NPASS Compound

Structure

NPC170978 OpenBabel07101718242D 34 37 0 0 1 0 0 0 0 0999 V2000 -1.7660 4.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4570 3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3840 6.3564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4593 2.4135 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 -3.4133 3.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1042 2.9680 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 2.5981 0.5000 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 -2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0313 5.8212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7441 4.6622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1261 2.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0531 5.6132 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8171 1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 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 2 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 2.5981 -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 2 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 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3403 6.7722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1261 -0.7601 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 2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 2 0 0 0 0 6 7 1 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 10 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 9 22 1 0 0 0 0 10 27 1 0 0 0 0 11 26 1 0 0 0 0 12 18 1 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 13 28 1 0 0 0 0 14 17 1 0 0 0 0 14 29 1 0 0 0 0 15 17 1 0 0 0 0 16 2 1 1 0 0 0 16 18 1 0 0 0 0 17 3 1 1 0 0 0 18 26 1 6 0 0 0 19 24 1 0 0 0 0 19 30 1 6 0 0 0 20 25 1 0 0 0 0 20 31 2 0 0 0 0 21 23 1 0 0 0 0 21 32 1 1 0 0 0 22 27 1 6 0 0 0 22 28 1 0 0 0 0 23 24 1 0 0 0 0 23 27 1 6 0 0 0 24 33 1 6 0 0 0 25 26 1 6 0 0 0 25 28 1 0 0 0 0 26 4 1 6 0 0 0 27 5 1 6 0 0 0 28 34 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	478.33
Volume:	506.087
LogP:	2.735
LogD:	3.006
LogS:	-3.495
# Rotatable Bonds:	6
TPSA:	118.22
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.375
Synthetic Accessibility Score:	5.367
Fsp3:	0.893
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:	-4.939
MDCK Permeability:	1.3809068150294479e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.968
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.638
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.271
Plasma Protein Binding (PPB):	68.6638412475586%
Volume Distribution (VD):	0.544
Pgp-substrate:	23.634689331054688%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.766
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.614
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.091
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.126
CYP3A4-inhibitor:	0.289
CYP3A4-substrate:	0.112

ADMET: Excretion

Clearance (CL):	6.259
Half-life (T1/2):	0.428

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.433
Drug-inuced Liver Injury (DILI):	0.1
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.58
Maximum Recommended Daily Dose:	0.654
Skin Sensitization:	0.165
Carcinogencity:	0.085
Eye Corrosion:	0.005
Eye Irritation:	0.014
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC170978

Natural Product ID:	NPC170978
*Common Name:**	Certonardosterol Q1
IUPAC Name:	(3S,4R,5S,6S,8S,9R,10S,13R,14R,17R)-3,4,6,8-tetrahydroxy-17-[(2R,6S)-7-hydroxy-6-methyl-5-methylideneheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,9,11,12,14,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-15-one
Synonyms:	Certonardosterol Q1
Standard InCHIKey:	MOTJMTZWHGETHI-OJLLBEGPSA-N
Standard InCHI:	InChI=1S/C28H46O6/c1-15(17(3)14-29)6-7-16(2)18-12-20(31)25-26(18,4)11-9-22-27(5)10-8-19(30)24(33)23(27)21(32)13-28(22,25)34/h16-19,21-25,29-30,32-34H,1,6-14H2,2-5H3/t16-,17-,18-,19+,21+,22-,23+,24+,25-,26-,27-,28+/m1/s1
SMILES:	C=C(CC[C@@H](C)[C@H]1CC(=O)[C@@H]2[C@]1(C)CC[C@@H]1[C@@]3(C)CC[C@@H]([C@@H]([C@@H]3[C@H](C[C@@]21O)O)O)O)[C@H](C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463167
PubChem CID:	21589760
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0001110] Tetrahydroxy bile acids, alcohols 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
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12444692]
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662097]
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104487]
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497935]

☑ 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
ED50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	11.6	ug ml-1	PMID[470803]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	4.95	ug ml-1	PMID[470803]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	5.57	ug ml-1	PMID[470803]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	10.9	ug ml-1	PMID[470803]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	12.0	ug ml-1	PMID[470803]

☑ 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 NPC170978 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	226
0.1-0.2	1762
0.2-0.3	5807
0.3-0.4	11131
0.4-0.5	10662
0.5-0.6	5471
0.6-0.7	5306
0.7-0.8	2037
0.8-0.85	218
0.85-0.9	73
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9158	High Similarity	NPC291785
0.9158	High Similarity	NPC127408
0.9	High Similarity	NPC263802
0.883	High Similarity	NPC91772
0.883	High Similarity	NPC104371
0.883	High Similarity	NPC29247
0.883	High Similarity	NPC289539
0.883	High Similarity	NPC101233
0.883	High Similarity	NPC292374
0.883	High Similarity	NPC215271
0.883	High Similarity	NPC129004
0.883	High Similarity	NPC261333
0.883	High Similarity	NPC111524
0.883	High Similarity	NPC153775
0.875	High Similarity	NPC111187
0.875	High Similarity	NPC190080
0.8737	High Similarity	NPC41070
0.8737	High Similarity	NPC138245
0.8737	High Similarity	NPC84018
0.8737	High Similarity	NPC288906
0.8737	High Similarity	NPC231060
0.8737	High Similarity	NPC263135
0.8723	High Similarity	NPC144739
0.8723	High Similarity	NPC181594
0.8713	High Similarity	NPC218123
0.8713	High Similarity	NPC273155
0.8713	High Similarity	NPC112895
0.8713	High Similarity	NPC231278
0.871	High Similarity	NPC46758
0.871	High Similarity	NPC80401
0.8667	High Similarity	NPC50438
0.8646	High Similarity	NPC264979
0.8646	High Similarity	NPC135548
0.8632	High Similarity	NPC302008
0.8632	High Similarity	NPC191094
0.8632	High Similarity	NPC277399
0.8617	High Similarity	NPC476168
0.8617	High Similarity	NPC299185
0.8614	High Similarity	NPC166993
0.8587	High Similarity	NPC57469
0.8587	High Similarity	NPC259009
0.8571	High Similarity	NPC470388
0.8556	High Similarity	NPC85095
0.8556	High Similarity	NPC216420
0.8556	High Similarity	NPC211135
0.8526	High Similarity	NPC291373
0.8526	High Similarity	NPC59170
0.8526	High Similarity	NPC472496
0.8515	High Similarity	NPC200957
0.8515	High Similarity	NPC138908
0.8511	High Similarity	NPC180849
0.8511	High Similarity	NPC149761
0.8511	High Similarity	NPC470378
0.8511	High Similarity	NPC261994
0.85	High Similarity	NPC277074
0.85	High Similarity	NPC209298
0.85	High Similarity	NPC191892
0.8485	Intermediate Similarity	NPC46848
0.8485	Intermediate Similarity	NPC71706
0.8478	Intermediate Similarity	NPC121981
0.8462	Intermediate Similarity	NPC94650
0.8454	Intermediate Similarity	NPC234564
0.8454	Intermediate Similarity	NPC140242
0.8438	Intermediate Similarity	NPC280804
0.8421	Intermediate Similarity	NPC211403
0.8421	Intermediate Similarity	NPC198242
0.8416	Intermediate Similarity	NPC301787
0.84	Intermediate Similarity	NPC304832
0.84	Intermediate Similarity	NPC275990
0.84	Intermediate Similarity	NPC76866
0.84	Intermediate Similarity	NPC246736
0.84	Intermediate Similarity	NPC88203
0.84	Intermediate Similarity	NPC214946
0.84	Intermediate Similarity	NPC148628
0.84	Intermediate Similarity	NPC286519
0.8387	Intermediate Similarity	NPC153604
0.8387	Intermediate Similarity	NPC174619
0.8384	Intermediate Similarity	NPC94906
0.8384	Intermediate Similarity	NPC180733
0.8384	Intermediate Similarity	NPC156324
0.8384	Intermediate Similarity	NPC55503
0.8384	Intermediate Similarity	NPC41971
0.8384	Intermediate Similarity	NPC37047
0.8384	Intermediate Similarity	NPC110149
0.837	Intermediate Similarity	NPC471034
0.837	Intermediate Similarity	NPC190704
0.8367	Intermediate Similarity	NPC253586
0.8367	Intermediate Similarity	NPC190554
0.8351	Intermediate Similarity	NPC29112
0.8351	Intermediate Similarity	NPC142352
0.8351	Intermediate Similarity	NPC266431
0.8351	Intermediate Similarity	NPC200702
0.835	Intermediate Similarity	NPC55973
0.8333	Intermediate Similarity	NPC166607
0.8333	Intermediate Similarity	NPC59350
0.8333	Intermediate Similarity	NPC37600
0.8333	Intermediate Similarity	NPC224060
0.8333	Intermediate Similarity	NPC244356
0.8333	Intermediate Similarity	NPC222833
0.8317	Intermediate Similarity	NPC117185
0.8317	Intermediate Similarity	NPC87927
0.8317	Intermediate Similarity	NPC122811
0.8317	Intermediate Similarity	NPC312900
0.8316	Intermediate Similarity	NPC136801
0.8316	Intermediate Similarity	NPC100313
0.83	Intermediate Similarity	NPC163963
0.83	Intermediate Similarity	NPC471790
0.83	Intermediate Similarity	NPC289148
0.83	Intermediate Similarity	NPC52899
0.8298	Intermediate Similarity	NPC193360
0.8283	Intermediate Similarity	NPC38296
0.8283	Intermediate Similarity	NPC472028
0.8283	Intermediate Similarity	NPC28864
0.8283	Intermediate Similarity	NPC38471
0.8283	Intermediate Similarity	NPC471038
0.8283	Intermediate Similarity	NPC98837
0.8283	Intermediate Similarity	NPC474793
0.8283	Intermediate Similarity	NPC20479
0.8283	Intermediate Similarity	NPC162459
0.8265	Intermediate Similarity	NPC329910
0.8261	Intermediate Similarity	NPC255882
0.8252	Intermediate Similarity	NPC475060
0.8252	Intermediate Similarity	NPC477916
0.8252	Intermediate Similarity	NPC471461
0.8252	Intermediate Similarity	NPC67745
0.8252	Intermediate Similarity	NPC220229
0.8252	Intermediate Similarity	NPC165873
0.8252	Intermediate Similarity	NPC83744
0.8247	Intermediate Similarity	NPC470385
0.8247	Intermediate Similarity	NPC470386
0.8247	Intermediate Similarity	NPC64006
0.8242	Intermediate Similarity	NPC110780
0.8235	Intermediate Similarity	NPC475036
0.8235	Intermediate Similarity	NPC160843
0.8229	Intermediate Similarity	NPC219516
0.8229	Intermediate Similarity	NPC278106
0.8229	Intermediate Similarity	NPC155304
0.8222	Intermediate Similarity	NPC164999
0.8218	Intermediate Similarity	NPC124544
0.8218	Intermediate Similarity	NPC193934
0.8218	Intermediate Similarity	NPC271980
0.8211	Intermediate Similarity	NPC57954
0.8211	Intermediate Similarity	NPC213832
0.8211	Intermediate Similarity	NPC220498
0.8211	Intermediate Similarity	NPC24705
0.8211	Intermediate Similarity	NPC32830
0.8211	Intermediate Similarity	NPC56962
0.8208	Intermediate Similarity	NPC471245
0.82	Intermediate Similarity	NPC477655
0.82	Intermediate Similarity	NPC108371
0.82	Intermediate Similarity	NPC15390
0.82	Intermediate Similarity	NPC293866
0.82	Intermediate Similarity	NPC287676
0.8191	Intermediate Similarity	NPC469314
0.8191	Intermediate Similarity	NPC4643
0.8191	Intermediate Similarity	NPC469317
0.8191	Intermediate Similarity	NPC165895
0.8191	Intermediate Similarity	NPC241875
0.819	Intermediate Similarity	NPC473324
0.819	Intermediate Similarity	NPC471093
0.8182	Intermediate Similarity	NPC10864
0.8173	Intermediate Similarity	NPC89860
0.8173	Intermediate Similarity	NPC217201
0.8173	Intermediate Similarity	NPC329417
0.8173	Intermediate Similarity	NPC189663
0.8173	Intermediate Similarity	NPC63841
0.8173	Intermediate Similarity	NPC9013
0.8163	Intermediate Similarity	NPC470232
0.8163	Intermediate Similarity	NPC473170
0.8163	Intermediate Similarity	NPC470229
0.8163	Intermediate Similarity	NPC472485
0.8163	Intermediate Similarity	NPC98639
0.8155	Intermediate Similarity	NPC307660
0.8155	Intermediate Similarity	NPC260268
0.8155	Intermediate Similarity	NPC150531
0.8155	Intermediate Similarity	NPC296945
0.8155	Intermediate Similarity	NPC48733
0.8155	Intermediate Similarity	NPC50692
0.8155	Intermediate Similarity	NPC476027
0.8155	Intermediate Similarity	NPC214264
0.8155	Intermediate Similarity	NPC295366
0.8155	Intermediate Similarity	NPC323834
0.8155	Intermediate Similarity	NPC470587
0.8155	Intermediate Similarity	NPC149047
0.8155	Intermediate Similarity	NPC171137
0.8155	Intermediate Similarity	NPC152695
0.8155	Intermediate Similarity	NPC202167
0.8155	Intermediate Similarity	NPC130511
0.8155	Intermediate Similarity	NPC85829
0.8155	Intermediate Similarity	NPC319077
0.8155	Intermediate Similarity	NPC302607
0.8155	Intermediate Similarity	NPC4115
0.8155	Intermediate Similarity	NPC97202
0.8155	Intermediate Similarity	NPC49958
0.8152	Intermediate Similarity	NPC475726
0.8152	Intermediate Similarity	NPC291320
0.8152	Intermediate Similarity	NPC232023
0.8152	Intermediate Similarity	NPC471036
0.8152	Intermediate Similarity	NPC472743
0.8131	Intermediate Similarity	NPC471248

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 NPC170978 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	2191
0.2-0.3	4090
0.3-0.4	1729
0.4-0.5	487
0.5-0.6	178
0.6-0.7	169
0.7-0.8	99
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8019	Intermediate Similarity	NPD4634	Approved
0.7835	Intermediate Similarity	NPD5328	Approved
0.7822	Intermediate Similarity	NPD4755	Approved
0.7789	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD4786	Approved
0.7677	Intermediate Similarity	NPD6079	Approved
0.767	Intermediate Similarity	NPD4696	Approved
0.767	Intermediate Similarity	NPD5285	Approved
0.767	Intermediate Similarity	NPD4700	Approved
0.767	Intermediate Similarity	NPD5286	Approved
0.7667	Intermediate Similarity	NPD3703	Phase 2
0.7664	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD4788	Approved
0.7524	Intermediate Similarity	NPD5224	Approved
0.7524	Intermediate Similarity	NPD5211	Phase 2
0.7524	Intermediate Similarity	NPD5225	Approved
0.7524	Intermediate Similarity	NPD5226	Approved
0.7524	Intermediate Similarity	NPD4633	Approved
0.75	Intermediate Similarity	NPD8035	Phase 2
0.75	Intermediate Similarity	NPD8034	Phase 2
0.7477	Intermediate Similarity	NPD5739	Approved
0.7477	Intermediate Similarity	NPD6675	Approved
0.7477	Intermediate Similarity	NPD7128	Approved
0.7477	Intermediate Similarity	NPD6402	Approved
0.7474	Intermediate Similarity	NPD3667	Approved
0.7453	Intermediate Similarity	NPD5175	Approved
0.7453	Intermediate Similarity	NPD5174	Approved
0.7447	Intermediate Similarity	NPD7525	Registered
0.7429	Intermediate Similarity	NPD5223	Approved
0.7426	Intermediate Similarity	NPD4202	Approved
0.7419	Intermediate Similarity	NPD6114	Approved
0.7419	Intermediate Similarity	NPD6697	Approved
0.7419	Intermediate Similarity	NPD6115	Approved
0.7419	Intermediate Similarity	NPD6118	Approved
0.7391	Intermediate Similarity	NPD6319	Approved
0.7391	Intermediate Similarity	NPD6054	Approved
0.7391	Intermediate Similarity	NPD6059	Approved
0.7383	Intermediate Similarity	NPD5141	Approved
0.7379	Intermediate Similarity	NPD5221	Approved
0.7379	Intermediate Similarity	NPD5222	Approved
0.7379	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD4697	Phase 3
0.7347	Intermediate Similarity	NPD3618	Phase 1
0.7339	Intermediate Similarity	NPD6881	Approved
0.7339	Intermediate Similarity	NPD6899	Approved
0.7339	Intermediate Similarity	NPD7320	Approved
0.7333	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD4632	Approved
0.7315	Intermediate Similarity	NPD4768	Approved
0.7315	Intermediate Similarity	NPD4767	Approved
0.7312	Intermediate Similarity	NPD6116	Phase 1
0.7308	Intermediate Similarity	NPD5173	Approved
0.729	Intermediate Similarity	NPD4754	Approved
0.7273	Intermediate Similarity	NPD6373	Approved
0.7273	Intermediate Similarity	NPD6372	Approved
0.7265	Intermediate Similarity	NPD6370	Approved
0.7255	Intermediate Similarity	NPD6399	Phase 3
0.7248	Intermediate Similarity	NPD5701	Approved
0.7248	Intermediate Similarity	NPD5697	Approved
0.7232	Intermediate Similarity	NPD8297	Approved
0.7207	Intermediate Similarity	NPD7290	Approved
0.7207	Intermediate Similarity	NPD6883	Approved
0.7207	Intermediate Similarity	NPD7102	Approved
0.7204	Intermediate Similarity	NPD6117	Approved
0.719	Intermediate Similarity	NPD7319	Approved
0.7182	Intermediate Similarity	NPD4729	Approved
0.7182	Intermediate Similarity	NPD4730	Approved
0.7182	Intermediate Similarity	NPD5128	Approved
0.7179	Intermediate Similarity	NPD6016	Approved
0.7179	Intermediate Similarity	NPD6015	Approved
0.7143	Intermediate Similarity	NPD8130	Phase 1
0.7143	Intermediate Similarity	NPD6869	Approved
0.7143	Intermediate Similarity	NPD6617	Approved
0.7143	Intermediate Similarity	NPD7492	Approved
0.7143	Intermediate Similarity	NPD6847	Approved
0.7143	Intermediate Similarity	NPD6649	Approved
0.7143	Intermediate Similarity	NPD6650	Approved
0.713	Intermediate Similarity	NPD7115	Discovery
0.7129	Intermediate Similarity	NPD4753	Phase 2
0.7119	Intermediate Similarity	NPD5988	Approved
0.7117	Intermediate Similarity	NPD6013	Approved
0.7117	Intermediate Similarity	NPD6014	Approved
0.7117	Intermediate Similarity	NPD6012	Approved
0.7111	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7736	Approved
0.7083	Intermediate Similarity	NPD6616	Approved
0.708	Intermediate Similarity	NPD6882	Approved
0.7054	Intermediate Similarity	NPD5249	Phase 3
0.7054	Intermediate Similarity	NPD5248	Approved
0.7054	Intermediate Similarity	NPD5250	Approved
0.7054	Intermediate Similarity	NPD5251	Approved
0.7054	Intermediate Similarity	NPD5247	Approved
0.7027	Intermediate Similarity	NPD6011	Approved
0.7025	Intermediate Similarity	NPD7078	Approved
0.7025	Intermediate Similarity	NPD8293	Discontinued
0.7018	Intermediate Similarity	NPD8133	Approved
0.7	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5360	Phase 3
0.7	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6008	Approved
0.6991	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD5215	Approved
0.6991	Remote Similarity	NPD5216	Approved
0.6991	Remote Similarity	NPD5217	Approved
0.699	Remote Similarity	NPD7515	Phase 2
0.6989	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD6009	Approved
0.697	Remote Similarity	NPD3668	Phase 3
0.697	Remote Similarity	NPD3666	Approved
0.697	Remote Similarity	NPD3133	Approved
0.697	Remote Similarity	NPD3665	Phase 1
0.6942	Remote Similarity	NPD7507	Approved
0.6937	Remote Similarity	NPD6412	Phase 2
0.6931	Remote Similarity	NPD7524	Approved
0.6916	Remote Similarity	NPD7638	Approved
0.6903	Remote Similarity	NPD5169	Approved
0.6903	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD5135	Approved
0.6891	Remote Similarity	NPD6921	Approved
0.6852	Remote Similarity	NPD7640	Approved
0.6852	Remote Similarity	NPD7639	Approved
0.6848	Remote Similarity	NPD4789	Approved
0.6848	Remote Similarity	NPD4244	Approved
0.6848	Remote Similarity	NPD4245	Approved
0.6842	Remote Similarity	NPD5127	Approved
0.6838	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6033	Approved
0.6822	Remote Similarity	NPD6083	Phase 2
0.6822	Remote Similarity	NPD6084	Phase 2
0.6814	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5210	Approved
0.6792	Remote Similarity	NPD4629	Approved
0.6777	Remote Similarity	NPD7604	Phase 2
0.6777	Remote Similarity	NPD8328	Phase 3
0.6768	Remote Similarity	NPD4221	Approved
0.6768	Remote Similarity	NPD4223	Phase 3
0.6757	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6274	Approved
0.675	Remote Similarity	NPD5983	Phase 2
0.6739	Remote Similarity	NPD3698	Phase 2
0.6737	Remote Similarity	NPD6942	Approved
0.6737	Remote Similarity	NPD7339	Approved
0.6735	Remote Similarity	NPD6930	Phase 2
0.6735	Remote Similarity	NPD6931	Approved
0.6733	Remote Similarity	NPD5329	Approved
0.6726	Remote Similarity	NPD5168	Approved
0.6723	Remote Similarity	NPD7100	Approved
0.6723	Remote Similarity	NPD4522	Approved
0.6723	Remote Similarity	NPD7101	Approved
0.67	Remote Similarity	NPD6695	Phase 3
0.6698	Remote Similarity	NPD7748	Approved
0.6667	Remote Similarity	NPD5167	Approved
0.6667	Remote Similarity	NPD5279	Phase 3
0.6667	Remote Similarity	NPD6933	Approved
0.6667	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD6411	Approved
0.6667	Remote Similarity	NPD7637	Suspended
0.6667	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6335	Approved
0.6634	Remote Similarity	NPD4197	Approved
0.6633	Remote Similarity	NPD6929	Approved
0.6612	Remote Similarity	NPD6909	Approved
0.6612	Remote Similarity	NPD6908	Approved
0.6598	Remote Similarity	NPD6932	Approved
0.6596	Remote Similarity	NPD4758	Discontinued
0.6583	Remote Similarity	NPD7516	Approved
0.6555	Remote Similarity	NPD6317	Approved
0.6531	Remote Similarity	NPD5364	Discontinued
0.6531	Remote Similarity	NPD3671	Phase 1
0.6505	Remote Similarity	NPD4690	Approved
0.6505	Remote Similarity	NPD4688	Approved
0.6505	Remote Similarity	NPD4689	Approved
0.6505	Remote Similarity	NPD5205	Approved
0.6505	Remote Similarity	NPD4138	Approved
0.6505	Remote Similarity	NPD4693	Phase 3
0.65	Remote Similarity	NPD6313	Approved
0.65	Remote Similarity	NPD7328	Approved
0.65	Remote Similarity	NPD7327	Approved
0.65	Remote Similarity	NPD6314	Approved
0.6495	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD1700	Approved
0.6481	Remote Similarity	NPD5695	Phase 3
0.6476	Remote Similarity	NPD6101	Approved
0.6476	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6868	Approved
0.6466	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD6683	Phase 2
0.6465	Remote Similarity	NPD7645	Phase 2
0.6458	Remote Similarity	NPD6926	Approved
0.6458	Remote Similarity	NPD6924	Approved
0.6455	Remote Similarity	NPD4225	Approved
0.6455	Remote Similarity	NPD5696	Approved
0.6449	Remote Similarity	NPD5778	Approved
0.6449	Remote Similarity	NPD5779	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