NPASS Compound

Structure

CID293917 OpenBabel06191716102D 44 47 0 0 1 0 0 0 0 0999 V2000 1.8116 5.6019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3116 6.4679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3601 5.2685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6473 4.1096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9318 -0.1808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9318 -1.1808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0657 0.3192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0657 -1.6808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3116 4.7359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9396 1.0793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9651 -1.5991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6609 -0.6808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8116 5.6019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 4.3175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2486 0.1282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1997 -0.1808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1997 -1.1808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8116 3.8698 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9615 1.2872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8605 -0.6045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8786 -2.0058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.5743 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5547 3.2007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5547 0.3736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7957 1.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.0743 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 5.2486 -1.4898 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.9615 2.2872 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.8605 4.1789 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.8116 -0.2955 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 2.7653 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.6876 -1.4180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9831 -3.0003 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3638 3.7885 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3638 -0.2142 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7957 1.7872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5570 5.0254 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5570 -1.4511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 17 1 0 0 0 0 5 6 2 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 19 2 0 0 0 0 9 20 2 0 0 0 0 11 37 1 0 0 0 0 12 16 1 0 0 0 0 13 18 1 0 0 0 0 14 25 1 0 0 0 0 15 18 2 0 0 0 0 15 32 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 32 1 0 0 0 0 21 12 1 1 0 0 0 21 27 1 0 0 0 0 21 34 1 0 0 0 0 22 13 1 6 0 0 0 22 28 1 0 0 0 0 22 33 1 0 0 0 0 23 14 1 1 0 0 0 23 31 1 0 0 0 0 23 35 1 0 0 0 0 24 10 1 1 0 0 0 24 29 1 0 0 0 0 24 37 1 0 0 0 0 25 38 2 0 0 0 0 25 39 1 0 0 0 0 26 17 1 6 0 0 0 26 30 1 0 0 0 0 26 36 1 0 0 0 0 27 33 2 3 0 0 0 27 40 1 0 0 0 0 28 35 2 3 0 0 0 28 41 1 0 0 0 0 29 36 2 3 0 0 0 29 42 1 0 0 0 0 30 34 2 3 0 0 0 30 43 1 0 0 0 0 31 37 1 0 0 0 0 31 44 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	610.31
Volume:	611.654
LogP:	1.174
LogD:	2.22
LogS:	-3.259
# Rotatable Bonds:	7
TPSA:	189.8
# H-Bond Aceptor:	13
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.268
Synthetic Accessibility Score:	4.687
Fsp3:	0.548
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:	-6.273
MDCK Permeability:	1.907351816043956e-06
Pgp-inhibitor:	0.008
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.149
20% Bioavailability (F20%):	0.161
30% Bioavailability (F30%):	0.869

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.064
Plasma Protein Binding (PPB):	67.7068862915039%
Volume Distribution (VD):	0.246
Pgp-substrate:	30.82737922668457%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.017
CYP2C19-inhibitor:	0.071
CYP2C19-substrate:	0.045
CYP2C9-inhibitor:	0.239
CYP2C9-substrate:	0.95
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.117
CYP3A4-inhibitor:	0.187
CYP3A4-substrate:	0.054

ADMET: Excretion

Clearance (CL):	2.704
Half-life (T1/2):	0.866

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.887
Drug-inuced Liver Injury (DILI):	0.789
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.691
Maximum Recommended Daily Dose:	0.9
Skin Sensitization:	0.097
Carcinogencity:	0.141
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.074

Download Data

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

Natural Product: NPC293917

Natural Product ID:	NPC293917
*Common Name:**	Bq-123
IUPAC Name:	2-[(3S,6R,9S,12R,15S)-6-(1H-indol-3-ylmethyl)-9-(2-methylpropyl)-2,5,8,11,14-pentaoxo-12-propan-2-yl-1,4,7,10,13-pentazabicyclo[13.3.0]octadecan-3-yl]acetic acid
Synonyms:	BQ-123
Standard InCHIKey:	VYCMAAOURFJIHD-AOYLRGCGSA-N
Standard InCHI:	InChI=1S/C31H42N6O7/c1-16(2)12-21-27(40)33-22(13-18-15-32-20-9-6-5-8-19(18)20)28(41)35-23(14-25(38)39)31(44)37-11-7-10-24(37)29(42)36-26(17(3)4)30(43)34-21/h5-6,8-9,15-17,21-24,26,32H,7,10-14H2,1-4H3,(H,33,40)(H,34,43)(H,35,41)(H,36,42)(H,38,39)/t21-,22+,23-,24-,26+/m0/s1
SMILES:	CC(C[C@@H]1N=C(O)[C@H](N=C(O)[C@@H]2CCCN2C(=O)[C@@H](N=C([C@H](N=C1O)Cc1c[nH]c2c1cccc2)O)CC(=O)O)C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1269102
PubChem CID:	52943236
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
NPO22874	Bombyx mori	Species	Bombycidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18071251]
NPO22874	Bombyx mori	Species	Bombycidae	Eukaryota	n.a.	faeces	n.a.	PMID[18323202]
NPO22874	Bombyx mori	Species	Bombycidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22874	Bombyx mori	Species	Bombycidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22874	Bombyx mori	Species	Bombycidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22874	Bombyx mori	Species	Bombycidae	Eukaryota	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	10
Ki	5
Others	6

Activity Type	# Activity
Individual Protein	16
ORGANISM	3
Others	1
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT247	Individual Protein	Endothelin receptor ET-A	Homo sapiens	IC50	=	22	nM	PMID[15055997]
NPT3951	Individual Protein	Endothelin receptor ET-A	Rattus norvegicus	IC50	=	14	nM	PMID[9667964]
NPT5168	Individual Protein	Endothelin receptor ET-B	Rattus norvegicus	IC50	>	30000	nM	PMID[9667964]
NPT247	Individual Protein	Endothelin receptor ET-A	Homo sapiens	Ki	=	18	nM	DOI[10.1016/0960-894X(95)00019-P]
NPT5168	Individual Protein	Endothelin receptor ET-B	Rattus norvegicus	Ki	=	7000	nM	DOI[10.1016/0960-894X(95)00019-P]
NPT3951	Individual Protein	Endothelin receptor ET-A	Rattus norvegicus	Ki	=	40	nM	PMID[9857090]
NPT5168	Individual Protein	Endothelin receptor ET-B	Rattus norvegicus	Ki	=	32000	nM	PMID[9857090]
NPT5167	Individual Protein	Endothelin receptor ET-A	Sus scrofa	IC50	=	22	nM	DOI[10.1016/0960-894X(95)00237-N]
NPT5792	Individual Protein	Endothelin receptor ET-B	Sus scrofa	IC50	=	18000	nM	DOI[10.1016/0960-894X(95)00237-N]
NPT247	Individual Protein	Endothelin receptor ET-A	Homo sapiens	Inhibition	=	25	%	PMID[15139753]
NPT5167	Individual Protein	Endothelin receptor ET-A	Sus scrofa	IC50	=	22000	nM	PMID[1315867]
NPT5792	Individual Protein	Endothelin receptor ET-B	Sus scrofa	IC50	=	23000	nM	PMID[1315867]
NPT247	Individual Protein	Endothelin receptor ET-A	Homo sapiens	IC50	=	24.8	nM	PMID[20932745]
NPT304	Individual Protein	Canalicular multispecific organic anion transporter 1	Rattus norvegicus	Ki	=	84100	nM	PMID[9918561]
NPT3952	Individual Protein	Endothelin receptor ET-B	Homo sapiens	IC50	>	1000	nM	PMID[22862294]
NPT247	Individual Protein	Endothelin receptor ET-A	Homo sapiens	IC50	=	20.5	nM	PMID[22862294]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-3.86	%	PMID[513030]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	3.245	%	PMID[513031]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.18	%	PMID[513032]
NPT2	Others	Unspecified		Inhibition	~	60	%	PMID[14980650]

☑ 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 NPC293917 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	318
0.1-0.2	2430
0.2-0.3	20036
0.3-0.4	12458
0.4-0.5	2602
0.5-0.6	2714
0.6-0.7	1487
0.7-0.8	543
0.8-0.85	72
0.85-0.9	29
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9489	High Similarity	NPC213629
0.9091	High Similarity	NPC473376
0.9076	High Similarity	NPC171317
0.9076	High Similarity	NPC473640
0.9032	High Similarity	NPC475506
0.9027	High Similarity	NPC100321
0.8984	High Similarity	NPC155143
0.886	High Similarity	NPC75634
0.884	High Similarity	NPC94752
0.8802	High Similarity	NPC478158
0.8718	High Similarity	NPC54744
0.8705	High Similarity	NPC223791
0.8705	High Similarity	NPC107077
0.8689	High Similarity	NPC17059
0.8615	High Similarity	NPC320968
0.8601	High Similarity	NPC54420
0.858	High Similarity	NPC160105
0.8579	High Similarity	NPC478157
0.8541	High Similarity	NPC321708
0.8525	High Similarity	NPC228835
0.8513	High Similarity	NPC162860
0.8508	High Similarity	NPC248041
0.8508	High Similarity	NPC126709
0.8508	High Similarity	NPC283219
0.85	High Similarity	NPC267885
0.8492	Intermediate Similarity	NPC314603
0.8477	Intermediate Similarity	NPC110602
0.8477	Intermediate Similarity	NPC31385
0.8477	Intermediate Similarity	NPC75726
0.8453	Intermediate Similarity	NPC145885
0.8453	Intermediate Similarity	NPC84827
0.8453	Intermediate Similarity	NPC14113
0.8444	Intermediate Similarity	NPC203468
0.8444	Intermediate Similarity	NPC149155
0.8444	Intermediate Similarity	NPC110500
0.8432	Intermediate Similarity	NPC235684
0.8424	Intermediate Similarity	NPC64216
0.8424	Intermediate Similarity	NPC165495
0.8358	Intermediate Similarity	NPC477714
0.8358	Intermediate Similarity	NPC281049
0.8343	Intermediate Similarity	NPC469938
0.8306	Intermediate Similarity	NPC11126
0.8299	Intermediate Similarity	NPC193761
0.8268	Intermediate Similarity	NPC474561
0.8268	Intermediate Similarity	NPC49954
0.8261	Intermediate Similarity	NPC91179
0.8254	Intermediate Similarity	NPC117244
0.8254	Intermediate Similarity	NPC473763
0.8222	Intermediate Similarity	NPC78020
0.8218	Intermediate Similarity	NPC477715
0.8205	Intermediate Similarity	NPC476874
0.8196	Intermediate Similarity	NPC470497
0.8164	Intermediate Similarity	NPC319232
0.8164	Intermediate Similarity	NPC24370
0.8158	Intermediate Similarity	NPC243716
0.8152	Intermediate Similarity	NPC59269
0.8108	Intermediate Similarity	NPC213468
0.8101	Intermediate Similarity	NPC282231
0.8093	Intermediate Similarity	NPC470499
0.8085	Intermediate Similarity	NPC15102
0.8069	Intermediate Similarity	NPC229348
0.8068	Intermediate Similarity	NPC259644
0.8068	Intermediate Similarity	NPC469760
0.8068	Intermediate Similarity	NPC469786
0.8068	Intermediate Similarity	NPC73952
0.8068	Intermediate Similarity	NPC25008
0.8068	Intermediate Similarity	NPC469763
0.8068	Intermediate Similarity	NPC469765
0.8057	Intermediate Similarity	NPC89987
0.8054	Intermediate Similarity	NPC111275
0.8048	Intermediate Similarity	NPC326363
0.8048	Intermediate Similarity	NPC69843
0.8045	Intermediate Similarity	NPC279918
0.8041	Intermediate Similarity	NPC262898
0.8038	Intermediate Similarity	NPC476491
0.8028	Intermediate Similarity	NPC478028
0.8023	Intermediate Similarity	NPC80597
0.8023	Intermediate Similarity	NPC212376
0.8023	Intermediate Similarity	NPC70922
0.8023	Intermediate Similarity	NPC75540
0.8023	Intermediate Similarity	NPC211572
0.8022	Intermediate Similarity	NPC63751
0.8021	Intermediate Similarity	NPC233936
0.8019	Intermediate Similarity	NPC155444
0.8011	Intermediate Similarity	NPC55772
0.8011	Intermediate Similarity	NPC219336
0.799	Intermediate Similarity	NPC179701
0.7957	Intermediate Similarity	NPC64436
0.7957	Intermediate Similarity	NPC217372
0.7957	Intermediate Similarity	NPC183662
0.7957	Intermediate Similarity	NPC15573
0.7956	Intermediate Similarity	NPC194640
0.7953	Intermediate Similarity	NPC478029
0.7947	Intermediate Similarity	NPC62749
0.7934	Intermediate Similarity	NPC323752
0.7933	Intermediate Similarity	NPC469762
0.7931	Intermediate Similarity	NPC6865
0.7931	Intermediate Similarity	NPC153980
0.7926	Intermediate Similarity	NPC71037
0.7897	Intermediate Similarity	NPC325976
0.7895	Intermediate Similarity	NPC280290
0.7883	Intermediate Similarity	NPC153400
0.7882	Intermediate Similarity	NPC72956
0.7877	Intermediate Similarity	NPC469785
0.7869	Intermediate Similarity	NPC54988
0.7861	Intermediate Similarity	NPC323927
0.7857	Intermediate Similarity	NPC311276
0.7853	Intermediate Similarity	NPC474707
0.7843	Intermediate Similarity	NPC471193
0.7843	Intermediate Similarity	NPC471194
0.7839	Intermediate Similarity	NPC476073
0.783	Intermediate Similarity	NPC191382
0.783	Intermediate Similarity	NPC56109
0.7806	Intermediate Similarity	NPC11445
0.7801	Intermediate Similarity	NPC308931
0.7801	Intermediate Similarity	NPC99939
0.7789	Intermediate Similarity	NPC300183
0.7778	Intermediate Similarity	NPC16659
0.7778	Intermediate Similarity	NPC469896
0.7772	Intermediate Similarity	NPC65215
0.7772	Intermediate Similarity	NPC173028
0.7766	Intermediate Similarity	NPC248454
0.7766	Intermediate Similarity	NPC227582
0.7766	Intermediate Similarity	NPC156704
0.776	Intermediate Similarity	NPC315555
0.7755	Intermediate Similarity	NPC195239
0.7755	Intermediate Similarity	NPC157828
0.7755	Intermediate Similarity	NPC294693
0.7734	Intermediate Similarity	NPC314957
0.773	Intermediate Similarity	NPC201700
0.7729	Intermediate Similarity	NPC471192
0.7727	Intermediate Similarity	NPC131887
0.7727	Intermediate Similarity	NPC314372
0.7725	Intermediate Similarity	NPC265710
0.7721	Intermediate Similarity	NPC63031
0.772	Intermediate Similarity	NPC317030
0.772	Intermediate Similarity	NPC204565
0.7696	Intermediate Similarity	NPC469358
0.7692	Intermediate Similarity	NPC230869
0.7674	Intermediate Similarity	NPC474877
0.7674	Intermediate Similarity	NPC475969
0.7674	Intermediate Similarity	NPC475859
0.7672	Intermediate Similarity	NPC473380
0.7672	Intermediate Similarity	NPC240088
0.7663	Intermediate Similarity	NPC40779
0.7661	Intermediate Similarity	NPC28945
0.7656	Intermediate Similarity	NPC472294
0.7656	Intermediate Similarity	NPC473310
0.7656	Intermediate Similarity	NPC475736
0.7654	Intermediate Similarity	NPC105818
0.7654	Intermediate Similarity	NPC24678
0.765	Intermediate Similarity	NPC45459
0.765	Intermediate Similarity	NPC315491
0.765	Intermediate Similarity	NPC252338
0.765	Intermediate Similarity	NPC131718
0.7635	Intermediate Similarity	NPC277350
0.7629	Intermediate Similarity	NPC278434
0.7628	Intermediate Similarity	NPC470729
0.7628	Intermediate Similarity	NPC477175
0.7628	Intermediate Similarity	NPC470730
0.7628	Intermediate Similarity	NPC477176
0.7621	Intermediate Similarity	NPC82370
0.7621	Intermediate Similarity	NPC54981
0.7614	Intermediate Similarity	NPC474177
0.7614	Intermediate Similarity	NPC190296
0.761	Intermediate Similarity	NPC271862
0.7606	Intermediate Similarity	NPC161861
0.7604	Intermediate Similarity	NPC163055
0.7604	Intermediate Similarity	NPC63279
0.7596	Intermediate Similarity	NPC313640
0.7593	Intermediate Similarity	NPC477177
0.759	Intermediate Similarity	NPC175474
0.7582	Intermediate Similarity	NPC285469
0.7576	Intermediate Similarity	NPC133366
0.7569	Intermediate Similarity	NPC200214
0.7569	Intermediate Similarity	NPC297642
0.7565	Intermediate Similarity	NPC477003
0.7565	Intermediate Similarity	NPC472119
0.7562	Intermediate Similarity	NPC205254
0.7562	Intermediate Similarity	NPC23420
0.7562	Intermediate Similarity	NPC106771
0.7562	Intermediate Similarity	NPC303820
0.7558	Intermediate Similarity	NPC165743
0.7551	Intermediate Similarity	NPC95783
0.755	Intermediate Similarity	NPC52557
0.755	Intermediate Similarity	NPC67288
0.7543	Intermediate Similarity	NPC263117
0.7543	Intermediate Similarity	NPC125181
0.7543	Intermediate Similarity	NPC242872
0.7539	Intermediate Similarity	NPC248462
0.7538	Intermediate Similarity	NPC472323
0.7526	Intermediate Similarity	NPC163421
0.7526	Intermediate Similarity	NPC188387
0.7525	Intermediate Similarity	NPC267343
0.7525	Intermediate Similarity	NPC475935
0.7525	Intermediate Similarity	NPC94211
0.7525	Intermediate Similarity	NPC52909
0.7524	Intermediate Similarity	NPC469743
0.7524	Intermediate Similarity	NPC79386
0.7513	Intermediate Similarity	NPC476460

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 NPC293917 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	455
0.2-0.3	1050
0.3-0.4	1758
0.4-0.5	2429
0.5-0.6	2303
0.6-0.7	831
0.7-0.8	118
0.8-0.85	19
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD7621	Clinical (unspecified phase)
0.88	High Similarity	NPD7711	Discontinued
0.8776	High Similarity	NPD8406	Clinical (unspecified phase)
0.8698	High Similarity	NPD8493	Clinical (unspecified phase)
0.8626	High Similarity	NPD2096	Phase 2
0.8626	High Similarity	NPD2091	Phase 2
0.8594	High Similarity	NPD8272	Phase 2
0.8579	High Similarity	NPD7970	Approved
0.8579	High Similarity	NPD7971	Clinical (unspecified phase)
0.8571	High Similarity	NPD2095	Phase 2
0.8571	High Similarity	NPD5728	Clinical (unspecified phase)
0.8571	High Similarity	NPD2092	Phase 2
0.8571	High Similarity	NPD2094	Phase 2
0.852	High Similarity	NPD7470	Discontinued
0.8444	Intermediate Similarity	NPD482	Approved
0.8426	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.8398	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.838	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.8287	Intermediate Similarity	NPD750	Phase 2
0.8256	Intermediate Similarity	NPD8072	Approved
0.8205	Intermediate Similarity	NPD8073	Approved
0.8204	Intermediate Similarity	NPD7271	Approved
0.82	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.8191	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.8162	Intermediate Similarity	NPD6595	Phase 3
0.8125	Intermediate Similarity	NPD7730	Approved
0.8125	Intermediate Similarity	NPD7731	Approved
0.8081	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD7957	Phase 1
0.8061	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.8053	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.8048	Intermediate Similarity	NPD7824	Approved
0.8031	Intermediate Similarity	NPD7619	Phase 3
0.8031	Intermediate Similarity	NPD7618	Phase 3
0.801	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.794	Intermediate Similarity	NPD5426	Phase 3
0.7938	Intermediate Similarity	NPD7944	Discontinued
0.7934	Intermediate Similarity	NPD7951	Approved
0.7934	Intermediate Similarity	NPD7950	Approved
0.7934	Intermediate Similarity	NPD7790	Approved
0.7934	Intermediate Similarity	NPD7789	Approved
0.7934	Intermediate Similarity	NPD7953	Approved
0.7934	Intermediate Similarity	NPD7952	Approved
0.7934	Intermediate Similarity	NPD7791	Approved
0.7897	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD8322	Phase 2
0.7833	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.783	Intermediate Similarity	NPD7781	Approved
0.783	Intermediate Similarity	NPD7780	Approved
0.7812	Intermediate Similarity	NPD8431	Approved
0.7812	Intermediate Similarity	NPD3961	Discontinued
0.7767	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD2144	Approved
0.7756	Intermediate Similarity	NPD8093	Discontinued
0.7744	Intermediate Similarity	NPD6665	Discontinued
0.7737	Intermediate Similarity	NPD3038	Discontinued
0.7734	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7713	Intermediate Similarity	NPD4075	Phase 2
0.7684	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD484	Approved
0.7629	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD6664	Approved
0.757	Intermediate Similarity	NPD7603	Discontinued
0.7566	Intermediate Similarity	NPD5322	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD2509	Approved
0.7561	Intermediate Similarity	NPD2510	Approved
0.7549	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD8094	Discontinued
0.7539	Intermediate Similarity	NPD4079	Approved
0.7539	Intermediate Similarity	NPD4076	Approved
0.7538	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD6217	Discontinued
0.7487	Intermediate Similarity	NPD3506	Approved
0.7487	Intermediate Similarity	NPD3505	Approved
0.7486	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD5065	Approved
0.7464	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD786	Approved
0.7426	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD6999	Discontinued
0.7415	Intermediate Similarity	NPD8098	Approved
0.7415	Intermediate Similarity	NPD5901	Discontinued
0.7415	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD7948	Phase 1
0.74	Intermediate Similarity	NPD4427	Phase 2
0.7389	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD7001	Phase 3
0.7374	Intermediate Similarity	NPD4499	Approved
0.7363	Intermediate Similarity	NPD2172	Phase 1
0.7358	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD2844	Phase 3
0.7353	Intermediate Similarity	NPD5017	Discontinued
0.7344	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD6578	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD7717	Approved
0.7315	Intermediate Similarity	NPD7716	Approved
0.7308	Intermediate Similarity	NPD7665	Phase 2
0.7308	Intermediate Similarity	NPD7666	Phase 3
0.7306	Intermediate Similarity	NPD4181	Approved
0.7304	Intermediate Similarity	NPD4601	Approved
0.7304	Intermediate Similarity	NPD4600	Approved
0.7292	Intermediate Similarity	NPD4128	Approved
0.7287	Intermediate Similarity	NPD5138	Approved
0.7287	Intermediate Similarity	NPD5140	Approved
0.7277	Intermediate Similarity	NPD5818	Discontinued
0.7273	Intermediate Similarity	NPD8372	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD1722	Approved
0.7251	Intermediate Similarity	NPD8097	Phase 3
0.7251	Intermediate Similarity	NPD8096	Phase 3
0.7235	Intermediate Similarity	NPD6173	Approved
0.723	Intermediate Similarity	NPD3394	Approved
0.723	Intermediate Similarity	NPD3393	Approved
0.723	Intermediate Similarity	NPD3389	Approved
0.7222	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD5505	Discontinued
0.7213	Intermediate Similarity	NPD3100	Discontinued
0.7211	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD2639	Approved
0.7211	Intermediate Similarity	NPD2642	Approved
0.7208	Intermediate Similarity	NPD6178	Phase 3
0.7196	Intermediate Similarity	NPD8258	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD8256	Approved
0.7196	Intermediate Similarity	NPD8257	Approved
0.7194	Intermediate Similarity	NPD3178	Discontinued
0.7179	Intermediate Similarity	NPD8386	Phase 2
0.7178	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD802	Phase 2
0.7171	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD8022	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD8169	Discontinued
0.7163	Intermediate Similarity	NPD8114	Approved
0.7163	Intermediate Similarity	NPD8115	Approved
0.7158	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD4703	Approved
0.7158	Intermediate Similarity	NPD4702	Approved
0.7143	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD6165	Phase 2
0.7136	Intermediate Similarity	NPD6164	Phase 2
0.7136	Intermediate Similarity	NPD8292	Phase 2
0.7135	Intermediate Similarity	NPD1325	Approved
0.7135	Intermediate Similarity	NPD1326	Approved
0.7129	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7865	Approved
0.712	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5487	Phase 1
0.7101	Intermediate Similarity	NPD7817	Phase 1
0.7094	Intermediate Similarity	NPD1038	Approved
0.7087	Intermediate Similarity	NPD6248	Phase 2
0.7087	Intermediate Similarity	NPD6249	Phase 2
0.7085	Intermediate Similarity	NPD4336	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4640	Approved
0.7083	Intermediate Similarity	NPD4639	Approved
0.7083	Intermediate Similarity	NPD4638	Approved
0.7073	Intermediate Similarity	NPD2880	Discontinued
0.7073	Intermediate Similarity	NPD5003	Discontinued
0.7065	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4602	Approved
0.7056	Intermediate Similarity	NPD6452	Discontinued
0.7053	Intermediate Similarity	NPD4500	Approved
0.7053	Intermediate Similarity	NPD4501	Approved
0.705	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD3717	Discontinued
0.7033	Intermediate Similarity	NPD6176	Phase 1
0.7019	Intermediate Similarity	NPD7727	Phase 2
0.7016	Intermediate Similarity	NPD3583	Phase 2
0.7016	Intermediate Similarity	NPD3323	Discontinued
0.7014	Intermediate Similarity	NPD8289	Discontinued
0.701	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD4852	Phase 2
0.7009	Intermediate Similarity	NPD8119	Discontinued
0.7	Intermediate Similarity	NPD8283	Approved
0.7	Intermediate Similarity	NPD56	Approved
0.7	Intermediate Similarity	NPD1403	Approved
0.7	Intermediate Similarity	NPD1404	Approved
0.7	Intermediate Similarity	NPD2511	Approved
0.7	Intermediate Similarity	NPD8282	Approved
0.6996	Remote Similarity	NPD8374	Phase 3
0.6995	Remote Similarity	NPD2641	Approved
0.6995	Remote Similarity	NPD2640	Approved
0.6995	Remote Similarity	NPD7465	Suspended
0.699	Remote Similarity	NPD6044	Discontinued
0.6989	Remote Similarity	NPD4463	Approved
0.6989	Remote Similarity	NPD4462	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