NPASS Compound

Structure

NPC46758 OpenBabel07101718292D 32 35 0 0 1 0 0 0 0 0999 V2000 6.1235 -5.1270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7707 -4.5917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1527 -2.6896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1890 -4.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1913 -3.4135 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 5.5054 -3.2248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8363 -3.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.1910 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 1.7321 -3.0000 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 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 6.7926 -4.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4836 -3.4328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8581 -3.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -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 1 0 0 0 0 0 0 0 0 0 3.5491 -2.8090 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 0.8660 -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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 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 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 2 0 0 0 0 6 27 1 0 0 0 0 7 8 1 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 26 1 0 0 0 0 13 19 1 0 0 0 0 13 24 1 0 0 0 0 14 25 1 0 0 0 0 15 19 1 0 0 0 0 15 28 1 0 0 0 0 16 17 1 0 0 0 0 18 4 1 1 0 0 0 18 21 1 0 0 0 0 19 29 1 6 0 0 0 20 14 1 1 0 0 0 20 22 1 0 0 0 0 20 23 1 0 0 0 0 21 26 1 6 0 0 0 22 26 1 6 0 0 0 23 27 1 6 0 0 0 24 27 1 1 0 0 0 24 30 1 0 0 0 0 25 28 1 0 0 0 0 25 31 2 0 0 0 0 26 5 1 6 0 0 0 27 28 1 6 0 0 0 28 32 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	322.18
Volume:	336.177
LogP:	1.678
LogD:	1.221
LogS:	-3.421
# Rotatable Bonds:	6
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.596
Synthetic Accessibility Score:	5.388
Fsp3:	0.722
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.584
MDCK Permeability:	4.626902591553517e-05
Pgp-inhibitor:	0.82
Pgp-substrate:	0.322
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.044
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.895
Plasma Protein Binding (PPB):	72.70902252197266%
Volume Distribution (VD):	0.706
Pgp-substrate:	26.766616821289062%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.356
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.805
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.07
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.055
CYP3A4-inhibitor:	0.624
CYP3A4-substrate:	0.512

ADMET: Excretion

Clearance (CL):	7.703
Half-life (T1/2):	0.517

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.098
Drug-inuced Liver Injury (DILI):	0.439
AMES Toxicity:	0.056
Rat Oral Acute Toxicity:	0.912
Maximum Recommended Daily Dose:	0.426
Skin Sensitization:	0.16
Carcinogencity:	0.918
Eye Corrosion:	0.949
Eye Irritation:	0.325
Respiratory Toxicity:	0.917

Download Data

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

Natural Product: NPC46758

Natural Product ID:	NPC46758
*Common Name:**	Gibberoketosterol
IUPAC Name:	(1S,3S,5S,8S,9S,10S,13R,14S,17R)-1,3,5-trihydroxy-10,13-dimethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-one
Synonyms:	Gibberoketosterol
Standard InCHIKey:	RQXFIFSIGRFXOD-GCNFEMQVSA-N
Standard InCHI:	InChI=1S/C28H46O4/c1-16(2)17(3)7-8-18(4)21-9-10-22-20-14-25(31)28(32)15-19(29)13-24(30)27(28,6)23(20)11-12-26(21,22)5/h16,18-24,29-30,32H,3,7-15H2,1-2,4-6H3/t18-,19+,20+,21-,22+,23+,24+,26-,27+,28-/m1/s1
SMILES:	O[C@H]1C[C@H](O)[C@]2([C@](C1)(O)C(=O)C[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](CCC(=C)C(C)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL522405
PubChem CID:	10993999
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols 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
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921403]
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	formosan soft coral	n.a.	PMID[16124762]
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[16989519]
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17917291]
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[18198839]
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561904]
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	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	4
Others	3

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	68.3	%	PMID[484683]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	44.5	%	PMID[484683]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	38.4	%	PMID[484683]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	14.1	ug.mL-1	PMID[484683]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	14.4	ug.mL-1	PMID[484683]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	14.5	ug.mL-1	PMID[484683]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	13.0	ug.mL-1	PMID[484683]

☑ 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 NPC46758 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	196
0.1-0.2	1737
0.2-0.3	6366
0.3-0.4	14918
0.4-0.5	7079
0.5-0.6	5043
0.6-0.7	5067
0.7-0.8	1987
0.8-0.85	246
0.85-0.9	56
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9231	High Similarity	NPC191565
0.8864	High Similarity	NPC193360
0.8837	High Similarity	NPC475745
0.8837	High Similarity	NPC474233
0.8837	High Similarity	NPC474482
0.883	High Similarity	NPC477053
0.883	High Similarity	NPC477051
0.883	High Similarity	NPC477052
0.8791	High Similarity	NPC209662
0.875	High Similarity	NPC153604
0.8737	High Similarity	NPC477054
0.8721	High Similarity	NPC475726
0.8721	High Similarity	NPC472743
0.871	High Similarity	NPC170978
0.8681	High Similarity	NPC224060
0.8681	High Similarity	NPC244356
0.8667	High Similarity	NPC261994
0.8667	High Similarity	NPC470378
0.8667	High Similarity	NPC149761
0.8652	High Similarity	NPC474719
0.8646	High Similarity	NPC247957
0.8646	High Similarity	NPC249187
0.8636	High Similarity	NPC472738
0.8602	High Similarity	NPC49371
0.8587	High Similarity	NPC153775
0.8587	High Similarity	NPC292374
0.8587	High Similarity	NPC91772
0.8587	High Similarity	NPC196485
0.8587	High Similarity	NPC289539
0.8587	High Similarity	NPC261333
0.8587	High Similarity	NPC129004
0.8587	High Similarity	NPC111524
0.8587	High Similarity	NPC245972
0.8587	High Similarity	NPC29247
0.8587	High Similarity	NPC215271
0.8587	High Similarity	NPC104371
0.8587	High Similarity	NPC101233
0.8571	High Similarity	NPC299185
0.8571	High Similarity	NPC31828
0.8557	High Similarity	NPC72255
0.8556	High Similarity	NPC474245
0.8539	High Similarity	NPC259009
0.8539	High Similarity	NPC269360
0.8539	High Similarity	NPC264005
0.8539	High Similarity	NPC174619
0.8526	High Similarity	NPC156324
0.8526	High Similarity	NPC55503
0.8523	High Similarity	NPC292553
0.8523	High Similarity	NPC471034
0.8523	High Similarity	NPC190704
0.8523	High Similarity	NPC76518
0.8511	High Similarity	NPC190080
0.8511	High Similarity	NPC111187
0.8495	Intermediate Similarity	NPC288906
0.8495	Intermediate Similarity	NPC263135
0.8478	Intermediate Similarity	NPC181594
0.8478	Intermediate Similarity	NPC144739
0.8469	Intermediate Similarity	NPC257353
0.8462	Intermediate Similarity	NPC80401
0.8462	Intermediate Similarity	NPC100313
0.8454	Intermediate Similarity	NPC191892
0.8444	Intermediate Similarity	NPC472739
0.8427	Intermediate Similarity	NPC2783
0.8421	Intermediate Similarity	NPC28864
0.8421	Intermediate Similarity	NPC38471
0.8421	Intermediate Similarity	NPC20479
0.8421	Intermediate Similarity	NPC119036
0.8421	Intermediate Similarity	NPC98837
0.8421	Intermediate Similarity	NPC162459
0.8421	Intermediate Similarity	NPC38296
0.8409	Intermediate Similarity	NPC146683
0.8409	Intermediate Similarity	NPC264665
0.8409	Intermediate Similarity	NPC74595
0.8404	Intermediate Similarity	NPC264979
0.8404	Intermediate Similarity	NPC135548
0.8391	Intermediate Similarity	NPC145143
0.8387	Intermediate Similarity	NPC277399
0.8387	Intermediate Similarity	NPC64006
0.8387	Intermediate Similarity	NPC280804
0.8372	Intermediate Similarity	NPC164999
0.837	Intermediate Similarity	NPC476168
0.837	Intermediate Similarity	NPC198054
0.8367	Intermediate Similarity	NPC47281
0.8352	Intermediate Similarity	NPC213832
0.8352	Intermediate Similarity	NPC57954
0.8333	Intermediate Similarity	NPC4643
0.8333	Intermediate Similarity	NPC293866
0.8333	Intermediate Similarity	NPC472497
0.8333	Intermediate Similarity	NPC165895
0.8333	Intermediate Similarity	NPC57469
0.8333	Intermediate Similarity	NPC15390
0.8333	Intermediate Similarity	NPC33768
0.8316	Intermediate Similarity	NPC253586
0.8316	Intermediate Similarity	NPC10864
0.8315	Intermediate Similarity	NPC294438
0.8315	Intermediate Similarity	NPC264317
0.8298	Intermediate Similarity	NPC271195
0.8298	Intermediate Similarity	NPC231060
0.8298	Intermediate Similarity	NPC138245
0.8298	Intermediate Similarity	NPC279974
0.8298	Intermediate Similarity	NPC98639
0.8298	Intermediate Similarity	NPC84018
0.8295	Intermediate Similarity	NPC291320
0.8295	Intermediate Similarity	NPC118800
0.8295	Intermediate Similarity	NPC85095
0.8295	Intermediate Similarity	NPC471036
0.8295	Intermediate Similarity	NPC216420
0.8295	Intermediate Similarity	NPC211135
0.8295	Intermediate Similarity	NPC232023
0.8283	Intermediate Similarity	NPC28791
0.8283	Intermediate Similarity	NPC50535
0.828	Intermediate Similarity	NPC291373
0.828	Intermediate Similarity	NPC12722
0.828	Intermediate Similarity	NPC294263
0.8276	Intermediate Similarity	NPC328264
0.8261	Intermediate Similarity	NPC180849
0.8256	Intermediate Similarity	NPC80297
0.8256	Intermediate Similarity	NPC475727
0.8256	Intermediate Similarity	NPC201459
0.8256	Intermediate Similarity	NPC116119
0.8256	Intermediate Similarity	NPC472742
0.8247	Intermediate Similarity	NPC71706
0.8247	Intermediate Similarity	NPC118964
0.8247	Intermediate Similarity	NPC121218
0.8247	Intermediate Similarity	NPC46848
0.8247	Intermediate Similarity	NPC253886
0.8242	Intermediate Similarity	NPC146937
0.8242	Intermediate Similarity	NPC471900
0.8242	Intermediate Similarity	NPC16377
0.8229	Intermediate Similarity	NPC89099
0.8229	Intermediate Similarity	NPC78427
0.8229	Intermediate Similarity	NPC16911
0.8222	Intermediate Similarity	NPC269396
0.8222	Intermediate Similarity	NPC12774
0.8222	Intermediate Similarity	NPC51014
0.8222	Intermediate Similarity	NPC98236
0.8211	Intermediate Similarity	NPC29410
0.8211	Intermediate Similarity	NPC140242
0.8211	Intermediate Similarity	NPC234564
0.8211	Intermediate Similarity	NPC200054
0.8202	Intermediate Similarity	NPC50438
0.82	Intermediate Similarity	NPC176949
0.82	Intermediate Similarity	NPC201908
0.82	Intermediate Similarity	NPC86852
0.82	Intermediate Similarity	NPC251824
0.82	Intermediate Similarity	NPC165873
0.8191	Intermediate Similarity	NPC47853
0.8191	Intermediate Similarity	NPC302008
0.8191	Intermediate Similarity	NPC111015
0.8191	Intermediate Similarity	NPC191094
0.8182	Intermediate Similarity	NPC477858
0.8182	Intermediate Similarity	NPC328007
0.8182	Intermediate Similarity	NPC110780
0.8172	Intermediate Similarity	NPC211403
0.8172	Intermediate Similarity	NPC168027
0.8172	Intermediate Similarity	NPC185936
0.8172	Intermediate Similarity	NPC198242
0.8163	Intermediate Similarity	NPC246736
0.8163	Intermediate Similarity	NPC304832
0.8163	Intermediate Similarity	NPC286519
0.8163	Intermediate Similarity	NPC214946
0.8163	Intermediate Similarity	NPC170615
0.8163	Intermediate Similarity	NPC275990
0.8163	Intermediate Similarity	NPC88203
0.8163	Intermediate Similarity	NPC76866
0.8163	Intermediate Similarity	NPC148628
0.8161	Intermediate Similarity	NPC475679
0.8152	Intermediate Similarity	NPC32830
0.8152	Intermediate Similarity	NPC76879
0.8152	Intermediate Similarity	NPC1015
0.8152	Intermediate Similarity	NPC475921
0.8152	Intermediate Similarity	NPC31985
0.8152	Intermediate Similarity	NPC220498
0.8152	Intermediate Similarity	NPC122116
0.8152	Intermediate Similarity	NPC474704
0.8144	Intermediate Similarity	NPC287676
0.8144	Intermediate Similarity	NPC108371
0.8144	Intermediate Similarity	NPC37047
0.8144	Intermediate Similarity	NPC41971
0.8144	Intermediate Similarity	NPC127408
0.8144	Intermediate Similarity	NPC291785
0.8144	Intermediate Similarity	NPC94906
0.8144	Intermediate Similarity	NPC180733
0.8144	Intermediate Similarity	NPC154072
0.8132	Intermediate Similarity	NPC474174
0.8132	Intermediate Similarity	NPC90652
0.8132	Intermediate Similarity	NPC469317
0.8132	Intermediate Similarity	NPC472495
0.8132	Intermediate Similarity	NPC251808
0.8132	Intermediate Similarity	NPC469314
0.8132	Intermediate Similarity	NPC241875
0.8125	Intermediate Similarity	NPC18509
0.8125	Intermediate Similarity	NPC190554
0.8111	Intermediate Similarity	NPC102292
0.8105	Intermediate Similarity	NPC272617
0.8105	Intermediate Similarity	NPC266431
0.8105	Intermediate Similarity	NPC472485
0.8105	Intermediate Similarity	NPC210214
0.81	Intermediate Similarity	NPC166607
0.8095	Intermediate Similarity	NPC254340

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 NPC46758 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	2161
0.2-0.3	4173
0.3-0.4	1788
0.4-0.5	419
0.5-0.6	134
0.6-0.7	165
0.7-0.8	118
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8315	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD4755	Approved
0.809	Intermediate Similarity	NPD4788	Approved
0.8022	Intermediate Similarity	NPD3618	Phase 1
0.8021	Intermediate Similarity	NPD4697	Phase 3
0.8	Intermediate Similarity	NPD4786	Approved
0.7979	Intermediate Similarity	NPD8035	Phase 2
0.7979	Intermediate Similarity	NPD8034	Phase 2
0.7959	Intermediate Similarity	NPD5286	Approved
0.7959	Intermediate Similarity	NPD4700	Approved
0.7959	Intermediate Similarity	NPD4696	Approved
0.7959	Intermediate Similarity	NPD5285	Approved
0.7957	Intermediate Similarity	NPD4753	Phase 2
0.7957	Intermediate Similarity	NPD5328	Approved
0.7931	Intermediate Similarity	NPD6115	Approved
0.7931	Intermediate Similarity	NPD6114	Approved
0.7931	Intermediate Similarity	NPD6697	Approved
0.7931	Intermediate Similarity	NPD6118	Approved
0.7857	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7835	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7835	Intermediate Similarity	NPD5222	Approved
0.7835	Intermediate Similarity	NPD5221	Approved
0.78	Intermediate Similarity	NPD5225	Approved
0.78	Intermediate Similarity	NPD5211	Phase 2
0.78	Intermediate Similarity	NPD4633	Approved
0.78	Intermediate Similarity	NPD5224	Approved
0.78	Intermediate Similarity	NPD5226	Approved
0.7791	Intermediate Similarity	NPD3703	Phase 2
0.7789	Intermediate Similarity	NPD6079	Approved
0.7778	Intermediate Similarity	NPD3667	Approved
0.7755	Intermediate Similarity	NPD5173	Approved
0.7753	Intermediate Similarity	NPD7525	Registered
0.7745	Intermediate Similarity	NPD6402	Approved
0.7745	Intermediate Similarity	NPD5739	Approved
0.7745	Intermediate Similarity	NPD7128	Approved
0.7745	Intermediate Similarity	NPD6675	Approved
0.7738	Intermediate Similarity	NPD4789	Approved
0.7732	Intermediate Similarity	NPD5210	Approved
0.7732	Intermediate Similarity	NPD4629	Approved
0.7723	Intermediate Similarity	NPD5175	Approved
0.7723	Intermediate Similarity	NPD5174	Approved
0.7708	Intermediate Similarity	NPD4202	Approved
0.7701	Intermediate Similarity	NPD6117	Approved
0.77	Intermediate Similarity	NPD5223	Approved
0.7692	Intermediate Similarity	NPD6372	Approved
0.7692	Intermediate Similarity	NPD6373	Approved
0.7647	Intermediate Similarity	NPD5141	Approved
0.7619	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4634	Approved
0.7619	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD6116	Phase 1
0.7596	Intermediate Similarity	NPD6881	Approved
0.7596	Intermediate Similarity	NPD7320	Approved
0.7596	Intermediate Similarity	NPD6899	Approved
0.7576	Intermediate Similarity	NPD6084	Phase 2
0.7576	Intermediate Similarity	NPD6083	Phase 2
0.7573	Intermediate Similarity	NPD4768	Approved
0.7573	Intermediate Similarity	NPD4767	Approved
0.7549	Intermediate Similarity	NPD4754	Approved
0.7547	Intermediate Similarity	NPD6650	Approved
0.7547	Intermediate Similarity	NPD6649	Approved
0.7527	Intermediate Similarity	NPD5329	Approved
0.7526	Intermediate Similarity	NPD6399	Phase 3
0.75	Intermediate Similarity	NPD5701	Approved
0.75	Intermediate Similarity	NPD5360	Phase 3
0.75	Intermediate Similarity	NPD5697	Approved
0.75	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD7102	Approved
0.7453	Intermediate Similarity	NPD6883	Approved
0.7453	Intermediate Similarity	NPD7290	Approved
0.7447	Intermediate Similarity	NPD5279	Phase 3
0.7429	Intermediate Similarity	NPD4729	Approved
0.7429	Intermediate Similarity	NPD5128	Approved
0.7429	Intermediate Similarity	NPD4730	Approved
0.7423	Intermediate Similarity	NPD7515	Phase 2
0.7419	Intermediate Similarity	NPD3665	Phase 1
0.7419	Intermediate Similarity	NPD3133	Approved
0.7419	Intermediate Similarity	NPD3666	Approved
0.7419	Intermediate Similarity	NPD4197	Approved
0.7383	Intermediate Similarity	NPD6847	Approved
0.7383	Intermediate Similarity	NPD6617	Approved
0.7383	Intermediate Similarity	NPD6869	Approved
0.7383	Intermediate Similarity	NPD8130	Phase 1
0.7358	Intermediate Similarity	NPD6012	Approved
0.7358	Intermediate Similarity	NPD6014	Approved
0.7358	Intermediate Similarity	NPD6013	Approved
0.7327	Intermediate Similarity	NPD5696	Approved
0.7327	Intermediate Similarity	NPD7638	Approved
0.7326	Intermediate Similarity	NPD4244	Approved
0.7326	Intermediate Similarity	NPD4245	Approved
0.7315	Intermediate Similarity	NPD8297	Approved
0.7315	Intermediate Similarity	NPD6882	Approved
0.729	Intermediate Similarity	NPD5251	Approved
0.729	Intermediate Similarity	NPD5249	Phase 3
0.729	Intermediate Similarity	NPD5248	Approved
0.729	Intermediate Similarity	NPD5250	Approved
0.729	Intermediate Similarity	NPD5247	Approved
0.7264	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD6011	Approved
0.7263	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7639	Approved
0.7255	Intermediate Similarity	NPD7640	Approved
0.7248	Intermediate Similarity	NPD4632	Approved
0.7234	Intermediate Similarity	NPD3668	Phase 3
0.7222	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5217	Approved
0.7222	Intermediate Similarity	NPD5216	Approved
0.7222	Intermediate Similarity	NPD5215	Approved
0.7209	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD3698	Phase 2
0.7204	Intermediate Similarity	NPD4221	Approved
0.7204	Intermediate Similarity	NPD4223	Phase 3
0.72	Intermediate Similarity	NPD5695	Phase 3
0.7168	Intermediate Similarity	NPD6054	Approved
0.7168	Intermediate Similarity	NPD6059	Approved
0.7143	Intermediate Similarity	NPD3617	Approved
0.7143	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5169	Approved
0.713	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5135	Approved
0.7113	Intermediate Similarity	NPD5737	Approved
0.7113	Intermediate Similarity	NPD6672	Approved
0.7103	Intermediate Similarity	NPD5168	Approved
0.71	Intermediate Similarity	NPD7748	Approved
0.7083	Intermediate Similarity	NPD4694	Approved
0.7083	Intermediate Similarity	NPD5690	Phase 2
0.7083	Intermediate Similarity	NPD5280	Approved
0.7064	Intermediate Similarity	NPD5127	Approved
0.7059	Intermediate Similarity	NPD7902	Approved
0.7054	Intermediate Similarity	NPD6009	Approved
0.7045	Intermediate Similarity	NPD4758	Discontinued
0.7043	Intermediate Similarity	NPD6370	Approved
0.7018	Intermediate Similarity	NPD6319	Approved
0.7	Intermediate Similarity	NPD6942	Approved
0.7	Intermediate Similarity	NPD7339	Approved
0.6989	Remote Similarity	NPD6931	Approved
0.6989	Remote Similarity	NPD6930	Phase 2
0.6964	Remote Similarity	NPD6274	Approved
0.6957	Remote Similarity	NPD3671	Phase 1
0.6957	Remote Similarity	NPD6016	Approved
0.6957	Remote Similarity	NPD5364	Discontinued
0.6957	Remote Similarity	NPD6015	Approved
0.6947	Remote Similarity	NPD6695	Phase 3
0.6937	Remote Similarity	NPD8133	Approved
0.693	Remote Similarity	NPD7101	Approved
0.693	Remote Similarity	NPD7100	Approved
0.6923	Remote Similarity	NPD7492	Approved
0.6916	Remote Similarity	NPD6008	Approved
0.6907	Remote Similarity	NPD6098	Approved
0.6907	Remote Similarity	NPD4689	Approved
0.6907	Remote Similarity	NPD4693	Phase 3
0.6907	Remote Similarity	NPD4138	Approved
0.6907	Remote Similarity	NPD4690	Approved
0.6907	Remote Similarity	NPD5205	Approved
0.6907	Remote Similarity	NPD4688	Approved
0.6903	Remote Similarity	NPD7115	Discovery
0.6897	Remote Similarity	NPD5988	Approved
0.6891	Remote Similarity	NPD7736	Approved
0.6882	Remote Similarity	NPD7645	Phase 2
0.6882	Remote Similarity	NPD6929	Approved
0.6875	Remote Similarity	NPD5167	Approved
0.6875	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD6673	Approved
0.6869	Remote Similarity	NPD6904	Approved
0.6869	Remote Similarity	NPD6080	Approved
0.6864	Remote Similarity	NPD6616	Approved
0.6863	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD6081	Approved
0.6852	Remote Similarity	NPD6412	Phase 2
0.6848	Remote Similarity	NPD6932	Approved
0.6842	Remote Similarity	NPD6335	Approved
0.6838	Remote Similarity	NPD7604	Phase 2
0.6814	Remote Similarity	NPD6868	Approved
0.681	Remote Similarity	NPD6908	Approved
0.681	Remote Similarity	NPD5983	Phase 2
0.681	Remote Similarity	NPD6909	Approved
0.6809	Remote Similarity	NPD4695	Discontinued
0.6807	Remote Similarity	NPD8293	Discontinued
0.6807	Remote Similarity	NPD7078	Approved
0.6792	Remote Similarity	NPD7632	Discontinued
0.6768	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7900	Approved
0.6765	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6317	Approved
0.6739	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD4692	Approved
0.6737	Remote Similarity	NPD4139	Approved
0.6735	Remote Similarity	NPD6409	Approved
0.6735	Remote Similarity	NPD5330	Approved
0.6735	Remote Similarity	NPD7521	Approved
0.6735	Remote Similarity	NPD6684	Approved
0.6735	Remote Similarity	NPD7334	Approved
0.6735	Remote Similarity	NPD7146	Approved
0.6733	Remote Similarity	NPD5281	Approved
0.6733	Remote Similarity	NPD5284	Approved
0.6723	Remote Similarity	NPD6336	Discontinued
0.6703	Remote Similarity	NPD6926	Approved
0.6703	Remote Similarity	NPD6924	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