NPASS Compound

Structure

CID209430 OpenBabel06191716002D 30 33 0 0 1 0 0 0 0 0999 V2000 -5.8142 2.0786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2757 2.9218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3020 4.6094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8922 3.7667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5343 2.4720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8405 3.7661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3532 2.9226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2220 1.4609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2217 0.4864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6879 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8450 1.4619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6896 1.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6888 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3015 2.9221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8147 3.7659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3790 2.9229 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6882 -0.9747 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6891 -0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3787 1.9488 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5338 0.4869 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8447 0.4873 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0003 -0.9752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8441 -1.4630 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5340 1.4614 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 2.5544 -1.4744 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -2.4630 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 2 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 22 1 0 0 0 0 10 23 1 0 0 0 0 11 13 1 0 0 0 0 11 20 1 0 0 0 0 12 14 1 0 0 0 0 12 24 1 0 0 0 0 13 28 1 0 0 0 0 14 27 1 0 0 0 0 15 20 1 0 0 0 0 15 25 2 0 0 0 0 16 26 1 0 0 0 0 17 18 1 0 0 0 0 19 4 1 1 0 0 0 19 22 1 0 0 0 0 20 29 1 6 0 0 0 21 16 1 1 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 22 27 1 6 0 0 0 23 27 1 6 0 0 0 24 28 1 6 0 0 0 25 26 1 0 0 0 0 25 28 1 0 0 0 0 26 30 1 6 0 0 0 27 5 1 6 0 0 0 28 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	150.1
Volume:	173.841
LogP:	2.581
LogD:	2.169
LogS:	-2.29
# Rotatable Bonds:	2
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.436
Synthetic Accessibility Score:	3.684
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.435
MDCK Permeability:	2.843814763764385e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.057
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.986
Plasma Protein Binding (PPB):	47.67475891113281%
Volume Distribution (VD):	1.732
Pgp-substrate:	61.6755256652832%

ADMET: Metabolism

CYP1A2-inhibitor:	0.314
CYP1A2-substrate:	0.68
CYP2C19-inhibitor:	0.202
CYP2C19-substrate:	0.598
CYP2C9-inhibitor:	0.03
CYP2C9-substrate:	0.829
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.88
CYP3A4-inhibitor:	0.032
CYP3A4-substrate:	0.253

ADMET: Excretion

Clearance (CL):	6.75
Half-life (T1/2):	0.674

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.707
Drug-inuced Liver Injury (DILI):	0.113
AMES Toxicity:	0.283
Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.92
Skin Sensitization:	0.951
Carcinogencity:	0.885
Eye Corrosion:	0.97
Eye Irritation:	0.986
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC209430

Natural Product ID:	NPC209430
*Common Name:**	24-Methylenecholest-4-En-3-Beta,6Beta-Diol
IUPAC Name:	(3S,6R,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,6-diol
Synonyms:
Standard InCHIKey:	HTLJJZSYTBKDHR-JOCBKWKSSA-N
Standard InCHI:	InChI=1S/C28H46O2/c1-17(2)18(3)7-8-19(4)22-9-10-23-21-16-26(30)25-15-20(29)11-13-28(25,6)24(21)12-14-27(22,23)5/h15,17,19-24,26,29-30H,3,7-14,16H2,1-2,4-6H3/t19-,20+,21+,22-,23+,24+,26-,27-,28-/m1/s1
SMILES:	C=C(C(C)C)CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2C[C@H](C2=C[C@H](CC[C@]12C)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479912
PubChem CID:	11486817
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
NPO10924	Stelletta globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10691710]
NPO8169	Delphinium elatum	Species	Ranunculaceae	Eukaryota	seeds	n.a.	n.a.	PMID[18044843]
NPO10924	Stelletta globostellata	Species	Ancorinidae	Eukaryota	n.a.	Kubat, Malaysia	1991	PMID[18327911]
NPO10924	Stelletta globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18327911]
NPO15032	Ptilonia australasica	Species	Bonnemaisoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26904921]
NPO14031	Alcyonium patagonicum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[7769395]
NPO14031	Alcyonium patagonicum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[7902863]
NPO10924	Stelletta globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8778241]
NPO8169	Delphinium elatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8169	Delphinium elatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18012	Pycnanthus kombo	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1188	Pteris wallichiana	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15525	Albertisia delagoensis	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14988	Chione glabra	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15196	Aframomum giganteum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14031	Alcyonium patagonicum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO9418	Kreysigia multiflora	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10924	Stelletta globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14753	Croton argyroglossum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9552	Phyllobates terribilis	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12810	Adenostyles alliariae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13917	Chondrilla juncea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14472	Sinularia ovispiculata	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13580	Ophiobolus rubellus	Species	Leptosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6175	Colletotrichum fragariae	Species	Glomerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8169	Delphinium elatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15032	Ptilonia australasica	Species	Bonnemaisoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14828	Iphigenia bechuanica	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10242	Cladia aggregata	Species	Cladoniaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	1.0	ug.mL-1	PMID[568517]

☑ 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 NPC209430 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	1291
0.2-0.3	5850
0.3-0.4	15760
0.4-0.5	7984
0.5-0.6	5670
0.6-0.7	4142
0.7-0.8	1396
0.8-0.85	251
0.85-0.9	120
0.9-0.95	74
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC30986
0.973	High Similarity	NPC84694
0.973	High Similarity	NPC28862
0.973	High Similarity	NPC47982
0.973	High Similarity	NPC109546
0.973	High Similarity	NPC81306
0.973	High Similarity	NPC143182
0.96	High Similarity	NPC234193
0.9595	High Similarity	NPC474216
0.9589	High Similarity	NPC244488
0.9589	High Similarity	NPC247325
0.9481	High Similarity	NPC317458
0.9474	High Similarity	NPC209620
0.9474	High Similarity	NPC264245
0.9474	High Similarity	NPC23852
0.9452	High Similarity	NPC471723
0.9452	High Similarity	NPC141071
0.9452	High Similarity	NPC257347
0.9359	High Similarity	NPC474047
0.9351	High Similarity	NPC101462
0.9351	High Similarity	NPC296701
0.9351	High Similarity	NPC50964
0.9351	High Similarity	NPC87489
0.9351	High Similarity	NPC470049
0.9351	High Similarity	NPC189972
0.9351	High Similarity	NPC49964
0.9351	High Similarity	NPC202389
0.9351	High Similarity	NPC218616
0.9342	High Similarity	NPC209944
0.9342	High Similarity	NPC241290
0.9342	High Similarity	NPC164840
0.9333	High Similarity	NPC473943
0.9324	High Similarity	NPC189883
0.9324	High Similarity	NPC107059
0.9324	High Similarity	NPC129165
0.9324	High Similarity	NPC321381
0.9324	High Similarity	NPC321016
0.9324	High Similarity	NPC134330
0.9315	High Similarity	NPC469534
0.9315	High Similarity	NPC469593
0.9315	High Similarity	NPC469533
0.9231	High Similarity	NPC474634
0.9231	High Similarity	NPC475789
0.9221	High Similarity	NPC47761
0.9221	High Similarity	NPC82986
0.9221	High Similarity	NPC474683
0.9221	High Similarity	NPC7505
0.9221	High Similarity	NPC474731
0.9221	High Similarity	NPC474752
0.9221	High Similarity	NPC474759
0.9211	High Similarity	NPC1319
0.92	High Similarity	NPC155986
0.92	High Similarity	NPC318495
0.92	High Similarity	NPC198968
0.92	High Similarity	NPC214570
0.9189	High Similarity	NPC22105
0.9189	High Similarity	NPC28657
0.9189	High Similarity	NPC134847
0.9189	High Similarity	NPC288035
0.9189	High Similarity	NPC304309
0.9189	High Similarity	NPC285893
0.9189	High Similarity	NPC162742
0.9189	High Similarity	NPC230301
0.9189	High Similarity	NPC136188
0.9125	High Similarity	NPC6391
0.9125	High Similarity	NPC261266
0.9114	High Similarity	NPC470077
0.9114	High Similarity	NPC231310
0.9114	High Similarity	NPC205845
0.9114	High Similarity	NPC238485
0.9114	High Similarity	NPC185568
0.9091	High Similarity	NPC236112
0.9079	High Similarity	NPC477522
0.9079	High Similarity	NPC477514
0.9079	High Similarity	NPC138621
0.9079	High Similarity	NPC87604
0.9079	High Similarity	NPC6978
0.9079	High Similarity	NPC275910
0.9079	High Similarity	NPC167037
0.9079	High Similarity	NPC285761
0.9079	High Similarity	NPC244385
0.9067	High Similarity	NPC237460
0.9067	High Similarity	NPC46160
0.9067	High Similarity	NPC240604
0.9067	High Similarity	NPC73875
0.9067	High Similarity	NPC202642
0.9067	High Similarity	NPC113733
0.9067	High Similarity	NPC470362
0.9067	High Similarity	NPC300324
0.9	High Similarity	NPC274448
0.9	High Similarity	NPC266511
0.9	High Similarity	NPC470360
0.9	High Similarity	NPC318390
0.8987	High Similarity	NPC82623
0.8987	High Similarity	NPC470384
0.8974	High Similarity	NPC474531
0.8961	High Similarity	NPC273410
0.8961	High Similarity	NPC80530
0.8961	High Similarity	NPC328714
0.8947	High Similarity	NPC470711
0.8947	High Similarity	NPC34019
0.8947	High Similarity	NPC470758
0.8947	High Similarity	NPC91594
0.8933	High Similarity	NPC185536
0.8933	High Similarity	NPC118508
0.8933	High Similarity	NPC322353
0.8933	High Similarity	NPC121744
0.8919	High Similarity	NPC474140
0.8904	High Similarity	NPC34834
0.8902	High Similarity	NPC133588
0.8902	High Similarity	NPC474668
0.8889	High Similarity	NPC299068
0.8889	High Similarity	NPC293287
0.8889	High Similarity	NPC152808
0.8861	High Similarity	NPC30166
0.8846	High Similarity	NPC295131
0.8846	High Similarity	NPC102253
0.8846	High Similarity	NPC26117
0.8846	High Similarity	NPC236237
0.8846	High Similarity	NPC13554
0.8846	High Similarity	NPC322313
0.8831	High Similarity	NPC476314
0.8831	High Similarity	NPC307965
0.8831	High Similarity	NPC167891
0.8831	High Similarity	NPC83351
0.8831	High Similarity	NPC65897
0.8831	High Similarity	NPC76931
0.8831	High Similarity	NPC205455
0.8831	High Similarity	NPC85346
0.8831	High Similarity	NPC11908
0.8831	High Similarity	NPC186191
0.8831	High Similarity	NPC302041
0.8831	High Similarity	NPC18603
0.8816	High Similarity	NPC470749
0.8816	High Similarity	NPC253190
0.8816	High Similarity	NPC96319
0.88	High Similarity	NPC201048
0.88	High Similarity	NPC306727
0.88	High Similarity	NPC476366
0.8795	High Similarity	NPC472240
0.8795	High Similarity	NPC473999
0.8795	High Similarity	NPC470361
0.8795	High Similarity	NPC309603
0.8795	High Similarity	NPC262858
0.8795	High Similarity	NPC477606
0.878	High Similarity	NPC149224
0.878	High Similarity	NPC470620
0.8765	High Similarity	NPC471224
0.8765	High Similarity	NPC157257
0.875	High Similarity	NPC134481
0.875	High Similarity	NPC470558
0.8734	High Similarity	NPC470383
0.8734	High Similarity	NPC476646
0.8701	High Similarity	NPC257191
0.8701	High Similarity	NPC119355
0.8701	High Similarity	NPC331618
0.8701	High Similarity	NPC248830
0.8701	High Similarity	NPC212241
0.869	High Similarity	NPC11216
0.869	High Similarity	NPC291484
0.869	High Similarity	NPC295668
0.869	High Similarity	NPC329596
0.869	High Similarity	NPC204188
0.869	High Similarity	NPC3345
0.869	High Similarity	NPC80561
0.8675	High Similarity	NPC67872
0.8675	High Similarity	NPC471952
0.8667	High Similarity	NPC474743
0.8667	High Similarity	NPC201373
0.8667	High Similarity	NPC182717
0.8667	High Similarity	NPC471799
0.8659	High Similarity	NPC139724
0.8642	High Similarity	NPC209802
0.8642	High Similarity	NPC478102
0.8642	High Similarity	NPC124172
0.863	High Similarity	NPC96484
0.863	High Similarity	NPC160209
0.8625	High Similarity	NPC248886
0.8625	High Similarity	NPC20853
0.8625	High Similarity	NPC5985
0.8625	High Similarity	NPC201852
0.8625	High Similarity	NPC470614
0.8625	High Similarity	NPC1272
0.8608	High Similarity	NPC96362
0.859	High Similarity	NPC472342
0.859	High Similarity	NPC301707
0.859	High Similarity	NPC318136
0.859	High Similarity	NPC312328
0.8588	High Similarity	NPC475806
0.8588	High Similarity	NPC41554
0.8588	High Similarity	NPC97404
0.8588	High Similarity	NPC473998
0.8571	High Similarity	NPC265588
0.8571	High Similarity	NPC38141
0.8571	High Similarity	NPC146554
0.8553	High Similarity	NPC91858
0.8553	High Similarity	NPC476736
0.8553	High Similarity	NPC477138
0.8553	High Similarity	NPC471797
0.8553	High Similarity	NPC100334

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 NPC209430 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	147
0.1-0.2	1515
0.2-0.3	4325
0.3-0.4	2225
0.4-0.5	489
0.5-0.6	171
0.6-0.7	166
0.7-0.8	86
0.8-0.85	21
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9189	High Similarity	NPD7339	Approved
0.9189	High Similarity	NPD6942	Approved
0.8846	High Similarity	NPD7525	Registered
0.8816	High Similarity	NPD3701	Clinical (unspecified phase)
0.8554	High Similarity	NPD4751	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD4786	Approved
0.8312	Intermediate Similarity	NPD6926	Approved
0.8312	Intermediate Similarity	NPD6924	Approved
0.8289	Intermediate Similarity	NPD4243	Approved
0.825	Intermediate Similarity	NPD6929	Approved
0.825	Intermediate Similarity	NPD7645	Phase 2
0.8171	Intermediate Similarity	NPD3667	Approved
0.8148	Intermediate Similarity	NPD6930	Phase 2
0.8148	Intermediate Similarity	NPD6931	Approved
0.814	Intermediate Similarity	NPD5328	Approved
0.8101	Intermediate Similarity	NPD6933	Approved
0.8077	Intermediate Similarity	NPD4784	Approved
0.8077	Intermediate Similarity	NPD4785	Approved
0.8052	Intermediate Similarity	NPD7151	Approved
0.8052	Intermediate Similarity	NPD7152	Approved
0.8052	Intermediate Similarity	NPD7150	Approved
0.8026	Intermediate Similarity	NPD6923	Approved
0.8026	Intermediate Similarity	NPD6922	Approved
0.8	Intermediate Similarity	NPD3618	Phase 1
0.8	Intermediate Similarity	NPD5776	Phase 2
0.8	Intermediate Similarity	NPD6925	Approved
0.7975	Intermediate Similarity	NPD8264	Approved
0.7955	Intermediate Similarity	NPD6079	Approved
0.7927	Intermediate Similarity	NPD4748	Discontinued
0.7927	Intermediate Similarity	NPD7514	Phase 3
0.7922	Intermediate Similarity	NPD7144	Approved
0.7922	Intermediate Similarity	NPD7143	Approved
0.7901	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD7145	Approved
0.7857	Intermediate Similarity	NPD6695	Phase 3
0.7831	Intermediate Similarity	NPD6902	Approved
0.7765	Intermediate Similarity	NPD3133	Approved
0.7765	Intermediate Similarity	NPD3666	Approved
0.7765	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD3665	Phase 1
0.775	Intermediate Similarity	NPD5275	Approved
0.775	Intermediate Similarity	NPD4190	Phase 3
0.7711	Intermediate Similarity	NPD7509	Discontinued
0.7711	Intermediate Similarity	NPD7332	Phase 2
0.7674	Intermediate Similarity	NPD6893	Approved
0.7667	Intermediate Similarity	NPD4202	Approved
0.759	Intermediate Similarity	NPD4195	Approved
0.7561	Intermediate Similarity	NPD6932	Approved
0.7553	Intermediate Similarity	NPD7639	Approved
0.7553	Intermediate Similarity	NPD7640	Approved
0.75	Intermediate Similarity	NPD7750	Discontinued
0.75	Intermediate Similarity	NPD7524	Approved
0.7473	Intermediate Similarity	NPD6399	Phase 3
0.7471	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD7638	Approved
0.7419	Intermediate Similarity	NPD5222	Approved
0.7419	Intermediate Similarity	NPD5221	Approved
0.7419	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4697	Phase 3
0.7412	Intermediate Similarity	NPD6898	Phase 1
0.7396	Intermediate Similarity	NPD5211	Phase 2
0.7386	Intermediate Similarity	NPD5279	Phase 3
0.7381	Intermediate Similarity	NPD6683	Phase 2
0.7356	Intermediate Similarity	NPD3668	Phase 3
0.734	Intermediate Similarity	NPD5173	Approved
0.734	Intermediate Similarity	NPD4755	Approved
0.7333	Intermediate Similarity	NPD4753	Phase 2
0.7333	Intermediate Similarity	NPD6051	Approved
0.7326	Intermediate Similarity	NPD4223	Phase 3
0.7326	Intermediate Similarity	NPD4221	Approved
0.7273	Intermediate Similarity	NPD5329	Approved
0.7245	Intermediate Similarity	NPD5141	Approved
0.7188	Intermediate Similarity	NPD5285	Approved
0.7188	Intermediate Similarity	NPD5286	Approved
0.7188	Intermediate Similarity	NPD4696	Approved
0.7188	Intermediate Similarity	NPD4700	Approved
0.7174	Intermediate Similarity	NPD7087	Discontinued
0.7174	Intermediate Similarity	NPD7515	Phase 2
0.7159	Intermediate Similarity	NPD4197	Approved
0.7125	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD5223	Approved
0.7105	Intermediate Similarity	NPD368	Approved
0.7083	Intermediate Similarity	NPD5290	Discontinued
0.7045	Intermediate Similarity	NPD4788	Approved
0.7041	Intermediate Similarity	NPD4633	Approved
0.7041	Intermediate Similarity	NPD5226	Approved
0.7041	Intermediate Similarity	NPD5224	Approved
0.7041	Intermediate Similarity	NPD5225	Approved
0.7037	Intermediate Similarity	NPD4787	Phase 1
0.7	Intermediate Similarity	NPD4138	Approved
0.7	Intermediate Similarity	NPD5205	Approved
0.7	Intermediate Similarity	NPD4688	Approved
0.7	Intermediate Similarity	NPD6402	Approved
0.7	Intermediate Similarity	NPD4519	Discontinued
0.7	Intermediate Similarity	NPD7521	Approved
0.7	Intermediate Similarity	NPD6409	Approved
0.7	Intermediate Similarity	NPD4689	Approved
0.7	Intermediate Similarity	NPD6675	Approved
0.7	Intermediate Similarity	NPD4693	Phase 3
0.7	Intermediate Similarity	NPD5739	Approved
0.7	Intermediate Similarity	NPD7146	Approved
0.7	Intermediate Similarity	NPD6684	Approved
0.7	Intermediate Similarity	NPD4690	Approved
0.7	Intermediate Similarity	NPD4623	Approved
0.7	Intermediate Similarity	NPD5330	Approved
0.7	Intermediate Similarity	NPD7334	Approved
0.7	Intermediate Similarity	NPD7128	Approved
0.6989	Remote Similarity	NPD7637	Suspended
0.6986	Remote Similarity	NPD342	Phase 1
0.6979	Remote Similarity	NPD6084	Phase 2
0.6979	Remote Similarity	NPD6083	Phase 2
0.697	Remote Similarity	NPD5175	Approved
0.697	Remote Similarity	NPD5174	Approved
0.697	Remote Similarity	NPD4754	Approved
0.6951	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5210	Approved
0.6947	Remote Similarity	NPD4629	Approved
0.6869	Remote Similarity	NPD7632	Discontinued
0.6863	Remote Similarity	NPD7320	Approved
0.6863	Remote Similarity	NPD6899	Approved
0.6863	Remote Similarity	NPD6881	Approved
0.686	Remote Similarity	NPD3617	Approved
0.686	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4723	Approved
0.6848	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5737	Approved
0.6848	Remote Similarity	NPD6903	Approved
0.6848	Remote Similarity	NPD4722	Approved
0.6848	Remote Similarity	NPD6672	Approved
0.6842	Remote Similarity	NPD7748	Approved
0.6832	Remote Similarity	NPD4768	Approved
0.6832	Remote Similarity	NPD4767	Approved
0.6822	Remote Similarity	NPD7115	Discovery
0.6813	Remote Similarity	NPD5690	Phase 2
0.6813	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4694	Approved
0.6813	Remote Similarity	NPD5280	Approved
0.6809	Remote Similarity	NPD8034	Phase 2
0.6809	Remote Similarity	NPD8035	Phase 2
0.6796	Remote Similarity	NPD6373	Approved
0.6796	Remote Similarity	NPD6372	Approved
0.6786	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD4159	Approved
0.6765	Remote Similarity	NPD5701	Approved
0.6765	Remote Similarity	NPD5697	Approved
0.6735	Remote Similarity	NPD4225	Approved
0.6731	Remote Similarity	NPD6883	Approved
0.6731	Remote Similarity	NPD7102	Approved
0.6731	Remote Similarity	NPD7290	Approved
0.6707	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7136	Phase 2
0.6699	Remote Similarity	NPD5168	Approved
0.6699	Remote Similarity	NPD4730	Approved
0.6699	Remote Similarity	NPD6011	Approved
0.6699	Remote Similarity	NPD4729	Approved
0.6699	Remote Similarity	NPD5128	Approved
0.6667	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6869	Approved
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD6617	Approved
0.6635	Remote Similarity	NPD6013	Approved
0.6635	Remote Similarity	NPD6012	Approved
0.6635	Remote Similarity	NPD6014	Approved
0.6633	Remote Similarity	NPD7902	Approved
0.663	Remote Similarity	NPD6098	Approved
0.6629	Remote Similarity	NPD4139	Approved
0.6629	Remote Similarity	NPD4692	Approved
0.6628	Remote Similarity	NPD6117	Approved
0.6627	Remote Similarity	NPD4747	Approved
0.6604	Remote Similarity	NPD6882	Approved
0.6604	Remote Similarity	NPD8297	Approved
0.6598	Remote Similarity	NPD5695	Phase 3
0.6571	Remote Similarity	NPD4634	Approved
0.6571	Remote Similarity	NPD5250	Approved
0.6571	Remote Similarity	NPD5169	Approved
0.6571	Remote Similarity	NPD5248	Approved
0.6571	Remote Similarity	NPD5251	Approved
0.6571	Remote Similarity	NPD5247	Approved
0.6571	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5249	Phase 3
0.6571	Remote Similarity	NPD5135	Approved
0.6566	Remote Similarity	NPD5696	Approved
0.6552	Remote Similarity	NPD6116	Phase 1
0.6522	Remote Similarity	NPD1696	Phase 3
0.6517	Remote Similarity	NPD4695	Discontinued
0.6509	Remote Similarity	NPD5127	Approved
0.6509	Remote Similarity	NPD5216	Approved
0.6509	Remote Similarity	NPD5215	Approved
0.6509	Remote Similarity	NPD5217	Approved
0.6506	Remote Similarity	NPD4137	Phase 3
0.65	Remote Similarity	NPD6404	Discontinued
0.6495	Remote Similarity	NPD5771	Approved
0.6484	Remote Similarity	NPD5362	Discontinued
0.6484	Remote Similarity	NPD5332	Approved
0.6484	Remote Similarity	NPD5331	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