NPASS Compound

Structure

NPC474216 OpenBabel07101718272D 29 32 0 0 1 0 0 0 0 0999 V2000 1.5417 4.0385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1816 5.7327 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 0.0000 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 3.1890 3.5032 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 -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 3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4980 4.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 2.0000 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 1.8508 4.9895 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 -0.0000 -1.0000 0.0000 C 0 0 0 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 1.7321 -0.0000 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 2.5981 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 2.8289 5.1974 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 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 3.1379 6.1485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 2 0 0 0 0 2 17 1 0 0 0 0 6 11 1 0 0 0 0 6 18 1 0 0 0 0 7 8 1 0 0 0 0 7 19 2 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 25 1 0 0 0 0 12 14 1 0 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 13 24 1 0 0 0 0 14 26 1 0 0 0 0 15 27 1 0 0 0 0 16 19 1 0 0 0 0 16 20 1 0 0 0 0 17 25 1 0 0 0 0 18 3 1 1 0 0 0 18 22 1 0 0 0 0 19 26 1 0 0 0 0 20 28 1 1 0 0 0 21 8 1 6 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 22 27 1 1 0 0 0 23 27 1 1 0 0 0 24 26 1 1 0 0 0 25 29 1 0 0 0 0 26 4 1 1 0 0 0 27 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	400.33
Volume:	453.63
LogP:	5.922
LogD:	5.282
LogS:	-5.147
# 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:	0.533
Synthetic Accessibility Score:	4.515
Fsp3:	0.852
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:	-4.661
MDCK Permeability:	1.6969073840300553e-05
Pgp-inhibitor:	0.977
Pgp-substrate:	0.3
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.971
30% Bioavailability (F30%):	0.578

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.309
Plasma Protein Binding (PPB):	95.87806701660156%
Volume Distribution (VD):	1.177
Pgp-substrate:	2.331589937210083%

ADMET: Metabolism

CYP1A2-inhibitor:	0.131
CYP1A2-substrate:	0.548
CYP2C19-inhibitor:	0.09
CYP2C19-substrate:	0.872
CYP2C9-inhibitor:	0.198
CYP2C9-substrate:	0.223
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.866
CYP3A4-inhibitor:	0.484
CYP3A4-substrate:	0.385

ADMET: Excretion

Clearance (CL):	8.789
Half-life (T1/2):	0.062

ADMET: Toxicity

hERG Blockers:	0.248
Human Hepatotoxicity (H-HT):	0.283
Drug-inuced Liver Injury (DILI):	0.166
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.882
Skin Sensitization:	0.942
Carcinogencity:	0.305
Eye Corrosion:	0.018
Eye Irritation:	0.315
Respiratory Toxicity:	0.92

Download Data

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

Natural Product: NPC474216

Natural Product ID:	NPC474216
*Common Name:**	Cholesta-5,25-Diene-3Beta,24Xi-Diol
IUPAC Name:	(3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-5-hydroxy-6-methylhept-6-en-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:	ZMXYZGGHZJZSCJ-GHMQSXNDSA-N
Standard InCHI:	InChI=1S/C27H44O2/c1-17(2)25(29)11-6-18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,18,20-25,28-29H,1,6,8-16H2,2-5H3/t18-,20+,21+,22-,23+,24+,25?,26+,27-/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](CCC(C(=C)C)O)C)C)C1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463573
PubChem CID:	13022702
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:0000516] Dihydroxy 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
NPO33302	galaxaura marginata	Species	Galaxauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8984148]
NPO33302	galaxaura marginata	Species	Galaxauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9322362]

☑ 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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.36	ug ml-1	PMID[513034]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.67	ug ml-1	PMID[513034]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	1.61	ug ml-1	PMID[513034]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	0.37	ug ml-1	PMID[513034]

☑ 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 NPC474216 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	146
0.1-0.2	1264
0.2-0.3	6059
0.3-0.4	15866
0.4-0.5	7751
0.5-0.6	5781
0.6-0.7	4134
0.7-0.8	1271
0.8-0.85	238
0.85-0.9	96
0.9-0.95	57
0.95-1	34

Similarity Score	Similarity Level	Natural Product ID
0.9863	High Similarity	NPC109546
0.9863	High Similarity	NPC84694
0.9863	High Similarity	NPC81306
0.9863	High Similarity	NPC47982
0.9863	High Similarity	NPC28862
0.9863	High Similarity	NPC143182
0.973	High Similarity	NPC234193
0.973	High Similarity	NPC241290
0.973	High Similarity	NPC164840
0.973	High Similarity	NPC209944
0.9726	High Similarity	NPC473943
0.9722	High Similarity	NPC107059
0.9722	High Similarity	NPC321016
0.9722	High Similarity	NPC321381
0.96	High Similarity	NPC264245
0.96	High Similarity	NPC23852
0.96	High Similarity	NPC209620
0.9595	High Similarity	NPC209430
0.9595	High Similarity	NPC30986
0.9589	High Similarity	NPC155986
0.9589	High Similarity	NPC198968
0.9589	High Similarity	NPC318495
0.9583	High Similarity	NPC136188
0.9583	High Similarity	NPC285893
0.9583	High Similarity	NPC288035
0.9583	High Similarity	NPC134847
0.9583	High Similarity	NPC28657
0.9583	High Similarity	NPC304309
0.9583	High Similarity	NPC162742
0.9583	High Similarity	NPC22105
0.9583	High Similarity	NPC230301
0.9474	High Similarity	NPC49964
0.9474	High Similarity	NPC50964
0.9474	High Similarity	NPC189972
0.9474	High Similarity	NPC101462
0.9459	High Similarity	NPC87604
0.9459	High Similarity	NPC477522
0.9452	High Similarity	NPC247325
0.9452	High Similarity	NPC240604
0.9452	High Similarity	NPC244488
0.9452	High Similarity	NPC300324
0.9452	High Similarity	NPC113733
0.9351	High Similarity	NPC475789
0.9351	High Similarity	NPC474634
0.9351	High Similarity	NPC317458
0.9342	High Similarity	NPC474683
0.9342	High Similarity	NPC474752
0.9342	High Similarity	NPC47761
0.9342	High Similarity	NPC474759
0.9342	High Similarity	NPC7505
0.9342	High Similarity	NPC82986
0.9342	High Similarity	NPC474731
0.9333	High Similarity	NPC328714
0.9324	High Similarity	NPC34019
0.9315	High Similarity	NPC257347
0.9315	High Similarity	NPC141071
0.9315	High Similarity	NPC471723
0.9231	High Similarity	NPC185568
0.9231	High Similarity	NPC205845
0.9211	High Similarity	NPC26117
0.92	High Similarity	NPC76931
0.92	High Similarity	NPC307965
0.92	High Similarity	NPC477514
0.92	High Similarity	NPC275910
0.92	High Similarity	NPC18603
0.9189	High Similarity	NPC129165
0.9189	High Similarity	NPC189883
0.9189	High Similarity	NPC96319
0.9189	High Similarity	NPC134330
0.9178	High Similarity	NPC469534
0.9178	High Similarity	NPC469593
0.9178	High Similarity	NPC469533
0.9114	High Similarity	NPC274448
0.9114	High Similarity	NPC266511
0.9091	High Similarity	NPC470383
0.9091	High Similarity	NPC474531
0.9079	High Similarity	NPC1319
0.9067	High Similarity	NPC214570
0.9041	High Similarity	NPC474140
0.9041	High Similarity	NPC471799
0.9	High Similarity	NPC261266
0.9	High Similarity	NPC152808
0.9	High Similarity	NPC293287
0.9	High Similarity	NPC6391
0.8987	High Similarity	NPC238485
0.8987	High Similarity	NPC474047
0.8974	High Similarity	NPC5985
0.8974	High Similarity	NPC202389
0.8974	High Similarity	NPC296701
0.8974	High Similarity	NPC470614
0.8974	High Similarity	NPC218616
0.8974	High Similarity	NPC470049
0.8974	High Similarity	NPC87489
0.8974	High Similarity	NPC1272
0.8961	High Similarity	NPC236112
0.8947	High Similarity	NPC83351
0.8947	High Similarity	NPC167891
0.8947	High Similarity	NPC167037
0.8947	High Similarity	NPC285761
0.8947	High Similarity	NPC6978
0.8947	High Similarity	NPC138621
0.8947	High Similarity	NPC244385
0.8933	High Similarity	NPC237460
0.8933	High Similarity	NPC73875
0.8933	High Similarity	NPC202642
0.8933	High Similarity	NPC470362
0.8933	High Similarity	NPC46160
0.8919	High Similarity	NPC471797
0.8889	High Similarity	NPC149224
0.8875	High Similarity	NPC157257
0.8861	High Similarity	NPC470384
0.8831	High Similarity	NPC273410
0.8831	High Similarity	NPC80530
0.8816	High Similarity	NPC91594
0.88	High Similarity	NPC322353
0.88	High Similarity	NPC121744
0.88	High Similarity	NPC185536
0.88	High Similarity	NPC118508
0.878	High Similarity	NPC474668
0.8767	High Similarity	NPC34834
0.875	High Similarity	NPC209802
0.875	High Similarity	NPC124172
0.875	High Similarity	NPC59453
0.875	High Similarity	NPC33913
0.875	High Similarity	NPC231310
0.875	High Similarity	NPC472265
0.875	High Similarity	NPC160209
0.875	High Similarity	NPC221758
0.875	High Similarity	NPC208999
0.875	High Similarity	NPC470077
0.8734	High Similarity	NPC201852
0.8734	High Similarity	NPC30166
0.8734	High Similarity	NPC248886
0.8718	High Similarity	NPC102253
0.8718	High Similarity	NPC13554
0.8718	High Similarity	NPC236237
0.8718	High Similarity	NPC322313
0.8701	High Similarity	NPC476314
0.8701	High Similarity	NPC85346
0.8701	High Similarity	NPC65897
0.8701	High Similarity	NPC186191
0.8701	High Similarity	NPC205455
0.8701	High Similarity	NPC302041
0.8684	High Similarity	NPC265588
0.8675	High Similarity	NPC146554
0.8675	High Similarity	NPC477606
0.8675	High Similarity	NPC470361
0.8667	High Similarity	NPC329090
0.8667	High Similarity	NPC243342
0.8667	High Similarity	NPC477138
0.8667	High Similarity	NPC27395
0.8649	High Similarity	NPC242001
0.8642	High Similarity	NPC474349
0.8642	High Similarity	NPC471224
0.8642	High Similarity	NPC470360
0.8642	High Similarity	NPC318390
0.8642	High Similarity	NPC474189
0.8625	High Similarity	NPC82623
0.8608	High Similarity	NPC476646
0.859	High Similarity	NPC472463
0.8571	High Similarity	NPC119355
0.8571	High Similarity	NPC470758
0.8571	High Similarity	NPC248830
0.8571	High Similarity	NPC204188
0.8571	High Similarity	NPC471798
0.8571	High Similarity	NPC331618
0.8571	High Similarity	NPC80561
0.8571	High Similarity	NPC329596
0.8571	High Similarity	NPC212241
0.8571	High Similarity	NPC470711
0.8571	High Similarity	NPC295668
0.8571	High Similarity	NPC3345
0.8571	High Similarity	NPC257191
0.8571	High Similarity	NPC291484
0.8571	High Similarity	NPC48010
0.8571	High Similarity	NPC11216
0.8554	High Similarity	NPC133588
0.8554	High Similarity	NPC67872
0.8554	High Similarity	NPC471952
0.8553	High Similarity	NPC291503
0.8553	High Similarity	NPC66566
0.8553	High Similarity	NPC319090
0.8553	High Similarity	NPC471468
0.8553	High Similarity	NPC477923
0.8553	High Similarity	NPC328104
0.8537	High Similarity	NPC299068
0.8537	High Similarity	NPC145879
0.8537	High Similarity	NPC51014
0.8537	High Similarity	NPC31564
0.8537	High Similarity	NPC24277
0.8537	High Similarity	NPC474732
0.8537	High Similarity	NPC477604
0.8537	High Similarity	NPC474778
0.8537	High Similarity	NPC469994
0.8537	High Similarity	NPC474733
0.8537	High Similarity	NPC155011
0.8537	High Similarity	NPC94462
0.8537	High Similarity	NPC474970
0.8533	High Similarity	NPC472506
0.8533	High Similarity	NPC182717

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 NPC474216 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	1487
0.2-0.3	4331
0.3-0.4	2210
0.4-0.5	532
0.5-0.6	177
0.6-0.7	161
0.7-0.8	70
0.8-0.85	25
0.85-0.9	9
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9583	High Similarity	NPD7339	Approved
0.9583	High Similarity	NPD6942	Approved
0.9189	High Similarity	NPD3701	Clinical (unspecified phase)
0.875	High Similarity	NPD4786	Approved
0.8718	High Similarity	NPD7525	Registered
0.8667	High Similarity	NPD6926	Approved
0.8667	High Similarity	NPD6924	Approved
0.8659	High Similarity	NPD4751	Clinical (unspecified phase)
0.859	High Similarity	NPD6929	Approved
0.85	High Similarity	NPD3667	Approved
0.8481	Intermediate Similarity	NPD6930	Phase 2
0.8481	Intermediate Similarity	NPD6931	Approved
0.8442	Intermediate Similarity	NPD6933	Approved
0.8421	Intermediate Similarity	NPD4785	Approved
0.8421	Intermediate Similarity	NPD4784	Approved
0.84	Intermediate Similarity	NPD7150	Approved
0.84	Intermediate Similarity	NPD4243	Approved
0.84	Intermediate Similarity	NPD7152	Approved
0.84	Intermediate Similarity	NPD7151	Approved
0.8378	Intermediate Similarity	NPD6923	Approved
0.8378	Intermediate Similarity	NPD6922	Approved
0.8333	Intermediate Similarity	NPD6925	Approved
0.8333	Intermediate Similarity	NPD5776	Phase 2
0.8267	Intermediate Similarity	NPD7144	Approved
0.8267	Intermediate Similarity	NPD7143	Approved
0.8228	Intermediate Similarity	NPD7145	Approved
0.8171	Intermediate Similarity	NPD6695	Phase 3
0.8125	Intermediate Similarity	NPD7645	Phase 2
0.8072	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD7514	Phase 3
0.8025	Intermediate Similarity	NPD4748	Discontinued
0.8023	Intermediate Similarity	NPD5328	Approved
0.8	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD6893	Approved
0.7927	Intermediate Similarity	NPD6902	Approved
0.7882	Intermediate Similarity	NPD3618	Phase 1
0.7875	Intermediate Similarity	NPD6932	Approved
0.7857	Intermediate Similarity	NPD3665	Phase 1
0.7857	Intermediate Similarity	NPD3133	Approved
0.7857	Intermediate Similarity	NPD3666	Approved
0.7848	Intermediate Similarity	NPD4190	Phase 3
0.7848	Intermediate Similarity	NPD5275	Approved
0.7848	Intermediate Similarity	NPD8264	Approved
0.7841	Intermediate Similarity	NPD6079	Approved
0.7805	Intermediate Similarity	NPD7332	Phase 2
0.7805	Intermediate Similarity	NPD7509	Discontinued
0.7791	Intermediate Similarity	NPD7524	Approved
0.7791	Intermediate Similarity	NPD7750	Discontinued
0.7753	Intermediate Similarity	NPD6399	Phase 3
0.7711	Intermediate Similarity	NPD6898	Phase 1
0.7683	Intermediate Similarity	NPD4195	Approved
0.7683	Intermediate Similarity	NPD6683	Phase 2
0.7647	Intermediate Similarity	NPD3668	Phase 3
0.7556	Intermediate Similarity	NPD4202	Approved
0.7471	Intermediate Similarity	NPD5279	Phase 3
0.7444	Intermediate Similarity	NPD7087	Discontinued
0.7416	Intermediate Similarity	NPD4753	Phase 2
0.7412	Intermediate Similarity	NPD4223	Phase 3
0.7412	Intermediate Similarity	NPD4221	Approved
0.7356	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD5329	Approved
0.7312	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5221	Approved
0.7312	Intermediate Similarity	NPD4697	Phase 3
0.7312	Intermediate Similarity	NPD5222	Approved
0.7292	Intermediate Similarity	NPD5211	Phase 2
0.7263	Intermediate Similarity	NPD7639	Approved
0.7263	Intermediate Similarity	NPD7640	Approved
0.7241	Intermediate Similarity	NPD4197	Approved
0.7234	Intermediate Similarity	NPD5173	Approved
0.7234	Intermediate Similarity	NPD4755	Approved
0.7222	Intermediate Similarity	NPD6051	Approved
0.7158	Intermediate Similarity	NPD7638	Approved
0.7143	Intermediate Similarity	NPD5141	Approved
0.7126	Intermediate Similarity	NPD4788	Approved
0.7083	Intermediate Similarity	NPD5285	Approved
0.7083	Intermediate Similarity	NPD5286	Approved
0.7083	Intermediate Similarity	NPD4700	Approved
0.7083	Intermediate Similarity	NPD4696	Approved
0.7079	Intermediate Similarity	NPD4688	Approved
0.7079	Intermediate Similarity	NPD6409	Approved
0.7079	Intermediate Similarity	NPD7146	Approved
0.7079	Intermediate Similarity	NPD6684	Approved
0.7079	Intermediate Similarity	NPD5330	Approved
0.7079	Intermediate Similarity	NPD4693	Phase 3
0.7079	Intermediate Similarity	NPD4689	Approved
0.7079	Intermediate Similarity	NPD4690	Approved
0.7079	Intermediate Similarity	NPD5205	Approved
0.7079	Intermediate Similarity	NPD4138	Approved
0.7079	Intermediate Similarity	NPD7521	Approved
0.7079	Intermediate Similarity	NPD7334	Approved
0.7065	Intermediate Similarity	NPD7637	Suspended
0.7065	Intermediate Similarity	NPD7515	Phase 2
0.7053	Intermediate Similarity	NPD6084	Phase 2
0.7053	Intermediate Similarity	NPD6083	Phase 2
0.7021	Intermediate Similarity	NPD5210	Approved
0.7021	Intermediate Similarity	NPD4629	Approved
0.701	Intermediate Similarity	NPD5223	Approved
0.7	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD5290	Discontinued
0.6974	Remote Similarity	NPD368	Approved
0.6957	Remote Similarity	NPD7136	Phase 2
0.6941	Remote Similarity	NPD3617	Approved
0.6939	Remote Similarity	NPD5226	Approved
0.6939	Remote Similarity	NPD4633	Approved
0.6939	Remote Similarity	NPD5224	Approved
0.6939	Remote Similarity	NPD5225	Approved
0.6923	Remote Similarity	NPD4723	Approved
0.6923	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6672	Approved
0.6923	Remote Similarity	NPD4722	Approved
0.6923	Remote Similarity	NPD6903	Approved
0.6923	Remote Similarity	NPD5737	Approved
0.6914	Remote Similarity	NPD4787	Phase 1
0.69	Remote Similarity	NPD6402	Approved
0.69	Remote Similarity	NPD7128	Approved
0.69	Remote Similarity	NPD5739	Approved
0.69	Remote Similarity	NPD6675	Approved
0.6889	Remote Similarity	NPD4694	Approved
0.6889	Remote Similarity	NPD5280	Approved
0.6889	Remote Similarity	NPD5690	Phase 2
0.6889	Remote Similarity	NPD4623	Approved
0.6889	Remote Similarity	NPD4519	Discontinued
0.6869	Remote Similarity	NPD5175	Approved
0.6869	Remote Similarity	NPD4754	Approved
0.6869	Remote Similarity	NPD5174	Approved
0.6849	Remote Similarity	NPD342	Phase 1
0.6829	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD4695	Discontinued
0.6765	Remote Similarity	NPD7320	Approved
0.6765	Remote Similarity	NPD6881	Approved
0.6765	Remote Similarity	NPD6899	Approved
0.6744	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD7748	Approved
0.6733	Remote Similarity	NPD4767	Approved
0.6733	Remote Similarity	NPD4768	Approved
0.6729	Remote Similarity	NPD7115	Discovery
0.6707	Remote Similarity	NPD4747	Approved
0.6705	Remote Similarity	NPD4139	Approved
0.6705	Remote Similarity	NPD4692	Approved
0.6703	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD6098	Approved
0.6702	Remote Similarity	NPD8035	Phase 2
0.6702	Remote Similarity	NPD8034	Phase 2
0.6699	Remote Similarity	NPD6373	Approved
0.6699	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD4159	Approved
0.6667	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6635	Remote Similarity	NPD6883	Approved
0.6635	Remote Similarity	NPD7102	Approved
0.6635	Remote Similarity	NPD7290	Approved
0.6633	Remote Similarity	NPD4225	Approved
0.6633	Remote Similarity	NPD5696	Approved
0.6602	Remote Similarity	NPD6011	Approved
0.6602	Remote Similarity	NPD5168	Approved
0.6602	Remote Similarity	NPD4730	Approved
0.6602	Remote Similarity	NPD5128	Approved
0.6602	Remote Similarity	NPD4729	Approved
0.66	Remote Similarity	NPD7632	Discontinued
0.6585	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4137	Phase 3
0.6585	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD8130	Phase 1
0.6571	Remote Similarity	NPD6847	Approved
0.6571	Remote Similarity	NPD6649	Approved
0.6571	Remote Similarity	NPD6650	Approved
0.6571	Remote Similarity	NPD6869	Approved
0.6571	Remote Similarity	NPD6617	Approved
0.6556	Remote Similarity	NPD5362	Discontinued
0.6556	Remote Similarity	NPD5332	Approved
0.6556	Remote Similarity	NPD5331	Approved
0.6538	Remote Similarity	NPD6012	Approved
0.6538	Remote Similarity	NPD6014	Approved
0.6538	Remote Similarity	NPD6013	Approved
0.6531	Remote Similarity	NPD7902	Approved
0.6526	Remote Similarity	NPD5284	Approved
0.6526	Remote Similarity	NPD5281	Approved
0.6517	Remote Similarity	NPD4790	Discontinued
0.6512	Remote Similarity	NPD6117	Approved
0.6509	Remote Similarity	NPD6882	Approved
0.6509	Remote Similarity	NPD8297	Approved
0.6506	Remote Similarity	NPD4244	Approved
0.6506	Remote Similarity	NPD4691	Approved
0.6506	Remote Similarity	NPD4789	Approved
0.6506	Remote Similarity	NPD4245	Approved
0.6505	Remote Similarity	NPD6412	Phase 2
0.65	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6904	Approved
0.6489	Remote Similarity	NPD6080	Approved
0.6489	Remote Similarity	NPD6673	Approved
0.6476	Remote Similarity	NPD5250	Approved
0.6476	Remote Similarity	NPD5248	Approved
0.6476	Remote Similarity	NPD5251	Approved
0.6476	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD4634	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