NPASS Compound

Structure

NPC472548 OpenBabel07101719252D 42 47 0 0 1 0 0 0 0 0999 V2000 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 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 -5.1962 4.0000 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 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 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0570 -1.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6750 -1.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3660 -2.0388 0.0000 C 0 0 0 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 -0.8660 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 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 -0.2218 -2.8479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -2.0388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 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 21 1 0 0 0 0 3 32 1 0 0 0 0 5 7 2 0 0 0 0 5 8 1 0 0 0 0 6 9 2 0 0 0 0 6 10 1 0 0 0 0 7 13 1 0 0 0 0 8 14 2 0 0 0 0 9 15 1 0 0 0 0 10 16 2 0 0 0 0 11 12 1 0 0 0 0 11 17 1 0 0 0 0 12 21 2 0 0 0 0 13 22 2 0 0 0 0 14 22 1 0 0 0 0 15 23 2 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 18 25 1 0 0 0 0 19 26 1 0 0 0 0 19 34 1 0 0 0 0 20 34 1 0 0 0 0 20 39 1 0 0 0 0 21 31 1 0 0 0 0 22 29 1 0 0 0 0 23 30 1 0 0 0 0 24 31 1 6 0 0 0 24 32 1 0 0 0 0 25 32 1 1 0 0 0 25 40 1 0 0 0 0 26 35 2 0 0 0 0 26 39 1 0 0 0 0 27 28 1 0 0 0 0 27 33 1 1 0 0 0 27 36 1 0 0 0 0 28 31 1 6 0 0 0 28 41 1 0 0 0 0 29 37 2 0 0 0 0 29 40 1 0 0 0 0 30 38 2 0 0 0 0 30 41 1 0 0 0 0 31 2 1 6 0 0 0 32 33 1 6 0 0 0 33 4 1 6 0 0 0 33 42 1 0 0 0 0 34 18 1 6 0 0 0 34 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	574.26
Volume:	589.238
LogP:	4.789
LogD:	3.556
LogS:	-5.204
# Rotatable Bonds:	6
TPSA:	108.36
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.307
Synthetic Accessibility Score:	5.287
Fsp3:	0.5
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:	-4.946
MDCK Permeability:	2.7784393751062453e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.048
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.916
30% Bioavailability (F30%):	0.955

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.3
Plasma Protein Binding (PPB):	98.00253295898438%
Volume Distribution (VD):	1.436
Pgp-substrate:	2.5339086055755615%

ADMET: Metabolism

CYP1A2-inhibitor:	0.257
CYP1A2-substrate:	0.111
CYP2C19-inhibitor:	0.524
CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.84
CYP2C9-substrate:	0.101
CYP2D6-inhibitor:	0.25
CYP2D6-substrate:	0.069
CYP3A4-inhibitor:	0.905
CYP3A4-substrate:	0.428

ADMET: Excretion

Clearance (CL):	12.162
Half-life (T1/2):	0.602

ADMET: Toxicity

hERG Blockers:	0.489
Human Hepatotoxicity (H-HT):	0.209
Drug-inuced Liver Injury (DILI):	0.795
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.044
Maximum Recommended Daily Dose:	0.694
Skin Sensitization:	0.754
Carcinogencity:	0.165
Eye Corrosion:	0.003
Eye Irritation:	0.142
Respiratory Toxicity:	0.532

Download Data

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

Natural Product: NPC472548

Natural Product ID:	NPC472548
*Common Name:**	ZAYKMDVKSXAHIM-ANYWXESPSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZAYKMDVKSXAHIM-ANYWXESPSA-N
Standard InCHI:	InChI=1S/C34H38O8/c1-21-12-11-17-24-31(21,2)28(41-30(38)23-15-9-6-10-16-23)27(36)33(4)32(24,3)25(18-34(42-33)19-26(35)39-20-34)40-29(37)22-13-7-5-8-14-22/h5-10,12-16,24-25,27-28,36H,11,17-20H2,1-4H3/t24-,25-,27-,28-,31-,32-,33-,34+/m0/s1
SMILES:	O=C1OC[C@]2(C1)C[C@H](OC(=O)c1ccccc1)[C@]1([C@](O2)(C)[C@@H](O)[C@@H]([C@@]2([C@@H]1CCC=C2C)C)OC(=O)c1ccccc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3577076
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	=	3.6	n.a.	PMID[513530]
NPT27	Others	Unspecified		CC50	=	66500.0	nM	PMID[513530]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	EC50	=	18300.0	nM	PMID[513530]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	>	50.0	%	PMID[513530]

☑ 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 NPC472548 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	316
0.1-0.2	1097
0.2-0.3	2398
0.3-0.4	4382
0.4-0.5	8723
0.5-0.6	11236
0.6-0.7	11305
0.7-0.8	2716
0.8-0.85	260
0.85-0.9	127
0.9-0.95	134
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9861	High Similarity	NPC472549
0.986	High Similarity	NPC477905
0.9392	High Similarity	NPC106895
0.9388	High Similarity	NPC1173
0.9388	High Similarity	NPC472030
0.9388	High Similarity	NPC473414
0.9388	High Similarity	NPC256142
0.9388	High Similarity	NPC304876
0.9388	High Similarity	NPC472005
0.9388	High Similarity	NPC257213
0.9388	High Similarity	NPC158333
0.9388	High Similarity	NPC249471
0.9388	High Similarity	NPC237549
0.9388	High Similarity	NPC472022
0.9388	High Similarity	NPC242262
0.9388	High Similarity	NPC265395
0.9324	High Similarity	NPC26033
0.9324	High Similarity	NPC114410
0.9324	High Similarity	NPC112523
0.9324	High Similarity	NPC282239
0.9324	High Similarity	NPC228204
0.9315	High Similarity	NPC7095
0.9306	High Similarity	NPC158663
0.9306	High Similarity	NPC472571
0.9306	High Similarity	NPC476973
0.9306	High Similarity	NPC177940
0.9306	High Similarity	NPC174982
0.9306	High Similarity	NPC470157
0.9306	High Similarity	NPC472572
0.9306	High Similarity	NPC473088
0.9306	High Similarity	NPC29704
0.9306	High Similarity	NPC96903
0.9306	High Similarity	NPC470159
0.9306	High Similarity	NPC70403
0.9306	High Similarity	NPC184817
0.9306	High Similarity	NPC472568
0.9306	High Similarity	NPC171525
0.9306	High Similarity	NPC469349
0.9306	High Similarity	NPC200471
0.9306	High Similarity	NPC472575
0.9306	High Similarity	NPC471104
0.9267	High Similarity	NPC469399
0.9267	High Similarity	NPC471102
0.9262	High Similarity	NPC217091
0.9257	High Similarity	NPC77719
0.9252	High Similarity	NPC471103
0.9252	High Similarity	NPC51602
0.9252	High Similarity	NPC470153
0.9247	High Similarity	NPC250046
0.9247	High Similarity	NPC471101
0.9247	High Similarity	NPC60509
0.9247	High Similarity	NPC301556
0.9247	High Similarity	NPC266265
0.9247	High Similarity	NPC270590
0.9247	High Similarity	NPC92293
0.9247	High Similarity	NPC81698
0.9241	High Similarity	NPC474935
0.9236	High Similarity	NPC95810
0.9236	High Similarity	NPC472570
0.9236	High Similarity	NPC125106
0.9236	High Similarity	NPC475759
0.9236	High Similarity	NPC57628
0.9236	High Similarity	NPC11685
0.9236	High Similarity	NPC70716
0.9236	High Similarity	NPC472569
0.9236	High Similarity	NPC470152
0.9236	High Similarity	NPC25768
0.9236	High Similarity	NPC188865
0.9236	High Similarity	NPC241951
0.9236	High Similarity	NPC475122
0.9236	High Similarity	NPC472573
0.9236	High Similarity	NPC95265
0.9236	High Similarity	NPC163719
0.9236	High Similarity	NPC476974
0.9225	High Similarity	NPC477904
0.9225	High Similarity	NPC183270
0.92	High Similarity	NPC472393
0.92	High Similarity	NPC469771
0.92	High Similarity	NPC469417
0.9195	High Similarity	NPC473670
0.9195	High Similarity	NPC21410
0.9184	High Similarity	NPC112216
0.9184	High Similarity	NPC161239
0.9184	High Similarity	NPC165260
0.9184	High Similarity	NPC198455
0.9178	High Similarity	NPC281717
0.9172	High Similarity	NPC127857
0.9172	High Similarity	NPC472556
0.9167	High Similarity	NPC163087
0.9161	High Similarity	NPC224491
0.9161	High Similarity	NPC472576
0.9161	High Similarity	NPC27377
0.9161	High Similarity	NPC16912
0.9161	High Similarity	NPC41481
0.9161	High Similarity	NPC97947
0.9161	High Similarity	NPC87448
0.9161	High Similarity	NPC291599
0.9161	High Similarity	NPC118080
0.9122	High Similarity	NPC306799
0.9122	High Similarity	NPC101043
0.9116	High Similarity	NPC476975
0.9091	High Similarity	NPC171207
0.9091	High Similarity	NPC90614
0.9091	High Similarity	NPC100913
0.9091	High Similarity	NPC472547
0.9091	High Similarity	NPC275592
0.9091	High Similarity	NPC97667
0.9054	High Similarity	NPC470245
0.9054	High Similarity	NPC91730
0.9054	High Similarity	NPC254558
0.9054	High Similarity	NPC473214
0.9038	High Similarity	NPC102465
0.9034	High Similarity	NPC477894
0.9026	High Similarity	NPC295408
0.9026	High Similarity	NPC329960
0.9026	High Similarity	NPC150893
0.9	High Similarity	NPC133430
0.9	High Similarity	NPC469477
0.8993	High Similarity	NPC197037
0.8986	High Similarity	NPC473215
0.8966	High Similarity	NPC34012
0.8958	High Similarity	NPC476094
0.8958	High Similarity	NPC184747
0.8958	High Similarity	NPC211137
0.8958	High Similarity	NPC473758
0.8958	High Similarity	NPC147880
0.8958	High Similarity	NPC200592
0.8958	High Similarity	NPC473109
0.8958	High Similarity	NPC473613
0.8958	High Similarity	NPC473060
0.8958	High Similarity	NPC4341
0.8958	High Similarity	NPC473081
0.8958	High Similarity	NPC48017
0.8958	High Similarity	NPC473085
0.8958	High Similarity	NPC43241
0.8958	High Similarity	NPC473112
0.8951	High Similarity	NPC39549
0.894	High Similarity	NPC5115
0.894	High Similarity	NPC469730
0.894	High Similarity	NPC473611
0.894	High Similarity	NPC473632
0.894	High Similarity	NPC132599
0.8926	High Similarity	NPC469448
0.8919	High Similarity	NPC217918
0.8917	High Similarity	NPC469420
0.8912	High Similarity	NPC471107
0.8912	High Similarity	NPC471100
0.8904	High Similarity	NPC177340
0.8904	High Similarity	NPC270498
0.8904	High Similarity	NPC246480
0.8904	High Similarity	NPC477468
0.8904	High Similarity	NPC147217
0.8904	High Similarity	NPC139067
0.8904	High Similarity	NPC191082
0.8904	High Similarity	NPC475429
0.8904	High Similarity	NPC473673
0.8903	High Similarity	NPC66193
0.8896	High Similarity	NPC476077
0.8889	High Similarity	NPC210591
0.8889	High Similarity	NPC475652
0.8889	High Similarity	NPC214550
0.8881	High Similarity	NPC472551
0.8881	High Similarity	NPC472545
0.8874	High Similarity	NPC248265
0.8874	High Similarity	NPC11588
0.8874	High Similarity	NPC134685
0.8874	High Similarity	NPC229545
0.8874	High Similarity	NPC219419
0.8861	High Similarity	NPC477471
0.8861	High Similarity	NPC477473
0.8861	High Similarity	NPC477469
0.8861	High Similarity	NPC477466
0.8851	High Similarity	NPC473602
0.8846	High Similarity	NPC471134
0.8844	High Similarity	NPC67777
0.8844	High Similarity	NPC51314
0.8836	High Similarity	NPC182869
0.8836	High Similarity	NPC472546
0.8819	High Similarity	NPC283375
0.8819	High Similarity	NPC183122
0.8816	High Similarity	NPC259144
0.8816	High Similarity	NPC114357
0.8816	High Similarity	NPC155329
0.8816	High Similarity	NPC34066
0.8812	High Similarity	NPC469421
0.8811	High Similarity	NPC472577
0.8811	High Similarity	NPC195647
0.8811	High Similarity	NPC477893
0.8811	High Similarity	NPC66761
0.8811	High Similarity	NPC17877
0.8811	High Similarity	NPC477896
0.8811	High Similarity	NPC291638
0.879	High Similarity	NPC61891
0.8784	High Similarity	NPC301946
0.8784	High Similarity	NPC277053
0.8776	High Similarity	NPC91703
0.8767	High Similarity	NPC213567
0.8741	High Similarity	NPC474608
0.8726	High Similarity	NPC471493
0.8725	High Similarity	NPC477737

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 NPC472548 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	261
0.1-0.2	698
0.2-0.3	1473
0.3-0.4	2776
0.4-0.5	2410
0.5-0.6	1099
0.6-0.7	381
0.7-0.8	49
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8232	Intermediate Similarity	NPD7799	Discontinued
0.817	Intermediate Similarity	NPD7236	Approved
0.8118	Intermediate Similarity	NPD8434	Phase 2
0.8107	Intermediate Similarity	NPD8407	Phase 2
0.8036	Intermediate Similarity	NPD8368	Discontinued
0.8025	Intermediate Similarity	NPD7239	Suspended
0.8023	Intermediate Similarity	NPD8361	Approved
0.8023	Intermediate Similarity	NPD8435	Approved
0.8023	Intermediate Similarity	NPD8360	Approved
0.7907	Intermediate Similarity	NPD8150	Discontinued
0.7857	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD8485	Approved
0.7803	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7057	Phase 3
0.7576	Intermediate Similarity	NPD7058	Phase 2
0.7468	Intermediate Similarity	NPD4628	Phase 3
0.7455	Intermediate Similarity	NPD7819	Suspended
0.7429	Intermediate Similarity	NPD8312	Approved
0.7429	Intermediate Similarity	NPD8313	Approved
0.7378	Intermediate Similarity	NPD4380	Phase 2
0.7365	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD8166	Discontinued
0.7349	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD5844	Phase 1
0.7326	Intermediate Similarity	NPD7473	Discontinued
0.7321	Intermediate Similarity	NPD7075	Discontinued
0.7318	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6190	Approved
0.7294	Intermediate Similarity	NPD8127	Discontinued
0.7283	Intermediate Similarity	NPD7228	Approved
0.7273	Intermediate Similarity	NPD8320	Phase 1
0.7273	Intermediate Similarity	NPD8319	Approved
0.7255	Intermediate Similarity	NPD7008	Discontinued
0.7251	Intermediate Similarity	NPD6232	Discontinued
0.7246	Intermediate Similarity	NPD5760	Phase 2
0.7246	Intermediate Similarity	NPD5761	Phase 2
0.7235	Intermediate Similarity	NPD5494	Approved
0.7228	Intermediate Similarity	NPD7700	Phase 2
0.7228	Intermediate Similarity	NPD7699	Phase 2
0.7216	Intermediate Similarity	NPD7685	Pre-registration
0.7212	Intermediate Similarity	NPD7458	Discontinued
0.7208	Intermediate Similarity	NPD3764	Approved
0.7202	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD8462	Phase 1
0.7186	Intermediate Similarity	NPD37	Approved
0.7178	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6599	Discontinued
0.7168	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6166	Phase 2
0.7168	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD5125	Phase 3
0.7162	Intermediate Similarity	NPD5126	Approved
0.7161	Intermediate Similarity	NPD7961	Discontinued
0.716	Intermediate Similarity	NPD4966	Approved
0.716	Intermediate Similarity	NPD4965	Approved
0.716	Intermediate Similarity	NPD4967	Phase 2
0.7159	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD6535	Approved
0.7158	Intermediate Similarity	NPD6534	Approved
0.7143	Intermediate Similarity	NPD7741	Discontinued
0.7143	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6273	Approved
0.7128	Intermediate Similarity	NPD7435	Discontinued
0.7126	Intermediate Similarity	NPD7411	Suspended
0.7119	Intermediate Similarity	NPD7240	Approved
0.7118	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD2629	Approved
0.7102	Intermediate Similarity	NPD7074	Phase 3
0.7086	Intermediate Similarity	NPD3818	Discontinued
0.7086	Intermediate Similarity	NPD3751	Discontinued
0.7083	Intermediate Similarity	NPD6801	Discontinued
0.7076	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD6234	Discontinued
0.7073	Intermediate Similarity	NPD2534	Approved
0.7073	Intermediate Similarity	NPD2533	Approved
0.7073	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD2532	Approved
0.7069	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4198	Discontinued
0.7047	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7054	Approved
0.7041	Intermediate Similarity	NPD8404	Phase 2
0.7041	Intermediate Similarity	NPD8455	Phase 2
0.7041	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7497	Discontinued
0.7022	Intermediate Similarity	NPD6559	Discontinued
0.7018	Intermediate Similarity	NPD3749	Approved
0.7006	Intermediate Similarity	NPD7472	Approved
0.7006	Intermediate Similarity	NPD3226	Approved
0.7006	Intermediate Similarity	NPD6591	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5402	Approved
0.7	Intermediate Similarity	NPD3817	Phase 2
0.6995	Remote Similarity	NPD7874	Approved
0.6995	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6959	Discontinued
0.6986	Remote Similarity	NPD5951	Approved
0.6983	Remote Similarity	NPD7808	Phase 3
0.6982	Remote Similarity	NPD1934	Approved
0.6968	Remote Similarity	NPD6777	Approved
0.6968	Remote Similarity	NPD6776	Approved
0.6968	Remote Similarity	NPD6779	Approved
0.6968	Remote Similarity	NPD6781	Approved
0.6968	Remote Similarity	NPD6778	Approved
0.6968	Remote Similarity	NPD6780	Approved
0.6968	Remote Similarity	NPD6782	Approved
0.6959	Remote Similarity	NPD7768	Phase 2
0.6957	Remote Similarity	NPD2346	Discontinued
0.6954	Remote Similarity	NPD3787	Discontinued
0.6947	Remote Similarity	NPD7698	Approved
0.6947	Remote Similarity	NPD7697	Approved
0.6947	Remote Similarity	NPD7696	Phase 3
0.6943	Remote Similarity	NPD8151	Discontinued
0.6933	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7003	Approved
0.6933	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6765	Approved
0.6927	Remote Similarity	NPD6764	Approved
0.6927	Remote Similarity	NPD7251	Discontinued
0.6918	Remote Similarity	NPD6010	Discontinued
0.6911	Remote Similarity	NPD7870	Phase 2
0.6911	Remote Similarity	NPD7871	Phase 2
0.6909	Remote Similarity	NPD6799	Approved
0.6905	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7199	Phase 2
0.6891	Remote Similarity	NPD7701	Phase 2
0.6889	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD5403	Approved
0.6872	Remote Similarity	NPD7801	Approved
0.6872	Remote Similarity	NPD6797	Phase 2
0.6871	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5401	Approved
0.6867	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.686	Remote Similarity	NPD3882	Suspended
0.6855	Remote Similarity	NPD230	Phase 1
0.6852	Remote Similarity	NPD7266	Discontinued
0.6842	Remote Similarity	NPD1465	Phase 2
0.6828	Remote Similarity	NPD6212	Phase 3
0.6828	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6213	Phase 3
0.6807	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD6823	Phase 2
0.6806	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD2182	Approved
0.679	Remote Similarity	NPD5406	Approved
0.679	Remote Similarity	NPD5405	Approved
0.679	Remote Similarity	NPD5408	Approved
0.679	Remote Similarity	NPD5404	Approved
0.6788	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7783	Phase 2
0.6786	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6784	Approved
0.6776	Remote Similarity	NPD6785	Approved
0.677	Remote Similarity	NPD7097	Phase 1
0.6755	Remote Similarity	NPD8517	Approved
0.6755	Remote Similarity	NPD8516	Approved
0.6755	Remote Similarity	NPD8515	Approved
0.6755	Remote Similarity	NPD8513	Phase 3
0.6744	Remote Similarity	NPD2801	Approved
0.6737	Remote Similarity	NPD8285	Discontinued
0.6735	Remote Similarity	NPD6858	Approved
0.6735	Remote Similarity	NPD7094	Approved
0.673	Remote Similarity	NPD7714	Approved
0.673	Remote Similarity	NPD7715	Approved
0.6728	Remote Similarity	NPD7033	Discontinued
0.6728	Remote Similarity	NPD2799	Discontinued
0.6727	Remote Similarity	NPD3750	Approved
0.6723	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD5048	Discontinued
0.6712	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7390	Discontinued
0.6707	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD1549	Phase 2
0.6687	Remote Similarity	NPD2796	Approved
0.6687	Remote Similarity	NPD2935	Discontinued
0.6667	Remote Similarity	NPD2313	Discontinued
0.6667	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7319	Approved
0.6667	Remote Similarity	NPD2800	Approved
0.6667	Remote Similarity	NPD5711	Approved
0.6667	Remote Similarity	NPD7229	Phase 3
0.6667	Remote Similarity	NPD5710	Approved
0.665	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6355	Discontinued
0.6646	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD7305	Phase 1
0.6626	Remote Similarity	NPD3748	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