NPASS Compound

Structure

NPC173544 OpenBabel07101718302D 42 45 0 0 1 0 0 0 0 0999 V2000 7.0981 -4.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0981 -4.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5981 1.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4641 -0.2679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4641 0.7321 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 3.5981 3.6962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5981 -3.2321 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 -0.9706 -2.4945 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 -1.9487 -2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5981 1.9641 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 5.0981 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5981 -3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 1.0981 0.0000 C 0 0 2 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 4.0981 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0981 1.0981 0.0000 C 0 0 2 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 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0981 2.8301 0.0000 C 0 0 0 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 3.5981 0.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5981 0.2321 0.0000 C 0 0 0 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 2.5981 -1.5000 0.0000 C 0 0 2 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 5.5981 3.6962 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 2.5981 0.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -0.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 2.8301 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4487 -1.8364 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 4.0981 -2.3660 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 4 30 1 0 0 0 0 5 30 1 0 0 0 0 7 39 1 0 0 0 0 8 17 2 0 0 0 0 9 11 1 0 0 0 0 9 23 1 0 0 0 0 10 12 2 0 0 0 0 10 19 1 0 0 0 0 11 31 1 0 0 0 0 12 40 1 0 0 0 0 13 24 1 0 0 0 0 14 22 2 0 0 0 0 14 25 1 0 0 0 0 15 20 2 0 0 0 0 15 30 1 0 0 0 0 16 19 2 0 0 0 0 16 40 1 0 0 0 0 17 29 1 0 0 0 0 18 3 1 6 0 0 0 18 21 1 0 0 0 0 18 26 1 0 0 0 0 19 27 1 0 0 0 0 20 26 1 0 0 0 0 20 28 1 0 0 0 0 21 13 1 1 0 0 0 21 30 1 0 0 0 0 22 31 1 0 0 0 0 22 32 1 0 0 0 0 23 32 1 0 0 0 0 23 33 2 0 0 0 0 24 34 2 0 0 0 0 24 39 1 0 0 0 0 25 35 2 0 0 0 0 25 41 1 0 0 0 0 26 36 2 0 0 0 0 27 31 1 6 0 0 0 27 41 1 0 0 0 0 28 32 1 0 0 0 0 28 42 1 1 0 0 0 29 37 2 0 0 0 0 29 42 1 0 0 0 0 31 6 1 6 0 0 0 32 38 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	582.25
Volume:	589.34
LogP:	3.542
LogD:	1.579
LogS:	-4.927
# Rotatable Bonds:	9
TPSA:	146.41
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.283
Synthetic Accessibility Score:	5.413
Fsp3:	0.531
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:	-5.016
MDCK Permeability:	1.2752115253533702e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.062
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.931

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.236
Plasma Protein Binding (PPB):	91.99263763427734%
Volume Distribution (VD):	2.16
Pgp-substrate:	5.6945109367370605%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.104
CYP2C19-inhibitor:	0.94
CYP2C19-substrate:	0.462
CYP2C9-inhibitor:	0.964
CYP2C9-substrate:	0.024
CYP2D6-inhibitor:	0.191
CYP2D6-substrate:	0.031
CYP3A4-inhibitor:	0.947
CYP3A4-substrate:	0.907

ADMET: Excretion

Clearance (CL):	3.24
Half-life (T1/2):	0.871

ADMET: Toxicity

hERG Blockers:	0.224
Human Hepatotoxicity (H-HT):	0.835
Drug-inuced Liver Injury (DILI):	0.828
AMES Toxicity:	0.538
Rat Oral Acute Toxicity:	0.995
Maximum Recommended Daily Dose:	0.949
Skin Sensitization:	0.333
Carcinogencity:	0.576
Eye Corrosion:	0.004
Eye Irritation:	0.022
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC173544

Natural Product ID:	NPC173544
*Common Name:**	Granaxylocarpin B
IUPAC Name:	[(R)-[(1R,5R,8aR)-1-(furan-3-yl)-5-hydroxy-8a-methyl-3,6-dioxo-7,8-dihydro-1H-isochromen-5-yl]-[(4R,5R)-4-(2-methoxy-2-oxoethyl)-3,3,5-trimethyl-6-oxocyclohexen-1-yl]methyl] (E)-2-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	ZBJPDPDKXYNWFV-PQAYMIJJSA-N
Standard InCHI:	InChI=1S/C32H38O10/c1-8-17(2)29(37)42-28(20-15-30(4,5)21(13-24(34)39-7)18(3)26(20)36)32(38)22-14-25(35)41-27(19-10-12-40-16-19)31(22,6)11-9-23(32)33/h8,10,12,14-16,18,21,27-28,38H,9,11,13H2,1-7H3/b17-8+/t18-,21-,27+,28-,31-,32+/m1/s1
SMILES:	C/C=C(/C(=O)O[C@@H]([C@@]1(O)C(=O)CC[C@@]2(C1=CC(=O)O[C@H]2c1cocc1)C)C1=CC(C)(C)[C@@H]([C@H](C1=O)C)CC(=O)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL390119
PubChem CID:	16216542
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001986] Tricarboxylic acids and derivatives

*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
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	rind	n.a.	DOI[10.1002/hlca.200800177]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[17323995]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	bark	n.a.	PMID[17450509]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	seed kernels	n.a.	n.a.	PMID[19908853]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20411928]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31895570]
NPO28813	Xylocarpus granatum	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
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	4900.0	nM	PMID[528401]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[528401]

☑ 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 NPC173544 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	329
0.1-0.2	1231
0.2-0.3	2989
0.3-0.4	5802
0.4-0.5	10796
0.5-0.6	9420
0.6-0.7	8256
0.7-0.8	3494
0.8-0.85	285
0.85-0.9	78
0.9-0.95	15
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC469485
0.9671	High Similarity	NPC329938
0.9605	High Similarity	NPC477402
0.9539	High Similarity	NPC477403
0.9419	High Similarity	NPC469849
0.9419	High Similarity	NPC470940
0.9359	High Similarity	NPC470875
0.9355	High Similarity	NPC292389
0.9355	High Similarity	NPC469338
0.9342	High Similarity	NPC264943
0.9295	High Similarity	NPC276551
0.929	High Similarity	NPC193798
0.929	High Similarity	NPC69028
0.9231	High Similarity	NPC477405
0.9226	High Similarity	NPC25255
0.9177	High Similarity	NPC173516
0.9177	High Similarity	NPC472282
0.9167	High Similarity	NPC263432
0.9119	High Similarity	NPC471397
0.9119	High Similarity	NPC160651
0.9097	High Similarity	NPC472283
0.9097	High Similarity	NPC45101
0.9097	High Similarity	NPC261597
0.9097	High Similarity	NPC36655
0.9091	High Similarity	NPC281258
0.9091	High Similarity	NPC214541
0.9091	High Similarity	NPC44675
0.9085	High Similarity	NPC44577
0.9057	High Similarity	NPC472775
0.9057	High Similarity	NPC472774
0.9051	High Similarity	NPC476858
0.9051	High Similarity	NPC123088
0.9051	High Similarity	NPC476857
0.9051	High Similarity	NPC476856
0.9045	High Similarity	NPC82851
0.9012	High Similarity	NPC471437
0.8987	High Similarity	NPC472773
0.8987	High Similarity	NPC224394
0.8987	High Similarity	NPC663
0.8981	High Similarity	NPC472653
0.8974	High Similarity	NPC249021
0.8968	High Similarity	NPC469336
0.8938	High Similarity	NPC476861
0.8938	High Similarity	NPC476853
0.8938	High Similarity	NPC476850
0.8931	High Similarity	NPC476860
0.8924	High Similarity	NPC5079
0.8924	High Similarity	NPC472771
0.8917	High Similarity	NPC237155
0.8917	High Similarity	NPC307383
0.891	High Similarity	NPC60973
0.8903	High Similarity	NPC178932
0.8903	High Similarity	NPC30222
0.8902	High Similarity	NPC478177
0.8875	High Similarity	NPC23387
0.8868	High Similarity	NPC51568
0.8868	High Similarity	NPC234660
0.8861	High Similarity	NPC191828
0.8854	High Similarity	NPC167142
0.8854	High Similarity	NPC472776
0.8854	High Similarity	NPC286722
0.8854	High Similarity	NPC472772
0.8854	High Similarity	NPC187149
0.8854	High Similarity	NPC472778
0.8854	High Similarity	NPC472777
0.8846	High Similarity	NPC35000
0.8846	High Similarity	NPC469850
0.8831	High Similarity	NPC159927
0.8831	High Similarity	NPC46551
0.8831	High Similarity	NPC469335
0.8812	High Similarity	NPC470182
0.8805	High Similarity	NPC149896
0.8805	High Similarity	NPC470939
0.8805	High Similarity	NPC200782
0.8797	High Similarity	NPC475967
0.8797	High Similarity	NPC475295
0.8797	High Similarity	NPC262872
0.8797	High Similarity	NPC473473
0.879	High Similarity	NPC263265
0.879	High Similarity	NPC209364
0.8782	High Similarity	NPC282445
0.878	High Similarity	NPC94763
0.8765	High Similarity	NPC472652
0.8758	High Similarity	NPC475779
0.8758	High Similarity	NPC250228
0.8758	High Similarity	NPC472141
0.875	High Similarity	NPC302369
0.875	High Similarity	NPC198047
0.875	High Similarity	NPC39986
0.875	High Similarity	NPC288602
0.875	High Similarity	NPC88841
0.875	High Similarity	NPC134254
0.8742	High Similarity	NPC305016
0.8742	High Similarity	NPC470789
0.8742	High Similarity	NPC335761
0.8727	High Similarity	NPC469633
0.8718	High Similarity	NPC75906
0.8718	High Similarity	NPC469503
0.871	High Similarity	NPC196864
0.871	High Similarity	NPC477404
0.8704	High Similarity	NPC472651
0.8704	High Similarity	NPC478179
0.8704	High Similarity	NPC473766
0.8704	High Similarity	NPC473753
0.8696	High Similarity	NPC271657
0.8693	High Similarity	NPC346
0.8693	High Similarity	NPC262198
0.8688	High Similarity	NPC207978
0.8688	High Similarity	NPC211777
0.8688	High Similarity	NPC188649
0.8688	High Similarity	NPC290400
0.8688	High Similarity	NPC96443
0.8688	High Similarity	NPC18347
0.8684	High Similarity	NPC137295
0.8679	High Similarity	NPC472779
0.8671	High Similarity	NPC107646
0.8671	High Similarity	NPC126723
0.8667	High Similarity	NPC469576
0.8667	High Similarity	NPC90296
0.8667	High Similarity	NPC471632
0.8667	High Similarity	NPC236004
0.8659	High Similarity	NPC160818
0.8659	High Similarity	NPC169299
0.865	High Similarity	NPC271235
0.8642	High Similarity	NPC149945
0.8642	High Similarity	NPC478178
0.8642	High Similarity	NPC121995
0.8636	High Similarity	NPC470941
0.8634	High Similarity	NPC476197
0.8625	High Similarity	NPC287559
0.8625	High Similarity	NPC475381
0.8616	High Similarity	NPC197137
0.8616	High Similarity	NPC470118
0.8616	High Similarity	NPC299038
0.8608	High Similarity	NPC92979
0.8608	High Similarity	NPC476262
0.8599	High Similarity	NPC476201
0.8599	High Similarity	NPC147168
0.8598	High Similarity	NPC82602
0.8589	High Similarity	NPC100333
0.858	High Similarity	NPC146991
0.8571	High Similarity	NPC117986
0.8571	High Similarity	NPC68848
0.8571	High Similarity	NPC18986
0.8562	High Similarity	NPC142113
0.8562	High Similarity	NPC476944
0.8545	High Similarity	NPC285227
0.8545	High Similarity	NPC159232
0.8544	High Similarity	NPC57998
0.8537	High Similarity	NPC472765
0.8537	High Similarity	NPC472766
0.8537	High Similarity	NPC296558
0.8535	High Similarity	NPC272590
0.8535	High Similarity	NPC18135
0.8529	High Similarity	NPC242068
0.8529	High Similarity	NPC247563
0.8526	High Similarity	NPC69647
0.8526	High Similarity	NPC125182
0.8519	High Similarity	NPC165218
0.8519	High Similarity	NPC419
0.8519	High Similarity	NPC472139
0.8519	High Similarity	NPC469846
0.8516	High Similarity	NPC255414
0.85	High Similarity	NPC88007
0.8497	Intermediate Similarity	NPC267632
0.8485	Intermediate Similarity	NPC470995
0.8481	Intermediate Similarity	NPC33938
0.8476	Intermediate Similarity	NPC476224
0.8476	Intermediate Similarity	NPC270312
0.8476	Intermediate Similarity	NPC472764
0.8471	Intermediate Similarity	NPC476122
0.8467	Intermediate Similarity	NPC310830
0.8466	Intermediate Similarity	NPC261184
0.8457	Intermediate Similarity	NPC470792
0.8457	Intermediate Similarity	NPC472767
0.8457	Intermediate Similarity	NPC197596
0.8456	Intermediate Similarity	NPC158525
0.8447	Intermediate Similarity	NPC473368
0.8447	Intermediate Similarity	NPC475226
0.8442	Intermediate Similarity	NPC86935
0.8438	Intermediate Similarity	NPC41880
0.8431	Intermediate Similarity	NPC121158
0.8424	Intermediate Similarity	NPC327922
0.8421	Intermediate Similarity	NPC105395
0.8418	Intermediate Similarity	NPC116717
0.8415	Intermediate Similarity	NPC214600
0.8415	Intermediate Similarity	NPC97574
0.8415	Intermediate Similarity	NPC93172
0.8411	Intermediate Similarity	NPC476943
0.8411	Intermediate Similarity	NPC220094
0.8408	Intermediate Similarity	NPC472654
0.8408	Intermediate Similarity	NPC329180
0.8408	Intermediate Similarity	NPC195325
0.8405	Intermediate Similarity	NPC285567
0.8397	Intermediate Similarity	NPC221809
0.8393	Intermediate Similarity	NPC262386
0.8387	Intermediate Similarity	NPC34056
0.8385	Intermediate Similarity	NPC195954
0.8385	Intermediate Similarity	NPC194499
0.8383	Intermediate Similarity	NPC469848

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 NPC173544 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	274
0.1-0.2	941
0.2-0.3	2113
0.3-0.4	2607
0.4-0.5	1946
0.5-0.6	948
0.6-0.7	273
0.7-0.8	47
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.858	High Similarity	NPD8434	Phase 2
0.8261	Intermediate Similarity	NPD5760	Phase 2
0.8261	Intermediate Similarity	NPD5761	Phase 2
0.8061	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD6764	Approved
0.7657	Intermediate Similarity	NPD6765	Approved
0.7574	Intermediate Similarity	NPD7075	Discontinued
0.7516	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD6784	Approved
0.7486	Intermediate Similarity	NPD6785	Approved
0.744	Intermediate Similarity	NPD6801	Discontinued
0.7425	Intermediate Similarity	NPD6599	Discontinued
0.736	Intermediate Similarity	NPD6559	Discontinued
0.7353	Intermediate Similarity	NPD5402	Approved
0.7347	Intermediate Similarity	NPD8404	Phase 2
0.7294	Intermediate Similarity	NPD7819	Suspended
0.7262	Intermediate Similarity	NPD3226	Approved
0.7251	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD3817	Phase 2
0.7246	Intermediate Similarity	NPD920	Approved
0.7246	Intermediate Similarity	NPD5403	Approved
0.7241	Intermediate Similarity	NPD1247	Approved
0.7225	Intermediate Similarity	NPD919	Approved
0.7198	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7411	Suspended
0.7169	Intermediate Similarity	NPD6799	Approved
0.7158	Intermediate Similarity	NPD8150	Discontinued
0.7135	Intermediate Similarity	NPD3818	Discontinued
0.7134	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5401	Approved
0.7126	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD4380	Phase 2
0.7117	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD3882	Suspended
0.7088	Intermediate Similarity	NPD8312	Approved
0.7088	Intermediate Similarity	NPD8313	Approved
0.7069	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD1471	Phase 3
0.7011	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5494	Approved
0.6983	Remote Similarity	NPD7473	Discontinued
0.6971	Remote Similarity	NPD3749	Approved
0.6957	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7799	Discontinued
0.6944	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7808	Phase 3
0.694	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD3268	Approved
0.6936	Remote Similarity	NPD1934	Approved
0.6928	Remote Similarity	NPD2800	Approved
0.6927	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6166	Phase 2
0.6927	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2534	Approved
0.6923	Remote Similarity	NPD2533	Approved
0.6923	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2532	Approved
0.6897	Remote Similarity	NPD2801	Approved
0.689	Remote Similarity	NPD7033	Discontinued
0.6885	Remote Similarity	NPD7685	Pre-registration
0.6885	Remote Similarity	NPD7251	Discontinued
0.6865	Remote Similarity	NPD8407	Phase 2
0.686	Remote Similarity	NPD7458	Discontinued
0.6854	Remote Similarity	NPD8127	Discontinued
0.6848	Remote Similarity	NPD2796	Approved
0.6848	Remote Similarity	NPD1551	Phase 2
0.6832	Remote Similarity	NPD2313	Discontinued
0.6831	Remote Similarity	NPD6797	Phase 2
0.6826	Remote Similarity	NPD1243	Approved
0.6824	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7768	Phase 2
0.6816	Remote Similarity	NPD6232	Discontinued
0.6813	Remote Similarity	NPD5844	Phase 1
0.6813	Remote Similarity	NPD7054	Approved
0.681	Remote Similarity	NPD6355	Discontinued
0.6809	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD2346	Discontinued
0.6805	Remote Similarity	NPD7236	Approved
0.6793	Remote Similarity	NPD8368	Discontinued
0.6788	Remote Similarity	NPD2799	Discontinued
0.6786	Remote Similarity	NPD3750	Approved
0.6784	Remote Similarity	NPD1512	Approved
0.6784	Remote Similarity	NPD6273	Approved
0.678	Remote Similarity	NPD7907	Approved
0.6778	Remote Similarity	NPD3926	Phase 2
0.6776	Remote Similarity	NPD7472	Approved
0.6776	Remote Similarity	NPD7074	Phase 3
0.6766	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD1549	Phase 2
0.6758	Remote Similarity	NPD3751	Discontinued
0.6747	Remote Similarity	NPD6100	Approved
0.6747	Remote Similarity	NPD6099	Approved
0.6735	Remote Similarity	NPD7435	Discontinued
0.6708	Remote Similarity	NPD6832	Phase 2
0.6707	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD2344	Approved
0.6707	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD447	Suspended
0.6705	Remote Similarity	NPD7239	Suspended
0.6701	Remote Similarity	NPD8285	Discontinued
0.6687	Remote Similarity	NPD1510	Phase 2
0.6687	Remote Similarity	NPD4308	Phase 3
0.6687	Remote Similarity	NPD5647	Approved
0.6686	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7095	Approved
0.6667	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1511	Approved
0.6667	Remote Similarity	NPD6959	Discontinued
0.6648	Remote Similarity	NPD6234	Discontinued
0.6648	Remote Similarity	NPD37	Approved
0.6648	Remote Similarity	NPD2403	Approved
0.6647	Remote Similarity	NPD2935	Discontinued
0.6647	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6190	Approved
0.6646	Remote Similarity	NPD1608	Approved
0.6635	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD8360	Approved
0.6632	Remote Similarity	NPD8361	Approved
0.6629	Remote Similarity	NPD4966	Approved
0.6629	Remote Similarity	NPD4967	Phase 2
0.6629	Remote Similarity	NPD4965	Approved
0.6625	Remote Similarity	NPD3267	Approved
0.6625	Remote Similarity	NPD2797	Approved
0.6625	Remote Similarity	NPD3266	Approved
0.6625	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD7874	Approved
0.6607	Remote Similarity	NPD6004	Phase 3
0.6607	Remote Similarity	NPD6005	Phase 3
0.6607	Remote Similarity	NPD5762	Approved
0.6607	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD5763	Approved
0.6607	Remote Similarity	NPD6002	Phase 3
0.6607	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD4111	Phase 1
0.6602	Remote Similarity	NPD4665	Approved
0.6593	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD8166	Discontinued
0.6587	Remote Similarity	NPD3748	Approved
0.6585	Remote Similarity	NPD6233	Phase 2
0.6582	Remote Similarity	NPD6781	Approved
0.6582	Remote Similarity	NPD6776	Approved
0.6582	Remote Similarity	NPD6782	Approved
0.6582	Remote Similarity	NPD6780	Approved
0.6582	Remote Similarity	NPD6779	Approved
0.6582	Remote Similarity	NPD6777	Approved
0.6582	Remote Similarity	NPD6778	Approved
0.6581	Remote Similarity	NPD9092	Discovery
0.657	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7698	Approved
0.6566	Remote Similarity	NPD7696	Phase 3
0.6566	Remote Similarity	NPD6653	Approved
0.6566	Remote Similarity	NPD6651	Approved
0.6566	Remote Similarity	NPD7697	Approved
0.6557	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.655	Remote Similarity	NPD2309	Approved
0.655	Remote Similarity	NPD3887	Approved
0.655	Remote Similarity	NPD2354	Approved
0.6545	Remote Similarity	NPD8435	Approved
0.6541	Remote Similarity	NPD9717	Approved
0.6538	Remote Similarity	NPD3787	Discontinued
0.6538	Remote Similarity	NPD6808	Phase 2
0.6533	Remote Similarity	NPD8319	Approved
0.6533	Remote Similarity	NPD7871	Phase 2
0.6533	Remote Similarity	NPD7870	Phase 2
0.6533	Remote Similarity	NPD8320	Phase 1
0.6524	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD3764	Approved
0.6524	Remote Similarity	NPD6798	Discontinued
0.6517	Remote Similarity	NPD7972	Discontinued
0.6517	Remote Similarity	NPD7701	Phase 2
0.6517	Remote Similarity	NPD1465	Phase 2
0.6517	Remote Similarity	NPD8455	Phase 2
0.6515	Remote Similarity	NPD3057	Approved
0.6506	Remote Similarity	NPD230	Phase 1
0.6502	Remote Similarity	NPD7801	Approved
0.6497	Remote Similarity	NPD4107	Approved
0.6491	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD4110	Phase 3
0.6486	Remote Similarity	NPD2163	Approved
0.6486	Remote Similarity	NPD7228	Approved
0.6485	Remote Similarity	NPD8032	Phase 2
0.6484	Remote Similarity	NPD7199	Phase 2
0.6481	Remote Similarity	NPD2798	Approved
0.6471	Remote Similarity	NPD5953	Discontinued
0.6467	Remote Similarity	NPD1607	Approved
0.6463	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD17	Approved
0.6452	Remote Similarity	NPD7286	Phase 2

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