NPASS Compound

Structure

CID92541 OpenBabel06191715432D 28 32 0 0 1 0 0 0 0 0999 V2000 -1.7321 6.0000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 5.0000 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 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 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 0.8660 0.5000 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 3.4641 3.0000 0.0000 C 0 0 1 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 0.8660 3.5000 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 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 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 1.7321 2.0000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -1.7321 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 27 1 0 0 0 0 3 28 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 9 1 0 0 0 0 6 15 1 0 0 0 0 7 8 2 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 25 1 0 0 0 0 10 15 1 0 0 0 0 10 18 1 0 0 0 0 11 16 2 0 0 0 0 11 19 1 0 0 0 0 12 20 2 0 0 0 0 12 23 1 0 0 0 0 13 21 2 0 0 0 0 13 24 1 0 0 0 0 14 22 1 0 0 0 0 14 25 1 0 0 0 0 15 25 1 6 0 0 0 16 26 1 0 0 0 0 17 18 1 0 0 0 0 17 19 2 0 0 0 0 18 22 2 0 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 23 24 2 0 0 0 0 23 27 1 0 0 0 0 24 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	377.2
Volume:	399.79
LogP:	5.193
LogD:	3.708
LogS:	-5.977
# Rotatable Bonds:	3
TPSA:	30.93
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.606
Synthetic Accessibility Score:	2.873
Fsp3:	0.417
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.007
MDCK Permeability:	2.877320184779819e-05
Pgp-inhibitor:	0.963
Pgp-substrate:	0.987
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.493
30% Bioavailability (F30%):	0.495

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.888
Plasma Protein Binding (PPB):	75.56981658935547%
Volume Distribution (VD):	1.515
Pgp-substrate:	7.1269402503967285%

ADMET: Metabolism

CYP1A2-inhibitor:	0.645
CYP1A2-substrate:	0.977
CYP2C19-inhibitor:	0.197
CYP2C19-substrate:	0.939
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.824
CYP2D6-inhibitor:	0.986
CYP2D6-substrate:	0.941
CYP3A4-inhibitor:	0.09
CYP3A4-substrate:	0.807

ADMET: Excretion

Clearance (CL):	9.781
Half-life (T1/2):	0.156

ADMET: Toxicity

hERG Blockers:	0.601
Human Hepatotoxicity (H-HT):	0.421
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.816
Rat Oral Acute Toxicity:	0.617
Maximum Recommended Daily Dose:	0.927
Skin Sensitization:	0.957
Carcinogencity:	0.22
Eye Corrosion:	0.004
Eye Irritation:	0.031
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC92541

Natural Product ID:	NPC92541
*Common Name:**	(14As)-3,6,7-Trimethoxy-11,12,13,14,14A,15-Hexahydro-9H-Phenanthro[9,10-B]Quinolizine
IUPAC Name:	(14aS)-3,6,7-trimethoxy-11,12,13,14,14a,15-hexahydro-9H-phenanthro[9,10-b]quinolizine
Synonyms:
Standard InCHIKey:	ANTGAFQZQJMDNP-HNNXBMFYSA-N
Standard InCHI:	InChI=1S/C24H27NO3/c1-26-16-7-8-17-18-10-15-6-4-5-9-25(15)14-22(18)21-13-24(28-3)23(27-2)12-20(21)19(17)11-16/h7-8,11-13,15H,4-6,9-10,14H2,1-3H3/t15-/m0/s1
SMILES:	COc1ccc2c(c1)c1cc(OC)c(cc1c1c2C[C@@H]2CCCCN2C1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1958070
PubChem CID:	52939850
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0001907] Phenanthroquinolizidines

*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
NPO23109	Boehmeria siamensis	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23109	Boehmeria siamensis	Species	Urticaceae	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
GI50	2
IC50	5
Others	4

Activity Type	# Activity
Cell Line	5
Individual Protein	4
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	GI50	=	600.0	nM	PMID[528309]
NPT81	Cell Line	A549	Homo sapiens	GI50	=	700.0	nM	PMID[528309]
NPT137	Cell Line	L1210	Mus musculus	IC50	=	111.0	nM	PMID[528310]
NPT333	Cell Line	CEM	Homo sapiens	IC50	=	201.0	nM	PMID[528310]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	182.0	nM	PMID[528310]
NPT1046	Individual Protein	NAD-dependent deacetylase sirtuin 1	Homo sapiens	Inhibition	=	10.0	%	PMID[528310]
NPT1158	Individual Protein	NAD-dependent deacetylase sirtuin 2	Homo sapiens	Inhibition	=	41.0	%	PMID[528310]
NPT1046	Individual Protein	NAD-dependent deacetylase sirtuin 1	Homo sapiens	Inhibition	=	10.0	%	PMID[528311]
NPT1158	Individual Protein	NAD-dependent deacetylase sirtuin 2	Homo sapiens	Inhibition	=	41.0	%	PMID[528311]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	23.0	nM	PMID[528310]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	82.0	nM	PMID[528310]

☑ 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 NPC92541 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	377
0.1-0.2	1691
0.2-0.3	8141
0.3-0.4	9650
0.4-0.5	6854
0.5-0.6	12246
0.6-0.7	2919
0.7-0.8	560
0.8-0.85	190
0.85-0.9	61
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9857	High Similarity	NPC144863
0.958	High Similarity	NPC219162
0.9441	High Similarity	NPC253883
0.9441	High Similarity	NPC95075
0.9441	High Similarity	NPC90844
0.9375	High Similarity	NPC130941
0.9184	High Similarity	NPC326316
0.9184	High Similarity	NPC81733
0.9161	High Similarity	NPC128019
0.9161	High Similarity	NPC476567
0.9161	High Similarity	NPC136860
0.9128	High Similarity	NPC244112
0.9122	High Similarity	NPC26601
0.9085	High Similarity	NPC314682
0.9041	High Similarity	NPC51957
0.9041	High Similarity	NPC16107
0.9041	High Similarity	NPC210437
0.9041	High Similarity	NPC476144
0.9041	High Similarity	NPC106295
0.9021	High Similarity	NPC328750
0.9021	High Similarity	NPC188163
0.9021	High Similarity	NPC474915
0.9021	High Similarity	NPC213206
0.9	High Similarity	NPC76079
0.898	High Similarity	NPC7467
0.8961	High Similarity	NPC169743
0.894	High Similarity	NPC25084
0.894	High Similarity	NPC247639
0.894	High Similarity	NPC186063
0.8896	High Similarity	NPC233650
0.8889	High Similarity	NPC470925
0.8882	High Similarity	NPC476572
0.8874	High Similarity	NPC325871
0.8874	High Similarity	NPC99659
0.8839	High Similarity	NPC134858
0.8824	High Similarity	NPC477080
0.8816	High Similarity	NPC170503
0.8816	High Similarity	NPC126519
0.8816	High Similarity	NPC203784
0.8776	High Similarity	NPC185838
0.8766	High Similarity	NPC232924
0.8766	High Similarity	NPC160298
0.8766	High Similarity	NPC266753
0.8766	High Similarity	NPC166014
0.8766	High Similarity	NPC306902
0.8766	High Similarity	NPC27410
0.8766	High Similarity	NPC477559
0.8733	High Similarity	NPC192768
0.8733	High Similarity	NPC151895
0.8733	High Similarity	NPC88249
0.8733	High Similarity	NPC220858
0.8733	High Similarity	NPC97221
0.8726	High Similarity	NPC150879
0.8726	High Similarity	NPC210140
0.871	High Similarity	NPC60186
0.8658	High Similarity	NPC179825
0.8658	High Similarity	NPC191376
0.8658	High Similarity	NPC321505
0.8658	High Similarity	NPC476151
0.8654	High Similarity	NPC475393
0.8627	High Similarity	NPC127674
0.8627	High Similarity	NPC5238
0.8627	High Similarity	NPC469817
0.8627	High Similarity	NPC276588
0.8627	High Similarity	NPC2413
0.8627	High Similarity	NPC193949
0.8627	High Similarity	NPC184026
0.8627	High Similarity	NPC172765
0.8627	High Similarity	NPC39701
0.8627	High Similarity	NPC295691
0.8627	High Similarity	NPC189266
0.8627	High Similarity	NPC80129
0.8627	High Similarity	NPC216459
0.8627	High Similarity	NPC249797
0.8627	High Similarity	NPC187022
0.8627	High Similarity	NPC138487
0.8627	High Similarity	NPC110416
0.8627	High Similarity	NPC54379
0.8627	High Similarity	NPC207757
0.8627	High Similarity	NPC278799
0.8627	High Similarity	NPC41178
0.8627	High Similarity	NPC204828
0.8618	High Similarity	NPC210148
0.8618	High Similarity	NPC233029
0.86	High Similarity	NPC476571
0.86	High Similarity	NPC24233
0.86	High Similarity	NPC475959
0.86	High Similarity	NPC147390
0.86	High Similarity	NPC246587
0.86	High Similarity	NPC428
0.86	High Similarity	NPC135538
0.8599	High Similarity	NPC225774
0.8582	High Similarity	NPC160193
0.8571	High Similarity	NPC146288
0.8544	High Similarity	NPC240841
0.8544	High Similarity	NPC476432
0.8544	High Similarity	NPC42549
0.8544	High Similarity	NPC317272
0.8544	High Similarity	NPC256012
0.8544	High Similarity	NPC219341
0.8544	High Similarity	NPC250846
0.8544	High Similarity	NPC268503
0.8544	High Similarity	NPC24264
0.8543	High Similarity	NPC103379
0.8543	High Similarity	NPC477565
0.8535	High Similarity	NPC324144
0.8523	High Similarity	NPC145304
0.8506	High Similarity	NPC123323
0.8491	Intermediate Similarity	NPC474931
0.8491	Intermediate Similarity	NPC306555
0.8491	Intermediate Similarity	NPC145832
0.8491	Intermediate Similarity	NPC247389
0.8491	Intermediate Similarity	NPC205421
0.8491	Intermediate Similarity	NPC12053
0.8491	Intermediate Similarity	NPC158376
0.8491	Intermediate Similarity	NPC298979
0.8491	Intermediate Similarity	NPC81218
0.8491	Intermediate Similarity	NPC117188
0.8481	Intermediate Similarity	NPC13504
0.8481	Intermediate Similarity	NPC306843
0.8481	Intermediate Similarity	NPC136508
0.8481	Intermediate Similarity	NPC16805
0.8481	Intermediate Similarity	NPC167546
0.8481	Intermediate Similarity	NPC196447
0.8481	Intermediate Similarity	NPC302527
0.8481	Intermediate Similarity	NPC253043
0.8481	Intermediate Similarity	NPC96603
0.8481	Intermediate Similarity	NPC212794
0.8481	Intermediate Similarity	NPC477563
0.8481	Intermediate Similarity	NPC78222
0.8462	Intermediate Similarity	NPC216816
0.8452	Intermediate Similarity	NPC234392
0.8452	Intermediate Similarity	NPC31311
0.844	Intermediate Similarity	NPC172403
0.8438	Intermediate Similarity	NPC241055
0.8431	Intermediate Similarity	NPC476579
0.8431	Intermediate Similarity	NPC476568
0.8428	Intermediate Similarity	NPC476573
0.8428	Intermediate Similarity	NPC35627
0.8428	Intermediate Similarity	NPC81247
0.8428	Intermediate Similarity	NPC304659
0.8428	Intermediate Similarity	NPC86144
0.8421	Intermediate Similarity	NPC60538
0.8421	Intermediate Similarity	NPC207824
0.8418	Intermediate Similarity	NPC1229
0.84	Intermediate Similarity	NPC130926
0.8395	Intermediate Similarity	NPC285941
0.8377	Intermediate Similarity	NPC470924
0.8375	Intermediate Similarity	NPC210918
0.8373	Intermediate Similarity	NPC302275
0.8365	Intermediate Similarity	NPC168409
0.8344	Intermediate Similarity	NPC221864
0.8344	Intermediate Similarity	NPC111485
0.8333	Intermediate Similarity	NPC317439
0.8333	Intermediate Similarity	NPC198498
0.8333	Intermediate Similarity	NPC317145
0.8333	Intermediate Similarity	NPC276890
0.8333	Intermediate Similarity	NPC63646
0.8333	Intermediate Similarity	NPC115284
0.8333	Intermediate Similarity	NPC227060
0.8333	Intermediate Similarity	NPC76682
0.8333	Intermediate Similarity	NPC10908
0.8312	Intermediate Similarity	NPC277669
0.8312	Intermediate Similarity	NPC76213
0.8302	Intermediate Similarity	NPC189470
0.8301	Intermediate Similarity	NPC44869
0.8301	Intermediate Similarity	NPC211296
0.8299	Intermediate Similarity	NPC253429
0.8293	Intermediate Similarity	NPC287588
0.8291	Intermediate Similarity	NPC205255
0.8291	Intermediate Similarity	NPC235143
0.8291	Intermediate Similarity	NPC230956
0.8291	Intermediate Similarity	NPC119649
0.8291	Intermediate Similarity	NPC271388
0.8288	Intermediate Similarity	NPC11147
0.8282	Intermediate Similarity	NPC12424
0.8282	Intermediate Similarity	NPC129518
0.8282	Intermediate Similarity	NPC41376
0.8282	Intermediate Similarity	NPC251580
0.828	Intermediate Similarity	NPC79328
0.8272	Intermediate Similarity	NPC118274
0.8272	Intermediate Similarity	NPC168753
0.8261	Intermediate Similarity	NPC204947
0.825	Intermediate Similarity	NPC121275
0.825	Intermediate Similarity	NPC284183
0.825	Intermediate Similarity	NPC232514
0.825	Intermediate Similarity	NPC238530
0.825	Intermediate Similarity	NPC4138
0.825	Intermediate Similarity	NPC276944
0.8239	Intermediate Similarity	NPC79402
0.8239	Intermediate Similarity	NPC80759
0.8228	Intermediate Similarity	NPC7393
0.8221	Intermediate Similarity	NPC108434
0.8221	Intermediate Similarity	NPC149090
0.8221	Intermediate Similarity	NPC239775
0.8221	Intermediate Similarity	NPC19520
0.8221	Intermediate Similarity	NPC475215
0.8214	Intermediate Similarity	NPC95426
0.8214	Intermediate Similarity	NPC16357
0.8214	Intermediate Similarity	NPC302245

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 NPC92541 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	227
0.1-0.2	814
0.2-0.3	900
0.3-0.4	1792
0.4-0.5	2728
0.5-0.6	1829
0.6-0.7	669
0.7-0.8	162
0.8-0.85	26
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9041	High Similarity	NPD4584	Approved
0.9021	High Similarity	NPD4664	Clinical (unspecified phase)
0.8627	High Similarity	NPD7298	Approved
0.8535	High Similarity	NPD7201	Clinical (unspecified phase)
0.8431	Intermediate Similarity	NPD4017	Approved
0.8421	Intermediate Similarity	NPD3640	Phase 3
0.8421	Intermediate Similarity	NPD3639	Approved
0.8421	Intermediate Similarity	NPD3641	Approved
0.8333	Intermediate Similarity	NPD8099	Discontinued
0.8333	Intermediate Similarity	NPD8252	Approved
0.8333	Intermediate Similarity	NPD8251	Approved
0.8299	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.8299	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD8156	Discontinued
0.8264	Intermediate Similarity	NPD5718	Phase 2
0.8217	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD4772	Phase 2
0.8205	Intermediate Similarity	NPD4773	Phase 2
0.8182	Intermediate Similarity	NPD6030	Approved
0.8182	Intermediate Similarity	NPD6031	Approved
0.8151	Intermediate Similarity	NPD3109	Approved
0.8151	Intermediate Similarity	NPD3110	Approved
0.8113	Intermediate Similarity	NPD6788	Approved
0.8105	Intermediate Similarity	NPD2420	Approved
0.8105	Intermediate Similarity	NPD2421	Approved
0.8105	Intermediate Similarity	NPD7598	Phase 2
0.8105	Intermediate Similarity	NPD3124	Discontinued
0.8092	Intermediate Similarity	NPD5241	Discontinued
0.8069	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD7833	Phase 2
0.8063	Intermediate Similarity	NPD7831	Phase 2
0.8025	Intermediate Similarity	NPD7802	Discontinued
0.8014	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD8054	Approved
0.7988	Intermediate Similarity	NPD8053	Approved
0.7974	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD4475	Approved
0.7959	Intermediate Similarity	NPD4474	Approved
0.7922	Intermediate Similarity	NPD3845	Phase 1
0.7922	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD6895	Approved
0.7867	Intermediate Similarity	NPD6896	Approved
0.7848	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD6107	Approved
0.7778	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD2898	Approved
0.7765	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD4010	Discontinued
0.7758	Intermediate Similarity	NPD3051	Approved
0.7758	Intermediate Similarity	NPD4166	Phase 2
0.7725	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD5978	Approved
0.7716	Intermediate Similarity	NPD5977	Approved
0.7683	Intermediate Similarity	NPD7400	Phase 3
0.7628	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD2969	Approved
0.7605	Intermediate Similarity	NPD2970	Approved
0.7603	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD6748	Discontinued
0.756	Intermediate Similarity	NPD4481	Phase 3
0.756	Intermediate Similarity	NPD2489	Approved
0.756	Intermediate Similarity	NPD27	Approved
0.7544	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD7291	Discontinued
0.7534	Intermediate Similarity	NPD1669	Approved
0.7533	Intermediate Similarity	NPD7294	Phase 1
0.7531	Intermediate Similarity	NPD7110	Phase 1
0.7531	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD5312	Approved
0.7529	Intermediate Similarity	NPD5313	Approved
0.7514	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6687	Approved
0.75	Intermediate Similarity	NPD6688	Approved
0.7484	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7124	Phase 2
0.7459	Intermediate Similarity	NPD8095	Phase 1
0.7452	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD6297	Approved
0.744	Intermediate Similarity	NPD6071	Discontinued
0.7394	Intermediate Similarity	NPD2563	Approved
0.7394	Intermediate Similarity	NPD2560	Approved
0.7391	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4727	Phase 1
0.7389	Intermediate Similarity	NPD5177	Phase 3
0.7389	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD7905	Discontinued
0.7378	Intermediate Similarity	NPD5720	Discontinued
0.7375	Intermediate Similarity	NPD1424	Approved
0.7371	Intermediate Similarity	NPD6618	Phase 2
0.7351	Intermediate Similarity	NPD5156	Approved
0.7351	Intermediate Similarity	NPD5155	Approved
0.7342	Intermediate Similarity	NPD6331	Phase 2
0.7337	Intermediate Similarity	NPD6747	Phase 1
0.7325	Intermediate Similarity	NPD7037	Approved
0.7315	Intermediate Similarity	NPD4098	Discontinued
0.7314	Intermediate Similarity	NPD2968	Approved
0.7314	Intermediate Similarity	NPD2971	Approved
0.7296	Intermediate Similarity	NPD3301	Approved
0.7285	Intermediate Similarity	NPD3595	Approved
0.7285	Intermediate Similarity	NPD3594	Approved
0.7285	Intermediate Similarity	NPD2606	Approved
0.7285	Intermediate Similarity	NPD2605	Approved
0.7284	Intermediate Similarity	NPD1914	Approved
0.7284	Intermediate Similarity	NPD5976	Discontinued
0.7283	Intermediate Similarity	NPD7479	Phase 2
0.7283	Intermediate Similarity	NPD3920	Phase 2
0.7278	Intermediate Similarity	NPD3060	Approved
0.7278	Intermediate Similarity	NPD4162	Approved
0.7273	Intermediate Similarity	NPD6853	Approved
0.7273	Intermediate Similarity	NPD6851	Approved
0.7273	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD2667	Approved
0.726	Intermediate Similarity	NPD2668	Approved
0.7256	Intermediate Similarity	NPD6876	Approved
0.7256	Intermediate Similarity	NPD6875	Approved
0.7255	Intermediate Similarity	NPD2674	Phase 3
0.7255	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD5283	Phase 1
0.7253	Intermediate Similarity	NPD7034	Discontinued
0.7251	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD7906	Approved
0.7233	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD5754	Discontinued
0.7222	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6090	Discontinued
0.7222	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3635	Approved
0.7219	Intermediate Similarity	NPD3637	Approved
0.7219	Intermediate Similarity	NPD3636	Approved
0.7216	Intermediate Similarity	NPD7311	Approved
0.7216	Intermediate Similarity	NPD7313	Approved
0.7216	Intermediate Similarity	NPD7310	Approved
0.7216	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD4577	Approved
0.7216	Intermediate Similarity	NPD7312	Approved
0.7216	Intermediate Similarity	NPD4578	Approved
0.7212	Intermediate Similarity	NPD7438	Suspended
0.7202	Intermediate Similarity	NPD4055	Discovery
0.7195	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD4093	Discontinued
0.7179	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD2122	Discontinued
0.7178	Intermediate Similarity	NPD7427	Discontinued
0.7175	Intermediate Similarity	NPD7309	Approved
0.717	Intermediate Similarity	NPD4237	Approved
0.717	Intermediate Similarity	NPD4236	Phase 3
0.7159	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3531	Approved
0.7143	Intermediate Similarity	NPD3530	Approved
0.7143	Intermediate Similarity	NPD3532	Approved
0.7135	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1753	Discontinued
0.7127	Intermediate Similarity	NPD3921	Approved
0.7127	Intermediate Similarity	NPD3923	Approved
0.7127	Intermediate Similarity	NPD3924	Approved
0.7127	Intermediate Similarity	NPD3922	Approved
0.7118	Intermediate Similarity	NPD5677	Discontinued
0.7115	Intermediate Similarity	NPD2492	Phase 1
0.7114	Intermediate Similarity	NPD2232	Approved
0.7114	Intermediate Similarity	NPD2233	Approved
0.7114	Intermediate Similarity	NPD2230	Approved
0.711	Intermediate Similarity	NPD5966	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD5938	Phase 3
0.7108	Intermediate Similarity	NPD6873	Phase 2
0.7095	Intermediate Similarity	NPD4663	Approved
0.7091	Intermediate Similarity	NPD4005	Discontinued
0.7089	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5160	Discontinued
0.7078	Intermediate Similarity	NPD3144	Approved
0.7078	Intermediate Similarity	NPD5109	Approved
0.7078	Intermediate Similarity	NPD5111	Phase 2
0.7078	Intermediate Similarity	NPD5110	Phase 2
0.7078	Intermediate Similarity	NPD3145	Approved
0.7075	Intermediate Similarity	NPD2594	Approved
0.7075	Intermediate Similarity	NPD2595	Approved
0.7072	Intermediate Similarity	NPD2490	Approved
0.7072	Intermediate Similarity	NPD2488	Approved
0.707	Intermediate Similarity	NPD6111	Discontinued
0.7069	Intermediate Similarity	NPD4498	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1420	Approved
0.7067	Intermediate Similarity	NPD1421	Approved
0.7063	Intermediate Similarity	NPD44	Approved
0.7063	Intermediate Similarity	NPD6364	Approved
0.7055	Intermediate Similarity	NPD4123	Phase 3
0.7039	Intermediate Similarity	NPD6584	Phase 3
0.7037	Intermediate Similarity	NPD6066	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD4108	Discontinued
0.7018	Intermediate Similarity	NPD6037	Discontinued
0.7007	Intermediate Similarity	NPD6580	Approved
0.7007	Intermediate Similarity	NPD6581	Approved
0.7006	Intermediate Similarity	NPD2989	Phase 2
0.7006	Intermediate Similarity	NPD2653	Approved
0.7006	Intermediate Similarity	NPD2986	Phase 2

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