NPASS Compound

Structure

NPC189972 OpenBabel07101718242D 27 30 0 0 1 0 0 0 0 0999 V2000 5.1116 0.7386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4570 3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4593 2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4425 1.4817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7734 2.2248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1042 2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 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 -2.5981 -1.5000 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 2.1261 2.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 2 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 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 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 -1.7321 0.0000 0.0000 C 0 0 2 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 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 6 3 0 0 0 0 6 7 1 0 0 0 0 7 16 1 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 12 1 0 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 11 21 1 0 0 0 0 12 24 1 0 0 0 0 13 25 1 0 0 0 0 14 17 1 0 0 0 0 14 18 1 0 0 0 0 15 17 2 0 0 0 0 15 22 1 0 0 0 0 16 2 1 6 0 0 0 16 19 1 0 0 0 0 17 24 1 0 0 0 0 18 26 1 1 0 0 0 19 25 1 1 0 0 0 20 23 1 0 0 0 0 20 25 1 1 0 0 0 21 23 1 0 0 0 0 21 24 1 1 0 0 0 22 23 1 0 0 0 0 22 27 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	370.29
Volume:	416.401
LogP:	4.72
LogD:	4.589
LogS:	-4.938
# Rotatable Bonds:	2
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.533
Synthetic Accessibility Score:	4.697
Fsp3:	0.84
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.668
MDCK Permeability:	1.7322981875622645e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.703
Human Intestinal Absorption (HIA):	0.036
20% Bioavailability (F20%):	0.776
30% Bioavailability (F30%):	0.383

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.655
Plasma Protein Binding (PPB):	92.85395050048828%
Volume Distribution (VD):	0.427
Pgp-substrate:	4.0816121101379395%

ADMET: Metabolism

CYP1A2-inhibitor:	0.656
CYP1A2-substrate:	0.555
CYP2C19-inhibitor:	0.848
CYP2C19-substrate:	0.91
CYP2C9-inhibitor:	0.699
CYP2C9-substrate:	0.216
CYP2D6-inhibitor:	0.101
CYP2D6-substrate:	0.596
CYP3A4-inhibitor:	0.776
CYP3A4-substrate:	0.375

ADMET: Excretion

Clearance (CL):	9.143
Half-life (T1/2):	0.245

ADMET: Toxicity

hERG Blockers:	0.195
Human Hepatotoxicity (H-HT):	0.209
Drug-inuced Liver Injury (DILI):	0.103
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.045
Maximum Recommended Daily Dose:	0.859
Skin Sensitization:	0.924
Carcinogencity:	0.301
Eye Corrosion:	0.15
Eye Irritation:	0.39
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC189972

Natural Product ID:	NPC189972
*Common Name:**	Gelliusterol A
IUPAC Name:	(3S,7S,8S,9S,10R,13R,14S,17R)-17-[(2R)-hex-4-yn-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol
Synonyms:
Standard InCHIKey:	HXKFBPDJHKTBKT-YTQPAVHCSA-N
Standard InCHI:	InChI=1S/C25H38O2/c1-5-6-7-16(2)19-8-9-20-23-21(11-13-25(19,20)4)24(3)12-10-18(26)14-17(24)15-22(23)27/h15-16,18-23,26-27H,7-14H2,1-4H3/t16-,18+,19-,20+,21+,22-,23+,24+,25-/m1/s1
SMILES:	CC#CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2[C@H](O)C=C2[C@]1(C)CC[C@@H](C2)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516472
PubChem CID:	10948675
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001295] Hydroxysteroids [CHEMONTID:0003238] 7-hydroxysteroids

*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
NPO33338	gellius sp.	Species	Chalinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11421735]

☑ 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	5

Activity Type	# Activity
Cell Line	5

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[568982]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	1.0	ug.mL-1	PMID[568982]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	1.0	ug.mL-1	PMID[568982]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	>	1.0	ug.mL-1	PMID[568982]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	>	1.0	ug.mL-1	PMID[568982]

☑ 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 NPC189972 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	153
0.1-0.2	1364
0.2-0.3	6098
0.3-0.4	16035
0.4-0.5	8008
0.5-0.6	5970
0.6-0.7	3794
0.7-0.8	1016
0.8-0.85	153
0.85-0.9	52
0.9-0.95	47
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9605	High Similarity	NPC143182
0.9605	High Similarity	NPC84694
0.9605	High Similarity	NPC28862
0.9605	High Similarity	NPC47982
0.9605	High Similarity	NPC81306
0.9605	High Similarity	NPC109546
0.9481	High Similarity	NPC234193
0.9474	High Similarity	NPC474216
0.9359	High Similarity	NPC209620
0.9359	High Similarity	NPC23852
0.9359	High Similarity	NPC264245
0.9351	High Similarity	NPC30986
0.9351	High Similarity	NPC209430
0.9241	High Similarity	NPC101462
0.9241	High Similarity	NPC50964
0.9241	High Similarity	NPC49964
0.9231	High Similarity	NPC241290
0.9231	High Similarity	NPC209944
0.9231	High Similarity	NPC164840
0.9221	High Similarity	NPC473943
0.9211	High Similarity	NPC321016
0.9211	High Similarity	NPC244488
0.9211	High Similarity	NPC247325
0.9211	High Similarity	NPC107059
0.9211	High Similarity	NPC321381
0.9125	High Similarity	NPC475789
0.9125	High Similarity	NPC317458
0.9125	High Similarity	NPC474634
0.9114	High Similarity	NPC474752
0.9114	High Similarity	NPC474759
0.9114	High Similarity	NPC474683
0.9114	High Similarity	NPC47761
0.9114	High Similarity	NPC82986
0.9114	High Similarity	NPC474731
0.9114	High Similarity	NPC7505
0.9091	High Similarity	NPC155986
0.9091	High Similarity	NPC198968
0.9091	High Similarity	NPC318495
0.9079	High Similarity	NPC162742
0.9079	High Similarity	NPC136188
0.9079	High Similarity	NPC285893
0.9079	High Similarity	NPC22105
0.9079	High Similarity	NPC134847
0.9079	High Similarity	NPC230301
0.9079	High Similarity	NPC304309
0.9079	High Similarity	NPC28657
0.9079	High Similarity	NPC288035
0.9012	High Similarity	NPC185568
0.9012	High Similarity	NPC205845
0.8974	High Similarity	NPC87604
0.8974	High Similarity	NPC477522
0.8961	High Similarity	NPC240604
0.8961	High Similarity	NPC300324
0.8961	High Similarity	NPC113733
0.8902	High Similarity	NPC274448
0.8902	High Similarity	NPC266511
0.8861	High Similarity	NPC328714
0.8846	High Similarity	NPC34019
0.8831	High Similarity	NPC141071
0.8831	High Similarity	NPC471723
0.8831	High Similarity	NPC257347
0.8795	High Similarity	NPC261266
0.8795	High Similarity	NPC152808
0.8795	High Similarity	NPC293287
0.8795	High Similarity	NPC6391
0.878	High Similarity	NPC238485
0.878	High Similarity	NPC474047
0.8765	High Similarity	NPC296701
0.8765	High Similarity	NPC87489
0.8765	High Similarity	NPC202389
0.8765	High Similarity	NPC470049
0.8765	High Similarity	NPC218616
0.875	High Similarity	NPC26117
0.8734	High Similarity	NPC307965
0.8734	High Similarity	NPC477514
0.8734	High Similarity	NPC18603
0.8734	High Similarity	NPC83351
0.8734	High Similarity	NPC76931
0.8734	High Similarity	NPC167891
0.8734	High Similarity	NPC275910
0.8718	High Similarity	NPC96319
0.8718	High Similarity	NPC189883
0.8718	High Similarity	NPC134330
0.8718	High Similarity	NPC129165
0.8701	High Similarity	NPC469534
0.8701	High Similarity	NPC469533
0.8701	High Similarity	NPC469593
0.869	High Similarity	NPC149224
0.8675	High Similarity	NPC157257
0.8659	High Similarity	NPC470384
0.8642	High Similarity	NPC474531
0.8642	High Similarity	NPC470383
0.8625	High Similarity	NPC1319
0.8608	High Similarity	NPC91594
0.8608	High Similarity	NPC214570
0.8588	High Similarity	NPC474668
0.8571	High Similarity	NPC474140
0.8571	High Similarity	NPC471799
0.8554	High Similarity	NPC231310
0.8554	High Similarity	NPC470077
0.8553	High Similarity	NPC34834
0.8537	High Similarity	NPC1272
0.8537	High Similarity	NPC5985
0.8537	High Similarity	NPC470614
0.8519	High Similarity	NPC236112
0.85	High Similarity	NPC476314
0.85	High Similarity	NPC167037
0.85	High Similarity	NPC138621
0.85	High Similarity	NPC244385
0.85	High Similarity	NPC6978
0.85	High Similarity	NPC285761
0.8488	Intermediate Similarity	NPC146554
0.8488	Intermediate Similarity	NPC268406
0.8488	Intermediate Similarity	NPC26959
0.8488	Intermediate Similarity	NPC477606
0.8488	Intermediate Similarity	NPC470361
0.8481	Intermediate Similarity	NPC202642
0.8481	Intermediate Similarity	NPC73875
0.8481	Intermediate Similarity	NPC470362
0.8481	Intermediate Similarity	NPC237460
0.8481	Intermediate Similarity	NPC46160
0.8462	Intermediate Similarity	NPC471797
0.8452	Intermediate Similarity	NPC470360
0.8452	Intermediate Similarity	NPC318390
0.8452	Intermediate Similarity	NPC471224
0.8434	Intermediate Similarity	NPC82623
0.8415	Intermediate Similarity	NPC476646
0.8395	Intermediate Similarity	NPC80530
0.8395	Intermediate Similarity	NPC273410
0.8391	Intermediate Similarity	NPC295668
0.8391	Intermediate Similarity	NPC3345
0.8391	Intermediate Similarity	NPC291484
0.8391	Intermediate Similarity	NPC80561
0.8391	Intermediate Similarity	NPC48010
0.8391	Intermediate Similarity	NPC329596
0.8391	Intermediate Similarity	NPC204188
0.8391	Intermediate Similarity	NPC11216
0.8375	Intermediate Similarity	NPC470711
0.8375	Intermediate Similarity	NPC470758
0.8372	Intermediate Similarity	NPC133588
0.8372	Intermediate Similarity	NPC471952
0.8372	Intermediate Similarity	NPC67872
0.8354	Intermediate Similarity	NPC185536
0.8354	Intermediate Similarity	NPC322353
0.8354	Intermediate Similarity	NPC121744
0.8354	Intermediate Similarity	NPC118508
0.8353	Intermediate Similarity	NPC299068
0.8333	Intermediate Similarity	NPC221758
0.8333	Intermediate Similarity	NPC33913
0.8333	Intermediate Similarity	NPC474743
0.8333	Intermediate Similarity	NPC472265
0.8333	Intermediate Similarity	NPC124172
0.8333	Intermediate Similarity	NPC209802
0.8333	Intermediate Similarity	NPC59453
0.8313	Intermediate Similarity	NPC248886
0.8313	Intermediate Similarity	NPC30166
0.8313	Intermediate Similarity	NPC201852
0.8295	Intermediate Similarity	NPC97404
0.8295	Intermediate Similarity	NPC41554
0.8293	Intermediate Similarity	NPC295131
0.8293	Intermediate Similarity	NPC236237
0.8293	Intermediate Similarity	NPC322313
0.8293	Intermediate Similarity	NPC13554
0.8293	Intermediate Similarity	NPC96362
0.8293	Intermediate Similarity	NPC102253
0.8289	Intermediate Similarity	NPC160209
0.8289	Intermediate Similarity	NPC208999
0.8276	Intermediate Similarity	NPC309603
0.8276	Intermediate Similarity	NPC473999
0.8276	Intermediate Similarity	NPC472240
0.8276	Intermediate Similarity	NPC262858
0.8272	Intermediate Similarity	NPC65897
0.8272	Intermediate Similarity	NPC85346
0.8272	Intermediate Similarity	NPC186191
0.8272	Intermediate Similarity	NPC302041
0.8272	Intermediate Similarity	NPC205455
0.8272	Intermediate Similarity	NPC11908
0.8256	Intermediate Similarity	NPC470620
0.825	Intermediate Similarity	NPC253190
0.825	Intermediate Similarity	NPC265588
0.825	Intermediate Similarity	NPC470749
0.8235	Intermediate Similarity	NPC474083
0.8235	Intermediate Similarity	NPC474349
0.8235	Intermediate Similarity	NPC474189
0.8228	Intermediate Similarity	NPC476366
0.8228	Intermediate Similarity	NPC243342
0.8228	Intermediate Similarity	NPC477138
0.8228	Intermediate Similarity	NPC306727
0.8228	Intermediate Similarity	NPC201048
0.8228	Intermediate Similarity	NPC329090
0.8228	Intermediate Similarity	NPC27395
0.8214	Intermediate Similarity	NPC134481
0.8214	Intermediate Similarity	NPC470558
0.8205	Intermediate Similarity	NPC242001
0.8171	Intermediate Similarity	NPC472463
0.8158	Intermediate Similarity	NPC114651
0.8158	Intermediate Similarity	NPC69649
0.8158	Intermediate Similarity	NPC68703
0.8148	Intermediate Similarity	NPC212241
0.8148	Intermediate Similarity	NPC248830

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 NPC189972 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	1577
0.2-0.3	4347
0.3-0.4	2163
0.4-0.5	484
0.5-0.6	183
0.6-0.7	159
0.7-0.8	57
0.8-0.85	22
0.85-0.9	1
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9146	High Similarity	NPD4751	Clinical (unspecified phase)
0.9079	High Similarity	NPD6942	Approved
0.9079	High Similarity	NPD7339	Approved
0.8718	High Similarity	NPD3701	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD4786	Approved
0.8293	Intermediate Similarity	NPD4748	Discontinued
0.8293	Intermediate Similarity	NPD7525	Registered
0.8228	Intermediate Similarity	NPD6926	Approved
0.8228	Intermediate Similarity	NPD6924	Approved
0.8171	Intermediate Similarity	NPD6929	Approved
0.8125	Intermediate Similarity	NPD4190	Phase 3
0.8125	Intermediate Similarity	NPD5275	Approved
0.8095	Intermediate Similarity	NPD3667	Approved
0.8072	Intermediate Similarity	NPD6930	Phase 2
0.8072	Intermediate Similarity	NPD6931	Approved
0.8046	Intermediate Similarity	NPD7750	Discontinued
0.8025	Intermediate Similarity	NPD6933	Approved
0.8	Intermediate Similarity	NPD4785	Approved
0.8	Intermediate Similarity	NPD4784	Approved
0.7976	Intermediate Similarity	NPD6898	Phase 1
0.7975	Intermediate Similarity	NPD7150	Approved
0.7975	Intermediate Similarity	NPD7152	Approved
0.7975	Intermediate Similarity	NPD4243	Approved
0.7975	Intermediate Similarity	NPD7151	Approved
0.7952	Intermediate Similarity	NPD6683	Phase 2
0.7949	Intermediate Similarity	NPD6923	Approved
0.7949	Intermediate Similarity	NPD6922	Approved
0.7927	Intermediate Similarity	NPD5776	Phase 2
0.7927	Intermediate Similarity	NPD6925	Approved
0.7857	Intermediate Similarity	NPD7514	Phase 3
0.7848	Intermediate Similarity	NPD7143	Approved
0.7848	Intermediate Similarity	NPD7144	Approved
0.7831	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD7145	Approved
0.7791	Intermediate Similarity	NPD6695	Phase 3
0.7765	Intermediate Similarity	NPD6902	Approved
0.7738	Intermediate Similarity	NPD7645	Phase 2
0.7701	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7087	Discontinued
0.7683	Intermediate Similarity	NPD8264	Approved
0.7667	Intermediate Similarity	NPD6051	Approved
0.7667	Intermediate Similarity	NPD5328	Approved
0.7647	Intermediate Similarity	NPD7332	Phase 2
0.7614	Intermediate Similarity	NPD6893	Approved
0.7528	Intermediate Similarity	NPD3618	Phase 1
0.75	Intermediate Similarity	NPD6932	Approved
0.75	Intermediate Similarity	NPD3665	Phase 1
0.75	Intermediate Similarity	NPD3133	Approved
0.75	Intermediate Similarity	NPD3666	Approved
0.75	Intermediate Similarity	NPD6079	Approved
0.7444	Intermediate Similarity	NPD7524	Approved
0.7442	Intermediate Similarity	NPD7509	Discontinued
0.7419	Intermediate Similarity	NPD6399	Phase 3
0.7333	Intermediate Similarity	NPD4519	Discontinued
0.7333	Intermediate Similarity	NPD4693	Phase 3
0.7333	Intermediate Similarity	NPD4138	Approved
0.7333	Intermediate Similarity	NPD5205	Approved
0.7333	Intermediate Similarity	NPD4690	Approved
0.7333	Intermediate Similarity	NPD4623	Approved
0.7333	Intermediate Similarity	NPD4688	Approved
0.7333	Intermediate Similarity	NPD4689	Approved
0.7326	Intermediate Similarity	NPD4195	Approved
0.7303	Intermediate Similarity	NPD3668	Phase 3
0.7234	Intermediate Similarity	NPD4202	Approved
0.7195	Intermediate Similarity	NPD4787	Phase 1
0.7174	Intermediate Similarity	NPD4722	Approved
0.7174	Intermediate Similarity	NPD4723	Approved
0.7143	Intermediate Similarity	NPD7640	Approved
0.7143	Intermediate Similarity	NPD7639	Approved
0.7143	Intermediate Similarity	NPD5279	Phase 3
0.7097	Intermediate Similarity	NPD4753	Phase 2
0.7079	Intermediate Similarity	NPD4223	Phase 3
0.7079	Intermediate Similarity	NPD4221	Approved
0.7041	Intermediate Similarity	NPD7638	Approved
0.7033	Intermediate Similarity	NPD5329	Approved
0.7033	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD4697	Phase 3
0.701	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5221	Approved
0.701	Intermediate Similarity	NPD5222	Approved
0.7	Intermediate Similarity	NPD5331	Approved
0.7	Intermediate Similarity	NPD5211	Phase 2
0.7	Intermediate Similarity	NPD5332	Approved
0.6966	Remote Similarity	NPD4692	Approved
0.6966	Remote Similarity	NPD4139	Approved
0.6947	Remote Similarity	NPD7637	Suspended
0.6939	Remote Similarity	NPD5173	Approved
0.6939	Remote Similarity	NPD4755	Approved
0.6923	Remote Similarity	NPD4197	Approved
0.6863	Remote Similarity	NPD5141	Approved
0.6835	Remote Similarity	NPD368	Approved
0.6813	Remote Similarity	NPD4788	Approved
0.68	Remote Similarity	NPD5285	Approved
0.68	Remote Similarity	NPD4696	Approved
0.68	Remote Similarity	NPD5286	Approved
0.68	Remote Similarity	NPD4700	Approved
0.6774	Remote Similarity	NPD6409	Approved
0.6774	Remote Similarity	NPD6684	Approved
0.6774	Remote Similarity	NPD5330	Approved
0.6774	Remote Similarity	NPD7521	Approved
0.6774	Remote Similarity	NPD7146	Approved
0.6774	Remote Similarity	NPD7334	Approved
0.6771	Remote Similarity	NPD7515	Phase 2
0.6768	Remote Similarity	NPD6084	Phase 2
0.6768	Remote Similarity	NPD6083	Phase 2
0.6735	Remote Similarity	NPD5210	Approved
0.6735	Remote Similarity	NPD4629	Approved
0.6733	Remote Similarity	NPD5223	Approved
0.6711	Remote Similarity	NPD342	Phase 1
0.67	Remote Similarity	NPD5290	Discontinued
0.6667	Remote Similarity	NPD5225	Approved
0.6667	Remote Similarity	NPD5224	Approved
0.6667	Remote Similarity	NPD7136	Phase 2
0.6667	Remote Similarity	NPD4633	Approved
0.6667	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5226	Approved
0.6636	Remote Similarity	NPD7115	Discovery
0.6635	Remote Similarity	NPD6675	Approved
0.6635	Remote Similarity	NPD6402	Approved
0.6635	Remote Similarity	NPD7128	Approved
0.6635	Remote Similarity	NPD5739	Approved
0.6632	Remote Similarity	NPD5737	Approved
0.6632	Remote Similarity	NPD4518	Approved
0.6632	Remote Similarity	NPD6903	Approved
0.6632	Remote Similarity	NPD5208	Approved
0.6632	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6672	Approved
0.6629	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD3617	Approved
0.6602	Remote Similarity	NPD5174	Approved
0.6602	Remote Similarity	NPD5175	Approved
0.6602	Remote Similarity	NPD4754	Approved
0.6596	Remote Similarity	NPD5280	Approved
0.6596	Remote Similarity	NPD5690	Phase 2
0.6596	Remote Similarity	NPD4694	Approved
0.6569	Remote Similarity	NPD4159	Approved
0.6535	Remote Similarity	NPD4225	Approved
0.6512	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6881	Approved
0.6509	Remote Similarity	NPD6899	Approved
0.6509	Remote Similarity	NPD7320	Approved
0.6505	Remote Similarity	NPD7632	Discontinued
0.6495	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4695	Discontinued
0.6476	Remote Similarity	NPD4767	Approved
0.6476	Remote Similarity	NPD4768	Approved
0.6465	Remote Similarity	NPD5707	Approved
0.6465	Remote Similarity	NPD7748	Approved
0.6452	Remote Similarity	NPD5362	Discontinued
0.6449	Remote Similarity	NPD6373	Approved
0.6449	Remote Similarity	NPD6372	Approved
0.6429	Remote Similarity	NPD8035	Phase 2
0.6429	Remote Similarity	NPD8034	Phase 2
0.6421	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD6098	Approved
0.6415	Remote Similarity	NPD5697	Approved
0.6415	Remote Similarity	NPD5701	Approved
0.6413	Remote Similarity	NPD4790	Discontinued
0.64	Remote Similarity	NPD5695	Phase 3
0.6395	Remote Similarity	NPD4747	Approved
0.6389	Remote Similarity	NPD7290	Approved
0.6389	Remote Similarity	NPD6883	Approved
0.6389	Remote Similarity	NPD7102	Approved
0.6373	Remote Similarity	NPD5696	Approved
0.6364	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD4730	Approved
0.6355	Remote Similarity	NPD5128	Approved
0.6355	Remote Similarity	NPD6011	Approved
0.6355	Remote Similarity	NPD5168	Approved
0.6355	Remote Similarity	NPD4729	Approved
0.633	Remote Similarity	NPD8130	Phase 1
0.633	Remote Similarity	NPD6649	Approved
0.633	Remote Similarity	NPD6869	Approved
0.633	Remote Similarity	NPD6847	Approved
0.633	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.633	Remote Similarity	NPD6617	Approved
0.633	Remote Similarity	NPD6650	Approved
0.6316	Remote Similarity	NPD1696	Phase 3
0.6311	Remote Similarity	NPD6404	Discontinued
0.6304	Remote Similarity	NPD4819	Approved
0.6304	Remote Similarity	NPD4821	Approved
0.6304	Remote Similarity	NPD4822	Approved
0.6304	Remote Similarity	NPD4820	Approved
0.63	Remote Similarity	NPD5771	Approved
0.6296	Remote Similarity	NPD6014	Approved
0.6296	Remote Similarity	NPD6013	Approved
0.6296	Remote Similarity	NPD6012	Approved
0.6279	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD4137	Phase 3
0.6275	Remote Similarity	NPD7902	Approved
0.6273	Remote Similarity	NPD8297	Approved
0.6273	Remote Similarity	NPD6882	Approved
0.6264	Remote Similarity	NPD4268	Approved
0.6264	Remote Similarity	NPD4271	Approved
0.6263	Remote Similarity	NPD5281	Approved
0.6263	Remote Similarity	NPD5284	Approved
0.6262	Remote Similarity	NPD6412	Phase 2

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