NPASS Compound

Structure

NPC135524 OpenBabel07101718312D 27 29 0 0 1 0 0 0 0 0999 V2000 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 12 1 0 0 0 0 6 9 2 0 0 0 0 6 10 1 0 0 0 0 7 9 1 0 0 0 0 7 13 2 0 0 0 0 8 11 2 0 0 0 0 8 14 1 0 0 0 0 9 21 1 0 0 0 0 10 15 2 0 0 0 0 10 18 1 0 0 0 0 11 16 1 0 0 0 0 11 18 1 0 0 0 0 12 17 1 0 0 0 0 12 22 1 6 0 0 0 13 15 1 0 0 0 0 13 23 1 0 0 0 0 14 17 2 0 0 0 0 14 24 1 0 0 0 0 15 19 1 0 0 0 0 16 19 1 0 0 0 0 16 20 2 0 0 0 0 17 20 1 0 0 0 0 18 25 2 0 0 0 0 19 26 2 0 0 0 0 20 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	372.12
Volume:	369.247
LogP:	5.155
LogD:	2.635
LogS:	-3.857
# Rotatable Bonds:	5
TPSA:	138.45
# H-Bond Aceptor:	7
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.172
Synthetic Accessibility Score:	2.876
Fsp3:	0.25
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.44
MDCK Permeability:	8.64376033860026e-06
Pgp-inhibitor:	0.011
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.973
20% Bioavailability (F20%):	0.797
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	97.84695434570312%
Volume Distribution (VD):	0.493
Pgp-substrate:	4.144292831420898%

ADMET: Metabolism

CYP1A2-inhibitor:	0.93
CYP1A2-substrate:	0.163
CYP2C19-inhibitor:	0.125
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.697
CYP2C9-substrate:	0.604
CYP2D6-inhibitor:	0.261
CYP2D6-substrate:	0.176
CYP3A4-inhibitor:	0.104
CYP3A4-substrate:	0.025

ADMET: Excretion

Clearance (CL):	6.96
Half-life (T1/2):	0.847

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.148
Drug-inuced Liver Injury (DILI):	0.969
AMES Toxicity:	0.643
Rat Oral Acute Toxicity:	0.021
Maximum Recommended Daily Dose:	0.812
Skin Sensitization:	0.953
Carcinogencity:	0.068
Eye Corrosion:	0.003
Eye Irritation:	0.923
Respiratory Toxicity:	0.09

Download Data

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

Natural Product: NPC135524

Natural Product ID:	NPC135524
*Common Name:**	(1's)-Averantin
IUPAC Name:	1,3,6,8-tetrahydroxy-2-[(1S)-1-hydroxyhexyl]anthracene-9,10-dione
Synonyms:
Standard InCHIKey:	WGPOPPKSQRZUTP-LBPRGKRZSA-N
Standard InCHI:	InChI=1S/C20H20O7/c1-2-3-4-5-12(22)17-14(24)8-11-16(20(17)27)19(26)15-10(18(11)25)6-9(21)7-13(15)23/h6-8,12,21-24,27H,2-5H2,1H3/t12-/m0/s1
SMILES:	CCCCC[C@@H](c1c(O)cc2c(c1O)C(=O)c1c(C2=O)cc(cc1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2071288
PubChem CID:	10044783
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
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	rhizosphere	Sonoran desert	n.a.	PMID[15620238]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17542490]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17564467]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19053517]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21366228]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21718031]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21854017]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	healthy leaf of Ginkgo biloba	campus of Nanjing University, Nanjing, China	2008-OCT	PMID[22196792]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	isolated from the sponge Xestospongia testudinaria	n.a.	n.a.	PMID[22225637]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	Isolated from a sandy-loam soil sample	50 m inland from Waikiki Beach, Honolulu, Hawaii	2010-JUL	PMID[22400916]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22703109]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23527875]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24050204]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25001296]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25581396]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26273902]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31012585]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33305943]

☑ 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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT395	Cell Line	SF-268	Homo sapiens	IC50	>	50000.0	nM	PMID[486756]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	45470.0	nM	PMID[486756]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	>	50000.0	nM	PMID[486756]

☑ 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 NPC135524 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	357
0.1-0.2	1425
0.2-0.3	3340
0.3-0.4	8802
0.4-0.5	10507
0.5-0.6	4580
0.6-0.7	6483
0.7-0.8	5664
0.8-0.85	1155
0.85-0.9	297
0.9-0.95	69
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
0.9926	High Similarity	NPC204045
0.9926	High Similarity	NPC305845
0.971	High Similarity	NPC244691
0.971	High Similarity	NPC471906
0.9708	High Similarity	NPC474961
0.964	High Similarity	NPC34482
0.9632	High Similarity	NPC138099
0.9632	High Similarity	NPC190457
0.9632	High Similarity	NPC242994
0.963	High Similarity	NPC471905
0.9571	High Similarity	NPC470570
0.9568	High Similarity	NPC48762
0.9562	High Similarity	NPC169452
0.9562	High Similarity	NPC181560
0.9556	High Similarity	NPC254847
0.9485	High Similarity	NPC53414
0.9485	High Similarity	NPC53206
0.9429	High Similarity	NPC193703
0.9429	High Similarity	NPC21599
0.9424	High Similarity	NPC193555
0.9412	High Similarity	NPC191976
0.9375	High Similarity	NPC470569
0.9353	High Similarity	NPC246638
0.9348	High Similarity	NPC143438
0.9333	High Similarity	NPC267205
0.9306	High Similarity	NPC470568
0.9286	High Similarity	NPC73061
0.9265	High Similarity	NPC44437
0.9265	High Similarity	NPC282780
0.9265	High Similarity	NPC166480
0.9172	High Similarity	NPC255641
0.9172	High Similarity	NPC147735
0.9172	High Similarity	NPC290954
0.9149	High Similarity	NPC137649
0.9103	High Similarity	NPC477221
0.9097	High Similarity	NPC290194
0.9097	High Similarity	NPC289042
0.9097	High Similarity	NPC118027
0.9097	High Similarity	NPC312929
0.9097	High Similarity	NPC245584
0.9097	High Similarity	NPC37709
0.9097	High Similarity	NPC190648
0.9097	High Similarity	NPC126767
0.9097	High Similarity	NPC56433
0.9078	High Similarity	NPC187843
0.9078	High Similarity	NPC290550
0.9051	High Similarity	NPC213485
0.9051	High Similarity	NPC314048
0.9051	High Similarity	NPC40524
0.9051	High Similarity	NPC139074
0.9051	High Similarity	NPC52407
0.9048	High Similarity	NPC40356
0.9048	High Similarity	NPC154683
0.9044	High Similarity	NPC93015
0.9044	High Similarity	NPC475042
0.9041	High Similarity	NPC280295
0.8993	High Similarity	NPC118919
0.8993	High Similarity	NPC315275
0.8978	High Similarity	NPC70622
0.8971	High Similarity	NPC147757
0.8971	High Similarity	NPC31799
0.8951	High Similarity	NPC313047
0.8951	High Similarity	NPC295712
0.8951	High Similarity	NPC474203
0.8951	High Similarity	NPC174905
0.8951	High Similarity	NPC293545
0.8951	High Similarity	NPC451542
0.8936	High Similarity	NPC162939
0.8929	High Similarity	NPC53001
0.8921	High Similarity	NPC283088
0.8921	High Similarity	NPC283590
0.8921	High Similarity	NPC70859
0.8921	High Similarity	NPC130899
0.8921	High Similarity	NPC61153
0.8912	High Similarity	NPC294646
0.8897	High Similarity	NPC92624
0.8897	High Similarity	NPC143685
0.8897	High Similarity	NPC99731
0.8897	High Similarity	NPC314437
0.8889	High Similarity	NPC227841
0.8889	High Similarity	NPC19896
0.8874	High Similarity	NPC470559
0.8874	High Similarity	NPC324736
0.8873	High Similarity	NPC203063
0.8865	High Similarity	NPC13715
0.8865	High Similarity	NPC4214
0.8865	High Similarity	NPC87723
0.8859	High Similarity	NPC470408
0.8859	High Similarity	NPC472211
0.8859	High Similarity	NPC208806
0.8859	High Similarity	NPC218870
0.8859	High Similarity	NPC474824
0.8859	High Similarity	NPC182921
0.8849	High Similarity	NPC474394
0.8849	High Similarity	NPC12070
0.8849	High Similarity	NPC474519
0.8841	High Similarity	NPC478190
0.8841	High Similarity	NPC175738
0.8836	High Similarity	NPC34802
0.8832	High Similarity	NPC62219
0.8832	High Similarity	NPC199253
0.8832	High Similarity	NPC136588
0.8832	High Similarity	NPC259942
0.8828	High Similarity	NPC478019
0.8828	High Similarity	NPC49282
0.8828	High Similarity	NPC12402
0.8824	High Similarity	NPC282923
0.8819	High Similarity	NPC167663
0.8811	High Similarity	NPC106519
0.8811	High Similarity	NPC110810
0.8811	High Similarity	NPC91019
0.88	High Similarity	NPC226656
0.88	High Similarity	NPC66508
0.8786	High Similarity	NPC161632
0.8786	High Similarity	NPC249272
0.8786	High Similarity	NPC290803
0.8784	High Similarity	NPC205766
0.8777	High Similarity	NPC114183
0.8777	High Similarity	NPC115458
0.8777	High Similarity	NPC180261
0.8777	High Similarity	NPC37299
0.8767	High Similarity	NPC110882
0.8767	High Similarity	NPC85393
0.8767	High Similarity	NPC271944
0.8767	High Similarity	NPC136878
0.8759	High Similarity	NPC10764
0.8759	High Similarity	NPC109123
0.8759	High Similarity	NPC474998
0.875	High Similarity	NPC469520
0.875	High Similarity	NPC98254
0.875	High Similarity	NPC162612
0.875	High Similarity	NPC72158
0.875	High Similarity	NPC190043
0.875	High Similarity	NPC239136
0.875	High Similarity	NPC23126
0.875	High Similarity	NPC19631
0.875	High Similarity	NPC85310
0.875	High Similarity	NPC105157
0.875	High Similarity	NPC266689
0.875	High Similarity	NPC169250
0.875	High Similarity	NPC103356
0.875	High Similarity	NPC100067
0.875	High Similarity	NPC30501
0.8742	High Similarity	NPC474861
0.8741	High Similarity	NPC156872
0.8741	High Similarity	NPC10926
0.8741	High Similarity	NPC315578
0.8741	High Similarity	NPC183345
0.8741	High Similarity	NPC477454
0.8733	High Similarity	NPC107109
0.8732	High Similarity	NPC61398
0.8732	High Similarity	NPC416
0.8725	High Similarity	NPC232645
0.8725	High Similarity	NPC474417
0.8725	High Similarity	NPC72958
0.8725	High Similarity	NPC46882
0.8725	High Similarity	NPC149526
0.8725	High Similarity	NPC132990
0.8725	High Similarity	NPC478148
0.8716	High Similarity	NPC329933
0.8714	High Similarity	NPC50924
0.8714	High Similarity	NPC270899
0.8714	High Similarity	NPC202225
0.869	High Similarity	NPC471682
0.869	High Similarity	NPC84266
0.869	High Similarity	NPC66593
0.869	High Similarity	NPC471731
0.869	High Similarity	NPC159721
0.869	High Similarity	NPC296752
0.869	High Similarity	NPC238629
0.8686	High Similarity	NPC221777
0.8686	High Similarity	NPC48248
0.8686	High Similarity	NPC473017
0.8686	High Similarity	NPC21305
0.8684	High Similarity	NPC199463
0.8684	High Similarity	NPC37543
0.8676	High Similarity	NPC473691
0.8676	High Similarity	NPC62952
0.8676	High Similarity	NPC8745
0.8676	High Similarity	NPC267846
0.8671	High Similarity	NPC26924
0.8667	High Similarity	NPC470338
0.8667	High Similarity	NPC470340
0.8667	High Similarity	NPC180944
0.8667	High Similarity	NPC87708
0.8667	High Similarity	NPC268992
0.8667	High Similarity	NPC470337
0.8667	High Similarity	NPC113608
0.8667	High Similarity	NPC51824
0.8662	High Similarity	NPC475957
0.8662	High Similarity	NPC305060
0.8662	High Similarity	NPC290030
0.8658	High Similarity	NPC202595
0.8652	High Similarity	NPC80035
0.8652	High Similarity	NPC278375
0.8649	High Similarity	NPC172329
0.8649	High Similarity	NPC2569
0.8649	High Similarity	NPC471907
0.8643	High Similarity	NPC78307
0.8643	High Similarity	NPC48036

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 NPC135524 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	318
0.1-0.2	938
0.2-0.3	1524
0.3-0.4	2753
0.4-0.5	2066
0.5-0.6	1063
0.6-0.7	364
0.7-0.8	109
0.8-0.85	12
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9556	High Similarity	NPD1509	Clinical (unspecified phase)
0.8889	High Similarity	NPD7390	Discontinued
0.8603	High Similarity	NPD1470	Approved
0.8403	Intermediate Similarity	NPD5405	Approved
0.8403	Intermediate Similarity	NPD5408	Approved
0.8403	Intermediate Similarity	NPD5404	Approved
0.8403	Intermediate Similarity	NPD5406	Approved
0.831	Intermediate Similarity	NPD943	Approved
0.8309	Intermediate Similarity	NPD1201	Approved
0.828	Intermediate Similarity	NPD6959	Discontinued
0.8228	Intermediate Similarity	NPD6232	Discontinued
0.8187	Intermediate Similarity	NPD7473	Discontinued
0.8129	Intermediate Similarity	NPD7819	Suspended
0.8082	Intermediate Similarity	NPD1510	Phase 2
0.8079	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD2534	Approved
0.8079	Intermediate Similarity	NPD2533	Approved
0.8079	Intermediate Similarity	NPD2532	Approved
0.8069	Intermediate Similarity	NPD1607	Approved
0.8052	Intermediate Similarity	NPD4380	Phase 2
0.8013	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD1240	Approved
0.7919	Intermediate Similarity	NPD1549	Phase 2
0.7852	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD2796	Approved
0.7771	Intermediate Similarity	NPD7411	Suspended
0.7758	Intermediate Similarity	NPD5844	Phase 1
0.7756	Intermediate Similarity	NPD3226	Approved
0.775	Intermediate Similarity	NPD7075	Discontinued
0.7737	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD1934	Approved
0.7673	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD2935	Discontinued
0.763	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD6801	Discontinued
0.7578	Intermediate Similarity	NPD3882	Suspended
0.7578	Intermediate Similarity	NPD7768	Phase 2
0.7576	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6166	Phase 2
0.7576	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD1164	Approved
0.7562	Intermediate Similarity	NPD2801	Approved
0.7546	Intermediate Similarity	NPD5494	Approved
0.7531	Intermediate Similarity	NPD3749	Approved
0.7531	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6559	Discontinued
0.75	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD8150	Discontinued
0.7485	Intermediate Similarity	NPD3818	Discontinued
0.7484	Intermediate Similarity	NPD6599	Discontinued
0.7469	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD3750	Approved
0.7468	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD5710	Approved
0.7455	Intermediate Similarity	NPD5711	Approved
0.7447	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD6534	Approved
0.7443	Intermediate Similarity	NPD6535	Approved
0.7436	Intermediate Similarity	NPD1511	Approved
0.7421	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD2800	Approved
0.7403	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3019	Approved
0.7351	Intermediate Similarity	NPD6651	Approved
0.7342	Intermediate Similarity	NPD1512	Approved
0.7337	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD6020	Phase 2
0.7333	Intermediate Similarity	NPD6782	Approved
0.7333	Intermediate Similarity	NPD6781	Approved
0.7333	Intermediate Similarity	NPD6778	Approved
0.7333	Intermediate Similarity	NPD6777	Approved
0.7333	Intermediate Similarity	NPD6780	Approved
0.7333	Intermediate Similarity	NPD6776	Approved
0.7333	Intermediate Similarity	NPD6779	Approved
0.7325	Intermediate Similarity	NPD6799	Approved
0.732	Intermediate Similarity	NPD6099	Approved
0.732	Intermediate Similarity	NPD1551	Phase 2
0.732	Intermediate Similarity	NPD6100	Approved
0.7318	Intermediate Similarity	NPD7699	Phase 2
0.7318	Intermediate Similarity	NPD7700	Phase 2
0.7315	Intermediate Similarity	NPD3764	Approved
0.7297	Intermediate Similarity	NPD8151	Discontinued
0.7294	Intermediate Similarity	NPD7074	Phase 3
0.7285	Intermediate Similarity	NPD230	Phase 1
0.7284	Intermediate Similarity	NPD37	Approved
0.7273	Intermediate Similarity	NPD2344	Approved
0.7273	Intermediate Similarity	NPD2932	Approved
0.7261	Intermediate Similarity	NPD3300	Phase 2
0.7255	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD2799	Discontinued
0.7251	Intermediate Similarity	NPD5953	Discontinued
0.7244	Intermediate Similarity	NPD7003	Approved
0.7244	Intermediate Similarity	NPD4628	Phase 3
0.7241	Intermediate Similarity	NPD9269	Phase 2
0.7235	Intermediate Similarity	NPD7054	Approved
0.7226	Intermediate Similarity	NPD4750	Phase 3
0.7225	Intermediate Similarity	NPD8312	Approved
0.7225	Intermediate Similarity	NPD8313	Approved
0.7216	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD7698	Approved
0.7213	Intermediate Similarity	NPD7696	Phase 3
0.7213	Intermediate Similarity	NPD7435	Discontinued
0.7213	Intermediate Similarity	NPD7697	Approved
0.7205	Intermediate Similarity	NPD7458	Discontinued
0.7203	Intermediate Similarity	NPD9268	Approved
0.7195	Intermediate Similarity	NPD5402	Approved
0.7195	Intermediate Similarity	NPD3817	Phase 2
0.7193	Intermediate Similarity	NPD7472	Approved
0.7191	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD6213	Phase 3
0.7191	Intermediate Similarity	NPD6212	Phase 3
0.7174	Intermediate Similarity	NPD7871	Phase 2
0.7174	Intermediate Similarity	NPD7870	Phase 2
0.7174	Intermediate Similarity	NPD8320	Phase 1
0.7174	Intermediate Similarity	NPD8319	Approved
0.7168	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4965	Approved
0.7152	Intermediate Similarity	NPD4967	Phase 2
0.7152	Intermediate Similarity	NPD4966	Approved
0.7151	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6797	Phase 2
0.7143	Intermediate Similarity	NPD3748	Approved
0.7134	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7251	Discontinued
0.7092	Intermediate Similarity	NPD5951	Approved
0.7089	Intermediate Similarity	NPD2309	Approved
0.7089	Intermediate Similarity	NPD6190	Approved
0.7081	Intermediate Similarity	NPD5403	Approved
0.7081	Intermediate Similarity	NPD920	Approved
0.7076	Intermediate Similarity	NPD3751	Discontinued
0.707	Intermediate Similarity	NPD1243	Approved
0.7069	Intermediate Similarity	NPD7808	Phase 3
0.7069	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6234	Discontinued
0.7063	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7701	Phase 2
0.7049	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD2798	Approved
0.7039	Intermediate Similarity	NPD6663	Approved
0.7035	Intermediate Similarity	NPD7286	Phase 2
0.703	Intermediate Similarity	NPD1465	Phase 2
0.702	Intermediate Similarity	NPD4625	Phase 3
0.7019	Intermediate Similarity	NPD6273	Approved
0.7014	Intermediate Similarity	NPD3091	Approved
0.7007	Intermediate Similarity	NPD3972	Approved
0.7005	Intermediate Similarity	NPD6973	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5736	Approved
0.7	Intermediate Similarity	NPD3926	Phase 2
0.6993	Remote Similarity	NPD9493	Approved
0.6986	Remote Similarity	NPD3026	Approved
0.6986	Remote Similarity	NPD3023	Approved
0.6984	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD7874	Approved
0.698	Remote Similarity	NPD3094	Phase 2
0.6975	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD2313	Discontinued
0.6973	Remote Similarity	NPD6823	Phase 2
0.6966	Remote Similarity	NPD1651	Approved
0.6966	Remote Similarity	NPD3024	Approved
0.6966	Remote Similarity	NPD3025	Approved
0.6957	Remote Similarity	NPD5401	Approved
0.6957	Remote Similarity	NPD2342	Discontinued
0.6957	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7801	Approved
0.6943	Remote Similarity	NPD1471	Phase 3
0.6941	Remote Similarity	NPD7229	Phase 3
0.6939	Remote Similarity	NPD3092	Approved
0.6937	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD8166	Discontinued
0.6918	Remote Similarity	NPD3400	Discontinued
0.6913	Remote Similarity	NPD1283	Approved
0.6906	Remote Similarity	NPD9266	Approved
0.6906	Remote Similarity	NPD74	Approved
0.6897	Remote Similarity	NPD9545	Approved
0.6886	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD1247	Approved
0.6879	Remote Similarity	NPD7177	Discontinued
0.6879	Remote Similarity	NPD7228	Approved
0.6875	Remote Similarity	NPD5034	Approved
0.6875	Remote Similarity	NPD4954	Approved
0.6875	Remote Similarity	NPD36	Approved
0.6875	Remote Similarity	NPD5026	Approved
0.6875	Remote Similarity	NPD5028	Approved
0.6875	Remote Similarity	NPD4955	Approved
0.6868	Remote Similarity	NPD4360	Phase 2
0.6868	Remote Similarity	NPD4363	Phase 3
0.6864	Remote Similarity	NPD919	Approved
0.6842	Remote Similarity	NPD3787	Discontinued
0.6842	Remote Similarity	NPD4908	Phase 1
0.6838	Remote Similarity	NPD846	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