NPASS Compound

Structure

NPC155304 OpenBabel07101719512D 33 36 0 0 1 0 0 0 0 0999 V2000 -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 -4.1161 6.3564 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 -2.1913 2.4135 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 -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 -1.7321 2.0000 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 -1.0000 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 -5.7633 5.8212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4762 4.6622 0.0000 C 0 0 0 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 -4.7852 5.6132 0.0000 C 0 0 2 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 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 1.7321 -1.0000 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 -3.5491 0.1910 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 -1.0000 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 0.0000 -0.0000 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 -6.0724 6.7722 0.0000 O 0 0 0 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 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8581 -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 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 21 1 0 0 0 0 10 28 1 0 0 0 0 11 27 1 0 0 0 0 12 18 1 0 0 0 0 12 22 1 0 0 0 0 13 20 1 0 0 0 0 13 23 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 20 1 0 0 0 0 17 3 1 1 0 0 0 18 19 1 0 0 0 0 18 24 2 0 0 0 0 19 27 1 6 0 0 0 20 28 1 6 0 0 0 21 26 1 0 0 0 0 21 30 1 6 0 0 0 22 25 1 0 0 0 0 22 31 1 1 0 0 0 23 24 1 0 0 0 0 23 32 2 0 0 0 0 24 28 1 0 0 0 0 25 26 1 0 0 0 0 25 27 1 6 0 0 0 26 33 1 6 0 0 0 27 4 1 6 0 0 0 28 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.32
Volume:	494.66
LogP:	3.267
LogD:	3.321
LogS:	-4.254
# Rotatable Bonds:	6
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.452
Synthetic Accessibility Score:	5.164
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:	-4.808
MDCK Permeability:	7.721412657701876e-06
Pgp-inhibitor:	0.584
Pgp-substrate:	0.278
Human Intestinal Absorption (HIA):	0.107
20% Bioavailability (F20%):	0.247
30% Bioavailability (F30%):	0.077

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.355
Plasma Protein Binding (PPB):	91.8908462524414%
Volume Distribution (VD):	0.543
Pgp-substrate:	4.436403751373291%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.197
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.715
CYP2C9-inhibitor:	0.036
CYP2C9-substrate:	0.085
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.095
CYP3A4-inhibitor:	0.136
CYP3A4-substrate:	0.23

ADMET: Excretion

Clearance (CL):	6.066
Half-life (T1/2):	0.343

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.206
Drug-inuced Liver Injury (DILI):	0.273
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.23
Maximum Recommended Daily Dose:	0.702
Skin Sensitization:	0.178
Carcinogencity:	0.165
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.946

Download Data

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

Natural Product: NPC155304

Natural Product ID:	NPC155304
*Common Name:**	Certonardosterol Q5
IUPAC Name:	(3S,4R,5S,6S,9R,10R,13R,17R)-3,4,6-trihydroxy-17-[(2R,6S)-7-hydroxy-6-methyl-5-methylideneheptan-2-yl]-10,13-dimethyl-1,2,3,4,5,6,7,9,11,12,16,17-dodecahydrocyclopenta[a]phenanthren-15-one
Synonyms:	Certonardosterol Q5
Standard InCHIKey:	ZQHSDLDNYVKIDE-OJTWWPIFSA-N
Standard InCHI:	InChI=1S/C28H44O5/c1-15(17(3)14-29)6-7-16(2)20-13-23(32)24-18-12-22(31)25-26(33)21(30)9-11-27(25,4)19(18)8-10-28(20,24)5/h16-17,19-22,25-26,29-31,33H,1,6-14H2,2-5H3/t16-,17-,19+,20-,21+,22+,25+,26+,27-,28-/m1/s1
SMILES:	C=C(CC[C@@H](C)[C@H]1CC(=O)C2=C3C[C@@H]([C@H]4[C@H]([C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O)O)O)[C@H](C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL456741
PubChem CID:	21589764
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	>	30.0	ug ml-1	PMID[510013]
NPT574	Cell Line	XF498	Homo sapiens	ED50	>	30.0	ug ml-1	PMID[510013]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	>	30.0	ug ml-1	PMID[510013]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	>	30.0	ug ml-1	PMID[510013]
NPT81	Cell Line	A549	Homo sapiens	ED50	>	30.0	ug ml-1	PMID[510013]

☑ 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 NPC155304 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	178
0.1-0.2	1142
0.2-0.3	4449
0.3-0.4	10952
0.4-0.5	11348
0.5-0.6	5994
0.6-0.7	5695
0.7-0.8	2663
0.8-0.85	222
0.85-0.9	45
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9765	High Similarity	NPC250592
0.9765	High Similarity	NPC77263
0.9294	High Similarity	NPC197823
0.9091	High Similarity	NPC1015
0.9091	High Similarity	NPC31985
0.907	High Similarity	NPC470574
0.9011	High Similarity	NPC473170
0.8876	High Similarity	NPC32830
0.8864	High Similarity	NPC475740
0.8791	High Similarity	NPC109305
0.8791	High Similarity	NPC475255
0.8764	High Similarity	NPC470417
0.8764	High Similarity	NPC471722
0.875	High Similarity	NPC145879
0.875	High Similarity	NPC474778
0.875	High Similarity	NPC474732
0.875	High Similarity	NPC72133
0.875	High Similarity	NPC474733
0.875	High Similarity	NPC31564
0.871	High Similarity	NPC473158
0.8696	High Similarity	NPC111015
0.8696	High Similarity	NPC196485
0.8696	High Similarity	NPC245972
0.8681	High Similarity	NPC189520
0.8667	High Similarity	NPC229871
0.8667	High Similarity	NPC469319
0.8652	High Similarity	NPC58063
0.8652	High Similarity	NPC90652
0.8652	High Similarity	NPC469314
0.8652	High Similarity	NPC138756
0.8652	High Similarity	NPC469317
0.8652	High Similarity	NPC241875
0.8632	High Similarity	NPC316964
0.8617	High Similarity	NPC474938
0.8617	High Similarity	NPC474785
0.8602	High Similarity	NPC200702
0.8571	High Similarity	NPC48010
0.8556	High Similarity	NPC292491
0.8556	High Similarity	NPC158778
0.8556	High Similarity	NPC310752
0.8556	High Similarity	NPC328539
0.8556	High Similarity	NPC143767
0.8556	High Similarity	NPC131470
0.8523	High Similarity	NPC221758
0.8523	High Similarity	NPC59453
0.8523	High Similarity	NPC85774
0.8523	High Similarity	NPC214043
0.8506	High Similarity	NPC151519
0.8506	High Similarity	NPC212083
0.8495	Intermediate Similarity	NPC472976
0.8495	Intermediate Similarity	NPC474690
0.8495	Intermediate Similarity	NPC166906
0.8495	Intermediate Similarity	NPC472977
0.8485	Intermediate Similarity	NPC475060
0.8485	Intermediate Similarity	NPC83744
0.8485	Intermediate Similarity	NPC220229
0.8478	Intermediate Similarity	NPC185936
0.8478	Intermediate Similarity	NPC272746
0.8478	Intermediate Similarity	NPC473998
0.8478	Intermediate Similarity	NPC168027
0.8462	Intermediate Similarity	NPC474704
0.8462	Intermediate Similarity	NPC119416
0.8462	Intermediate Similarity	NPC268406
0.8462	Intermediate Similarity	NPC26959
0.8462	Intermediate Similarity	NPC275740
0.8462	Intermediate Similarity	NPC309603
0.8462	Intermediate Similarity	NPC86319
0.8462	Intermediate Similarity	NPC475921
0.8462	Intermediate Similarity	NPC473999
0.8462	Intermediate Similarity	NPC474245
0.8462	Intermediate Similarity	NPC186688
0.8454	Intermediate Similarity	NPC477915
0.8444	Intermediate Similarity	NPC141292
0.8444	Intermediate Similarity	NPC477926
0.8438	Intermediate Similarity	NPC110149
0.8427	Intermediate Similarity	NPC469948
0.8421	Intermediate Similarity	NPC108078
0.8421	Intermediate Similarity	NPC18509
0.8404	Intermediate Similarity	NPC470016
0.8404	Intermediate Similarity	NPC32118
0.8404	Intermediate Similarity	NPC317586
0.84	Intermediate Similarity	NPC217201
0.84	Intermediate Similarity	NPC329417
0.8387	Intermediate Similarity	NPC474736
0.8387	Intermediate Similarity	NPC12722
0.8384	Intermediate Similarity	NPC319077
0.8384	Intermediate Similarity	NPC260268
0.8384	Intermediate Similarity	NPC152695
0.8384	Intermediate Similarity	NPC323834
0.8384	Intermediate Similarity	NPC476027
0.8384	Intermediate Similarity	NPC149047
0.8384	Intermediate Similarity	NPC85829
0.8384	Intermediate Similarity	NPC171137
0.8384	Intermediate Similarity	NPC49958
0.8384	Intermediate Similarity	NPC202167
0.8384	Intermediate Similarity	NPC48733
0.8384	Intermediate Similarity	NPC97202
0.8384	Intermediate Similarity	NPC214264
0.8384	Intermediate Similarity	NPC296945
0.8384	Intermediate Similarity	NPC50692
0.8384	Intermediate Similarity	NPC302607
0.8384	Intermediate Similarity	NPC150531
0.837	Intermediate Similarity	NPC191684
0.837	Intermediate Similarity	NPC85173
0.837	Intermediate Similarity	NPC126993
0.837	Intermediate Similarity	NPC136801
0.837	Intermediate Similarity	NPC183283
0.8367	Intermediate Similarity	NPC191892
0.8352	Intermediate Similarity	NPC242864
0.8352	Intermediate Similarity	NPC471724
0.8333	Intermediate Similarity	NPC475022
0.8333	Intermediate Similarity	NPC51014
0.8333	Intermediate Similarity	NPC222613
0.8333	Intermediate Similarity	NPC158393
0.8333	Intermediate Similarity	NPC118648
0.8317	Intermediate Similarity	NPC214644
0.8317	Intermediate Similarity	NPC11710
0.8316	Intermediate Similarity	NPC305483
0.8316	Intermediate Similarity	NPC328162
0.8316	Intermediate Similarity	NPC73004
0.8316	Intermediate Similarity	NPC96859
0.8316	Intermediate Similarity	NPC117133
0.8316	Intermediate Similarity	NPC471463
0.8316	Intermediate Similarity	NPC204961
0.8316	Intermediate Similarity	NPC173744
0.8315	Intermediate Similarity	NPC473246
0.8315	Intermediate Similarity	NPC161423
0.8315	Intermediate Similarity	NPC58841
0.8315	Intermediate Similarity	NPC227064
0.8315	Intermediate Similarity	NPC321187
0.8315	Intermediate Similarity	NPC329043
0.8315	Intermediate Similarity	NPC472265
0.83	Intermediate Similarity	NPC477916
0.8298	Intermediate Similarity	NPC8993
0.8298	Intermediate Similarity	NPC145667
0.8298	Intermediate Similarity	NPC473172
0.8298	Intermediate Similarity	NPC67831
0.8298	Intermediate Similarity	NPC282395
0.8298	Intermediate Similarity	NPC20235
0.8298	Intermediate Similarity	NPC88116
0.8298	Intermediate Similarity	NPC299996
0.8298	Intermediate Similarity	NPC231063
0.8298	Intermediate Similarity	NPC174051
0.8298	Intermediate Similarity	NPC263548
0.8298	Intermediate Similarity	NPC32407
0.8295	Intermediate Similarity	NPC48362
0.8283	Intermediate Similarity	NPC204833
0.8283	Intermediate Similarity	NPC209502
0.828	Intermediate Similarity	NPC473167
0.828	Intermediate Similarity	NPC233116
0.828	Intermediate Similarity	NPC475806
0.828	Intermediate Similarity	NPC472978
0.828	Intermediate Similarity	NPC473166
0.828	Intermediate Similarity	NPC63748
0.828	Intermediate Similarity	NPC131872
0.8276	Intermediate Similarity	NPC2482
0.8265	Intermediate Similarity	NPC473424
0.8261	Intermediate Similarity	NPC473100
0.8261	Intermediate Similarity	NPC477943
0.8247	Intermediate Similarity	NPC154072
0.8247	Intermediate Similarity	NPC144956
0.8242	Intermediate Similarity	NPC474684
0.8242	Intermediate Similarity	NPC472324
0.8242	Intermediate Similarity	NPC99909
0.8242	Intermediate Similarity	NPC142361
0.8229	Intermediate Similarity	NPC253826
0.8229	Intermediate Similarity	NPC247139
0.8229	Intermediate Similarity	NPC190554
0.8229	Intermediate Similarity	NPC9613
0.8229	Intermediate Similarity	NPC320306
0.8229	Intermediate Similarity	NPC170978
0.8211	Intermediate Similarity	NPC271195
0.8211	Intermediate Similarity	NPC88310
0.8211	Intermediate Similarity	NPC53565
0.8211	Intermediate Similarity	NPC180950
0.8211	Intermediate Similarity	NPC96916
0.8202	Intermediate Similarity	NPC86370
0.82	Intermediate Similarity	NPC166607
0.8191	Intermediate Similarity	NPC472930
0.8191	Intermediate Similarity	NPC274046
0.8191	Intermediate Similarity	NPC470376
0.8191	Intermediate Similarity	NPC198074
0.8191	Intermediate Similarity	NPC470375
0.8191	Intermediate Similarity	NPC69454
0.8191	Intermediate Similarity	NPC133579
0.8191	Intermediate Similarity	NPC474806
0.8182	Intermediate Similarity	NPC264048
0.8182	Intermediate Similarity	NPC474531
0.8182	Intermediate Similarity	NPC475050
0.8182	Intermediate Similarity	NPC249187
0.8182	Intermediate Similarity	NPC136150
0.8182	Intermediate Similarity	NPC247957
0.8173	Intermediate Similarity	NPC73300
0.8173	Intermediate Similarity	NPC108721
0.8172	Intermediate Similarity	NPC473099
0.8172	Intermediate Similarity	NPC472325
0.8172	Intermediate Similarity	NPC171441
0.8163	Intermediate Similarity	NPC476897
0.8161	Intermediate Similarity	NPC229204
0.8152	Intermediate Similarity	NPC230387

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 NPC155304 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	1481
0.2-0.3	3940
0.3-0.4	2463
0.4-0.5	624
0.5-0.6	169
0.6-0.7	152
0.7-0.8	133
0.8-0.85	29
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD3618	Phase 1
0.8667	High Similarity	NPD5328	Approved
0.8523	High Similarity	NPD4786	Approved
0.8506	High Similarity	NPD3667	Approved
0.8478	Intermediate Similarity	NPD6079	Approved
0.8421	Intermediate Similarity	NPD4755	Approved
0.8387	Intermediate Similarity	NPD4202	Approved
0.8315	Intermediate Similarity	NPD3666	Approved
0.8315	Intermediate Similarity	NPD3133	Approved
0.8315	Intermediate Similarity	NPD3665	Phase 1
0.8247	Intermediate Similarity	NPD5286	Approved
0.8247	Intermediate Similarity	NPD5285	Approved
0.8247	Intermediate Similarity	NPD4700	Approved
0.8247	Intermediate Similarity	NPD4696	Approved
0.8125	Intermediate Similarity	NPD4697	Phase 3
0.8125	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD5221	Approved
0.8125	Intermediate Similarity	NPD5222	Approved
0.8085	Intermediate Similarity	NPD7515	Phase 2
0.8081	Intermediate Similarity	NPD4633	Approved
0.8081	Intermediate Similarity	NPD5224	Approved
0.8081	Intermediate Similarity	NPD5211	Phase 2
0.8081	Intermediate Similarity	NPD5225	Approved
0.8081	Intermediate Similarity	NPD5226	Approved
0.8065	Intermediate Similarity	NPD4753	Phase 2
0.8041	Intermediate Similarity	NPD5173	Approved
0.802	Intermediate Similarity	NPD6675	Approved
0.802	Intermediate Similarity	NPD5739	Approved
0.802	Intermediate Similarity	NPD7128	Approved
0.802	Intermediate Similarity	NPD6402	Approved
0.8	Intermediate Similarity	NPD5174	Approved
0.8	Intermediate Similarity	NPD5175	Approved
0.8	Intermediate Similarity	NPD6399	Phase 3
0.798	Intermediate Similarity	NPD5223	Approved
0.7935	Intermediate Similarity	NPD5279	Phase 3
0.7921	Intermediate Similarity	NPD5141	Approved
0.7912	Intermediate Similarity	NPD3668	Phase 3
0.7885	Intermediate Similarity	NPD4634	Approved
0.7864	Intermediate Similarity	NPD6899	Approved
0.7864	Intermediate Similarity	NPD6881	Approved
0.7864	Intermediate Similarity	NPD7320	Approved
0.7843	Intermediate Similarity	NPD4767	Approved
0.7843	Intermediate Similarity	NPD4768	Approved
0.7822	Intermediate Similarity	NPD4754	Approved
0.7788	Intermediate Similarity	NPD6372	Approved
0.7788	Intermediate Similarity	NPD6373	Approved
0.7767	Intermediate Similarity	NPD5697	Approved
0.7767	Intermediate Similarity	NPD6412	Phase 2
0.7767	Intermediate Similarity	NPD5701	Approved
0.7742	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD8297	Approved
0.7732	Intermediate Similarity	NPD7748	Approved
0.7714	Intermediate Similarity	NPD6883	Approved
0.7714	Intermediate Similarity	NPD7102	Approved
0.7714	Intermediate Similarity	NPD7290	Approved
0.7692	Intermediate Similarity	NPD4223	Phase 3
0.7692	Intermediate Similarity	NPD5128	Approved
0.7692	Intermediate Similarity	NPD4729	Approved
0.7692	Intermediate Similarity	NPD4730	Approved
0.7692	Intermediate Similarity	NPD4221	Approved
0.7677	Intermediate Similarity	NPD7902	Approved
0.7677	Intermediate Similarity	NPD6083	Phase 2
0.7677	Intermediate Similarity	NPD6084	Phase 2
0.7667	Intermediate Similarity	NPD4695	Discontinued
0.7667	Intermediate Similarity	NPD7525	Registered
0.7653	Intermediate Similarity	NPD5210	Approved
0.7653	Intermediate Similarity	NPD4629	Approved
0.7642	Intermediate Similarity	NPD8130	Phase 1
0.7642	Intermediate Similarity	NPD6650	Approved
0.7642	Intermediate Similarity	NPD6869	Approved
0.7642	Intermediate Similarity	NPD6847	Approved
0.7642	Intermediate Similarity	NPD6649	Approved
0.7642	Intermediate Similarity	NPD6617	Approved
0.764	Intermediate Similarity	NPD3617	Approved
0.7634	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD5329	Approved
0.7619	Intermediate Similarity	NPD6012	Approved
0.7619	Intermediate Similarity	NPD6013	Approved
0.7619	Intermediate Similarity	NPD6014	Approved
0.7615	Intermediate Similarity	NPD7115	Discovery
0.757	Intermediate Similarity	NPD6882	Approved
0.7553	Intermediate Similarity	NPD6409	Approved
0.7553	Intermediate Similarity	NPD6684	Approved
0.7553	Intermediate Similarity	NPD7146	Approved
0.7553	Intermediate Similarity	NPD7521	Approved
0.7553	Intermediate Similarity	NPD7334	Approved
0.7553	Intermediate Similarity	NPD5330	Approved
0.7547	Intermediate Similarity	NPD5248	Approved
0.7547	Intermediate Similarity	NPD5251	Approved
0.7547	Intermediate Similarity	NPD5250	Approved
0.7547	Intermediate Similarity	NPD5247	Approved
0.7547	Intermediate Similarity	NPD5249	Phase 3
0.7527	Intermediate Similarity	NPD4197	Approved
0.7524	Intermediate Similarity	NPD6011	Approved
0.75	Intermediate Similarity	NPD4632	Approved
0.75	Intermediate Similarity	NPD6942	Approved
0.75	Intermediate Similarity	NPD7339	Approved
0.7477	Intermediate Similarity	NPD5217	Approved
0.7477	Intermediate Similarity	NPD5216	Approved
0.7477	Intermediate Similarity	NPD5215	Approved
0.7477	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD7638	Approved
0.7419	Intermediate Similarity	NPD4788	Approved
0.7416	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD5737	Approved
0.7396	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6903	Approved
0.7396	Intermediate Similarity	NPD6672	Approved
0.7383	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD5135	Approved
0.7383	Intermediate Similarity	NPD5169	Approved
0.7374	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7900	Approved
0.7368	Intermediate Similarity	NPD4690	Approved
0.7368	Intermediate Similarity	NPD5205	Approved
0.7368	Intermediate Similarity	NPD4693	Phase 3
0.7368	Intermediate Similarity	NPD4689	Approved
0.7368	Intermediate Similarity	NPD4138	Approved
0.7368	Intermediate Similarity	NPD4688	Approved
0.7358	Intermediate Similarity	NPD5168	Approved
0.7353	Intermediate Similarity	NPD7640	Approved
0.7353	Intermediate Similarity	NPD7639	Approved
0.7347	Intermediate Similarity	NPD8034	Phase 2
0.7347	Intermediate Similarity	NPD8035	Phase 2
0.7315	Intermediate Similarity	NPD5127	Approved
0.73	Intermediate Similarity	NPD5695	Phase 3
0.729	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD6054	Approved
0.7257	Intermediate Similarity	NPD6059	Approved
0.7257	Intermediate Similarity	NPD6319	Approved
0.7255	Intermediate Similarity	NPD4225	Approved
0.7255	Intermediate Similarity	NPD5696	Approved
0.7222	Intermediate Similarity	NPD6933	Approved
0.7207	Intermediate Similarity	NPD6274	Approved
0.7188	Intermediate Similarity	NPD4694	Approved
0.7188	Intermediate Similarity	NPD5690	Phase 2
0.7188	Intermediate Similarity	NPD5280	Approved
0.7174	Intermediate Similarity	NPD7645	Phase 2
0.7172	Intermediate Similarity	NPD5284	Approved
0.7172	Intermediate Similarity	NPD5281	Approved
0.717	Intermediate Similarity	NPD6008	Approved
0.7168	Intermediate Similarity	NPD7100	Approved
0.7168	Intermediate Similarity	NPD7101	Approved
0.7159	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6009	Approved
0.7143	Intermediate Similarity	NPD6116	Phase 1
0.713	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6370	Approved
0.7129	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4137	Phase 3
0.7126	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD5167	Approved
0.7097	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6335	Approved
0.7054	Intermediate Similarity	NPD6868	Approved
0.7045	Intermediate Similarity	NPD4747	Approved
0.7045	Intermediate Similarity	NPD4691	Approved
0.7043	Intermediate Similarity	NPD6908	Approved
0.7043	Intermediate Similarity	NPD6015	Approved
0.7043	Intermediate Similarity	NPD6016	Approved
0.7043	Intermediate Similarity	NPD6909	Approved
0.7037	Intermediate Similarity	NPD6686	Approved
0.7033	Intermediate Similarity	NPD6117	Approved
0.701	Intermediate Similarity	NPD4519	Discontinued
0.701	Intermediate Similarity	NPD4623	Approved
0.7009	Intermediate Similarity	NPD7492	Approved
0.7	Intermediate Similarity	NPD6924	Approved
0.7	Intermediate Similarity	NPD6926	Approved
0.7	Intermediate Similarity	NPD6411	Approved
0.6991	Remote Similarity	NPD6317	Approved
0.6989	Remote Similarity	NPD4195	Approved
0.6983	Remote Similarity	NPD5988	Approved
0.697	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6673	Approved
0.697	Remote Similarity	NPD6080	Approved
0.697	Remote Similarity	NPD6904	Approved
0.6949	Remote Similarity	NPD6616	Approved
0.6939	Remote Similarity	NPD7524	Approved
0.693	Remote Similarity	NPD6314	Approved
0.693	Remote Similarity	NPD6313	Approved
0.6923	Remote Similarity	NPD7604	Phase 2
0.6923	Remote Similarity	NPD3703	Phase 2
0.6923	Remote Similarity	NPD5290	Discontinued
0.6923	Remote Similarity	NPD6067	Discontinued
0.6909	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.69	Remote Similarity	NPD4096	Approved
0.6897	Remote Similarity	NPD5983	Phase 2
0.6891	Remote Similarity	NPD7078	Approved
0.6891	Remote Similarity	NPD8293	Discontinued
0.6887	Remote Similarity	NPD7632	Discontinued
0.6882	Remote Similarity	NPD6118	Approved
0.6882	Remote Similarity	NPD6115	Approved
0.6882	Remote Similarity	NPD6114	Approved
0.6882	Remote Similarity	NPD6697	Approved
0.687	Remote Similarity	NPD4522	Approved
0.6869	Remote Similarity	NPD4518	Approved
0.6854	Remote Similarity	NPD4245	Approved
0.6854	Remote Similarity	NPD4244	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