NPASS Compound

Structure

NPC472545 OpenBabel07101719252D 38 41 0 0 1 0 0 0 0 0999 V2000 3.3816 -0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 -2.4405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 3.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7180 -0.4797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 2.4405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4881 -0.8454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0724 2.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2270 3.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0724 1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 2.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 3.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3816 2.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2270 1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4786 0.0505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7883 0.7408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7714 1.2145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1802 -0.3112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4215 0.3031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3816 1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 1.4643 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7462 1.1634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 1.4643 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8454 0.4881 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6908 -0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 0.4881 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.9524 0.0000 C 0 0 2 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 -5.3606 1.9220 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 -1.4643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 0.4881 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9762 -1.6908 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9989 0.2205 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 1.9524 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 29 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 12 1 0 0 0 0 9 13 2 0 0 0 0 10 11 1 0 0 0 0 10 14 1 0 0 0 0 11 20 2 0 0 0 0 12 22 2 0 0 0 0 13 22 1 0 0 0 0 14 23 1 0 0 0 0 15 16 2 0 0 0 0 15 21 1 0 0 0 0 16 29 1 0 0 0 0 17 21 2 0 0 0 0 17 24 1 0 0 0 0 18 21 1 0 0 0 0 18 36 1 0 0 0 0 19 27 1 0 0 0 0 20 30 1 0 0 0 0 22 28 1 0 0 0 0 23 29 1 1 0 0 0 23 30 1 0 0 0 0 24 32 2 0 0 0 0 24 36 1 0 0 0 0 25 26 1 0 0 0 0 25 30 1 1 0 0 0 25 37 1 0 0 0 0 26 31 1 6 0 0 0 26 38 1 0 0 0 0 27 33 2 0 0 0 0 27 38 1 0 0 0 0 28 34 2 0 0 0 0 28 37 1 0 0 0 0 29 31 1 6 0 0 0 30 5 1 1 0 0 0 31 6 1 1 0 0 0 31 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	522.26
Volume:	548.31
LogP:	4.464
LogD:	3.588
LogS:	-4.66
# Rotatable Bonds:	8
TPSA:	106.2
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.358
Synthetic Accessibility Score:	4.95
Fsp3:	0.484
Lipinski Rule-of-5:	Accepted
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:	-4.85
MDCK Permeability:	1.9251679987064563e-05
Pgp-inhibitor:	0.974
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.599
30% Bioavailability (F30%):	0.819

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.342
Plasma Protein Binding (PPB):	98.9607162475586%
Volume Distribution (VD):	1.434
Pgp-substrate:	5.443643569946289%

ADMET: Metabolism

CYP1A2-inhibitor:	0.452
CYP1A2-substrate:	0.129
CYP2C19-inhibitor:	0.775
CYP2C19-substrate:	0.117
CYP2C9-inhibitor:	0.659
CYP2C9-substrate:	0.941
CYP2D6-inhibitor:	0.947
CYP2D6-substrate:	0.209
CYP3A4-inhibitor:	0.894
CYP3A4-substrate:	0.346

ADMET: Excretion

Clearance (CL):	9.471
Half-life (T1/2):	0.484

ADMET: Toxicity

hERG Blockers:	0.192
Human Hepatotoxicity (H-HT):	0.2
Drug-inuced Liver Injury (DILI):	0.643
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.163
Maximum Recommended Daily Dose:	0.012
Skin Sensitization:	0.608
Carcinogencity:	0.173
Eye Corrosion:	0.003
Eye Irritation:	0.064
Respiratory Toxicity:	0.165

Download Data

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

Natural Product: NPC472545

Natural Product ID:	NPC472545
*Common Name:**	WZRBVWLPCKNBQX-HSUYODJOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WZRBVWLPCKNBQX-HSUYODJOSA-N
Standard InCHI:	InChI=1S/C31H38O7/c1-19(2)27(33)38-26-25(37-28(34)22-12-8-7-9-13-22)30(5)20(3)11-10-14-23(30)29(4,31(26,6)35)16-15-21-17-24(32)36-18-21/h7-9,11-13,15-17,19,23,25-26,35H,10,14,18H2,1-6H3/b16-15+/t23-,25+,26+,29-,30+,31+/m1/s1
SMILES:	O=C1OCC(=C1)/C=C/[C@]1(C)[C@H]2CCC=C([C@]2(C)[C@H]([C@@H]([C@]1(C)O)OC(=O)C(C)C)OC(=O)c1ccccc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3577073
PubChem CID:	n.a.
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
EC50	1
Others	3

Activity Type	# Activity
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Ratio CC50/EC50	=	5.4	n.a.	PMID[456050]
NPT27	Others	Unspecified		CC50	=	49700.0	nM	PMID[456050]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	EC50	=	9200.0	nM	PMID[456050]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	>	50.0	%	PMID[456050]

☑ 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 NPC472545 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	266
0.1-0.2	1035
0.2-0.3	2167
0.3-0.4	4335
0.4-0.5	8512
0.5-0.6	11197
0.6-0.7	12593
0.7-0.8	2188
0.8-0.85	217
0.85-0.9	154
0.9-0.95	27
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472551
0.9922	High Similarity	NPC39549
0.9771	High Similarity	NPC472547
0.9697	High Similarity	NPC224491
0.9624	High Similarity	NPC472546
0.9474	High Similarity	NPC97667
0.9474	High Similarity	NPC171207
0.9474	High Similarity	NPC100913
0.9474	High Similarity	NPC275592
0.9407	High Similarity	NPC91703
0.9403	High Similarity	NPC87448
0.9403	High Similarity	NPC97947
0.9403	High Similarity	NPC16912
0.9403	High Similarity	NPC291599
0.9403	High Similarity	NPC118080
0.9403	High Similarity	NPC27377
0.9403	High Similarity	NPC472576
0.9403	High Similarity	NPC41481
0.9333	High Similarity	NPC34012
0.9328	High Similarity	NPC90614
0.927	High Similarity	NPC472556
0.9242	High Similarity	NPC474608
0.9203	High Similarity	NPC474935
0.9197	High Similarity	NPC125106
0.9197	High Similarity	NPC188865
0.9197	High Similarity	NPC38696
0.9197	High Similarity	NPC475122
0.9197	High Similarity	NPC472569
0.9197	High Similarity	NPC11685
0.9197	High Similarity	NPC163719
0.9197	High Similarity	NPC476974
0.9197	High Similarity	NPC241951
0.9197	High Similarity	NPC57628
0.9197	High Similarity	NPC470152
0.9197	High Similarity	NPC25768
0.9197	High Similarity	NPC95265
0.9197	High Similarity	NPC95810
0.9197	High Similarity	NPC472570
0.9197	High Similarity	NPC70716
0.9197	High Similarity	NPC475759
0.9197	High Similarity	NPC472573
0.9173	High Similarity	NPC472577
0.9173	High Similarity	NPC291638
0.9173	High Similarity	NPC66761
0.9173	High Similarity	NPC195647
0.9173	High Similarity	NPC17877
0.913	High Similarity	NPC174982
0.913	High Similarity	NPC96903
0.913	High Similarity	NPC473088
0.913	High Similarity	NPC472571
0.913	High Similarity	NPC29704
0.913	High Similarity	NPC472575
0.913	High Similarity	NPC470157
0.913	High Similarity	NPC171525
0.913	High Similarity	NPC476973
0.913	High Similarity	NPC471104
0.913	High Similarity	NPC177940
0.913	High Similarity	NPC158663
0.913	High Similarity	NPC200471
0.913	High Similarity	NPC472572
0.913	High Similarity	NPC472568
0.913	High Similarity	NPC184817
0.913	High Similarity	NPC469349
0.913	High Similarity	NPC70403
0.913	High Similarity	NPC470159
0.9124	High Similarity	NPC163087
0.9084	High Similarity	NPC147561
0.9044	High Similarity	NPC477904
0.9044	High Similarity	NPC183270
0.9037	High Similarity	NPC283375
0.9037	High Similarity	NPC183122
0.9	High Similarity	NPC217918
0.9	High Similarity	NPC281717
0.8993	High Similarity	NPC127857
0.8986	High Similarity	NPC477894
0.8971	High Similarity	NPC475652
0.8971	High Similarity	NPC214550
0.8971	High Similarity	NPC210591
0.8963	High Similarity	NPC472374
0.8963	High Similarity	NPC472372
0.8936	High Similarity	NPC301556
0.8936	High Similarity	NPC473215
0.8936	High Similarity	NPC270590
0.8936	High Similarity	NPC471101
0.8936	High Similarity	NPC92293
0.8936	High Similarity	NPC266265
0.8936	High Similarity	NPC476975
0.8929	High Similarity	NPC478263
0.8929	High Similarity	NPC473602
0.8921	High Similarity	NPC34943
0.8913	High Similarity	NPC192658
0.8913	High Similarity	NPC182869
0.8905	High Similarity	NPC48017
0.8905	High Similarity	NPC43241
0.8905	High Similarity	NPC473758
0.8905	High Similarity	NPC473081
0.8905	High Similarity	NPC473085
0.8905	High Similarity	NPC184747
0.8905	High Similarity	NPC473112
0.8905	High Similarity	NPC476094
0.8905	High Similarity	NPC211137
0.8905	High Similarity	NPC200592
0.8905	High Similarity	NPC473613
0.8905	High Similarity	NPC147880
0.8905	High Similarity	NPC473109
0.8905	High Similarity	NPC473060
0.8905	High Similarity	NPC4341
0.8889	High Similarity	NPC477896
0.8889	High Similarity	NPC477893
0.8881	High Similarity	NPC472548
0.8873	High Similarity	NPC470245
0.8873	High Similarity	NPC91730
0.8873	High Similarity	NPC473214
0.8857	High Similarity	NPC92867
0.8857	High Similarity	NPC311825
0.8857	High Similarity	NPC478264
0.8841	High Similarity	NPC266374
0.8832	High Similarity	NPC9905
0.8815	High Similarity	NPC48929
0.8811	High Similarity	NPC51602
0.8811	High Similarity	NPC471103
0.8811	High Similarity	NPC197037
0.8811	High Similarity	NPC470153
0.8811	High Similarity	NPC101043
0.8811	High Similarity	NPC306799
0.8806	High Similarity	NPC238370
0.8803	High Similarity	NPC81698
0.8803	High Similarity	NPC250046
0.8803	High Similarity	NPC60509
0.8794	High Similarity	NPC20255
0.8794	High Similarity	NPC209592
0.8794	High Similarity	NPC48599
0.8794	High Similarity	NPC240115
0.8768	High Similarity	NPC87934
0.8768	High Similarity	NPC162613
0.8759	High Similarity	NPC472549
0.875	High Similarity	NPC477905
0.8741	High Similarity	NPC161239
0.8741	High Similarity	NPC476173
0.8741	High Similarity	NPC198455
0.8741	High Similarity	NPC7095
0.8741	High Similarity	NPC112216
0.8741	High Similarity	NPC165260
0.8741	High Similarity	NPC469448
0.8732	High Similarity	NPC132652
0.8732	High Similarity	NPC473760
0.8723	High Similarity	NPC125882
0.8714	High Similarity	NPC177340
0.8714	High Similarity	NPC191082
0.8714	High Similarity	NPC139067
0.8714	High Similarity	NPC246480
0.8714	High Similarity	NPC147217
0.8714	High Similarity	NPC270498
0.8714	High Similarity	NPC473673
0.8714	High Similarity	NPC475429
0.8712	High Similarity	NPC473220
0.8712	High Similarity	NPC470753
0.869	High Similarity	NPC229545
0.869	High Similarity	NPC219419
0.869	High Similarity	NPC248265
0.869	High Similarity	NPC11588
0.869	High Similarity	NPC134685
0.8681	High Similarity	NPC469415
0.8667	High Similarity	NPC472394
0.8667	High Similarity	NPC80599
0.8662	High Similarity	NPC312393
0.8652	High Similarity	NPC470231
0.8652	High Similarity	NPC51314
0.8652	High Similarity	NPC67777
0.8636	High Similarity	NPC275576
0.8636	High Similarity	NPC470765
0.863	High Similarity	NPC34066
0.863	High Similarity	NPC155329
0.863	High Similarity	NPC473670
0.863	High Similarity	NPC473611
0.863	High Similarity	NPC114357
0.863	High Similarity	NPC473632
0.863	High Similarity	NPC132599
0.863	High Similarity	NPC469730
0.863	High Similarity	NPC21410
0.863	High Similarity	NPC469422
0.863	High Similarity	NPC282239
0.863	High Similarity	NPC259144
0.8613	High Similarity	NPC473216
0.8613	High Similarity	NPC473399
0.8611	High Similarity	NPC222102
0.8611	High Similarity	NPC31829
0.8611	High Similarity	NPC303429
0.8601	High Similarity	NPC327031
0.8593	High Similarity	NPC72915
0.8592	High Similarity	NPC471100
0.8592	High Similarity	NPC471107
0.8582	High Similarity	NPC95449
0.8571	High Similarity	NPC217091
0.8571	High Similarity	NPC169913
0.8571	High Similarity	NPC106895
0.8562	High Similarity	NPC473414
0.8562	High Similarity	NPC1173
0.8562	High Similarity	NPC472030
0.8562	High Similarity	NPC472022

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 NPC472545 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	231
0.1-0.2	742
0.2-0.3	1362
0.3-0.4	2613
0.4-0.5	2288
0.5-0.6	1376
0.6-0.7	494
0.7-0.8	44
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8207	Intermediate Similarity	NPD7236	Approved
0.8116	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD7239	Suspended
0.7875	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD8368	Discontinued
0.7727	Intermediate Similarity	NPD2629	Approved
0.7703	Intermediate Similarity	NPD4628	Phase 3
0.7702	Intermediate Similarity	NPD7799	Discontinued
0.7697	Intermediate Similarity	NPD8407	Phase 2
0.7669	Intermediate Similarity	NPD4198	Discontinued
0.7647	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD7008	Discontinued
0.7605	Intermediate Similarity	NPD8434	Phase 2
0.7584	Intermediate Similarity	NPD8166	Discontinued
0.7557	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7741	Discontinued
0.7468	Intermediate Similarity	NPD7058	Phase 2
0.7468	Intermediate Similarity	NPD7057	Phase 3
0.7467	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD5951	Approved
0.7431	Intermediate Similarity	NPD3764	Approved
0.7412	Intermediate Similarity	NPD8361	Approved
0.7412	Intermediate Similarity	NPD8360	Approved
0.7412	Intermediate Similarity	NPD8435	Approved
0.7396	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6273	Approved
0.7338	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD7274	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD8127	Discontinued
0.7273	Intermediate Similarity	NPD2182	Approved
0.7266	Intermediate Similarity	NPD5126	Approved
0.7266	Intermediate Similarity	NPD5125	Phase 3
0.7266	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6599	Discontinued
0.726	Intermediate Similarity	NPD7961	Discontinued
0.7233	Intermediate Similarity	NPD7819	Suspended
0.7211	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD7075	Discontinued
0.7197	Intermediate Similarity	NPD7458	Discontinued
0.7185	Intermediate Similarity	NPD6858	Approved
0.7185	Intermediate Similarity	NPD7094	Approved
0.7163	Intermediate Similarity	NPD6287	Discontinued
0.7162	Intermediate Similarity	NPD6355	Discontinued
0.7159	Intermediate Similarity	NPD8485	Approved
0.7152	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6663	Approved
0.7135	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5844	Phase 1
0.7124	Intermediate Similarity	NPD3750	Approved
0.7124	Intermediate Similarity	NPD7003	Approved
0.7103	Intermediate Similarity	NPD5736	Approved
0.7093	Intermediate Similarity	NPD8150	Discontinued
0.7089	Intermediate Similarity	NPD6591	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6190	Approved
0.7063	Intermediate Similarity	NPD37	Approved
0.7059	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6234	Discontinued
0.7054	Intermediate Similarity	NPD1238	Approved
0.7051	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD7610	Discontinued
0.7047	Intermediate Similarity	NPD230	Phase 1
0.7039	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4966	Approved
0.7037	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4965	Approved
0.7037	Intermediate Similarity	NPD4967	Phase 2
0.7023	Intermediate Similarity	NPD1930	Approved
0.7023	Intermediate Similarity	NPD1929	Approved
0.7023	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD3748	Approved
0.7013	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4110	Phase 3
0.7006	Intermediate Similarity	NPD7473	Discontinued
0.7	Intermediate Similarity	NPD6764	Approved
0.7	Intermediate Similarity	NPD6765	Approved
0.7	Intermediate Similarity	NPD9545	Approved
0.6987	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6799	Approved
0.6985	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.697	Remote Similarity	NPD164	Approved
0.6963	Remote Similarity	NPD2067	Discontinued
0.6957	Remote Similarity	NPD6801	Discontinued
0.6943	Remote Similarity	NPD2532	Approved
0.6943	Remote Similarity	NPD2534	Approved
0.6943	Remote Similarity	NPD2533	Approved
0.6937	Remote Similarity	NPD4380	Phase 2
0.6933	Remote Similarity	NPD7768	Phase 2
0.6928	Remote Similarity	NPD6232	Discontinued
0.6928	Remote Similarity	NPD2346	Discontinued
0.6928	Remote Similarity	NPD5762	Approved
0.6928	Remote Similarity	NPD5763	Approved
0.6923	Remote Similarity	NPD4806	Approved
0.6923	Remote Similarity	NPD4807	Approved
0.6923	Remote Similarity	NPD7497	Discontinued
0.6923	Remote Similarity	NPD2066	Phase 3
0.6914	Remote Similarity	NPD5760	Phase 2
0.6914	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5761	Phase 2
0.6908	Remote Similarity	NPD2799	Discontinued
0.6901	Remote Similarity	NPD5305	Approved
0.6901	Remote Similarity	NPD5306	Approved
0.6894	Remote Similarity	NPD6647	Phase 2
0.6892	Remote Similarity	NPD7095	Approved
0.6889	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD6010	Discontinued
0.6883	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD3817	Phase 2
0.6864	Remote Similarity	NPD7228	Approved
0.6863	Remote Similarity	NPD2935	Discontinued
0.6863	Remote Similarity	NPD5404	Approved
0.6863	Remote Similarity	NPD5408	Approved
0.6863	Remote Similarity	NPD5405	Approved
0.6863	Remote Similarity	NPD6099	Approved
0.6863	Remote Similarity	NPD5406	Approved
0.6863	Remote Similarity	NPD2438	Suspended
0.6863	Remote Similarity	NPD6100	Approved
0.6855	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5403	Approved
0.6852	Remote Similarity	NPD1934	Approved
0.6846	Remote Similarity	NPD6798	Discontinued
0.6846	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5909	Discontinued
0.6839	Remote Similarity	NPD6784	Approved
0.6839	Remote Similarity	NPD6785	Approved
0.6836	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD5401	Approved
0.6832	Remote Similarity	NPD7028	Phase 2
0.6821	Remote Similarity	NPD8312	Approved
0.6821	Remote Similarity	NPD8313	Approved
0.6818	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7266	Discontinued
0.6818	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD5494	Approved
0.6802	Remote Similarity	NPD7685	Pre-registration
0.6802	Remote Similarity	NPD6559	Discontinued
0.68	Remote Similarity	NPD8032	Phase 2
0.6797	Remote Similarity	NPD4308	Phase 3
0.6792	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.679	Remote Similarity	NPD7411	Suspended
0.6783	Remote Similarity	NPD2932	Approved
0.6781	Remote Similarity	NPD1283	Approved
0.677	Remote Similarity	NPD3226	Approved
0.6768	Remote Similarity	NPD5402	Approved
0.6768	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7199	Phase 2
0.6761	Remote Similarity	NPD7009	Phase 2
0.6759	Remote Similarity	NPD1608	Approved
0.6755	Remote Similarity	NPD4140	Approved
0.6753	Remote Similarity	NPD2796	Approved
0.6753	Remote Similarity	NPD1551	Phase 2
0.6747	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD6685	Approved
0.6736	Remote Similarity	NPD4106	Approved
0.6736	Remote Similarity	NPD4135	Approved
0.6736	Remote Similarity	NPD4136	Approved
0.6735	Remote Similarity	NPD2797	Approved
0.6733	Remote Similarity	NPD2313	Discontinued
0.673	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD3882	Suspended
0.672	Remote Similarity	NPD8462	Phase 1
0.6716	Remote Similarity	NPD1237	Approved
0.6715	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD6832	Phase 2
0.671	Remote Similarity	NPD6002	Phase 3
0.671	Remote Similarity	NPD6005	Phase 3
0.671	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.671	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.671	Remote Similarity	NPD6004	Phase 3
0.6707	Remote Similarity	NPD8455	Phase 2
0.6705	Remote Similarity	NPD7240	Approved
0.6689	Remote Similarity	NPD7714	Approved
0.6689	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD2798	Approved
0.6689	Remote Similarity	NPD6085	Phase 2
0.6689	Remote Similarity	NPD7713	Phase 3
0.6689	Remote Similarity	NPD6233	Phase 2
0.6689	Remote Similarity	NPD7715	Approved
0.6688	Remote Similarity	NPD1510	Phase 2
0.6688	Remote Similarity	NPD7305	Phase 1
0.6688	Remote Similarity	NPD7033	Discontinued
0.6687	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD1549	Phase 2
0.6667	Remote Similarity	NPD3818	Discontinued
0.6667	Remote Similarity	NPD3019	Approved
0.6667	Remote Similarity	NPD3455	Phase 2
0.6667	Remote Similarity	NPD7798	Approved
0.6667	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5048	Discontinued
0.6667	Remote Similarity	NPD5667	Approved
0.6645	Remote Similarity	NPD4307	Phase 2
0.6645	Remote Similarity	NPD4060	Phase 1

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