NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	238.19
Volume:	265.827
LogP:	2.48
LogD:	2.193
LogS:	-2.941
# Rotatable Bonds:	1
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.69
Synthetic Accessibility Score:	4.315
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.418
MDCK Permeability:	2.035691613855306e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.455
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.286
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.814
Plasma Protein Binding (PPB):	46.825828552246094%
Volume Distribution (VD):	1.145
Pgp-substrate:	53.35954284667969%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.155
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.8
CYP2C9-inhibitor:	0.026
CYP2C9-substrate:	0.138
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.221
CYP3A4-inhibitor:	0.203
CYP3A4-substrate:	0.264

ADMET: Excretion

Clearance (CL):	9.548
Half-life (T1/2):	0.26

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.184
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.088
Rat Oral Acute Toxicity:	0.945
Maximum Recommended Daily Dose:	0.983
Skin Sensitization:	0.171
Carcinogencity:	0.266
Eye Corrosion:	0.078
Eye Irritation:	0.834
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC253303

Natural Product ID:	NPC253303
*Common Name:**	4(15)-Eudesmene-1Beta,7Alpha-Diol
IUPAC Name:	(1R,4aS,6S,8aR)-8a-methyl-4-methylidene-6-propan-2-yl-2,3,4a,5,7,8-hexahydro-1H-naphthalene-1,6-diol
Synonyms:
Standard InCHIKey:	SWIPEIJPNVNEPT-YJNKXOJESA-N
Standard InCHI:	InChI=1S/C15H26O2/c1-10(2)15(17)8-7-14(4)12(9-15)11(3)5-6-13(14)16/h10,12-13,16-17H,3,5-9H2,1-2,4H3/t12-,13+,14+,15-/m0/s1
SMILES:	C=C1CC[C@H]([C@]2([C@H]1C[C@@](O)(CC2)C(C)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL501913
PubChem CID:	11470456
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0000101] Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids

*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
NPO25111	Streptomyces tanashiensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(01)84249-0]
NPO4501	Caragana intermedia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15620236]
NPO24121	Vernoniopsis caudata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[15921436]
NPO20815	Lindera fruticosa	Species	Lauraceae	Eukaryota	roots	n.a.	n.a.	PMID[16724860]
NPO29956	Sanicula lamelligera	Species	Apiaceae	Eukaryota	Whole plants	Mountain Emei, Sichuan Province, China	2008-OCT	PMID[21561060]
NPO29956	Sanicula lamelligera	Species	Apiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21561060]
NPO24560	Ricinus communis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26509914]
NPO20362	Ruta montana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22722	Ranunculus japonicus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21787	Betula pubescens	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24560	Ricinus communis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22722	Ranunculus japonicus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24560	Ricinus communis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20362	Ruta montana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21787	Betula pubescens	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20362	Ruta montana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24560	Ricinus communis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24560	Ricinus communis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23948	Serratia plymuthica	Species	Yersiniaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO20936	Arecastrum romanzoffianum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO21683	Selaginella lepidophylla	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14448	Laurencia venusta	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22722	Ranunculus japonicus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21787	Betula pubescens	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23843	Clerodendrum grayi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18589	Allopora californica	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16184	Asclepias asperula	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24560	Ricinus communis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20362	Ruta montana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24776	Euryops jacksonii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21121	Ips japonicus	Species	Curculionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23158	Penicillium carminoviolaceum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16971	Sparassis crispa	Species	Sparassidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23445	Vernonia triflosculosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24121	Vernoniopsis caudata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO13388	Lithophyllum incrustans	Species	Corallinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23376	Genista aetnensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17668	Artemisia gmelinii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4501	Caragana intermedia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23676	Fleroya rubrostipulata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25111	Streptomyces tanashiensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO24411	Pentaspadon motleyi	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20226	Artemisia filatovae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22713	Aquilegia flabellata	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20815	Lindera fruticosa	Species	Lauraceae	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
EC50	1
IC50	6
MIC	1
Others	1

Activity Type	# Activity
Cell Line	7
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	64400.0	nM	PMID[491845]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	64400.0	nM	PMID[491845]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	64400.0	nM	PMID[491845]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	64400.0	nM	PMID[491845]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	64400.0	nM	PMID[491845]
NPT1452	Cell Line	C8166	Homo sapiens	CC50	>	420200.0	nM	PMID[491845]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	64400.0	nM	PMID[491845]
NPT826	Organism	Magnaporthe oryzae	Magnaporthe oryzae	MIC	=	12.0	ug.mL-1	PMID[491844]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	>	420200.0	nM	PMID[491845]

☑ 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 NPC253303 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	195
0.1-0.2	2176
0.2-0.3	8355
0.3-0.4	16332
0.4-0.5	6282
0.5-0.6	5750
0.6-0.7	2867
0.7-0.8	632
0.8-0.85	78
0.85-0.9	11
0.9-0.95	14
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC269077
0.9531	High Similarity	NPC245795
0.9516	High Similarity	NPC101128
0.9375	High Similarity	NPC185874
0.9375	High Similarity	NPC139207
0.9254	High Similarity	NPC95165
0.9242	High Similarity	NPC283316
0.9231	High Similarity	NPC244790
0.9206	High Similarity	NPC144650
0.9062	High Similarity	NPC208198
0.9062	High Similarity	NPC11555
0.9062	High Similarity	NPC172613
0.9062	High Similarity	NPC258595
0.9062	High Similarity	NPC60837
0.9062	High Similarity	NPC2728
0.9062	High Similarity	NPC282619
0.8939	High Similarity	NPC266578
0.8939	High Similarity	NPC276616
0.8923	High Similarity	NPC473929
0.8906	High Similarity	NPC68656
0.8857	High Similarity	NPC63958
0.8841	High Similarity	NPC308440
0.8841	High Similarity	NPC472503
0.8824	High Similarity	NPC167706
0.8806	High Similarity	NPC234511
0.871	High Similarity	NPC474769
0.871	High Similarity	NPC189290
0.8636	High Similarity	NPC475897
0.8611	High Similarity	NPC31828
0.8551	High Similarity	NPC164022
0.8529	High Similarity	NPC210323
0.8529	High Similarity	NPC9942
0.8485	Intermediate Similarity	NPC300442
0.8472	Intermediate Similarity	NPC471798
0.8472	Intermediate Similarity	NPC202540
0.8451	Intermediate Similarity	NPC3403
0.8451	Intermediate Similarity	NPC32832
0.8429	Intermediate Similarity	NPC211009
0.8406	Intermediate Similarity	NPC92801
0.8406	Intermediate Similarity	NPC45296
0.8387	Intermediate Similarity	NPC264779
0.8382	Intermediate Similarity	NPC2648
0.8356	Intermediate Similarity	NPC472500
0.8356	Intermediate Similarity	NPC472499
0.8356	Intermediate Similarity	NPC477819
0.8356	Intermediate Similarity	NPC477817
0.8333	Intermediate Similarity	NPC219940
0.8333	Intermediate Similarity	NPC91573
0.831	Intermediate Similarity	NPC201048
0.831	Intermediate Similarity	NPC306727
0.831	Intermediate Similarity	NPC476366
0.8286	Intermediate Similarity	NPC111234
0.8286	Intermediate Similarity	NPC301226
0.8243	Intermediate Similarity	NPC24504
0.8243	Intermediate Similarity	NPC472463
0.8243	Intermediate Similarity	NPC476316
0.8243	Intermediate Similarity	NPC472742
0.8243	Intermediate Similarity	NPC116119
0.8243	Intermediate Similarity	NPC475727
0.8243	Intermediate Similarity	NPC80297
0.8235	Intermediate Similarity	NPC88454
0.8235	Intermediate Similarity	NPC117607
0.8235	Intermediate Similarity	NPC101307
0.8219	Intermediate Similarity	NPC130136
0.8219	Intermediate Similarity	NPC470711
0.8219	Intermediate Similarity	NPC470758
0.8209	Intermediate Similarity	NPC64123
0.8194	Intermediate Similarity	NPC212879
0.8194	Intermediate Similarity	NPC240235
0.8194	Intermediate Similarity	NPC70982
0.8194	Intermediate Similarity	NPC185536
0.8194	Intermediate Similarity	NPC144075
0.8194	Intermediate Similarity	NPC178383
0.8194	Intermediate Similarity	NPC230704
0.8194	Intermediate Similarity	NPC231256
0.8194	Intermediate Similarity	NPC104387
0.8194	Intermediate Similarity	NPC103822
0.8169	Intermediate Similarity	NPC182717
0.8133	Intermediate Similarity	NPC47149
0.8133	Intermediate Similarity	NPC78545
0.8133	Intermediate Similarity	NPC475679
0.8133	Intermediate Similarity	NPC71535
0.8108	Intermediate Similarity	NPC472502
0.8108	Intermediate Similarity	NPC475
0.8108	Intermediate Similarity	NPC285761
0.8108	Intermediate Similarity	NPC472342
0.8108	Intermediate Similarity	NPC301707
0.8108	Intermediate Similarity	NPC472501
0.8108	Intermediate Similarity	NPC42853
0.8108	Intermediate Similarity	NPC52755
0.8088	Intermediate Similarity	NPC476406
0.8082	Intermediate Similarity	NPC470766
0.8082	Intermediate Similarity	NPC253190
0.8082	Intermediate Similarity	NPC278091
0.8082	Intermediate Similarity	NPC93662
0.8082	Intermediate Similarity	NPC78067
0.8082	Intermediate Similarity	NPC470749
0.8082	Intermediate Similarity	NPC86305
0.8082	Intermediate Similarity	NPC265588
0.8082	Intermediate Similarity	NPC14112
0.8056	Intermediate Similarity	NPC91858
0.8056	Intermediate Similarity	NPC49168
0.8056	Intermediate Similarity	NPC62657
0.8056	Intermediate Similarity	NPC100334
0.8056	Intermediate Similarity	NPC192638
0.8056	Intermediate Similarity	NPC25511
0.8056	Intermediate Similarity	NPC5046
0.8056	Intermediate Similarity	NPC145552
0.8056	Intermediate Similarity	NPC243342
0.8056	Intermediate Similarity	NPC196358
0.8056	Intermediate Similarity	NPC254509
0.8056	Intermediate Similarity	NPC476736
0.8056	Intermediate Similarity	NPC477138
0.8052	Intermediate Similarity	NPC85095
0.8052	Intermediate Similarity	NPC211135
0.8052	Intermediate Similarity	NPC216420
0.8052	Intermediate Similarity	NPC232023
0.8052	Intermediate Similarity	NPC470929
0.8028	Intermediate Similarity	NPC23954
0.8028	Intermediate Similarity	NPC242992
0.8026	Intermediate Similarity	NPC249423
0.8026	Intermediate Similarity	NPC242350
0.8026	Intermediate Similarity	NPC476646
0.8	Intermediate Similarity	NPC273410
0.8	Intermediate Similarity	NPC49599
0.8	Intermediate Similarity	NPC49627
0.8	Intermediate Similarity	NPC291379
0.8	Intermediate Similarity	NPC80530
0.7973	Intermediate Similarity	NPC157996
0.7973	Intermediate Similarity	NPC212241
0.7973	Intermediate Similarity	NPC90979
0.7973	Intermediate Similarity	NPC119355
0.7973	Intermediate Similarity	NPC260301
0.7973	Intermediate Similarity	NPC248830
0.7973	Intermediate Similarity	NPC40394
0.7973	Intermediate Similarity	NPC34177
0.7973	Intermediate Similarity	NPC257191
0.7973	Intermediate Similarity	NPC138502
0.7973	Intermediate Similarity	NPC472805
0.7973	Intermediate Similarity	NPC101475
0.7973	Intermediate Similarity	NPC331618
0.7973	Intermediate Similarity	NPC307336
0.7969	Intermediate Similarity	NPC236588
0.7969	Intermediate Similarity	NPC135438
0.7949	Intermediate Similarity	NPC474493
0.7949	Intermediate Similarity	NPC86238
0.7945	Intermediate Similarity	NPC291503
0.7945	Intermediate Similarity	NPC477923
0.7945	Intermediate Similarity	NPC66566
0.7945	Intermediate Similarity	NPC200243
0.7937	Intermediate Similarity	NPC84824
0.7937	Intermediate Similarity	NPC67508
0.7922	Intermediate Similarity	NPC472504
0.7922	Intermediate Similarity	NPC248886
0.7917	Intermediate Similarity	NPC220939
0.7917	Intermediate Similarity	NPC471799
0.7917	Intermediate Similarity	NPC195489
0.7917	Intermediate Similarity	NPC265485
0.7917	Intermediate Similarity	NPC68443
0.7903	Intermediate Similarity	NPC102336
0.7903	Intermediate Similarity	NPC36002
0.7895	Intermediate Similarity	NPC13554
0.7895	Intermediate Similarity	NPC96362
0.7895	Intermediate Similarity	NPC236237
0.7895	Intermediate Similarity	NPC102253
0.7895	Intermediate Similarity	NPC322313
0.7895	Intermediate Similarity	NPC287749
0.7867	Intermediate Similarity	NPC98386
0.7867	Intermediate Similarity	NPC102708
0.7867	Intermediate Similarity	NPC87604
0.7867	Intermediate Similarity	NPC253807
0.7867	Intermediate Similarity	NPC167037
0.7867	Intermediate Similarity	NPC196753
0.7867	Intermediate Similarity	NPC300499
0.7867	Intermediate Similarity	NPC138621
0.7867	Intermediate Similarity	NPC158662
0.7867	Intermediate Similarity	NPC470396
0.7867	Intermediate Similarity	NPC244385
0.7867	Intermediate Similarity	NPC148977
0.7867	Intermediate Similarity	NPC22955
0.7867	Intermediate Similarity	NPC230295
0.7867	Intermediate Similarity	NPC99168
0.7867	Intermediate Similarity	NPC474989
0.7867	Intermediate Similarity	NPC6978
0.7857	Intermediate Similarity	NPC96484
0.7857	Intermediate Similarity	NPC94192
0.7857	Intermediate Similarity	NPC208999
0.7848	Intermediate Similarity	NPC164424
0.7838	Intermediate Similarity	NPC30590
0.7838	Intermediate Similarity	NPC120098
0.7838	Intermediate Similarity	NPC265328
0.7838	Intermediate Similarity	NPC106432
0.7838	Intermediate Similarity	NPC189883
0.7838	Intermediate Similarity	NPC290598
0.7838	Intermediate Similarity	NPC73875
0.7838	Intermediate Similarity	NPC27765
0.7838	Intermediate Similarity	NPC38141
0.7838	Intermediate Similarity	NPC122418
0.7838	Intermediate Similarity	NPC237460
0.7821	Intermediate Similarity	NPC110778

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 NPC253303 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	2692
0.2-0.3	3971
0.3-0.4	1670
0.4-0.5	318
0.5-0.6	212
0.6-0.7	105
0.7-0.8	16
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
0.7895	Intermediate Similarity	NPD7525	Registered
0.7763	Intermediate Similarity	NPD7645	Phase 2
0.76	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD6942	Approved
0.7467	Intermediate Similarity	NPD7339	Approved
0.7333	Intermediate Similarity	NPD6924	Approved
0.7333	Intermediate Similarity	NPD6926	Approved
0.7229	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6931	Approved
0.7215	Intermediate Similarity	NPD6930	Phase 2
0.7195	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6933	Approved
0.7108	Intermediate Similarity	NPD3618	Phase 1
0.7089	Intermediate Similarity	NPD6929	Approved
0.7051	Intermediate Similarity	NPD6932	Approved
0.7037	Intermediate Similarity	NPD3667	Approved
0.7027	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4748	Discontinued
0.7	Intermediate Similarity	NPD7509	Discontinued
0.6951	Remote Similarity	NPD6695	Phase 3
0.6935	Remote Similarity	NPD385	Approved
0.6935	Remote Similarity	NPD384	Approved
0.6875	Remote Similarity	NPD6683	Phase 2
0.6867	Remote Similarity	NPD4786	Approved
0.6867	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5328	Approved
0.6842	Remote Similarity	NPD7150	Approved
0.6842	Remote Similarity	NPD7151	Approved
0.6842	Remote Similarity	NPD7152	Approved
0.6842	Remote Similarity	NPD4243	Approved
0.6835	Remote Similarity	NPD6925	Approved
0.6835	Remote Similarity	NPD5776	Phase 2
0.6818	Remote Similarity	NPD4202	Approved
0.6806	Remote Similarity	NPD371	Approved
0.68	Remote Similarity	NPD6922	Approved
0.68	Remote Similarity	NPD6923	Approved
0.6795	Remote Similarity	NPD8264	Approved
0.6795	Remote Similarity	NPD3703	Phase 2
0.679	Remote Similarity	NPD7514	Phase 3
0.679	Remote Similarity	NPD7332	Phase 2
0.6786	Remote Similarity	NPD6893	Approved
0.6774	Remote Similarity	NPD386	Approved
0.6774	Remote Similarity	NPD388	Approved
0.6761	Remote Similarity	NPD368	Approved
0.675	Remote Similarity	NPD7145	Approved
0.6747	Remote Similarity	NPD4788	Approved
0.6711	Remote Similarity	NPD4787	Phase 1
0.6711	Remote Similarity	NPD7143	Approved
0.6711	Remote Similarity	NPD7144	Approved
0.6707	Remote Similarity	NPD6898	Phase 1
0.6705	Remote Similarity	NPD6079	Approved
0.6705	Remote Similarity	NPD7515	Phase 2
0.6667	Remote Similarity	NPD4784	Approved
0.6667	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD4785	Approved
0.6667	Remote Similarity	NPD3666	Approved
0.6667	Remote Similarity	NPD3665	Phase 1
0.663	Remote Similarity	NPD7638	Approved
0.6628	Remote Similarity	NPD7750	Discontinued
0.6628	Remote Similarity	NPD7524	Approved
0.6582	Remote Similarity	NPD4190	Phase 3
0.6582	Remote Similarity	NPD5275	Approved
0.6579	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD7640	Approved
0.6559	Remote Similarity	NPD7639	Approved
0.6543	Remote Similarity	NPD6115	Approved
0.6543	Remote Similarity	NPD6118	Approved
0.6543	Remote Similarity	NPD6114	Approved
0.6543	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD6697	Approved
0.6522	Remote Similarity	NPD4755	Approved
0.6517	Remote Similarity	NPD8035	Phase 2
0.6517	Remote Similarity	NPD8034	Phase 2
0.6506	Remote Similarity	NPD6902	Approved
0.6463	Remote Similarity	NPD4195	Approved
0.6413	Remote Similarity	NPD5222	Approved
0.6413	Remote Similarity	NPD5221	Approved
0.6413	Remote Similarity	NPD4697	Phase 3
0.6413	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.641	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.641	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD1145	Discontinued
0.6383	Remote Similarity	NPD5286	Approved
0.6383	Remote Similarity	NPD5285	Approved
0.6383	Remote Similarity	NPD4700	Approved
0.6383	Remote Similarity	NPD4696	Approved
0.6374	Remote Similarity	NPD7748	Approved
0.6344	Remote Similarity	NPD5173	Approved
0.6333	Remote Similarity	NPD7087	Discontinued
0.6316	Remote Similarity	NPD5223	Approved
0.6296	Remote Similarity	NPD6117	Approved
0.6292	Remote Similarity	NPD4753	Phase 2
0.6279	Remote Similarity	NPD3668	Phase 3
0.6277	Remote Similarity	NPD5290	Discontinued
0.6267	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5225	Approved
0.625	Remote Similarity	NPD5224	Approved
0.625	Remote Similarity	NPD4633	Approved
0.625	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5211	Phase 2
0.625	Remote Similarity	NPD5226	Approved
0.6235	Remote Similarity	NPD4223	Phase 3
0.6235	Remote Similarity	NPD4221	Approved
0.622	Remote Similarity	NPD6116	Phase 1
0.619	Remote Similarity	NPD6928	Phase 2
0.6186	Remote Similarity	NPD5174	Approved
0.6186	Remote Similarity	NPD5175	Approved
0.6186	Remote Similarity	NPD4754	Approved
0.617	Remote Similarity	NPD7902	Approved
0.6154	Remote Similarity	NPD3698	Phase 2
0.6143	Remote Similarity	NPD342	Phase 1
0.6139	Remote Similarity	NPD4634	Approved
0.6136	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD5279	Phase 3
0.6122	Remote Similarity	NPD5141	Approved
0.6105	Remote Similarity	NPD4225	Approved
0.6092	Remote Similarity	NPD4197	Approved
0.6087	Remote Similarity	NPD6399	Phase 3
0.6082	Remote Similarity	NPD7632	Discontinued
0.6076	Remote Similarity	NPD4245	Approved
0.6076	Remote Similarity	NPD4244	Approved
0.6061	Remote Similarity	NPD7128	Approved
0.6061	Remote Similarity	NPD4767	Approved
0.6061	Remote Similarity	NPD5739	Approved
0.6061	Remote Similarity	NPD4768	Approved
0.6061	Remote Similarity	NPD6675	Approved
0.6061	Remote Similarity	NPD6402	Approved
0.6049	Remote Similarity	NPD1810	Approved
0.6049	Remote Similarity	NPD1811	Approved
0.6026	Remote Similarity	NPD5360	Phase 3
0.6026	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD5329	Approved
0.6	Remote Similarity	NPD5701	Approved
0.6	Remote Similarity	NPD5697	Approved
0.6	Remote Similarity	NPD4695	Discontinued
0.5979	Remote Similarity	NPD4159	Approved
0.5962	Remote Similarity	NPD4632	Approved
0.5957	Remote Similarity	NPD5210	Approved
0.5957	Remote Similarity	NPD4629	Approved
0.5955	Remote Similarity	NPD5205	Approved
0.5955	Remote Similarity	NPD4623	Approved
0.5955	Remote Similarity	NPD4519	Discontinued
0.5955	Remote Similarity	NPD4690	Approved
0.5955	Remote Similarity	NPD4689	Approved
0.5955	Remote Similarity	NPD4693	Phase 3
0.5955	Remote Similarity	NPD4688	Approved
0.5955	Remote Similarity	NPD4138	Approved
0.5952	Remote Similarity	NPD3617	Approved
0.5952	Remote Similarity	NPD3671	Phase 1
0.5941	Remote Similarity	NPD5128	Approved
0.5941	Remote Similarity	NPD6899	Approved
0.5941	Remote Similarity	NPD4730	Approved
0.5941	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD6011	Approved
0.5941	Remote Similarity	NPD7320	Approved
0.5941	Remote Similarity	NPD6881	Approved
0.5941	Remote Similarity	NPD4729	Approved
0.5926	Remote Similarity	NPD4732	Discontinued
0.5889	Remote Similarity	NPD3573	Approved
0.5882	Remote Similarity	NPD6013	Approved
0.5882	Remote Similarity	NPD6373	Approved
0.5882	Remote Similarity	NPD6012	Approved
0.5882	Remote Similarity	NPD6372	Approved
0.5882	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6014	Approved
0.5875	Remote Similarity	NPD4789	Approved
0.587	Remote Similarity	NPD7136	Phase 2
0.587	Remote Similarity	NPD3168	Discontinued
0.5851	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD7900	Approved
0.5843	Remote Similarity	NPD1696	Phase 3
0.5833	Remote Similarity	NPD6083	Phase 2
0.5833	Remote Similarity	NPD6084	Phase 2
0.5825	Remote Similarity	NPD5248	Approved
0.5825	Remote Similarity	NPD5247	Approved
0.5825	Remote Similarity	NPD5251	Approved
0.5825	Remote Similarity	NPD5169	Approved
0.5825	Remote Similarity	NPD5250	Approved
0.5825	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD7102	Approved
0.5825	Remote Similarity	NPD6883	Approved
0.5825	Remote Similarity	NPD5135	Approved
0.5825	Remote Similarity	NPD5249	Phase 3
0.5825	Remote Similarity	NPD7290	Approved
0.5824	Remote Similarity	NPD4723	Approved
0.5824	Remote Similarity	NPD4722	Approved
0.5823	Remote Similarity	NPD6705	Phase 1
0.581	Remote Similarity	NPD8133	Approved
0.5806	Remote Similarity	NPD7637	Suspended
0.5802	Remote Similarity	NPD4758	Discontinued
0.5794	Remote Similarity	NPD6009	Approved
0.5784	Remote Similarity	NPD5168	Approved
0.5781	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD5280	Approved
0.5778	Remote Similarity	NPD5330	Approved
0.5778	Remote Similarity	NPD7521	Approved
0.5778	Remote Similarity	NPD7334	Approved
0.5778	Remote Similarity	NPD7146	Approved
0.5778	Remote Similarity	NPD5690	Phase 2

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