NPASS Compound

Structure

NPC274026 OpenBabel07101719242D 22 25 0 0 1 0 0 0 0 0999 V2000 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1590 2.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4158 2.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5352 2.6473 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 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 -1.2784 3.3164 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 4 2 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 7 1 0 0 0 0 5 12 1 0 0 0 0 6 8 1 0 0 0 0 6 13 2 0 0 0 0 7 19 1 0 0 0 0 8 19 1 0 0 0 0 9 12 2 0 0 0 0 9 16 1 0 0 0 0 10 15 2 0 0 0 0 10 17 1 0 0 0 0 11 14 1 0 0 0 0 11 18 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:	299.15
Volume:	309.844
LogP:	1.888
LogD:	1.455
LogS:	-2.824
# Rotatable Bonds:	2
TPSA:	41.93
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.907
Synthetic Accessibility Score:	4.32
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:	-4.802
MDCK Permeability:	2.1897401893511415e-05
Pgp-inhibitor:	0.079
Pgp-substrate:	0.989
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.552
30% Bioavailability (F30%):	0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.992
Plasma Protein Binding (PPB):	51.96552658081055%
Volume Distribution (VD):	2.82
Pgp-substrate:	36.048606872558594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.577
CYP2C19-inhibitor:	0.148
CYP2C19-substrate:	0.934
CYP2C9-inhibitor:	0.261
CYP2C9-substrate:	0.703
CYP2D6-inhibitor:	0.026
CYP2D6-substrate:	0.685
CYP3A4-inhibitor:	0.464
CYP3A4-substrate:	0.937

ADMET: Excretion

Clearance (CL):	11.142
Half-life (T1/2):	0.723

ADMET: Toxicity

hERG Blockers:	0.324
Human Hepatotoxicity (H-HT):	0.848
Drug-inuced Liver Injury (DILI):	0.186
AMES Toxicity:	0.256
Rat Oral Acute Toxicity:	0.297
Maximum Recommended Daily Dose:	0.965
Skin Sensitization:	0.749
Carcinogencity:	0.869
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.941

Download Data

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

Natural Product: NPC274026

Natural Product ID:	NPC274026
*Common Name:**	(+)-Erythravine
IUPAC Name:	(2R,13bS)-11,12-dimethoxy-2,6,8,9-tetrahydro-1H-indolo[7a,1-a]isoquinolin-2-ol
Synonyms:	(+)-Erythravine
Standard InCHIKey:	JEBFJSHKHYDVNP-KSSFIOAISA-N
Standard InCHI:	InChI=1S/C18H21NO3/c1-21-16-9-12-5-7-19-8-6-13-3-4-14(20)11-18(13,19)15(12)10-17(16)22-2/h3-4,6,9-10,14,20H,5,7-8,11H2,1-2H3/t14-,18-/m0/s1
SMILES:	COc1cc2CCN3CC=C4C=C[C@@H](C[C@]34c2cc1OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL218381
PubChem CID:	11231853
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
NPO11659	Erythrina mulungu	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17253849]
NPO11659	Erythrina mulungu	Species	Fabaceae	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
Others	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	157.33	n.a.	PMID[513099]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	37.07	n.a.	PMID[513099]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	157.93	n.a.	PMID[513099]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	31.71	n.a.	PMID[513099]

☑ 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 NPC274026 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	253
0.1-0.2	1355
0.2-0.3	5918
0.3-0.4	11962
0.4-0.5	6581
0.5-0.6	12152
0.6-0.7	3557
0.7-0.8	645
0.8-0.85	176
0.85-0.9	88
0.9-0.95	4
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9722	High Similarity	NPC133011
0.9722	High Similarity	NPC82285
0.9645	High Similarity	NPC130926
0.9527	High Similarity	NPC92191
0.9527	High Similarity	NPC59028
0.9262	High Similarity	NPC147091
0.92	High Similarity	NPC475326
0.9189	High Similarity	NPC148898
0.9103	High Similarity	NPC185838
0.898	High Similarity	NPC476151
0.898	High Similarity	NPC321505
0.898	High Similarity	NPC179825
0.898	High Similarity	NPC191376
0.8954	High Similarity	NPC205167
0.8954	High Similarity	NPC97072
0.8954	High Similarity	NPC249274
0.8954	High Similarity	NPC215829
0.8919	High Similarity	NPC147390
0.8919	High Similarity	NPC246587
0.8919	High Similarity	NPC24233
0.8919	High Similarity	NPC428
0.8919	High Similarity	NPC135538
0.8919	High Similarity	NPC476571
0.8889	High Similarity	NPC314682
0.8859	High Similarity	NPC103379
0.8859	High Similarity	NPC477565
0.8828	High Similarity	NPC213206
0.8828	High Similarity	NPC474915
0.8828	High Similarity	NPC188163
0.8828	High Similarity	NPC328750
0.875	High Similarity	NPC49353
0.8733	High Similarity	NPC60538
0.8733	High Similarity	NPC207824
0.8693	High Similarity	NPC193949
0.8693	High Similarity	NPC207757
0.8693	High Similarity	NPC295691
0.8693	High Similarity	NPC278799
0.8693	High Similarity	NPC78733
0.8693	High Similarity	NPC54379
0.8693	High Similarity	NPC5238
0.8693	High Similarity	NPC110416
0.8693	High Similarity	NPC172765
0.8693	High Similarity	NPC204828
0.8693	High Similarity	NPC39701
0.8693	High Similarity	NPC127674
0.8693	High Similarity	NPC184026
0.8693	High Similarity	NPC469817
0.8693	High Similarity	NPC189266
0.8693	High Similarity	NPC276588
0.8693	High Similarity	NPC2413
0.8693	High Similarity	NPC249797
0.8681	High Similarity	NPC131204
0.8681	High Similarity	NPC301050
0.8675	High Similarity	NPC151895
0.8675	High Similarity	NPC88249
0.8675	High Similarity	NPC97221
0.8675	High Similarity	NPC220858
0.8675	High Similarity	NPC192768
0.8671	High Similarity	NPC100566
0.8662	High Similarity	NPC231198
0.8652	High Similarity	NPC160193
0.8625	High Similarity	NPC477640
0.8625	High Similarity	NPC225597
0.8625	High Similarity	NPC470739
0.8618	High Similarity	NPC277669
0.8618	High Similarity	NPC76213
0.8616	High Similarity	NPC266176
0.8616	High Similarity	NPC475686
0.8616	High Similarity	NPC158148
0.8616	High Similarity	NPC82533
0.8616	High Similarity	NPC58766
0.8616	High Similarity	NPC290759
0.86	High Similarity	NPC106295
0.86	High Similarity	NPC210437
0.86	High Similarity	NPC16107
0.86	High Similarity	NPC476144
0.86	High Similarity	NPC51957
0.8599	High Similarity	NPC320104
0.8599	High Similarity	NPC233650
0.8581	High Similarity	NPC136860
0.8581	High Similarity	NPC476567
0.8581	High Similarity	NPC128019
0.8562	High Similarity	NPC474475
0.8553	High Similarity	NPC181653
0.8553	High Similarity	NPC190332
0.8544	High Similarity	NPC134858
0.8543	High Similarity	NPC7467
0.8543	High Similarity	NPC475959
0.8519	High Similarity	NPC187678
0.8506	High Similarity	NPC2295
0.8506	High Similarity	NPC477564
0.8491	Intermediate Similarity	NPC476002
0.8462	Intermediate Similarity	NPC315707
0.8462	Intermediate Similarity	NPC148014
0.8462	Intermediate Similarity	NPC78359
0.8462	Intermediate Similarity	NPC65490
0.8462	Intermediate Similarity	NPC40389
0.8457	Intermediate Similarity	NPC2314
0.8442	Intermediate Similarity	NPC37272
0.8438	Intermediate Similarity	NPC210140
0.8438	Intermediate Similarity	NPC150879
0.8428	Intermediate Similarity	NPC276944
0.8428	Intermediate Similarity	NPC232514
0.8428	Intermediate Similarity	NPC238530
0.8408	Intermediate Similarity	NPC111485
0.84	Intermediate Similarity	NPC294249
0.8395	Intermediate Similarity	NPC476331
0.8377	Intermediate Similarity	NPC476579
0.8367	Intermediate Similarity	NPC253429
0.8354	Intermediate Similarity	NPC166014
0.8354	Intermediate Similarity	NPC27410
0.8354	Intermediate Similarity	NPC4304
0.8354	Intermediate Similarity	NPC18402
0.8354	Intermediate Similarity	NPC237044
0.8354	Intermediate Similarity	NPC474470
0.8333	Intermediate Similarity	NPC138487
0.8333	Intermediate Similarity	NPC216459
0.8333	Intermediate Similarity	NPC41178
0.8323	Intermediate Similarity	NPC223124
0.8323	Intermediate Similarity	NPC26601
0.8303	Intermediate Similarity	NPC474325
0.8299	Intermediate Similarity	NPC7018
0.8293	Intermediate Similarity	NPC304675
0.828	Intermediate Similarity	NPC146288
0.8272	Intermediate Similarity	NPC470324
0.8261	Intermediate Similarity	NPC124657
0.8261	Intermediate Similarity	NPC13916
0.8261	Intermediate Similarity	NPC264850
0.8258	Intermediate Similarity	NPC81733
0.8258	Intermediate Similarity	NPC326316
0.8253	Intermediate Similarity	NPC244554
0.8253	Intermediate Similarity	NPC474745
0.8252	Intermediate Similarity	NPC172403
0.825	Intermediate Similarity	NPC59567
0.8247	Intermediate Similarity	NPC219162
0.8228	Intermediate Similarity	NPC129603
0.8221	Intermediate Similarity	NPC311991
0.8219	Intermediate Similarity	NPC160692
0.821	Intermediate Similarity	NPC298979
0.8205	Intermediate Similarity	NPC210148
0.8205	Intermediate Similarity	NPC233029
0.8199	Intermediate Similarity	NPC169743
0.8199	Intermediate Similarity	NPC24465
0.8199	Intermediate Similarity	NPC76116
0.8194	Intermediate Similarity	NPC223125
0.8193	Intermediate Similarity	NPC294790
0.8193	Intermediate Similarity	NPC118633
0.8193	Intermediate Similarity	NPC148693
0.8187	Intermediate Similarity	NPC60186
0.8176	Intermediate Similarity	NPC118804
0.8165	Intermediate Similarity	NPC31311
0.8165	Intermediate Similarity	NPC180756
0.8165	Intermediate Similarity	NPC234392
0.8165	Intermediate Similarity	NPC323443
0.8165	Intermediate Similarity	NPC186063
0.816	Intermediate Similarity	NPC83198
0.816	Intermediate Similarity	NPC204908
0.8148	Intermediate Similarity	NPC240841
0.8148	Intermediate Similarity	NPC256012
0.8148	Intermediate Similarity	NPC268503
0.8148	Intermediate Similarity	NPC317272
0.8148	Intermediate Similarity	NPC250846
0.8148	Intermediate Similarity	NPC42549
0.8144	Intermediate Similarity	NPC126284
0.8141	Intermediate Similarity	NPC476568
0.8137	Intermediate Similarity	NPC124433
0.8137	Intermediate Similarity	NPC293871
0.8137	Intermediate Similarity	NPC324144
0.8133	Intermediate Similarity	NPC241704
0.8129	Intermediate Similarity	NPC92541
0.8125	Intermediate Similarity	NPC165797
0.8121	Intermediate Similarity	NPC193528
0.8117	Intermediate Similarity	NPC253883
0.8117	Intermediate Similarity	NPC95075
0.8117	Intermediate Similarity	NPC90844
0.811	Intermediate Similarity	NPC75958
0.8107	Intermediate Similarity	NPC474746
0.8107	Intermediate Similarity	NPC475981
0.8101	Intermediate Similarity	NPC93593
0.8098	Intermediate Similarity	NPC474324
0.8098	Intermediate Similarity	NPC12053
0.8098	Intermediate Similarity	NPC57812
0.8098	Intermediate Similarity	NPC117188
0.8098	Intermediate Similarity	NPC205421
0.8098	Intermediate Similarity	NPC252960
0.8098	Intermediate Similarity	NPC145832
0.8098	Intermediate Similarity	NPC158376
0.8098	Intermediate Similarity	NPC474931
0.8098	Intermediate Similarity	NPC81218
0.8098	Intermediate Similarity	NPC306555
0.8089	Intermediate Similarity	NPC470924
0.8086	Intermediate Similarity	NPC253043
0.8086	Intermediate Similarity	NPC247972
0.8086	Intermediate Similarity	NPC96603
0.8086	Intermediate Similarity	NPC196447
0.8086	Intermediate Similarity	NPC477563
0.8086	Intermediate Similarity	NPC4138
0.8086	Intermediate Similarity	NPC121275
0.8086	Intermediate Similarity	NPC306843
0.8086	Intermediate Similarity	NPC212794

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 NPC274026 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	700
0.2-0.3	955
0.3-0.4	1974
0.4-0.5	2696
0.5-0.6	1761
0.6-0.7	711
0.7-0.8	163
0.8-0.85	17
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8874	High Similarity	NPD4772	Phase 2
0.8874	High Similarity	NPD4773	Phase 2
0.8828	High Similarity	NPD4664	Clinical (unspecified phase)
0.86	High Similarity	NPD4584	Approved
0.8523	High Similarity	NPD5241	Discontinued
0.8491	Intermediate Similarity	NPD6071	Discontinued
0.8462	Intermediate Similarity	NPD2560	Approved
0.8462	Intermediate Similarity	NPD2563	Approved
0.828	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD2898	Approved
0.8258	Intermediate Similarity	NPD4017	Approved
0.8247	Intermediate Similarity	NPD3640	Phase 3
0.8247	Intermediate Similarity	NPD3641	Approved
0.8247	Intermediate Similarity	NPD3639	Approved
0.821	Intermediate Similarity	NPD2969	Approved
0.821	Intermediate Similarity	NPD2970	Approved
0.816	Intermediate Similarity	NPD27	Approved
0.816	Intermediate Similarity	NPD2489	Approved
0.8138	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD6031	Approved
0.8129	Intermediate Similarity	NPD6030	Approved
0.8125	Intermediate Similarity	NPD7833	Phase 2
0.8125	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD7831	Phase 2
0.8037	Intermediate Similarity	NPD3051	Approved
0.8037	Intermediate Similarity	NPD4010	Discontinued
0.8026	Intermediate Similarity	NPD5177	Phase 3
0.8	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7298	Approved
0.7975	Intermediate Similarity	NPD6107	Approved
0.7959	Intermediate Similarity	NPD5718	Phase 2
0.7881	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD2161	Phase 2
0.7823	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD4237	Approved
0.7792	Intermediate Similarity	NPD4236	Phase 3
0.7792	Intermediate Similarity	NPD3060	Approved
0.7785	Intermediate Similarity	NPD2674	Phase 3
0.7756	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD8054	Approved
0.7733	Intermediate Similarity	NPD8053	Approved
0.7733	Intermediate Similarity	NPD2238	Phase 2
0.7716	Intermediate Similarity	NPD5773	Approved
0.7716	Intermediate Similarity	NPD5772	Approved
0.7711	Intermediate Similarity	NPD4166	Phase 2
0.7707	Intermediate Similarity	NPD3124	Discontinued
0.7692	Intermediate Similarity	NPD8156	Discontinued
0.7692	Intermediate Similarity	NPD5312	Approved
0.7692	Intermediate Similarity	NPD5313	Approved
0.7677	Intermediate Similarity	NPD4162	Approved
0.7647	Intermediate Similarity	NPD1753	Discontinued
0.7633	Intermediate Similarity	NPD8251	Approved
0.7633	Intermediate Similarity	NPD8099	Discontinued
0.7633	Intermediate Similarity	NPD8252	Approved
0.7622	Intermediate Similarity	NPD6788	Approved
0.7619	Intermediate Similarity	NPD4481	Phase 3
0.7602	Intermediate Similarity	NPD6297	Approved
0.76	Intermediate Similarity	NPD3145	Approved
0.76	Intermediate Similarity	NPD3144	Approved
0.7595	Intermediate Similarity	NPD2420	Approved
0.7595	Intermediate Similarity	NPD2421	Approved
0.7582	Intermediate Similarity	NPD6896	Approved
0.7582	Intermediate Similarity	NPD6895	Approved
0.758	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD7313	Approved
0.7572	Intermediate Similarity	NPD7311	Approved
0.7572	Intermediate Similarity	NPD7310	Approved
0.7572	Intermediate Similarity	NPD7312	Approved
0.7569	Intermediate Similarity	NPD2668	Approved
0.7569	Intermediate Similarity	NPD2667	Approved
0.7561	Intermediate Similarity	NPD5977	Approved
0.7561	Intermediate Similarity	NPD5978	Approved
0.7547	Intermediate Similarity	NPD1424	Approved
0.7545	Intermediate Similarity	NPD7802	Discontinued
0.7534	Intermediate Similarity	NPD2230	Approved
0.7534	Intermediate Similarity	NPD2233	Approved
0.7534	Intermediate Similarity	NPD2232	Approved
0.7532	Intermediate Similarity	NPD3845	Phase 1
0.7529	Intermediate Similarity	NPD6853	Approved
0.7529	Intermediate Similarity	NPD7309	Approved
0.7529	Intermediate Similarity	NPD6851	Approved
0.7516	Intermediate Similarity	NPD6331	Phase 2
0.7515	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7906	Approved
0.75	Intermediate Similarity	NPD2977	Approved
0.75	Intermediate Similarity	NPD2978	Approved
0.7484	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD4577	Approved
0.7471	Intermediate Similarity	NPD4578	Approved
0.7469	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD3692	Discontinued
0.7443	Intermediate Similarity	NPD4663	Approved
0.7434	Intermediate Similarity	NPD4474	Approved
0.7434	Intermediate Similarity	NPD4475	Approved
0.7421	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7153	Discontinued
0.7386	Intermediate Similarity	NPD3110	Approved
0.7386	Intermediate Similarity	NPD3109	Approved
0.7362	Intermediate Similarity	NPD4005	Discontinued
0.7353	Intermediate Similarity	NPD6688	Approved
0.7353	Intermediate Similarity	NPD6687	Approved
0.7347	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4123	Phase 3
0.7325	Intermediate Similarity	NPD1375	Discontinued
0.7325	Intermediate Similarity	NPD3656	Approved
0.732	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD2490	Approved
0.7318	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD2488	Approved
0.7315	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD4210	Discontinued
0.729	Intermediate Similarity	NPD823	Approved
0.729	Intermediate Similarity	NPD817	Approved
0.7284	Intermediate Similarity	NPD7526	Approved
0.7284	Intermediate Similarity	NPD6090	Discontinued
0.7284	Intermediate Similarity	NPD52	Approved
0.7284	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7280	Phase 3
0.7273	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7281	Phase 3
0.7273	Intermediate Similarity	NPD7110	Phase 1
0.7273	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4098	Discontinued
0.7267	Intermediate Similarity	NPD4103	Phase 2
0.7262	Intermediate Similarity	NPD5604	Discontinued
0.7256	Intermediate Similarity	NPD824	Approved
0.7256	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5160	Discontinued
0.725	Intermediate Similarity	NPD2677	Approved
0.7246	Intermediate Similarity	NPD5967	Approved
0.7239	Intermediate Similarity	NPD2122	Discontinued
0.7216	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD3530	Approved
0.7208	Intermediate Similarity	NPD3532	Approved
0.7208	Intermediate Similarity	NPD3531	Approved
0.7205	Intermediate Similarity	NPD7124	Phase 2
0.7197	Intermediate Similarity	NPD3693	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD3687	Approved
0.7195	Intermediate Similarity	NPD3686	Approved
0.7188	Intermediate Similarity	NPD6748	Discontinued
0.7179	Intermediate Similarity	NPD2492	Phase 1
0.7179	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD2904	Discontinued
0.7175	Intermediate Similarity	NPD2971	Approved
0.7175	Intermediate Similarity	NPD2968	Approved
0.7171	Intermediate Similarity	NPD3635	Approved
0.7171	Intermediate Similarity	NPD3637	Approved
0.7171	Intermediate Similarity	NPD3636	Approved
0.717	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7037	Approved
0.7161	Intermediate Similarity	NPD3620	Phase 2
0.7161	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4055	Discovery
0.7158	Intermediate Similarity	NPD5582	Discontinued
0.7152	Intermediate Similarity	NPD3156	Discontinued
0.7143	Intermediate Similarity	NPD4093	Discontinued
0.7143	Intermediate Similarity	NPD1039	Discontinued
0.7134	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1669	Approved
0.7133	Intermediate Similarity	NPD4659	Approved
0.7126	Intermediate Similarity	NPD5720	Discontinued
0.7111	Intermediate Similarity	NPD7291	Discontinued
0.7108	Intermediate Similarity	NPD4678	Approved
0.7108	Intermediate Similarity	NPD4675	Approved
0.7107	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7905	Discontinued
0.7105	Intermediate Similarity	NPD6584	Phase 3
0.7102	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1132	Approved
0.7097	Intermediate Similarity	NPD1136	Approved
0.7097	Intermediate Similarity	NPD1130	Approved
0.7089	Intermediate Similarity	NPD2156	Approved
0.7089	Intermediate Similarity	NPD2155	Approved
0.7089	Intermediate Similarity	NPD2154	Approved
0.7081	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4420	Approved
0.7079	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD2041	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD2042	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD5938	Phase 3
0.7052	Intermediate Similarity	NPD4083	Discontinued
0.7045	Intermediate Similarity	NPD3920	Phase 2
0.7045	Intermediate Similarity	NPD7479	Phase 2
0.7041	Intermediate Similarity	NPD6063	Approved
0.7039	Intermediate Similarity	NPD3055	Approved
0.7039	Intermediate Similarity	NPD3053	Approved
0.7032	Intermediate Similarity	NPD1336	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