NPASS Compound

Structure

NPC472059 OpenBabel07101718192D 46 51 0 0 1 0 0 0 0 0999 V2000 6.1015 6.5781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4904 -0.8494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3975 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3975 5.8846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6443 4.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8494 1.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0962 0.9808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6987 4.9038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7950 3.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9456 1.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8494 4.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2469 1.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5481 4.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6443 5.3942 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8494 0.4904 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9456 4.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8494 1.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9456 2.4519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8494 3.4327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2469 2.4519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5481 3.4327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0962 2.9423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6987 2.9423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7950 2.9423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.9423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0962 3.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6987 1.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9456 5.3942 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8494 0.4904 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7950 5.8846 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7950 0.9808 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.9038 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4937 5.8846 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6987 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6443 2.4519 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8494 3.4327 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2469 4.4135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5481 1.4712 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0962 5.8846 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6987 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7011 6.2599 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4904 -0.8494 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3975 0.9808 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3975 4.9038 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 45 1 0 0 0 0 4 46 1 0 0 0 0 5 9 1 0 0 0 0 5 15 1 0 0 0 0 6 10 1 0 0 0 0 6 16 1 0 0 0 0 7 11 2 0 0 0 0 7 13 1 0 0 0 0 8 12 2 0 0 0 0 8 14 1 0 0 0 0 9 17 2 0 0 0 0 9 25 1 0 0 0 0 10 18 2 0 0 0 0 10 26 1 0 0 0 0 11 19 1 0 0 0 0 11 33 1 0 0 0 0 12 20 1 0 0 0 0 12 34 1 0 0 0 0 13 21 2 0 0 0 0 13 45 1 0 0 0 0 14 22 2 0 0 0 0 14 46 1 0 0 0 0 15 31 1 6 0 0 0 15 35 1 0 0 0 0 16 32 1 6 0 0 0 16 36 1 0 0 0 0 17 27 1 0 0 0 0 17 29 1 0 0 0 0 18 28 1 0 0 0 0 18 30 1 0 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 20 24 2 0 0 0 0 20 26 1 0 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 22 24 1 0 0 0 0 23 27 1 0 0 0 0 24 28 1 0 0 0 0 25 37 2 0 0 0 0 26 38 2 0 0 0 0 27 39 2 0 0 0 0 28 40 2 0 0 0 0 29 31 1 1 0 0 0 29 41 1 0 0 0 0 30 32 1 1 0 0 0 30 42 1 0 0 0 0 31 1 1 1 0 0 0 31 43 1 0 0 0 0 32 2 1 1 0 0 0 32 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	638.16
Volume:	602.115
LogP:	4.406
LogD:	1.35
LogS:	-3.327
# Rotatable Bonds:	3
TPSA:	254.9
# H-Bond Aceptor:	14
# H-Bond Donor:	10
# Rings:	6
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.143
Synthetic Accessibility Score:	4.962
Fsp3:	0.312
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.653
MDCK Permeability:	4.634223842003848e-06
Pgp-inhibitor:	0.378
Pgp-substrate:	0.355
Human Intestinal Absorption (HIA):	0.998
20% Bioavailability (F20%):	0.023
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	85.97284698486328%
Volume Distribution (VD):	0.566
Pgp-substrate:	18.1900691986084%

ADMET: Metabolism

CYP1A2-inhibitor:	0.114
CYP1A2-substrate:	0.707
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.072
CYP2C9-substrate:	0.211
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.137
CYP3A4-inhibitor:	0.026
CYP3A4-substrate:	0.02

ADMET: Excretion

Clearance (CL):	1.217
Half-life (T1/2):	0.422

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.053
Drug-inuced Liver Injury (DILI):	0.974
AMES Toxicity:	0.414
Rat Oral Acute Toxicity:	0.094
Maximum Recommended Daily Dose:	0.936
Skin Sensitization:	0.729
Carcinogencity:	0.008
Eye Corrosion:	0.003
Eye Irritation:	0.409
Respiratory Toxicity:	0.039

Download Data

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

Natural Product: NPC472059

Natural Product ID:	NPC472059
*Common Name:**	Alterporriol N
IUPAC Name:	(2R,3R,4R)-2,3,4,8-tetrahydroxy-6-methoxy-3-methyl-5-[(6R,7R,8R)-4,6,7,8-tetrahydroxy-2-methoxy-7-methyl-9,10-dioxo-6,8-dihydro-5H-anthracen-1-yl]-2,4-dihydro-1H-anthracene-9,10-dione
Synonyms:
Standard InCHIKey:	HPRQIJBYHJQTCF-WQQAWHSESA-N
Standard InCHI:	InChI=1S/C32H30O14/c1-31(43)15(35)5-9-17(29(31)41)27(39)23-19(25(9)37)11(33)7-13(45-3)21(23)22-14(46-4)8-12(34)20-24(22)28(40)18-10(26(20)38)6-16(36)32(2,44)30(18)42/h7-8,15-16,29-30,33-36,41-44H,5-6H2,1-4H3/t15-,16-,29-,30-,31-,32-/m1/s1
SMILES:	COc1cc(O)c2c(c1c1c(OC)cc(c3c1C(=O)C1=C(C3=O)C[C@H]([C@@]([C@@H]1O)(C)O)O)O)C(=O)C1=C(C2=O)C[C@H]([C@@]([C@@H]1O)(C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3335131
PubChem CID:	57332378
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones [CHEMONTID:0001598] Hydroxyanthraquinones

*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
NPO33215	Stemphylium sp. 33231	Species	Pleosporaceae	Eukaryota	n.a.	South China Sea	n.a.	PMID[25136754]

☑ 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	7

Activity Type	# Activity
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3146	Organism	Micrococcus	Micrococcus	MIC	>	10000.0	nM	PMID[507392]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	10000.0	nM	PMID[507392]
NPT1238	Organism	Staphylococcus	Staphylococcus	MIC	>	10000.0	nM	PMID[507392]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	>	10000.0	nM	PMID[507392]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	10000.0	nM	PMID[507392]
NPT3147	Organism	Kocuria rhizophila	Kocuria rhizophila	MIC	>	10000.0	nM	PMID[507392]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	10000.0	nM	PMID[507392]

☑ 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 NPC472059 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	407
0.1-0.2	1559
0.2-0.3	3456
0.3-0.4	8625
0.4-0.5	10131
0.5-0.6	3929
0.6-0.7	5668
0.7-0.8	6232
0.8-0.85	2233
0.85-0.9	431
0.9-0.95	22
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9935	High Similarity	NPC472053
0.9871	High Similarity	NPC472051
0.9871	High Similarity	NPC472057
0.9497	High Similarity	NPC234497
0.9497	High Similarity	NPC105414
0.9497	High Similarity	NPC472058
0.9497	High Similarity	NPC324522
0.9497	High Similarity	NPC470341
0.9325	High Similarity	NPC477992
0.9325	High Similarity	NPC477991
0.929	High Similarity	NPC155686
0.9161	High Similarity	NPC132990
0.9161	High Similarity	NPC46882
0.9103	High Similarity	NPC470340
0.9074	High Similarity	NPC178173
0.8987	High Similarity	NPC68727
0.8981	High Similarity	NPC268992
0.8981	High Similarity	NPC51824
0.8981	High Similarity	NPC470338
0.8981	High Similarity	NPC470337
0.8981	High Similarity	NPC113608
0.8938	High Similarity	NPC324736
0.8917	High Similarity	NPC470569
0.8916	High Similarity	NPC154986
0.8882	High Similarity	NPC472052
0.8882	High Similarity	NPC470342
0.8882	High Similarity	NPC472060
0.8869	High Similarity	NPC477682
0.8869	High Similarity	NPC477683
0.8861	High Similarity	NPC180944
0.8854	High Similarity	NPC470568
0.8854	High Similarity	NPC147735
0.8827	High Similarity	NPC472261
0.8827	High Similarity	NPC219686
0.882	High Similarity	NPC228654
0.8812	High Similarity	NPC472050
0.8795	High Similarity	NPC251144
0.8795	High Similarity	NPC241387
0.8782	High Similarity	NPC34802
0.878	High Similarity	NPC469664
0.8765	High Similarity	NPC472055
0.8765	High Similarity	NPC470810
0.8758	High Similarity	NPC474637
0.875	High Similarity	NPC86809
0.875	High Similarity	NPC98667
0.875	High Similarity	NPC226656
0.875	High Similarity	NPC232412
0.875	High Similarity	NPC66508
0.8735	High Similarity	NPC264063
0.8735	High Similarity	NPC469486
0.8734	High Similarity	NPC255641
0.8734	High Similarity	NPC290954
0.8734	High Similarity	NPC225854
0.8727	High Similarity	NPC469394
0.8712	High Similarity	NPC87431
0.8704	High Similarity	NPC470339
0.8698	High Similarity	NPC469345
0.869	High Similarity	NPC469393
0.8679	High Similarity	NPC72958
0.8679	High Similarity	NPC232645
0.8679	High Similarity	NPC149526
0.8679	High Similarity	NPC474417
0.8675	High Similarity	NPC473094
0.8675	High Similarity	NPC474024
0.8671	High Similarity	NPC329933
0.8667	High Similarity	NPC472049
0.8662	High Similarity	NPC126767
0.8662	High Similarity	NPC190648
0.8662	High Similarity	NPC289042
0.8662	High Similarity	NPC312929
0.8662	High Similarity	NPC222298
0.8662	High Similarity	NPC118027
0.8662	High Similarity	NPC245584
0.8662	High Similarity	NPC56433
0.8662	High Similarity	NPC51070
0.8659	High Similarity	NPC472402
0.8659	High Similarity	NPC473961
0.8659	High Similarity	NPC15374
0.865	High Similarity	NPC472618
0.865	High Similarity	NPC155302
0.865	High Similarity	NPC161947
0.865	High Similarity	NPC284495
0.8647	High Similarity	NPC470334
0.8645	High Similarity	NPC84266
0.8639	High Similarity	NPC294149
0.8631	High Similarity	NPC5029
0.8631	High Similarity	NPC271385
0.8631	High Similarity	NPC472620
0.8631	High Similarity	NPC76128
0.8631	High Similarity	NPC30432
0.8631	High Similarity	NPC477836
0.8631	High Similarity	NPC473113
0.8631	High Similarity	NPC111536
0.8625	High Similarity	NPC40356
0.8625	High Similarity	NPC154683
0.8625	High Similarity	NPC87708
0.8623	High Similarity	NPC207574
0.8623	High Similarity	NPC473096
0.8623	High Similarity	NPC291795
0.8623	High Similarity	NPC297195
0.8623	High Similarity	NPC54903
0.8623	High Similarity	NPC259905
0.8623	High Similarity	NPC473095
0.8623	High Similarity	NPC286074
0.8616	High Similarity	NPC294646
0.8616	High Similarity	NPC202595
0.8614	High Similarity	NPC477835
0.8614	High Similarity	NPC178851
0.8613	High Similarity	NPC197972
0.8599	High Similarity	NPC316769
0.8598	High Similarity	NPC137232
0.8598	High Similarity	NPC189552
0.8598	High Similarity	NPC117985
0.8598	High Similarity	NPC18380
0.8598	High Similarity	NPC273467
0.8596	High Similarity	NPC299149
0.8596	High Similarity	NPC277710
0.8596	High Similarity	NPC153578
0.8596	High Similarity	NPC114257
0.859	High Similarity	NPC19896
0.8589	High Similarity	NPC85121
0.8589	High Similarity	NPC472617
0.8588	High Similarity	NPC475246
0.8588	High Similarity	NPC46958
0.8588	High Similarity	NPC475233
0.8588	High Similarity	NPC312630
0.8588	High Similarity	NPC324220
0.8581	High Similarity	NPC182255
0.8581	High Similarity	NPC94076
0.858	High Similarity	NPC472054
0.858	High Similarity	NPC470333
0.858	High Similarity	NPC470335
0.858	High Similarity	NPC131862
0.858	High Similarity	NPC229051
0.858	High Similarity	NPC470336
0.858	High Similarity	NPC164427
0.858	High Similarity	NPC478223
0.858	High Similarity	NPC213052
0.858	High Similarity	NPC98776
0.8571	High Similarity	NPC107109
0.8571	High Similarity	NPC93552
0.8571	High Similarity	NPC469405
0.8571	High Similarity	NPC329844
0.8571	High Similarity	NPC210942
0.8571	High Similarity	NPC169990
0.8563	High Similarity	NPC6588
0.8563	High Similarity	NPC477154
0.8563	High Similarity	NPC117854
0.8563	High Similarity	NPC225419
0.8562	High Similarity	NPC474023
0.8562	High Similarity	NPC478148
0.8562	High Similarity	NPC474021
0.8553	High Similarity	NPC97028
0.8553	High Similarity	NPC89442
0.8553	High Similarity	NPC288036
0.8553	High Similarity	NPC158338
0.8553	High Similarity	NPC65589
0.8553	High Similarity	NPC97029
0.8553	High Similarity	NPC270160
0.8553	High Similarity	NPC237440
0.8553	High Similarity	NPC100985
0.8547	High Similarity	NPC208069
0.8547	High Similarity	NPC315221
0.8545	High Similarity	NPC478229
0.8537	High Similarity	NPC312993
0.8537	High Similarity	NPC186325
0.8537	High Similarity	NPC321399
0.8537	High Similarity	NPC184326
0.8537	High Similarity	NPC292863
0.8537	High Similarity	NPC471976
0.8535	High Similarity	NPC478019
0.8535	High Similarity	NPC34482
0.8529	High Similarity	NPC3718
0.8529	High Similarity	NPC68381
0.8528	High Similarity	NPC199463
0.8528	High Similarity	NPC37543
0.8528	High Similarity	NPC246466
0.8528	High Similarity	NPC263483
0.8519	High Similarity	NPC470681
0.8519	High Similarity	NPC166054
0.8519	High Similarity	NPC55662
0.8512	High Similarity	NPC472619
0.8512	High Similarity	NPC300307
0.8512	High Similarity	NPC222455
0.8512	High Similarity	NPC188079
0.8512	High Similarity	NPC326877
0.8509	High Similarity	NPC150123
0.8509	High Similarity	NPC244583
0.8509	High Similarity	NPC323626
0.8509	High Similarity	NPC161881
0.8509	High Similarity	NPC56232
0.8509	High Similarity	NPC324233
0.8509	High Similarity	NPC474843
0.8509	High Similarity	NPC475790
0.8509	High Similarity	NPC10807
0.8506	High Similarity	NPC87583
0.8503	High Similarity	NPC17274
0.8503	High Similarity	NPC120857
0.8503	High Similarity	NPC85047
0.8503	High Similarity	NPC43319

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 NPC472059 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	356
0.1-0.2	960
0.2-0.3	1847
0.3-0.4	2646
0.4-0.5	1851
0.5-0.6	976
0.6-0.7	354
0.7-0.8	133
0.8-0.85	24
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8712	High Similarity	NPD6959	Discontinued
0.85	High Similarity	NPD4380	Phase 2
0.8434	Intermediate Similarity	NPD6232	Discontinued
0.8393	Intermediate Similarity	NPD7473	Discontinued
0.8344	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD7819	Suspended
0.8182	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD7390	Discontinued
0.8118	Intermediate Similarity	NPD6166	Phase 2
0.8118	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD2534	Approved
0.8075	Intermediate Similarity	NPD2533	Approved
0.8075	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD2532	Approved
0.8061	Intermediate Similarity	NPD1934	Approved
0.7976	Intermediate Similarity	NPD7075	Discontinued
0.7976	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD1510	Phase 2
0.7952	Intermediate Similarity	NPD6801	Discontinued
0.7933	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD7074	Phase 3
0.7907	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD2801	Approved
0.7874	Intermediate Similarity	NPD7054	Approved
0.7874	Intermediate Similarity	NPD5844	Phase 1
0.7862	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD6559	Discontinued
0.7834	Intermediate Similarity	NPD1607	Approved
0.7829	Intermediate Similarity	NPD7472	Approved
0.7821	Intermediate Similarity	NPD8150	Discontinued
0.7821	Intermediate Similarity	NPD1240	Approved
0.7816	Intermediate Similarity	NPD3818	Discontinued
0.7812	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD1549	Phase 2
0.7811	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD7808	Phase 3
0.7791	Intermediate Similarity	NPD1511	Approved
0.7789	Intermediate Similarity	NPD8151	Discontinued
0.7784	Intermediate Similarity	NPD7411	Suspended
0.7784	Intermediate Similarity	NPD6797	Phase 2
0.7778	Intermediate Similarity	NPD5494	Approved
0.7764	Intermediate Similarity	NPD2800	Approved
0.7742	Intermediate Similarity	NPD6776	Approved
0.7742	Intermediate Similarity	NPD6778	Approved
0.7742	Intermediate Similarity	NPD6781	Approved
0.7742	Intermediate Similarity	NPD6782	Approved
0.7742	Intermediate Similarity	NPD6777	Approved
0.7742	Intermediate Similarity	NPD6780	Approved
0.7742	Intermediate Similarity	NPD6779	Approved
0.774	Intermediate Similarity	NPD7251	Discontinued
0.7722	Intermediate Similarity	NPD6651	Approved
0.7714	Intermediate Similarity	NPD3751	Discontinued
0.7706	Intermediate Similarity	NPD3882	Suspended
0.7706	Intermediate Similarity	NPD7768	Phase 2
0.7697	Intermediate Similarity	NPD1512	Approved
0.7692	Intermediate Similarity	NPD1465	Phase 2
0.7688	Intermediate Similarity	NPD2796	Approved
0.7684	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD3226	Approved
0.7661	Intermediate Similarity	NPD3749	Approved
0.7654	Intermediate Similarity	NPD8313	Approved
0.7654	Intermediate Similarity	NPD8312	Approved
0.7647	Intermediate Similarity	NPD5402	Approved
0.7647	Intermediate Similarity	NPD3817	Phase 2
0.7619	Intermediate Similarity	NPD7435	Discontinued
0.7619	Intermediate Similarity	NPD7698	Approved
0.7619	Intermediate Similarity	NPD7697	Approved
0.7619	Intermediate Similarity	NPD7696	Phase 3
0.7607	Intermediate Similarity	NPD3750	Approved
0.7598	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD7871	Phase 2
0.7579	Intermediate Similarity	NPD7870	Phase 2
0.7578	Intermediate Similarity	NPD2935	Discontinued
0.7552	Intermediate Similarity	NPD7701	Phase 2
0.753	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD37	Approved
0.7515	Intermediate Similarity	NPD6599	Discontinued
0.7486	Intermediate Similarity	NPD5711	Approved
0.7486	Intermediate Similarity	NPD5710	Approved
0.7486	Intermediate Similarity	NPD3787	Discontinued
0.7474	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7874	Approved
0.7473	Intermediate Similarity	NPD6535	Approved
0.7473	Intermediate Similarity	NPD6534	Approved
0.747	Intermediate Similarity	NPD6799	Approved
0.7447	Intermediate Similarity	NPD7699	Phase 2
0.7447	Intermediate Similarity	NPD7700	Phase 2
0.744	Intermediate Similarity	NPD5403	Approved
0.7436	Intermediate Similarity	NPD7801	Approved
0.7436	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7783	Phase 2
0.7432	Intermediate Similarity	NPD8434	Phase 2
0.7416	Intermediate Similarity	NPD7228	Approved
0.7414	Intermediate Similarity	NPD6234	Discontinued
0.7399	Intermediate Similarity	NPD4966	Approved
0.7399	Intermediate Similarity	NPD4965	Approved
0.7399	Intermediate Similarity	NPD4967	Phase 2
0.7394	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD6823	Phase 2
0.7375	Intermediate Similarity	NPD943	Approved
0.7362	Intermediate Similarity	NPD6099	Approved
0.7362	Intermediate Similarity	NPD6100	Approved
0.7337	Intermediate Similarity	NPD920	Approved
0.7321	Intermediate Similarity	NPD5401	Approved
0.7317	Intermediate Similarity	NPD2346	Discontinued
0.7306	Intermediate Similarity	NPD8319	Approved
0.7306	Intermediate Similarity	NPD8320	Phase 1
0.7301	Intermediate Similarity	NPD3748	Approved
0.7293	Intermediate Similarity	NPD5953	Discontinued
0.7289	Intermediate Similarity	NPD4628	Phase 3
0.7283	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1470	Approved
0.7256	Intermediate Similarity	NPD5404	Approved
0.7256	Intermediate Similarity	NPD5406	Approved
0.7256	Intermediate Similarity	NPD5405	Approved
0.7256	Intermediate Similarity	NPD5408	Approved
0.7251	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD3926	Phase 2
0.7229	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD2344	Approved
0.7195	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4625	Phase 3
0.7186	Intermediate Similarity	NPD7003	Approved
0.7186	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD7286	Phase 2
0.7152	Intermediate Similarity	NPD1551	Phase 2
0.7151	Intermediate Similarity	NPD7458	Discontinued
0.7143	Intermediate Similarity	NPD6212	Phase 3
0.7143	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6213	Phase 3
0.7135	Intermediate Similarity	NPD1247	Approved
0.7126	Intermediate Similarity	NPD1243	Approved
0.712	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD230	Phase 1
0.7115	Intermediate Similarity	NPD1201	Approved
0.7108	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4363	Phase 3
0.7105	Intermediate Similarity	NPD4360	Phase 2
0.7101	Intermediate Similarity	NPD3300	Phase 2
0.7098	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7229	Phase 3
0.7091	Intermediate Similarity	NPD2799	Discontinued
0.7086	Intermediate Similarity	NPD8455	Phase 2
0.7081	Intermediate Similarity	NPD3027	Phase 3
0.7065	Intermediate Similarity	NPD7240	Approved
0.7041	Intermediate Similarity	NPD2309	Approved
0.7039	Intermediate Similarity	NPD7199	Phase 2
0.7037	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD919	Approved
0.7	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD7685	Pre-registration
0.697	Remote Similarity	NPD7584	Approved
0.6959	Remote Similarity	NPD8285	Discontinued
0.6951	Remote Similarity	NPD1613	Approved
0.6951	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6190	Approved
0.6938	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD8059	Phase 3
0.6933	Remote Similarity	NPD2313	Discontinued
0.6933	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1651	Approved
0.6919	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4908	Phase 1
0.6897	Remote Similarity	NPD7930	Approved
0.6894	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD2798	Approved
0.6893	Remote Similarity	NPD5761	Phase 2
0.6893	Remote Similarity	NPD5760	Phase 2
0.6886	Remote Similarity	NPD7033	Discontinued
0.6879	Remote Similarity	NPD6273	Approved
0.6875	Remote Similarity	NPD1283	Approved
0.6868	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7177	Discontinued
0.6848	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD36	Approved
0.6845	Remote Similarity	NPD4955	Approved
0.6845	Remote Similarity	NPD5028	Approved
0.6845	Remote Similarity	NPD4954	Approved
0.6845	Remote Similarity	NPD5034	Approved
0.6845	Remote Similarity	NPD5026	Approved
0.6845	Remote Similarity	NPD2438	Suspended
0.6833	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD2403	Approved
0.6829	Remote Similarity	NPD3764	Approved
0.6824	Remote Similarity	NPD2654	Approved
0.6813	Remote Similarity	NPD4749	Approved
0.6809	Remote Similarity	NPD5035	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