NPASS Compound

Structure

NPC473908 OpenBabel07101718322D 44 48 0 0 1 0 0 0 0 0999 V2000 -4.6665 1.9173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3986 1.9173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2599 0.0135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0714 -2.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2757 -3.8698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2268 -3.5608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9456 0.2045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 0.8736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5296 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5326 0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6665 -0.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5657 0.3736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3578 -0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5326 1.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5168 0.6826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0714 -2.0827 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.6665 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -2.5827 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.8005 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5326 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6665 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8005 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5326 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7247 1.6608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1499 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4836 -2.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9345 -4.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6665 -4.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6757 1.9698 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9815 2.3299 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1009 -1.2737 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9420 -2.5608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5296 -3.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4836 -1.2737 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 -1.0827 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 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 32 1 0 0 0 0 6 32 1 0 0 0 0 7 33 1 0 0 0 0 8 33 1 0 0 0 0 9 41 1 0 0 0 0 10 11 1 0 0 0 0 10 15 2 0 0 0 0 11 18 1 0 0 0 0 12 13 1 0 0 0 0 12 16 2 0 0 0 0 14 19 1 0 0 0 0 14 20 1 0 0 0 0 16 30 1 0 0 0 0 17 32 1 0 0 0 0 17 42 1 0 0 0 0 18 27 2 0 0 0 0 18 28 1 0 0 0 0 19 25 1 0 0 0 0 19 29 2 0 0 0 0 20 22 1 0 0 0 0 20 41 1 0 0 0 0 21 25 1 0 0 0 0 21 26 2 0 0 0 0 21 27 1 0 0 0 0 22 23 2 0 0 0 0 22 34 1 0 0 0 0 23 29 1 0 0 0 0 23 33 1 0 0 0 0 24 26 1 0 0 0 0 24 28 2 0 0 0 0 24 32 1 0 0 0 0 25 35 2 0 0 0 0 26 36 1 0 0 0 0 27 43 1 0 0 0 0 28 42 1 0 0 0 0 29 43 1 0 0 0 0 30 37 2 0 0 0 0 30 38 1 0 0 0 0 31 34 1 0 0 0 0 31 39 2 0 0 0 0 31 40 1 0 0 0 0 33 44 1 0 0 0 0 34 13 1 1 0 0 0 34 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	608.26
Volume:	615.375
LogP:	6.151
LogD:	2.516
LogS:	-3.224
# Rotatable Bonds:	7
TPSA:	152.73
# H-Bond Aceptor:	10
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.343
Synthetic Accessibility Score:	5.521
Fsp3:	0.5
Lipinski Rule-of-5:	Rejected
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:	-5.61
MDCK Permeability:	1.9186139979865402e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.483
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.387

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.2
Plasma Protein Binding (PPB):	86.78115844726562%
Volume Distribution (VD):	1.51
Pgp-substrate:	8.347724914550781%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.767
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.836
CYP2C9-inhibitor:	0.163
CYP2C9-substrate:	0.324
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.088
CYP3A4-inhibitor:	0.068
CYP3A4-substrate:	0.784

ADMET: Excretion

Clearance (CL):	1.16
Half-life (T1/2):	0.125

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.888
Drug-inuced Liver Injury (DILI):	0.993
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.988
Maximum Recommended Daily Dose:	0.406
Skin Sensitization:	0.514
Carcinogencity:	0.449
Eye Corrosion:	0.003
Eye Irritation:	0.028
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC473908

Natural Product ID:	NPC473908
*Common Name:**	Scortechinone X
IUPAC Name:	n.a.
Synonyms:	Scortechinone X
Standard InCHIKey:	CDEHIYLRKGRKGU-MVXUOOCWSA-N
Standard InCHI:	InChI=1S/C34H40O10/c1-15(2)10-11-18-27-21(26(36)24-28(18)42-17(4)32(24,5)6)25(35)19-14-20(41-9)22-23(29(19)43-27)33(7,8)44-34(22,31(39)40)13-12-16(3)30(37)38/h10,12,17,20,36H,11,13-14H2,1-9H3,(H,37,38)(H,39,40)/b16-12+/t17?,20?,34-/m0/s1
SMILES:	COC1Cc2c(C3=C1[C@](C/C=C(/C(=O)O)C)(OC3(C)C)C(=O)O)oc1c(c2=O)c(O)c2c(c1CC=C(C)C)OC(C2(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454955
PubChem CID:	44559178
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO13968	Garcinia scortechinii	Species	Clusiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[16038540]
NPO13968	Garcinia scortechinii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13968	Garcinia scortechinii	Species	Clusiaceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	210000.0	nM	PMID[560313]

☑ 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 NPC473908 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	377
0.1-0.2	1473
0.2-0.3	3236
0.3-0.4	7270
0.4-0.5	10875
0.5-0.6	5745
0.6-0.7	5834
0.7-0.8	5766
0.8-0.85	1961
0.85-0.9	157
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9273	High Similarity	NPC227275
0.9102	High Similarity	NPC233978
0.9096	High Similarity	NPC162248
0.9048	High Similarity	NPC473607
0.8982	High Similarity	NPC475398
0.8981	High Similarity	NPC321387
0.8981	High Similarity	NPC327059
0.8941	High Similarity	NPC475656
0.8941	High Similarity	NPC475148
0.8935	High Similarity	NPC473729
0.8929	High Similarity	NPC98943
0.8862	High Similarity	NPC169018
0.8861	High Similarity	NPC476509
0.8861	High Similarity	NPC470908
0.881	High Similarity	NPC476311
0.881	High Similarity	NPC476152
0.881	High Similarity	NPC476229
0.8788	High Similarity	NPC189689
0.8765	High Similarity	NPC476199
0.8765	High Similarity	NPC476210
0.8758	High Similarity	NPC279218
0.8758	High Similarity	NPC108937
0.875	High Similarity	NPC256141
0.8743	High Similarity	NPC75141
0.8743	High Similarity	NPC40089
0.8743	High Similarity	NPC158329
0.8743	High Similarity	NPC47634
0.8743	High Similarity	NPC476146
0.8743	High Similarity	NPC55422
0.8743	High Similarity	NPC102810
0.8742	High Similarity	NPC180351
0.8734	High Similarity	NPC472345
0.872	High Similarity	NPC92589
0.8712	High Similarity	NPC125969
0.871	High Similarity	NPC74397
0.8704	High Similarity	NPC470625
0.8704	High Similarity	NPC474738
0.8704	High Similarity	NPC109967
0.8704	High Similarity	NPC78554
0.8704	High Similarity	NPC475797
0.8704	High Similarity	NPC321372
0.8704	High Similarity	NPC129053
0.8704	High Similarity	NPC469936
0.8704	High Similarity	NPC474609
0.8698	High Similarity	NPC475080
0.8698	High Similarity	NPC476139
0.869	High Similarity	NPC313717
0.869	High Similarity	NPC315306
0.869	High Similarity	NPC476196
0.8654	High Similarity	NPC472344
0.8654	High Similarity	NPC112829
0.8642	High Similarity	NPC469934
0.8642	High Similarity	NPC471116
0.8639	High Similarity	NPC476159
0.8634	High Similarity	NPC327269
0.8634	High Similarity	NPC476238
0.8634	High Similarity	NPC31627
0.8631	High Similarity	NPC476216
0.8631	High Similarity	NPC41598
0.8608	High Similarity	NPC470910
0.8599	High Similarity	NPC307895
0.8599	High Similarity	NPC33653
0.8599	High Similarity	NPC470553
0.8599	High Similarity	NPC184738
0.8588	High Similarity	NPC469393
0.858	High Similarity	NPC193698
0.858	High Similarity	NPC100134
0.858	High Similarity	NPC209760
0.8571	High Similarity	NPC476162
0.8571	High Similarity	NPC471675
0.8571	High Similarity	NPC223413
0.8563	High Similarity	NPC316262
0.8563	High Similarity	NPC314653
0.8563	High Similarity	NPC106700
0.8553	High Similarity	NPC285748
0.8553	High Similarity	NPC202494
0.8545	High Similarity	NPC172687
0.8545	High Similarity	NPC313368
0.8545	High Similarity	NPC286422
0.8545	High Similarity	NPC306978
0.8544	High Similarity	NPC470554
0.8544	High Similarity	NPC133060
0.8544	High Similarity	NPC71184
0.8544	High Similarity	NPC118059
0.8544	High Similarity	NPC206212
0.8544	High Similarity	NPC288910
0.8537	High Similarity	NPC246466
0.8537	High Similarity	NPC161650
0.8537	High Similarity	NPC476930
0.8535	High Similarity	NPC321148
0.8535	High Similarity	NPC276565
0.8535	High Similarity	NPC321629
0.8535	High Similarity	NPC294432
0.8535	High Similarity	NPC470556
0.8535	High Similarity	NPC326193
0.8535	High Similarity	NPC323884
0.8529	High Similarity	NPC477529
0.8528	High Similarity	NPC476169
0.8526	High Similarity	NPC164697
0.8526	High Similarity	NPC82920
0.8526	High Similarity	NPC289660
0.8521	High Similarity	NPC54903
0.8521	High Similarity	NPC286074
0.8519	High Similarity	NPC477957
0.8519	High Similarity	NPC210597
0.8519	High Similarity	NPC473996
0.8519	High Similarity	NPC285623
0.8519	High Similarity	NPC470353
0.8512	High Similarity	NPC323137
0.8512	High Similarity	NPC476255
0.8509	High Similarity	NPC476185
0.8509	High Similarity	NPC321896
0.8509	High Similarity	NPC472421
0.8503	High Similarity	NPC131578
0.85	High Similarity	NPC211811
0.85	High Similarity	NPC10097
0.8494	Intermediate Similarity	NPC117985
0.8494	Intermediate Similarity	NPC187354
0.8485	Intermediate Similarity	NPC311574
0.8485	Intermediate Similarity	NPC264932
0.8485	Intermediate Similarity	NPC470607
0.8481	Intermediate Similarity	NPC474939
0.8481	Intermediate Similarity	NPC470909
0.8481	Intermediate Similarity	NPC96216
0.8481	Intermediate Similarity	NPC18886
0.8476	Intermediate Similarity	NPC20530
0.8476	Intermediate Similarity	NPC215917
0.8476	Intermediate Similarity	NPC10754
0.8471	Intermediate Similarity	NPC316911
0.8471	Intermediate Similarity	NPC316560
0.8471	Intermediate Similarity	NPC111201
0.8471	Intermediate Similarity	NPC120220
0.8466	Intermediate Similarity	NPC469405
0.8466	Intermediate Similarity	NPC293286
0.8466	Intermediate Similarity	NPC248793
0.8466	Intermediate Similarity	NPC311579
0.8466	Intermediate Similarity	NPC180301
0.8466	Intermediate Similarity	NPC282636
0.8466	Intermediate Similarity	NPC236756
0.8466	Intermediate Similarity	NPC294863
0.8462	Intermediate Similarity	NPC270913
0.8462	Intermediate Similarity	NPC193222
0.8462	Intermediate Similarity	NPC476459
0.8457	Intermediate Similarity	NPC474772
0.8457	Intermediate Similarity	NPC472636
0.8457	Intermediate Similarity	NPC474744
0.8457	Intermediate Similarity	NPC472580
0.8457	Intermediate Similarity	NPC81474
0.8457	Intermediate Similarity	NPC471229
0.8457	Intermediate Similarity	NPC472423
0.8457	Intermediate Similarity	NPC290671
0.8452	Intermediate Similarity	NPC259007
0.8452	Intermediate Similarity	NPC204088
0.8452	Intermediate Similarity	NPC329215
0.8452	Intermediate Similarity	NPC294722
0.8447	Intermediate Similarity	NPC317492
0.8447	Intermediate Similarity	NPC139966
0.8447	Intermediate Similarity	NPC307052
0.8443	Intermediate Similarity	NPC93215
0.8443	Intermediate Similarity	NPC219861
0.8443	Intermediate Similarity	NPC475106
0.8438	Intermediate Similarity	NPC177995
0.8438	Intermediate Similarity	NPC91902
0.8438	Intermediate Similarity	NPC474108
0.8438	Intermediate Similarity	NPC85773
0.8438	Intermediate Similarity	NPC129650
0.843	Intermediate Similarity	NPC294149
0.8428	Intermediate Similarity	NPC297788
0.8428	Intermediate Similarity	NPC472446
0.8428	Intermediate Similarity	NPC171656
0.8428	Intermediate Similarity	NPC472447
0.8428	Intermediate Similarity	NPC316535
0.8424	Intermediate Similarity	NPC196448
0.8424	Intermediate Similarity	NPC472889
0.8424	Intermediate Similarity	NPC470606
0.8424	Intermediate Similarity	NPC210048
0.8421	Intermediate Similarity	NPC472584
0.8421	Intermediate Similarity	NPC118128
0.8415	Intermediate Similarity	NPC111341
0.8415	Intermediate Similarity	NPC207809
0.8415	Intermediate Similarity	NPC304207
0.8415	Intermediate Similarity	NPC470681
0.8415	Intermediate Similarity	NPC478221
0.8415	Intermediate Similarity	NPC217706
0.8415	Intermediate Similarity	NPC259710
0.8415	Intermediate Similarity	NPC473241
0.8415	Intermediate Similarity	NPC48579
0.8415	Intermediate Similarity	NPC304745
0.8412	Intermediate Similarity	NPC473095
0.8412	Intermediate Similarity	NPC473096
0.8412	Intermediate Similarity	NPC288813
0.8412	Intermediate Similarity	NPC165456
0.8412	Intermediate Similarity	NPC63514
0.8405	Intermediate Similarity	NPC288534
0.8405	Intermediate Similarity	NPC275878
0.8405	Intermediate Similarity	NPC171651
0.8405	Intermediate Similarity	NPC243171
0.8405	Intermediate Similarity	NPC35567
0.8405	Intermediate Similarity	NPC138288
0.8402	Intermediate Similarity	NPC469394

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 NPC473908 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	326
0.1-0.2	947
0.2-0.3	1995
0.3-0.4	2613
0.4-0.5	1958
0.5-0.6	859
0.6-0.7	313
0.7-0.8	121
0.8-0.85	15
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8765	High Similarity	NPD7075	Discontinued
0.858	High Similarity	NPD7096	Clinical (unspecified phase)
0.8519	High Similarity	NPD6801	Discontinued
0.8462	Intermediate Similarity	NPD2800	Approved
0.8304	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD6599	Discontinued
0.8199	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD2533	Approved
0.8199	Intermediate Similarity	NPD2532	Approved
0.8199	Intermediate Similarity	NPD2534	Approved
0.8171	Intermediate Similarity	NPD4380	Phase 2
0.8137	Intermediate Similarity	NPD6799	Approved
0.8133	Intermediate Similarity	NPD7819	Suspended
0.8084	Intermediate Similarity	NPD3817	Phase 2
0.8036	Intermediate Similarity	NPD3882	Suspended
0.7988	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD5403	Approved
0.7976	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD5402	Approved
0.7975	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD6651	Approved
0.7933	Intermediate Similarity	NPD8434	Phase 2
0.7931	Intermediate Similarity	NPD3818	Discontinued
0.7917	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD7411	Suspended
0.7866	Intermediate Similarity	NPD5401	Approved
0.7824	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD7768	Phase 2
0.7816	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD7808	Phase 3
0.7809	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD920	Approved
0.776	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD6559	Discontinued
0.7753	Intermediate Similarity	NPD7251	Discontinued
0.7751	Intermediate Similarity	NPD1934	Approved
0.7733	Intermediate Similarity	NPD919	Approved
0.7733	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD1549	Phase 2
0.7714	Intermediate Similarity	NPD6166	Phase 2
0.7714	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD2801	Approved
0.7702	Intermediate Similarity	NPD2796	Approved
0.7697	Intermediate Similarity	NPD6797	Phase 2
0.7697	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD5494	Approved
0.7688	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD3749	Approved
0.767	Intermediate Similarity	NPD7473	Discontinued
0.7669	Intermediate Similarity	NPD1243	Approved
0.7654	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1510	Phase 2
0.7622	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD3750	Approved
0.7622	Intermediate Similarity	NPD4628	Phase 3
0.7607	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD1512	Approved
0.76	Intermediate Similarity	NPD6232	Discontinued
0.76	Intermediate Similarity	NPD5710	Approved
0.76	Intermediate Similarity	NPD5711	Approved
0.7584	Intermediate Similarity	NPD7054	Approved
0.7543	Intermediate Similarity	NPD1247	Approved
0.7543	Intermediate Similarity	NPD6959	Discontinued
0.7542	Intermediate Similarity	NPD7074	Phase 3
0.7542	Intermediate Similarity	NPD7472	Approved
0.753	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1511	Approved
0.7455	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD5953	Discontinued
0.7391	Intermediate Similarity	NPD1240	Approved
0.7389	Intermediate Similarity	NPD7286	Phase 2
0.7389	Intermediate Similarity	NPD5844	Phase 1
0.7375	Intermediate Similarity	NPD2313	Discontinued
0.7351	Intermediate Similarity	NPD8150	Discontinued
0.7346	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD5124	Phase 1
0.7318	Intermediate Similarity	NPD2403	Approved
0.7317	Intermediate Similarity	NPD2799	Discontinued
0.7317	Intermediate Similarity	NPD3748	Approved
0.7301	Intermediate Similarity	NPD1607	Approved
0.7299	Intermediate Similarity	NPD1465	Phase 2
0.7283	Intermediate Similarity	NPD8312	Approved
0.7283	Intermediate Similarity	NPD8313	Approved
0.7273	Intermediate Similarity	NPD2935	Discontinued
0.7273	Intermediate Similarity	NPD1551	Phase 2
0.7273	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7435	Discontinued
0.7267	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3226	Approved
0.7263	Intermediate Similarity	NPD3926	Phase 2
0.7263	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6355	Discontinued
0.7238	Intermediate Similarity	NPD3751	Discontinued
0.7232	Intermediate Similarity	NPD6234	Discontinued
0.7228	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6099	Approved
0.7169	Intermediate Similarity	NPD6100	Approved
0.7168	Intermediate Similarity	NPD7458	Discontinued
0.7136	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7874	Approved
0.7134	Intermediate Similarity	NPD230	Phase 1
0.7126	Intermediate Similarity	NPD2344	Approved
0.7126	Intermediate Similarity	NPD2346	Discontinued
0.7122	Intermediate Similarity	NPD8366	Approved
0.7119	Intermediate Similarity	NPD4965	Approved
0.7119	Intermediate Similarity	NPD4967	Phase 2
0.7119	Intermediate Similarity	NPD4966	Approved
0.7108	Intermediate Similarity	NPD7033	Discontinued
0.7102	Intermediate Similarity	NPD5760	Phase 2
0.7102	Intermediate Similarity	NPD5761	Phase 2
0.7085	Intermediate Similarity	NPD8151	Discontinued
0.7081	Intermediate Similarity	NPD6764	Approved
0.7081	Intermediate Similarity	NPD6765	Approved
0.7071	Intermediate Similarity	NPD7584	Approved
0.7067	Intermediate Similarity	NPD8491	Approved
0.7059	Intermediate Similarity	NPD6190	Approved
0.7056	Intermediate Similarity	NPD7199	Phase 2
0.7055	Intermediate Similarity	NPD6798	Discontinued
0.7052	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD7799	Discontinued
0.7049	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD7228	Approved
0.7045	Intermediate Similarity	NPD37	Approved
0.7037	Intermediate Similarity	NPD6832	Phase 2
0.7026	Intermediate Similarity	NPD6782	Approved
0.7026	Intermediate Similarity	NPD6780	Approved
0.7026	Intermediate Similarity	NPD6781	Approved
0.7026	Intermediate Similarity	NPD6778	Approved
0.7026	Intermediate Similarity	NPD6777	Approved
0.7026	Intermediate Similarity	NPD6779	Approved
0.7026	Intermediate Similarity	NPD6776	Approved
0.7024	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6005	Phase 3
0.7024	Intermediate Similarity	NPD6004	Phase 3
0.7024	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6002	Phase 3
0.7017	Intermediate Similarity	NPD3787	Discontinued
0.7017	Intermediate Similarity	NPD7229	Phase 3
0.7006	Intermediate Similarity	NPD8455	Phase 2
0.7005	Intermediate Similarity	NPD7696	Phase 3
0.7005	Intermediate Similarity	NPD7697	Approved
0.7005	Intermediate Similarity	NPD7698	Approved
0.6994	Remote Similarity	NPD5049	Phase 3
0.6989	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7685	Pre-registration
0.697	Remote Similarity	NPD8320	Phase 1
0.697	Remote Similarity	NPD7870	Phase 2
0.697	Remote Similarity	NPD8319	Approved
0.697	Remote Similarity	NPD7871	Phase 2
0.6968	Remote Similarity	NPD8407	Phase 2
0.6959	Remote Similarity	NPD2309	Approved
0.6957	Remote Similarity	NPD7907	Approved
0.6952	Remote Similarity	NPD8469	Approved
0.6951	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.695	Remote Similarity	NPD7701	Phase 2
0.6936	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6784	Approved
0.6931	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7783	Phase 2
0.6931	Remote Similarity	NPD6785	Approved
0.6928	Remote Similarity	NPD447	Suspended
0.6927	Remote Similarity	NPD8404	Phase 2
0.6923	Remote Similarity	NPD7699	Phase 2
0.6923	Remote Similarity	NPD7700	Phase 2
0.6911	Remote Similarity	NPD4287	Approved
0.6909	Remote Similarity	NPD6233	Phase 2
0.6905	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD8368	Discontinued
0.689	Remote Similarity	NPD7095	Approved
0.6882	Remote Similarity	NPD2424	Discontinued
0.6879	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD9717	Approved
0.6868	Remote Similarity	NPD8127	Discontinued
0.6867	Remote Similarity	NPD4060	Phase 1
0.6867	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7585	Approved
0.686	Remote Similarity	NPD2354	Approved
0.686	Remote Similarity	NPD3887	Approved
0.6856	Remote Similarity	NPD4360	Phase 2
0.6856	Remote Similarity	NPD6534	Approved
0.6856	Remote Similarity	NPD6535	Approved
0.6856	Remote Similarity	NPD4363	Phase 3
0.6853	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD1203	Approved
0.6848	Remote Similarity	NPD3268	Approved
0.6848	Remote Similarity	NPD3764	Approved
0.6848	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD7801	Approved
0.6842	Remote Similarity	NPD1652	Phase 2
0.6821	Remote Similarity	NPD4361	Phase 2
0.6821	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7236	Approved
0.6818	Remote Similarity	NPD1653	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