NPASS Compound

Structure

CID279833 OpenBabel06191716082D 21 22 0 0 1 0 0 0 0 0999 V2000 -1.0507 2.5140 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4493 3.3800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3153 3.1479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0453 -1.0547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0141 -3.3418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2532 -2.0328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9804 -3.4464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5507 -0.0841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0507 2.5140 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3153 2.1479 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0507 -0.9502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2220 -2.3637 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6440 -1.8637 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9493 0.7819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4493 1.6479 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3872 -2.5328 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 2.1813 1.6479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1356 -1.9570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9493 0.7819 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4168 1.1479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4493 -0.0841 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 9 1 0 0 0 0 4 6 1 0 0 0 0 4 11 2 0 0 0 0 5 7 1 0 0 0 0 5 12 1 0 0 0 0 6 16 1 0 0 0 0 7 16 1 0 0 0 0 8 11 1 0 0 0 0 8 21 1 0 0 0 0 9 15 1 0 0 0 0 10 3 1 1 0 0 0 10 15 1 0 0 0 0 10 17 1 0 0 0 0 11 13 1 0 0 0 0 12 13 1 0 0 0 0 12 18 1 6 0 0 0 13 16 1 6 0 0 0 14 15 1 0 0 0 0 14 19 2 0 0 0 0 14 21 1 0 0 0 0 15 20 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	299.17
Volume:	300.558
LogP:	0.825
LogD:	0.858
LogS:	-1.594
# Rotatable Bonds:	6
TPSA:	90.23
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.476
Synthetic Accessibility Score:	4.347
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.967
MDCK Permeability:	0.00010045950330095366
Pgp-inhibitor:	0.002
Pgp-substrate:	0.698
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.429
30% Bioavailability (F30%):	0.22

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.542
Plasma Protein Binding (PPB):	32.964534759521484%
Volume Distribution (VD):	1.108
Pgp-substrate:	68.30086517333984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.081
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.547
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.124
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.346
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.267

ADMET: Excretion

Clearance (CL):	2.315
Half-life (T1/2):	0.791

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.153
Drug-inuced Liver Injury (DILI):	0.431
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.842
Maximum Recommended Daily Dose:	0.876
Skin Sensitization:	0.082
Carcinogencity:	0.943
Eye Corrosion:	0.004
Eye Irritation:	0.133
Respiratory Toxicity:	0.854

Download Data

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

Natural Product: NPC279833

Natural Product ID:	NPC279833
*Common Name:**	Lycopsamine
IUPAC Name:	[(7R,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2R)-2-hydroxy-2-[(1R)-1-hydroxyethyl]-3-methylbutanoate
Synonyms:	Lycopsamine
Standard InCHIKey:	SFVVQRJOGUKCEG-BPGGGUHBSA-N
Standard InCHI:	InChI=1S/C15H25NO5/c1-9(2)15(20,10(3)17)14(19)21-8-11-4-6-16-7-5-12(18)13(11)16/h4,9-10,12-13,17-18,20H,5-8H2,1-3H3/t10-,12-,13-,15-/m1/s1
SMILES:	CC(C)[C@@]([C@@H](C)O)(C(=O)OCC1=CCN2CC[C@H]([C@@H]12)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL450265
PubChem CID:	44584035
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives

*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
NPO26180	Heliotropium megalanthum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834169]
NPO19080	Borago officinalis	Species	Boraginaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO19080	Borago officinalis	Species	Boraginaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19080	Borago officinalis	Species	Boraginaceae	Eukaryota	Fruit Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO19080	Borago officinalis	Species	Boraginaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO19080	Borago officinalis	Species	Boraginaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO19080	Borago officinalis	Species	Boraginaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO19080	Borago officinalis	Species	Boraginaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO19080	Borago officinalis	Species	Boraginaceae	Eukaryota	Seed Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO19080	Borago officinalis	Species	Boraginaceae	Eukaryota	Seed Oil	n.a.	n.a.	Database[FooDB]
NPO19408	Eupatorium compositifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7288	Heliotropium steudneri	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10937	Symphytum x uplandicum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19080	Borago officinalis	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21824	Lycopus lucidus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24601	Rumex dentatus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10937	Symphytum x uplandicum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19408	Eupatorium compositifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21824	Lycopus lucidus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24601	Rumex dentatus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7288	Heliotropium steudneri	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19080	Borago officinalis	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21824	Lycopus lucidus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24601	Rumex dentatus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21824	Lycopus lucidus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26180	Heliotropium megalanthum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19080	Borago officinalis	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19408	Eupatorium compositifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24601	Rumex dentatus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21824	Lycopus lucidus	Species	Lamiaceae	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
EC50	2
Others	6

Activity Type	# Activity
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	Activity	=	61.08	%	PMID[505152]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	Activity	=	27.53	%	PMID[505152]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	Activity	=	68.4	%	PMID[505152]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	EC50	=	31.62	microg/cm2	PMID[505152]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	EC50	=	25.97	microg/cm2	PMID[505152]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	Activity	=	21.19	mg	PMID[505152]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	Activity	=	3.32	mg	PMID[505152]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	Activity	=	12.0	%	PMID[505152]

☑ 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 NPC279833 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	90
0.1-0.2	593
0.2-0.3	5836
0.3-0.4	20894
0.4-0.5	11447
0.5-0.6	3532
0.6-0.7	279
0.7-0.8	10
0.8-0.85	7
0.85-0.9	2
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC80439
1.0	High Similarity	NPC173690
0.9896	High Similarity	NPC64168
0.9792	High Similarity	NPC6271
0.9126	High Similarity	NPC316984
0.9126	High Similarity	NPC30911
0.8796	High Similarity	NPC201889
0.8796	High Similarity	NPC106791
0.8426	Intermediate Similarity	NPC130124
0.8426	Intermediate Similarity	NPC193471
0.8393	Intermediate Similarity	NPC23963
0.8125	Intermediate Similarity	NPC284656
0.8073	Intermediate Similarity	NPC168758
0.8073	Intermediate Similarity	NPC181510
0.8073	Intermediate Similarity	NPC47857
0.7807	Intermediate Similarity	NPC235625
0.7522	Intermediate Similarity	NPC275100
0.7426	Intermediate Similarity	NPC52533
0.7368	Intermediate Similarity	NPC474497
0.7345	Intermediate Similarity	NPC195435
0.7345	Intermediate Similarity	NPC196073
0.7182	Intermediate Similarity	NPC473289
0.708	Intermediate Similarity	NPC271562
0.7059	Intermediate Similarity	NPC200412
0.7059	Intermediate Similarity	NPC156336
0.7059	Intermediate Similarity	NPC120599
0.7027	Intermediate Similarity	NPC474244
0.7009	Intermediate Similarity	NPC469597
0.6972	Remote Similarity	NPC52820
0.6937	Remote Similarity	NPC188785
0.687	Remote Similarity	NPC474099
0.6838	Remote Similarity	NPC474411
0.6838	Remote Similarity	NPC474431
0.6814	Remote Similarity	NPC474828
0.6814	Remote Similarity	NPC68001
0.6814	Remote Similarity	NPC474827
0.6814	Remote Similarity	NPC199831
0.68	Remote Similarity	NPC474371
0.6754	Remote Similarity	NPC469604
0.6721	Remote Similarity	NPC471261
0.6696	Remote Similarity	NPC93179
0.6693	Remote Similarity	NPC471086
0.6667	Remote Similarity	NPC11379
0.6636	Remote Similarity	NPC150041
0.6634	Remote Similarity	NPC99651
0.661	Remote Similarity	NPC469603
0.6609	Remote Similarity	NPC44514
0.66	Remote Similarity	NPC233108
0.6589	Remote Similarity	NPC477988
0.6587	Remote Similarity	NPC471087
0.6587	Remote Similarity	NPC477985
0.6587	Remote Similarity	NPC326386
0.6557	Remote Similarity	NPC65045
0.6532	Remote Similarity	NPC230849
0.6529	Remote Similarity	NPC472536
0.6529	Remote Similarity	NPC103391
0.6522	Remote Similarity	NPC471260
0.6518	Remote Similarity	NPC476344
0.6514	Remote Similarity	NPC299808
0.6514	Remote Similarity	NPC72183
0.6514	Remote Similarity	NPC118844
0.6514	Remote Similarity	NPC110875
0.6509	Remote Similarity	NPC469861
0.6509	Remote Similarity	NPC478112
0.6509	Remote Similarity	NPC130436
0.6509	Remote Similarity	NPC469860
0.6489	Remote Similarity	NPC133089
0.6475	Remote Similarity	NPC30196
0.6471	Remote Similarity	NPC113012
0.6471	Remote Similarity	NPC122926
0.6462	Remote Similarity	NPC215507
0.6439	Remote Similarity	NPC120420
0.6436	Remote Similarity	NPC474278
0.6423	Remote Similarity	NPC6531
0.6417	Remote Similarity	NPC58281
0.6412	Remote Similarity	NPC120335
0.641	Remote Similarity	NPC471259
0.6406	Remote Similarity	NPC329401
0.6406	Remote Similarity	NPC477987
0.6391	Remote Similarity	NPC99864
0.6391	Remote Similarity	NPC471256
0.6389	Remote Similarity	NPC476803
0.6389	Remote Similarity	NPC287089
0.6378	Remote Similarity	NPC293550
0.6378	Remote Similarity	NPC477990
0.6378	Remote Similarity	NPC477989
0.6378	Remote Similarity	NPC323168
0.6378	Remote Similarity	NPC111162
0.6378	Remote Similarity	NPC471255
0.6378	Remote Similarity	NPC318445
0.6378	Remote Similarity	NPC316133
0.6371	Remote Similarity	NPC174463
0.6364	Remote Similarity	NPC1111
0.6364	Remote Similarity	NPC261750
0.6357	Remote Similarity	NPC314282
0.6355	Remote Similarity	NPC469910
0.6349	Remote Similarity	NPC470000
0.6348	Remote Similarity	NPC185141
0.6348	Remote Similarity	NPC133907
0.6348	Remote Similarity	NPC110443
0.6348	Remote Similarity	NPC46998
0.6348	Remote Similarity	NPC128733
0.6325	Remote Similarity	NPC75523
0.6316	Remote Similarity	NPC471144
0.6311	Remote Similarity	NPC475210
0.6306	Remote Similarity	NPC469692
0.6306	Remote Similarity	NPC469645
0.6293	Remote Similarity	NPC471258
0.6281	Remote Similarity	NPC476875
0.6279	Remote Similarity	NPC471263
0.6273	Remote Similarity	NPC474232
0.6261	Remote Similarity	NPC475949
0.6261	Remote Similarity	NPC26597
0.625	Remote Similarity	NPC121825
0.6239	Remote Similarity	NPC475945
0.6239	Remote Similarity	NPC4620
0.6239	Remote Similarity	NPC475871
0.623	Remote Similarity	NPC43648
0.623	Remote Similarity	NPC314550
0.623	Remote Similarity	NPC60432
0.6228	Remote Similarity	NPC4834
0.6228	Remote Similarity	NPC241426
0.6228	Remote Similarity	NPC167380
0.6216	Remote Similarity	NPC9447
0.6212	Remote Similarity	NPC307165
0.6207	Remote Similarity	NPC472753
0.6204	Remote Similarity	NPC278283
0.6202	Remote Similarity	NPC313333
0.6202	Remote Similarity	NPC313342
0.6202	Remote Similarity	NPC314451
0.6202	Remote Similarity	NPC314512
0.619	Remote Similarity	NPC52861
0.6186	Remote Similarity	NPC220964
0.6186	Remote Similarity	NPC475676
0.6183	Remote Similarity	NPC329919
0.6183	Remote Similarity	NPC477793
0.6182	Remote Similarity	NPC473564
0.6172	Remote Similarity	NPC471262
0.6168	Remote Similarity	NPC212363
0.6168	Remote Similarity	NPC32676
0.6168	Remote Similarity	NPC158756
0.6165	Remote Similarity	NPC316401
0.6161	Remote Similarity	NPC156553
0.6154	Remote Similarity	NPC472754
0.6154	Remote Similarity	NPC471148
0.6154	Remote Similarity	NPC474747
0.6148	Remote Similarity	NPC147238
0.6148	Remote Similarity	NPC29501
0.6147	Remote Similarity	NPC266957
0.614	Remote Similarity	NPC121857
0.6139	Remote Similarity	NPC474280
0.6139	Remote Similarity	NPC473489
0.6132	Remote Similarity	NPC474252
0.6132	Remote Similarity	NPC89555
0.6126	Remote Similarity	NPC316228
0.6116	Remote Similarity	NPC38154
0.6111	Remote Similarity	NPC470755
0.6107	Remote Similarity	NPC476951
0.6106	Remote Similarity	NPC469632
0.6102	Remote Similarity	NPC472755
0.6102	Remote Similarity	NPC265094
0.6098	Remote Similarity	NPC474995
0.6098	Remote Similarity	NPC276995
0.6098	Remote Similarity	NPC279383
0.6098	Remote Similarity	NPC478024
0.6098	Remote Similarity	NPC76660
0.6091	Remote Similarity	NPC476805
0.6091	Remote Similarity	NPC119740
0.6091	Remote Similarity	NPC150063
0.6087	Remote Similarity	NPC218064
0.6083	Remote Similarity	NPC324327
0.6083	Remote Similarity	NPC72813
0.6083	Remote Similarity	NPC326994
0.6083	Remote Similarity	NPC474421
0.6083	Remote Similarity	NPC26617
0.6083	Remote Similarity	NPC194620
0.6078	Remote Similarity	NPC329852
0.6078	Remote Similarity	NPC473582
0.6068	Remote Similarity	NPC474742
0.6068	Remote Similarity	NPC474339
0.6068	Remote Similarity	NPC474873
0.6068	Remote Similarity	NPC164598
0.6063	Remote Similarity	NPC477986
0.6063	Remote Similarity	NPC138534
0.6055	Remote Similarity	NPC469483
0.6055	Remote Similarity	NPC261721
0.6053	Remote Similarity	NPC220221
0.605	Remote Similarity	NPC474741
0.605	Remote Similarity	NPC472756
0.605	Remote Similarity	NPC205176
0.6048	Remote Similarity	NPC475988
0.6038	Remote Similarity	NPC474894
0.6038	Remote Similarity	NPC24417
0.6036	Remote Similarity	NPC225283
0.6036	Remote Similarity	NPC478110
0.6034	Remote Similarity	NPC473326
0.6033	Remote Similarity	NPC327286
0.6033	Remote Similarity	NPC55972
0.6033	Remote Similarity	NPC14862
0.6033	Remote Similarity	NPC474664

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 NPC279833 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	85
0.1-0.2	494
0.2-0.3	3228
0.3-0.4	3859
0.4-0.5	1221
0.5-0.6	247
0.6-0.7	15
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9126	High Similarity	NPD2204	Approved
0.648	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD8273	Phase 1
0.6406	Remote Similarity	NPD8451	Approved
0.6391	Remote Similarity	NPD8415	Approved
0.6378	Remote Similarity	NPD7642	Approved
0.6357	Remote Similarity	NPD8448	Approved
0.6343	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD1376	Discontinued
0.6299	Remote Similarity	NPD8080	Discontinued
0.6241	Remote Similarity	NPD2575	Approved
0.6212	Remote Similarity	NPD8392	Approved
0.6212	Remote Similarity	NPD8391	Approved
0.6212	Remote Similarity	NPD8390	Approved
0.6202	Remote Similarity	NPD8341	Approved
0.6202	Remote Similarity	NPD8340	Approved
0.6202	Remote Similarity	NPD8342	Approved
0.6202	Remote Similarity	NPD8299	Approved
0.614	Remote Similarity	NPD4228	Discovery
0.6083	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6045	Remote Similarity	NPD3662	Phase 3
0.6045	Remote Similarity	NPD3663	Approved
0.6045	Remote Similarity	NPD3664	Approved
0.6045	Remote Similarity	NPD3661	Approved
0.6	Remote Similarity	NPD777	Phase 3
0.6	Remote Similarity	NPD8384	Approved
0.6	Remote Similarity	NPD2613	Approved
0.5984	Remote Similarity	NPD7641	Discontinued
0.5984	Remote Similarity	NPD1773	Discontinued
0.5935	Remote Similarity	NPD6421	Discontinued
0.5897	Remote Similarity	NPD4225	Approved
0.5896	Remote Similarity	NPD2159	Approved
0.5896	Remote Similarity	NPD2625	Approved
0.5896	Remote Similarity	NPD2627	Approved
0.5896	Remote Similarity	NPD2160	Approved
0.5896	Remote Similarity	NPD2628	Approved
0.5896	Remote Similarity	NPD2626	Approved
0.5877	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.587	Remote Similarity	NPD2566	Approved
0.587	Remote Similarity	NPD3088	Approved
0.587	Remote Similarity	NPD2570	Approved
0.587	Remote Similarity	NPD3089	Approved
0.587	Remote Similarity	NPD3087	Approved
0.587	Remote Similarity	NPD3614	Approved
0.587	Remote Similarity	NPD4746	Phase 3
0.587	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.587	Remote Similarity	NPD2574	Discontinued
0.587	Remote Similarity	NPD3615	Approved
0.587	Remote Similarity	NPD3090	Approved
0.587	Remote Similarity	NPD3616	Approved
0.587	Remote Similarity	NPD4745	Approved
0.587	Remote Similarity	NPD2573	Approved
0.587	Remote Similarity	NPD2571	Approved
0.5846	Remote Similarity	NPD8444	Approved
0.5833	Remote Similarity	NPD2611	Approved
0.5833	Remote Similarity	NPD2612	Approved
0.5833	Remote Similarity	NPD4217	Approved
0.5833	Remote Similarity	NPD4218	Approved
0.5833	Remote Similarity	NPD4216	Approved
0.5833	Remote Similarity	NPD4215	Approved
0.5833	Remote Similarity	NPD883	Phase 2
0.5833	Remote Similarity	NPD2610	Approved
0.5833	Remote Similarity	NPD2608	Approved
0.5833	Remote Similarity	NPD882	Phase 2
0.5833	Remote Similarity	NPD3132	Approved
0.5833	Remote Similarity	NPD2609	Approved
0.5833	Remote Similarity	NPD3131	Approved
0.5818	Remote Similarity	NPD9512	Approved
0.5814	Remote Similarity	NPD3159	Discontinued
0.5814	Remote Similarity	NPD2495	Phase 3
0.5809	Remote Similarity	NPD5204	Approved
0.5806	Remote Similarity	NPD6420	Discontinued
0.58	Remote Similarity	NPD8414	Discontinued
0.5797	Remote Similarity	NPD4621	Approved
0.5797	Remote Similarity	NPD4619	Approved
0.5786	Remote Similarity	NPD4686	Approved
0.5786	Remote Similarity	NPD4685	Phase 3
0.5786	Remote Similarity	NPD4684	Phase 3
0.5781	Remote Similarity	NPD7505	Discontinued
0.5776	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD2645	Approved
0.5758	Remote Similarity	NPD7829	Approved
0.5758	Remote Similarity	NPD7830	Approved
0.5758	Remote Similarity	NPD616	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD4211	Phase 1
0.5727	Remote Similarity	NPD9511	Approved
0.5726	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6310	Approved
0.5714	Remote Similarity	NPD6309	Approved
0.5714	Remote Similarity	NPD6311	Approved
0.5702	Remote Similarity	NPD6698	Approved
0.5702	Remote Similarity	NPD46	Approved
0.5682	Remote Similarity	NPD1748	Approved
0.5682	Remote Similarity	NPD1806	Approved
0.5676	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD7983	Approved
0.5652	Remote Similarity	NPD6845	Suspended
0.5648	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.5635	Remote Similarity	NPD1719	Phase 1
0.5625	Remote Similarity	NPD4249	Approved
0.5619	Remote Similarity	NPD1452	Discontinued
0.5606	Remote Similarity	NPD6921	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