NPASS Compound

Structure

NPC472599 OpenBabel07101719242D 23 24 0 0 1 0 0 0 0 0999 V2000 -7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 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 -6.0622 -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 -4.3301 -1.5000 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 -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 0.0000 -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 2 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 -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 0.0000 -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 1.7321 -2.0000 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 2.5981 -0.5000 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 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 11 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 9 12 1 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 10 23 1 0 0 0 0 11 13 2 0 0 0 0 11 16 1 0 0 0 0 12 8 1 1 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 14 17 2 0 0 0 0 15 16 2 0 0 0 0 15 17 1 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	322.18
Volume:	336.177
LogP:	5.865
LogD:	2.587
LogS:	-3.684
# Rotatable Bonds:	7
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.663
Synthetic Accessibility Score:	3.262
Fsp3:	0.611
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.185
MDCK Permeability:	1.5198937944660429e-05
Pgp-inhibitor:	0.029
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.03
20% Bioavailability (F20%):	0.128
30% Bioavailability (F30%):	0.949

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.129
Plasma Protein Binding (PPB):	98.78398895263672%
Volume Distribution (VD):	0.136
Pgp-substrate:	1.7149990797042847%

ADMET: Metabolism

CYP1A2-inhibitor:	0.066
CYP1A2-substrate:	0.735
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.084
CYP2C9-inhibitor:	0.239
CYP2C9-substrate:	0.09
CYP2D6-inhibitor:	0.091
CYP2D6-substrate:	0.108
CYP3A4-inhibitor:	0.023
CYP3A4-substrate:	0.029

ADMET: Excretion

Clearance (CL):	1.138
Half-life (T1/2):	0.727

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.526
Drug-inuced Liver Injury (DILI):	0.941
AMES Toxicity:	0.421
Rat Oral Acute Toxicity:	0.449
Maximum Recommended Daily Dose:	0.619
Skin Sensitization:	0.627
Carcinogencity:	0.665
Eye Corrosion:	0.003
Eye Irritation:	0.242
Respiratory Toxicity:	0.879

Download Data

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

Natural Product: NPC472599

Natural Product ID:	NPC472599
*Common Name:**	SNWYHMYDWIFBON-GFCCVEGCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SNWYHMYDWIFBON-GFCCVEGCSA-N
Standard InCHI:	InChI=1S/C18H26O5/c1-3-4-5-6-7-8-12-9-13-11(2)16(19)15(18(21)22)17(20)14(13)10-23-12/h12,19-20H,3-10H2,1-2H3,(H,21,22)/t12-/m1/s1
SMILES:	CCCCCCCC1CC2=C(C(=C(C(=C2CO1)O)C(=O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3580978
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001248] Hydroxybenzoic acid derivatives [CHEMONTID:0000487] Salicylic acid and derivatives

*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
NPO32981	cadophora sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[26035018]

☑ 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
MIC	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	100.0	ug.mL-1	PMID[496937]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	35.0	ug.mL-1	PMID[496937]

☑ 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 NPC472599 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	312
0.1-0.2	1456
0.2-0.3	3515
0.3-0.4	8349
0.4-0.5	11081
0.5-0.6	4702
0.6-0.7	7871
0.7-0.8	4873
0.8-0.85	397
0.85-0.9	112
0.9-0.95	26
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9846	High Similarity	NPC156967
0.9621	High Similarity	NPC245058
0.9485	High Similarity	NPC471731
0.9485	High Similarity	NPC159721
0.9416	High Similarity	NPC42540
0.9416	High Similarity	NPC151607
0.9412	High Similarity	NPC471733
0.9407	High Similarity	NPC472601
0.9407	High Similarity	NPC472600
0.9394	High Similarity	NPC475645
0.9385	High Similarity	NPC296158
0.9338	High Similarity	NPC472603
0.9338	High Similarity	NPC472605
0.9338	High Similarity	NPC472604
0.9214	High Similarity	NPC471734
0.9203	High Similarity	NPC472610
0.9191	High Similarity	NPC88269
0.9143	High Similarity	NPC471735
0.9118	High Similarity	NPC472602
0.9058	High Similarity	NPC53649
0.9044	High Similarity	NPC70380
0.9007	High Similarity	NPC473023
0.8978	High Similarity	NPC212693
0.8978	High Similarity	NPC94248
0.8978	High Similarity	NPC191835
0.8971	High Similarity	NPC158481
0.8971	High Similarity	NPC235115
0.8944	High Similarity	NPC8817
0.8936	High Similarity	NPC75694
0.8921	High Similarity	NPC37530
0.8905	High Similarity	NPC194579
0.8881	High Similarity	NPC470359
0.8873	High Similarity	NPC470357
0.8849	High Similarity	NPC99441
0.8841	High Similarity	NPC478200
0.8841	High Similarity	NPC221104
0.8841	High Similarity	NPC33144
0.8836	High Similarity	NPC471695
0.8832	High Similarity	NPC50455
0.8832	High Similarity	NPC291454
0.8811	High Similarity	NPC137296
0.8794	High Similarity	NPC469542
0.8794	High Similarity	NPC478202
0.8786	High Similarity	NPC1704
0.8786	High Similarity	NPC478217
0.8786	High Similarity	NPC313123
0.8786	High Similarity	NPC158634
0.8786	High Similarity	NPC67650
0.8777	High Similarity	NPC105456
0.8777	High Similarity	NPC32360
0.8777	High Similarity	NPC275356
0.8777	High Similarity	NPC139634
0.8768	High Similarity	NPC71256
0.875	High Similarity	NPC153783
0.8741	High Similarity	NPC163846
0.8741	High Similarity	NPC225173
0.8723	High Similarity	NPC469579
0.8723	High Similarity	NPC82913
0.8714	High Similarity	NPC187690
0.8714	High Similarity	NPC155205
0.8714	High Similarity	NPC165172
0.8714	High Similarity	NPC168471
0.8714	High Similarity	NPC158472
0.8707	High Similarity	NPC472799
0.869	High Similarity	NPC291049
0.869	High Similarity	NPC233267
0.8686	High Similarity	NPC474394
0.8681	High Similarity	NPC125801
0.8681	High Similarity	NPC53362
0.8681	High Similarity	NPC166583
0.8676	High Similarity	NPC476389
0.8671	High Similarity	NPC473692
0.8662	High Similarity	NPC51106
0.8662	High Similarity	NPC472006
0.8652	High Similarity	NPC472035
0.8652	High Similarity	NPC478201
0.8652	High Similarity	NPC470842
0.8643	High Similarity	NPC268052
0.8639	High Similarity	NPC273483
0.8633	High Similarity	NPC474771
0.8633	High Similarity	NPC178467
0.8633	High Similarity	NPC149372
0.8633	High Similarity	NPC474849
0.8633	High Similarity	NPC65837
0.863	High Similarity	NPC150928
0.8623	High Similarity	NPC27407
0.8623	High Similarity	NPC290803
0.8623	High Similarity	NPC142027
0.8621	High Similarity	NPC105415
0.8621	High Similarity	NPC37139
0.8613	High Similarity	NPC37299
0.8613	High Similarity	NPC180261
0.8613	High Similarity	NPC470988
0.8611	High Similarity	NPC470570
0.8603	High Similarity	NPC189823
0.8603	High Similarity	NPC219892
0.8592	High Similarity	NPC322112
0.8592	High Similarity	NPC474385
0.8582	High Similarity	NPC64664
0.8571	High Similarity	NPC72958
0.8571	High Similarity	NPC475974
0.8571	High Similarity	NPC232645
0.8571	High Similarity	NPC133856
0.8571	High Similarity	NPC477673
0.8571	High Similarity	NPC477672
0.8561	High Similarity	NPC118919
0.8551	High Similarity	NPC470984
0.8551	High Similarity	NPC175943
0.8543	High Similarity	NPC470358
0.8542	High Similarity	NPC83272
0.8542	High Similarity	NPC34482
0.8529	High Similarity	NPC21378
0.8529	High Similarity	NPC470987
0.8523	High Similarity	NPC89625
0.8523	High Similarity	NPC477687
0.8523	High Similarity	NPC477671
0.8523	High Similarity	NPC149618
0.8521	High Similarity	NPC475730
0.8521	High Similarity	NPC244923
0.8521	High Similarity	NPC149533
0.8514	High Similarity	NPC87708
0.8514	High Similarity	NPC217447
0.8503	High Similarity	NPC119929
0.8503	High Similarity	NPC158866
0.85	High Similarity	NPC261292
0.85	High Similarity	NPC301915
0.85	High Similarity	NPC470983
0.85	High Similarity	NPC135837
0.85	High Similarity	NPC470982
0.8493	Intermediate Similarity	NPC221352
0.8489	Intermediate Similarity	NPC278375
0.8483	Intermediate Similarity	NPC107625
0.8483	Intermediate Similarity	NPC260946
0.8472	Intermediate Similarity	NPC478203
0.8472	Intermediate Similarity	NPC277426
0.8472	Intermediate Similarity	NPC210966
0.8472	Intermediate Similarity	NPC86373
0.8472	Intermediate Similarity	NPC48762
0.8472	Intermediate Similarity	NPC210425
0.8472	Intermediate Similarity	NPC126882
0.8472	Intermediate Similarity	NPC280404
0.8467	Intermediate Similarity	NPC214702
0.8467	Intermediate Similarity	NPC477675
0.8467	Intermediate Similarity	NPC470831
0.8467	Intermediate Similarity	NPC477674
0.8462	Intermediate Similarity	NPC250755
0.8456	Intermediate Similarity	NPC477669
0.8456	Intermediate Similarity	NPC470102
0.8446	Intermediate Similarity	NPC215921
0.8446	Intermediate Similarity	NPC70016
0.844	Intermediate Similarity	NPC9121
0.844	Intermediate Similarity	NPC472403
0.844	Intermediate Similarity	NPC177307
0.8435	Intermediate Similarity	NPC237440
0.8435	Intermediate Similarity	NPC270160
0.8429	Intermediate Similarity	NPC471690
0.8425	Intermediate Similarity	NPC474108
0.8425	Intermediate Similarity	NPC177995
0.8414	Intermediate Similarity	NPC257558
0.8414	Intermediate Similarity	NPC472034
0.8414	Intermediate Similarity	NPC471689
0.8414	Intermediate Similarity	NPC134621
0.8406	Intermediate Similarity	NPC185624
0.8403	Intermediate Similarity	NPC294432
0.8403	Intermediate Similarity	NPC472344
0.8403	Intermediate Similarity	NPC112829
0.8403	Intermediate Similarity	NPC84266
0.8403	Intermediate Similarity	NPC470556
0.8392	Intermediate Similarity	NPC469818
0.8389	Intermediate Similarity	NPC175978
0.8389	Intermediate Similarity	NPC115249
0.8389	Intermediate Similarity	NPC271681
0.838	Intermediate Similarity	NPC92655
0.838	Intermediate Similarity	NPC52358
0.838	Intermediate Similarity	NPC474655
0.838	Intermediate Similarity	NPC247409
0.8378	Intermediate Similarity	NPC472891
0.8378	Intermediate Similarity	NPC179178
0.8378	Intermediate Similarity	NPC470568
0.8369	Intermediate Similarity	NPC470985
0.8369	Intermediate Similarity	NPC470989
0.8367	Intermediate Similarity	NPC172329
0.8367	Intermediate Similarity	NPC471641
0.8367	Intermediate Similarity	NPC240622
0.8367	Intermediate Similarity	NPC240253
0.8367	Intermediate Similarity	NPC2569
0.8367	Intermediate Similarity	NPC471642
0.8366	Intermediate Similarity	NPC117985
0.8357	Intermediate Similarity	NPC182496
0.8357	Intermediate Similarity	NPC180905
0.8356	Intermediate Similarity	NPC472033
0.8356	Intermediate Similarity	NPC237208
0.8345	Intermediate Similarity	NPC33653
0.8345	Intermediate Similarity	NPC193703
0.8345	Intermediate Similarity	NPC470553
0.8345	Intermediate Similarity	NPC95123
0.8345	Intermediate Similarity	NPC48036
0.8345	Intermediate Similarity	NPC470909
0.8345	Intermediate Similarity	NPC184738
0.8345	Intermediate Similarity	NPC21599

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 NPC472599 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	273
0.1-0.2	1039
0.2-0.3	2009
0.3-0.4	2686
0.4-0.5	1758
0.5-0.6	1015
0.6-0.7	285
0.7-0.8	77
0.8-0.85	5
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8936	High Similarity	NPD2532	Approved
0.8936	High Similarity	NPD2534	Approved
0.8936	High Similarity	NPD2533	Approved
0.838	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD5711	Approved
0.8312	Intermediate Similarity	NPD5710	Approved
0.8212	Intermediate Similarity	NPD7819	Suspended
0.8129	Intermediate Similarity	NPD6959	Discontinued
0.8028	Intermediate Similarity	NPD6651	Approved
0.7962	Intermediate Similarity	NPD6232	Discontinued
0.7917	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD5404	Approved
0.7862	Intermediate Similarity	NPD5405	Approved
0.7862	Intermediate Similarity	NPD5406	Approved
0.7862	Intermediate Similarity	NPD5408	Approved
0.7857	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD2800	Approved
0.7821	Intermediate Similarity	NPD7075	Discontinued
0.7812	Intermediate Similarity	NPD7473	Discontinued
0.7742	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD2935	Discontinued
0.7733	Intermediate Similarity	NPD7390	Discontinued
0.7727	Intermediate Similarity	NPD7411	Suspended
0.7716	Intermediate Similarity	NPD5844	Phase 1
0.7692	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD4380	Phase 2
0.7655	Intermediate Similarity	NPD1607	Approved
0.7651	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD7768	Phase 2
0.7635	Intermediate Similarity	NPD1549	Phase 2
0.7619	Intermediate Similarity	NPD1551	Phase 2
0.7586	Intermediate Similarity	NPD230	Phase 1
0.7568	Intermediate Similarity	NPD2346	Discontinued
0.7564	Intermediate Similarity	NPD1934	Approved
0.7564	Intermediate Similarity	NPD6801	Discontinued
0.7551	Intermediate Similarity	NPD1510	Phase 2
0.7548	Intermediate Similarity	NPD6599	Discontinued
0.7533	Intermediate Similarity	NPD3750	Approved
0.7531	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1240	Approved
0.7484	Intermediate Similarity	NPD3226	Approved
0.747	Intermediate Similarity	NPD6559	Discontinued
0.7451	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6799	Approved
0.7383	Intermediate Similarity	NPD2796	Approved
0.7375	Intermediate Similarity	NPD3749	Approved
0.7372	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5124	Phase 1
0.7319	Intermediate Similarity	NPD9545	Approved
0.7303	Intermediate Similarity	NPD4628	Phase 3
0.7299	Intermediate Similarity	NPD9493	Approved
0.7283	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6100	Approved
0.7267	Intermediate Similarity	NPD6099	Approved
0.726	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD3764	Approved
0.7251	Intermediate Similarity	NPD8150	Discontinued
0.725	Intermediate Similarity	NPD3817	Phase 2
0.7244	Intermediate Similarity	NPD920	Approved
0.7237	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD1243	Approved
0.7234	Intermediate Similarity	NPD1201	Approved
0.7226	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD4626	Approved
0.7212	Intermediate Similarity	NPD6166	Phase 2
0.7212	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD3882	Suspended
0.72	Intermediate Similarity	NPD3748	Approved
0.72	Intermediate Similarity	NPD2799	Discontinued
0.7188	Intermediate Similarity	NPD2801	Approved
0.7188	Intermediate Similarity	NPD1465	Phase 2
0.7186	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD5494	Approved
0.7162	Intermediate Similarity	NPD943	Approved
0.7161	Intermediate Similarity	NPD1511	Approved
0.7153	Intermediate Similarity	NPD1164	Approved
0.7153	Intermediate Similarity	NPD1470	Approved
0.7143	Intermediate Similarity	NPD7074	Phase 3
0.7143	Intermediate Similarity	NPD5691	Approved
0.7125	Intermediate Similarity	NPD37	Approved
0.7117	Intermediate Similarity	NPD6234	Discontinued
0.7115	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5953	Discontinued
0.7099	Intermediate Similarity	NPD4965	Approved
0.7099	Intermediate Similarity	NPD4966	Approved
0.7099	Intermediate Similarity	NPD4967	Phase 2
0.7097	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7286	Phase 2
0.7083	Intermediate Similarity	NPD1283	Approved
0.7083	Intermediate Similarity	NPD7054	Approved
0.7078	Intermediate Similarity	NPD7003	Approved
0.7076	Intermediate Similarity	NPD8312	Approved
0.7076	Intermediate Similarity	NPD8313	Approved
0.7075	Intermediate Similarity	NPD4625	Phase 3
0.707	Intermediate Similarity	NPD1512	Approved
0.7069	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7472	Approved
0.7037	Intermediate Similarity	NPD5402	Approved
0.7027	Intermediate Similarity	NPD411	Approved
0.7025	Intermediate Similarity	NPD5403	Approved
0.7024	Intermediate Similarity	NPD3818	Discontinued
0.7018	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD919	Approved
0.7006	Intermediate Similarity	NPD6535	Approved
0.7006	Intermediate Similarity	NPD6534	Approved
0.7006	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6797	Phase 2
0.6973	Remote Similarity	NPD8151	Discontinued
0.6959	Remote Similarity	NPD7251	Discontinued
0.6944	Remote Similarity	NPD9717	Approved
0.6933	Remote Similarity	NPD2979	Phase 3
0.6928	Remote Similarity	NPD2438	Suspended
0.6923	Remote Similarity	NPD7228	Approved
0.6919	Remote Similarity	NPD7808	Phase 3
0.6918	Remote Similarity	NPD1203	Approved
0.6913	Remote Similarity	NPD2313	Discontinued
0.6913	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD7985	Registered
0.6913	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD5401	Approved
0.6897	Remote Similarity	NPD4749	Approved
0.6892	Remote Similarity	NPD6832	Phase 2
0.6889	Remote Similarity	NPD7700	Phase 2
0.6889	Remote Similarity	NPD7699	Phase 2
0.6886	Remote Similarity	NPD7229	Phase 3
0.6885	Remote Similarity	NPD7435	Discontinued
0.6875	Remote Similarity	NPD1281	Approved
0.6875	Remote Similarity	NPD422	Phase 1
0.6871	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6663	Approved
0.6855	Remote Similarity	NPD6273	Approved
0.6852	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD8319	Approved
0.6848	Remote Similarity	NPD8320	Phase 1
0.6846	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1398	Phase 1
0.6832	Remote Similarity	NPD7458	Discontinued
0.6828	Remote Similarity	NPD9269	Phase 2
0.6824	Remote Similarity	NPD7177	Discontinued
0.6824	Remote Similarity	NPD5736	Approved
0.6821	Remote Similarity	NPD4060	Phase 1
0.6821	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6782	Approved
0.6813	Remote Similarity	NPD6777	Approved
0.6813	Remote Similarity	NPD6776	Approved
0.6813	Remote Similarity	NPD6779	Approved
0.6813	Remote Similarity	NPD6781	Approved
0.6813	Remote Similarity	NPD6778	Approved
0.6813	Remote Similarity	NPD6780	Approved
0.6809	Remote Similarity	NPD7340	Approved
0.6809	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD4750	Phase 3
0.6783	Remote Similarity	NPD9268	Approved
0.6783	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD4908	Phase 1
0.6776	Remote Similarity	NPD447	Suspended
0.6776	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6002	Phase 3
0.6774	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6004	Phase 3
0.6774	Remote Similarity	NPD6005	Phase 3
0.6774	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7644	Approved
0.676	Remote Similarity	NPD6212	Phase 3
0.676	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.676	Remote Similarity	NPD6213	Phase 3
0.6753	Remote Similarity	NPD7033	Discontinued
0.6753	Remote Similarity	NPD4308	Phase 3
0.6752	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD8166	Discontinued
0.6736	Remote Similarity	NPD1778	Approved
0.6733	Remote Similarity	NPD7008	Discontinued
0.6727	Remote Similarity	NPD4288	Approved
0.6726	Remote Similarity	NPD7199	Phase 2
0.672	Remote Similarity	NPD7783	Phase 2
0.672	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD74	Approved
0.6715	Remote Similarity	NPD9266	Approved
0.6712	Remote Similarity	NPD1608	Approved
0.671	Remote Similarity	NPD4476	Approved
0.671	Remote Similarity	NPD4477	Approved
0.671	Remote Similarity	NPD2531	Phase 2
0.6709	Remote Similarity	NPD6190	Approved
0.6708	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD7698	Approved
0.6703	Remote Similarity	NPD7697	Approved
0.6703	Remote Similarity	NPD7696	Phase 3
0.6689	Remote Similarity	NPD3268	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