NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	122.04
Volume:	128.107
LogP:	1.153
LogD:	1.013
LogS:	-1.082
# Rotatable Bonds:	1
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.568
Synthetic Accessibility Score:	1.872
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.436
MDCK Permeability:	1.4238377843867056e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.54
30% Bioavailability (F30%):	0.456

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.332
Plasma Protein Binding (PPB):	59.1812744140625%
Volume Distribution (VD):	0.852
Pgp-substrate:	38.87885665893555%

ADMET: Metabolism

CYP1A2-inhibitor:	0.823
CYP1A2-substrate:	0.114
CYP2C19-inhibitor:	0.108
CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.849
CYP2D6-inhibitor:	0.029
CYP2D6-substrate:	0.457
CYP3A4-inhibitor:	0.048
CYP3A4-substrate:	0.181

ADMET: Excretion

Clearance (CL):	10.094
Half-life (T1/2):	0.881

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.039
Drug-inuced Liver Injury (DILI):	0.03
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.054
Skin Sensitization:	0.412
Carcinogencity:	0.035
Eye Corrosion:	0.988
Eye Irritation:	0.992
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC163734

Natural Product ID:	NPC163734
*Common Name:**	3-Hydroxybenzaldehyde
IUPAC Name:	3-hydroxybenzaldehyde
Synonyms:	3-Hydroxybenzaldehyd; 3-Hydroxybenzaldehyde
Standard InCHIKey:	IAVREABSGIHHMO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C7H6O2/c8-5-6-2-1-3-7(9)4-6/h1-5,9H
SMILES:	O=Cc1cccc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL243816
PubChem CID:	101
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000124] Aldehydes [CHEMONTID:0003213] Aryl-aldehydes [CHEMONTID:0001345] Benzaldehydes [CHEMONTID:0003978] Hydroxybenzaldehydes

*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
NPO25813	Salvia przewalskii	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17217287]
NPO19581	Marchantia polymorpha	Species	Marchantiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21625478]
NPO40074	Cleistochlamys kirkii	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[28001067]
NPO25507	Spongia agaricina	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9548857]
NPO19581	Marchantia polymorpha	Species	Marchantiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25813	Salvia przewalskii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25813	Salvia przewalskii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19581	Marchantia polymorpha	Species	Marchantiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25446	Acia oblonga	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO25567	Dichilus reflexus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19581	Marchantia polymorpha	Species	Marchantiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25332	Polyalthia acuminata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25813	Salvia przewalskii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25507	Spongia agaricina	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28244	Trichocereus peruvianus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25676	Stereospermum acuminatissimum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21053	Oenanthe pimpinelloides	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24945	Hoya carnosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
EC50	1
IC50	3
LD50	3
Others	12

Activity Type	# Activity
Cell Line	2
CELL-LINE	1
Organism	3
Others	13

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	8200.0	nM	PMID[549771]
NPT76	Cell Line	C6	Rattus norvegicus	Activity	=	30.0	%	PMID[549772]
NPT2	Others	Unspecified		IC50	=	9620000.0	nM	PMID[549766]
NPT2	Others	Unspecified		IC50	=	104712854805.09	nM	PMID[549766]
NPT450	Organism	Meloidogyne incognita	Meloidogyne incognita	EC100	>	250.0	mg/L	PMID[549768]
NPT450	Organism	Meloidogyne incognita	Meloidogyne incognita	EC50	=	31.0	ug.mL-1	PMID[549768]
NPT2	Others	Unspecified		LD50	=	6.0	ug	PMID[549769]
NPT2	Others	Unspecified		FC	=	2.6	n.a.	PMID[549769]
NPT2	Others	Unspecified		LD50	=	3.0	ug	PMID[549769]
NPT2	Others	Unspecified		FC	=	1.0	n.a.	PMID[549769]
NPT2	Others	Unspecified		MHC	=	30.0	ug	PMID[549769]
NPT2	Others	Unspecified		FC	=	6.0	n.a.	PMID[549769]
NPT35	Others	n.a.		LogP	=	1.15	n.a.	PMID[549769]
NPT2	Others	Unspecified		LD50	=	50.0	ug	PMID[549769]
NPT2	Others	Unspecified		FC	=	1.25	n.a.	PMID[549769]
NPT2	Others	Unspecified		MHC	=	15.0	ug	PMID[549769]
NPT2	Others	Unspecified		FC	=	3.0	n.a.	PMID[549769]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	GI	=	25.0	%	PMID[549771]
NPT27802	CELL-LINE	U138-MG	Homo sapiens	Activity	=	30.0	%	PMID[549772]

☑ 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 NPC163734 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	330
0.1-0.2	2279
0.2-0.3	5470
0.3-0.4	12654
0.4-0.5	5628
0.5-0.6	9584
0.6-0.7	5758
0.7-0.8	921
0.8-0.85	63
0.85-0.9	3
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9208	High Similarity	NPC219913
0.9151	High Similarity	NPC163154
0.9118	High Similarity	NPC187913
0.9065	High Similarity	NPC278102
0.9029	High Similarity	NPC34715
0.9029	High Similarity	NPC303264
0.8899	High Similarity	NPC28169
0.8624	High Similarity	NPC81808
0.8519	High Similarity	NPC54626
0.844	Intermediate Similarity	NPC231717
0.8416	Intermediate Similarity	NPC286006
0.8396	Intermediate Similarity	NPC6984
0.8378	Intermediate Similarity	NPC161304
0.8378	Intermediate Similarity	NPC240163
0.8364	Intermediate Similarity	NPC98543
0.8349	Intermediate Similarity	NPC114682
0.8349	Intermediate Similarity	NPC212718
0.8333	Intermediate Similarity	NPC283711
0.8319	Intermediate Similarity	NPC41567
0.8318	Intermediate Similarity	NPC29883
0.8318	Intermediate Similarity	NPC141523
0.8318	Intermediate Similarity	NPC226699
0.8304	Intermediate Similarity	NPC108288
0.8304	Intermediate Similarity	NPC312800
0.8291	Intermediate Similarity	NPC4012
0.8241	Intermediate Similarity	NPC17525
0.8241	Intermediate Similarity	NPC100551
0.8241	Intermediate Similarity	NPC224584
0.8235	Intermediate Similarity	NPC257182
0.823	Intermediate Similarity	NPC150919
0.823	Intermediate Similarity	NPC269414
0.823	Intermediate Similarity	NPC160199
0.823	Intermediate Similarity	NPC240664
0.8224	Intermediate Similarity	NPC19149
0.8224	Intermediate Similarity	NPC184658
0.8198	Intermediate Similarity	NPC11824
0.8174	Intermediate Similarity	NPC7151
0.8174	Intermediate Similarity	NPC216297
0.8174	Intermediate Similarity	NPC294964
0.8174	Intermediate Similarity	NPC473662
0.8165	Intermediate Similarity	NPC98392
0.8165	Intermediate Similarity	NPC95172
0.8158	Intermediate Similarity	NPC283844
0.8158	Intermediate Similarity	NPC184527
0.8142	Intermediate Similarity	NPC316062
0.812	Intermediate Similarity	NPC217756
0.8103	Intermediate Similarity	NPC216216
0.8091	Intermediate Similarity	NPC471535
0.8091	Intermediate Similarity	NPC116842
0.8087	Intermediate Similarity	NPC156654
0.8083	Intermediate Similarity	NPC203719
0.8083	Intermediate Similarity	NPC117237
0.8083	Intermediate Similarity	NPC473787
0.8056	Intermediate Similarity	NPC317592
0.8034	Intermediate Similarity	NPC295034
0.802	Intermediate Similarity	NPC312304
0.8019	Intermediate Similarity	NPC94343
0.8018	Intermediate Similarity	NPC268388
0.8017	Intermediate Similarity	NPC260837
0.8017	Intermediate Similarity	NPC206778
0.8017	Intermediate Similarity	NPC285829
0.8	Intermediate Similarity	NPC227741
0.8	Intermediate Similarity	NPC280869
0.8	Intermediate Similarity	NPC136342
0.8	Intermediate Similarity	NPC295202
0.8	Intermediate Similarity	NPC49647
0.7983	Intermediate Similarity	NPC117794
0.7982	Intermediate Similarity	NPC477453
0.7951	Intermediate Similarity	NPC261759
0.7949	Intermediate Similarity	NPC165197
0.7944	Intermediate Similarity	NPC13426
0.7931	Intermediate Similarity	NPC232178
0.7931	Intermediate Similarity	NPC473767
0.7925	Intermediate Similarity	NPC52472
0.7921	Intermediate Similarity	NPC62765
0.7917	Intermediate Similarity	NPC131799
0.7917	Intermediate Similarity	NPC472592
0.7913	Intermediate Similarity	NPC125252
0.7913	Intermediate Similarity	NPC174087
0.7913	Intermediate Similarity	NPC230349
0.7905	Intermediate Similarity	NPC260000
0.7895	Intermediate Similarity	NPC322197
0.789	Intermediate Similarity	NPC29989
0.789	Intermediate Similarity	NPC95178
0.789	Intermediate Similarity	NPC69332
0.7886	Intermediate Similarity	NPC298268
0.7881	Intermediate Similarity	NPC120545
0.7881	Intermediate Similarity	NPC25168
0.7879	Intermediate Similarity	NPC150837
0.7876	Intermediate Similarity	NPC242136
0.7869	Intermediate Similarity	NPC214553
0.7864	Intermediate Similarity	NPC181709
0.7857	Intermediate Similarity	NPC57879
0.7845	Intermediate Similarity	NPC94298
0.7845	Intermediate Similarity	NPC27633
0.7845	Intermediate Similarity	NPC249435
0.7845	Intermediate Similarity	NPC94637
0.7833	Intermediate Similarity	NPC74507
0.7833	Intermediate Similarity	NPC234890
0.783	Intermediate Similarity	NPC245561
0.7826	Intermediate Similarity	NPC128825
0.7826	Intermediate Similarity	NPC131192
0.7818	Intermediate Similarity	NPC211439
0.7815	Intermediate Similarity	NPC300274
0.7815	Intermediate Similarity	NPC46634
0.7815	Intermediate Similarity	NPC307174
0.7815	Intermediate Similarity	NPC297193
0.7815	Intermediate Similarity	NPC91478
0.7807	Intermediate Similarity	NPC197513
0.7797	Intermediate Similarity	NPC248363
0.7797	Intermediate Similarity	NPC295317
0.7797	Intermediate Similarity	NPC190971
0.7788	Intermediate Similarity	NPC81010
0.7788	Intermediate Similarity	NPC32977
0.7778	Intermediate Similarity	NPC100395
0.7778	Intermediate Similarity	NPC90522
0.7778	Intermediate Similarity	NPC328459
0.7778	Intermediate Similarity	NPC233165
0.7778	Intermediate Similarity	NPC184579
0.7769	Intermediate Similarity	NPC287473
0.775	Intermediate Similarity	NPC477153
0.775	Intermediate Similarity	NPC375356
0.7739	Intermediate Similarity	NPC160179
0.7727	Intermediate Similarity	NPC70843
0.7724	Intermediate Similarity	NPC3009
0.7719	Intermediate Similarity	NPC53953
0.7719	Intermediate Similarity	NPC223004
0.7719	Intermediate Similarity	NPC211421
0.7714	Intermediate Similarity	NPC246679
0.7714	Intermediate Similarity	NPC61944
0.7712	Intermediate Similarity	NPC233282
0.7712	Intermediate Similarity	NPC72977
0.7706	Intermediate Similarity	NPC79672
0.7706	Intermediate Similarity	NPC93831
0.7705	Intermediate Similarity	NPC51037
0.7699	Intermediate Similarity	NPC228609
0.7686	Intermediate Similarity	NPC152525
0.7686	Intermediate Similarity	NPC310540
0.7686	Intermediate Similarity	NPC68756
0.7685	Intermediate Similarity	NPC472585
0.7679	Intermediate Similarity	NPC88141
0.7672	Intermediate Similarity	NPC61062
0.7672	Intermediate Similarity	NPC277394
0.7672	Intermediate Similarity	NPC299252
0.7667	Intermediate Similarity	NPC139171
0.7667	Intermediate Similarity	NPC225710
0.7661	Intermediate Similarity	NPC226855
0.7661	Intermediate Similarity	NPC474546
0.7652	Intermediate Similarity	NPC118288
0.7652	Intermediate Similarity	NPC285350
0.7652	Intermediate Similarity	NPC276111
0.7652	Intermediate Similarity	NPC252004
0.7647	Intermediate Similarity	NPC272454
0.7647	Intermediate Similarity	NPC35856
0.7647	Intermediate Similarity	NPC159760
0.7647	Intermediate Similarity	NPC27974
0.7647	Intermediate Similarity	NPC26433
0.7647	Intermediate Similarity	NPC178395
0.7647	Intermediate Similarity	NPC301987
0.7647	Intermediate Similarity	NPC292665
0.7647	Intermediate Similarity	NPC244994
0.7647	Intermediate Similarity	NPC222876
0.7647	Intermediate Similarity	NPC115188
0.7647	Intermediate Similarity	NPC104216
0.7647	Intermediate Similarity	NPC179092
0.7642	Intermediate Similarity	NPC71525
0.7642	Intermediate Similarity	NPC158654
0.7642	Intermediate Similarity	NPC32163
0.7642	Intermediate Similarity	NPC16651
0.7642	Intermediate Similarity	NPC253423
0.7638	Intermediate Similarity	NPC274876
0.7638	Intermediate Similarity	NPC144662
0.7636	Intermediate Similarity	NPC13495
0.7623	Intermediate Similarity	NPC103540
0.7623	Intermediate Similarity	NPC240744
0.7623	Intermediate Similarity	NPC167055
0.7615	Intermediate Similarity	NPC304638
0.7615	Intermediate Similarity	NPC68269
0.7611	Intermediate Similarity	NPC21162
0.7611	Intermediate Similarity	NPC222084
0.7607	Intermediate Similarity	NPC76308
0.7607	Intermediate Similarity	NPC325295
0.7603	Intermediate Similarity	NPC275145
0.7603	Intermediate Similarity	NPC135062
0.76	Intermediate Similarity	NPC199253
0.76	Intermediate Similarity	NPC136588
0.7593	Intermediate Similarity	NPC253746
0.7589	Intermediate Similarity	NPC31274
0.7589	Intermediate Similarity	NPC317305
0.7586	Intermediate Similarity	NPC23402
0.7583	Intermediate Similarity	NPC198336
0.7581	Intermediate Similarity	NPC247250
0.7581	Intermediate Similarity	NPC767
0.7581	Intermediate Similarity	NPC237225
0.7581	Intermediate Similarity	NPC165257
0.757	Intermediate Similarity	NPC474073
0.757	Intermediate Similarity	NPC201967
0.757	Intermediate Similarity	NPC88420
0.7568	Intermediate Similarity	NPC294902
0.7568	Intermediate Similarity	NPC1075

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 NPC163734 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	341
0.1-0.2	1031
0.2-0.3	1478
0.3-0.4	2977
0.4-0.5	1944
0.5-0.6	1063
0.6-0.7	276
0.7-0.8	33
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8318	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8241	Intermediate Similarity	NPD74	Approved
0.8241	Intermediate Similarity	NPD9266	Approved
0.8148	Intermediate Similarity	NPD9264	Approved
0.8148	Intermediate Similarity	NPD9263	Approved
0.8148	Intermediate Similarity	NPD9267	Approved
0.8083	Intermediate Similarity	NPD9494	Approved
0.7921	Intermediate Similarity	NPD9258	Approved
0.7921	Intermediate Similarity	NPD9256	Approved
0.7845	Intermediate Similarity	NPD9545	Approved
0.7826	Intermediate Similarity	NPD9493	Approved
0.7778	Intermediate Similarity	NPD9261	Approved
0.7667	Intermediate Similarity	NPD9269	Phase 2
0.7652	Intermediate Similarity	NPD9281	Approved
0.7627	Intermediate Similarity	NPD9268	Approved
0.7623	Intermediate Similarity	NPD1470	Approved
0.7583	Intermediate Similarity	NPD1201	Approved
0.7545	Intermediate Similarity	NPD1237	Approved
0.7525	Intermediate Similarity	NPD9257	Approved
0.7525	Intermediate Similarity	NPD9259	Approved
0.7426	Intermediate Similarity	NPD111	Approved
0.7287	Intermediate Similarity	NPD230	Phase 1
0.7222	Intermediate Similarity	NPD844	Approved
0.7209	Intermediate Similarity	NPD943	Approved
0.72	Intermediate Similarity	NPD1164	Approved
0.719	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD288	Approved
0.7119	Intermediate Similarity	NPD1241	Discontinued
0.7117	Intermediate Similarity	NPD1242	Phase 1
0.7117	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD9717	Approved
0.7091	Intermediate Similarity	NPD9495	Approved
0.7068	Intermediate Similarity	NPD1551	Phase 2
0.7063	Intermediate Similarity	NPD1203	Approved
0.7054	Intermediate Similarity	NPD3764	Approved
0.7054	Intermediate Similarity	NPD411	Approved
0.7037	Intermediate Similarity	NPD1202	Approved
0.7027	Intermediate Similarity	NPD1238	Approved
0.7023	Intermediate Similarity	NPD447	Suspended
0.701	Intermediate Similarity	NPD9087	Approved
0.7	Intermediate Similarity	NPD520	Approved
0.6992	Remote Similarity	NPD3019	Approved
0.6992	Remote Similarity	NPD2932	Approved
0.6992	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD9260	Approved
0.6972	Remote Similarity	NPD2934	Approved
0.6972	Remote Similarity	NPD2933	Approved
0.694	Remote Similarity	NPD2935	Discontinued
0.6909	Remote Similarity	NPD2859	Approved
0.6909	Remote Similarity	NPD2860	Approved
0.6905	Remote Similarity	NPD1755	Approved
0.6905	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.69	Remote Similarity	NPD9088	Approved
0.688	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3020	Approved
0.6866	Remote Similarity	NPD1510	Phase 2
0.6866	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.686	Remote Similarity	NPD255	Approved
0.686	Remote Similarity	NPD256	Approved
0.6838	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1240	Approved
0.6807	Remote Similarity	NPD9508	Approved
0.6803	Remote Similarity	NPD9568	Approved
0.68	Remote Similarity	NPD9294	Approved
0.6786	Remote Similarity	NPD9273	Approved
0.6783	Remote Similarity	NPD164	Approved
0.6765	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD2798	Approved
0.6739	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD9491	Approved
0.6727	Remote Similarity	NPD845	Approved
0.6723	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.672	Remote Similarity	NPD1778	Approved
0.6719	Remote Similarity	NPD1283	Approved
0.6719	Remote Similarity	NPD1876	Approved
0.6716	Remote Similarity	NPD1607	Approved
0.6696	Remote Similarity	NPD1930	Approved
0.6696	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD9500	Approved
0.6696	Remote Similarity	NPD1929	Approved
0.6695	Remote Similarity	NPD2182	Approved
0.6694	Remote Similarity	NPD1759	Phase 1
0.6693	Remote Similarity	NPD1608	Approved
0.6693	Remote Similarity	NPD3972	Approved
0.6691	Remote Similarity	NPD5406	Approved
0.6691	Remote Similarity	NPD5405	Approved
0.6691	Remote Similarity	NPD5408	Approved
0.6691	Remote Similarity	NPD5404	Approved
0.6667	Remote Similarity	NPD2313	Discontinued
0.6667	Remote Similarity	NPD3134	Approved
0.6667	Remote Similarity	NPD968	Approved
0.6667	Remote Similarity	NPD1445	Approved
0.6667	Remote Similarity	NPD1444	Approved
0.6667	Remote Similarity	NPD228	Approved
0.6667	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD2344	Approved
0.6642	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD3022	Approved
0.6639	Remote Similarity	NPD9614	Approved
0.6639	Remote Similarity	NPD3021	Approved
0.6639	Remote Similarity	NPD9618	Approved
0.6639	Remote Similarity	NPD5951	Approved
0.6635	Remote Similarity	NPD9089	Approved
0.6617	Remote Similarity	NPD6663	Approved
0.6615	Remote Similarity	NPD258	Approved
0.6615	Remote Similarity	NPD1019	Discontinued
0.6615	Remote Similarity	NPD257	Approved
0.6613	Remote Similarity	NPD5536	Phase 2
0.6613	Remote Similarity	NPD1758	Phase 1
0.6612	Remote Similarity	NPD5277	Phase 2
0.661	Remote Similarity	NPD1358	Approved
0.6609	Remote Similarity	NPD940	Approved
0.6609	Remote Similarity	NPD1932	Approved
0.6609	Remote Similarity	NPD846	Approved
0.6594	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD1549	Phase 2
0.6583	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6190	Approved
0.6567	Remote Similarity	NPD826	Approved
0.6567	Remote Similarity	NPD825	Approved
0.6565	Remote Similarity	NPD5736	Approved
0.6565	Remote Similarity	NPD9569	Approved
0.6562	Remote Similarity	NPD1481	Phase 2
0.656	Remote Similarity	NPD1894	Discontinued
0.6552	Remote Similarity	NPD3684	Discontinued
0.6544	Remote Similarity	NPD9279	Approved
0.6538	Remote Similarity	NPD9093	Approved
0.6538	Remote Similarity	NPD226	Approved
0.6535	Remote Similarity	NPD3496	Discontinued
0.6529	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD2346	Discontinued
0.6519	Remote Similarity	NPD555	Phase 2
0.6515	Remote Similarity	NPD6832	Phase 2
0.6508	Remote Similarity	NPD1651	Approved
0.6507	Remote Similarity	NPD2672	Discontinued
0.6505	Remote Similarity	NPD9490	Approved
0.6504	Remote Similarity	NPD2629	Approved
0.65	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.65	Remote Similarity	NPD1792	Phase 2
0.65	Remote Similarity	NPD8166	Discontinued
0.65	Remote Similarity	NPD4750	Phase 3
0.65	Remote Similarity	NPD4628	Phase 3
0.6496	Remote Similarity	NPD4308	Phase 3
0.6496	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD2799	Discontinued
0.6493	Remote Similarity	NPD259	Phase 1
0.6484	Remote Similarity	NPD1535	Discovery
0.6484	Remote Similarity	NPD1281	Approved
0.6483	Remote Similarity	NPD3455	Phase 2
0.6483	Remote Similarity	NPD824	Approved
0.648	Remote Similarity	NPD9616	Approved
0.648	Remote Similarity	NPD9615	Approved
0.648	Remote Similarity	NPD9613	Approved
0.6475	Remote Similarity	NPD9377	Approved
0.6475	Remote Similarity	NPD9379	Approved
0.6471	Remote Similarity	NPD2342	Discontinued
0.646	Remote Similarity	NPD1809	Phase 2
0.6457	Remote Similarity	NPD4626	Approved
0.6457	Remote Similarity	NPD17	Approved
0.6454	Remote Similarity	NPD2309	Approved
0.6441	Remote Similarity	NPD9697	Approved
0.6435	Remote Similarity	NPD2066	Phase 3
0.6434	Remote Similarity	NPD4878	Approved
0.6429	Remote Similarity	NPD316	Approved
0.6429	Remote Similarity	NPD3091	Approved
0.6429	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD2797	Approved
0.6408	Remote Similarity	NPD3300	Phase 2
0.6406	Remote Similarity	NPD3023	Approved
0.6406	Remote Similarity	NPD3026	Approved
0.6389	Remote Similarity	NPD6273	Approved
0.6385	Remote Similarity	NPD5157	Phase 1
0.6385	Remote Similarity	NPD5159	Phase 2
0.6385	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD3750	Approved
0.6383	Remote Similarity	NPD7003	Approved
0.6381	Remote Similarity	NPD942	Approved
0.6378	Remote Similarity	NPD3025	Approved
0.6378	Remote Similarity	NPD3024	Approved
0.6378	Remote Similarity	NPD5585	Approved
0.6371	Remote Similarity	NPD690	Clinical (unspecified phase)
0.637	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD800	Approved
0.6364	Remote Similarity	NPD1511	Approved
0.6364	Remote Similarity	NPD9295	Approved
0.6364	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD75	Approved
0.6357	Remote Similarity	NPD9277	Approved
0.6356	Remote Similarity	NPD9608	Approved
0.6356	Remote Similarity	NPD9244	Approved
0.6356	Remote Similarity	NPD9610	Approved
0.6349	Remote Similarity	NPD9092	Discovery
0.6343	Remote Similarity	NPD9537	Phase 1
0.6343	Remote Similarity	NPD9536	Phase 1
0.6341	Remote Similarity	NPD7635	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