NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	109.05
Volume:	115.654
LogP:	-0.052
LogD:	0.121
LogS:	0.827
# Rotatable Bonds:	1
TPSA:	33.12
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.572
Synthetic Accessibility Score:	1.752
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.073
MDCK Permeability:	3.6581099266186357e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.063
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.217
Plasma Protein Binding (PPB):	14.177574157714844%
Volume Distribution (VD):	1.511
Pgp-substrate:	84.14163970947266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.397
CYP1A2-substrate:	0.62
CYP2C19-inhibitor:	0.105
CYP2C19-substrate:	0.655
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.185
CYP2D6-inhibitor:	0.03
CYP2D6-substrate:	0.345
CYP3A4-inhibitor:	0.047
CYP3A4-substrate:	0.352

ADMET: Excretion

Clearance (CL):	7.202
Half-life (T1/2):	0.79

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.038
Drug-inuced Liver Injury (DILI):	0.657
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.337
Maximum Recommended Daily Dose:	0.021
Skin Sensitization:	0.917
Carcinogencity:	0.392
Eye Corrosion:	0.061
Eye Irritation:	0.99
Respiratory Toxicity:	0.249

Download Data

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

Natural Product: NPC165370

Natural Product ID:	NPC165370
*Common Name:**	Nicotinyl Alcohol
IUPAC Name:	pyridin-3-ylmethanol
Synonyms:	Nicotinyl Alcohol; Nicotinyl alcohol (pyridylcarbinol); Nicotinyl Alcohol Tartrate; NU-2121; Pyridylcarbinol; Pyridylmethanol; Ro-15155; Roniacol
Standard InCHIKey:	MVQVNTPHUGQQHK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C6H7NO/c8-5-6-2-1-3-7-4-6/h1-4,8H,5H2
SMILES:	OCc1cccnc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1235535
PubChem CID:	7510
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines 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
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1002/hlca.19270100148]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	Petals	n.a.	n.a.	PMID[15043425]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19757853]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21370894]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24338885]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[8482946]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	Silk Stigma Style	n.a.	n.a.	Database[FooDB]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO15308	Stigma croci	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15308	Stigma croci	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9445	Crocus sativus	Species	Iridaceae	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
AC50	1
IC50	2
Others	12
Potency	8

Activity Type	# Activity
Individual Protein	2
Organism	13
Others	7
Protein-Protein Interaction	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[548998]
NPT2	Others	Unspecified		Potency	n.a.	3348.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	225.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	5625.8	nM	PubChem BioAssay data set
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	Potency	n.a.	30106.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	89.2	nM	PubChem BioAssay data set
NPT533	Protein-Protein Interaction	Runt-related transcription factor 1/Core-binding factor subunit beta	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[548998]
NPT2	Others	Unspecified		Potency	n.a.	35481.3	nM	PMID[548998]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	11.0	%	PMID[548999]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	-3.0	%	PMID[548999]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	-19.0	%	PMID[548999]
NPT2	Others	Unspecified		AC50	n.a.	2511.9	nM	PMID[549000]
NPT2	Others	Unspecified		Ac50	n.a.	2.512	uM	PMID[549000]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Hit score	=	0.2034	n.a.	PMID[549001]
NPT20	Organism	Candida albicans	Candida albicans	Inhibition	=	2.84	%	PMID[549002]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	-7.14	%	PMID[549002]
NPT19	Organism	Escherichia coli	Escherichia coli	Inhibition	=	0.45	%	PMID[549002]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	Inhibition	=	6.16	%	PMID[549002]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	13.13	%	PMID[549002]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	Inhibition	=	12.41	%	PMID[549002]
NPT2922	Organism	Staphylococcus aureus subsp. aureus	Staphylococcus aureus subsp. aureus	Inhibition	=	10.46	%	PMID[549002]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[549003]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[549003]

☑ 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 NPC165370 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	651
0.1-0.2	9906
0.2-0.3	12648
0.3-0.4	12705
0.4-0.5	3859
0.5-0.6	2147
0.6-0.7	679
0.7-0.8	86
0.8-0.85	10
0.85-0.9	2
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9512	High Similarity	NPC306397
0.9512	High Similarity	NPC212125
0.8931	High Similarity	NPC29702
0.8594	High Similarity	NPC151489
0.8478	Intermediate Similarity	NPC471323
0.8417	Intermediate Similarity	NPC167400
0.8276	Intermediate Similarity	NPC138018
0.8209	Intermediate Similarity	NPC256893
0.8182	Intermediate Similarity	NPC76540
0.8175	Intermediate Similarity	NPC114310
0.8138	Intermediate Similarity	NPC263455
0.8134	Intermediate Similarity	NPC315320
0.8045	Intermediate Similarity	NPC471313
0.8045	Intermediate Similarity	NPC471311
0.8015	Intermediate Similarity	NPC322488
0.7984	Intermediate Similarity	NPC27802
0.7958	Intermediate Similarity	NPC230085
0.7958	Intermediate Similarity	NPC159630
0.7941	Intermediate Similarity	NPC174421
0.7917	Intermediate Similarity	NPC112741
0.7895	Intermediate Similarity	NPC319456
0.7852	Intermediate Similarity	NPC113812
0.7842	Intermediate Similarity	NPC328029
0.7833	Intermediate Similarity	NPC83987
0.7823	Intermediate Similarity	NPC107287
0.7823	Intermediate Similarity	NPC312860
0.781	Intermediate Similarity	NPC324611
0.7746	Intermediate Similarity	NPC318935
0.7724	Intermediate Similarity	NPC220523
0.7717	Intermediate Similarity	NPC235843
0.7697	Intermediate Similarity	NPC97367
0.7651	Intermediate Similarity	NPC63562
0.7647	Intermediate Similarity	NPC471178
0.7597	Intermediate Similarity	NPC98187
0.7591	Intermediate Similarity	NPC471589
0.7582	Intermediate Similarity	NPC473057
0.7582	Intermediate Similarity	NPC102423
0.7557	Intermediate Similarity	NPC471402
0.7557	Intermediate Similarity	NPC297486
0.7557	Intermediate Similarity	NPC240136
0.755	Intermediate Similarity	NPC132680
0.755	Intermediate Similarity	NPC269919
0.7535	Intermediate Similarity	NPC471312
0.7516	Intermediate Similarity	NPC471177
0.7516	Intermediate Similarity	NPC59779
0.7516	Intermediate Similarity	NPC124542
0.75	Intermediate Similarity	NPC91958
0.75	Intermediate Similarity	NPC317010
0.75	Intermediate Similarity	NPC143603
0.7484	Intermediate Similarity	NPC108469
0.7483	Intermediate Similarity	NPC161292
0.7481	Intermediate Similarity	NPC290094
0.746	Intermediate Similarity	NPC231655
0.7452	Intermediate Similarity	NPC273532
0.7451	Intermediate Similarity	NPC322976
0.7451	Intermediate Similarity	NPC324203
0.7451	Intermediate Similarity	NPC63338
0.7365	Intermediate Similarity	NPC302159
0.7362	Intermediate Similarity	NPC207851
0.7355	Intermediate Similarity	NPC263439
0.7338	Intermediate Similarity	NPC131718
0.7338	Intermediate Similarity	NPC89490
0.7333	Intermediate Similarity	NPC265605
0.7333	Intermediate Similarity	NPC48564
0.7333	Intermediate Similarity	NPC182570
0.7319	Intermediate Similarity	NPC169625
0.7319	Intermediate Similarity	NPC202957
0.7312	Intermediate Similarity	NPC203754
0.7312	Intermediate Similarity	NPC150048
0.7305	Intermediate Similarity	NPC471322
0.7296	Intermediate Similarity	NPC313791
0.729	Intermediate Similarity	NPC71079
0.7286	Intermediate Similarity	NPC475105
0.7286	Intermediate Similarity	NPC329896
0.7286	Intermediate Similarity	NPC475090
0.7285	Intermediate Similarity	NPC153769
0.7273	Intermediate Similarity	NPC230869
0.7261	Intermediate Similarity	NPC41717
0.7244	Intermediate Similarity	NPC211187
0.7244	Intermediate Similarity	NPC474217
0.7226	Intermediate Similarity	NPC46358
0.7197	Intermediate Similarity	NPC85918
0.7195	Intermediate Similarity	NPC48938
0.7174	Intermediate Similarity	NPC27740
0.7174	Intermediate Similarity	NPC476322
0.717	Intermediate Similarity	NPC314940
0.717	Intermediate Similarity	NPC473764
0.7161	Intermediate Similarity	NPC84508
0.7152	Intermediate Similarity	NPC127730
0.7152	Intermediate Similarity	NPC278366
0.7122	Intermediate Similarity	NPC166424
0.7122	Intermediate Similarity	NPC146373
0.7122	Intermediate Similarity	NPC245244
0.7121	Intermediate Similarity	NPC473901
0.7099	Intermediate Similarity	NPC476419
0.7097	Intermediate Similarity	NPC212742
0.7095	Intermediate Similarity	NPC60553
0.7063	Intermediate Similarity	NPC256828
0.7055	Intermediate Similarity	NPC96890
0.7019	Intermediate Similarity	NPC249614
0.7019	Intermediate Similarity	NPC158129
0.7015	Intermediate Similarity	NPC84268
0.7014	Intermediate Similarity	NPC330326
0.7006	Intermediate Similarity	NPC25899
0.6987	Remote Similarity	NPC129721
0.6972	Remote Similarity	NPC313823
0.6962	Remote Similarity	NPC48192
0.6954	Remote Similarity	NPC159856
0.6951	Remote Similarity	NPC184964
0.6939	Remote Similarity	NPC65408
0.6934	Remote Similarity	NPC11863
0.6923	Remote Similarity	NPC469785
0.6923	Remote Similarity	NPC476131
0.6918	Remote Similarity	NPC162268
0.6909	Remote Similarity	NPC164340
0.6906	Remote Similarity	NPC329825
0.6905	Remote Similarity	NPC295158
0.6887	Remote Similarity	NPC471598
0.6882	Remote Similarity	NPC472289
0.6879	Remote Similarity	NPC469762
0.6875	Remote Similarity	NPC282398
0.6875	Remote Similarity	NPC69914
0.6867	Remote Similarity	NPC52831
0.6867	Remote Similarity	NPC325705
0.6832	Remote Similarity	NPC54988
0.6828	Remote Similarity	NPC101165
0.6821	Remote Similarity	NPC289786
0.6818	Remote Similarity	NPC288445
0.681	Remote Similarity	NPC252590
0.6786	Remote Similarity	NPC220765
0.6786	Remote Similarity	NPC56856
0.6783	Remote Similarity	NPC278451
0.6774	Remote Similarity	NPC24678
0.6774	Remote Similarity	NPC105818
0.6752	Remote Similarity	NPC33229
0.6752	Remote Similarity	NPC209362
0.6746	Remote Similarity	NPC204717
0.6746	Remote Similarity	NPC284559
0.6733	Remote Similarity	NPC280853
0.6732	Remote Similarity	NPC314372
0.6726	Remote Similarity	NPC219963
0.6725	Remote Similarity	NPC46580
0.6711	Remote Similarity	NPC470404
0.6711	Remote Similarity	NPC470394
0.6711	Remote Similarity	NPC190296
0.6711	Remote Similarity	NPC470403
0.6708	Remote Similarity	NPC40779
0.6708	Remote Similarity	NPC311276
0.6706	Remote Similarity	NPC314002
0.6706	Remote Similarity	NPC62510
0.6705	Remote Similarity	NPC114974
0.6689	Remote Similarity	NPC245657
0.6689	Remote Similarity	NPC285016
0.6688	Remote Similarity	NPC25008
0.6688	Remote Similarity	NPC469760
0.6688	Remote Similarity	NPC259644
0.6688	Remote Similarity	NPC469763
0.6688	Remote Similarity	NPC73952
0.6688	Remote Similarity	NPC469765
0.6688	Remote Similarity	NPC469786
0.6687	Remote Similarity	NPC279918
0.6687	Remote Similarity	NPC134586
0.6686	Remote Similarity	NPC44354
0.6686	Remote Similarity	NPC327373
0.6667	Remote Similarity	NPC477975
0.6667	Remote Similarity	NPC213914
0.6667	Remote Similarity	NPC471596
0.6667	Remote Similarity	NPC24864
0.6667	Remote Similarity	NPC171171
0.6647	Remote Similarity	NPC284678
0.6647	Remote Similarity	NPC211997
0.6647	Remote Similarity	NPC95783
0.6646	Remote Similarity	NPC212376
0.6646	Remote Similarity	NPC164664
0.6646	Remote Similarity	NPC211572
0.6646	Remote Similarity	NPC75540
0.6646	Remote Similarity	NPC70922
0.6646	Remote Similarity	NPC282231
0.6646	Remote Similarity	NPC177404
0.6646	Remote Similarity	NPC80597
0.6629	Remote Similarity	NPC329541
0.6627	Remote Similarity	NPC71037
0.6623	Remote Similarity	NPC470395
0.661	Remote Similarity	NPC329024
0.6606	Remote Similarity	NPC470498
0.6606	Remote Similarity	NPC253810
0.6605	Remote Similarity	NPC469813
0.6605	Remote Similarity	NPC78375
0.6605	Remote Similarity	NPC476446
0.6604	Remote Similarity	NPC141353
0.66	Remote Similarity	NPC314102
0.66	Remote Similarity	NPC251722
0.6599	Remote Similarity	NPC82295
0.6597	Remote Similarity	NPC135488
0.6591	Remote Similarity	NPC146724
0.6588	Remote Similarity	NPC322043
0.6588	Remote Similarity	NPC325093
0.6585	Remote Similarity	NPC201700
0.6573	Remote Similarity	NPC59033
0.6573	Remote Similarity	NPC317672

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 NPC165370 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	271
0.1-0.2	1019
0.2-0.3	656
0.3-0.4	1982
0.4-0.5	3256
0.5-0.6	1518
0.6-0.7	384
0.7-0.8	52
0.8-0.85	6
0.85-0.9	3
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9512	High Similarity	NPD9284	Approved
0.9512	High Similarity	NPD9080	Approved
0.9154	High Similarity	NPD9506	Approved
0.8797	High Similarity	NPD203	Clinical (unspecified phase)
0.8667	High Similarity	NPD1649	Discontinued
0.8478	Intermediate Similarity	NPD3813	Approved
0.8478	Intermediate Similarity	NPD1352	Discontinued
0.8417	Intermediate Similarity	NPD9075	Approved
0.8417	Intermediate Similarity	NPD9074	Approved
0.8134	Intermediate Similarity	NPD9207	Approved
0.8134	Intermediate Similarity	NPD9206	Approved
0.8129	Intermediate Similarity	NPD107	Approved
0.8116	Intermediate Similarity	NPD9076	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD9271	Approved
0.7674	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD820	Phase 3
0.7606	Intermediate Similarity	NPD1380	Discovery
0.755	Intermediate Similarity	NPD9383	Approved
0.755	Intermediate Similarity	NPD9382	Approved
0.75	Intermediate Similarity	NPD704	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5255	Approved
0.7484	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2896	Discontinued
0.746	Intermediate Similarity	NPD9099	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD9098	Phase 3
0.7451	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD1383	Phase 3
0.7448	Intermediate Similarity	NPD1382	Phase 2
0.7432	Intermediate Similarity	NPD4703	Approved
0.7432	Intermediate Similarity	NPD4702	Approved
0.7429	Intermediate Similarity	NPD9726	Discontinued
0.7419	Intermediate Similarity	NPD925	Approved
0.7419	Intermediate Similarity	NPD926	Approved
0.7405	Intermediate Similarity	NPD1599	Approved
0.74	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD3717	Discontinued
0.7397	Intermediate Similarity	NPD1427	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD425	Approved
0.7372	Intermediate Similarity	NPD424	Approved
0.7347	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD8823	Approved
0.7346	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2511	Approved
0.7338	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD268	Approved
0.7333	Intermediate Similarity	NPD271	Approved
0.7333	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD2581	Approved
0.732	Intermediate Similarity	NPD2582	Approved
0.7312	Intermediate Similarity	NPD5100	Phase 3
0.7255	Intermediate Similarity	NPD6026	Approved
0.7248	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD5352	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4824	Approved
0.7176	Intermediate Similarity	NPD4823	Approved
0.7174	Intermediate Similarity	NPD9357	Approved
0.7171	Intermediate Similarity	NPD3262	Approved
0.7152	Intermediate Similarity	NPD1096	Discontinued
0.7143	Intermediate Similarity	NPD60	Approved
0.7143	Intermediate Similarity	NPD1395	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5088	Discontinued
0.7133	Intermediate Similarity	NPD7469	Discontinued
0.7133	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD852	Discontinued
0.7115	Intermediate Similarity	NPD687	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD3082	Discontinued
0.7083	Intermediate Similarity	NPD4021	Phase 2
0.7078	Intermediate Similarity	NPD2809	Approved
0.7071	Intermediate Similarity	NPD9583	Approved
0.7059	Intermediate Similarity	NPD2882	Phase 1
0.7059	Intermediate Similarity	NPD510	Phase 1
0.7047	Intermediate Similarity	NPD3525	Discontinued
0.7041	Intermediate Similarity	NPD8063	Discontinued
0.7041	Intermediate Similarity	NPD2544	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD9690	Approved
0.7037	Intermediate Similarity	NPD8840	Approved
0.7037	Intermediate Similarity	NPD5065	Approved
0.7034	Intermediate Similarity	NPD272	Approved
0.7021	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD2119	Approved
0.7021	Intermediate Similarity	NPD1598	Discontinued
0.7021	Intermediate Similarity	NPD2118	Approved
0.7021	Intermediate Similarity	NPD991	Phase 2
0.7014	Intermediate Similarity	NPD9100	Approved
0.7012	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD112	Approved
0.7006	Intermediate Similarity	NPD9705	Discontinued
0.7006	Intermediate Similarity	NPD2814	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4699	Discontinued
0.7	Intermediate Similarity	NPD5862	Discovery
0.6987	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD206	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1661	Suspended
0.6948	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD604	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD201	Phase 2
0.6939	Remote Similarity	NPD200	Phase 2
0.6928	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD9392	Approved
0.6912	Remote Similarity	NPD9396	Approved
0.6894	Remote Similarity	NPD2781	Approved
0.6875	Remote Similarity	NPD2780	Approved
0.6875	Remote Similarity	NPD3475	Approved
0.6875	Remote Similarity	NPD715	Phase 3
0.6875	Remote Similarity	NPD2782	Approved
0.6875	Remote Similarity	NPD3476	Approved
0.6871	Remote Similarity	NPD2076	Approved
0.6871	Remote Similarity	NPD2077	Approved
0.6867	Remote Similarity	NPD4805	Approved
0.6867	Remote Similarity	NPD9510	Approved
0.6864	Remote Similarity	NPD706	Phase 1
0.6863	Remote Similarity	NPD2089	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD5358	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD8026	Phase 1
0.6848	Remote Similarity	NPD4072	Approved
0.6848	Remote Similarity	NPD4071	Approved
0.6842	Remote Similarity	NPD3321	Discontinued
0.6839	Remote Similarity	NPD6158	Phase 2
0.6839	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD1570	Approved
0.6815	Remote Similarity	NPD1274	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5925	Phase 1
0.681	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.681	Remote Similarity	NPD485	Clinical (unspecified phase)
0.681	Remote Similarity	NPD2123	Phase 3
0.681	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1622	Discontinued
0.68	Remote Similarity	NPD2952	Discontinued
0.6795	Remote Similarity	NPD2012	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD1418	Phase 2
0.6786	Remote Similarity	NPD748	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD1994	Approved
0.6781	Remote Similarity	NPD1995	Approved
0.6781	Remote Similarity	NPD1993	Approved
0.6772	Remote Similarity	NPD5541	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD2601	Approved
0.6766	Remote Similarity	NPD2600	Approved
0.6766	Remote Similarity	NPD2599	Approved
0.6765	Remote Similarity	NPD4375	Approved
0.6763	Remote Similarity	NPD4376	Phase 3
0.6763	Remote Similarity	NPD3406	Suspended
0.6763	Remote Similarity	NPD3404	Approved
0.6763	Remote Similarity	NPD6665	Discontinued
0.6763	Remote Similarity	NPD981	Phase 2
0.6757	Remote Similarity	NPD792	Discontinued
0.6752	Remote Similarity	NPD2061	Approved
0.6747	Remote Similarity	NPD1032	Phase 2
0.6735	Remote Similarity	NPD3942	Approved
0.6735	Remote Similarity	NPD4029	Approved
0.6735	Remote Similarity	NPD4028	Approved
0.6735	Remote Similarity	NPD4030	Approved
0.6735	Remote Similarity	NPD3944	Approved
0.6733	Remote Similarity	NPD4804	Approved
0.673	Remote Similarity	NPD3433	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD1923	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD8020	Approved
0.6725	Remote Similarity	NPD8021	Approved
0.6724	Remote Similarity	NPD4551	Phase 2
0.6724	Remote Similarity	NPD1173	Approved
0.6714	Remote Similarity	NPD9598	Discontinued
0.671	Remote Similarity	NPD1183	Approved
0.671	Remote Similarity	NPD3576	Approved
0.671	Remote Similarity	NPD3575	Approved
0.6689	Remote Similarity	NPD9599	Approved
0.6689	Remote Similarity	NPD2141	Approved
0.6689	Remote Similarity	NPD2142	Approved
0.6689	Remote Similarity	NPD2140	Approved
0.6687	Remote Similarity	NPD4639	Approved
0.6687	Remote Similarity	NPD4638	Approved
0.6687	Remote Similarity	NPD4640	Approved
0.6686	Remote Similarity	NPD4999	Phase 3
0.6686	Remote Similarity	NPD2391	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD4998	Phase 3
0.6667	Remote Similarity	NPD6569	Phase 2
0.6667	Remote Similarity	NPD9574	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3039	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2323	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD3439	Approved
0.6646	Remote Similarity	NPD4239	Clinical (unspecified phase)
0.663	Remote Similarity	NPD1915	Phase 1
0.6629	Remote Similarity	NPD4528	Approved
0.6629	Remote Similarity	NPD4529	Approved
0.6629	Remote Similarity	NPD4526	Approved
0.6627	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD9596	Approved
0.6624	Remote Similarity	NPD9595	Approved
0.6623	Remote Similarity	NPD175	Clinical (unspecified phase)
0.661	Remote Similarity	NPD7021	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD6022	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD1235	Phase 3
0.6608	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD2993	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD6635	Approved
0.6599	Remote Similarity	NPD803	Phase 1

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