NPASS Compound

Structure

NPC469845 OpenBabel07101719252D 37 41 0 0 1 0 0 0 0 0999 V2000 7.4527 1.8478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9886 -4.1522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4527 -1.1522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9527 -0.2862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5348 -0.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8546 1.3478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8546 -1.6522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7861 1.9305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7807 1.8259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9886 -1.1522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1226 -0.6522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5867 0.3478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5867 -2.6522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5867 2.3478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8546 -3.6522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3794 1.0169 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9886 0.8478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8546 -0.6522 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5867 -0.6522 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4527 -2.1522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7206 0.8478 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7206 -2.1522 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2079 0.9781 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.4527 -1.1522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1226 0.3478 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8546 0.3478 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7206 -1.1522 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5867 3.3478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7206 -4.1522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3187 -2.6522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1215 1.3849 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 5.7206 1.8478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8546 -2.6522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 17 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 9 20 2 0 0 0 0 10 11 1 0 0 0 0 10 21 1 0 0 0 0 11 28 1 0 0 0 0 12 26 1 0 0 0 0 13 22 1 0 0 0 0 13 24 1 0 0 0 0 14 23 1 0 0 0 0 14 25 1 0 0 0 0 15 18 1 0 0 0 0 15 35 1 0 0 0 0 16 31 2 0 0 0 0 16 36 1 0 0 0 0 17 32 2 0 0 0 0 17 37 1 0 0 0 0 18 12 1 6 0 0 0 18 19 1 0 0 0 0 19 28 1 6 0 0 0 20 28 1 0 0 0 0 20 29 1 0 0 0 0 21 29 1 1 0 0 0 21 30 1 0 0 0 0 22 27 1 0 0 0 0 22 30 1 1 0 0 0 23 27 1 0 0 0 0 23 33 2 0 0 0 0 24 29 1 6 0 0 0 24 36 1 0 0 0 0 25 30 1 6 0 0 0 25 37 1 0 0 0 0 26 34 1 0 0 0 0 26 35 1 0 0 0 0 28 5 1 6 0 0 0 29 6 1 1 0 0 0 30 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	516.31
Volume:	535.639
LogP:	3.054
LogD:	2.886
LogS:	-4.459
# Rotatable Bonds:	5
TPSA:	99.13
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.432
Synthetic Accessibility Score:	5.298
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.006
MDCK Permeability:	4.9818270781543106e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.034
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.033
30% Bioavailability (F30%):	0.407

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.788
Plasma Protein Binding (PPB):	72.19165802001953%
Volume Distribution (VD):	1.275
Pgp-substrate:	23.25359535217285%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.096
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.782
CYP2C9-inhibitor:	0.071
CYP2C9-substrate:	0.045
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.094
CYP3A4-inhibitor:	0.439
CYP3A4-substrate:	0.655

ADMET: Excretion

Clearance (CL):	2.593
Half-life (T1/2):	0.725

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.522
Drug-inuced Liver Injury (DILI):	0.387
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.092
Maximum Recommended Daily Dose:	0.942
Skin Sensitization:	0.79
Carcinogencity:	0.042
Eye Corrosion:	0.2
Eye Irritation:	0.116
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC469845

Natural Product ID:	NPC469845
*Common Name:**	Neemfruitin A
IUPAC Name:	[(1S,5R,7R,8R,9R,10R,13S,17S)-1-acetyloxy-17-[(3R)-5-hydroxyoxolan-3-yl]-4,4,8,10,13-pentamethyl-3-oxo-1,2,5,6,7,9,11,12,16,17-decahydrocyclopenta[a]phenanthren-7-yl] acetate
Synonyms:
Standard InCHIKey:	DENYEIJQEJNMOG-CLFBBFECSA-N
Standard InCHI:	InChI=1S/C30H44O7/c1-16(31)36-24-13-22-27(3,4)23(33)14-25(37-17(2)32)30(22,7)21-10-11-28(5)19(18-12-26(34)35-15-18)8-9-20(28)29(21,24)6/h9,18-19,21-22,24-26,34H,8,10-15H2,1-7H3/t18-,19-,21-,22-,24+,25-,26?,28-,29-,30+/m0/s1
SMILES:	CC(=O)O[C@@H]1C[C@@H]2[C@]([C@@H]3[C@]1(C)C1=CC[C@H]([C@@]1(CC3)C)[C@@H]1COC(C1)O)(C)[C@@H](OC(=O)C)CC(=O)C2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1214757
PubChem CID:	49864006
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.	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.	bark	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
IC50	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	2820.0	nM	PMID[554083]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1740.0	nM	PMID[554083]

☑ 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 NPC469845 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	217
0.1-0.2	1436
0.2-0.3	4810
0.3-0.4	9380
0.4-0.5	11784
0.5-0.6	6276
0.6-0.7	5056
0.7-0.8	3469
0.8-0.85	247
0.85-0.9	20
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9048	High Similarity	NPC470065
0.8857	High Similarity	NPC469844
0.8667	High Similarity	NPC472655
0.8571	High Similarity	NPC161065
0.8534	High Similarity	NPC298841
0.8496	Intermediate Similarity	NPC241192
0.8491	Intermediate Similarity	NPC231530
0.8491	Intermediate Similarity	NPC278628
0.8476	Intermediate Similarity	NPC140723
0.8468	Intermediate Similarity	NPC302471
0.8426	Intermediate Similarity	NPC218853
0.8411	Intermediate Similarity	NPC61071
0.8411	Intermediate Similarity	NPC96333
0.8411	Intermediate Similarity	NPC88833
0.8396	Intermediate Similarity	NPC222161
0.8396	Intermediate Similarity	NPC470064
0.8396	Intermediate Similarity	NPC470058
0.8396	Intermediate Similarity	NPC470062
0.8396	Intermediate Similarity	NPC470057
0.8396	Intermediate Similarity	NPC101842
0.8396	Intermediate Similarity	NPC470043
0.8396	Intermediate Similarity	NPC470059
0.8396	Intermediate Similarity	NPC470060
0.8396	Intermediate Similarity	NPC470061
0.8378	Intermediate Similarity	NPC472274
0.8364	Intermediate Similarity	NPC12046
0.8364	Intermediate Similarity	NPC194951
0.835	Intermediate Similarity	NPC253586
0.8349	Intermediate Similarity	NPC42776
0.8349	Intermediate Similarity	NPC250956
0.8349	Intermediate Similarity	NPC101450
0.8333	Intermediate Similarity	NPC94529
0.8318	Intermediate Similarity	NPC164600
0.8318	Intermediate Similarity	NPC285927
0.8318	Intermediate Similarity	NPC470055
0.8318	Intermediate Similarity	NPC470056
0.8318	Intermediate Similarity	NPC103172
0.8318	Intermediate Similarity	NPC470587
0.8302	Intermediate Similarity	NPC471005
0.8291	Intermediate Similarity	NPC47113
0.8291	Intermediate Similarity	NPC174367
0.8288	Intermediate Similarity	NPC52634
0.8288	Intermediate Similarity	NPC157441
0.8273	Intermediate Similarity	NPC329953
0.8269	Intermediate Similarity	NPC471038
0.8257	Intermediate Similarity	NPC471250
0.8252	Intermediate Similarity	NPC329910
0.8241	Intermediate Similarity	NPC59530
0.8224	Intermediate Similarity	NPC96268
0.8224	Intermediate Similarity	NPC13149
0.8224	Intermediate Similarity	NPC29705
0.822	Intermediate Similarity	NPC42399
0.8208	Intermediate Similarity	NPC124544
0.819	Intermediate Similarity	NPC108371
0.8182	Intermediate Similarity	NPC130302
0.8182	Intermediate Similarity	NPC49730
0.8182	Intermediate Similarity	NPC98069
0.8182	Intermediate Similarity	NPC5284
0.8165	Intermediate Similarity	NPC258323
0.8158	Intermediate Similarity	NPC239293
0.8155	Intermediate Similarity	NPC470229
0.8155	Intermediate Similarity	NPC279974
0.8155	Intermediate Similarity	NPC470232
0.8142	Intermediate Similarity	NPC243981
0.8137	Intermediate Similarity	NPC470656
0.8131	Intermediate Similarity	NPC159442
0.8131	Intermediate Similarity	NPC87927
0.8131	Intermediate Similarity	NPC312900
0.8131	Intermediate Similarity	NPC139347
0.8125	Intermediate Similarity	NPC255017
0.8125	Intermediate Similarity	NPC471173
0.8125	Intermediate Similarity	NPC471627
0.8113	Intermediate Similarity	NPC163963
0.8113	Intermediate Similarity	NPC52899
0.8113	Intermediate Similarity	NPC289148
0.8113	Intermediate Similarity	NPC46848
0.8108	Intermediate Similarity	NPC471251
0.8108	Intermediate Similarity	NPC272242
0.8095	Intermediate Similarity	NPC474793
0.8095	Intermediate Similarity	NPC58942
0.8095	Intermediate Similarity	NPC475876
0.8095	Intermediate Similarity	NPC119036
0.8095	Intermediate Similarity	NPC260149
0.8091	Intermediate Similarity	NPC118225
0.8091	Intermediate Similarity	NPC31522
0.8087	Intermediate Similarity	NPC258592
0.8087	Intermediate Similarity	NPC178548
0.8077	Intermediate Similarity	NPC200054
0.8077	Intermediate Similarity	NPC193785
0.8077	Intermediate Similarity	NPC29410
0.8073	Intermediate Similarity	NPC293512
0.8058	Intermediate Similarity	NPC47853
0.8058	Intermediate Similarity	NPC470386
0.8058	Intermediate Similarity	NPC470385
0.8058	Intermediate Similarity	NPC475118
0.8056	Intermediate Similarity	NPC121566
0.8056	Intermediate Similarity	NPC475036
0.8056	Intermediate Similarity	NPC100955
0.8056	Intermediate Similarity	NPC471293
0.8053	Intermediate Similarity	NPC243354
0.8053	Intermediate Similarity	NPC477580
0.8037	Intermediate Similarity	NPC148628
0.8037	Intermediate Similarity	NPC275990
0.8037	Intermediate Similarity	NPC88203
0.8037	Intermediate Similarity	NPC286519
0.8037	Intermediate Similarity	NPC246736
0.8037	Intermediate Similarity	NPC214946
0.8037	Intermediate Similarity	NPC193934
0.8037	Intermediate Similarity	NPC76866
0.8037	Intermediate Similarity	NPC304832
0.8037	Intermediate Similarity	NPC271980
0.8036	Intermediate Similarity	NPC152117
0.8036	Intermediate Similarity	NPC234042
0.8019	Intermediate Similarity	NPC477968
0.8019	Intermediate Similarity	NPC471041
0.8019	Intermediate Similarity	NPC94906
0.8019	Intermediate Similarity	NPC219285
0.8019	Intermediate Similarity	NPC267921
0.8019	Intermediate Similarity	NPC161527
0.8019	Intermediate Similarity	NPC287676
0.8019	Intermediate Similarity	NPC477971
0.8019	Intermediate Similarity	NPC477972
0.8019	Intermediate Similarity	NPC228251
0.8019	Intermediate Similarity	NPC20113
0.8018	Intermediate Similarity	NPC255655
0.8018	Intermediate Similarity	NPC124053
0.8018	Intermediate Similarity	NPC197428
0.8018	Intermediate Similarity	NPC98633
0.8	Intermediate Similarity	NPC297179
0.8	Intermediate Similarity	NPC90946
0.8	Intermediate Similarity	NPC275539
0.8	Intermediate Similarity	NPC469729
0.8	Intermediate Similarity	NPC295389
0.8	Intermediate Similarity	NPC189075
0.8	Intermediate Similarity	NPC469733
0.8	Intermediate Similarity	NPC473620
0.8	Intermediate Similarity	NPC19412
0.8	Intermediate Similarity	NPC311534
0.8	Intermediate Similarity	NPC232133
0.8	Intermediate Similarity	NPC300614
0.8	Intermediate Similarity	NPC292133
0.8	Intermediate Similarity	NPC190554
0.7982	Intermediate Similarity	NPC210178
0.7982	Intermediate Similarity	NPC37600
0.7982	Intermediate Similarity	NPC102352
0.7982	Intermediate Similarity	NPC63023
0.7982	Intermediate Similarity	NPC12823
0.7982	Intermediate Similarity	NPC95243
0.7981	Intermediate Similarity	NPC98639
0.7981	Intermediate Similarity	NPC473240
0.7965	Intermediate Similarity	NPC102619
0.7965	Intermediate Similarity	NPC194273
0.7963	Intermediate Similarity	NPC95899
0.7963	Intermediate Similarity	NPC277074
0.7963	Intermediate Similarity	NPC122811
0.7963	Intermediate Similarity	NPC36688
0.7963	Intermediate Similarity	NPC469985
0.7963	Intermediate Similarity	NPC90177
0.7963	Intermediate Similarity	NPC209298
0.7961	Intermediate Similarity	NPC170220
0.7961	Intermediate Similarity	NPC277721
0.7961	Intermediate Similarity	NPC470224
0.7961	Intermediate Similarity	NPC267266
0.7961	Intermediate Similarity	NPC107674
0.7961	Intermediate Similarity	NPC141497
0.7949	Intermediate Similarity	NPC131841
0.7949	Intermediate Similarity	NPC169727
0.7949	Intermediate Similarity	NPC258815
0.7949	Intermediate Similarity	NPC194310
0.7949	Intermediate Similarity	NPC241310
0.7949	Intermediate Similarity	NPC258789
0.7949	Intermediate Similarity	NPC47567
0.7949	Intermediate Similarity	NPC412
0.7946	Intermediate Similarity	NPC270586
0.7946	Intermediate Similarity	NPC285410
0.7946	Intermediate Similarity	NPC250481
0.7946	Intermediate Similarity	NPC471243
0.7946	Intermediate Similarity	NPC31839
0.7946	Intermediate Similarity	NPC201992
0.7946	Intermediate Similarity	NPC263827
0.7946	Intermediate Similarity	NPC470311
0.7944	Intermediate Similarity	NPC75941
0.7944	Intermediate Similarity	NPC471790
0.7944	Intermediate Similarity	NPC470054
0.7944	Intermediate Similarity	NPC236585
0.7931	Intermediate Similarity	NPC477071
0.7928	Intermediate Similarity	NPC476759
0.7928	Intermediate Similarity	NPC112457
0.7928	Intermediate Similarity	NPC143706
0.7928	Intermediate Similarity	NPC472534
0.7928	Intermediate Similarity	NPC469744
0.7928	Intermediate Similarity	NPC469983
0.7925	Intermediate Similarity	NPC162459
0.7925	Intermediate Similarity	NPC16911
0.7925	Intermediate Similarity	NPC38471
0.7925	Intermediate Similarity	NPC98837
0.7925	Intermediate Similarity	NPC78427
0.7925	Intermediate Similarity	NPC28864
0.7925	Intermediate Similarity	NPC20479
0.7925	Intermediate Similarity	NPC114274

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 NPC469845 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	1719
0.2-0.3	3907
0.3-0.4	2199
0.4-0.5	614
0.5-0.6	257
0.6-0.7	183
0.7-0.8	92
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
0.8151	Intermediate Similarity	NPD7736	Approved
0.8067	Intermediate Similarity	NPD8293	Discontinued
0.8034	Intermediate Similarity	NPD6370	Approved
0.7899	Intermediate Similarity	NPD7492	Approved
0.7863	Intermediate Similarity	NPD6054	Approved
0.7863	Intermediate Similarity	NPD6059	Approved
0.7833	Intermediate Similarity	NPD6616	Approved
0.7818	Intermediate Similarity	NPD6008	Approved
0.7788	Intermediate Similarity	NPD6399	Phase 3
0.7787	Intermediate Similarity	NPD7319	Approved
0.7769	Intermediate Similarity	NPD7078	Approved
0.7759	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7686	Intermediate Similarity	NPD7507	Approved
0.7679	Intermediate Similarity	NPD7320	Approved
0.7667	Intermediate Similarity	NPD8328	Phase 3
0.7658	Intermediate Similarity	NPD7128	Approved
0.7658	Intermediate Similarity	NPD6675	Approved
0.7658	Intermediate Similarity	NPD5739	Approved
0.7658	Intermediate Similarity	NPD6402	Approved
0.7647	Intermediate Similarity	NPD6015	Approved
0.7647	Intermediate Similarity	NPD6016	Approved
0.7593	Intermediate Similarity	NPD7638	Approved
0.7583	Intermediate Similarity	NPD5988	Approved
0.7565	Intermediate Similarity	NPD6882	Approved
0.7523	Intermediate Similarity	NPD7640	Approved
0.7523	Intermediate Similarity	NPD7639	Approved
0.7522	Intermediate Similarity	NPD6899	Approved
0.7522	Intermediate Similarity	NPD6881	Approved
0.75	Intermediate Similarity	NPD5328	Approved
0.7458	Intermediate Similarity	NPD6009	Approved
0.7456	Intermediate Similarity	NPD6373	Approved
0.7456	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD6372	Approved
0.7434	Intermediate Similarity	NPD5701	Approved
0.7434	Intermediate Similarity	NPD5697	Approved
0.7434	Intermediate Similarity	NPD6412	Phase 2
0.7419	Intermediate Similarity	NPD6033	Approved
0.7417	Intermediate Similarity	NPD6319	Approved
0.7391	Intermediate Similarity	NPD6883	Approved
0.7391	Intermediate Similarity	NPD7102	Approved
0.7391	Intermediate Similarity	NPD7290	Approved
0.7383	Intermediate Similarity	NPD7748	Approved
0.7368	Intermediate Similarity	NPD6011	Approved
0.7358	Intermediate Similarity	NPD8035	Phase 2
0.7358	Intermediate Similarity	NPD8034	Phase 2
0.7358	Intermediate Similarity	NPD6079	Approved
0.7358	Intermediate Similarity	NPD7515	Phase 2
0.7353	Intermediate Similarity	NPD4786	Approved
0.735	Intermediate Similarity	NPD4632	Approved
0.7339	Intermediate Similarity	NPD7902	Approved
0.7328	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD8130	Phase 1
0.7328	Intermediate Similarity	NPD6617	Approved
0.7328	Intermediate Similarity	NPD6650	Approved
0.7328	Intermediate Similarity	NPD6869	Approved
0.7328	Intermediate Similarity	NPD6847	Approved
0.7328	Intermediate Similarity	NPD6649	Approved
0.7304	Intermediate Similarity	NPD6012	Approved
0.7304	Intermediate Similarity	NPD6014	Approved
0.7304	Intermediate Similarity	NPD6013	Approved
0.7282	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD8297	Approved
0.7236	Intermediate Similarity	NPD6067	Discontinued
0.7217	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD6686	Approved
0.7196	Intermediate Similarity	NPD6411	Approved
0.7182	Intermediate Similarity	NPD4755	Approved
0.7157	Intermediate Similarity	NPD3667	Approved
0.7107	Intermediate Similarity	NPD7327	Approved
0.7107	Intermediate Similarity	NPD7328	Approved
0.7105	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD6114	Approved
0.71	Intermediate Similarity	NPD6118	Approved
0.71	Intermediate Similarity	NPD6697	Approved
0.71	Intermediate Similarity	NPD6115	Approved
0.7097	Intermediate Similarity	NPD7604	Phase 2
0.7094	Intermediate Similarity	NPD4634	Approved
0.7091	Intermediate Similarity	NPD5222	Approved
0.7091	Intermediate Similarity	NPD5221	Approved
0.7091	Intermediate Similarity	NPD4697	Phase 3
0.7091	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD7632	Discontinued
0.7073	Intermediate Similarity	NPD5983	Phase 2
0.7073	Intermediate Similarity	NPD8033	Approved
0.7064	Intermediate Similarity	NPD7900	Approved
0.7064	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD8133	Approved
0.7054	Intermediate Similarity	NPD4700	Approved
0.7054	Intermediate Similarity	NPD5286	Approved
0.7054	Intermediate Similarity	NPD5285	Approved
0.7054	Intermediate Similarity	NPD4696	Approved
0.7049	Intermediate Similarity	NPD7516	Approved
0.7048	Intermediate Similarity	NPD3618	Phase 1
0.7027	Intermediate Similarity	NPD6083	Phase 2
0.7027	Intermediate Similarity	NPD5173	Approved
0.7027	Intermediate Similarity	NPD6084	Phase 2
0.7025	Intermediate Similarity	NPD7115	Discovery
0.7009	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6101	Approved
0.7	Intermediate Similarity	NPD6116	Phase 1
0.7	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD8377	Approved
0.6992	Remote Similarity	NPD8294	Approved
0.6991	Remote Similarity	NPD5223	Approved
0.6984	Remote Similarity	NPD6336	Discontinued
0.6972	Remote Similarity	NPD5779	Approved
0.6972	Remote Similarity	NPD5778	Approved
0.6972	Remote Similarity	NPD4202	Approved
0.6967	Remote Similarity	NPD6335	Approved
0.6961	Remote Similarity	NPD7525	Registered
0.6942	Remote Similarity	NPD6274	Approved
0.6942	Remote Similarity	NPD6868	Approved
0.6935	Remote Similarity	NPD8517	Approved
0.6935	Remote Similarity	NPD8296	Approved
0.6935	Remote Similarity	NPD8378	Approved
0.6935	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD8335	Approved
0.6935	Remote Similarity	NPD8515	Approved
0.6935	Remote Similarity	NPD8380	Approved
0.6935	Remote Similarity	NPD8516	Approved
0.6935	Remote Similarity	NPD8379	Approved
0.6935	Remote Similarity	NPD8513	Phase 3
0.693	Remote Similarity	NPD5226	Approved
0.693	Remote Similarity	NPD5225	Approved
0.693	Remote Similarity	NPD4633	Approved
0.693	Remote Similarity	NPD5224	Approved
0.693	Remote Similarity	NPD5211	Phase 2
0.6916	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD5737	Approved
0.6916	Remote Similarity	NPD6903	Approved
0.6916	Remote Similarity	NPD6672	Approved
0.6911	Remote Similarity	NPD7100	Approved
0.6911	Remote Similarity	NPD7101	Approved
0.69	Remote Similarity	NPD6117	Approved
0.6887	Remote Similarity	NPD6684	Approved
0.6887	Remote Similarity	NPD7334	Approved
0.6887	Remote Similarity	NPD7521	Approved
0.6887	Remote Similarity	NPD5330	Approved
0.6887	Remote Similarity	NPD7146	Approved
0.6887	Remote Similarity	NPD6409	Approved
0.6885	Remote Similarity	NPD6317	Approved
0.6881	Remote Similarity	NPD7637	Suspended
0.687	Remote Similarity	NPD5174	Approved
0.687	Remote Similarity	NPD4754	Approved
0.687	Remote Similarity	NPD5175	Approved
0.6847	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6053	Discontinued
0.6829	Remote Similarity	NPD6314	Approved
0.6829	Remote Similarity	NPD6313	Approved
0.6814	Remote Similarity	NPD4225	Approved
0.681	Remote Similarity	NPD5141	Approved
0.68	Remote Similarity	NPD6909	Approved
0.68	Remote Similarity	NPD6908	Approved
0.68	Remote Similarity	NPD3703	Phase 2
0.6757	Remote Similarity	NPD5282	Discontinued
0.6752	Remote Similarity	NPD4768	Approved
0.6752	Remote Similarity	NPD4767	Approved
0.6729	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.67	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD3668	Phase 3
0.6698	Remote Similarity	NPD3665	Phase 1
0.6698	Remote Similarity	NPD3133	Approved
0.6698	Remote Similarity	NPD3666	Approved
0.6696	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD6334	Approved
0.6667	Remote Similarity	NPD5696	Approved
0.6667	Remote Similarity	NPD6333	Approved
0.6667	Remote Similarity	NPD3573	Approved
0.6639	Remote Similarity	NPD5128	Approved
0.6639	Remote Similarity	NPD4729	Approved
0.6639	Remote Similarity	NPD4730	Approved
0.6607	Remote Similarity	NPD6001	Approved
0.6574	Remote Similarity	NPD6098	Approved
0.6562	Remote Similarity	NPD7122	Discontinued
0.6545	Remote Similarity	NPD6673	Approved
0.6545	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD4753	Phase 2
0.6545	Remote Similarity	NPD6080	Approved
0.6545	Remote Similarity	NPD6904	Approved
0.6535	Remote Similarity	NPD7503	Approved
0.6535	Remote Similarity	NPD6921	Approved
0.6529	Remote Similarity	NPD5135	Approved
0.6529	Remote Similarity	NPD5249	Phase 3
0.6529	Remote Similarity	NPD5169	Approved
0.6529	Remote Similarity	NPD5247	Approved
0.6529	Remote Similarity	NPD5250	Approved
0.6529	Remote Similarity	NPD5251	Approved
0.6529	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD5248	Approved
0.6529	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD5956	Approved
0.6509	Remote Similarity	NPD6435	Approved
0.65	Remote Similarity	NPD5168	Approved
0.65	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6928	Phase 2
0.6475	Remote Similarity	NPD5217	Approved
0.6475	Remote Similarity	NPD5215	Approved
0.6475	Remote Similarity	NPD5127	Approved

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