NPASS Compound

Structure

CID64168 OpenBabel06191715402D 22 23 0 0 1 0 0 0 0 0999 V2000 3.4652 4.8082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6261 6.2498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7913 6.4704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1347 6.4636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4615 0.8563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4618 0.8306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9741 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9744 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4527 2.5226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6295 5.2868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3128 5.6347 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9741 1.6869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9744 1.6869 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.6869 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9649 4.3179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7972 4.8024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -1.4775 2.5512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1292 4.7965 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2816 3.9701 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3497 5.6313 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9683 3.3549 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 4 21 1 0 0 0 0 5 7 1 0 0 0 0 5 12 2 0 0 0 0 6 8 1 0 0 0 0 6 13 1 0 0 0 0 7 17 1 0 0 0 0 8 17 1 0 0 0 0 9 12 1 0 0 0 0 9 22 1 0 0 0 0 10 16 1 0 0 0 0 11 3 1 6 0 0 0 11 16 1 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 13 14 1 0 0 0 0 13 18 1 6 0 0 0 14 17 1 1 0 0 0 15 16 1 0 0 0 0 15 19 2 0 0 0 0 15 22 1 0 0 0 0 16 20 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	313.19
Volume:	317.854
LogP:	1.272
LogD:	1.288
LogS:	-1.804
# Rotatable Bonds:	7
TPSA:	79.23
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.543
Synthetic Accessibility Score:	4.402
Fsp3:	0.812
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:	-4.552
MDCK Permeability:	8.30983481137082e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.134
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.548
30% Bioavailability (F30%):	0.919

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.683
Plasma Protein Binding (PPB):	28.407466888427734%
Volume Distribution (VD):	1.333
Pgp-substrate:	68.43570709228516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.089
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.765
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.06
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.322
CYP3A4-inhibitor:	0.013
CYP3A4-substrate:	0.374

ADMET: Excretion

Clearance (CL):	6.802
Half-life (T1/2):	0.341

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.156
Drug-inuced Liver Injury (DILI):	0.211
AMES Toxicity:	0.353
Rat Oral Acute Toxicity:	0.504
Maximum Recommended Daily Dose:	0.373
Skin Sensitization:	0.072
Carcinogencity:	0.966
Eye Corrosion:	0.004
Eye Irritation:	0.041
Respiratory Toxicity:	0.528

Download Data

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

Natural Product: NPC64168

Natural Product ID:	NPC64168
*Common Name:**	Heliotrine
IUPAC Name:	[(7S,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-2-hydroxy-2-[(1R)-1-methoxyethyl]-3-methylbutanoate
Synonyms:	Heliotrine
Standard InCHIKey:	LMFKRLGHEKVMNT-UJDVCPFMSA-N
Standard InCHI:	InChI=1S/C16H27NO5/c1-10(2)16(20,11(3)21-4)15(19)22-9-12-5-7-17-8-6-13(18)14(12)17/h5,10-11,13-14,18,20H,6-9H2,1-4H3/t11-,13+,14-,16+/m1/s1
SMILES:	CO[C@@H]([C@](C(=O)OCC1=CCN2[C@H]1[C@@H](O)CC2)(C(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2165593
PubChem CID:	906426
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
NPO25275	Cynoglossum officinale	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8442	Heliotropium curassavicum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO149	Heliotropium europaeum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO146	Heliotropium indicum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO146	Heliotropium indicum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO149	Heliotropium europaeum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25275	Cynoglossum officinale	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8442	Heliotropium curassavicum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO149	Heliotropium europaeum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25275	Cynoglossum officinale	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO146	Heliotropium indicum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10701	Indigofera aspalathoides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO146	Heliotropium indicum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO149	Heliotropium europaeum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25275	Cynoglossum officinale	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7915	Simarouba amara	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8442	Heliotropium curassavicum	Species	Heliotropiaceae	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	2
Others	14

Activity Type	# Activity
Individual Protein	2
Organism	14

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	21.27	%	PMID[558891]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	1.48	%	PMID[558891]
NPT2529	Organism	Rhabditis sp.	Rhabditis sp.	Activity	=	58.0	%	PMID[558892]
NPT2529	Organism	Rhabditis sp.	Rhabditis sp.	Activity	=	32.0	%	PMID[558892]
NPT2529	Organism	Rhabditis sp.	Rhabditis sp.	Activity	=	0.0	%	PMID[558892]
NPT2530	Organism	Pratylenchus penetrans	Pratylenchus penetrans	MIC50	=	3300.0	ug.mL-1	PMID[558892]
NPT450	Organism	Meloidogyne incognita	Meloidogyne incognita	MIC50	=	800.0	ug.mL-1	PMID[558892]
NPT2531	Organism	Heterodera schachtii	Heterodera schachtii	MIC50	=	1100.0	ug.mL-1	PMID[558892]
NPT2529	Organism	Rhabditis sp.	Rhabditis sp.	MIC50	=	100.0	ug.mL-1	PMID[558892]
NPT2530	Organism	Pratylenchus penetrans	Pratylenchus penetrans	MIC50	=	4800.0	ug.mL-1	PMID[558892]
NPT450	Organism	Meloidogyne incognita	Meloidogyne incognita	MIC50	=	300.0	ug.mL-1	PMID[558892]
NPT2531	Organism	Heterodera schachtii	Heterodera schachtii	MIC50	=	2100.0	ug.mL-1	PMID[558892]
NPT2530	Organism	Pratylenchus penetrans	Pratylenchus penetrans	MIC50	=	49800.0	ug.mL-1	PMID[558892]
NPT450	Organism	Meloidogyne incognita	Meloidogyne incognita	MIC50	=	57900.0	ug.mL-1	PMID[558892]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[558893]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[558893]

☑ 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 NPC64168 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	89
0.1-0.2	601
0.2-0.3	5873
0.3-0.4	20304
0.4-0.5	11515
0.5-0.6	3906
0.6-0.7	382
0.7-0.8	11
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
0.9896	High Similarity	NPC6271
0.9896	High Similarity	NPC80439
0.9896	High Similarity	NPC173690
0.9896	High Similarity	NPC279833
0.9223	High Similarity	NPC316984
0.9223	High Similarity	NPC30911
0.8889	High Similarity	NPC201889
0.8889	High Similarity	NPC106791
0.8519	High Similarity	NPC130124
0.8519	High Similarity	NPC193471
0.8482	Intermediate Similarity	NPC23963
0.8214	Intermediate Similarity	NPC284656
0.8165	Intermediate Similarity	NPC181510
0.8165	Intermediate Similarity	NPC47857
0.8165	Intermediate Similarity	NPC168758
0.7895	Intermediate Similarity	NPC235625
0.7611	Intermediate Similarity	NPC275100
0.7456	Intermediate Similarity	NPC474497
0.7434	Intermediate Similarity	NPC195435
0.7434	Intermediate Similarity	NPC196073
0.7353	Intermediate Similarity	NPC52533
0.7168	Intermediate Similarity	NPC271562
0.7143	Intermediate Similarity	NPC200412
0.7143	Intermediate Similarity	NPC120599
0.7143	Intermediate Similarity	NPC156336
0.7117	Intermediate Similarity	NPC474244
0.7117	Intermediate Similarity	NPC473289
0.7094	Intermediate Similarity	NPC469597
0.7064	Intermediate Similarity	NPC52820
0.7027	Intermediate Similarity	NPC188785
0.6957	Remote Similarity	NPC474099
0.6923	Remote Similarity	NPC474431
0.6923	Remote Similarity	NPC474411
0.6903	Remote Similarity	NPC68001
0.6903	Remote Similarity	NPC474827
0.6903	Remote Similarity	NPC199831
0.6903	Remote Similarity	NPC474828
0.688	Remote Similarity	NPC474371
0.6842	Remote Similarity	NPC469604
0.6772	Remote Similarity	NPC471086
0.6748	Remote Similarity	NPC11379
0.6733	Remote Similarity	NPC99651
0.6727	Remote Similarity	NPC150041
0.6695	Remote Similarity	NPC469603
0.6667	Remote Similarity	NPC477988
0.6667	Remote Similarity	NPC471261
0.6667	Remote Similarity	NPC477985
0.6667	Remote Similarity	NPC471087
0.6667	Remote Similarity	NPC326386
0.6639	Remote Similarity	NPC65045
0.6638	Remote Similarity	NPC93179
0.6613	Remote Similarity	NPC230849
0.6612	Remote Similarity	NPC472536
0.6612	Remote Similarity	NPC103391
0.6607	Remote Similarity	NPC476344
0.6604	Remote Similarity	NPC469860
0.6604	Remote Similarity	NPC469861
0.6604	Remote Similarity	NPC130436
0.6565	Remote Similarity	NPC133089
0.6557	Remote Similarity	NPC30196
0.6555	Remote Similarity	NPC122926
0.6555	Remote Similarity	NPC113012
0.6552	Remote Similarity	NPC44514
0.6538	Remote Similarity	NPC215507
0.6535	Remote Similarity	NPC233108
0.6515	Remote Similarity	NPC120420
0.6504	Remote Similarity	NPC6531
0.65	Remote Similarity	NPC58281
0.6489	Remote Similarity	NPC120335
0.6484	Remote Similarity	NPC329401
0.6484	Remote Similarity	NPC477987
0.6481	Remote Similarity	NPC287089
0.6481	Remote Similarity	NPC476803
0.6466	Remote Similarity	NPC471260
0.6466	Remote Similarity	NPC99864
0.6466	Remote Similarity	NPC471256
0.6457	Remote Similarity	NPC471255
0.6457	Remote Similarity	NPC316133
0.6457	Remote Similarity	NPC477989
0.6457	Remote Similarity	NPC293550
0.6457	Remote Similarity	NPC323168
0.6457	Remote Similarity	NPC477990
0.6457	Remote Similarity	NPC111162
0.6457	Remote Similarity	NPC318445
0.6455	Remote Similarity	NPC110875
0.6455	Remote Similarity	NPC299808
0.6455	Remote Similarity	NPC118844
0.6455	Remote Similarity	NPC72183
0.6452	Remote Similarity	NPC174463
0.6449	Remote Similarity	NPC469910
0.6449	Remote Similarity	NPC478112
0.6446	Remote Similarity	NPC1111
0.6446	Remote Similarity	NPC261750
0.6435	Remote Similarity	NPC185141
0.6435	Remote Similarity	NPC133907
0.6435	Remote Similarity	NPC46998
0.6435	Remote Similarity	NPC110443
0.6435	Remote Similarity	NPC128733
0.6434	Remote Similarity	NPC314282
0.6429	Remote Similarity	NPC470000
0.6404	Remote Similarity	NPC471144
0.6396	Remote Similarity	NPC469645
0.6396	Remote Similarity	NPC469692
0.6373	Remote Similarity	NPC474278
0.6364	Remote Similarity	NPC474232
0.6364	Remote Similarity	NPC476875
0.6357	Remote Similarity	NPC471263
0.6356	Remote Similarity	NPC471259
0.6348	Remote Similarity	NPC475949
0.6348	Remote Similarity	NPC26597
0.6339	Remote Similarity	NPC121825
0.6325	Remote Similarity	NPC4620
0.6325	Remote Similarity	NPC475871
0.6325	Remote Similarity	NPC475945
0.6316	Remote Similarity	NPC4834
0.6316	Remote Similarity	NPC241426
0.6316	Remote Similarity	NPC167380
0.6311	Remote Similarity	NPC314550
0.6311	Remote Similarity	NPC60432
0.6311	Remote Similarity	NPC43648
0.6306	Remote Similarity	NPC9447
0.6296	Remote Similarity	NPC278283
0.6293	Remote Similarity	NPC472753
0.6288	Remote Similarity	NPC307165
0.6279	Remote Similarity	NPC313333
0.6279	Remote Similarity	NPC313342
0.6279	Remote Similarity	NPC314451
0.6279	Remote Similarity	NPC314512
0.6271	Remote Similarity	NPC75523
0.6271	Remote Similarity	NPC220964
0.6271	Remote Similarity	NPC475676
0.6262	Remote Similarity	NPC158756
0.626	Remote Similarity	NPC329919
0.626	Remote Similarity	NPC477793
0.625	Remote Similarity	NPC471262
0.625	Remote Similarity	NPC475210
0.6241	Remote Similarity	NPC316401
0.6239	Remote Similarity	NPC471148
0.6239	Remote Similarity	NPC471258
0.6239	Remote Similarity	NPC474747
0.6239	Remote Similarity	NPC472754
0.6239	Remote Similarity	NPC266957
0.623	Remote Similarity	NPC29501
0.6228	Remote Similarity	NPC121857
0.6226	Remote Similarity	NPC474252
0.6216	Remote Similarity	NPC316228
0.6204	Remote Similarity	NPC470755
0.6198	Remote Similarity	NPC38154
0.6195	Remote Similarity	NPC469632
0.6186	Remote Similarity	NPC472755
0.6186	Remote Similarity	NPC265094
0.6183	Remote Similarity	NPC476951
0.6182	Remote Similarity	NPC476805
0.6179	Remote Similarity	NPC478024
0.6179	Remote Similarity	NPC474995
0.6179	Remote Similarity	NPC76660
0.6179	Remote Similarity	NPC279383
0.6179	Remote Similarity	NPC276995
0.6176	Remote Similarity	NPC329852
0.6174	Remote Similarity	NPC218064
0.6167	Remote Similarity	NPC326994
0.6167	Remote Similarity	NPC26617
0.6167	Remote Similarity	NPC194620
0.6167	Remote Similarity	NPC72813
0.6167	Remote Similarity	NPC474421
0.6167	Remote Similarity	NPC324327
0.6154	Remote Similarity	NPC474742
0.6154	Remote Similarity	NPC474873
0.6154	Remote Similarity	NPC474339
0.6154	Remote Similarity	NPC164598
0.6147	Remote Similarity	NPC469483
0.6147	Remote Similarity	NPC261721
0.6142	Remote Similarity	NPC477986
0.6142	Remote Similarity	NPC138534
0.6134	Remote Similarity	NPC205176
0.6134	Remote Similarity	NPC474741
0.6134	Remote Similarity	NPC472756
0.6132	Remote Similarity	NPC474894
0.6132	Remote Similarity	NPC52861
0.6129	Remote Similarity	NPC475988
0.6126	Remote Similarity	NPC473564
0.6116	Remote Similarity	NPC70235
0.6116	Remote Similarity	NPC14862
0.6116	Remote Similarity	NPC169888
0.6116	Remote Similarity	NPC327286
0.6116	Remote Similarity	NPC55972
0.6116	Remote Similarity	NPC474664
0.6116	Remote Similarity	NPC233379
0.6111	Remote Similarity	NPC32676
0.6111	Remote Similarity	NPC469997
0.6111	Remote Similarity	NPC212363
0.6111	Remote Similarity	NPC476804
0.6107	Remote Similarity	NPC309525
0.6106	Remote Similarity	NPC475912
0.6106	Remote Similarity	NPC59646
0.6106	Remote Similarity	NPC179746
0.6106	Remote Similarity	NPC475302
0.6106	Remote Similarity	NPC156553
0.6106	Remote Similarity	NPC81419
0.6102	Remote Similarity	NPC149371

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 NPC64168 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	512
0.2-0.3	3243
0.3-0.4	3812
0.4-0.5	1218
0.5-0.6	259
0.6-0.7	20
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
0.9223	High Similarity	NPD2204	Approved
0.656	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD8273	Phase 1
0.6484	Remote Similarity	NPD8451	Approved
0.6466	Remote Similarity	NPD8415	Approved
0.6457	Remote Similarity	NPD7642	Approved
0.6434	Remote Similarity	NPD8448	Approved
0.6418	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD8080	Discontinued
0.6312	Remote Similarity	NPD2575	Approved
0.6288	Remote Similarity	NPD8391	Approved
0.6288	Remote Similarity	NPD8390	Approved
0.6288	Remote Similarity	NPD8392	Approved
0.6279	Remote Similarity	NPD8340	Approved
0.6279	Remote Similarity	NPD8299	Approved
0.6279	Remote Similarity	NPD8342	Approved
0.6279	Remote Similarity	NPD8341	Approved
0.626	Remote Similarity	NPD1376	Discontinued
0.6228	Remote Similarity	NPD4228	Discovery
0.6167	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD3663	Approved
0.6119	Remote Similarity	NPD3664	Approved
0.6119	Remote Similarity	NPD3662	Phase 3
0.6119	Remote Similarity	NPD3661	Approved
0.6074	Remote Similarity	NPD2613	Approved
0.6071	Remote Similarity	NPD8384	Approved
0.6063	Remote Similarity	NPD7641	Discontinued
0.6016	Remote Similarity	NPD6421	Discontinued
0.5983	Remote Similarity	NPD4225	Approved
0.597	Remote Similarity	NPD2625	Approved
0.597	Remote Similarity	NPD2628	Approved
0.597	Remote Similarity	NPD2627	Approved
0.597	Remote Similarity	NPD2159	Approved
0.597	Remote Similarity	NPD2160	Approved
0.597	Remote Similarity	NPD2626	Approved
0.5965	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.595	Remote Similarity	NPD777	Phase 3
0.5942	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.5942	Remote Similarity	NPD3090	Approved
0.5942	Remote Similarity	NPD3615	Approved
0.5942	Remote Similarity	NPD3088	Approved
0.5942	Remote Similarity	NPD4746	Phase 3
0.5942	Remote Similarity	NPD2571	Approved
0.5942	Remote Similarity	NPD3616	Approved
0.5942	Remote Similarity	NPD3089	Approved
0.5942	Remote Similarity	NPD3087	Approved
0.5942	Remote Similarity	NPD2566	Approved
0.5942	Remote Similarity	NPD2570	Approved
0.5942	Remote Similarity	NPD2573	Approved
0.5942	Remote Similarity	NPD4745	Approved
0.5942	Remote Similarity	NPD3614	Approved
0.5942	Remote Similarity	NPD2574	Discontinued
0.5938	Remote Similarity	NPD1773	Discontinued
0.5923	Remote Similarity	NPD8444	Approved
0.5909	Remote Similarity	NPD4215	Approved
0.5909	Remote Similarity	NPD4218	Approved
0.5909	Remote Similarity	NPD4216	Approved
0.5909	Remote Similarity	NPD2611	Approved
0.5909	Remote Similarity	NPD2609	Approved
0.5909	Remote Similarity	NPD2608	Approved
0.5909	Remote Similarity	NPD4217	Approved
0.5909	Remote Similarity	NPD2612	Approved
0.5909	Remote Similarity	NPD3132	Approved
0.5909	Remote Similarity	NPD3131	Approved
0.5909	Remote Similarity	NPD2610	Approved
0.5891	Remote Similarity	NPD2495	Phase 3
0.5891	Remote Similarity	NPD3159	Discontinued
0.5887	Remote Similarity	NPD6420	Discontinued
0.5882	Remote Similarity	NPD5204	Approved
0.587	Remote Similarity	NPD4619	Approved
0.587	Remote Similarity	NPD4621	Approved
0.5867	Remote Similarity	NPD8414	Discontinued
0.5859	Remote Similarity	NPD7505	Discontinued
0.5857	Remote Similarity	NPD4684	Phase 3
0.5857	Remote Similarity	NPD4685	Phase 3
0.5857	Remote Similarity	NPD4686	Approved
0.5846	Remote Similarity	NPD2645	Approved
0.5833	Remote Similarity	NPD7829	Approved
0.5833	Remote Similarity	NPD7830	Approved
0.582	Remote Similarity	NPD4211	Phase 1
0.5812	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD6698	Approved
0.5789	Remote Similarity	NPD46	Approved
0.5786	Remote Similarity	NPD6310	Approved
0.5786	Remote Similarity	NPD6309	Approved
0.5786	Remote Similarity	NPD6311	Approved
0.578	Remote Similarity	NPD883	Phase 2
0.578	Remote Similarity	NPD882	Phase 2
0.5766	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD9512	Approved
0.5741	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD7983	Approved
0.5726	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5725	Remote Similarity	NPD6845	Suspended
0.5714	Remote Similarity	NPD4249	Approved
0.5705	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.57	Remote Similarity	NPD616	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD6921	Approved
0.5676	Remote Similarity	NPD9511	Approved
0.5664	Remote Similarity	NPD4250	Approved
0.5664	Remote Similarity	NPD4251	Approved
0.5652	Remote Similarity	NPD7838	Discovery
0.5639	Remote Similarity	NPD1748	Approved
0.5639	Remote Similarity	NPD1806	Approved
0.5635	Remote Similarity	NPD6371	Approved
0.563	Remote Similarity	NPD3677	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD5202	Clinical (unspecified phase)

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