NPASS Compound

Structure

CID118078 OpenBabel06191715472D 38 41 0 0 1 0 0 0 0 0999 V2000 -8.6328 0.7062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4090 -4.4318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3655 -0.6028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2316 -0.1028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9588 -1.5164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9099 -3.1637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9044 -3.2682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9692 -0.8765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3007 -2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2872 -1.2459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2261 -0.2074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5135 -3.4373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1667 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7704 -2.7682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1771 -1.8546 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8366 -2.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8366 -3.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7026 -4.4945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5686 -3.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8090 -1.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.3796 -2.9373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 -2.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1045 -0.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4781 -0.6581 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2007 -0.8392 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -4.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 -5.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 -4.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0169 -2.3794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.2931 -3.3440 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3917 -0.2514 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 -2.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -1.4945 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 -10.1717 -1.9592 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 -2.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 13 2 0 0 0 0 5 15 1 0 0 0 0 6 7 1 0 0 0 0 6 15 2 0 0 0 0 7 16 1 0 0 0 0 8 13 1 0 0 0 0 9 15 1 0 0 0 0 9 34 1 0 0 0 0 10 35 1 0 0 0 0 11 26 1 0 0 0 0 11 27 1 0 0 0 0 12 26 1 0 0 0 0 12 36 1 0 0 0 0 14 16 2 0 0 0 0 14 23 1 0 0 0 0 16 17 1 0 0 0 0 17 8 1 1 0 0 0 17 37 1 0 0 0 0 18 10 1 6 0 0 0 18 19 1 0 0 0 0 18 38 1 0 0 0 0 19 20 1 0 0 0 0 19 28 1 1 0 0 0 20 21 1 0 0 0 0 20 29 1 6 0 0 0 21 24 1 0 0 0 0 21 30 1 1 0 0 0 22 25 1 0 0 0 0 22 26 1 1 0 0 0 22 31 1 0 0 0 0 23 32 2 0 0 0 0 23 37 1 0 0 0 0 24 34 1 6 0 0 0 24 38 1 0 0 0 0 25 35 1 6 0 0 0 25 36 1 0 0 0 0 26 33 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	542.24
Volume:	518.963
LogP:	0.662
LogD:	0.22
LogS:	-2.604
# Rotatable Bonds:	7
TPSA:	191.67
# H-Bond Aceptor:	12
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.215
Synthetic Accessibility Score:	5.764
Fsp3:	0.692
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:	-5.934
MDCK Permeability:	8.657742000650615e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.974
Human Intestinal Absorption (HIA):	0.913
20% Bioavailability (F20%):	0.987
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.099
Plasma Protein Binding (PPB):	86.39270782470703%
Volume Distribution (VD):	0.473
Pgp-substrate:	8.243790626525879%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.053
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.035
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.117
CYP3A4-inhibitor:	0.02
CYP3A4-substrate:	0.046

ADMET: Excretion

Clearance (CL):	1.143
Half-life (T1/2):	0.821

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.19
Drug-inuced Liver Injury (DILI):	0.963
AMES Toxicity:	0.783
Rat Oral Acute Toxicity:	0.193
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.645
Carcinogencity:	0.707
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.035

Download Data

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

Natural Product: NPC118078

Natural Product ID:	NPC118078
*Common Name:**	Sarcaglaboside E
IUPAC Name:	(5Z,9E,11aS)-6-[[(2R,3R,4S,5S,6R)-6-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxymethyl]-3,10-dimethyl-7,8,11,11a-tetrahydro-4H-cyclodeca[b]furan-2-one
Synonyms:	sarcaglaboside E
Standard InCHIKey:	NWJVERSQVLPTOS-FSONPFIFSA-N
Standard InCHI:	InChI=1S/C26H38O12/c1-13-4-3-5-15(6-7-16-14(2)23(32)37-17(16)8-13)9-34-24-21(30)20(29)19(28)18(38-24)10-35-25-22(31)26(33,11-27)12-36-25/h4,6,17-22,24-25,27-31,33H,3,5,7-12H2,1-2H3/b13-4+,15-6-/t17-,18+,19+,20-,21+,22-,24+,25+,26+/m0/s1
SMILES:	OC[C@@]1(O)CO[C@H]([C@@H]1O)OC[C@H]1O[C@@H](OC/C/2=CCC3=C(C)C(=O)O[C@H]3C/C(=C/CC2)/C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL475673
PubChem CID:	11526742
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001771] Germacranolides and derivatives

*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
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	Whole plant	n.a.	n.a.	PMID[16643038]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20038159]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	aerial part	n.a.	n.a.	PMID[25442304]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	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
Others	2

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	21.7	%	PMID[522961]
NPT27	Others	Unspecified		Activity	=	42.4	%	PMID[522961]

☑ 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 NPC118078 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	162
0.1-0.2	1481
0.2-0.3	6017
0.3-0.4	14360
0.4-0.5	10644
0.5-0.6	6905
0.6-0.7	2666
0.7-0.8	438
0.8-0.85	22
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8409	Intermediate Similarity	NPC475035
0.8404	Intermediate Similarity	NPC306041
0.8333	Intermediate Similarity	NPC475037
0.8315	Intermediate Similarity	NPC470124
0.828	Intermediate Similarity	NPC238090
0.828	Intermediate Similarity	NPC472195
0.828	Intermediate Similarity	NPC472196
0.8276	Intermediate Similarity	NPC469469
0.8211	Intermediate Similarity	NPC54731
0.8202	Intermediate Similarity	NPC266718
0.8202	Intermediate Similarity	NPC473308
0.8191	Intermediate Similarity	NPC159698
0.8182	Intermediate Similarity	NPC251026
0.8172	Intermediate Similarity	NPC477749
0.8161	Intermediate Similarity	NPC127295
0.8161	Intermediate Similarity	NPC163362
0.8152	Intermediate Similarity	NPC477748
0.8111	Intermediate Similarity	NPC475034
0.81	Intermediate Similarity	NPC239961
0.809	Intermediate Similarity	NPC473315
0.809	Intermediate Similarity	NPC142111
0.8085	Intermediate Similarity	NPC471483
0.8065	Intermediate Similarity	NPC202886
0.8022	Intermediate Similarity	NPC208473
0.8	Intermediate Similarity	NPC288471
0.7979	Intermediate Similarity	NPC9447
0.7935	Intermediate Similarity	NPC475186
0.7935	Intermediate Similarity	NPC118077
0.7895	Intermediate Similarity	NPC320089
0.7895	Intermediate Similarity	NPC473663
0.7895	Intermediate Similarity	NPC475173
0.7895	Intermediate Similarity	NPC473723
0.7895	Intermediate Similarity	NPC473561
0.7872	Intermediate Similarity	NPC473311
0.7872	Intermediate Similarity	NPC327253
0.7872	Intermediate Similarity	NPC473904
0.7849	Intermediate Similarity	NPC280621
0.7849	Intermediate Similarity	NPC470137
0.7849	Intermediate Similarity	NPC233551
0.7849	Intermediate Similarity	NPC48338
0.7849	Intermediate Similarity	NPC20339
0.7849	Intermediate Similarity	NPC21208
0.7849	Intermediate Similarity	NPC40376
0.7822	Intermediate Similarity	NPC86095
0.7812	Intermediate Similarity	NPC294293
0.7812	Intermediate Similarity	NPC256368
0.7789	Intermediate Similarity	NPC473707
0.7766	Intermediate Similarity	NPC139418
0.7766	Intermediate Similarity	NPC249408
0.7766	Intermediate Similarity	NPC285588
0.7766	Intermediate Similarity	NPC104129
0.7742	Intermediate Similarity	NPC178215
0.7717	Intermediate Similarity	NPC471494
0.7717	Intermediate Similarity	NPC329838
0.7717	Intermediate Similarity	NPC470658
0.7717	Intermediate Similarity	NPC477014
0.7717	Intermediate Similarity	NPC477013
0.7717	Intermediate Similarity	NPC120398
0.7717	Intermediate Similarity	NPC471567
0.7717	Intermediate Similarity	NPC329615
0.7708	Intermediate Similarity	NPC473520
0.7708	Intermediate Similarity	NPC320552
0.7701	Intermediate Similarity	NPC229655
0.7701	Intermediate Similarity	NPC326661
0.77	Intermediate Similarity	NPC219038
0.77	Intermediate Similarity	NPC198992
0.7684	Intermediate Similarity	NPC303451
0.7684	Intermediate Similarity	NPC239517
0.7684	Intermediate Similarity	NPC6414
0.7677	Intermediate Similarity	NPC203627
0.7667	Intermediate Similarity	NPC280367
0.766	Intermediate Similarity	NPC320458
0.766	Intermediate Similarity	NPC89001
0.766	Intermediate Similarity	NPC473905
0.764	Intermediate Similarity	NPC179933
0.7634	Intermediate Similarity	NPC142117
0.7634	Intermediate Similarity	NPC62118
0.7634	Intermediate Similarity	NPC231096
0.7634	Intermediate Similarity	NPC232555
0.7634	Intermediate Similarity	NPC477015
0.7634	Intermediate Similarity	NPC240695
0.7634	Intermediate Similarity	NPC171174
0.7634	Intermediate Similarity	NPC114694
0.7634	Intermediate Similarity	NPC47937
0.7634	Intermediate Similarity	NPC107717
0.7634	Intermediate Similarity	NPC134865
0.7634	Intermediate Similarity	NPC475581
0.7634	Intermediate Similarity	NPC103523
0.7634	Intermediate Similarity	NPC311163
0.7624	Intermediate Similarity	NPC201191
0.7624	Intermediate Similarity	NPC310804
0.7624	Intermediate Similarity	NPC471599
0.7624	Intermediate Similarity	NPC261117
0.7609	Intermediate Similarity	NPC156804
0.7609	Intermediate Similarity	NPC163093
0.7604	Intermediate Similarity	NPC472199
0.7604	Intermediate Similarity	NPC472197
0.7604	Intermediate Similarity	NPC110072
0.76	Intermediate Similarity	NPC244878
0.7579	Intermediate Similarity	NPC473504
0.7579	Intermediate Similarity	NPC20621
0.7579	Intermediate Similarity	NPC40066
0.7579	Intermediate Similarity	NPC318963
0.7579	Intermediate Similarity	NPC93794
0.7579	Intermediate Similarity	NPC477011
0.7579	Intermediate Similarity	NPC477017
0.7579	Intermediate Similarity	NPC477016
0.7579	Intermediate Similarity	NPC42598
0.7579	Intermediate Similarity	NPC81778
0.7579	Intermediate Similarity	NPC91067
0.7576	Intermediate Similarity	NPC2666
0.7576	Intermediate Similarity	NPC471490
0.7553	Intermediate Similarity	NPC476583
0.7553	Intermediate Similarity	NPC20533
0.7553	Intermediate Similarity	NPC258068
0.7553	Intermediate Similarity	NPC473995
0.7551	Intermediate Similarity	NPC469543
0.7551	Intermediate Similarity	NPC471492
0.7528	Intermediate Similarity	NPC133377
0.7528	Intermediate Similarity	NPC477314
0.7527	Intermediate Similarity	NPC103284
0.7527	Intermediate Similarity	NPC1083
0.7527	Intermediate Similarity	NPC132496
0.7527	Intermediate Similarity	NPC473651
0.7527	Intermediate Similarity	NPC322529
0.7527	Intermediate Similarity	NPC283085
0.7527	Intermediate Similarity	NPC477747
0.7527	Intermediate Similarity	NPC82795
0.7527	Intermediate Similarity	NPC286338
0.7527	Intermediate Similarity	NPC223871
0.7527	Intermediate Similarity	NPC473669
0.7527	Intermediate Similarity	NPC473478
0.7527	Intermediate Similarity	NPC66346
0.7527	Intermediate Similarity	NPC107986
0.7527	Intermediate Similarity	NPC231009
0.7527	Intermediate Similarity	NPC110710
0.7527	Intermediate Similarity	NPC477746
0.7527	Intermediate Similarity	NPC182383
0.7526	Intermediate Similarity	NPC11456
0.7526	Intermediate Similarity	NPC61201
0.7525	Intermediate Similarity	NPC20673
0.7524	Intermediate Similarity	NPC206618
0.75	Intermediate Similarity	NPC473619
0.75	Intermediate Similarity	NPC177668
0.75	Intermediate Similarity	NPC229799
0.75	Intermediate Similarity	NPC116543
0.75	Intermediate Similarity	NPC471569
0.75	Intermediate Similarity	NPC151093
0.75	Intermediate Similarity	NPC284472
0.75	Intermediate Similarity	NPC254538
0.75	Intermediate Similarity	NPC286770
0.75	Intermediate Similarity	NPC474285
0.7475	Intermediate Similarity	NPC473333
0.7475	Intermediate Similarity	NPC256230
0.7474	Intermediate Similarity	NPC100454
0.7474	Intermediate Similarity	NPC234077
0.7474	Intermediate Similarity	NPC61257
0.7474	Intermediate Similarity	NPC151403
0.7474	Intermediate Similarity	NPC39754
0.7474	Intermediate Similarity	NPC169511
0.7474	Intermediate Similarity	NPC171135
0.7474	Intermediate Similarity	NPC133730
0.7474	Intermediate Similarity	NPC261952
0.7474	Intermediate Similarity	NPC137368
0.7474	Intermediate Similarity	NPC320569
0.7474	Intermediate Similarity	NPC287164
0.7474	Intermediate Similarity	NPC172821
0.7474	Intermediate Similarity	NPC191929
0.7474	Intermediate Similarity	NPC242364
0.7474	Intermediate Similarity	NPC274446
0.7474	Intermediate Similarity	NPC81045
0.7451	Intermediate Similarity	NPC250545
0.7451	Intermediate Similarity	NPC222062
0.7451	Intermediate Similarity	NPC121423
0.7451	Intermediate Similarity	NPC195510
0.7451	Intermediate Similarity	NPC13171
0.7449	Intermediate Similarity	NPC472198
0.7447	Intermediate Similarity	NPC132940
0.7447	Intermediate Similarity	NPC293136
0.7447	Intermediate Similarity	NPC219498
0.7447	Intermediate Similarity	NPC25703
0.7447	Intermediate Similarity	NPC219652
0.7447	Intermediate Similarity	NPC210218
0.7447	Intermediate Similarity	NPC204686
0.7447	Intermediate Similarity	NPC473840
0.7447	Intermediate Similarity	NPC308412
0.7447	Intermediate Similarity	NPC473687
0.7447	Intermediate Similarity	NPC69082
0.7447	Intermediate Similarity	NPC134885
0.7447	Intermediate Similarity	NPC241360
0.7447	Intermediate Similarity	NPC282815
0.7447	Intermediate Similarity	NPC134807
0.7447	Intermediate Similarity	NPC112685
0.7447	Intermediate Similarity	NPC279267
0.7444	Intermediate Similarity	NPC180725
0.7429	Intermediate Similarity	NPC219900
0.7429	Intermediate Similarity	NPC392
0.7429	Intermediate Similarity	NPC177524
0.7429	Intermediate Similarity	NPC38948
0.7426	Intermediate Similarity	NPC255677

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 NPC118078 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	133
0.1-0.2	1933
0.2-0.3	4237
0.3-0.4	2018
0.4-0.5	594
0.5-0.6	200
0.6-0.7	34
0.7-0.8	1
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
0.75	Intermediate Similarity	NPD46	Approved
0.75	Intermediate Similarity	NPD6698	Approved
0.7429	Intermediate Similarity	NPD6686	Approved
0.7327	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7838	Discovery
0.7053	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD7327	Approved
0.6991	Remote Similarity	NPD7328	Approved
0.6957	Remote Similarity	NPD8033	Approved
0.693	Remote Similarity	NPD7516	Approved
0.6909	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.687	Remote Similarity	NPD8294	Approved
0.687	Remote Similarity	NPD8377	Approved
0.681	Remote Similarity	NPD8379	Approved
0.681	Remote Similarity	NPD8378	Approved
0.681	Remote Similarity	NPD8296	Approved
0.681	Remote Similarity	NPD8380	Approved
0.681	Remote Similarity	NPD8335	Approved
0.6723	Remote Similarity	NPD7507	Approved
0.6697	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8513	Phase 3
0.6667	Remote Similarity	NPD8516	Approved
0.6667	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD8515	Approved
0.6557	Remote Similarity	NPD7319	Approved
0.6542	Remote Similarity	NPD5344	Discontinued
0.6525	Remote Similarity	NPD7503	Approved
0.6408	Remote Similarity	NPD7983	Approved
0.6337	Remote Similarity	NPD4250	Approved
0.6337	Remote Similarity	NPD4251	Approved
0.63	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD7830	Approved
0.6281	Remote Similarity	NPD7642	Approved
0.6281	Remote Similarity	NPD7829	Approved
0.625	Remote Similarity	NPD6412	Phase 2
0.6238	Remote Similarity	NPD4249	Approved
0.6228	Remote Similarity	NPD6371	Approved
0.6204	Remote Similarity	NPD4225	Approved
0.6154	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD6648	Approved
0.6134	Remote Similarity	NPD7641	Discontinued
0.6129	Remote Similarity	NPD8074	Phase 3
0.6116	Remote Similarity	NPD8444	Approved
0.6068	Remote Similarity	NPD8133	Approved
0.6048	Remote Similarity	NPD8451	Approved
0.6019	Remote Similarity	NPD7839	Suspended
0.6	Remote Similarity	NPD8448	Approved
0.6	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD6053	Discontinued
0.5983	Remote Similarity	NPD969	Suspended
0.598	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.596	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD6110	Phase 1
0.5935	Remote Similarity	NPD8080	Discontinued
0.5917	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD7505	Discontinued
0.5909	Remote Similarity	NPD7638	Approved
0.5862	Remote Similarity	NPD9119	Approved
0.5862	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD69	Approved
0.5859	Remote Similarity	NPD8390	Approved
0.5859	Remote Similarity	NPD8392	Approved
0.5859	Remote Similarity	NPD8391	Approved
0.5856	Remote Similarity	NPD7639	Approved
0.5856	Remote Similarity	NPD7640	Approved
0.5841	Remote Similarity	NPD1407	Approved
0.584	Remote Similarity	NPD8341	Approved
0.584	Remote Similarity	NPD8340	Approved
0.584	Remote Similarity	NPD8342	Approved
0.584	Remote Similarity	NPD8299	Approved
0.5833	Remote Similarity	NPD5282	Discontinued
0.5833	Remote Similarity	NPD887	Approved
0.5833	Remote Similarity	NPD895	Approved
0.5833	Remote Similarity	NPD889	Approved
0.5833	Remote Similarity	NPD894	Approved
0.5833	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD2267	Suspended
0.58	Remote Similarity	NPD4820	Approved
0.58	Remote Similarity	NPD4819	Approved
0.58	Remote Similarity	NPD4821	Approved
0.58	Remote Similarity	NPD4822	Approved
0.5794	Remote Similarity	NPD7637	Suspended
0.5784	Remote Similarity	NPD7154	Phase 3
0.578	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD2204	Approved
0.576	Remote Similarity	NPD8328	Phase 3
0.5758	Remote Similarity	NPD4271	Approved
0.5758	Remote Similarity	NPD4268	Approved
0.5755	Remote Similarity	NPD1695	Approved
0.5748	Remote Similarity	NPD8293	Discontinued
0.5747	Remote Similarity	NPD9118	Approved
0.5739	Remote Similarity	NPD4211	Phase 1
0.5726	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD2269	Approved
0.5703	Remote Similarity	NPD7736	Approved
0.5699	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.568	Remote Similarity	NPD6370	Approved
0.5678	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD5362	Discontinued

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