NPASS Compound

Structure

CID320104 OpenBabel06191716152D 20 24 0 0 1 0 0 0 0 0999 V2000 0.7541 2.1777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0001 2.6132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5085 0.8710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7542 -0.4355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2633 -0.4355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2631 1.3067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7546 -0.4355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3581 0.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7543 1.3065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5088 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5088 0.8711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7545 2.1775 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0176 0.0002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0175 0.8712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7546 1.3064 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0003 0.8710 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 -1.5328 2.6269 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8461 -0.2689 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8460 1.1405 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 9 2 0 0 0 0 2 12 1 0 0 0 0 3 4 1 0 0 0 0 3 9 1 0 0 0 0 4 17 1 0 0 0 0 5 10 2 0 0 0 0 5 13 1 0 0 0 0 6 11 2 0 0 0 0 6 14 1 0 0 0 0 7 10 1 0 0 0 0 7 17 1 0 0 0 0 8 19 1 0 0 0 0 8 20 1 0 0 0 0 9 16 1 0 0 0 0 10 11 1 0 0 0 0 12 15 1 0 0 0 0 12 18 1 6 0 0 0 13 14 2 0 0 0 0 13 19 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 16 17 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	271.12
Volume:	269.332
LogP:	1.939
LogD:	1.922
LogS:	-2.291
# Rotatable Bonds:	0
TPSA:	41.93
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.73
Synthetic Accessibility Score:	4.013
Fsp3:	0.5
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:	-4.553
MDCK Permeability:	2.6796888050739653e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.861
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.994
Plasma Protein Binding (PPB):	77.69564056396484%
Volume Distribution (VD):	2.856
Pgp-substrate:	15.813992500305176%

ADMET: Metabolism

CYP1A2-inhibitor:	0.795
CYP1A2-substrate:	0.474
CYP2C19-inhibitor:	0.308
CYP2C19-substrate:	0.828
CYP2C9-inhibitor:	0.029
CYP2C9-substrate:	0.418
CYP2D6-inhibitor:	0.969
CYP2D6-substrate:	0.809
CYP3A4-inhibitor:	0.656
CYP3A4-substrate:	0.555

ADMET: Excretion

Clearance (CL):	17.444
Half-life (T1/2):	0.412

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.101
Drug-inuced Liver Injury (DILI):	0.125
AMES Toxicity:	0.143
Rat Oral Acute Toxicity:	0.728
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.053
Carcinogencity:	0.954
Eye Corrosion:	0.004
Eye Irritation:	0.018
Respiratory Toxicity:	0.946

Download Data

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

Natural Product: NPC320104

Natural Product ID:	NPC320104
*Common Name:**	Caranine
IUPAC Name:	n.a.
Synonyms:	Caranine
Standard InCHIKey:	XKYSLILSDJBMCU-DAXOMENPSA-N
Standard InCHI:	InChI=1S/C16H17NO3/c18-12-2-1-9-3-4-17-7-10-5-13-14(20-8-19-13)6-11(10)15(12)16(9)17/h1,5-6,12,15-16,18H,2-4,7-8H2/t12-,15-,16-/m1/s1
SMILES:	O[C@@H]1CC=C2[C@@H]3[C@@H]1c1cc4OCOc4cc1CN3CC2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL575125
PubChem CID:	441589
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
NPO18113	Crinum bulbispermum	Species	Amaryllidaceae	Eukaryota	n.a.	bulb	n.a.	DOI[10.1016/S0031-9422(00)00184-9]
NPO18113	Crinum bulbispermum	Species	Amaryllidaceae	Eukaryota	n.a.	bulb	n.a.	PMID[15587597]
NPO18113	Crinum bulbispermum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18113	Crinum bulbispermum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18113	Crinum bulbispermum	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	12
MIC	1

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	6
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[502102]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	>	10000.0	nM	PMID[502102]
NPT169	Cell Line	B16-F10	Mus musculus	IC50	>	10000.0	nM	PMID[502102]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[502103]
NPT916	Cell Line	SK-MEL	Homo sapiens	IC50	>	10000.0	nM	PMID[502103]
NPT169	Cell Line	B16-F10	Mus musculus	IC50	>	10000.0	nM	PMID[502103]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[502102]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[502103]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	2048.0	ug.mL-1	PMID[502104]

☑ 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 NPC320104 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	292
0.1-0.2	1278
0.2-0.3	4552
0.3-0.4	12730
0.4-0.5	7551
0.5-0.6	12254
0.6-0.7	3082
0.7-0.8	747
0.8-0.85	116
0.85-0.9	45
0.9-0.95	45
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9805	High Similarity	NPC181653
0.9805	High Similarity	NPC190332
0.9551	High Similarity	NPC100566
0.9497	High Similarity	NPC304675
0.9437	High Similarity	NPC237044
0.9379	High Similarity	NPC474325
0.9367	High Similarity	NPC82533
0.9367	High Similarity	NPC58766
0.9367	High Similarity	NPC266176
0.9367	High Similarity	NPC290759
0.9367	High Similarity	NPC158148
0.9367	High Similarity	NPC475686
0.9355	High Similarity	NPC97072
0.9355	High Similarity	NPC215829
0.9321	High Similarity	NPC474745
0.9308	High Similarity	NPC311991
0.9308	High Similarity	NPC474475
0.9304	High Similarity	NPC57812
0.9304	High Similarity	NPC474324
0.925	High Similarity	NPC225597
0.925	High Similarity	NPC477640
0.925	High Similarity	NPC470739
0.9245	High Similarity	NPC475845
0.9231	High Similarity	NPC249274
0.9187	High Similarity	NPC474708
0.9152	High Similarity	NPC474746
0.9152	High Similarity	NPC475981
0.9141	High Similarity	NPC294790
0.9141	High Similarity	NPC118633
0.9141	High Similarity	NPC148693
0.9119	High Similarity	NPC476002
0.9108	High Similarity	NPC4304
0.9108	High Similarity	NPC205167
0.9097	High Similarity	NPC78733
0.908	High Similarity	NPC474470
0.9042	High Similarity	NPC230098
0.9024	High Similarity	NPC15919
0.9018	High Similarity	NPC187678
0.897	High Similarity	NPC244554
0.8938	High Similarity	NPC247972
0.8862	High Similarity	NPC275132
0.8846	High Similarity	NPC148898
0.8846	High Similarity	NPC223124
0.8834	High Similarity	NPC75958
0.878	High Similarity	NPC65403
0.8758	High Similarity	NPC218614
0.8727	High Similarity	NPC2314
0.8718	High Similarity	NPC223125
0.8712	High Similarity	NPC252960
0.8679	High Similarity	NPC147091
0.8647	High Similarity	NPC9867
0.8631	High Similarity	NPC126284
0.8608	High Similarity	NPC233029
0.8608	High Similarity	NPC210148
0.8599	High Similarity	NPC274026
0.8598	High Similarity	NPC210918
0.859	High Similarity	NPC475959
0.8589	High Similarity	NPC180306
0.8571	High Similarity	NPC477080
0.8571	High Similarity	NPC92191
0.8571	High Similarity	NPC59028
0.8563	High Similarity	NPC49353
0.8562	High Similarity	NPC234392
0.8562	High Similarity	NPC31311
0.8529	High Similarity	NPC248642
0.848	Intermediate Similarity	NPC156576
0.8476	Intermediate Similarity	NPC302527
0.8476	Intermediate Similarity	NPC225774
0.8476	Intermediate Similarity	NPC167546
0.8476	Intermediate Similarity	NPC16805
0.8457	Intermediate Similarity	NPC111485
0.8452	Intermediate Similarity	NPC229166
0.8452	Intermediate Similarity	NPC128560
0.8452	Intermediate Similarity	NPC199465
0.8447	Intermediate Similarity	NPC146288
0.8424	Intermediate Similarity	NPC24264
0.8424	Intermediate Similarity	NPC219341
0.8424	Intermediate Similarity	NPC476432
0.8397	Intermediate Similarity	NPC130926
0.8385	Intermediate Similarity	NPC216459
0.8385	Intermediate Similarity	NPC138487
0.8385	Intermediate Similarity	NPC41178
0.8375	Intermediate Similarity	NPC133011
0.8375	Intermediate Similarity	NPC82285
0.8373	Intermediate Similarity	NPC247389
0.8373	Intermediate Similarity	NPC298979
0.8373	Intermediate Similarity	NPC150879
0.8364	Intermediate Similarity	NPC232514
0.8364	Intermediate Similarity	NPC238530
0.8364	Intermediate Similarity	NPC231198
0.8364	Intermediate Similarity	NPC276944
0.8355	Intermediate Similarity	NPC7018
0.8353	Intermediate Similarity	NPC114364
0.8353	Intermediate Similarity	NPC320223
0.8314	Intermediate Similarity	NPC233718
0.8314	Intermediate Similarity	NPC476575
0.8305	Intermediate Similarity	NPC33256
0.8294	Intermediate Similarity	NPC283999
0.8293	Intermediate Similarity	NPC160298
0.8293	Intermediate Similarity	NPC232924
0.8293	Intermediate Similarity	NPC266753
0.8293	Intermediate Similarity	NPC165797
0.8293	Intermediate Similarity	NPC306902
0.8293	Intermediate Similarity	NPC477559
0.828	Intermediate Similarity	NPC185838
0.8276	Intermediate Similarity	NPC214116
0.8272	Intermediate Similarity	NPC76079
0.8263	Intermediate Similarity	NPC301189
0.8263	Intermediate Similarity	NPC298186
0.8239	Intermediate Similarity	NPC59907
0.8239	Intermediate Similarity	NPC37144
0.8235	Intermediate Similarity	NPC477558
0.8225	Intermediate Similarity	NPC149090
0.8225	Intermediate Similarity	NPC19520
0.8208	Intermediate Similarity	NPC116284
0.8194	Intermediate Similarity	NPC314682
0.8193	Intermediate Similarity	NPC59567
0.8193	Intermediate Similarity	NPC233650
0.8176	Intermediate Similarity	NPC191376
0.8176	Intermediate Similarity	NPC179825
0.8176	Intermediate Similarity	NPC476151
0.8176	Intermediate Similarity	NPC321505
0.8166	Intermediate Similarity	NPC6152
0.815	Intermediate Similarity	NPC476574
0.815	Intermediate Similarity	NPC312918
0.815	Intermediate Similarity	NPC477561
0.815	Intermediate Similarity	NPC155442
0.8144	Intermediate Similarity	NPC134858
0.8141	Intermediate Similarity	NPC188163
0.8141	Intermediate Similarity	NPC213206
0.8141	Intermediate Similarity	NPC328750
0.8141	Intermediate Similarity	NPC474915
0.8125	Intermediate Similarity	NPC428
0.8125	Intermediate Similarity	NPC24233
0.8125	Intermediate Similarity	NPC476571
0.8125	Intermediate Similarity	NPC135538
0.8125	Intermediate Similarity	NPC147390
0.8125	Intermediate Similarity	NPC246587
0.8121	Intermediate Similarity	NPC69360
0.8118	Intermediate Similarity	NPC57272
0.811	Intermediate Similarity	NPC180756
0.811	Intermediate Similarity	NPC323443
0.8103	Intermediate Similarity	NPC102760
0.8095	Intermediate Similarity	NPC124657
0.8092	Intermediate Similarity	NPC99179
0.8092	Intermediate Similarity	NPC267408
0.8075	Intermediate Similarity	NPC103379
0.8075	Intermediate Similarity	NPC477565
0.8061	Intermediate Similarity	NPC78359
0.8061	Intermediate Similarity	NPC315707
0.8061	Intermediate Similarity	NPC65490
0.8061	Intermediate Similarity	NPC148014
0.8061	Intermediate Similarity	NPC40389
0.8059	Intermediate Similarity	NPC152212
0.8057	Intermediate Similarity	NPC135772
0.8049	Intermediate Similarity	NPC93593
0.8049	Intermediate Similarity	NPC325871
0.8049	Intermediate Similarity	NPC99659
0.8047	Intermediate Similarity	NPC210140
0.8038	Intermediate Similarity	NPC136860
0.8038	Intermediate Similarity	NPC476567
0.8038	Intermediate Similarity	NPC128019
0.8036	Intermediate Similarity	NPC13504
0.8036	Intermediate Similarity	NPC136508
0.8036	Intermediate Similarity	NPC168409
0.8036	Intermediate Similarity	NPC253043
0.8036	Intermediate Similarity	NPC96603
0.8036	Intermediate Similarity	NPC78222
0.8036	Intermediate Similarity	NPC196447
0.8036	Intermediate Similarity	NPC477563
0.8036	Intermediate Similarity	NPC306843
0.8036	Intermediate Similarity	NPC212794
0.8025	Intermediate Similarity	NPC220858
0.8025	Intermediate Similarity	NPC97221
0.8025	Intermediate Similarity	NPC88249
0.8025	Intermediate Similarity	NPC151895
0.8025	Intermediate Similarity	NPC192768
0.8012	Intermediate Similarity	NPC7467
0.8012	Intermediate Similarity	NPC106786
0.8	Intermediate Similarity	NPC160570
0.8	Intermediate Similarity	NPC241055
0.7989	Intermediate Similarity	NPC117717
0.7988	Intermediate Similarity	NPC304659
0.7988	Intermediate Similarity	NPC86144
0.7978	Intermediate Similarity	NPC82763
0.7977	Intermediate Similarity	NPC241704
0.7976	Intermediate Similarity	NPC324144
0.7976	Intermediate Similarity	NPC189470
0.7966	Intermediate Similarity	NPC57036
0.7963	Intermediate Similarity	NPC207824
0.7963	Intermediate Similarity	NPC60538
0.7963	Intermediate Similarity	NPC219162
0.7961	Intermediate Similarity	NPC160193
0.7952	Intermediate Similarity	NPC476572
0.7952	Intermediate Similarity	NPC129603
0.7952	Intermediate Similarity	NPC475326
0.795	Intermediate Similarity	NPC210437
0.795	Intermediate Similarity	NPC16107
0.795	Intermediate Similarity	NPC51957
0.795	Intermediate Similarity	NPC106295

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 NPC320104 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	188
0.1-0.2	636
0.2-0.3	953
0.3-0.4	2357
0.4-0.5	2716
0.5-0.6	1639
0.6-0.7	546
0.7-0.8	108
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8438	Intermediate Similarity	NPD4773	Phase 2
0.8438	Intermediate Similarity	NPD4772	Phase 2
0.8263	Intermediate Similarity	NPD2970	Approved
0.8263	Intermediate Similarity	NPD2969	Approved
0.8217	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD3051	Approved
0.8141	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD27	Approved
0.8107	Intermediate Similarity	NPD2489	Approved
0.8095	Intermediate Similarity	NPD6071	Discontinued
0.8061	Intermediate Similarity	NPD2563	Approved
0.8061	Intermediate Similarity	NPD2560	Approved
0.795	Intermediate Similarity	NPD4584	Approved
0.7895	Intermediate Similarity	NPD4481	Phase 3
0.7892	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD3639	Approved
0.7853	Intermediate Similarity	NPD3641	Approved
0.7853	Intermediate Similarity	NPD3640	Phase 3
0.7826	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD5241	Discontinued
0.775	Intermediate Similarity	NPD4236	Phase 3
0.775	Intermediate Similarity	NPD4237	Approved
0.774	Intermediate Similarity	NPD7280	Phase 3
0.774	Intermediate Similarity	NPD7281	Phase 3
0.7719	Intermediate Similarity	NPD6107	Approved
0.7688	Intermediate Similarity	NPD2898	Approved
0.7679	Intermediate Similarity	NPD2978	Approved
0.7679	Intermediate Similarity	NPD2977	Approved
0.7651	Intermediate Similarity	NPD4017	Approved
0.7647	Intermediate Similarity	NPD5604	Discontinued
0.764	Intermediate Similarity	NPD7311	Approved
0.764	Intermediate Similarity	NPD7312	Approved
0.764	Intermediate Similarity	NPD4578	Approved
0.764	Intermediate Similarity	NPD7310	Approved
0.764	Intermediate Similarity	NPD7313	Approved
0.764	Intermediate Similarity	NPD4577	Approved
0.7637	Intermediate Similarity	NPD7296	Approved
0.7622	Intermediate Similarity	NPD4420	Approved
0.7619	Intermediate Similarity	NPD7298	Approved
0.7613	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD4663	Approved
0.7609	Intermediate Similarity	NPD5582	Discontinued
0.7598	Intermediate Similarity	NPD7309	Approved
0.7574	Intermediate Similarity	NPD5773	Approved
0.7574	Intermediate Similarity	NPD5772	Approved
0.7572	Intermediate Similarity	NPD4166	Phase 2
0.7558	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD5005	Approved
0.7553	Intermediate Similarity	NPD5006	Approved
0.7544	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD7833	Phase 2
0.7544	Intermediate Similarity	NPD7831	Phase 2
0.7485	Intermediate Similarity	NPD4210	Discontinued
0.7473	Intermediate Similarity	NPD7906	Approved
0.7471	Intermediate Similarity	NPD4010	Discontinued
0.7458	Intermediate Similarity	NPD5312	Approved
0.7458	Intermediate Similarity	NPD5313	Approved
0.7458	Intermediate Similarity	NPD8156	Discontinued
0.7425	Intermediate Similarity	NPD6030	Approved
0.7425	Intermediate Similarity	NPD6031	Approved
0.741	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD8054	Approved
0.7403	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD8053	Approved
0.7401	Intermediate Similarity	NPD8252	Approved
0.7401	Intermediate Similarity	NPD8099	Discontinued
0.7401	Intermediate Similarity	NPD8251	Approved
0.7384	Intermediate Similarity	NPD6788	Approved
0.7377	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD2971	Approved
0.7348	Intermediate Similarity	NPD2968	Approved
0.7317	Intermediate Similarity	NPD5177	Phase 3
0.7297	Intermediate Similarity	NPD2488	Approved
0.7297	Intermediate Similarity	NPD2490	Approved
0.7284	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2492	Phase 1
0.725	Intermediate Similarity	NPD2238	Phase 2
0.7246	Intermediate Similarity	NPD3124	Discontinued
0.7235	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD4005	Discontinued
0.7234	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD5718	Phase 2
0.7219	Intermediate Similarity	NPD4727	Phase 1
0.7212	Intermediate Similarity	NPD3060	Approved
0.7208	Intermediate Similarity	NPD7827	Phase 1
0.7202	Intermediate Similarity	NPD1424	Approved
0.7186	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD6297	Approved
0.7151	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3110	Approved
0.7143	Intermediate Similarity	NPD2420	Approved
0.7143	Intermediate Similarity	NPD2421	Approved
0.7143	Intermediate Similarity	NPD3109	Approved
0.7134	Intermediate Similarity	NPD2161	Phase 2
0.7126	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6853	Approved
0.712	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6851	Approved
0.7118	Intermediate Similarity	NPD2122	Discontinued
0.7112	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD3384	Approved
0.711	Intermediate Similarity	NPD3383	Approved
0.711	Intermediate Similarity	NPD3382	Approved
0.7107	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD2975	Approved
0.7105	Intermediate Similarity	NPD2974	Approved
0.7105	Intermediate Similarity	NPD2973	Approved
0.7098	Intermediate Similarity	NPD3057	Approved
0.7097	Intermediate Similarity	NPD3705	Approved
0.7091	Intermediate Similarity	NPD1375	Discontinued
0.7083	Intermediate Similarity	NPD4580	Approved
0.7083	Intermediate Similarity	NPD3845	Phase 1
0.7066	Intermediate Similarity	NPD5754	Discontinued
0.7066	Intermediate Similarity	NPD6331	Phase 2
0.7047	Intermediate Similarity	NPD3452	Approved
0.7047	Intermediate Similarity	NPD3450	Approved
0.7045	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6688	Approved
0.7039	Intermediate Similarity	NPD6687	Approved
0.7029	Intermediate Similarity	NPD5977	Approved
0.7029	Intermediate Similarity	NPD5978	Approved
0.7018	Intermediate Similarity	NPD5976	Discontinued
0.7012	Intermediate Similarity	NPD6896	Approved
0.7012	Intermediate Similarity	NPD6895	Approved
0.7011	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD3533	Approved
0.701	Intermediate Similarity	NPD3448	Approved
0.701	Intermediate Similarity	NPD2972	Approved
0.7006	Intermediate Similarity	NPD4162	Approved
0.7	Intermediate Similarity	NPD7019	Approved
0.7	Intermediate Similarity	NPD7020	Approved
0.7	Intermediate Similarity	NPD6365	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD7124	Phase 2
0.6982	Remote Similarity	NPD6667	Approved
0.6982	Remote Similarity	NPD6666	Approved
0.6976	Remote Similarity	NPD6997	Phase 2
0.6975	Remote Similarity	NPD2674	Phase 3
0.6974	Remote Similarity	NPD4002	Approved
0.6974	Remote Similarity	NPD4004	Approved
0.6973	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4108	Discontinued
0.697	Remote Similarity	NPD1753	Discontinued
0.6968	Remote Similarity	NPD2668	Approved
0.6968	Remote Similarity	NPD2667	Approved
0.6959	Remote Similarity	NPD2493	Approved
0.6959	Remote Similarity	NPD2494	Approved
0.6951	Remote Similarity	NPD817	Approved
0.6951	Remote Similarity	NPD823	Approved
0.6949	Remote Similarity	NPD4055	Discovery
0.6946	Remote Similarity	NPD7037	Approved
0.6939	Remote Similarity	NPD4040	Phase 1
0.6939	Remote Similarity	NPD4583	Approved
0.6939	Remote Similarity	NPD4582	Approved
0.6936	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7802	Discontinued
0.6923	Remote Similarity	NPD5160	Discontinued
0.6923	Remote Similarity	NPD2491	Approved
0.6919	Remote Similarity	NPD4859	Phase 1
0.6914	Remote Similarity	NPD3145	Approved
0.6914	Remote Similarity	NPD3144	Approved
0.691	Remote Similarity	NPD7400	Phase 3
0.6909	Remote Similarity	NPD6111	Discontinued
0.6907	Remote Similarity	NPD4107	Approved
0.6901	Remote Similarity	NPD4123	Phase 3
0.6893	Remote Similarity	NPD4965	Approved
0.6893	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD4967	Phase 2
0.6893	Remote Similarity	NPD4966	Approved
0.6879	Remote Similarity	NPD3686	Approved
0.6879	Remote Similarity	NPD3687	Approved
0.6872	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4475	Approved
0.6871	Remote Similarity	NPD4474	Approved
0.6865	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7526	Approved
0.686	Remote Similarity	NPD52	Approved
0.686	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6090	Discontinued
0.6848	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD3885	Approved
0.6847	Remote Similarity	NPD7047	Phase 3
0.6845	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD2230	Approved
0.6835	Remote Similarity	NPD2232	Approved
0.6835	Remote Similarity	NPD2233	Approved
0.6832	Remote Similarity	NPD3635	Approved
0.6832	Remote Similarity	NPD3636	Approved
0.6832	Remote Similarity	NPD3637	Approved
0.6825	Remote Similarity	NPD6842	Approved
0.6825	Remote Similarity	NPD6843	Phase 3
0.6825	Remote Similarity	NPD6841	Approved
0.6824	Remote Similarity	NPD2677	Approved
0.6824	Remote Similarity	NPD3692	Discontinued
0.6818	Remote Similarity	NPD37	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