NPASS Compound

Structure

NPC42042 OpenBabel07101719252D 38 41 0 0 1 0 0 0 0 0999 V2000 -0.1293 -6.3916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5180 -5.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7473 -4.4895 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 -2.9641 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 2.8660 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 -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 0.9000 -3.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5909 -3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5398 -5.6485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2308 -4.6974 0.0000 C 0 0 0 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 1.2601 -2.2601 0.0000 C 0 0 2 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 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 -2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 1 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 -0.0000 -0.0000 0.0000 C 0 0 1 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 -5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5472 -3.4190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9074 -1.7248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 2 0 0 0 0 4 21 1 0 0 0 0 5 30 1 0 0 0 0 6 30 1 0 0 0 0 8 32 1 0 0 0 0 10 11 1 0 0 0 0 10 20 1 0 0 0 0 12 13 1 0 0 0 0 12 24 1 0 0 0 0 13 26 1 0 0 0 0 14 17 1 0 0 0 0 14 23 1 0 0 0 0 15 16 1 0 0 0 0 15 27 1 0 0 0 0 16 31 1 0 0 0 0 17 32 1 0 0 0 0 18 25 1 0 0 0 0 18 28 1 0 0 0 0 19 20 1 0 0 0 0 21 34 2 0 0 0 0 21 38 1 0 0 0 0 22 11 1 6 0 0 0 22 25 1 0 0 0 0 22 29 1 0 0 0 0 23 24 2 0 0 0 0 23 31 1 0 0 0 0 24 33 1 0 0 0 0 25 32 1 6 0 0 0 26 30 1 0 0 0 0 26 31 1 6 0 0 0 27 30 1 0 0 0 0 27 35 2 0 0 0 0 28 33 1 1 0 0 0 28 38 1 0 0 0 0 29 36 2 0 0 0 0 29 37 1 0 0 0 0 31 7 1 6 0 0 0 32 33 1 6 0 0 0 33 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	526.37
Volume:	575.867
LogP:	5.158
LogD:	4.135
LogS:	-5.148
# Rotatable Bonds:	8
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.274
Synthetic Accessibility Score:	5.054
Fsp3:	0.788
Lipinski Rule-of-5:	Rejected
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:	-5.31
MDCK Permeability:	1.694587444944773e-05
Pgp-inhibitor:	0.611
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.162
30% Bioavailability (F30%):	0.922

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.211
Plasma Protein Binding (PPB):	88.30542755126953%
Volume Distribution (VD):	0.657
Pgp-substrate:	4.579935073852539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.384
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.955
CYP2C9-inhibitor:	0.159
CYP2C9-substrate:	0.976
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.545
CYP3A4-inhibitor:	0.151
CYP3A4-substrate:	0.47

ADMET: Excretion

Clearance (CL):	3.985
Half-life (T1/2):	0.461

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.496
Drug-inuced Liver Injury (DILI):	0.465
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.116
Maximum Recommended Daily Dose:	0.819
Skin Sensitization:	0.043
Carcinogencity:	0.214
Eye Corrosion:	0.005
Eye Irritation:	0.071
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC42042

Natural Product ID:	NPC42042
*Common Name:**	Acetyl-3-Oxo-Sulfurenic Acid
IUPAC Name:	(2R)-2-[(5R,10S,13R,14R,15S,17R)-15-acetyloxy-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,7,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-6-methyl-5-methylideneheptanoic acid
Synonyms:
Standard InCHIKey:	HGKYZLMBDDTARR-VPDRPMEHSA-N
Standard InCHI:	InChI=1S/C33H50O5/c1-19(2)20(3)10-11-22(29(36)37)25-18-28(38-21(4)34)33(9)24-12-13-26-30(5,6)27(35)15-16-31(26,7)23(24)14-17-32(25,33)8/h19,22,25-26,28H,3,10-18H2,1-2,4-9H3,(H,36,37)/t22-,25-,26+,28+,31-,32-,33-/m1/s1
SMILES:	CC(=O)O[C@H]1C[C@@H]([C@@]2([C@]1(C)C1=C(CC2)[C@@]2([C@@H](CC1)C(C)(C)C(=O)CC2)C)C)[C@H](C(=O)O)CCC(=C)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL485850
PubChem CID:	10602203
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO8498	Laetiporus sulphureus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15620242]
NPO8498	Laetiporus sulphureus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19842686]
NPO8498	Laetiporus sulphureus	Species	Coriolaceae	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
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	25000.0	nM	PMID[547702]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	25000.0	nM	PMID[547703]

☑ 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 NPC42042 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	179
0.1-0.2	1186
0.2-0.3	5160
0.3-0.4	12592
0.4-0.5	9088
0.5-0.6	6000
0.6-0.7	6648
0.7-0.8	1615
0.8-0.85	171
0.85-0.9	52
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9444	High Similarity	NPC206810
0.9032	High Similarity	NPC48330
0.898	High Similarity	NPC231530
0.898	High Similarity	NPC278628
0.8936	High Similarity	NPC173272
0.8854	High Similarity	NPC218383
0.883	High Similarity	NPC469599
0.8812	High Similarity	NPC197428
0.88	High Similarity	NPC94529
0.8788	High Similarity	NPC196528
0.8776	High Similarity	NPC140723
0.875	High Similarity	NPC271387
0.875	High Similarity	NPC153792
0.8713	High Similarity	NPC304495
0.871	High Similarity	NPC26888
0.8696	High Similarity	NPC54689
0.8696	High Similarity	NPC474889
0.8687	High Similarity	NPC96268
0.8632	High Similarity	NPC470016
0.8632	High Similarity	NPC317586
0.8632	High Similarity	NPC184848
0.8632	High Similarity	NPC69548
0.8617	High Similarity	NPC25750
0.8602	High Similarity	NPC111585
0.8602	High Similarity	NPC148414
0.8602	High Similarity	NPC289213
0.8602	High Similarity	NPC175628
0.8587	High Similarity	NPC183546
0.8586	High Similarity	NPC159442
0.8571	High Similarity	NPC99411
0.8557	High Similarity	NPC477854
0.8557	High Similarity	NPC197386
0.8544	High Similarity	NPC118860
0.8544	High Similarity	NPC231589
0.8544	High Similarity	NPC214797
0.8542	High Similarity	NPC328371
0.8542	High Similarity	NPC125622
0.8529	High Similarity	NPC258543
0.8529	High Similarity	NPC241927
0.8526	High Similarity	NPC166906
0.8511	High Similarity	NPC150383
0.8511	High Similarity	NPC154101
0.8495	Intermediate Similarity	NPC474570
0.8485	Intermediate Similarity	NPC22388
0.8485	Intermediate Similarity	NPC475558
0.8485	Intermediate Similarity	NPC473788
0.8485	Intermediate Similarity	NPC56498
0.8485	Intermediate Similarity	NPC473928
0.8469	Intermediate Similarity	NPC167974
0.8469	Intermediate Similarity	NPC83709
0.8462	Intermediate Similarity	NPC170487
0.8462	Intermediate Similarity	NPC280782
0.8454	Intermediate Similarity	NPC18319
0.8438	Intermediate Similarity	NPC173875
0.8438	Intermediate Similarity	NPC174948
0.8438	Intermediate Similarity	NPC241156
0.8438	Intermediate Similarity	NPC318282
0.8438	Intermediate Similarity	NPC469995
0.8421	Intermediate Similarity	NPC66429
0.8421	Intermediate Similarity	NPC152897
0.8421	Intermediate Similarity	NPC243866
0.8416	Intermediate Similarity	NPC181265
0.8416	Intermediate Similarity	NPC475571
0.8404	Intermediate Similarity	NPC471896
0.84	Intermediate Similarity	NPC236390
0.8387	Intermediate Similarity	NPC294480
0.8387	Intermediate Similarity	NPC242864
0.8384	Intermediate Similarity	NPC474327
0.8381	Intermediate Similarity	NPC202889
0.837	Intermediate Similarity	NPC212843
0.8367	Intermediate Similarity	NPC477813
0.8352	Intermediate Similarity	NPC109512
0.8351	Intermediate Similarity	NPC111684
0.8351	Intermediate Similarity	NPC305483
0.8351	Intermediate Similarity	NPC95565
0.8351	Intermediate Similarity	NPC328162
0.8351	Intermediate Similarity	NPC96859
0.8351	Intermediate Similarity	NPC477853
0.8351	Intermediate Similarity	NPC120708
0.8351	Intermediate Similarity	NPC58052
0.8333	Intermediate Similarity	NPC260956
0.8333	Intermediate Similarity	NPC184870
0.8317	Intermediate Similarity	NPC29705
0.8317	Intermediate Similarity	NPC235889
0.8317	Intermediate Similarity	NPC477812
0.8317	Intermediate Similarity	NPC310586
0.8317	Intermediate Similarity	NPC28656
0.8316	Intermediate Similarity	NPC23434
0.83	Intermediate Similarity	NPC15396
0.83	Intermediate Similarity	NPC195290
0.83	Intermediate Similarity	NPC204450
0.83	Intermediate Similarity	NPC475320
0.8286	Intermediate Similarity	NPC71348
0.8283	Intermediate Similarity	NPC241221
0.8283	Intermediate Similarity	NPC205899
0.828	Intermediate Similarity	NPC167877
0.828	Intermediate Similarity	NPC312215
0.8269	Intermediate Similarity	NPC114961
0.8269	Intermediate Similarity	NPC27551
0.8265	Intermediate Similarity	NPC320306
0.8265	Intermediate Similarity	NPC43747
0.8265	Intermediate Similarity	NPC475894
0.8265	Intermediate Similarity	NPC190554
0.8252	Intermediate Similarity	NPC470269
0.8247	Intermediate Similarity	NPC472932
0.8247	Intermediate Similarity	NPC263347
0.8247	Intermediate Similarity	NPC279974
0.8242	Intermediate Similarity	NPC168188
0.8242	Intermediate Similarity	NPC470015
0.8235	Intermediate Similarity	NPC96377
0.8229	Intermediate Similarity	NPC470254
0.8224	Intermediate Similarity	NPC270958
0.8224	Intermediate Similarity	NPC190286
0.8222	Intermediate Similarity	NPC38350
0.8222	Intermediate Similarity	NPC201912
0.8218	Intermediate Similarity	NPC55872
0.8211	Intermediate Similarity	NPC20388
0.8211	Intermediate Similarity	NPC123854
0.8208	Intermediate Similarity	NPC52634
0.8208	Intermediate Similarity	NPC472926
0.82	Intermediate Similarity	NPC472924
0.82	Intermediate Similarity	NPC473514
0.8191	Intermediate Similarity	NPC470612
0.8191	Intermediate Similarity	NPC28227
0.8191	Intermediate Similarity	NPC470613
0.8182	Intermediate Similarity	NPC166745
0.8182	Intermediate Similarity	NPC114274
0.8182	Intermediate Similarity	NPC10364
0.8182	Intermediate Similarity	NPC235464
0.8182	Intermediate Similarity	NPC119036
0.8173	Intermediate Similarity	NPC118225
0.8172	Intermediate Similarity	NPC155011
0.8172	Intermediate Similarity	NPC55309
0.8172	Intermediate Similarity	NPC195640
0.8172	Intermediate Similarity	NPC264127
0.8172	Intermediate Similarity	NPC28252
0.8163	Intermediate Similarity	NPC49371
0.8163	Intermediate Similarity	NPC7124
0.8163	Intermediate Similarity	NPC253115
0.8163	Intermediate Similarity	NPC155676
0.8163	Intermediate Similarity	NPC304899
0.8155	Intermediate Similarity	NPC59530
0.8155	Intermediate Similarity	NPC220974
0.8152	Intermediate Similarity	NPC82902
0.8144	Intermediate Similarity	NPC159410
0.8144	Intermediate Similarity	NPC474922
0.8137	Intermediate Similarity	NPC255309
0.8137	Intermediate Similarity	NPC223741
0.8137	Intermediate Similarity	NPC164835
0.8137	Intermediate Similarity	NPC228669
0.8132	Intermediate Similarity	NPC327969
0.8132	Intermediate Similarity	NPC321289
0.8131	Intermediate Similarity	NPC473898
0.8125	Intermediate Similarity	NPC107690
0.8125	Intermediate Similarity	NPC297265
0.8119	Intermediate Similarity	NPC53222
0.8119	Intermediate Similarity	NPC308351
0.8119	Intermediate Similarity	NPC271266
0.8119	Intermediate Similarity	NPC119601
0.8119	Intermediate Similarity	NPC308726
0.8113	Intermediate Similarity	NPC221144
0.8105	Intermediate Similarity	NPC215029
0.8105	Intermediate Similarity	NPC476733
0.8105	Intermediate Similarity	NPC155479
0.8105	Intermediate Similarity	NPC477943
0.8105	Intermediate Similarity	NPC186688
0.81	Intermediate Similarity	NPC316964
0.81	Intermediate Similarity	NPC15390
0.81	Intermediate Similarity	NPC474720
0.81	Intermediate Similarity	NPC327431
0.8095	Intermediate Similarity	NPC129689
0.8085	Intermediate Similarity	NPC317590
0.8085	Intermediate Similarity	NPC159046
0.8085	Intermediate Similarity	NPC233836
0.8085	Intermediate Similarity	NPC96496
0.8085	Intermediate Similarity	NPC187376
0.8081	Intermediate Similarity	NPC107243
0.8081	Intermediate Similarity	NPC57416
0.8081	Intermediate Similarity	NPC121339
0.8081	Intermediate Similarity	NPC108078
0.8073	Intermediate Similarity	NPC153440
0.8073	Intermediate Similarity	NPC118638
0.8065	Intermediate Similarity	NPC123319
0.8065	Intermediate Similarity	NPC94531
0.8065	Intermediate Similarity	NPC323765
0.8065	Intermediate Similarity	NPC311702
0.8065	Intermediate Similarity	NPC474218
0.8061	Intermediate Similarity	NPC162001
0.8061	Intermediate Similarity	NPC473648
0.8061	Intermediate Similarity	NPC222845
0.8061	Intermediate Similarity	NPC45324
0.8061	Intermediate Similarity	NPC470229
0.8061	Intermediate Similarity	NPC127063
0.8058	Intermediate Similarity	NPC162033
0.8058	Intermediate Similarity	NPC470309
0.8058	Intermediate Similarity	NPC323834
0.8058	Intermediate Similarity	NPC210178
0.8056	Intermediate Similarity	NPC148458
0.8043	Intermediate Similarity	NPC476082
0.8043	Intermediate Similarity	NPC245866

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 NPC42042 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	1604
0.2-0.3	4036
0.3-0.4	2269
0.4-0.5	562
0.5-0.6	200
0.6-0.7	194
0.7-0.8	130
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
0.8421	Intermediate Similarity	NPD6399	Phase 3
0.8247	Intermediate Similarity	NPD5695	Phase 3
0.8172	Intermediate Similarity	NPD5330	Approved
0.8172	Intermediate Similarity	NPD7334	Approved
0.8172	Intermediate Similarity	NPD7521	Approved
0.8172	Intermediate Similarity	NPD7146	Approved
0.8172	Intermediate Similarity	NPD6684	Approved
0.8172	Intermediate Similarity	NPD6409	Approved
0.8081	Intermediate Similarity	NPD6083	Phase 2
0.8081	Intermediate Similarity	NPD6084	Phase 2
0.8058	Intermediate Similarity	NPD6008	Approved
0.8058	Intermediate Similarity	NPD6675	Approved
0.8058	Intermediate Similarity	NPD6402	Approved
0.8058	Intermediate Similarity	NPD5739	Approved
0.8058	Intermediate Similarity	NPD7128	Approved
0.8	Intermediate Similarity	NPD6903	Approved
0.8	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7957	Intermediate Similarity	NPD4786	Approved
0.7905	Intermediate Similarity	NPD6899	Approved
0.7905	Intermediate Similarity	NPD6881	Approved
0.7905	Intermediate Similarity	NPD7320	Approved
0.785	Intermediate Similarity	NPD8130	Phase 1
0.783	Intermediate Similarity	NPD6373	Approved
0.783	Intermediate Similarity	NPD6372	Approved
0.7822	Intermediate Similarity	NPD5696	Approved
0.7812	Intermediate Similarity	NPD5737	Approved
0.7812	Intermediate Similarity	NPD6672	Approved
0.781	Intermediate Similarity	NPD5701	Approved
0.781	Intermediate Similarity	NPD5697	Approved
0.7789	Intermediate Similarity	NPD6098	Approved
0.7778	Intermediate Similarity	NPD8297	Approved
0.7766	Intermediate Similarity	NPD3133	Approved
0.7766	Intermediate Similarity	NPD3666	Approved
0.7766	Intermediate Similarity	NPD3665	Phase 1
0.7757	Intermediate Similarity	NPD7290	Approved
0.7757	Intermediate Similarity	NPD6883	Approved
0.7757	Intermediate Similarity	NPD7102	Approved
0.7755	Intermediate Similarity	NPD5284	Approved
0.7755	Intermediate Similarity	NPD6050	Approved
0.7755	Intermediate Similarity	NPD5281	Approved
0.7742	Intermediate Similarity	NPD3667	Approved
0.7736	Intermediate Similarity	NPD6011	Approved
0.7732	Intermediate Similarity	NPD6673	Approved
0.7732	Intermediate Similarity	NPD5328	Approved
0.7732	Intermediate Similarity	NPD6904	Approved
0.7732	Intermediate Similarity	NPD6080	Approved
0.7706	Intermediate Similarity	NPD4632	Approved
0.7685	Intermediate Similarity	NPD6847	Approved
0.7685	Intermediate Similarity	NPD6869	Approved
0.7685	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD6649	Approved
0.7685	Intermediate Similarity	NPD6617	Approved
0.7685	Intermediate Similarity	NPD6650	Approved
0.7664	Intermediate Similarity	NPD6013	Approved
0.7664	Intermediate Similarity	NPD6012	Approved
0.7664	Intermediate Similarity	NPD6014	Approved
0.7653	Intermediate Similarity	NPD5692	Phase 3
0.7647	Intermediate Similarity	NPD7638	Approved
0.7642	Intermediate Similarity	NPD6412	Phase 2
0.7615	Intermediate Similarity	NPD6053	Discontinued
0.7615	Intermediate Similarity	NPD6882	Approved
0.76	Intermediate Similarity	NPD7748	Approved
0.7576	Intermediate Similarity	NPD6079	Approved
0.7576	Intermediate Similarity	NPD8034	Phase 2
0.7576	Intermediate Similarity	NPD8035	Phase 2
0.7576	Intermediate Similarity	NPD5694	Approved
0.7576	Intermediate Similarity	NPD6411	Approved
0.7573	Intermediate Similarity	NPD7640	Approved
0.7573	Intermediate Similarity	NPD7639	Approved
0.7553	Intermediate Similarity	NPD4223	Phase 3
0.7553	Intermediate Similarity	NPD4221	Approved
0.7551	Intermediate Similarity	NPD4753	Phase 2
0.7549	Intermediate Similarity	NPD4755	Approved
0.7525	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6009	Approved
0.75	Intermediate Similarity	NPD5329	Approved
0.7475	Intermediate Similarity	NPD5207	Approved
0.7456	Intermediate Similarity	NPD6319	Approved
0.7449	Intermediate Similarity	NPD5208	Approved
0.7447	Intermediate Similarity	NPD4692	Approved
0.7447	Intermediate Similarity	NPD4139	Approved
0.7423	Intermediate Similarity	NPD5690	Phase 2
0.7423	Intermediate Similarity	NPD5280	Approved
0.7423	Intermediate Similarity	NPD5279	Phase 3
0.7423	Intermediate Similarity	NPD4694	Approved
0.7414	Intermediate Similarity	NPD7604	Phase 2
0.7404	Intermediate Similarity	NPD5286	Approved
0.7404	Intermediate Similarity	NPD4700	Approved
0.7404	Intermediate Similarity	NPD4696	Approved
0.7404	Intermediate Similarity	NPD5285	Approved
0.74	Intermediate Similarity	NPD5693	Phase 1
0.7396	Intermediate Similarity	NPD4197	Approved
0.7396	Intermediate Similarity	NPD3668	Phase 3
0.7391	Intermediate Similarity	NPD5983	Phase 2
0.7379	Intermediate Similarity	NPD7902	Approved
0.7374	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD6101	Approved
0.7373	Intermediate Similarity	NPD8293	Discontinued
0.7368	Intermediate Similarity	NPD6435	Approved
0.735	Intermediate Similarity	NPD7492	Approved
0.7333	Intermediate Similarity	NPD5223	Approved
0.7327	Intermediate Similarity	NPD5779	Approved
0.7327	Intermediate Similarity	NPD4202	Approved
0.7327	Intermediate Similarity	NPD5778	Approved
0.732	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD7736	Approved
0.7304	Intermediate Similarity	NPD6054	Approved
0.7304	Intermediate Similarity	NPD6059	Approved
0.7292	Intermediate Similarity	NPD4788	Approved
0.7288	Intermediate Similarity	NPD6336	Discontinued
0.7288	Intermediate Similarity	NPD6616	Approved
0.7282	Intermediate Similarity	NPD4697	Phase 3
0.7282	Intermediate Similarity	NPD5222	Approved
0.7282	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD5221	Approved
0.7281	Intermediate Similarity	NPD6335	Approved
0.7264	Intermediate Similarity	NPD5224	Approved
0.7264	Intermediate Similarity	NPD5226	Approved
0.7264	Intermediate Similarity	NPD4633	Approved
0.7264	Intermediate Similarity	NPD5225	Approved
0.7264	Intermediate Similarity	NPD5211	Phase 2
0.7257	Intermediate Similarity	NPD6274	Approved
0.7245	Intermediate Similarity	NPD4138	Approved
0.7245	Intermediate Similarity	NPD4690	Approved
0.7245	Intermediate Similarity	NPD4693	Phase 3
0.7245	Intermediate Similarity	NPD3618	Phase 1
0.7245	Intermediate Similarity	NPD5205	Approved
0.7245	Intermediate Similarity	NPD4689	Approved
0.7245	Intermediate Similarity	NPD4688	Approved
0.7228	Intermediate Similarity	NPD7515	Phase 2
0.7227	Intermediate Similarity	NPD7078	Approved
0.7217	Intermediate Similarity	NPD7100	Approved
0.7217	Intermediate Similarity	NPD7101	Approved
0.7212	Intermediate Similarity	NPD5173	Approved
0.72	Intermediate Similarity	NPD6051	Approved
0.7196	Intermediate Similarity	NPD5175	Approved
0.7196	Intermediate Similarity	NPD5174	Approved
0.7196	Intermediate Similarity	NPD4754	Approved
0.7193	Intermediate Similarity	NPD6317	Approved
0.7184	Intermediate Similarity	NPD5210	Approved
0.7184	Intermediate Similarity	NPD5654	Approved
0.7184	Intermediate Similarity	NPD4629	Approved
0.7179	Intermediate Similarity	NPD6370	Approved
0.7174	Intermediate Similarity	NPD3702	Approved
0.7158	Intermediate Similarity	NPD5368	Approved
0.713	Intermediate Similarity	NPD6313	Approved
0.713	Intermediate Similarity	NPD5141	Approved
0.713	Intermediate Similarity	NPD6314	Approved
0.7117	Intermediate Similarity	NPD4634	Approved
0.7113	Intermediate Similarity	NPD5362	Discontinued
0.7105	Intermediate Similarity	NPD6868	Approved
0.7103	Intermediate Similarity	NPD7632	Discontinued
0.7097	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD6016	Approved
0.7094	Intermediate Similarity	NPD6909	Approved
0.7094	Intermediate Similarity	NPD6015	Approved
0.7094	Intermediate Similarity	NPD6908	Approved
0.7087	Intermediate Similarity	NPD7900	Approved
0.7087	Intermediate Similarity	NPD6001	Approved
0.7087	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5369	Approved
0.7071	Intermediate Similarity	NPD5786	Approved
0.7064	Intermediate Similarity	NPD4767	Approved
0.7064	Intermediate Similarity	NPD4768	Approved
0.7059	Intermediate Similarity	NPD7637	Suspended
0.7048	Intermediate Similarity	NPD5959	Approved
0.7034	Intermediate Similarity	NPD5988	Approved
0.7033	Intermediate Similarity	NPD5777	Approved
0.703	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7507	Approved
0.6989	Remote Similarity	NPD6942	Approved
0.6989	Remote Similarity	NPD7339	Approved
0.6961	Remote Similarity	NPD4096	Approved
0.6949	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6115	Approved
0.6947	Remote Similarity	NPD6114	Approved
0.6947	Remote Similarity	NPD3617	Approved
0.6947	Remote Similarity	NPD6697	Approved
0.6947	Remote Similarity	NPD6118	Approved
0.6947	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4729	Approved
0.6937	Remote Similarity	NPD4730	Approved
0.6937	Remote Similarity	NPD5128	Approved
0.6931	Remote Similarity	NPD4518	Approved
0.69	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7115	Discovery
0.6885	Remote Similarity	NPD6033	Approved
0.6882	Remote Similarity	NPD4784	Approved
0.6882	Remote Similarity	NPD4785	Approved
0.6881	Remote Similarity	NPD6052	Approved
0.6875	Remote Similarity	NPD4195	Approved
0.6848	Remote Similarity	NPD4243	Approved
0.6837	Remote Similarity	NPD4269	Approved
0.6837	Remote Similarity	NPD4270	Approved
0.6832	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD3573	Approved
0.6829	Remote Similarity	NPD7319	Approved
0.6827	Remote Similarity	NPD5133	Approved
0.6814	Remote Similarity	NPD5251	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