NPASS Compound

Structure

NPC103051 OpenBabel07101719512D 31 34 0 0 1 0 0 0 0 0999 V2000 -5.7633 -5.8212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1161 -6.3564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1453 -3.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8363 -2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 -2.4135 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 1.7321 1.0000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4980 -4.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1890 -3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.1910 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 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7852 -5.6132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4762 -4.6622 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8581 -2.7601 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 -3.5491 -1.8090 0.0000 C 0 0 2 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 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 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 -0.8660 -0.5000 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 0.0000 -0.0000 0.0000 C 0 0 1 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 -0.0000 -2.0000 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 1 16 1 0 0 0 0 2 16 1 0 0 0 0 7 8 1 0 0 0 0 7 9 2 0 0 0 0 8 22 2 0 0 0 0 9 25 1 0 0 0 0 10 11 1 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 13 1 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 23 1 0 0 0 0 15 24 1 0 0 0 0 15 27 1 0 0 0 0 16 17 1 0 0 0 0 17 3 1 1 0 0 0 18 4 1 1 0 0 0 18 20 1 0 0 0 0 19 14 1 6 0 0 0 19 21 1 0 0 0 0 19 26 1 0 0 0 0 20 27 1 1 0 0 0 21 27 1 1 0 0 0 22 23 1 0 0 0 0 22 28 1 0 0 0 0 23 29 1 1 0 0 0 24 26 1 0 0 0 0 24 30 1 6 0 0 0 25 28 1 0 0 0 0 25 31 2 0 0 0 0 26 28 1 1 0 0 0 27 5 1 1 0 0 0 28 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	428.33
Volume:	477.08
LogP:	5.937
LogD:	5.572
LogS:	-5.614
# Rotatable Bonds:	5
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.585
Synthetic Accessibility Score:	4.879
Fsp3:	0.857
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.76
MDCK Permeability:	1.6872150808922015e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.993
30% Bioavailability (F30%):	0.952

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.778
Plasma Protein Binding (PPB):	94.57196807861328%
Volume Distribution (VD):	0.734
Pgp-substrate:	1.473222017288208%

ADMET: Metabolism

CYP1A2-inhibitor:	0.092
CYP1A2-substrate:	0.583
CYP2C19-inhibitor:	0.393
CYP2C19-substrate:	0.922
CYP2C9-inhibitor:	0.688
CYP2C9-substrate:	0.335
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.111
CYP3A4-inhibitor:	0.875
CYP3A4-substrate:	0.843

ADMET: Excretion

Clearance (CL):	7.433
Half-life (T1/2):	0.364

ADMET: Toxicity

hERG Blockers:	0.431
Human Hepatotoxicity (H-HT):	0.36
Drug-inuced Liver Injury (DILI):	0.57
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.071
Maximum Recommended Daily Dose:	0.096
Skin Sensitization:	0.894
Carcinogencity:	0.374
Eye Corrosion:	0.185
Eye Irritation:	0.193
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC103051

Natural Product ID:	NPC103051
*Common Name:**	Stoloniferone E
IUPAC Name:	(6R,8S,9S,10R,11R,13R,14S,17R)-17-[(2R,5S)-5,6-dimethylheptan-2-yl]-6,11-dihydroxy-10,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-1-one
Synonyms:	stoloniferone E
Standard InCHIKey:	RYMHLKHGLSCOPD-BONNHHEPSA-N
Standard InCHI:	InChI=1S/C28H44O3/c1-16(2)17(3)10-11-18(4)20-12-13-21-19-14-23(29)22-8-7-9-25(31)28(22,6)26(19)24(30)15-27(20,21)5/h7-9,16-21,23-24,26,29-30H,10-15H2,1-6H3/t17-,18+,19-,20+,21-,23+,24+,26+,27+,28+/m0/s1
SMILES:	C[C@H](C(C)C)CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)C[C@@H](O)[C@H]1[C@H]2C[C@H](C2=CC=CC(=O)[C@]12C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491589
PubChem CID:	11122837
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids

*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
NPO3077	Clavularia viridis	Species	Clavulariidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[11720524]
NPO3077	Clavularia viridis	Species	Clavulariidae	Eukaryota	n.a.	Formosan soft corals	n.a.	PMID[12444673]
NPO33409	clavularia violacea	Species	Clavulariidae	Eukaryota	n.a.	Formosan soft corals	n.a.	PMID[12444673]
NPO3077	Clavularia viridis	Species	Clavulariidae	Eukaryota	n.a.	Taiwanese octocoral	n.a.	PMID[15104481]
NPO3077	Clavularia viridis	Species	Clavulariidae	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
ED50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	3.2	10'-4 ug/ml	PMID[504516]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	9.1	10'-3 ug/ml	PMID[504516]
NPT168	Cell Line	P388	Mus musculus	ED50	=	1.2	10'-4 ug/ml	PMID[504516]

☑ 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 NPC103051 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	183
0.1-0.2	991
0.2-0.3	3718
0.3-0.4	8286
0.4-0.5	13821
0.5-0.6	7317
0.6-0.7	5566
0.7-0.8	2490
0.8-0.85	219
0.85-0.9	94
0.9-0.95	11
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9457	High Similarity	NPC271195
0.914	High Similarity	NPC299100
0.913	High Similarity	NPC233116
0.913	High Similarity	NPC475806
0.9121	High Similarity	NPC473999
0.9121	High Similarity	NPC309603
0.9062	High Similarity	NPC154072
0.9043	High Similarity	NPC180950
0.9022	High Similarity	NPC48010
0.898	High Similarity	NPC247957
0.898	High Similarity	NPC249187
0.8947	High Similarity	NPC301534
0.8947	High Similarity	NPC250757
0.8936	High Similarity	NPC8993
0.8936	High Similarity	NPC209662
0.8936	High Similarity	NPC474690
0.8925	High Similarity	NPC272746
0.8925	High Similarity	NPC473998
0.8901	High Similarity	NPC141292
0.8878	High Similarity	NPC293753
0.8854	High Similarity	NPC108078
0.8842	High Similarity	NPC259286
0.883	High Similarity	NPC69454
0.883	High Similarity	NPC474736
0.883	High Similarity	NPC134826
0.8804	High Similarity	NPC310752
0.8804	High Similarity	NPC292491
0.88	High Similarity	NPC257353
0.8791	High Similarity	NPC472986
0.8791	High Similarity	NPC472985
0.875	High Similarity	NPC249954
0.8737	High Similarity	NPC111015
0.8737	High Similarity	NPC245972
0.8737	High Similarity	NPC196485
0.8723	High Similarity	NPC63748
0.871	High Similarity	NPC119416
0.871	High Similarity	NPC186688
0.87	High Similarity	NPC209502
0.87	High Similarity	NPC72255
0.87	High Similarity	NPC204833
0.8696	High Similarity	NPC475740
0.8696	High Similarity	NPC58063
0.8696	High Similarity	NPC136548
0.8687	High Similarity	NPC234892
0.8681	High Similarity	NPC471224
0.8681	High Similarity	NPC470574
0.866	High Similarity	NPC474785
0.866	High Similarity	NPC320306
0.866	High Similarity	NPC99726
0.866	High Similarity	NPC474938
0.8646	High Similarity	NPC297199
0.8632	High Similarity	NPC109305
0.8617	High Similarity	NPC191684
0.8617	High Similarity	NPC126993
0.8617	High Similarity	NPC85173
0.8614	High Similarity	NPC260268
0.8614	High Similarity	NPC49958
0.8614	High Similarity	NPC302607
0.8614	High Similarity	NPC48733
0.8614	High Similarity	NPC171137
0.8614	High Similarity	NPC152695
0.8614	High Similarity	NPC202167
0.8614	High Similarity	NPC85829
0.8614	High Similarity	NPC296945
0.8614	High Similarity	NPC476027
0.8614	High Similarity	NPC97202
0.8614	High Similarity	NPC50692
0.8614	High Similarity	NPC150531
0.8614	High Similarity	NPC214264
0.8614	High Similarity	NPC319077
0.8614	High Similarity	NPC149047
0.8602	High Similarity	NPC193360
0.8602	High Similarity	NPC471722
0.8602	High Similarity	NPC328539
0.8587	High Similarity	NPC474733
0.8587	High Similarity	NPC31564
0.8587	High Similarity	NPC474732
0.8587	High Similarity	NPC145879
0.8587	High Similarity	NPC474778
0.8587	High Similarity	NPC72133
0.8586	High Similarity	NPC282524
0.8571	High Similarity	NPC57079
0.8571	High Similarity	NPC214043
0.8571	High Similarity	NPC108368
0.8571	High Similarity	NPC114274
0.8571	High Similarity	NPC191565
0.8571	High Similarity	NPC85774
0.8557	High Similarity	NPC117133
0.8557	High Similarity	NPC78473
0.8542	High Similarity	NPC471207
0.8542	High Similarity	NPC292793
0.8542	High Similarity	NPC469406
0.8529	High Similarity	NPC475060
0.8529	High Similarity	NPC83744
0.8529	High Similarity	NPC477916
0.8529	High Similarity	NPC220229
0.8526	High Similarity	NPC131872
0.8526	High Similarity	NPC212948
0.8511	High Similarity	NPC275740
0.8511	High Similarity	NPC86319
0.8511	High Similarity	NPC31985
0.8511	High Similarity	NPC1015
0.8511	High Similarity	NPC472973
0.8511	High Similarity	NPC262858
0.8511	High Similarity	NPC472240
0.8511	High Similarity	NPC2983
0.85	High Similarity	NPC477915
0.8495	Intermediate Similarity	NPC93778
0.8495	Intermediate Similarity	NPC287079
0.8485	Intermediate Similarity	NPC327431
0.8485	Intermediate Similarity	NPC266955
0.8478	Intermediate Similarity	NPC474083
0.8469	Intermediate Similarity	NPC253826
0.8469	Intermediate Similarity	NPC122294
0.8454	Intermediate Similarity	NPC127063
0.8447	Intermediate Similarity	NPC217201
0.8447	Intermediate Similarity	NPC329417
0.8438	Intermediate Similarity	NPC475255
0.8438	Intermediate Similarity	NPC214697
0.8438	Intermediate Similarity	NPC472930
0.8431	Intermediate Similarity	NPC166607
0.8421	Intermediate Similarity	NPC69622
0.8416	Intermediate Similarity	NPC311612
0.8404	Intermediate Similarity	NPC471724
0.8404	Intermediate Similarity	NPC143767
0.8404	Intermediate Similarity	NPC474677
0.8404	Intermediate Similarity	NPC131470
0.84	Intermediate Similarity	NPC476240
0.84	Intermediate Similarity	NPC115899
0.84	Intermediate Similarity	NPC472924
0.84	Intermediate Similarity	NPC476223
0.84	Intermediate Similarity	NPC224720
0.8387	Intermediate Similarity	NPC118648
0.8387	Intermediate Similarity	NPC475022
0.8387	Intermediate Similarity	NPC469994
0.8387	Intermediate Similarity	NPC222613
0.8384	Intermediate Similarity	NPC16021
0.8384	Intermediate Similarity	NPC235464
0.8384	Intermediate Similarity	NPC166745
0.8384	Intermediate Similarity	NPC48647
0.8381	Intermediate Similarity	NPC474315
0.837	Intermediate Similarity	NPC59453
0.837	Intermediate Similarity	NPC33913
0.837	Intermediate Similarity	NPC472265
0.837	Intermediate Similarity	NPC473246
0.837	Intermediate Similarity	NPC221758
0.8367	Intermediate Similarity	NPC7124
0.8367	Intermediate Similarity	NPC472941
0.8367	Intermediate Similarity	NPC456
0.8365	Intermediate Similarity	NPC214644
0.8365	Intermediate Similarity	NPC11710
0.8351	Intermediate Similarity	NPC279410
0.8351	Intermediate Similarity	NPC49670
0.8351	Intermediate Similarity	NPC119562
0.835	Intermediate Similarity	NPC472925
0.835	Intermediate Similarity	NPC185
0.8333	Intermediate Similarity	NPC185936
0.8333	Intermediate Similarity	NPC160843
0.8333	Intermediate Similarity	NPC472978
0.8333	Intermediate Similarity	NPC19114
0.8333	Intermediate Similarity	NPC168027
0.8317	Intermediate Similarity	NPC473424
0.8317	Intermediate Similarity	NPC136289
0.8317	Intermediate Similarity	NPC87351
0.8316	Intermediate Similarity	NPC84271
0.8316	Intermediate Similarity	NPC268406
0.8316	Intermediate Similarity	NPC102414
0.8316	Intermediate Similarity	NPC477943
0.8316	Intermediate Similarity	NPC472983
0.8316	Intermediate Similarity	NPC77168
0.8316	Intermediate Similarity	NPC146554
0.8316	Intermediate Similarity	NPC26959
0.8316	Intermediate Similarity	NPC472971
0.8316	Intermediate Similarity	NPC472970
0.83	Intermediate Similarity	NPC144660
0.83	Intermediate Similarity	NPC299971
0.83	Intermediate Similarity	NPC470074
0.83	Intermediate Similarity	NPC287833
0.83	Intermediate Similarity	NPC307954
0.83	Intermediate Similarity	NPC476274
0.8298	Intermediate Similarity	NPC475772
0.8298	Intermediate Similarity	NPC474684
0.8298	Intermediate Similarity	NPC142361
0.8286	Intermediate Similarity	NPC76084
0.8283	Intermediate Similarity	NPC161147
0.8283	Intermediate Similarity	NPC126815
0.828	Intermediate Similarity	NPC469948
0.828	Intermediate Similarity	NPC476426
0.828	Intermediate Similarity	NPC474218
0.8273	Intermediate Similarity	NPC476962
0.8269	Intermediate Similarity	NPC65941
0.8265	Intermediate Similarity	NPC476174
0.8265	Intermediate Similarity	NPC280725
0.8265	Intermediate Similarity	NPC476245
0.8265	Intermediate Similarity	NPC88310
0.8252	Intermediate Similarity	NPC266570
0.8252	Intermediate Similarity	NPC189863
0.8247	Intermediate Similarity	NPC250575
0.8247	Intermediate Similarity	NPC474807
0.8247	Intermediate Similarity	NPC12722

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 NPC103051 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	156
0.1-0.2	1203
0.2-0.3	3557
0.3-0.4	2802
0.4-0.5	900
0.5-0.6	207
0.6-0.7	136
0.7-0.8	159
0.8-0.85	24
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8925	High Similarity	NPD6079	Approved
0.8791	High Similarity	NPD3618	Phase 1
0.871	High Similarity	NPD5328	Approved
0.837	Intermediate Similarity	NPD4786	Approved
0.8367	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8367	Intermediate Similarity	NPD5222	Approved
0.8367	Intermediate Similarity	NPD5221	Approved
0.8317	Intermediate Similarity	NPD5211	Phase 2
0.8283	Intermediate Similarity	NPD5173	Approved
0.8247	Intermediate Similarity	NPD4202	Approved
0.8191	Intermediate Similarity	NPD5279	Phase 3
0.8182	Intermediate Similarity	NPD4697	Phase 3
0.8172	Intermediate Similarity	NPD3666	Approved
0.8172	Intermediate Similarity	NPD3133	Approved
0.8172	Intermediate Similarity	NPD3665	Phase 1
0.8155	Intermediate Similarity	NPD5141	Approved
0.8152	Intermediate Similarity	NPD3667	Approved
0.8119	Intermediate Similarity	NPD5286	Approved
0.8119	Intermediate Similarity	NPD5285	Approved
0.8119	Intermediate Similarity	NPD4696	Approved
0.8039	Intermediate Similarity	NPD5223	Approved
0.7961	Intermediate Similarity	NPD5224	Approved
0.7961	Intermediate Similarity	NPD5226	Approved
0.7961	Intermediate Similarity	NPD5225	Approved
0.7961	Intermediate Similarity	NPD4633	Approved
0.7941	Intermediate Similarity	NPD7639	Approved
0.7941	Intermediate Similarity	NPD7640	Approved
0.7921	Intermediate Similarity	NPD4755	Approved
0.79	Intermediate Similarity	NPD4629	Approved
0.79	Intermediate Similarity	NPD5210	Approved
0.7885	Intermediate Similarity	NPD5174	Approved
0.7885	Intermediate Similarity	NPD5175	Approved
0.7843	Intermediate Similarity	NPD7638	Approved
0.7838	Intermediate Similarity	NPD7115	Discovery
0.7812	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4634	Approved
0.7778	Intermediate Similarity	NPD7515	Phase 2
0.7767	Intermediate Similarity	NPD4700	Approved
0.7766	Intermediate Similarity	NPD4221	Approved
0.7766	Intermediate Similarity	NPD4223	Phase 3
0.7757	Intermediate Similarity	NPD6899	Approved
0.7757	Intermediate Similarity	NPD6881	Approved
0.7755	Intermediate Similarity	NPD4753	Phase 2
0.7708	Intermediate Similarity	NPD5329	Approved
0.7706	Intermediate Similarity	NPD6649	Approved
0.7706	Intermediate Similarity	NPD6650	Approved
0.77	Intermediate Similarity	NPD6399	Phase 3
0.7664	Intermediate Similarity	NPD5697	Approved
0.7629	Intermediate Similarity	NPD5690	Phase 2
0.7629	Intermediate Similarity	NPD4519	Discontinued
0.7629	Intermediate Similarity	NPD4623	Approved
0.7629	Intermediate Similarity	NPD4694	Approved
0.7629	Intermediate Similarity	NPD5280	Approved
0.7615	Intermediate Similarity	NPD6883	Approved
0.7615	Intermediate Similarity	NPD7290	Approved
0.7615	Intermediate Similarity	NPD7102	Approved
0.7604	Intermediate Similarity	NPD4197	Approved
0.76	Intermediate Similarity	NPD5281	Approved
0.76	Intermediate Similarity	NPD5284	Approved
0.7593	Intermediate Similarity	NPD4729	Approved
0.7593	Intermediate Similarity	NPD5168	Approved
0.7593	Intermediate Similarity	NPD4730	Approved
0.7593	Intermediate Similarity	NPD6011	Approved
0.757	Intermediate Similarity	NPD7128	Approved
0.757	Intermediate Similarity	NPD6675	Approved
0.757	Intermediate Similarity	NPD5739	Approved
0.757	Intermediate Similarity	NPD6402	Approved
0.7568	Intermediate Similarity	NPD4632	Approved
0.7547	Intermediate Similarity	NPD4754	Approved
0.7545	Intermediate Similarity	NPD6617	Approved
0.7545	Intermediate Similarity	NPD6847	Approved
0.7545	Intermediate Similarity	NPD6869	Approved
0.7545	Intermediate Similarity	NPD8130	Phase 1
0.7526	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD6012	Approved
0.7523	Intermediate Similarity	NPD6372	Approved
0.7523	Intermediate Similarity	NPD6373	Approved
0.7523	Intermediate Similarity	NPD6013	Approved
0.7523	Intermediate Similarity	NPD6014	Approved
0.75	Intermediate Similarity	NPD4788	Approved
0.7477	Intermediate Similarity	NPD6882	Approved
0.7477	Intermediate Similarity	NPD8297	Approved
0.7473	Intermediate Similarity	NPD4058	Approved
0.7455	Intermediate Similarity	NPD5251	Approved
0.7455	Intermediate Similarity	NPD5250	Approved
0.7455	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD5249	Phase 3
0.7455	Intermediate Similarity	NPD5248	Approved
0.7455	Intermediate Similarity	NPD5247	Approved
0.7455	Intermediate Similarity	NPD5169	Approved
0.7455	Intermediate Similarity	NPD5135	Approved
0.7451	Intermediate Similarity	NPD7748	Approved
0.7449	Intermediate Similarity	NPD6684	Approved
0.7449	Intermediate Similarity	NPD4690	Approved
0.7449	Intermediate Similarity	NPD5330	Approved
0.7449	Intermediate Similarity	NPD5205	Approved
0.7449	Intermediate Similarity	NPD7334	Approved
0.7449	Intermediate Similarity	NPD7521	Approved
0.7449	Intermediate Similarity	NPD4688	Approved
0.7449	Intermediate Similarity	NPD7146	Approved
0.7449	Intermediate Similarity	NPD6409	Approved
0.7449	Intermediate Similarity	NPD4138	Approved
0.7449	Intermediate Similarity	NPD4693	Phase 3
0.7449	Intermediate Similarity	NPD4689	Approved
0.7447	Intermediate Similarity	NPD6929	Approved
0.7447	Intermediate Similarity	NPD4195	Approved
0.7431	Intermediate Similarity	NPD5128	Approved
0.7431	Intermediate Similarity	NPD7320	Approved
0.7423	Intermediate Similarity	NPD3668	Phase 3
0.7407	Intermediate Similarity	NPD4767	Approved
0.7407	Intermediate Similarity	NPD4768	Approved
0.7404	Intermediate Similarity	NPD6084	Phase 2
0.7404	Intermediate Similarity	NPD7902	Approved
0.7404	Intermediate Similarity	NPD6083	Phase 2
0.7391	Intermediate Similarity	NPD6942	Approved
0.7391	Intermediate Similarity	NPD7339	Approved
0.7387	Intermediate Similarity	NPD5217	Approved
0.7387	Intermediate Similarity	NPD5216	Approved
0.7387	Intermediate Similarity	NPD5127	Approved
0.7387	Intermediate Similarity	NPD5215	Approved
0.7374	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6930	Phase 2
0.7368	Intermediate Similarity	NPD7525	Registered
0.7368	Intermediate Similarity	NPD6009	Approved
0.7368	Intermediate Similarity	NPD6931	Approved
0.7368	Intermediate Similarity	NPD7514	Phase 3
0.734	Intermediate Similarity	NPD7145	Approved
0.734	Intermediate Similarity	NPD3617	Approved
0.7339	Intermediate Similarity	NPD5701	Approved
0.7328	Intermediate Similarity	NPD6054	Approved
0.73	Intermediate Similarity	NPD6903	Approved
0.73	Intermediate Similarity	NPD6672	Approved
0.73	Intermediate Similarity	NPD5737	Approved
0.73	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6902	Approved
0.729	Intermediate Similarity	NPD7632	Discontinued
0.7283	Intermediate Similarity	NPD4687	Approved
0.7283	Intermediate Similarity	NPD5733	Approved
0.7281	Intermediate Similarity	NPD6868	Approved
0.7264	Intermediate Similarity	NPD6404	Discontinued
0.7255	Intermediate Similarity	NPD7637	Suspended
0.7248	Intermediate Similarity	NPD6008	Approved
0.7234	Intermediate Similarity	NPD6925	Approved
0.7234	Intermediate Similarity	NPD5776	Phase 2
0.7232	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD6370	Approved
0.7193	Intermediate Similarity	NPD5167	Approved
0.7188	Intermediate Similarity	NPD7332	Phase 2
0.7188	Intermediate Similarity	NPD4695	Discontinued
0.7182	Intermediate Similarity	NPD6412	Phase 2
0.7179	Intermediate Similarity	NPD6319	Approved
0.7172	Intermediate Similarity	NPD1696	Phase 3
0.7172	Intermediate Similarity	NPD1694	Approved
0.717	Intermediate Similarity	NPD5696	Approved
0.717	Intermediate Similarity	NPD5290	Discontinued
0.7158	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD4096	Approved
0.7157	Intermediate Similarity	NPD5207	Approved
0.7155	Intermediate Similarity	NPD6335	Approved
0.7143	Intermediate Similarity	NPD6695	Phase 3
0.7143	Intermediate Similarity	NPD4691	Approved
0.7143	Intermediate Similarity	NPD7604	Phase 2
0.7143	Intermediate Similarity	NPD4747	Approved
0.7129	Intermediate Similarity	NPD4518	Approved
0.7128	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6015	Approved
0.7119	Intermediate Similarity	NPD6016	Approved
0.7119	Intermediate Similarity	NPD5983	Phase 2
0.7115	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7900	Approved
0.7097	Intermediate Similarity	NPD6926	Approved
0.7097	Intermediate Similarity	NPD6924	Approved
0.7094	Intermediate Similarity	NPD7101	Approved
0.7094	Intermediate Similarity	NPD7100	Approved
0.7087	Intermediate Similarity	NPD8034	Phase 2
0.7087	Intermediate Similarity	NPD8035	Phase 2
0.7083	Intermediate Similarity	NPD7492	Approved
0.7071	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6317	Approved
0.7065	Intermediate Similarity	NPD5276	Approved
0.7065	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7152	Approved
0.7065	Intermediate Similarity	NPD7150	Approved
0.7065	Intermediate Similarity	NPD7151	Approved
0.7059	Intermediate Similarity	NPD5988	Approved
0.7053	Intermediate Similarity	NPD6932	Approved
0.7048	Intermediate Similarity	NPD5695	Phase 3
0.7034	Intermediate Similarity	NPD6059	Approved
0.7033	Intermediate Similarity	NPD4137	Phase 3
0.703	Intermediate Similarity	NPD3573	Approved
0.7025	Intermediate Similarity	NPD6336	Discontinued
0.7025	Intermediate Similarity	NPD6616	Approved
0.7021	Intermediate Similarity	NPD3703	Phase 2
0.7021	Intermediate Similarity	NPD8264	Approved
0.7019	Intermediate Similarity	NPD5133	Approved
0.7019	Intermediate Similarity	NPD5778	Approved
0.7019	Intermediate Similarity	NPD5779	Approved
0.701	Intermediate Similarity	NPD8259	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