NPASS Compound

Structure

NPC191565 OpenBabel07101719252D 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 2 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:	444.32
Volume:	485.87
LogP:	4.423
LogD:	4.689
LogS:	-4.697
# Rotatable Bonds:	4
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.551
Synthetic Accessibility Score:	5.219
Fsp3:	0.821
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.747
MDCK Permeability:	2.7473339287098497e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.021

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.787
Plasma Protein Binding (PPB):	92.65499877929688%
Volume Distribution (VD):	0.58
Pgp-substrate:	3.222146987915039%

ADMET: Metabolism

CYP1A2-inhibitor:	0.112
CYP1A2-substrate:	0.426
CYP2C19-inhibitor:	0.057
CYP2C19-substrate:	0.788
CYP2C9-inhibitor:	0.166
CYP2C9-substrate:	0.049
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.072
CYP3A4-inhibitor:	0.902
CYP3A4-substrate:	0.773

ADMET: Excretion

Clearance (CL):	11.68
Half-life (T1/2):	0.223

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.296
Drug-inuced Liver Injury (DILI):	0.051
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.845
Maximum Recommended Daily Dose:	0.98
Skin Sensitization:	0.749
Carcinogencity:	0.91
Eye Corrosion:	0.043
Eye Irritation:	0.068
Respiratory Toxicity:	0.99

Download Data

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

Natural Product: NPC191565

Natural Product ID:	NPC191565
*Common Name:**	Gibberoketosterol B
IUPAC Name:	(1S,3S,5S,8S,9S,10S,13R,14S,17R)-1,3,5-trihydroxy-10,13-dimethyl-17-[(E,2R)-6-methyl-5-methylidenehept-3-en-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-one
Synonyms:	gibberoketosterol B
Standard InCHIKey:	GGUKDEVDQIQJKX-FBLPJEGZSA-N
Standard InCHI:	InChI=1S/C28H44O4/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/h7-8,16,18-24,29-30,32H,3,9-15H2,1-2,4-6H3/b8-7+/t18-,19+,20+,21-,22+,23+,24+,26-,27+,28-/m1/s1
SMILES:	CC(C)C(=C)/C=C/[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC(=O)[C@@]4(C[C@H](C[C@@H]([C@]4(C)[C@H]3CC[C@]12C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL496244
PubChem CID:	16086526
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

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	30.0	ug.mL-1	PMID[537698]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	30.0	ug.mL-1	PMID[537698]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	30.0	ug.mL-1	PMID[537698]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	30.0	ug.mL-1	PMID[537698]

☑ 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 NPC191565 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	195
0.1-0.2	1082
0.2-0.3	4415
0.3-0.4	10126
0.4-0.5	12610
0.5-0.6	6048
0.6-0.7	5763
0.7-0.8	2306
0.8-0.85	132
0.85-0.9	12
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.956	High Similarity	NPC209662
0.9231	High Similarity	NPC46758
0.9167	High Similarity	NPC477051
0.9167	High Similarity	NPC477053
0.9167	High Similarity	NPC477052
0.9072	High Similarity	NPC477054
0.9011	High Similarity	NPC193360
0.898	High Similarity	NPC247957
0.898	High Similarity	NPC249187
0.88	High Similarity	NPC257353
0.875	High Similarity	NPC49371
0.8737	High Similarity	NPC245972
0.8737	High Similarity	NPC196485
0.871	High Similarity	NPC474245
0.87	High Similarity	NPC72255
0.8602	High Similarity	NPC292491
0.8602	High Similarity	NPC310752
0.86	High Similarity	NPC191892
0.8571	High Similarity	NPC119036
0.8571	High Similarity	NPC103051
0.8526	High Similarity	NPC473167
0.8495	Intermediate Similarity	NPC141292
0.8485	Intermediate Similarity	NPC15390
0.8454	Intermediate Similarity	NPC127063
0.8454	Intermediate Similarity	NPC271195
0.8454	Intermediate Similarity	NPC279974
0.8454	Intermediate Similarity	NPC180950
0.8454	Intermediate Similarity	NPC272617
0.8438	Intermediate Similarity	NPC12722
0.8431	Intermediate Similarity	NPC166607
0.8426	Intermediate Similarity	NPC146786
0.84	Intermediate Similarity	NPC118964
0.8387	Intermediate Similarity	NPC51014
0.8351	Intermediate Similarity	NPC474690
0.8351	Intermediate Similarity	NPC49670
0.8351	Intermediate Similarity	NPC111015
0.8351	Intermediate Similarity	NPC299100
0.835	Intermediate Similarity	NPC165873
0.8333	Intermediate Similarity	NPC29705
0.8333	Intermediate Similarity	NPC185936
0.8333	Intermediate Similarity	NPC272746
0.8333	Intermediate Similarity	NPC160843
0.8333	Intermediate Similarity	NPC168027
0.8316	Intermediate Similarity	NPC1015
0.8316	Intermediate Similarity	NPC475921
0.8316	Intermediate Similarity	NPC474704
0.8316	Intermediate Similarity	NPC76879
0.8316	Intermediate Similarity	NPC32830
0.8316	Intermediate Similarity	NPC31985
0.83	Intermediate Similarity	NPC144956
0.83	Intermediate Similarity	NPC154072
0.8298	Intermediate Similarity	NPC90652
0.8283	Intermediate Similarity	NPC474785
0.8283	Intermediate Similarity	NPC18509
0.8283	Intermediate Similarity	NPC474938
0.8283	Intermediate Similarity	NPC108078
0.8283	Intermediate Similarity	NPC190554
0.8265	Intermediate Similarity	NPC280725
0.8265	Intermediate Similarity	NPC88310
0.8265	Intermediate Similarity	NPC472485
0.8235	Intermediate Similarity	NPC222153
0.8235	Intermediate Similarity	NPC312900
0.8235	Intermediate Similarity	NPC117185
0.8229	Intermediate Similarity	NPC126993
0.8211	Intermediate Similarity	NPC44181
0.8211	Intermediate Similarity	NPC470417
0.8208	Intermediate Similarity	NPC207689
0.8191	Intermediate Similarity	NPC6605
0.8191	Intermediate Similarity	NPC473168
0.8191	Intermediate Similarity	NPC201273
0.8182	Intermediate Similarity	NPC471153
0.8182	Intermediate Similarity	NPC192428
0.8173	Intermediate Similarity	NPC477916
0.8172	Intermediate Similarity	NPC474233
0.8172	Intermediate Similarity	NPC59453
0.8172	Intermediate Similarity	NPC474493
0.8172	Intermediate Similarity	NPC474482
0.8172	Intermediate Similarity	NPC475745
0.8172	Intermediate Similarity	NPC221758
0.8163	Intermediate Similarity	NPC8993
0.8163	Intermediate Similarity	NPC103527
0.8163	Intermediate Similarity	NPC292793
0.8155	Intermediate Similarity	NPC201763
0.8152	Intermediate Similarity	NPC48362
0.8144	Intermediate Similarity	NPC86266
0.8144	Intermediate Similarity	NPC131872
0.8144	Intermediate Similarity	NPC212301
0.8144	Intermediate Similarity	NPC110657
0.8144	Intermediate Similarity	NPC475806
0.8137	Intermediate Similarity	NPC271980
0.8137	Intermediate Similarity	NPC193934
0.8125	Intermediate Similarity	NPC122116
0.8125	Intermediate Similarity	NPC77168
0.8125	Intermediate Similarity	NPC326627
0.8125	Intermediate Similarity	NPC310010
0.8125	Intermediate Similarity	NPC186688
0.8125	Intermediate Similarity	NPC84271
0.8125	Intermediate Similarity	NPC102414
0.8119	Intermediate Similarity	NPC474720
0.8119	Intermediate Similarity	NPC83709
0.8105	Intermediate Similarity	NPC142361
0.8105	Intermediate Similarity	NPC241875
0.8105	Intermediate Similarity	NPC475740
0.8105	Intermediate Similarity	NPC469314
0.8105	Intermediate Similarity	NPC136548
0.8105	Intermediate Similarity	NPC153604
0.8105	Intermediate Similarity	NPC58063
0.8105	Intermediate Similarity	NPC469317
0.8105	Intermediate Similarity	NPC474684
0.81	Intermediate Similarity	NPC170978
0.8085	Intermediate Similarity	NPC474218
0.8085	Intermediate Similarity	NPC470574
0.8081	Intermediate Similarity	NPC222845
0.8081	Intermediate Similarity	NPC476245
0.8081	Intermediate Similarity	NPC162001
0.8081	Intermediate Similarity	NPC45324
0.8077	Intermediate Similarity	NPC196528
0.8065	Intermediate Similarity	NPC475726
0.8065	Intermediate Similarity	NPC113978
0.8065	Intermediate Similarity	NPC472743
0.8061	Intermediate Similarity	NPC224060
0.8061	Intermediate Similarity	NPC107674
0.8061	Intermediate Similarity	NPC170220
0.8061	Intermediate Similarity	NPC475255
0.8061	Intermediate Similarity	NPC141497
0.8061	Intermediate Similarity	NPC233118
0.8061	Intermediate Similarity	NPC470375
0.8061	Intermediate Similarity	NPC244356
0.8061	Intermediate Similarity	NPC470376
0.8061	Intermediate Similarity	NPC134826
0.8058	Intermediate Similarity	NPC311612
0.8056	Intermediate Similarity	NPC108721
0.8056	Intermediate Similarity	NPC73300
0.8041	Intermediate Similarity	NPC470378
0.8041	Intermediate Similarity	NPC149761
0.8041	Intermediate Similarity	NPC136801
0.8041	Intermediate Similarity	NPC129913
0.8041	Intermediate Similarity	NPC320026
0.8041	Intermediate Similarity	NPC85173
0.8041	Intermediate Similarity	NPC261994
0.8041	Intermediate Similarity	NPC171441
0.8039	Intermediate Similarity	NPC282524
0.8039	Intermediate Similarity	NPC476897
0.8022	Intermediate Similarity	NPC215843
0.8021	Intermediate Similarity	NPC474719
0.8021	Intermediate Similarity	NPC471722
0.8021	Intermediate Similarity	NPC474677
0.8021	Intermediate Similarity	NPC328539
0.802	Intermediate Similarity	NPC186810
0.802	Intermediate Similarity	NPC114274
0.802	Intermediate Similarity	NPC477854
0.8019	Intermediate Similarity	NPC214644
0.8	Intermediate Similarity	NPC74363
0.8	Intermediate Similarity	NPC474732
0.8	Intermediate Similarity	NPC472738
0.8	Intermediate Similarity	NPC157113
0.8	Intermediate Similarity	NPC94666
0.8	Intermediate Similarity	NPC160056
0.8	Intermediate Similarity	NPC131665
0.8	Intermediate Similarity	NPC474778
0.8	Intermediate Similarity	NPC475862
0.8	Intermediate Similarity	NPC64844
0.8	Intermediate Similarity	NPC89077
0.8	Intermediate Similarity	NPC250757
0.8	Intermediate Similarity	NPC42847
0.8	Intermediate Similarity	NPC83744
0.8	Intermediate Similarity	NPC185
0.8	Intermediate Similarity	NPC20688
0.8	Intermediate Similarity	NPC477853
0.8	Intermediate Similarity	NPC263729
0.8	Intermediate Similarity	NPC255387
0.8	Intermediate Similarity	NPC31564
0.8	Intermediate Similarity	NPC249954
0.8	Intermediate Similarity	NPC62516
0.8	Intermediate Similarity	NPC72133
0.8	Intermediate Similarity	NPC474733
0.8	Intermediate Similarity	NPC301534
0.8	Intermediate Similarity	NPC213412
0.8	Intermediate Similarity	NPC94755
0.8	Intermediate Similarity	NPC78473
0.8	Intermediate Similarity	NPC145879
0.7981	Intermediate Similarity	NPC471293
0.7981	Intermediate Similarity	NPC209502
0.7981	Intermediate Similarity	NPC204833
0.7981	Intermediate Similarity	NPC137657
0.798	Intermediate Similarity	NPC159365
0.798	Intermediate Similarity	NPC104371
0.798	Intermediate Similarity	NPC111524
0.798	Intermediate Similarity	NPC91772
0.798	Intermediate Similarity	NPC469406
0.798	Intermediate Similarity	NPC473172
0.798	Intermediate Similarity	NPC153775
0.798	Intermediate Similarity	NPC29247
0.798	Intermediate Similarity	NPC80365
0.798	Intermediate Similarity	NPC261333
0.798	Intermediate Similarity	NPC289539
0.798	Intermediate Similarity	NPC129004
0.798	Intermediate Similarity	NPC101233
0.798	Intermediate Similarity	NPC215271
0.798	Intermediate Similarity	NPC471207

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 NPC191565 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	1305
0.2-0.3	3903
0.3-0.4	2501
0.4-0.5	772
0.5-0.6	186
0.6-0.7	141
0.7-0.8	150
0.8-0.85	26
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.83	Intermediate Similarity	NPD5286	Approved
0.83	Intermediate Similarity	NPD4696	Approved
0.83	Intermediate Similarity	NPD5285	Approved
0.8283	Intermediate Similarity	NPD4755	Approved
0.8191	Intermediate Similarity	NPD3618	Phase 1
0.8182	Intermediate Similarity	NPD5221	Approved
0.8182	Intermediate Similarity	NPD4697	Phase 3
0.8182	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD5222	Approved
0.8172	Intermediate Similarity	NPD4786	Approved
0.8144	Intermediate Similarity	NPD6079	Approved
0.8137	Intermediate Similarity	NPD5211	Phase 2
0.8137	Intermediate Similarity	NPD5225	Approved
0.8137	Intermediate Similarity	NPD5224	Approved
0.8137	Intermediate Similarity	NPD5226	Approved
0.8137	Intermediate Similarity	NPD4633	Approved
0.8125	Intermediate Similarity	NPD5328	Approved
0.8125	Intermediate Similarity	NPD4753	Phase 2
0.8119	Intermediate Similarity	NPD4700	Approved
0.81	Intermediate Similarity	NPD5173	Approved
0.8081	Intermediate Similarity	NPD5210	Approved
0.8081	Intermediate Similarity	NPD4629	Approved
0.8058	Intermediate Similarity	NPD5175	Approved
0.8058	Intermediate Similarity	NPD5174	Approved
0.8039	Intermediate Similarity	NPD5223	Approved
0.8	Intermediate Similarity	NPD5279	Phase 3
0.7981	Intermediate Similarity	NPD5141	Approved
0.7957	Intermediate Similarity	NPD3667	Approved
0.7944	Intermediate Similarity	NPD4634	Approved
0.7935	Intermediate Similarity	NPD7525	Registered
0.7925	Intermediate Similarity	NPD6899	Approved
0.7925	Intermediate Similarity	NPD6881	Approved
0.7905	Intermediate Similarity	NPD5739	Approved
0.7905	Intermediate Similarity	NPD6675	Approved
0.7905	Intermediate Similarity	NPD6402	Approved
0.7905	Intermediate Similarity	NPD7128	Approved
0.7879	Intermediate Similarity	NPD4202	Approved
0.787	Intermediate Similarity	NPD6650	Approved
0.787	Intermediate Similarity	NPD6649	Approved
0.785	Intermediate Similarity	NPD6373	Approved
0.785	Intermediate Similarity	NPD6372	Approved
0.783	Intermediate Similarity	NPD5697	Approved
0.7778	Intermediate Similarity	NPD7102	Approved
0.7778	Intermediate Similarity	NPD6883	Approved
0.7778	Intermediate Similarity	NPD7290	Approved
0.7757	Intermediate Similarity	NPD4730	Approved
0.7757	Intermediate Similarity	NPD4729	Approved
0.7757	Intermediate Similarity	NPD7320	Approved
0.7745	Intermediate Similarity	NPD6084	Phase 2
0.7745	Intermediate Similarity	NPD6083	Phase 2
0.7736	Intermediate Similarity	NPD4768	Approved
0.7736	Intermediate Similarity	NPD4767	Approved
0.7714	Intermediate Similarity	NPD4754	Approved
0.7708	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD5329	Approved
0.7706	Intermediate Similarity	NPD8130	Phase 1
0.7706	Intermediate Similarity	NPD6617	Approved
0.7706	Intermediate Similarity	NPD6847	Approved
0.7706	Intermediate Similarity	NPD6869	Approved
0.77	Intermediate Similarity	NPD6399	Phase 3
0.7685	Intermediate Similarity	NPD6014	Approved
0.7685	Intermediate Similarity	NPD6012	Approved
0.7685	Intermediate Similarity	NPD6013	Approved
0.7664	Intermediate Similarity	NPD5701	Approved
0.7636	Intermediate Similarity	NPD6882	Approved
0.7636	Intermediate Similarity	NPD8297	Approved
0.7629	Intermediate Similarity	NPD4694	Approved
0.7629	Intermediate Similarity	NPD5280	Approved
0.7615	Intermediate Similarity	NPD5247	Approved
0.7615	Intermediate Similarity	NPD5248	Approved
0.7615	Intermediate Similarity	NPD5251	Approved
0.7615	Intermediate Similarity	NPD5250	Approved
0.7615	Intermediate Similarity	NPD5249	Phase 3
0.7609	Intermediate Similarity	NPD6932	Approved
0.7604	Intermediate Similarity	NPD3665	Phase 1
0.7604	Intermediate Similarity	NPD3666	Approved
0.7604	Intermediate Similarity	NPD3133	Approved
0.7604	Intermediate Similarity	NPD4197	Approved
0.76	Intermediate Similarity	NPD7515	Phase 2
0.7593	Intermediate Similarity	NPD5128	Approved
0.7593	Intermediate Similarity	NPD6011	Approved
0.7568	Intermediate Similarity	NPD4632	Approved
0.7553	Intermediate Similarity	NPD6930	Phase 2
0.7553	Intermediate Similarity	NPD6931	Approved
0.7545	Intermediate Similarity	NPD5216	Approved
0.7545	Intermediate Similarity	NPD5217	Approved
0.7545	Intermediate Similarity	NPD5215	Approved
0.75	Intermediate Similarity	NPD5696	Approved
0.75	Intermediate Similarity	NPD6695	Phase 3
0.75	Intermediate Similarity	NPD7638	Approved
0.75	Intermediate Similarity	NPD4788	Approved
0.7478	Intermediate Similarity	NPD6054	Approved
0.7455	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD5169	Approved
0.7455	Intermediate Similarity	NPD5135	Approved
0.7449	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD5690	Phase 2
0.7447	Intermediate Similarity	NPD6929	Approved
0.7431	Intermediate Similarity	NPD5168	Approved
0.7429	Intermediate Similarity	NPD7639	Approved
0.7429	Intermediate Similarity	NPD7640	Approved
0.7426	Intermediate Similarity	NPD8035	Phase 2
0.7426	Intermediate Similarity	NPD5284	Approved
0.7426	Intermediate Similarity	NPD5281	Approved
0.7426	Intermediate Similarity	NPD8034	Phase 2
0.7423	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD3668	Phase 3
0.7396	Intermediate Similarity	NPD4223	Phase 3
0.7396	Intermediate Similarity	NPD4221	Approved
0.7387	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD5127	Approved
0.7379	Intermediate Similarity	NPD5695	Phase 3
0.7368	Intermediate Similarity	NPD6009	Approved
0.7368	Intermediate Similarity	NPD7514	Phase 3
0.735	Intermediate Similarity	NPD6370	Approved
0.734	Intermediate Similarity	NPD6697	Approved
0.734	Intermediate Similarity	NPD7145	Approved
0.734	Intermediate Similarity	NPD6115	Approved
0.734	Intermediate Similarity	NPD6114	Approved
0.734	Intermediate Similarity	NPD6118	Approved
0.7328	Intermediate Similarity	NPD6059	Approved
0.7328	Intermediate Similarity	NPD6319	Approved
0.73	Intermediate Similarity	NPD6672	Approved
0.73	Intermediate Similarity	NPD5737	Approved
0.7283	Intermediate Similarity	NPD6924	Approved
0.7283	Intermediate Similarity	NPD6926	Approved
0.7282	Intermediate Similarity	NPD7748	Approved
0.7265	Intermediate Similarity	NPD6016	Approved
0.7265	Intermediate Similarity	NPD6015	Approved
0.7263	Intermediate Similarity	NPD6683	Phase 2
0.7255	Intermediate Similarity	NPD7637	Suspended
0.7253	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7100	Approved
0.7241	Intermediate Similarity	NPD7101	Approved
0.7238	Intermediate Similarity	NPD7902	Approved
0.7234	Intermediate Similarity	NPD6925	Approved
0.7234	Intermediate Similarity	NPD5776	Phase 2
0.7227	Intermediate Similarity	NPD7492	Approved
0.7217	Intermediate Similarity	NPD7115	Discovery
0.7204	Intermediate Similarity	NPD3703	Phase 2
0.7204	Intermediate Similarity	NPD7339	Approved
0.7204	Intermediate Similarity	NPD6942	Approved
0.7203	Intermediate Similarity	NPD5988	Approved
0.72	Intermediate Similarity	NPD7750	Discontinued
0.72	Intermediate Similarity	NPD7524	Approved
0.7193	Intermediate Similarity	NPD5167	Approved
0.719	Intermediate Similarity	NPD7736	Approved
0.7188	Intermediate Similarity	NPD7332	Phase 2
0.7172	Intermediate Similarity	NPD6893	Approved
0.7167	Intermediate Similarity	NPD6616	Approved
0.7158	Intermediate Similarity	NPD3617	Approved
0.7155	Intermediate Similarity	NPD6335	Approved
0.7143	Intermediate Similarity	NPD4789	Approved
0.7143	Intermediate Similarity	NPD7604	Phase 2
0.713	Intermediate Similarity	NPD6868	Approved
0.713	Intermediate Similarity	NPD6274	Approved
0.7128	Intermediate Similarity	NPD6117	Approved
0.7128	Intermediate Similarity	NPD6933	Approved
0.7119	Intermediate Similarity	NPD5983	Phase 2
0.7117	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6902	Approved
0.7107	Intermediate Similarity	NPD7078	Approved
0.71	Intermediate Similarity	NPD6098	Approved
0.71	Intermediate Similarity	NPD4693	Phase 3
0.71	Intermediate Similarity	NPD4690	Approved
0.71	Intermediate Similarity	NPD5205	Approved
0.71	Intermediate Similarity	NPD4689	Approved
0.71	Intermediate Similarity	NPD4688	Approved
0.71	Intermediate Similarity	NPD4138	Approved
0.7091	Intermediate Similarity	NPD6008	Approved
0.7087	Intermediate Similarity	NPD5694	Approved
0.7087	Intermediate Similarity	NPD6050	Approved
0.7083	Intermediate Similarity	NPD7645	Phase 2
0.7069	Intermediate Similarity	NPD6317	Approved
0.7065	Intermediate Similarity	NPD7152	Approved
0.7065	Intermediate Similarity	NPD7150	Approved
0.7065	Intermediate Similarity	NPD7151	Approved
0.7059	Intermediate Similarity	NPD6904	Approved
0.7059	Intermediate Similarity	NPD6673	Approved
0.7059	Intermediate Similarity	NPD6080	Approved
0.7059	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD6116	Phase 1
0.7048	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6412	Phase 2
0.7025	Intermediate Similarity	NPD6336	Discontinued
0.7019	Intermediate Similarity	NPD5133	Approved
0.701	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD4695	Discontinued
0.7009	Intermediate Similarity	NPD6314	Approved
0.7009	Intermediate Similarity	NPD6313	Approved
0.699	Remote Similarity	NPD5692	Phase 3
0.6975	Remote Similarity	NPD6909	Approved
0.6975	Remote Similarity	NPD6908	Approved
0.6975	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD5091	Approved
0.6967	Remote Similarity	NPD8293	Discontinued
0.6961	Remote Similarity	NPD7513	Clinical (unspecified phase)

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