NPASS Compound

Structure

NPC475294 OpenBabel07101718222D 39 42 0 0 1 0 0 0 0 0999 V2000 -4.6057 2.4557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5057 0.1194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2978 -0.8587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0522 -2.2382 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 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9074 -0.7248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8855 -0.9328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 -4.9147 1.5046 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 2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 1 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 -0.9511 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2382 -1.4680 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 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5546 -0.1896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 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 1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2601 -1.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8929 1.2967 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 -2.4190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -1.5691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2456 0.7614 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 27 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 6 29 1 0 0 0 0 10 11 1 0 0 0 0 10 19 2 0 0 0 0 11 22 1 0 0 0 0 12 15 1 0 0 0 0 12 23 1 0 0 0 0 13 14 2 0 0 0 0 13 24 1 0 0 0 0 14 27 1 0 0 0 0 15 29 1 0 0 0 0 16 20 1 0 0 0 0 16 21 1 0 0 0 0 17 25 1 0 0 0 0 17 30 1 0 0 0 0 18 33 2 0 0 0 0 18 39 1 0 0 0 0 19 20 1 0 0 0 0 19 28 1 0 0 0 0 20 31 1 1 0 0 0 21 26 1 0 0 0 0 21 34 1 1 0 0 0 22 29 1 6 0 0 0 22 31 1 0 0 0 0 23 30 1 1 0 0 0 23 32 1 0 0 0 0 24 32 1 0 0 0 0 24 35 2 0 0 0 0 25 31 1 0 0 0 0 25 36 2 0 0 0 0 26 28 1 0 0 0 0 26 37 2 0 0 0 0 27 39 1 0 0 0 0 29 30 1 6 0 0 0 30 7 1 1 0 0 0 31 8 1 1 0 0 0 32 9 1 1 0 0 0 32 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	542.32
Volume:	573.515
LogP:	3.638
LogD:	2.322
LogS:	-4.548
# Rotatable Bonds:	6
TPSA:	117.97
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.298
Synthetic Accessibility Score:	5.345
Fsp3:	0.75
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:	-5.014
MDCK Permeability:	1.960091685759835e-05
Pgp-inhibitor:	0.98
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.049
20% Bioavailability (F20%):	0.619
30% Bioavailability (F30%):	0.895

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.986
Plasma Protein Binding (PPB):	68.38245391845703%
Volume Distribution (VD):	0.516
Pgp-substrate:	23.122892379760742%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.117
CYP2C19-inhibitor:	0.071
CYP2C19-substrate:	0.778
CYP2C9-inhibitor:	0.08
CYP2C9-substrate:	0.097
CYP2D6-inhibitor:	0.032
CYP2D6-substrate:	0.09
CYP3A4-inhibitor:	0.832
CYP3A4-substrate:	0.687

ADMET: Excretion

Clearance (CL):	5.045
Half-life (T1/2):	0.283

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.074
Drug-inuced Liver Injury (DILI):	0.111
AMES Toxicity:	0.034
Rat Oral Acute Toxicity:	0.964
Maximum Recommended Daily Dose:	0.898
Skin Sensitization:	0.22
Carcinogencity:	0.943
Eye Corrosion:	0.004
Eye Irritation:	0.01
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC475294

Natural Product ID:	NPC475294
*Common Name:**	16-Deoxycucurbitacin B
IUPAC Name:	[(E,6S)-6-hydroxy-6-[(2S,8S,9R,10R,13R,14S,17S)-2-hydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-5-oxohept-3-en-2-yl] acetate
Synonyms:
Standard InCHIKey:	BXYMOPHDFDLMEA-TZDKCZRXSA-N
Standard InCHI:	InChI=1S/C32H46O7/c1-18(33)39-27(2,3)14-13-24(35)32(9,38)23-12-15-29(6)22-11-10-19-20(16-21(34)26(37)28(19,4)5)31(22,8)25(36)17-30(23,29)7/h10,13-14,20-23,34,38H,11-12,15-17H2,1-9H3/b14-13+/t20-,21+,22+,23+,29+,30-,31+,32+/m1/s1
SMILES:	CC(=O)OC(C)(C)C=CC(=O)C(C)(C1CCC2(C1(CC(=O)C3(C2CC=C4C3CC(C(=O)C4(C)C)O)C)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503027
PubChem CID:	44566407
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001686] Cucurbitacins

*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
NPO658	Leucopaxillus gentianeus	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568769]
NPO658	Leucopaxillus gentianeus	Species	Tricholomataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[17190463]
NPO658	Leucopaxillus gentianeus	Species	Tricholomataceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	0.06	ug.mL-1	PMID[524133]

☑ 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 NPC475294 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	193
0.1-0.2	1107
0.2-0.3	3860
0.3-0.4	8322
0.4-0.5	12814
0.5-0.6	6238
0.6-0.7	6649
0.7-0.8	3072
0.8-0.85	375
0.85-0.9	58
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9515	High Similarity	NPC475524
0.9515	High Similarity	NPC100267
0.9245	High Similarity	NPC148458
0.9159	High Similarity	NPC239273
0.9143	High Similarity	NPC221144
0.9074	High Similarity	NPC311554
0.9074	High Similarity	NPC257457
0.8932	High Similarity	NPC181265
0.8835	High Similarity	NPC235889
0.8824	High Similarity	NPC308726
0.8824	High Similarity	NPC119601
0.8807	High Similarity	NPC471854
0.8785	High Similarity	NPC147180
0.8785	High Similarity	NPC264634
0.8774	High Similarity	NPC473627
0.8774	High Similarity	NPC37116
0.8738	High Similarity	NPC311612
0.8725	High Similarity	NPC310981
0.8725	High Similarity	NPC302537
0.8725	High Similarity	NPC476240
0.8725	High Similarity	NPC224720
0.8725	High Similarity	NPC476223
0.8725	High Similarity	NPC163372
0.8713	High Similarity	NPC98868
0.8679	High Similarity	NPC241927
0.8679	High Similarity	NPC258543
0.8667	High Similarity	NPC44063
0.8641	High Similarity	NPC32577
0.8641	High Similarity	NPC114540
0.8641	High Similarity	NPC155332
0.8641	High Similarity	NPC136289
0.8641	High Similarity	NPC475320
0.8641	High Similarity	NPC87351
0.8627	High Similarity	NPC476274
0.8614	High Similarity	NPC253826
0.8611	High Similarity	NPC71348
0.8558	High Similarity	NPC180204
0.8558	High Similarity	NPC112009
0.8544	High Similarity	NPC81530
0.8532	High Similarity	NPC472926
0.8532	High Similarity	NPC472929
0.8532	High Similarity	NPC122056
0.8529	High Similarity	NPC108368
0.8529	High Similarity	NPC114274
0.8529	High Similarity	NPC197386
0.8529	High Similarity	NPC57079
0.8529	High Similarity	NPC222011
0.8519	High Similarity	NPC214797
0.8519	High Similarity	NPC231589
0.8519	High Similarity	NPC474315
0.8519	High Similarity	NPC118860
0.8515	High Similarity	NPC328371
0.8515	High Similarity	NPC96859
0.8515	High Similarity	NPC305483
0.8515	High Similarity	NPC328162
0.8505	High Similarity	NPC2766
0.8491	Intermediate Similarity	NPC472925
0.8491	Intermediate Similarity	NPC91034
0.8476	Intermediate Similarity	NPC189616
0.8476	Intermediate Similarity	NPC118911
0.8469	Intermediate Similarity	NPC177141
0.8468	Intermediate Similarity	NPC472934
0.8468	Intermediate Similarity	NPC470959
0.8468	Intermediate Similarity	NPC243065
0.8468	Intermediate Similarity	NPC476965
0.8462	Intermediate Similarity	NPC271266
0.8462	Intermediate Similarity	NPC308351
0.8455	Intermediate Similarity	NPC474181
0.8455	Intermediate Similarity	NPC67259
0.8455	Intermediate Similarity	NPC147912
0.8447	Intermediate Similarity	NPC201406
0.8447	Intermediate Similarity	NPC266955
0.844	Intermediate Similarity	NPC170487
0.8431	Intermediate Similarity	NPC108078
0.8431	Intermediate Similarity	NPC38530
0.8431	Intermediate Similarity	NPC474343
0.8431	Intermediate Similarity	NPC43747
0.8431	Intermediate Similarity	NPC69385
0.8431	Intermediate Similarity	NPC84335
0.8426	Intermediate Similarity	NPC197428
0.8416	Intermediate Similarity	NPC318282
0.8416	Intermediate Similarity	NPC171395
0.8416	Intermediate Similarity	NPC317586
0.8416	Intermediate Similarity	NPC293052
0.8416	Intermediate Similarity	NPC173875
0.8416	Intermediate Similarity	NPC469995
0.8416	Intermediate Similarity	NPC33473
0.8416	Intermediate Similarity	NPC174948
0.8416	Intermediate Similarity	NPC470016
0.8411	Intermediate Similarity	NPC472825
0.8411	Intermediate Similarity	NPC295244
0.8411	Intermediate Similarity	NPC177064
0.8411	Intermediate Similarity	NPC220155
0.8396	Intermediate Similarity	NPC60681
0.8396	Intermediate Similarity	NPC196528
0.8396	Intermediate Similarity	NPC189863
0.8396	Intermediate Similarity	NPC266570
0.8381	Intermediate Similarity	NPC111323
0.8378	Intermediate Similarity	NPC190286
0.8378	Intermediate Similarity	NPC270958
0.8365	Intermediate Similarity	NPC471412
0.8365	Intermediate Similarity	NPC99411
0.8365	Intermediate Similarity	NPC115899
0.8365	Intermediate Similarity	NPC474327
0.835	Intermediate Similarity	NPC316598
0.835	Intermediate Similarity	NPC176845
0.8349	Intermediate Similarity	NPC43775
0.8333	Intermediate Similarity	NPC472216
0.8333	Intermediate Similarity	NPC41405
0.8333	Intermediate Similarity	NPC214644
0.8333	Intermediate Similarity	NPC304495
0.8333	Intermediate Similarity	NPC173905
0.8333	Intermediate Similarity	NPC5475
0.8333	Intermediate Similarity	NPC284828
0.8333	Intermediate Similarity	NPC249954
0.8333	Intermediate Similarity	NPC475065
0.8319	Intermediate Similarity	NPC476960
0.8319	Intermediate Similarity	NPC472933
0.8318	Intermediate Similarity	NPC185
0.8317	Intermediate Similarity	NPC166906
0.8317	Intermediate Similarity	NPC8993
0.8317	Intermediate Similarity	NPC184870
0.8317	Intermediate Similarity	NPC476415
0.8304	Intermediate Similarity	NPC472927
0.8304	Intermediate Similarity	NPC167606
0.8304	Intermediate Similarity	NPC286528
0.8304	Intermediate Similarity	NPC20302
0.8304	Intermediate Similarity	NPC284068
0.8304	Intermediate Similarity	NPC140055
0.8302	Intermediate Similarity	NPC255309
0.8302	Intermediate Similarity	NPC472868
0.83	Intermediate Similarity	NPC218301
0.83	Intermediate Similarity	NPC472975
0.83	Intermediate Similarity	NPC168027
0.83	Intermediate Similarity	NPC185936
0.83	Intermediate Similarity	NPC475806
0.8288	Intermediate Similarity	NPC470953
0.8286	Intermediate Similarity	NPC473163
0.8286	Intermediate Similarity	NPC185530
0.8283	Intermediate Similarity	NPC5509
0.8283	Intermediate Similarity	NPC262043
0.8273	Intermediate Similarity	NPC236217
0.8273	Intermediate Similarity	NPC191620
0.8269	Intermediate Similarity	NPC117685
0.8269	Intermediate Similarity	NPC241221
0.8269	Intermediate Similarity	NPC327431
0.8269	Intermediate Similarity	NPC287833
0.8269	Intermediate Similarity	NPC472644
0.8269	Intermediate Similarity	NPC471413
0.8269	Intermediate Similarity	NPC144956
0.8257	Intermediate Similarity	NPC16270
0.8257	Intermediate Similarity	NPC29133
0.8257	Intermediate Similarity	NPC5284
0.8252	Intermediate Similarity	NPC291634
0.8252	Intermediate Similarity	NPC107243
0.8252	Intermediate Similarity	NPC285513
0.8252	Intermediate Similarity	NPC202705
0.8252	Intermediate Similarity	NPC110937
0.8252	Intermediate Similarity	NPC254496
0.8252	Intermediate Similarity	NPC57416
0.8252	Intermediate Similarity	NPC208094
0.8246	Intermediate Similarity	NPC476962
0.8246	Intermediate Similarity	NPC79579
0.8246	Intermediate Similarity	NPC476961
0.8241	Intermediate Similarity	NPC473482
0.8241	Intermediate Similarity	NPC318363
0.8241	Intermediate Similarity	NPC475418
0.8241	Intermediate Similarity	NPC275539
0.8241	Intermediate Similarity	NPC189075
0.8241	Intermediate Similarity	NPC94529
0.8235	Intermediate Similarity	NPC295347
0.8235	Intermediate Similarity	NPC259286
0.8235	Intermediate Similarity	NPC469599
0.8235	Intermediate Similarity	NPC476174
0.823	Intermediate Similarity	NPC709
0.823	Intermediate Similarity	NPC118638
0.823	Intermediate Similarity	NPC50774
0.823	Intermediate Similarity	NPC153440
0.8224	Intermediate Similarity	NPC173172
0.8224	Intermediate Similarity	NPC470267
0.8224	Intermediate Similarity	NPC475414
0.8224	Intermediate Similarity	NPC96377
0.8218	Intermediate Similarity	NPC79117
0.8218	Intermediate Similarity	NPC472871
0.8218	Intermediate Similarity	NPC474736
0.8218	Intermediate Similarity	NPC38232
0.8214	Intermediate Similarity	NPC270929
0.8214	Intermediate Similarity	NPC176840
0.8208	Intermediate Similarity	NPC470954
0.8208	Intermediate Similarity	NPC26478
0.8208	Intermediate Similarity	NPC36688
0.8208	Intermediate Similarity	NPC476889
0.8208	Intermediate Similarity	NPC297617
0.8208	Intermediate Similarity	NPC72151
0.8208	Intermediate Similarity	NPC249187
0.8208	Intermediate Similarity	NPC473283
0.8208	Intermediate Similarity	NPC329345
0.8208	Intermediate Similarity	NPC476237
0.8208	Intermediate Similarity	NPC264048
0.8208	Intermediate Similarity	NPC475526

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 NPC475294 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	1294
0.2-0.3	3507
0.3-0.4	2689
0.4-0.5	933
0.5-0.6	210
0.6-0.7	174
0.7-0.8	115
0.8-0.85	47
0.85-0.9	21
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8762	High Similarity	NPD6881	Approved
0.8762	High Similarity	NPD6899	Approved
0.8692	High Similarity	NPD8130	Phase 1
0.8667	High Similarity	NPD5697	Approved
0.8611	High Similarity	NPD8297	Approved
0.8598	High Similarity	NPD7102	Approved
0.8598	High Similarity	NPD6883	Approved
0.8598	High Similarity	NPD7290	Approved
0.8585	High Similarity	NPD6011	Approved
0.8571	High Similarity	NPD6675	Approved
0.8571	High Similarity	NPD6402	Approved
0.8571	High Similarity	NPD5739	Approved
0.8571	High Similarity	NPD7128	Approved
0.8519	High Similarity	NPD6617	Approved
0.8519	High Similarity	NPD6650	Approved
0.8519	High Similarity	NPD6869	Approved
0.8519	High Similarity	NPD6649	Approved
0.8519	High Similarity	NPD6847	Approved
0.8505	High Similarity	NPD6012	Approved
0.8505	High Similarity	NPD6013	Approved
0.8505	High Similarity	NPD6014	Approved
0.844	Intermediate Similarity	NPD6882	Approved
0.8431	Intermediate Similarity	NPD6083	Phase 2
0.8431	Intermediate Similarity	NPD6084	Phase 2
0.8411	Intermediate Similarity	NPD7320	Approved
0.8333	Intermediate Similarity	NPD6373	Approved
0.8333	Intermediate Similarity	NPD5221	Approved
0.8333	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD5222	Approved
0.8333	Intermediate Similarity	NPD6372	Approved
0.8318	Intermediate Similarity	NPD5701	Approved
0.8304	Intermediate Similarity	NPD7115	Discovery
0.83	Intermediate Similarity	NPD6079	Approved
0.8286	Intermediate Similarity	NPD5211	Phase 2
0.8269	Intermediate Similarity	NPD4696	Approved
0.8269	Intermediate Similarity	NPD5286	Approved
0.8269	Intermediate Similarity	NPD5285	Approved
0.8252	Intermediate Similarity	NPD5173	Approved
0.819	Intermediate Similarity	NPD5223	Approved
0.8182	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD6672	Approved
0.8182	Intermediate Similarity	NPD5737	Approved
0.8131	Intermediate Similarity	NPD5141	Approved
0.8119	Intermediate Similarity	NPD5693	Phase 1
0.8113	Intermediate Similarity	NPD4633	Approved
0.8113	Intermediate Similarity	NPD5225	Approved
0.8113	Intermediate Similarity	NPD5224	Approved
0.8113	Intermediate Similarity	NPD5226	Approved
0.81	Intermediate Similarity	NPD5328	Approved
0.8077	Intermediate Similarity	NPD4755	Approved
0.807	Intermediate Similarity	NPD6335	Approved
0.8058	Intermediate Similarity	NPD5695	Phase 3
0.8053	Intermediate Similarity	NPD6868	Approved
0.8039	Intermediate Similarity	NPD6399	Phase 3
0.8037	Intermediate Similarity	NPD5174	Approved
0.8037	Intermediate Similarity	NPD5175	Approved
0.8036	Intermediate Similarity	NPD4632	Approved
0.8	Intermediate Similarity	NPD7100	Approved
0.8	Intermediate Similarity	NPD7638	Approved
0.8	Intermediate Similarity	NPD7101	Approved
0.8	Intermediate Similarity	NPD5696	Approved
0.7982	Intermediate Similarity	NPD6317	Approved
0.7981	Intermediate Similarity	NPD4697	Phase 3
0.7925	Intermediate Similarity	NPD4700	Approved
0.7925	Intermediate Similarity	NPD7640	Approved
0.7925	Intermediate Similarity	NPD7639	Approved
0.7921	Intermediate Similarity	NPD6673	Approved
0.7921	Intermediate Similarity	NPD4753	Phase 2
0.7921	Intermediate Similarity	NPD6904	Approved
0.7921	Intermediate Similarity	NPD6080	Approved
0.7913	Intermediate Similarity	NPD6314	Approved
0.7913	Intermediate Similarity	NPD6313	Approved
0.7895	Intermediate Similarity	NPD6274	Approved
0.7885	Intermediate Similarity	NPD4629	Approved
0.7885	Intermediate Similarity	NPD5210	Approved
0.7826	Intermediate Similarity	NPD6009	Approved
0.78	Intermediate Similarity	NPD6684	Approved
0.78	Intermediate Similarity	NPD7334	Approved
0.78	Intermediate Similarity	NPD7146	Approved
0.78	Intermediate Similarity	NPD7521	Approved
0.78	Intermediate Similarity	NPD6409	Approved
0.78	Intermediate Similarity	NPD5330	Approved
0.7788	Intermediate Similarity	NPD7748	Approved
0.7778	Intermediate Similarity	NPD4786	Approved
0.7778	Intermediate Similarity	NPD6319	Approved
0.7748	Intermediate Similarity	NPD4729	Approved
0.7748	Intermediate Similarity	NPD4730	Approved
0.7731	Intermediate Similarity	NPD7604	Phase 2
0.7712	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD5983	Phase 2
0.7706	Intermediate Similarity	NPD4754	Approved
0.77	Intermediate Similarity	NPD5329	Approved
0.7667	Intermediate Similarity	NPD7492	Approved
0.7647	Intermediate Similarity	NPD6903	Approved
0.7647	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD6053	Discontinued
0.7627	Intermediate Similarity	NPD6054	Approved
0.7624	Intermediate Similarity	NPD5690	Phase 2
0.7624	Intermediate Similarity	NPD5279	Phase 3
0.7624	Intermediate Similarity	NPD6098	Approved
0.7624	Intermediate Similarity	NPD3618	Phase 1
0.7623	Intermediate Similarity	NPD7736	Approved
0.7611	Intermediate Similarity	NPD5247	Approved
0.7611	Intermediate Similarity	NPD5135	Approved
0.7611	Intermediate Similarity	NPD5169	Approved
0.7611	Intermediate Similarity	NPD5248	Approved
0.7611	Intermediate Similarity	NPD4634	Approved
0.7611	Intermediate Similarity	NPD5251	Approved
0.7611	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD5250	Approved
0.7611	Intermediate Similarity	NPD5249	Phase 3
0.7603	Intermediate Similarity	NPD6336	Discontinued
0.7603	Intermediate Similarity	NPD6616	Approved
0.76	Intermediate Similarity	NPD4197	Approved
0.76	Intermediate Similarity	NPD3665	Phase 1
0.76	Intermediate Similarity	NPD3133	Approved
0.76	Intermediate Similarity	NPD3666	Approved
0.7596	Intermediate Similarity	NPD5694	Approved
0.7596	Intermediate Similarity	NPD6050	Approved
0.7596	Intermediate Similarity	NPD7515	Phase 2
0.7589	Intermediate Similarity	NPD5128	Approved
0.7589	Intermediate Similarity	NPD5168	Approved
0.7576	Intermediate Similarity	NPD3667	Approved
0.7576	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD7902	Approved
0.7568	Intermediate Similarity	NPD4768	Approved
0.7568	Intermediate Similarity	NPD4767	Approved
0.7568	Intermediate Similarity	NPD6008	Approved
0.7563	Intermediate Similarity	NPD6909	Approved
0.7563	Intermediate Similarity	NPD6908	Approved
0.7549	Intermediate Similarity	NPD3573	Approved
0.7547	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD5127	Approved
0.7544	Intermediate Similarity	NPD5216	Approved
0.7544	Intermediate Similarity	NPD5217	Approved
0.7544	Intermediate Similarity	NPD5215	Approved
0.7541	Intermediate Similarity	NPD7078	Approved
0.7525	Intermediate Similarity	NPD1694	Approved
0.7524	Intermediate Similarity	NPD4202	Approved
0.75	Intermediate Similarity	NPD5692	Phase 3
0.75	Intermediate Similarity	NPD6370	Approved
0.75	Intermediate Similarity	NPD5785	Approved
0.7429	Intermediate Similarity	NPD6411	Approved
0.7429	Intermediate Similarity	NPD5284	Approved
0.7429	Intermediate Similarity	NPD5281	Approved
0.7417	Intermediate Similarity	NPD6016	Approved
0.7417	Intermediate Similarity	NPD6015	Approved
0.7404	Intermediate Similarity	NPD6051	Approved
0.74	Intermediate Similarity	NPD4221	Approved
0.74	Intermediate Similarity	NPD4223	Phase 3
0.7398	Intermediate Similarity	NPD8293	Discontinued
0.7374	Intermediate Similarity	NPD4695	Discontinued
0.7355	Intermediate Similarity	NPD5988	Approved
0.735	Intermediate Similarity	NPD5167	Approved
0.7339	Intermediate Similarity	NPD4225	Approved
0.7333	Intermediate Similarity	NPD6059	Approved
0.7317	Intermediate Similarity	NPD7507	Approved
0.7308	Intermediate Similarity	NPD5208	Approved
0.7297	Intermediate Similarity	NPD7632	Discontinued
0.729	Intermediate Similarity	NPD7900	Approved
0.729	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD4694	Approved
0.7282	Intermediate Similarity	NPD5280	Approved
0.7281	Intermediate Similarity	NPD6686	Approved
0.7264	Intermediate Similarity	NPD8034	Phase 2
0.7264	Intermediate Similarity	NPD8035	Phase 2
0.7238	Intermediate Similarity	NPD6101	Approved
0.7238	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD5778	Approved
0.7196	Intermediate Similarity	NPD5779	Approved
0.7193	Intermediate Similarity	NPD6614	Approved
0.7184	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD3617	Approved
0.717	Intermediate Similarity	NPD5207	Approved
0.7165	Intermediate Similarity	NPD7260	Phase 2
0.7157	Intermediate Similarity	NPD4788	Approved
0.7143	Intermediate Similarity	NPD7319	Approved
0.713	Intermediate Similarity	NPD6001	Approved
0.713	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4689	Approved
0.7115	Intermediate Similarity	NPD4623	Approved
0.7115	Intermediate Similarity	NPD4693	Phase 3
0.7115	Intermediate Similarity	NPD4519	Discontinued
0.7115	Intermediate Similarity	NPD4690	Approved
0.7115	Intermediate Similarity	NPD4138	Approved
0.7115	Intermediate Similarity	NPD5205	Approved
0.7115	Intermediate Similarity	NPD4688	Approved
0.7103	Intermediate Similarity	NPD7637	Suspended
0.71	Intermediate Similarity	NPD4195	Approved
0.7087	Intermediate Similarity	NPD3668	Phase 3
0.708	Intermediate Similarity	NPD7236	Approved
0.7069	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD5654	Approved
0.7043	Intermediate Similarity	NPD6412	Phase 2
0.7019	Intermediate Similarity	NPD5363	Approved
0.6992	Remote Similarity	NPD7503	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