NPASS Compound

Structure

CID210086 OpenBabel06191716002D 24 26 0 0 0 0 0 0 0 0999 V2000 1.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1340 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1340 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1340 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 14 2 0 0 0 0 8 16 2 0 0 0 0 9 10 2 0 0 0 0 9 14 1 0 0 0 0 10 17 1 0 0 0 0 11 12 1 0 0 0 0 11 15 1 0 0 0 0 12 21 1 0 0 0 0 13 15 2 0 0 0 0 13 18 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 16 19 1 0 0 0 0 17 19 2 0 0 0 0 18 20 2 0 0 0 0 18 23 1 0 0 0 0 19 20 1 0 0 0 0 20 24 1 0 0 0 0 21 22 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	325.17
Volume:	347.719
LogP:	2.625
LogD:	1.542
LogS:	0.108
# Rotatable Bonds:	5
TPSA:	41.52
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.402
Synthetic Accessibility Score:	2.573
Fsp3:	0.3
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:	-5.14
MDCK Permeability:	3.835973984678276e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.16
20% Bioavailability (F20%):	0.898
30% Bioavailability (F30%):	0.926

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.952
Plasma Protein Binding (PPB):	85.01764678955078%
Volume Distribution (VD):	2.122
Pgp-substrate:	7.506755828857422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.898
CYP1A2-substrate:	0.983
CYP2C19-inhibitor:	0.063
CYP2C19-substrate:	0.876
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.899
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.931
CYP3A4-inhibitor:	0.263
CYP3A4-substrate:	0.219

ADMET: Excretion

Clearance (CL):	11.011
Half-life (T1/2):	0.899

ADMET: Toxicity

hERG Blockers:	0.358
Human Hepatotoxicity (H-HT):	0.218
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.616
Rat Oral Acute Toxicity:	0.591
Maximum Recommended Daily Dose:	0.857
Skin Sensitization:	0.113
Carcinogencity:	0.282
Eye Corrosion:	0.005
Eye Irritation:	0.305
Respiratory Toxicity:	0.571

Download Data

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

Natural Product: NPC210086

Natural Product ID:	NPC210086
*Common Name:**	Atherosperminine N-Oxide
IUPAC Name:	2-(3,4-dimethoxyphenanthren-1-yl)-N,N-dimethylethanamine oxide
Synonyms:
Standard InCHIKey:	HIGPYKBZLWYMDX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H23NO3/c1-21(2,22)12-11-15-13-18(23-3)20(24-4)19-16-8-6-5-7-14(16)9-10-17(15)19/h5-10,13H,11-12H2,1-4H3
SMILES:	CN(=O)(C)CCc1cc(c(c2c3ccccc3ccc12)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3706995
PubChem CID:	10404054
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003332] 6,6a-secoaporphines

*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
NPO22118	Euodia vitiflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18541	Aglaia spectabilis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22573	Rhus cotinus	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22696	Lactarius chrysorrheus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19918	Lessingianthus rubricaulis	Species	Asteraceae	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	7

Activity Type	# Activity
CELL-LINE	4
Tissue	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	37.4	%	PMID[519477]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	0.0	%	PMID[519477]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	61.1	%	PMID[519477]
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	=	5.8	%	PMID[519477]
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	=	30.0	%	PMID[519477]
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	=	27.5	%	PMID[519477]

☑ 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 NPC210086 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	345
0.1-0.2	2081
0.2-0.3	9037
0.3-0.4	9328
0.4-0.5	5816
0.5-0.6	11025
0.6-0.7	4103
0.7-0.8	870
0.8-0.85	71
0.85-0.9	16
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.8828	High Similarity	NPC470924
0.8776	High Similarity	NPC477132
0.8776	High Similarity	NPC477133
0.875	High Similarity	NPC44869
0.8601	High Similarity	NPC145304
0.8367	Intermediate Similarity	NPC211296
0.8357	Intermediate Similarity	NPC475828
0.8312	Intermediate Similarity	NPC76116
0.8217	Intermediate Similarity	NPC329911
0.8153	Intermediate Similarity	NPC160570
0.8153	Intermediate Similarity	NPC164429
0.8133	Intermediate Similarity	NPC81733
0.8133	Intermediate Similarity	NPC326316
0.8121	Intermediate Similarity	NPC219162
0.8121	Intermediate Similarity	NPC92541
0.8079	Intermediate Similarity	NPC114124
0.8	Intermediate Similarity	NPC160193
0.8	Intermediate Similarity	NPC314682
0.7987	Intermediate Similarity	NPC144863
0.7987	Intermediate Similarity	NPC95075
0.7987	Intermediate Similarity	NPC253883
0.7987	Intermediate Similarity	NPC90844
0.7974	Intermediate Similarity	NPC244112
0.7961	Intermediate Similarity	NPC37272
0.7945	Intermediate Similarity	NPC328750
0.7945	Intermediate Similarity	NPC474915
0.7945	Intermediate Similarity	NPC188163
0.7945	Intermediate Similarity	NPC213206
0.7933	Intermediate Similarity	NPC130941
0.7883	Intermediate Similarity	NPC298486
0.7871	Intermediate Similarity	NPC475326
0.7871	Intermediate Similarity	NPC476572
0.7867	Intermediate Similarity	NPC106295
0.7867	Intermediate Similarity	NPC51957
0.7867	Intermediate Similarity	NPC476151
0.7867	Intermediate Similarity	NPC16107
0.7867	Intermediate Similarity	NPC476144
0.7867	Intermediate Similarity	NPC210437
0.7857	Intermediate Similarity	NPC99659
0.7857	Intermediate Similarity	NPC325871
0.7857	Intermediate Similarity	NPC172403
0.7853	Intermediate Similarity	NPC477560
0.7852	Intermediate Similarity	NPC130926
0.7847	Intermediate Similarity	NPC11147
0.7834	Intermediate Similarity	NPC60186
0.7817	Intermediate Similarity	NPC476570
0.7815	Intermediate Similarity	NPC7467
0.7806	Intermediate Similarity	NPC170503
0.7806	Intermediate Similarity	NPC203784
0.7806	Intermediate Similarity	NPC126519
0.7793	Intermediate Similarity	NPC42793
0.7793	Intermediate Similarity	NPC231884
0.7793	Intermediate Similarity	NPC167944
0.7771	Intermediate Similarity	NPC160298
0.7771	Intermediate Similarity	NPC266753
0.7771	Intermediate Similarity	NPC27410
0.7771	Intermediate Similarity	NPC477559
0.7771	Intermediate Similarity	NPC232924
0.7771	Intermediate Similarity	NPC166014
0.7771	Intermediate Similarity	NPC306902
0.7763	Intermediate Similarity	NPC103379
0.7763	Intermediate Similarity	NPC477565
0.7762	Intermediate Similarity	NPC118419
0.7733	Intermediate Similarity	NPC185838
0.7727	Intermediate Similarity	NPC26601
0.7718	Intermediate Similarity	NPC136860
0.7718	Intermediate Similarity	NPC476567
0.7718	Intermediate Similarity	NPC128019
0.7716	Intermediate Similarity	NPC10871
0.7711	Intermediate Similarity	NPC233718
0.7707	Intermediate Similarity	NPC118804
0.7692	Intermediate Similarity	NPC323443
0.7692	Intermediate Similarity	NPC180756
0.7682	Intermediate Similarity	NPC473934
0.7632	Intermediate Similarity	NPC321505
0.7632	Intermediate Similarity	NPC179825
0.7632	Intermediate Similarity	NPC191376
0.7628	Intermediate Similarity	NPC76079
0.7625	Intermediate Similarity	NPC225774
0.7597	Intermediate Similarity	NPC274026
0.7586	Intermediate Similarity	NPC160692
0.7584	Intermediate Similarity	NPC470925
0.7582	Intermediate Similarity	NPC147390
0.7582	Intermediate Similarity	NPC24233
0.7582	Intermediate Similarity	NPC476571
0.7582	Intermediate Similarity	NPC428
0.7582	Intermediate Similarity	NPC246587
0.7582	Intermediate Similarity	NPC475959
0.7582	Intermediate Similarity	NPC135538
0.758	Intermediate Similarity	NPC186063
0.7578	Intermediate Similarity	NPC24264
0.7578	Intermediate Similarity	NPC476432
0.7578	Intermediate Similarity	NPC219341
0.7574	Intermediate Similarity	NPC120075
0.7562	Intermediate Similarity	NPC233650
0.7562	Intermediate Similarity	NPC324144
0.7551	Intermediate Similarity	NPC131204
0.7551	Intermediate Similarity	NPC301050
0.7551	Intermediate Similarity	NPC7018
0.7548	Intermediate Similarity	NPC476579
0.7548	Intermediate Similarity	NPC8337
0.7548	Intermediate Similarity	NPC85747
0.7535	Intermediate Similarity	NPC301713
0.7531	Intermediate Similarity	NPC81218
0.7531	Intermediate Similarity	NPC158376
0.7531	Intermediate Similarity	NPC306555
0.7531	Intermediate Similarity	NPC117188
0.7531	Intermediate Similarity	NPC205421
0.7531	Intermediate Similarity	NPC12053
0.7531	Intermediate Similarity	NPC145832
0.7531	Intermediate Similarity	NPC247389
0.7531	Intermediate Similarity	NPC474931
0.7531	Intermediate Similarity	NPC298979
0.7519	Intermediate Similarity	NPC470723
0.7517	Intermediate Similarity	NPC471983
0.7517	Intermediate Similarity	NPC149337
0.7516	Intermediate Similarity	NPC13504
0.7516	Intermediate Similarity	NPC302527
0.7516	Intermediate Similarity	NPC127674
0.7516	Intermediate Similarity	NPC249797
0.7516	Intermediate Similarity	NPC477563
0.7516	Intermediate Similarity	NPC39701
0.7516	Intermediate Similarity	NPC216459
0.7516	Intermediate Similarity	NPC167546
0.7516	Intermediate Similarity	NPC189266
0.7516	Intermediate Similarity	NPC196447
0.7516	Intermediate Similarity	NPC172765
0.7516	Intermediate Similarity	NPC253043
0.7516	Intermediate Similarity	NPC5238
0.7516	Intermediate Similarity	NPC136508
0.7516	Intermediate Similarity	NPC184026
0.7516	Intermediate Similarity	NPC41178
0.7516	Intermediate Similarity	NPC134858
0.7516	Intermediate Similarity	NPC2413
0.7516	Intermediate Similarity	NPC138487
0.7516	Intermediate Similarity	NPC295691
0.7516	Intermediate Similarity	NPC193949
0.7516	Intermediate Similarity	NPC306843
0.7516	Intermediate Similarity	NPC16805
0.7516	Intermediate Similarity	NPC96603
0.7516	Intermediate Similarity	NPC204828
0.7516	Intermediate Similarity	NPC276588
0.7516	Intermediate Similarity	NPC54379
0.7516	Intermediate Similarity	NPC110416
0.7516	Intermediate Similarity	NPC278799
0.7516	Intermediate Similarity	NPC207757
0.7516	Intermediate Similarity	NPC78222
0.7516	Intermediate Similarity	NPC212794
0.7516	Intermediate Similarity	NPC469817
0.75	Intermediate Similarity	NPC193528
0.75	Intermediate Similarity	NPC253429
0.75	Intermediate Similarity	NPC30462
0.75	Intermediate Similarity	NPC312105
0.75	Intermediate Similarity	NPC148898
0.75	Intermediate Similarity	NPC82285
0.75	Intermediate Similarity	NPC133011
0.7485	Intermediate Similarity	NPC241055
0.7484	Intermediate Similarity	NPC477080
0.7483	Intermediate Similarity	NPC100129
0.7469	Intermediate Similarity	NPC476573
0.7469	Intermediate Similarity	NPC35627
0.7469	Intermediate Similarity	NPC81247
0.7469	Intermediate Similarity	NPC86144
0.7469	Intermediate Similarity	NPC304659
0.7468	Intermediate Similarity	NPC146288
0.7467	Intermediate Similarity	NPC323204
0.7466	Intermediate Similarity	NPC325568
0.7455	Intermediate Similarity	NPC285941
0.7453	Intermediate Similarity	NPC1229
0.7452	Intermediate Similarity	NPC477564
0.7452	Intermediate Similarity	NPC2295
0.7445	Intermediate Similarity	NPC25648
0.7436	Intermediate Similarity	NPC52475
0.7429	Intermediate Similarity	NPC211992
0.7426	Intermediate Similarity	NPC47194
0.7423	Intermediate Similarity	NPC150879
0.7423	Intermediate Similarity	NPC210140
0.7423	Intermediate Similarity	NPC210918
0.7421	Intermediate Similarity	NPC40389
0.7421	Intermediate Similarity	NPC78359
0.7421	Intermediate Similarity	NPC315707
0.7421	Intermediate Similarity	NPC65490
0.7421	Intermediate Similarity	NPC148014
0.7419	Intermediate Similarity	NPC207824
0.7419	Intermediate Similarity	NPC60538
0.741	Intermediate Similarity	NPC321133
0.7407	Intermediate Similarity	NPC2770
0.7407	Intermediate Similarity	NPC39103
0.7407	Intermediate Similarity	NPC255607
0.7407	Intermediate Similarity	NPC168409
0.7407	Intermediate Similarity	NPC3375
0.7405	Intermediate Similarity	NPC78733
0.7405	Intermediate Similarity	NPC93593
0.7405	Intermediate Similarity	NPC123323
0.7389	Intermediate Similarity	NPC18614
0.7379	Intermediate Similarity	NPC262641
0.7378	Intermediate Similarity	NPC470324
0.7372	Intermediate Similarity	NPC192768
0.7372	Intermediate Similarity	NPC97221
0.7372	Intermediate Similarity	NPC88249

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 NPC210086 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	219
0.1-0.2	998
0.2-0.3	1020
0.3-0.4	2351
0.4-0.5	2366
0.5-0.6	1395
0.6-0.7	636
0.7-0.8	154
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8027	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD5718	Phase 2
0.7929	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD4584	Approved
0.7793	Intermediate Similarity	NPD6896	Approved
0.7793	Intermediate Similarity	NPD6895	Approved
0.7692	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD5241	Discontinued
0.7571	Intermediate Similarity	NPD1669	Approved
0.7466	Intermediate Similarity	NPD3110	Approved
0.7466	Intermediate Similarity	NPD3109	Approved
0.7448	Intermediate Similarity	NPD1039	Discontinued
0.7436	Intermediate Similarity	NPD4017	Approved
0.7423	Intermediate Similarity	NPD2970	Approved
0.7423	Intermediate Similarity	NPD2969	Approved
0.7421	Intermediate Similarity	NPD2563	Approved
0.7421	Intermediate Similarity	NPD2560	Approved
0.7419	Intermediate Similarity	NPD3640	Phase 3
0.7419	Intermediate Similarity	NPD3641	Approved
0.7419	Intermediate Similarity	NPD3639	Approved
0.741	Intermediate Similarity	NPD2668	Approved
0.741	Intermediate Similarity	NPD2667	Approved
0.7386	Intermediate Similarity	NPD7124	Phase 2
0.7378	Intermediate Similarity	NPD2489	Approved
0.7378	Intermediate Similarity	NPD4481	Phase 3
0.7378	Intermediate Similarity	NPD2898	Approved
0.7378	Intermediate Similarity	NPD27	Approved
0.7376	Intermediate Similarity	NPD2233	Approved
0.7376	Intermediate Similarity	NPD2230	Approved
0.7376	Intermediate Similarity	NPD2232	Approved
0.7368	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6331	Phase 2
0.7365	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD3051	Approved
0.7355	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD7831	Phase 2
0.7329	Intermediate Similarity	NPD7833	Phase 2
0.7308	Intermediate Similarity	NPD6031	Approved
0.7308	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6030	Approved
0.7303	Intermediate Similarity	NPD5177	Phase 3
0.7292	Intermediate Similarity	NPD7905	Discontinued
0.729	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4474	Approved
0.7279	Intermediate Similarity	NPD4475	Approved
0.7279	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD5283	Phase 1
0.7273	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6071	Discontinued
0.7248	Intermediate Similarity	NPD2653	Approved
0.7244	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD4772	Phase 2
0.7233	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7110	Phase 1
0.7233	Intermediate Similarity	NPD4773	Phase 2
0.723	Intermediate Similarity	NPD2238	Phase 2
0.7214	Intermediate Similarity	NPD3445	Approved
0.7214	Intermediate Similarity	NPD3443	Approved
0.7214	Intermediate Similarity	NPD3444	Approved
0.72	Intermediate Similarity	NPD6111	Discontinued
0.719	Intermediate Similarity	NPD4162	Approved
0.719	Intermediate Similarity	NPD3060	Approved
0.7188	Intermediate Similarity	NPD7298	Approved
0.717	Intermediate Similarity	NPD6875	Approved
0.717	Intermediate Similarity	NPD6876	Approved
0.7162	Intermediate Similarity	NPD2674	Phase 3
0.7143	Intermediate Similarity	NPD5754	Discontinued
0.7135	Intermediate Similarity	NPD7313	Approved
0.7135	Intermediate Similarity	NPD7310	Approved
0.7135	Intermediate Similarity	NPD7311	Approved
0.7135	Intermediate Similarity	NPD7312	Approved
0.7124	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2420	Approved
0.7115	Intermediate Similarity	NPD2421	Approved
0.7107	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD2161	Phase 2
0.7097	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7309	Approved
0.7092	Intermediate Similarity	NPD5691	Approved
0.7081	Intermediate Similarity	NPD7248	Discontinued
0.707	Intermediate Similarity	NPD1424	Approved
0.7055	Intermediate Similarity	NPD6788	Approved
0.7044	Intermediate Similarity	NPD4210	Discontinued
0.7042	Intermediate Similarity	NPD4626	Approved
0.7035	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD2922	Phase 1
0.702	Intermediate Similarity	NPD2157	Approved
0.7019	Intermediate Similarity	NPD6873	Phase 2
0.7006	Intermediate Similarity	NPD3124	Discontinued
0.6994	Remote Similarity	NPD5978	Approved
0.6994	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD5977	Approved
0.6988	Remote Similarity	NPD7802	Discontinued
0.6986	Remote Similarity	NPD4098	Discontinued
0.6982	Remote Similarity	NPD8099	Discontinued
0.6982	Remote Similarity	NPD8251	Approved
0.6982	Remote Similarity	NPD8252	Approved
0.6981	Remote Similarity	NPD1914	Approved
0.6981	Remote Similarity	NPD5976	Discontinued
0.698	Remote Similarity	NPD3145	Approved
0.698	Remote Similarity	NPD5111	Phase 2
0.698	Remote Similarity	NPD5110	Phase 2
0.698	Remote Similarity	NPD5109	Approved
0.698	Remote Similarity	NPD3144	Approved
0.698	Remote Similarity	NPD7294	Phase 1
0.6975	Remote Similarity	NPD5720	Discontinued
0.6972	Remote Similarity	NPD4093	Discontinued
0.6972	Remote Similarity	NPD1651	Approved
0.697	Remote Similarity	NPD7400	Phase 3
0.6968	Remote Similarity	NPD4237	Approved
0.6968	Remote Similarity	NPD4236	Phase 3
0.6948	Remote Similarity	NPD1375	Discontinued
0.6941	Remote Similarity	NPD8156	Discontinued
0.6936	Remote Similarity	NPD2968	Approved
0.6936	Remote Similarity	NPD2971	Approved
0.6933	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4585	Approved
0.6928	Remote Similarity	NPD4108	Discontinued
0.6918	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD8651	Approved
0.6918	Remote Similarity	NPD6090	Discontinued
0.6909	Remote Similarity	NPD4055	Discovery
0.6908	Remote Similarity	NPD4097	Suspended
0.6908	Remote Similarity	NPD2492	Phase 1
0.6905	Remote Similarity	NPD6688	Approved
0.6905	Remote Similarity	NPD6687	Approved
0.6903	Remote Similarity	NPD7037	Approved
0.6901	Remote Similarity	NPD2486	Discontinued
0.6894	Remote Similarity	NPD4005	Discontinued
0.6886	Remote Similarity	NPD6107	Approved
0.6883	Remote Similarity	NPD4476	Approved
0.6883	Remote Similarity	NPD4477	Approved
0.6879	Remote Similarity	NPD3692	Discontinued
0.6867	Remote Similarity	NPD5709	Phase 3
0.6857	Remote Similarity	NPD595	Approved
0.6857	Remote Similarity	NPD593	Approved
0.6855	Remote Similarity	NPD7020	Approved
0.6855	Remote Similarity	NPD7019	Approved
0.6845	Remote Similarity	NPD4166	Phase 2
0.6845	Remote Similarity	NPD6747	Phase 1
0.6845	Remote Similarity	NPD4010	Discontinued
0.6842	Remote Similarity	NPD3657	Discovery
0.6839	Remote Similarity	NPD4577	Approved
0.6839	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4578	Approved
0.6835	Remote Similarity	NPD6666	Approved
0.6835	Remote Similarity	NPD6667	Approved
0.6826	Remote Similarity	NPD4666	Phase 3
0.6824	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6584	Phase 3
0.6821	Remote Similarity	NPD3530	Approved
0.6821	Remote Similarity	NPD3531	Approved
0.6821	Remote Similarity	NPD3532	Approved
0.6818	Remote Similarity	NPD2156	Approved
0.6818	Remote Similarity	NPD1753	Discontinued
0.6818	Remote Similarity	NPD2154	Approved
0.6818	Remote Similarity	NPD2155	Approved
0.6809	Remote Similarity	NPD2557	Approved
0.6809	Remote Similarity	NPD709	Approved
0.68	Remote Similarity	NPD1024	Discontinued
0.6795	Remote Similarity	NPD2170	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD7153	Discontinued
0.6795	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD5304	Approved
0.6783	Remote Similarity	NPD5303	Approved
0.6783	Remote Similarity	NPD6581	Approved
0.6783	Remote Similarity	NPD6580	Approved
0.678	Remote Similarity	NPD7906	Approved
0.6779	Remote Similarity	NPD2237	Approved
0.6779	Remote Similarity	NPD1712	Approved
0.6776	Remote Similarity	NPD2979	Phase 3
0.6776	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6225	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD3620	Phase 2
0.6774	Remote Similarity	NPD2438	Suspended
0.677	Remote Similarity	NPD4727	Phase 1
0.6763	Remote Similarity	NPD228	Approved
0.6761	Remote Similarity	NPD3596	Phase 2
0.6759	Remote Similarity	NPD3294	Phase 2
0.6755	Remote Similarity	NPD1336	Approved
0.6755	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.675	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.675	Remote Similarity	NPD4123	Phase 3
0.6739	Remote Similarity	NPD4482	Phase 3
0.6736	Remote Similarity	NPD3049	Approved
0.6736	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD3687	Approved
0.6728	Remote Similarity	NPD3686	Approved
0.6726	Remote Similarity	NPD3365	Discontinued
0.6723	Remote Similarity	NPD4663	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