NPASS Compound

Structure

NPC221864 OpenBabel07101718312D 29 32 0 0 1 0 0 0 0 0999 V2000 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 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 -5.1962 -0.0000 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 -0.0000 -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 -0.0000 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 -2.5981 -0.5000 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 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 2 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 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 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 N 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 -4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 4 25 1 0 0 0 0 5 29 1 0 0 0 0 6 7 2 0 0 0 0 6 15 1 0 0 0 0 7 18 1 0 0 0 0 8 12 2 0 0 0 0 8 16 1 0 0 0 0 9 12 1 0 0 0 0 9 21 2 0 0 0 0 10 13 1 0 0 0 0 10 17 1 0 0 0 0 11 19 2 0 0 0 0 11 20 1 0 0 0 0 13 2 1 6 0 0 0 13 25 1 0 0 0 0 14 3 1 1 0 0 0 14 22 1 0 0 0 0 14 25 1 0 0 0 0 15 16 2 0 0 0 0 15 23 1 0 0 0 0 16 24 1 0 0 0 0 17 22 2 0 0 0 0 17 23 1 0 0 0 0 18 24 2 0 0 0 0 18 26 1 0 0 0 0 19 22 1 0 0 0 0 19 27 1 0 0 0 0 20 23 2 0 0 0 0 20 28 1 0 0 0 0 21 24 1 0 0 0 0 21 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	393.19
Volume:	414.5
LogP:	5.067
LogD:	3.611
LogS:	-3.94
# Rotatable Bonds:	2
TPSA:	73.16
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.579
Synthetic Accessibility Score:	3.664
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.141
MDCK Permeability:	9.866455002338625e-06
Pgp-inhibitor:	0.68
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.821

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	96.88220977783203%
Volume Distribution (VD):	0.618
Pgp-substrate:	2.2752504348754883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.875
CYP1A2-substrate:	0.959
CYP2C19-inhibitor:	0.284
CYP2C19-substrate:	0.228
CYP2C9-inhibitor:	0.273
CYP2C9-substrate:	0.811
CYP2D6-inhibitor:	0.404
CYP2D6-substrate:	0.876
CYP3A4-inhibitor:	0.11
CYP3A4-substrate:	0.797

ADMET: Excretion

Clearance (CL):	4.665
Half-life (T1/2):	0.266

ADMET: Toxicity

hERG Blockers:	0.208
Human Hepatotoxicity (H-HT):	0.086
Drug-inuced Liver Injury (DILI):	0.872
AMES Toxicity:	0.675
Rat Oral Acute Toxicity:	0.384
Maximum Recommended Daily Dose:	0.988
Skin Sensitization:	0.879
Carcinogencity:	0.066
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.887

Download Data

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

Natural Product: NPC221864

Natural Product ID:	NPC221864
*Common Name:**	Ancistrocongoline A
IUPAC Name:	(1R,3R)-5-(4-hydroxy-5-methoxy-7-methylnaphthalen-1-yl)-1,2,3-trimethyl-3,4-dihydro-1H-isoquinoline-6,8-diol
Synonyms:
Standard InCHIKey:	GWJJRDKEDFSIDL-ZIAGYGMSSA-N
Standard InCHI:	InChI=1S/C24H27NO4/c1-12-8-16-15(6-7-18(26)24(16)21(9-12)29-5)23-17-10-13(2)25(4)14(3)22(17)19(27)11-20(23)28/h6-9,11,13-14,26-28H,10H2,1-5H3/t13-,14-/m1/s1
SMILES:	COc1cc(C)cc2c1c(O)ccc2c1c(O)cc(c2c1C[C@@H](C)N([C@@H]2C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL520005
PubChem CID:	392424
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002566] Isoquinolines and derivatives [CHEMONTID:0002195] Naphthylisoquinolines

*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
NPO33285	ancistrocladus congolensis	Species	Ancistrocladaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193010]

☑ 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	3
MIC	1

Activity Type	# Activity
Cell Line	1
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT839	Cell Line	L6	Rattus norvegicus	MIC	=	90.0	ug.mL-1	PMID[568954]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	39.9	ug.mL-1	PMID[568954]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	2.97	ug.mL-1	PMID[568954]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	0.214	ug.mL-1	PMID[568954]

☑ 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 NPC221864 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	308
0.1-0.2	1560
0.2-0.3	7099
0.3-0.4	10869
0.4-0.5	5093
0.5-0.6	9869
0.6-0.7	6607
0.7-0.8	997
0.8-0.85	221
0.85-0.9	37
0.9-0.95	18
0.95-1	19

Similarity Score	Similarity Level	Natural Product ID
0.9933	High Similarity	NPC235143
0.9933	High Similarity	NPC230956
0.9933	High Similarity	NPC271388
0.9933	High Similarity	NPC205255
0.9933	High Similarity	NPC119649
0.9867	High Similarity	NPC80759
0.9867	High Similarity	NPC79402
0.9608	High Similarity	NPC209377
0.9545	High Similarity	NPC223077
0.9545	High Similarity	NPC56887
0.9545	High Similarity	NPC193853
0.9533	High Similarity	NPC123323
0.9295	High Similarity	NPC195392
0.9281	High Similarity	NPC79328
0.9221	High Similarity	NPC7393
0.9091	High Similarity	NPC29647
0.8963	High Similarity	NPC230276
0.8944	High Similarity	NPC239775
0.8902	High Similarity	NPC119068
0.8902	High Similarity	NPC40496
0.8882	High Similarity	NPC118274
0.8882	High Similarity	NPC168753
0.8861	High Similarity	NPC60186
0.8848	High Similarity	NPC257269
0.8812	High Similarity	NPC264850
0.8812	High Similarity	NPC13916
0.875	High Similarity	NPC24465
0.869	High Similarity	NPC95426
0.869	High Similarity	NPC16357
0.869	High Similarity	NPC302245
0.8688	High Similarity	NPC324144
0.8688	High Similarity	NPC1229
0.8675	High Similarity	NPC474507
0.8642	High Similarity	NPC117188
0.8642	High Similarity	NPC205421
0.8642	High Similarity	NPC474931
0.8642	High Similarity	NPC158376
0.8642	High Similarity	NPC81218
0.8642	High Similarity	NPC12053
0.8642	High Similarity	NPC145832
0.8642	High Similarity	NPC306555
0.8639	High Similarity	NPC65312
0.8639	High Similarity	NPC139783
0.8634	High Similarity	NPC136508
0.8634	High Similarity	NPC212794
0.8634	High Similarity	NPC196447
0.8634	High Similarity	NPC13504
0.8634	High Similarity	NPC96603
0.8634	High Similarity	NPC306843
0.8634	High Similarity	NPC477563
0.8634	High Similarity	NPC78222
0.8634	High Similarity	NPC253043
0.8589	High Similarity	NPC83198
0.8589	High Similarity	NPC204908
0.8588	High Similarity	NPC22115
0.8588	High Similarity	NPC275680
0.8562	High Similarity	NPC166014
0.8562	High Similarity	NPC27410
0.8554	High Similarity	NPC476577
0.8554	High Similarity	NPC173416
0.8554	High Similarity	NPC148709
0.8553	High Similarity	NPC206736
0.8553	High Similarity	NPC195766
0.8547	High Similarity	NPC476565
0.8544	High Similarity	NPC244112
0.8543	High Similarity	NPC470925
0.8535	High Similarity	NPC26601
0.8491	Intermediate Similarity	NPC186063
0.8488	Intermediate Similarity	NPC259350
0.8488	Intermediate Similarity	NPC223236
0.8462	Intermediate Similarity	NPC49075
0.8462	Intermediate Similarity	NPC290582
0.8462	Intermediate Similarity	NPC217748
0.8462	Intermediate Similarity	NPC90998
0.8462	Intermediate Similarity	NPC104196
0.8462	Intermediate Similarity	NPC271013
0.8462	Intermediate Similarity	NPC285931
0.8462	Intermediate Similarity	NPC311973
0.8462	Intermediate Similarity	NPC290005
0.8462	Intermediate Similarity	NPC181796
0.8462	Intermediate Similarity	NPC185639
0.8462	Intermediate Similarity	NPC15414
0.8462	Intermediate Similarity	NPC42663
0.8462	Intermediate Similarity	NPC8836
0.8462	Intermediate Similarity	NPC328155
0.8462	Intermediate Similarity	NPC251735
0.8462	Intermediate Similarity	NPC182052
0.8462	Intermediate Similarity	NPC239824
0.8462	Intermediate Similarity	NPC7715
0.8462	Intermediate Similarity	NPC54654
0.8462	Intermediate Similarity	NPC222661
0.8462	Intermediate Similarity	NPC279228
0.8462	Intermediate Similarity	NPC258657
0.8462	Intermediate Similarity	NPC223690
0.8462	Intermediate Similarity	NPC229373
0.8452	Intermediate Similarity	NPC476151
0.8439	Intermediate Similarity	NPC478093
0.8438	Intermediate Similarity	NPC476572
0.8434	Intermediate Similarity	NPC152680
0.8434	Intermediate Similarity	NPC190783
0.8434	Intermediate Similarity	NPC232386
0.843	Intermediate Similarity	NPC206900
0.8428	Intermediate Similarity	NPC54379
0.8428	Intermediate Similarity	NPC110416
0.8428	Intermediate Similarity	NPC276588
0.8428	Intermediate Similarity	NPC207757
0.8428	Intermediate Similarity	NPC39701
0.8428	Intermediate Similarity	NPC172765
0.8428	Intermediate Similarity	NPC189266
0.8428	Intermediate Similarity	NPC295691
0.8428	Intermediate Similarity	NPC5238
0.8428	Intermediate Similarity	NPC469817
0.8428	Intermediate Similarity	NPC249797
0.8428	Intermediate Similarity	NPC325871
0.8428	Intermediate Similarity	NPC127674
0.8428	Intermediate Similarity	NPC193949
0.8428	Intermediate Similarity	NPC278799
0.8428	Intermediate Similarity	NPC99659
0.8428	Intermediate Similarity	NPC2413
0.8428	Intermediate Similarity	NPC204828
0.8428	Intermediate Similarity	NPC184026
0.8415	Intermediate Similarity	NPC204947
0.8415	Intermediate Similarity	NPC150879
0.8412	Intermediate Similarity	NPC274716
0.8412	Intermediate Similarity	NPC254441
0.8412	Intermediate Similarity	NPC167116
0.8405	Intermediate Similarity	NPC134858
0.8402	Intermediate Similarity	NPC286119
0.8391	Intermediate Similarity	NPC478091
0.8391	Intermediate Similarity	NPC473589
0.8391	Intermediate Similarity	NPC30182
0.8391	Intermediate Similarity	NPC478092
0.8391	Intermediate Similarity	NPC256124
0.8373	Intermediate Similarity	NPC149090
0.8373	Intermediate Similarity	NPC19520
0.8354	Intermediate Similarity	NPC81733
0.8354	Intermediate Similarity	NPC326316
0.8353	Intermediate Similarity	NPC30779
0.8344	Intermediate Similarity	NPC219162
0.8344	Intermediate Similarity	NPC477565
0.8344	Intermediate Similarity	NPC92541
0.8344	Intermediate Similarity	NPC103379
0.8344	Intermediate Similarity	NPC233650
0.8324	Intermediate Similarity	NPC82763
0.8323	Intermediate Similarity	NPC477020
0.8323	Intermediate Similarity	NPC185838
0.8323	Intermediate Similarity	NPC66341
0.8323	Intermediate Similarity	NPC192135
0.8314	Intermediate Similarity	NPC57036
0.8314	Intermediate Similarity	NPC116465
0.8314	Intermediate Similarity	NPC212237
0.8314	Intermediate Similarity	NPC214116
0.8313	Intermediate Similarity	NPC69712
0.8313	Intermediate Similarity	NPC26240
0.8313	Intermediate Similarity	NPC477562
0.8303	Intermediate Similarity	NPC210140
0.8303	Intermediate Similarity	NPC298979
0.8293	Intermediate Similarity	NPC169743
0.8291	Intermediate Similarity	NPC265473
0.8291	Intermediate Similarity	NPC276665
0.8284	Intermediate Similarity	NPC320223
0.8284	Intermediate Similarity	NPC114364
0.828	Intermediate Similarity	NPC130941
0.828	Intermediate Similarity	NPC476571
0.828	Intermediate Similarity	NPC147390
0.828	Intermediate Similarity	NPC428
0.828	Intermediate Similarity	NPC135538
0.828	Intermediate Similarity	NPC246587
0.828	Intermediate Similarity	NPC24233
0.8274	Intermediate Similarity	NPC128560
0.8274	Intermediate Similarity	NPC229166
0.8274	Intermediate Similarity	NPC199465
0.8266	Intermediate Similarity	NPC186546
0.8266	Intermediate Similarity	NPC476576
0.8263	Intermediate Similarity	NPC76682
0.8263	Intermediate Similarity	NPC276890
0.8263	Intermediate Similarity	NPC317439
0.8263	Intermediate Similarity	NPC198498
0.8263	Intermediate Similarity	NPC317145
0.8263	Intermediate Similarity	NPC115284
0.8263	Intermediate Similarity	NPC10908
0.8263	Intermediate Similarity	NPC227060
0.8263	Intermediate Similarity	NPC63646
0.8242	Intermediate Similarity	NPC476573
0.8242	Intermediate Similarity	NPC35627
0.8242	Intermediate Similarity	NPC81247
0.8225	Intermediate Similarity	NPC241704
0.8218	Intermediate Similarity	NPC274661
0.8218	Intermediate Similarity	NPC11296
0.8218	Intermediate Similarity	NPC82457
0.8218	Intermediate Similarity	NPC175890
0.8218	Intermediate Similarity	NPC48490
0.8217	Intermediate Similarity	NPC253883
0.8217	Intermediate Similarity	NPC191376
0.8217	Intermediate Similarity	NPC16107
0.8217	Intermediate Similarity	NPC210437
0.8217	Intermediate Similarity	NPC321505
0.8217	Intermediate Similarity	NPC90844
0.8217	Intermediate Similarity	NPC179825
0.8217	Intermediate Similarity	NPC95075

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 NPC221864 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	199
0.1-0.2	757
0.2-0.3	975
0.3-0.4	1870
0.4-0.5	2605
0.5-0.6	1733
0.6-0.7	842
0.7-0.8	160
0.8-0.85	8
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8902	High Similarity	NPD8453	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD8053	Approved
0.8462	Intermediate Similarity	NPD8054	Approved
0.8263	Intermediate Similarity	NPD8251	Approved
0.8263	Intermediate Similarity	NPD8099	Discontinued
0.8263	Intermediate Similarity	NPD8252	Approved
0.8217	Intermediate Similarity	NPD4584	Approved
0.8214	Intermediate Similarity	NPD8156	Discontinued
0.816	Intermediate Similarity	NPD6788	Approved
0.8153	Intermediate Similarity	NPD2420	Approved
0.8153	Intermediate Similarity	NPD2421	Approved
0.8065	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7447	Phase 1
0.7925	Intermediate Similarity	NPD7213	Phase 3
0.7925	Intermediate Similarity	NPD7212	Phase 2
0.7904	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD4474	Approved
0.7895	Intermediate Similarity	NPD4475	Approved
0.7826	Intermediate Similarity	NPD6090	Discontinued
0.7818	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD3845	Phase 1
0.7727	Intermediate Similarity	NPD3109	Approved
0.7727	Intermediate Similarity	NPD2238	Phase 2
0.7727	Intermediate Similarity	NPD3110	Approved
0.7702	Intermediate Similarity	NPD7598	Phase 2
0.7692	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4625	Phase 3
0.7644	Intermediate Similarity	NPD7479	Phase 2
0.7616	Intermediate Similarity	NPD2489	Approved
0.7616	Intermediate Similarity	NPD2898	Approved
0.7616	Intermediate Similarity	NPD27	Approved
0.7602	Intermediate Similarity	NPD6747	Phase 1
0.7602	Intermediate Similarity	NPD3051	Approved
0.7598	Intermediate Similarity	NPD7906	Approved
0.7597	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD3124	Discontinued
0.7578	Intermediate Similarity	NPD5241	Discontinued
0.7576	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD4055	Discovery
0.7574	Intermediate Similarity	NPD7831	Phase 2
0.7574	Intermediate Similarity	NPD7833	Phase 2
0.7558	Intermediate Similarity	NPD2970	Approved
0.7558	Intermediate Similarity	NPD2969	Approved
0.7532	Intermediate Similarity	NPD1753	Discontinued
0.7532	Intermediate Similarity	NPD5155	Approved
0.7532	Intermediate Similarity	NPD5156	Approved
0.7529	Intermediate Similarity	NPD7400	Phase 3
0.7516	Intermediate Similarity	NPD6748	Discontinued
0.7514	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4010	Discontinued
0.75	Intermediate Similarity	NPD7037	Approved
0.7486	Intermediate Similarity	NPD42	Phase 2
0.7486	Intermediate Similarity	NPD6042	Phase 2
0.7485	Intermediate Similarity	NPD4773	Phase 2
0.7485	Intermediate Similarity	NPD4772	Phase 2
0.7472	Intermediate Similarity	NPD4577	Approved
0.7472	Intermediate Similarity	NPD4578	Approved
0.747	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD4017	Approved
0.7469	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2605	Approved
0.7468	Intermediate Similarity	NPD2606	Approved
0.7468	Intermediate Similarity	NPD3595	Approved
0.7468	Intermediate Similarity	NPD3594	Approved
0.7468	Intermediate Similarity	NPD4908	Phase 1
0.7444	Intermediate Similarity	NPD4663	Approved
0.744	Intermediate Similarity	NPD7298	Approved
0.7439	Intermediate Similarity	NPD1424	Approved
0.7429	Intermediate Similarity	NPD7493	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD5709	Phase 3
0.7423	Intermediate Similarity	NPD6667	Approved
0.7423	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6666	Approved
0.7419	Intermediate Similarity	NPD8095	Phase 1
0.7417	Intermediate Similarity	NPD2233	Approved
0.7417	Intermediate Similarity	NPD2232	Approved
0.7417	Intermediate Similarity	NPD2230	Approved
0.7407	Intermediate Similarity	NPD7466	Approved
0.7405	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD3635	Approved
0.7403	Intermediate Similarity	NPD3637	Approved
0.7403	Intermediate Similarity	NPD3636	Approved
0.7399	Intermediate Similarity	NPD6071	Discontinued
0.7391	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD4666	Phase 3
0.7383	Intermediate Similarity	NPD4093	Discontinued
0.7374	Intermediate Similarity	NPD7310	Approved
0.7374	Intermediate Similarity	NPD7313	Approved
0.7374	Intermediate Similarity	NPD7311	Approved
0.7374	Intermediate Similarity	NPD7312	Approved
0.7368	Intermediate Similarity	NPD1669	Approved
0.7365	Intermediate Similarity	NPD4005	Discontinued
0.7358	Intermediate Similarity	NPD2200	Suspended
0.7353	Intermediate Similarity	NPD2563	Approved
0.7353	Intermediate Similarity	NPD2560	Approved
0.7349	Intermediate Similarity	NPD1914	Approved
0.7349	Intermediate Similarity	NPD7427	Discontinued
0.7333	Intermediate Similarity	NPD2667	Approved
0.7333	Intermediate Similarity	NPD2668	Approved
0.7333	Intermediate Similarity	NPD7309	Approved
0.7329	Intermediate Similarity	NPD4721	Approved
0.7329	Intermediate Similarity	NPD4725	Approved
0.7329	Intermediate Similarity	NPD4726	Approved
0.7317	Intermediate Similarity	NPD7124	Phase 2
0.7315	Intermediate Similarity	NPD5304	Approved
0.7315	Intermediate Similarity	NPD5303	Approved
0.7314	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD2568	Approved
0.7294	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD6020	Phase 2
0.7283	Intermediate Similarity	NPD6746	Phase 2
0.7278	Intermediate Similarity	NPD7438	Suspended
0.7273	Intermediate Similarity	NPD4103	Phase 2
0.7273	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD8051	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD3692	Discontinued
0.7246	Intermediate Similarity	NPD3639	Approved
0.7246	Intermediate Similarity	NPD6031	Approved
0.7246	Intermediate Similarity	NPD6030	Approved
0.7246	Intermediate Similarity	NPD3640	Phase 3
0.7246	Intermediate Similarity	NPD3641	Approved
0.7239	Intermediate Similarity	NPD5177	Phase 3
0.7232	Intermediate Similarity	NPD7177	Discontinued
0.7232	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6584	Phase 3
0.7222	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7030	Discontinued
0.7222	Intermediate Similarity	NPD7549	Discontinued
0.7216	Intermediate Similarity	NPD4481	Phase 3
0.7208	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD5754	Discontinued
0.7195	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4097	Suspended
0.7182	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD4256	Phase 2
0.7178	Intermediate Similarity	NPD4257	Approved
0.7176	Intermediate Similarity	NPD6072	Discontinued
0.716	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5718	Phase 2
0.7152	Intermediate Similarity	NPD7294	Phase 1
0.7152	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4727	Phase 1
0.7143	Intermediate Similarity	NPD4659	Approved
0.7143	Intermediate Similarity	NPD7802	Discontinued
0.7135	Intermediate Similarity	NPD2488	Approved
0.7135	Intermediate Similarity	NPD2490	Approved
0.7134	Intermediate Similarity	NPD3060	Approved
0.7128	Intermediate Similarity	NPD6284	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7020	Approved
0.7126	Intermediate Similarity	NPD7019	Approved
0.7118	Intermediate Similarity	NPD4678	Approved
0.7118	Intermediate Similarity	NPD4675	Approved
0.7107	Intermediate Similarity	NPD7477	Discontinued
0.7105	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD4108	Discontinued
0.7089	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD5938	Phase 3
0.7069	Intermediate Similarity	NPD8005	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD3452	Approved
0.7068	Intermediate Similarity	NPD3450	Approved
0.7068	Intermediate Similarity	NPD2493	Approved
0.7068	Intermediate Similarity	NPD2494	Approved
0.7053	Intermediate Similarity	NPD3837	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4098	Discontinued
0.7049	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5160	Discontinued
0.7037	Intermediate Similarity	NPD2975	Approved
0.7037	Intermediate Similarity	NPD2974	Approved
0.7037	Intermediate Similarity	NPD2973	Approved
0.7032	Intermediate Similarity	NPD6583	Phase 3
0.7032	Intermediate Similarity	NPD6582	Phase 2
0.7032	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4749	Approved
0.7031	Intermediate Similarity	NPD5005	Approved
0.7031	Intermediate Similarity	NPD5006	Approved
0.7018	Intermediate Similarity	NPD6502	Phase 2
0.7017	Intermediate Similarity	NPD6297	Approved
0.7016	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1610	Phase 2
0.7006	Intermediate Similarity	NPD7905	Discontinued
0.7	Intermediate Similarity	NPD6405	Approved
0.7	Intermediate Similarity	NPD6407	Approved
0.6995	Remote Similarity	NPD6146	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6064	Phase 1
0.6994	Remote Similarity	NPD4585	Approved
0.6989	Remote Similarity	NPD5677	Discontinued
0.6989	Remote Similarity	NPD6037	Discontinued
0.6989	Remote Similarity	NPD3365	Discontinued
0.6977	Remote Similarity	NPD5089	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