NPASS Compound

Structure

NPC474746 OpenBabel07101719242D 27 31 0 0 1 0 0 0 0 0999 V2000 3.6655 -5.2165 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 3.0812 -3.5860 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 2.9027 -4.5699 0.0000 C 0 0 2 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 1 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 1.9613 -4.9072 0.0000 O 0 0 0 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 2 3 1 0 0 0 0 2 11 1 0 0 0 0 3 21 1 0 0 0 0 4 10 1 0 0 0 0 4 17 1 0 0 0 0 5 11 2 0 0 0 0 5 14 1 0 0 0 0 6 12 2 0 0 0 0 6 15 1 0 0 0 0 7 13 2 0 0 0 0 7 16 1 0 0 0 0 8 12 1 0 0 0 0 8 21 1 0 0 0 0 9 25 1 0 0 0 0 9 26 1 0 0 0 0 10 1 1 1 0 0 0 10 22 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 23 1 1 0 0 0 15 16 2 0 0 0 0 15 25 1 0 0 0 0 16 26 1 0 0 0 0 17 24 2 0 0 0 0 17 27 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 27 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	373.15
Volume:	362.25
LogP:	1.408
LogD:	1.097
LogS:	-2.566
# Rotatable Bonds:	4
TPSA:	88.46
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.605
Synthetic Accessibility Score:	4.447
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:	-5.097
MDCK Permeability:	5.0859522161772475e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.586
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.204

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.939
Plasma Protein Binding (PPB):	61.64345169067383%
Volume Distribution (VD):	2.948
Pgp-substrate:	41.49609375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.666
CYP1A2-substrate:	0.352
CYP2C19-inhibitor:	0.151
CYP2C19-substrate:	0.762
CYP2C9-inhibitor:	0.066
CYP2C9-substrate:	0.427
CYP2D6-inhibitor:	0.926
CYP2D6-substrate:	0.433
CYP3A4-inhibitor:	0.694
CYP3A4-substrate:	0.487

ADMET: Excretion

Clearance (CL):	14.058
Half-life (T1/2):	0.751

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.307
Drug-inuced Liver Injury (DILI):	0.237
AMES Toxicity:	0.061
Rat Oral Acute Toxicity:	0.719
Maximum Recommended Daily Dose:	0.948
Skin Sensitization:	0.045
Carcinogencity:	0.918
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.912

Download Data

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

Natural Product: NPC474746

Natural Product ID:	NPC474746
*Common Name:**	AMVDLCRDRNPXIY-ZNOCGUAXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	AMVDLCRDRNPXIY-ZNOCGUAXSA-N
Standard InCHI:	InChI=1S/C20H23NO6/c1-10(22)4-17(24)27-20-14(23)5-11-2-3-21-8-12-6-15-16(26-9-25-15)7-13(12)18(20)19(11)21/h5-7,10,14,18-20,22-23H,2-4,8-9H2,1H3/t10-,14+,18+,19-,20+/m1/s1
SMILES:	CC(CC(=O)OC1C(C=C2CCN3C2C1C4=CC5=C(C=C4C3)OCO5)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481181
PubChem CID:	44570382
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	=	6.35	ug.mL-1	PMID[490261]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	2.45	ug.mL-1	PMID[490261]
NPT2	Others	Unspecified		Ratio IC50	=	2.6	n.a.	PMID[490261]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	0.62	ug.mL-1	PMID[490261]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.49	ug.mL-1	PMID[490261]
NPT2	Others	Unspecified		Ratio IC50	=	10.2	n.a.	PMID[490261]
NPT2	Others	Unspecified		Ratio IC50	=	13.0	n.a.	PMID[490261]

☑ 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 NPC474746 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	225
0.1-0.2	1088
0.2-0.3	3020
0.3-0.4	9709
0.4-0.5	9285
0.5-0.6	12255
0.6-0.7	6079
0.7-0.8	873
0.8-0.85	93
0.85-0.9	46
0.9-0.95	14
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475981
0.9818	High Similarity	NPC474745
0.9758	High Similarity	NPC474325
0.9697	High Similarity	NPC237044
0.9636	High Similarity	NPC304675
0.9529	High Similarity	NPC230098
0.9455	High Similarity	NPC474708
0.9394	High Similarity	NPC475845
0.9333	High Similarity	NPC181653
0.9333	High Similarity	NPC57812
0.9333	High Similarity	NPC474324
0.9333	High Similarity	NPC190332
0.9217	High Similarity	NPC100566
0.9152	High Similarity	NPC320104
0.9118	High Similarity	NPC474470
0.8837	High Similarity	NPC187678
0.883	High Similarity	NPC470739
0.883	High Similarity	NPC477640
0.883	High Similarity	NPC225597
0.8824	High Similarity	NPC290759
0.8824	High Similarity	NPC475686
0.8824	High Similarity	NPC82533
0.8824	High Similarity	NPC266176
0.8824	High Similarity	NPC158148
0.8824	High Similarity	NPC58766
0.8802	High Similarity	NPC205167
0.8802	High Similarity	NPC4304
0.8802	High Similarity	NPC249274
0.8778	High Similarity	NPC33256
0.8772	High Similarity	NPC311991
0.8772	High Similarity	NPC474475
0.8736	High Similarity	NPC15919
0.8706	High Similarity	NPC476002
0.869	High Similarity	NPC97072
0.869	High Similarity	NPC215829
0.8656	High Similarity	NPC80472
0.8629	High Similarity	NPC148693
0.8629	High Similarity	NPC118633
0.8629	High Similarity	NPC294790
0.858	High Similarity	NPC244554
0.8506	High Similarity	NPC65403
0.8492	Intermediate Similarity	NPC9867
0.8452	Intermediate Similarity	NPC78733
0.8448	Intermediate Similarity	NPC75958
0.8439	Intermediate Similarity	NPC252960
0.8409	Intermediate Similarity	NPC49353
0.8372	Intermediate Similarity	NPC218614
0.8352	Intermediate Similarity	NPC2314
0.8333	Intermediate Similarity	NPC223124
0.8324	Intermediate Similarity	NPC180306
0.8324	Intermediate Similarity	NPC247972
0.8306	Intermediate Similarity	NPC319549
0.8294	Intermediate Similarity	NPC147091
0.8278	Intermediate Similarity	NPC275132
0.8261	Intermediate Similarity	NPC94499
0.8242	Intermediate Similarity	NPC162694
0.8225	Intermediate Similarity	NPC148898
0.8214	Intermediate Similarity	NPC223125
0.8207	Intermediate Similarity	NPC226708
0.8202	Intermediate Similarity	NPC229166
0.8202	Intermediate Similarity	NPC199465
0.8202	Intermediate Similarity	NPC128560
0.8198	Intermediate Similarity	NPC59028
0.8198	Intermediate Similarity	NPC92191
0.8198	Intermediate Similarity	NPC111485
0.8182	Intermediate Similarity	NPC73020
0.8182	Intermediate Similarity	NPC70290
0.8182	Intermediate Similarity	NPC215098
0.8182	Intermediate Similarity	NPC46744
0.8182	Intermediate Similarity	NPC14622
0.8182	Intermediate Similarity	NPC124302
0.8177	Intermediate Similarity	NPC116284
0.8177	Intermediate Similarity	NPC248642
0.8167	Intermediate Similarity	NPC32154
0.8167	Intermediate Similarity	NPC126284
0.8156	Intermediate Similarity	NPC241704
0.8136	Intermediate Similarity	NPC474953
0.8132	Intermediate Similarity	NPC156576
0.8125	Intermediate Similarity	NPC210918
0.8118	Intermediate Similarity	NPC210148
0.8118	Intermediate Similarity	NPC233029
0.8114	Intermediate Similarity	NPC238530
0.8114	Intermediate Similarity	NPC231198
0.8114	Intermediate Similarity	NPC232514
0.8114	Intermediate Similarity	NPC276944
0.8111	Intermediate Similarity	NPC320223
0.8111	Intermediate Similarity	NPC114364
0.8107	Intermediate Similarity	NPC274026
0.8105	Intermediate Similarity	NPC286135
0.8105	Intermediate Similarity	NPC328700
0.8105	Intermediate Similarity	NPC119818
0.8105	Intermediate Similarity	NPC202771
0.8105	Intermediate Similarity	NPC2173
0.8098	Intermediate Similarity	NPC166979
0.8095	Intermediate Similarity	NPC314100
0.8095	Intermediate Similarity	NPC120671
0.8095	Intermediate Similarity	NPC72788
0.8095	Intermediate Similarity	NPC475959
0.8095	Intermediate Similarity	NPC226652
0.8092	Intermediate Similarity	NPC477080
0.8077	Intermediate Similarity	NPC102760
0.8056	Intermediate Similarity	NPC283999
0.8056	Intermediate Similarity	NPC35680
0.8054	Intermediate Similarity	NPC82763
0.8046	Intermediate Similarity	NPC165797
0.8043	Intermediate Similarity	NPC214116
0.8042	Intermediate Similarity	NPC267414
0.8023	Intermediate Similarity	NPC301189
0.8023	Intermediate Similarity	NPC298186
0.8023	Intermediate Similarity	NPC150879
0.8012	Intermediate Similarity	NPC133011
0.8012	Intermediate Similarity	NPC82285
0.8011	Intermediate Similarity	NPC302527
0.8011	Intermediate Similarity	NPC16805
0.8011	Intermediate Similarity	NPC63152
0.8011	Intermediate Similarity	NPC167546
0.8	Intermediate Similarity	NPC237579
0.7978	Intermediate Similarity	NPC233718
0.7977	Intermediate Similarity	NPC146288
0.7977	Intermediate Similarity	NPC234392
0.7977	Intermediate Similarity	NPC31311
0.7967	Intermediate Similarity	NPC99179
0.7966	Intermediate Similarity	NPC476432
0.7966	Intermediate Similarity	NPC24264
0.7955	Intermediate Similarity	NPC59567
0.7923	Intermediate Similarity	NPC476574
0.7923	Intermediate Similarity	NPC155442
0.7923	Intermediate Similarity	NPC312918
0.7923	Intermediate Similarity	NPC474607
0.7923	Intermediate Similarity	NPC477561
0.7921	Intermediate Similarity	NPC247389
0.7921	Intermediate Similarity	NPC298979
0.7919	Intermediate Similarity	NPC216459
0.7919	Intermediate Similarity	NPC41178
0.7919	Intermediate Similarity	NPC138487
0.791	Intermediate Similarity	NPC225774
0.7903	Intermediate Similarity	NPC141440
0.7889	Intermediate Similarity	NPC57272
0.7889	Intermediate Similarity	NPC149090
0.7889	Intermediate Similarity	NPC19520
0.7886	Intermediate Similarity	NPC69360
0.7884	Intermediate Similarity	NPC125924
0.7882	Intermediate Similarity	NPC246587
0.7882	Intermediate Similarity	NPC476571
0.7882	Intermediate Similarity	NPC135538
0.7882	Intermediate Similarity	NPC24233
0.7882	Intermediate Similarity	NPC147390
0.7882	Intermediate Similarity	NPC428
0.788	Intermediate Similarity	NPC474650
0.7865	Intermediate Similarity	NPC219341
0.7865	Intermediate Similarity	NPC124657
0.7853	Intermediate Similarity	NPC233650
0.7838	Intermediate Similarity	NPC135772
0.7831	Intermediate Similarity	NPC469815
0.7831	Intermediate Similarity	NPC469816
0.7829	Intermediate Similarity	NPC65490
0.7829	Intermediate Similarity	NPC78359
0.7829	Intermediate Similarity	NPC148014
0.7829	Intermediate Similarity	NPC315707
0.7829	Intermediate Similarity	NPC40389
0.7824	Intermediate Similarity	NPC321505
0.7824	Intermediate Similarity	NPC191376
0.7824	Intermediate Similarity	NPC179825
0.7821	Intermediate Similarity	NPC210140
0.7819	Intermediate Similarity	NPC475754
0.7811	Intermediate Similarity	NPC185838
0.7811	Intermediate Similarity	NPC130926
0.7809	Intermediate Similarity	NPC13504
0.7809	Intermediate Similarity	NPC477563
0.7809	Intermediate Similarity	NPC196447
0.7809	Intermediate Similarity	NPC253043
0.7809	Intermediate Similarity	NPC24465
0.7809	Intermediate Similarity	NPC78222
0.7809	Intermediate Similarity	NPC136508
0.7809	Intermediate Similarity	NPC306843
0.7809	Intermediate Similarity	NPC134858
0.7809	Intermediate Similarity	NPC96603
0.7809	Intermediate Similarity	NPC212794
0.7807	Intermediate Similarity	NPC476576
0.7807	Intermediate Similarity	NPC186546
0.7791	Intermediate Similarity	NPC151895
0.7791	Intermediate Similarity	NPC220858
0.7791	Intermediate Similarity	NPC88249
0.7791	Intermediate Similarity	NPC192768
0.7791	Intermediate Similarity	NPC97221
0.7784	Intermediate Similarity	NPC106786
0.7784	Intermediate Similarity	NPC476575
0.7778	Intermediate Similarity	NPC204908
0.7778	Intermediate Similarity	NPC83198
0.7778	Intermediate Similarity	NPC59907
0.7778	Intermediate Similarity	NPC117717
0.7778	Intermediate Similarity	NPC24260
0.7778	Intermediate Similarity	NPC37144
0.7772	Intermediate Similarity	NPC475794
0.7772	Intermediate Similarity	NPC27887
0.7766	Intermediate Similarity	NPC46990
0.7765	Intermediate Similarity	NPC13916
0.7765	Intermediate Similarity	NPC264850
0.7758	Intermediate Similarity	NPC7018
0.7754	Intermediate Similarity	NPC57036

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 NPC474746 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	151
0.1-0.2	525
0.2-0.3	1023
0.3-0.4	2218
0.4-0.5	2630
0.5-0.6	1806
0.6-0.7	693
0.7-0.8	98
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8306	Intermediate Similarity	NPD7296	Approved
0.8182	Intermediate Similarity	NPD4420	Approved
0.8105	Intermediate Similarity	NPD5005	Approved
0.8105	Intermediate Similarity	NPD5006	Approved
0.8023	Intermediate Similarity	NPD2969	Approved
0.8023	Intermediate Similarity	NPD2970	Approved
0.8011	Intermediate Similarity	NPD6107	Approved
0.7978	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD4481	Phase 3
0.7965	Intermediate Similarity	NPD4773	Phase 2
0.7965	Intermediate Similarity	NPD4772	Phase 2
0.7944	Intermediate Similarity	NPD5313	Approved
0.7944	Intermediate Similarity	NPD5312	Approved
0.7923	Intermediate Similarity	NPD7280	Phase 3
0.7923	Intermediate Similarity	NPD7281	Phase 3
0.7877	Intermediate Similarity	NPD27	Approved
0.7877	Intermediate Similarity	NPD2489	Approved
0.7865	Intermediate Similarity	NPD6071	Discontinued
0.7865	Intermediate Similarity	NPD3051	Approved
0.7829	Intermediate Similarity	NPD2563	Approved
0.7829	Intermediate Similarity	NPD2560	Approved
0.7739	Intermediate Similarity	NPD7827	Phase 1
0.7733	Intermediate Similarity	NPD3641	Approved
0.7733	Intermediate Similarity	NPD3640	Phase 3
0.7733	Intermediate Similarity	NPD3639	Approved
0.7679	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7668	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD7312	Approved
0.7634	Intermediate Similarity	NPD7311	Approved
0.7634	Intermediate Similarity	NPD7313	Approved
0.7634	Intermediate Similarity	NPD7310	Approved
0.7594	Intermediate Similarity	NPD7309	Approved
0.7582	Intermediate Similarity	NPD2898	Approved
0.7544	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4584	Approved
0.7513	Intermediate Similarity	NPD5582	Discontinued
0.7513	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD4663	Approved
0.7487	Intermediate Similarity	NPD2488	Approved
0.7487	Intermediate Similarity	NPD2490	Approved
0.7474	Intermediate Similarity	NPD7906	Approved
0.7473	Intermediate Similarity	NPD4166	Phase 2
0.7472	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD2977	Approved
0.7472	Intermediate Similarity	NPD2978	Approved
0.7452	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD4577	Approved
0.7447	Intermediate Similarity	NPD4578	Approved
0.7427	Intermediate Similarity	NPD4236	Phase 3
0.7427	Intermediate Similarity	NPD4237	Approved
0.7407	Intermediate Similarity	NPD8054	Approved
0.7407	Intermediate Similarity	NPD6853	Approved
0.7407	Intermediate Similarity	NPD6851	Approved
0.7407	Intermediate Similarity	NPD8053	Approved
0.7389	Intermediate Similarity	NPD4965	Approved
0.7389	Intermediate Similarity	NPD4967	Phase 2
0.7389	Intermediate Similarity	NPD4966	Approved
0.7386	Intermediate Similarity	NPD4210	Discontinued
0.738	Intermediate Similarity	NPD6297	Approved
0.7374	Intermediate Similarity	NPD5773	Approved
0.7374	Intermediate Similarity	NPD5772	Approved
0.7354	Intermediate Similarity	NPD2971	Approved
0.7354	Intermediate Similarity	NPD2968	Approved
0.7341	Intermediate Similarity	NPD5241	Discontinued
0.7323	Intermediate Similarity	NPD2493	Approved
0.7323	Intermediate Similarity	NPD2494	Approved
0.7323	Intermediate Similarity	NPD3452	Approved
0.7323	Intermediate Similarity	NPD3450	Approved
0.7308	Intermediate Similarity	NPD6234	Discontinued
0.73	Intermediate Similarity	NPD4582	Approved
0.73	Intermediate Similarity	NPD4583	Approved
0.7299	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD2975	Approved
0.7296	Intermediate Similarity	NPD2974	Approved
0.7296	Intermediate Similarity	NPD2973	Approved
0.7286	Intermediate Similarity	NPD3057	Approved
0.7283	Intermediate Similarity	NPD4010	Discontinued
0.7273	Intermediate Similarity	NPD4580	Approved
0.7273	Intermediate Similarity	NPD8156	Discontinued
0.7256	Intermediate Similarity	NPD6723	Discontinued
0.7253	Intermediate Similarity	NPD7831	Phase 2
0.7253	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD7833	Phase 2
0.725	Intermediate Similarity	NPD4002	Approved
0.725	Intermediate Similarity	NPD4004	Approved
0.724	Intermediate Similarity	NPD3857	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6997	Phase 2
0.7222	Intermediate Similarity	NPD7298	Approved
0.7222	Intermediate Similarity	NPD37	Approved
0.7219	Intermediate Similarity	NPD8251	Approved
0.7219	Intermediate Similarity	NPD8252	Approved
0.7219	Intermediate Similarity	NPD7228	Approved
0.7219	Intermediate Similarity	NPD8099	Discontinued
0.7216	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6666	Approved
0.72	Intermediate Similarity	NPD6667	Approved
0.72	Intermediate Similarity	NPD3533	Approved
0.72	Intermediate Similarity	NPD2972	Approved
0.7198	Intermediate Similarity	NPD7047	Phase 3
0.7191	Intermediate Similarity	NPD3687	Approved
0.7191	Intermediate Similarity	NPD3686	Approved
0.7186	Intermediate Similarity	NPD4107	Approved
0.7173	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD5604	Discontinued
0.7151	Intermediate Similarity	NPD4017	Approved
0.7135	Intermediate Similarity	NPD6030	Approved
0.7135	Intermediate Similarity	NPD6031	Approved
0.712	Intermediate Similarity	NPD3936	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD2491	Approved
0.7114	Intermediate Similarity	NPD3448	Approved
0.7098	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD4482	Phase 3
0.7044	Intermediate Similarity	NPD4040	Phase 1
0.7041	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4727	Phase 1
0.7033	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD5177	Phase 3
0.7018	Intermediate Similarity	NPD6625	Approved
0.7014	Intermediate Similarity	NPD4665	Approved
0.7014	Intermediate Similarity	NPD4111	Phase 1
0.7011	Intermediate Similarity	NPD6788	Approved
0.7011	Intermediate Similarity	NPD3656	Approved
0.701	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7315	Approved
0.7005	Intermediate Similarity	NPD5676	Approved
0.6995	Remote Similarity	NPD7497	Discontinued
0.6989	Remote Similarity	NPD4666	Phase 3
0.6989	Remote Similarity	NPD5677	Discontinued
0.6989	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD7930	Approved
0.6983	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD7240	Approved
0.6978	Remote Similarity	NPD6386	Approved
0.6978	Remote Similarity	NPD6385	Approved
0.6961	Remote Similarity	NPD4005	Discontinued
0.6959	Remote Similarity	NPD2238	Phase 2
0.6957	Remote Similarity	NPD5978	Approved
0.6957	Remote Similarity	NPD5977	Approved
0.6952	Remote Similarity	NPD7199	Phase 2
0.6949	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD7907	Approved
0.6943	Remote Similarity	NPD7549	Discontinued
0.6943	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD4859	Phase 1
0.6939	Remote Similarity	NPD6842	Approved
0.6939	Remote Similarity	NPD6841	Approved
0.6939	Remote Similarity	NPD6843	Phase 3
0.6935	Remote Similarity	NPD5709	Phase 3
0.6932	Remote Similarity	NPD3060	Approved
0.6927	Remote Similarity	NPD7999	Approved
0.6923	Remote Similarity	NPD7048	Phase 3
0.6901	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD2904	Discontinued
0.6897	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD7039	Approved
0.6891	Remote Similarity	NPD7038	Approved
0.6879	Remote Similarity	NPD2492	Phase 1
0.6878	Remote Similarity	NPD5242	Approved
0.6872	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD2420	Approved
0.6872	Remote Similarity	NPD2421	Approved
0.6868	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD8153	Approved
0.6842	Remote Similarity	NPD8152	Approved
0.6836	Remote Similarity	NPD4162	Approved
0.6833	Remote Similarity	NPD1424	Approved
0.6833	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1375	Discontinued
0.6816	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD3705	Approved
0.68	Remote Similarity	NPD4108	Discontinued
0.6798	Remote Similarity	NPD5754	Discontinued
0.6793	Remote Similarity	NPD7110	Phase 1
0.6793	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6688	Approved
0.6789	Remote Similarity	NPD6687	Approved
0.6789	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD2653	Approved
0.678	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD3124	Discontinued
0.6774	Remote Similarity	NPD5353	Approved
0.6768	Remote Similarity	NPD7291	Discontinued
0.6761	Remote Similarity	NPD2161	Phase 2
0.6758	Remote Similarity	NPD7427	Discontinued
0.6758	Remote Similarity	NPD2122	Discontinued
0.6757	Remote Similarity	NPD3383	Approved
0.6757	Remote Similarity	NPD3382	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