NPASS Compound

Structure

CID53896 OpenBabel06191715392D 28 31 0 0 0 0 0 0 0 0999 V2000 -6.0622 -1.5000 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 -1.0000 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 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 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 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 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 -3.4641 -1.0000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 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 -4.3301 0.5000 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 -0.8660 0.5000 0.0000 C 0 0 0 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 0.5000 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 -2.5981 0.5000 0.0000 C 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 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 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 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 10 1 0 0 0 0 3 4 2 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 9 2 0 0 0 0 5 11 1 0 0 0 0 6 9 1 0 0 0 0 6 16 2 0 0 0 0 7 10 1 0 0 0 0 7 17 2 0 0 0 0 8 12 2 0 0 0 0 8 15 1 0 0 0 0 10 18 2 0 0 0 0 11 15 1 0 0 0 0 11 19 2 0 0 0 0 12 18 1 0 0 0 0 12 22 1 0 0 0 0 13 20 1 0 0 0 0 13 23 2 0 0 0 0 14 21 1 0 0 0 0 14 24 2 0 0 0 0 15 25 2 0 0 0 0 16 19 1 0 0 0 0 16 26 1 0 0 0 0 17 20 1 0 0 0 0 17 27 1 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 20 21 2 0 0 0 0 22 28 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.08
Volume:	375.946
LogP:	4.397
LogD:	2.62
LogS:	-5.036
# Rotatable Bonds:	0
TPSA:	115.06
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.445
Synthetic Accessibility Score:	3.817
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.039
MDCK Permeability:	4.060331775690429e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.359
20% Bioavailability (F20%):	0.874
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	92.56575775146484%
Volume Distribution (VD):	0.68
Pgp-substrate:	9.758460998535156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.981
CYP1A2-substrate:	0.081
CYP2C19-inhibitor:	0.057
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.615
CYP2C9-substrate:	0.352
CYP2D6-inhibitor:	0.164
CYP2D6-substrate:	0.166
CYP3A4-inhibitor:	0.164
CYP3A4-substrate:	0.04

ADMET: Excretion

Clearance (CL):	7.953
Half-life (T1/2):	0.431

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.453
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.6
Rat Oral Acute Toxicity:	0.19
Maximum Recommended Daily Dose:	0.941
Skin Sensitization:	0.968
Carcinogencity:	0.481
Eye Corrosion:	0.019
Eye Irritation:	0.952
Respiratory Toxicity:	0.181

Download Data

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

Natural Product: NPC53896

Natural Product ID:	NPC53896
*Common Name:**	Neodiospyrin
IUPAC Name:	8-hydroxy-5-(8-hydroxy-6-methyl-1,4-dioxonaphthalen-2-yl)-6-methylnaphthalene-1,4-dione
Synonyms:	neodiospyrin
Standard InCHIKey:	LZAXNDGRDVWTFX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H14O6/c1-9-5-11-15(25)8-12(22(28)19(11)16(26)6-9)18-10(2)7-17(27)20-13(23)3-4-14(24)21(18)20/h3-8,26-27H,1-2H3
SMILES:	Cc1cc(O)c2c(c1)C(=O)C=C(C2=O)c1c(C)cc(c2c1C(=O)C=CC2=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL241392
PubChem CID:	16072922
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0000153] Naphthoquinones

*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
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	calyx	n.a.	PMID[21561086]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	fruit	n.a.	PMID[24086493]
NPO5082	Cycas revoluta	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5082	Cycas revoluta	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5082	Cycas revoluta	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5082	Cycas revoluta	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18296	Diospyros kaki	Species	Ebenaceae	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	3
MIC	1
Others	4

Activity Type	# Activity
Cell Line	1
Organism	1
Others	5
PROTEIN COMPLEX	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	32.0	ug.mL-1	PMID[510310]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	10.0	ug.mL-1	PMID[510310]
NPT2	Others	Unspecified		Ratio	=	3.2	n.a.	PMID[510310]
NPT2	Others	Unspecified		Km	=	63000.0	nM	PMID[510310]
NPT2	Others	Unspecified		Kcat	=	0.308	/s	PMID[510310]
NPT2	Others	Unspecified		Kcat/Km	=	48800000.0	n.a.	PMID[510310]
NPT22359	PROTEIN COMPLEX	DNA gyrase subunit A/DNA gyrase subunit B	Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)	IC50	=	50000.0	nM	PMID[510311]
NPT2	Others	Unspecified		IC50	=	50000.0	nM	PMID[510312]

☑ 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 NPC53896 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	360
0.1-0.2	1613
0.2-0.3	3667
0.3-0.4	10422
0.4-0.5	8631
0.5-0.6	5798
0.6-0.7	8024
0.7-0.8	3649
0.8-0.85	357
0.85-0.9	136
0.9-0.95	27
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9685	High Similarity	NPC244699
0.9683	High Similarity	NPC34414
0.9683	High Similarity	NPC146647
0.9612	High Similarity	NPC50924
0.9453	High Similarity	NPC55949
0.9389	High Similarity	NPC283088
0.9389	High Similarity	NPC80035
0.9323	High Similarity	NPC13715
0.9308	High Similarity	NPC58685
0.9237	High Similarity	NPC115458
0.9225	High Similarity	NPC99731
0.9179	High Similarity	NPC4214
0.9147	High Similarity	NPC48248
0.9147	High Similarity	NPC282923
0.9134	High Similarity	NPC142956
0.9127	High Similarity	NPC307174
0.9091	High Similarity	NPC225051
0.9055	High Similarity	NPC375356
0.903	High Similarity	NPC272268
0.903	High Similarity	NPC193358
0.8992	High Similarity	NPC3224
0.8976	High Similarity	NPC300274
0.8963	High Similarity	NPC305060
0.8947	High Similarity	NPC52407
0.8939	High Similarity	NPC72669
0.8939	High Similarity	NPC474517
0.8939	High Similarity	NPC17083
0.8939	High Similarity	NPC205992
0.8915	High Similarity	NPC103540
0.8913	High Similarity	NPC193555
0.8889	High Similarity	NPC474813
0.8889	High Similarity	NPC206778
0.8889	High Similarity	NPC155211
0.8889	High Similarity	NPC285829
0.8881	High Similarity	NPC288089
0.8864	High Similarity	NPC199253
0.8864	High Similarity	NPC136588
0.8855	High Similarity	NPC96024
0.8849	High Similarity	NPC66593
0.8846	High Similarity	NPC306765
0.8846	High Similarity	NPC96915
0.8837	High Similarity	NPC173978
0.8832	High Similarity	NPC26924
0.8832	High Similarity	NPC242994
0.8832	High Similarity	NPC138099
0.8824	High Similarity	NPC245923
0.8824	High Similarity	NPC53414
0.8824	High Similarity	NPC471905
0.8824	High Similarity	NPC53206
0.8815	High Similarity	NPC258502
0.8786	High Similarity	NPC79627
0.8777	High Similarity	NPC239136
0.8777	High Similarity	NPC19631
0.8768	High Similarity	NPC169452
0.8768	High Similarity	NPC315578
0.8768	High Similarity	NPC181560
0.8768	High Similarity	NPC96421
0.8759	High Similarity	NPC61398
0.8759	High Similarity	NPC416
0.875	High Similarity	NPC474311
0.875	High Similarity	NPC254847
0.8731	High Similarity	NPC70622
0.8722	High Similarity	NPC31799
0.8705	High Similarity	NPC246638
0.8702	High Similarity	NPC254492
0.8702	High Similarity	NPC231774
0.8692	High Similarity	NPC199273
0.8692	High Similarity	NPC310540
0.8686	High Similarity	NPC36868
0.8682	High Similarity	NPC91478
0.8667	High Similarity	NPC294226
0.8667	High Similarity	NPC314048
0.8662	High Similarity	NPC314437
0.8657	High Similarity	NPC93015
0.8657	High Similarity	NPC85342
0.8643	High Similarity	NPC73061
0.8636	High Similarity	NPC72667
0.8636	High Similarity	NPC471530
0.8613	High Similarity	NPC86524
0.8613	High Similarity	NPC315275
0.8605	High Similarity	NPC120545
0.8603	High Similarity	NPC161964
0.8603	High Similarity	NPC472262
0.8603	High Similarity	NPC282780
0.8603	High Similarity	NPC44437
0.8603	High Similarity	NPC287604
0.8603	High Similarity	NPC166480
0.8582	High Similarity	NPC27659
0.8582	High Similarity	NPC198305
0.8582	High Similarity	NPC53016
0.8582	High Similarity	NPC117609
0.8571	High Similarity	NPC305845
0.8571	High Similarity	NPC108288
0.8571	High Similarity	NPC204045
0.8571	High Similarity	NPC290550
0.8571	High Similarity	NPC95537
0.8561	High Similarity	NPC1268
0.8561	High Similarity	NPC143438
0.8561	High Similarity	NPC160499
0.8551	High Similarity	NPC53001
0.8551	High Similarity	NPC471452
0.855	High Similarity	NPC164014
0.855	High Similarity	NPC68756
0.855	High Similarity	NPC152525
0.854	High Similarity	NPC161632
0.8538	High Similarity	NPC282577
0.8529	High Similarity	NPC254603
0.8529	High Similarity	NPC267205
0.8521	High Similarity	NPC193703
0.8521	High Similarity	NPC21599
0.8511	High Similarity	NPC69755
0.8511	High Similarity	NPC135524
0.8507	High Similarity	NPC278928
0.8507	High Similarity	NPC276238
0.8507	High Similarity	NPC25736
0.8507	High Similarity	NPC171460
0.8496	Intermediate Similarity	NPC69424
0.8496	Intermediate Similarity	NPC84672
0.8496	Intermediate Similarity	NPC176130
0.8496	Intermediate Similarity	NPC78364
0.8493	Intermediate Similarity	NPC144283
0.8492	Intermediate Similarity	NPC161304
0.8489	Intermediate Similarity	NPC87723
0.8478	Intermediate Similarity	NPC191976
0.8478	Intermediate Similarity	NPC472308
0.8467	Intermediate Similarity	NPC12070
0.8462	Intermediate Similarity	NPC154696
0.8456	Intermediate Similarity	NPC309430
0.8456	Intermediate Similarity	NPC110609
0.8456	Intermediate Similarity	NPC242358
0.8456	Intermediate Similarity	NPC246693
0.8451	Intermediate Similarity	NPC471682
0.8444	Intermediate Similarity	NPC108129
0.8444	Intermediate Similarity	NPC31539
0.844	Intermediate Similarity	NPC124365
0.844	Intermediate Similarity	NPC187843
0.8433	Intermediate Similarity	NPC237225
0.8429	Intermediate Similarity	NPC470407
0.8429	Intermediate Similarity	NPC190457
0.8425	Intermediate Similarity	NPC477453
0.8425	Intermediate Similarity	NPC315520
0.8421	Intermediate Similarity	NPC71610
0.8421	Intermediate Similarity	NPC15837
0.8417	Intermediate Similarity	NPC62272
0.8417	Intermediate Similarity	NPC475957
0.8409	Intermediate Similarity	NPC234890
0.8409	Intermediate Similarity	NPC236189
0.8409	Intermediate Similarity	NPC74507
0.8406	Intermediate Similarity	NPC249272
0.8403	Intermediate Similarity	NPC143685
0.8403	Intermediate Similarity	NPC147250
0.8397	Intermediate Similarity	NPC176208
0.8397	Intermediate Similarity	NPC283514
0.8394	Intermediate Similarity	NPC114183
0.8394	Intermediate Similarity	NPC171968
0.8394	Intermediate Similarity	NPC477139
0.8392	Intermediate Similarity	NPC244691
0.8392	Intermediate Similarity	NPC471906
0.8392	Intermediate Similarity	NPC48762
0.8392	Intermediate Similarity	NPC10764
0.8385	Intermediate Similarity	NPC259703
0.8385	Intermediate Similarity	NPC32322
0.838	Intermediate Similarity	NPC469520
0.838	Intermediate Similarity	NPC257644
0.8372	Intermediate Similarity	NPC232178
0.8369	Intermediate Similarity	NPC225243
0.8357	Intermediate Similarity	NPC206207
0.8346	Intermediate Similarity	NPC123506
0.8345	Intermediate Similarity	NPC141934
0.8345	Intermediate Similarity	NPC37709
0.8345	Intermediate Similarity	NPC118919
0.8345	Intermediate Similarity	NPC478018
0.8345	Intermediate Similarity	NPC119767
0.8333	Intermediate Similarity	NPC471683
0.8333	Intermediate Similarity	NPC135062
0.8333	Intermediate Similarity	NPC275145
0.8333	Intermediate Similarity	NPC478019
0.8333	Intermediate Similarity	NPC12402
0.8333	Intermediate Similarity	NPC270899
0.8333	Intermediate Similarity	NPC34482
0.8333	Intermediate Similarity	NPC202225
0.8322	Intermediate Similarity	NPC451542
0.8322	Intermediate Similarity	NPC296752
0.8322	Intermediate Similarity	NPC318270
0.8322	Intermediate Similarity	NPC313047
0.8322	Intermediate Similarity	NPC199936
0.8322	Intermediate Similarity	NPC474203
0.8322	Intermediate Similarity	NPC295712
0.8321	Intermediate Similarity	NPC198336
0.8321	Intermediate Similarity	NPC175738
0.831	Intermediate Similarity	NPC477275
0.8309	Intermediate Similarity	NPC475741
0.8299	Intermediate Similarity	NPC205766
0.8298	Intermediate Similarity	NPC162939
0.8296	Intermediate Similarity	NPC234175
0.8286	Intermediate Similarity	NPC147418
0.8284	Intermediate Similarity	NPC474106
0.8284	Intermediate Similarity	NPC295202
0.8284	Intermediate Similarity	NPC227741
0.8284	Intermediate Similarity	NPC49647

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 NPC53896 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	333
0.1-0.2	963
0.2-0.3	1279
0.3-0.4	2659
0.4-0.5	2213
0.5-0.6	1163
0.6-0.7	450
0.7-0.8	82
0.8-0.85	4
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8915	High Similarity	NPD1470	Approved
0.875	High Similarity	NPD1509	Clinical (unspecified phase)
0.8605	High Similarity	NPD1201	Approved
0.8571	High Similarity	NPD405	Clinical (unspecified phase)
0.8417	Intermediate Similarity	NPD5405	Approved
0.8417	Intermediate Similarity	NPD5406	Approved
0.8417	Intermediate Similarity	NPD5408	Approved
0.8417	Intermediate Similarity	NPD5404	Approved
0.8138	Intermediate Similarity	NPD7390	Discontinued
0.8108	Intermediate Similarity	NPD3226	Approved
0.8099	Intermediate Similarity	NPD2346	Discontinued
0.7959	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD1164	Approved
0.7895	Intermediate Similarity	NPD2932	Approved
0.7832	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD3300	Phase 2
0.7801	Intermediate Similarity	NPD943	Approved
0.7778	Intermediate Similarity	NPD2935	Discontinued
0.7761	Intermediate Similarity	NPD3019	Approved
0.7708	Intermediate Similarity	NPD2799	Discontinued
0.7603	Intermediate Similarity	NPD2344	Approved
0.7568	Intermediate Similarity	NPD7003	Approved
0.7556	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD3764	Approved
0.7535	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD2798	Approved
0.7483	Intermediate Similarity	NPD1471	Phase 3
0.7466	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD3750	Approved
0.7448	Intermediate Similarity	NPD1607	Approved
0.7444	Intermediate Similarity	NPD5951	Approved
0.7442	Intermediate Similarity	NPD2342	Discontinued
0.7438	Intermediate Similarity	NPD6232	Discontinued
0.7407	Intermediate Similarity	NPD7473	Discontinued
0.74	Intermediate Similarity	NPD2309	Approved
0.7372	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD1283	Approved
0.7347	Intermediate Similarity	NPD1510	Phase 2
0.7325	Intermediate Similarity	NPD7819	Suspended
0.7319	Intermediate Similarity	NPD3026	Approved
0.7319	Intermediate Similarity	NPD3023	Approved
0.731	Intermediate Similarity	NPD1240	Approved
0.7299	Intermediate Similarity	NPD3025	Approved
0.7299	Intermediate Similarity	NPD1651	Approved
0.7299	Intermediate Similarity	NPD3024	Approved
0.7293	Intermediate Similarity	NPD7635	Approved
0.7278	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6959	Discontinued
0.7267	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD9266	Approved
0.7252	Intermediate Similarity	NPD74	Approved
0.7234	Intermediate Similarity	NPD1876	Approved
0.7219	Intermediate Similarity	NPD8166	Discontinued
0.7206	Intermediate Similarity	NPD9493	Approved
0.7197	Intermediate Similarity	NPD7411	Suspended
0.7193	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7458	Discontinued
0.7179	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD9267	Approved
0.7176	Intermediate Similarity	NPD9263	Approved
0.7176	Intermediate Similarity	NPD9264	Approved
0.7143	Intermediate Similarity	NPD1281	Approved
0.7143	Intermediate Similarity	NPD2533	Approved
0.7143	Intermediate Similarity	NPD2534	Approved
0.7143	Intermediate Similarity	NPD2532	Approved
0.7134	Intermediate Similarity	NPD4380	Phase 2
0.7122	Intermediate Similarity	NPD4626	Approved
0.7114	Intermediate Similarity	NPD3748	Approved
0.7107	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD4878	Approved
0.7092	Intermediate Similarity	NPD3972	Approved
0.7086	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1549	Phase 2
0.7081	Intermediate Similarity	NPD3749	Approved
0.7076	Intermediate Similarity	NPD8150	Discontinued
0.7063	Intermediate Similarity	NPD1203	Approved
0.7031	Intermediate Similarity	NPD3020	Approved
0.703	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7768	Phase 2
0.7008	Intermediate Similarity	NPD288	Approved
0.7007	Intermediate Similarity	NPD6663	Approved
0.7	Intermediate Similarity	NPD1930	Approved
0.7	Intermediate Similarity	NPD2286	Discontinued
0.7	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1929	Approved
0.7	Intermediate Similarity	NPD4308	Phase 3
0.6992	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6273	Approved
0.6968	Remote Similarity	NPD1511	Approved
0.6966	Remote Similarity	NPD5736	Approved
0.6957	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.694	Remote Similarity	NPD3021	Approved
0.694	Remote Similarity	NPD3022	Approved
0.6939	Remote Similarity	NPD3268	Approved
0.6939	Remote Similarity	NPD411	Approved
0.6937	Remote Similarity	NPD1934	Approved
0.6934	Remote Similarity	NPD9281	Approved
0.6929	Remote Similarity	NPD2860	Approved
0.6929	Remote Similarity	NPD2859	Approved
0.6929	Remote Similarity	NPD844	Approved
0.6928	Remote Similarity	NPD2800	Approved
0.6923	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1932	Approved
0.6917	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD8313	Approved
0.6901	Remote Similarity	NPD8312	Approved
0.6894	Remote Similarity	NPD2801	Approved
0.6889	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5029	Approved
0.6882	Remote Similarity	NPD5031	Approved
0.6882	Remote Similarity	NPD5027	Approved
0.6879	Remote Similarity	NPD1512	Approved
0.6879	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7008	Discontinued
0.6871	Remote Similarity	NPD7075	Discontinued
0.687	Remote Similarity	NPD9261	Approved
0.6857	Remote Similarity	NPD3091	Approved
0.6853	Remote Similarity	NPD9717	Approved
0.6852	Remote Similarity	NPD2296	Approved
0.685	Remote Similarity	NPD2933	Approved
0.685	Remote Similarity	NPD2934	Approved
0.6846	Remote Similarity	NPD2979	Phase 3
0.6842	Remote Similarity	NPD2796	Approved
0.6842	Remote Similarity	NPD4955	Approved
0.6842	Remote Similarity	NPD5028	Approved
0.6842	Remote Similarity	NPD36	Approved
0.6842	Remote Similarity	NPD5026	Approved
0.6842	Remote Similarity	NPD1551	Phase 2
0.6842	Remote Similarity	NPD5034	Approved
0.6842	Remote Similarity	NPD4954	Approved
0.6838	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1237	Approved
0.6815	Remote Similarity	NPD4750	Phase 3
0.6812	Remote Similarity	NPD497	Approved
0.681	Remote Similarity	NPD3882	Suspended
0.6809	Remote Similarity	NPD5691	Approved
0.6805	Remote Similarity	NPD6020	Phase 2
0.6805	Remote Similarity	NPD5844	Phase 1
0.68	Remote Similarity	NPD447	Suspended
0.679	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD5494	Approved
0.6784	Remote Similarity	NPD6559	Discontinued
0.6784	Remote Similarity	NPD5030	Phase 2
0.6774	Remote Similarity	NPD4628	Phase 3
0.6774	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD4059	Approved
0.6744	Remote Similarity	NPD5032	Approved
0.6742	Remote Similarity	NPD6534	Approved
0.6742	Remote Similarity	NPD6535	Approved
0.6741	Remote Similarity	NPD2329	Discontinued
0.6739	Remote Similarity	NPD498	Approved
0.6739	Remote Similarity	NPD495	Approved
0.6739	Remote Similarity	NPD496	Approved
0.6738	Remote Similarity	NPD9545	Approved
0.6733	Remote Similarity	NPD4307	Phase 2
0.6733	Remote Similarity	NPD4060	Phase 1
0.6728	Remote Similarity	NPD6844	Discontinued
0.6723	Remote Similarity	NPD5968	Phase 3
0.6718	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD4879	Approved
0.6712	Remote Similarity	NPD3266	Approved
0.6712	Remote Similarity	NPD3267	Approved
0.6712	Remote Similarity	NPD2797	Approved
0.6708	Remote Similarity	NPD6599	Discontinued
0.6705	Remote Similarity	NPD5035	Approved
0.669	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.669	Remote Similarity	NPD4093	Discontinued
0.6689	Remote Similarity	NPD6832	Phase 2
0.6689	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5037	Approved
0.6686	Remote Similarity	NPD5033	Approved
0.6686	Remote Similarity	NPD5038	Approved
0.6685	Remote Similarity	NPD6212	Phase 3
0.6685	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6213	Phase 3
0.6667	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7610	Discontinued
0.6667	Remote Similarity	NPD3092	Approved
0.6667	Remote Similarity	NPD1809	Phase 2
0.6648	Remote Similarity	NPD6782	Approved
0.6648	Remote Similarity	NPD6778	Approved
0.6648	Remote Similarity	NPD6777	Approved
0.6648	Remote Similarity	NPD6781	Approved
0.6648	Remote Similarity	NPD6780	Approved
0.6648	Remote Similarity	NPD6776	Approved
0.6648	Remote Similarity	NPD6779	Approved
0.6647	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7177	Discontinued
0.6645	Remote Similarity	NPD6651	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