NPASS Compound

Structure

NPC66761 OpenBabel07101719402D 37 40 0 0 1 0 0 0 0 0999 V2000 -2.3976 0.0125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3070 -2.5872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5464 3.3724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0545 3.1192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2750 1.4160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3768 0.4474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8898 0.7573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5146 -1.0701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6711 -1.5572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5146 -0.0961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8276 -1.0701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6711 0.3909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3108 -0.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6406 -1.1651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4669 -0.2746 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0210 -1.9247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3079 2.7651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8981 2.6322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8276 -0.0961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1264 -0.6880 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1647 1.5674 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3494 1.0903 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0545 1.1712 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2970 0.3909 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9840 0.3909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4870 0.8435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2825 -0.0042 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9527 0.2025 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9518 -2.2118 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2146 3.1210 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7416 3.1192 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9840 1.3649 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8043 -0.9751 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1628 1.8020 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8981 1.6582 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1405 -0.0961 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 15 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 26 1 0 0 0 0 6 26 1 0 0 0 0 7 27 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 2 0 0 0 0 11 19 2 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 13 15 1 0 0 0 0 14 20 1 0 0 0 0 15 28 1 1 0 0 0 16 29 2 0 0 0 0 16 33 1 0 0 0 0 17 30 2 0 0 0 0 17 34 1 0 0 0 0 18 31 2 0 0 0 0 18 35 1 0 0 0 0 19 25 1 0 0 0 0 20 27 1 1 0 0 0 20 33 1 0 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 21 26 1 6 0 0 0 22 24 1 0 0 0 0 22 34 1 1 0 0 0 23 28 1 6 0 0 0 23 35 1 0 0 0 0 24 27 1 6 0 0 0 24 36 1 0 0 0 0 25 32 2 0 0 0 0 25 36 1 0 0 0 0 26 37 1 0 0 0 0 27 28 1 6 0 0 0 28 37 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	516.24
Volume:	519.275
LogP:	3.779
LogD:	2.362
LogS:	-4.34
# Rotatable Bonds:	9
TPSA:	114.43
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.427
Synthetic Accessibility Score:	5.627
Fsp3:	0.643
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:	-5.197
MDCK Permeability:	7.504180393880233e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.819
30% Bioavailability (F30%):	0.955

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.395
Plasma Protein Binding (PPB):	62.135520935058594%
Volume Distribution (VD):	2.084
Pgp-substrate:	21.317224502563477%

ADMET: Metabolism

CYP1A2-inhibitor:	0.097
CYP1A2-substrate:	0.034
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.069
CYP2C9-inhibitor:	0.225
CYP2C9-substrate:	0.028
CYP2D6-inhibitor:	0.842
CYP2D6-substrate:	0.077
CYP3A4-inhibitor:	0.393
CYP3A4-substrate:	0.332

ADMET: Excretion

Clearance (CL):	3.278
Half-life (T1/2):	0.807

ADMET: Toxicity

hERG Blockers:	0.274
Human Hepatotoxicity (H-HT):	0.977
Drug-inuced Liver Injury (DILI):	0.975
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.285
Maximum Recommended Daily Dose:	0.017
Skin Sensitization:	0.339
Carcinogencity:	0.06
Eye Corrosion:	0.007
Eye Irritation:	0.06
Respiratory Toxicity:	0.942

Download Data

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

Natural Product: NPC66761

Natural Product ID:	NPC66761
*Common Name:**	ZFYHVMQCJIKTLP-LLWUNBJKSA-N
IUPAC Name:	n.a.
Synonyms:	Celafolin C-1
Standard InCHIKey:	ZFYHVMQCJIKTLP-LLWUNBJKSA-N
Standard InCHI:	InChI=1S/C28H36O9/c1-15-13-14-20(33-16(2)29)27(7)24(36-25(32)19-11-9-8-10-12-19)22(34-17(3)30)21-23(35-18(4)31)28(15,27)37-26(21,5)6/h8-12,15,20-24H,13-14H2,1-7H3/t15-,20+,21-,22-,23-,24+,27+,28-/m1/s1
SMILES:	CC(=O)O[C@@H]1[C@@H]2[C@@H](OC(=O)C)[C@]3([C@@]([C@H]1OC(=O)c1ccccc1)(C)[C@H](CC[C@H]3C)OC(=O)C)OC2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL511093
PubChem CID:	44593422
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.	root	n.a.	PMID[10346948]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	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]
NPO31542	Celastrus stephanotiifolius	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8350085]
NPO31542	Celastrus stephanotiifolius	Species	Celastraceae	Eukaryota	n.a.	seed	n.a.	PMID[8350085]
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
Others	8

Activity Type	# Activity
Cell Line	5
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[451622]
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[451622]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	6800.0	nM	PMID[451623]
NPT2	Others	Unspecified		Activity	=	15.3	%	PMID[451622]
NPT2	Others	Unspecified		Activity	=	52.8	%	PMID[451622]
NPT2	Others	Unspecified		Activity	=	90.6	%	PMID[451622]
NPT2	Others	Unspecified		Activity	=	100.0	%	PMID[451622]

☑ 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 NPC66761 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	327
0.1-0.2	1179
0.2-0.3	2230
0.3-0.4	4561
0.4-0.5	9216
0.5-0.6	12395
0.6-0.7	10832
0.7-0.8	1485
0.8-0.85	230
0.85-0.9	84
0.9-0.95	97
0.95-1	61

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC17877
1.0	High Similarity	NPC195647
1.0	High Similarity	NPC291638
1.0	High Similarity	NPC472577
0.9921	High Similarity	NPC474608
0.9695	High Similarity	NPC97667
0.9695	High Similarity	NPC90614
0.9695	High Similarity	NPC473613
0.9695	High Similarity	NPC473085
0.9695	High Similarity	NPC476094
0.9695	High Similarity	NPC473060
0.9695	High Similarity	NPC4341
0.9695	High Similarity	NPC473081
0.9695	High Similarity	NPC211137
0.9695	High Similarity	NPC200592
0.9695	High Similarity	NPC147880
0.9695	High Similarity	NPC43241
0.9695	High Similarity	NPC473758
0.9695	High Similarity	NPC48017
0.9695	High Similarity	NPC473109
0.9695	High Similarity	NPC171207
0.9695	High Similarity	NPC473112
0.9695	High Similarity	NPC184747
0.9692	High Similarity	NPC283375
0.9692	High Similarity	NPC183122
0.9621	High Similarity	NPC27377
0.9621	High Similarity	NPC291599
0.9621	High Similarity	NPC472576
0.9621	High Similarity	NPC41481
0.9621	High Similarity	NPC16912
0.9621	High Similarity	NPC87448
0.9621	High Similarity	NPC118080
0.9621	High Similarity	NPC97947
0.9618	High Similarity	NPC214550
0.9618	High Similarity	NPC475652
0.9618	High Similarity	NPC210591
0.9606	High Similarity	NPC147561
0.9545	High Similarity	NPC100913
0.9545	High Similarity	NPC275592
0.9478	High Similarity	NPC139067
0.9478	High Similarity	NPC475429
0.9478	High Similarity	NPC473673
0.9478	High Similarity	NPC270498
0.9478	High Similarity	NPC147217
0.9478	High Similarity	NPC177340
0.9478	High Similarity	NPC163087
0.9478	High Similarity	NPC191082
0.9478	High Similarity	NPC246480
0.9407	High Similarity	NPC95810
0.9407	High Similarity	NPC241951
0.9407	High Similarity	NPC188865
0.9407	High Similarity	NPC25768
0.9407	High Similarity	NPC51314
0.9407	High Similarity	NPC67777
0.9407	High Similarity	NPC70716
0.9407	High Similarity	NPC57628
0.9407	High Similarity	NPC470231
0.9407	High Similarity	NPC472573
0.9407	High Similarity	NPC125106
0.9407	High Similarity	NPC475759
0.9407	High Similarity	NPC163719
0.9407	High Similarity	NPC472569
0.9407	High Similarity	NPC472570
0.9407	High Similarity	NPC11685
0.9407	High Similarity	NPC476974
0.9407	High Similarity	NPC470152
0.9407	High Similarity	NPC95265
0.9398	High Similarity	NPC183270
0.9398	High Similarity	NPC477904
0.9338	High Similarity	NPC470159
0.9338	High Similarity	NPC70403
0.9338	High Similarity	NPC184817
0.9338	High Similarity	NPC472568
0.9338	High Similarity	NPC471107
0.9338	High Similarity	NPC471100
0.9338	High Similarity	NPC470157
0.9338	High Similarity	NPC96903
0.9338	High Similarity	NPC200471
0.9338	High Similarity	NPC469349
0.9338	High Similarity	NPC473088
0.9338	High Similarity	NPC472575
0.9338	High Similarity	NPC471104
0.9338	High Similarity	NPC158663
0.9338	High Similarity	NPC472571
0.9338	High Similarity	NPC174982
0.9338	High Similarity	NPC476973
0.9338	High Similarity	NPC171525
0.9338	High Similarity	NPC472572
0.9338	High Similarity	NPC29704
0.9338	High Similarity	NPC177940
0.927	High Similarity	NPC474935
0.9265	High Similarity	NPC475122
0.9254	High Similarity	NPC472547
0.9203	High Similarity	NPC281717
0.9173	High Similarity	NPC472545
0.9173	High Similarity	NPC472551
0.9141	High Similarity	NPC473082
0.9137	High Similarity	NPC266265
0.9137	High Similarity	NPC270590
0.9137	High Similarity	NPC471101
0.9137	High Similarity	NPC92293
0.9137	High Similarity	NPC476975
0.9137	High Similarity	NPC301556
0.9118	High Similarity	NPC34012
0.9104	High Similarity	NPC39549
0.9071	High Similarity	NPC473214
0.9071	High Similarity	NPC254558
0.9071	High Similarity	NPC470245
0.9062	High Similarity	NPC473083
0.9058	High Similarity	NPC472556
0.9051	High Similarity	NPC477894
0.9044	High Similarity	NPC224491
0.9015	High Similarity	NPC238370
0.9007	High Similarity	NPC471103
0.9007	High Similarity	NPC51602
0.9007	High Similarity	NPC470153
0.9	High Similarity	NPC473215
0.8993	High Similarity	NPC48599
0.8993	High Similarity	NPC209592
0.8986	High Similarity	NPC38696
0.8978	High Similarity	NPC472546
0.8976	High Similarity	NPC70973
0.8963	High Similarity	NPC475373
0.8955	High Similarity	NPC473399
0.8955	High Similarity	NPC473216
0.8929	High Similarity	NPC473760
0.8921	High Similarity	NPC127857
0.8913	High Similarity	NPC91703
0.8905	High Similarity	NPC266374
0.8898	High Similarity	NPC37641
0.8898	High Similarity	NPC311175
0.8872	High Similarity	NPC472394
0.8857	High Similarity	NPC473602
0.8857	High Similarity	NPC240115
0.8849	High Similarity	NPC34943
0.8819	High Similarity	NPC282239
0.8819	High Similarity	NPC34066
0.8815	High Similarity	NPC477893
0.8811	High Similarity	NPC472548
0.8811	High Similarity	NPC477905
0.8803	High Similarity	NPC31829
0.8803	High Similarity	NPC469448
0.8794	High Similarity	NPC217918
0.8786	High Similarity	NPC125882
0.8786	High Similarity	NPC92867
0.8786	High Similarity	NPC311825
0.8777	High Similarity	NPC191387
0.8777	High Similarity	NPC131966
0.8759	High Similarity	NPC9905
0.8759	High Similarity	NPC106895
0.875	High Similarity	NPC472372
0.875	High Similarity	NPC472374
0.8741	High Similarity	NPC469415
0.8741	High Similarity	NPC48929
0.8732	High Similarity	NPC250046
0.8732	High Similarity	NPC60509
0.8732	High Similarity	NPC76103
0.8732	High Similarity	NPC81698
0.8723	High Similarity	NPC478263
0.8723	High Similarity	NPC20255
0.8705	High Similarity	NPC182869
0.8705	High Similarity	NPC192658
0.8702	High Similarity	NPC473110
0.8702	High Similarity	NPC473111
0.8702	High Similarity	NPC476970
0.8699	High Similarity	NPC472393
0.8696	High Similarity	NPC162613
0.8696	High Similarity	NPC87934
0.8696	High Similarity	NPC475400
0.869	High Similarity	NPC473670
0.869	High Similarity	NPC473611
0.869	High Similarity	NPC473632
0.869	High Similarity	NPC472549
0.869	High Similarity	NPC132599
0.869	High Similarity	NPC469730
0.869	High Similarity	NPC21410
0.869	High Similarity	NPC469422
0.8676	High Similarity	NPC477896
0.8671	High Similarity	NPC303429
0.8671	High Similarity	NPC222102
0.8671	High Similarity	NPC112216
0.8671	High Similarity	NPC161239
0.8671	High Similarity	NPC91730
0.8671	High Similarity	NPC476173
0.8671	High Similarity	NPC165260
0.8671	High Similarity	NPC198455
0.8671	High Similarity	NPC7095
0.8662	High Similarity	NPC132652
0.8661	High Similarity	NPC473860
0.8652	High Similarity	NPC478264
0.8639	High Similarity	NPC469399
0.8639	High Similarity	NPC471102
0.8636	High Similarity	NPC476971
0.8636	High Similarity	NPC476972
0.863	High Similarity	NPC217091
0.8626	High Similarity	NPC125053
0.8626	High Similarity	NPC114927
0.8623	High Similarity	NPC472395
0.8623	High Similarity	NPC472371
0.8621	High Similarity	NPC133430

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 NPC66761 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	264
0.1-0.2	744
0.2-0.3	1351
0.3-0.4	2821
0.4-0.5	2307
0.5-0.6	1261
0.6-0.7	378
0.7-0.8	23
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
0.8043	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD7236	Approved
0.7867	Intermediate Similarity	NPD7239	Suspended
0.7752	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD7799	Discontinued
0.7702	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD8407	Phase 2
0.7561	Intermediate Similarity	NPD8368	Discontinued
0.7545	Intermediate Similarity	NPD8434	Phase 2
0.7462	Intermediate Similarity	NPD2182	Approved
0.7447	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD7008	Discontinued
0.7405	Intermediate Similarity	NPD7057	Phase 3
0.7405	Intermediate Similarity	NPD7058	Phase 2
0.7391	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD3764	Approved
0.7353	Intermediate Similarity	NPD8435	Approved
0.7353	Intermediate Similarity	NPD8360	Approved
0.7353	Intermediate Similarity	NPD8361	Approved
0.7333	Intermediate Similarity	NPD4198	Discontinued
0.7329	Intermediate Similarity	NPD8127	Discontinued
0.7299	Intermediate Similarity	NPD7741	Discontinued
0.7285	Intermediate Similarity	NPD4628	Phase 3
0.7278	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD5951	Approved
0.7259	Intermediate Similarity	NPD2629	Approved
0.7239	Intermediate Similarity	NPD6858	Approved
0.7239	Intermediate Similarity	NPD7094	Approved
0.7235	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD37	Approved
0.7214	Intermediate Similarity	NPD6287	Discontinued
0.7192	Intermediate Similarity	NPD7961	Discontinued
0.7188	Intermediate Similarity	NPD4966	Approved
0.7188	Intermediate Similarity	NPD4967	Phase 2
0.7188	Intermediate Similarity	NPD4965	Approved
0.7171	Intermediate Similarity	NPD8166	Discontinued
0.7169	Intermediate Similarity	NPD5844	Phase 1
0.7161	Intermediate Similarity	NPD6273	Approved
0.716	Intermediate Similarity	NPD5494	Approved
0.7154	Intermediate Similarity	NPD164	Approved
0.7143	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD6190	Approved
0.7109	Intermediate Similarity	NPD1238	Approved
0.7102	Intermediate Similarity	NPD8485	Approved
0.7099	Intermediate Similarity	NPD6234	Discontinued
0.7071	Intermediate Similarity	NPD5125	Phase 3
0.7071	Intermediate Similarity	NPD5126	Approved
0.7068	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7819	Suspended
0.7059	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7473	Discontinued
0.7035	Intermediate Similarity	NPD8150	Discontinued
0.7025	Intermediate Similarity	NPD7458	Discontinued
0.702	Intermediate Similarity	NPD2438	Suspended
0.7015	Intermediate Similarity	NPD2067	Discontinued
0.6994	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6599	Discontinued
0.6975	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6232	Discontinued
0.6959	Remote Similarity	NPD8032	Phase 2
0.6959	Remote Similarity	NPD6663	Approved
0.6957	Remote Similarity	NPD5760	Phase 2
0.6957	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5761	Phase 2
0.6954	Remote Similarity	NPD3748	Approved
0.695	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD7003	Approved
0.6933	Remote Similarity	NPD7075	Discontinued
0.6918	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD5736	Approved
0.6912	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7228	Approved
0.6903	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2534	Approved
0.6879	Remote Similarity	NPD2532	Approved
0.6879	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2533	Approved
0.6875	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6832	Phase 2
0.6868	Remote Similarity	NPD7497	Discontinued
0.6857	Remote Similarity	NPD7610	Discontinued
0.6846	Remote Similarity	NPD7798	Approved
0.6846	Remote Similarity	NPD7713	Phase 3
0.6842	Remote Similarity	NPD6765	Approved
0.6842	Remote Similarity	NPD6764	Approved
0.6815	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD3226	Approved
0.681	Remote Similarity	NPD5402	Approved
0.681	Remote Similarity	NPD3817	Phase 2
0.68	Remote Similarity	NPD2979	Phase 3
0.6797	Remote Similarity	NPD2935	Discontinued
0.6797	Remote Similarity	NPD2796	Approved
0.679	Remote Similarity	NPD6801	Discontinued
0.677	Remote Similarity	NPD4380	Phase 2
0.6768	Remote Similarity	NPD7768	Phase 2
0.6763	Remote Similarity	NPD8313	Approved
0.6763	Remote Similarity	NPD8312	Approved
0.6761	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD230	Phase 1
0.6755	Remote Similarity	NPD6355	Discontinued
0.6753	Remote Similarity	NPD2346	Discontinued
0.6753	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD7240	Approved
0.6744	Remote Similarity	NPD6559	Discontinued
0.6731	Remote Similarity	NPD4110	Phase 3
0.6731	Remote Similarity	NPD3750	Approved
0.6731	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD7411	Suspended
0.6715	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD5667	Approved
0.6709	Remote Similarity	NPD6799	Approved
0.6707	Remote Similarity	NPD7199	Phase 2
0.6707	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD1930	Approved
0.6692	Remote Similarity	NPD1929	Approved
0.669	Remote Similarity	NPD6637	Approved
0.669	Remote Similarity	NPD3972	Approved
0.669	Remote Similarity	NPD9545	Approved
0.6689	Remote Similarity	NPD4307	Phase 2
0.6688	Remote Similarity	NPD5408	Approved
0.6688	Remote Similarity	NPD5404	Approved
0.6688	Remote Similarity	NPD5405	Approved
0.6688	Remote Similarity	NPD5406	Approved
0.6687	Remote Similarity	NPD5403	Approved
0.6686	Remote Similarity	NPD6784	Approved
0.6686	Remote Similarity	NPD6785	Approved
0.6667	Remote Similarity	NPD8462	Phase 1
0.6667	Remote Similarity	NPD5401	Approved
0.6667	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2569	Approved
0.6667	Remote Similarity	NPD7097	Phase 1
0.6667	Remote Similarity	NPD2567	Approved
0.6647	Remote Similarity	NPD7685	Pre-registration
0.6646	Remote Similarity	NPD8455	Phase 2
0.6646	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD6005	Phase 3
0.6645	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD6004	Phase 3
0.6645	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD6002	Phase 3
0.6645	Remote Similarity	NPD7266	Discontinued
0.6643	Remote Similarity	NPD3024	Approved
0.6643	Remote Similarity	NPD3025	Approved
0.6642	Remote Similarity	NPD5909	Discontinued
0.6627	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD6385	Approved
0.6626	Remote Similarity	NPD6386	Approved
0.6626	Remote Similarity	NPD6873	Phase 2
0.6623	Remote Similarity	NPD2799	Discontinued
0.6623	Remote Similarity	NPD6233	Phase 2
0.6621	Remote Similarity	NPD1281	Approved
0.6615	Remote Similarity	NPD1989	Approved
0.6608	Remote Similarity	NPD3818	Discontinued
0.6606	Remote Similarity	NPD5353	Approved
0.6603	Remote Similarity	NPD970	Clinical (unspecified phase)
0.66	Remote Similarity	NPD7095	Approved
0.6599	Remote Similarity	NPD1876	Approved
0.6597	Remote Similarity	NPD17	Approved
0.6591	Remote Similarity	NPD2066	Phase 3
0.6589	Remote Similarity	NPD1202	Approved
0.6587	Remote Similarity	NPD919	Approved
0.6585	Remote Similarity	NPD1934	Approved
0.6584	Remote Similarity	NPD920	Approved
0.6581	Remote Similarity	NPD6099	Approved
0.6581	Remote Similarity	NPD6100	Approved
0.6579	Remote Similarity	NPD4140	Approved
0.6568	Remote Similarity	NPD7229	Phase 3
0.6567	Remote Similarity	NPD6647	Phase 2
0.6564	Remote Similarity	NPD7028	Phase 2
0.6562	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD6798	Discontinued
0.6556	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD2313	Discontinued
0.6552	Remote Similarity	NPD3023	Approved
0.6552	Remote Similarity	NPD3026	Approved
0.6544	Remote Similarity	NPD6685	Approved
0.6538	Remote Similarity	NPD5763	Approved
0.6538	Remote Similarity	NPD5762	Approved
0.6536	Remote Similarity	NPD1933	Approved
0.6536	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD5327	Phase 3
0.6529	Remote Similarity	NPD5242	Approved
0.6528	Remote Similarity	NPD5585	Approved
0.6528	Remote Similarity	NPD8404	Phase 2
0.6528	Remote Similarity	NPD5691	Approved
0.6527	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD3749	Approved
0.6522	Remote Similarity	NPD5955	Clinical (unspecified phase)

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