NPASS Compound

Structure

NPC163087 OpenBabel07101718202D 39 43 0 0 1 0 0 0 0 0999 V2000 1.8271 3.3584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5628 -1.7322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2877 -1.3535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6831 0.1616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2677 3.3048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0860 -2.4798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2677 2.3738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4614 3.7703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2798 -2.0143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8923 -2.0143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4614 1.9083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6551 3.3048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2798 -1.0833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8923 -1.0833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2807 1.8015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9213 1.9991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8676 -0.1567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7581 0.8734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5096 2.7252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6551 2.3738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0860 -0.6178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1315 1.1479 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3762 -0.6127 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4128 1.5431 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8175 0.5118 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4735 0.3132 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8489 1.9083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0860 0.3132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4655 -0.8063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2636 0.8895 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6230 0.6919 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9653 -0.0342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3992 2.9996 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8489 0.9773 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8923 0.7787 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3024 1.8175 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0426 2.3738 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2798 0.7787 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 19 1 0 0 0 0 2 29 1 0 0 0 0 3 29 1 0 0 0 0 4 30 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 11 1 0 0 0 0 8 12 2 0 0 0 0 9 13 1 0 0 0 0 10 14 2 0 0 0 0 11 20 2 0 0 0 0 12 20 1 0 0 0 0 13 21 2 0 0 0 0 14 21 1 0 0 0 0 15 16 1 0 0 0 0 15 22 1 0 0 0 0 16 24 1 0 0 0 0 17 25 1 0 0 0 0 18 22 1 0 0 0 0 18 32 1 0 0 0 0 19 33 2 0 0 0 0 19 36 1 0 0 0 0 20 27 1 0 0 0 0 21 28 1 0 0 0 0 22 31 1 6 0 0 0 23 17 1 1 0 0 0 23 26 1 0 0 0 0 23 29 1 0 0 0 0 24 30 1 6 0 0 0 24 36 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 34 2 0 0 0 0 27 37 1 0 0 0 0 28 35 2 0 0 0 0 28 38 1 0 0 0 0 29 39 1 0 0 0 0 30 31 1 1 0 0 0 31 39 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	536.24
Volume:	548.543
LogP:	4.736
LogD:	3.411
LogS:	-4.635
# Rotatable Bonds:	9
TPSA:	108.36
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.429
Synthetic Accessibility Score:	5.492
Fsp3:	0.516
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:	-5.061
MDCK Permeability:	3.527629451127723e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.965
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.336
Plasma Protein Binding (PPB):	91.31700897216797%
Volume Distribution (VD):	1.902
Pgp-substrate:	8.519113540649414%

ADMET: Metabolism

CYP1A2-inhibitor:	0.11
CYP1A2-substrate:	0.044
CYP2C19-inhibitor:	0.063
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.415
CYP2C9-substrate:	0.064
CYP2D6-inhibitor:	0.062
CYP2D6-substrate:	0.08
CYP3A4-inhibitor:	0.38
CYP3A4-substrate:	0.324

ADMET: Excretion

Clearance (CL):	8.837
Half-life (T1/2):	0.518

ADMET: Toxicity

hERG Blockers:	0.834
Human Hepatotoxicity (H-HT):	0.827
Drug-inuced Liver Injury (DILI):	0.966
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.067
Maximum Recommended Daily Dose:	0.085
Skin Sensitization:	0.234
Carcinogencity:	0.322
Eye Corrosion:	0.004
Eye Irritation:	0.202
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC163087

Natural Product ID:	NPC163087
*Common Name:**	PGZSQQPPVDUMHW-VCBFDHLISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PGZSQQPPVDUMHW-VCBFDHLISA-N
Standard InCHI:	InChI=1S/C31H36O8/c1-19(33)36-24-16-15-22(18-32)31-26(38-28(35)21-13-9-6-10-14-21)23(29(2,3)39-31)17-25(30(24,31)4)37-27(34)20-11-7-5-8-12-20/h5-14,22-26,32H,15-18H2,1-4H3/t22-,23+,24-,25-,26+,30-,31+/m0/s1
SMILES:	CC(=O)O[C@H]1CC[C@@H](CO)[C@@]23[C@@H]([C@@H](C[C@@H]([C@]12C)OC(=O)c1ccccc1)C(C)(C)O3)OC(=O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454600
PubChem CID:	24898242
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
Others	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	Activity	<	50.0	%	PMID[493510]

☑ 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 NPC163087 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	284
0.1-0.2	1030
0.2-0.3	2205
0.3-0.4	4068
0.4-0.5	8211
0.5-0.6	11855
0.6-0.7	12439
0.7-0.8	2059
0.8-0.85	223
0.85-0.9	157
0.9-0.95	52
0.95-1	114

Similarity Score	Similarity Level	Natural Product ID
0.9926	High Similarity	NPC470152
0.9926	High Similarity	NPC475759
0.9926	High Similarity	NPC241951
0.9853	High Similarity	NPC473088
0.9853	High Similarity	NPC470159
0.9853	High Similarity	NPC471104
0.9853	High Similarity	NPC476973
0.9853	High Similarity	NPC472572
0.9853	High Similarity	NPC184817
0.9853	High Similarity	NPC472575
0.9853	High Similarity	NPC158663
0.9853	High Similarity	NPC177940
0.9853	High Similarity	NPC472571
0.9853	High Similarity	NPC29704
0.9853	High Similarity	NPC174982
0.9853	High Similarity	NPC70403
0.9853	High Similarity	NPC171525
0.9853	High Similarity	NPC469349
0.9853	High Similarity	NPC96903
0.9853	High Similarity	NPC472568
0.9853	High Similarity	NPC200471
0.9853	High Similarity	NPC470157
0.9779	High Similarity	NPC476974
0.9779	High Similarity	NPC163719
0.9779	High Similarity	NPC472570
0.9779	High Similarity	NPC11685
0.9779	High Similarity	NPC25768
0.9779	High Similarity	NPC188865
0.9779	High Similarity	NPC472569
0.9779	High Similarity	NPC57628
0.9779	High Similarity	NPC472573
0.9779	High Similarity	NPC95810
0.9779	High Similarity	NPC70716
0.9779	High Similarity	NPC95265
0.9779	High Similarity	NPC475122
0.9779	High Similarity	NPC125106
0.9776	High Similarity	NPC90614
0.9704	High Similarity	NPC41481
0.9704	High Similarity	NPC472576
0.9704	High Similarity	NPC97947
0.9704	High Similarity	NPC87448
0.9704	High Similarity	NPC118080
0.9704	High Similarity	NPC291599
0.9704	High Similarity	NPC27377
0.964	High Similarity	NPC471101
0.964	High Similarity	NPC476975
0.964	High Similarity	NPC301556
0.964	High Similarity	NPC270590
0.964	High Similarity	NPC92293
0.964	High Similarity	NPC266265
0.963	High Similarity	NPC48017
0.963	High Similarity	NPC184747
0.963	High Similarity	NPC4341
0.963	High Similarity	NPC211137
0.963	High Similarity	NPC473613
0.963	High Similarity	NPC473060
0.963	High Similarity	NPC473081
0.963	High Similarity	NPC97667
0.963	High Similarity	NPC171207
0.963	High Similarity	NPC473109
0.963	High Similarity	NPC200592
0.963	High Similarity	NPC473758
0.963	High Similarity	NPC473112
0.963	High Similarity	NPC275592
0.963	High Similarity	NPC476094
0.963	High Similarity	NPC100913
0.963	High Similarity	NPC473085
0.963	High Similarity	NPC147880
0.963	High Similarity	NPC43241
0.9627	High Similarity	NPC183122
0.9627	High Similarity	NPC283375
0.9571	High Similarity	NPC473214
0.9571	High Similarity	NPC470245
0.9568	High Similarity	NPC281717
0.9565	High Similarity	NPC472556
0.9559	High Similarity	NPC16912
0.9556	High Similarity	NPC210591
0.9556	High Similarity	NPC214550
0.9556	High Similarity	NPC475652
0.9504	High Similarity	NPC470153
0.95	High Similarity	NPC473215
0.9496	High Similarity	NPC474935
0.9478	High Similarity	NPC291638
0.9478	High Similarity	NPC195647
0.9478	High Similarity	NPC66761
0.9478	High Similarity	NPC472577
0.9478	High Similarity	NPC17877
0.942	High Similarity	NPC270498
0.942	High Similarity	NPC246480
0.942	High Similarity	NPC147217
0.942	High Similarity	NPC139067
0.942	High Similarity	NPC177340
0.942	High Similarity	NPC475429
0.942	High Similarity	NPC191082
0.942	High Similarity	NPC473673
0.9403	High Similarity	NPC474608
0.9353	High Similarity	NPC470231
0.9353	High Similarity	NPC51314
0.9353	High Similarity	NPC67777
0.9343	High Similarity	NPC472547
0.9301	High Similarity	NPC477905
0.9281	High Similarity	NPC91703
0.9275	High Similarity	NPC224491
0.9241	High Similarity	NPC106895
0.922	High Similarity	NPC473602
0.9209	High Similarity	NPC34012
0.9197	High Similarity	NPC39549
0.9172	High Similarity	NPC34066
0.9172	High Similarity	NPC282239
0.9167	High Similarity	NPC472548
0.9161	High Similarity	NPC469448
0.9161	High Similarity	NPC31829
0.9155	High Similarity	NPC473760
0.9143	High Similarity	NPC477894
0.9124	High Similarity	NPC472551
0.9124	High Similarity	NPC472545
0.9118	High Similarity	NPC48929
0.9104	High Similarity	NPC147561
0.9097	High Similarity	NPC471103
0.9091	High Similarity	NPC250046
0.9091	High Similarity	NPC60509
0.9091	High Similarity	NPC81698
0.9085	High Similarity	NPC209592
0.9085	High Similarity	NPC48599
0.9078	High Similarity	NPC38696
0.9065	High Similarity	NPC477904
0.9065	High Similarity	NPC183270
0.9048	High Similarity	NPC472393
0.9041	High Similarity	NPC472549
0.9041	High Similarity	NPC228204
0.9041	High Similarity	NPC469422
0.9041	High Similarity	NPC26033
0.9028	High Similarity	NPC198455
0.9028	High Similarity	NPC254558
0.9028	High Similarity	NPC161239
0.9028	High Similarity	NPC7095
0.9028	High Similarity	NPC165260
0.9	High Similarity	NPC266374
0.8986	High Similarity	NPC471102
0.8986	High Similarity	NPC469399
0.898	High Similarity	NPC217091
0.8973	High Similarity	NPC472030
0.8973	High Similarity	NPC1173
0.8973	High Similarity	NPC304876
0.8973	High Similarity	NPC472022
0.8973	High Similarity	NPC473414
0.8973	High Similarity	NPC249471
0.8973	High Similarity	NPC257213
0.8973	High Similarity	NPC472005
0.8973	High Similarity	NPC242262
0.8973	High Similarity	NPC265395
0.8973	High Similarity	NPC158333
0.8973	High Similarity	NPC256142
0.8973	High Similarity	NPC237549
0.8966	High Similarity	NPC51602
0.8951	High Similarity	NPC240115
0.8944	High Similarity	NPC34943
0.8936	High Similarity	NPC472546
0.8913	High Similarity	NPC477893
0.8912	High Similarity	NPC473632
0.8912	High Similarity	NPC114410
0.8912	High Similarity	NPC132599
0.8912	High Similarity	NPC469730
0.8912	High Similarity	NPC112523
0.8897	High Similarity	NPC112216
0.8889	High Similarity	NPC217918
0.8881	High Similarity	NPC471100
0.8881	High Similarity	NPC125882
0.8881	High Similarity	NPC92867
0.8881	High Similarity	NPC471107
0.8881	High Similarity	NPC127857
0.8881	High Similarity	NPC311825
0.8857	High Similarity	NPC9905
0.8849	High Similarity	NPC472372
0.8849	High Similarity	NPC472374
0.8844	High Similarity	NPC77719
0.8844	High Similarity	NPC472657
0.8844	High Similarity	NPC472658
0.8836	High Similarity	NPC469415
0.8828	High Similarity	NPC76103
0.8819	High Similarity	NPC478263
0.8819	High Similarity	NPC20255
0.8803	High Similarity	NPC192658
0.8803	High Similarity	NPC182869
0.88	High Similarity	NPC477623
0.8794	High Similarity	NPC87934
0.8794	High Similarity	NPC162613
0.8792	High Similarity	NPC469417
0.8792	High Similarity	NPC469771
0.8792	High Similarity	NPC318447
0.8792	High Similarity	NPC322048
0.8786	High Similarity	NPC475373
0.8784	High Similarity	NPC473670
0.8784	High Similarity	NPC473611
0.8784	High Similarity	NPC469398
0.8784	High Similarity	NPC21410
0.8777	High Similarity	NPC477896
0.8767	High Similarity	NPC476173
0.8767	High Similarity	NPC91730
0.8767	High Similarity	NPC303429

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 NPC163087 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	240
0.1-0.2	675
0.2-0.3	1351
0.3-0.4	2646
0.4-0.5	2442
0.5-0.6	1303
0.6-0.7	439
0.7-0.8	52
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8243	Intermediate Similarity	NPD7236	Approved
0.8156	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD7239	Suspended
0.7963	Intermediate Similarity	NPD7799	Discontinued
0.7914	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7008	Discontinued
0.7751	Intermediate Similarity	NPD8434	Phase 2
0.7738	Intermediate Similarity	NPD8407	Phase 2
0.7665	Intermediate Similarity	NPD8368	Discontinued
0.7661	Intermediate Similarity	NPD8360	Approved
0.7661	Intermediate Similarity	NPD8361	Approved
0.7661	Intermediate Similarity	NPD8435	Approved
0.7654	Intermediate Similarity	NPD8127	Discontinued
0.7625	Intermediate Similarity	NPD7057	Phase 3
0.7625	Intermediate Similarity	NPD7058	Phase 2
0.7613	Intermediate Similarity	NPD6273	Approved
0.7569	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD8485	Approved
0.7485	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5844	Phase 1
0.7483	Intermediate Similarity	NPD3764	Approved
0.7438	Intermediate Similarity	NPD37	Approved
0.7432	Intermediate Similarity	NPD7961	Discontinued
0.7429	Intermediate Similarity	NPD7741	Discontinued
0.7407	Intermediate Similarity	NPD4966	Approved
0.7407	Intermediate Similarity	NPD4967	Phase 2
0.7407	Intermediate Similarity	NPD4965	Approved
0.7403	Intermediate Similarity	NPD8166	Discontinued
0.7391	Intermediate Similarity	NPD2629	Approved
0.7391	Intermediate Similarity	NPD5951	Approved
0.7374	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7458	Discontinued
0.7355	Intermediate Similarity	NPD6190	Approved
0.7353	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD8150	Discontinued
0.7338	Intermediate Similarity	NPD4198	Discontinued
0.7324	Intermediate Similarity	NPD5126	Approved
0.7324	Intermediate Similarity	NPD5125	Phase 3
0.729	Intermediate Similarity	NPD7003	Approved
0.7273	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7228	Approved
0.7215	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6234	Discontinued
0.7208	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7819	Suspended
0.7168	Intermediate Similarity	NPD8313	Approved
0.7168	Intermediate Similarity	NPD8312	Approved
0.716	Intermediate Similarity	NPD7473	Discontinued
0.7153	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6591	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7610	Discontinued
0.7099	Intermediate Similarity	NPD4380	Phase 2
0.7091	Intermediate Similarity	NPD7768	Phase 2
0.7083	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6232	Discontinued
0.708	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD2182	Approved
0.7073	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5761	Phase 2
0.7073	Intermediate Similarity	NPD5760	Phase 2
0.7073	Intermediate Similarity	NPD8455	Phase 2
0.707	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD5494	Approved
0.7065	Intermediate Similarity	NPD7497	Discontinued
0.7062	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7240	Approved
0.7048	Intermediate Similarity	NPD7075	Discontinued
0.7032	Intermediate Similarity	NPD5408	Approved
0.7032	Intermediate Similarity	NPD5405	Approved
0.7032	Intermediate Similarity	NPD5404	Approved
0.7032	Intermediate Similarity	NPD5406	Approved
0.703	Intermediate Similarity	NPD5402	Approved
0.7025	Intermediate Similarity	NPD7274	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6858	Approved
0.7	Intermediate Similarity	NPD7094	Approved
0.6994	Remote Similarity	NPD6599	Discontinued
0.6987	Remote Similarity	NPD7266	Discontinued
0.6986	Remote Similarity	NPD6287	Discontinued
0.6974	Remote Similarity	NPD6663	Approved
0.6962	Remote Similarity	NPD3750	Approved
0.6954	Remote Similarity	NPD6764	Approved
0.6954	Remote Similarity	NPD7685	Pre-registration
0.6954	Remote Similarity	NPD6559	Discontinued
0.6954	Remote Similarity	NPD6765	Approved
0.6951	Remote Similarity	NPD7411	Suspended
0.6937	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3226	Approved
0.6933	Remote Similarity	NPD5736	Approved
0.6928	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7199	Phase 2
0.6923	Remote Similarity	NPD2935	Discontinued
0.6914	Remote Similarity	NPD5403	Approved
0.6909	Remote Similarity	NPD6801	Discontinued
0.6906	Remote Similarity	NPD6534	Approved
0.6906	Remote Similarity	NPD6535	Approved
0.6903	Remote Similarity	NPD7097	Phase 1
0.6897	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD2532	Approved
0.6894	Remote Similarity	NPD5401	Approved
0.6894	Remote Similarity	NPD2534	Approved
0.6894	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD2533	Approved
0.6885	Remote Similarity	NPD7699	Phase 2
0.6885	Remote Similarity	NPD7700	Phase 2
0.6883	Remote Similarity	NPD6355	Discontinued
0.6882	Remote Similarity	NPD7435	Discontinued
0.6879	Remote Similarity	NPD2346	Discontinued
0.6879	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD1238	Approved
0.6863	Remote Similarity	NPD7715	Approved
0.6863	Remote Similarity	NPD7714	Approved
0.6859	Remote Similarity	NPD8462	Phase 1
0.6859	Remote Similarity	NPD3748	Approved
0.6857	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD8319	Approved
0.6845	Remote Similarity	NPD8320	Phase 1
0.6838	Remote Similarity	NPD1929	Approved
0.6838	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD1930	Approved
0.6826	Remote Similarity	NPD3817	Phase 2
0.6824	Remote Similarity	NPD6959	Discontinued
0.6821	Remote Similarity	NPD3818	Discontinued
0.6815	Remote Similarity	NPD2438	Suspended
0.6802	Remote Similarity	NPD6166	Phase 2
0.6802	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD6785	Approved
0.6798	Remote Similarity	NPD6784	Approved
0.679	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD164	Approved
0.6783	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD230	Phase 1
0.6772	Remote Similarity	NPD6002	Phase 3
0.6772	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6004	Phase 3
0.6772	Remote Similarity	NPD6005	Phase 3
0.6772	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD7713	Phase 3
0.6753	Remote Similarity	NPD6233	Phase 2
0.6752	Remote Similarity	NPD2799	Discontinued
0.675	Remote Similarity	NPD4110	Phase 3
0.675	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD3749	Approved
0.6744	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD7074	Phase 3
0.6738	Remote Similarity	NPD6823	Phase 2
0.6732	Remote Similarity	NPD7095	Approved
0.6728	Remote Similarity	NPD6799	Approved
0.672	Remote Similarity	NPD6780	Approved
0.672	Remote Similarity	NPD6779	Approved
0.672	Remote Similarity	NPD6782	Approved
0.672	Remote Similarity	NPD6777	Approved
0.672	Remote Similarity	NPD6781	Approved
0.672	Remote Similarity	NPD6778	Approved
0.672	Remote Similarity	NPD6776	Approved
0.6718	Remote Similarity	NPD8404	Phase 2
0.6715	Remote Similarity	NPD6647	Phase 2
0.6713	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD9545	Approved
0.671	Remote Similarity	NPD4140	Approved
0.6707	Remote Similarity	NPD1934	Approved
0.6706	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7697	Approved
0.6702	Remote Similarity	NPD7698	Approved
0.6702	Remote Similarity	NPD7696	Phase 3
0.6691	Remote Similarity	NPD6685	Approved
0.6688	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD2313	Discontinued
0.6688	Remote Similarity	NPD6798	Discontinued
0.6687	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7028	Phase 2
0.6686	Remote Similarity	NPD3787	Discontinued
0.6686	Remote Similarity	NPD7229	Phase 3
0.6686	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7054	Approved
0.6667	Remote Similarity	NPD2067	Discontinued
0.6667	Remote Similarity	NPD6832	Phase 2
0.6667	Remote Similarity	NPD5909	Discontinued
0.6667	Remote Similarity	NPD7874	Approved
0.6667	Remote Similarity	NPD7871	Phase 2
0.6667	Remote Similarity	NPD1237	Approved
0.6667	Remote Similarity	NPD5762	Approved
0.6667	Remote Similarity	NPD5763	Approved
0.6667	Remote Similarity	NPD7870	Phase 2
0.6667	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1465	Phase 2
0.6648	Remote Similarity	NPD7472	Approved
0.6646	Remote Similarity	NPD7033	Discontinued

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