NPASS Compound

Structure

NPC239097 OpenBabel07101718242D 33 37 0 0 1 0 0 0 0 0999 V2000 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3198 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 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 -2.0685 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -1.4781 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 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1965 -1.1303 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 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0625 -0.6303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8601 0.4523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4533 -0.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4752 -0.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 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 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 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 -4.8546 0.3478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 7 8 1 0 0 0 0 7 18 1 0 0 0 0 8 19 2 0 0 0 0 9 12 1 0 0 0 0 9 20 1 0 0 0 0 10 13 2 0 0 0 0 10 21 1 0 0 0 0 11 14 1 0 0 0 0 11 17 1 0 0 0 0 12 26 1 0 0 0 0 13 27 1 0 0 0 0 14 32 1 0 0 0 0 15 17 2 0 0 0 0 15 32 1 0 0 0 0 16 29 2 0 0 0 0 16 33 1 0 0 0 0 17 18 1 0 0 0 0 18 26 1 1 0 0 0 19 26 1 0 0 0 0 19 28 1 0 0 0 0 20 27 1 6 0 0 0 20 28 1 0 0 0 0 21 25 1 0 0 0 0 21 30 2 0 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 22 31 1 1 0 0 0 23 25 1 0 0 0 0 23 27 1 6 0 0 0 24 28 1 1 0 0 0 24 33 1 0 0 0 0 26 4 1 1 0 0 0 27 5 1 6 0 0 0 28 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.27
Volume:	480.831
LogP:	3.03
LogD:	2.427
LogS:	-4.641
# Rotatable Bonds:	3
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.481
Synthetic Accessibility Score:	5.221
Fsp3:	0.714
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.058
MDCK Permeability:	3.244782783440314e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.859
30% Bioavailability (F30%):	0.339

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.221
Plasma Protein Binding (PPB):	79.02289581298828%
Volume Distribution (VD):	1.658
Pgp-substrate:	19.644145965576172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.121
CYP2C19-inhibitor:	0.086
CYP2C19-substrate:	0.765
CYP2C9-inhibitor:	0.162
CYP2C9-substrate:	0.053
CYP2D6-inhibitor:	0.265
CYP2D6-substrate:	0.049
CYP3A4-inhibitor:	0.837
CYP3A4-substrate:	0.68

ADMET: Excretion

Clearance (CL):	1.797
Half-life (T1/2):	0.665

ADMET: Toxicity

hERG Blockers:	0.503
Human Hepatotoxicity (H-HT):	0.621
Drug-inuced Liver Injury (DILI):	0.05
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.295
Maximum Recommended Daily Dose:	0.964
Skin Sensitization:	0.878
Carcinogencity:	0.125
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC239097

Natural Product ID:	NPC239097
*Common Name:**	24-Norchola-1,14,20-Trien-3-One,7(Acetoxy)-21,23-Epoxy-6-Hydroxy,4,4,8-Trimethyl-(5Alpha,6Alpha,7Alpha,17Alpha)
IUPAC Name:	[(5R,6R,7S,8R,9R,10R,13S,17R)-17-(2,3-dihydrofuran-4-yl)-6-hydroxy-4,4,8,10,13-pentamethyl-3-oxo-5,6,7,9,11,12,16,17-octahydrocyclopenta[a]phenanthren-7-yl] acetate
Synonyms:
Standard InCHIKey:	DQHRAIFEHNKZSV-XMLHTYRRSA-N
Standard InCHI:	InChI=1S/C28H38O5/c1-16(29)33-24-22(31)23-25(2,3)21(30)10-13-27(23,5)20-9-12-26(4)18(17-11-14-32-15-17)7-8-19(26)28(20,24)6/h8,10,13,15,18,20,22-24,31H,7,9,11-12,14H2,1-6H3/t18-,20+,22+,23-,24+,26-,27+,28-/m0/s1
SMILES:	CC(=O)O[C@@H]1[C@@H]([C@H]2C(C)(C)C(=O)C=C[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](CC=C3[C@]12C)C1=COCC1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491379
PubChem CID:	636837
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193038]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1593280]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18816111]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	fruits	n.a.	n.a.	PMID[20669933]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[21381696]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	seed	n.a.	PMID[21381696]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2607354]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2614419]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26339153]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[28493718]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	bark	n.a.	PMID[9134742]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	fruit	n.a.	PMID[9134742]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[9134742]
NPO4406	Azadirachta indica	Species	Meliaceae	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4532	Organism	Anopheles stephensi	Anopheles stephensi	LC50	=	60.0	ppm	PMID[550507]

☑ 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 NPC239097 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	210
0.1-0.2	1173
0.2-0.3	3897
0.3-0.4	7675
0.4-0.5	13780
0.5-0.6	7674
0.6-0.7	5816
0.7-0.8	2360
0.8-0.85	96
0.85-0.9	13
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9406	High Similarity	NPC264048
0.9083	High Similarity	NPC284068
0.8879	High Similarity	NPC5284
0.8785	High Similarity	NPC41405
0.8762	High Similarity	NPC255309
0.8725	High Similarity	NPC292133
0.8692	High Similarity	NPC469844
0.8679	High Similarity	NPC96377
0.8585	High Similarity	NPC189616
0.8558	High Similarity	NPC316964
0.8545	High Similarity	NPC234042
0.8545	High Similarity	NPC152117
0.8519	High Similarity	NPC19412
0.8515	High Similarity	NPC79117
0.8505	High Similarity	NPC102352
0.8468	Intermediate Similarity	NPC255017
0.8462	Intermediate Similarity	NPC114274
0.8455	Intermediate Similarity	NPC43775
0.8426	Intermediate Similarity	NPC3316
0.8426	Intermediate Similarity	NPC144854
0.8411	Intermediate Similarity	NPC471293
0.8407	Intermediate Similarity	NPC471854
0.8407	Intermediate Similarity	NPC470959
0.8407	Intermediate Similarity	NPC476965
0.8396	Intermediate Similarity	NPC473163
0.8396	Intermediate Similarity	NPC136289
0.8365	Intermediate Similarity	NPC108078
0.835	Intermediate Similarity	NPC473170
0.835	Intermediate Similarity	NPC317586
0.835	Intermediate Similarity	NPC470016
0.8349	Intermediate Similarity	NPC154608
0.8349	Intermediate Similarity	NPC192813
0.8349	Intermediate Similarity	NPC277017
0.8333	Intermediate Similarity	NPC311554
0.8333	Intermediate Similarity	NPC257457
0.8333	Intermediate Similarity	NPC107674
0.8333	Intermediate Similarity	NPC141497
0.8333	Intermediate Similarity	NPC170220
0.8319	Intermediate Similarity	NPC270929
0.8318	Intermediate Similarity	NPC471005
0.8317	Intermediate Similarity	NPC472325
0.8304	Intermediate Similarity	NPC250109
0.8302	Intermediate Similarity	NPC81530
0.8302	Intermediate Similarity	NPC224720
0.8302	Intermediate Similarity	NPC476240
0.8302	Intermediate Similarity	NPC476223
0.8291	Intermediate Similarity	NPC473979
0.8288	Intermediate Similarity	NPC474229
0.8273	Intermediate Similarity	NPC153239
0.8273	Intermediate Similarity	NPC27814
0.8269	Intermediate Similarity	NPC104568
0.8269	Intermediate Similarity	NPC471039
0.8252	Intermediate Similarity	NPC166906
0.8252	Intermediate Similarity	NPC159410
0.8246	Intermediate Similarity	NPC183580
0.8246	Intermediate Similarity	NPC312824
0.8246	Intermediate Similarity	NPC470493
0.8235	Intermediate Similarity	NPC189520
0.8235	Intermediate Similarity	NPC212301
0.8235	Intermediate Similarity	NPC86266
0.8235	Intermediate Similarity	NPC110657
0.823	Intermediate Similarity	NPC147912
0.823	Intermediate Similarity	NPC67259
0.8218	Intermediate Similarity	NPC119416
0.8214	Intermediate Similarity	NPC90769
0.8214	Intermediate Similarity	NPC71348
0.8214	Intermediate Similarity	NPC470063
0.8208	Intermediate Similarity	NPC476274
0.8198	Intermediate Similarity	NPC37116
0.8198	Intermediate Similarity	NPC197428
0.819	Intermediate Similarity	NPC476961
0.8174	Intermediate Similarity	NPC329736
0.8173	Intermediate Similarity	NPC469599
0.8158	Intermediate Similarity	NPC266728
0.8158	Intermediate Similarity	NPC49492
0.8155	Intermediate Similarity	NPC470224
0.8148	Intermediate Similarity	NPC239716
0.8142	Intermediate Similarity	NPC198539
0.8142	Intermediate Similarity	NPC962
0.8136	Intermediate Similarity	NPC11895
0.8131	Intermediate Similarity	NPC469327
0.8119	Intermediate Similarity	NPC158778
0.8113	Intermediate Similarity	NPC478056
0.8113	Intermediate Similarity	NPC194196
0.8108	Intermediate Similarity	NPC310546
0.8108	Intermediate Similarity	NPC214644
0.8103	Intermediate Similarity	NPC475041
0.8103	Intermediate Similarity	NPC161065
0.8103	Intermediate Similarity	NPC61520
0.8099	Intermediate Similarity	NPC231529
0.8095	Intermediate Similarity	NPC328162
0.8095	Intermediate Similarity	NPC117133
0.8095	Intermediate Similarity	NPC472733
0.8095	Intermediate Similarity	NPC96859
0.8095	Intermediate Similarity	NPC472734
0.8095	Intermediate Similarity	NPC305483
0.8091	Intermediate Similarity	NPC220974
0.8091	Intermediate Similarity	NPC44063
0.8091	Intermediate Similarity	NPC475294
0.8091	Intermediate Similarity	NPC9457
0.8091	Intermediate Similarity	NPC471783
0.8091	Intermediate Similarity	NPC230541
0.8091	Intermediate Similarity	NPC59530
0.8087	Intermediate Similarity	NPC140055
0.8087	Intermediate Similarity	NPC167606
0.8087	Intermediate Similarity	NPC20302
0.8087	Intermediate Similarity	NPC286528
0.8077	Intermediate Similarity	NPC240617
0.8077	Intermediate Similarity	NPC49670
0.8077	Intermediate Similarity	NPC471040
0.8073	Intermediate Similarity	NPC235889
0.807	Intermediate Similarity	NPC471398
0.807	Intermediate Similarity	NPC243354
0.8067	Intermediate Similarity	NPC473255
0.8067	Intermediate Similarity	NPC8369
0.8056	Intermediate Similarity	NPC477915
0.8053	Intermediate Similarity	NPC280782
0.8053	Intermediate Similarity	NPC205534
0.8053	Intermediate Similarity	NPC207251
0.8051	Intermediate Similarity	NPC170538
0.8037	Intermediate Similarity	NPC201406
0.8037	Intermediate Similarity	NPC112167
0.8036	Intermediate Similarity	NPC210005
0.8036	Intermediate Similarity	NPC473627
0.8034	Intermediate Similarity	NPC241192
0.802	Intermediate Similarity	NPC472324
0.8019	Intermediate Similarity	NPC473456
0.8019	Intermediate Similarity	NPC472732
0.8019	Intermediate Similarity	NPC23680
0.8019	Intermediate Similarity	NPC226986
0.8019	Intermediate Similarity	NPC472731
0.8018	Intermediate Similarity	NPC293850
0.8017	Intermediate Similarity	NPC50774
0.8017	Intermediate Similarity	NPC709
0.8	Intermediate Similarity	NPC181357
0.8	Intermediate Similarity	NPC478052
0.8	Intermediate Similarity	NPC96312
0.8	Intermediate Similarity	NPC266570
0.8	Intermediate Similarity	NPC37787
0.8	Intermediate Similarity	NPC251236
0.8	Intermediate Similarity	NPC176840
0.8	Intermediate Similarity	NPC207217
0.8	Intermediate Similarity	NPC180557
0.8	Intermediate Similarity	NPC328374
0.8	Intermediate Similarity	NPC302471
0.8	Intermediate Similarity	NPC40632
0.8	Intermediate Similarity	NPC149047
0.8	Intermediate Similarity	NPC469329
0.8	Intermediate Similarity	NPC473415
0.8	Intermediate Similarity	NPC472655
0.8	Intermediate Similarity	NPC139459
0.8	Intermediate Similarity	NPC270958
0.8	Intermediate Similarity	NPC293112
0.8	Intermediate Similarity	NPC323834
0.8	Intermediate Similarity	NPC64318
0.8	Intermediate Similarity	NPC196931
0.8	Intermediate Similarity	NPC30677
0.8	Intermediate Similarity	NPC181265
0.7983	Intermediate Similarity	NPC120724
0.7983	Intermediate Similarity	NPC469789
0.7982	Intermediate Similarity	NPC140723
0.7982	Intermediate Similarity	NPC179208
0.7982	Intermediate Similarity	NPC49451
0.7982	Intermediate Similarity	NPC282233
0.7982	Intermediate Similarity	NPC277074
0.7982	Intermediate Similarity	NPC95585
0.7982	Intermediate Similarity	NPC112009
0.7982	Intermediate Similarity	NPC194273
0.7982	Intermediate Similarity	NPC209298
0.7981	Intermediate Similarity	NPC134826
0.7981	Intermediate Similarity	NPC294263
0.7981	Intermediate Similarity	NPC474185
0.7965	Intermediate Similarity	NPC471243
0.7965	Intermediate Similarity	NPC201992
0.7965	Intermediate Similarity	NPC188738
0.7963	Intermediate Similarity	NPC233012
0.7963	Intermediate Similarity	NPC303559
0.7963	Intermediate Similarity	NPC252614
0.7963	Intermediate Similarity	NPC54909
0.7961	Intermediate Similarity	NPC126993
0.7961	Intermediate Similarity	NPC471896
0.7961	Intermediate Similarity	NPC85173
0.7949	Intermediate Similarity	NPC264954
0.7949	Intermediate Similarity	NPC473203
0.7946	Intermediate Similarity	NPC10064
0.7946	Intermediate Similarity	NPC170221
0.7946	Intermediate Similarity	NPC2766
0.7946	Intermediate Similarity	NPC241927
0.7946	Intermediate Similarity	NPC258543
0.7946	Intermediate Similarity	NPC141350
0.7944	Intermediate Similarity	NPC153776
0.7944	Intermediate Similarity	NPC472730
0.7944	Intermediate Similarity	NPC471717
0.7944	Intermediate Similarity	NPC477854
0.7944	Intermediate Similarity	NPC177680
0.7944	Intermediate Similarity	NPC472729
0.7941	Intermediate Similarity	NPC328539
0.7941	Intermediate Similarity	NPC474677
0.7934	Intermediate Similarity	NPC470882
0.7931	Intermediate Similarity	NPC470492

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 NPC239097 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	1429
0.2-0.3	3581
0.3-0.4	2519
0.4-0.5	946
0.5-0.6	242
0.6-0.7	144
0.7-0.8	111
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
0.8235	Intermediate Similarity	NPD6079	Approved
0.8214	Intermediate Similarity	NPD8297	Approved
0.8182	Intermediate Similarity	NPD6899	Approved
0.8182	Intermediate Similarity	NPD6881	Approved
0.8125	Intermediate Similarity	NPD6650	Approved
0.8125	Intermediate Similarity	NPD6649	Approved
0.8091	Intermediate Similarity	NPD5697	Approved
0.8087	Intermediate Similarity	NPD7115	Discovery
0.8039	Intermediate Similarity	NPD5328	Approved
0.8036	Intermediate Similarity	NPD7102	Approved
0.8036	Intermediate Similarity	NPD7290	Approved
0.8036	Intermediate Similarity	NPD6883	Approved
0.8018	Intermediate Similarity	NPD6011	Approved
0.8018	Intermediate Similarity	NPD7320	Approved
0.8	Intermediate Similarity	NPD6402	Approved
0.8	Intermediate Similarity	NPD6675	Approved
0.8	Intermediate Similarity	NPD5739	Approved
0.8	Intermediate Similarity	NPD7128	Approved
0.7982	Intermediate Similarity	NPD4632	Approved
0.7981	Intermediate Similarity	NPD6399	Phase 3
0.7965	Intermediate Similarity	NPD8130	Phase 1
0.7965	Intermediate Similarity	NPD6617	Approved
0.7965	Intermediate Similarity	NPD6869	Approved
0.7965	Intermediate Similarity	NPD6847	Approved
0.7946	Intermediate Similarity	NPD6012	Approved
0.7946	Intermediate Similarity	NPD6373	Approved
0.7946	Intermediate Similarity	NPD6372	Approved
0.7946	Intermediate Similarity	NPD6014	Approved
0.7946	Intermediate Similarity	NPD6013	Approved
0.7925	Intermediate Similarity	NPD5221	Approved
0.7925	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD5222	Approved
0.7895	Intermediate Similarity	NPD6882	Approved
0.785	Intermediate Similarity	NPD5173	Approved
0.7768	Intermediate Similarity	NPD5701	Approved
0.7757	Intermediate Similarity	NPD4697	Phase 3
0.7745	Intermediate Similarity	NPD3618	Phase 1
0.7736	Intermediate Similarity	NPD7748	Approved
0.7731	Intermediate Similarity	NPD6319	Approved
0.7714	Intermediate Similarity	NPD7515	Phase 2
0.7706	Intermediate Similarity	NPD5285	Approved
0.7706	Intermediate Similarity	NPD5286	Approved
0.7706	Intermediate Similarity	NPD4696	Approved
0.7692	Intermediate Similarity	NPD6868	Approved
0.7685	Intermediate Similarity	NPD7902	Approved
0.7679	Intermediate Similarity	NPD6008	Approved
0.7652	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD5223	Approved
0.7627	Intermediate Similarity	NPD6009	Approved
0.7623	Intermediate Similarity	NPD7492	Approved
0.7583	Intermediate Similarity	NPD6054	Approved
0.7568	Intermediate Similarity	NPD5224	Approved
0.7568	Intermediate Similarity	NPD5211	Phase 2
0.7568	Intermediate Similarity	NPD5225	Approved
0.7568	Intermediate Similarity	NPD4633	Approved
0.7568	Intermediate Similarity	NPD5226	Approved
0.7563	Intermediate Similarity	NPD6335	Approved
0.7561	Intermediate Similarity	NPD6616	Approved
0.7549	Intermediate Similarity	NPD4786	Approved
0.7541	Intermediate Similarity	NPD7604	Phase 2
0.7523	Intermediate Similarity	NPD6083	Phase 2
0.7523	Intermediate Similarity	NPD6084	Phase 2
0.7523	Intermediate Similarity	NPD4755	Approved
0.7521	Intermediate Similarity	NPD5983	Phase 2
0.7521	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7100	Approved
0.75	Intermediate Similarity	NPD7101	Approved
0.75	Intermediate Similarity	NPD5175	Approved
0.75	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3573	Approved
0.75	Intermediate Similarity	NPD5174	Approved
0.75	Intermediate Similarity	NPD7078	Approved
0.7479	Intermediate Similarity	NPD6317	Approved
0.7459	Intermediate Similarity	NPD6370	Approved
0.7455	Intermediate Similarity	NPD4225	Approved
0.744	Intermediate Similarity	NPD7736	Approved
0.7434	Intermediate Similarity	NPD5141	Approved
0.7429	Intermediate Similarity	NPD6903	Approved
0.7429	Intermediate Similarity	NPD5737	Approved
0.7429	Intermediate Similarity	NPD6672	Approved
0.7419	Intermediate Similarity	NPD6336	Discontinued
0.7417	Intermediate Similarity	NPD6313	Approved
0.7417	Intermediate Similarity	NPD6314	Approved
0.7414	Intermediate Similarity	NPD4634	Approved
0.7407	Intermediate Similarity	NPD7900	Approved
0.7407	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD7334	Approved
0.7404	Intermediate Similarity	NPD7146	Approved
0.7404	Intermediate Similarity	NPD7521	Approved
0.7404	Intermediate Similarity	NPD5330	Approved
0.7404	Intermediate Similarity	NPD6409	Approved
0.7404	Intermediate Similarity	NPD6684	Approved
0.7395	Intermediate Similarity	NPD6274	Approved
0.7387	Intermediate Similarity	NPD4700	Approved
0.7377	Intermediate Similarity	NPD6015	Approved
0.7377	Intermediate Similarity	NPD6016	Approved
0.7353	Intermediate Similarity	NPD3667	Approved
0.7317	Intermediate Similarity	NPD5988	Approved
0.7315	Intermediate Similarity	NPD4202	Approved
0.7297	Intermediate Similarity	NPD5696	Approved
0.7297	Intermediate Similarity	NPD7638	Approved
0.7295	Intermediate Similarity	NPD6059	Approved
0.728	Intermediate Similarity	NPD7507	Approved
0.7264	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4730	Approved
0.7241	Intermediate Similarity	NPD4729	Approved
0.7241	Intermediate Similarity	NPD5168	Approved
0.7232	Intermediate Similarity	NPD7640	Approved
0.7232	Intermediate Similarity	NPD7639	Approved
0.7222	Intermediate Similarity	NPD8293	Discontinued
0.7222	Intermediate Similarity	NPD8034	Phase 2
0.7222	Intermediate Similarity	NPD6411	Approved
0.7222	Intermediate Similarity	NPD8035	Phase 2
0.7212	Intermediate Similarity	NPD3665	Phase 1
0.7212	Intermediate Similarity	NPD3666	Approved
0.7212	Intermediate Similarity	NPD3133	Approved
0.7193	Intermediate Similarity	NPD4754	Approved
0.7182	Intermediate Similarity	NPD5210	Approved
0.7182	Intermediate Similarity	NPD5695	Phase 3
0.7182	Intermediate Similarity	NPD4629	Approved
0.7179	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD6412	Phase 2
0.7143	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD8328	Phase 3
0.7119	Intermediate Similarity	NPD5169	Approved
0.7119	Intermediate Similarity	NPD5250	Approved
0.7119	Intermediate Similarity	NPD5251	Approved
0.7119	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD5247	Approved
0.7119	Intermediate Similarity	NPD5248	Approved
0.7119	Intermediate Similarity	NPD5249	Phase 3
0.7119	Intermediate Similarity	NPD5135	Approved
0.7109	Intermediate Similarity	NPD7319	Approved
0.7097	Intermediate Similarity	NPD6909	Approved
0.7097	Intermediate Similarity	NPD6908	Approved
0.7094	Intermediate Similarity	NPD5128	Approved
0.7094	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD6686	Approved
0.7091	Intermediate Similarity	NPD6001	Approved
0.7075	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD4767	Approved
0.7069	Intermediate Similarity	NPD4768	Approved
0.7064	Intermediate Similarity	NPD5284	Approved
0.7064	Intermediate Similarity	NPD5281	Approved
0.7059	Intermediate Similarity	NPD5217	Approved
0.7059	Intermediate Similarity	NPD5127	Approved
0.7059	Intermediate Similarity	NPD5216	Approved
0.7059	Intermediate Similarity	NPD5215	Approved
0.7037	Intermediate Similarity	NPD4753	Phase 2
0.7037	Intermediate Similarity	NPD6101	Approved
0.7037	Intermediate Similarity	NPD6904	Approved
0.7037	Intermediate Similarity	NPD6673	Approved
0.7037	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6080	Approved
0.7034	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6053	Discontinued
0.699	Remote Similarity	NPD4695	Discontinued
0.6981	Remote Similarity	NPD1694	Approved
0.6975	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD5207	Approved
0.6916	Remote Similarity	NPD5279	Phase 3
0.6899	Remote Similarity	NPD6033	Approved
0.6887	Remote Similarity	NPD3668	Phase 3
0.6885	Remote Similarity	NPD5167	Approved
0.6881	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4223	Phase 3
0.6857	Remote Similarity	NPD4221	Approved
0.6825	Remote Similarity	NPD7503	Approved
0.6822	Remote Similarity	NPD5329	Approved
0.68	Remote Similarity	NPD7516	Approved
0.6792	Remote Similarity	NPD4788	Approved
0.6789	Remote Similarity	NPD5208	Approved
0.6774	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6098	Approved
0.6759	Remote Similarity	NPD5690	Phase 2
0.6757	Remote Similarity	NPD5694	Approved
0.6757	Remote Similarity	NPD6050	Approved
0.6757	Remote Similarity	NPD5693	Phase 1
0.6742	Remote Similarity	NPD7260	Phase 2
0.6729	Remote Similarity	NPD4197	Approved
0.6723	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7328	Approved
0.672	Remote Similarity	NPD7327	Approved
0.6719	Remote Similarity	NPD6067	Discontinued
0.6696	Remote Similarity	NPD5779	Approved
0.6696	Remote Similarity	NPD5778	Approved
0.6693	Remote Similarity	NPD8033	Approved
0.6691	Remote Similarity	NPD6334	Approved
0.6691	Remote Similarity	NPD6333	Approved
0.6667	Remote Similarity	NPD6942	Approved
0.6667	Remote Similarity	NPD7339	Approved
0.6667	Remote Similarity	NPD7525	Registered
0.6667	Remote Similarity	NPD7632	Discontinued
0.6667	Remote Similarity	NPD5785	Approved
0.6667	Remote Similarity	NPD5692	Phase 3
0.6637	Remote Similarity	NPD5282	Discontinued
0.6636	Remote Similarity	NPD5362	Discontinued
0.6636	Remote Similarity	NPD7154	Phase 3

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