NPASS Compound

Structure

NPC474745 OpenBabel07101719242D 26 30 0 0 1 0 0 0 0 0999 V2000 -1.9613 4.9072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9027 4.5699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0812 3.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5232 0.5458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9599 -0.2804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0900 2.3208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1327 -0.0805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1327 1.5457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7927 -0.1809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0881 0.7326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9115 1.3369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4285 0.3260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4285 1.1392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3272 2.9674 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8369 0.3260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8369 1.1392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3184 2.9394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7927 1.6462 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0299 0.9996 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6142 2.6301 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 0.5058 3.9513 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4970 1.9554 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6102 0.0748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6102 1.3904 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3770 3.2767 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 17 1 0 0 0 0 4 5 1 0 0 0 0 4 11 1 0 0 0 0 5 21 1 0 0 0 0 6 11 2 0 0 0 0 6 14 1 0 0 0 0 7 12 2 0 0 0 0 7 15 1 0 0 0 0 8 13 2 0 0 0 0 8 16 1 0 0 0 0 9 12 1 0 0 0 0 9 21 1 0 0 0 0 10 24 1 0 0 0 0 10 25 1 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 14 20 1 0 0 0 0 14 22 1 1 0 0 0 15 16 2 0 0 0 0 15 24 1 0 0 0 0 16 25 1 0 0 0 0 17 23 2 0 0 0 0 17 26 1 0 0 0 0 18 13 1 6 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 19 21 1 1 0 0 0 20 26 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	357.16
Volume:	353.459
LogP:	2.838
LogD:	2.442
LogS:	-3.442
# Rotatable Bonds:	4
TPSA:	68.23
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.66
Synthetic Accessibility Score:	4.212
Fsp3:	0.55
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:	-4.766
MDCK Permeability:	4.480949428398162e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.61
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.526

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.988
Plasma Protein Binding (PPB):	74.98222351074219%
Volume Distribution (VD):	2.352
Pgp-substrate:	14.89853572845459%

ADMET: Metabolism

CYP1A2-inhibitor:	0.748
CYP1A2-substrate:	0.316
CYP2C19-inhibitor:	0.365
CYP2C19-substrate:	0.714
CYP2C9-inhibitor:	0.056
CYP2C9-substrate:	0.567
CYP2D6-inhibitor:	0.972
CYP2D6-substrate:	0.641
CYP3A4-inhibitor:	0.819
CYP3A4-substrate:	0.35

ADMET: Excretion

Clearance (CL):	17.483
Half-life (T1/2):	0.451

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.185
Drug-inuced Liver Injury (DILI):	0.276
AMES Toxicity:	0.057
Rat Oral Acute Toxicity:	0.876
Maximum Recommended Daily Dose:	0.93
Skin Sensitization:	0.053
Carcinogencity:	0.879
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC474745

Natural Product ID:	NPC474745
*Common Name:**	HSXFFYXJBILABT-VVHHDAOASA-N
IUPAC Name:	n.a.
Synonyms:	1-O-Butanoyllycorine
Standard InCHIKey:	HSXFFYXJBILABT-VVHHDAOASA-N
Standard InCHI:	InChI=1S/C20H23NO5/c1-2-3-17(23)26-20-14(22)6-11-4-5-21-9-12-7-15-16(25-10-24-15)8-13(12)18(20)19(11)21/h6-8,14,18-20,22H,2-5,9-10H2,1H3/t14-,18-,19+,20+/m0/s1
SMILES:	CCCC(=O)O[C@@H]1[C@@H](O)C=C2[C@@H]3[C@@H]1c1cc4OCOc4cc1CN3CC2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481180
PubChem CID:	25147571
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001775] Amaryllidaceae alkaloids [CHEMONTID:0004120] Lycorine-type amaryllidaceae alkaloids

*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
NPO25024	Lycoris traubii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19013823]
NPO25024	Lycoris traubii	Species	Amaryllidaceae	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
IC50	4
Others	3

Activity Type	# Activity
Cell Line	1
Organism	3
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT171	Cell Line	MRC5	Homo sapiens	IC50	=	3.6	ug.mL-1	PMID[554485]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	1.38	ug.mL-1	PMID[554485]
NPT2	Others	Unspecified		Ratio IC50	=	2.6	n.a.	PMID[554485]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	0.41	ug.mL-1	PMID[554485]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.32	ug.mL-1	PMID[554485]
NPT2	Others	Unspecified		Ratio IC50	=	8.8	n.a.	PMID[554485]
NPT2	Others	Unspecified		Ratio IC50	=	11.3	n.a.	PMID[554485]

☑ 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 NPC474745 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	215
0.1-0.2	1062
0.2-0.3	3036
0.3-0.4	10109
0.4-0.5	8986
0.5-0.6	12915
0.6-0.7	5245
0.7-0.8	953
0.8-0.85	98
0.85-0.9	32
0.9-0.95	33
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9938	High Similarity	NPC474325
0.9877	High Similarity	NPC237044
0.9818	High Similarity	NPC475981
0.9818	High Similarity	NPC474746
0.9815	High Similarity	NPC304675
0.9701	High Similarity	NPC230098
0.963	High Similarity	NPC474708
0.9568	High Similarity	NPC475845
0.9506	High Similarity	NPC181653
0.9506	High Similarity	NPC190332
0.9506	High Similarity	NPC474324
0.9506	High Similarity	NPC57812
0.9387	High Similarity	NPC100566
0.9321	High Similarity	NPC320104
0.9281	High Similarity	NPC474470
0.8988	High Similarity	NPC477640
0.8988	High Similarity	NPC225597
0.8988	High Similarity	NPC470739
0.8982	High Similarity	NPC475686
0.8982	High Similarity	NPC82533
0.8982	High Similarity	NPC158148
0.8982	High Similarity	NPC266176
0.8982	High Similarity	NPC58766
0.8982	High Similarity	NPC290759
0.8963	High Similarity	NPC249274
0.8963	High Similarity	NPC4304
0.8963	High Similarity	NPC205167
0.8929	High Similarity	NPC474475
0.8929	High Similarity	NPC311991
0.8927	High Similarity	NPC33256
0.8882	High Similarity	NPC187678
0.8862	High Similarity	NPC476002
0.8848	High Similarity	NPC97072
0.8848	High Similarity	NPC215829
0.8779	High Similarity	NPC118633
0.8779	High Similarity	NPC294790
0.8779	High Similarity	NPC15919
0.8779	High Similarity	NPC148693
0.8621	High Similarity	NPC244554
0.8606	High Similarity	NPC78733
0.8588	High Similarity	NPC252960
0.8547	High Similarity	NPC65403
0.8531	High Similarity	NPC9867
0.8521	High Similarity	NPC218614
0.8497	Intermediate Similarity	NPC2314
0.8495	Intermediate Similarity	NPC80472
0.8488	Intermediate Similarity	NPC75958
0.8485	Intermediate Similarity	NPC223124
0.8471	Intermediate Similarity	NPC247972
0.8448	Intermediate Similarity	NPC49353
0.8443	Intermediate Similarity	NPC147091
0.8418	Intermediate Similarity	NPC275132
0.838	Intermediate Similarity	NPC162694
0.8373	Intermediate Similarity	NPC148898
0.8364	Intermediate Similarity	NPC223125
0.8363	Intermediate Similarity	NPC180306
0.8343	Intermediate Similarity	NPC59028
0.8343	Intermediate Similarity	NPC199465
0.8343	Intermediate Similarity	NPC92191
0.8343	Intermediate Similarity	NPC128560
0.8343	Intermediate Similarity	NPC229166
0.8343	Intermediate Similarity	NPC111485
0.8315	Intermediate Similarity	NPC116284
0.8315	Intermediate Similarity	NPC248642
0.8305	Intermediate Similarity	NPC126284
0.8305	Intermediate Similarity	NPC32154
0.8297	Intermediate Similarity	NPC94499
0.8295	Intermediate Similarity	NPC241704
0.8268	Intermediate Similarity	NPC156576
0.8266	Intermediate Similarity	NPC210918
0.8263	Intermediate Similarity	NPC210148
0.8263	Intermediate Similarity	NPC233029
0.8256	Intermediate Similarity	NPC232514
0.8256	Intermediate Similarity	NPC231198
0.8256	Intermediate Similarity	NPC238530
0.8256	Intermediate Similarity	NPC276944
0.8253	Intermediate Similarity	NPC274026
0.8249	Intermediate Similarity	NPC114364
0.8249	Intermediate Similarity	NPC320223
0.8242	Intermediate Similarity	NPC475959
0.8235	Intermediate Similarity	NPC477080
0.8212	Intermediate Similarity	NPC102760
0.8192	Intermediate Similarity	NPC35680
0.8187	Intermediate Similarity	NPC165797
0.8171	Intermediate Similarity	NPC474953
0.8161	Intermediate Similarity	NPC150879
0.8161	Intermediate Similarity	NPC301189
0.8161	Intermediate Similarity	NPC298186
0.8155	Intermediate Similarity	NPC133011
0.8155	Intermediate Similarity	NPC82285
0.815	Intermediate Similarity	NPC167546
0.815	Intermediate Similarity	NPC16805
0.815	Intermediate Similarity	NPC302527
0.8142	Intermediate Similarity	NPC319549
0.8132	Intermediate Similarity	NPC237579
0.8118	Intermediate Similarity	NPC234392
0.8118	Intermediate Similarity	NPC31311
0.8118	Intermediate Similarity	NPC146288
0.8111	Intermediate Similarity	NPC233718
0.8103	Intermediate Similarity	NPC476432
0.8103	Intermediate Similarity	NPC24264
0.8101	Intermediate Similarity	NPC99179
0.8092	Intermediate Similarity	NPC59567
0.809	Intermediate Similarity	NPC283999
0.8087	Intermediate Similarity	NPC82763
0.8077	Intermediate Similarity	NPC214116
0.8075	Intermediate Similarity	NPC267414
0.8059	Intermediate Similarity	NPC41178
0.8059	Intermediate Similarity	NPC138487
0.8059	Intermediate Similarity	NPC216459
0.8057	Intermediate Similarity	NPC247389
0.8057	Intermediate Similarity	NPC298979
0.8056	Intermediate Similarity	NPC476574
0.8056	Intermediate Similarity	NPC155442
0.8056	Intermediate Similarity	NPC312918
0.8056	Intermediate Similarity	NPC477561
0.8046	Intermediate Similarity	NPC225774
0.8043	Intermediate Similarity	NPC226708
0.8043	Intermediate Similarity	NPC63152
0.8033	Intermediate Similarity	NPC141440
0.8024	Intermediate Similarity	NPC246587
0.8024	Intermediate Similarity	NPC135538
0.8024	Intermediate Similarity	NPC428
0.8024	Intermediate Similarity	NPC476571
0.8024	Intermediate Similarity	NPC24233
0.8024	Intermediate Similarity	NPC147390
0.8023	Intermediate Similarity	NPC57272
0.8021	Intermediate Similarity	NPC73020
0.8021	Intermediate Similarity	NPC124302
0.8021	Intermediate Similarity	NPC70290
0.8021	Intermediate Similarity	NPC14622
0.8021	Intermediate Similarity	NPC46744
0.8021	Intermediate Similarity	NPC215098
0.8	Intermediate Similarity	NPC124657
0.8	Intermediate Similarity	NPC219341
0.7989	Intermediate Similarity	NPC233650
0.7967	Intermediate Similarity	NPC135772
0.7964	Intermediate Similarity	NPC321505
0.7964	Intermediate Similarity	NPC179825
0.7964	Intermediate Similarity	NPC191376
0.7956	Intermediate Similarity	NPC474607
0.7955	Intermediate Similarity	NPC210140
0.7952	Intermediate Similarity	NPC185838
0.7952	Intermediate Similarity	NPC130926
0.7947	Intermediate Similarity	NPC286135
0.7947	Intermediate Similarity	NPC328700
0.7947	Intermediate Similarity	NPC202771
0.7947	Intermediate Similarity	NPC2173
0.7947	Intermediate Similarity	NPC119818
0.7943	Intermediate Similarity	NPC253043
0.7943	Intermediate Similarity	NPC196447
0.7943	Intermediate Similarity	NPC78222
0.7943	Intermediate Similarity	NPC134858
0.7943	Intermediate Similarity	NPC136508
0.7943	Intermediate Similarity	NPC477563
0.7943	Intermediate Similarity	NPC212794
0.7943	Intermediate Similarity	NPC306843
0.7943	Intermediate Similarity	NPC96603
0.7943	Intermediate Similarity	NPC13504
0.7937	Intermediate Similarity	NPC72788
0.7937	Intermediate Similarity	NPC226652
0.7937	Intermediate Similarity	NPC314100
0.7937	Intermediate Similarity	NPC120671
0.7935	Intermediate Similarity	NPC166979
0.7929	Intermediate Similarity	NPC88249
0.7929	Intermediate Similarity	NPC97221
0.7929	Intermediate Similarity	NPC192768
0.7929	Intermediate Similarity	NPC220858
0.7929	Intermediate Similarity	NPC151895
0.7921	Intermediate Similarity	NPC149090
0.7921	Intermediate Similarity	NPC19520
0.7919	Intermediate Similarity	NPC106786
0.7919	Intermediate Similarity	NPC69360
0.7912	Intermediate Similarity	NPC476575
0.7912	Intermediate Similarity	NPC474650
0.7901	Intermediate Similarity	NPC7018
0.7886	Intermediate Similarity	NPC324144
0.7874	Intermediate Similarity	NPC232924
0.7874	Intermediate Similarity	NPC306902
0.7874	Intermediate Similarity	NPC160298
0.7874	Intermediate Similarity	NPC266753
0.7874	Intermediate Similarity	NPC477559
0.787	Intermediate Similarity	NPC103379
0.787	Intermediate Similarity	NPC477565
0.7865	Intermediate Similarity	NPC6152
0.7861	Intermediate Similarity	NPC315707
0.7861	Intermediate Similarity	NPC40389
0.7861	Intermediate Similarity	NPC148014
0.7861	Intermediate Similarity	NPC65490
0.7861	Intermediate Similarity	NPC475326
0.7861	Intermediate Similarity	NPC78359
0.7857	Intermediate Similarity	NPC476151
0.7853	Intermediate Similarity	NPC12053
0.7853	Intermediate Similarity	NPC117188
0.7853	Intermediate Similarity	NPC474931
0.7853	Intermediate Similarity	NPC145832
0.7853	Intermediate Similarity	NPC306555
0.7853	Intermediate Similarity	NPC81218
0.7853	Intermediate Similarity	NPC158376
0.7853	Intermediate Similarity	NPC205421

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 NPC474745 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	526
0.2-0.3	984
0.3-0.4	2178
0.4-0.5	2644
0.5-0.6	1848
0.6-0.7	698
0.7-0.8	112
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8161	Intermediate Similarity	NPD2969	Approved
0.8161	Intermediate Similarity	NPD2970	Approved
0.815	Intermediate Similarity	NPD6107	Approved
0.8142	Intermediate Similarity	NPD7296	Approved
0.8114	Intermediate Similarity	NPD4481	Phase 3
0.8107	Intermediate Similarity	NPD4773	Phase 2
0.8107	Intermediate Similarity	NPD4772	Phase 2
0.8056	Intermediate Similarity	NPD7281	Phase 3
0.8056	Intermediate Similarity	NPD7280	Phase 3
0.8021	Intermediate Similarity	NPD4420	Approved
0.8011	Intermediate Similarity	NPD2489	Approved
0.8011	Intermediate Similarity	NPD27	Approved
0.8011	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3051	Approved
0.7947	Intermediate Similarity	NPD5005	Approved
0.7947	Intermediate Similarity	NPD5006	Approved
0.7898	Intermediate Similarity	NPD6071	Discontinued
0.7877	Intermediate Similarity	NPD5312	Approved
0.7877	Intermediate Similarity	NPD5313	Approved
0.787	Intermediate Similarity	NPD3641	Approved
0.787	Intermediate Similarity	NPD3639	Approved
0.787	Intermediate Similarity	NPD3640	Phase 3
0.7861	Intermediate Similarity	NPD2563	Approved
0.7861	Intermediate Similarity	NPD2560	Approved
0.7818	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD7827	Phase 1
0.7709	Intermediate Similarity	NPD2898	Approved
0.7696	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7663	Intermediate Similarity	NPD7310	Approved
0.7663	Intermediate Similarity	NPD7312	Approved
0.7663	Intermediate Similarity	NPD7313	Approved
0.7663	Intermediate Similarity	NPD7311	Approved
0.7647	Intermediate Similarity	NPD4584	Approved
0.7632	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD5582	Discontinued
0.7622	Intermediate Similarity	NPD7309	Approved
0.7606	Intermediate Similarity	NPD2488	Approved
0.7606	Intermediate Similarity	NPD2490	Approved
0.76	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD2977	Approved
0.76	Intermediate Similarity	NPD2978	Approved
0.7598	Intermediate Similarity	NPD4166	Phase 2
0.756	Intermediate Similarity	NPD4237	Approved
0.756	Intermediate Similarity	NPD4236	Phase 3
0.754	Intermediate Similarity	NPD4663	Approved
0.7527	Intermediate Similarity	NPD6853	Approved
0.7527	Intermediate Similarity	NPD6851	Approved
0.7514	Intermediate Similarity	NPD4210	Discontinued
0.75	Intermediate Similarity	NPD5773	Approved
0.75	Intermediate Similarity	NPD7906	Approved
0.75	Intermediate Similarity	NPD6297	Approved
0.75	Intermediate Similarity	NPD5772	Approved
0.7473	Intermediate Similarity	NPD4577	Approved
0.7473	Intermediate Similarity	NPD4578	Approved
0.7473	Intermediate Similarity	NPD2968	Approved
0.7473	Intermediate Similarity	NPD2971	Approved
0.7471	Intermediate Similarity	NPD5241	Discontinued
0.7433	Intermediate Similarity	NPD8054	Approved
0.7433	Intermediate Similarity	NPD8053	Approved
0.7427	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD4965	Approved
0.7416	Intermediate Similarity	NPD4967	Phase 2
0.7416	Intermediate Similarity	NPD4966	Approved
0.7403	Intermediate Similarity	NPD4010	Discontinued
0.7398	Intermediate Similarity	NPD3057	Approved
0.7374	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7831	Phase 2
0.7374	Intermediate Similarity	NPD7833	Phase 2
0.7347	Intermediate Similarity	NPD3450	Approved
0.7347	Intermediate Similarity	NPD2494	Approved
0.7347	Intermediate Similarity	NPD2493	Approved
0.7347	Intermediate Similarity	NPD3452	Approved
0.7345	Intermediate Similarity	NPD7298	Approved
0.7341	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6234	Discontinued
0.733	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6667	Approved
0.7326	Intermediate Similarity	NPD6666	Approved
0.7323	Intermediate Similarity	NPD4583	Approved
0.7323	Intermediate Similarity	NPD4582	Approved
0.732	Intermediate Similarity	NPD2975	Approved
0.732	Intermediate Similarity	NPD2974	Approved
0.732	Intermediate Similarity	NPD2973	Approved
0.7316	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD3686	Approved
0.7314	Intermediate Similarity	NPD3687	Approved
0.731	Intermediate Similarity	NPD3533	Approved
0.731	Intermediate Similarity	NPD2972	Approved
0.7308	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD8156	Discontinued
0.7296	Intermediate Similarity	NPD4107	Approved
0.7296	Intermediate Similarity	NPD4580	Approved
0.7287	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5604	Discontinued
0.7277	Intermediate Similarity	NPD6723	Discontinued
0.7273	Intermediate Similarity	NPD4004	Approved
0.7273	Intermediate Similarity	NPD4017	Approved
0.7273	Intermediate Similarity	NPD4002	Approved
0.726	Intermediate Similarity	NPD6997	Phase 2
0.7257	Intermediate Similarity	NPD6031	Approved
0.7257	Intermediate Similarity	NPD6030	Approved
0.7247	Intermediate Similarity	NPD37	Approved
0.7243	Intermediate Similarity	NPD8252	Approved
0.7243	Intermediate Similarity	NPD7228	Approved
0.7243	Intermediate Similarity	NPD8251	Approved
0.7243	Intermediate Similarity	NPD8099	Discontinued
0.7222	Intermediate Similarity	NPD2491	Approved
0.7222	Intermediate Similarity	NPD3448	Approved
0.722	Intermediate Similarity	NPD7047	Phase 3
0.7212	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4482	Phase 3
0.7159	Intermediate Similarity	NPD4727	Phase 1
0.7151	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD4040	Phase 1
0.715	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD3656	Approved
0.7108	Intermediate Similarity	NPD5676	Approved
0.7104	Intermediate Similarity	NPD4666	Phase 3
0.7104	Intermediate Similarity	NPD2042	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD2041	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6385	Approved
0.7095	Intermediate Similarity	NPD6386	Approved
0.7083	Intermediate Similarity	NPD3857	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD5978	Approved
0.7072	Intermediate Similarity	NPD5977	Approved
0.7052	Intermediate Similarity	NPD5177	Phase 3
0.7052	Intermediate Similarity	NPD3060	Approved
0.7049	Intermediate Similarity	NPD5709	Phase 3
0.7044	Intermediate Similarity	NPD4859	Phase 1
0.7037	Intermediate Similarity	NPD6625	Approved
0.7033	Intermediate Similarity	NPD6788	Approved
0.7024	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD7497	Discontinued
0.7011	Intermediate Similarity	NPD5677	Discontinued
0.7011	Intermediate Similarity	NPD2904	Discontinued
0.7	Intermediate Similarity	NPD7039	Approved
0.7	Intermediate Similarity	NPD7240	Approved
0.7	Intermediate Similarity	NPD2492	Phase 1
0.7	Intermediate Similarity	NPD7038	Approved
0.6989	Remote Similarity	NPD2420	Approved
0.6989	Remote Similarity	NPD2421	Approved
0.6989	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD4005	Discontinued
0.6982	Remote Similarity	NPD2238	Phase 2
0.6973	Remote Similarity	NPD7199	Phase 2
0.6971	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7549	Discontinued
0.6963	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6842	Approved
0.6959	Remote Similarity	NPD6841	Approved
0.6959	Remote Similarity	NPD6843	Phase 3
0.6954	Remote Similarity	NPD4162	Approved
0.6946	Remote Similarity	NPD7999	Approved
0.6946	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD1375	Discontinued
0.6933	Remote Similarity	NPD3705	Approved
0.6932	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5754	Discontinued
0.6906	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD7110	Phase 1
0.6901	Remote Similarity	NPD2653	Approved
0.6901	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD6687	Approved
0.6898	Remote Similarity	NPD5242	Approved
0.6898	Remote Similarity	NPD6688	Approved
0.6893	Remote Similarity	NPD3124	Discontinued
0.6889	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2161	Phase 2
0.6872	Remote Similarity	NPD4111	Phase 1
0.6872	Remote Similarity	NPD2122	Discontinued
0.6872	Remote Similarity	NPD7427	Discontinued
0.6872	Remote Similarity	NPD7291	Discontinued
0.6872	Remote Similarity	NPD4665	Approved
0.6865	Remote Similarity	NPD6315	Phase 2
0.6864	Remote Similarity	NPD5718	Phase 2
0.6858	Remote Similarity	NPD8153	Approved
0.6858	Remote Similarity	NPD8152	Approved
0.6854	Remote Similarity	NPD4123	Phase 3
0.6854	Remote Similarity	NPD3536	Discontinued
0.6854	Remote Similarity	NPD1424	Approved
0.6848	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7315	Approved
0.6845	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7930	Approved
0.6836	Remote Similarity	NPD3845	Phase 1
0.6825	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD2674	Phase 3
0.6821	Remote Similarity	NPD4108	Discontinued
0.6821	Remote Similarity	NPD1753	Discontinued
0.6818	Remote Similarity	NPD6331	Phase 2
0.6816	Remote Similarity	NPD6090	Discontinued

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