NPASS Compound

Structure

NPC472671 OpenBabel07101718322D 41 46 0 0 1 0 0 0 0 0999 V2000 2.2326 -4.7589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5396 -3.7815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0174 2.3411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0792 2.5721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2048 1.2081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1954 -1.3190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7456 -0.6320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2326 -3.7815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0618 1.4739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5825 -1.3084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0260 1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0534 -1.7851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9300 -0.7289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0792 -0.3603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7903 0.0701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0294 2.0620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3861 -3.2927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3376 0.4126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9257 2.0834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9161 0.5073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0485 0.0571 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1460 -0.8591 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6063 -0.5139 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0792 0.6171 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2326 -0.8491 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7798 -0.1536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6597 1.2712 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3861 0.6171 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0238 0.7945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3861 -2.3153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2326 1.1059 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3861 -0.3603 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7722 2.5721 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 1.2447 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5396 -1.8265 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4763 0.7664 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8227 -1.5852 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0573 2.1642 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9257 1.1059 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2326 -1.8265 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 8 17 2 0 0 0 0 9 11 2 0 0 0 0 9 20 1 0 0 0 0 10 12 2 0 0 0 0 10 23 1 0 0 0 0 11 37 1 0 0 0 0 12 38 1 0 0 0 0 13 21 1 0 0 0 0 14 24 1 0 0 0 0 14 25 1 0 0 0 0 15 20 2 0 0 0 0 15 37 1 0 0 0 0 16 31 1 0 0 0 0 16 39 1 0 0 0 0 17 30 1 0 0 0 0 18 21 1 0 0 0 0 18 26 2 0 0 0 0 19 34 2 0 0 0 0 19 40 1 0 0 0 0 21 20 1 1 0 0 0 22 13 1 1 0 0 0 22 26 1 0 0 0 0 22 38 1 0 0 0 0 23 32 1 1 0 0 0 23 33 1 0 0 0 0 24 31 1 6 0 0 0 24 40 1 0 0 0 0 25 32 1 6 0 0 0 25 41 1 0 0 0 0 26 33 1 0 0 0 0 27 28 1 0 0 0 0 27 29 1 0 0 0 0 27 39 1 6 0 0 0 28 31 1 1 0 0 0 28 32 1 0 0 0 0 29 33 1 6 0 0 0 29 35 1 0 0 0 0 30 36 2 0 0 0 0 30 41 1 0 0 0 0 31 5 1 1 0 0 0 32 6 1 1 0 0 0 33 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	566.29
Volume:	579.852
LogP:	4.035
LogD:	3.636
LogS:	-4.81
# Rotatable Bonds:	6
TPSA:	104.43
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.3
Synthetic Accessibility Score:	5.773
Fsp3:	0.636
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:	-4.983
MDCK Permeability:	2.700995173654519e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.956
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.124
Plasma Protein Binding (PPB):	92.01604461669922%
Volume Distribution (VD):	3.487
Pgp-substrate:	7.0852532386779785%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.079
CYP2C19-inhibitor:	0.688
CYP2C19-substrate:	0.333
CYP2C9-inhibitor:	0.881
CYP2C9-substrate:	0.025
CYP2D6-inhibitor:	0.14
CYP2D6-substrate:	0.08
CYP3A4-inhibitor:	0.893
CYP3A4-substrate:	0.679

ADMET: Excretion

Clearance (CL):	6.814
Half-life (T1/2):	0.528

ADMET: Toxicity

hERG Blockers:	0.779
Human Hepatotoxicity (H-HT):	0.963
Drug-inuced Liver Injury (DILI):	0.749
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.772
Maximum Recommended Daily Dose:	0.997
Skin Sensitization:	0.067
Carcinogencity:	0.031
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC472671

Natural Product ID:	NPC472671
*Common Name:**	FELAVPUOQIPQFP-KKALZLLWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FELAVPUOQIPQFP-KKALZLLWSA-N
Standard InCHI:	InChI=1S/C33H42O8/c1-8-17(2)30(36)41-25-14-24(40-19(4)34)31(5)16-39-27-28(31)32(25,6)23-10-12-38-22-13-21(20-9-11-37-15-20)18(3)26(22)33(23,7)29(27)35/h8-12,15,21-25,27-29,35H,13-14,16H2,1-7H3/b17-8+/t21-,22+,23-,24-,25+,27-,28+,29-,31-,32+,33-/m1/s1
SMILES:	CC=C(C)C(=O)OC1CC(C2(COC3C2C1(C4C=COC5CC(C(=C5C4(C3O)C)C)C6=COC=C6)C)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581416
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000324] Fatty acid esters

*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
NPO9173	Munronia henryi	Species	Meliaceae	Eukaryota	whole plants	Wenshan, Yunnan Province, China	2012-Nov	PMID[25798528]
NPO9173	Munronia henryi	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	5
Others	4

Activity Type	# Activity
Cell Line	5
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[509842]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	10000.0	nM	PMID[509842]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[509842]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[509842]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	10000.0	nM	PMID[509842]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	49.3	%	PMID[509842]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	38.5	%	PMID[509842]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	24.7	%	PMID[509842]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	20.1	%	PMID[509842]

☑ 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 NPC472671 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	323
0.1-0.2	1190
0.2-0.3	2939
0.3-0.4	5073
0.4-0.5	9982
0.5-0.6	10729
0.6-0.7	10575
0.7-0.8	1411
0.8-0.85	311
0.85-0.9	125
0.9-0.95	34
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.98	High Similarity	NPC475066
0.9669	High Similarity	NPC214495
0.9669	High Similarity	NPC470119
0.9605	High Similarity	NPC475226
0.9548	High Similarity	NPC307781
0.9548	High Similarity	NPC472670
0.9533	High Similarity	NPC29695
0.9533	High Similarity	NPC182427
0.9481	High Similarity	NPC470792
0.9404	High Similarity	NPC322546
0.9404	High Similarity	NPC308205
0.9342	High Similarity	NPC237259
0.9342	High Similarity	NPC98206
0.9342	High Similarity	NPC34421
0.9342	High Similarity	NPC253201
0.9342	High Similarity	NPC302054
0.9304	High Similarity	NPC472673
0.9286	High Similarity	NPC197137
0.9276	High Similarity	NPC472672
0.9245	High Similarity	NPC118086
0.9205	High Similarity	NPC69647
0.9205	High Similarity	NPC125182
0.9167	High Similarity	NPC470789
0.9161	High Similarity	NPC470118
0.9156	High Similarity	NPC296807
0.9156	High Similarity	NPC155939
0.9156	High Similarity	NPC141538
0.9073	High Similarity	NPC255414
0.9068	High Similarity	NPC475237
0.9068	High Similarity	NPC475641
0.9026	High Similarity	NPC268905
0.9024	High Similarity	NPC11062
0.9013	High Similarity	NPC471007
0.8994	High Similarity	NPC62692
0.8994	High Similarity	NPC126984
0.8994	High Similarity	NPC27541
0.8961	High Similarity	NPC116717
0.8954	High Similarity	NPC472654
0.894	High Similarity	NPC5676
0.8938	High Similarity	NPC472141
0.8917	High Similarity	NPC472778
0.8917	High Similarity	NPC472776
0.8917	High Similarity	NPC472777
0.8917	High Similarity	NPC469847
0.891	High Similarity	NPC92979
0.8903	High Similarity	NPC33938
0.8896	High Similarity	NPC470997
0.8896	High Similarity	NPC196846
0.8882	High Similarity	NPC310572
0.8875	High Similarity	NPC61967
0.8861	High Similarity	NPC475967
0.8834	High Similarity	NPC285227
0.8831	High Similarity	NPC195325
0.8831	High Similarity	NPC470790
0.8831	High Similarity	NPC471001
0.8831	High Similarity	NPC470791
0.8831	High Similarity	NPC234494
0.8827	High Similarity	NPC472652
0.8824	High Similarity	NPC216755
0.8824	High Similarity	NPC471174
0.8812	High Similarity	NPC472139
0.8812	High Similarity	NPC472773
0.8797	High Similarity	NPC194499
0.8797	High Similarity	NPC299038
0.8797	High Similarity	NPC88007
0.8765	High Similarity	NPC472651
0.8758	High Similarity	NPC259943
0.875	High Similarity	NPC200782
0.875	High Similarity	NPC251865
0.875	High Similarity	NPC472771
0.875	High Similarity	NPC472668
0.8742	High Similarity	NPC121158
0.8718	High Similarity	NPC291150
0.8718	High Similarity	NPC18135
0.8712	High Similarity	NPC472766
0.8712	High Similarity	NPC271235
0.8712	High Similarity	NPC472765
0.8696	High Similarity	NPC283209
0.8696	High Similarity	NPC471168
0.8696	High Similarity	NPC285567
0.8696	High Similarity	NPC472669
0.8679	High Similarity	NPC195954
0.8662	High Similarity	NPC469503
0.8662	High Similarity	NPC470996
0.8662	High Similarity	NPC294511
0.8662	High Similarity	NPC121615
0.8659	High Similarity	NPC472659
0.8659	High Similarity	NPC470995
0.8654	High Similarity	NPC5180
0.8654	High Similarity	NPC156189
0.865	High Similarity	NPC472774
0.865	High Similarity	NPC472775
0.865	High Similarity	NPC472764
0.8636	High Similarity	NPC470999
0.8634	High Similarity	NPC5741
0.8634	High Similarity	NPC68848
0.8634	High Similarity	NPC471166
0.8634	High Similarity	NPC471167
0.8631	High Similarity	NPC470938
0.8625	High Similarity	NPC84349
0.8614	High Similarity	NPC471632
0.8614	High Similarity	NPC94763
0.8609	High Similarity	NPC67003
0.859	High Similarity	NPC470998
0.8589	High Similarity	NPC470875
0.8589	High Similarity	NPC97574
0.8589	High Similarity	NPC93172
0.8588	High Similarity	NPC242068
0.8588	High Similarity	NPC105395
0.8588	High Similarity	NPC247563
0.8571	High Similarity	NPC472653
0.8562	High Similarity	NPC36655
0.8562	High Similarity	NPC261597
0.8562	High Similarity	NPC167142
0.8562	High Similarity	NPC45101
0.8562	High Similarity	NPC472772
0.8553	High Similarity	NPC44675
0.8553	High Similarity	NPC476262
0.8553	High Similarity	NPC214541
0.8545	High Similarity	NPC472650
0.8545	High Similarity	NPC82602
0.8544	High Similarity	NPC471002
0.8544	High Similarity	NPC476201
0.8544	High Similarity	NPC84063
0.8537	High Similarity	NPC100333
0.8528	High Similarity	NPC470182
0.8528	High Similarity	NPC469849
0.8528	High Similarity	NPC276551
0.8519	High Similarity	NPC82851
0.8519	High Similarity	NPC69028
0.8519	High Similarity	NPC79571
0.8519	High Similarity	NPC472767
0.8519	High Similarity	NPC188649
0.8519	High Similarity	NPC329938
0.8509	High Similarity	NPC307383
0.8503	High Similarity	NPC471437
0.8503	High Similarity	NPC236004
0.8491	Intermediate Similarity	NPC282445
0.8485	Intermediate Similarity	NPC160651
0.8485	Intermediate Similarity	NPC471397
0.8481	Intermediate Similarity	NPC471000
0.8476	Intermediate Similarity	NPC121995
0.8466	Intermediate Similarity	NPC134254
0.8466	Intermediate Similarity	NPC288602
0.8466	Intermediate Similarity	NPC477405
0.8466	Intermediate Similarity	NPC292389
0.8466	Intermediate Similarity	NPC39986
0.8466	Intermediate Similarity	NPC88841
0.8466	Intermediate Similarity	NPC469846
0.8466	Intermediate Similarity	NPC469338
0.8466	Intermediate Similarity	NPC302369
0.8466	Intermediate Similarity	NPC165218
0.8462	Intermediate Similarity	NPC221809
0.8462	Intermediate Similarity	NPC302987
0.8457	Intermediate Similarity	NPC191828
0.8457	Intermediate Similarity	NPC8389
0.8452	Intermediate Similarity	NPC34056
0.8452	Intermediate Similarity	NPC469633
0.8447	Intermediate Similarity	NPC187149
0.8447	Intermediate Similarity	NPC304692
0.8443	Intermediate Similarity	NPC469848
0.8442	Intermediate Similarity	NPC243577
0.8442	Intermediate Similarity	NPC80635
0.8438	Intermediate Similarity	NPC469336
0.8438	Intermediate Similarity	NPC264943
0.8428	Intermediate Similarity	NPC246164
0.8428	Intermediate Similarity	NPC75906
0.8424	Intermediate Similarity	NPC476850
0.8424	Intermediate Similarity	NPC476861
0.8424	Intermediate Similarity	NPC173516
0.8424	Intermediate Similarity	NPC472282
0.8421	Intermediate Similarity	NPC90953
0.8418	Intermediate Similarity	NPC212257
0.8418	Intermediate Similarity	NPC228842
0.8415	Intermediate Similarity	NPC470940
0.8415	Intermediate Similarity	NPC123088
0.8415	Intermediate Similarity	NPC271657
0.8405	Intermediate Similarity	NPC211777
0.8405	Intermediate Similarity	NPC471003
0.8405	Intermediate Similarity	NPC18986
0.8405	Intermediate Similarity	NPC207978
0.8402	Intermediate Similarity	NPC478177
0.84	Intermediate Similarity	NPC476947
0.8395	Intermediate Similarity	NPC472779
0.8393	Intermediate Similarity	NPC469576
0.8385	Intermediate Similarity	NPC175964
0.8385	Intermediate Similarity	NPC104736
0.8385	Intermediate Similarity	NPC126723
0.8385	Intermediate Similarity	NPC471169
0.8385	Intermediate Similarity	NPC41880
0.8383	Intermediate Similarity	NPC160818
0.8383	Intermediate Similarity	NPC169299
0.8383	Intermediate Similarity	NPC159232
0.8383	Intermediate Similarity	NPC294512
0.8375	Intermediate Similarity	NPC57998
0.8375	Intermediate Similarity	NPC178932
0.8373	Intermediate Similarity	NPC327922
0.8366	Intermediate Similarity	NPC56197
0.8365	Intermediate Similarity	NPC272590
0.8364	Intermediate Similarity	NPC23387

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 NPC472671 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	278
0.1-0.2	846
0.2-0.3	2108
0.3-0.4	2660
0.4-0.5	1954
0.5-0.6	986
0.6-0.7	297
0.7-0.8	19
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8323	Intermediate Similarity	NPD5760	Phase 2
0.8323	Intermediate Similarity	NPD5761	Phase 2
0.8103	Intermediate Similarity	NPD8434	Phase 2
0.7714	Intermediate Similarity	NPD6765	Approved
0.7714	Intermediate Similarity	NPD6764	Approved
0.7688	Intermediate Similarity	NPD4628	Phase 3
0.7542	Intermediate Similarity	NPD6785	Approved
0.7542	Intermediate Similarity	NPD6784	Approved
0.7399	Intermediate Similarity	NPD8127	Discontinued
0.7384	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7819	Suspended
0.7246	Intermediate Similarity	NPD6273	Approved
0.7222	Intermediate Similarity	NPD6559	Discontinued
0.7176	Intermediate Similarity	NPD6599	Discontinued
0.7151	Intermediate Similarity	NPD5844	Phase 1
0.7151	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7075	Discontinued
0.7102	Intermediate Similarity	NPD7199	Phase 2
0.7073	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD4965	Approved
0.7069	Intermediate Similarity	NPD4966	Approved
0.7069	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD4967	Phase 2
0.705	Intermediate Similarity	NPD8404	Phase 2
0.6994	Remote Similarity	NPD6801	Discontinued
0.6989	Remote Similarity	NPD6234	Discontinued
0.6982	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6005	Phase 3
0.697	Remote Similarity	NPD5763	Approved
0.697	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5762	Approved
0.697	Remote Similarity	NPD6004	Phase 3
0.697	Remote Similarity	NPD6002	Phase 3
0.697	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7685	Pre-registration
0.6927	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6799	Approved
0.6914	Remote Similarity	NPD3817	Phase 2
0.6906	Remote Similarity	NPD7799	Discontinued
0.6906	Remote Similarity	NPD3818	Discontinued
0.6906	Remote Similarity	NPD7228	Approved
0.6901	Remote Similarity	NPD920	Approved
0.6897	Remote Similarity	NPD37	Approved
0.6893	Remote Similarity	NPD919	Approved
0.6886	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4380	Phase 2
0.6872	Remote Similarity	NPD7497	Discontinued
0.6871	Remote Similarity	NPD6355	Discontinued
0.6865	Remote Similarity	NPD8313	Approved
0.6865	Remote Similarity	NPD8312	Approved
0.6864	Remote Similarity	NPD7236	Approved
0.6857	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD5494	Approved
0.6851	Remote Similarity	NPD7473	Discontinued
0.6845	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7458	Discontinued
0.6818	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1934	Approved
0.679	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD2532	Approved
0.6784	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD2534	Approved
0.6784	Remote Similarity	NPD2533	Approved
0.678	Remote Similarity	NPD3882	Suspended
0.6778	Remote Similarity	NPD6232	Discontinued
0.6776	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7239	Suspended
0.6761	Remote Similarity	NPD8455	Phase 2
0.6757	Remote Similarity	NPD7240	Approved
0.675	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD2799	Discontinued
0.6746	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD4110	Phase 3
0.6743	Remote Similarity	NPD7411	Suspended
0.6739	Remote Similarity	NPD7074	Phase 3
0.6727	Remote Similarity	NPD6653	Approved
0.6725	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD3226	Approved
0.6723	Remote Similarity	NPD5402	Approved
0.6709	Remote Similarity	NPD1608	Approved
0.6707	Remote Similarity	NPD4140	Approved
0.6707	Remote Similarity	NPD1551	Phase 2
0.6705	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5403	Approved
0.6703	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD6166	Phase 2
0.6703	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5401	Approved
0.6685	Remote Similarity	NPD7054	Approved
0.6685	Remote Similarity	NPD7768	Phase 2
0.6667	Remote Similarity	NPD5735	Approved
0.6667	Remote Similarity	NPD1465	Phase 2
0.6649	Remote Similarity	NPD8407	Phase 2
0.6649	Remote Similarity	NPD7472	Approved
0.6648	Remote Similarity	NPD3749	Approved
0.6647	Remote Similarity	NPD3750	Approved
0.6646	Remote Similarity	NPD8032	Phase 2
0.6631	Remote Similarity	NPD7808	Phase 3
0.663	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.663	Remote Similarity	NPD1247	Approved
0.6627	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6100	Approved
0.6607	Remote Similarity	NPD2796	Approved
0.6607	Remote Similarity	NPD6099	Approved
0.6597	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7229	Phase 3
0.659	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD1243	Approved
0.6579	Remote Similarity	NPD8150	Discontinued
0.6578	Remote Similarity	NPD7251	Discontinued
0.6578	Remote Similarity	NPD8368	Discontinued
0.6573	Remote Similarity	NPD2801	Approved
0.6568	Remote Similarity	NPD2346	Discontinued
0.6568	Remote Similarity	NPD1471	Phase 3
0.6564	Remote Similarity	NPD6832	Phase 2
0.6557	Remote Similarity	NPD3926	Phase 2
0.6552	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.655	Remote Similarity	NPD8166	Discontinued
0.655	Remote Similarity	NPD7003	Approved
0.6548	Remote Similarity	NPD7033	Discontinued
0.6548	Remote Similarity	NPD3748	Approved
0.6543	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6959	Discontinued
0.6529	Remote Similarity	NPD1549	Phase 2
0.6524	Remote Similarity	NPD6797	Phase 2
0.6519	Remote Similarity	NPD17	Approved
0.6512	Remote Similarity	NPD6190	Approved
0.6509	Remote Similarity	NPD2935	Discontinued
0.6509	Remote Similarity	NPD2438	Suspended
0.6505	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD7315	Approved
0.6497	Remote Similarity	NPD7028	Phase 2
0.6491	Remote Similarity	NPD2800	Approved
0.6485	Remote Similarity	NPD6798	Discontinued
0.6471	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD2344	Approved
0.6471	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD7999	Approved
0.6467	Remote Similarity	NPD230	Phase 1
0.6453	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.645	Remote Similarity	NPD7680	Approved
0.6446	Remote Similarity	NPD6663	Approved
0.6446	Remote Similarity	NPD6233	Phase 2
0.6442	Remote Similarity	NPD5647	Approved
0.6437	Remote Similarity	NPD1511	Approved
0.6432	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD7095	Approved
0.6424	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD1778	Approved
0.6409	Remote Similarity	NPD7058	Phase 2
0.6409	Remote Similarity	NPD7057	Phase 3
0.6407	Remote Similarity	NPD4060	Phase 1
0.64	Remote Similarity	NPD3057	Approved
0.64	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD3972	Approved
0.6391	Remote Similarity	NPD7097	Phase 1
0.6386	Remote Similarity	NPD2313	Discontinued
0.6386	Remote Similarity	NPD3764	Approved
0.6386	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD3268	Approved
0.6382	Remote Similarity	NPD4107	Approved
0.638	Remote Similarity	NPD2797	Approved
0.638	Remote Similarity	NPD6362	Approved
0.6377	Remote Similarity	NPD7930	Approved
0.6369	Remote Similarity	NPD6385	Approved
0.6369	Remote Similarity	NPD6386	Approved
0.6369	Remote Similarity	NPD447	Suspended
0.6368	Remote Similarity	NPD7435	Discontinued
0.6364	Remote Similarity	NPD7177	Discontinued
0.6364	Remote Similarity	NPD3751	Discontinued
0.6364	Remote Similarity	NPD1512	Approved
0.6354	Remote Similarity	NPD5353	Approved
0.6353	Remote Similarity	NPD1510	Phase 2
0.6353	Remote Similarity	NPD4308	Phase 3
0.6346	Remote Similarity	NPD7047	Phase 3
0.634	Remote Similarity	NPD8361	Approved
0.634	Remote Similarity	NPD8435	Approved
0.634	Remote Similarity	NPD8360	Approved
0.6337	Remote Similarity	NPD4534	Discontinued
0.6337	Remote Similarity	NPD2424	Discontinued
0.6331	Remote Similarity	NPD1607	Approved
0.6324	Remote Similarity	NPD3787	Discontinued
0.6324	Remote Similarity	NPD5711	Approved
0.6324	Remote Similarity	NPD5710	Approved
0.6322	Remote Similarity	NPD3887	Approved
0.6322	Remote Similarity	NPD2354	Approved
0.6322	Remote Similarity	NPD2309	Approved
0.6321	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD1283	Approved
0.6319	Remote Similarity	NPD8651	Approved
0.6318	Remote Similarity	NPD2972	Approved
0.6318	Remote Similarity	NPD3533	Approved
0.6316	Remote Similarity	NPD4476	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