NPASS Compound

Structure

NPC166607 OpenBabel07101719512D 33 36 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 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 -1.7321 -0.0000 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 -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 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 1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 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 1.5000 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 2 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 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 0.8660 2.5000 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 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 2 0 0 0 0 6 27 1 0 0 0 0 7 8 1 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 12 2 0 0 0 0 11 21 1 0 0 0 0 12 28 1 0 0 0 0 13 23 1 0 0 0 0 14 22 1 0 0 0 0 14 26 1 0 0 0 0 15 16 1 0 0 0 0 17 4 1 1 0 0 0 17 19 1 0 0 0 0 18 13 1 1 0 0 0 18 20 1 0 0 0 0 18 24 1 0 0 0 0 19 26 1 6 0 0 0 20 26 1 6 0 0 0 21 25 1 0 0 0 0 21 29 1 6 0 0 0 22 24 1 0 0 0 0 22 30 1 1 0 0 0 23 28 1 6 0 0 0 23 31 1 0 0 0 0 24 27 1 6 0 0 0 25 27 1 0 0 0 0 25 32 2 0 0 0 0 26 5 1 6 0 0 0 27 28 1 6 0 0 0 28 33 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.32
Volume:	494.66
LogP:	4.065
LogD:	4.232
LogS:	-4.51
# Rotatable Bonds:	5
TPSA:	94.83
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.424
Synthetic Accessibility Score:	5.04
Fsp3:	0.857
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.757
MDCK Permeability:	1.7840564396465197e-05
Pgp-inhibitor:	0.298
Pgp-substrate:	0.065
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.049
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.45
Plasma Protein Binding (PPB):	91.87728881835938%
Volume Distribution (VD):	0.561
Pgp-substrate:	4.5367512702941895%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.457
CYP2C19-inhibitor:	0.066
CYP2C19-substrate:	0.828
CYP2C9-inhibitor:	0.155
CYP2C9-substrate:	0.665
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.264
CYP3A4-inhibitor:	0.538
CYP3A4-substrate:	0.395

ADMET: Excretion

Clearance (CL):	4.911
Half-life (T1/2):	0.347

ADMET: Toxicity

hERG Blockers:	0.291
Human Hepatotoxicity (H-HT):	0.199
Drug-inuced Liver Injury (DILI):	0.48
AMES Toxicity:	0.106
Rat Oral Acute Toxicity:	0.246
Maximum Recommended Daily Dose:	0.097
Skin Sensitization:	0.663
Carcinogencity:	0.109
Eye Corrosion:	0.011
Eye Irritation:	0.12
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC166607

Natural Product ID:	NPC166607
*Common Name:**	Stoloniferone G
IUPAC Name:	(2R,5R,6R,8S,9S,10R,11R,13R,14S,17R)-2,5,6,11-tetrahydroxy-10,13-dimethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-6,7,8,9,11,12,14,15,16,17-decahydro-2H-cyclopenta[a]phenanthren-1-one
Synonyms:	stoloniferone G
Standard InCHIKey:	XLUAFUWMFZEETH-QFEHSGLGSA-N
Standard InCHI:	InChI=1S/C28H44O5/c1-15(2)16(3)7-8-17(4)19-9-10-20-18-13-23(31)28(33)12-11-21(29)25(32)27(28,6)24(18)22(30)14-26(19,20)5/h11-12,15,17-24,29-31,33H,3,7-10,13-14H2,1-2,4-6H3/t17-,18+,19-,20+,21-,22-,23-,24-,26-,27+,28+/m1/s1
SMILES:	CC(C)C(=C)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@H]([C@]4(C=C[C@H](C(=O)[C@]4(C)[C@H]3[C@@H](C[C@]12C)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL484046
PubChem CID:	11733238
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	=	3.58	ug ml-1	PMID[527978]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	5.86	ug ml-1	PMID[527978]
NPT168	Cell Line	P388	Mus musculus	ED50	=	2.12	ug ml-1	PMID[527978]

☑ 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 NPC166607 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	193
0.1-0.2	1199
0.2-0.3	4087
0.3-0.4	8229
0.4-0.5	13300
0.5-0.6	6853
0.6-0.7	6084
0.7-0.8	2521
0.8-0.85	175
0.85-0.9	52
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9897	High Similarity	NPC160843
0.901	High Similarity	NPC247957
0.901	High Similarity	NPC249187
0.8932	High Similarity	NPC475060
0.8932	High Similarity	NPC220229
0.8846	High Similarity	NPC217201
0.8835	High Similarity	NPC97202
0.8835	High Similarity	NPC296945
0.8835	High Similarity	NPC476027
0.8835	High Similarity	NPC319077
0.8835	High Similarity	NPC149047
0.8835	High Similarity	NPC260268
0.8835	High Similarity	NPC48733
0.8835	High Similarity	NPC49958
0.8835	High Similarity	NPC85829
0.8835	High Similarity	NPC302607
0.8835	High Similarity	NPC214264
0.8835	High Similarity	NPC171137
0.8835	High Similarity	NPC152695
0.8835	High Similarity	NPC50692
0.8835	High Similarity	NPC257353
0.8835	High Similarity	NPC202167
0.8835	High Similarity	NPC150531
0.8824	High Similarity	NPC191892
0.8785	High Similarity	NPC73300
0.8785	High Similarity	NPC108721
0.8762	High Similarity	NPC214644
0.8762	High Similarity	NPC11710
0.875	High Similarity	NPC83744
0.8738	High Similarity	NPC209502
0.8738	High Similarity	NPC72255
0.8738	High Similarity	NPC204833
0.8713	High Similarity	NPC154072
0.8687	High Similarity	NPC271195
0.8687	High Similarity	NPC472485
0.8667	High Similarity	NPC329417
0.8641	High Similarity	NPC117185
0.8586	High Similarity	NPC196485
0.8586	High Similarity	NPC245972
0.8586	High Similarity	NPC292793
0.8585	High Similarity	NPC87335
0.8571	High Similarity	NPC477916
0.8571	High Similarity	NPC165873
0.8557	High Similarity	NPC474245
0.8557	High Similarity	NPC32830
0.8544	High Similarity	NPC477915
0.85	High Similarity	NPC53565
0.8491	Intermediate Similarity	NPC472217
0.8491	Intermediate Similarity	NPC472219
0.8491	Intermediate Similarity	NPC472218
0.8476	Intermediate Similarity	NPC323834
0.8454	Intermediate Similarity	NPC133588
0.8454	Intermediate Similarity	NPC474668
0.8431	Intermediate Similarity	NPC191565
0.8431	Intermediate Similarity	NPC103051
0.84	Intermediate Similarity	NPC8993
0.8396	Intermediate Similarity	NPC472925
0.8384	Intermediate Similarity	NPC97404
0.8384	Intermediate Similarity	NPC41554
0.8384	Intermediate Similarity	NPC475806
0.8364	Intermediate Similarity	NPC67259
0.8364	Intermediate Similarity	NPC147912
0.835	Intermediate Similarity	NPC327431
0.835	Intermediate Similarity	NPC15390
0.835	Intermediate Similarity	NPC110149
0.8349	Intermediate Similarity	NPC207251
0.8333	Intermediate Similarity	NPC170978
0.8333	Intermediate Similarity	NPC126815
0.8333	Intermediate Similarity	NPC474938
0.8333	Intermediate Similarity	NPC474785
0.8333	Intermediate Similarity	NPC235077
0.8333	Intermediate Similarity	NPC76084
0.8318	Intermediate Similarity	NPC65941
0.8317	Intermediate Similarity	NPC272617
0.83	Intermediate Similarity	NPC109305
0.83	Intermediate Similarity	NPC474736
0.8286	Intermediate Similarity	NPC311612
0.8286	Intermediate Similarity	NPC475050
0.8283	Intermediate Similarity	NPC291484
0.8283	Intermediate Similarity	NPC48010
0.8283	Intermediate Similarity	NPC11216
0.8283	Intermediate Similarity	NPC204188
0.8283	Intermediate Similarity	NPC80561
0.8283	Intermediate Similarity	NPC329596
0.8283	Intermediate Similarity	NPC3345
0.8283	Intermediate Similarity	NPC136801
0.8273	Intermediate Similarity	NPC317210
0.8273	Intermediate Similarity	NPC962
0.8273	Intermediate Similarity	NPC250109
0.8269	Intermediate Similarity	NPC476897
0.8265	Intermediate Similarity	NPC193360
0.8265	Intermediate Similarity	NPC470417
0.8257	Intermediate Similarity	NPC472928
0.8247	Intermediate Similarity	NPC470955
0.8247	Intermediate Similarity	NPC261266
0.8247	Intermediate Similarity	NPC51014
0.8246	Intermediate Similarity	NPC67569
0.8241	Intermediate Similarity	NPC141350
0.8241	Intermediate Similarity	NPC5475
0.8241	Intermediate Similarity	NPC173905
0.8241	Intermediate Similarity	NPC472216
0.8241	Intermediate Similarity	NPC284828
0.8235	Intermediate Similarity	NPC249954
0.8235	Intermediate Similarity	NPC49371
0.8235	Intermediate Similarity	NPC117133
0.8224	Intermediate Similarity	NPC185
0.8218	Intermediate Similarity	NPC111015
0.8218	Intermediate Similarity	NPC196227
0.8214	Intermediate Similarity	NPC471854
0.8208	Intermediate Similarity	NPC284865
0.8205	Intermediate Similarity	NPC470882
0.82	Intermediate Similarity	NPC155304
0.82	Intermediate Similarity	NPC233116
0.82	Intermediate Similarity	NPC116726
0.82	Intermediate Similarity	NPC73457
0.82	Intermediate Similarity	NPC473998
0.82	Intermediate Similarity	NPC189520
0.8198	Intermediate Similarity	NPC326542
0.819	Intermediate Similarity	NPC473424
0.819	Intermediate Similarity	NPC87351
0.819	Intermediate Similarity	NPC477054
0.8182	Intermediate Similarity	NPC309603
0.8182	Intermediate Similarity	NPC76879
0.8182	Intermediate Similarity	NPC472971
0.8182	Intermediate Similarity	NPC2983
0.8182	Intermediate Similarity	NPC472970
0.8182	Intermediate Similarity	NPC473999
0.8182	Intermediate Similarity	NPC469319
0.8182	Intermediate Similarity	NPC280782
0.8182	Intermediate Similarity	NPC470361
0.8182	Intermediate Similarity	NPC229871
0.8174	Intermediate Similarity	NPC470265
0.8174	Intermediate Similarity	NPC222688
0.8174	Intermediate Similarity	NPC23786
0.8174	Intermediate Similarity	NPC269642
0.8163	Intermediate Similarity	NPC90652
0.8163	Intermediate Similarity	NPC138756
0.8158	Intermediate Similarity	NPC109973
0.8155	Intermediate Similarity	NPC190554
0.8155	Intermediate Similarity	NPC108078
0.8155	Intermediate Similarity	NPC320306
0.8155	Intermediate Similarity	NPC291634
0.8155	Intermediate Similarity	NPC107243
0.8144	Intermediate Similarity	NPC471224
0.8142	Intermediate Similarity	NPC50774
0.8142	Intermediate Similarity	NPC709
0.8137	Intermediate Similarity	NPC259286
0.8137	Intermediate Similarity	NPC200702
0.8131	Intermediate Similarity	NPC475494
0.8125	Intermediate Similarity	NPC179626
0.8125	Intermediate Similarity	NPC266728
0.8125	Intermediate Similarity	NPC49492
0.812	Intermediate Similarity	NPC293112
0.8119	Intermediate Similarity	NPC474807
0.8113	Intermediate Similarity	NPC131366
0.8103	Intermediate Similarity	NPC469789
0.81	Intermediate Similarity	NPC46758
0.81	Intermediate Similarity	NPC320026
0.8095	Intermediate Similarity	NPC477053
0.8095	Intermediate Similarity	NPC477052
0.8095	Intermediate Similarity	NPC163372
0.8095	Intermediate Similarity	NPC477051
0.8095	Intermediate Similarity	NPC302537
0.8081	Intermediate Similarity	NPC53911
0.8081	Intermediate Similarity	NPC328313
0.807	Intermediate Similarity	NPC473270
0.807	Intermediate Similarity	NPC475041
0.8061	Intermediate Similarity	NPC6391
0.8058	Intermediate Similarity	NPC288970
0.8058	Intermediate Similarity	NPC235053
0.8058	Intermediate Similarity	NPC471463
0.8056	Intermediate Similarity	NPC473284
0.8056	Intermediate Similarity	NPC58370
0.8056	Intermediate Similarity	NPC64844
0.8056	Intermediate Similarity	NPC43285
0.8056	Intermediate Similarity	NPC42847
0.8056	Intermediate Similarity	NPC230541
0.8053	Intermediate Similarity	NPC176513
0.8053	Intermediate Similarity	NPC167606
0.8053	Intermediate Similarity	NPC470775
0.8053	Intermediate Similarity	NPC286528
0.8053	Intermediate Similarity	NPC20302
0.8053	Intermediate Similarity	NPC140055
0.8051	Intermediate Similarity	NPC473265
0.8051	Intermediate Similarity	NPC473253
0.8041	Intermediate Similarity	NPC59453
0.8041	Intermediate Similarity	NPC221758
0.8039	Intermediate Similarity	NPC470958
0.8039	Intermediate Similarity	NPC472976
0.8039	Intermediate Similarity	NPC209662
0.8039	Intermediate Similarity	NPC470957
0.8039	Intermediate Similarity	NPC474690
0.8039	Intermediate Similarity	NPC472977
0.8039	Intermediate Similarity	NPC299100
0.8037	Intermediate Similarity	NPC474281
0.8037	Intermediate Similarity	NPC75531
0.8037	Intermediate Similarity	NPC201763
0.8037	Intermediate Similarity	NPC149124
0.8036	Intermediate Similarity	NPC117712
0.8034	Intermediate Similarity	NPC8374

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 NPC166607 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	1448
0.2-0.3	3810
0.3-0.4	2462
0.4-0.5	754
0.5-0.6	190
0.6-0.7	177
0.7-0.8	129
0.8-0.85	13
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD4634	Approved
0.819	Intermediate Similarity	NPD5211	Phase 2
0.8053	Intermediate Similarity	NPD7115	Discovery
0.8041	Intermediate Similarity	NPD4786	Approved
0.8037	Intermediate Similarity	NPD5141	Approved
0.8	Intermediate Similarity	NPD5286	Approved
0.8	Intermediate Similarity	NPD4696	Approved
0.8	Intermediate Similarity	NPD5285	Approved
0.7981	Intermediate Similarity	NPD4755	Approved
0.7925	Intermediate Similarity	NPD5223	Approved
0.7885	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD4697	Phase 3
0.7885	Intermediate Similarity	NPD5221	Approved
0.7885	Intermediate Similarity	NPD5222	Approved
0.7879	Intermediate Similarity	NPD3618	Phase 1
0.785	Intermediate Similarity	NPD5225	Approved
0.785	Intermediate Similarity	NPD5226	Approved
0.785	Intermediate Similarity	NPD5224	Approved
0.785	Intermediate Similarity	NPD4633	Approved
0.7843	Intermediate Similarity	NPD6079	Approved
0.7835	Intermediate Similarity	NPD3667	Approved
0.783	Intermediate Similarity	NPD4700	Approved
0.7822	Intermediate Similarity	NPD5328	Approved
0.781	Intermediate Similarity	NPD5173	Approved
0.7788	Intermediate Similarity	NPD4632	Approved
0.7778	Intermediate Similarity	NPD5174	Approved
0.7778	Intermediate Similarity	NPD5175	Approved
0.7767	Intermediate Similarity	NPD4202	Approved
0.7767	Intermediate Similarity	NPD6399	Phase 3
0.7692	Intermediate Similarity	NPD6054	Approved
0.7692	Intermediate Similarity	NPD6319	Approved
0.7658	Intermediate Similarity	NPD6881	Approved
0.7658	Intermediate Similarity	NPD6899	Approved
0.7647	Intermediate Similarity	NPD4753	Phase 2
0.7636	Intermediate Similarity	NPD6402	Approved
0.7636	Intermediate Similarity	NPD5739	Approved
0.7636	Intermediate Similarity	NPD7128	Approved
0.7636	Intermediate Similarity	NPD6675	Approved
0.7619	Intermediate Similarity	NPD4629	Approved
0.7619	Intermediate Similarity	NPD5210	Approved
0.7615	Intermediate Similarity	NPD4754	Approved
0.7611	Intermediate Similarity	NPD6649	Approved
0.7611	Intermediate Similarity	NPD6650	Approved
0.7589	Intermediate Similarity	NPD6373	Approved
0.7589	Intermediate Similarity	NPD6372	Approved
0.7568	Intermediate Similarity	NPD5697	Approved
0.7563	Intermediate Similarity	NPD6370	Approved
0.7544	Intermediate Similarity	NPD8297	Approved
0.7542	Intermediate Similarity	NPD6059	Approved
0.7525	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD7102	Approved
0.7522	Intermediate Similarity	NPD6883	Approved
0.7522	Intermediate Similarity	NPD7290	Approved
0.75	Intermediate Similarity	NPD6011	Approved
0.75	Intermediate Similarity	NPD4730	Approved
0.75	Intermediate Similarity	NPD7320	Approved
0.75	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4729	Approved
0.7479	Intermediate Similarity	NPD6016	Approved
0.7479	Intermediate Similarity	NPD6015	Approved
0.7477	Intermediate Similarity	NPD4768	Approved
0.7477	Intermediate Similarity	NPD4767	Approved
0.7456	Intermediate Similarity	NPD6869	Approved
0.7456	Intermediate Similarity	NPD8130	Phase 1
0.7456	Intermediate Similarity	NPD6617	Approved
0.7456	Intermediate Similarity	NPD6847	Approved
0.7449	Intermediate Similarity	NPD7525	Registered
0.7438	Intermediate Similarity	NPD7492	Approved
0.7436	Intermediate Similarity	NPD6009	Approved
0.7434	Intermediate Similarity	NPD6013	Approved
0.7434	Intermediate Similarity	NPD6014	Approved
0.7434	Intermediate Similarity	NPD6012	Approved
0.7426	Intermediate Similarity	NPD5329	Approved
0.7417	Intermediate Similarity	NPD5988	Approved
0.7411	Intermediate Similarity	NPD5701	Approved
0.7391	Intermediate Similarity	NPD6882	Approved
0.7377	Intermediate Similarity	NPD6616	Approved
0.7368	Intermediate Similarity	NPD5169	Approved
0.7368	Intermediate Similarity	NPD5249	Phase 3
0.7368	Intermediate Similarity	NPD5135	Approved
0.7368	Intermediate Similarity	NPD5251	Approved
0.7368	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5250	Approved
0.7368	Intermediate Similarity	NPD5248	Approved
0.7368	Intermediate Similarity	NPD5247	Approved
0.7353	Intermediate Similarity	NPD5279	Phase 3
0.7345	Intermediate Similarity	NPD5128	Approved
0.7339	Intermediate Similarity	NPD7640	Approved
0.7339	Intermediate Similarity	NPD7639	Approved
0.7327	Intermediate Similarity	NPD3665	Phase 1
0.7327	Intermediate Similarity	NPD3668	Phase 3
0.7327	Intermediate Similarity	NPD3133	Approved
0.7327	Intermediate Similarity	NPD3666	Approved
0.7327	Intermediate Similarity	NPD4197	Approved
0.7317	Intermediate Similarity	NPD7078	Approved
0.7315	Intermediate Similarity	NPD6084	Phase 2
0.7315	Intermediate Similarity	NPD6083	Phase 2
0.7311	Intermediate Similarity	NPD4522	Approved
0.7304	Intermediate Similarity	NPD5216	Approved
0.7304	Intermediate Similarity	NPD5217	Approved
0.7304	Intermediate Similarity	NPD5215	Approved
0.7304	Intermediate Similarity	NPD5127	Approved
0.7304	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD7736	Approved
0.7248	Intermediate Similarity	NPD7638	Approved
0.7213	Intermediate Similarity	NPD7604	Phase 2
0.7193	Intermediate Similarity	NPD5168	Approved
0.719	Intermediate Similarity	NPD5983	Phase 2
0.7184	Intermediate Similarity	NPD5690	Phase 2
0.7177	Intermediate Similarity	NPD8293	Discontinued
0.717	Intermediate Similarity	NPD7515	Phase 2
0.717	Intermediate Similarity	NPD7637	Suspended
0.7168	Intermediate Similarity	NPD6008	Approved
0.7129	Intermediate Similarity	NPD4221	Approved
0.7129	Intermediate Similarity	NPD4223	Phase 3
0.712	Intermediate Similarity	NPD6033	Approved
0.7119	Intermediate Similarity	NPD5167	Approved
0.7115	Intermediate Similarity	NPD7524	Approved
0.7113	Intermediate Similarity	NPD7339	Approved
0.7113	Intermediate Similarity	NPD6942	Approved
0.7105	Intermediate Similarity	NPD6412	Phase 2
0.7097	Intermediate Similarity	NPD6336	Discontinued
0.7091	Intermediate Similarity	NPD5696	Approved
0.7091	Intermediate Similarity	NPD4225	Approved
0.7087	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6335	Approved
0.7048	Intermediate Similarity	NPD6672	Approved
0.7048	Intermediate Similarity	NPD5737	Approved
0.7025	Intermediate Similarity	NPD7100	Approved
0.7025	Intermediate Similarity	NPD7101	Approved
0.7019	Intermediate Similarity	NPD4623	Approved
0.7019	Intermediate Similarity	NPD4694	Approved
0.7019	Intermediate Similarity	NPD4519	Discontinued
0.7019	Intermediate Similarity	NPD5280	Approved
0.7009	Intermediate Similarity	NPD8035	Phase 2
0.7009	Intermediate Similarity	NPD5284	Approved
0.7009	Intermediate Similarity	NPD5281	Approved
0.7009	Intermediate Similarity	NPD8034	Phase 2
0.7	Intermediate Similarity	NPD7902	Approved
0.7	Intermediate Similarity	NPD6317	Approved
0.699	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD5695	Phase 3
0.6961	Remote Similarity	NPD4269	Approved
0.6961	Remote Similarity	NPD4270	Approved
0.6944	Remote Similarity	NPD5778	Approved
0.6944	Remote Similarity	NPD5779	Approved
0.6942	Remote Similarity	NPD6314	Approved
0.6942	Remote Similarity	NPD6313	Approved
0.6935	Remote Similarity	NPD8328	Phase 3
0.6931	Remote Similarity	NPD4695	Discontinued
0.6931	Remote Similarity	NPD6930	Phase 2
0.6931	Remote Similarity	NPD7514	Phase 3
0.6931	Remote Similarity	NPD6931	Approved
0.6929	Remote Similarity	NPD7319	Approved
0.6917	Remote Similarity	NPD6274	Approved
0.6917	Remote Similarity	NPD6868	Approved
0.6911	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.69	Remote Similarity	NPD3617	Approved
0.69	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD4788	Approved
0.6893	Remote Similarity	NPD6695	Phase 3
0.6881	Remote Similarity	NPD7748	Approved
0.6881	Remote Similarity	NPD5282	Discontinued
0.6869	Remote Similarity	NPD6933	Approved
0.6869	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.686	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4688	Approved
0.6857	Remote Similarity	NPD4693	Phase 3
0.6857	Remote Similarity	NPD4689	Approved
0.6857	Remote Similarity	NPD6098	Approved
0.6857	Remote Similarity	NPD5205	Approved
0.6857	Remote Similarity	NPD4138	Approved
0.6857	Remote Similarity	NPD4690	Approved
0.6838	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6929	Approved
0.6825	Remote Similarity	NPD7507	Approved
0.6822	Remote Similarity	NPD6673	Approved
0.6822	Remote Similarity	NPD6904	Approved
0.6822	Remote Similarity	NPD6080	Approved
0.6818	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.678	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6908	Approved
0.6774	Remote Similarity	NPD6921	Approved
0.6774	Remote Similarity	NPD6909	Approved
0.6765	Remote Similarity	NPD7332	Phase 2
0.6765	Remote Similarity	NPD4252	Approved
0.6762	Remote Similarity	NPD5363	Approved
0.6759	Remote Similarity	NPD5785	Approved
0.6754	Remote Similarity	NPD5091	Approved
0.6754	Remote Similarity	NPD7632	Discontinued
0.6733	Remote Similarity	NPD7145	Approved
0.6733	Remote Similarity	NPD6114	Approved
0.6733	Remote Similarity	NPD6118	Approved
0.6733	Remote Similarity	NPD6115	Approved
0.6733	Remote Similarity	NPD6697	Approved
0.6727	Remote Similarity	NPD7900	Approved
0.6727	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5369	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