NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	258.16
Volume:	301.713
LogP:	3.505
LogD:	3.605
LogS:	-3.982
# Rotatable Bonds:	8
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	0
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.399
Synthetic Accessibility Score:	4.354
Fsp3:	0.412
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.679
MDCK Permeability:	2.1697089323424734e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.138
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.212
Plasma Protein Binding (PPB):	101.27320098876953%
Volume Distribution (VD):	1.263
Pgp-substrate:	1.6869789361953735%

ADMET: Metabolism

CYP1A2-inhibitor:	0.348
CYP1A2-substrate:	0.178
CYP2C19-inhibitor:	0.901
CYP2C19-substrate:	0.69
CYP2C9-inhibitor:	0.917
CYP2C9-substrate:	0.979
CYP2D6-inhibitor:	0.149
CYP2D6-substrate:	0.579
CYP3A4-inhibitor:	0.925
CYP3A4-substrate:	0.218

ADMET: Excretion

Clearance (CL):	7.942
Half-life (T1/2):	0.851

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.086
Drug-inuced Liver Injury (DILI):	0.855
AMES Toxicity:	0.821
Rat Oral Acute Toxicity:	0.997
Maximum Recommended Daily Dose:	1.0
Skin Sensitization:	0.962
Carcinogencity:	0.387
Eye Corrosion:	0.972
Eye Irritation:	0.976
Respiratory Toxicity:	0.992

Download Data

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

Natural Product: NPC124183

Natural Product ID:	NPC124183
*Common Name:**	(3S,8S)-16,17-Didehydrofalcarindiol
IUPAC Name:	(3S,8S,9Z)-heptadeca-1,9,16-trien-4,6-diyne-3,8-diol
Synonyms:	(3S,8S)-16,17-Didehydrofalcarindiol
Standard InCHIKey:	OLUQMFYBNOJBQQ-RCQSYPNMSA-N
Standard InCHI:	InChI=1S/C17H22O2/c1-3-5-6-7-8-9-10-14-17(19)15-12-11-13-16(18)4-2/h3-4,10,14,16-19H,1-2,5-9H2/b14-10-/t16-,17-/m0/s1
SMILES:	C=CCCCCC/C=C[C@@H](C#CC#C[C@H](C=C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459266
PubChem CID:	5469786
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002951] Long-chain fatty alcohols

*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
NPO22011	Myrmekioderma styx	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[1431947]
NPO22011	Myrmekioderma styx	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[1453179]
NPO7728	Vitex agnus-castus	Species	Lamiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[17262892]
NPO7728	Vitex agnus-castus	Species	Lamiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21163339]
NPO17800	Isodon rosthornii	Species	Lamiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[23819871]
NPO12187	Convolvulus arvensis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31181918]
NPO4031.1	Cynara cardunculus var. scolymus	Varieties	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3430163]
NPO4031.1	Cynara cardunculus var. scolymus	Varieties	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6821187]
NPO21711	Dendropanax arboreus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8792622]
NPO4031.1	Cynara cardunculus var. scolymus	Varieties	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO4031.1	Cynara cardunculus var. scolymus	Varieties	Asteraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO19250	Digitalis orientalis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22185	Cocculus indicus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17800	Isodon rosthornii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4031.1	Cynara cardunculus var. scolymus	Varieties	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO12187	Convolvulus arvensis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4031.1	Cynara cardunculus var. scolymus	Varieties	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22185	Cocculus indicus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19250	Digitalis orientalis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17800	Isodon rosthornii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12187	Convolvulus arvensis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22300	Soulamea amara	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13870	Podocarpium podocarpum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO21369	Paullinia scarlatina	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5406	Veronica chamaedrys	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21236	Annona crassiflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21711	Dendropanax arboreus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9385	Glycosmis ovoidea	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19250	Digitalis orientalis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12139	Cylindrotheca closterium	Species	Bacillariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14084	Roccella fucoides	Species	Roccellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3495	Matsucoccus feytaudi	Species	Margarodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18274	Centaurea deusta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2509	Strombus gigas	Species	Strombidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12902	Alstonia undulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17800	Isodon rosthornii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14730	Bonnetia dinizii	Species	Bonnetiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4031.1	Cynara cardunculus var. scolymus	Varieties	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7728	Vitex agnus-castus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17649	Eugenia caryophyllus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2090	Baccharis thesioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18065	Siparuna gilgiana	Species	Siparunaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO368	Dendroaspis angusticeps	Species	Elapidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17123	Delphinium roylei	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22011	Myrmekioderma styx	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO18458	Raukaua simplex	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18448	Hamelia patens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19387	Hazardia squarrosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22185	Cocculus indicus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12187	Convolvulus arvensis	Species	Convolvulaceae	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
GI50	1
Others	11

Activity Type	# Activity
NON-MOLECULAR	4
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	2100.0	nM	PMID[489136]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	TGI	=	3000.0	nM	PMID[489136]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	LC50	=	10000.0	nM	PMID[489136]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	14.5	day	PMID[489136]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	14.0	day	PMID[489136]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	15.5	day	PMID[489136]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	15.0	day	PMID[489136]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	3.0	%	PMID[489136]

☑ 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 NPC124183 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	141
0.1-0.2	8191
0.2-0.3	22183
0.3-0.4	8546
0.4-0.5	2642
0.5-0.6	706
0.6-0.7	132
0.7-0.8	47
0.8-0.85	30
0.85-0.9	35
0.9-0.95	26
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC35141
0.9556	High Similarity	NPC471280
0.9556	High Similarity	NPC31194
0.9556	High Similarity	NPC85079
0.9556	High Similarity	NPC248884
0.9556	High Similarity	NPC471275
0.9556	High Similarity	NPC153538
0.9556	High Similarity	NPC125122
0.9556	High Similarity	NPC471276
0.9535	High Similarity	NPC101616
0.9348	High Similarity	NPC477727
0.9348	High Similarity	NPC72699
0.9348	High Similarity	NPC471281
0.9348	High Similarity	NPC199286
0.9149	High Similarity	NPC256656
0.9149	High Similarity	NPC475477
0.9149	High Similarity	NPC170776
0.9149	High Similarity	NPC294278
0.9149	High Similarity	NPC165447
0.9149	High Similarity	NPC329608
0.9149	High Similarity	NPC151782
0.9149	High Similarity	NPC224148
0.9149	High Similarity	NPC89824
0.9149	High Similarity	NPC477723
0.9149	High Similarity	NPC93639
0.9149	High Similarity	NPC76198
0.9149	High Similarity	NPC55383
0.9149	High Similarity	NPC9273
0.9149	High Similarity	NPC197272
0.9149	High Similarity	NPC471959
0.9111	High Similarity	NPC55063
0.9111	High Similarity	NPC19834
0.8958	High Similarity	NPC142092
0.8936	High Similarity	NPC249670
0.8936	High Similarity	NPC473913
0.8936	High Similarity	NPC474642
0.8889	High Similarity	NPC269074
0.875	High Similarity	NPC71053
0.875	High Similarity	NPC59408
0.8696	High Similarity	NPC180575
0.8636	High Similarity	NPC304151
0.86	High Similarity	NPC49059
0.86	High Similarity	NPC110732
0.86	High Similarity	NPC48058
0.86	High Similarity	NPC256209
0.86	High Similarity	NPC473532
0.8542	High Similarity	NPC328784
0.8542	High Similarity	NPC291437
0.8431	Intermediate Similarity	NPC477725
0.8431	Intermediate Similarity	NPC473735
0.8431	Intermediate Similarity	NPC477726
0.8431	Intermediate Similarity	NPC470963
0.8431	Intermediate Similarity	NPC474513
0.8431	Intermediate Similarity	NPC146551
0.8431	Intermediate Similarity	NPC152668
0.8431	Intermediate Similarity	NPC473725
0.8431	Intermediate Similarity	NPC471239
0.8431	Intermediate Similarity	NPC475353
0.8431	Intermediate Similarity	NPC473910
0.8431	Intermediate Similarity	NPC473896
0.8431	Intermediate Similarity	NPC473721
0.8367	Intermediate Similarity	NPC129263
0.8333	Intermediate Similarity	NPC302310
0.8298	Intermediate Similarity	NPC157096
0.8269	Intermediate Similarity	NPC473847
0.8269	Intermediate Similarity	NPC470969
0.8269	Intermediate Similarity	NPC470964
0.8269	Intermediate Similarity	NPC475384
0.8269	Intermediate Similarity	NPC470966
0.8269	Intermediate Similarity	NPC471960
0.8269	Intermediate Similarity	NPC161838
0.8269	Intermediate Similarity	NPC470968
0.8269	Intermediate Similarity	NPC470967
0.8269	Intermediate Similarity	NPC477661
0.8269	Intermediate Similarity	NPC311648
0.8222	Intermediate Similarity	NPC149668
0.8182	Intermediate Similarity	NPC103236
0.8182	Intermediate Similarity	NPC329762
0.8182	Intermediate Similarity	NPC27444
0.8113	Intermediate Similarity	NPC212730
0.8113	Intermediate Similarity	NPC594
0.8113	Intermediate Similarity	NPC470970
0.8113	Intermediate Similarity	NPC48968
0.8113	Intermediate Similarity	NPC265551
0.8113	Intermediate Similarity	NPC193975
0.8077	Intermediate Similarity	NPC474644
0.8039	Intermediate Similarity	NPC34577
0.8039	Intermediate Similarity	NPC61177
0.7955	Intermediate Similarity	NPC15934
0.7925	Intermediate Similarity	NPC473865
0.7925	Intermediate Similarity	NPC474643
0.7872	Intermediate Similarity	NPC108195
0.7826	Intermediate Similarity	NPC206906
0.7818	Intermediate Similarity	NPC473652
0.78	Intermediate Similarity	NPC473768
0.7778	Intermediate Similarity	NPC44542
0.7708	Intermediate Similarity	NPC276825
0.7692	Intermediate Similarity	NPC187361
0.7692	Intermediate Similarity	NPC26102
0.7692	Intermediate Similarity	NPC477724
0.7679	Intermediate Similarity	NPC471278
0.7674	Intermediate Similarity	NPC213767
0.7647	Intermediate Similarity	NPC473672
0.7647	Intermediate Similarity	NPC474495
0.7544	Intermediate Similarity	NPC66460
0.7544	Intermediate Similarity	NPC168407
0.7544	Intermediate Similarity	NPC271282
0.7544	Intermediate Similarity	NPC325929
0.7544	Intermediate Similarity	NPC475984
0.75	Intermediate Similarity	NPC216416
0.7455	Intermediate Similarity	NPC472445
0.7414	Intermediate Similarity	NPC470965
0.7414	Intermediate Similarity	NPC29697
0.7358	Intermediate Similarity	NPC284224
0.7358	Intermediate Similarity	NPC474496
0.7308	Intermediate Similarity	NPC29234
0.7292	Intermediate Similarity	NPC116934
0.7255	Intermediate Similarity	NPC475153
0.7234	Intermediate Similarity	NPC269823
0.7193	Intermediate Similarity	NPC222852
0.7174	Intermediate Similarity	NPC182840
0.7174	Intermediate Similarity	NPC306850
0.7174	Intermediate Similarity	NPC29091
0.7174	Intermediate Similarity	NPC255042
0.7174	Intermediate Similarity	NPC103213
0.717	Intermediate Similarity	NPC35756
0.7143	Intermediate Similarity	NPC138935
0.7115	Intermediate Similarity	NPC475071
0.7115	Intermediate Similarity	NPC474460
0.7091	Intermediate Similarity	NPC317899
0.7083	Intermediate Similarity	NPC31121
0.7083	Intermediate Similarity	NPC256766
0.7083	Intermediate Similarity	NPC213538
0.7083	Intermediate Similarity	NPC46248
0.7083	Intermediate Similarity	NPC249801
0.7045	Intermediate Similarity	NPC58957
0.7037	Intermediate Similarity	NPC217188
0.7018	Intermediate Similarity	NPC181872
0.7	Intermediate Similarity	NPC474202
0.7	Intermediate Similarity	NPC226592
0.7	Intermediate Similarity	NPC470320
0.7	Intermediate Similarity	NPC160628
0.7	Intermediate Similarity	NPC474362
0.7	Intermediate Similarity	NPC140501
0.6949	Remote Similarity	NPC477829
0.6935	Remote Similarity	NPC473752
0.6923	Remote Similarity	NPC267110
0.6852	Remote Similarity	NPC473705
0.6842	Remote Similarity	NPC471279
0.6842	Remote Similarity	NPC121034
0.6842	Remote Similarity	NPC471277
0.6818	Remote Similarity	NPC250734
0.6792	Remote Similarity	NPC182102
0.6792	Remote Similarity	NPC26960
0.6792	Remote Similarity	NPC473487
0.6792	Remote Similarity	NPC20934
0.6792	Remote Similarity	NPC288381
0.6786	Remote Similarity	NPC329686
0.6786	Remote Similarity	NPC227135
0.678	Remote Similarity	NPC327112
0.6727	Remote Similarity	NPC475723
0.6724	Remote Similarity	NPC226848
0.6667	Remote Similarity	NPC76976
0.6667	Remote Similarity	NPC200772
0.6667	Remote Similarity	NPC472808
0.6667	Remote Similarity	NPC324224
0.661	Remote Similarity	NPC473866
0.661	Remote Similarity	NPC475931
0.661	Remote Similarity	NPC474267
0.661	Remote Similarity	NPC122239
0.6607	Remote Similarity	NPC300121
0.6607	Remote Similarity	NPC269615
0.6607	Remote Similarity	NPC189677
0.66	Remote Similarity	NPC252978
0.6596	Remote Similarity	NPC40434
0.6596	Remote Similarity	NPC34873
0.6557	Remote Similarity	NPC55068
0.6552	Remote Similarity	NPC474577
0.6545	Remote Similarity	NPC106531
0.6522	Remote Similarity	NPC79544
0.6491	Remote Similarity	NPC474913
0.6491	Remote Similarity	NPC251666
0.6491	Remote Similarity	NPC232247
0.6471	Remote Similarity	NPC474413
0.6471	Remote Similarity	NPC473539
0.6471	Remote Similarity	NPC267514
0.6471	Remote Similarity	NPC145755
0.6444	Remote Similarity	NPC62779
0.6444	Remote Similarity	NPC81989
0.6441	Remote Similarity	NPC469373
0.6441	Remote Similarity	NPC155025
0.6415	Remote Similarity	NPC471958
0.6393	Remote Similarity	NPC26810
0.6393	Remote Similarity	NPC113293
0.6383	Remote Similarity	NPC174396
0.6379	Remote Similarity	NPC48891
0.6379	Remote Similarity	NPC249645
0.6379	Remote Similarity	NPC55412
0.6364	Remote Similarity	NPC244038
0.6364	Remote Similarity	NPC196831

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 NPC124183 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	143
0.1-0.2	5004
0.2-0.3	3343
0.3-0.4	513
0.4-0.5	109
0.5-0.6	33
0.6-0.7	5
0.7-0.8	0
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
0.7	Intermediate Similarity	NPD4265	Approved
0.678	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD3210	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD4219	Approved
0.6167	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD368	Approved
0.6	Remote Similarity	NPD4220	Pre-registration
0.5932	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD342	Phase 1
0.5909	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD3212	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD39	Approved
0.5714	Remote Similarity	NPD4732	Discontinued
0.5692	Remote Similarity	NPD3197	Phase 1
0.5614	Remote Similarity	NPD2268	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