NPASS Compound

Structure

NPC56197 OpenBabel07101718202D 32 36 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 3.5981 -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 -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 -3.8601 -0.4523 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 -4.8546 -0.3478 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 -4.1965 1.1303 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 1.7321 -1.0000 0.0000 C 0 0 1 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 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 -5.0625 0.6303 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 17 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 19 1 0 0 0 0 8 20 2 0 0 0 0 9 12 1 0 0 0 0 9 21 1 0 0 0 0 10 13 2 0 0 0 0 10 23 1 0 0 0 0 11 14 2 0 0 0 0 11 18 1 0 0 0 0 12 26 1 0 0 0 0 13 27 1 0 0 0 0 14 31 1 0 0 0 0 15 22 1 0 0 0 0 15 24 1 0 0 0 0 16 18 2 0 0 0 0 16 31 1 0 0 0 0 17 29 2 0 0 0 0 17 32 1 0 0 0 0 18 19 1 0 0 0 0 19 26 1 6 0 0 0 20 26 1 0 0 0 0 20 28 1 0 0 0 0 21 27 1 1 0 0 0 21 28 1 0 0 0 0 22 25 1 0 0 0 0 22 27 1 1 0 0 0 23 25 1 0 0 0 0 23 30 2 0 0 0 0 24 28 1 6 0 0 0 24 32 1 0 0 0 0 26 4 1 6 0 0 0 27 5 1 1 0 0 0 28 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	436.26
Volume:	469.404
LogP:	4.539
LogD:	3.762
LogS:	-5.015
# Rotatable Bonds:	3
TPSA:	56.51
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.407
Synthetic Accessibility Score:	4.858
Fsp3:	0.643
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:	-5.072
MDCK Permeability:	3.9391648897435516e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.317
30% Bioavailability (F30%):	0.956

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038
Plasma Protein Binding (PPB):	97.82886505126953%
Volume Distribution (VD):	2.077
Pgp-substrate:	5.031197547912598%

ADMET: Metabolism

CYP1A2-inhibitor:	0.066
CYP1A2-substrate:	0.152
CYP2C19-inhibitor:	0.59
CYP2C19-substrate:	0.775
CYP2C9-inhibitor:	0.723
CYP2C9-substrate:	0.085
CYP2D6-inhibitor:	0.464
CYP2D6-substrate:	0.057
CYP3A4-inhibitor:	0.852
CYP3A4-substrate:	0.726

ADMET: Excretion

Clearance (CL):	4.309
Half-life (T1/2):	0.357

ADMET: Toxicity

hERG Blockers:	0.063
Human Hepatotoxicity (H-HT):	0.466
Drug-inuced Liver Injury (DILI):	0.108
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.952
Maximum Recommended Daily Dose:	0.972
Skin Sensitization:	0.153
Carcinogencity:	0.111
Eye Corrosion:	0.01
Eye Irritation:	0.101
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC56197

Natural Product ID:	NPC56197
*Common Name:**	Azadirone
IUPAC Name:	[(5R,7R,8R,9R,10R,13S,17R)-17-(furan-3-yl)-4,4,8,10,13-pentamethyl-3-oxo-5,6,7,9,11,12,16,17-octahydrocyclopenta[a]phenanthren-7-yl] acetate
Synonyms:	Azadirone
Standard InCHIKey:	XXIKKMLIDXLAIK-RFKFVWFBSA-N
Standard InCHI:	InChI=1S/C28H36O4/c1-17(29)32-24-15-22-25(2,3)23(30)10-13-27(22,5)21-9-12-26(4)19(18-11-14-31-16-18)7-8-20(26)28(21,24)6/h8,10-11,13-14,16,19,21-22,24H,7,9,12,15H2,1-6H3/t19-,21+,22-,24+,26-,27+,28-/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)c1ccoc1)(C)C=CC(=O)C2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1215753
PubChem CID:	10906239
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
IC50	2
Others	3

Activity Type	# Activity
Organism	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1210.0	nM	PMID[527133]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1630.0	nM	PMID[527133]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	AFI	=	48.3	%	PMID[527134]
NPT610	Others	Molecular identity unknown		FC	=	2.3	n.a.	PMID[527135]
NPT610	Others	Molecular identity unknown		FC	=	2.7	n.a.	PMID[527135]

☑ 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 NPC56197 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	326
0.1-0.2	1452
0.2-0.3	2818
0.3-0.4	6137
0.4-0.5	11589
0.5-0.6	11029
0.6-0.7	8208
0.7-0.8	805
0.8-0.85	218
0.85-0.9	96
0.9-0.95	15
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9706	High Similarity	NPC199044
0.9706	High Similarity	NPC238843
0.9565	High Similarity	NPC471292
0.9496	High Similarity	NPC471174
0.9362	High Similarity	NPC234494
0.9362	High Similarity	NPC471001
0.9357	High Similarity	NPC216755
0.9296	High Similarity	NPC470997
0.9231	High Similarity	NPC272590
0.9214	High Similarity	NPC185456
0.9167	High Similarity	NPC33938
0.9167	High Similarity	NPC246164
0.9149	High Similarity	NPC470999
0.9085	High Similarity	NPC302987
0.9041	High Similarity	NPC92979
0.9041	High Similarity	NPC141538
0.9041	High Similarity	NPC155939
0.9041	High Similarity	NPC25351
0.9041	High Similarity	NPC296807
0.9034	High Similarity	NPC471002
0.9028	High Similarity	NPC156189
0.8966	High Similarity	NPC471000
0.8958	High Similarity	NPC470791
0.8958	High Similarity	NPC470790
0.8958	High Similarity	NPC472654
0.8958	High Similarity	NPC470998
0.8944	High Similarity	NPC34056
0.8897	High Similarity	NPC471006
0.8897	High Similarity	NPC196846
0.8889	High Similarity	NPC298190
0.8881	High Similarity	NPC198904
0.8865	High Similarity	NPC121158
0.8864	High Similarity	NPC179354
0.8849	High Similarity	NPC476943
0.8836	High Similarity	NPC291150
0.8836	High Similarity	NPC116717
0.8819	High Similarity	NPC71821
0.8811	High Similarity	NPC56731
0.8797	High Similarity	NPC74612
0.8777	High Similarity	NPC307401
0.8777	High Similarity	NPC310830
0.8767	High Similarity	NPC469335
0.8767	High Similarity	NPC5180
0.8767	High Similarity	NPC159927
0.8742	High Similarity	NPC471003
0.8741	High Similarity	NPC251865
0.8741	High Similarity	NPC142113
0.8714	High Similarity	NPC236532
0.8714	High Similarity	NPC220094
0.8712	High Similarity	NPC16922
0.8705	High Similarity	NPC146872
0.8684	High Similarity	NPC224394
0.8684	High Similarity	NPC663
0.8667	High Similarity	NPC469847
0.8652	High Similarity	NPC202260
0.8649	High Similarity	NPC470996
0.8649	High Similarity	NPC182427
0.8649	High Similarity	NPC308205
0.8649	High Similarity	NPC29695
0.8649	High Similarity	NPC472672
0.8649	High Similarity	NPC322546
0.8643	High Similarity	NPC470742
0.8643	High Similarity	NPC310043
0.8639	High Similarity	NPC477404
0.8639	High Similarity	NPC196864
0.8639	High Similarity	NPC212257
0.863	High Similarity	NPC93666
0.8621	High Similarity	NPC262198
0.8621	High Similarity	NPC346
0.8618	High Similarity	NPC197596
0.8613	High Similarity	NPC61788
0.8611	High Similarity	NPC476944
0.8609	High Similarity	NPC474932
0.8592	High Similarity	NPC67003
0.8591	High Similarity	NPC30222
0.8591	High Similarity	NPC237259
0.8591	High Similarity	NPC253201
0.8591	High Similarity	NPC98206
0.8591	High Similarity	NPC34421
0.8591	High Similarity	NPC178932
0.8591	High Similarity	NPC302054
0.8571	High Similarity	NPC214572
0.8562	High Similarity	NPC221809
0.8562	High Similarity	NPC255414
0.8551	High Similarity	NPC471817
0.8543	High Similarity	NPC470118
0.8543	High Similarity	NPC197137
0.8542	High Similarity	NPC223415
0.8542	High Similarity	NPC80635
0.8533	High Similarity	NPC469336
0.8533	High Similarity	NPC35000
0.8533	High Similarity	NPC469850
0.8529	High Similarity	NPC112706
0.8529	High Similarity	NPC207294
0.8529	High Similarity	NPC327527
0.8529	High Similarity	NPC476917
0.8523	High Similarity	NPC121615
0.8523	High Similarity	NPC469503
0.8523	High Similarity	NPC294511
0.8519	High Similarity	NPC46536
0.8519	High Similarity	NPC138139
0.8514	High Similarity	NPC476122
0.8511	High Similarity	NPC42400
0.8503	High Similarity	NPC471007
0.85	High Similarity	NPC476947
0.85	High Similarity	NPC92941
0.8497	Intermediate Similarity	NPC470792
0.8496	Intermediate Similarity	NPC36255
0.8493	Intermediate Similarity	NPC233763
0.8489	Intermediate Similarity	NPC218838
0.8478	Intermediate Similarity	NPC89133
0.8477	Intermediate Similarity	NPC209364
0.8467	Intermediate Similarity	NPC59502
0.8467	Intermediate Similarity	NPC471863
0.8456	Intermediate Similarity	NPC18135
0.8456	Intermediate Similarity	NPC83178
0.8446	Intermediate Similarity	NPC69647
0.8446	Intermediate Similarity	NPC125182
0.8446	Intermediate Similarity	NPC195325
0.8444	Intermediate Similarity	NPC230979
0.8442	Intermediate Similarity	NPC165218
0.844	Intermediate Similarity	NPC46896
0.8435	Intermediate Similarity	NPC470941
0.8435	Intermediate Similarity	NPC224418
0.8431	Intermediate Similarity	NPC470789
0.8421	Intermediate Similarity	NPC472283
0.8421	Intermediate Similarity	NPC470119
0.8421	Intermediate Similarity	NPC286722
0.8421	Intermediate Similarity	NPC214495
0.8421	Intermediate Similarity	NPC475066
0.8414	Intermediate Similarity	NPC470741
0.8414	Intermediate Similarity	NPC243577
0.8414	Intermediate Similarity	NPC267632
0.8406	Intermediate Similarity	NPC476925
0.8403	Intermediate Similarity	NPC20500
0.8403	Intermediate Similarity	NPC205765
0.84	Intermediate Similarity	NPC476201
0.8397	Intermediate Similarity	NPC478179
0.8394	Intermediate Similarity	NPC477966
0.8394	Intermediate Similarity	NPC477040
0.8394	Intermediate Similarity	NPC477123
0.8392	Intermediate Similarity	NPC90953
0.8389	Intermediate Similarity	NPC46551
0.8389	Intermediate Similarity	NPC228842
0.8377	Intermediate Similarity	NPC471167
0.8377	Intermediate Similarity	NPC472668
0.8377	Intermediate Similarity	NPC471166
0.837	Intermediate Similarity	NPC83115
0.8369	Intermediate Similarity	NPC158525
0.8366	Intermediate Similarity	NPC475226
0.8366	Intermediate Similarity	NPC472671
0.8366	Intermediate Similarity	NPC307383
0.8366	Intermediate Similarity	NPC84349
0.8366	Intermediate Similarity	NPC473473
0.8366	Intermediate Similarity	NPC475295
0.8357	Intermediate Similarity	NPC293253
0.8357	Intermediate Similarity	NPC470740
0.8355	Intermediate Similarity	NPC104736
0.8355	Intermediate Similarity	NPC204663
0.8355	Intermediate Similarity	NPC41880
0.8355	Intermediate Similarity	NPC107646
0.8345	Intermediate Similarity	NPC263337
0.8344	Intermediate Similarity	NPC282445
0.8344	Intermediate Similarity	NPC57998
0.8333	Intermediate Similarity	NPC243704
0.8333	Intermediate Similarity	NPC208389
0.8333	Intermediate Similarity	NPC478178
0.8323	Intermediate Similarity	NPC472669
0.8323	Intermediate Similarity	NPC471168
0.8311	Intermediate Similarity	NPC250228
0.8311	Intermediate Similarity	NPC10088
0.8301	Intermediate Similarity	NPC195131
0.8301	Intermediate Similarity	NPC167142
0.8301	Intermediate Similarity	NPC304692
0.8301	Intermediate Similarity	NPC195954
0.8301	Intermediate Similarity	NPC88007
0.8301	Intermediate Similarity	NPC194499
0.8301	Intermediate Similarity	NPC7059
0.8301	Intermediate Similarity	NPC249021
0.8301	Intermediate Similarity	NPC472772
0.8299	Intermediate Similarity	NPC5676
0.8291	Intermediate Similarity	NPC470995
0.8289	Intermediate Similarity	NPC264943
0.8289	Intermediate Similarity	NPC476262
0.8289	Intermediate Similarity	NPC471175
0.8289	Intermediate Similarity	NPC214541
0.8289	Intermediate Similarity	NPC44675
0.8288	Intermediate Similarity	NPC470273
0.8278	Intermediate Similarity	NPC268905
0.8278	Intermediate Similarity	NPC75906
0.8273	Intermediate Similarity	NPC21460
0.8269	Intermediate Similarity	NPC27541
0.8269	Intermediate Similarity	NPC62692
0.8269	Intermediate Similarity	NPC126984
0.8269	Intermediate Similarity	NPC61967
0.8264	Intermediate Similarity	NPC474722
0.8261	Intermediate Similarity	NPC477039
0.8258	Intermediate Similarity	NPC5079
0.8258	Intermediate Similarity	NPC69028
0.8248	Intermediate Similarity	NPC23086

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 NPC56197 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	293
0.1-0.2	1010
0.2-0.3	1736
0.3-0.4	2709
0.4-0.5	2025
0.5-0.6	1081
0.6-0.7	276
0.7-0.8	20
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
0.8289	Intermediate Similarity	NPD5761	Phase 2
0.8289	Intermediate Similarity	NPD5760	Phase 2
0.7866	Intermediate Similarity	NPD6764	Approved
0.7866	Intermediate Similarity	NPD6765	Approved
0.7679	Intermediate Similarity	NPD6784	Approved
0.7679	Intermediate Similarity	NPD6785	Approved
0.7625	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD6273	Approved
0.7534	Intermediate Similarity	NPD8032	Phase 2
0.7533	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD8434	Phase 2
0.7417	Intermediate Similarity	NPD1471	Phase 3
0.7386	Intermediate Similarity	NPD4628	Phase 3
0.729	Intermediate Similarity	NPD7236	Approved
0.7273	Intermediate Similarity	NPD3972	Approved
0.7233	Intermediate Similarity	NPD7458	Discontinued
0.7208	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD1876	Approved
0.7171	Intermediate Similarity	NPD2799	Discontinued
0.716	Intermediate Similarity	NPD7819	Suspended
0.7117	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD8127	Discontinued
0.7107	Intermediate Similarity	NPD920	Approved
0.7095	Intermediate Similarity	NPD6832	Phase 2
0.7078	Intermediate Similarity	NPD2346	Discontinued
0.707	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7239	Suspended
0.7063	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3748	Approved
0.7051	Intermediate Similarity	NPD7003	Approved
0.702	Intermediate Similarity	NPD4140	Approved
0.7019	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD2796	Approved
0.7007	Intermediate Similarity	NPD3266	Approved
0.7007	Intermediate Similarity	NPD3267	Approved
0.7	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD5327	Phase 3
0.6981	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6599	Discontinued
0.6974	Remote Similarity	NPD6355	Discontinued
0.6968	Remote Similarity	NPD2344	Approved
0.6966	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD17	Approved
0.6943	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD1241	Discontinued
0.6908	Remote Similarity	NPD4307	Phase 2
0.6908	Remote Similarity	NPD2979	Phase 3
0.6899	Remote Similarity	NPD3887	Approved
0.6897	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD2313	Discontinued
0.6887	Remote Similarity	NPD3268	Approved
0.6886	Remote Similarity	NPD919	Approved
0.6879	Remote Similarity	NPD1243	Approved
0.6875	Remote Similarity	NPD5585	Approved
0.6871	Remote Similarity	NPD7028	Phase 2
0.6864	Remote Similarity	NPD6808	Phase 2
0.6849	Remote Similarity	NPD1281	Approved
0.6846	Remote Similarity	NPD2798	Approved
0.6845	Remote Similarity	NPD5494	Approved
0.6842	Remote Similarity	NPD6663	Approved
0.6835	Remote Similarity	NPD3750	Approved
0.6835	Remote Similarity	NPD8166	Discontinued
0.6835	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4110	Phase 3
0.6826	Remote Similarity	NPD7075	Discontinued
0.681	Remote Similarity	NPD3226	Approved
0.6803	Remote Similarity	NPD1608	Approved
0.6795	Remote Similarity	NPD2438	Suspended
0.6792	Remote Similarity	NPD2309	Approved
0.678	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD2797	Approved
0.6759	Remote Similarity	NPD5691	Approved
0.6753	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD5763	Approved
0.6752	Remote Similarity	NPD5762	Approved
0.6743	Remote Similarity	NPD6559	Discontinued
0.6731	Remote Similarity	NPD4308	Phase 3
0.6727	Remote Similarity	NPD7411	Suspended
0.6726	Remote Similarity	NPD3749	Approved
0.6714	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD1283	Approved
0.671	Remote Similarity	NPD6353	Approved
0.6708	Remote Similarity	NPD6799	Approved
0.6707	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4107	Approved
0.6689	Remote Similarity	NPD5736	Approved
0.6688	Remote Similarity	NPD6099	Approved
0.6688	Remote Similarity	NPD6100	Approved
0.6688	Remote Similarity	NPD2531	Phase 2
0.6688	Remote Similarity	NPD2935	Discontinued
0.6687	Remote Similarity	NPD6280	Approved
0.6687	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6279	Approved
0.6687	Remote Similarity	NPD6801	Discontinued
0.6667	Remote Similarity	NPD7057	Phase 3
0.6667	Remote Similarity	NPD6798	Discontinued
0.6667	Remote Similarity	NPD7058	Phase 2
0.6667	Remote Similarity	NPD5844	Phase 1
0.6667	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6002	Phase 3
0.6646	Remote Similarity	NPD6005	Phase 3
0.6646	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6004	Phase 3
0.6646	Remote Similarity	NPD2353	Approved
0.6646	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD5735	Approved
0.6644	Remote Similarity	NPD1651	Approved
0.6644	Remote Similarity	NPD4359	Approved
0.6609	Remote Similarity	NPD7799	Discontinued
0.6608	Remote Similarity	NPD7199	Phase 2
0.6605	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD1549	Phase 2
0.6601	Remote Similarity	NPD7095	Approved
0.6599	Remote Similarity	NPD1778	Approved
0.6582	Remote Similarity	NPD4476	Approved
0.6582	Remote Similarity	NPD4477	Approved
0.6582	Remote Similarity	NPD1551	Phase 2
0.6581	Remote Similarity	NPD3140	Approved
0.6581	Remote Similarity	NPD3142	Approved
0.6578	Remote Similarity	NPD4482	Phase 3
0.6568	Remote Similarity	NPD7768	Phase 2
0.6564	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD2532	Approved
0.6564	Remote Similarity	NPD2534	Approved
0.6564	Remote Similarity	NPD2533	Approved
0.6558	Remote Similarity	NPD3764	Approved
0.6556	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4618	Approved
0.6538	Remote Similarity	NPD1933	Approved
0.6538	Remote Similarity	NPD4622	Approved
0.6532	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD3025	Approved
0.6531	Remote Similarity	NPD3024	Approved
0.6531	Remote Similarity	NPD8404	Phase 2
0.6527	Remote Similarity	NPD6873	Phase 2
0.6519	Remote Similarity	NPD7033	Discontinued
0.6516	Remote Similarity	NPD4870	Approved
0.6514	Remote Similarity	NPD7177	Discontinued
0.6513	Remote Similarity	NPD1019	Discontinued
0.6512	Remote Similarity	NPD1247	Approved
0.6509	Remote Similarity	NPD3817	Phase 2
0.6503	Remote Similarity	NPD7094	Approved
0.6503	Remote Similarity	NPD5535	Approved
0.6503	Remote Similarity	NPD6858	Approved
0.65	Remote Similarity	NPD970	Clinical (unspecified phase)
0.65	Remote Similarity	NPD2897	Discontinued
0.6494	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD4626	Approved
0.6486	Remote Similarity	NPD2932	Approved
0.6481	Remote Similarity	NPD2354	Approved
0.6474	Remote Similarity	NPD7229	Phase 3
0.6474	Remote Similarity	NPD4060	Phase 1
0.6471	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD9717	Approved
0.646	Remote Similarity	NPD2800	Approved
0.6457	Remote Similarity	NPD7473	Discontinued
0.6456	Remote Similarity	NPD5689	Approved
0.6456	Remote Similarity	NPD7097	Phase 1
0.6456	Remote Similarity	NPD5688	Approved
0.6447	Remote Similarity	NPD1203	Approved
0.6443	Remote Similarity	NPD3496	Discontinued
0.6443	Remote Similarity	NPD3023	Approved
0.6443	Remote Similarity	NPD3026	Approved
0.6442	Remote Similarity	NPD7440	Discontinued
0.6437	Remote Similarity	NPD3926	Phase 2
0.6429	Remote Similarity	NPD3134	Approved
0.6429	Remote Similarity	NPD5889	Approved
0.6429	Remote Similarity	NPD6677	Suspended
0.6429	Remote Similarity	NPD5890	Approved
0.6421	Remote Similarity	NPD7497	Discontinued
0.6416	Remote Similarity	NPD6959	Discontinued
0.6415	Remote Similarity	NPD1510	Phase 2
0.6412	Remote Similarity	NPD5977	Approved
0.6412	Remote Similarity	NPD5978	Approved
0.641	Remote Similarity	NPD6233	Phase 2
0.6405	Remote Similarity	NPD5647	Approved
0.6405	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6287	Discontinued
0.64	Remote Similarity	NPD1611	Approved
0.6398	Remote Similarity	NPD4534	Discontinued
0.6392	Remote Similarity	NPD6653	Approved
0.6391	Remote Similarity	NPD1934	Approved
0.6391	Remote Similarity	NPD7577	Discontinued
0.6389	Remote Similarity	NPD8313	Approved
0.6389	Remote Similarity	NPD8312	Approved
0.6387	Remote Similarity	NPD7008	Discontinued
0.6386	Remote Similarity	NPD5403	Approved
0.6386	Remote Similarity	NPD3869	Phase 3
0.6386	Remote Similarity	NPD3873	Phase 3
0.6379	Remote Similarity	NPD7315	Approved
0.6376	Remote Similarity	NPD3019	Approved
0.6374	Remote Similarity	NPD3882	Suspended

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