NPASS Compound

Structure

CID311991 OpenBabel06191716122D 21 25 0 0 1 0 0 0 0 0999 V2000 -1.4996 0.8657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4996 -0.0001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8658 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1827 -0.5489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4996 -1.7315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4996 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.7316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5817 -0.8658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7498 -1.2987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7498 -0.4329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7499 1.2987 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2494 -1.2987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2494 -0.4329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7498 -0.4329 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 0.8658 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7498 -1.2987 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -0.7499 2.1387 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7274 1.2858 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0728 -1.5662 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0728 -0.1653 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 11 1 0 0 0 0 2 14 1 0 0 0 0 3 4 1 0 0 0 0 4 17 1 0 0 0 0 5 9 2 0 0 0 0 5 12 1 0 0 0 0 6 10 2 0 0 0 0 6 13 1 0 0 0 0 7 9 1 0 0 0 0 7 17 1 0 0 0 0 8 20 1 0 0 0 0 8 21 1 0 0 0 0 9 10 1 0 0 0 0 10 16 1 0 0 0 0 11 15 1 0 0 0 0 11 18 1 1 0 0 0 12 13 2 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 16 1 6 0 0 0 14 17 1 0 0 0 0 15 16 1 1 0 0 0 15 19 1 0 0 0 0 16 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	289.13
Volume:	280.758
LogP:	0.84
LogD:	0.626
LogS:	-2.08
# Rotatable Bonds:	0
TPSA:	62.16
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.738
Synthetic Accessibility Score:	4.897
Fsp3:	0.625
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:	-5.194
MDCK Permeability:	9.448332093597855e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.041
30% Bioavailability (F30%):	0.296

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.973
Plasma Protein Binding (PPB):	33.89954376220703%
Volume Distribution (VD):	3.567
Pgp-substrate:	46.810455322265625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.372
CYP1A2-substrate:	0.324
CYP2C19-inhibitor:	0.045
CYP2C19-substrate:	0.828
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.153
CYP2D6-inhibitor:	0.948
CYP2D6-substrate:	0.81
CYP3A4-inhibitor:	0.208
CYP3A4-substrate:	0.456

ADMET: Excretion

Clearance (CL):	14.429
Half-life (T1/2):	0.504

ADMET: Toxicity

hERG Blockers:	0.07
Human Hepatotoxicity (H-HT):	0.294
Drug-inuced Liver Injury (DILI):	0.055
AMES Toxicity:	0.093
Rat Oral Acute Toxicity:	0.322
Maximum Recommended Daily Dose:	0.916
Skin Sensitization:	0.069
Carcinogencity:	0.945
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.856

Download Data

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

Natural Product: NPC311991

Natural Product ID:	NPC311991
*Common Name:**	DLYIURZCCWSUKD-MPESAESLSA-N
IUPAC Name:	n.a.
Synonyms:	(-)-Amabiline
Standard InCHIKey:	DLYIURZCCWSUKD-MPESAESLSA-N
Standard InCHI:	InChI=1S/C16H19NO4/c18-11-1-2-14-16(15(11)19)3-4-17(14)7-9-5-12-13(6-10(9)16)21-8-20-12/h5-6,11,14-15,18-19H,1-4,7-8H2/t11-,14-,15-,16+/m1/s1
SMILES:	O[C@@H]1CC[C@@H]2[C@]3([C@@H]1O)CCN2Cc1c3cc2OCOc2c1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL456315
PubChem CID:	399199
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001908] Benzoquinolines [CHEMONTID:0000100] Phenanthridines and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO24293	Neorautanenia mitis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562843]
NPO22317	Crinum amabile	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8229016]
NPO22317	Crinum amabile	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22317	Crinum amabile	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24293	Neorautanenia mitis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22317	Crinum amabile	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24293	Neorautanenia mitis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23091	Halocarpus bidwillii	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21398	Jasminum laurifolium f. nitidum	Species	Oleaceae	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
ED50	14
IC50	1

Activity Type	# Activity
Cell Line	7
NON-MOLECULAR	5
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[450185]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[450185]
NPT168	Cell Line	P388	Mus musculus	ED50	>	5.0	ug ml-1	PMID[450185]
NPT762	Cell Line	A-431	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[450185]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[450185]
NPT133	Cell Line	ZR-75-1	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[450185]
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[450185]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	20.0	ug ml-1	PMID[450185]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	ED50	>	10000.0	ug ml-1	PMID[450185]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	31.9	ug.mL-1	PMID[450186]

☑ 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 NPC311991 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	329
0.1-0.2	1353
0.2-0.3	4122
0.3-0.4	11671
0.4-0.5	8607
0.5-0.6	12377
0.6-0.7	3410
0.7-0.8	647
0.8-0.85	112
0.85-0.9	44
0.9-0.95	22
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9689	High Similarity	NPC15919
0.9375	High Similarity	NPC100566
0.9375	High Similarity	NPC181653
0.9375	High Similarity	NPC190332
0.9325	High Similarity	NPC187678
0.9321	High Similarity	NPC65403
0.9317	High Similarity	NPC475686
0.9317	High Similarity	NPC82533
0.9317	High Similarity	NPC58766
0.9317	High Similarity	NPC290759
0.9317	High Similarity	NPC266176
0.9317	High Similarity	NPC158148
0.9308	High Similarity	NPC320104
0.9259	High Similarity	NPC474475
0.9202	High Similarity	NPC477640
0.9202	High Similarity	NPC470739
0.9202	High Similarity	NPC225597
0.9182	High Similarity	NPC97072
0.9182	High Similarity	NPC215829
0.9167	High Similarity	NPC9867
0.9096	High Similarity	NPC118633
0.9096	High Similarity	NPC148693
0.9096	High Similarity	NPC294790
0.9091	High Similarity	NPC304675
0.9042	High Similarity	NPC244554
0.9036	High Similarity	NPC474470
0.9036	High Similarity	NPC237044
0.8982	High Similarity	NPC474325
0.8931	High Similarity	NPC78733
0.8929	High Similarity	NPC474745
0.8909	High Similarity	NPC75958
0.8841	High Similarity	NPC476002
0.8824	High Similarity	NPC275132
0.8802	High Similarity	NPC2314
0.8788	High Similarity	NPC57812
0.8788	High Similarity	NPC474324
0.878	High Similarity	NPC247972
0.8772	High Similarity	NPC474746
0.8772	High Similarity	NPC475981
0.8735	High Similarity	NPC475845
0.872	High Similarity	NPC218614
0.8712	High Similarity	NPC205167
0.8712	High Similarity	NPC249274
0.8683	High Similarity	NPC474708
0.8675	High Similarity	NPC252960
0.8671	High Similarity	NPC230098
0.8642	High Similarity	NPC31311
0.8642	High Similarity	NPC147091
0.8642	High Similarity	NPC234392
0.8598	High Similarity	NPC4304
0.8571	High Similarity	NPC210148
0.8571	High Similarity	NPC233029
0.8563	High Similarity	NPC210918
0.8554	High Similarity	NPC232514
0.8554	High Similarity	NPC276944
0.8554	High Similarity	NPC238530
0.8553	High Similarity	NPC475959
0.8537	High Similarity	NPC111485
0.8529	High Similarity	NPC128560
0.8529	High Similarity	NPC199465
0.8529	High Similarity	NPC229166
0.8497	Intermediate Similarity	NPC248642
0.8488	Intermediate Similarity	NPC126284
0.8466	Intermediate Similarity	NPC216459
0.8466	Intermediate Similarity	NPC41178
0.8466	Intermediate Similarity	NPC138487
0.8457	Intermediate Similarity	NPC148898
0.8457	Intermediate Similarity	NPC223124
0.8448	Intermediate Similarity	NPC156576
0.8443	Intermediate Similarity	NPC167546
0.8443	Intermediate Similarity	NPC16805
0.8443	Intermediate Similarity	NPC302527
0.843	Intermediate Similarity	NPC320223
0.843	Intermediate Similarity	NPC114364
0.8421	Intermediate Similarity	NPC49353
0.8415	Intermediate Similarity	NPC146288
0.8393	Intermediate Similarity	NPC476432
0.8393	Intermediate Similarity	NPC24264
0.8382	Intermediate Similarity	NPC99179
0.8343	Intermediate Similarity	NPC247389
0.8333	Intermediate Similarity	NPC225774
0.8333	Intermediate Similarity	NPC223125
0.8313	Intermediate Similarity	NPC477080
0.8313	Intermediate Similarity	NPC59028
0.8313	Intermediate Similarity	NPC92191
0.8286	Intermediate Similarity	NPC116284
0.8284	Intermediate Similarity	NPC219341
0.8263	Intermediate Similarity	NPC165797
0.8249	Intermediate Similarity	NPC214116
0.8235	Intermediate Similarity	NPC298979
0.8235	Intermediate Similarity	NPC150879
0.8229	Intermediate Similarity	NPC155442
0.8229	Intermediate Similarity	NPC312918
0.8229	Intermediate Similarity	NPC476574
0.8229	Intermediate Similarity	NPC477561
0.8225	Intermediate Similarity	NPC180306
0.8221	Intermediate Similarity	NPC274026
0.821	Intermediate Similarity	NPC135538
0.821	Intermediate Similarity	NPC476571
0.821	Intermediate Similarity	NPC147390
0.821	Intermediate Similarity	NPC428
0.821	Intermediate Similarity	NPC246587
0.821	Intermediate Similarity	NPC24233
0.8198	Intermediate Similarity	NPC149090
0.8198	Intermediate Similarity	NPC19520
0.8182	Intermediate Similarity	NPC476575
0.8176	Intermediate Similarity	NPC124657
0.816	Intermediate Similarity	NPC103379
0.816	Intermediate Similarity	NPC477565
0.8155	Intermediate Similarity	NPC306902
0.8155	Intermediate Similarity	NPC477559
0.8155	Intermediate Similarity	NPC160298
0.8155	Intermediate Similarity	NPC232924
0.8155	Intermediate Similarity	NPC266753
0.8148	Intermediate Similarity	NPC476151
0.8148	Intermediate Similarity	NPC321505
0.8148	Intermediate Similarity	NPC191376
0.8148	Intermediate Similarity	NPC179825
0.8144	Intermediate Similarity	NPC129603
0.814	Intermediate Similarity	NPC6152
0.8137	Intermediate Similarity	NPC185838
0.8136	Intermediate Similarity	NPC135772
0.8133	Intermediate Similarity	NPC276588
0.8133	Intermediate Similarity	NPC127674
0.8133	Intermediate Similarity	NPC39701
0.8133	Intermediate Similarity	NPC207757
0.8133	Intermediate Similarity	NPC278799
0.8133	Intermediate Similarity	NPC184026
0.8133	Intermediate Similarity	NPC189266
0.8133	Intermediate Similarity	NPC172765
0.8133	Intermediate Similarity	NPC93593
0.8133	Intermediate Similarity	NPC2413
0.8133	Intermediate Similarity	NPC204828
0.8133	Intermediate Similarity	NPC249797
0.8133	Intermediate Similarity	NPC295691
0.8133	Intermediate Similarity	NPC5238
0.8133	Intermediate Similarity	NPC110416
0.8133	Intermediate Similarity	NPC469817
0.8133	Intermediate Similarity	NPC54379
0.8133	Intermediate Similarity	NPC193949
0.8121	Intermediate Similarity	NPC82285
0.8121	Intermediate Similarity	NPC133011
0.8118	Intermediate Similarity	NPC212794
0.8118	Intermediate Similarity	NPC13504
0.8118	Intermediate Similarity	NPC96603
0.8118	Intermediate Similarity	NPC136508
0.8118	Intermediate Similarity	NPC477563
0.8118	Intermediate Similarity	NPC24465
0.8118	Intermediate Similarity	NPC253043
0.8118	Intermediate Similarity	NPC231198
0.8118	Intermediate Similarity	NPC306843
0.8118	Intermediate Similarity	NPC78222
0.8118	Intermediate Similarity	NPC196447
0.8113	Intermediate Similarity	NPC328750
0.8113	Intermediate Similarity	NPC474915
0.8113	Intermediate Similarity	NPC188163
0.8113	Intermediate Similarity	NPC213206
0.8111	Intermediate Similarity	NPC63152
0.811	Intermediate Similarity	NPC220858
0.811	Intermediate Similarity	NPC88249
0.811	Intermediate Similarity	NPC192768
0.811	Intermediate Similarity	NPC97221
0.811	Intermediate Similarity	NPC151895
0.8103	Intermediate Similarity	NPC477558
0.8098	Intermediate Similarity	NPC37144
0.8098	Intermediate Similarity	NPC59907
0.8089	Intermediate Similarity	NPC7018
0.8084	Intermediate Similarity	NPC180756
0.8084	Intermediate Similarity	NPC323443
0.8079	Intermediate Similarity	NPC102760
0.8079	Intermediate Similarity	NPC233718
0.807	Intermediate Similarity	NPC264850
0.807	Intermediate Similarity	NPC13916
0.8059	Intermediate Similarity	NPC324144
0.8059	Intermediate Similarity	NPC233650
0.8057	Intermediate Similarity	NPC283999
0.8056	Intermediate Similarity	NPC82763
0.805	Intermediate Similarity	NPC314682
0.8037	Intermediate Similarity	NPC476144
0.8037	Intermediate Similarity	NPC51957
0.8037	Intermediate Similarity	NPC106295
0.8037	Intermediate Similarity	NPC16107
0.8037	Intermediate Similarity	NPC210437
0.8036	Intermediate Similarity	NPC65490
0.8036	Intermediate Similarity	NPC148014
0.8036	Intermediate Similarity	NPC40389
0.8036	Intermediate Similarity	NPC315707
0.8036	Intermediate Similarity	NPC78359
0.8025	Intermediate Similarity	NPC130926
0.8024	Intermediate Similarity	NPC325871
0.8024	Intermediate Similarity	NPC76079
0.8024	Intermediate Similarity	NPC99659
0.8023	Intermediate Similarity	NPC145832
0.8023	Intermediate Similarity	NPC117188
0.8023	Intermediate Similarity	NPC205421
0.8023	Intermediate Similarity	NPC158376
0.8023	Intermediate Similarity	NPC306555
0.8023	Intermediate Similarity	NPC301189
0.8023	Intermediate Similarity	NPC81218
0.8023	Intermediate Similarity	NPC304846

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 NPC311991 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	634
0.2-0.3	902
0.3-0.4	2447
0.4-0.5	2677
0.5-0.6	1680
0.6-0.7	500
0.7-0.8	106
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8284	Intermediate Similarity	NPD3051	Approved
0.8235	Intermediate Similarity	NPD2970	Approved
0.8235	Intermediate Similarity	NPD2969	Approved
0.8113	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD2489	Approved
0.8081	Intermediate Similarity	NPD27	Approved
0.8072	Intermediate Similarity	NPD4773	Phase 2
0.8072	Intermediate Similarity	NPD4772	Phase 2
0.807	Intermediate Similarity	NPD6071	Discontinued
0.8037	Intermediate Similarity	NPD4584	Approved
0.8036	Intermediate Similarity	NPD2563	Approved
0.8036	Intermediate Similarity	NPD2560	Approved
0.7963	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD4481	Phase 3
0.779	Intermediate Similarity	NPD4663	Approved
0.7765	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD2977	Approved
0.7765	Intermediate Similarity	NPD2978	Approved
0.7747	Intermediate Similarity	NPD7906	Approved
0.773	Intermediate Similarity	NPD4236	Phase 3
0.773	Intermediate Similarity	NPD4237	Approved
0.7722	Intermediate Similarity	NPD7313	Approved
0.7722	Intermediate Similarity	NPD7311	Approved
0.7722	Intermediate Similarity	NPD7312	Approved
0.7722	Intermediate Similarity	NPD7310	Approved
0.7722	Intermediate Similarity	NPD4577	Approved
0.7722	Intermediate Similarity	NPD4578	Approved
0.7701	Intermediate Similarity	NPD4420	Approved
0.7697	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD5582	Discontinued
0.768	Intermediate Similarity	NPD7309	Approved
0.767	Intermediate Similarity	NPD2898	Approved
0.7636	Intermediate Similarity	NPD5241	Discontinued
0.7632	Intermediate Similarity	NPD5005	Approved
0.7632	Intermediate Similarity	NPD5006	Approved
0.7624	Intermediate Similarity	NPD7280	Phase 3
0.7624	Intermediate Similarity	NPD7281	Phase 3
0.7582	Intermediate Similarity	NPD8053	Approved
0.7582	Intermediate Similarity	NPD8054	Approved
0.7557	Intermediate Similarity	NPD4010	Discontinued
0.7542	Intermediate Similarity	NPD8156	Discontinued
0.7529	Intermediate Similarity	NPD4017	Approved
0.7527	Intermediate Similarity	NPD7296	Approved
0.7515	Intermediate Similarity	NPD3641	Approved
0.7515	Intermediate Similarity	NPD3639	Approved
0.7515	Intermediate Similarity	NPD3640	Phase 3
0.75	Intermediate Similarity	NPD7298	Approved
0.75	Intermediate Similarity	NPD6107	Approved
0.7486	Intermediate Similarity	NPD8251	Approved
0.7486	Intermediate Similarity	NPD8099	Discontinued
0.7486	Intermediate Similarity	NPD8252	Approved
0.7457	Intermediate Similarity	NPD5772	Approved
0.7457	Intermediate Similarity	NPD5773	Approved
0.7443	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7833	Phase 2
0.7429	Intermediate Similarity	NPD5604	Discontinued
0.7429	Intermediate Similarity	NPD7831	Phase 2
0.7412	Intermediate Similarity	NPD6030	Approved
0.7412	Intermediate Similarity	NPD6031	Approved
0.738	Intermediate Similarity	NPD2490	Approved
0.738	Intermediate Similarity	NPD2488	Approved
0.7375	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD6788	Approved
0.7366	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD2971	Approved
0.7337	Intermediate Similarity	NPD2968	Approved
0.7306	Intermediate Similarity	NPD3450	Approved
0.7306	Intermediate Similarity	NPD3452	Approved
0.7297	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD2974	Approved
0.7277	Intermediate Similarity	NPD2973	Approved
0.7277	Intermediate Similarity	NPD2975	Approved
0.7267	Intermediate Similarity	NPD4210	Discontinued
0.7263	Intermediate Similarity	NPD4166	Phase 2
0.7253	Intermediate Similarity	NPD5312	Approved
0.7253	Intermediate Similarity	NPD5313	Approved
0.7225	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD4005	Discontinued
0.722	Intermediate Similarity	NPD6997	Phase 2
0.7216	Intermediate Similarity	NPD2493	Approved
0.7216	Intermediate Similarity	NPD2494	Approved
0.7209	Intermediate Similarity	NPD4727	Phase 1
0.7202	Intermediate Similarity	NPD5177	Phase 3
0.7202	Intermediate Similarity	NPD3060	Approved
0.7178	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD6297	Approved
0.7169	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD4580	Approved
0.7143	Intermediate Similarity	NPD4002	Approved
0.7143	Intermediate Similarity	NPD4004	Approved
0.7135	Intermediate Similarity	NPD2421	Approved
0.7135	Intermediate Similarity	NPD2420	Approved
0.7134	Intermediate Similarity	NPD2238	Phase 2
0.7118	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD5718	Phase 2
0.7114	Intermediate Similarity	NPD7827	Phase 1
0.7113	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD6853	Approved
0.7112	Intermediate Similarity	NPD6851	Approved
0.7108	Intermediate Similarity	NPD6896	Approved
0.7108	Intermediate Similarity	NPD6895	Approved
0.7107	Intermediate Similarity	NPD4582	Approved
0.7107	Intermediate Similarity	NPD4583	Approved
0.7107	Intermediate Similarity	NPD4040	Phase 1
0.7105	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD4162	Approved
0.7094	Intermediate Similarity	NPD7047	Phase 3
0.7093	Intermediate Similarity	NPD1424	Approved
0.7088	Intermediate Similarity	NPD6365	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD7124	Phase 2
0.7059	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD2492	Phase 1
0.7039	Intermediate Similarity	NPD4055	Discovery
0.7039	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6688	Approved
0.7033	Intermediate Similarity	NPD6687	Approved
0.703	Intermediate Similarity	NPD3110	Approved
0.703	Intermediate Similarity	NPD3109	Approved
0.7029	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5160	Discontinued
0.7018	Intermediate Similarity	NPD2677	Approved
0.7016	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD3057	Approved
0.6994	Remote Similarity	NPD7020	Approved
0.6994	Remote Similarity	NPD7019	Approved
0.6994	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7007	Discovery
0.6983	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD1375	Discontinued
0.6981	Remote Similarity	NPD3705	Approved
0.6977	Remote Similarity	NPD3845	Phase 1
0.6977	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD1753	Discontinued
0.6957	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD3124	Discontinued
0.6923	Remote Similarity	NPD7802	Discontinued
0.6923	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3983	Phase 3
0.6919	Remote Similarity	NPD2972	Approved
0.6919	Remote Similarity	NPD3448	Approved
0.6919	Remote Similarity	NPD3533	Approved
0.6916	Remote Similarity	NPD6625	Approved
0.6914	Remote Similarity	NPD5976	Discontinued
0.6911	Remote Similarity	NPD6842	Approved
0.6911	Remote Similarity	NPD6841	Approved
0.6911	Remote Similarity	NPD6843	Phase 3
0.691	Remote Similarity	NPD3382	Approved
0.691	Remote Similarity	NPD3384	Approved
0.691	Remote Similarity	NPD3383	Approved
0.69	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4123	Phase 3
0.6882	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3686	Approved
0.6875	Remote Similarity	NPD3687	Approved
0.6875	Remote Similarity	NPD2843	Phase 2
0.6875	Remote Similarity	NPD2845	Phase 2
0.6867	Remote Similarity	NPD4474	Approved
0.6867	Remote Similarity	NPD4475	Approved
0.6867	Remote Similarity	NPD2674	Phase 3
0.686	Remote Similarity	NPD5754	Discontinued
0.6845	Remote Similarity	NPD817	Approved
0.6845	Remote Similarity	NPD3885	Approved
0.6845	Remote Similarity	NPD823	Approved
0.6834	Remote Similarity	NPD2491	Approved
0.6833	Remote Similarity	NPD5977	Approved
0.6833	Remote Similarity	NPD5978	Approved
0.6824	Remote Similarity	NPD2161	Phase 2
0.6818	Remote Similarity	NPD2122	Discontinued
0.6818	Remote Similarity	NPD4107	Approved
0.6813	Remote Similarity	NPD4796	Discontinued
0.6806	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD6111	Discontinued
0.6802	Remote Similarity	NPD6877	Discontinued
0.6802	Remote Similarity	NPD6674	Discontinued
0.68	Remote Similarity	NPD7497	Discontinued
0.68	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD19	Approved
0.6796	Remote Similarity	NPD1742	Approved
0.6796	Remote Similarity	NPD1743	Approved
0.6796	Remote Similarity	NPD4967	Phase 2
0.6796	Remote Similarity	NPD4965	Approved
0.6796	Remote Similarity	NPD4966	Approved
0.6792	Remote Similarity	NPD1357	Approved
0.6791	Remote Similarity	NPD5600	Discontinued
0.6788	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD3656	Approved
0.6782	Remote Similarity	NPD6666	Approved
0.6782	Remote Similarity	NPD6667	Approved
0.6777	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD5677	Discontinued
0.6776	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD4666	Phase 3
0.6768	Remote Similarity	NPD8095	Phase 1

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