NPASS Compound

Structure

CID148898 OpenBabel06191715522D 22 26 0 0 1 0 0 0 0 0999 V2000 -3.3984 2.0613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0098 2.0144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8314 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8506 -1.4977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0308 1.0026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0049 -1.0072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0259 -0.0050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5894 -1.4983 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5796 0.5161 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7049 1.0159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0066 -0.4793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7147 -0.9989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0049 1.0076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7000 2.0227 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7098 0.0083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4592 -0.9904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4543 0.0167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8410 0.4991 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 -2.5381 2.5323 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4186 -1.2970 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4107 0.3326 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 3 2 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 6 1 0 0 0 0 4 12 1 0 0 0 0 5 7 1 0 0 0 0 5 13 2 0 0 0 0 6 19 1 0 0 0 0 7 19 1 0 0 0 0 8 12 2 0 0 0 0 8 16 1 0 0 0 0 9 15 2 0 0 0 0 9 17 1 0 0 0 0 10 14 1 0 0 0 0 10 18 1 0 0 0 0 11 21 1 0 0 0 0 11 22 1 0 0 0 0 12 15 1 0 0 0 0 13 18 1 0 0 0 0 14 20 1 1 0 0 0 15 18 1 0 0 0 0 16 17 2 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 19 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	297.14
Volume:	301.287
LogP:	2.804
LogD:	2.191
LogS:	-3.492
# Rotatable Bonds:	1
TPSA:	30.93
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.796
Synthetic Accessibility Score:	4.573
Fsp3:	0.444
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:	-4.883
MDCK Permeability:	2.9638818887178786e-05
Pgp-inhibitor:	0.385
Pgp-substrate:	0.597
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.935
30% Bioavailability (F30%):	0.069

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.997
Plasma Protein Binding (PPB):	80.19405364990234%
Volume Distribution (VD):	2.671
Pgp-substrate:	12.871342658996582%

ADMET: Metabolism

CYP1A2-inhibitor:	0.342
CYP1A2-substrate:	0.568
CYP2C19-inhibitor:	0.359
CYP2C19-substrate:	0.911
CYP2C9-inhibitor:	0.5
CYP2C9-substrate:	0.601
CYP2D6-inhibitor:	0.931
CYP2D6-substrate:	0.42
CYP3A4-inhibitor:	0.949
CYP3A4-substrate:	0.934

ADMET: Excretion

Clearance (CL):	17.464
Half-life (T1/2):	0.452

ADMET: Toxicity

hERG Blockers:	0.436
Human Hepatotoxicity (H-HT):	0.843
Drug-inuced Liver Injury (DILI):	0.235
AMES Toxicity:	0.914
Rat Oral Acute Toxicity:	0.224
Maximum Recommended Daily Dose:	0.962
Skin Sensitization:	0.841
Carcinogencity:	0.883
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.877

Download Data

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

Natural Product: NPC148898

Natural Product ID:	NPC148898
*Common Name:**	Erythraline
IUPAC Name:	n.a.
Synonyms:	Erythraline
Standard InCHIKey:	TVOFUERNMZTYRM-KSSFIOAISA-N
Standard InCHI:	InChI=1S/C18H19NO3/c1-20-14-3-2-13-5-7-19-6-4-12-8-16-17(22-11-21-16)9-15(12)18(13,19)10-14/h2-3,5,8-9,14H,4,6-7,10-11H2,1H3/t14-,18-/m0/s1
SMILES:	CO[C@H]1C=CC2=CCN3CCc4cc5c(cc4[C@]23C1)OCO5
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518262
PubChem CID:	5317205
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001782] Erythrina alkaloids [CHEMONTID:0002780] Erythrinanes

*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
NPO20031	Erythrina velutina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19026536]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26767291]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	bark	n.a.	PMID[26767291]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5703	Isotoma longiflora	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14905.1	Erythrina variegata var. orientalis	Varieties	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20031	Erythrina velutina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7483	Doona congestiflora	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1498	Helichrysum thapsus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7297	Erythrina vespertilio	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5703	Isotoma longiflora	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9901	Aspergillus avenaceus	Species	Aspergillaceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	23.0	ug.mL-1	PMID[470308]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	5.0	ug.mL-1	PMID[470308]

☑ 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 NPC148898 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	291
0.1-0.2	1491
0.2-0.3	7656
0.3-0.4	10618
0.4-0.5	9221
0.5-0.6	10248
0.6-0.7	2346
0.7-0.8	599
0.8-0.85	151
0.85-0.9	63
0.9-0.95	11
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.951	High Similarity	NPC130926
0.9459	High Similarity	NPC78733
0.9408	High Similarity	NPC231198
0.9189	High Similarity	NPC274026
0.9184	High Similarity	NPC475959
0.9085	High Similarity	NPC215829
0.9085	High Similarity	NPC97072
0.9067	High Similarity	NPC82285
0.9067	High Similarity	NPC133011
0.8951	High Similarity	NPC7018
0.8947	High Similarity	NPC138487
0.8947	High Similarity	NPC216459
0.8947	High Similarity	NPC41178
0.894	High Similarity	NPC210148
0.894	High Similarity	NPC233029
0.8933	High Similarity	NPC223125
0.8889	High Similarity	NPC31311
0.8889	High Similarity	NPC234392
0.8889	High Similarity	NPC146288
0.8861	High Similarity	NPC266176
0.8861	High Similarity	NPC290759
0.8861	High Similarity	NPC158148
0.8861	High Similarity	NPC82533
0.8846	High Similarity	NPC320104
0.8816	High Similarity	NPC223124
0.8805	High Similarity	NPC75958
0.8797	High Similarity	NPC474324
0.8797	High Similarity	NPC100566
0.8797	High Similarity	NPC57812
0.879	High Similarity	NPC247972
0.8774	High Similarity	NPC477080
0.8774	High Similarity	NPC59028
0.8774	High Similarity	NPC92191
0.8767	High Similarity	NPC314682
0.8758	High Similarity	NPC49353
0.875	High Similarity	NPC470739
0.875	High Similarity	NPC477640
0.875	High Similarity	NPC225597
0.8742	High Similarity	NPC58766
0.8742	High Similarity	NPC475686
0.8742	High Similarity	NPC475845
0.8707	High Similarity	NPC474915
0.8707	High Similarity	NPC213206
0.8707	High Similarity	NPC328750
0.8707	High Similarity	NPC188163
0.8701	High Similarity	NPC93593
0.8688	High Similarity	NPC474475
0.8688	High Similarity	NPC474708
0.8679	High Similarity	NPC181653
0.8679	High Similarity	NPC190332
0.8654	High Similarity	NPC106786
0.8645	High Similarity	NPC147091
0.8642	High Similarity	NPC187678
0.8616	High Similarity	NPC476002
0.8608	High Similarity	NPC59567
0.8599	High Similarity	NPC477559
0.8599	High Similarity	NPC160298
0.8599	High Similarity	NPC232924
0.8599	High Similarity	NPC306902
0.8599	High Similarity	NPC266753
0.859	High Similarity	NPC475326
0.8589	High Similarity	NPC474470
0.8553	High Similarity	NPC238530
0.8553	High Similarity	NPC232514
0.8553	High Similarity	NPC276944
0.8535	High Similarity	NPC111485
0.8531	High Similarity	NPC160193
0.8528	High Similarity	NPC304675
0.8519	High Similarity	NPC65403
0.8487	Intermediate Similarity	NPC106295
0.8487	Intermediate Similarity	NPC476144
0.8487	Intermediate Similarity	NPC16107
0.8487	Intermediate Similarity	NPC210437
0.8487	Intermediate Similarity	NPC51957
0.8485	Intermediate Similarity	NPC244554
0.8477	Intermediate Similarity	NPC185838
0.8476	Intermediate Similarity	NPC237044
0.8467	Intermediate Similarity	NPC128019
0.8467	Intermediate Similarity	NPC136860
0.8467	Intermediate Similarity	NPC476567
0.8466	Intermediate Similarity	NPC2314
0.8462	Intermediate Similarity	NPC76079
0.8457	Intermediate Similarity	NPC311991
0.8438	Intermediate Similarity	NPC225774
0.8431	Intermediate Similarity	NPC37144
0.8431	Intermediate Similarity	NPC59907
0.8431	Intermediate Similarity	NPC7467
0.8424	Intermediate Similarity	NPC118633
0.8424	Intermediate Similarity	NPC148693
0.8424	Intermediate Similarity	NPC294790
0.8424	Intermediate Similarity	NPC474325
0.8385	Intermediate Similarity	NPC24264
0.8385	Intermediate Similarity	NPC476432
0.8385	Intermediate Similarity	NPC219341
0.8383	Intermediate Similarity	NPC102760
0.8375	Intermediate Similarity	NPC218614
0.8373	Intermediate Similarity	NPC474745
0.8366	Intermediate Similarity	NPC179825
0.8366	Intermediate Similarity	NPC476151
0.8366	Intermediate Similarity	NPC191376
0.8366	Intermediate Similarity	NPC321505
0.8365	Intermediate Similarity	NPC205167
0.8365	Intermediate Similarity	NPC249274
0.8333	Intermediate Similarity	NPC210918
0.8333	Intermediate Similarity	NPC247389
0.8333	Intermediate Similarity	NPC298979
0.8323	Intermediate Similarity	NPC302527
0.8323	Intermediate Similarity	NPC16805
0.8323	Intermediate Similarity	NPC167546
0.8313	Intermediate Similarity	NPC24954
0.8312	Intermediate Similarity	NPC246587
0.8312	Intermediate Similarity	NPC428
0.8312	Intermediate Similarity	NPC147390
0.8312	Intermediate Similarity	NPC135538
0.8312	Intermediate Similarity	NPC476571
0.8312	Intermediate Similarity	NPC24233
0.8311	Intermediate Similarity	NPC416184
0.8282	Intermediate Similarity	NPC241055
0.8272	Intermediate Similarity	NPC304659
0.8272	Intermediate Similarity	NPC86144
0.8269	Intermediate Similarity	NPC476579
0.8258	Intermediate Similarity	NPC103379
0.8258	Intermediate Similarity	NPC219162
0.8258	Intermediate Similarity	NPC477565
0.8255	Intermediate Similarity	NPC253429
0.825	Intermediate Similarity	NPC4304
0.825	Intermediate Similarity	NPC165797
0.8225	Intermediate Similarity	NPC475981
0.8225	Intermediate Similarity	NPC474746
0.8221	Intermediate Similarity	NPC252960
0.821	Intermediate Similarity	NPC168409
0.821	Intermediate Similarity	NPC180306
0.8204	Intermediate Similarity	NPC15919
0.8176	Intermediate Similarity	NPC180756
0.8176	Intermediate Similarity	NPC323443
0.8155	Intermediate Similarity	NPC126284
0.8153	Intermediate Similarity	NPC326316
0.8153	Intermediate Similarity	NPC81733
0.8148	Intermediate Similarity	NPC189470
0.8144	Intermediate Similarity	NPC283999
0.8141	Intermediate Similarity	NPC60538
0.8141	Intermediate Similarity	NPC207824
0.8138	Intermediate Similarity	NPC172403
0.8129	Intermediate Similarity	NPC95075
0.8129	Intermediate Similarity	NPC90844
0.8129	Intermediate Similarity	NPC230098
0.8129	Intermediate Similarity	NPC253883
0.8117	Intermediate Similarity	NPC145304
0.8113	Intermediate Similarity	NPC193949
0.8113	Intermediate Similarity	NPC184026
0.8113	Intermediate Similarity	NPC5238
0.8113	Intermediate Similarity	NPC249797
0.8113	Intermediate Similarity	NPC204828
0.8113	Intermediate Similarity	NPC54379
0.8113	Intermediate Similarity	NPC469817
0.8113	Intermediate Similarity	NPC172765
0.8113	Intermediate Similarity	NPC276588
0.8113	Intermediate Similarity	NPC110416
0.8113	Intermediate Similarity	NPC295691
0.8113	Intermediate Similarity	NPC207757
0.8113	Intermediate Similarity	NPC278799
0.8113	Intermediate Similarity	NPC2413
0.8113	Intermediate Similarity	NPC189266
0.8113	Intermediate Similarity	NPC127674
0.8113	Intermediate Similarity	NPC39701
0.8108	Intermediate Similarity	NPC160692
0.8098	Intermediate Similarity	NPC306669
0.8089	Intermediate Similarity	NPC220858
0.8089	Intermediate Similarity	NPC192768
0.8089	Intermediate Similarity	NPC151895
0.8089	Intermediate Similarity	NPC97221
0.8089	Intermediate Similarity	NPC88249
0.8077	Intermediate Similarity	NPC130941
0.8075	Intermediate Similarity	NPC118804
0.8072	Intermediate Similarity	NPC149090
0.8072	Intermediate Similarity	NPC19520
0.8067	Intermediate Similarity	NPC301050
0.8067	Intermediate Similarity	NPC131204
0.8059	Intermediate Similarity	NPC275132
0.8059	Intermediate Similarity	NPC248642
0.8047	Intermediate Similarity	NPC27887
0.8047	Intermediate Similarity	NPC267408
0.8038	Intermediate Similarity	NPC76213
0.8038	Intermediate Similarity	NPC476568
0.8038	Intermediate Similarity	NPC277669
0.8037	Intermediate Similarity	NPC233650
0.8036	Intermediate Similarity	NPC287588
0.8025	Intermediate Similarity	NPC92541
0.8012	Intermediate Similarity	NPC156576
0.8012	Intermediate Similarity	NPC6152
0.8	Intermediate Similarity	NPC11147
0.8	Intermediate Similarity	NPC179704
0.8	Intermediate Similarity	NPC301189
0.8	Intermediate Similarity	NPC298186
0.7988	Intermediate Similarity	NPC114364
0.7988	Intermediate Similarity	NPC320223
0.7988	Intermediate Similarity	NPC134858
0.7987	Intermediate Similarity	NPC470924
0.7976	Intermediate Similarity	NPC229166
0.7976	Intermediate Similarity	NPC199465

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 NPC148898 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	754
0.2-0.3	1037
0.3-0.4	2122
0.4-0.5	2734
0.5-0.6	1608
0.6-0.7	575
0.7-0.8	111
0.8-0.85	13
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8707	High Similarity	NPD4664	Clinical (unspecified phase)
0.8487	Intermediate Similarity	NPD4584	Approved
0.8355	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD4773	Phase 2
0.828	Intermediate Similarity	NPD4772	Phase 2
0.8153	Intermediate Similarity	NPD4017	Approved
0.8141	Intermediate Similarity	NPD3639	Approved
0.8141	Intermediate Similarity	NPD3640	Phase 3
0.8141	Intermediate Similarity	NPD3641	Approved
0.8027	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD6030	Approved
0.8025	Intermediate Similarity	NPD6031	Approved
0.7988	Intermediate Similarity	NPD6107	Approved
0.7939	Intermediate Similarity	NPD6071	Discontinued
0.7919	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD2563	Approved
0.7901	Intermediate Similarity	NPD2560	Approved
0.7888	Intermediate Similarity	NPD7298	Approved
0.7852	Intermediate Similarity	NPD5718	Phase 2
0.7821	Intermediate Similarity	NPD5241	Discontinued
0.7778	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD2492	Phase 1
0.7738	Intermediate Similarity	NPD4481	Phase 3
0.7738	Intermediate Similarity	NPD2898	Approved
0.7725	Intermediate Similarity	NPD4166	Phase 2
0.7718	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD5313	Approved
0.7706	Intermediate Similarity	NPD5312	Approved
0.7679	Intermediate Similarity	NPD2969	Approved
0.7679	Intermediate Similarity	NPD2970	Approved
0.7667	Intermediate Similarity	NPD4420	Approved
0.7633	Intermediate Similarity	NPD2489	Approved
0.7633	Intermediate Similarity	NPD27	Approved
0.7622	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3051	Approved
0.761	Intermediate Similarity	NPD3124	Discontinued
0.7602	Intermediate Similarity	NPD8156	Discontinued
0.7596	Intermediate Similarity	NPD5005	Approved
0.7596	Intermediate Similarity	NPD5006	Approved
0.759	Intermediate Similarity	NPD7833	Phase 2
0.759	Intermediate Similarity	NPD7831	Phase 2
0.759	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7280	Phase 3
0.7586	Intermediate Similarity	NPD7281	Phase 3
0.7544	Intermediate Similarity	NPD8099	Discontinued
0.7544	Intermediate Similarity	NPD8252	Approved
0.7544	Intermediate Similarity	NPD8251	Approved
0.7531	Intermediate Similarity	NPD4210	Discontinued
0.753	Intermediate Similarity	NPD6788	Approved
0.7515	Intermediate Similarity	NPD2978	Approved
0.7515	Intermediate Similarity	NPD4010	Discontinued
0.7515	Intermediate Similarity	NPD2977	Approved
0.75	Intermediate Similarity	NPD2161	Phase 2
0.7484	Intermediate Similarity	NPD6896	Approved
0.7484	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6895	Approved
0.747	Intermediate Similarity	NPD5977	Approved
0.747	Intermediate Similarity	NPD5978	Approved
0.7456	Intermediate Similarity	NPD7802	Discontinued
0.7453	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD1424	Approved
0.7381	Intermediate Similarity	NPD5604	Discontinued
0.7378	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD5582	Discontinued
0.7362	Intermediate Similarity	NPD4727	Phase 1
0.7358	Intermediate Similarity	NPD4236	Phase 3
0.7358	Intermediate Similarity	NPD4237	Approved
0.7358	Intermediate Similarity	NPD5177	Phase 3
0.7349	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD1375	Discontinued
0.7338	Intermediate Similarity	NPD4474	Approved
0.7338	Intermediate Similarity	NPD4475	Approved
0.7314	Intermediate Similarity	NPD6297	Approved
0.7312	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD7296	Approved
0.729	Intermediate Similarity	NPD3110	Approved
0.729	Intermediate Similarity	NPD3109	Approved
0.7283	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6687	Approved
0.7267	Intermediate Similarity	NPD6688	Approved
0.7257	Intermediate Similarity	NPD3885	Approved
0.725	Intermediate Similarity	NPD4162	Approved
0.7248	Intermediate Similarity	NPD3705	Approved
0.7247	Intermediate Similarity	NPD6853	Approved
0.7247	Intermediate Similarity	NPD8054	Approved
0.7247	Intermediate Similarity	NPD6851	Approved
0.7247	Intermediate Similarity	NPD8053	Approved
0.7226	Intermediate Similarity	NPD2674	Phase 3
0.7225	Intermediate Similarity	NPD6365	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD5773	Approved
0.7202	Intermediate Similarity	NPD5772	Approved
0.7191	Intermediate Similarity	NPD2971	Approved
0.7191	Intermediate Similarity	NPD7310	Approved
0.7191	Intermediate Similarity	NPD7311	Approved
0.7191	Intermediate Similarity	NPD7312	Approved
0.7191	Intermediate Similarity	NPD2968	Approved
0.7191	Intermediate Similarity	NPD7313	Approved
0.7186	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7110	Phase 1
0.7171	Intermediate Similarity	NPD4098	Discontinued
0.7152	Intermediate Similarity	NPD5976	Discontinued
0.7151	Intermediate Similarity	NPD7309	Approved
0.7143	Intermediate Similarity	NPD3383	Approved
0.7143	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3384	Approved
0.7143	Intermediate Similarity	NPD3382	Approved
0.7143	Intermediate Similarity	NPD3060	Approved
0.7127	Intermediate Similarity	NPD3349	Phase 2
0.7127	Intermediate Similarity	NPD7906	Approved
0.7126	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD3656	Approved
0.7117	Intermediate Similarity	NPD7124	Phase 2
0.7115	Intermediate Similarity	NPD3532	Approved
0.7115	Intermediate Similarity	NPD3531	Approved
0.7115	Intermediate Similarity	NPD3530	Approved
0.7114	Intermediate Similarity	NPD2668	Approved
0.7114	Intermediate Similarity	NPD2667	Approved
0.7107	Intermediate Similarity	NPD1753	Discontinued
0.7107	Intermediate Similarity	NPD4108	Discontinued
0.7099	Intermediate Similarity	NPD6748	Discontinued
0.7099	Intermediate Similarity	NPD5754	Discontinued
0.7099	Intermediate Similarity	NPD6331	Phase 2
0.7095	Intermediate Similarity	NPD4578	Approved
0.7095	Intermediate Similarity	NPD4577	Approved
0.7091	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD2420	Approved
0.7073	Intermediate Similarity	NPD2421	Approved
0.707	Intermediate Similarity	NPD2238	Phase 2
0.7051	Intermediate Similarity	NPD3145	Approved
0.7051	Intermediate Similarity	NPD3144	Approved
0.7048	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5720	Discontinued
0.7039	Intermediate Similarity	NPD1421	Approved
0.7039	Intermediate Similarity	NPD1420	Approved
0.7035	Intermediate Similarity	NPD7400	Phase 3
0.7033	Intermediate Similarity	NPD7291	Discontinued
0.7031	Intermediate Similarity	NPD4859	Phase 1
0.703	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD7247	Discontinued
0.7013	Intermediate Similarity	NPD7905	Discontinued
0.7012	Intermediate Similarity	NPD3845	Phase 1
0.7012	Intermediate Similarity	NPD2120	Phase 2
0.7	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD5677	Discontinued
0.6994	Remote Similarity	NPD3977	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD2653	Approved
0.6981	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD4663	Approved
0.6975	Remote Similarity	NPD7153	Discontinued
0.6974	Remote Similarity	NPD2233	Approved
0.6974	Remote Similarity	NPD3816	Phase 1
0.6974	Remote Similarity	NPD2232	Approved
0.6974	Remote Similarity	NPD2230	Approved
0.6974	Remote Similarity	NPD3815	Phase 1
0.6966	Remote Similarity	NPD3920	Phase 2
0.6961	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5967	Approved
0.6959	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2490	Approved
0.6957	Remote Similarity	NPD2488	Approved
0.6957	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD3692	Discontinued
0.6943	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1336	Approved
0.694	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6111	Discontinued
0.6933	Remote Similarity	NPD1357	Approved
0.6927	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6875	Approved
0.6923	Remote Similarity	NPD6876	Approved
0.6909	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4055	Discovery
0.6871	Remote Similarity	NPD5283	Phase 1
0.6868	Remote Similarity	NPD6618	Phase 2
0.6867	Remote Similarity	NPD7598	Phase 2
0.6864	Remote Similarity	NPD4005	Discontinued
0.6864	Remote Similarity	NPD6357	Discontinued
0.6854	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD5708	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD3156	Discontinued
0.6851	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5160	Discontinued
0.6835	Remote Similarity	NPD1039	Discontinued
0.6832	Remote Similarity	NPD7119	Phase 2
0.6828	Remote Similarity	NPD3923	Approved
0.6828	Remote Similarity	NPD3922	Approved
0.6828	Remote Similarity	NPD3924	Approved
0.6828	Remote Similarity	NPD3921	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