NPASS Compound

Structure

NPC245923 OpenBabel07101719152D 26 29 0 0 0 0 0 0 0 0999 V2000 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -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 -5.1962 -2.0000 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 2.5981 -0.5000 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 -3.4641 -0.0000 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 -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 -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 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 -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 -1.7321 -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 -2.0000 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 1.0000 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 -3.0000 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 0.0000 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 4 1 0 0 0 0 3 5 2 0 0 0 0 3 6 1 0 0 0 0 4 10 1 0 0 0 0 5 12 1 0 0 0 0 6 14 2 0 0 0 0 7 8 2 0 0 0 0 7 10 1 0 0 0 0 8 11 1 0 0 0 0 9 10 2 0 0 0 0 9 13 1 0 0 0 0 11 13 1 0 0 0 0 11 18 2 0 0 0 0 12 15 2 0 0 0 0 12 19 1 0 0 0 0 13 20 2 0 0 0 0 14 15 1 0 0 0 0 14 22 1 0 0 0 0 15 21 1 0 0 0 0 16 17 2 0 0 0 0 16 19 1 0 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 23 1 0 0 0 0 19 24 2 0 0 0 0 20 25 1 0 0 0 0 21 26 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.1
Volume:	355.133
LogP:	5.534
LogD:	2.84
LogS:	-3.413
# Rotatable Bonds:	1
TPSA:	101.15
# H-Bond Aceptor:	5
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.253
Synthetic Accessibility Score:	2.847
Fsp3:	0.048
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.279
MDCK Permeability:	8.208146937249694e-06
Pgp-inhibitor:	0.01
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.741
20% Bioavailability (F20%):	0.058
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	97.77272033691406%
Volume Distribution (VD):	0.496
Pgp-substrate:	7.7612690925598145%

ADMET: Metabolism

CYP1A2-inhibitor:	0.928
CYP1A2-substrate:	0.268
CYP2C19-inhibitor:	0.056
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.64
CYP2C9-substrate:	0.622
CYP2D6-inhibitor:	0.082
CYP2D6-substrate:	0.374
CYP3A4-inhibitor:	0.043
CYP3A4-substrate:	0.041

ADMET: Excretion

Clearance (CL):	5.439
Half-life (T1/2):	0.564

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.141
Drug-inuced Liver Injury (DILI):	0.933
AMES Toxicity:	0.751
Rat Oral Acute Toxicity:	0.14
Maximum Recommended Daily Dose:	0.894
Skin Sensitization:	0.965
Carcinogencity:	0.717
Eye Corrosion:	0.003
Eye Irritation:	0.923
Respiratory Toxicity:	0.506

Download Data

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

Natural Product: NPC245923

Natural Product ID:	NPC245923
*Common Name:**	1,6,11-Trihydroxy-8-Propyltetracene-5,12-Dione
IUPAC Name:	1,6,11-trihydroxy-8-propyltetracene-5,12-dione
Synonyms:
Standard InCHIKey:	YFRSOTKZPUMXIQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H16O5/c1-2-4-10-7-8-11-13(9-10)20(25)16-17(18(11)23)21(26)15-12(19(16)24)5-3-6-14(15)22/h3,5-9,22-23,25H,2,4H2,1H3
SMILES:	CCCc1ccc2c(c1)c(O)c1c(c2O)C(=O)c2c(C1=O)cccc2O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2024355
PubChem CID:	57381513
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000022] Naphthacenes [CHEMONTID:0000155] Tetracenequinones

*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
NPO32815	micromonospora sp.	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22250891]
NPO32815	micromonospora sp.	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25375258]
NPO32815	micromonospora sp.	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26444379]
NPO32815	micromonospora sp.	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27813411]
NPO32815	micromonospora sp.	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31794218]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	12700.0	nM	PMID[512857]

☑ 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 NPC245923 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	377
0.1-0.2	1688
0.2-0.3	3699
0.3-0.4	10748
0.4-0.5	8561
0.5-0.6	5843
0.6-0.7	7671
0.7-0.8	3720
0.8-0.85	262
0.85-0.9	89
0.9-0.95	35
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9923	High Similarity	NPC474813
0.9621	High Similarity	NPC155211
0.9538	High Similarity	NPC205992
0.9474	High Similarity	NPC272268
0.9398	High Similarity	NPC283088
0.9394	High Similarity	NPC225051
0.9308	High Similarity	NPC48248
0.9308	High Similarity	NPC282923
0.9281	High Similarity	NPC471683
0.9248	High Similarity	NPC115458
0.9242	High Similarity	NPC474517
0.9242	High Similarity	NPC72669
0.9209	High Similarity	NPC10764
0.9203	High Similarity	NPC19631
0.9203	High Similarity	NPC239136
0.9179	High Similarity	NPC161964
0.9179	High Similarity	NPC287604
0.9179	High Similarity	NPC472262
0.9173	High Similarity	NPC58685
0.9167	High Similarity	NPC55949
0.9154	High Similarity	NPC96915
0.9137	High Similarity	NPC471682
0.9118	High Similarity	NPC305060
0.9091	High Similarity	NPC34414
0.9091	High Similarity	NPC99731
0.9091	High Similarity	NPC146647
0.9077	High Similarity	NPC103540
0.9065	High Similarity	NPC257644
0.9058	High Similarity	NPC96421
0.9058	High Similarity	NPC225243
0.9051	High Similarity	NPC13715
0.903	High Similarity	NPC70622
0.9008	High Similarity	NPC306765
0.9	High Similarity	NPC142956
0.9	High Similarity	NPC173978
0.8993	High Similarity	NPC246638
0.8993	High Similarity	NPC124365
0.8971	High Similarity	NPC80035
0.8955	High Similarity	NPC244699
0.8923	High Similarity	NPC375356
0.8897	High Similarity	NPC50924
0.8897	High Similarity	NPC288089
0.8889	High Similarity	NPC242358
0.8889	High Similarity	NPC246693
0.8889	High Similarity	NPC110609
0.8881	High Similarity	NPC136588
0.8881	High Similarity	NPC37709
0.8881	High Similarity	NPC199253
0.8864	High Similarity	NPC3224
0.8849	High Similarity	NPC138099
0.8849	High Similarity	NPC143438
0.8849	High Similarity	NPC242994
0.8846	High Similarity	NPC300274
0.8844	High Similarity	NPC66029
0.8841	High Similarity	NPC62272
0.8828	High Similarity	NPC315520
0.8824	High Similarity	NPC314048
0.8824	High Similarity	NPC53896
0.8811	High Similarity	NPC147250
0.8806	High Similarity	NPC278928
0.8797	High Similarity	NPC471530
0.8794	High Similarity	NPC69755
0.8786	High Similarity	NPC169452
0.8786	High Similarity	NPC315578
0.8786	High Similarity	NPC181560
0.8741	High Similarity	NPC31539
0.8732	High Similarity	NPC296752
0.8723	High Similarity	NPC187843
0.8714	High Similarity	NPC1268
0.8714	High Similarity	NPC26924
0.8705	High Similarity	NPC471905
0.8705	High Similarity	NPC53206
0.8705	High Similarity	NPC53414
0.8702	High Similarity	NPC307174
0.8699	High Similarity	NPC205766
0.8696	High Similarity	NPC161632
0.8686	High Similarity	NPC52407
0.8681	High Similarity	NPC300540
0.8676	High Similarity	NPC85342
0.8671	High Similarity	NPC227841
0.8662	High Similarity	NPC474300
0.8662	High Similarity	NPC193555
0.8649	High Similarity	NPC218870
0.8649	High Similarity	NPC474824
0.8649	High Similarity	NPC470408
0.8649	High Similarity	NPC182921
0.8643	High Similarity	NPC416
0.8643	High Similarity	NPC61398
0.8633	High Similarity	NPC254847
0.8633	High Similarity	NPC472308
0.8623	High Similarity	NPC12070
0.8621	High Similarity	NPC119767
0.8603	High Similarity	NPC31799
0.8601	High Similarity	NPC451542
0.8601	High Similarity	NPC476473
0.8601	High Similarity	NPC313047
0.8601	High Similarity	NPC474203
0.8601	High Similarity	NPC295712
0.8592	High Similarity	NPC477275
0.8582	High Similarity	NPC1991
0.8582	High Similarity	NPC49647
0.8582	High Similarity	NPC231774
0.8582	High Similarity	NPC295202
0.8582	High Similarity	NPC227741
0.8582	High Similarity	NPC136342
0.8571	High Similarity	NPC147418
0.8561	High Similarity	NPC249272
0.8551	High Similarity	NPC114183
0.854	High Similarity	NPC17083
0.8533	High Similarity	NPC474861
0.8531	High Similarity	NPC85310
0.8531	High Similarity	NPC135524
0.8531	High Similarity	NPC469520
0.8511	High Similarity	NPC4214
0.8507	High Similarity	NPC131799
0.85	High Similarity	NPC141934
0.85	High Similarity	NPC191976
0.85	High Similarity	NPC193358
0.8493	Intermediate Similarity	NPC290194
0.8489	Intermediate Similarity	NPC44437
0.8489	Intermediate Similarity	NPC282780
0.8489	Intermediate Similarity	NPC166480
0.8489	Intermediate Similarity	NPC270899
0.8483	Intermediate Similarity	NPC68441
0.8483	Intermediate Similarity	NPC12402
0.8473	Intermediate Similarity	NPC206778
0.8473	Intermediate Similarity	NPC285829
0.8472	Intermediate Similarity	NPC174905
0.8472	Intermediate Similarity	NPC293545
0.8467	Intermediate Similarity	NPC66508
0.8467	Intermediate Similarity	NPC226656
0.8462	Intermediate Similarity	NPC305845
0.8462	Intermediate Similarity	NPC204045
0.8456	Intermediate Similarity	NPC96024
0.8451	Intermediate Similarity	NPC216312
0.8451	Intermediate Similarity	NPC29771
0.8451	Intermediate Similarity	NPC190457
0.8451	Intermediate Similarity	NPC256463
0.8451	Intermediate Similarity	NPC476477
0.8451	Intermediate Similarity	NPC471602
0.8451	Intermediate Similarity	NPC111422
0.8451	Intermediate Similarity	NPC306835
0.8451	Intermediate Similarity	NPC299405
0.8444	Intermediate Similarity	NPC160499
0.844	Intermediate Similarity	NPC44960
0.844	Intermediate Similarity	NPC474110
0.844	Intermediate Similarity	NPC53001
0.8433	Intermediate Similarity	NPC68756
0.8433	Intermediate Similarity	NPC152525
0.8433	Intermediate Similarity	NPC310540
0.8429	Intermediate Similarity	NPC258502
0.8429	Intermediate Similarity	NPC22222
0.8429	Intermediate Similarity	NPC281513
0.8425	Intermediate Similarity	NPC314437
0.8425	Intermediate Similarity	NPC285122
0.8425	Intermediate Similarity	NPC271944
0.8425	Intermediate Similarity	NPC110882
0.8425	Intermediate Similarity	NPC85393
0.8421	Intermediate Similarity	NPC324736
0.8417	Intermediate Similarity	NPC267205
0.8414	Intermediate Similarity	NPC244691
0.8414	Intermediate Similarity	NPC193703
0.8414	Intermediate Similarity	NPC471906
0.8414	Intermediate Similarity	NPC21599
0.8414	Intermediate Similarity	NPC79627
0.8409	Intermediate Similarity	NPC472046
0.8403	Intermediate Similarity	NPC474961
0.84	Intermediate Similarity	NPC474622
0.84	Intermediate Similarity	NPC474621
0.8397	Intermediate Similarity	NPC232178
0.8394	Intermediate Similarity	NPC276238
0.8392	Intermediate Similarity	NPC241349
0.8392	Intermediate Similarity	NPC220496
0.8392	Intermediate Similarity	NPC42262
0.8392	Intermediate Similarity	NPC37992
0.8392	Intermediate Similarity	NPC327916
0.8392	Intermediate Similarity	NPC147542
0.8392	Intermediate Similarity	NPC32749
0.8389	Intermediate Similarity	NPC35
0.8385	Intermediate Similarity	NPC269414
0.838	Intermediate Similarity	NPC87723
0.838	Intermediate Similarity	NPC206207
0.8366	Intermediate Similarity	NPC284495
0.8366	Intermediate Similarity	NPC476506
0.8358	Intermediate Similarity	NPC477153
0.8358	Intermediate Similarity	NPC275145
0.8357	Intermediate Similarity	NPC1249
0.8356	Intermediate Similarity	NPC34482
0.8356	Intermediate Similarity	NPC170055
0.8355	Intermediate Similarity	NPC67197
0.8345	Intermediate Similarity	NPC53016
0.8345	Intermediate Similarity	NPC309430
0.8345	Intermediate Similarity	NPC238629
0.8344	Intermediate Similarity	NPC266469
0.8333	Intermediate Similarity	NPC108129
0.8333	Intermediate Similarity	NPC198305
0.8333	Intermediate Similarity	NPC471444
0.8333	Intermediate Similarity	NPC474534
0.8333	Intermediate Similarity	NPC91019
0.8333	Intermediate Similarity	NPC257003

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 NPC245923 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	355
0.1-0.2	975
0.2-0.3	1299
0.3-0.4	2793
0.4-0.5	2180
0.5-0.6	1097
0.6-0.7	371
0.7-0.8	71
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
0.9077	High Similarity	NPD1470	Approved
0.8841	High Similarity	NPD5408	Approved
0.8841	High Similarity	NPD5405	Approved
0.8841	High Similarity	NPD5406	Approved
0.8841	High Similarity	NPD5404	Approved
0.8769	High Similarity	NPD1201	Approved
0.8671	High Similarity	NPD7390	Discontinued
0.8633	High Similarity	NPD1509	Clinical (unspecified phase)
0.8483	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8168	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD3226	Approved
0.8	Intermediate Similarity	NPD2346	Discontinued
0.7852	Intermediate Similarity	NPD3300	Phase 2
0.7808	Intermediate Similarity	NPD2935	Discontinued
0.7799	Intermediate Similarity	NPD6232	Discontinued
0.7764	Intermediate Similarity	NPD7473	Discontinued
0.7736	Intermediate Similarity	NPD6959	Discontinued
0.7727	Intermediate Similarity	NPD7635	Approved
0.7718	Intermediate Similarity	NPD7003	Approved
0.7633	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD2342	Discontinued
0.7589	Intermediate Similarity	NPD1164	Approved
0.7586	Intermediate Similarity	NPD943	Approved
0.7569	Intermediate Similarity	NPD3764	Approved
0.7536	Intermediate Similarity	NPD3019	Approved
0.7481	Intermediate Similarity	NPD5951	Approved
0.7448	Intermediate Similarity	NPD2313	Discontinued
0.7442	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD8312	Approved
0.744	Intermediate Similarity	NPD8313	Approved
0.7436	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD2798	Approved
0.741	Intermediate Similarity	NPD2932	Approved
0.741	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD2344	Approved
0.7383	Intermediate Similarity	NPD2799	Discontinued
0.7383	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD7768	Phase 2
0.7349	Intermediate Similarity	NPD5844	Phase 1
0.731	Intermediate Similarity	NPD8150	Discontinued
0.729	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD7008	Discontinued
0.7257	Intermediate Similarity	NPD6535	Approved
0.7257	Intermediate Similarity	NPD6534	Approved
0.725	Intermediate Similarity	NPD7819	Suspended
0.7248	Intermediate Similarity	NPD1607	Approved
0.7222	Intermediate Similarity	NPD3749	Approved
0.7214	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD2309	Approved
0.7205	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6213	Phase 3
0.72	Intermediate Similarity	NPD6212	Phase 3
0.72	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7177	Discontinued
0.7179	Intermediate Similarity	NPD2534	Approved
0.7179	Intermediate Similarity	NPD2533	Approved
0.7179	Intermediate Similarity	NPD2532	Approved
0.717	Intermediate Similarity	NPD4380	Phase 2
0.7169	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1510	Phase 2
0.7151	Intermediate Similarity	NPD6778	Approved
0.7151	Intermediate Similarity	NPD6781	Approved
0.7151	Intermediate Similarity	NPD6782	Approved
0.7151	Intermediate Similarity	NPD6780	Approved
0.7151	Intermediate Similarity	NPD6777	Approved
0.7151	Intermediate Similarity	NPD6779	Approved
0.7151	Intermediate Similarity	NPD6776	Approved
0.7143	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3750	Approved
0.7143	Intermediate Similarity	NPD2801	Approved
0.7135	Intermediate Similarity	NPD7699	Phase 2
0.7135	Intermediate Similarity	NPD7700	Phase 2
0.7125	Intermediate Similarity	NPD7411	Suspended
0.7114	Intermediate Similarity	NPD1240	Approved
0.7113	Intermediate Similarity	NPD3023	Approved
0.7113	Intermediate Similarity	NPD3026	Approved
0.7107	Intermediate Similarity	NPD7458	Discontinued
0.7101	Intermediate Similarity	NPD497	Approved
0.7092	Intermediate Similarity	NPD3024	Approved
0.7092	Intermediate Similarity	NPD3025	Approved
0.7092	Intermediate Similarity	NPD1651	Approved
0.7088	Intermediate Similarity	NPD7871	Phase 2
0.7088	Intermediate Similarity	NPD7870	Phase 2
0.7059	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD9266	Approved
0.7037	Intermediate Similarity	NPD74	Approved
0.7034	Intermediate Similarity	NPD1283	Approved
0.7033	Intermediate Similarity	NPD7696	Phase 3
0.7033	Intermediate Similarity	NPD7435	Discontinued
0.7033	Intermediate Similarity	NPD7698	Approved
0.7033	Intermediate Similarity	NPD7697	Approved
0.7032	Intermediate Similarity	NPD8166	Discontinued
0.703	Intermediate Similarity	NPD5494	Approved
0.7029	Intermediate Similarity	NPD495	Approved
0.7029	Intermediate Similarity	NPD498	Approved
0.7029	Intermediate Similarity	NPD496	Approved
0.7018	Intermediate Similarity	NPD5029	Approved
0.7018	Intermediate Similarity	NPD6559	Discontinued
0.7018	Intermediate Similarity	NPD5027	Approved
0.7018	Intermediate Similarity	NPD5031	Approved
0.7014	Intermediate Similarity	NPD4878	Approved
0.7	Intermediate Similarity	NPD9493	Approved
0.6994	Remote Similarity	NPD5402	Approved
0.6978	Remote Similarity	NPD6823	Phase 2
0.6975	Remote Similarity	NPD6844	Discontinued
0.6963	Remote Similarity	NPD9264	Approved
0.6963	Remote Similarity	NPD9267	Approved
0.6963	Remote Similarity	NPD9263	Approved
0.6948	Remote Similarity	NPD1471	Phase 3
0.6923	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2286	Discontinued
0.6918	Remote Similarity	NPD6273	Approved
0.6913	Remote Similarity	NPD4625	Phase 3
0.6913	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD1549	Phase 2
0.6899	Remote Similarity	NPD1511	Approved
0.6894	Remote Similarity	NPD289	Clinical (unspecified phase)
0.689	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD1551	Phase 2
0.6882	Remote Similarity	NPD7701	Phase 2
0.6879	Remote Similarity	NPD5034	Approved
0.6879	Remote Similarity	NPD4954	Approved
0.6879	Remote Similarity	NPD36	Approved
0.6879	Remote Similarity	NPD5026	Approved
0.6879	Remote Similarity	NPD5028	Approved
0.6879	Remote Similarity	NPD4955	Approved
0.6871	Remote Similarity	NPD1934	Approved
0.6871	Remote Similarity	NPD1203	Approved
0.6865	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6166	Phase 2
0.6864	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD4750	Phase 3
0.6855	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD844	Approved
0.6842	Remote Similarity	NPD1932	Approved
0.6839	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1281	Approved
0.6828	Remote Similarity	NPD1611	Approved
0.6828	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6663	Approved
0.6821	Remote Similarity	NPD5030	Phase 2
0.6818	Remote Similarity	NPD5038	Approved
0.6818	Remote Similarity	NPD4308	Phase 3
0.6818	Remote Similarity	NPD3748	Approved
0.6818	Remote Similarity	NPD5037	Approved
0.6815	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD1512	Approved
0.6811	Remote Similarity	NPD8320	Phase 1
0.6811	Remote Similarity	NPD8319	Approved
0.6809	Remote Similarity	NPD7874	Approved
0.6809	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7075	Discontinued
0.6806	Remote Similarity	NPD4626	Approved
0.6803	Remote Similarity	NPD1876	Approved
0.6794	Remote Similarity	NPD288	Approved
0.6791	Remote Similarity	NPD1930	Approved
0.6791	Remote Similarity	NPD1929	Approved
0.6791	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD3972	Approved
0.6779	Remote Similarity	NPD5736	Approved
0.6776	Remote Similarity	NPD2979	Phase 3
0.6774	Remote Similarity	NPD6100	Approved
0.6774	Remote Similarity	NPD2796	Approved
0.6774	Remote Similarity	NPD6099	Approved
0.6772	Remote Similarity	NPD7801	Approved
0.6761	Remote Similarity	NPD5036	Approved
0.6755	Remote Similarity	NPD411	Approved
0.6755	Remote Similarity	NPD8151	Discontinued
0.6752	Remote Similarity	NPD2800	Approved
0.6747	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD3882	Suspended
0.6744	Remote Similarity	NPD6020	Phase 2
0.6742	Remote Similarity	NPD6836	Approved
0.6738	Remote Similarity	NPD9281	Approved
0.6732	Remote Similarity	NPD447	Suspended
0.6727	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD5033	Approved
0.6715	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD7610	Discontinued
0.6709	Remote Similarity	NPD4628	Phase 3
0.6709	Remote Similarity	NPD3400	Discontinued
0.6707	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD3020	Approved
0.6691	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.669	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD6696	Suspended
0.6687	Remote Similarity	NPD2296	Approved
0.6687	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD3751	Discontinued
0.6667	Remote Similarity	NPD9717	Approved
0.6667	Remote Similarity	NPD3091	Approved
0.6667	Remote Similarity	NPD9261	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