NPASS Compound

Structure

CID198968 OpenBabel06191715592D 30 33 0 0 1 0 0 0 0 0999 V2000 -2.8089 3.7142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2057 4.6047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3611 6.1698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4627 5.2001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5364 2.4740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3514 3.0269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7482 3.9175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8448 -1.4642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6902 -0.9764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2254 1.4621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2251 0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6893 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8456 1.4631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8445 0.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6910 1.9508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8451 -1.4637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3817 2.9253 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1753 4.7064 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0003 -0.9759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6895 -0.9755 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6905 -0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3815 1.9503 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5358 0.4872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8454 0.4877 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5721 5.5969 0.0000 C 0 0 0 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 -2.5361 1.4626 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5557 -1.4752 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9993 6.3858 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 7 8 1 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 10 1 0 0 0 0 9 20 2 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 15 1 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 14 25 1 0 0 0 0 15 27 1 0 0 0 0 16 28 1 0 0 0 0 17 20 1 0 0 0 0 17 21 1 0 0 0 0 18 1 1 1 0 0 0 18 23 1 0 0 0 0 19 2 1 1 0 0 0 19 26 1 0 0 0 0 20 27 1 0 0 0 0 21 29 1 6 0 0 0 22 10 1 1 0 0 0 22 24 1 0 0 0 0 22 25 1 0 0 0 0 23 28 1 6 0 0 0 24 28 1 6 0 0 0 25 27 1 6 0 0 0 26 30 1 0 0 0 0 27 5 1 6 0 0 0 28 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.37
Volume:	473.562
LogP:	6.754
LogD:	5.669
LogS:	-5.372
# Rotatable Bonds:	5
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.487
Synthetic Accessibility Score:	4.502
Fsp3:	0.929
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:	-4.613
MDCK Permeability:	1.2410603630996775e-05
Pgp-inhibitor:	0.967
Pgp-substrate:	0.139
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.97
30% Bioavailability (F30%):	0.026

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.351
Plasma Protein Binding (PPB):	94.69429016113281%
Volume Distribution (VD):	1.177
Pgp-substrate:	1.0653347969055176%

ADMET: Metabolism

CYP1A2-inhibitor:	0.106
CYP1A2-substrate:	0.4
CYP2C19-inhibitor:	0.111
CYP2C19-substrate:	0.86
CYP2C9-inhibitor:	0.275
CYP2C9-substrate:	0.253
CYP2D6-inhibitor:	0.041
CYP2D6-substrate:	0.453
CYP3A4-inhibitor:	0.481
CYP3A4-substrate:	0.359

ADMET: Excretion

Clearance (CL):	7.967
Half-life (T1/2):	0.057

ADMET: Toxicity

hERG Blockers:	0.235
Human Hepatotoxicity (H-HT):	0.246
Drug-inuced Liver Injury (DILI):	0.253
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.615
Skin Sensitization:	0.957
Carcinogencity:	0.267
Eye Corrosion:	0.676
Eye Irritation:	0.716
Respiratory Toxicity:	0.893

Download Data

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

Natural Product: NPC198968

Natural Product ID:	NPC198968
*Common Name:**	(24S)-24-Methylcholest-5-Ene-3Beta,25-Diol
IUPAC Name:	(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5S)-6-hydroxy-5,6-dimethylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Synonyms:
Standard InCHIKey:	VTJZYXUUWSKREG-WEBRBZGQSA-N
Standard InCHI:	InChI=1S/C28H48O2/c1-18(7-8-19(2)26(3,4)30)23-11-12-24-22-10-9-20-17-21(29)13-15-27(20,5)25(22)14-16-28(23,24)6/h9,18-19,21-25,29-30H,7-8,10-17H2,1-6H3/t18-,19+,21+,22+,23-,24+,25+,27+,28-/m1/s1
SMILES:	O[C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@H]3CC[C@@H]2[C@@H](CC[C@@H](C(O)(C)C)C)C)C)C1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1784243
PubChem CID:	14632863
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO24056	Sinularia grandilobata	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18447385]
NPO9888	Lobophytum laevigatum	Species	Alcyoniidae	Eukaryota	n.a.	Vietnamese	n.a.	PMID[21458279]
NPO9888	Lobophytum laevigatum	Species	Alcyoniidae	Eukaryota	n.a.	Vietnamese soft coral	n.a.	PMID[21507644]
NPO24255	Chaetomium elatum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23586920]
NPO4192	Gynochthodes umbellata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23968	Paris verticillata	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17563	Chroococcus turgidus	Species	Chroococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO23762	Callicarpa dichotoma	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24099	Isodon oresbius	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24012	Senecio longiflorus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24255	Chaetomium elatum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24056	Sinularia grandilobata	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9888	Lobophytum laevigatum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22167	Fossombronia pusilla	Species	Fossombroniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23635	Ehretia aspera	Species	Ehretiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21715	Leymus mollis	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4192	Gynochthodes umbellata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	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	IC50	>	20000.0	nM	PMID[495247]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	18100.0	nM	PMID[495247]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	20000.0	nM	PMID[495247]

☑ 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 NPC198968 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	147
0.1-0.2	1303
0.2-0.3	7176
0.3-0.4	15665
0.4-0.5	6836
0.5-0.6	5723
0.6-0.7	4162
0.7-0.8	1255
0.8-0.85	246
0.85-0.9	96
0.9-0.95	58
0.95-1	30

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC318495
1.0	High Similarity	NPC155986
0.9859	High Similarity	NPC107059
0.9859	High Similarity	NPC321381
0.9859	High Similarity	NPC321016
0.9726	High Similarity	NPC328714
0.9718	High Similarity	NPC134847
0.9718	High Similarity	NPC136188
0.9718	High Similarity	NPC285893
0.9718	High Similarity	NPC28657
0.9718	High Similarity	NPC230301
0.9718	High Similarity	NPC304309
0.9718	High Similarity	NPC22105
0.9718	High Similarity	NPC162742
0.9718	High Similarity	NPC288035
0.9595	High Similarity	NPC241290
0.9595	High Similarity	NPC209944
0.9595	High Similarity	NPC164840
0.9589	High Similarity	NPC477522
0.9589	High Similarity	NPC473943
0.9589	High Similarity	NPC474216
0.9589	High Similarity	NPC87604
0.9583	High Similarity	NPC240604
0.9583	High Similarity	NPC300324
0.9583	High Similarity	NPC113733
0.9467	High Similarity	NPC264245
0.9467	High Similarity	NPC47761
0.9459	High Similarity	NPC81306
0.9459	High Similarity	NPC109546
0.9459	High Similarity	NPC84694
0.9459	High Similarity	NPC28862
0.9459	High Similarity	NPC143182
0.9459	High Similarity	NPC47982
0.9452	High Similarity	NPC34019
0.9444	High Similarity	NPC471723
0.9444	High Similarity	NPC141071
0.9444	High Similarity	NPC257347
0.9342	High Similarity	NPC49964
0.9333	High Similarity	NPC234193
0.9333	High Similarity	NPC26117
0.9324	High Similarity	NPC307965
0.9324	High Similarity	NPC18603
0.9324	High Similarity	NPC285761
0.9324	High Similarity	NPC76931
0.9324	High Similarity	NPC275910
0.9315	High Similarity	NPC134330
0.9315	High Similarity	NPC129165
0.9315	High Similarity	NPC96319
0.9315	High Similarity	NPC189883
0.9221	High Similarity	NPC475789
0.9221	High Similarity	NPC474634
0.9211	High Similarity	NPC7505
0.9211	High Similarity	NPC474752
0.9211	High Similarity	NPC474731
0.9211	High Similarity	NPC474683
0.9211	High Similarity	NPC474759
0.9211	High Similarity	NPC474531
0.9211	High Similarity	NPC82986
0.9211	High Similarity	NPC23852
0.9211	High Similarity	NPC209620
0.9211	High Similarity	NPC470383
0.92	High Similarity	NPC273410
0.92	High Similarity	NPC209430
0.92	High Similarity	NPC1319
0.92	High Similarity	NPC30986
0.92	High Similarity	NPC80530
0.9189	High Similarity	NPC214570
0.9167	High Similarity	NPC474140
0.9167	High Similarity	NPC471799
0.9103	High Similarity	NPC205845
0.9091	High Similarity	NPC1272
0.9091	High Similarity	NPC5985
0.9091	High Similarity	NPC50964
0.9091	High Similarity	NPC30166
0.9091	High Similarity	NPC101462
0.9091	High Similarity	NPC189972
0.9091	High Similarity	NPC470614
0.9079	High Similarity	NPC13554
0.9079	High Similarity	NPC236237
0.9079	High Similarity	NPC102253
0.9079	High Similarity	NPC322313
0.9079	High Similarity	NPC236112
0.9067	High Similarity	NPC167037
0.9067	High Similarity	NPC244385
0.9067	High Similarity	NPC477514
0.9067	High Similarity	NPC138621
0.9067	High Similarity	NPC6978
0.9054	High Similarity	NPC73875
0.9054	High Similarity	NPC247325
0.9054	High Similarity	NPC470362
0.9054	High Similarity	NPC202642
0.9054	High Similarity	NPC237460
0.9054	High Similarity	NPC46160
0.9054	High Similarity	NPC244488
0.9041	High Similarity	NPC471797
0.9041	High Similarity	NPC27395
0.9041	High Similarity	NPC329090
0.8987	High Similarity	NPC157257
0.8987	High Similarity	NPC274448
0.8987	High Similarity	NPC474189
0.8987	High Similarity	NPC474349
0.8974	High Similarity	NPC317458
0.8919	High Similarity	NPC322353
0.8919	High Similarity	NPC328104
0.8919	High Similarity	NPC118508
0.8919	High Similarity	NPC121744
0.8919	High Similarity	NPC319090
0.8889	High Similarity	NPC475728
0.8875	High Similarity	NPC152808
0.8875	High Similarity	NPC293287
0.8875	High Similarity	NPC94462
0.8875	High Similarity	NPC261266
0.8875	High Similarity	NPC6391
0.8873	High Similarity	NPC208999
0.8873	High Similarity	NPC160209
0.8861	High Similarity	NPC209802
0.8861	High Similarity	NPC221758
0.8861	High Similarity	NPC238485
0.8861	High Similarity	NPC124172
0.8861	High Similarity	NPC185568
0.8861	High Similarity	NPC33913
0.8861	High Similarity	NPC474047
0.8861	High Similarity	NPC59453
0.8861	High Similarity	NPC470077
0.8861	High Similarity	NPC472265
0.8846	High Similarity	NPC470049
0.8846	High Similarity	NPC87489
0.8846	High Similarity	NPC296701
0.8846	High Similarity	NPC248886
0.8846	High Similarity	NPC201852
0.8846	High Similarity	NPC218616
0.8816	High Similarity	NPC65897
0.8816	High Similarity	NPC205455
0.8816	High Similarity	NPC85346
0.8816	High Similarity	NPC186191
0.8816	High Similarity	NPC302041
0.88	High Similarity	NPC315261
0.8784	High Similarity	NPC477138
0.8784	High Similarity	NPC469534
0.8784	High Similarity	NPC469533
0.8784	High Similarity	NPC469593
0.8784	High Similarity	NPC243342
0.8767	High Similarity	NPC242001
0.8767	High Similarity	NPC167706
0.8765	High Similarity	NPC149224
0.875	High Similarity	NPC266511
0.875	High Similarity	NPC318390
0.8734	High Similarity	NPC207013
0.8718	High Similarity	NPC6707
0.8701	High Similarity	NPC472463
0.8701	High Similarity	NPC291379
0.8684	High Similarity	NPC471798
0.8667	High Similarity	NPC477923
0.8667	High Similarity	NPC66566
0.8667	High Similarity	NPC291503
0.8667	High Similarity	NPC3403
0.8667	High Similarity	NPC471468
0.8659	High Similarity	NPC474668
0.8649	High Similarity	NPC201373
0.8649	High Similarity	NPC182717
0.8642	High Similarity	NPC474733
0.8642	High Similarity	NPC31564
0.8642	High Similarity	NPC474778
0.8642	High Similarity	NPC145879
0.8642	High Similarity	NPC477604
0.8642	High Similarity	NPC24277
0.8642	High Similarity	NPC51014
0.8642	High Similarity	NPC474732
0.8642	High Similarity	NPC474970
0.8642	High Similarity	NPC155011
0.8642	High Similarity	NPC125399
0.863	High Similarity	NPC145498
0.8625	High Similarity	NPC231310
0.8625	High Similarity	NPC474493
0.8625	High Similarity	NPC478102
0.8608	High Similarity	NPC151519
0.8608	High Similarity	NPC202389
0.8608	High Similarity	NPC20853
0.859	High Similarity	NPC22403
0.8571	High Similarity	NPC475337
0.8571	High Similarity	NPC83351
0.8571	High Similarity	NPC318136
0.8571	High Similarity	NPC474989
0.8571	High Similarity	NPC22955
0.8571	High Similarity	NPC312328
0.8571	High Similarity	NPC470396
0.8571	High Similarity	NPC99168
0.8571	High Similarity	NPC167891
0.8554	High Similarity	NPC76879
0.8554	High Similarity	NPC474245
0.8554	High Similarity	NPC470361
0.8554	High Similarity	NPC32830
0.8553	High Similarity	NPC106364
0.8553	High Similarity	NPC91573
0.8553	High Similarity	NPC265588
0.8553	High Similarity	NPC274079
0.8553	High Similarity	NPC477925
0.8537	High Similarity	NPC58063
0.8537	High Similarity	NPC475313
0.8537	High Similarity	NPC475740

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 NPC198968 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	139
0.1-0.2	1552
0.2-0.3	4461
0.3-0.4	2098
0.4-0.5	460
0.5-0.6	161
0.6-0.7	158
0.7-0.8	82
0.8-0.85	21
0.85-0.9	13
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9718	High Similarity	NPD6942	Approved
0.9718	High Similarity	NPD7339	Approved
0.9315	High Similarity	NPD3701	Clinical (unspecified phase)
0.9079	High Similarity	NPD7525	Registered
0.9041	High Similarity	NPD6924	Approved
0.9041	High Similarity	NPD6926	Approved
0.8861	High Similarity	NPD4786	Approved
0.88	High Similarity	NPD6933	Approved
0.8784	High Similarity	NPD4784	Approved
0.8784	High Similarity	NPD4785	Approved
0.8767	High Similarity	NPD4243	Approved
0.8608	High Similarity	NPD3667	Approved
0.8537	High Similarity	NPD4751	Clinical (unspecified phase)
0.8514	High Similarity	NPD7152	Approved
0.8514	High Similarity	NPD7150	Approved
0.8514	High Similarity	NPD7151	Approved
0.8493	Intermediate Similarity	NPD6923	Approved
0.8493	Intermediate Similarity	NPD6922	Approved
0.8378	Intermediate Similarity	NPD7143	Approved
0.8378	Intermediate Similarity	NPD7144	Approved
0.8354	Intermediate Similarity	NPD6930	Phase 2
0.8354	Intermediate Similarity	NPD6931	Approved
0.8354	Intermediate Similarity	NPD4748	Discontinued
0.8228	Intermediate Similarity	NPD6929	Approved
0.8228	Intermediate Similarity	NPD7645	Phase 2
0.8205	Intermediate Similarity	NPD6932	Approved
0.8182	Intermediate Similarity	NPD5275	Approved
0.8182	Intermediate Similarity	NPD4190	Phase 3
0.8125	Intermediate Similarity	NPD7509	Discontinued
0.8118	Intermediate Similarity	NPD5328	Approved
0.8049	Intermediate Similarity	NPD6695	Phase 3
0.8	Intermediate Similarity	NPD4195	Approved
0.8	Intermediate Similarity	NPD6683	Phase 2
0.7976	Intermediate Similarity	NPD3618	Phase 1
0.7975	Intermediate Similarity	NPD6925	Approved
0.7975	Intermediate Similarity	NPD5776	Phase 2
0.7952	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD3665	Phase 1
0.7952	Intermediate Similarity	NPD3666	Approved
0.7952	Intermediate Similarity	NPD3133	Approved
0.7931	Intermediate Similarity	NPD6079	Approved
0.7901	Intermediate Similarity	NPD7514	Phase 3
0.7875	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD7145	Approved
0.7857	Intermediate Similarity	NPD6893	Approved
0.7841	Intermediate Similarity	NPD4202	Approved
0.7841	Intermediate Similarity	NPD6399	Phase 3
0.7738	Intermediate Similarity	NPD3668	Phase 3
0.7711	Intermediate Similarity	NPD4221	Approved
0.7711	Intermediate Similarity	NPD4223	Phase 3
0.7701	Intermediate Similarity	NPD4753	Phase 2
0.7683	Intermediate Similarity	NPD7332	Phase 2
0.7674	Intermediate Similarity	NPD7524	Approved
0.7674	Intermediate Similarity	NPD7750	Discontinued
0.7647	Intermediate Similarity	NPD5329	Approved
0.759	Intermediate Similarity	NPD6898	Phase 1
0.759	Intermediate Similarity	NPD6902	Approved
0.7558	Intermediate Similarity	NPD5279	Phase 3
0.7529	Intermediate Similarity	NPD4197	Approved
0.75	Intermediate Similarity	NPD8264	Approved
0.75	Intermediate Similarity	NPD4755	Approved
0.7442	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD4788	Approved
0.7391	Intermediate Similarity	NPD5222	Approved
0.7391	Intermediate Similarity	NPD5221	Approved
0.7391	Intermediate Similarity	NPD4697	Phase 3
0.7391	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD4688	Approved
0.7356	Intermediate Similarity	NPD4689	Approved
0.7356	Intermediate Similarity	NPD5205	Approved
0.7356	Intermediate Similarity	NPD4690	Approved
0.7356	Intermediate Similarity	NPD4693	Phase 3
0.7356	Intermediate Similarity	NPD4138	Approved
0.734	Intermediate Similarity	NPD4700	Approved
0.734	Intermediate Similarity	NPD5285	Approved
0.734	Intermediate Similarity	NPD5286	Approved
0.734	Intermediate Similarity	NPD4696	Approved
0.7333	Intermediate Similarity	NPD7087	Discontinued
0.7312	Intermediate Similarity	NPD6083	Phase 2
0.7312	Intermediate Similarity	NPD6084	Phase 2
0.7312	Intermediate Similarity	NPD5173	Approved
0.7308	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6051	Approved
0.7283	Intermediate Similarity	NPD5210	Approved
0.7283	Intermediate Similarity	NPD4629	Approved
0.7263	Intermediate Similarity	NPD5223	Approved
0.7215	Intermediate Similarity	NPD4787	Phase 1
0.7191	Intermediate Similarity	NPD4723	Approved
0.7191	Intermediate Similarity	NPD4722	Approved
0.7188	Intermediate Similarity	NPD5226	Approved
0.7188	Intermediate Similarity	NPD4633	Approved
0.7188	Intermediate Similarity	NPD5211	Phase 2
0.7188	Intermediate Similarity	NPD5225	Approved
0.7188	Intermediate Similarity	NPD5224	Approved
0.7159	Intermediate Similarity	NPD4694	Approved
0.7159	Intermediate Similarity	NPD7146	Approved
0.7159	Intermediate Similarity	NPD7521	Approved
0.7159	Intermediate Similarity	NPD5280	Approved
0.7159	Intermediate Similarity	NPD7334	Approved
0.7159	Intermediate Similarity	NPD5690	Phase 2
0.7159	Intermediate Similarity	NPD6409	Approved
0.7159	Intermediate Similarity	NPD6684	Approved
0.7159	Intermediate Similarity	NPD5330	Approved
0.7143	Intermediate Similarity	NPD6402	Approved
0.7143	Intermediate Similarity	NPD7128	Approved
0.7143	Intermediate Similarity	NPD7515	Phase 2
0.7143	Intermediate Similarity	NPD5739	Approved
0.7143	Intermediate Similarity	NPD6675	Approved
0.7113	Intermediate Similarity	NPD5174	Approved
0.7113	Intermediate Similarity	NPD5175	Approved
0.7113	Intermediate Similarity	NPD4754	Approved
0.7053	Intermediate Similarity	NPD7638	Approved
0.7053	Intermediate Similarity	NPD5290	Discontinued
0.7041	Intermediate Similarity	NPD5141	Approved
0.7024	Intermediate Similarity	NPD3617	Approved
0.7	Intermediate Similarity	NPD6899	Approved
0.7	Intermediate Similarity	NPD6903	Approved
0.7	Intermediate Similarity	NPD6672	Approved
0.7	Intermediate Similarity	NPD5737	Approved
0.7	Intermediate Similarity	NPD6881	Approved
0.7	Intermediate Similarity	NPD7320	Approved
0.7	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD7640	Approved
0.6979	Remote Similarity	NPD7639	Approved
0.6977	Remote Similarity	NPD4692	Approved
0.6977	Remote Similarity	NPD4139	Approved
0.697	Remote Similarity	NPD4768	Approved
0.697	Remote Similarity	NPD4767	Approved
0.6966	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6098	Approved
0.6931	Remote Similarity	NPD6373	Approved
0.6931	Remote Similarity	NPD6372	Approved
0.6915	Remote Similarity	NPD5695	Phase 3
0.6914	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5697	Approved
0.69	Remote Similarity	NPD5701	Approved
0.6875	Remote Similarity	NPD5696	Approved
0.6863	Remote Similarity	NPD7102	Approved
0.6863	Remote Similarity	NPD7290	Approved
0.6863	Remote Similarity	NPD6883	Approved
0.686	Remote Similarity	NPD4695	Discontinued
0.6842	Remote Similarity	NPD368	Approved
0.6832	Remote Similarity	NPD4729	Approved
0.6832	Remote Similarity	NPD4730	Approved
0.6832	Remote Similarity	NPD6011	Approved
0.6832	Remote Similarity	NPD5128	Approved
0.6809	Remote Similarity	NPD7748	Approved
0.6796	Remote Similarity	NPD6847	Approved
0.6796	Remote Similarity	NPD6617	Approved
0.6796	Remote Similarity	NPD6650	Approved
0.6796	Remote Similarity	NPD6869	Approved
0.6796	Remote Similarity	NPD8130	Phase 1
0.6796	Remote Similarity	NPD6649	Approved
0.6796	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.679	Remote Similarity	NPD4747	Approved
0.6778	Remote Similarity	NPD4623	Approved
0.6778	Remote Similarity	NPD4519	Discontinued
0.6774	Remote Similarity	NPD8035	Phase 2
0.6774	Remote Similarity	NPD7637	Suspended
0.6774	Remote Similarity	NPD8034	Phase 2
0.6774	Remote Similarity	NPD5281	Approved
0.6774	Remote Similarity	NPD5284	Approved
0.6765	Remote Similarity	NPD6013	Approved
0.6765	Remote Similarity	NPD6014	Approved
0.6765	Remote Similarity	NPD6012	Approved
0.6747	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6904	Approved
0.6739	Remote Similarity	NPD6673	Approved
0.6739	Remote Similarity	NPD6080	Approved
0.6735	Remote Similarity	NPD4159	Approved
0.6731	Remote Similarity	NPD8297	Approved
0.6731	Remote Similarity	NPD6882	Approved
0.6699	Remote Similarity	NPD5251	Approved
0.6699	Remote Similarity	NPD5248	Approved
0.6699	Remote Similarity	NPD5249	Phase 3
0.6699	Remote Similarity	NPD4634	Approved
0.6699	Remote Similarity	NPD5169	Approved
0.6699	Remote Similarity	NPD5247	Approved
0.6699	Remote Similarity	NPD5250	Approved
0.6699	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5135	Approved
0.6667	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7136	Phase 2
0.6667	Remote Similarity	NPD4137	Phase 3
0.6667	Remote Similarity	NPD5168	Approved
0.6667	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4096	Approved
0.6636	Remote Similarity	NPD7115	Discovery
0.6635	Remote Similarity	NPD5216	Approved
0.6635	Remote Similarity	NPD5217	Approved
0.6635	Remote Similarity	NPD5215	Approved
0.6635	Remote Similarity	NPD5127	Approved
0.663	Remote Similarity	NPD5208	Approved
0.663	Remote Similarity	NPD4518	Approved
0.6598	Remote Similarity	NPD7902	Approved
0.6588	Remote Similarity	NPD6117	Approved
0.6585	Remote Similarity	NPD4691	Approved
0.6585	Remote Similarity	NPD4789	Approved
0.6585	Remote Similarity	NPD4245	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