NPASS Compound

Structure

CID50658 OpenBabel06191715382D 33 38 0 0 1 0 0 0 0 0999 V2000 1.2188 4.1237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2260 4.0043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5074 3.8848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5074 3.8848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3838 0.9386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2705 2.4386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0504 0.7523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7601 3.0187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7601 0.8584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6310 1.9386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0074 1.5785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1365 2.6587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1365 0.4984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7453 2.8112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8647 1.8183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0256 2.6044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0501 2.0275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3838 2.6587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7601 1.5785 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1450 1.6115 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6310 2.6587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7521 1.8673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8258 3.2042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0074 3.0187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3838 1.9386 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1365 1.9386 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5129 1.5785 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0646 1.2185 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5129 0.8584 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4970 3.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3756 2.6491 0.0000 O 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 1 24 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 6 27 1 0 0 0 0 7 28 1 0 0 0 0 8 12 1 0 0 0 0 8 19 1 0 0 0 0 9 13 1 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 26 1 0 0 0 0 12 27 1 0 0 0 0 14 15 1 0 0 0 0 14 24 1 0 0 0 0 16 21 1 0 0 0 0 16 24 1 0 0 0 0 17 23 1 0 0 0 0 17 28 1 0 0 0 0 18 29 1 0 0 0 0 18 33 1 0 0 0 0 19 25 1 0 0 0 0 19 26 1 6 0 0 0 20 26 1 6 0 0 0 20 27 1 0 0 0 0 21 29 1 6 0 0 0 21 30 1 0 0 0 0 22 25 1 0 0 0 0 22 31 1 6 0 0 0 23 29 1 0 0 0 0 23 32 2 0 0 0 0 26 5 1 6 0 0 0 27 28 1 1 0 0 0 28 30 1 6 0 0 0 29 15 1 1 0 0 0 30 13 1 1 0 0 0 30 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.36
Volume:	499.831
LogP:	5.577
LogD:	4.858
LogS:	-5.383
# Rotatable Bonds:	0
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.449
Synthetic Accessibility Score:	6.192
Fsp3:	0.967
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:	-5.275
MDCK Permeability:	1.67860634974204e-05
Pgp-inhibitor:	0.305
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.299
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.226
Plasma Protein Binding (PPB):	91.01893615722656%
Volume Distribution (VD):	1.167
Pgp-substrate:	3.6655778884887695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.721
CYP2C19-inhibitor:	0.082
CYP2C19-substrate:	0.936
CYP2C9-inhibitor:	0.245
CYP2C9-substrate:	0.191
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.269
CYP3A4-inhibitor:	0.616
CYP3A4-substrate:	0.443

ADMET: Excretion

Clearance (CL):	8.604
Half-life (T1/2):	0.21

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.617
Drug-inuced Liver Injury (DILI):	0.011
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.75
Maximum Recommended Daily Dose:	0.936
Skin Sensitization:	0.114
Carcinogencity:	0.066
Eye Corrosion:	0.031
Eye Irritation:	0.079
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC50658

Natural Product ID:	NPC50658
*Common Name:**	Aegicerin
IUPAC Name:	n.a.
Synonyms:	Aegicerin
Standard InCHIKey:	HAORCLCFRZGQJZ-FZUFEACKSA-N
Standard InCHI:	InChI=1S/C30H48O3/c1-24(2)14-15-29-18-33-30(21(29)16-24)13-9-20-26(5)11-10-22(31)25(3,4)19(26)8-12-27(20,6)28(30,7)17-23(29)32/h19-22,31H,8-18H2,1-7H3/t19-,20+,21+,22-,26-,27+,28-,29+,30-/m0/s1
SMILES:	CC1(C)CC[C@@]23CO[C@@]4(CC[C@@H]5[C@@]6(C)CC[C@@H](C(C)(C)[C@@H]6CC[C@@]5(C)[C@]4(C)CC3=O)O)[C@@H]2C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL522394
PubChem CID:	15558423
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO1872	Picramnia latifolia	Species	Picramniaceae	Eukaryota	n.a.	Peru	n.a.	PMID[15043409]
NPO40818	Clavija procera	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[16724857]
NPO24324	Halobacterium salinarum	Species	Halobacteriaceae	Archaea	n.a.	n.a.	n.a.	PMID[24823651]
NPO20080	Lepisorus thunbergianus	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10403	Ficus nitida	Species	Ficidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21437	Rhododendron aureum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20080	Lepisorus thunbergianus	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21935	Exallage auricularia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20080	Lepisorus thunbergianus	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21437	Rhododendron aureum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24324	Halobacterium salinarum	Species	Halobacteriaceae	Archaea	n.a.	n.a.	n.a.	Database[UNPD]
NPO1872	Picramnia latifolia	Species	Picramniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21935	Exallage auricularia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10581	Allium erubescens	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11826	Arctotis revoluta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO807	Lasiolaena morii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10403	Ficus nitida	Species	Ficidae	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	1
MIC	4

Activity Type	# Activity
Cell Line	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	GI50	>	40.0	ug.mL-1	PMID[520193]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	3.1	ug.mL-1	PMID[520193]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	1.6	ug.mL-1	PMID[520193]

☑ 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 NPC50658 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	380
0.1-0.2	3429
0.2-0.3	12035
0.3-0.4	12572
0.4-0.5	5818
0.5-0.6	4538
0.6-0.7	3143
0.7-0.8	691
0.8-0.85	65
0.85-0.9	21
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9615	High Similarity	NPC25037
0.9615	High Similarity	NPC34984
0.9231	High Similarity	NPC280781
0.9231	High Similarity	NPC48756
0.9067	High Similarity	NPC168511
0.9067	High Similarity	NPC159325
0.8933	High Similarity	NPC282905
0.8933	High Similarity	NPC477229
0.8933	High Similarity	NPC68426
0.8889	High Similarity	NPC105895
0.8831	High Similarity	NPC108840
0.878	High Similarity	NPC62572
0.8718	High Similarity	NPC23884
0.8701	High Similarity	NPC267753
0.8571	High Similarity	NPC130011
0.85	High Similarity	NPC73013
0.8462	Intermediate Similarity	NPC195155
0.8462	Intermediate Similarity	NPC174964
0.8462	Intermediate Similarity	NPC97534
0.8442	Intermediate Similarity	NPC81759
0.8434	Intermediate Similarity	NPC474996
0.84	Intermediate Similarity	NPC2568
0.84	Intermediate Similarity	NPC180777
0.84	Intermediate Similarity	NPC103647
0.84	Intermediate Similarity	NPC260319
0.8375	Intermediate Similarity	NPC243594
0.8375	Intermediate Similarity	NPC31031
0.8375	Intermediate Similarity	NPC472608
0.8372	Intermediate Similarity	NPC67653
0.8372	Intermediate Similarity	NPC471459
0.8354	Intermediate Similarity	NPC475742
0.8354	Intermediate Similarity	NPC5767
0.8312	Intermediate Similarity	NPC247195
0.8312	Intermediate Similarity	NPC89310
0.8295	Intermediate Similarity	NPC472148
0.8295	Intermediate Similarity	NPC472147
0.8293	Intermediate Similarity	NPC58631
0.8293	Intermediate Similarity	NPC271572
0.8293	Intermediate Similarity	NPC474870
0.8276	Intermediate Similarity	NPC185529
0.8276	Intermediate Similarity	NPC472146
0.825	Intermediate Similarity	NPC221420
0.8214	Intermediate Similarity	NPC473299
0.8214	Intermediate Similarity	NPC219535
0.8214	Intermediate Similarity	NPC237938
0.8205	Intermediate Similarity	NPC232112
0.8205	Intermediate Similarity	NPC253805
0.8193	Intermediate Similarity	NPC289486
0.8193	Intermediate Similarity	NPC61107
0.8161	Intermediate Similarity	NPC61688
0.8158	Intermediate Similarity	NPC475977
0.8152	Intermediate Similarity	NPC80417
0.8148	Intermediate Similarity	NPC26029
0.8125	Intermediate Similarity	NPC472486
0.8125	Intermediate Similarity	NPC472487
0.8095	Intermediate Similarity	NPC269684
0.8077	Intermediate Similarity	NPC290058
0.8077	Intermediate Similarity	NPC320549
0.8077	Intermediate Similarity	NPC151018
0.8077	Intermediate Similarity	NPC58057
0.8077	Intermediate Similarity	NPC156277
0.8072	Intermediate Similarity	NPC476071
0.8052	Intermediate Similarity	NPC213178
0.8052	Intermediate Similarity	NPC131892
0.8052	Intermediate Similarity	NPC327728
0.8052	Intermediate Similarity	NPC6120
0.8046	Intermediate Similarity	NPC473319
0.8046	Intermediate Similarity	NPC3032
0.8046	Intermediate Similarity	NPC131104
0.8025	Intermediate Similarity	NPC298168
0.8025	Intermediate Similarity	NPC143133
0.8025	Intermediate Similarity	NPC475031
0.8023	Intermediate Similarity	NPC83242
0.8022	Intermediate Similarity	NPC163685
0.8	Intermediate Similarity	NPC125767
0.8	Intermediate Similarity	NPC21220
0.8	Intermediate Similarity	NPC273366
0.8	Intermediate Similarity	NPC477434
0.8	Intermediate Similarity	NPC471044
0.8	Intermediate Similarity	NPC473336
0.7979	Intermediate Similarity	NPC80640
0.7952	Intermediate Similarity	NPC261616
0.7912	Intermediate Similarity	NPC82633
0.7882	Intermediate Similarity	NPC217559
0.7882	Intermediate Similarity	NPC268578
0.7882	Intermediate Similarity	NPC292458
0.7875	Intermediate Similarity	NPC254340
0.7865	Intermediate Similarity	NPC18536
0.7865	Intermediate Similarity	NPC475211
0.7865	Intermediate Similarity	NPC50443
0.7865	Intermediate Similarity	NPC88337
0.7826	Intermediate Similarity	NPC235109
0.7816	Intermediate Similarity	NPC80700
0.7816	Intermediate Similarity	NPC120395
0.7812	Intermediate Similarity	NPC267637
0.7805	Intermediate Similarity	NPC307865
0.7802	Intermediate Similarity	NPC309127
0.7802	Intermediate Similarity	NPC247877
0.7792	Intermediate Similarity	NPC472984
0.7791	Intermediate Similarity	NPC474482
0.7791	Intermediate Similarity	NPC319909
0.7791	Intermediate Similarity	NPC50438
0.7791	Intermediate Similarity	NPC475745
0.7778	Intermediate Similarity	NPC159789
0.7778	Intermediate Similarity	NPC212733
0.7765	Intermediate Similarity	NPC268040
0.7765	Intermediate Similarity	NPC13494
0.7765	Intermediate Similarity	NPC30583
0.775	Intermediate Similarity	NPC475230
0.7733	Intermediate Similarity	NPC290791
0.7733	Intermediate Similarity	NPC292419
0.7732	Intermediate Similarity	NPC273189
0.7732	Intermediate Similarity	NPC184805
0.7727	Intermediate Similarity	NPC252714
0.7727	Intermediate Similarity	NPC57469
0.7722	Intermediate Similarity	NPC476731
0.7711	Intermediate Similarity	NPC475725
0.7701	Intermediate Similarity	NPC131350
0.7701	Intermediate Similarity	NPC477445
0.7692	Intermediate Similarity	NPC474954
0.7692	Intermediate Similarity	NPC49776
0.7692	Intermediate Similarity	NPC473225
0.7692	Intermediate Similarity	NPC281203
0.7692	Intermediate Similarity	NPC475893
0.7692	Intermediate Similarity	NPC31187
0.7692	Intermediate Similarity	NPC100917
0.7692	Intermediate Similarity	NPC63118
0.7692	Intermediate Similarity	NPC469724
0.7692	Intermediate Similarity	NPC474436
0.7683	Intermediate Similarity	NPC4209
0.7674	Intermediate Similarity	NPC475726
0.7674	Intermediate Similarity	NPC472743
0.766	Intermediate Similarity	NPC472144
0.766	Intermediate Similarity	NPC164349
0.7654	Intermediate Similarity	NPC133922
0.7654	Intermediate Similarity	NPC280026
0.7654	Intermediate Similarity	NPC167702
0.7654	Intermediate Similarity	NPC477508
0.7653	Intermediate Similarity	NPC471430
0.764	Intermediate Similarity	NPC471221
0.764	Intermediate Similarity	NPC226491
0.764	Intermediate Similarity	NPC90676
0.764	Intermediate Similarity	NPC477614
0.7625	Intermediate Similarity	NPC473267
0.7619	Intermediate Similarity	NPC275243
0.7619	Intermediate Similarity	NPC201276
0.7619	Intermediate Similarity	NPC245029
0.7619	Intermediate Similarity	NPC31302
0.7619	Intermediate Similarity	NPC320144
0.7619	Intermediate Similarity	NPC80891
0.7614	Intermediate Similarity	NPC472738
0.7614	Intermediate Similarity	NPC475862
0.7614	Intermediate Similarity	NPC74363
0.7609	Intermediate Similarity	NPC206878
0.7595	Intermediate Similarity	NPC324607
0.7595	Intermediate Similarity	NPC321732
0.759	Intermediate Similarity	NPC317913
0.759	Intermediate Similarity	NPC472746
0.759	Intermediate Similarity	NPC112463
0.759	Intermediate Similarity	NPC207010
0.759	Intermediate Similarity	NPC477918
0.7586	Intermediate Similarity	NPC181871
0.7586	Intermediate Similarity	NPC9060
0.7582	Intermediate Similarity	NPC475416
0.7564	Intermediate Similarity	NPC204233
0.7564	Intermediate Similarity	NPC41542
0.7564	Intermediate Similarity	NPC48079
0.7561	Intermediate Similarity	NPC179858
0.7561	Intermediate Similarity	NPC72444
0.7558	Intermediate Similarity	NPC328007
0.7558	Intermediate Similarity	NPC317066
0.7556	Intermediate Similarity	NPC477443
0.7556	Intermediate Similarity	NPC477440
0.7556	Intermediate Similarity	NPC69627
0.7553	Intermediate Similarity	NPC472145
0.7532	Intermediate Similarity	NPC260116
0.7532	Intermediate Similarity	NPC80463
0.7531	Intermediate Similarity	NPC474755
0.7531	Intermediate Similarity	NPC310766
0.7531	Intermediate Similarity	NPC109510
0.7529	Intermediate Similarity	NPC470609
0.7528	Intermediate Similarity	NPC73064
0.7528	Intermediate Similarity	NPC263802
0.75	Intermediate Similarity	NPC324700
0.75	Intermediate Similarity	NPC87393
0.75	Intermediate Similarity	NPC80089
0.75	Intermediate Similarity	NPC34046
0.75	Intermediate Similarity	NPC171426
0.75	Intermediate Similarity	NPC133954
0.75	Intermediate Similarity	NPC476189
0.75	Intermediate Similarity	NPC282454
0.75	Intermediate Similarity	NPC292553
0.75	Intermediate Similarity	NPC471902
0.75	Intermediate Similarity	NPC473690
0.75	Intermediate Similarity	NPC287118
0.75	Intermediate Similarity	NPC185465
0.75	Intermediate Similarity	NPC474572
0.75	Intermediate Similarity	NPC224802
0.7474	Intermediate Similarity	NPC234617
0.7474	Intermediate Similarity	NPC124703

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 NPC50658 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	409
0.1-0.2	3643
0.2-0.3	3573
0.3-0.4	939
0.4-0.5	252
0.5-0.6	247
0.6-0.7	60
0.7-0.8	23
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8077	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3703	Phase 2
0.7722	Intermediate Similarity	NPD4245	Approved
0.7722	Intermediate Similarity	NPD4244	Approved
0.7692	Intermediate Similarity	NPD5360	Phase 3
0.7692	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD6117	Approved
0.7654	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD3698	Phase 2
0.759	Intermediate Similarity	NPD6116	Phase 1
0.75	Intermediate Similarity	NPD6114	Approved
0.75	Intermediate Similarity	NPD6118	Approved
0.75	Intermediate Similarity	NPD6115	Approved
0.75	Intermediate Similarity	NPD4789	Approved
0.75	Intermediate Similarity	NPD6697	Approved
0.7308	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD3671	Phase 1
0.7204	Intermediate Similarity	NPD8034	Phase 2
0.7204	Intermediate Similarity	NPD8035	Phase 2
0.7195	Intermediate Similarity	NPD5777	Approved
0.7195	Intermediate Similarity	NPD4758	Discontinued
0.7053	Intermediate Similarity	NPD7748	Approved
0.7021	Intermediate Similarity	NPD7515	Phase 2
0.701	Intermediate Similarity	NPD7902	Approved
0.7	Intermediate Similarity	NPD4224	Phase 2
0.6951	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD3702	Approved
0.6897	Remote Similarity	NPD5364	Discontinued
0.6848	Remote Similarity	NPD3618	Phase 1
0.6786	Remote Similarity	NPD6081	Approved
0.6703	Remote Similarity	NPD4788	Approved
0.6701	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD4787	Phase 1
0.6632	Remote Similarity	NPD5328	Approved
0.663	Remote Similarity	NPD4786	Approved
0.6629	Remote Similarity	NPD7645	Phase 2
0.6602	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD3667	Approved
0.6556	Remote Similarity	NPD6928	Phase 2
0.6495	Remote Similarity	NPD6079	Approved
0.6489	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6399	Phase 3
0.6429	Remote Similarity	NPD4202	Approved
0.6415	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD6920	Discontinued
0.6277	Remote Similarity	NPD3665	Phase 1
0.6277	Remote Similarity	NPD3133	Approved
0.6277	Remote Similarity	NPD3666	Approved
0.625	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7115	Discovery
0.6238	Remote Similarity	NPD4697	Phase 3
0.6226	Remote Similarity	NPD6675	Approved
0.6226	Remote Similarity	NPD6402	Approved
0.6226	Remote Similarity	NPD7128	Approved
0.6226	Remote Similarity	NPD5739	Approved
0.6204	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD6373	Approved
0.6204	Remote Similarity	NPD6372	Approved
0.6196	Remote Similarity	NPD7525	Registered
0.6186	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD4755	Approved
0.6117	Remote Similarity	NPD7638	Approved
0.6111	Remote Similarity	NPD6881	Approved
0.6111	Remote Similarity	NPD6899	Approved
0.6111	Remote Similarity	NPD6415	Discontinued
0.6111	Remote Similarity	NPD7320	Approved
0.6091	Remote Similarity	NPD6650	Approved
0.6091	Remote Similarity	NPD6649	Approved
0.6078	Remote Similarity	NPD5221	Approved
0.6078	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD5222	Approved
0.6068	Remote Similarity	NPD8328	Phase 3
0.6058	Remote Similarity	NPD5286	Approved
0.6058	Remote Similarity	NPD8418	Phase 2
0.6058	Remote Similarity	NPD7639	Approved
0.6058	Remote Similarity	NPD4700	Approved
0.6058	Remote Similarity	NPD7640	Approved
0.6058	Remote Similarity	NPD5285	Approved
0.6058	Remote Similarity	NPD4696	Approved
0.6047	Remote Similarity	NPD229	Approved
0.6019	Remote Similarity	NPD5701	Approved
0.6019	Remote Similarity	NPD6083	Phase 2
0.6019	Remote Similarity	NPD5697	Approved
0.6019	Remote Similarity	NPD6084	Phase 2
0.6019	Remote Similarity	NPD5173	Approved
0.6	Remote Similarity	NPD7102	Approved
0.6	Remote Similarity	NPD1700	Approved
0.6	Remote Similarity	NPD5223	Approved
0.6	Remote Similarity	NPD7290	Approved
0.6	Remote Similarity	NPD6883	Approved
0.5982	Remote Similarity	NPD8133	Approved
0.598	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD5330	Approved
0.5979	Remote Similarity	NPD7334	Approved
0.5979	Remote Similarity	NPD7146	Approved
0.5979	Remote Similarity	NPD7521	Approved
0.5979	Remote Similarity	NPD6409	Approved
0.5979	Remote Similarity	NPD6684	Approved
0.5978	Remote Similarity	NPD4802	Phase 2
0.5978	Remote Similarity	NPD3617	Approved
0.5978	Remote Similarity	NPD4238	Approved
0.5963	Remote Similarity	NPD6011	Approved
0.5962	Remote Similarity	NPD4225	Approved
0.596	Remote Similarity	NPD4753	Phase 2
0.5948	Remote Similarity	NPD6054	Approved
0.5948	Remote Similarity	NPD6059	Approved
0.5946	Remote Similarity	NPD6847	Approved
0.5946	Remote Similarity	NPD8130	Phase 1
0.5946	Remote Similarity	NPD6869	Approved
0.5946	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD6617	Approved
0.5943	Remote Similarity	NPD4633	Approved
0.5943	Remote Similarity	NPD5211	Phase 2
0.5943	Remote Similarity	NPD5224	Approved
0.5943	Remote Similarity	NPD5225	Approved
0.5943	Remote Similarity	NPD5226	Approved
0.5943	Remote Similarity	NPD7632	Discontinued
0.5941	Remote Similarity	NPD8171	Discontinued
0.5938	Remote Similarity	NPD3668	Phase 3
0.5918	Remote Similarity	NPD3573	Approved
0.5909	Remote Similarity	NPD6014	Approved
0.5909	Remote Similarity	NPD6012	Approved
0.5909	Remote Similarity	NPD6013	Approved
0.5895	Remote Similarity	NPD4223	Phase 3
0.5895	Remote Similarity	NPD4221	Approved
0.5893	Remote Similarity	NPD6882	Approved
0.5893	Remote Similarity	NPD8297	Approved
0.5888	Remote Similarity	NPD4754	Approved
0.5888	Remote Similarity	NPD5175	Approved
0.5888	Remote Similarity	NPD5174	Approved
0.5876	Remote Similarity	NPD5329	Approved
0.5868	Remote Similarity	NPD7736	Approved
0.5859	Remote Similarity	NPD6903	Approved
0.5856	Remote Similarity	NPD4634	Approved
0.5854	Remote Similarity	NPD3198	Approved
0.5847	Remote Similarity	NPD6370	Approved
0.5842	Remote Similarity	NPD6411	Approved
0.5833	Remote Similarity	NPD5141	Approved
0.5825	Remote Similarity	NPD5210	Approved
0.5825	Remote Similarity	NPD4629	Approved
0.5823	Remote Similarity	NPD615	Clinical (unspecified phase)
0.5823	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD5279	Phase 3
0.581	Remote Similarity	NPD5696	Approved
0.58	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD4139	Approved
0.5789	Remote Similarity	NPD4692	Approved
0.578	Remote Similarity	NPD4768	Approved
0.578	Remote Similarity	NPD4767	Approved
0.578	Remote Similarity	NPD6008	Approved
0.5773	Remote Similarity	NPD4197	Approved
0.5766	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD371	Approved
0.5763	Remote Similarity	NPD6016	Approved
0.5763	Remote Similarity	NPD6921	Approved
0.5763	Remote Similarity	NPD6015	Approved
0.575	Remote Similarity	NPD7492	Approved
0.5733	Remote Similarity	NPD384	Approved
0.5733	Remote Similarity	NPD385	Approved
0.5728	Remote Similarity	NPD6001	Approved
0.5727	Remote Similarity	NPD6412	Phase 2
0.5714	Remote Similarity	NPD1694	Approved
0.5714	Remote Similarity	NPD5988	Approved
0.5714	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD6616	Approved
0.57	Remote Similarity	NPD5737	Approved
0.57	Remote Similarity	NPD6672	Approved
0.5698	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD6319	Approved
0.5676	Remote Similarity	NPD4730	Approved
0.5676	Remote Similarity	NPD4729	Approved
0.5676	Remote Similarity	NPD5128	Approved
0.5673	Remote Similarity	NPD5695	Phase 3
0.567	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.567	Remote Similarity	NPD3669	Approved
0.5657	Remote Similarity	NPD5205	Approved
0.5657	Remote Similarity	NPD4689	Approved
0.5657	Remote Similarity	NPD4138	Approved
0.5657	Remote Similarity	NPD6098	Approved
0.5657	Remote Similarity	NPD4519	Discontinued
0.5657	Remote Similarity	NPD4693	Phase 3
0.5657	Remote Similarity	NPD4690	Approved
0.5657	Remote Similarity	NPD4623	Approved
0.5657	Remote Similarity	NPD4688	Approved
0.5656	Remote Similarity	NPD7078	Approved
0.5656	Remote Similarity	NPD8293	Discontinued
0.5652	Remote Similarity	NPD7339	Approved
0.5652	Remote Similarity	NPD6942	Approved
0.5644	Remote Similarity	NPD6101	Approved
0.5644	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD6335	Approved
0.563	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD5369	Approved
0.5625	Remote Similarity	NPD1780	Approved
0.5625	Remote Similarity	NPD1779	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