NPASS Compound

Structure

NPC142244 OpenBabel07101718222D 33 36 0 0 1 0 0 0 0 0999 V2000 -4.4649 -0.4533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9850 1.0788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5008 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0143 -0.6168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5279 2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3561 -2.3021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 -3.1447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3291 -2.3021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2131 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3705 1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3705 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5279 0.4865 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6852 -0.9730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3291 -3.9873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2131 0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5279 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5279 1.4595 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8426 -1.4595 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8426 0.4865 0.0000 C 0 0 1 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 2.3021 -3.9873 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 -4.8299 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5279 -2.4324 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 7 29 1 0 0 0 0 9 10 1 0 0 0 0 9 20 2 0 0 0 0 10 23 2 0 0 0 0 11 14 1 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 12 24 1 0 0 0 0 13 28 1 0 0 0 0 14 30 1 0 0 0 0 15 16 1 0 0 0 0 15 25 1 0 0 0 0 16 27 1 0 0 0 0 17 18 1 0 0 0 0 17 27 1 0 0 0 0 18 29 1 0 0 0 0 19 21 1 0 0 0 0 19 25 1 0 0 0 0 20 21 1 0 0 0 0 20 29 1 0 0 0 0 21 27 1 6 0 0 0 22 26 1 0 0 0 0 22 28 1 1 0 0 0 23 28 1 0 0 0 0 23 30 1 0 0 0 0 24 31 2 0 0 0 0 24 32 1 0 0 0 0 26 33 1 0 0 0 0 27 5 1 1 0 0 0 28 6 1 1 0 0 0 29 30 1 1 0 0 0 30 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.36
Volume:	511.671
LogP:	6.145
LogD:	4.699
LogS:	-4.771
# Rotatable Bonds:	4
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.459
Synthetic Accessibility Score:	4.868
Fsp3:	0.833
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:	-5.373
MDCK Permeability:	1.361308113700943e-05
Pgp-inhibitor:	0.219
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.256
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.907

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.134
Plasma Protein Binding (PPB):	96.9259033203125%
Volume Distribution (VD):	0.607
Pgp-substrate:	3.3666582107543945%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.565
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.914
CYP2C9-inhibitor:	0.139
CYP2C9-substrate:	0.875
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.088
CYP3A4-inhibitor:	0.13
CYP3A4-substrate:	0.747

ADMET: Excretion

Clearance (CL):	1.371
Half-life (T1/2):	0.23

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.594
Drug-inuced Liver Injury (DILI):	0.018
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.228
Maximum Recommended Daily Dose:	0.667
Skin Sensitization:	0.3
Carcinogencity:	0.304
Eye Corrosion:	0.012
Eye Irritation:	0.045
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC142244

Natural Product ID:	NPC142244
*Common Name:**	Dysoxyhainic Acid J
IUPAC Name:	3-[(1S,2R,4aS,4bR,6aR,10aR)-2-(2-hydroxypropan-2-yl)-1,4a,4b,6a,9,9-hexamethyl-3,4,5,6,7,8,10,10a-octahydro-2H-chrysen-1-yl]propanoic acid
Synonyms:	Dysoxyhainic Acid J
Standard InCHIKey:	GAWVZHKNUSCPAY-YSFYVZBISA-N
Standard InCHI:	InChI=1S/C30H48O3/c1-25(2)15-16-27(5)17-18-29(7)20(21(27)19-25)9-10-23-28(6,13-12-24(31)32)22(26(3,4)33)11-14-30(23,29)8/h9-10,21-22,33H,11-19H2,1-8H3,(H,31,32)/t21-,22-,27+,28-,29+,30+/m0/s1
SMILES:	OC(=O)CC[C@@]1(C)[C@@H](CC[C@@]2(C1=CC=C1[C@@]2(C)CC[C@@]2([C@H]1CC(C)(C)CC2)C)C)C(O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1642043
PubChem CID:	53321763
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003364] Steroid acids

*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
NPO144	Dysoxylum hainanense	Species	Meliaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[18771268]
NPO144	Dysoxylum hainanense	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21131198]
NPO144	Dysoxylum hainanense	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO144	Dysoxylum hainanense	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO144	Dysoxylum hainanense	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO144	Dysoxylum hainanense	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
MIC	11

Activity Type	# Activity
Organism	11

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	50.0	ug.mL-1	PMID[564991]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	50.0	ug.mL-1	PMID[564991]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	50.0	ug.mL-1	PMID[564991]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	50.0	ug.mL-1	PMID[564991]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	50.0	ug.mL-1	PMID[564991]
NPT2909	Organism	Shigella flexneri	Shigella flexneri	MIC	>	50.0	ug.mL-1	PMID[564991]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	50.0	ug.mL-1	PMID[564991]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	50.0	ug.mL-1	PMID[564991]
NPT1533	Organism	Saccharomyces	Saccharomyces	MIC	>	50.0	ug.mL-1	PMID[564991]
NPT327	Organism	Microsporum gypseum	Microsporum gypseum	MIC	>	50.0	ug.mL-1	PMID[564991]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	>	50.0	ug.mL-1	PMID[564991]

☑ 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 NPC142244 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	183
0.1-0.2	1078
0.2-0.3	5098
0.3-0.4	15801
0.4-0.5	8526
0.5-0.6	6408
0.6-0.7	4206
0.7-0.8	1114
0.8-0.85	225
0.85-0.9	38
0.9-0.95	17
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9733	High Similarity	NPC231431
0.9605	High Similarity	NPC37038
0.9487	High Similarity	NPC70834
0.9467	High Similarity	NPC471899
0.9467	High Similarity	NPC471897
0.9467	High Similarity	NPC107039
0.9342	High Similarity	NPC110094
0.9342	High Similarity	NPC260385
0.9342	High Similarity	NPC280654
0.9333	High Similarity	NPC89294
0.9231	High Similarity	NPC274050
0.9231	High Similarity	NPC162632
0.9231	High Similarity	NPC471898
0.9231	High Similarity	NPC263272
0.9231	High Similarity	NPC267691
0.9221	High Similarity	NPC16394
0.9221	High Similarity	NPC199595
0.9125	High Similarity	NPC156981
0.9114	High Similarity	NPC251779
0.9114	High Similarity	NPC69101
0.9103	High Similarity	NPC104545
0.9079	High Similarity	NPC309399
0.8987	High Similarity	NPC221647
0.8947	High Similarity	NPC192540
0.8947	High Similarity	NPC476844
0.8947	High Similarity	NPC279666
0.8902	High Similarity	NPC324063
0.8889	High Similarity	NPC96095
0.8861	High Similarity	NPC477057
0.8846	High Similarity	NPC321514
0.8846	High Similarity	NPC179028
0.8831	High Similarity	NPC69143
0.8816	High Similarity	NPC283908
0.8816	High Similarity	NPC161923
0.8816	High Similarity	NPC251970
0.8816	High Similarity	NPC476046
0.8816	High Similarity	NPC241854
0.8816	High Similarity	NPC103958
0.8816	High Similarity	NPC3753
0.8816	High Similarity	NPC301065
0.8816	High Similarity	NPC237591
0.8816	High Similarity	NPC183503
0.881	High Similarity	NPC95246
0.881	High Similarity	NPC161751
0.881	High Similarity	NPC474972
0.88	High Similarity	NPC160817
0.878	High Similarity	NPC474537
0.8765	High Similarity	NPC200752
0.8765	High Similarity	NPC69279
0.8765	High Similarity	NPC83569
0.875	High Similarity	NPC278459
0.875	High Similarity	NPC147066
0.8718	High Similarity	NPC165711
0.8684	High Similarity	NPC36310
0.8659	High Similarity	NPC477289
0.8625	High Similarity	NPC267517
0.8605	High Similarity	NPC301244
0.859	High Similarity	NPC899
0.8588	High Similarity	NPC112454
0.8588	High Similarity	NPC474686
0.8571	High Similarity	NPC71507
0.8571	High Similarity	NPC18064
0.8571	High Similarity	NPC171203
0.8571	High Similarity	NPC307426
0.8571	High Similarity	NPC88716
0.8571	High Similarity	NPC293564
0.8571	High Similarity	NPC102683
0.8571	High Similarity	NPC68160
0.8571	High Similarity	NPC158141
0.8571	High Similarity	NPC142415
0.8571	High Similarity	NPC130577
0.8571	High Similarity	NPC255168
0.8571	High Similarity	NPC98442
0.8571	High Similarity	NPC51700
0.8571	High Similarity	NPC173089
0.8571	High Similarity	NPC242468
0.8537	High Similarity	NPC102197
0.8519	High Similarity	NPC38350
0.8519	High Similarity	NPC327002
0.8519	High Similarity	NPC3915
0.8519	High Similarity	NPC201912
0.8506	High Similarity	NPC263780
0.85	High Similarity	NPC477371
0.85	High Similarity	NPC215843
0.8481	Intermediate Similarity	NPC66105
0.8471	Intermediate Similarity	NPC473242
0.8471	Intermediate Similarity	NPC474474
0.8471	Intermediate Similarity	NPC181225
0.8471	Intermediate Similarity	NPC40552
0.8471	Intermediate Similarity	NPC17733
0.8471	Intermediate Similarity	NPC474511
0.8471	Intermediate Similarity	NPC246708
0.8471	Intermediate Similarity	NPC470629
0.8471	Intermediate Similarity	NPC1753
0.8471	Intermediate Similarity	NPC52169
0.8471	Intermediate Similarity	NPC290690
0.8471	Intermediate Similarity	NPC182797
0.8471	Intermediate Similarity	NPC474512
0.8462	Intermediate Similarity	NPC201027
0.8452	Intermediate Similarity	NPC72638
0.8452	Intermediate Similarity	NPC73038
0.8415	Intermediate Similarity	NPC310989
0.8415	Intermediate Similarity	NPC260956
0.8415	Intermediate Similarity	NPC320514
0.8409	Intermediate Similarity	NPC80365
0.8391	Intermediate Similarity	NPC174167
0.8391	Intermediate Similarity	NPC470036
0.8375	Intermediate Similarity	NPC4827
0.8372	Intermediate Similarity	NPC293048
0.8372	Intermediate Similarity	NPC274330
0.8372	Intermediate Similarity	NPC198664
0.8372	Intermediate Similarity	NPC59263
0.8372	Intermediate Similarity	NPC130520
0.8372	Intermediate Similarity	NPC121798
0.8372	Intermediate Similarity	NPC263393
0.8372	Intermediate Similarity	NPC477973
0.8372	Intermediate Similarity	NPC61543
0.8372	Intermediate Similarity	NPC225585
0.8372	Intermediate Similarity	NPC470588
0.8372	Intermediate Similarity	NPC234346
0.8372	Intermediate Similarity	NPC281524
0.8372	Intermediate Similarity	NPC25906
0.8372	Intermediate Similarity	NPC127689
0.8372	Intermediate Similarity	NPC64872
0.8372	Intermediate Similarity	NPC143232
0.8372	Intermediate Similarity	NPC290972
0.8372	Intermediate Similarity	NPC474700
0.8372	Intermediate Similarity	NPC270768
0.8354	Intermediate Similarity	NPC104806
0.8354	Intermediate Similarity	NPC180886
0.8353	Intermediate Similarity	NPC136948
0.8333	Intermediate Similarity	NPC76333
0.8333	Intermediate Similarity	NPC306928
0.8333	Intermediate Similarity	NPC46610
0.8333	Intermediate Similarity	NPC166797
0.8333	Intermediate Similarity	NPC18819
0.8333	Intermediate Similarity	NPC29447
0.8313	Intermediate Similarity	NPC477373
0.8313	Intermediate Similarity	NPC477852
0.8313	Intermediate Similarity	NPC53733
0.8313	Intermediate Similarity	NPC167103
0.8313	Intermediate Similarity	NPC310470
0.8295	Intermediate Similarity	NPC275809
0.8295	Intermediate Similarity	NPC118490
0.8295	Intermediate Similarity	NPC202728
0.8295	Intermediate Similarity	NPC158059
0.8295	Intermediate Similarity	NPC118519
0.8293	Intermediate Similarity	NPC474955
0.8293	Intermediate Similarity	NPC477372
0.8293	Intermediate Similarity	NPC121984
0.8293	Intermediate Similarity	NPC473217
0.8276	Intermediate Similarity	NPC290614
0.8276	Intermediate Similarity	NPC291028
0.8276	Intermediate Similarity	NPC113989
0.8276	Intermediate Similarity	NPC18872
0.8276	Intermediate Similarity	NPC227467
0.8276	Intermediate Similarity	NPC477872
0.8276	Intermediate Similarity	NPC111110
0.8276	Intermediate Similarity	NPC7260
0.8276	Intermediate Similarity	NPC198818
0.8276	Intermediate Similarity	NPC273621
0.8276	Intermediate Similarity	NPC120840
0.8276	Intermediate Similarity	NPC86372
0.8276	Intermediate Similarity	NPC474728
0.8276	Intermediate Similarity	NPC130278
0.8276	Intermediate Similarity	NPC46441
0.8276	Intermediate Similarity	NPC470589
0.8276	Intermediate Similarity	NPC120968
0.8276	Intermediate Similarity	NPC172361
0.8276	Intermediate Similarity	NPC126369
0.8276	Intermediate Similarity	NPC193750
0.8276	Intermediate Similarity	NPC210037
0.8272	Intermediate Similarity	NPC274996
0.8272	Intermediate Similarity	NPC327674
0.8272	Intermediate Similarity	NPC158846
0.8272	Intermediate Similarity	NPC474113
0.8272	Intermediate Similarity	NPC192744
0.8272	Intermediate Similarity	NPC196827
0.8256	Intermediate Similarity	NPC72397
0.8256	Intermediate Similarity	NPC24816
0.825	Intermediate Similarity	NPC68828
0.825	Intermediate Similarity	NPC472300
0.8235	Intermediate Similarity	NPC473168
0.8235	Intermediate Similarity	NPC325594
0.8235	Intermediate Similarity	NPC155011
0.8235	Intermediate Similarity	NPC262085
0.8228	Intermediate Similarity	NPC476795
0.8222	Intermediate Similarity	NPC9487
0.8214	Intermediate Similarity	NPC171789
0.8214	Intermediate Similarity	NPC312660
0.8214	Intermediate Similarity	NPC180834
0.8205	Intermediate Similarity	NPC244708
0.8205	Intermediate Similarity	NPC330659
0.8205	Intermediate Similarity	NPC161187
0.8202	Intermediate Similarity	NPC6818
0.8202	Intermediate Similarity	NPC148964
0.8202	Intermediate Similarity	NPC191412
0.8202	Intermediate Similarity	NPC114159
0.8193	Intermediate Similarity	NPC133391
0.8193	Intermediate Similarity	NPC302661

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 NPC142244 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	1375
0.2-0.3	3812
0.3-0.4	2501
0.4-0.5	786
0.5-0.6	235
0.6-0.7	189
0.7-0.8	62
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8588	High Similarity	NPD7285	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7515	Phase 2
0.8	Intermediate Similarity	NPD7748	Approved
0.7978	Intermediate Similarity	NPD5281	Approved
0.7978	Intermediate Similarity	NPD5284	Approved
0.7976	Intermediate Similarity	NPD4223	Phase 3
0.7976	Intermediate Similarity	NPD4221	Approved
0.7907	Intermediate Similarity	NPD5329	Approved
0.7841	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD4694	Approved
0.7816	Intermediate Similarity	NPD6098	Approved
0.7816	Intermediate Similarity	NPD5280	Approved
0.7791	Intermediate Similarity	NPD4197	Approved
0.7791	Intermediate Similarity	NPD4786	Approved
0.7765	Intermediate Similarity	NPD3667	Approved
0.7742	Intermediate Similarity	NPD7902	Approved
0.7738	Intermediate Similarity	NPD4695	Discontinued
0.7727	Intermediate Similarity	NPD3573	Approved
0.7701	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6399	Phase 3
0.7634	Intermediate Similarity	NPD7614	Phase 1
0.7614	Intermediate Similarity	NPD5205	Approved
0.7614	Intermediate Similarity	NPD7146	Approved
0.7614	Intermediate Similarity	NPD4690	Approved
0.7614	Intermediate Similarity	NPD4688	Approved
0.7614	Intermediate Similarity	NPD4519	Discontinued
0.7614	Intermediate Similarity	NPD7521	Approved
0.7614	Intermediate Similarity	NPD7334	Approved
0.7614	Intermediate Similarity	NPD4623	Approved
0.7614	Intermediate Similarity	NPD4693	Phase 3
0.7614	Intermediate Similarity	NPD6684	Approved
0.7614	Intermediate Similarity	NPD4138	Approved
0.7614	Intermediate Similarity	NPD6409	Approved
0.7614	Intermediate Similarity	NPD4689	Approved
0.7614	Intermediate Similarity	NPD5330	Approved
0.7586	Intermediate Similarity	NPD3665	Phase 1
0.7586	Intermediate Similarity	NPD3666	Approved
0.7586	Intermediate Similarity	NPD3133	Approved
0.7582	Intermediate Similarity	NPD6050	Approved
0.7556	Intermediate Similarity	NPD6904	Approved
0.7556	Intermediate Similarity	NPD6673	Approved
0.7556	Intermediate Similarity	NPD6080	Approved
0.7553	Intermediate Similarity	NPD6083	Phase 2
0.7553	Intermediate Similarity	NPD6084	Phase 2
0.75	Intermediate Similarity	NPD3617	Approved
0.7473	Intermediate Similarity	NPD5692	Phase 3
0.7473	Intermediate Similarity	NPD5207	Approved
0.7444	Intermediate Similarity	NPD6903	Approved
0.7444	Intermediate Similarity	NPD5208	Approved
0.7444	Intermediate Similarity	NPD5737	Approved
0.7444	Intermediate Similarity	NPD6672	Approved
0.7419	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7900	Approved
0.7416	Intermediate Similarity	NPD3618	Phase 1
0.7416	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD5690	Phase 2
0.7416	Intermediate Similarity	NPD5279	Phase 3
0.7407	Intermediate Similarity	NPD4243	Approved
0.7391	Intermediate Similarity	NPD6411	Approved
0.7391	Intermediate Similarity	NPD5694	Approved
0.7363	Intermediate Similarity	NPD4753	Phase 2
0.7363	Intermediate Similarity	NPD5328	Approved
0.734	Intermediate Similarity	NPD5695	Phase 3
0.7292	Intermediate Similarity	NPD5696	Approved
0.7283	Intermediate Similarity	NPD4096	Approved
0.7273	Intermediate Similarity	NPD4788	Approved
0.7241	Intermediate Similarity	NPD4692	Approved
0.7241	Intermediate Similarity	NPD4139	Approved
0.7229	Intermediate Similarity	NPD5733	Approved
0.7229	Intermediate Similarity	NPD4784	Approved
0.7229	Intermediate Similarity	NPD4785	Approved
0.7229	Intermediate Similarity	NPD4058	Approved
0.7216	Intermediate Similarity	NPD6404	Discontinued
0.7215	Intermediate Similarity	NPD4224	Phase 2
0.7209	Intermediate Similarity	NPD4195	Approved
0.7209	Intermediate Similarity	NPD7645	Phase 2
0.7204	Intermediate Similarity	NPD5693	Phase 1
0.7204	Intermediate Similarity	NPD6079	Approved
0.7204	Intermediate Similarity	NPD8035	Phase 2
0.7204	Intermediate Similarity	NPD8034	Phase 2
0.7191	Intermediate Similarity	NPD3668	Phase 3
0.7174	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD6101	Approved
0.716	Intermediate Similarity	NPD4137	Phase 3
0.7158	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD5133	Approved
0.7128	Intermediate Similarity	NPD4202	Approved
0.7083	Intermediate Similarity	NPD7732	Phase 3
0.7073	Intermediate Similarity	NPD4747	Approved
0.7073	Intermediate Similarity	NPD4691	Approved
0.7065	Intermediate Similarity	NPD4518	Approved
0.7053	Intermediate Similarity	NPD6001	Approved
0.7037	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6402	Approved
0.703	Intermediate Similarity	NPD5739	Approved
0.703	Intermediate Similarity	NPD6675	Approved
0.703	Intermediate Similarity	NPD7128	Approved
0.7024	Intermediate Similarity	NPD6924	Approved
0.7024	Intermediate Similarity	NPD4687	Approved
0.7024	Intermediate Similarity	NPD6926	Approved
0.7	Intermediate Similarity	NPD7331	Phase 2
0.6988	Remote Similarity	NPD5276	Approved
0.6988	Remote Similarity	NPD6081	Approved
0.6979	Remote Similarity	NPD5210	Approved
0.6979	Remote Similarity	NPD4629	Approved
0.6979	Remote Similarity	NPD5654	Approved
0.6966	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6942	Approved
0.6941	Remote Similarity	NPD5275	Approved
0.6941	Remote Similarity	NPD7339	Approved
0.6941	Remote Similarity	NPD8039	Approved
0.6941	Remote Similarity	NPD4190	Phase 3
0.6939	Remote Similarity	NPD7638	Approved
0.6932	Remote Similarity	NPD7525	Registered
0.6893	Remote Similarity	NPD6899	Approved
0.6893	Remote Similarity	NPD6881	Approved
0.6893	Remote Similarity	NPD7320	Approved
0.6875	Remote Similarity	NPD7341	Phase 2
0.6869	Remote Similarity	NPD7640	Approved
0.6869	Remote Similarity	NPD7639	Approved
0.686	Remote Similarity	NPD6933	Approved
0.686	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5959	Approved
0.6837	Remote Similarity	NPD4755	Approved
0.6829	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5360	Phase 3
0.6827	Remote Similarity	NPD6373	Approved
0.6827	Remote Similarity	NPD6372	Approved
0.6824	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5701	Approved
0.6796	Remote Similarity	NPD5697	Approved
0.6771	Remote Similarity	NPD5778	Approved
0.6771	Remote Similarity	NPD5779	Approved
0.6762	Remote Similarity	NPD7290	Approved
0.6762	Remote Similarity	NPD7102	Approved
0.6762	Remote Similarity	NPD6883	Approved
0.6735	Remote Similarity	NPD4697	Phase 3
0.6735	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5222	Approved
0.6735	Remote Similarity	NPD5221	Approved
0.6731	Remote Similarity	NPD6011	Approved
0.67	Remote Similarity	NPD5285	Approved
0.67	Remote Similarity	NPD4696	Approved
0.67	Remote Similarity	NPD5286	Approved
0.67	Remote Similarity	NPD4700	Approved
0.6698	Remote Similarity	NPD6847	Approved
0.6698	Remote Similarity	NPD6650	Approved
0.6698	Remote Similarity	NPD6617	Approved
0.6698	Remote Similarity	NPD6869	Approved
0.6698	Remote Similarity	NPD6649	Approved
0.6698	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD8028	Phase 2
0.6667	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD6052	Approved
0.6667	Remote Similarity	NPD6117	Approved
0.6667	Remote Similarity	NPD6013	Approved
0.6636	Remote Similarity	NPD6882	Approved
0.6636	Remote Similarity	NPD8297	Approved
0.6635	Remote Similarity	NPD6412	Phase 2
0.6634	Remote Similarity	NPD5223	Approved
0.6632	Remote Similarity	NPD6051	Approved
0.6591	Remote Similarity	NPD6116	Phase 1
0.6574	Remote Similarity	NPD6858	Approved
0.6574	Remote Similarity	NPD7094	Approved
0.6569	Remote Similarity	NPD5224	Approved
0.6569	Remote Similarity	NPD4633	Approved
0.6569	Remote Similarity	NPD5211	Phase 2
0.6569	Remote Similarity	NPD5091	Approved
0.6569	Remote Similarity	NPD5226	Approved
0.6569	Remote Similarity	NPD5225	Approved
0.6556	Remote Similarity	NPD6931	Approved
0.6556	Remote Similarity	NPD6930	Phase 2
0.6556	Remote Similarity	NPD7509	Discontinued
0.6552	Remote Similarity	NPD3702	Approved
0.6548	Remote Similarity	NPD6922	Approved
0.6548	Remote Similarity	NPD6923	Approved
0.6545	Remote Similarity	NPD7115	Discovery
0.6517	Remote Similarity	NPD6114	Approved
0.6517	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6697	Approved
0.6517	Remote Similarity	NPD6118	Approved
0.6517	Remote Similarity	NPD6115	Approved
0.6505	Remote Similarity	NPD5175	Approved
0.6505	Remote Similarity	NPD4754	Approved
0.6505	Remote Similarity	NPD5174	Approved
0.6495	Remote Similarity	NPD7637	Suspended
0.6476	Remote Similarity	NPD6614	Approved
0.6471	Remote Similarity	NPD4244	Approved
0.6471	Remote Similarity	NPD4789	Approved
0.6471	Remote Similarity	NPD7144	Approved
0.6471	Remote Similarity	NPD4245	Approved
0.6471	Remote Similarity	NPD7143	Approved
0.6447	Remote Similarity	NPD4266	Approved
0.6447	Remote Similarity	NPD3194	Approved
0.6447	Remote Similarity	NPD3196	Approved
0.6447	Remote Similarity	NPD3195	Phase 2
0.6444	Remote Similarity	NPD6929	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