NPASS Compound

Structure

CID97614 OpenBabel06191715432D 27 26 0 0 1 0 0 0 0 0999 V2000 13.8564 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.8564 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9904 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 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 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 24 1 0 0 0 0 3 27 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 2 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 23 1 0 0 0 0 20 25 1 0 0 0 0 21 22 1 0 0 0 0 21 27 1 0 0 0 0 22 20 1 1 0 0 0 22 24 1 0 0 0 0 23 24 1 0 0 0 0 23 26 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	383.34
Volume:	438.459
LogP:	5.594
LogD:	4.282
LogS:	-5.337
# Rotatable Bonds:	20
TPSA:	49.77
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	0
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.237
Synthetic Accessibility Score:	3.048
Fsp3:	0.87
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.706
MDCK Permeability:	2.6929112209472805e-05
Pgp-inhibitor:	0.326
Pgp-substrate:	0.348
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.642
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.58
Plasma Protein Binding (PPB):	97.81057739257812%
Volume Distribution (VD):	1.003
Pgp-substrate:	1.43435537815094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.082
CYP1A2-substrate:	0.619
CYP2C19-inhibitor:	0.316
CYP2C19-substrate:	0.45
CYP2C9-inhibitor:	0.325
CYP2C9-substrate:	0.751
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.075
CYP3A4-inhibitor:	0.636
CYP3A4-substrate:	0.13

ADMET: Excretion

Clearance (CL):	3.871
Half-life (T1/2):	0.366

ADMET: Toxicity

hERG Blockers:	0.236
Human Hepatotoxicity (H-HT):	0.05
Drug-inuced Liver Injury (DILI):	0.033
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.054
Skin Sensitization:	0.956
Carcinogencity:	0.031
Eye Corrosion:	0.006
Eye Irritation:	0.343
Respiratory Toxicity:	0.036

Download Data

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

Natural Product: NPC97614

Natural Product ID:	NPC97614
*Common Name:**	Serinolamide A
IUPAC Name:	(E)-N-[(2R)-1-hydroxy-3-methoxypropan-2-yl]-N-methyloctadec-4-enamide
Synonyms:	Serinolamide A
Standard InCHIKey:	CJAVPRNATZCNLN-NBRGKURFSA-N
Standard InCHI:	InChI=1S/C23H45NO3/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(26)24(2)22(20-25)21-27-3/h16-17,22,25H,4-15,18-21H2,1-3H3/b17-16+/t22-/m1/s1
SMILES:	CCCCCCCCCCCCC/C=C/CCC(=O)N(C)[C@H](CO)COC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1928586
PubChem CID:	56597771
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000331] Fatty amides [CHEMONTID:0001096] N-acyl amines

*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
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10514329]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10654420]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10691708]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	palauan	n.a.	PMID[10691729]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10843570]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10924172]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10978206]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11076571]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11076573]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11076574]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11277744]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11389621]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11430000]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11473443]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11922791]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12762816]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Papua New Guinea	n.a.	PMID[12828459]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[14575437]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[1517734]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Papua New Guinea	n.a.	PMID[16643028]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17125217]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17441769]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18444683]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Singapore	n.a.	PMID[19093843]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19489598]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	eastern Caribbean	n.a.	PMID[19739598]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19839606]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20030365]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	panamanian	n.a.	PMID[20158242]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Floridian	n.a.	PMID[20166701]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20936843]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21138309]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[2128518]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21341718]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21539315]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21806011]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21999614]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22035372]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29792428]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[3924698]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Caribbean	n.a.	PMID[7623050]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Caribbean	n.a.	PMID[8699186]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9584405]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9599278]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9599279]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9784156]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2
Ki	1
Others	3

Activity Type	# Activity
Cell Line	2
Individual Protein	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Ki	=	1300.0	nM	PMID[510834]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	IC50	=	2300.0	nM	PMID[510834]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	IC50	>	10000.0	nM	PMID[510834]
NPT397	Cell Line	NCI-H460	Homo sapiens	Activity	=	0.0	%	PMID[510834]
NPT397	Cell Line	NCI-H460	Homo sapiens	Activity	=	60.0	%	PMID[510834]
NPT2	Others	Unspecified		Ratio IC50	>	5.0	n.a.	PMID[510834]

☑ 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 NPC97614 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	52
0.1-0.2	1998
0.2-0.3	25750
0.3-0.4	11844
0.4-0.5	2658
0.5-0.6	339
0.6-0.7	48
0.7-0.8	6
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7821	Intermediate Similarity	NPC477523
0.7722	Intermediate Similarity	NPC477524
0.7176	Intermediate Similarity	NPC324506
0.6962	Remote Similarity	NPC34672
0.6951	Remote Similarity	NPC209232
0.6632	Remote Similarity	NPC188785
0.6628	Remote Similarity	NPC475975
0.6623	Remote Similarity	NPC23721
0.6533	Remote Similarity	NPC206660
0.6486	Remote Similarity	NPC252684
0.6471	Remote Similarity	NPC277341
0.6471	Remote Similarity	NPC226982
0.642	Remote Similarity	NPC470993
0.642	Remote Similarity	NPC470994
0.642	Remote Similarity	NPC470992
0.64	Remote Similarity	NPC55068
0.6374	Remote Similarity	NPC53240
0.6364	Remote Similarity	NPC476328
0.6354	Remote Similarity	NPC233932
0.6353	Remote Similarity	NPC19497
0.6329	Remote Similarity	NPC475930
0.6329	Remote Similarity	NPC137620
0.6329	Remote Similarity	NPC127145
0.6329	Remote Similarity	NPC474675
0.6329	Remote Similarity	NPC280065
0.6329	Remote Similarity	NPC45060
0.6327	Remote Similarity	NPC476877
0.6277	Remote Similarity	NPC469739
0.6267	Remote Similarity	NPC29468
0.625	Remote Similarity	NPC474674
0.6238	Remote Similarity	NPC476276
0.6234	Remote Similarity	NPC477525
0.6216	Remote Similarity	NPC133923
0.6216	Remote Similarity	NPC326524
0.6216	Remote Similarity	NPC329003
0.6216	Remote Similarity	NPC325550
0.6207	Remote Similarity	NPC474312
0.6203	Remote Similarity	NPC96272
0.6203	Remote Similarity	NPC249713
0.62	Remote Similarity	NPC476876
0.6184	Remote Similarity	NPC477106
0.6154	Remote Similarity	NPC113224
0.6145	Remote Similarity	NPC3094
0.6136	Remote Similarity	NPC196102
0.6136	Remote Similarity	NPC178758
0.6133	Remote Similarity	NPC130807
0.6133	Remote Similarity	NPC42477
0.6125	Remote Similarity	NPC103712
0.6125	Remote Similarity	NPC291196
0.6118	Remote Similarity	NPC474833
0.6111	Remote Similarity	NPC242930
0.6098	Remote Similarity	NPC26932
0.6098	Remote Similarity	NPC305223
0.6081	Remote Similarity	NPC321030
0.6081	Remote Similarity	NPC385
0.6078	Remote Similarity	NPC207820
0.6064	Remote Similarity	NPC38172
0.6058	Remote Similarity	NPC476875
0.6053	Remote Similarity	NPC47333
0.6047	Remote Similarity	NPC471768
0.6022	Remote Similarity	NPC17143
0.6022	Remote Similarity	NPC47230
0.6	Remote Similarity	NPC46268
0.6	Remote Similarity	NPC325936
0.6	Remote Similarity	NPC163537
0.6	Remote Similarity	NPC474812
0.5962	Remote Similarity	NPC251122
0.5952	Remote Similarity	NPC217095
0.5952	Remote Similarity	NPC264417
0.5952	Remote Similarity	NPC281154
0.593	Remote Similarity	NPC473972
0.593	Remote Similarity	NPC475363
0.593	Remote Similarity	NPC473971
0.5914	Remote Similarity	NPC81195
0.5914	Remote Similarity	NPC39290
0.5914	Remote Similarity	NPC159369
0.5909	Remote Similarity	NPC82799
0.5888	Remote Similarity	NPC472536
0.5888	Remote Similarity	NPC103391
0.5854	Remote Similarity	NPC470662
0.5854	Remote Similarity	NPC324638
0.5849	Remote Similarity	NPC314550
0.5833	Remote Similarity	NPC78562
0.5833	Remote Similarity	NPC473588
0.5833	Remote Similarity	NPC288086
0.5824	Remote Similarity	NPC319913
0.5824	Remote Similarity	NPC264014
0.5816	Remote Similarity	NPC91036
0.5804	Remote Similarity	NPC273185
0.58	Remote Similarity	NPC77703
0.5795	Remote Similarity	NPC79367
0.5784	Remote Similarity	NPC205176
0.5769	Remote Similarity	NPC171734
0.5769	Remote Similarity	NPC316674
0.5765	Remote Similarity	NPC62293
0.5765	Remote Similarity	NPC212008
0.5765	Remote Similarity	NPC51055
0.5765	Remote Similarity	NPC140327
0.5761	Remote Similarity	NPC322672
0.5758	Remote Similarity	NPC475758
0.5743	Remote Similarity	NPC474244
0.573	Remote Similarity	NPC6902
0.573	Remote Similarity	NPC184473
0.573	Remote Similarity	NPC284456
0.5714	Remote Similarity	NPC326126
0.5714	Remote Similarity	NPC470943
0.57	Remote Similarity	NPC475791
0.57	Remote Similarity	NPC13175
0.5699	Remote Similarity	NPC473525
0.5696	Remote Similarity	NPC476658
0.5667	Remote Similarity	NPC473810
0.5658	Remote Similarity	NPC325734
0.5657	Remote Similarity	NPC52820
0.5644	Remote Similarity	NPC144714
0.5644	Remote Similarity	NPC100810
0.5641	Remote Similarity	NPC477459
0.5641	Remote Similarity	NPC201939
0.5641	Remote Similarity	NPC477461
0.5641	Remote Similarity	NPC51166
0.5638	Remote Similarity	NPC155230
0.5634	Remote Similarity	NPC59051
0.5632	Remote Similarity	NPC308050
0.5631	Remote Similarity	NPC476921
0.5625	Remote Similarity	NPC176215
0.5625	Remote Similarity	NPC476654
0.5625	Remote Similarity	NPC476655
0.5625	Remote Similarity	NPC476657
0.5625	Remote Similarity	NPC145707
0.5625	Remote Similarity	NPC296436
0.5619	Remote Similarity	NPC474099
0.5616	Remote Similarity	NPC284224

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 NPC97614 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	63
0.1-0.2	816
0.2-0.3	5182
0.3-0.4	2519
0.4-0.5	544
0.5-0.6	24
0.6-0.7	2
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
0.64	Remote Similarity	NPD3210	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD6949	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD1452	Discontinued
0.5854	Remote Similarity	NPD3212	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD9512	Approved
0.5747	Remote Similarity	NPD3732	Approved
0.5714	Remote Similarity	NPD9511	Approved
0.5676	Remote Similarity	NPD4281	Clinical (unspecified phase)

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