NPASS Compound

Structure

NPC473155 OpenBabel07101718322D 35 40 0 0 1 0 0 0 0 0999 V2000 -0.9271 -6.0892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5491 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9432 -0.6670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3578 -3.8406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 -4.9303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0491 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -4.1871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5491 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -2.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -3.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0511 -5.8813 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -6.0491 0.0570 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6342 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.2361 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5491 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 -1.9271 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6831 -2.9271 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 -1.9271 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2219 -2.4271 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 0.9511 -2.9271 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7202 -6.6245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5491 0.9230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2219 -2.4271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6342 -3.2361 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 14 1 0 0 0 0 3 16 2 0 0 0 0 5 7 1 0 0 0 0 5 14 1 0 0 0 0 6 8 1 0 0 0 0 6 15 1 0 0 0 0 7 17 1 0 0 0 0 9 22 1 0 0 0 0 11 25 1 0 0 0 0 12 17 1 0 0 0 0 13 28 1 0 0 0 0 14 30 1 0 0 0 0 15 2 1 6 0 0 0 15 31 1 0 0 0 0 16 19 1 0 0 0 0 16 26 1 0 0 0 0 17 28 1 1 0 0 0 18 8 1 6 0 0 0 18 20 1 0 0 0 0 18 21 1 0 0 0 0 19 11 1 6 0 0 0 19 24 1 0 0 0 0 20 9 1 1 0 0 0 20 21 1 0 0 0 0 21 10 1 1 0 0 0 22 23 1 0 0 0 0 22 29 1 1 0 0 0 23 10 1 1 0 0 0 23 35 1 0 0 0 0 24 13 1 6 0 0 0 24 34 1 0 0 0 0 25 28 1 6 0 0 0 25 29 1 0 0 0 0 26 32 2 0 0 0 0 26 34 1 0 0 0 0 27 29 1 0 0 0 0 27 33 2 0 0 0 0 27 35 1 0 0 0 0 28 4 1 1 0 0 0 29 12 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.3
Volume:	503.633
LogP:	3.566
LogD:	3.587
LogS:	-4.196
# Rotatable Bonds:	6
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.435
Synthetic Accessibility Score:	6.154
Fsp3:	0.862
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.967
MDCK Permeability:	6.906730413902551e-05
Pgp-inhibitor:	0.646
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.098

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	92.54106903076172%
Volume Distribution (VD):	0.857
Pgp-substrate:	2.9139323234558105%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.162
CYP2C19-inhibitor:	0.163
CYP2C19-substrate:	0.568
CYP2C9-inhibitor:	0.636
CYP2C9-substrate:	0.325
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.139
CYP3A4-inhibitor:	0.809
CYP3A4-substrate:	0.606

ADMET: Excretion

Clearance (CL):	8.156
Half-life (T1/2):	0.346

ADMET: Toxicity

hERG Blockers:	0.457
Human Hepatotoxicity (H-HT):	0.744
Drug-inuced Liver Injury (DILI):	0.808
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.069
Maximum Recommended Daily Dose:	0.436
Skin Sensitization:	0.948
Carcinogencity:	0.143
Eye Corrosion:	0.042
Eye Irritation:	0.095
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC473155

Natural Product ID:	NPC473155
*Common Name:**	HDHAFLPMEFZPKI-SYNCWSQBSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HDHAFLPMEFZPKI-SYNCWSQBSA-N
Standard InCHI:	InChI=1S/C29H42O6/c1-14(30)5-7-17-12-29(25-11-19-16(3)26(32)34-24(19)13-28(17,25)4)22-9-20-18(8-6-15(2)31)21(20)10-23(22)35-27(29)33/h14-15,17-25,30-31H,3,5-13H2,1-2,4H3/t14?,15-,17-,18-,19+,20-,21+,22-,23+,24+,25+,28+,29-/m0/s1
SMILES:	CC(CCC1CC2(C3CC4C(C4CCC(C)O)CC3OC2=O)C5C1(CC6C(C5)C(=C)C(=O)O6)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3623292
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO26335	Carpesium abrotanoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26316467]
NPO26335	Carpesium abrotanoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26335	Carpesium abrotanoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26335	Carpesium abrotanoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26335	Carpesium abrotanoides	Species	Asteraceae	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	12
MIC	1

Activity Type	# Activity
Cell Line	9
NON-MOLECULAR	1
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	3300.0	nM	PMID[525421]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	1200.0	nM	PMID[525421]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	610.0	nM	PMID[525421]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	310.0	nM	PMID[525421]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	150.0	nM	PMID[525421]
NPT2341	Cell Line	NCI-H1975	Homo sapiens	IC50	=	1400.0	nM	PMID[525421]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	2700.0	nM	PMID[525421]
NPT112	Cell Line	MOLT-4	Homo sapiens	IC50	=	1300.0	nM	PMID[525421]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	100.0	nM	PMID[525421]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	710.0	nM	PMID[525421]
NPT742	Organism	Influenza A virus	Influenza A virus	IC50	=	15900.0	nM	PMID[525421]
NPT742	Organism	Influenza A virus	Influenza A virus	IC50	=	30000.0	nM	PMID[525421]
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	=	3700.0	nM	PMID[525421]

☑ 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 NPC473155 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	228
0.1-0.2	1605
0.2-0.3	5950
0.3-0.4	15012
0.4-0.5	6794
0.5-0.6	7095
0.6-0.7	5104
0.7-0.8	871
0.8-0.85	29
0.85-0.9	5
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9263	High Similarity	NPC476303
0.9175	High Similarity	NPC476237
0.898	High Similarity	NPC176883
0.8947	High Similarity	NPC307164
0.8901	High Similarity	NPC470012
0.8791	High Similarity	NPC477920
0.8763	High Similarity	NPC252295
0.8696	High Similarity	NPC305029
0.8696	High Similarity	NPC181103
0.8673	High Similarity	NPC470906
0.8587	High Similarity	NPC85698
0.8587	High Similarity	NPC185638
0.8571	High Similarity	NPC470011
0.8511	High Similarity	NPC116620
0.8454	Intermediate Similarity	NPC157686
0.8454	Intermediate Similarity	NPC259042
0.8387	Intermediate Similarity	NPC9231
0.837	Intermediate Similarity	NPC219011
0.8352	Intermediate Similarity	NPC226988
0.8351	Intermediate Similarity	NPC24861
0.8351	Intermediate Similarity	NPC225474
0.8351	Intermediate Similarity	NPC469596
0.8351	Intermediate Similarity	NPC148000
0.835	Intermediate Similarity	NPC470952
0.8316	Intermediate Similarity	NPC288699
0.83	Intermediate Similarity	NPC201406
0.8298	Intermediate Similarity	NPC175293
0.8283	Intermediate Similarity	NPC473963
0.8283	Intermediate Similarity	NPC136781
0.8269	Intermediate Similarity	NPC255082
0.8265	Intermediate Similarity	NPC210214
0.8261	Intermediate Similarity	NPC194637
0.8247	Intermediate Similarity	NPC294263
0.8247	Intermediate Similarity	NPC470224
0.8235	Intermediate Similarity	NPC112009
0.8235	Intermediate Similarity	NPC221421
0.8235	Intermediate Similarity	NPC36688
0.8235	Intermediate Similarity	NPC470310
0.82	Intermediate Similarity	NPC98868
0.8182	Intermediate Similarity	NPC473964
0.8182	Intermediate Similarity	NPC93245
0.8163	Intermediate Similarity	NPC471720
0.8144	Intermediate Similarity	NPC186363
0.8144	Intermediate Similarity	NPC233345
0.8125	Intermediate Similarity	NPC128496
0.8119	Intermediate Similarity	NPC47024
0.8105	Intermediate Similarity	NPC33768
0.8085	Intermediate Similarity	NPC76518
0.8081	Intermediate Similarity	NPC280877
0.8081	Intermediate Similarity	NPC183012
0.8081	Intermediate Similarity	NPC98639
0.8065	Intermediate Similarity	NPC471037
0.8061	Intermediate Similarity	NPC475700
0.8058	Intermediate Similarity	NPC180204
0.8043	Intermediate Similarity	NPC232625
0.8043	Intermediate Similarity	NPC209318
0.8043	Intermediate Similarity	NPC223330
0.8041	Intermediate Similarity	NPC475776
0.8039	Intermediate Similarity	NPC475958
0.8037	Intermediate Similarity	NPC470311
0.8021	Intermediate Similarity	NPC474719
0.8021	Intermediate Similarity	NPC277771
0.8021	Intermediate Similarity	NPC4309
0.8021	Intermediate Similarity	NPC16377
0.8021	Intermediate Similarity	NPC146937
0.802	Intermediate Similarity	NPC476807
0.802	Intermediate Similarity	NPC108368
0.802	Intermediate Similarity	NPC57079
0.802	Intermediate Similarity	NPC78427
0.802	Intermediate Similarity	NPC16911
0.802	Intermediate Similarity	NPC476806
0.8	Intermediate Similarity	NPC2783
0.8	Intermediate Similarity	NPC470275
0.8	Intermediate Similarity	NPC12774
0.8	Intermediate Similarity	NPC13949
0.8	Intermediate Similarity	NPC104568
0.8	Intermediate Similarity	NPC473656
0.8	Intermediate Similarity	NPC475007
0.8	Intermediate Similarity	NPC70661
0.8	Intermediate Similarity	NPC472505
0.8	Intermediate Similarity	NPC284518
0.8	Intermediate Similarity	NPC29410
0.8	Intermediate Similarity	NPC200054
0.8	Intermediate Similarity	NPC131665
0.8	Intermediate Similarity	NPC255387
0.7982	Intermediate Similarity	NPC123117
0.7981	Intermediate Similarity	NPC472228
0.7981	Intermediate Similarity	NPC472227
0.798	Intermediate Similarity	NPC47853
0.7979	Intermediate Similarity	NPC97505
0.7961	Intermediate Similarity	NPC155332
0.7961	Intermediate Similarity	NPC136289
0.7961	Intermediate Similarity	NPC32577
0.7961	Intermediate Similarity	NPC114540
0.7961	Intermediate Similarity	NPC124544
0.7959	Intermediate Similarity	NPC160506
0.7959	Intermediate Similarity	NPC250753
0.7959	Intermediate Similarity	NPC471747
0.7959	Intermediate Similarity	NPC72845
0.7944	Intermediate Similarity	NPC179642
0.7941	Intermediate Similarity	NPC287676
0.7938	Intermediate Similarity	NPC194642
0.7935	Intermediate Similarity	NPC170038
0.7928	Intermediate Similarity	NPC470276
0.7925	Intermediate Similarity	NPC211224
0.7921	Intermediate Similarity	NPC253826
0.7921	Intermediate Similarity	NPC253586
0.7921	Intermediate Similarity	NPC474343
0.7917	Intermediate Similarity	NPC269360
0.7917	Intermediate Similarity	NPC167877
0.7917	Intermediate Similarity	NPC264005
0.7905	Intermediate Similarity	NPC265127
0.7905	Intermediate Similarity	NPC475414
0.7905	Intermediate Similarity	NPC173172
0.79	Intermediate Similarity	NPC90014
0.79	Intermediate Similarity	NPC33473
0.79	Intermediate Similarity	NPC293052
0.7895	Intermediate Similarity	NPC264317
0.7895	Intermediate Similarity	NPC294438
0.789	Intermediate Similarity	NPC122056
0.7885	Intermediate Similarity	NPC61442
0.7885	Intermediate Similarity	NPC297617
0.7879	Intermediate Similarity	NPC139692
0.7879	Intermediate Similarity	NPC287118
0.7879	Intermediate Similarity	NPC471902
0.7879	Intermediate Similarity	NPC473690
0.7864	Intermediate Similarity	NPC118174
0.7864	Intermediate Similarity	NPC52899
0.7864	Intermediate Similarity	NPC163963
0.7864	Intermediate Similarity	NPC289148
0.7864	Intermediate Similarity	NPC75941
0.7864	Intermediate Similarity	NPC81530
0.7857	Intermediate Similarity	NPC471896
0.7849	Intermediate Similarity	NPC38642
0.7843	Intermediate Similarity	NPC471038
0.7843	Intermediate Similarity	NPC162459
0.7843	Intermediate Similarity	NPC28864
0.7843	Intermediate Similarity	NPC38471
0.7843	Intermediate Similarity	NPC98837
0.7843	Intermediate Similarity	NPC38296
0.7843	Intermediate Similarity	NPC20479
0.7843	Intermediate Similarity	NPC216478
0.7838	Intermediate Similarity	NPC284068
0.7835	Intermediate Similarity	NPC254572
0.7835	Intermediate Similarity	NPC250687
0.7835	Intermediate Similarity	NPC242864
0.7835	Intermediate Similarity	NPC48824
0.7835	Intermediate Similarity	NPC229407
0.783	Intermediate Similarity	NPC475176
0.7826	Intermediate Similarity	NPC263951
0.7826	Intermediate Similarity	NPC118987
0.7822	Intermediate Similarity	NPC228766
0.7822	Intermediate Similarity	NPC165528
0.7822	Intermediate Similarity	NPC329910
0.7822	Intermediate Similarity	NPC327788
0.7812	Intermediate Similarity	NPC471042
0.781	Intermediate Similarity	NPC294259
0.78	Intermediate Similarity	NPC303863
0.78	Intermediate Similarity	NPC476186
0.78	Intermediate Similarity	NPC57117
0.7798	Intermediate Similarity	NPC69291
0.7788	Intermediate Similarity	NPC15396
0.7788	Intermediate Similarity	NPC164551
0.7788	Intermediate Similarity	NPC476081
0.7788	Intermediate Similarity	NPC148628
0.7788	Intermediate Similarity	NPC214946
0.7788	Intermediate Similarity	NPC88203
0.7788	Intermediate Similarity	NPC170615
0.7788	Intermediate Similarity	NPC246736
0.7788	Intermediate Similarity	NPC286519
0.7788	Intermediate Similarity	NPC304832
0.7788	Intermediate Similarity	NPC76866
0.7778	Intermediate Similarity	NPC476187
0.7778	Intermediate Similarity	NPC26888
0.7778	Intermediate Similarity	NPC470113
0.7778	Intermediate Similarity	NPC471901
0.7778	Intermediate Similarity	NPC475416
0.7768	Intermediate Similarity	NPC475372
0.7767	Intermediate Similarity	NPC180733
0.7767	Intermediate Similarity	NPC267921
0.7767	Intermediate Similarity	NPC293866
0.7767	Intermediate Similarity	NPC41971
0.7767	Intermediate Similarity	NPC37047
0.7767	Intermediate Similarity	NPC266955
0.7767	Intermediate Similarity	NPC470074
0.7767	Intermediate Similarity	NPC94906
0.7767	Intermediate Similarity	NPC108371
0.7767	Intermediate Similarity	NPC476274
0.7757	Intermediate Similarity	NPC275539
0.7757	Intermediate Similarity	NPC189075
0.7755	Intermediate Similarity	NPC213832
0.7755	Intermediate Similarity	NPC50488
0.7755	Intermediate Similarity	NPC253618
0.7755	Intermediate Similarity	NPC474396
0.7755	Intermediate Similarity	NPC57954
0.7755	Intermediate Similarity	NPC77001
0.7755	Intermediate Similarity	NPC475921
0.7755	Intermediate Similarity	NPC269267
0.7755	Intermediate Similarity	NPC474889
0.7755	Intermediate Similarity	NPC474704

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 NPC473155 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	1974
0.2-0.3	4089
0.3-0.4	2011
0.4-0.5	445
0.5-0.6	214
0.6-0.7	188
0.7-0.8	13
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7959	Intermediate Similarity	NPD8035	Phase 2
0.7959	Intermediate Similarity	NPD8034	Phase 2
0.7895	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD6399	Phase 3
0.7679	Intermediate Similarity	NPD7115	Discovery
0.767	Intermediate Similarity	NPD7638	Approved
0.7596	Intermediate Similarity	NPD7639	Approved
0.7596	Intermediate Similarity	NPD7640	Approved
0.7549	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4225	Approved
0.7312	Intermediate Similarity	NPD6117	Approved
0.7273	Intermediate Similarity	NPD6881	Approved
0.7273	Intermediate Similarity	NPD3618	Phase 1
0.7273	Intermediate Similarity	NPD7320	Approved
0.7273	Intermediate Similarity	NPD6899	Approved
0.7255	Intermediate Similarity	NPD6079	Approved
0.7248	Intermediate Similarity	NPD7128	Approved
0.7248	Intermediate Similarity	NPD6675	Approved
0.7248	Intermediate Similarity	NPD6008	Approved
0.7248	Intermediate Similarity	NPD6402	Approved
0.7248	Intermediate Similarity	NPD5739	Approved
0.7245	Intermediate Similarity	NPD4786	Approved
0.7234	Intermediate Similarity	NPD6116	Phase 1
0.7232	Intermediate Similarity	NPD6650	Approved
0.7232	Intermediate Similarity	NPD6649	Approved
0.7228	Intermediate Similarity	NPD5328	Approved
0.7207	Intermediate Similarity	NPD6372	Approved
0.7207	Intermediate Similarity	NPD6373	Approved
0.7182	Intermediate Similarity	NPD5697	Approved
0.7158	Intermediate Similarity	NPD6697	Approved
0.7158	Intermediate Similarity	NPD6118	Approved
0.7158	Intermediate Similarity	NPD6115	Approved
0.7158	Intermediate Similarity	NPD6114	Approved
0.7143	Intermediate Similarity	NPD7102	Approved
0.7143	Intermediate Similarity	NPD6883	Approved
0.7143	Intermediate Similarity	NPD4788	Approved
0.7143	Intermediate Similarity	NPD7290	Approved
0.713	Intermediate Similarity	NPD7632	Discontinued
0.7117	Intermediate Similarity	NPD6011	Approved
0.7115	Intermediate Similarity	NPD6001	Approved
0.7115	Intermediate Similarity	NPD7748	Approved
0.7097	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7515	Phase 2
0.708	Intermediate Similarity	NPD6617	Approved
0.708	Intermediate Similarity	NPD8130	Phase 1
0.708	Intermediate Similarity	NPD6847	Approved
0.708	Intermediate Similarity	NPD6869	Approved
0.7075	Intermediate Similarity	NPD6084	Phase 2
0.7075	Intermediate Similarity	NPD6083	Phase 2
0.7075	Intermediate Similarity	NPD7902	Approved
0.7054	Intermediate Similarity	NPD6014	Approved
0.7054	Intermediate Similarity	NPD6012	Approved
0.7054	Intermediate Similarity	NPD6013	Approved
0.7041	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD3667	Approved
0.7027	Intermediate Similarity	NPD5701	Approved
0.7018	Intermediate Similarity	NPD8297	Approved
0.7018	Intermediate Similarity	NPD6882	Approved
0.7	Intermediate Similarity	NPD1694	Approved
0.6981	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4697	Phase 3
0.6981	Remote Similarity	NPD5221	Approved
0.6981	Remote Similarity	NPD5222	Approved
0.6961	Remote Similarity	NPD6672	Approved
0.6961	Remote Similarity	NPD5737	Approved
0.6961	Remote Similarity	NPD6903	Approved
0.6931	Remote Similarity	NPD7521	Approved
0.6931	Remote Similarity	NPD7334	Approved
0.6931	Remote Similarity	NPD6684	Approved
0.6931	Remote Similarity	NPD7146	Approved
0.6931	Remote Similarity	NPD6409	Approved
0.6931	Remote Similarity	NPD5330	Approved
0.693	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD5173	Approved
0.6857	Remote Similarity	NPD4202	Approved
0.6852	Remote Similarity	NPD5696	Approved
0.6838	Remote Similarity	NPD6868	Approved
0.6833	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD5785	Approved
0.6818	Remote Similarity	NPD5211	Phase 2
0.681	Remote Similarity	NPD8133	Approved
0.6796	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7900	Approved
0.6792	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD4696	Approved
0.6789	Remote Similarity	NPD5285	Approved
0.6789	Remote Similarity	NPD5286	Approved
0.6762	Remote Similarity	NPD5693	Phase 1
0.6759	Remote Similarity	NPD4755	Approved
0.6754	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7507	Approved
0.6733	Remote Similarity	NPD3666	Approved
0.6733	Remote Similarity	NPD3133	Approved
0.6733	Remote Similarity	NPD3665	Phase 1
0.6729	Remote Similarity	NPD5695	Phase 3
0.6729	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5223	Approved
0.6723	Remote Similarity	NPD6335	Approved
0.6721	Remote Similarity	NPD7604	Phase 2
0.6702	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5141	Approved
0.6696	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6274	Approved
0.6694	Remote Similarity	NPD7078	Approved
0.6667	Remote Similarity	NPD7100	Approved
0.6667	Remote Similarity	NPD5225	Approved
0.6667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD5224	Approved
0.6667	Remote Similarity	NPD4633	Approved
0.6667	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD5226	Approved
0.6667	Remote Similarity	NPD7525	Registered
0.6667	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD4632	Approved
0.6639	Remote Similarity	NPD6317	Approved
0.6636	Remote Similarity	NPD4700	Approved
0.6634	Remote Similarity	NPD5362	Discontinued
0.6613	Remote Similarity	NPD6616	Approved
0.6612	Remote Similarity	NPD6054	Approved
0.6607	Remote Similarity	NPD5175	Approved
0.6607	Remote Similarity	NPD5174	Approved
0.6604	Remote Similarity	NPD7637	Suspended
0.6602	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD7319	Approved
0.6583	Remote Similarity	NPD6314	Approved
0.6583	Remote Similarity	NPD6313	Approved
0.6581	Remote Similarity	NPD6053	Discontinued
0.6574	Remote Similarity	NPD4629	Approved
0.6574	Remote Similarity	NPD5210	Approved
0.6571	Remote Similarity	NPD6904	Approved
0.6571	Remote Similarity	NPD6051	Approved
0.6571	Remote Similarity	NPD6673	Approved
0.6571	Remote Similarity	NPD6080	Approved
0.6571	Remote Similarity	NPD4753	Phase 2
0.6569	Remote Similarity	NPD3668	Phase 3
0.6509	Remote Similarity	NPD5207	Approved
0.6508	Remote Similarity	NPD7736	Approved
0.6505	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD6370	Approved
0.65	Remote Similarity	NPD6009	Approved
0.6495	Remote Similarity	NPD3702	Approved
0.6495	Remote Similarity	NPD7339	Approved
0.6495	Remote Similarity	NPD6942	Approved
0.6489	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD6059	Approved
0.6475	Remote Similarity	NPD6319	Approved
0.6465	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.646	Remote Similarity	NPD4754	Approved
0.6449	Remote Similarity	NPD5284	Approved
0.6449	Remote Similarity	NPD6411	Approved
0.6449	Remote Similarity	NPD5281	Approved
0.6446	Remote Similarity	NPD7327	Approved
0.6446	Remote Similarity	NPD7328	Approved
0.6442	Remote Similarity	NPD5279	Phase 3
0.6442	Remote Similarity	NPD6098	Approved
0.6435	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8293	Discontinued
0.6423	Remote Similarity	NPD6908	Approved
0.6423	Remote Similarity	NPD6015	Approved
0.6423	Remote Similarity	NPD8033	Approved
0.6423	Remote Similarity	NPD5983	Phase 2
0.6423	Remote Similarity	NPD6909	Approved
0.6423	Remote Similarity	NPD6016	Approved
0.6415	Remote Similarity	NPD1695	Approved
0.6413	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.641	Remote Similarity	NPD6371	Approved
0.6393	Remote Similarity	NPD7516	Approved
0.6381	Remote Similarity	NPD3573	Approved
0.6379	Remote Similarity	NPD5168	Approved
0.6379	Remote Similarity	NPD4730	Approved
0.6379	Remote Similarity	NPD4729	Approved
0.6379	Remote Similarity	NPD5128	Approved
0.6373	Remote Similarity	NPD4223	Phase 3
0.6373	Remote Similarity	NPD4221	Approved
0.6371	Remote Similarity	NPD5988	Approved
0.6354	Remote Similarity	NPD6081	Approved
0.6354	Remote Similarity	NPD5777	Approved
0.6349	Remote Similarity	NPD6336	Discontinued
0.6348	Remote Similarity	NPD4767	Approved
0.6348	Remote Similarity	NPD4768	Approved
0.6346	Remote Similarity	NPD5363	Approved
0.6346	Remote Similarity	NPD5329	Approved
0.6341	Remote Similarity	NPD8294	Approved
0.6341	Remote Similarity	NPD8377	Approved
0.6327	Remote Similarity	NPD3703	Phase 2
0.6321	Remote Similarity	NPD5208	Approved
0.6316	Remote Similarity	NPD6052	Approved
0.6311	Remote Similarity	NPD6695	Phase 3
0.6296	Remote Similarity	NPD6050	Approved
0.6293	Remote Similarity	NPD6412	Phase 2
0.629	Remote Similarity	NPD8380	Approved
0.629	Remote Similarity	NPD8379	Approved
0.629	Remote Similarity	NPD8335	Approved
0.629	Remote Similarity	NPD8378	Approved
0.629	Remote Similarity	NPD8296	Approved
0.6283	Remote Similarity	NPD1700	Approved
0.6275	Remote Similarity	NPD5369	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