NPASS Compound

Structure

NPC473869 OpenBabel07101719132D 30 33 0 0 1 0 0 0 0 0999 V2000 -1.2196 2.1382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9647 -2.8708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1045 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9135 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2166 1.1799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -0.0634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -1.0634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 0.4366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -1.0634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -1.5634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -0.0634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -1.5634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5250 0.6735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3647 -0.0285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -1.5634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1488 0.2490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9971 1.1633 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1872 -1.8959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -1.0634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6766 -0.2408 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5000 -0.0634 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1488 0.2490 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1428 -1.6011 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.0634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4541 -1.2157 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 19 1 0 0 0 0 3 24 1 0 0 0 0 4 24 1 0 0 0 0 5 25 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 10 1 0 0 0 0 8 11 2 0 0 0 0 9 12 2 0 0 0 0 9 15 1 0 0 0 0 10 20 2 0 0 0 0 11 20 1 0 0 0 0 12 20 1 0 0 0 0 13 14 1 0 0 0 0 13 18 1 0 0 0 0 14 22 1 0 0 0 0 15 28 1 0 0 0 0 16 23 1 0 0 0 0 17 21 1 0 0 0 0 18 26 1 1 0 0 0 19 27 2 0 0 0 0 19 29 1 0 0 0 0 21 16 1 1 0 0 0 21 24 1 0 0 0 0 22 25 1 1 0 0 0 22 29 1 0 0 0 0 23 25 1 6 0 0 0 23 28 1 0 0 0 0 24 30 1 0 0 0 0 25 26 1 6 0 0 0 26 17 1 1 0 0 0 26 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	412.26
Volume:	446.005
LogP:	4.893
LogD:	4.032
LogS:	-4.646
# Rotatable Bonds:	6
TPSA:	44.76
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.607
Synthetic Accessibility Score:	5.55
Fsp3:	0.654
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:	-4.792
MDCK Permeability:	2.3858341592131183e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.157

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.53
Plasma Protein Binding (PPB):	95.0577163696289%
Volume Distribution (VD):	1.164
Pgp-substrate:	4.1738128662109375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.14
CYP1A2-substrate:	0.124
CYP2C19-inhibitor:	0.138
CYP2C19-substrate:	0.818
CYP2C9-inhibitor:	0.538
CYP2C9-substrate:	0.081
CYP2D6-inhibitor:	0.08
CYP2D6-substrate:	0.315
CYP3A4-inhibitor:	0.712
CYP3A4-substrate:	0.654

ADMET: Excretion

Clearance (CL):	5.537
Half-life (T1/2):	0.175

ADMET: Toxicity

hERG Blockers:	0.958
Human Hepatotoxicity (H-HT):	0.802
Drug-inuced Liver Injury (DILI):	0.921
AMES Toxicity:	0.231
Rat Oral Acute Toxicity:	0.114
Maximum Recommended Daily Dose:	0.949
Skin Sensitization:	0.939
Carcinogencity:	0.383
Eye Corrosion:	0.099
Eye Irritation:	0.697
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC473869

Natural Product ID:	NPC473869
*Common Name:**	MJGSNPALXVHNAT-RJEOBRGXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MJGSNPALXVHNAT-RJEOBRGXSA-N
Standard InCHI:	InChI=1S/C26H36O4/c1-18-13-14-22(29-19(2)27)25(5)23(16-21-17-26(18,25)30-24(21,3)4)28-15-9-12-20-10-7-6-8-11-20/h6-12,18,21-23H,13-17H2,1-5H3/b12-9+/t18-,21-,22+,23+,25+,26+/m1/s1
SMILES:	CC(=O)O[C@H]1CC[C@H]([C@]23[C@]1(C)[C@@H](OC/C=C/c1ccccc1)C[C@H](C2)C(O3)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453836
PubChem CID:	44561218
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002051] Agarofurans

*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
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10346948]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[10346948]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170672]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[11809076]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[18507472]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23421714]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27791375]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[9461657]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461657]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	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
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	6800.0	nM	PMID[465891]

☑ 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 NPC473869 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	227
0.1-0.2	1081
0.2-0.3	2100
0.3-0.4	5343
0.4-0.5	10236
0.5-0.6	18575
0.6-0.7	4585
0.7-0.8	433
0.8-0.85	82
0.85-0.9	13
0.9-0.95	19
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9725	High Similarity	NPC84129
0.9636	High Similarity	NPC473860
0.9381	High Similarity	NPC311175
0.9381	High Similarity	NPC37641
0.9298	High Similarity	NPC473889
0.9298	High Similarity	NPC70973
0.9217	High Similarity	NPC473871
0.9217	High Similarity	NPC473870
0.906	High Similarity	NPC114927
0.906	High Similarity	NPC473083
0.8983	High Similarity	NPC473110
0.8983	High Similarity	NPC475933
0.8983	High Similarity	NPC476970
0.8983	High Similarity	NPC473082
0.8983	High Similarity	NPC470158
0.8983	High Similarity	NPC473111
0.8908	High Similarity	NPC476972
0.8908	High Similarity	NPC476971
0.8718	High Similarity	NPC473439
0.8718	High Similarity	NPC300827
0.8707	High Similarity	NPC470814
0.8689	High Similarity	NPC147561
0.8618	High Similarity	NPC476977
0.8548	High Similarity	NPC476976
0.8487	Intermediate Similarity	NPC473749
0.8462	Intermediate Similarity	NPC89324
0.8448	Intermediate Similarity	NPC470820
0.843	Intermediate Similarity	NPC471758
0.8413	Intermediate Similarity	NPC474608
0.8374	Intermediate Similarity	NPC230331
0.8361	Intermediate Similarity	NPC45821
0.8347	Intermediate Similarity	NPC307139
0.8347	Intermediate Similarity	NPC470815
0.8346	Intermediate Similarity	NPC291638
0.8346	Intermediate Similarity	NPC17877
0.8346	Intermediate Similarity	NPC66761
0.8346	Intermediate Similarity	NPC195647
0.8346	Intermediate Similarity	NPC472577
0.8306	Intermediate Similarity	NPC93632
0.8293	Intermediate Similarity	NPC5486
0.8279	Intermediate Similarity	NPC284022
0.8264	Intermediate Similarity	NPC12016
0.8226	Intermediate Similarity	NPC195224
0.8217	Intermediate Similarity	NPC283375
0.8217	Intermediate Similarity	NPC183122
0.8211	Intermediate Similarity	NPC470816
0.8205	Intermediate Similarity	NPC476476
0.8197	Intermediate Similarity	NPC472373
0.8197	Intermediate Similarity	NPC77691
0.8154	Intermediate Similarity	NPC214550
0.8154	Intermediate Similarity	NPC210591
0.8154	Intermediate Similarity	NPC475652
0.8115	Intermediate Similarity	NPC273336
0.8115	Intermediate Similarity	NPC182333
0.8092	Intermediate Similarity	NPC97667
0.8092	Intermediate Similarity	NPC476094
0.8092	Intermediate Similarity	NPC275592
0.8092	Intermediate Similarity	NPC211137
0.8092	Intermediate Similarity	NPC90614
0.8092	Intermediate Similarity	NPC473081
0.8092	Intermediate Similarity	NPC4341
0.8092	Intermediate Similarity	NPC473112
0.8092	Intermediate Similarity	NPC48017
0.8092	Intermediate Similarity	NPC473085
0.8092	Intermediate Similarity	NPC200592
0.8092	Intermediate Similarity	NPC147880
0.8092	Intermediate Similarity	NPC43241
0.8092	Intermediate Similarity	NPC473613
0.8092	Intermediate Similarity	NPC184747
0.8092	Intermediate Similarity	NPC473758
0.8092	Intermediate Similarity	NPC473109
0.8092	Intermediate Similarity	NPC171207
0.8092	Intermediate Similarity	NPC100913
0.8092	Intermediate Similarity	NPC473060
0.808	Intermediate Similarity	NPC58061
0.8065	Intermediate Similarity	NPC470818
0.8049	Intermediate Similarity	NPC469742
0.8031	Intermediate Similarity	NPC472418
0.803	Intermediate Similarity	NPC87448
0.803	Intermediate Similarity	NPC291599
0.803	Intermediate Similarity	NPC16912
0.803	Intermediate Similarity	NPC97947
0.803	Intermediate Similarity	NPC41481
0.803	Intermediate Similarity	NPC118080
0.803	Intermediate Similarity	NPC472576
0.803	Intermediate Similarity	NPC27377
0.8	Intermediate Similarity	NPC473423
0.7969	Intermediate Similarity	NPC238370
0.7969	Intermediate Similarity	NPC80599
0.7969	Intermediate Similarity	NPC475493
0.7955	Intermediate Similarity	NPC183270
0.7955	Intermediate Similarity	NPC477904
0.7939	Intermediate Similarity	NPC475373
0.7923	Intermediate Similarity	NPC473216
0.7923	Intermediate Similarity	NPC473399
0.791	Intermediate Similarity	NPC177340
0.791	Intermediate Similarity	NPC147217
0.791	Intermediate Similarity	NPC270498
0.791	Intermediate Similarity	NPC246480
0.791	Intermediate Similarity	NPC139067
0.791	Intermediate Similarity	NPC475429
0.791	Intermediate Similarity	NPC473673
0.791	Intermediate Similarity	NPC163087
0.791	Intermediate Similarity	NPC191082
0.7886	Intermediate Similarity	NPC475328
0.7863	Intermediate Similarity	NPC472545
0.7863	Intermediate Similarity	NPC472551
0.7857	Intermediate Similarity	NPC253681
0.7852	Intermediate Similarity	NPC25768
0.7852	Intermediate Similarity	NPC470152
0.7852	Intermediate Similarity	NPC472569
0.7852	Intermediate Similarity	NPC475759
0.7852	Intermediate Similarity	NPC470231
0.7852	Intermediate Similarity	NPC188865
0.7852	Intermediate Similarity	NPC475122
0.7852	Intermediate Similarity	NPC57628
0.7852	Intermediate Similarity	NPC163719
0.7852	Intermediate Similarity	NPC472570
0.7852	Intermediate Similarity	NPC472573
0.7852	Intermediate Similarity	NPC471912
0.7852	Intermediate Similarity	NPC80895
0.7852	Intermediate Similarity	NPC11685
0.7852	Intermediate Similarity	NPC95810
0.7852	Intermediate Similarity	NPC241951
0.7852	Intermediate Similarity	NPC70716
0.7852	Intermediate Similarity	NPC125106
0.7852	Intermediate Similarity	NPC51314
0.7852	Intermediate Similarity	NPC95265
0.7852	Intermediate Similarity	NPC67777
0.7852	Intermediate Similarity	NPC476974
0.7851	Intermediate Similarity	NPC254233
0.7846	Intermediate Similarity	NPC48929
0.782	Intermediate Similarity	NPC472547
0.7803	Intermediate Similarity	NPC39549
0.7803	Intermediate Similarity	NPC184109
0.7794	Intermediate Similarity	NPC70403
0.7794	Intermediate Similarity	NPC470159
0.7794	Intermediate Similarity	NPC471100
0.7794	Intermediate Similarity	NPC476973
0.7794	Intermediate Similarity	NPC200471
0.7794	Intermediate Similarity	NPC473088
0.7794	Intermediate Similarity	NPC471104
0.7794	Intermediate Similarity	NPC472572
0.7794	Intermediate Similarity	NPC158663
0.7794	Intermediate Similarity	NPC184817
0.7794	Intermediate Similarity	NPC472575
0.7794	Intermediate Similarity	NPC472571
0.7794	Intermediate Similarity	NPC301946
0.7794	Intermediate Similarity	NPC96903
0.7794	Intermediate Similarity	NPC171525
0.7794	Intermediate Similarity	NPC470157
0.7794	Intermediate Similarity	NPC29704
0.7794	Intermediate Similarity	NPC177940
0.7794	Intermediate Similarity	NPC469349
0.7794	Intermediate Similarity	NPC471107
0.7794	Intermediate Similarity	NPC472568
0.7794	Intermediate Similarity	NPC277053
0.7794	Intermediate Similarity	NPC174982
0.7786	Intermediate Similarity	NPC471864
0.7769	Intermediate Similarity	NPC152812
0.7761	Intermediate Similarity	NPC224491
0.7759	Intermediate Similarity	NPC475006
0.7752	Intermediate Similarity	NPC472361
0.7737	Intermediate Similarity	NPC474935
0.7734	Intermediate Similarity	NPC225103
0.771	Intermediate Similarity	NPC4242
0.771	Intermediate Similarity	NPC471911
0.7704	Intermediate Similarity	NPC473755
0.7704	Intermediate Similarity	NPC475513
0.7698	Intermediate Similarity	NPC265413
0.7698	Intermediate Similarity	NPC10154
0.7692	Intermediate Similarity	NPC209851
0.7686	Intermediate Similarity	NPC242764
0.7686	Intermediate Similarity	NPC105141
0.7686	Intermediate Similarity	NPC472862
0.7681	Intermediate Similarity	NPC281717
0.768	Intermediate Similarity	NPC108286
0.7674	Intermediate Similarity	NPC473443
0.7674	Intermediate Similarity	NPC472388
0.7672	Intermediate Similarity	NPC21929
0.7669	Intermediate Similarity	NPC262324
0.7664	Intermediate Similarity	NPC472556
0.7647	Intermediate Similarity	NPC91703
0.7647	Intermediate Similarity	NPC477894
0.7638	Intermediate Similarity	NPC275576
0.7634	Intermediate Similarity	NPC472437
0.7634	Intermediate Similarity	NPC15850
0.763	Intermediate Similarity	NPC266374
0.7626	Intermediate Similarity	NPC473215
0.7626	Intermediate Similarity	NPC301556
0.7626	Intermediate Similarity	NPC471101
0.7626	Intermediate Similarity	NPC270590
0.7626	Intermediate Similarity	NPC266265
0.7626	Intermediate Similarity	NPC92293
0.7626	Intermediate Similarity	NPC476975
0.7623	Intermediate Similarity	NPC45794
0.7615	Intermediate Similarity	NPC470278
0.7609	Intermediate Similarity	NPC473602
0.76	Intermediate Similarity	NPC369
0.76	Intermediate Similarity	NPC293831

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 NPC473869 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	760
0.2-0.3	1243
0.3-0.4	3237
0.4-0.5	2282
0.5-0.6	1246
0.6-0.7	178
0.7-0.8	9
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
0.7851	Intermediate Similarity	NPD7741	Discontinued
0.75	Intermediate Similarity	NPD7094	Approved
0.75	Intermediate Similarity	NPD6858	Approved
0.7459	Intermediate Similarity	NPD4198	Discontinued
0.7302	Intermediate Similarity	NPD5126	Approved
0.7302	Intermediate Similarity	NPD5125	Phase 3
0.7288	Intermediate Similarity	NPD6685	Approved
0.7214	Intermediate Similarity	NPD7274	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD7236	Approved
0.7121	Intermediate Similarity	NPD5736	Approved
0.7069	Intermediate Similarity	NPD7798	Approved
0.7034	Intermediate Similarity	NPD5765	Approved
0.7016	Intermediate Similarity	NPD6010	Discontinued
0.6985	Remote Similarity	NPD4140	Approved
0.6977	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5327	Phase 3
0.6918	Remote Similarity	NPD7239	Suspended
0.6917	Remote Similarity	NPD5048	Discontinued
0.6912	Remote Similarity	NPD6663	Approved
0.6912	Remote Similarity	NPD7961	Discontinued
0.6891	Remote Similarity	NPD6647	Phase 2
0.6889	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6912	Phase 3
0.6838	Remote Similarity	NPD5926	Approved
0.6833	Remote Similarity	NPD5909	Discontinued
0.6825	Remote Similarity	NPD2629	Approved
0.6797	Remote Similarity	NPD6065	Approved
0.6788	Remote Similarity	NPD8032	Phase 2
0.6774	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD3317	Approved
0.675	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6637	Approved
0.6724	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6049	Phase 2
0.6716	Remote Similarity	NPD3094	Phase 2
0.6696	Remote Similarity	NPD1282	Approved
0.6695	Remote Similarity	NPD7638	Approved
0.6694	Remote Similarity	NPD2067	Discontinued
0.6692	Remote Similarity	NPD5691	Approved
0.669	Remote Similarity	NPD5762	Approved
0.669	Remote Similarity	NPD5763	Approved
0.6667	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1989	Approved
0.6667	Remote Similarity	NPD3673	Approved
0.6667	Remote Similarity	NPD3672	Approved
0.6646	Remote Similarity	NPD7799	Discontinued
0.6641	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD3095	Discontinued
0.6639	Remote Similarity	NPD7639	Approved
0.6639	Remote Similarity	NPD7640	Approved
0.6623	Remote Similarity	NPD37	Approved
0.6615	Remote Similarity	NPD3091	Approved
0.6601	Remote Similarity	NPD4966	Approved
0.6601	Remote Similarity	NPD4965	Approved
0.6601	Remote Similarity	NPD4967	Phase 2
0.6599	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD4230	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5706	Approved
0.6585	Remote Similarity	NPD5705	Approved
0.6585	Remote Similarity	NPD5704	Approved
0.6571	Remote Similarity	NPD5735	Approved
0.6569	Remote Similarity	NPD7055	Discontinued
0.6565	Remote Similarity	NPD5585	Approved
0.6565	Remote Similarity	NPD3024	Approved
0.6565	Remote Similarity	NPD3025	Approved
0.656	Remote Similarity	NPD5240	Approved
0.656	Remote Similarity	NPD5236	Approved
0.656	Remote Similarity	NPD5235	Approved
0.656	Remote Similarity	NPD5237	Approved
0.656	Remote Similarity	NPD5239	Approved
0.6552	Remote Similarity	NPD8166	Discontinued
0.6552	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD3092	Approved
0.6538	Remote Similarity	NPD7610	Discontinued
0.6535	Remote Similarity	NPD5535	Approved
0.6525	Remote Similarity	NPD6353	Approved
0.6522	Remote Similarity	NPD7008	Discontinued
0.6522	Remote Similarity	NPD7095	Approved
0.6518	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD6234	Discontinued
0.65	Remote Similarity	NPD2979	Phase 3
0.6494	Remote Similarity	NPD7057	Phase 3
0.6494	Remote Similarity	NPD7058	Phase 2
0.6484	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.648	Remote Similarity	NPD2182	Approved
0.6479	Remote Similarity	NPD7097	Phase 1
0.6475	Remote Similarity	NPD3764	Approved
0.6475	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD3023	Approved
0.6466	Remote Similarity	NPD3026	Approved
0.6458	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD6002	Phase 3
0.6458	Remote Similarity	NPD6004	Phase 3
0.6458	Remote Similarity	NPD6005	Phase 3
0.6458	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD5124	Phase 1
0.6454	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD4908	Phase 1
0.6434	Remote Similarity	NPD5951	Approved
0.6434	Remote Similarity	NPD7305	Phase 1
0.6433	Remote Similarity	NPD8127	Discontinued
0.6423	Remote Similarity	NPD4624	Approved
0.6418	Remote Similarity	NPD1611	Approved
0.6398	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD6696	Suspended
0.6392	Remote Similarity	NPD7229	Phase 3
0.6391	Remote Similarity	NPD3019	Approved
0.6391	Remote Similarity	NPD4626	Approved
0.6389	Remote Similarity	NPD6099	Approved
0.6389	Remote Similarity	NPD2438	Suspended
0.6389	Remote Similarity	NPD6100	Approved
0.6383	Remote Similarity	NPD4060	Phase 1
0.6378	Remote Similarity	NPD2201	Approved
0.6377	Remote Similarity	NPD2861	Phase 2
0.6364	Remote Similarity	NPD8407	Phase 2
0.6364	Remote Similarity	NPD6648	Approved
0.6357	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD7266	Discontinued
0.6341	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD3971	Phase 1
0.6338	Remote Similarity	NPD6355	Discontinued
0.6336	Remote Similarity	NPD7327	Approved
0.6336	Remote Similarity	NPD7328	Approved
0.6335	Remote Similarity	NPD7228	Approved
0.6333	Remote Similarity	NPD6273	Approved
0.6324	Remote Similarity	NPD4359	Approved
0.6319	Remote Similarity	NPD7033	Discontinued
0.6312	Remote Similarity	NPD7714	Approved
0.6312	Remote Similarity	NPD7715	Approved
0.6308	Remote Similarity	NPD4766	Approved
0.6296	Remote Similarity	NPD6287	Discontinued
0.6296	Remote Similarity	NPD1281	Approved
0.6296	Remote Similarity	NPD3705	Approved
0.6293	Remote Similarity	NPD6051	Approved
0.629	Remote Similarity	NPD3048	Approved
0.629	Remote Similarity	NPD3046	Approved
0.629	Remote Similarity	NPD3047	Approved
0.6288	Remote Similarity	NPD7644	Approved
0.6288	Remote Similarity	NPD7516	Approved
0.6287	Remote Similarity	NPD8434	Phase 2
0.6286	Remote Similarity	NPD4625	Phase 3
0.628	Remote Similarity	NPD8368	Discontinued
0.6277	Remote Similarity	NPD8651	Approved
0.6271	Remote Similarity	NPD1088	Approved
0.6269	Remote Similarity	NPD17	Approved
0.6269	Remote Similarity	NPD2932	Approved
0.6269	Remote Similarity	NPD4059	Approved
0.6269	Remote Similarity	NPD1778	Approved
0.6268	Remote Similarity	NPD2238	Phase 2
0.6267	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD1087	Approved
0.6259	Remote Similarity	NPD6674	Discontinued
0.6259	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5886	Approved
0.625	Remote Similarity	NPD41	Approved
0.625	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.623	Remote Similarity	NPD2066	Phase 3
0.6228	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD3657	Discovery
0.6222	Remote Similarity	NPD7815	Approved
0.6222	Remote Similarity	NPD7813	Approved
0.6222	Remote Similarity	NPD3496	Discontinued
0.622	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD7466	Approved
0.6216	Remote Similarity	NPD4628	Phase 3
0.6216	Remote Similarity	NPD4110	Phase 3
0.6216	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD2613	Approved
0.6211	Remote Similarity	NPD4481	Phase 3
0.6204	Remote Similarity	NPD4749	Approved
0.6204	Remote Similarity	NPD6025	Phase 1
0.6202	Remote Similarity	NPD969	Suspended
0.6197	Remote Similarity	NPD4870	Approved
0.6194	Remote Similarity	NPD8296	Approved
0.6194	Remote Similarity	NPD8380	Approved
0.6194	Remote Similarity	NPD8379	Approved
0.6194	Remote Similarity	NPD8378	Approved
0.6194	Remote Similarity	NPD8335	Approved
0.6194	Remote Similarity	NPD7503	Approved
0.619	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.619	Remote Similarity	NPD3134	Approved
0.6187	Remote Similarity	NPD6085	Phase 2
0.6187	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD7240	Approved
0.6181	Remote Similarity	NPD4097	Suspended
0.6181	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD2558	Approved
0.6179	Remote Similarity	NPD2553	Approved
0.6179	Remote Similarity	NPD2555	Approved
0.6179	Remote Similarity	NPD2549	Approved
0.6179	Remote Similarity	NPD2552	Approved
0.6179	Remote Similarity	NPD2550	Approved
0.6176	Remote Similarity	NPD1610	Phase 2
0.6174	Remote Similarity	NPD6190	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