NPASS Compound

Structure

CID313453 OpenBabel06191716122D 49 52 0 0 1 0 0 0 0 0999 V2000 -6.0376 -0.2331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7744 -2.9686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2275 3.6835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4775 -1.6751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2920 -2.6688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7267 2.4202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2049 -2.5881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9155 -1.3805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9318 0.9364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6706 1.4042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0684 0.4183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3013 1.7924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8160 -1.6755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4009 -1.3367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0719 -0.1175 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8292 -1.9975 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1525 2.7138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6869 -1.1085 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8722 -1.7915 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1156 1.9339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4727 -3.2284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3023 -1.9005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8471 2.0765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3819 1.5897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7925 1.9339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0698 1.1542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8015 2.2690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9420 -0.6373 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3227 -1.5015 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4427 2.3742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9541 2.4180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2758 2.1652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3637 -1.9604 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1156 0.9657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5439 0.3049 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8827 -0.4084 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3364 2.2388 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.6612 -4.1826 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0077 -2.8274 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2555 2.9593 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8486 -0.9895 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9475 -2.2468 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6404 2.9241 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9541 3.3906 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9693 3.0882 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5096 0.1893 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0832 -0.9053 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5522 -2.9145 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 3 17 1 0 0 0 0 6 20 1 0 0 0 0 7 21 1 0 0 0 0 9 10 1 0 0 0 0 9 11 2 0 0 0 0 10 12 2 0 0 0 0 11 15 1 0 0 0 0 12 23 1 0 0 0 0 13 14 2 0 0 0 0 13 22 1 0 0 0 0 14 47 1 0 0 0 0 15 1 1 1 0 0 0 15 28 1 0 0 0 0 16 2 1 1 0 0 0 16 22 1 0 0 0 0 16 33 1 0 0 0 0 17 27 2 0 0 0 0 17 30 1 0 0 0 0 18 4 1 6 0 0 0 18 28 1 0 0 0 0 18 29 1 0 0 0 0 19 5 1 6 0 0 0 19 29 1 0 0 0 0 19 33 1 0 0 0 0 20 31 2 0 0 0 0 20 34 1 0 0 0 0 21 38 2 0 0 0 0 21 48 1 0 0 0 0 22 39 1 6 0 0 0 23 37 2 3 0 0 0 23 40 1 0 0 0 0 24 25 2 0 0 0 0 24 26 1 0 0 0 0 24 30 1 0 0 0 0 25 31 1 0 0 0 0 25 32 1 0 0 0 0 26 34 2 0 0 0 0 26 35 1 0 0 0 0 27 32 1 0 0 0 0 27 37 1 0 0 0 0 28 41 1 1 0 0 0 29 42 1 6 0 0 0 30 43 2 0 0 0 0 31 44 1 0 0 0 0 32 45 2 0 0 0 0 33 48 1 1 0 0 0 34 49 1 0 0 0 0 35 36 1 1 0 0 0 35 46 1 0 0 0 0 36 8 1 6 0 0 0 36 47 1 0 0 0 0 36 49 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	683.29
Volume:	684.465
LogP:	4.182
LogD:	1.663
LogS:	-2.334
# Rotatable Bonds:	2
TPSA:	212.64
# H-Bond Aceptor:	13
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.145
Synthetic Accessibility Score:	7.107
Fsp3:	0.5
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.64
MDCK Permeability:	1.0583111361484043e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.954
Human Intestinal Absorption (HIA):	0.116
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	72.63169860839844%
Volume Distribution (VD):	1.477
Pgp-substrate:	14.877528190612793%

ADMET: Metabolism

CYP1A2-inhibitor:	0.065
CYP1A2-substrate:	0.765
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.674
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.348
CYP2D6-inhibitor:	0.042
CYP2D6-substrate:	0.083
CYP3A4-inhibitor:	0.193
CYP3A4-substrate:	0.532

ADMET: Excretion

Clearance (CL):	1.058
Half-life (T1/2):	0.839

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.89
Drug-inuced Liver Injury (DILI):	0.987
AMES Toxicity:	0.297
Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.011
Skin Sensitization:	0.124
Carcinogencity:	0.068
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.233

Download Data

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

Natural Product: NPC313453

Natural Product ID:	NPC313453
*Common Name:**	Chaxamycin D
IUPAC Name:	n.a.
Synonyms:	Chaxamycin D
Standard InCHIKey:	QWIHJIQXNOWSHR-MIWIPQMRSA-N
Standard InCHI:	InChI=1S/C36H45NO12/c1-15-11-9-10-12-23(40)37-27-17(3)30(43)24-25(32(27)45)31(44)20(6)34-26(24)35(46)36(8,49-34)47-14-13-22(39)16(2)33(48-21(7)38)19(5)29(42)18(4)28(15)41/h9-16,18-19,22,28-29,33,35,39,41-42,44,46H,1-8H3,(H,37,40)/b11-9+,12-10-,14-13+/t15-,16+,18+,19+,22-,28-,29+,33+,35-,36+/m0/s1
SMILES:	CC1C=CC=CC(=O)NC2=C(C(=O)C3=C(C2=O)C(=C(C4=C3C(C(O4)(OC=CC(C(C(C(C(C(C1O)C)O)C)OC(=O)C)C)O)C)O)C)O)C
Synthetic Gene Cluster:	BGC0001287;
ChEMBL Identifier:	CHEMBL1814387
PubChem CID:	53344649
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000064] Macrolactams

*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
NPO31293	Streptomyces sp. c34	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21553813]

☑ 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
MIC	13
Others	1

Activity Type	# Activity
Individual Protein	1
Organism	13

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT918	Individual Protein	Heat shock protein HSP 90-alpha	Homo sapiens	Inhibition	=	15.0	%	PMID[468437]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32.0	ug.mL-1	PMID[468437]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.13	ug.mL-1	PMID[468437]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.25	ug.mL-1	PMID[468437]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.06	ug.mL-1	PMID[468437]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	1.21	ug.mL-1	PMID[468437]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.05	ug.mL-1	PMID[468437]

☑ 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 NPC313453 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	279
0.1-0.2	1195
0.2-0.3	3392
0.3-0.4	9090
0.4-0.5	9903
0.5-0.6	6737
0.6-0.7	8765
0.7-0.8	3323
0.8-0.85	11
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8492	Intermediate Similarity	NPC163924
0.8492	Intermediate Similarity	NPC54661
0.8268	Intermediate Similarity	NPC470358
0.8251	Intermediate Similarity	NPC315406
0.8213	Intermediate Similarity	NPC314987
0.8122	Intermediate Similarity	NPC101207
0.8065	Intermediate Similarity	NPC313708
0.8021	Intermediate Similarity	NPC98776
0.8011	Intermediate Similarity	NPC221792
0.8	Intermediate Similarity	NPC475161
0.8	Intermediate Similarity	NPC477860
0.7979	Intermediate Similarity	NPC68381
0.7957	Intermediate Similarity	NPC102810
0.7957	Intermediate Similarity	NPC292213
0.7957	Intermediate Similarity	NPC191653
0.7957	Intermediate Similarity	NPC117713
0.7955	Intermediate Similarity	NPC8817
0.7937	Intermediate Similarity	NPC475233
0.7937	Intermediate Similarity	NPC312630
0.7937	Intermediate Similarity	NPC324220
0.7923	Intermediate Similarity	NPC117985
0.7914	Intermediate Similarity	NPC315306
0.7914	Intermediate Similarity	NPC313717
0.7914	Intermediate Similarity	NPC298778
0.791	Intermediate Similarity	NPC470359
0.7898	Intermediate Similarity	NPC470357
0.7884	Intermediate Similarity	NPC474345
0.7877	Intermediate Similarity	NPC240768
0.7877	Intermediate Similarity	NPC200773
0.7872	Intermediate Similarity	NPC30432
0.7872	Intermediate Similarity	NPC271385
0.7872	Intermediate Similarity	NPC5029
0.7872	Intermediate Similarity	NPC111536
0.7872	Intermediate Similarity	NPC76128
0.7865	Intermediate Similarity	NPC473631
0.7865	Intermediate Similarity	NPC475662
0.7865	Intermediate Similarity	NPC293227
0.7865	Intermediate Similarity	NPC473717
0.7861	Intermediate Similarity	NPC473202
0.7853	Intermediate Similarity	NPC137296
0.7849	Intermediate Similarity	NPC178851
0.7842	Intermediate Similarity	NPC46958
0.7842	Intermediate Similarity	NPC475246
0.7842	Intermediate Similarity	NPC477816
0.7841	Intermediate Similarity	NPC75694
0.784	Intermediate Similarity	NPC227033
0.7826	Intermediate Similarity	NPC316368
0.7826	Intermediate Similarity	NPC284236
0.7821	Intermediate Similarity	NPC321387
0.7821	Intermediate Similarity	NPC470908
0.7821	Intermediate Similarity	NPC476509
0.7821	Intermediate Similarity	NPC327059
0.7819	Intermediate Similarity	NPC477571
0.7819	Intermediate Similarity	NPC477670
0.7819	Intermediate Similarity	NPC477573
0.7819	Intermediate Similarity	NPC477572
0.7816	Intermediate Similarity	NPC478048
0.7814	Intermediate Similarity	NPC279732
0.7802	Intermediate Similarity	NPC477674
0.7796	Intermediate Similarity	NPC7752
0.7789	Intermediate Similarity	NPC63105
0.7789	Intermediate Similarity	NPC3718
0.7789	Intermediate Similarity	NPC470454
0.7789	Intermediate Similarity	NPC294149
0.7789	Intermediate Similarity	NPC162248
0.7789	Intermediate Similarity	NPC199533
0.7784	Intermediate Similarity	NPC221140
0.7784	Intermediate Similarity	NPC475220
0.7784	Intermediate Similarity	NPC475352
0.7784	Intermediate Similarity	NPC87583
0.7784	Intermediate Similarity	NPC229817
0.7784	Intermediate Similarity	NPC473686
0.7778	Intermediate Similarity	NPC478047
0.7778	Intermediate Similarity	NPC70016
0.7778	Intermediate Similarity	NPC314914
0.7778	Intermediate Similarity	NPC215921
0.7778	Intermediate Similarity	NPC478046
0.7778	Intermediate Similarity	NPC321226
0.7778	Intermediate Similarity	NPC180210
0.7778	Intermediate Similarity	NPC328856
0.7772	Intermediate Similarity	NPC472055
0.7772	Intermediate Similarity	NPC470810
0.7766	Intermediate Similarity	NPC222455
0.7766	Intermediate Similarity	NPC259905
0.776	Intermediate Similarity	NPC84494
0.776	Intermediate Similarity	NPC277710
0.776	Intermediate Similarity	NPC114257
0.776	Intermediate Similarity	NPC153578
0.776	Intermediate Similarity	NPC299149
0.776	Intermediate Similarity	NPC245059
0.7751	Intermediate Similarity	NPC170101
0.7747	Intermediate Similarity	NPC477687
0.7747	Intermediate Similarity	NPC267242
0.7747	Intermediate Similarity	NPC477671
0.7744	Intermediate Similarity	NPC105591
0.7737	Intermediate Similarity	NPC472054
0.7737	Intermediate Similarity	NPC476311
0.7737	Intermediate Similarity	NPC213052
0.7735	Intermediate Similarity	NPC271681
0.7727	Intermediate Similarity	NPC314020
0.7722	Intermediate Similarity	NPC179178
0.772	Intermediate Similarity	NPC470453
0.772	Intermediate Similarity	NPC208069
0.772	Intermediate Similarity	NPC470448
0.772	Intermediate Similarity	NPC470452
0.772	Intermediate Similarity	NPC164047
0.7717	Intermediate Similarity	NPC470339
0.7716	Intermediate Similarity	NPC48474
0.7713	Intermediate Similarity	NPC473094
0.7713	Intermediate Similarity	NPC249977
0.7708	Intermediate Similarity	NPC476210
0.7708	Intermediate Similarity	NPC476199
0.7705	Intermediate Similarity	NPC472050
0.7701	Intermediate Similarity	NPC314653
0.7701	Intermediate Similarity	NPC475979
0.7701	Intermediate Similarity	NPC473908
0.7701	Intermediate Similarity	NPC294722
0.7701	Intermediate Similarity	NPC316262
0.7697	Intermediate Similarity	NPC470910
0.7692	Intermediate Similarity	NPC477669
0.7692	Intermediate Similarity	NPC60084
0.7692	Intermediate Similarity	NPC472799
0.7688	Intermediate Similarity	NPC314693
0.7688	Intermediate Similarity	NPC474763
0.7688	Intermediate Similarity	NPC216752
0.7684	Intermediate Similarity	NPC472620
0.7684	Intermediate Similarity	NPC471181
0.768	Intermediate Similarity	NPC475148
0.768	Intermediate Similarity	NPC475656
0.7676	Intermediate Similarity	NPC313368
0.7672	Intermediate Similarity	NPC473095
0.7672	Intermediate Similarity	NPC473096
0.7668	Intermediate Similarity	NPC212290
0.7668	Intermediate Similarity	NPC473607
0.7665	Intermediate Similarity	NPC314672
0.7663	Intermediate Similarity	NPC470606
0.766	Intermediate Similarity	NPC329119
0.7654	Intermediate Similarity	NPC53362
0.7654	Intermediate Similarity	NPC166583
0.7653	Intermediate Similarity	NPC174486
0.7647	Intermediate Similarity	NPC471286
0.7647	Intermediate Similarity	NPC475055
0.7647	Intermediate Similarity	NPC91288
0.7644	Intermediate Similarity	NPC476152
0.7644	Intermediate Similarity	NPC476229
0.7642	Intermediate Similarity	NPC252156
0.7641	Intermediate Similarity	NPC106700
0.764	Intermediate Similarity	NPC118059
0.764	Intermediate Similarity	NPC288910
0.764	Intermediate Similarity	NPC133060
0.764	Intermediate Similarity	NPC470554
0.7637	Intermediate Similarity	NPC273483
0.7637	Intermediate Similarity	NPC180388
0.7635	Intermediate Similarity	NPC80472
0.7634	Intermediate Similarity	NPC92589
0.7634	Intermediate Similarity	NPC65746
0.7634	Intermediate Similarity	NPC474779
0.7634	Intermediate Similarity	NPC478041
0.7632	Intermediate Similarity	NPC241387
0.7632	Intermediate Similarity	NPC241874
0.7632	Intermediate Similarity	NPC251144
0.7632	Intermediate Similarity	NPC17219
0.7629	Intermediate Similarity	NPC18306
0.7627	Intermediate Similarity	NPC472344
0.7624	Intermediate Similarity	NPC38775
0.7624	Intermediate Similarity	NPC469670
0.7624	Intermediate Similarity	NPC158866
0.7624	Intermediate Similarity	NPC469619
0.7622	Intermediate Similarity	NPC470607
0.7619	Intermediate Similarity	NPC471180
0.7617	Intermediate Similarity	NPC477683
0.7617	Intermediate Similarity	NPC233978
0.7617	Intermediate Similarity	NPC477682
0.7612	Intermediate Similarity	NPC476662
0.7611	Intermediate Similarity	NPC472345
0.7609	Intermediate Similarity	NPC78554
0.7609	Intermediate Similarity	NPC474738
0.7609	Intermediate Similarity	NPC109967
0.7609	Intermediate Similarity	NPC469936
0.7609	Intermediate Similarity	NPC129053
0.7609	Intermediate Similarity	NPC477675
0.7609	Intermediate Similarity	NPC475797
0.7609	Intermediate Similarity	NPC321372
0.7609	Intermediate Similarity	NPC474609
0.7609	Intermediate Similarity	NPC272550
0.7606	Intermediate Similarity	NPC327652
0.7606	Intermediate Similarity	NPC12890
0.7606	Intermediate Similarity	NPC178281
0.7606	Intermediate Similarity	NPC189689
0.7604	Intermediate Similarity	NPC146803
0.7602	Intermediate Similarity	NPC241847
0.7602	Intermediate Similarity	NPC197972
0.76	Intermediate Similarity	NPC470194
0.76	Intermediate Similarity	NPC470195
0.76	Intermediate Similarity	NPC282474
0.76	Intermediate Similarity	NPC470197
0.76	Intermediate Similarity	NPC470196
0.76	Intermediate Similarity	NPC316274
0.76	Intermediate Similarity	NPC470198
0.76	Intermediate Similarity	NPC470193

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 NPC313453 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	216
0.1-0.2	617
0.2-0.3	1550
0.3-0.4	2486
0.4-0.5	2481
0.5-0.6	1308
0.6-0.7	405
0.7-0.8	85
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8235	Intermediate Similarity	NPD8366	Approved
0.8213	Intermediate Similarity	NPD8469	Approved
0.8077	Intermediate Similarity	NPD8491	Approved
0.796	Intermediate Similarity	NPD8151	Discontinued
0.7841	Intermediate Similarity	NPD2533	Approved
0.7841	Intermediate Similarity	NPD2532	Approved
0.7841	Intermediate Similarity	NPD2534	Approved
0.784	Intermediate Similarity	NPD8067	Phase 3
0.7688	Intermediate Similarity	NPD5710	Approved
0.7688	Intermediate Similarity	NPD5711	Approved
0.7659	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7659	Intermediate Similarity	NPD7874	Approved
0.7621	Intermediate Similarity	NPD7801	Approved
0.7566	Intermediate Similarity	NPD7473	Discontinued
0.7552	Intermediate Similarity	NPD6559	Discontinued
0.7536	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD7783	Phase 2
0.7512	Intermediate Similarity	NPD7584	Approved
0.75	Intermediate Similarity	NPD7819	Suspended
0.7475	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD8150	Discontinued
0.7435	Intermediate Similarity	NPD3818	Discontinued
0.7407	Intermediate Similarity	NPD6232	Discontinued
0.7396	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD8313	Approved
0.7385	Intermediate Similarity	NPD8312	Approved
0.738	Intermediate Similarity	NPD7075	Discontinued
0.7358	Intermediate Similarity	NPD8404	Phase 2
0.7333	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD8320	Phase 1
0.733	Intermediate Similarity	NPD8319	Approved
0.7325	Intermediate Similarity	NPD8367	Approved
0.7317	Intermediate Similarity	NPD6823	Phase 2
0.7308	Intermediate Similarity	NPD7701	Phase 2
0.7304	Intermediate Similarity	NPD6779	Approved
0.7304	Intermediate Similarity	NPD6782	Approved
0.7304	Intermediate Similarity	NPD6776	Approved
0.7304	Intermediate Similarity	NPD6777	Approved
0.7304	Intermediate Similarity	NPD6780	Approved
0.7304	Intermediate Similarity	NPD6778	Approved
0.7304	Intermediate Similarity	NPD6781	Approved
0.7287	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7696	Phase 3
0.7282	Intermediate Similarity	NPD7435	Discontinued
0.7282	Intermediate Similarity	NPD7698	Approved
0.7282	Intermediate Similarity	NPD7697	Approved
0.7268	Intermediate Similarity	NPD7074	Phase 3
0.7264	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD6213	Phase 3
0.7264	Intermediate Similarity	NPD7930	Approved
0.7264	Intermediate Similarity	NPD6212	Phase 3
0.7263	Intermediate Similarity	NPD2800	Approved
0.7246	Intermediate Similarity	NPD7870	Phase 2
0.7246	Intermediate Similarity	NPD7871	Phase 2
0.7225	Intermediate Similarity	NPD7585	Approved
0.7222	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7054	Approved
0.7206	Intermediate Similarity	NPD7699	Phase 2
0.7206	Intermediate Similarity	NPD7700	Phase 2
0.72	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD8492	Approved
0.7181	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7472	Approved
0.7177	Intermediate Similarity	NPD7583	Approved
0.7173	Intermediate Similarity	NPD6959	Discontinued
0.7171	Intermediate Similarity	NPD7565	Approved
0.7166	Intermediate Similarity	NPD6801	Discontinued
0.7157	Intermediate Similarity	NPD7808	Phase 3
0.7157	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD4380	Phase 2
0.7143	Intermediate Similarity	NPD6534	Approved
0.7143	Intermediate Similarity	NPD6535	Approved
0.7136	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD8059	Phase 3
0.7128	Intermediate Similarity	NPD5844	Phase 1
0.7111	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7251	Discontinued
0.71	Intermediate Similarity	NPD8434	Phase 2
0.7078	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD1934	Approved
0.7074	Intermediate Similarity	NPD37	Approved
0.7068	Intermediate Similarity	NPD6234	Discontinued
0.7064	Intermediate Similarity	NPD8461	Discontinued
0.7059	Intermediate Similarity	NPD6599	Discontinued
0.7056	Intermediate Similarity	NPD6797	Phase 2
0.7053	Intermediate Similarity	NPD4965	Approved
0.7053	Intermediate Similarity	NPD4967	Phase 2
0.7053	Intermediate Similarity	NPD3882	Suspended
0.7053	Intermediate Similarity	NPD4966	Approved
0.7053	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7972	Discontinued
0.7031	Intermediate Similarity	NPD5494	Approved
0.7021	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD3226	Approved
0.7005	Intermediate Similarity	NPD8285	Discontinued
0.7	Intermediate Similarity	NPD8407	Phase 2
0.7	Intermediate Similarity	NPD3817	Phase 2
0.6995	Remote Similarity	NPD7199	Phase 2
0.699	Remote Similarity	NPD7228	Approved
0.6974	Remote Similarity	NPD6166	Phase 2
0.6974	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD7999	Approved
0.6965	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD2801	Approved
0.6942	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD4361	Phase 2
0.694	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7411	Suspended
0.6927	Remote Similarity	NPD6651	Approved
0.6923	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6799	Approved
0.6911	Remote Similarity	NPD5402	Approved
0.6909	Remote Similarity	NPD7907	Approved
0.6905	Remote Similarity	NPD5005	Approved
0.6905	Remote Similarity	NPD5006	Approved
0.6888	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7768	Phase 2
0.6872	Remote Similarity	NPD7315	Approved
0.6863	Remote Similarity	NPD8360	Approved
0.6863	Remote Similarity	NPD8361	Approved
0.6856	Remote Similarity	NPD6746	Phase 2
0.685	Remote Similarity	NPD8368	Discontinued
0.685	Remote Similarity	NPD6104	Discontinued
0.6848	Remote Similarity	NPD4628	Phase 3
0.6839	Remote Similarity	NPD3749	Approved
0.6837	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4111	Phase 1
0.6818	Remote Similarity	NPD4665	Approved
0.6818	Remote Similarity	NPD3751	Discontinued
0.6814	Remote Similarity	NPD6841	Approved
0.6814	Remote Similarity	NPD6843	Phase 3
0.6814	Remote Similarity	NPD6842	Approved
0.6812	Remote Similarity	NPD4360	Phase 2
0.6812	Remote Similarity	NPD4363	Phase 3
0.681	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD920	Approved
0.68	Remote Similarity	NPD3823	Discontinued
0.68	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD4420	Approved
0.6791	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.678	Remote Similarity	NPD8435	Approved
0.6776	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD2346	Discontinued
0.6774	Remote Similarity	NPD7827	Phase 1
0.6757	Remote Similarity	NPD3750	Approved
0.6757	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD1549	Phase 2
0.6738	Remote Similarity	NPD1511	Approved
0.6734	Remote Similarity	NPD7177	Discontinued
0.6729	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.672	Remote Similarity	NPD5403	Approved
0.6718	Remote Similarity	NPD919	Approved
0.6716	Remote Similarity	NPD5953	Discontinued
0.6704	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7229	Phase 3
0.6684	Remote Similarity	NPD1465	Phase 2
0.6683	Remote Similarity	NPD7240	Approved
0.6682	Remote Similarity	NPD6874	Approved
0.6667	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1729	Discontinued
0.6667	Remote Similarity	NPD8485	Approved
0.6667	Remote Similarity	NPD3057	Approved
0.6667	Remote Similarity	NPD1512	Approved
0.6667	Remote Similarity	NPD5242	Approved
0.665	Remote Similarity	NPD1898	Discontinued
0.6649	Remote Similarity	NPD7458	Discontinued
0.6648	Remote Similarity	NPD1607	Approved
0.6635	Remote Similarity	NPD7296	Approved
0.6633	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.663	Remote Similarity	NPD2935	Discontinued
0.663	Remote Similarity	NPD1551	Phase 2
0.663	Remote Similarity	NPD2796	Approved
0.662	Remote Similarity	NPD2493	Approved
0.662	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.662	Remote Similarity	NPD2494	Approved
0.6618	Remote Similarity	NPD5035	Approved
0.6617	Remote Similarity	NPD7286	Phase 2
0.6616	Remote Similarity	NPD3787	Discontinued
0.6614	Remote Similarity	NPD5401	Approved
0.6613	Remote Similarity	NPD1243	Approved
0.6605	Remote Similarity	NPD4583	Approved
0.6605	Remote Similarity	NPD4582	Approved
0.6602	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD7685	Pre-registration
0.6601	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD4666	Phase 3
0.6598	Remote Similarity	NPD8455	Phase 2
0.6596	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD3533	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