NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	634.25
Volume:	632.096
LogP:	2.555
LogD:	1.7
LogS:	-3.605
# Rotatable Bonds:	11
TPSA:	178.51
# H-Bond Aceptor:	12
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.179
Synthetic Accessibility Score:	5.146
Fsp3:	0.441
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
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:	-5.885
MDCK Permeability:	1.4950835065974388e-05
Pgp-inhibitor:	0.903
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.278
20% Bioavailability (F20%):	0.95
30% Bioavailability (F30%):	0.894

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.093
Plasma Protein Binding (PPB):	97.42737579345703%
Volume Distribution (VD):	0.752
Pgp-substrate:	8.630934715270996%

ADMET: Metabolism

CYP1A2-inhibitor:	0.396
CYP1A2-substrate:	0.081
CYP2C19-inhibitor:	0.197
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.734
CYP2C9-substrate:	0.587
CYP2D6-inhibitor:	0.872
CYP2D6-substrate:	0.112
CYP3A4-inhibitor:	0.873
CYP3A4-substrate:	0.239

ADMET: Excretion

Clearance (CL):	8.531
Half-life (T1/2):	0.892

ADMET: Toxicity

hERG Blockers:	0.179
Human Hepatotoxicity (H-HT):	0.232
Drug-inuced Liver Injury (DILI):	0.947
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.254
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.672
Carcinogencity:	0.049
Eye Corrosion:	0.003
Eye Irritation:	0.054
Respiratory Toxicity:	0.036

Download Data

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

Natural Product: NPC477911

Natural Product ID:	NPC477911
*Common Name:**	[(1R,2S,3R,4S,8aR)-4-[(1S)-1-acetyloxy-2-(4-hydroxy-5-oxo-2H-furan-3-yl)ethyl]-3-hydroxy-3,4,8,8a-tetramethyl-2-(pyridine-3-carbonyloxy)-2,4a,5,6-tetrahydro-1H-naphthalen-1-yl] pyridine-3-carboxylate
IUPAC Name:	[(1R,2S,3R,4S,8aR)-4-[(1S)-1-acetyloxy-2-(4-hydroxy-5-oxo-2H-furan-3-yl)ethyl]-3-hydroxy-3,4,8,8a-tetramethyl-2-(pyridine-3-carbonyloxy)-2,4a,5,6-tetrahydro-1H-naphthalen-1-yl] pyridine-3-carboxylate
Synonyms:
Standard InCHIKey:	LOVZWLNTNWLURP-NRBCNPROSA-N
Standard InCHI:	InChI=1S/C34H38N2O10/c1-19-9-6-12-24-32(19,3)27(45-29(39)21-10-7-13-35-16-21)28(46-30(40)22-11-8-14-36-17-22)34(5,42)33(24,4)25(44-20(2)37)15-23-18-43-31(41)26(23)38/h7-11,13-14,16-17,24-25,27-28,38,42H,6,12,15,18H2,1-5H3/t24?,25-,27-,28-,32-,33-,34-/m0/s1
SMILES:	CC1=CCCC2[C@]1([C@H]([C@@H]([C@]([C@]2(C)[C@H](CC3=C(C(=O)OC3)O)OC(=O)C)(C)O)OC(=O)C4=CN=CC=C4)OC(=O)C5=CN=CC=C5)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122186902
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16755060]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17666848]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[18239311]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19785430]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19962306]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20078074]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	whole plants	Nanning District, Guangxi Province, China	2012-Sep	PMID[25647077]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	aerial parts	Seoul, Korea	n.a.	PMID[26331882]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16039	Scutellaria barbata	Species	Lamiaceae	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
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000	nM	PMID[26331882]

☑ 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 NPC477911 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	323
0.1-0.2	1390
0.2-0.3	3528
0.3-0.4	10405
0.4-0.5	18224
0.5-0.6	7110
0.6-0.7	1440
0.7-0.8	99
0.8-0.85	54
0.85-0.9	64
0.9-0.95	46
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9848	High Similarity	NPC472555
0.9746	High Similarity	NPC477908
0.9746	High Similarity	NPC206343
0.965	High Similarity	NPC477912
0.9596	High Similarity	NPC477910
0.9545	High Similarity	NPC319128
0.9543	High Similarity	NPC472553
0.95	High Similarity	NPC62367
0.9461	High Similarity	NPC148860
0.9453	High Similarity	NPC216428
0.9447	High Similarity	NPC228331
0.94	High Similarity	NPC42678
0.94	High Similarity	NPC477909
0.94	High Similarity	NPC477907
0.9391	High Similarity	NPC48042
0.9391	High Similarity	NPC472550
0.9391	High Similarity	NPC304179
0.9353	High Similarity	NPC6981
0.9307	High Similarity	NPC294579
0.9307	High Similarity	NPC144779
0.9279	High Similarity	NPC477906
0.9261	High Similarity	NPC301368
0.9261	High Similarity	NPC84815
0.9242	High Similarity	NPC63041
0.9223	High Similarity	NPC328154
0.9223	High Similarity	NPC477902
0.922	High Similarity	NPC235364
0.9208	High Similarity	NPC470306
0.9163	High Similarity	NPC475408
0.9163	High Similarity	NPC471014
0.9163	High Similarity	NPC471016
0.9135	High Similarity	NPC124029
0.913	High Similarity	NPC26881
0.913	High Similarity	NPC477899
0.913	High Similarity	NPC477900
0.9126	High Similarity	NPC127026
0.9126	High Similarity	NPC127720
0.9122	High Similarity	NPC477901
0.9082	High Similarity	NPC471980
0.9064	High Similarity	NPC4421
0.9064	High Similarity	NPC264674
0.9057	High Similarity	NPC327769
0.9043	High Similarity	NPC211920
0.9005	High Similarity	NPC292416
0.9005	High Similarity	NPC473689
0.9005	High Similarity	NPC150698
0.9005	High Similarity	NPC96801
0.8995	High Similarity	NPC289086
0.8986	High Similarity	NPC477903
0.8962	High Similarity	NPC244839
0.8962	High Similarity	NPC319880
0.8962	High Similarity	NPC320324
0.8957	High Similarity	NPC91125
0.8952	High Similarity	NPC475600
0.8952	High Similarity	NPC475631
0.8952	High Similarity	NPC328186
0.8952	High Similarity	NPC477787
0.8952	High Similarity	NPC475601
0.8952	High Similarity	NPC228377
0.8952	High Similarity	NPC87152
0.8952	High Similarity	NPC476110
0.8952	High Similarity	NPC122968
0.8952	High Similarity	NPC146824
0.8932	High Similarity	NPC473089
0.8932	High Similarity	NPC6576
0.8932	High Similarity	NPC158020
0.8932	High Similarity	NPC473115
0.8932	High Similarity	NPC212768
0.8932	High Similarity	NPC75600
0.892	High Similarity	NPC237702
0.891	High Similarity	NPC470486
0.891	High Similarity	NPC471977
0.891	High Similarity	NPC475644
0.891	High Similarity	NPC475362
0.891	High Similarity	NPC471190
0.89	High Similarity	NPC57797
0.89	High Similarity	NPC250807
0.89	High Similarity	NPC76565
0.8879	High Similarity	NPC475406
0.8857	High Similarity	NPC475137
0.8857	High Similarity	NPC473850
0.8857	High Similarity	NPC475498
0.8837	High Similarity	NPC38959
0.8837	High Similarity	NPC327904
0.8826	High Similarity	NPC475596
0.8826	High Similarity	NPC316841
0.8826	High Similarity	NPC475303
0.8815	High Similarity	NPC473506
0.8785	High Similarity	NPC469748
0.8785	High Similarity	NPC30456
0.8762	High Similarity	NPC477788
0.8716	High Similarity	NPC253482
0.8704	High Similarity	NPC170751
0.8704	High Similarity	NPC35208
0.8647	High Similarity	NPC165837
0.8604	High Similarity	NPC475533
0.8599	High Similarity	NPC476467
0.8598	High Similarity	NPC14116
0.8598	High Similarity	NPC285411
0.8597	High Similarity	NPC475648
0.8565	High Similarity	NPC475315
0.8565	High Similarity	NPC324619
0.8565	High Similarity	NPC30570
0.8558	High Similarity	NPC311196
0.8558	High Similarity	NPC134384
0.8532	High Similarity	NPC475426
0.8524	High Similarity	NPC162812
0.851	High Similarity	NPC292517
0.8486	Intermediate Similarity	NPC238278
0.8483	Intermediate Similarity	NPC319556
0.8475	Intermediate Similarity	NPC148896
0.8475	Intermediate Similarity	NPC471013
0.8475	Intermediate Similarity	NPC180668
0.8454	Intermediate Similarity	NPC472752
0.8447	Intermediate Similarity	NPC475835
0.8442	Intermediate Similarity	NPC328928
0.8421	Intermediate Similarity	NPC323551
0.8421	Intermediate Similarity	NPC280473
0.8389	Intermediate Similarity	NPC207531
0.8381	Intermediate Similarity	NPC51008
0.8381	Intermediate Similarity	NPC41724
0.8377	Intermediate Similarity	NPC471015
0.8356	Intermediate Similarity	NPC213143
0.8341	Intermediate Similarity	NPC475301
0.8341	Intermediate Similarity	NPC53255
0.8341	Intermediate Similarity	NPC85879
0.8341	Intermediate Similarity	NPC326930
0.8333	Intermediate Similarity	NPC233727
0.8326	Intermediate Similarity	NPC10904
0.8304	Intermediate Similarity	NPC13603
0.8224	Intermediate Similarity	NPC187494
0.8221	Intermediate Similarity	NPC309498
0.8199	Intermediate Similarity	NPC40919
0.8199	Intermediate Similarity	NPC470189
0.8197	Intermediate Similarity	NPC473833
0.8143	Intermediate Similarity	NPC470190
0.8128	Intermediate Similarity	NPC471978
0.8047	Intermediate Similarity	NPC62844
0.8047	Intermediate Similarity	NPC193361
0.8025	Intermediate Similarity	NPC471979
0.7991	Intermediate Similarity	NPC476090
0.7951	Intermediate Similarity	NPC103230
0.7885	Intermediate Similarity	NPC324245
0.7885	Intermediate Similarity	NPC320748
0.7857	Intermediate Similarity	NPC32451
0.781	Intermediate Similarity	NPC470279
0.781	Intermediate Similarity	NPC79223
0.7773	Intermediate Similarity	NPC328559
0.7751	Intermediate Similarity	NPC329024
0.7742	Intermediate Similarity	NPC111732
0.7709	Intermediate Similarity	NPC471004
0.7703	Intermediate Similarity	NPC253314
0.7674	Intermediate Similarity	NPC156044
0.763	Intermediate Similarity	NPC59033
0.763	Intermediate Similarity	NPC317672
0.7581	Intermediate Similarity	NPC12944
0.7581	Intermediate Similarity	NPC25442
0.7453	Intermediate Similarity	NPC109922
0.7416	Intermediate Similarity	NPC44354
0.7415	Intermediate Similarity	NPC471997
0.7404	Intermediate Similarity	NPC37473
0.7387	Intermediate Similarity	NPC317752
0.7349	Intermediate Similarity	NPC123395
0.7342	Intermediate Similarity	NPC318299
0.7333	Intermediate Similarity	NPC141385
0.733	Intermediate Similarity	NPC317010
0.7286	Intermediate Similarity	NPC328798
0.7286	Intermediate Similarity	NPC325775
0.7261	Intermediate Similarity	NPC476516
0.726	Intermediate Similarity	NPC327373
0.7243	Intermediate Similarity	NPC135950
0.7208	Intermediate Similarity	NPC107287
0.7208	Intermediate Similarity	NPC107123
0.7202	Intermediate Similarity	NPC155792
0.7189	Intermediate Similarity	NPC103361
0.7189	Intermediate Similarity	NPC50997
0.7189	Intermediate Similarity	NPC160127
0.7149	Intermediate Similarity	NPC70155
0.7122	Intermediate Similarity	NPC249614
0.7116	Intermediate Similarity	NPC289786
0.7105	Intermediate Similarity	NPC314270
0.7103	Intermediate Similarity	NPC127647
0.7095	Intermediate Similarity	NPC325093
0.7095	Intermediate Similarity	NPC322043
0.7083	Intermediate Similarity	NPC146724
0.7072	Intermediate Similarity	NPC317373
0.707	Intermediate Similarity	NPC471546
0.7069	Intermediate Similarity	NPC235885
0.7056	Intermediate Similarity	NPC106593
0.7043	Intermediate Similarity	NPC54066
0.7043	Intermediate Similarity	NPC140311
0.7033	Intermediate Similarity	NPC164340
0.7028	Intermediate Similarity	NPC318020
0.7027	Intermediate Similarity	NPC327592
0.7026	Intermediate Similarity	NPC473667
0.7025	Intermediate Similarity	NPC476517
0.7023	Intermediate Similarity	NPC114974
0.7022	Intermediate Similarity	NPC314834
0.7013	Intermediate Similarity	NPC2395
0.7009	Intermediate Similarity	NPC327699

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 NPC477911 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	218
0.1-0.2	539
0.2-0.3	701
0.3-0.4	1643
0.4-0.5	3446
0.5-0.6	2127
0.6-0.7	454
0.7-0.8	21
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
0.8194	Intermediate Similarity	NPD8468	Phase 2
0.8086	Intermediate Similarity	NPD7396	Approved
0.7889	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD5891	Approved
0.7406	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD820	Phase 3
0.7309	Intermediate Similarity	NPD3795	Approved
0.7309	Intermediate Similarity	NPD3794	Approved
0.7297	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD7885	Phase 2
0.7288	Intermediate Similarity	NPD7886	Phase 2
0.7214	Intermediate Similarity	NPD6635	Approved
0.7169	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD1483	Discontinued
0.715	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD7010	Phase 3
0.7137	Intermediate Similarity	NPD8325	Phase 3
0.7137	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD4989	Phase 2
0.7137	Intermediate Similarity	NPD8326	Phase 3
0.7136	Intermediate Similarity	NPD8063	Discontinued
0.7104	Intermediate Similarity	NPD2831	Approved
0.7093	Intermediate Similarity	NPD3393	Approved
0.7093	Intermediate Similarity	NPD3389	Approved
0.7093	Intermediate Similarity	NPD3394	Approved
0.7067	Intermediate Similarity	NPD4417	Approved
0.7054	Intermediate Similarity	NPD6529	Discontinued
0.7044	Intermediate Similarity	NPD5088	Discontinued
0.7043	Intermediate Similarity	NPD8479	Phase 2
0.7039	Intermediate Similarity	NPD485	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7069	Discontinued
0.7014	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD9271	Approved
0.697	Remote Similarity	NPD3280	Approved
0.6933	Remote Similarity	NPD2509	Approved
0.6933	Remote Similarity	NPD2510	Approved
0.6923	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD7708	Approved
0.6881	Remote Similarity	NPD6026	Approved
0.6881	Remote Similarity	NPD6361	Phase 2
0.6878	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3947	Discontinued
0.6852	Remote Similarity	NPD7233	Approved
0.6852	Remote Similarity	NPD7234	Approved
0.685	Remote Similarity	NPD7803	Approved
0.6849	Remote Similarity	NPD4427	Phase 2
0.6837	Remote Similarity	NPD4375	Approved
0.683	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD4506	Discontinued
0.6822	Remote Similarity	NPD5640	Discontinued
0.6818	Remote Similarity	NPD9074	Approved
0.6818	Remote Similarity	NPD9075	Approved
0.6818	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD4529	Approved
0.6804	Remote Similarity	NPD4526	Approved
0.6804	Remote Similarity	NPD4528	Approved
0.6802	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6987	Phase 1
0.6798	Remote Similarity	NPD6262	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD6298	Discontinued
0.6789	Remote Similarity	NPD2336	Approved
0.6787	Remote Similarity	NPD8485	Approved
0.6786	Remote Similarity	NPD7955	Approved
0.6786	Remote Similarity	NPD7956	Approved
0.677	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD7707	Approved
0.6751	Remote Similarity	NPD8289	Discontinued
0.675	Remote Similarity	NPD1270	Approved
0.674	Remote Similarity	NPD3371	Approved
0.6736	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD8021	Approved
0.6728	Remote Similarity	NPD8020	Approved
0.6728	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5147	Discontinued
0.6723	Remote Similarity	NPD4301	Approved
0.6709	Remote Similarity	NPD6770	Approved
0.6708	Remote Similarity	NPD8409	Suspended
0.6701	Remote Similarity	NPD107	Approved
0.6696	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5475	Discontinued
0.6682	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD4376	Phase 3
0.668	Remote Similarity	NPD7967	Discontinued
0.668	Remote Similarity	NPD8091	Phase 3
0.6667	Remote Similarity	NPD6642	Approved
0.6667	Remote Similarity	NPD8361	Approved
0.6667	Remote Similarity	NPD8360	Approved
0.6667	Remote Similarity	NPD2307	Discontinued
0.6667	Remote Similarity	NPD6641	Approved
0.6667	Remote Similarity	NPD8435	Approved
0.6667	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD5490	Discontinued
0.6651	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD3925	Approved
0.6639	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD7404	Approved
0.6636	Remote Similarity	NPD4889	Approved
0.6627	Remote Similarity	NPD6276	Discontinued
0.6624	Remote Similarity	NPD8356	Approved
0.6623	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD2511	Approved
0.6609	Remote Similarity	NPD4897	Phase 2
0.6607	Remote Similarity	NPD7778	Approved
0.6607	Remote Similarity	NPD53	Approved
0.6607	Remote Similarity	NPD7777	Approved
0.6606	Remote Similarity	NPD6569	Phase 2
0.6602	Remote Similarity	NPD2581	Approved
0.6602	Remote Similarity	NPD2582	Approved
0.6599	Remote Similarity	NPD8412	Phase 1
0.6596	Remote Similarity	NPD1926	Approved
0.6596	Remote Similarity	NPD7878	Phase 2
0.6594	Remote Similarity	NPD7562	Approved
0.6589	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD5506	Approved
0.6582	Remote Similarity	NPD5507	Approved
0.6579	Remote Similarity	NPD4034	Approved
0.6579	Remote Similarity	NPD4039	Approved
0.6579	Remote Similarity	NPD4122	Approved
0.6579	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD32	Approved
0.6579	Remote Similarity	NPD4033	Approved
0.6579	Remote Similarity	NPD31	Approved
0.6579	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD4038	Approved
0.6579	Remote Similarity	NPD4037	Approved
0.6579	Remote Similarity	NPD4036	Approved
0.6579	Remote Similarity	NPD4035	Approved
0.6577	Remote Similarity	NPD4551	Phase 2
0.6575	Remote Similarity	NPD6791	Phase 2
0.6574	Remote Similarity	NPD3386	Phase 2
0.6571	Remote Similarity	NPD6446	Discontinued
0.6565	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD7187	Phase 2
0.6562	Remote Similarity	NPD6206	Phase 1
0.6558	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6825	Phase 1
0.6545	Remote Similarity	NPD4021	Phase 2
0.6543	Remote Similarity	NPD7797	Approved
0.6543	Remote Similarity	NPD7796	Approved
0.6542	Remote Similarity	NPD7426	Phase 1
0.654	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD3924	Approved
0.6532	Remote Similarity	NPD3923	Approved
0.6532	Remote Similarity	NPD3922	Approved
0.6532	Remote Similarity	NPD3921	Approved
0.6531	Remote Similarity	NPD3006	Discontinued
0.6529	Remote Similarity	NPD5022	Discontinued
0.6525	Remote Similarity	NPD7395	Discontinued
0.6524	Remote Similarity	NPD3815	Phase 1
0.6524	Remote Similarity	NPD5866	Approved
0.6524	Remote Similarity	NPD3816	Phase 1
0.6516	Remote Similarity	NPD4373	Phase 2
0.6516	Remote Similarity	NPD6281	Approved
0.6515	Remote Similarity	NPD8430	Approved
0.6515	Remote Similarity	NPD2896	Discontinued
0.6509	Remote Similarity	NPD8321	Discontinued
0.6508	Remote Similarity	NPD8101	Phase 3
0.6508	Remote Similarity	NPD5482	Discontinued
0.6507	Remote Similarity	NPD5901	Discontinued
0.6502	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD6962	Phase 2
0.65	Remote Similarity	NPD4948	Discontinued
0.6498	Remote Similarity	NPD8408	Discontinued
0.6496	Remote Similarity	NPD8370	Discontinued
0.6492	Remote Similarity	NPD7417	Discontinued
0.6492	Remote Similarity	NPD6790	Phase 1
0.6491	Remote Similarity	NPD8467	Approved
0.6491	Remote Similarity	NPD8466	Approved
0.6491	Remote Similarity	NPD8465	Approved
0.649	Remote Similarity	NPD5255	Approved
0.6488	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD7169	Suspended
0.6481	Remote Similarity	NPD7470	Discontinued
0.6478	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD7957	Phase 1
0.6478	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD4600	Approved
0.6476	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD4500	Approved
0.6476	Remote Similarity	NPD4501	Approved
0.6476	Remote Similarity	NPD4601	Approved
0.6466	Remote Similarity	NPD5583	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD5100	Phase 3
0.6461	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6494	Phase 2
0.6446	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD4923	Phase 1
0.6444	Remote Similarity	NPD6226	Phase 3
0.6441	Remote Similarity	NPD2544	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD5805	Approved
0.6436	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD3813	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