NPASS Compound

Structure

NPC330659 OpenBabel07101719152D 22 25 0 0 1 0 0 0 0 0999 V2000 -1.4576 -2.1380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2424 -1.5801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8709 -1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2472 -2.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2650 -1.0088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5630 -1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2472 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 -1.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8709 -1.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 0.3600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0896 -0.9960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9195 0.3930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0646 -1.2185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5775 -0.3600 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.2472 -0.7201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.7201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3709 -0.2141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 -1.0801 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8709 -1.0801 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3709 -0.2141 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8709 0.6519 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 4 8 1 0 0 0 0 4 9 1 0 0 0 0 5 6 1 0 0 0 0 5 14 1 0 0 0 0 6 16 1 0 0 0 0 7 10 1 0 0 0 0 7 15 1 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 11 13 1 0 0 0 0 11 20 1 0 0 0 0 12 14 1 0 0 0 0 12 20 1 0 0 0 0 13 14 1 0 0 0 0 15 18 1 6 0 0 0 15 19 1 0 0 0 0 16 18 1 6 0 0 0 16 20 1 0 0 0 0 17 19 1 0 0 0 0 17 21 2 0 0 0 0 17 22 1 0 0 0 0 18 2 1 6 0 0 0 19 3 1 6 0 0 0 20 10 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.22
Volume:	332.558
LogP:	4.802
LogD:	3.578
LogS:	-3.521
# Rotatable Bonds:	1
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.689
Synthetic Accessibility Score:	5.468
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.691
MDCK Permeability:	6.256664164538961e-06
Pgp-inhibitor:	0.022
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.206
30% Bioavailability (F30%):	0.427

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.297
Plasma Protein Binding (PPB):	82.4222412109375%
Volume Distribution (VD):	0.383
Pgp-substrate:	11.938313484191895%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.566
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.777
CYP2C9-inhibitor:	0.077
CYP2C9-substrate:	0.146
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.224
CYP3A4-inhibitor:	0.682
CYP3A4-substrate:	0.158

ADMET: Excretion

Clearance (CL):	2.795
Half-life (T1/2):	0.145

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.662
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.42
Maximum Recommended Daily Dose:	0.757
Skin Sensitization:	0.093
Carcinogencity:	0.846
Eye Corrosion:	0.02
Eye Irritation:	0.049
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC330659

Natural Product ID:	NPC330659
*Common Name:**	NIKHGUQULKYIGE-LFVVLLIQSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NIKHGUQULKYIGE-LFVVLLIQSA-N
Standard InCHI:	InChI=1S/C20H30O2/c1-13-11-20-10-7-15-18(2,16(20)6-5-14(13)12-20)8-4-9-19(15,3)17(21)22/h14-16H,1,4-12H2,2-3H3,(H,21,22)/t14?,15-,16-,18+,19-,20+/m0/s1
SMILES:	C=C1C[C@]23CC[C@H]4[C@@](C)(CCC[C@]4(C)C(=O)O)[C@@H]3CCC1C2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL480983
PubChem CID:	159887
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	small food enterprises (Zvijezda d.d., Zagreb, Croatia)	n.a.	DOI[10.1002/EJLT.200900231]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11746-997-0093-1]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16660462]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	flower petals	n.a.	n.a.	PMID[17480100]
NPO33321	aristolochia constricta	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18570470]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO26659	Annona bullata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2778448]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[6361218]
NPO26659	Annona bullata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8350089]
NPO33321	aristolochia constricta	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9392875]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Flower Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Pollen Or Spore	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26659	Annona bullata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26659	Annona bullata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26659	Annona bullata	Species	Annonaceae	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
MIC	2
Others	3

Activity Type	# Activity
Organism	3
Tissue	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	12.5	ug.mL-1	PMID[521027]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	6.25	ug.mL-1	PMID[521027]
NPT140	Organism	Artemia	Artemia	LC50	=	0.87	ug.mL-1	PMID[521028]
NPT548	Tissue	Ileum	Cavia porcellus	Inhibition	=	28.2	%	PMID[521029]
NPT548	Tissue	Ileum	Cavia porcellus	Inhibition	=	25.4	%	PMID[521029]

☑ 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 NPC330659 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	143
0.1-0.2	1573
0.2-0.3	10084
0.3-0.4	13830
0.4-0.5	6296
0.5-0.6	6010
0.6-0.7	3427
0.7-0.8	1147
0.8-0.85	147
0.85-0.9	26
0.9-0.95	8
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC161187
1.0	High Similarity	NPC244708
0.9571	High Similarity	NPC246445
0.9437	High Similarity	NPC66105
0.9437	High Similarity	NPC212661
0.9437	High Similarity	NPC471035
0.9437	High Similarity	NPC68828
0.9178	High Similarity	NPC192744
0.9143	High Similarity	NPC279241
0.9143	High Similarity	NPC36310
0.8904	High Similarity	NPC238227
0.8841	High Similarity	NPC290445
0.8841	High Similarity	NPC36616
0.8816	High Similarity	NPC170985
0.8784	High Similarity	NPC321690
0.8767	High Similarity	NPC89294
0.8767	High Similarity	NPC20466
0.875	High Similarity	NPC255168
0.8701	High Similarity	NPC245866
0.8701	High Similarity	NPC167103
0.8701	High Similarity	NPC471037
0.8701	High Similarity	NPC472740
0.8684	High Similarity	NPC147066
0.8667	High Similarity	NPC158846
0.8649	High Similarity	NPC106078
0.8649	High Similarity	NPC471899
0.8649	High Similarity	NPC107039
0.8649	High Similarity	NPC471897
0.863	High Similarity	NPC192540
0.863	High Similarity	NPC201027
0.863	High Similarity	NPC279666
0.8592	High Similarity	NPC235586
0.8592	High Similarity	NPC91369
0.859	High Similarity	NPC263974
0.8551	High Similarity	NPC477931
0.8551	High Similarity	NPC42060
0.8551	High Similarity	NPC268736
0.8533	High Similarity	NPC63020
0.8533	High Similarity	NPC110094
0.8533	High Similarity	NPC280654
0.8533	High Similarity	NPC260385
0.8514	High Similarity	NPC69143
0.8493	Intermediate Similarity	NPC251970
0.8493	Intermediate Similarity	NPC161923
0.8493	Intermediate Similarity	NPC241854
0.8493	Intermediate Similarity	NPC283908
0.8493	Intermediate Similarity	NPC183503
0.8493	Intermediate Similarity	NPC476046
0.8493	Intermediate Similarity	NPC103958
0.8481	Intermediate Similarity	NPC201655
0.8481	Intermediate Similarity	NPC264317
0.8481	Intermediate Similarity	NPC294438
0.8472	Intermediate Similarity	NPC72343
0.8442	Intermediate Similarity	NPC38350
0.8442	Intermediate Similarity	NPC201912
0.8442	Intermediate Similarity	NPC232625
0.8429	Intermediate Similarity	NPC474221
0.8429	Intermediate Similarity	NPC478180
0.8429	Intermediate Similarity	NPC130459
0.8421	Intermediate Similarity	NPC471475
0.8421	Intermediate Similarity	NPC199595
0.8421	Intermediate Similarity	NPC16394
0.8421	Intermediate Similarity	NPC231431
0.8421	Intermediate Similarity	NPC477371
0.8421	Intermediate Similarity	NPC201459
0.8421	Intermediate Similarity	NPC215843
0.8375	Intermediate Similarity	NPC472505
0.8375	Intermediate Similarity	NPC2783
0.8375	Intermediate Similarity	NPC12774
0.8375	Intermediate Similarity	NPC80590
0.8375	Intermediate Similarity	NPC70661
0.8333	Intermediate Similarity	NPC260956
0.8333	Intermediate Similarity	NPC320514
0.8312	Intermediate Similarity	NPC37038
0.8312	Intermediate Similarity	NPC104545
0.8289	Intermediate Similarity	NPC476810
0.8286	Intermediate Similarity	NPC103734
0.8272	Intermediate Similarity	NPC264005
0.8272	Intermediate Similarity	NPC134197
0.8272	Intermediate Similarity	NPC33768
0.8272	Intermediate Similarity	NPC269360
0.8267	Intermediate Similarity	NPC476601
0.8267	Intermediate Similarity	NPC104806
0.8267	Intermediate Similarity	NPC309399
0.825	Intermediate Similarity	NPC29447
0.8243	Intermediate Similarity	NPC237591
0.8243	Intermediate Similarity	NPC3753
0.8243	Intermediate Similarity	NPC46610
0.8243	Intermediate Similarity	NPC18819
0.8228	Intermediate Similarity	NPC69279
0.8228	Intermediate Similarity	NPC215893
0.8228	Intermediate Similarity	NPC477852
0.8228	Intermediate Similarity	NPC83569
0.8219	Intermediate Similarity	NPC160817
0.8205	Intermediate Similarity	NPC267691
0.8205	Intermediate Similarity	NPC221647
0.8205	Intermediate Similarity	NPC103754
0.8205	Intermediate Similarity	NPC142244
0.8205	Intermediate Similarity	NPC263272
0.8205	Intermediate Similarity	NPC474484
0.8205	Intermediate Similarity	NPC477372
0.8205	Intermediate Similarity	NPC164210
0.8205	Intermediate Similarity	NPC471898
0.8205	Intermediate Similarity	NPC274050
0.8205	Intermediate Similarity	NPC162632
0.8194	Intermediate Similarity	NPC476734
0.8194	Intermediate Similarity	NPC469941
0.8194	Intermediate Similarity	NPC196197
0.8194	Intermediate Similarity	NPC64466
0.8194	Intermediate Similarity	NPC319671
0.8194	Intermediate Similarity	NPC252032
0.8171	Intermediate Similarity	NPC183374
0.8171	Intermediate Similarity	NPC4309
0.8171	Intermediate Similarity	NPC474719
0.8171	Intermediate Similarity	NPC16377
0.8171	Intermediate Similarity	NPC471900
0.8171	Intermediate Similarity	NPC211162
0.8171	Intermediate Similarity	NPC146937
0.8158	Intermediate Similarity	NPC165711
0.8148	Intermediate Similarity	NPC155011
0.8133	Intermediate Similarity	NPC476844
0.8133	Intermediate Similarity	NPC39362
0.8125	Intermediate Similarity	NPC248758
0.8125	Intermediate Similarity	NPC194937
0.8125	Intermediate Similarity	NPC476038
0.8108	Intermediate Similarity	NPC177826
0.8108	Intermediate Similarity	NPC472813
0.8101	Intermediate Similarity	NPC476458
0.8101	Intermediate Similarity	NPC145143
0.8101	Intermediate Similarity	NPC477858
0.8101	Intermediate Similarity	NPC258153
0.8101	Intermediate Similarity	NPC251779
0.8101	Intermediate Similarity	NPC69101
0.8101	Intermediate Similarity	NPC46881
0.8101	Intermediate Similarity	NPC110780
0.8101	Intermediate Similarity	NPC133391
0.8082	Intermediate Similarity	NPC108131
0.8082	Intermediate Similarity	NPC477850
0.8082	Intermediate Similarity	NPC477929
0.8077	Intermediate Similarity	NPC477057
0.8072	Intermediate Similarity	NPC57954
0.8072	Intermediate Similarity	NPC247312
0.8072	Intermediate Similarity	NPC271974
0.8072	Intermediate Similarity	NPC213832
0.8072	Intermediate Similarity	NPC24772
0.8072	Intermediate Similarity	NPC220498
0.8072	Intermediate Similarity	NPC116146
0.8049	Intermediate Similarity	NPC142361
0.8049	Intermediate Similarity	NPC96496
0.8049	Intermediate Similarity	NPC474684
0.8049	Intermediate Similarity	NPC136948
0.8025	Intermediate Similarity	NPC269638
0.8025	Intermediate Similarity	NPC283733
0.8	Intermediate Similarity	NPC475726
0.8	Intermediate Similarity	NPC70834
0.8	Intermediate Similarity	NPC301065
0.8	Intermediate Similarity	NPC291320
0.8	Intermediate Similarity	NPC470015
0.8	Intermediate Similarity	NPC472743
0.8	Intermediate Similarity	NPC118800
0.8	Intermediate Similarity	NPC175410
0.8	Intermediate Similarity	NPC168188
0.8	Intermediate Similarity	NPC477373
0.8	Intermediate Similarity	NPC170862
0.8	Intermediate Similarity	NPC200752
0.8	Intermediate Similarity	NPC471036
0.8	Intermediate Similarity	NPC472498
0.7976	Intermediate Similarity	NPC169933
0.7975	Intermediate Similarity	NPC278459
0.7973	Intermediate Similarity	NPC472309
0.7973	Intermediate Similarity	NPC469940
0.7952	Intermediate Similarity	NPC56413
0.7952	Intermediate Similarity	NPC255176
0.7949	Intermediate Similarity	NPC263951
0.7949	Intermediate Similarity	NPC118987
0.7949	Intermediate Similarity	NPC274996
0.7949	Intermediate Similarity	NPC196827
0.7945	Intermediate Similarity	NPC474962
0.7927	Intermediate Similarity	NPC475007
0.7927	Intermediate Similarity	NPC186975
0.7927	Intermediate Similarity	NPC55309
0.7927	Intermediate Similarity	NPC28252
0.7922	Intermediate Similarity	NPC74685
0.7922	Intermediate Similarity	NPC474433
0.7922	Intermediate Similarity	NPC61952
0.7901	Intermediate Similarity	NPC156981
0.7901	Intermediate Similarity	NPC96095
0.7901	Intermediate Similarity	NPC475509
0.7901	Intermediate Similarity	NPC264665
0.7901	Intermediate Similarity	NPC165064
0.7901	Intermediate Similarity	NPC474233
0.7901	Intermediate Similarity	NPC19849
0.7901	Intermediate Similarity	NPC477289
0.7901	Intermediate Similarity	NPC475745
0.7901	Intermediate Similarity	NPC146683
0.7901	Intermediate Similarity	NPC164577
0.7901	Intermediate Similarity	NPC472864
0.7901	Intermediate Similarity	NPC74595
0.7901	Intermediate Similarity	NPC474482
0.7895	Intermediate Similarity	NPC476795

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 NPC330659 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	140
0.1-0.2	2067
0.2-0.3	4314
0.3-0.4	1744
0.4-0.5	456
0.5-0.6	191
0.6-0.7	158
0.7-0.8	75
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8551	High Similarity	NPD4224	Phase 2
0.8481	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4788	Approved
0.7973	Intermediate Similarity	NPD6081	Approved
0.7882	Intermediate Similarity	NPD8034	Phase 2
0.7882	Intermediate Similarity	NPD8035	Phase 2
0.7875	Intermediate Similarity	NPD4221	Approved
0.7875	Intermediate Similarity	NPD4223	Phase 3
0.7763	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD4786	Approved
0.7683	Intermediate Similarity	NPD4197	Approved
0.7654	Intermediate Similarity	NPD3667	Approved
0.7595	Intermediate Similarity	NPD3617	Approved
0.759	Intermediate Similarity	NPD5329	Approved
0.7586	Intermediate Similarity	NPD6399	Phase 3
0.7568	Intermediate Similarity	NPD5360	Phase 3
0.7568	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD6117	Approved
0.75	Intermediate Similarity	NPD4688	Approved
0.75	Intermediate Similarity	NPD4690	Approved
0.75	Intermediate Similarity	NPD4138	Approved
0.75	Intermediate Similarity	NPD5205	Approved
0.75	Intermediate Similarity	NPD4689	Approved
0.75	Intermediate Similarity	NPD6098	Approved
0.75	Intermediate Similarity	NPD4693	Phase 3
0.7471	Intermediate Similarity	NPD5281	Approved
0.7471	Intermediate Similarity	NPD5284	Approved
0.747	Intermediate Similarity	NPD3665	Phase 1
0.747	Intermediate Similarity	NPD3133	Approved
0.747	Intermediate Similarity	NPD3666	Approved
0.7468	Intermediate Similarity	NPD6116	Phase 1
0.7436	Intermediate Similarity	NPD3702	Approved
0.7397	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD6114	Approved
0.7375	Intermediate Similarity	NPD6697	Approved
0.7375	Intermediate Similarity	NPD6118	Approved
0.7375	Intermediate Similarity	NPD6115	Approved
0.7368	Intermediate Similarity	NPD4789	Approved
0.7326	Intermediate Similarity	NPD5737	Approved
0.7326	Intermediate Similarity	NPD6672	Approved
0.7326	Intermediate Similarity	NPD5208	Approved
0.7326	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD4692	Approved
0.7317	Intermediate Similarity	NPD4139	Approved
0.7294	Intermediate Similarity	NPD5690	Phase 2
0.7294	Intermediate Similarity	NPD3618	Phase 1
0.7294	Intermediate Similarity	NPD6409	Approved
0.7294	Intermediate Similarity	NPD6684	Approved
0.7294	Intermediate Similarity	NPD5330	Approved
0.7294	Intermediate Similarity	NPD5280	Approved
0.7294	Intermediate Similarity	NPD4694	Approved
0.7294	Intermediate Similarity	NPD7521	Approved
0.7294	Intermediate Similarity	NPD7146	Approved
0.7294	Intermediate Similarity	NPD7334	Approved
0.7273	Intermediate Similarity	NPD4758	Discontinued
0.7273	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7515	Phase 2
0.7253	Intermediate Similarity	NPD6084	Phase 2
0.7253	Intermediate Similarity	NPD6083	Phase 2
0.7241	Intermediate Similarity	NPD5328	Approved
0.7241	Intermediate Similarity	NPD4753	Phase 2
0.7241	Intermediate Similarity	NPD6673	Approved
0.7241	Intermediate Similarity	NPD6080	Approved
0.7241	Intermediate Similarity	NPD6904	Approved
0.7241	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD3698	Phase 2
0.7222	Intermediate Similarity	NPD5695	Phase 3
0.7195	Intermediate Similarity	NPD4695	Discontinued
0.7174	Intermediate Similarity	NPD5696	Approved
0.7143	Intermediate Similarity	NPD4244	Approved
0.7143	Intermediate Similarity	NPD4245	Approved
0.7143	Intermediate Similarity	NPD4747	Approved
0.7126	Intermediate Similarity	NPD6903	Approved
0.7111	Intermediate Similarity	NPD7748	Approved
0.7093	Intermediate Similarity	NPD5279	Phase 3
0.7093	Intermediate Similarity	NPD4519	Discontinued
0.7093	Intermediate Similarity	NPD4623	Approved
0.7093	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6079	Approved
0.7079	Intermediate Similarity	NPD5693	Phase 1
0.7073	Intermediate Similarity	NPD4195	Approved
0.7059	Intermediate Similarity	NPD3668	Phase 3
0.7051	Intermediate Similarity	NPD4243	Approved
0.7051	Intermediate Similarity	NPD5777	Approved
0.7024	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4137	Phase 3
0.7	Intermediate Similarity	NPD4202	Approved
0.6966	Remote Similarity	NPD5207	Approved
0.6966	Remote Similarity	NPD5692	Phase 3
0.6923	Remote Similarity	NPD6001	Approved
0.6923	Remote Similarity	NPD4691	Approved
0.6915	Remote Similarity	NPD6404	Discontinued
0.6889	Remote Similarity	NPD5694	Approved
0.6889	Remote Similarity	NPD6050	Approved
0.6883	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7902	Approved
0.6875	Remote Similarity	NPD4785	Approved
0.6875	Remote Similarity	NPD4784	Approved
0.6848	Remote Similarity	NPD4629	Approved
0.6848	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5210	Approved
0.6818	Remote Similarity	NPD3573	Approved
0.6809	Remote Similarity	NPD7638	Approved
0.679	Remote Similarity	NPD3703	Phase 2
0.679	Remote Similarity	NPD5275	Approved
0.679	Remote Similarity	NPD6942	Approved
0.679	Remote Similarity	NPD7339	Approved
0.679	Remote Similarity	NPD4190	Phase 3
0.6786	Remote Similarity	NPD7525	Registered
0.6778	Remote Similarity	NPD4096	Approved
0.6774	Remote Similarity	NPD4697	Phase 3
0.6774	Remote Similarity	NPD5221	Approved
0.6774	Remote Similarity	NPD5222	Approved
0.6774	Remote Similarity	NPD7614	Phase 1
0.6774	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD5364	Discontinued
0.6737	Remote Similarity	NPD7639	Approved
0.6737	Remote Similarity	NPD7640	Approved
0.6735	Remote Similarity	NPD6402	Approved
0.6735	Remote Similarity	NPD7128	Approved
0.6735	Remote Similarity	NPD5739	Approved
0.6735	Remote Similarity	NPD6675	Approved
0.6707	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4755	Approved
0.6702	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD4687	Approved
0.6667	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD5733	Approved
0.6667	Remote Similarity	NPD4058	Approved
0.663	Remote Similarity	NPD5133	Approved
0.6625	Remote Similarity	NPD5276	Approved
0.66	Remote Similarity	NPD6881	Approved
0.66	Remote Similarity	NPD6011	Approved
0.66	Remote Similarity	NPD6899	Approved
0.66	Remote Similarity	NPD7320	Approved
0.6562	Remote Similarity	NPD5285	Approved
0.6562	Remote Similarity	NPD5286	Approved
0.6562	Remote Similarity	NPD4700	Approved
0.6562	Remote Similarity	NPD4696	Approved
0.6559	Remote Similarity	NPD7900	Approved
0.6559	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD4518	Approved
0.6548	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD3671	Phase 1
0.6535	Remote Similarity	NPD6014	Approved
0.6535	Remote Similarity	NPD6012	Approved
0.6535	Remote Similarity	NPD6373	Approved
0.6535	Remote Similarity	NPD6013	Approved
0.6535	Remote Similarity	NPD6372	Approved
0.6512	Remote Similarity	NPD857	Phase 3
0.6495	Remote Similarity	NPD5223	Approved
0.6489	Remote Similarity	NPD5654	Approved
0.6479	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7290	Approved
0.6471	Remote Similarity	NPD7102	Approved
0.6471	Remote Similarity	NPD6883	Approved
0.6463	Remote Similarity	NPD6924	Approved
0.6463	Remote Similarity	NPD6926	Approved
0.6442	Remote Similarity	NPD8133	Approved
0.6429	Remote Similarity	NPD5226	Approved
0.6429	Remote Similarity	NPD5211	Phase 2
0.6429	Remote Similarity	NPD5224	Approved
0.6429	Remote Similarity	NPD4633	Approved
0.6429	Remote Similarity	NPD5225	Approved
0.6429	Remote Similarity	NPD5091	Approved
0.6408	Remote Similarity	NPD6617	Approved
0.6408	Remote Similarity	NPD6869	Approved
0.6408	Remote Similarity	NPD6847	Approved
0.6408	Remote Similarity	NPD6649	Approved
0.6408	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD8130	Phase 1
0.6408	Remote Similarity	NPD6650	Approved
0.6364	Remote Similarity	NPD5175	Approved
0.6364	Remote Similarity	NPD4754	Approved
0.6364	Remote Similarity	NPD6052	Approved
0.6364	Remote Similarity	NPD5174	Approved
0.6354	Remote Similarity	NPD5959	Approved
0.6346	Remote Similarity	NPD6882	Approved
0.6346	Remote Similarity	NPD8297	Approved
0.6344	Remote Similarity	NPD6411	Approved
0.631	Remote Similarity	NPD6933	Approved
0.6304	Remote Similarity	NPD6051	Approved
0.63	Remote Similarity	NPD5141	Approved
0.6286	Remote Similarity	NPD4632	Approved
0.6279	Remote Similarity	NPD7645	Phase 2
0.6269	Remote Similarity	NPD634	Phase 3
0.6263	Remote Similarity	NPD7632	Discontinued
0.625	Remote Similarity	NPD7732	Phase 3
0.6238	Remote Similarity	NPD6008	Approved
0.6238	Remote Similarity	NPD4767	Approved
0.6238	Remote Similarity	NPD4768	Approved
0.6211	Remote Similarity	NPD5707	Approved
0.618	Remote Similarity	NPD5362	Discontinued
0.6176	Remote Similarity	NPD6614	Approved
0.6176	Remote Similarity	NPD6412	Phase 2
0.6173	Remote Similarity	NPD6923	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