NPASS Compound

Structure

NPC119767 OpenBabel07101718192D 29 32 0 0 0 0 0 0 0 0999 V2000 2.5981 -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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 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 -6.9282 -3.0000 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 -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 -3.4641 -2.0000 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 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 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 -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 -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 -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 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 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 -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 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 14 1 0 0 0 0 3 16 2 0 0 0 0 4 6 1 0 0 0 0 4 12 2 0 0 0 0 5 7 2 0 0 0 0 5 12 1 0 0 0 0 6 13 2 0 0 0 0 7 13 1 0 0 0 0 8 11 2 0 0 0 0 8 15 1 0 0 0 0 9 11 1 0 0 0 0 9 17 2 0 0 0 0 10 11 1 0 0 0 0 10 29 1 0 0 0 0 12 22 1 0 0 0 0 13 23 1 0 0 0 0 14 18 2 0 0 0 0 14 20 1 0 0 0 0 15 19 2 0 0 0 0 15 20 1 0 0 0 0 16 18 1 0 0 0 0 16 24 1 0 0 0 0 17 19 1 0 0 0 0 17 25 1 0 0 0 0 18 21 1 0 0 0 0 19 21 1 0 0 0 0 20 26 2 0 0 0 0 21 27 2 0 0 0 0 22 28 2 0 0 0 0 22 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	390.07
Volume:	384.736
LogP:	4.6
LogD:	2.76
LogS:	-5.056
# Rotatable Bonds:	4
TPSA:	121.13
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.46
Synthetic Accessibility Score:	2.333
Fsp3:	0.045
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:	-5.069
MDCK Permeability:	1.2995197721465956e-05
Pgp-inhibitor:	0.025
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.156
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.108
Plasma Protein Binding (PPB):	101.43535614013672%
Volume Distribution (VD):	0.57
Pgp-substrate:	0.7851291298866272%

ADMET: Metabolism

CYP1A2-inhibitor:	0.942
CYP1A2-substrate:	0.071
CYP2C19-inhibitor:	0.78
CYP2C19-substrate:	0.046
CYP2C9-inhibitor:	0.649
CYP2C9-substrate:	0.576
CYP2D6-inhibitor:	0.529
CYP2D6-substrate:	0.183
CYP3A4-inhibitor:	0.711
CYP3A4-substrate:	0.106

ADMET: Excretion

Clearance (CL):	9.492
Half-life (T1/2):	0.592

ADMET: Toxicity

hERG Blockers:	0.06
Human Hepatotoxicity (H-HT):	0.055
Drug-inuced Liver Injury (DILI):	0.966
AMES Toxicity:	0.885
Rat Oral Acute Toxicity:	0.075
Maximum Recommended Daily Dose:	0.043
Skin Sensitization:	0.25
Carcinogencity:	0.839
Eye Corrosion:	0.003
Eye Irritation:	0.947
Respiratory Toxicity:	0.014

Download Data

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

Natural Product: NPC119767

Natural Product ID:	NPC119767
*Common Name:**	(4,5-Dihydroxy-9,10-Dioxoanthracen-2-Yl)Methyl 4-Hydroxybenzoate
IUPAC Name:	(4,5-dihydroxy-9,10-dioxoanthracen-2-yl)methyl 4-hydroxybenzoate
Synonyms:
Standard InCHIKey:	JNAZKJLAUIOKDJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H14O7/c23-13-6-4-12(5-7-13)22(28)29-10-11-8-15-19(17(25)9-11)21(27)18-14(20(15)26)2-1-3-16(18)24/h1-9,23-25H,10H2
SMILES:	c1cc2c(c(c1)O)C(=O)c1c(cc(cc1O)COC(=O)c1ccc(cc1)O)C2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3104873
PubChem CID:	73058259
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
NPO33246	kniphofia ensifolia	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24326280]

☑ 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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	60000.0	nM	PMID[566524]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	26000.0	nM	PMID[566524]

☑ 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 NPC119767 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	359
0.1-0.2	1595
0.2-0.3	3346
0.3-0.4	7761
0.4-0.5	10602
0.5-0.6	4295
0.6-0.7	6533
0.7-0.8	7172
0.8-0.85	855
0.85-0.9	173
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9787	High Similarity	NPC147250
0.9384	High Similarity	NPC205766
0.9262	High Similarity	NPC66029
0.9034	High Similarity	NPC66593
0.9021	High Similarity	NPC26924
0.8973	High Similarity	NPC193703
0.8973	High Similarity	NPC21599
0.8958	High Similarity	NPC315578
0.8904	High Similarity	NPC476473
0.8889	High Similarity	NPC317580
0.8882	High Similarity	NPC318270
0.8867	High Similarity	NPC315520
0.8865	High Similarity	NPC52407
0.8851	High Similarity	NPC470570
0.8851	High Similarity	NPC314437
0.8844	High Similarity	NPC48762
0.8836	High Similarity	NPC474300
0.8836	High Similarity	NPC69755
0.8831	High Similarity	NPC324736
0.8831	High Similarity	NPC326084
0.8824	High Similarity	NPC313299
0.8819	High Similarity	NPC13715
0.8816	High Similarity	NPC474622
0.8816	High Similarity	NPC470408
0.8816	High Similarity	NPC182921
0.8816	High Similarity	NPC474824
0.8816	High Similarity	NPC218870
0.8816	High Similarity	NPC474621
0.8803	High Similarity	NPC288089
0.88	High Similarity	NPC478219
0.8794	High Similarity	NPC70622
0.8784	High Similarity	NPC34482
0.8774	High Similarity	NPC475449
0.8759	High Similarity	NPC1268
0.8758	High Similarity	NPC226656
0.8758	High Similarity	NPC66508
0.875	High Similarity	NPC474534
0.875	High Similarity	NPC261292
0.875	High Similarity	NPC301915
0.875	High Similarity	NPC474533
0.8742	High Similarity	NPC147735
0.8742	High Similarity	NPC290954
0.8742	High Similarity	NPC255641
0.8734	High Similarity	NPC477835
0.8732	High Similarity	NPC225051
0.8707	High Similarity	NPC239136
0.8707	High Similarity	NPC19631
0.8701	High Similarity	NPC474861
0.8699	High Similarity	NPC168471
0.8699	High Similarity	NPC225243
0.869	High Similarity	NPC61590
0.869	High Similarity	NPC4214
0.8681	High Similarity	NPC155211
0.8681	High Similarity	NPC474813
0.8667	High Similarity	NPC190648
0.8667	High Similarity	NPC289042
0.8667	High Similarity	NPC312929
0.8667	High Similarity	NPC472135
0.8667	High Similarity	NPC126767
0.8667	High Similarity	NPC118027
0.8667	High Similarity	NPC245584
0.8667	High Similarity	NPC56433
0.8662	High Similarity	NPC187934
0.8662	High Similarity	NPC97637
0.8652	High Similarity	NPC199253
0.8652	High Similarity	NPC136588
0.8645	High Similarity	NPC263483
0.8639	High Similarity	NPC124365
0.8639	High Similarity	NPC290550
0.8639	High Similarity	NPC246638
0.8636	High Similarity	NPC472835
0.8634	High Similarity	NPC477836
0.863	High Similarity	NPC295339
0.863	High Similarity	NPC216312
0.863	High Similarity	NPC471602
0.863	High Similarity	NPC29771
0.863	High Similarity	NPC111422
0.863	High Similarity	NPC306835
0.863	High Similarity	NPC476477
0.863	High Similarity	NPC190457
0.863	High Similarity	NPC299405
0.863	High Similarity	NPC256463
0.8627	High Similarity	NPC40356
0.8627	High Similarity	NPC154683
0.8621	High Similarity	NPC245923
0.8621	High Similarity	NPC62272
0.8618	High Similarity	NPC477914
0.8618	High Similarity	NPC470568
0.8618	High Similarity	NPC294646
0.8611	High Similarity	NPC283088
0.8611	High Similarity	NPC80035
0.8609	High Similarity	NPC172329
0.8609	High Similarity	NPC2569
0.86	High Similarity	NPC300540
0.8592	High Similarity	NPC474517
0.8592	High Similarity	NPC72669
0.8591	High Similarity	NPC151607
0.8591	High Similarity	NPC42540
0.8582	High Similarity	NPC99731
0.8581	High Similarity	NPC469520
0.8581	High Similarity	NPC146211
0.8581	High Similarity	NPC257644
0.8571	High Similarity	NPC32749
0.8571	High Similarity	NPC155205
0.8571	High Similarity	NPC96421
0.8571	High Similarity	NPC37992
0.8571	High Similarity	NPC147542
0.8571	High Similarity	NPC42262
0.8571	High Similarity	NPC241349
0.8571	High Similarity	NPC220496
0.8571	High Similarity	NPC327916
0.8571	High Similarity	NPC208806
0.8562	High Similarity	NPC473201
0.8562	High Similarity	NPC470569
0.8562	High Similarity	NPC302783
0.8562	High Similarity	NPC221104
0.8562	High Similarity	NPC76647
0.8553	High Similarity	NPC478022
0.8553	High Similarity	NPC478020
0.8552	High Similarity	NPC291454
0.8552	High Similarity	NPC141934
0.8543	High Similarity	NPC215593
0.8543	High Similarity	NPC478018
0.8542	High Similarity	NPC50924
0.8535	High Similarity	NPC472060
0.8535	High Similarity	NPC284495
0.8535	High Similarity	NPC472052
0.8535	High Similarity	NPC470342
0.8533	High Similarity	NPC478019
0.8526	High Similarity	NPC206641
0.8526	High Similarity	NPC67197
0.8526	High Similarity	NPC208651
0.8526	High Similarity	NPC167098
0.8526	High Similarity	NPC296044
0.8523	High Similarity	NPC471682
0.8523	High Similarity	NPC159721
0.8523	High Similarity	NPC53016
0.8516	High Similarity	NPC82190
0.8516	High Similarity	NPC266469
0.8516	High Similarity	NPC478133
0.8516	High Similarity	NPC174599
0.8516	High Similarity	NPC192219
0.8514	High Similarity	NPC305845
0.8514	High Similarity	NPC471444
0.8514	High Similarity	NPC204045
0.8514	High Similarity	NPC257003
0.8514	High Similarity	NPC470842
0.8511	High Similarity	NPC282923
0.8506	High Similarity	NPC175978
0.8503	High Similarity	NPC138099
0.8503	High Similarity	NPC19622
0.8503	High Similarity	NPC242994
0.8503	High Similarity	NPC112789
0.85	High Similarity	NPC30027
0.8497	Intermediate Similarity	NPC119929
0.8497	Intermediate Similarity	NPC295036
0.8497	Intermediate Similarity	NPC470107
0.8493	Intermediate Similarity	NPC53206
0.8493	Intermediate Similarity	NPC53414
0.8493	Intermediate Similarity	NPC471905
0.8487	Intermediate Similarity	NPC290695
0.8487	Intermediate Similarity	NPC142846
0.8487	Intermediate Similarity	NPC94781
0.8487	Intermediate Similarity	NPC106524
0.8481	Intermediate Similarity	NPC472261
0.8477	Intermediate Similarity	NPC225173
0.8477	Intermediate Similarity	NPC472134
0.8477	Intermediate Similarity	NPC285122
0.8477	Intermediate Similarity	NPC163846
0.8472	Intermediate Similarity	NPC314048
0.8467	Intermediate Similarity	NPC244691
0.8467	Intermediate Similarity	NPC84568
0.8467	Intermediate Similarity	NPC48130
0.8467	Intermediate Similarity	NPC471906
0.8467	Intermediate Similarity	NPC300684
0.8467	Intermediate Similarity	NPC19896
0.8467	Intermediate Similarity	NPC274085
0.8467	Intermediate Similarity	NPC218866
0.8467	Intermediate Similarity	NPC477913
0.8467	Intermediate Similarity	NPC103910
0.8467	Intermediate Similarity	NPC89664
0.8462	Intermediate Similarity	NPC205992
0.8462	Intermediate Similarity	NPC478223
0.8462	Intermediate Similarity	NPC283480
0.8462	Intermediate Similarity	NPC93015
0.8462	Intermediate Similarity	NPC148323
0.8462	Intermediate Similarity	NPC478027
0.8456	Intermediate Similarity	NPC85310
0.8456	Intermediate Similarity	NPC471733
0.8456	Intermediate Similarity	NPC73061
0.8456	Intermediate Similarity	NPC135524
0.8452	Intermediate Similarity	NPC214632
0.8452	Intermediate Similarity	NPC477691
0.8447	Intermediate Similarity	NPC234331
0.8446	Intermediate Similarity	NPC275903
0.8446	Intermediate Similarity	NPC183345
0.8446	Intermediate Similarity	NPC169452
0.8446	Intermediate Similarity	NPC181560
0.8442	Intermediate Similarity	NPC39819
0.8442	Intermediate Similarity	NPC477276

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 NPC119767 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	336
0.1-0.2	945
0.2-0.3	1458
0.3-0.4	2565
0.4-0.5	2077
0.5-0.6	1150
0.6-0.7	432
0.7-0.8	166
0.8-0.85	19
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8675	High Similarity	NPD3226	Approved
0.8621	High Similarity	NPD5406	Approved
0.8621	High Similarity	NPD5405	Approved
0.8621	High Similarity	NPD5404	Approved
0.8621	High Similarity	NPD5408	Approved
0.8429	Intermediate Similarity	NPD1470	Approved
0.8428	Intermediate Similarity	NPD6232	Discontinued
0.8425	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8392	Intermediate Similarity	NPD3764	Approved
0.8385	Intermediate Similarity	NPD7473	Discontinued
0.8311	Intermediate Similarity	NPD2346	Discontinued
0.825	Intermediate Similarity	NPD6959	Discontinued
0.8224	Intermediate Similarity	NPD7390	Discontinued
0.8217	Intermediate Similarity	NPD7819	Suspended
0.82	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD2534	Approved
0.817	Intermediate Similarity	NPD2532	Approved
0.817	Intermediate Similarity	NPD2533	Approved
0.8143	Intermediate Similarity	NPD1201	Approved
0.8118	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD7411	Suspended
0.8063	Intermediate Similarity	NPD3749	Approved
0.8052	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD8312	Approved
0.8036	Intermediate Similarity	NPD8313	Approved
0.8026	Intermediate Similarity	NPD7003	Approved
0.8023	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2935	Discontinued
0.8	Intermediate Similarity	NPD7768	Phase 2
0.7988	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD5844	Phase 1
0.7933	Intermediate Similarity	NPD1510	Phase 2
0.7911	Intermediate Similarity	NPD4380	Phase 2
0.7908	Intermediate Similarity	NPD3750	Approved
0.7895	Intermediate Similarity	NPD8150	Discontinued
0.7895	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD2313	Discontinued
0.7848	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD7458	Discontinued
0.7826	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD2799	Discontinued
0.78	Intermediate Similarity	NPD1607	Approved
0.7784	Intermediate Similarity	NPD7177	Discontinued
0.7778	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1549	Phase 2
0.7764	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD7075	Discontinued
0.773	Intermediate Similarity	NPD9545	Approved
0.7712	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD2344	Approved
0.7677	Intermediate Similarity	NPD4628	Phase 3
0.7667	Intermediate Similarity	NPD1240	Approved
0.7654	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1551	Phase 2
0.7627	Intermediate Similarity	NPD6535	Approved
0.7627	Intermediate Similarity	NPD6534	Approved
0.7595	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD1934	Approved
0.7589	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD3748	Approved
0.7582	Intermediate Similarity	NPD7435	Discontinued
0.7578	Intermediate Similarity	NPD6599	Discontinued
0.7564	Intermediate Similarity	NPD8166	Discontinued
0.7551	Intermediate Similarity	NPD1164	Approved
0.755	Intermediate Similarity	NPD943	Approved
0.7547	Intermediate Similarity	NPD6273	Approved
0.7545	Intermediate Similarity	NPD5710	Approved
0.7545	Intermediate Similarity	NPD5711	Approved
0.7541	Intermediate Similarity	NPD8320	Phase 1
0.7541	Intermediate Similarity	NPD8319	Approved
0.7532	Intermediate Similarity	NPD1511	Approved
0.7516	Intermediate Similarity	NPD2309	Approved
0.7515	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6782	Approved
0.7514	Intermediate Similarity	NPD6777	Approved
0.7514	Intermediate Similarity	NPD6779	Approved
0.7514	Intermediate Similarity	NPD6778	Approved
0.7514	Intermediate Similarity	NPD6776	Approved
0.7514	Intermediate Similarity	NPD6780	Approved
0.7514	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD7699	Phase 2
0.75	Intermediate Similarity	NPD6559	Discontinued
0.75	Intermediate Similarity	NPD7700	Phase 2
0.75	Intermediate Similarity	NPD230	Phase 1
0.7485	Intermediate Similarity	NPD6801	Discontinued
0.7484	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1283	Approved
0.7473	Intermediate Similarity	NPD8151	Discontinued
0.7472	Intermediate Similarity	NPD6213	Phase 3
0.7472	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD6212	Phase 3
0.7467	Intermediate Similarity	NPD7008	Discontinued
0.7456	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD6166	Phase 2
0.7456	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD7870	Phase 2
0.7446	Intermediate Similarity	NPD7871	Phase 2
0.7442	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD2801	Approved
0.7439	Intermediate Similarity	NPD1465	Phase 2
0.7438	Intermediate Similarity	NPD1512	Approved
0.7425	Intermediate Similarity	NPD5494	Approved
0.7421	Intermediate Similarity	NPD6799	Approved
0.7419	Intermediate Similarity	NPD2796	Approved
0.7405	Intermediate Similarity	NPD6190	Approved
0.7394	Intermediate Similarity	NPD3817	Phase 2
0.7394	Intermediate Similarity	NPD5402	Approved
0.7391	Intermediate Similarity	NPD7698	Approved
0.7391	Intermediate Similarity	NPD920	Approved
0.7391	Intermediate Similarity	NPD7696	Phase 3
0.7391	Intermediate Similarity	NPD7697	Approved
0.7375	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3818	Discontinued
0.7368	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD3882	Suspended
0.7343	Intermediate Similarity	NPD9493	Approved
0.7341	Intermediate Similarity	NPD5953	Discontinued
0.734	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD7874	Approved
0.732	Intermediate Similarity	NPD2979	Phase 3
0.7315	Intermediate Similarity	NPD1203	Approved
0.7312	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1281	Approved
0.7278	Intermediate Similarity	NPD2800	Approved
0.7267	Intermediate Similarity	NPD3751	Discontinued
0.7267	Intermediate Similarity	NPD2798	Approved
0.7261	Intermediate Similarity	NPD1471	Phase 3
0.726	Intermediate Similarity	NPD4626	Approved
0.7257	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD3300	Phase 2
0.7235	Intermediate Similarity	NPD7229	Phase 3
0.7234	Intermediate Similarity	NPD7701	Phase 2
0.7232	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1608	Approved
0.7225	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7286	Phase 2
0.7219	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD5691	Approved
0.7184	Intermediate Similarity	NPD7074	Phase 3
0.7181	Intermediate Similarity	NPD6973	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD5403	Approved
0.717	Intermediate Similarity	NPD1243	Approved
0.7162	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5401	Approved
0.7151	Intermediate Similarity	NPD6823	Phase 2
0.7143	Intermediate Similarity	NPD6663	Approved
0.7134	Intermediate Similarity	NPD4308	Phase 3
0.7126	Intermediate Similarity	NPD8455	Phase 2
0.7126	Intermediate Similarity	NPD7054	Approved
0.7125	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7801	Approved
0.712	Intermediate Similarity	NPD7783	Phase 2
0.712	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD3972	Approved
0.7111	Intermediate Similarity	NPD4287	Approved
0.7105	Intermediate Similarity	NPD5736	Approved
0.7097	Intermediate Similarity	NPD4060	Phase 1
0.7095	Intermediate Similarity	NPD8434	Phase 2
0.7086	Intermediate Similarity	NPD7472	Approved
0.7083	Intermediate Similarity	NPD5951	Approved
0.7078	Intermediate Similarity	NPD411	Approved
0.7078	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1651	Approved
0.7073	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD37	Approved
0.7059	Intermediate Similarity	NPD6832	Phase 2
0.7059	Intermediate Similarity	NPD919	Approved
0.7059	Intermediate Similarity	NPD6234	Discontinued
0.7056	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD447	Suspended
0.7045	Intermediate Similarity	NPD6797	Phase 2
0.7041	Intermediate Similarity	NPD4965	Approved
0.7041	Intermediate Similarity	NPD4967	Phase 2
0.7041	Intermediate Similarity	NPD4966	Approved
0.7037	Intermediate Similarity	NPD7236	Approved
0.7035	Intermediate Similarity	NPD3787	Discontinued
0.7027	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3019	Approved
0.7027	Intermediate Similarity	NPD17	Approved
0.7025	Intermediate Similarity	NPD7033	Discontinued
0.702	Intermediate Similarity	NPD1876	Approved
0.7006	Intermediate Similarity	NPD7251	Discontinued
0.7	Intermediate Similarity	NPD9717	Approved
0.6989	Remote Similarity	NPD8285	Discontinued
0.6982	Remote Similarity	NPD2296	Approved
0.6982	Remote Similarity	NPD4288	Approved
0.6981	Remote Similarity	NPD4477	Approved
0.6981	Remote Similarity	NPD2438	Suspended
0.6981	Remote Similarity	NPD2531	Phase 2
0.6981	Remote Similarity	NPD6099	Approved
0.6981	Remote Similarity	NPD6100	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