NPASS Compound

Structure

NPC471512 OpenBabel07101719522D 32 37 0 0 1 0 0 0 0 0999 V2000 -0.8038 2.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7806 4.8997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4164 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4164 -0.1631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9592 -0.9550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9592 0.1008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7107 -2.1892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5998 -0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9058 -0.0143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2234 -1.8975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9635 -2.6747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3375 -2.5899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5021 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5021 -0.1631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6638 -1.2993 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1225 -1.3805 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6825 -0.1027 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3195 1.4283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1015 3.3900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8697 -0.8950 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2617 -1.1500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3103 -0.4271 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9028 0.1312 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1694 -2.2703 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4111 -0.8138 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3310 0.5084 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1867 1.2233 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9731 3.5752 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1588 0.9847 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0634 2.2818 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5052 4.0522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 31 1 0 0 0 0 2 32 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 13 2 0 0 0 0 6 14 2 0 0 0 0 7 11 1 0 0 0 0 7 15 1 0 0 0 0 8 9 1 0 0 0 0 9 22 1 0 0 0 0 10 12 1 0 0 0 0 10 21 1 0 0 0 0 11 24 1 0 0 0 0 12 24 1 0 0 0 0 13 14 1 0 0 0 0 13 21 1 0 0 0 0 14 25 1 0 0 0 0 15 20 1 6 0 0 0 15 26 1 0 0 0 0 16 20 1 1 0 0 0 16 21 1 0 0 0 0 16 24 1 0 0 0 0 17 20 1 6 0 0 0 17 23 1 0 0 0 0 17 27 1 0 0 0 0 18 23 1 0 0 0 0 18 28 2 0 0 0 0 18 31 1 0 0 0 0 19 25 1 0 0 0 0 19 29 2 0 0 0 0 19 32 1 0 0 0 0 20 8 1 1 0 0 0 21 22 1 1 0 0 0 22 23 1 1 0 0 0 22 25 1 0 0 0 0 23 30 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	444.19
Volume:	425.368
LogP:	0.991
LogD:	0.901
LogS:	-3.872
# Rotatable Bonds:	4
TPSA:	119.77
# H-Bond Aceptor:	9
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.524
Synthetic Accessibility Score:	6.419
Fsp3:	0.652
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.349
MDCK Permeability:	2.151683838746976e-05
Pgp-inhibitor:	0.102
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.056
30% Bioavailability (F30%):	0.947

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.587
Plasma Protein Binding (PPB):	26.839580535888672%
Volume Distribution (VD):	0.648
Pgp-substrate:	72.85169219970703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.831
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.924
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.052
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.456
CYP3A4-inhibitor:	0.023
CYP3A4-substrate:	0.928

ADMET: Excretion

Clearance (CL):	2.572
Half-life (T1/2):	0.282

ADMET: Toxicity

hERG Blockers:	0.344
Human Hepatotoxicity (H-HT):	0.38
Drug-inuced Liver Injury (DILI):	0.058
AMES Toxicity:	0.175
Rat Oral Acute Toxicity:	0.989
Maximum Recommended Daily Dose:	0.996
Skin Sensitization:	0.427
Carcinogencity:	0.937
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC471512

Natural Product ID:	NPC471512
*Common Name:**	Kopsiloscine C
IUPAC Name:	n.a.
Synonyms:	Kopsiloscine C
Standard InCHIKey:	IICJDWBFZMYHKV-IFDKZNJJSA-N
Standard InCHI:	InChI=1S/C23H28N2O7/c1-31-18(28)23(30)17(27)20-8-9-22(23)21(10-12-24(16(20)21)11-7-15(20)26)13-5-3-4-6-14(13)25(22)19(29)32-2/h3-6,15-17,26-27,30H,7-12H2,1-2H3/t15-,16-,17-,20-,21+,22-,23+/m0/s1
SMILES:	COC(=O)C1(C(C23CCC14C5(C2N(CCC3O)CC5)C6=CC=CC=C6N4C(=O)OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL253772
PubChem CID:	44445381
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003755] Aspidofractine alkaloids

*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
NPO19270	Kopsia singapurensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17939738]
NPO19270	Kopsia singapurensis	Species	Apocynaceae	Eukaryota	leaf and stem-bark	Pahang, Malaysia	1996-JUL	PMID[18078327]
NPO19270	Kopsia singapurensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	3

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[469264]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[469264]

☑ 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 NPC471512 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	281
0.1-0.2	1329
0.2-0.3	3257
0.3-0.4	13707
0.4-0.5	18833
0.5-0.6	4459
0.6-0.7	716
0.7-0.8	99
0.8-0.85	8
0.85-0.9	4
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9663	High Similarity	NPC221687
0.9392	High Similarity	NPC473375
0.9392	High Similarity	NPC97100
0.8856	High Similarity	NPC473458
0.867	High Similarity	NPC471513
0.86	High Similarity	NPC288110
0.839	Intermediate Similarity	NPC477394
0.8289	Intermediate Similarity	NPC52262
0.8235	Intermediate Similarity	NPC222046
0.823	Intermediate Similarity	NPC477397
0.8156	Intermediate Similarity	NPC225319
0.8102	Intermediate Similarity	NPC477395
0.8028	Intermediate Similarity	NPC477393
0.8021	Intermediate Similarity	NPC22689
0.8021	Intermediate Similarity	NPC105055
0.7959	Intermediate Similarity	NPC90967
0.7955	Intermediate Similarity	NPC477396
0.7854	Intermediate Similarity	NPC127996
0.7814	Intermediate Similarity	NPC99632
0.7814	Intermediate Similarity	NPC282339
0.775	Intermediate Similarity	NPC475489
0.7653	Intermediate Similarity	NPC473298
0.7644	Intermediate Similarity	NPC218594
0.7644	Intermediate Similarity	NPC99043
0.7614	Intermediate Similarity	NPC25401
0.7588	Intermediate Similarity	NPC34717
0.7577	Intermediate Similarity	NPC97584
0.7551	Intermediate Similarity	NPC14994
0.7551	Intermediate Similarity	NPC181928
0.754	Intermediate Similarity	NPC472106
0.7539	Intermediate Similarity	NPC203202
0.7539	Intermediate Similarity	NPC264482
0.7527	Intermediate Similarity	NPC472120
0.7527	Intermediate Similarity	NPC472101
0.7526	Intermediate Similarity	NPC139085
0.7526	Intermediate Similarity	NPC251212
0.7526	Intermediate Similarity	NPC214626
0.7526	Intermediate Similarity	NPC159963
0.7489	Intermediate Similarity	NPC475316
0.7489	Intermediate Similarity	NPC473486
0.7488	Intermediate Similarity	NPC234772
0.7443	Intermediate Similarity	NPC35390
0.7443	Intermediate Similarity	NPC473781
0.7443	Intermediate Similarity	NPC470631
0.743	Intermediate Similarity	NPC10653
0.743	Intermediate Similarity	NPC318525
0.7371	Intermediate Similarity	NPC6974
0.7358	Intermediate Similarity	NPC129624
0.7358	Intermediate Similarity	NPC476441
0.734	Intermediate Similarity	NPC472117
0.732	Intermediate Similarity	NPC186669
0.7287	Intermediate Similarity	NPC201424
0.7287	Intermediate Similarity	NPC472102
0.7287	Intermediate Similarity	NPC309531
0.7259	Intermediate Similarity	NPC477159
0.7246	Intermediate Similarity	NPC1464
0.7232	Intermediate Similarity	NPC291173
0.7231	Intermediate Similarity	NPC260075
0.7209	Intermediate Similarity	NPC473837
0.7181	Intermediate Similarity	NPC113946
0.7176	Intermediate Similarity	NPC77777
0.7165	Intermediate Similarity	NPC476425
0.7165	Intermediate Similarity	NPC96901
0.7157	Intermediate Similarity	NPC11149
0.715	Intermediate Similarity	NPC282092
0.7143	Intermediate Similarity	NPC246140
0.7143	Intermediate Similarity	NPC195787
0.7143	Intermediate Similarity	NPC223590
0.7121	Intermediate Similarity	NPC476428
0.7111	Intermediate Similarity	NPC160113
0.7111	Intermediate Similarity	NPC476220
0.711	Intermediate Similarity	NPC140311
0.7103	Intermediate Similarity	NPC159815
0.7095	Intermediate Similarity	NPC329833
0.7087	Intermediate Similarity	NPC162440
0.7077	Intermediate Similarity	NPC21752
0.7077	Intermediate Similarity	NPC210415
0.7077	Intermediate Similarity	NPC276993
0.7077	Intermediate Similarity	NPC298851
0.7077	Intermediate Similarity	NPC181138
0.7077	Intermediate Similarity	NPC293255
0.7067	Intermediate Similarity	NPC138830
0.7065	Intermediate Similarity	NPC264589
0.7062	Intermediate Similarity	NPC469915
0.7059	Intermediate Similarity	NPC19175
0.7053	Intermediate Similarity	NPC36495
0.705	Intermediate Similarity	NPC245741
0.7045	Intermediate Similarity	NPC106593
0.7016	Intermediate Similarity	NPC248117
0.7015	Intermediate Similarity	NPC476095
0.7014	Intermediate Similarity	NPC87714
0.7014	Intermediate Similarity	NPC473667
0.701	Intermediate Similarity	NPC224970
0.701	Intermediate Similarity	NPC223595
0.701	Intermediate Similarity	NPC167724
0.7009	Intermediate Similarity	NPC234999
0.7005	Intermediate Similarity	NPC475559
0.7005	Intermediate Similarity	NPC302548
0.7004	Intermediate Similarity	NPC154922
0.7	Intermediate Similarity	NPC61013
0.7	Intermediate Similarity	NPC128476
0.6995	Remote Similarity	NPC284706
0.6987	Remote Similarity	NPC304837
0.6987	Remote Similarity	NPC476258
0.6986	Remote Similarity	NPC67904
0.6982	Remote Similarity	NPC231924
0.6972	Remote Similarity	NPC195636
0.6963	Remote Similarity	NPC193410
0.6959	Remote Similarity	NPC279527
0.6959	Remote Similarity	NPC214960
0.695	Remote Similarity	NPC475962
0.6946	Remote Similarity	NPC285841
0.6942	Remote Similarity	NPC470485
0.6935	Remote Similarity	NPC321211
0.6935	Remote Similarity	NPC475094
0.6931	Remote Similarity	NPC478076
0.6927	Remote Similarity	NPC315368
0.6926	Remote Similarity	NPC469452
0.692	Remote Similarity	NPC470480
0.6904	Remote Similarity	NPC285622
0.6891	Remote Similarity	NPC293458
0.6884	Remote Similarity	NPC476326
0.6881	Remote Similarity	NPC189661
0.6878	Remote Similarity	NPC476069
0.6872	Remote Similarity	NPC472114
0.6872	Remote Similarity	NPC472115
0.6867	Remote Similarity	NPC329932
0.6866	Remote Similarity	NPC475778
0.6859	Remote Similarity	NPC29285
0.6856	Remote Similarity	NPC313757
0.6853	Remote Similarity	NPC469722
0.6853	Remote Similarity	NPC113455
0.6845	Remote Similarity	NPC470483
0.6845	Remote Similarity	NPC212799
0.684	Remote Similarity	NPC469450
0.6839	Remote Similarity	NPC474058
0.6838	Remote Similarity	NPC120239
0.6825	Remote Similarity	NPC475763
0.6823	Remote Similarity	NPC123241
0.681	Remote Similarity	NPC132874
0.681	Remote Similarity	NPC265642
0.681	Remote Similarity	NPC218733
0.681	Remote Similarity	NPC138615
0.6806	Remote Similarity	NPC473297
0.6797	Remote Similarity	NPC301501
0.6789	Remote Similarity	NPC10732
0.6784	Remote Similarity	NPC469726
0.6784	Remote Similarity	NPC329338
0.6784	Remote Similarity	NPC13367
0.6781	Remote Similarity	NPC469451
0.6774	Remote Similarity	NPC269449
0.6771	Remote Similarity	NPC477157
0.6771	Remote Similarity	NPC477156
0.6765	Remote Similarity	NPC322621
0.6753	Remote Similarity	NPC131977
0.675	Remote Similarity	NPC475427
0.6745	Remote Similarity	NPC127178
0.6737	Remote Similarity	NPC154602
0.6736	Remote Similarity	NPC153694
0.6736	Remote Similarity	NPC211525
0.6735	Remote Similarity	NPC52059
0.6735	Remote Similarity	NPC470069
0.6735	Remote Similarity	NPC471124
0.6734	Remote Similarity	NPC473743
0.6728	Remote Similarity	NPC477160
0.6718	Remote Similarity	NPC286871
0.6715	Remote Similarity	NPC474059
0.6715	Remote Similarity	NPC5630
0.6714	Remote Similarity	NPC232600
0.6712	Remote Similarity	NPC119722
0.6701	Remote Similarity	NPC243673
0.6701	Remote Similarity	NPC63210
0.6701	Remote Similarity	NPC310403
0.6701	Remote Similarity	NPC263709
0.6701	Remote Similarity	NPC148468
0.6701	Remote Similarity	NPC97380
0.6701	Remote Similarity	NPC471122
0.6696	Remote Similarity	NPC46259
0.6683	Remote Similarity	NPC203628
0.6683	Remote Similarity	NPC472209
0.6682	Remote Similarity	NPC36607
0.6682	Remote Similarity	NPC475223
0.6667	Remote Similarity	NPC49196
0.6667	Remote Similarity	NPC249150
0.6667	Remote Similarity	NPC126556
0.6667	Remote Similarity	NPC79129
0.6667	Remote Similarity	NPC81654
0.6667	Remote Similarity	NPC195461
0.6667	Remote Similarity	NPC313985
0.6667	Remote Similarity	NPC18661
0.6652	Remote Similarity	NPC476436
0.6651	Remote Similarity	NPC246983
0.6651	Remote Similarity	NPC475448
0.665	Remote Similarity	NPC473880
0.6649	Remote Similarity	NPC243756
0.6638	Remote Similarity	NPC223242
0.6635	Remote Similarity	NPC303214
0.6633	Remote Similarity	NPC472118
0.6633	Remote Similarity	NPC176983
0.6624	Remote Similarity	NPC253482

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 NPC471512 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	171
0.1-0.2	503
0.2-0.3	770
0.3-0.4	2416
0.4-0.5	3858
0.5-0.6	1333
0.6-0.7	94
0.7-0.8	5
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6915	Remote Similarity	NPD7962	Phase 2
0.6915	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4601	Approved
0.6667	Remote Similarity	NPD4600	Approved
0.6614	Remote Similarity	NPD8459	Approved
0.6614	Remote Similarity	NPD8460	Approved
0.6604	Remote Similarity	NPD2973	Approved
0.6604	Remote Similarity	NPD2974	Approved
0.6604	Remote Similarity	NPD2975	Approved
0.6598	Remote Similarity	NPD1663	Discontinued
0.6589	Remote Similarity	NPD6805	Discontinued
0.6588	Remote Similarity	NPD4602	Approved
0.6587	Remote Similarity	NPD8465	Approved
0.6587	Remote Similarity	NPD8466	Approved
0.6587	Remote Similarity	NPD8467	Approved
0.6582	Remote Similarity	NPD7600	Phase 2
0.658	Remote Similarity	NPD4121	Phase 3
0.658	Remote Similarity	NPD4120	Approved
0.6564	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD2493	Approved
0.6558	Remote Similarity	NPD3450	Approved
0.6558	Remote Similarity	NPD2494	Approved
0.6558	Remote Similarity	NPD3452	Approved
0.6546	Remote Similarity	NPD5742	Approved
0.6546	Remote Similarity	NPD5743	Approved
0.6546	Remote Similarity	NPD5741	Approved
0.6538	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD3422	Phase 3
0.6535	Remote Similarity	NPD3423	Phase 2
0.6512	Remote Similarity	NPD4580	Approved
0.6484	Remote Similarity	NPD8426	Approved
0.6484	Remote Similarity	NPD8425	Approved
0.6479	Remote Similarity	NPD5582	Discontinued
0.6477	Remote Similarity	NPD7606	Phase 3
0.6468	Remote Similarity	NPD4583	Approved
0.6468	Remote Similarity	NPD4582	Approved
0.6465	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD8427	Approved
0.6457	Remote Similarity	NPD8429	Approved
0.6457	Remote Similarity	NPD8428	Approved
0.6447	Remote Similarity	NPD7599	Phase 2
0.6435	Remote Similarity	NPD7186	Phase 3
0.6422	Remote Similarity	NPD4004	Approved
0.6422	Remote Similarity	NPD4002	Approved
0.6421	Remote Similarity	NPD2575	Approved
0.6414	Remote Similarity	NPD8363	Approved
0.6414	Remote Similarity	NPD8364	Approved
0.6389	Remote Similarity	NPD5608	Approved
0.6389	Remote Similarity	NPD5609	Approved
0.6387	Remote Similarity	NPD7295	Approved
0.638	Remote Similarity	NPD7300	Phase 3
0.638	Remote Similarity	NPD7302	Phase 3
0.6364	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD2093	Discontinued
0.6347	Remote Similarity	NPD7205	Discontinued
0.6339	Remote Similarity	NPD2613	Approved
0.6321	Remote Similarity	NPD7478	Approved
0.6305	Remote Similarity	NPD7795	Phase 2
0.6305	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD6997	Phase 2
0.6291	Remote Similarity	NPD5504	Discontinued
0.6283	Remote Similarity	NPD7082	Approved
0.6279	Remote Similarity	NPD5947	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD6625	Approved
0.6267	Remote Similarity	NPD7301	Phase 3
0.6261	Remote Similarity	NPD7048	Phase 3
0.625	Remote Similarity	NPD7487	Discontinued
0.6245	Remote Similarity	NPD8329	Phase 3
0.6244	Remote Similarity	NPD8361	Approved
0.6244	Remote Similarity	NPD8435	Approved
0.6244	Remote Similarity	NPD8360	Approved
0.6237	Remote Similarity	NPD3614	Approved
0.6237	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD2570	Approved
0.6237	Remote Similarity	NPD3090	Approved
0.6237	Remote Similarity	NPD4746	Phase 3
0.6237	Remote Similarity	NPD2566	Approved
0.6237	Remote Similarity	NPD4745	Approved
0.6237	Remote Similarity	NPD3087	Approved
0.6237	Remote Similarity	NPD3089	Approved
0.6237	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD3088	Approved
0.6237	Remote Similarity	NPD3616	Approved
0.6237	Remote Similarity	NPD2571	Approved
0.6237	Remote Similarity	NPD2574	Discontinued
0.6237	Remote Similarity	NPD2573	Approved
0.6237	Remote Similarity	NPD3615	Approved
0.6233	Remote Similarity	NPD5610	Approved
0.6221	Remote Similarity	NPD3828	Approved
0.6221	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6217	Remote Similarity	NPD8489	Phase 1
0.6216	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD2488	Approved
0.6215	Remote Similarity	NPD2490	Approved
0.6214	Remote Similarity	NPD8468	Phase 2
0.6205	Remote Similarity	NPD4520	Approved
0.6205	Remote Similarity	NPD5941	Approved
0.6205	Remote Similarity	NPD5942	Approved
0.6202	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.6201	Remote Similarity	NPD7292	Approved
0.6199	Remote Similarity	NPD7497	Discontinued
0.6193	Remote Similarity	NPD53	Approved
0.6193	Remote Similarity	NPD7777	Approved
0.6193	Remote Similarity	NPD7778	Approved
0.6186	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD4329	Approved
0.6172	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD4330	Approved
0.617	Remote Similarity	NPD4684	Phase 3
0.617	Remote Similarity	NPD4685	Phase 3
0.617	Remote Similarity	NPD4686	Approved
0.6169	Remote Similarity	NPD2506	Approved
0.6165	Remote Similarity	NPD3377	Discontinued
0.6161	Remote Similarity	NPD2968	Approved
0.6161	Remote Similarity	NPD2971	Approved
0.6157	Remote Similarity	NPD8325	Phase 3
0.6157	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6157	Remote Similarity	NPD8326	Phase 3
0.615	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6144	Remote Similarity	NPD8374	Phase 3
0.6143	Remote Similarity	NPD3471	Approved
0.6143	Remote Similarity	NPD3470	Approved
0.6141	Remote Similarity	NPD5993	Phase 1
0.614	Remote Similarity	NPD7707	Approved
0.6134	Remote Similarity	NPD6723	Discontinued
0.613	Remote Similarity	NPD7293	Approved
0.6121	Remote Similarity	NPD7805	Phase 3
0.6119	Remote Similarity	NPD4668	Phase 2
0.6117	Remote Similarity	NPD6310	Approved
0.6117	Remote Similarity	NPD5185	Approved
0.6117	Remote Similarity	NPD6309	Approved
0.6117	Remote Similarity	NPD5184	Approved
0.6117	Remote Similarity	NPD5182	Approved
0.6117	Remote Similarity	NPD6311	Approved
0.6114	Remote Similarity	NPD2820	Phase 3
0.6114	Remote Similarity	NPD5024	Approved
0.6099	Remote Similarity	NPD519	Approved
0.6099	Remote Similarity	NPD4040	Phase 1
0.6095	Remote Similarity	NPD5898	Approved
0.6095	Remote Similarity	NPD5899	Approved
0.6095	Remote Similarity	NPD5897	Approved
0.6095	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD7259	Approved
0.6079	Remote Similarity	NPD7595	Discontinued
0.6077	Remote Similarity	NPD3792	Approved
0.6074	Remote Similarity	NPD7560	Approved
0.6073	Remote Similarity	NPD8485	Approved
0.6071	Remote Similarity	NPD8165	Discontinued
0.6063	Remote Similarity	NPD4500	Approved
0.6063	Remote Similarity	NPD4501	Approved
0.6062	Remote Similarity	NPD2365	Approved
0.6058	Remote Similarity	NPD5466	Approved
0.6052	Remote Similarity	NPD7907	Approved
0.6052	Remote Similarity	NPD5506	Approved
0.6052	Remote Similarity	NPD5507	Approved
0.6048	Remote Similarity	NPD5190	Phase 2
0.6045	Remote Similarity	NPD4420	Approved
0.6043	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6043	Remote Similarity	NPD7047	Phase 3
0.6041	Remote Similarity	NPD4682	Phase 2
0.604	Remote Similarity	NPD2427	Approved
0.6036	Remote Similarity	NPD6238	Discontinued
0.6034	Remote Similarity	NPD4665	Approved
0.6034	Remote Similarity	NPD4111	Phase 1
0.6034	Remote Similarity	NPD2899	Discontinued
0.6029	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD3790	Phase 2
0.602	Remote Similarity	NPD7105	Phase 1
0.602	Remote Similarity	NPD6416	Phase 2
0.6019	Remote Similarity	NPD6878	Phase 2
0.6019	Remote Similarity	NPD6879	Phase 2
0.6019	Remote Similarity	NPD2037	Approved
0.6018	Remote Similarity	NPD6874	Approved
0.601	Remote Similarity	NPD3625	Discontinued
0.6009	Remote Similarity	NPD5005	Approved
0.6009	Remote Similarity	NPD5006	Approved
0.6	Remote Similarity	NPD5600	Discontinued
0.6	Remote Similarity	NPD7035	Approved
0.6	Remote Similarity	NPD7820	Phase 3
0.6	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7036	Phase 3
0.6	Remote Similarity	NPD6807	Phase 3
0.6	Remote Similarity	NPD4897	Phase 2
0.6	Remote Similarity	NPD4603	Phase 2
0.5991	Remote Similarity	NPD8240	Discontinued
0.5991	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD7878	Phase 2
0.599	Remote Similarity	NPD8630	Approved
0.5982	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD8407	Phase 2
0.5976	Remote Similarity	NPD7921	Approved
0.5972	Remote Similarity	NPD7233	Approved
0.5972	Remote Similarity	NPD7234	Approved
0.5972	Remote Similarity	NPD7906	Approved
0.5972	Remote Similarity	NPD3782	Discontinued

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