity	NPD4576	Approved
0.7042	Intermediate Similarity	NPD5323	Approved
0.7034	Intermediate Similarity	NPD7450	Phase 2
0.7013	Intermediate Similarity	NPD7495	Discontinued
0.7013	Intermediate Similarity	NPD8019	Approved
0.7008	Intermediate Similarity	NPD6038	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD6406	Approved
0.7007	Intermediate Similarity	NPD5158	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD5159	Phase 2
0.7007	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD5157	Phase 1
0.7	Intermediate Similarity	NPD6359	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4125	Approved
0.6993	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD7715	Approved
0.6972	Remote Similarity	NPD7714	Approved
0.6972	Remote Similarity	NPD8118	Discontinued
0.6968	Remote Similarity	NPD7972	Discontinued
0.6963	Remote Similarity	NPD7342	Discontinued
0.6957	Remote Similarity	NPD5367	Discontinued
0.6947	Remote Similarity	NPD1370	Approved
0.6947	Remote Similarity	NPD1374	Approved
0.6947	Remote Similarity	NPD1373	Approved
0.6947	Remote Similarity	NPD2652	Approved
0.6947	Remote Similarity	NPD1371	Approved
0.6947	Remote Similarity	NPD2650	Approved
0.6942	Remote Similarity	NPD4814	Discontinued
0.694	Remote Similarity	NPD6093	Discontinued
0.6939	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD5706	Approved
0.6929	Remote Similarity	NPD3626	Phase 3
0.6929	Remote Similarity	NPD5705	Approved
0.6929	Remote Similarity	NPD5704	Approved
0.6917	Remote Similarity	NPD6690	Approved
0.6917	Remote Similarity	NPD3123	Discovery
0.6906	Remote Similarity	NPD2628	Approved
0.6906	Remote Similarity	NPD2627	Approved
0.6906	Remote Similarity	NPD2625	Approved
0.6906	Remote Similarity	NPD2626	Approved
0.6906	Remote Similarity	NPD2159	Approved
0.6906	Remote Similarity	NPD2160	Approved
0.6901	Remote Similarity	NPD5299	Approved
0.6889	Remote Similarity	NPD4209	Clinical (unspecified phase)
0.688	Remote Similarity	NPD4719	Phase 2
0.6866	Remote Similarity	NPD6065	Approved
0.6866	Remote Similarity	NPD6360	Discontinued
0.6866	Remote Similarity	NPD1758	Phase 1
0.6863	Remote Similarity	NPD8315	Phase 1
0.6861	Remote Similarity	NPD4480	Approved
0.686	Remote Similarity	NPD1066	Discontinued
0.6859	Remote Similarity	NPD7460	Discontinued
0.6857	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1067	Discontinued
0.6842	Remote Similarity	NPD6390	Discontinued
0.6839	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6681	Discovery
0.6815	Remote Similarity	NPD1759	Phase 1
0.6806	Remote Similarity	NPD6346	Approved
0.6797	Remote Similarity	NPD467	Phase 1
0.6795	Remote Similarity	NPD7029	Discontinued
0.6783	Remote Similarity	NPD7908	Discontinued
0.6777	Remote Similarity	NPD1812	Approved
0.6777	Remote Similarity	NPD1814	Approved
0.6776	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.677	Remote Similarity	NPD7608	Discontinued
0.6767	Remote Similarity	NPD1711	Phase 2
0.6763	Remote Similarity	NPD4677	Discontinued
0.6761	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD181	Approved
0.6739	Remote Similarity	NPD4807	Approved
0.6739	Remote Similarity	NPD4806	Approved
0.6735	Remote Similarity	NPD4158	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7105	Phase 1
0.6721	Remote Similarity	NPD1080	Approved
0.672	Remote Similarity	NPD7798	Approved
0.6719	Remote Similarity	NPD5717	Approved
0.6713	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7892	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD7814	Approved
0.669	Remote Similarity	NPD6623	Phase 3
0.669	Remote Similarity	NPD5204	Approved
0.6689	Remote Similarity	NPD2887	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5162	Approved
0.6667	Remote Similarity	NPD4214	Discontinued
0.6667	Remote Similarity	NPD6564	Approved
0.6667	Remote Similarity	NPD3881	Discontinued
0.6667	Remote Similarity	NPD6565	Approved
0.6667	Remote Similarity	NPD4619	Approved
0.6667	Remote Similarity	NPD4135	Approved
0.6667	Remote Similarity	NPD4136	Approved
0.6667	Remote Similarity	NPD4106	Approved
0.6667	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4621	Approved
0.6667	Remote Similarity	NPD6563	Approved
0.6647	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD7599	Phase 2
0.6644	Remote Similarity	NPD7720	Phase 2
0.6644	Remote Similarity	NPD4152	Approved
0.6644	Remote Similarity	NPD8302	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD5203	Approved
0.6643	Remote Similarity	NPD4620	Approved
0.6643	Remote Similarity	NPD5201	Approved
0.6643	Remote Similarity	NPD4617	Approved
0.664	Remote Similarity	NPD253	Approved
0.6624	Remote Similarity	NPD6913	Approved
0.6623	Remote Similarity	NPD2575	Approved
0.6623	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.662	Remote Similarity	NPD7451	Discontinued
0.6619	Remote Similarity	NPD3603	Phase 3
0.6614	Remote Similarity	NPD855	Approved
0.6614	Remote Similarity	NPD854	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