NPASS Compound

Structure

CID194740 OpenBabel06191715582D 29 32 0 0 1 0 0 0 0 0999 V2000 -5.0014 -3.3412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3072 -3.7013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8266 4.5908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2085 2.6887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8995 1.7377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8424 -2.0540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8558 2.1535 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 -4.0503 -3.0322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1867 2.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 0.9945 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 -4.5468 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5856 -1.3849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 -0.4067 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 -5.0468 0.3364 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.5366 -1.6939 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 -4.4957 3.8477 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 29 1 0 0 0 0 4 5 1 0 0 0 0 4 8 1 0 0 0 0 6 7 2 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 8 25 1 0 0 0 0 9 12 2 0 0 0 0 9 19 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 15 1 0 0 0 0 13 29 1 0 0 0 0 14 15 1 0 0 0 0 14 16 2 0 0 0 0 15 20 2 0 0 0 0 16 23 1 0 0 0 0 17 11 1 6 0 0 0 17 22 1 0 0 0 0 17 24 1 0 0 0 0 18 5 1 6 0 0 0 18 21 1 0 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 19 26 2 0 0 0 0 20 23 1 0 0 0 0 21 24 2 0 0 0 0 21 27 1 0 0 0 0 22 25 1 0 0 0 0 22 28 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	395.18
Volume:	401.902
LogP:	2.754
LogD:	2.018
LogS:	-3.775
# Rotatable Bonds:	5
TPSA:	100.37
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.577
Synthetic Accessibility Score:	3.78
Fsp3:	0.364
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.978
MDCK Permeability:	9.957664588000625e-06
Pgp-inhibitor:	0.514
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.802
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.05
Plasma Protein Binding (PPB):	93.24031829833984%
Volume Distribution (VD):	0.733
Pgp-substrate:	3.463179349899292%

ADMET: Metabolism

CYP1A2-inhibitor:	0.413
CYP1A2-substrate:	0.915
CYP2C19-inhibitor:	0.599
CYP2C19-substrate:	0.31
CYP2C9-inhibitor:	0.808
CYP2C9-substrate:	0.909
CYP2D6-inhibitor:	0.71
CYP2D6-substrate:	0.84
CYP3A4-inhibitor:	0.338
CYP3A4-substrate:	0.542

ADMET: Excretion

Clearance (CL):	5.646
Half-life (T1/2):	0.791

ADMET: Toxicity

hERG Blockers:	0.106
Human Hepatotoxicity (H-HT):	0.957
Drug-inuced Liver Injury (DILI):	0.837
AMES Toxicity:	0.068
Rat Oral Acute Toxicity:	0.23
Maximum Recommended Daily Dose:	0.922
Skin Sensitization:	0.056
Carcinogencity:	0.63
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC194740

Natural Product ID:	NPC194740
*Common Name:**	18-Oxotryprostatin A
IUPAC Name:	(3S,8aS)-3-[[6-methoxy-2-(3-methylbut-2-enoyl)-1H-indol-3-yl]methyl]-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
Synonyms:
Standard InCHIKey:	UJAJXFUZWQQKAG-ROUUACIJSA-N
Standard InCHI:	InChI=1S/C22H25N3O4/c1-12(2)9-19(26)20-15(14-7-6-13(29-3)10-16(14)23-20)11-17-22(28)25-8-4-5-18(25)21(27)24-17/h6-7,9-10,17-18,23H,4-5,8,11H2,1-3H3,(H,24,27)/t17-,18-/m0/s1
SMILES:	CC(=CC(=O)c1c(C[C@H]2C(=O)N3CCC[C@H]3C(=N2)O)c2ccc(cc2[nH]1)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL488641
PubChem CID:	24900162
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids 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
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18505285]
NPO32792	aspergillus sydowi	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18505285]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21718031]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23647825]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24057165]

☑ 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
NPT81	Cell Line	A549	Homo sapiens	IC50	=	1280.0	nM	PMID[549119]

☑ 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 NPC194740 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	413
0.1-0.2	2871
0.2-0.3	13402
0.3-0.4	5571
0.4-0.5	14201
0.5-0.6	3475
0.6-0.7	2133
0.7-0.8	599
0.8-0.85	23
0.85-0.9	5
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9554	High Similarity	NPC303658
0.9034	High Similarity	NPC305984
0.8853	High Similarity	NPC184680
0.8813	High Similarity	NPC470784
0.8813	High Similarity	NPC470785
0.8447	Intermediate Similarity	NPC471762
0.8355	Intermediate Similarity	NPC244543
0.8317	Intermediate Similarity	NPC295898
0.8295	Intermediate Similarity	NPC323969
0.8281	Intermediate Similarity	NPC66777
0.8271	Intermediate Similarity	NPC469592
0.8271	Intermediate Similarity	NPC471080
0.8265	Intermediate Similarity	NPC122436
0.8263	Intermediate Similarity	NPC87413
0.823	Intermediate Similarity	NPC131486
0.823	Intermediate Similarity	NPC101350
0.823	Intermediate Similarity	NPC474183
0.8227	Intermediate Similarity	NPC21638
0.8213	Intermediate Similarity	NPC306376
0.8203	Intermediate Similarity	NPC469594
0.8194	Intermediate Similarity	NPC152768
0.8194	Intermediate Similarity	NPC148183
0.8186	Intermediate Similarity	NPC235685
0.816	Intermediate Similarity	NPC4687
0.816	Intermediate Similarity	NPC249583
0.816	Intermediate Similarity	NPC270918
0.8128	Intermediate Similarity	NPC150239
0.8125	Intermediate Similarity	NPC260434
0.8103	Intermediate Similarity	NPC63971
0.8103	Intermediate Similarity	NPC91868
0.8075	Intermediate Similarity	NPC321428
0.8069	Intermediate Similarity	NPC84478
0.8056	Intermediate Similarity	NPC264176
0.8045	Intermediate Similarity	NPC174760
0.8037	Intermediate Similarity	NPC473041
0.8037	Intermediate Similarity	NPC247803
0.8037	Intermediate Similarity	NPC39679
0.8034	Intermediate Similarity	NPC133609
0.8009	Intermediate Similarity	NPC60621
0.8009	Intermediate Similarity	NPC146418
0.8	Intermediate Similarity	NPC189079
0.7991	Intermediate Similarity	NPC169402
0.7991	Intermediate Similarity	NPC157931
0.7982	Intermediate Similarity	NPC179287
0.7972	Intermediate Similarity	NPC308137
0.7972	Intermediate Similarity	NPC310211
0.7945	Intermediate Similarity	NPC322064
0.7932	Intermediate Similarity	NPC303374
0.7928	Intermediate Similarity	NPC198503
0.7921	Intermediate Similarity	NPC91179
0.7919	Intermediate Similarity	NPC288987
0.7919	Intermediate Similarity	NPC208084
0.7911	Intermediate Similarity	NPC478078
0.7904	Intermediate Similarity	NPC473187
0.79	Intermediate Similarity	NPC116238
0.7895	Intermediate Similarity	NPC473105
0.7892	Intermediate Similarity	NPC220851
0.7873	Intermediate Similarity	NPC264285
0.787	Intermediate Similarity	NPC15801
0.787	Intermediate Similarity	NPC475910
0.7867	Intermediate Similarity	NPC24370
0.7867	Intermediate Similarity	NPC319232
0.7851	Intermediate Similarity	NPC196718
0.785	Intermediate Similarity	NPC134848
0.7834	Intermediate Similarity	NPC469589
0.7832	Intermediate Similarity	NPC118559
0.7832	Intermediate Similarity	NPC304307
0.7832	Intermediate Similarity	NPC261251
0.7832	Intermediate Similarity	NPC124920
0.7832	Intermediate Similarity	NPC34580
0.7821	Intermediate Similarity	NPC78609
0.7817	Intermediate Similarity	NPC284888
0.7812	Intermediate Similarity	NPC16352
0.7797	Intermediate Similarity	NPC100547
0.7797	Intermediate Similarity	NPC311906
0.7793	Intermediate Similarity	NPC46561
0.7793	Intermediate Similarity	NPC329747
0.7788	Intermediate Similarity	NPC214142
0.7783	Intermediate Similarity	NPC3207
0.7783	Intermediate Similarity	NPC330009
0.7783	Intermediate Similarity	NPC39370
0.7773	Intermediate Similarity	NPC473186
0.7773	Intermediate Similarity	NPC102593
0.7767	Intermediate Similarity	NPC476098
0.7764	Intermediate Similarity	NPC165964
0.7763	Intermediate Similarity	NPC322135
0.7763	Intermediate Similarity	NPC23294
0.7763	Intermediate Similarity	NPC326363
0.7763	Intermediate Similarity	NPC223409
0.7763	Intermediate Similarity	NPC95240
0.7757	Intermediate Similarity	NPC471944
0.7753	Intermediate Similarity	NPC257851
0.7738	Intermediate Similarity	NPC477979
0.7736	Intermediate Similarity	NPC70956
0.7736	Intermediate Similarity	NPC243834
0.7729	Intermediate Similarity	NPC14288
0.7725	Intermediate Similarity	NPC475816
0.7723	Intermediate Similarity	NPC128115
0.7719	Intermediate Similarity	NPC274640
0.7718	Intermediate Similarity	NPC258048
0.7717	Intermediate Similarity	NPC303951
0.7717	Intermediate Similarity	NPC471304
0.7713	Intermediate Similarity	NPC184408
0.7696	Intermediate Similarity	NPC321592
0.7696	Intermediate Similarity	NPC300156
0.7696	Intermediate Similarity	NPC45190
0.7696	Intermediate Similarity	NPC72980
0.7696	Intermediate Similarity	NPC54803
0.7676	Intermediate Similarity	NPC53534
0.7671	Intermediate Similarity	NPC174758
0.7668	Intermediate Similarity	NPC312645
0.7662	Intermediate Similarity	NPC323752
0.7662	Intermediate Similarity	NPC323198
0.7658	Intermediate Similarity	NPC50562
0.7657	Intermediate Similarity	NPC67401
0.7655	Intermediate Similarity	NPC144452
0.765	Intermediate Similarity	NPC285558
0.7644	Intermediate Similarity	NPC225279
0.7644	Intermediate Similarity	NPC472099
0.7639	Intermediate Similarity	NPC6786
0.7634	Intermediate Similarity	NPC96321
0.7633	Intermediate Similarity	NPC152620
0.763	Intermediate Similarity	NPC204970
0.7629	Intermediate Similarity	NPC325976
0.7629	Intermediate Similarity	NPC33064
0.7629	Intermediate Similarity	NPC245055
0.7626	Intermediate Similarity	NPC86834
0.7626	Intermediate Similarity	NPC210828
0.7623	Intermediate Similarity	NPC67658
0.7623	Intermediate Similarity	NPC36405
0.7619	Intermediate Similarity	NPC132329
0.7613	Intermediate Similarity	NPC39500
0.7613	Intermediate Similarity	NPC89508
0.7602	Intermediate Similarity	NPC187501
0.76	Intermediate Similarity	NPC269270
0.7598	Intermediate Similarity	NPC473185
0.7595	Intermediate Similarity	NPC81939
0.7593	Intermediate Similarity	NPC232727
0.7591	Intermediate Similarity	NPC325297
0.7585	Intermediate Similarity	NPC176127
0.7574	Intermediate Similarity	NPC41501
0.7571	Intermediate Similarity	NPC221873
0.7569	Intermediate Similarity	NPC132539
0.7568	Intermediate Similarity	NPC472098
0.7566	Intermediate Similarity	NPC14686
0.7563	Intermediate Similarity	NPC475666
0.7563	Intermediate Similarity	NPC469734
0.7558	Intermediate Similarity	NPC475112
0.7558	Intermediate Similarity	NPC475085
0.7558	Intermediate Similarity	NPC291535
0.7557	Intermediate Similarity	NPC207620
0.7544	Intermediate Similarity	NPC51388
0.7543	Intermediate Similarity	NPC475720
0.7543	Intermediate Similarity	NPC474192
0.7542	Intermediate Similarity	NPC26543
0.7535	Intermediate Similarity	NPC100863
0.7535	Intermediate Similarity	NPC72211
0.7534	Intermediate Similarity	NPC472286
0.7534	Intermediate Similarity	NPC472287
0.7532	Intermediate Similarity	NPC82472
0.7529	Intermediate Similarity	NPC169716
0.7524	Intermediate Similarity	NPC17059
0.7523	Intermediate Similarity	NPC165599
0.7522	Intermediate Similarity	NPC168209
0.7522	Intermediate Similarity	NPC473179
0.7521	Intermediate Similarity	NPC477549
0.7521	Intermediate Similarity	NPC314882
0.7511	Intermediate Similarity	NPC61038
0.7511	Intermediate Similarity	NPC472285
0.7511	Intermediate Similarity	NPC122886
0.751	Intermediate Similarity	NPC181081
0.75	Intermediate Similarity	NPC118228
0.75	Intermediate Similarity	NPC183777
0.749	Intermediate Similarity	NPC260909
0.7489	Intermediate Similarity	NPC12344
0.7488	Intermediate Similarity	NPC141454
0.7477	Intermediate Similarity	NPC276517
0.7468	Intermediate Similarity	NPC475844
0.7468	Intermediate Similarity	NPC148889
0.7467	Intermediate Similarity	NPC170114
0.7467	Intermediate Similarity	NPC274982
0.7465	Intermediate Similarity	NPC472292
0.7459	Intermediate Similarity	NPC478083
0.7456	Intermediate Similarity	NPC477532
0.7456	Intermediate Similarity	NPC280799
0.7455	Intermediate Similarity	NPC476106
0.7455	Intermediate Similarity	NPC175602
0.7453	Intermediate Similarity	NPC472112
0.7447	Intermediate Similarity	NPC272549
0.7445	Intermediate Similarity	NPC193267
0.7445	Intermediate Similarity	NPC213530
0.7444	Intermediate Similarity	NPC82370
0.7443	Intermediate Similarity	NPC223427
0.7442	Intermediate Similarity	NPC472293
0.7442	Intermediate Similarity	NPC70259
0.7439	Intermediate Similarity	NPC89549
0.7432	Intermediate Similarity	NPC174672
0.743	Intermediate Similarity	NPC81802
0.743	Intermediate Similarity	NPC247735
0.743	Intermediate Similarity	NPC472295

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 NPC194740 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	227
0.1-0.2	579
0.2-0.3	903
0.3-0.4	1230
0.4-0.5	2644
0.5-0.6	2407
0.6-0.7	1009
0.7-0.8	149
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.817	Intermediate Similarity	NPD4885	Approved
0.8136	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.8035	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD3259	Approved
0.7873	Intermediate Similarity	NPD5632	Approved
0.7839	Intermediate Similarity	NPD5482	Discontinued
0.7817	Intermediate Similarity	NPD4373	Phase 2
0.7803	Intermediate Similarity	NPD6242	Discontinued
0.7793	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD4368	Phase 2
0.7768	Intermediate Similarity	NPD6790	Phase 1
0.7763	Intermediate Similarity	NPD5479	Discontinued
0.7763	Intermediate Similarity	NPD4952	Phase 3
0.7749	Intermediate Similarity	NPD7853	Phase 2
0.7745	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD5658	Approved
0.7699	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7696	Intermediate Similarity	NPD3003	Approved
0.7682	Intermediate Similarity	NPD7470	Discontinued
0.7682	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD6376	Discontinued
0.7589	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD1768	Approved
0.7573	Intermediate Similarity	NPD4558	Phase 2
0.754	Intermediate Similarity	NPD7393	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD3507	Phase 2
0.7522	Intermediate Similarity	NPD3258	Approved
0.7522	Intermediate Similarity	NPD7994	Phase 2
0.7521	Intermediate Similarity	NPD8463	Approved
0.7511	Intermediate Similarity	NPD6517	Phase 3
0.751	Intermediate Similarity	NPD8364	Approved
0.751	Intermediate Similarity	NPD8363	Approved
0.75	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.749	Intermediate Similarity	NPD8460	Approved
0.749	Intermediate Similarity	NPD8459	Approved
0.7489	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7489	Intermediate Similarity	NPD7180	Phase 3
0.7489	Intermediate Similarity	NPD5866	Approved
0.7479	Intermediate Similarity	NPD2951	Discontinued
0.7478	Intermediate Similarity	NPD7603	Discontinued
0.7468	Intermediate Similarity	NPD6263	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD2916	Discontinued
0.746	Intermediate Similarity	NPD5450	Discontinued
0.7455	Intermediate Similarity	NPD3945	Discontinued
0.745	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7437	Intermediate Similarity	NPD6716	Phase 1
0.7435	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD8016	Phase 3
0.7426	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD6995	Phase 1
0.7422	Intermediate Similarity	NPD5293	Phase 2
0.7422	Intermediate Similarity	NPD5903	Approved
0.7422	Intermediate Similarity	NPD5902	Approved
0.7403	Intermediate Similarity	NPD3263	Phase 3
0.7402	Intermediate Similarity	NPD8429	Approved
0.7402	Intermediate Similarity	NPD8466	Approved
0.7402	Intermediate Similarity	NPD8467	Approved
0.7402	Intermediate Similarity	NPD8428	Approved
0.7402	Intermediate Similarity	NPD8427	Approved
0.7402	Intermediate Similarity	NPD8465	Approved
0.739	Intermediate Similarity	NPD7803	Approved
0.739	Intermediate Similarity	NPD8284	Discontinued
0.7388	Intermediate Similarity	NPD8255	Phase 2
0.7382	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7194	Discontinued
0.7353	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD7688	Phase 1
0.735	Intermediate Similarity	NPD6962	Phase 2
0.735	Intermediate Similarity	NPD1867	Approved
0.7349	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD1038	Approved
0.7348	Intermediate Similarity	NPD6209	Approved
0.7345	Intermediate Similarity	NPD3257	Approved
0.7342	Intermediate Similarity	NPD1392	Approved
0.7339	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD7955	Approved
0.7328	Intermediate Similarity	NPD7426	Phase 1
0.7328	Intermediate Similarity	NPD7956	Approved
0.7321	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD3243	Approved
0.73	Intermediate Similarity	NPD3006	Discontinued
0.7293	Intermediate Similarity	NPD7690	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD8426	Approved
0.7287	Intermediate Similarity	NPD8425	Approved
0.7276	Intermediate Similarity	NPD7181	Phase 3
0.7265	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD8279	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD5901	Discontinued
0.7249	Intermediate Similarity	NPD6985	Discontinued
0.7246	Intermediate Similarity	NPD7031	Phase 1
0.7244	Intermediate Similarity	NPD3392	Approved
0.7237	Intermediate Similarity	NPD5612	Discontinued
0.7235	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD2510	Approved
0.7232	Intermediate Similarity	NPD2509	Approved
0.7229	Intermediate Similarity	NPD7708	Approved
0.7227	Intermediate Similarity	NPD4500	Approved
0.7227	Intermediate Similarity	NPD4501	Approved
0.7227	Intermediate Similarity	NPD484	Approved
0.7222	Intermediate Similarity	NPD4328	Approved
0.722	Intermediate Similarity	NPD8403	Phase 1
0.7218	Intermediate Similarity	NPD8091	Phase 3
0.7203	Intermediate Similarity	NPD7284	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD5512	Phase 3
0.7196	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD4897	Phase 2
0.7193	Intermediate Similarity	NPD3757	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD4539	Phase 1
0.7178	Intermediate Similarity	NPD7417	Discontinued
0.7175	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD4429	Discontinued
0.7173	Intermediate Similarity	NPD7797	Approved
0.7173	Intermediate Similarity	NPD7796	Approved
0.7172	Intermediate Similarity	NPD8358	Approved
0.7161	Intermediate Similarity	NPD5924	Discontinued
0.716	Intermediate Similarity	NPD6530	Approved
0.716	Intermediate Similarity	NPD6531	Approved
0.7159	Intermediate Similarity	NPD8349	Phase 1
0.7156	Intermediate Similarity	NPD4418	Discontinued
0.7155	Intermediate Similarity	NPD4923	Phase 1
0.7143	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7558	Phase 2
0.7143	Intermediate Similarity	NPD6974	Phase 3
0.7137	Intermediate Similarity	NPD5416	Discontinued
0.7131	Intermediate Similarity	NPD1505	Phase 2
0.7131	Intermediate Similarity	NPD8359	Phase 2
0.7131	Intermediate Similarity	NPD5488	Discontinued
0.713	Intermediate Similarity	NPD3326	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6176	Phase 1
0.7124	Intermediate Similarity	NPD2285	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4203	Approved
0.7123	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4204	Approved
0.7119	Intermediate Similarity	NPD5559	Phase 2
0.7112	Intermediate Similarity	NPD5850	Phase 3
0.7111	Intermediate Similarity	NPD7222	Phase 2
0.7111	Intermediate Similarity	NPD7452	Approved
0.7111	Intermediate Similarity	NPD7453	Approved
0.7109	Intermediate Similarity	NPD7689	Approved
0.7104	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7395	Discontinued
0.7098	Intermediate Similarity	NPD4795	Phase 2
0.7098	Intermediate Similarity	NPD3947	Discontinued
0.7097	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5532	Phase 2
0.7093	Intermediate Similarity	NPD1166	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7948	Phase 1
0.7091	Intermediate Similarity	NPD5003	Discontinued
0.7089	Intermediate Similarity	NPD1659	Phase 1
0.7085	Intermediate Similarity	NPD2779	Approved
0.7078	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD4845	Discontinued
0.7073	Intermediate Similarity	NPD8102	Discontinued
0.7067	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD7001	Phase 3
0.7067	Intermediate Similarity	NPD7174	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6745	Discontinued
0.7059	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4499	Approved
0.7048	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD8289	Discontinued
0.7032	Intermediate Similarity	NPD802	Phase 2
0.7031	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD3746	Discontinued
0.7028	Intermediate Similarity	NPD6252	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD8114	Approved
0.7022	Intermediate Similarity	NPD8115	Approved
0.7017	Intermediate Similarity	NPD5022	Discontinued
0.7013	Intermediate Similarity	NPD3394	Approved
0.7013	Intermediate Similarity	NPD3393	Approved
0.7013	Intermediate Similarity	NPD3389	Approved
0.7009	Intermediate Similarity	NPD5507	Approved
0.7009	Intermediate Similarity	NPD5506	Approved
0.7005	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD6770	Approved
0.6996	Remote Similarity	NPD1739	Approved
0.6996	Remote Similarity	NPD1740	Approved
0.6996	Remote Similarity	NPD4600	Approved
0.6996	Remote Similarity	NPD4601	Approved
0.6989	Remote Similarity	NPD8489	Phase 1
0.6987	Remote Similarity	NPD5066	Phase 2
0.6987	Remote Similarity	NPD4502	Phase 2
0.6987	Remote Similarity	NPD5067	Phase 2
0.6986	Remote Similarity	NPD5183	Approved
0.6986	Remote Similarity	NPD5186	Approved
0.6978	Remote Similarity	NPD5513	Phase 2
0.6972	Remote Similarity	NPD2565	Phase 2
0.6972	Remote Similarity	NPD2564	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