NPASS Compound

Structure

NPC152718 OpenBabel07101718202D 32 35 0 0 1 0 0 0 0 0999 V2000 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7023 -4.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0574 -3.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3641 -5.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0769 -4.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 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 -3.5000 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 4.7242 -4.2601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4152 -3.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 1 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 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 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 3.4641 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.0550 -5.0032 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 17 1 0 0 0 0 6 30 1 0 0 0 0 7 30 1 0 0 0 0 8 17 2 0 0 0 0 9 10 1 0 0 0 0 10 23 2 0 0 0 0 11 12 1 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 14 24 1 0 0 0 0 15 27 1 0 0 0 0 16 28 1 0 0 0 0 17 26 1 0 0 0 0 18 3 1 6 0 0 0 18 20 1 0 0 0 0 18 30 1 0 0 0 0 19 9 1 1 0 0 0 19 21 1 0 0 0 0 19 22 1 0 0 0 0 20 27 1 6 0 0 0 21 27 1 6 0 0 0 22 28 1 6 0 0 0 23 25 1 0 0 0 0 23 28 1 0 0 0 0 24 25 1 0 0 0 0 24 29 1 6 0 0 0 25 31 2 0 0 0 0 26 29 2 3 0 0 0 26 32 1 0 0 0 0 27 4 1 6 0 0 0 28 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.34
Volume:	487.646
LogP:	4.172
LogD:	4.268
LogS:	-4.864
# Rotatable Bonds:	4
TPSA:	49.74
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.528
Synthetic Accessibility Score:	4.901
Fsp3:	0.821
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.773
MDCK Permeability:	1.4164282220008317e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.102
30% Bioavailability (F30%):	0.499

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.22
Plasma Protein Binding (PPB):	89.48851013183594%
Volume Distribution (VD):	0.809
Pgp-substrate:	4.324038505554199%

ADMET: Metabolism

CYP1A2-inhibitor:	0.125
CYP1A2-substrate:	0.627
CYP2C19-inhibitor:	0.115
CYP2C19-substrate:	0.974
CYP2C9-inhibitor:	0.348
CYP2C9-substrate:	0.177
CYP2D6-inhibitor:	0.887
CYP2D6-substrate:	0.911
CYP3A4-inhibitor:	0.77
CYP3A4-substrate:	0.776

ADMET: Excretion

Clearance (CL):	7.009
Half-life (T1/2):	0.121

ADMET: Toxicity

hERG Blockers:	0.277
Human Hepatotoxicity (H-HT):	0.383
Drug-inuced Liver Injury (DILI):	0.795
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.529
Maximum Recommended Daily Dose:	0.402
Skin Sensitization:	0.925
Carcinogencity:	0.364
Eye Corrosion:	0.004
Eye Irritation:	0.011
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC152718

Natural Product ID:	NPC152718
*Common Name:**	(E)-N-[(3S,8S,9S,10R,13S,14S,17S)-17-[(1S)-1-(Dimethylamino)Ethyl]-10,13-Dimethyl-4-Oxo-1,2,3,7,8,9,11,12,14,15,16,17-Dodecahydrocyclopenta[A]Phenanthren-3-Yl]-2-Methylbut-2-Enamide
IUPAC Name:	(E)-N-[(3S,8S,9S,10R,13S,14S,17S)-17-[(1S)-1-(dimethylamino)ethyl]-10,13-dimethyl-4-oxo-1,2,3,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-yl]-2-methylbut-2-enamide
Synonyms:
Standard InCHIKey:	HZOTXNIDOKRKQY-KQFGCDFKSA-N
Standard InCHI:	InChI=1S/C28H44N2O2/c1-8-17(2)26(32)29-24-14-16-28(5)22-13-15-27(4)20(18(3)30(6)7)11-12-21(27)19(22)9-10-23(28)25(24)31/h8,10,18-22,24H,9,11-16H2,1-7H3,(H,29,32)/b17-8+/t18-,19-,20+,21-,22-,24-,27+,28+/m0/s1
SMILES:	C/C=C(/C(=N[C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@H]3CC[C@@H]2[C@@H](N(C)C)C)C)C1=O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL343780
PubChem CID:	44358068
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001194] Oxosteroids

*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
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14584959]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14643329]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9548847]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27888	Sarcococca saligna	Species	Buxaceae	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
Ki	2

Activity Type	# Activity
Individual Protein	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2668	Individual Protein	Acetylcholinesterase	Torpedo californica	IC50	=	7100.0	nM	PMID[567419]
NPT2668	Individual Protein	Acetylcholinesterase	Torpedo californica	Ki	=	5400.0	nM	PMID[567419]
NPT439	Individual Protein	Butyrylcholinesterase	Homo sapiens	IC50	=	2100.0	nM	PMID[567419]
NPT439	Individual Protein	Butyrylcholinesterase	Homo sapiens	Ki	=	3080.0	nM	PMID[567419]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	=	7079.46	nM	PMID[567420]

☑ 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 NPC152718 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	95
0.1-0.2	772
0.2-0.3	8295
0.3-0.4	18100
0.4-0.5	10585
0.5-0.6	4154
0.6-0.7	644
0.7-0.8	44
0.8-0.85	3
0.85-0.9	1
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9789	High Similarity	NPC226509
0.9588	High Similarity	NPC469958
0.91	High Similarity	NPC230677
0.8835	High Similarity	NPC175585
0.84	Intermediate Similarity	NPC184033
0.8317	Intermediate Similarity	NPC140685
0.8125	Intermediate Similarity	NPC166458
0.8119	Intermediate Similarity	NPC247220
0.8021	Intermediate Similarity	NPC311769
0.8021	Intermediate Similarity	NPC182106
0.7879	Intermediate Similarity	NPC249312
0.7835	Intermediate Similarity	NPC152684
0.7778	Intermediate Similarity	NPC259252
0.7736	Intermediate Similarity	NPC471083
0.757	Intermediate Similarity	NPC50815
0.7526	Intermediate Similarity	NPC472239
0.7477	Intermediate Similarity	NPC474001
0.7449	Intermediate Similarity	NPC21667
0.7423	Intermediate Similarity	NPC257962
0.7407	Intermediate Similarity	NPC247060
0.7404	Intermediate Similarity	NPC476754
0.7347	Intermediate Similarity	NPC472867
0.7347	Intermediate Similarity	NPC3511
0.7347	Intermediate Similarity	NPC142253
0.7339	Intermediate Similarity	NPC90538
0.7339	Intermediate Similarity	NPC474563
0.7308	Intermediate Similarity	NPC476752
0.7308	Intermediate Similarity	NPC476753
0.7257	Intermediate Similarity	NPC328052
0.7248	Intermediate Similarity	NPC58200
0.72	Intermediate Similarity	NPC181743
0.72	Intermediate Similarity	NPC16287
0.72	Intermediate Similarity	NPC87552
0.72	Intermediate Similarity	NPC178025
0.7172	Intermediate Similarity	NPC215474
0.7154	Intermediate Similarity	NPC153007
0.7129	Intermediate Similarity	NPC8571
0.7129	Intermediate Similarity	NPC60350
0.7128	Intermediate Similarity	NPC474228
0.7128	Intermediate Similarity	NPC303613
0.7117	Intermediate Similarity	NPC119329
0.71	Intermediate Similarity	NPC41539
0.708	Intermediate Similarity	NPC140251
0.708	Intermediate Similarity	NPC307903
0.7054	Intermediate Similarity	NPC55462
0.7021	Intermediate Similarity	NPC21773
0.701	Intermediate Similarity	NPC91665
0.7	Intermediate Similarity	NPC34193
0.699	Remote Similarity	NPC476293
0.6975	Remote Similarity	NPC474006
0.6961	Remote Similarity	NPC472931
0.6961	Remote Similarity	NPC472940
0.6961	Remote Similarity	NPC147513
0.6957	Remote Similarity	NPC472359
0.6947	Remote Similarity	NPC251705
0.6931	Remote Similarity	NPC3856
0.6931	Remote Similarity	NPC279639
0.6915	Remote Similarity	NPC265782
0.6915	Remote Similarity	NPC159577
0.6915	Remote Similarity	NPC2634
0.6915	Remote Similarity	NPC282593
0.6915	Remote Similarity	NPC35734
0.6915	Remote Similarity	NPC307176
0.6915	Remote Similarity	NPC251929
0.6909	Remote Similarity	NPC275686
0.6907	Remote Similarity	NPC69408
0.69	Remote Similarity	NPC4166
0.6893	Remote Similarity	NPC157479
0.6881	Remote Similarity	NPC167419
0.6875	Remote Similarity	NPC309852
0.6875	Remote Similarity	NPC476904
0.6875	Remote Similarity	NPC255021
0.6875	Remote Similarity	NPC98765
0.6857	Remote Similarity	NPC309603
0.6857	Remote Similarity	NPC473999
0.6857	Remote Similarity	NPC262043
0.6847	Remote Similarity	NPC77703
0.6842	Remote Similarity	NPC169375
0.6842	Remote Similarity	NPC234707
0.6842	Remote Similarity	NPC305501
0.6842	Remote Similarity	NPC115023
0.6842	Remote Similarity	NPC54123
0.6842	Remote Similarity	NPC25340
0.6838	Remote Similarity	NPC80834
0.6838	Remote Similarity	NPC469968
0.6832	Remote Similarity	NPC224072
0.6832	Remote Similarity	NPC311092
0.6832	Remote Similarity	NPC320514
0.6832	Remote Similarity	NPC469799
0.6832	Remote Similarity	NPC469806
0.6832	Remote Similarity	NPC469805
0.6832	Remote Similarity	NPC469804
0.6827	Remote Similarity	NPC136948
0.6822	Remote Similarity	NPC474736
0.6814	Remote Similarity	NPC475239
0.6809	Remote Similarity	NPC139397
0.6804	Remote Similarity	NPC293803
0.6796	Remote Similarity	NPC471224
0.6796	Remote Similarity	NPC29447
0.6792	Remote Similarity	NPC48010
0.6786	Remote Similarity	NPC469598
0.6786	Remote Similarity	NPC476755
0.6783	Remote Similarity	NPC24596
0.6777	Remote Similarity	NPC35037
0.6771	Remote Similarity	NPC470044
0.6771	Remote Similarity	NPC470045
0.6768	Remote Similarity	NPC82635
0.6754	Remote Similarity	NPC185929
0.6754	Remote Similarity	NPC476328
0.6737	Remote Similarity	NPC260040
0.6735	Remote Similarity	NPC7214
0.6729	Remote Similarity	NPC475806
0.6729	Remote Similarity	NPC23217
0.6729	Remote Similarity	NPC473998
0.6726	Remote Similarity	NPC474583
0.6723	Remote Similarity	NPC476813
0.6723	Remote Similarity	NPC476814
0.6702	Remote Similarity	NPC20610
0.6699	Remote Similarity	NPC214043
0.6699	Remote Similarity	NPC85774
0.6699	Remote Similarity	NPC164577
0.6695	Remote Similarity	NPC56796
0.6667	Remote Similarity	NPC193347
0.6667	Remote Similarity	NPC265789
0.6667	Remote Similarity	NPC242692
0.6667	Remote Similarity	NPC39966
0.6667	Remote Similarity	NPC93778
0.6667	Remote Similarity	NPC476290
0.6638	Remote Similarity	NPC476276
0.6636	Remote Similarity	NPC476903
0.6635	Remote Similarity	NPC469948
0.6635	Remote Similarity	NPC24733
0.6635	Remote Similarity	NPC474083
0.6634	Remote Similarity	NPC250632
0.6634	Remote Similarity	NPC469797
0.6634	Remote Similarity	NPC474509
0.6634	Remote Similarity	NPC472478
0.6634	Remote Similarity	NPC469798
0.6633	Remote Similarity	NPC469803
0.6633	Remote Similarity	NPC476346
0.6633	Remote Similarity	NPC255650
0.6632	Remote Similarity	NPC182815
0.6614	Remote Similarity	NPC471586
0.6613	Remote Similarity	NPC472458
0.6609	Remote Similarity	NPC36497
0.6609	Remote Similarity	NPC233256
0.6609	Remote Similarity	NPC195841
0.6606	Remote Similarity	NPC8993
0.6606	Remote Similarity	NPC477290
0.6604	Remote Similarity	NPC117122
0.6602	Remote Similarity	NPC97913
0.66	Remote Similarity	NPC470052
0.6598	Remote Similarity	NPC56747
0.6598	Remote Similarity	NPC109576
0.6598	Remote Similarity	NPC180015
0.6598	Remote Similarity	NPC130016
0.6579	Remote Similarity	NPC45365
0.6579	Remote Similarity	NPC293299
0.6574	Remote Similarity	NPC204341
0.6571	Remote Similarity	NPC474732
0.6571	Remote Similarity	NPC186975
0.6571	Remote Similarity	NPC469994
0.6571	Remote Similarity	NPC474733
0.6571	Remote Similarity	NPC31564
0.6571	Remote Similarity	NPC145879
0.6571	Remote Similarity	NPC472869
0.6571	Remote Similarity	NPC474778
0.6569	Remote Similarity	NPC147066
0.6569	Remote Similarity	NPC90150
0.6569	Remote Similarity	NPC477372
0.6555	Remote Similarity	NPC124358
0.6555	Remote Similarity	NPC476269
0.6545	Remote Similarity	NPC476174
0.6545	Remote Similarity	NPC271195
0.6542	Remote Similarity	NPC2983
0.6538	Remote Similarity	NPC472865
0.6538	Remote Similarity	NPC237712
0.6538	Remote Similarity	NPC144258
0.6538	Remote Similarity	NPC476412
0.6538	Remote Similarity	NPC473246
0.6538	Remote Similarity	NPC472864
0.6538	Remote Similarity	NPC19849
0.6535	Remote Similarity	NPC170793
0.6535	Remote Similarity	NPC90965
0.6535	Remote Similarity	NPC215843
0.6531	Remote Similarity	NPC474797
0.6531	Remote Similarity	NPC329866
0.6531	Remote Similarity	NPC474796
0.6529	Remote Similarity	NPC288629
0.6525	Remote Similarity	NPC72688
0.6518	Remote Similarity	NPC103051
0.6514	Remote Similarity	NPC69454
0.6514	Remote Similarity	NPC109305
0.6514	Remote Similarity	NPC472930
0.6509	Remote Similarity	NPC58063
0.6509	Remote Similarity	NPC236618
0.6509	Remote Similarity	NPC475740
0.6505	Remote Similarity	NPC477583
0.6505	Remote Similarity	NPC283277
0.6505	Remote Similarity	NPC477581

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 NPC152718 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	89
0.1-0.2	412
0.2-0.3	2534
0.3-0.4	4497
0.4-0.5	1272
0.5-0.6	261
0.6-0.7	80
0.7-0.8	4
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.81	Intermediate Similarity	NPD5769	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD6404	Discontinued
0.7075	Intermediate Similarity	NPD5771	Approved
0.6964	Remote Similarity	NPD7812	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD4691	Approved
0.6915	Remote Similarity	NPD4747	Approved
0.6809	Remote Similarity	NPD4137	Phase 3
0.6765	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4058	Approved
0.6701	Remote Similarity	NPD5733	Approved
0.6667	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD4221	Approved
0.6635	Remote Similarity	NPD5329	Approved
0.6609	Remote Similarity	NPD7333	Discontinued
0.6538	Remote Similarity	NPD4197	Approved
0.6531	Remote Similarity	NPD4687	Approved
0.6495	Remote Similarity	NPD5276	Approved
0.6422	Remote Similarity	NPD6079	Approved
0.6415	Remote Similarity	NPD4138	Approved
0.6415	Remote Similarity	NPD4690	Approved
0.6415	Remote Similarity	NPD4693	Phase 3
0.6415	Remote Similarity	NPD4519	Discontinued
0.6415	Remote Similarity	NPD5690	Phase 2
0.6415	Remote Similarity	NPD5205	Approved
0.6415	Remote Similarity	NPD4688	Approved
0.6415	Remote Similarity	NPD4689	Approved
0.6415	Remote Similarity	NPD4623	Approved
0.6389	Remote Similarity	NPD5328	Approved
0.6385	Remote Similarity	NPD6914	Discontinued
0.6381	Remote Similarity	NPD3666	Approved
0.6381	Remote Similarity	NPD4786	Approved
0.6381	Remote Similarity	NPD3665	Phase 1
0.6381	Remote Similarity	NPD3133	Approved
0.6354	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.633	Remote Similarity	NPD4096	Approved
0.6275	Remote Similarity	NPD3617	Approved
0.6262	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD3618	Phase 1
0.6262	Remote Similarity	NPD4694	Approved
0.6262	Remote Similarity	NPD5280	Approved
0.625	Remote Similarity	NPD8028	Phase 2
0.6239	Remote Similarity	NPD4753	Phase 2
0.6224	Remote Similarity	NPD6939	Phase 2
0.6224	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD4195	Approved
0.619	Remote Similarity	NPD3667	Approved
0.6182	Remote Similarity	NPD6934	Discontinued
0.6154	Remote Similarity	NPD4695	Discontinued
0.6142	Remote Similarity	NPD6908	Approved
0.6142	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD6909	Approved
0.6111	Remote Similarity	NPD5279	Phase 3
0.6106	Remote Similarity	NPD4629	Approved
0.6106	Remote Similarity	NPD5210	Approved
0.6071	Remote Similarity	NPD4202	Approved
0.6068	Remote Similarity	NPD5211	Phase 2
0.6053	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD5222	Approved
0.6053	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD5221	Approved
0.6	Remote Similarity	NPD5737	Approved
0.6	Remote Similarity	NPD6083	Phase 2
0.6	Remote Similarity	NPD4723	Approved
0.6	Remote Similarity	NPD5173	Approved
0.6	Remote Similarity	NPD6672	Approved
0.6	Remote Similarity	NPD6084	Phase 2
0.6	Remote Similarity	NPD4722	Approved
0.5984	Remote Similarity	NPD6420	Discontinued
0.5982	Remote Similarity	NPD5284	Approved
0.5982	Remote Similarity	NPD5281	Approved
0.5981	Remote Similarity	NPD4788	Approved
0.5969	Remote Similarity	NPD7623	Phase 3
0.5969	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD5141	Approved
0.5963	Remote Similarity	NPD7334	Approved
0.5963	Remote Similarity	NPD6684	Approved
0.5963	Remote Similarity	NPD7521	Approved
0.5963	Remote Similarity	NPD7146	Approved
0.5963	Remote Similarity	NPD6409	Approved
0.5963	Remote Similarity	NPD5330	Approved
0.5946	Remote Similarity	NPD6904	Approved
0.5946	Remote Similarity	NPD6080	Approved
0.5946	Remote Similarity	NPD6673	Approved
0.5935	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD6399	Phase 3
0.5913	Remote Similarity	NPD7614	Phase 1
0.5913	Remote Similarity	NPD4697	Phase 3
0.5909	Remote Similarity	NPD7747	Phase 1
0.5909	Remote Similarity	NPD7746	Phase 1
0.5905	Remote Similarity	NPD7155	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD4696	Approved
0.5897	Remote Similarity	NPD5285	Approved
0.5897	Remote Similarity	NPD5286	Approved
0.5862	Remote Similarity	NPD4755	Approved
0.5856	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD6903	Approved
0.5856	Remote Similarity	NPD5208	Approved
0.5847	Remote Similarity	NPD5223	Approved
0.5841	Remote Similarity	NPD5693	Phase 1
0.584	Remote Similarity	NPD8298	Phase 2
0.5826	Remote Similarity	NPD5695	Phase 3
0.5818	Remote Similarity	NPD6098	Approved
0.5812	Remote Similarity	NPD5696	Approved
0.5798	Remote Similarity	NPD5224	Approved
0.5798	Remote Similarity	NPD5091	Approved
0.5798	Remote Similarity	NPD5226	Approved
0.5798	Remote Similarity	NPD5225	Approved
0.5798	Remote Similarity	NPD4633	Approved
0.5794	Remote Similarity	NPD4139	Approved
0.5794	Remote Similarity	NPD4692	Approved
0.5789	Remote Similarity	NPD5133	Approved
0.578	Remote Similarity	NPD3668	Phase 3
0.5763	Remote Similarity	NPD8418	Phase 2
0.5763	Remote Similarity	NPD4700	Approved
0.5752	Remote Similarity	NPD790	Approved
0.575	Remote Similarity	NPD5175	Approved
0.575	Remote Similarity	NPD5174	Approved
0.5739	Remote Similarity	NPD5707	Approved
0.5714	Remote Similarity	NPD6333	Approved
0.5714	Remote Similarity	NPD6334	Approved
0.5714	Remote Similarity	NPD4518	Approved
0.5703	Remote Similarity	NPD7115	Discovery
0.5703	Remote Similarity	NPD7500	Approved
0.5702	Remote Similarity	NPD6050	Approved
0.5702	Remote Similarity	NPD7515	Phase 2
0.5691	Remote Similarity	NPD6899	Approved
0.5691	Remote Similarity	NPD6881	Approved
0.569	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD4243	Approved
0.5664	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.566	Remote Similarity	NPD4776	Phase 2
0.566	Remote Similarity	NPD4777	Suspended
0.566	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD7128	Approved
0.5656	Remote Similarity	NPD6675	Approved
0.5656	Remote Similarity	NPD5739	Approved
0.5656	Remote Similarity	NPD6402	Approved
0.563	Remote Similarity	NPD7640	Approved
0.563	Remote Similarity	NPD7639	Approved
0.562	Remote Similarity	NPD7260	Phase 2
0.562	Remote Similarity	NPD4754	Approved
0.5619	Remote Similarity	NPD1346	Approved
0.5614	Remote Similarity	NPD5207	Approved
0.5614	Remote Similarity	NPD5692	Phase 3
0.561	Remote Similarity	NPD5697	Approved
0.5603	Remote Similarity	NPD6001	Approved
0.5603	Remote Similarity	NPD7748	Approved
0.56	Remote Similarity	NPD7102	Approved
0.56	Remote Similarity	NPD6883	Approved
0.56	Remote Similarity	NPD7290	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