NPASS Compound

Structure

NPC19747 OpenBabel07101719242D 24 27 0 0 1 0 0 0 0 0999 V2000 -2.5053 -6.2679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8351 -5.3036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1832 -4.0607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8351 -3.3750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.8929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5053 -5.3036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6702 -1.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6702 -0.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8351 -0.4821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1541 -1.4464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6702 -4.8214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5873 -2.2266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8351 -2.4107 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6702 -0.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8351 -0.4821 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6702 -1.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8351 -2.4107 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6702 -3.8571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9286 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.9643 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5053 -3.3750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5873 -0.6663 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8351 -3.3750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 5 19 1 0 0 0 0 6 11 2 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 8 15 1 0 0 0 0 9 14 1 0 0 0 0 10 12 2 0 0 0 0 10 22 1 0 0 0 0 11 18 1 0 0 0 0 12 16 1 0 0 0 0 13 19 1 6 0 0 0 14 16 2 0 0 0 0 14 22 1 0 0 0 0 15 20 1 6 0 0 0 15 24 1 0 0 0 0 16 17 1 0 0 0 0 17 19 1 6 0 0 0 17 23 1 0 0 0 0 18 21 2 0 0 0 0 18 23 1 0 0 0 0 19 20 1 6 0 0 0 20 9 1 6 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.18
Volume:	344.865
LogP:	4.018
LogD:	3.939
LogS:	-4.712
# Rotatable Bonds:	3
TPSA:	51.97
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.462
Synthetic Accessibility Score:	5.335
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.685
MDCK Permeability:	2.657917320902925e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.816
30% Bioavailability (F30%):	0.492

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.348
Plasma Protein Binding (PPB):	90.85132598876953%
Volume Distribution (VD):	3.133
Pgp-substrate:	11.268933296203613%

ADMET: Metabolism

CYP1A2-inhibitor:	0.384
CYP1A2-substrate:	0.651
CYP2C19-inhibitor:	0.81
CYP2C19-substrate:	0.792
CYP2C9-inhibitor:	0.844
CYP2C9-substrate:	0.077
CYP2D6-inhibitor:	0.339
CYP2D6-substrate:	0.574
CYP3A4-inhibitor:	0.919
CYP3A4-substrate:	0.553

ADMET: Excretion

Clearance (CL):	13.332
Half-life (T1/2):	0.192

ADMET: Toxicity

hERG Blockers:	0.333
Human Hepatotoxicity (H-HT):	0.814
Drug-inuced Liver Injury (DILI):	0.82
AMES Toxicity:	0.106
Rat Oral Acute Toxicity:	0.853
Maximum Recommended Daily Dose:	0.604
Skin Sensitization:	0.756
Carcinogencity:	0.695
Eye Corrosion:	0.221
Eye Irritation:	0.091
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC19747

Natural Product ID:	NPC19747
*Common Name:**	BAHLYRYDRNWKKI-GDIVAPDVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BAHLYRYDRNWKKI-GDIVAPDVSA-N
Standard InCHI:	InChI=1S/C20H26O4/c1-6-11(2)18(21)23-17-16-12(3)10-22-14(16)9-20-15(24-20)8-7-13(4)19(17,20)5/h6,10,13,15,17H,7-9H2,1-5H3/b11-6-/t13-,15-,17+,19-,20-/m0/s1
SMILES:	C/C=C(C(=O)O[C@@H]1c2c(C)coc2C[C@]23[C@@]1(C)[C@@H](C)CC[C@@H]3O2)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL253986
PubChem CID:	44445652
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO1183	Ligularia macrophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17672504]
NPO1183	Ligularia macrophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18044832]
NPO1183	Ligularia macrophylla	Species	Asteraceae	Eukaryota	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
EC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	EC50	=	9.4	ug.mL-1	PMID[515911]
NPT83	Cell Line	MCF7	Homo sapiens	EC50	>	20.0	ug.mL-1	PMID[515911]

☑ 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 NPC19747 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	399
0.1-0.2	1447
0.2-0.3	3034
0.3-0.4	6570
0.4-0.5	11347
0.5-0.6	8063
0.6-0.7	8219
0.7-0.8	3384
0.8-0.85	208
0.85-0.9	20
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9716	High Similarity	NPC62799
0.9655	High Similarity	NPC114880
0.965	High Similarity	NPC211625
0.9366	High Similarity	NPC205071
0.9301	High Similarity	NPC84479
0.9195	High Similarity	NPC75310
0.9172	High Similarity	NPC97904
0.911	High Similarity	NPC221809
0.906	High Similarity	NPC475777
0.9013	High Similarity	NPC474611
0.8966	High Similarity	NPC64568
0.8926	High Similarity	NPC212257
0.891	High Similarity	NPC473766
0.891	High Similarity	NPC473753
0.8896	High Similarity	NPC188649
0.8882	High Similarity	NPC41880
0.8882	High Similarity	NPC104736
0.8867	High Similarity	NPC18135
0.8839	High Similarity	NPC288602
0.8839	High Similarity	NPC88841
0.8824	High Similarity	NPC304692
0.8824	High Similarity	NPC81405
0.8816	High Similarity	NPC469850
0.8808	High Similarity	NPC75906
0.88	High Similarity	NPC476122
0.88	High Similarity	NPC477404
0.88	High Similarity	NPC196864
0.8797	High Similarity	NPC302392
0.8794	High Similarity	NPC293253
0.8774	High Similarity	NPC18986
0.8766	High Similarity	NPC473368
0.8766	High Similarity	NPC140952
0.8758	High Similarity	NPC209364
0.8758	High Similarity	NPC107646
0.8734	High Similarity	NPC296558
0.8726	High Similarity	NPC121995
0.8725	High Similarity	NPC71821
0.871	High Similarity	NPC287559
0.8701	High Similarity	NPC299038
0.8701	High Similarity	NPC286722
0.8701	High Similarity	NPC195954
0.8701	High Similarity	NPC88007
0.8701	High Similarity	NPC194499
0.8684	High Similarity	NPC476201
0.8681	High Similarity	NPC286130
0.8675	High Similarity	NPC159927
0.8675	High Similarity	NPC156189
0.8675	High Similarity	NPC469335
0.8662	High Similarity	NPC56358
0.8654	High Similarity	NPC68848
0.8654	High Similarity	NPC470939
0.8645	High Similarity	NPC475295
0.8645	High Similarity	NPC473473
0.8636	High Similarity	NPC126723
0.8636	High Similarity	NPC60973
0.8636	High Similarity	NPC263265
0.8627	High Similarity	NPC57998
0.8627	High Similarity	NPC282445
0.8621	High Similarity	NPC476943
0.8609	High Similarity	NPC195325
0.86	High Similarity	NPC470941
0.8599	High Similarity	NPC283209
0.8599	High Similarity	NPC476197
0.8599	High Similarity	NPC285567
0.8591	High Similarity	NPC41182
0.859	High Similarity	NPC475381
0.8581	High Similarity	NPC472772
0.8581	High Similarity	NPC167142
0.8581	High Similarity	NPC223415
0.8581	High Similarity	NPC249021
0.8571	High Similarity	NPC476262
0.8562	High Similarity	NPC268905
0.8562	High Similarity	NPC469503
0.8553	High Similarity	NPC270312
0.8553	High Similarity	NPC228842
0.8552	High Similarity	NPC307401
0.8552	High Similarity	NPC310043
0.8544	High Similarity	NPC276735
0.8535	High Similarity	NPC5079
0.8535	High Similarity	NPC472668
0.8533	High Similarity	NPC233763
0.8526	High Similarity	NPC237155
0.8523	High Similarity	NPC251865
0.8514	High Similarity	NPC263337
0.8514	High Similarity	NPC121158
0.8506	High Similarity	NPC30222
0.8506	High Similarity	NPC178932
0.8487	Intermediate Similarity	NPC470791
0.8487	Intermediate Similarity	NPC470790
0.8487	Intermediate Similarity	NPC472654
0.8483	Intermediate Similarity	NPC214572
0.8481	Intermediate Similarity	NPC472669
0.8481	Intermediate Similarity	NPC134254
0.8481	Intermediate Similarity	NPC39986
0.8481	Intermediate Similarity	NPC234660
0.8481	Intermediate Similarity	NPC51568
0.8481	Intermediate Similarity	NPC302369
0.8481	Intermediate Similarity	NPC469846
0.8477	Intermediate Similarity	NPC255414
0.8471	Intermediate Similarity	NPC305016
0.8471	Intermediate Similarity	NPC25255
0.8471	Intermediate Similarity	NPC335761
0.8471	Intermediate Similarity	NPC472653
0.8471	Intermediate Similarity	NPC8389
0.8467	Intermediate Similarity	NPC56731
0.8466	Intermediate Similarity	NPC167340
0.8462	Intermediate Similarity	NPC187149
0.8456	Intermediate Similarity	NPC243577
0.8456	Intermediate Similarity	NPC470741
0.8452	Intermediate Similarity	NPC469336
0.8452	Intermediate Similarity	NPC35000
0.8446	Intermediate Similarity	NPC20500
0.8442	Intermediate Similarity	NPC121615
0.8442	Intermediate Similarity	NPC294511
0.8438	Intermediate Similarity	NPC173516
0.8435	Intermediate Similarity	NPC474722
0.8435	Intermediate Similarity	NPC474615
0.8428	Intermediate Similarity	NPC476856
0.8428	Intermediate Similarity	NPC476857
0.8428	Intermediate Similarity	NPC476858
0.8428	Intermediate Similarity	NPC472664
0.8428	Intermediate Similarity	NPC476860
0.8425	Intermediate Similarity	NPC310830
0.8418	Intermediate Similarity	NPC82851
0.8418	Intermediate Similarity	NPC18347
0.8418	Intermediate Similarity	NPC79571
0.8418	Intermediate Similarity	NPC471166
0.8418	Intermediate Similarity	NPC472771
0.8418	Intermediate Similarity	NPC193798
0.8418	Intermediate Similarity	NPC149896
0.8418	Intermediate Similarity	NPC197596
0.8418	Intermediate Similarity	NPC471167
0.8411	Intermediate Similarity	NPC262198
0.8408	Intermediate Similarity	NPC474932
0.8408	Intermediate Similarity	NPC475967
0.84	Intermediate Similarity	NPC86935
0.84	Intermediate Similarity	NPC476944
0.8397	Intermediate Similarity	NPC204663
0.8385	Intermediate Similarity	NPC471397
0.8385	Intermediate Similarity	NPC160651
0.8378	Intermediate Similarity	NPC282973
0.8375	Intermediate Similarity	NPC23387
0.8367	Intermediate Similarity	NPC220094
0.8366	Intermediate Similarity	NPC125182
0.8366	Intermediate Similarity	NPC69647
0.8365	Intermediate Similarity	NPC476035
0.8365	Intermediate Similarity	NPC472773
0.8365	Intermediate Similarity	NPC471168
0.8365	Intermediate Similarity	NPC14499
0.8365	Intermediate Similarity	NPC475039
0.8356	Intermediate Similarity	NPC46896
0.8355	Intermediate Similarity	NPC224418
0.8355	Intermediate Similarity	NPC286038
0.8354	Intermediate Similarity	NPC191828
0.8354	Intermediate Similarity	NPC333139
0.8344	Intermediate Similarity	NPC472283
0.8344	Intermediate Similarity	NPC7059
0.8344	Intermediate Similarity	NPC261597
0.8344	Intermediate Similarity	NPC195131
0.8333	Intermediate Similarity	NPC44675
0.8333	Intermediate Similarity	NPC264943
0.8333	Intermediate Similarity	NPC214541
0.8333	Intermediate Similarity	NPC472785
0.8323	Intermediate Similarity	NPC476850
0.8323	Intermediate Similarity	NPC246164
0.8323	Intermediate Similarity	NPC472282
0.8323	Intermediate Similarity	NPC279768
0.8323	Intermediate Similarity	NPC476861
0.8323	Intermediate Similarity	NPC476853
0.8322	Intermediate Similarity	NPC248795
0.8313	Intermediate Similarity	NPC123088
0.8313	Intermediate Similarity	NPC261184
0.8313	Intermediate Similarity	NPC271657
0.8311	Intermediate Similarity	NPC202260
0.8302	Intermediate Similarity	NPC117986
0.8302	Intermediate Similarity	NPC329938
0.8302	Intermediate Similarity	NPC200782
0.8301	Intermediate Similarity	NPC66991
0.8301	Intermediate Similarity	NPC93666
0.8299	Intermediate Similarity	NPC470742
0.8291	Intermediate Similarity	NPC123153
0.8291	Intermediate Similarity	NPC84349
0.8291	Intermediate Similarity	NPC307383
0.8289	Intermediate Similarity	NPC346
0.8286	Intermediate Similarity	NPC178382
0.8282	Intermediate Similarity	NPC475237
0.8282	Intermediate Similarity	NPC294512
0.8282	Intermediate Similarity	NPC475641
0.828	Intermediate Similarity	NPC278010
0.828	Intermediate Similarity	NPC250769
0.828	Intermediate Similarity	NPC295608
0.8278	Intermediate Similarity	NPC142113
0.8272	Intermediate Similarity	NPC271235
0.8267	Intermediate Similarity	NPC62103
0.8267	Intermediate Similarity	NPC20578
0.8261	Intermediate Similarity	NPC475779
0.8261	Intermediate Similarity	NPC277618
0.8258	Intermediate Similarity	NPC191104
0.8255	Intermediate Similarity	NPC148374
0.8255	Intermediate Similarity	NPC67003

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 NPC19747 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	342
0.1-0.2	949
0.2-0.3	1872
0.3-0.4	2698
0.4-0.5	2036
0.5-0.6	896
0.6-0.7	304
0.7-0.8	53
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8354	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD8434	Phase 2
0.8101	Intermediate Similarity	NPD5760	Phase 2
0.8101	Intermediate Similarity	NPD5761	Phase 2
0.8065	Intermediate Similarity	NPD920	Approved
0.7935	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD2533	Approved
0.7821	Intermediate Similarity	NPD2532	Approved
0.7821	Intermediate Similarity	NPD2534	Approved
0.7806	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD1243	Approved
0.7712	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6599	Discontinued
0.7654	Intermediate Similarity	NPD7819	Suspended
0.7647	Intermediate Similarity	NPD2796	Approved
0.7636	Intermediate Similarity	NPD5494	Approved
0.7613	Intermediate Similarity	NPD2800	Approved
0.7602	Intermediate Similarity	NPD6765	Approved
0.7602	Intermediate Similarity	NPD6764	Approved
0.7597	Intermediate Similarity	NPD1471	Phase 3
0.7576	Intermediate Similarity	NPD919	Approved
0.7564	Intermediate Similarity	NPD4628	Phase 3
0.7515	Intermediate Similarity	NPD3749	Approved
0.7439	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6785	Approved
0.7429	Intermediate Similarity	NPD6784	Approved
0.7421	Intermediate Similarity	NPD6799	Approved
0.7399	Intermediate Similarity	NPD6559	Discontinued
0.7381	Intermediate Similarity	NPD1247	Approved
0.7372	Intermediate Similarity	NPD2346	Discontinued
0.7368	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD3748	Approved
0.7355	Intermediate Similarity	NPD2799	Discontinued
0.7342	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7411	Suspended
0.7308	Intermediate Similarity	NPD1551	Phase 2
0.7305	Intermediate Similarity	NPD7075	Discontinued
0.7301	Intermediate Similarity	NPD3226	Approved
0.7285	Intermediate Similarity	NPD6832	Phase 2
0.7278	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6801	Discontinued
0.7267	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD5710	Approved
0.7235	Intermediate Similarity	NPD5711	Approved
0.7229	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6273	Approved
0.7215	Intermediate Similarity	NPD1549	Phase 2
0.7197	Intermediate Similarity	NPD6100	Approved
0.7197	Intermediate Similarity	NPD6099	Approved
0.7193	Intermediate Similarity	NPD3926	Phase 2
0.719	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2313	Discontinued
0.7186	Intermediate Similarity	NPD3817	Phase 2
0.7186	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6959	Discontinued
0.7161	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2344	Approved
0.7152	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD17	Approved
0.7143	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3882	Suspended
0.7135	Intermediate Similarity	NPD6808	Phase 2
0.7126	Intermediate Similarity	NPD5844	Phase 1
0.7125	Intermediate Similarity	NPD3750	Approved
0.7114	Intermediate Similarity	NPD3972	Approved
0.711	Intermediate Similarity	NPD7473	Discontinued
0.7089	Intermediate Similarity	NPD2935	Discontinued
0.7083	Intermediate Similarity	NPD5402	Approved
0.7078	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD3818	Discontinued
0.7066	Intermediate Similarity	NPD1934	Approved
0.7052	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD4380	Phase 2
0.7041	Intermediate Similarity	NPD7768	Phase 2
0.7037	Intermediate Similarity	NPD7236	Approved
0.7035	Intermediate Similarity	NPD6232	Discontinued
0.7032	Intermediate Similarity	NPD8032	Phase 2
0.7026	Intermediate Similarity	NPD8404	Phase 2
0.7025	Intermediate Similarity	NPD7033	Discontinued
0.7025	Intermediate Similarity	NPD1510	Phase 2
0.7012	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1607	Approved
0.7006	Intermediate Similarity	NPD6651	Approved
0.7	Intermediate Similarity	NPD1608	Approved
0.7	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1240	Approved
0.6987	Remote Similarity	NPD4307	Phase 2
0.6975	Remote Similarity	NPD2309	Approved
0.6974	Remote Similarity	NPD3266	Approved
0.6974	Remote Similarity	NPD3267	Approved
0.697	Remote Similarity	NPD5403	Approved
0.6964	Remote Similarity	NPD37	Approved
0.6959	Remote Similarity	NPD5585	Approved
0.6951	Remote Similarity	NPD5401	Approved
0.6944	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD4965	Approved
0.6941	Remote Similarity	NPD4967	Phase 2
0.6941	Remote Similarity	NPD4966	Approved
0.694	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6004	Phase 3
0.6937	Remote Similarity	NPD6002	Phase 3
0.6937	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6005	Phase 3
0.6937	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD7229	Phase 3
0.6933	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1019	Discontinued
0.6923	Remote Similarity	NPD2801	Approved
0.6914	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD8285	Discontinued
0.6886	Remote Similarity	NPD7458	Discontinued
0.6882	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD8127	Discontinued
0.6879	Remote Similarity	NPD2979	Phase 3
0.6875	Remote Similarity	NPD3751	Discontinued
0.6871	Remote Similarity	NPD3887	Approved
0.6864	Remote Similarity	NPD6280	Approved
0.6864	Remote Similarity	NPD6279	Approved
0.686	Remote Similarity	NPD6234	Discontinued
0.6859	Remote Similarity	NPD3268	Approved
0.6859	Remote Similarity	NPD3764	Approved
0.6857	Remote Similarity	NPD2403	Approved
0.6854	Remote Similarity	NPD5953	Discontinued
0.6839	Remote Similarity	NPD3787	Discontinued
0.6836	Remote Similarity	NPD7286	Phase 2
0.6833	Remote Similarity	NPD8313	Approved
0.6833	Remote Similarity	NPD8312	Approved
0.6826	Remote Similarity	NPD7239	Suspended
0.6818	Remote Similarity	NPD2798	Approved
0.6813	Remote Similarity	NPD4308	Phase 3
0.681	Remote Similarity	NPD7003	Approved
0.6806	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD1876	Approved
0.6788	Remote Similarity	NPD1511	Approved
0.6784	Remote Similarity	NPD5353	Approved
0.678	Remote Similarity	NPD7799	Discontinued
0.6776	Remote Similarity	NPD9717	Approved
0.677	Remote Similarity	NPD2438	Suspended
0.6761	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6166	Phase 2
0.676	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD2797	Approved
0.6753	Remote Similarity	NPD1203	Approved
0.6748	Remote Similarity	NPD2654	Approved
0.6742	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4287	Approved
0.6732	Remote Similarity	NPD4359	Approved
0.673	Remote Similarity	NPD1933	Approved
0.673	Remote Similarity	NPD447	Suspended
0.673	Remote Similarity	NPD230	Phase 1
0.673	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.673	Remote Similarity	NPD6355	Discontinued
0.673	Remote Similarity	NPD5124	Phase 1
0.6725	Remote Similarity	NPD1465	Phase 2
0.6711	Remote Similarity	NPD1281	Approved
0.671	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4110	Phase 3
0.6707	Remote Similarity	NPD1512	Approved
0.6706	Remote Similarity	NPD5890	Approved
0.6706	Remote Similarity	NPD5889	Approved
0.6706	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5242	Approved
0.6704	Remote Similarity	NPD7074	Phase 3
0.6703	Remote Similarity	NPD8407	Phase 2
0.6689	Remote Similarity	NPD1778	Approved
0.6686	Remote Similarity	NPD7199	Phase 2
0.6685	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD4107	Approved
0.6667	Remote Similarity	NPD4140	Approved
0.6667	Remote Similarity	NPD1241	Discontinued
0.6648	Remote Similarity	NPD7054	Approved
0.6647	Remote Similarity	NPD6585	Discontinued
0.6646	Remote Similarity	NPD411	Approved
0.6645	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7685	Pre-registration
0.663	Remote Similarity	NPD8368	Discontinued
0.663	Remote Similarity	NPD8150	Discontinued
0.6626	Remote Similarity	NPD2353	Approved
0.6626	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD5691	Approved
0.6611	Remote Similarity	NPD7472	Approved
0.661	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD6386	Approved
0.6608	Remote Similarity	NPD6385	Approved
0.6605	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD4870	Approved
0.6592	Remote Similarity	NPD7228	Approved
0.6592	Remote Similarity	NPD7177	Discontinued
0.6587	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD5952	Clinical (unspecified phase)

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