NPASS Compound

Structure

CID100566 OpenBabel06191715442D 22 26 0 0 1 0 0 0 0 0999 V2000 -0.4405 4.2857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5254 0.8807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7627 -0.4403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7626 2.2020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2886 -0.4403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2884 1.3213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7630 -0.4403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4067 0.4407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7627 1.3211 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5257 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5256 0.8808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0513 0.0002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0512 0.8810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0001 2.6424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7630 1.3210 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.8807 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7629 2.2019 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 -1.5480 2.6552 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0002 3.5230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8891 -0.2719 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8889 1.1533 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 3 1 0 0 0 0 3 18 1 0 0 0 0 4 9 1 0 0 0 0 4 14 2 0 0 0 0 5 10 2 0 0 0 0 5 12 1 0 0 0 0 6 11 2 0 0 0 0 6 13 1 0 0 0 0 7 10 1 0 0 0 0 7 18 1 0 0 0 0 8 21 1 0 0 0 0 8 22 1 0 0 0 0 9 2 1 6 0 0 0 9 16 1 0 0 0 0 10 11 1 0 0 0 0 12 13 2 0 0 0 0 12 21 1 0 0 0 0 13 22 1 0 0 0 0 14 17 1 0 0 0 0 14 20 1 0 0 0 0 15 11 1 6 0 0 0 15 16 1 0 0 0 0 15 17 1 0 0 0 0 16 18 1 6 0 0 0 17 19 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	301.13
Volume:	295.418
LogP:	1.957
LogD:	2.217
LogS:	-2.239
# Rotatable Bonds:	1
TPSA:	51.16
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.854
Synthetic Accessibility Score:	4.353
Fsp3:	0.529
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:	-4.721
MDCK Permeability:	4.9167490942636505e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.577
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.439
30% Bioavailability (F30%):	0.607

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.993
Plasma Protein Binding (PPB):	69.3815689086914%
Volume Distribution (VD):	2.745
Pgp-substrate:	31.1849422454834%

ADMET: Metabolism

CYP1A2-inhibitor:	0.781
CYP1A2-substrate:	0.888
CYP2C19-inhibitor:	0.128
CYP2C19-substrate:	0.906
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.352
CYP2D6-inhibitor:	0.949
CYP2D6-substrate:	0.837
CYP3A4-inhibitor:	0.245
CYP3A4-substrate:	0.746

ADMET: Excretion

Clearance (CL):	17.157
Half-life (T1/2):	0.428

ADMET: Toxicity

hERG Blockers:	0.084
Human Hepatotoxicity (H-HT):	0.708
Drug-inuced Liver Injury (DILI):	0.23
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.85
Maximum Recommended Daily Dose:	0.924
Skin Sensitization:	0.885
Carcinogencity:	0.83
Eye Corrosion:	0.007
Eye Irritation:	0.022
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC100566

Natural Product ID:	NPC100566
*Common Name:**	Amarbellisine
IUPAC Name:	n.a.
Synonyms:	Amarbellisine
Standard InCHIKey:	FKVRMQNEWFZVGO-VHYHWGNDSA-N
Standard InCHI:	InChI=1S/C17H19NO4/c1-20-14-4-9-2-3-18-7-10-5-12-13(22-8-21-12)6-11(10)15(16(9)18)17(14)19/h4-6,9,15-17,19H,2-3,7-8H2,1H3/t9-,15-,16-,17+/m0/s1
SMILES:	COC1=C[C@@H]2CCN3[C@@H]2[C@@H]([C@@H]1O)c1cc2OCOc2cc1C3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL575533
PubChem CID:	10017737
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
NPO23239	Amaryllis belladonna	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/ja01076a047]
NPO23239	Amaryllis belladonna	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6512532]
NPO23239	Amaryllis belladonna	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23239	Amaryllis belladonna	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23239	Amaryllis belladonna	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23239	Amaryllis belladonna	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	15
Others	2

Activity Type	# Activity
Cell Line	7
NON-MOLECULAR	6
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT169	Cell Line	B16-F10	Mus musculus	IC50	=	6700.0	nM	PMID[511841]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	7200.0	nM	PMID[511841]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	=	8300.0	nM	PMID[511841]
NPT3190	Cell Line	NHDF	Homo sapiens	IC50	>	100000.0	nM	PMID[511841]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	7200.0	nM	PMID[511842]
NPT916	Cell Line	SK-MEL	Homo sapiens	IC50	=	8300.0	nM	PMID[511842]
NPT169	Cell Line	B16-F10	Mus musculus	IC50	=	6700.0	nM	PMID[511842]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6700.0	nM	PMID[511841]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7300.0	nM	PMID[511841]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	8300.0	nM	PMID[511841]
NPT27	Others	Unspecified		IC50	=	97600.0	nM	PMID[511841]
NPT27	Others	Unspecified		IC50	>	100000.0	nM	PMID[511841]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6700.0	nM	PMID[511842]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	8200.0	nM	PMID[511842]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7200.0	nM	PMID[511842]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	22.0	mm	PMID[511843]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	22.0	mm	PMID[511843]

☑ 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 NPC100566 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	252
0.1-0.2	1247
0.2-0.3	4050
0.3-0.4	12067
0.4-0.5	7760
0.5-0.6	12395
0.6-0.7	3801
0.7-0.8	839
0.8-0.85	179
0.85-0.9	51
0.9-0.95	44
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9744	High Similarity	NPC181653
0.9744	High Similarity	NPC190332
0.9551	High Similarity	NPC320104
0.9503	High Similarity	NPC237044
0.9444	High Similarity	NPC474325
0.9441	High Similarity	NPC304675
0.9437	High Similarity	NPC477640
0.9437	High Similarity	NPC225597
0.9437	High Similarity	NPC470739
0.9434	High Similarity	NPC290759
0.9434	High Similarity	NPC266176
0.9434	High Similarity	NPC82533
0.9434	High Similarity	NPC475686
0.9434	High Similarity	NPC58766
0.9434	High Similarity	NPC158148
0.9387	High Similarity	NPC474745
0.9375	High Similarity	NPC474475
0.9375	High Similarity	NPC311991
0.9321	High Similarity	NPC187678
0.9299	High Similarity	NPC215829
0.9299	High Similarity	NPC97072
0.9217	High Similarity	NPC474746
0.9217	High Similarity	NPC475981
0.9187	High Similarity	NPC476002
0.9177	High Similarity	NPC249274
0.9177	High Similarity	NPC205167
0.9146	High Similarity	NPC474470
0.913	High Similarity	NPC57812
0.913	High Similarity	NPC474324
0.9107	High Similarity	NPC230098
0.9091	High Similarity	NPC15919
0.9074	High Similarity	NPC475845
0.9057	High Similarity	NPC4304
0.9045	High Similarity	NPC78733
0.9036	High Similarity	NPC244554
0.9018	High Similarity	NPC474708
0.8976	High Similarity	NPC148693
0.8976	High Similarity	NPC118633
0.8976	High Similarity	NPC294790
0.8909	High Similarity	NPC2314
0.8902	High Similarity	NPC75958
0.8896	High Similarity	NPC252960
0.8868	High Similarity	NPC147091
0.8848	High Similarity	NPC65403
0.8827	High Similarity	NPC218614
0.8824	High Similarity	NPC9867
0.8797	High Similarity	NPC148898
0.8773	High Similarity	NPC247972
0.8758	High Similarity	NPC59028
0.8758	High Similarity	NPC92191
0.8758	High Similarity	NPC111485
0.8743	High Similarity	NPC49353
0.8679	High Similarity	NPC223124
0.8679	High Similarity	NPC210148
0.8679	High Similarity	NPC233029
0.8671	High Similarity	NPC274026
0.8662	High Similarity	NPC475959
0.8659	High Similarity	NPC276944
0.8659	High Similarity	NPC238530
0.8659	High Similarity	NPC232514
0.8596	High Similarity	NPC275132
0.8589	High Similarity	NPC165797
0.8562	High Similarity	NPC133011
0.8562	High Similarity	NPC82285
0.8554	High Similarity	NPC298186
0.8554	High Similarity	NPC301189
0.8553	High Similarity	NPC223125
0.8521	High Similarity	NPC128560
0.8521	High Similarity	NPC199465
0.8521	High Similarity	NPC229166
0.8519	High Similarity	NPC234392
0.8519	High Similarity	NPC31311
0.8519	High Similarity	NPC146288
0.8488	Intermediate Similarity	NPC248642
0.848	Intermediate Similarity	NPC126284
0.8457	Intermediate Similarity	NPC41178
0.8457	Intermediate Similarity	NPC138487
0.8457	Intermediate Similarity	NPC216459
0.8443	Intermediate Similarity	NPC150879
0.8443	Intermediate Similarity	NPC210918
0.8439	Intermediate Similarity	NPC156576
0.8434	Intermediate Similarity	NPC231198
0.8434	Intermediate Similarity	NPC180306
0.8428	Intermediate Similarity	NPC24233
0.8428	Intermediate Similarity	NPC147390
0.8428	Intermediate Similarity	NPC246587
0.8428	Intermediate Similarity	NPC135538
0.8428	Intermediate Similarity	NPC428
0.8428	Intermediate Similarity	NPC476571
0.8421	Intermediate Similarity	NPC114364
0.8421	Intermediate Similarity	NPC320223
0.8415	Intermediate Similarity	NPC477080
0.8402	Intermediate Similarity	NPC57272
0.8371	Intermediate Similarity	NPC33256
0.8365	Intermediate Similarity	NPC179825
0.8365	Intermediate Similarity	NPC321505
0.8365	Intermediate Similarity	NPC191376
0.8354	Intermediate Similarity	NPC130926
0.8354	Intermediate Similarity	NPC185838
0.8323	Intermediate Similarity	NPC167546
0.8323	Intermediate Similarity	NPC97221
0.8323	Intermediate Similarity	NPC220858
0.8323	Intermediate Similarity	NPC16805
0.8323	Intermediate Similarity	NPC302527
0.8323	Intermediate Similarity	NPC88249
0.8323	Intermediate Similarity	NPC192768
0.8323	Intermediate Similarity	NPC151895
0.8312	Intermediate Similarity	NPC7018
0.8276	Intermediate Similarity	NPC116284
0.8276	Intermediate Similarity	NPC233718
0.8274	Intermediate Similarity	NPC476432
0.8274	Intermediate Similarity	NPC24264
0.8263	Intermediate Similarity	NPC59567
0.8263	Intermediate Similarity	NPC233650
0.8261	Intermediate Similarity	NPC103379
0.8261	Intermediate Similarity	NPC477565
0.8256	Intermediate Similarity	NPC283999
0.825	Intermediate Similarity	NPC476151
0.8242	Intermediate Similarity	NPC475326
0.8239	Intermediate Similarity	NPC214116
0.8232	Intermediate Similarity	NPC189266
0.8232	Intermediate Similarity	NPC54379
0.8232	Intermediate Similarity	NPC2413
0.8232	Intermediate Similarity	NPC193949
0.8232	Intermediate Similarity	NPC207757
0.8232	Intermediate Similarity	NPC204828
0.8232	Intermediate Similarity	NPC249797
0.8232	Intermediate Similarity	NPC184026
0.8232	Intermediate Similarity	NPC110416
0.8232	Intermediate Similarity	NPC295691
0.8232	Intermediate Similarity	NPC469817
0.8232	Intermediate Similarity	NPC276588
0.8232	Intermediate Similarity	NPC278799
0.8232	Intermediate Similarity	NPC127674
0.8232	Intermediate Similarity	NPC5238
0.8232	Intermediate Similarity	NPC39701
0.8232	Intermediate Similarity	NPC172765
0.8225	Intermediate Similarity	NPC298979
0.8225	Intermediate Similarity	NPC210140
0.8225	Intermediate Similarity	NPC247389
0.8218	Intermediate Similarity	NPC312918
0.8218	Intermediate Similarity	NPC476574
0.8218	Intermediate Similarity	NPC155442
0.8218	Intermediate Similarity	NPC477561
0.8217	Intermediate Similarity	NPC474915
0.8217	Intermediate Similarity	NPC328750
0.8217	Intermediate Similarity	NPC213206
0.8217	Intermediate Similarity	NPC188163
0.8214	Intermediate Similarity	NPC225774
0.8214	Intermediate Similarity	NPC134858
0.8214	Intermediate Similarity	NPC24465
0.8199	Intermediate Similarity	NPC59907
0.8199	Intermediate Similarity	NPC37144
0.8193	Intermediate Similarity	NPC69360
0.8171	Intermediate Similarity	NPC102760
0.8166	Intermediate Similarity	NPC219341
0.8166	Intermediate Similarity	NPC264850
0.8166	Intermediate Similarity	NPC13916
0.8166	Intermediate Similarity	NPC124657
0.8161	Intermediate Similarity	NPC99179
0.8153	Intermediate Similarity	NPC314682
0.8133	Intermediate Similarity	NPC148014
0.8133	Intermediate Similarity	NPC315707
0.8133	Intermediate Similarity	NPC40389
0.8133	Intermediate Similarity	NPC78359
0.8133	Intermediate Similarity	NPC65490
0.8125	Intermediate Similarity	NPC135772
0.8121	Intermediate Similarity	NPC76079
0.8121	Intermediate Similarity	NPC93593
0.8113	Intermediate Similarity	NPC128019
0.8113	Intermediate Similarity	NPC136860
0.8113	Intermediate Similarity	NPC476567
0.811	Intermediate Similarity	NPC37272
0.8107	Intermediate Similarity	NPC306843
0.8107	Intermediate Similarity	NPC78222
0.8107	Intermediate Similarity	NPC196447
0.8107	Intermediate Similarity	NPC212794
0.8107	Intermediate Similarity	NPC253043
0.8107	Intermediate Similarity	NPC96603
0.8107	Intermediate Similarity	NPC13504
0.8107	Intermediate Similarity	NPC136508
0.8107	Intermediate Similarity	NPC477563
0.8086	Intermediate Similarity	NPC7467
0.8084	Intermediate Similarity	NPC106786
0.8081	Intermediate Similarity	NPC149090
0.8081	Intermediate Similarity	NPC19520
0.8077	Intermediate Similarity	NPC301050
0.8077	Intermediate Similarity	NPC131204
0.8072	Intermediate Similarity	NPC37205
0.8072	Intermediate Similarity	NPC160931
0.8072	Intermediate Similarity	NPC186063
0.807	Intermediate Similarity	NPC204908
0.807	Intermediate Similarity	NPC160570
0.807	Intermediate Similarity	NPC83198
0.8068	Intermediate Similarity	NPC476575
0.8057	Intermediate Similarity	NPC32154
0.8056	Intermediate Similarity	NPC24260
0.8049	Intermediate Similarity	NPC277669
0.8049	Intermediate Similarity	NPC76213
0.8047	Intermediate Similarity	NPC324144

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 NPC100566 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	616
0.2-0.3	941
0.3-0.4	2321
0.4-0.5	2710
0.5-0.6	1660
0.6-0.7	600
0.7-0.8	123
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8395	Intermediate Similarity	NPD4772	Phase 2
0.8395	Intermediate Similarity	NPD4773	Phase 2
0.8225	Intermediate Similarity	NPD2969	Approved
0.8225	Intermediate Similarity	NPD2970	Approved
0.8217	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD6071	Discontinued
0.8133	Intermediate Similarity	NPD2560	Approved
0.8133	Intermediate Similarity	NPD2563	Approved
0.807	Intermediate Similarity	NPD27	Approved
0.807	Intermediate Similarity	NPD2489	Approved
0.8059	Intermediate Similarity	NPD3051	Approved
0.8025	Intermediate Similarity	NPD4584	Approved
0.7964	Intermediate Similarity	NPD2978	Approved
0.7964	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD2977	Approved
0.795	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD5582	Discontinued
0.784	Intermediate Similarity	NPD5241	Discontinued
0.7826	Intermediate Similarity	NPD4237	Approved
0.7826	Intermediate Similarity	NPD4236	Phase 3
0.7818	Intermediate Similarity	NPD3640	Phase 3
0.7818	Intermediate Similarity	NPD3639	Approved
0.7818	Intermediate Similarity	NPD3641	Approved
0.7809	Intermediate Similarity	NPD7281	Phase 3
0.7809	Intermediate Similarity	NPD7280	Phase 3
0.7802	Intermediate Similarity	NPD7296	Approved
0.7791	Intermediate Similarity	NPD6107	Approved
0.7759	Intermediate Similarity	NPD2898	Approved
0.7759	Intermediate Similarity	NPD4481	Phase 3
0.7751	Intermediate Similarity	NPD5773	Approved
0.7751	Intermediate Similarity	NPD5772	Approved
0.7746	Intermediate Similarity	NPD4010	Discontinued
0.7709	Intermediate Similarity	NPD7312	Approved
0.7709	Intermediate Similarity	NPD7313	Approved
0.7709	Intermediate Similarity	NPD7310	Approved
0.7709	Intermediate Similarity	NPD7311	Approved
0.7692	Intermediate Similarity	NPD7298	Approved
0.7688	Intermediate Similarity	NPD4420	Approved
0.7683	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD8054	Approved
0.7667	Intermediate Similarity	NPD7309	Approved
0.7667	Intermediate Similarity	NPD8053	Approved
0.7619	Intermediate Similarity	NPD5006	Approved
0.7619	Intermediate Similarity	NPD4017	Approved
0.7619	Intermediate Similarity	NPD5005	Approved
0.7616	Intermediate Similarity	NPD5604	Discontinued
0.759	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD4663	Approved
0.758	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD4210	Discontinued
0.7543	Intermediate Similarity	NPD4166	Phase 2
0.7541	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD7906	Approved
0.7529	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD5312	Approved
0.7528	Intermediate Similarity	NPD5313	Approved
0.7528	Intermediate Similarity	NPD8156	Discontinued
0.7514	Intermediate Similarity	NPD4578	Approved
0.7514	Intermediate Similarity	NPD7831	Phase 2
0.7514	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7833	Phase 2
0.7514	Intermediate Similarity	NPD4577	Approved
0.75	Intermediate Similarity	NPD6031	Approved
0.75	Intermediate Similarity	NPD6030	Approved
0.7472	Intermediate Similarity	NPD8251	Approved
0.7472	Intermediate Similarity	NPD8252	Approved
0.7472	Intermediate Similarity	NPD8099	Discontinued
0.7394	Intermediate Similarity	NPD3060	Approved
0.7394	Intermediate Similarity	NPD5177	Phase 3
0.7375	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD6788	Approved
0.7329	Intermediate Similarity	NPD2238	Phase 2
0.731	Intermediate Similarity	NPD4005	Discontinued
0.7302	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7827	Phase 1
0.7273	Intermediate Similarity	NPD2490	Approved
0.7273	Intermediate Similarity	NPD2488	Approved
0.7256	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD6297	Approved
0.7219	Intermediate Similarity	NPD3124	Discontinued
0.7209	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD5718	Phase 2
0.7202	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD6853	Approved
0.7189	Intermediate Similarity	NPD6851	Approved
0.7186	Intermediate Similarity	NPD4162	Approved
0.7184	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD3705	Approved
0.7176	Intermediate Similarity	NPD1424	Approved
0.7169	Intermediate Similarity	NPD1375	Discontinued
0.716	Intermediate Similarity	NPD2674	Phase 3
0.7135	Intermediate Similarity	NPD2968	Approved
0.7135	Intermediate Similarity	NPD2971	Approved
0.7134	Intermediate Similarity	NPD2492	Phase 1
0.7127	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD2421	Approved
0.7118	Intermediate Similarity	NPD2420	Approved
0.7108	Intermediate Similarity	NPD2161	Phase 2
0.7108	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD3144	Approved
0.7099	Intermediate Similarity	NPD3145	Approved
0.7093	Intermediate Similarity	NPD2122	Discontinued
0.7093	Intermediate Similarity	NPD4727	Phase 1
0.7091	Intermediate Similarity	NPD6895	Approved
0.7091	Intermediate Similarity	NPD6896	Approved
0.7081	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD3057	Approved
0.7076	Intermediate Similarity	NPD4123	Phase 3
0.7072	Intermediate Similarity	NPD6365	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7007	Discovery
0.7059	Intermediate Similarity	NPD3845	Phase 1
0.7059	Intermediate Similarity	NPD7124	Phase 2
0.7059	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD3686	Approved
0.7052	Intermediate Similarity	NPD3687	Approved
0.7048	Intermediate Similarity	NPD1753	Discontinued
0.7043	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6997	Phase 2
0.703	Intermediate Similarity	NPD823	Approved
0.703	Intermediate Similarity	NPD817	Approved
0.7026	Intermediate Similarity	NPD3452	Approved
0.7026	Intermediate Similarity	NPD2494	Approved
0.7026	Intermediate Similarity	NPD3450	Approved
0.7026	Intermediate Similarity	NPD2493	Approved
0.7022	Intermediate Similarity	NPD4055	Discovery
0.7017	Intermediate Similarity	NPD6688	Approved
0.7017	Intermediate Similarity	NPD6687	Approved
0.7006	Intermediate Similarity	NPD5978	Approved
0.7006	Intermediate Similarity	NPD5977	Approved
0.7005	Intermediate Similarity	NPD4582	Approved
0.7005	Intermediate Similarity	NPD4583	Approved
0.7	Intermediate Similarity	NPD7802	Discontinued
0.7	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2677	Approved
0.6995	Remote Similarity	NPD7047	Phase 3
0.6995	Remote Similarity	NPD2975	Approved
0.6995	Remote Similarity	NPD2974	Approved
0.6995	Remote Similarity	NPD2973	Approved
0.699	Remote Similarity	NPD3533	Approved
0.699	Remote Similarity	NPD2972	Approved
0.6989	Remote Similarity	NPD3383	Approved
0.6989	Remote Similarity	NPD3384	Approved
0.6989	Remote Similarity	NPD3382	Approved
0.6984	Remote Similarity	NPD6841	Approved
0.6984	Remote Similarity	NPD6843	Phase 3
0.6984	Remote Similarity	NPD6842	Approved
0.6974	Remote Similarity	NPD4580	Approved
0.6966	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4967	Phase 2
0.6966	Remote Similarity	NPD4965	Approved
0.6966	Remote Similarity	NPD4966	Approved
0.6964	Remote Similarity	NPD3656	Approved
0.6959	Remote Similarity	NPD6667	Approved
0.6959	Remote Similarity	NPD6666	Approved
0.6954	Remote Similarity	NPD4002	Approved
0.6954	Remote Similarity	NPD4004	Approved
0.6946	Remote Similarity	NPD4108	Discontinued
0.6943	Remote Similarity	NPD2667	Approved
0.6943	Remote Similarity	NPD2668	Approved
0.6941	Remote Similarity	NPD6331	Phase 2
0.6936	Remote Similarity	NPD52	Approved
0.6936	Remote Similarity	NPD6090	Discontinued
0.6936	Remote Similarity	NPD7526	Approved
0.6936	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD2230	Approved
0.6918	Remote Similarity	NPD2233	Approved
0.6918	Remote Similarity	NPD2232	Approved
0.6914	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD3109	Approved
0.6909	Remote Similarity	NPD3110	Approved
0.6904	Remote Similarity	NPD2491	Approved
0.6904	Remote Similarity	NPD3448	Approved
0.6901	Remote Similarity	NPD3692	Discontinued
0.6897	Remote Similarity	NPD5976	Discontinued
0.6894	Remote Similarity	NPD4103	Phase 2
0.6894	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD37	Approved
0.6889	Remote Similarity	NPD6234	Discontinued
0.6886	Remote Similarity	NPD6111	Discontinued
0.6882	Remote Similarity	NPD6674	Discontinued
0.6879	Remote Similarity	NPD1357	Approved
0.6878	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4675	Approved
0.6875	Remote Similarity	NPD4659	Approved
0.6875	Remote Similarity	NPD4678	Approved
0.6864	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.686	Remote Similarity	NPD3122	Phase 3
0.6859	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD5677	Discontinued
0.6851	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD4666	Phase 3
0.6851	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD1132	Approved
0.6848	Remote Similarity	NPD1130	Approved
0.6848	Remote Similarity	NPD4474	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