NPASS Compound

Structure

CID55949 OpenBabel06191715392D 28 31 0 0 0 0 0 0 0 0999 V2000 -5.1962 -3.0000 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 -2.5981 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 -3.4641 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 -3.4641 -3.0000 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 -4.3301 -2.5000 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 -1.7321 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 -3.4641 -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 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 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 0.5000 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 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 0.0000 0.0000 0.0000 C 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 -5.1962 -1.0000 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 -0.8660 -1.5000 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 9 1 0 0 0 0 2 10 1 0 0 0 0 3 5 2 0 0 0 0 3 11 1 0 0 0 0 4 6 2 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 6 14 1 0 0 0 0 7 9 2 0 0 0 0 7 15 1 0 0 0 0 8 10 2 0 0 0 0 8 16 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 21 2 0 0 0 0 12 22 2 0 0 0 0 13 17 2 0 0 0 0 13 19 1 0 0 0 0 14 18 2 0 0 0 0 14 20 1 0 0 0 0 15 17 1 0 0 0 0 15 23 2 0 0 0 0 16 18 1 0 0 0 0 16 24 2 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 19 25 2 0 0 0 0 20 26 2 0 0 0 0 21 27 1 0 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.08
Volume:	375.946
LogP:	3.671
LogD:	2.476
LogS:	-4.251
# Rotatable Bonds:	0
TPSA:	111.9
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.361
Synthetic Accessibility Score:	3.567
Fsp3:	0.045
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.487
MDCK Permeability:	1.0363347428210545e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	98.15995025634766%
Volume Distribution (VD):	0.36
Pgp-substrate:	6.830906867980957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.967
CYP1A2-substrate:	0.152
CYP2C19-inhibitor:	0.571
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.853
CYP2C9-substrate:	0.199
CYP2D6-inhibitor:	0.78
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.194
CYP3A4-substrate:	0.058

ADMET: Excretion

Clearance (CL):	2.267
Half-life (T1/2):	0.311

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.298
Drug-inuced Liver Injury (DILI):	0.963
AMES Toxicity:	0.805
Rat Oral Acute Toxicity:	0.795
Maximum Recommended Daily Dose:	0.926
Skin Sensitization:	0.953
Carcinogencity:	0.739
Eye Corrosion:	0.003
Eye Irritation:	0.903
Respiratory Toxicity:	0.529

Download Data

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

Natural Product: NPC55949

Natural Product ID:	NPC55949
*Common Name:**	Elliptinone
IUPAC Name:	5-hydroxy-6-(1-hydroxy-6-methyl-5,8-dioxonaphthalen-2-yl)-2-methylnaphthalene-1,4-dione
Synonyms:	Elliptinone
Standard InCHIKey:	TXVAHWOABLOYCD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H14O6/c1-9-7-15(23)17-13(19(9)25)5-3-11(21(17)27)12-4-6-14-18(22(12)28)16(24)8-10(2)20(14)26/h3-8,27-28H,1-2H3
SMILES:	CC1=CC(=O)c2c(ccc(c3ccc4c(C(=O)C=C(C)C4=O)c3O)c2O)C1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2023568
PubChem CID:	146680
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	bark	Indonesia	n.a.	PMID[15270571]
NPO13608	Plumbago zeylanica	Species	Plumbaginaceae	Eukaryota	n.a.	root	n.a.	PMID[16078700]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	calyx	n.a.	PMID[21561086]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22313254]
NPO33133	barleria alluaudii	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22313254]
NPO13608	Plumbago zeylanica	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23848163]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	fruit	n.a.	PMID[24086493]
NPO13608	Plumbago zeylanica	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13608	Plumbago zeylanica	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18296	Diospyros kaki	Species	Ebenaceae	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]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13608	Plumbago zeylanica	Species	Plumbaginaceae	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
EC50	2
Others	1

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT369	Cell Line	ACHN	Homo sapiens	EC50	=	3800.0	nM	PMID[515342]
NPT369	Cell Line	ACHN	Homo sapiens	EC50	=	13200.0	nM	PMID[515342]
NPT369	Cell Line	ACHN	Homo sapiens	Ratio EC50	=	3.5	n.a.	PMID[515342]

☑ 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 NPC55949 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	326
0.1-0.2	1535
0.2-0.3	3285
0.3-0.4	9671
0.4-0.5	9871
0.5-0.6	6073
0.6-0.7	8310
0.7-0.8	3144
0.8-0.85	317
0.85-0.9	124
0.9-0.95	30
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9758	High Similarity	NPC34414
0.9758	High Similarity	NPC146647
0.9603	High Similarity	NPC244699
0.9531	High Similarity	NPC50924
0.9528	High Similarity	NPC58685
0.9453	High Similarity	NPC53896
0.9365	High Similarity	NPC48248
0.9355	High Similarity	NPC142956
0.9308	High Similarity	NPC283088
0.9302	High Similarity	NPC225051
0.9237	High Similarity	NPC474813
0.9237	High Similarity	NPC155211
0.9213	High Similarity	NPC282923
0.9194	High Similarity	NPC307174
0.9167	High Similarity	NPC305060
0.9167	High Similarity	NPC245923
0.9147	High Similarity	NPC205992
0.912	High Similarity	NPC375356
0.907	High Similarity	NPC199253
0.907	High Similarity	NPC136588
0.9055	High Similarity	NPC306765
0.9055	High Similarity	NPC3224
0.9055	High Similarity	NPC96915
0.904	High Similarity	NPC300274
0.9015	High Similarity	NPC80035
0.9008	High Similarity	NPC115458
0.8992	High Similarity	NPC99731
0.8976	High Similarity	NPC103540
0.8952	High Similarity	NPC206778
0.8952	High Similarity	NPC285829
0.8947	High Similarity	NPC272268
0.8931	High Similarity	NPC70622
0.8923	High Similarity	NPC31799
0.8898	High Similarity	NPC310540
0.8898	High Similarity	NPC173978
0.8864	High Similarity	NPC52407
0.8855	High Similarity	NPC17083
0.8855	High Similarity	NPC474517
0.8855	High Similarity	NPC72669
0.8837	High Similarity	NPC471530
0.8815	High Similarity	NPC13715
0.8806	High Similarity	NPC193358
0.8797	High Similarity	NPC288089
0.8779	High Similarity	NPC31539
0.8779	High Similarity	NPC198305
0.8769	High Similarity	NPC96024
0.876	High Similarity	NPC160499
0.876	High Similarity	NPC231774
0.875	High Similarity	NPC68756
0.875	High Similarity	NPC152525
0.875	High Similarity	NPC236189
0.8731	High Similarity	NPC258502
0.8731	High Similarity	NPC161632
0.8722	High Similarity	NPC314048
0.8722	High Similarity	NPC114183
0.8702	High Similarity	NPC278928
0.8696	High Similarity	NPC239136
0.8696	High Similarity	NPC19631
0.8696	High Similarity	NPC69755
0.8686	High Similarity	NPC96421
0.8676	High Similarity	NPC4214
0.8667	High Similarity	NPC474311
0.8657	High Similarity	NPC12070
0.8657	High Similarity	NPC161964
0.8657	High Similarity	NPC472262
0.8657	High Similarity	NPC287604
0.8657	High Similarity	NPC270899
0.8647	High Similarity	NPC246693
0.8647	High Similarity	NPC242358
0.8647	High Similarity	NPC110609
0.8633	High Similarity	NPC471682
0.8629	High Similarity	NPC108288
0.8626	High Similarity	NPC237225
0.8623	High Similarity	NPC246638
0.8623	High Similarity	NPC124365
0.8613	High Similarity	NPC242994
0.8613	High Similarity	NPC26924
0.8613	High Similarity	NPC138099
0.8613	High Similarity	NPC1268
0.8605	High Similarity	NPC74507
0.8605	High Similarity	NPC234890
0.8603	High Similarity	NPC53414
0.8603	High Similarity	NPC471905
0.8603	High Similarity	NPC53206
0.8593	High Similarity	NPC249272
0.8583	High Similarity	NPC472046
0.8582	High Similarity	NPC171968
0.8571	High Similarity	NPC85342
0.8571	High Similarity	NPC232178
0.8561	High Similarity	NPC257644
0.8551	High Similarity	NPC225243
0.8551	High Similarity	NPC315578
0.8551	High Similarity	NPC181560
0.8551	High Similarity	NPC169452
0.8548	High Similarity	NPC161304
0.854	High Similarity	NPC416
0.854	High Similarity	NPC61398
0.8529	High Similarity	NPC315275
0.8529	High Similarity	NPC254847
0.8527	High Similarity	NPC275145
0.8511	High Similarity	NPC471683
0.8507	High Similarity	NPC309430
0.8496	Intermediate Similarity	NPC27659
0.848	Intermediate Similarity	NPC477453
0.8478	Intermediate Similarity	NPC470407
0.8478	Intermediate Similarity	NPC143438
0.8473	Intermediate Similarity	NPC227741
0.8473	Intermediate Similarity	NPC254492
0.8473	Intermediate Similarity	NPC51037
0.8473	Intermediate Similarity	NPC136342
0.8473	Intermediate Similarity	NPC49647
0.8473	Intermediate Similarity	NPC1991
0.8473	Intermediate Similarity	NPC295202
0.8467	Intermediate Similarity	NPC36868
0.8467	Intermediate Similarity	NPC53001
0.8467	Intermediate Similarity	NPC62272
0.8462	Intermediate Similarity	NPC199273
0.8462	Intermediate Similarity	NPC164014
0.8456	Intermediate Similarity	NPC281513
0.8456	Intermediate Similarity	NPC22222
0.845	Intermediate Similarity	NPC91478
0.8444	Intermediate Similarity	NPC294226
0.8444	Intermediate Similarity	NPC254603
0.844	Intermediate Similarity	NPC79627
0.844	Intermediate Similarity	NPC10764
0.8433	Intermediate Similarity	NPC93015
0.8429	Intermediate Similarity	NPC469520
0.8429	Intermediate Similarity	NPC474300
0.8429	Intermediate Similarity	NPC193555
0.8421	Intermediate Similarity	NPC57552
0.8421	Intermediate Similarity	NPC276238
0.8409	Intermediate Similarity	NPC72667
0.8406	Intermediate Similarity	NPC87723
0.8397	Intermediate Similarity	NPC131799
0.8394	Intermediate Similarity	NPC141934
0.8394	Intermediate Similarity	NPC472308
0.8392	Intermediate Similarity	NPC37709
0.8385	Intermediate Similarity	NPC135062
0.8382	Intermediate Similarity	NPC282780
0.8382	Intermediate Similarity	NPC44437
0.8382	Intermediate Similarity	NPC166480
0.8372	Intermediate Similarity	NPC120545
0.8369	Intermediate Similarity	NPC476473
0.8369	Intermediate Similarity	NPC66593
0.8359	Intermediate Similarity	NPC7151
0.8359	Intermediate Similarity	NPC216297
0.8359	Intermediate Similarity	NPC473662
0.8358	Intermediate Similarity	NPC108129
0.8358	Intermediate Similarity	NPC117609
0.8358	Intermediate Similarity	NPC475741
0.8357	Intermediate Similarity	NPC204045
0.8357	Intermediate Similarity	NPC305845
0.8357	Intermediate Similarity	NPC187843
0.8346	Intermediate Similarity	NPC41567
0.8345	Intermediate Similarity	NPC190457
0.8322	Intermediate Similarity	NPC147250
0.8322	Intermediate Similarity	NPC300540
0.831	Intermediate Similarity	NPC477913
0.831	Intermediate Similarity	NPC29932
0.831	Intermediate Similarity	NPC471906
0.831	Intermediate Similarity	NPC244691
0.831	Intermediate Similarity	NPC193703
0.831	Intermediate Similarity	NPC21599
0.8309	Intermediate Similarity	NPC267205
0.8308	Intermediate Similarity	NPC282577
0.8308	Intermediate Similarity	NPC176208
0.8298	Intermediate Similarity	NPC135524
0.8288	Intermediate Similarity	NPC144283
0.8286	Intermediate Similarity	NPC183345
0.8284	Intermediate Similarity	NPC171460
0.8284	Intermediate Similarity	NPC25736
0.8273	Intermediate Similarity	NPC61590
0.8273	Intermediate Similarity	NPC173980
0.8273	Intermediate Similarity	NPC206207
0.8271	Intermediate Similarity	NPC176130
0.8271	Intermediate Similarity	NPC78364
0.8271	Intermediate Similarity	NPC84672
0.8271	Intermediate Similarity	NPC69424
0.8268	Intermediate Similarity	NPC269414
0.8264	Intermediate Similarity	NPC119767
0.8261	Intermediate Similarity	NPC475549
0.8261	Intermediate Similarity	NPC191976
0.8254	Intermediate Similarity	NPC240163
0.8248	Intermediate Similarity	NPC202225
0.8248	Intermediate Similarity	NPC1249
0.8244	Intermediate Similarity	NPC477153
0.8239	Intermediate Similarity	NPC53016
0.8239	Intermediate Similarity	NPC296752
0.8235	Intermediate Similarity	NPC88864
0.8231	Intermediate Similarity	NPC154696
0.8227	Intermediate Similarity	NPC290550
0.8227	Intermediate Similarity	NPC477275
0.8227	Intermediate Similarity	NPC110810
0.8219	Intermediate Similarity	NPC205766
0.8219	Intermediate Similarity	NPC315520
0.8214	Intermediate Similarity	NPC216312
0.8214	Intermediate Similarity	NPC471602
0.8214	Intermediate Similarity	NPC29771
0.8214	Intermediate Similarity	NPC306835
0.8214	Intermediate Similarity	NPC111422

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 NPC55949 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	951
0.2-0.3	1215
0.3-0.4	2578
0.4-0.5	2338
0.5-0.6	1210
0.6-0.7	451
0.7-0.8	80
0.8-0.85	5
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8976	High Similarity	NPD1470	Approved
0.8661	High Similarity	NPD1201	Approved
0.8629	High Similarity	NPD405	Clinical (unspecified phase)
0.8529	High Similarity	NPD1509	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD5406	Approved
0.8467	Intermediate Similarity	NPD5404	Approved
0.8467	Intermediate Similarity	NPD5405	Approved
0.8467	Intermediate Similarity	NPD5408	Approved
0.8406	Intermediate Similarity	NPD2346	Discontinued
0.8182	Intermediate Similarity	NPD7390	Discontinued
0.8125	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD3226	Approved
0.7986	Intermediate Similarity	NPD3300	Phase 2
0.7852	Intermediate Similarity	NPD1164	Approved
0.7826	Intermediate Similarity	NPD2313	Discontinued
0.776	Intermediate Similarity	NPD2342	Discontinued
0.7734	Intermediate Similarity	NPD7635	Approved
0.7692	Intermediate Similarity	NPD2935	Discontinued
0.7669	Intermediate Similarity	NPD2932	Approved
0.7615	Intermediate Similarity	NPD5951	Approved
0.7589	Intermediate Similarity	NPD943	Approved
0.7537	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD3019	Approved
0.7536	Intermediate Similarity	NPD2798	Approved
0.7517	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2799	Discontinued
0.7483	Intermediate Similarity	NPD7003	Approved
0.7468	Intermediate Similarity	NPD6232	Discontinued
0.7463	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD7473	Discontinued
0.7379	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD3764	Approved
0.732	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD2309	Approved
0.7296	Intermediate Similarity	NPD6959	Discontinued
0.7287	Intermediate Similarity	NPD74	Approved
0.7287	Intermediate Similarity	NPD9266	Approved
0.7279	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD1283	Approved
0.7248	Intermediate Similarity	NPD3750	Approved
0.7246	Intermediate Similarity	NPD4878	Approved
0.7241	Intermediate Similarity	NPD1607	Approved
0.7239	Intermediate Similarity	NPD9493	Approved
0.7222	Intermediate Similarity	NPD1932	Approved
0.7219	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD9267	Approved
0.7209	Intermediate Similarity	NPD9263	Approved
0.7209	Intermediate Similarity	NPD9264	Approved
0.7206	Intermediate Similarity	NPD1651	Approved
0.7202	Intermediate Similarity	NPD8150	Discontinued
0.7171	Intermediate Similarity	NPD2534	Approved
0.7171	Intermediate Similarity	NPD2533	Approved
0.7171	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2532	Approved
0.7165	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD1929	Approved
0.7165	Intermediate Similarity	NPD1930	Approved
0.7162	Intermediate Similarity	NPD1471	Phase 3
0.7154	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1510	Phase 2
0.7134	Intermediate Similarity	NPD7819	Suspended
0.7133	Intermediate Similarity	NPD7008	Discontinued
0.7103	Intermediate Similarity	NPD1240	Approved
0.7101	Intermediate Similarity	NPD3026	Approved
0.7101	Intermediate Similarity	NPD3023	Approved
0.7092	Intermediate Similarity	NPD1203	Approved
0.709	Intermediate Similarity	NPD497	Approved
0.708	Intermediate Similarity	NPD3024	Approved
0.708	Intermediate Similarity	NPD3025	Approved
0.7051	Intermediate Similarity	NPD4380	Phase 2
0.705	Intermediate Similarity	NPD1281	Approved
0.705	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD288	Approved
0.7029	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4308	Phase 3
0.7025	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD8313	Approved
0.7024	Intermediate Similarity	NPD8312	Approved
0.7023	Intermediate Similarity	NPD2329	Discontinued
0.7021	Intermediate Similarity	NPD1876	Approved
0.702	Intermediate Similarity	NPD8166	Discontinued
0.7015	Intermediate Similarity	NPD496	Approved
0.7015	Intermediate Similarity	NPD498	Approved
0.7015	Intermediate Similarity	NPD495	Approved
0.7014	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5031	Approved
0.7006	Intermediate Similarity	NPD5027	Approved
0.7006	Intermediate Similarity	NPD5029	Approved
0.7	Intermediate Similarity	NPD3749	Approved
0.6992	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7458	Discontinued
0.6977	Remote Similarity	NPD1237	Approved
0.6966	Remote Similarity	NPD411	Approved
0.6964	Remote Similarity	NPD5026	Approved
0.6964	Remote Similarity	NPD36	Approved
0.6964	Remote Similarity	NPD4955	Approved
0.6964	Remote Similarity	NPD5034	Approved
0.6964	Remote Similarity	NPD4954	Approved
0.6964	Remote Similarity	NPD5028	Approved
0.6963	Remote Similarity	NPD9281	Approved
0.696	Remote Similarity	NPD844	Approved
0.6954	Remote Similarity	NPD2800	Approved
0.6939	Remote Similarity	NPD447	Suspended
0.6937	Remote Similarity	NPD7768	Phase 2
0.6936	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD3748	Approved
0.6908	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD4626	Approved
0.6906	Remote Similarity	NPD2286	Discontinued
0.6905	Remote Similarity	NPD5030	Phase 2
0.6899	Remote Similarity	NPD9261	Approved
0.6897	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6212	Phase 3
0.6897	Remote Similarity	NPD6213	Phase 3
0.6887	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD1549	Phase 2
0.6883	Remote Similarity	NPD1511	Approved
0.6879	Remote Similarity	NPD3972	Approved
0.6879	Remote Similarity	NPD9717	Approved
0.6875	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD2979	Phase 3
0.6867	Remote Similarity	NPD1551	Phase 2
0.6861	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4879	Approved
0.6857	Remote Similarity	NPD6534	Approved
0.6857	Remote Similarity	NPD6535	Approved
0.6855	Remote Similarity	NPD6844	Discontinued
0.6855	Remote Similarity	NPD1934	Approved
0.6842	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4750	Phase 3
0.6826	Remote Similarity	NPD5844	Phase 1
0.6824	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD2801	Approved
0.6809	Remote Similarity	NPD1611	Approved
0.6805	Remote Similarity	NPD6559	Discontinued
0.6803	Remote Similarity	NPD6663	Approved
0.6802	Remote Similarity	NPD5037	Approved
0.6802	Remote Similarity	NPD5038	Approved
0.68	Remote Similarity	NPD845	Approved
0.6797	Remote Similarity	NPD3020	Approved
0.6797	Remote Similarity	NPD2066	Phase 3
0.6797	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD6273	Approved
0.6795	Remote Similarity	NPD1512	Approved
0.6792	Remote Similarity	NPD7411	Suspended
0.6781	Remote Similarity	NPD4625	Phase 3
0.6772	Remote Similarity	NPD3495	Discontinued
0.677	Remote Similarity	NPD2296	Approved
0.6766	Remote Similarity	NPD7177	Discontinued
0.6765	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7009	Phase 2
0.6759	Remote Similarity	NPD5736	Approved
0.6757	Remote Similarity	NPD4307	Phase 2
0.6753	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5036	Approved
0.6742	Remote Similarity	NPD7699	Phase 2
0.6742	Remote Similarity	NPD7700	Phase 2
0.6736	Remote Similarity	NPD2797	Approved
0.6735	Remote Similarity	NPD3268	Approved
0.6724	Remote Similarity	NPD6836	Approved
0.6718	Remote Similarity	NPD164	Approved
0.6716	Remote Similarity	NPD3021	Approved
0.6716	Remote Similarity	NPD3022	Approved
0.6713	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD6832	Phase 2
0.671	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5494	Approved
0.6693	Remote Similarity	NPD2860	Approved
0.6693	Remote Similarity	NPD2859	Approved
0.6692	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD7610	Discontinued
0.6687	Remote Similarity	NPD7075	Discontinued
0.6667	Remote Similarity	NPD6777	Approved
0.6667	Remote Similarity	NPD6781	Approved
0.6667	Remote Similarity	NPD6780	Approved
0.6667	Remote Similarity	NPD3317	Approved
0.6667	Remote Similarity	NPD6776	Approved
0.6667	Remote Similarity	NPD6779	Approved
0.6667	Remote Similarity	NPD5402	Approved
0.6667	Remote Similarity	NPD6782	Approved
0.6667	Remote Similarity	NPD6778	Approved
0.6648	Remote Similarity	NPD5968	Phase 3
0.6645	Remote Similarity	NPD6100	Approved
0.6645	Remote Similarity	NPD6099	Approved
0.6645	Remote Similarity	NPD2796	Approved
0.6643	Remote Similarity	NPD3091	Approved
0.6642	Remote Similarity	NPD2182	Approved
0.664	Remote Similarity	NPD7609	Phase 3
0.6627	Remote Similarity	NPD5710	Approved
0.6627	Remote Similarity	NPD5711	Approved
0.6627	Remote Similarity	NPD6020	Phase 2

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