NPASS Compound

Structure

CID305060 OpenBabel06191716112D 25 28 0 0 1 0 0 0 0 0999 V2000 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 -2.5981 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 2.5981 -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 3.4641 -1.0000 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 -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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 2 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 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 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 -0.0000 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 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 0.8660 -1.5000 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 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 7 1 0 0 0 0 2 3 2 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 4 7 2 0 0 0 0 4 8 1 0 0 0 0 5 7 1 0 0 0 0 5 11 2 0 0 0 0 6 8 1 0 0 0 0 6 12 1 0 0 0 0 8 13 2 0 0 0 0 9 14 2 0 0 0 0 9 20 1 0 0 0 0 10 15 2 0 0 0 0 10 21 1 0 0 0 0 11 13 1 0 0 0 0 11 22 1 0 0 0 0 12 16 1 0 0 0 0 12 23 1 6 0 0 0 13 17 1 0 0 0 0 14 15 1 0 0 0 0 14 18 1 0 0 0 0 15 19 1 0 0 0 0 16 17 2 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 18 24 2 0 0 0 0 19 25 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.08
Volume:	331.968
LogP:	5.217
LogD:	2.984
LogS:	-3.962
# Rotatable Bonds:	0
TPSA:	121.38
# H-Bond Aceptor:	6
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.165
Synthetic Accessibility Score:	2.893
Fsp3:	0.053
Lipinski Rule-of-5:	Rejected
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:	-5.313
MDCK Permeability:	4.327790520619601e-06
Pgp-inhibitor:	0.007
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.924
20% Bioavailability (F20%):	0.149
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	95.95368194580078%
Volume Distribution (VD):	0.461
Pgp-substrate:	8.02392292022705%

ADMET: Metabolism

CYP1A2-inhibitor:	0.961
CYP1A2-substrate:	0.326
CYP2C19-inhibitor:	0.069
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.617
CYP2C9-substrate:	0.746
CYP2D6-inhibitor:	0.043
CYP2D6-substrate:	0.234
CYP3A4-inhibitor:	0.033
CYP3A4-substrate:	0.043

ADMET: Excretion

Clearance (CL):	7.56
Half-life (T1/2):	0.777

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.04
Drug-inuced Liver Injury (DILI):	0.953
AMES Toxicity:	0.532
Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.876
Skin Sensitization:	0.958
Carcinogencity:	0.155
Eye Corrosion:	0.31
Eye Irritation:	0.947
Respiratory Toxicity:	0.129

Download Data

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

Natural Product: NPC305060

Natural Product ID:	NPC305060
*Common Name:**	Landomycinone
IUPAC Name:	n.a.
Synonyms:	Landomycinone
Standard InCHIKey:	DMGKSWBAQZKXEJ-GFCCVEGCSA-N
Standard InCHI:	InChI=1S/C19H14O6/c1-7-4-8-6-12(23)16-17(13(8)11(22)5-7)19(25)15-10(21)3-2-9(20)14(15)18(16)24/h2-5,12,20-23H,6H2,1H3/t12-/m1/s1
SMILES:	Cc1cc2C[C@H](C3=C(c2c(c1)O)C(=O)c1c(ccc(c1C3=O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1668765
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones

*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
NPO19685	Streptomyces cyanogenus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21188999]
NPO19685	Streptomyces cyanogenus	Species	Streptomycetaceae	Bacteria	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	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	2100.0	nM	PMID[494245]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1400.0	nM	PMID[494245]

☑ 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 NPC305060 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	321
0.1-0.2	1416
0.2-0.3	3125
0.3-0.4	8793
0.4-0.5	10890
0.5-0.6	5032
0.6-0.7	8727
0.7-0.8	3937
0.8-0.85	289
0.85-0.9	138
0.9-0.95	28
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9318	High Similarity	NPC110609
0.9318	High Similarity	NPC242358
0.9318	High Similarity	NPC246693
0.9242	High Similarity	NPC205992
0.9237	High Similarity	NPC146647
0.9237	High Similarity	NPC34414
0.9185	High Similarity	NPC474813
0.9173	High Similarity	NPC70622
0.9173	High Similarity	NPC58685
0.9167	High Similarity	NPC55949
0.9118	High Similarity	NPC245923
0.9104	High Similarity	NPC314048
0.9044	High Similarity	NPC272268
0.9023	High Similarity	NPC136588
0.9023	High Similarity	NPC199253
0.9015	High Similarity	NPC282923
0.9	High Similarity	NPC152525
0.9	High Similarity	NPC68756
0.8971	High Similarity	NPC283088
0.8963	High Similarity	NPC53896
0.8955	High Similarity	NPC244699
0.8947	High Similarity	NPC278928
0.8929	High Similarity	NPC474300
0.8905	High Similarity	NPC315275
0.8905	High Similarity	NPC155211
0.8897	High Similarity	NPC50924
0.8865	High Similarity	NPC476473
0.8864	High Similarity	NPC96915
0.8864	High Similarity	NPC306765
0.8864	High Similarity	NPC3224
0.8857	High Similarity	NPC187843
0.8857	High Similarity	NPC124365
0.8855	High Similarity	NPC173978
0.8855	High Similarity	NPC74507
0.8855	High Similarity	NPC234890
0.8824	High Similarity	NPC52407
0.8824	High Similarity	NPC115458
0.8815	High Similarity	NPC85342
0.8811	High Similarity	NPC300540
0.8806	High Similarity	NPC99731
0.8797	High Similarity	NPC471530
0.8788	High Similarity	NPC103540
0.8741	High Similarity	NPC31799
0.8731	High Similarity	NPC48248
0.8723	High Similarity	NPC305845
0.8723	High Similarity	NPC204045
0.8722	High Similarity	NPC136342
0.8722	High Similarity	NPC295202
0.8722	High Similarity	NPC1991
0.8722	High Similarity	NPC49647
0.8722	High Similarity	NPC227741
0.8714	High Similarity	NPC476477
0.8714	High Similarity	NPC111422
0.8714	High Similarity	NPC306835
0.8714	High Similarity	NPC216312
0.8714	High Similarity	NPC256463
0.8714	High Similarity	NPC299405
0.8714	High Similarity	NPC29771
0.8714	High Similarity	NPC471602
0.8712	High Similarity	NPC142956
0.8702	High Similarity	NPC307174
0.8686	High Similarity	NPC225051
0.8681	High Similarity	NPC285122
0.8676	High Similarity	NPC72669
0.8676	High Similarity	NPC474517
0.8671	High Similarity	NPC471906
0.8671	High Similarity	NPC244691
0.8662	High Similarity	NPC469520
0.8662	High Similarity	NPC474961
0.8662	High Similarity	NPC135524
0.8652	High Similarity	NPC241349
0.8652	High Similarity	NPC327916
0.8652	High Similarity	NPC37992
0.8652	High Similarity	NPC32749
0.8652	High Similarity	NPC220496
0.8652	High Similarity	NPC42262
0.8652	High Similarity	NPC147542
0.8649	High Similarity	NPC218870
0.8649	High Similarity	NPC474824
0.8649	High Similarity	NPC470408
0.8649	High Similarity	NPC182921
0.8647	High Similarity	NPC131799
0.8643	High Similarity	NPC13715
0.8636	High Similarity	NPC375356
0.8623	High Similarity	NPC161964
0.8623	High Similarity	NPC288089
0.8623	High Similarity	NPC472262
0.8623	High Similarity	NPC287604
0.8615	High Similarity	NPC473662
0.8615	High Similarity	NPC7151
0.8615	High Similarity	NPC216297
0.8611	High Similarity	NPC170055
0.8611	High Similarity	NPC471683
0.8592	High Similarity	NPC471444
0.8592	High Similarity	NPC257003
0.8582	High Similarity	NPC190457
0.8582	High Similarity	NPC1268
0.8582	High Similarity	NPC143438
0.8582	High Similarity	NPC26924
0.8582	High Similarity	NPC231774
0.8561	High Similarity	NPC161632
0.8561	High Similarity	NPC300274
0.8561	High Similarity	NPC80035
0.8542	High Similarity	NPC48130
0.8542	High Similarity	NPC29932
0.8542	High Similarity	NPC10764
0.8542	High Similarity	NPC300684
0.8542	High Similarity	NPC79627
0.8542	High Similarity	NPC477409
0.8542	High Similarity	NPC218866
0.8542	High Similarity	NPC84568
0.854	High Similarity	NPC17083
0.8533	High Similarity	NPC474861
0.8531	High Similarity	NPC85310
0.8521	High Similarity	NPC315578
0.8511	High Similarity	NPC61590
0.8511	High Similarity	NPC206207
0.8489	Intermediate Similarity	NPC12070
0.8478	Intermediate Similarity	NPC309430
0.8473	Intermediate Similarity	NPC206778
0.8473	Intermediate Similarity	NPC285829
0.8472	Intermediate Similarity	NPC471682
0.8472	Intermediate Similarity	NPC143898
0.8467	Intermediate Similarity	NPC475741
0.8467	Intermediate Similarity	NPC198305
0.8467	Intermediate Similarity	NPC31539
0.8462	Intermediate Similarity	NPC91019
0.8462	Intermediate Similarity	NPC106519
0.8456	Intermediate Similarity	NPC247250
0.8456	Intermediate Similarity	NPC767
0.8451	Intermediate Similarity	NPC295339
0.8451	Intermediate Similarity	NPC138099
0.8451	Intermediate Similarity	NPC242994
0.8446	Intermediate Similarity	NPC315520
0.8444	Intermediate Similarity	NPC472047
0.844	Intermediate Similarity	NPC471905
0.844	Intermediate Similarity	NPC53206
0.844	Intermediate Similarity	NPC53414
0.8433	Intermediate Similarity	NPC310540
0.8429	Intermediate Similarity	NPC22222
0.8429	Intermediate Similarity	NPC281513
0.8429	Intermediate Similarity	NPC249272
0.8425	Intermediate Similarity	NPC147250
0.8425	Intermediate Similarity	NPC136878
0.8417	Intermediate Similarity	NPC114183
0.8414	Intermediate Similarity	NPC89664
0.8414	Intermediate Similarity	NPC274085
0.8414	Intermediate Similarity	NPC477913
0.8414	Intermediate Similarity	NPC193703
0.8414	Intermediate Similarity	NPC103910
0.8414	Intermediate Similarity	NPC48762
0.8414	Intermediate Similarity	NPC21599
0.8409	Intermediate Similarity	NPC472046
0.8406	Intermediate Similarity	NPC93015
0.8403	Intermediate Similarity	NPC257644
0.8403	Intermediate Similarity	NPC239136
0.8403	Intermediate Similarity	NPC19631
0.8397	Intermediate Similarity	NPC232178
0.8392	Intermediate Similarity	NPC181560
0.8392	Intermediate Similarity	NPC225243
0.8392	Intermediate Similarity	NPC169452
0.8392	Intermediate Similarity	NPC96421
0.8392	Intermediate Similarity	NPC183345
0.838	Intermediate Similarity	NPC416
0.838	Intermediate Similarity	NPC173980
0.838	Intermediate Similarity	NPC61398
0.8369	Intermediate Similarity	NPC141934
0.8369	Intermediate Similarity	NPC86524
0.8369	Intermediate Similarity	NPC193358
0.8369	Intermediate Similarity	NPC472308
0.8369	Intermediate Similarity	NPC254847
0.8367	Intermediate Similarity	NPC119767
0.8366	Intermediate Similarity	NPC284495
0.8357	Intermediate Similarity	NPC270899
0.8356	Intermediate Similarity	NPC34482
0.8345	Intermediate Similarity	NPC88864
0.8333	Intermediate Similarity	NPC246638
0.8322	Intermediate Similarity	NPC114620
0.8322	Intermediate Similarity	NPC103337
0.8321	Intermediate Similarity	NPC41567
0.8321	Intermediate Similarity	NPC237225
0.831	Intermediate Similarity	NPC53001
0.831	Intermediate Similarity	NPC147418
0.8309	Intermediate Similarity	NPC160499
0.8301	Intermediate Similarity	NPC186113
0.8299	Intermediate Similarity	NPC470570
0.8299	Intermediate Similarity	NPC314437
0.8286	Intermediate Similarity	NPC267205
0.8286	Intermediate Similarity	NPC193169
0.8286	Intermediate Similarity	NPC254603
0.8278	Intermediate Similarity	NPC474622
0.8278	Intermediate Similarity	NPC474621
0.8278	Intermediate Similarity	NPC135522
0.8276	Intermediate Similarity	NPC193555
0.8276	Intermediate Similarity	NPC69755
0.8276	Intermediate Similarity	NPC329493
0.8276	Intermediate Similarity	NPC73061
0.8273	Intermediate Similarity	NPC41847
0.8269	Intermediate Similarity	NPC71390
0.8255	Intermediate Similarity	NPC478219

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 NPC305060 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	298
0.1-0.2	918
0.2-0.3	1377
0.3-0.4	2699
0.4-0.5	2196
0.5-0.6	1160
0.6-0.7	408
0.7-0.8	86
0.8-0.85	5
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8788	High Similarity	NPD1470	Approved
0.8626	High Similarity	NPD1201	Approved
0.8369	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8168	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD5406	Approved
0.8056	Intermediate Similarity	NPD5405	Approved
0.8056	Intermediate Similarity	NPD5404	Approved
0.8056	Intermediate Similarity	NPD5408	Approved
0.8041	Intermediate Similarity	NPD7390	Discontinued
0.7973	Intermediate Similarity	NPD3300	Phase 2
0.7895	Intermediate Similarity	NPD3226	Approved
0.7877	Intermediate Similarity	NPD2346	Discontinued
0.7687	Intermediate Similarity	NPD2935	Discontinued
0.7619	Intermediate Similarity	NPD8150	Discontinued
0.7529	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6959	Discontinued
0.7469	Intermediate Similarity	NPD6232	Discontinued
0.7466	Intermediate Similarity	NPD943	Approved
0.7463	Intermediate Similarity	NPD7635	Approved
0.7442	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD7473	Discontinued
0.741	Intermediate Similarity	NPD2932	Approved
0.7389	Intermediate Similarity	NPD4380	Phase 2
0.7381	Intermediate Similarity	NPD4955	Approved
0.7381	Intermediate Similarity	NPD4954	Approved
0.7381	Intermediate Similarity	NPD5028	Approved
0.7381	Intermediate Similarity	NPD5026	Approved
0.7381	Intermediate Similarity	NPD5034	Approved
0.7381	Intermediate Similarity	NPD36	Approved
0.7358	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD1164	Approved
0.7337	Intermediate Similarity	NPD8313	Approved
0.7337	Intermediate Similarity	NPD8312	Approved
0.7329	Intermediate Similarity	NPD2313	Discontinued
0.7325	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD5030	Phase 2
0.731	Intermediate Similarity	NPD5038	Approved
0.731	Intermediate Similarity	NPD5037	Approved
0.729	Intermediate Similarity	NPD2534	Approved
0.729	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD2532	Approved
0.729	Intermediate Similarity	NPD2533	Approved
0.7286	Intermediate Similarity	NPD3019	Approved
0.7267	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1510	Phase 2
0.7267	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD6535	Approved
0.7257	Intermediate Similarity	NPD6534	Approved
0.7251	Intermediate Similarity	NPD5036	Approved
0.725	Intermediate Similarity	NPD7819	Suspended
0.7248	Intermediate Similarity	NPD1607	Approved
0.7246	Intermediate Similarity	NPD5844	Phase 1
0.7218	Intermediate Similarity	NPD2342	Discontinued
0.7211	Intermediate Similarity	NPD3764	Approved
0.7205	Intermediate Similarity	NPD5402	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)
0.7188	Intermediate Similarity	NPD1934	Approved
0.7188	Intermediate Similarity	NPD6844	Discontinued
0.7172	Intermediate Similarity	NPD2798	Approved
0.7171	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2799	Discontinued
0.7151	Intermediate Similarity	NPD6778	Approved
0.7151	Intermediate Similarity	NPD6781	Approved
0.7151	Intermediate Similarity	NPD6780	Approved
0.7151	Intermediate Similarity	NPD6782	Approved
0.7151	Intermediate Similarity	NPD6779	Approved
0.7151	Intermediate Similarity	NPD6777	Approved
0.7151	Intermediate Similarity	NPD6776	Approved
0.7143	Intermediate Similarity	NPD7003	Approved
0.7143	Intermediate Similarity	NPD1878	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
0.7134	Intermediate Similarity	NPD5494	Approved
0.7124	Intermediate Similarity	NPD1549	Phase 2
0.7118	Intermediate Similarity	NPD5029	Approved
0.7118	Intermediate Similarity	NPD5031	Approved
0.7118	Intermediate Similarity	NPD5027	Approved
0.7114	Intermediate Similarity	NPD1240	Approved
0.7101	Intermediate Similarity	NPD5951	Approved
0.7063	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2344	Approved
0.7059	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
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
0.7018	Intermediate Similarity	NPD6559	Discontinued
0.7013	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9493	Approved
0.6995	Remote Similarity	NPD7870	Phase 2
0.6995	Remote Similarity	NPD7871	Phase 2
0.6993	Remote Similarity	NPD1551	Phase 2
0.6992	Remote Similarity	NPD1237	Approved
0.6978	Remote Similarity	NPD497	Approved
0.6978	Remote Similarity	NPD6823	Phase 2
0.6972	Remote Similarity	NPD1651	Approved
0.6972	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6166	Phase 2
0.6962	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7768	Phase 2
0.6948	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD5035	Approved
0.6933	Remote Similarity	NPD6663	Approved
0.6923	Remote Similarity	NPD4628	Phase 3
0.6923	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8166	Discontinued
0.6923	Remote Similarity	NPD3400	Discontinued
0.6918	Remote Similarity	NPD6273	Approved
0.6914	Remote Similarity	NPD7411	Suspended
0.6913	Remote Similarity	NPD7008	Discontinued
0.6912	Remote Similarity	NPD9266	Approved
0.6912	Remote Similarity	NPD74	Approved
0.6909	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7075	Discontinued
0.6906	Remote Similarity	NPD496	Approved
0.6906	Remote Similarity	NPD495	Approved
0.6906	Remote Similarity	NPD498	Approved
0.6901	Remote Similarity	NPD3091	Approved
0.6899	Remote Similarity	NPD1511	Approved
0.6894	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7458	Discontinued
0.6892	Remote Similarity	NPD5736	Approved
0.6883	Remote Similarity	NPD2796	Approved
0.6882	Remote Similarity	NPD7701	Phase 2
0.6882	Remote Similarity	NPD3751	Discontinued
0.6879	Remote Similarity	NPD2309	Approved
0.6875	Remote Similarity	NPD3026	Approved
0.6875	Remote Similarity	NPD3023	Approved
0.6871	Remote Similarity	NPD3094	Phase 2
0.6867	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD4750	Phase 3
0.6859	Remote Similarity	NPD2800	Approved
0.6855	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD3025	Approved
0.6853	Remote Similarity	NPD3024	Approved
0.6842	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1471	Phase 3
0.6838	Remote Similarity	NPD9263	Approved
0.6838	Remote Similarity	NPD9267	Approved
0.6838	Remote Similarity	NPD9264	Approved
0.6836	Remote Similarity	NPD6836	Approved
0.6829	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD3092	Approved
0.6828	Remote Similarity	NPD1281	Approved
0.6821	Remote Similarity	NPD5039	Approved
0.6818	Remote Similarity	NPD3748	Approved
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	NPD3749	Approved
0.6806	Remote Similarity	NPD4626	Approved
0.6803	Remote Similarity	NPD1876	Approved
0.6802	Remote Similarity	NPD7074	Phase 3
0.68	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD288	Approved
0.6786	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7177	Discontinued
0.6784	Remote Similarity	NPD3818	Discontinued
0.6782	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD4878	Approved
0.6776	Remote Similarity	NPD2979	Phase 3
0.6776	Remote Similarity	NPD4914	Approved
0.6774	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7801	Approved
0.677	Remote Similarity	NPD5403	Approved
0.6768	Remote Similarity	NPD6801	Discontinued
0.6765	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.676	Remote Similarity	NPD5968	Phase 3
0.6757	Remote Similarity	NPD1203	Approved
0.675	Remote Similarity	NPD5401	Approved
0.6747	Remote Similarity	NPD3882	Suspended
0.6746	Remote Similarity	NPD5711	Approved
0.6746	Remote Similarity	NPD5710	Approved
0.6744	Remote Similarity	NPD7054	Approved
0.6732	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD8434	Phase 2
0.6718	Remote Similarity	NPD844	Approved
0.6712	Remote Similarity	NPD1611	Approved
0.6711	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.671	Remote Similarity	NPD4308	Phase 3
0.6709	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4956	Approved
0.6705	Remote Similarity	NPD7472	Approved
0.6703	Remote Similarity	NPD4386	Approved
0.6703	Remote Similarity	NPD4387	Approved
0.669	Remote Similarity	NPD3317	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