NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	183.09
Volume:	185.122
LogP:	0.119
LogD:	0.46
LogS:	-0.576
# Rotatable Bonds:	3
TPSA:	62.58
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.725
Synthetic Accessibility Score:	2.529
Fsp3:	0.444
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:	-4.576
MDCK Permeability:	7.356796231761109e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.089
30% Bioavailability (F30%):	0.148

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.1
Plasma Protein Binding (PPB):	14.773356437683105%
Volume Distribution (VD):	1.351
Pgp-substrate:	73.13582611083984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.049
CYP1A2-substrate:	0.392
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.511
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.148
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.521
CYP3A4-inhibitor:	0.004
CYP3A4-substrate:	0.283

ADMET: Excretion

Clearance (CL):	7.471
Half-life (T1/2):	0.889

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.157
Drug-inuced Liver Injury (DILI):	0.103
AMES Toxicity:	0.349
Rat Oral Acute Toxicity:	0.052
Maximum Recommended Daily Dose:	0.021
Skin Sensitization:	0.878
Carcinogencity:	0.496
Eye Corrosion:	0.003
Eye Irritation:	0.056
Respiratory Toxicity:	0.068

Download Data

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

Natural Product: NPC263439

Natural Product ID:	NPC263439
*Common Name:**	Ginkgotoxin
IUPAC Name:	5-(hydroxymethyl)-4-(methoxymethyl)-2-methylpyridin-3-ol
Synonyms:	Ginkgotoxin
Standard InCHIKey:	SVINQHQHARVZFF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H13NO3/c1-6-9(12)8(5-13-2)7(4-11)3-10-6/h3,11-12H,4-5H2,1-2H3
SMILES:	Cc1c(c(COC)c(cn1)CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1076875
PubChem CID:	76581
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0001948] Pyridoxines

*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
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(01)00320-X]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11738417]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21462031]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	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
LD50	1
Others	4

Activity Type	# Activity
Organism	1
Others	1
SINGLE PROTEIN	1
Tissue	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT24311	SINGLE PROTEIN	Pyridoxal kinase	Homo sapiens	Km	=	5000.0	nM	PMID[483484]
NPT35	Others	n.a.		LogP	=	-0.299	n.a.	PMID[483484]
NPT614	Tissue	Plasma	Rattus norvegicus	Cp	=	1.31	uM	PMID[483484]
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	LD50	=	30.0	mg.kg-1	PMID[483484]
NPT621	Tissue	Plasma	Homo sapiens	Drug uptake	=	53.0	nM	PMID[483484]

☑ 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 NPC263439 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	336
0.1-0.2	3902
0.2-0.3	13363
0.3-0.4	13161
0.4-0.5	7930
0.5-0.6	3077
0.6-0.7	822
0.7-0.8	93
0.8-0.85	3
0.85-0.9	2
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9732	High Similarity	NPC132680
0.9732	High Similarity	NPC269919
0.9597	High Similarity	NPC63562
0.9346	High Similarity	NPC322976
0.9346	High Similarity	NPC63338
0.9346	High Similarity	NPC324203
0.9103	High Similarity	NPC211187
0.8875	High Similarity	NPC256828
0.8614	High Similarity	NPC325705
0.8614	High Similarity	NPC52831
0.8208	Intermediate Similarity	NPC36498
0.8101	Intermediate Similarity	NPC220523
0.7791	Intermediate Similarity	NPC153769
0.7791	Intermediate Similarity	NPC194724
0.775	Intermediate Similarity	NPC471598
0.7709	Intermediate Similarity	NPC3715
0.7658	Intermediate Similarity	NPC471596
0.7616	Intermediate Similarity	NPC252590
0.761	Intermediate Similarity	NPC280853
0.7562	Intermediate Similarity	NPC285016
0.7562	Intermediate Similarity	NPC245657
0.7558	Intermediate Similarity	NPC473764
0.7558	Intermediate Similarity	NPC314940
0.7554	Intermediate Similarity	NPC224928
0.7546	Intermediate Similarity	NPC161292
0.7529	Intermediate Similarity	NPC473057
0.7514	Intermediate Similarity	NPC219963
0.75	Intermediate Similarity	NPC174421
0.7469	Intermediate Similarity	NPC470403
0.7469	Intermediate Similarity	NPC470394
0.7469	Intermediate Similarity	NPC470404
0.7453	Intermediate Similarity	NPC318935
0.7442	Intermediate Similarity	NPC108469
0.7438	Intermediate Similarity	NPC471594
0.7389	Intermediate Similarity	NPC42591
0.7378	Intermediate Similarity	NPC470395
0.7355	Intermediate Similarity	NPC165370
0.7333	Intermediate Similarity	NPC320394
0.7318	Intermediate Similarity	NPC266551
0.7318	Intermediate Similarity	NPC161887
0.7317	Intermediate Similarity	NPC471323
0.7297	Intermediate Similarity	NPC226202
0.7294	Intermediate Similarity	NPC138018
0.7292	Intermediate Similarity	NPC316403
0.7283	Intermediate Similarity	NPC471178
0.7273	Intermediate Similarity	NPC314270
0.7259	Intermediate Similarity	NPC470799
0.7259	Intermediate Similarity	NPC8022
0.7244	Intermediate Similarity	NPC212125
0.7238	Intermediate Similarity	NPC284559
0.7219	Intermediate Similarity	NPC251090
0.7216	Intermediate Similarity	NPC253810
0.7204	Intermediate Similarity	NPC289786
0.7193	Intermediate Similarity	NPC116573
0.7181	Intermediate Similarity	NPC267928
0.7172	Intermediate Similarity	NPC477110
0.7167	Intermediate Similarity	NPC478032
0.716	Intermediate Similarity	NPC284348
0.7151	Intermediate Similarity	NPC283152
0.7128	Intermediate Similarity	NPC473053
0.7127	Intermediate Similarity	NPC470474
0.7119	Intermediate Similarity	NPC249614
0.711	Intermediate Similarity	NPC25899
0.7105	Intermediate Similarity	NPC476167
0.7102	Intermediate Similarity	NPC44161
0.71	Intermediate Similarity	NPC173080
0.7099	Intermediate Similarity	NPC29702
0.7099	Intermediate Similarity	NPC328029
0.7098	Intermediate Similarity	NPC329708
0.7098	Intermediate Similarity	NPC47059
0.7098	Intermediate Similarity	NPC118832
0.7098	Intermediate Similarity	NPC165349
0.7098	Intermediate Similarity	NPC274291
0.7098	Intermediate Similarity	NPC264166
0.7069	Intermediate Similarity	NPC471177
0.7069	Intermediate Similarity	NPC177404
0.7069	Intermediate Similarity	NPC124542
0.7069	Intermediate Similarity	NPC59779
0.7065	Intermediate Similarity	NPC315804
0.7065	Intermediate Similarity	NPC313804
0.7059	Intermediate Similarity	NPC133140
0.7059	Intermediate Similarity	NPC195268
0.7053	Intermediate Similarity	NPC192315
0.7052	Intermediate Similarity	NPC84508
0.7049	Intermediate Similarity	NPC62069
0.7049	Intermediate Similarity	NPC207851
0.7047	Intermediate Similarity	NPC475774
0.7029	Intermediate Similarity	NPC97367
0.7027	Intermediate Similarity	NPC46580
0.7025	Intermediate Similarity	NPC306397
0.7011	Intermediate Similarity	NPC20249
0.7011	Intermediate Similarity	NPC314002
0.7006	Intermediate Similarity	NPC151489
0.7006	Intermediate Similarity	NPC319456
0.7005	Intermediate Similarity	NPC5145
0.7	Intermediate Similarity	NPC288943
0.6982	Remote Similarity	NPC257142
0.6979	Remote Similarity	NPC19872
0.6971	Remote Similarity	NPC48192
0.6961	Remote Similarity	NPC96890
0.6957	Remote Similarity	NPC256893
0.6957	Remote Similarity	NPC204717
0.6954	Remote Similarity	NPC185782
0.6935	Remote Similarity	NPC26679
0.6935	Remote Similarity	NPC202605
0.6935	Remote Similarity	NPC112206
0.6935	Remote Similarity	NPC66083
0.6931	Remote Similarity	NPC307963
0.6931	Remote Similarity	NPC473822
0.6927	Remote Similarity	NPC121658
0.6927	Remote Similarity	NPC14651
0.6919	Remote Similarity	NPC295158
0.6919	Remote Similarity	NPC62510
0.6915	Remote Similarity	NPC469390
0.6907	Remote Similarity	NPC470678
0.6906	Remote Similarity	NPC203754
0.6906	Remote Similarity	NPC134586
0.6906	Remote Similarity	NPC150048
0.6904	Remote Similarity	NPC18348
0.6904	Remote Similarity	NPC477111
0.6902	Remote Similarity	NPC220765
0.6898	Remote Similarity	NPC110741
0.6898	Remote Similarity	NPC75544
0.6898	Remote Similarity	NPC44354
0.6888	Remote Similarity	NPC472287
0.6888	Remote Similarity	NPC472286
0.6882	Remote Similarity	NPC171171
0.6882	Remote Similarity	NPC61350
0.6875	Remote Similarity	NPC71079
0.6872	Remote Similarity	NPC476138
0.6872	Remote Similarity	NPC245816
0.6872	Remote Similarity	NPC476518
0.6868	Remote Similarity	NPC184964
0.6868	Remote Similarity	NPC211997
0.6854	Remote Similarity	NPC41717
0.6842	Remote Similarity	NPC79293
0.6842	Remote Similarity	NPC329541
0.6842	Remote Similarity	NPC279401
0.6839	Remote Similarity	NPC476582
0.6839	Remote Similarity	NPC4071
0.6839	Remote Similarity	NPC476578
0.6837	Remote Similarity	NPC164374
0.6837	Remote Similarity	NPC137929
0.6837	Remote Similarity	NPC470500
0.6836	Remote Similarity	NPC118511
0.6836	Remote Similarity	NPC102423
0.6836	Remote Similarity	NPC474217
0.6833	Remote Similarity	NPC158129
0.6833	Remote Similarity	NPC273532
0.6832	Remote Similarity	NPC288349
0.6831	Remote Similarity	NPC472168
0.6831	Remote Similarity	NPC42979
0.6828	Remote Similarity	NPC241025
0.6827	Remote Similarity	NPC244536
0.6825	Remote Similarity	NPC114974
0.6821	Remote Similarity	NPC66815
0.6818	Remote Similarity	NPC287208
0.6813	Remote Similarity	NPC224764
0.6809	Remote Similarity	NPC296527
0.6804	Remote Similarity	NPC477019
0.6802	Remote Similarity	NPC477113
0.6798	Remote Similarity	NPC85918
0.6791	Remote Similarity	NPC314573
0.6789	Remote Similarity	NPC141915
0.6789	Remote Similarity	NPC114335
0.6789	Remote Similarity	NPC280964
0.6786	Remote Similarity	NPC317572
0.6786	Remote Similarity	NPC60553
0.6784	Remote Similarity	NPC469589
0.678	Remote Similarity	NPC174049
0.678	Remote Similarity	NPC79911
0.6772	Remote Similarity	NPC76748
0.6771	Remote Similarity	NPC109922
0.6771	Remote Similarity	NPC13880
0.6769	Remote Similarity	NPC31930
0.6769	Remote Similarity	NPC155792
0.6766	Remote Similarity	NPC316981
0.676	Remote Similarity	NPC278366
0.676	Remote Similarity	NPC127730
0.6753	Remote Similarity	NPC287437
0.6753	Remote Similarity	NPC128823
0.6751	Remote Similarity	NPC16452
0.6751	Remote Similarity	NPC472259
0.6751	Remote Similarity	NPC36229
0.6751	Remote Similarity	NPC476581
0.675	Remote Similarity	NPC11464
0.674	Remote Similarity	NPC302647
0.6737	Remote Similarity	NPC92111
0.6733	Remote Similarity	NPC162530
0.6732	Remote Similarity	NPC193267
0.6732	Remote Similarity	NPC213530
0.6724	Remote Similarity	NPC107287
0.6724	Remote Similarity	NPC26872
0.6723	Remote Similarity	NPC120798
0.672	Remote Similarity	NPC32771
0.672	Remote Similarity	NPC48938
0.6718	Remote Similarity	NPC315957
0.6718	Remote Similarity	NPC176538
0.6718	Remote Similarity	NPC234197
0.6717	Remote Similarity	NPC304183

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 NPC263439 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	704
0.2-0.3	907
0.3-0.4	1733
0.4-0.5	3252
0.5-0.6	1921
0.6-0.7	401
0.7-0.8	38
0.8-0.85	3
0.85-0.9	2
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9732	High Similarity	NPD9382	Approved
0.9732	High Similarity	NPD9383	Approved
0.9346	High Similarity	NPD9398	Clinical (unspecified phase)
0.8614	High Similarity	NPD9510	Approved
0.8476	Intermediate Similarity	NPD2123	Phase 3
0.8457	Intermediate Similarity	NPD1229	Phase 2
0.8208	Intermediate Similarity	NPD9364	Phase 2
0.8208	Intermediate Similarity	NPD9363	Approved
0.8023	Intermediate Similarity	NPD5317	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD9362	Approved
0.7791	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD5256	Discontinued
0.7429	Intermediate Similarity	NPD9690	Approved
0.7427	Intermediate Similarity	NPD862	Approved
0.7427	Intermediate Similarity	NPD861	Approved
0.7427	Intermediate Similarity	NPD863	Approved
0.7418	Intermediate Similarity	NPD1213	Phase 3
0.7396	Intermediate Similarity	NPD2581	Approved
0.7396	Intermediate Similarity	NPD2582	Approved
0.7384	Intermediate Similarity	NPD925	Approved
0.7384	Intermediate Similarity	NPD926	Approved
0.731	Intermediate Similarity	NPD1418	Phase 2
0.7308	Intermediate Similarity	NPD1034	Phase 3
0.7308	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1622	Discontinued
0.7267	Intermediate Similarity	NPD9506	Approved
0.7257	Intermediate Similarity	NPD565	Phase 2
0.7251	Intermediate Similarity	NPD5255	Approved
0.7247	Intermediate Similarity	NPD6159	Phase 2
0.7244	Intermediate Similarity	NPD9284	Approved
0.7243	Intermediate Similarity	NPD6569	Phase 2
0.7241	Intermediate Similarity	NPD425	Approved
0.7241	Intermediate Similarity	NPD424	Approved
0.7209	Intermediate Similarity	NPD112	Approved
0.7209	Intermediate Similarity	NPD9705	Discontinued
0.7207	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD158	Discontinued
0.7135	Intermediate Similarity	NPD5316	Approved
0.7135	Intermediate Similarity	NPD8063	Discontinued
0.711	Intermediate Similarity	NPD687	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD4036	Approved
0.7098	Intermediate Similarity	NPD31	Approved
0.7098	Intermediate Similarity	NPD4035	Approved
0.7098	Intermediate Similarity	NPD4037	Approved
0.7098	Intermediate Similarity	NPD4034	Approved
0.7098	Intermediate Similarity	NPD4038	Approved
0.7098	Intermediate Similarity	NPD4033	Approved
0.7098	Intermediate Similarity	NPD32	Approved
0.7098	Intermediate Similarity	NPD4122	Approved
0.7098	Intermediate Similarity	NPD4039	Approved
0.709	Intermediate Similarity	NPD2952	Discontinued
0.7059	Intermediate Similarity	NPD3922	Approved
0.7059	Intermediate Similarity	NPD3923	Approved
0.7059	Intermediate Similarity	NPD3924	Approved
0.7059	Intermediate Similarity	NPD3921	Approved
0.7037	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3477	Phase 2
0.7033	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD4204	Approved
0.7033	Intermediate Similarity	NPD4203	Approved
0.703	Intermediate Similarity	NPD1649	Discontinued
0.7025	Intermediate Similarity	NPD9080	Approved
0.7022	Intermediate Similarity	NPD485	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD9695	Approved
0.7012	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD9076	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1352	Discontinued
0.6989	Remote Similarity	NPD4021	Phase 2
0.6984	Remote Similarity	NPD3395	Approved
0.6984	Remote Similarity	NPD3396	Approved
0.6979	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD4375	Approved
0.697	Remote Similarity	NPD4131	Phase 3
0.6959	Remote Similarity	NPD9595	Approved
0.6959	Remote Similarity	NPD9596	Approved
0.694	Remote Similarity	NPD3386	Phase 2
0.6939	Remote Similarity	NPD1392	Approved
0.6931	Remote Similarity	NPD4551	Phase 2
0.6931	Remote Similarity	NPD1038	Approved
0.6927	Remote Similarity	NPD2177	Approved
0.6927	Remote Similarity	NPD2176	Approved
0.6927	Remote Similarity	NPD2175	Phase 3
0.691	Remote Similarity	NPD2781	Approved
0.6905	Remote Similarity	NPD3813	Approved
0.6897	Remote Similarity	NPD537	Phase 2
0.6897	Remote Similarity	NPD9574	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD534	Phase 2
0.6893	Remote Similarity	NPD2780	Approved
0.6893	Remote Similarity	NPD2782	Approved
0.6889	Remote Similarity	NPD2077	Approved
0.6889	Remote Similarity	NPD2076	Approved
0.6884	Remote Similarity	NPD3570	Phase 2
0.6884	Remote Similarity	NPD4502	Phase 2
0.6882	Remote Similarity	NPD3039	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD9689	Approved
0.6872	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD1032	Phase 2
0.6865	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD796	Phase 2
0.6845	Remote Similarity	NPD3525	Discontinued
0.6845	Remote Similarity	NPD2383	Phase 1
0.6842	Remote Similarity	NPD6361	Phase 2
0.6839	Remote Similarity	NPD1274	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD4889	Approved
0.6827	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD4086	Phase 1
0.6813	Remote Similarity	NPD5100	Phase 3
0.6805	Remote Similarity	NPD8823	Approved
0.68	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD4372	Phase 1
0.6784	Remote Similarity	NPD4703	Approved
0.6784	Remote Similarity	NPD4702	Approved
0.6776	Remote Similarity	NPD4071	Approved
0.6776	Remote Similarity	NPD4072	Approved
0.6776	Remote Similarity	NPD2414	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD1096	Discontinued
0.6768	Remote Similarity	NPD7222	Phase 2
0.6758	Remote Similarity	NPD1923	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD4529	Approved
0.6754	Remote Similarity	NPD4526	Approved
0.6754	Remote Similarity	NPD4528	Approved
0.6753	Remote Similarity	NPD5999	Phase 2
0.6737	Remote Similarity	NPD4699	Discontinued
0.6737	Remote Similarity	NPD4148	Approved
0.6718	Remote Similarity	NPD1739	Approved
0.6718	Remote Similarity	NPD1740	Approved
0.6715	Remote Similarity	NPD8356	Approved
0.6703	Remote Similarity	NPD2599	Approved
0.6703	Remote Similarity	NPD2600	Approved
0.6703	Remote Similarity	NPD2601	Approved
0.67	Remote Similarity	NPD4437	Phase 3
0.6699	Remote Similarity	NPD5640	Discontinued
0.6687	Remote Similarity	NPD9207	Approved
0.6687	Remote Similarity	NPD9206	Approved
0.6685	Remote Similarity	NPD6641	Approved
0.6685	Remote Similarity	NPD6642	Approved
0.6684	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD3321	Discontinued
0.6683	Remote Similarity	NPD6290	Phase 2
0.6667	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4795	Phase 2
0.6667	Remote Similarity	NPD5612	Discontinued
0.6667	Remote Similarity	NPD9687	Approved
0.6667	Remote Similarity	NPD9688	Approved
0.6649	Remote Similarity	NPD2334	Discontinued
0.6649	Remote Similarity	NPD3082	Discontinued
0.6647	Remote Similarity	NPD3717	Discontinued
0.6635	Remote Similarity	NPD1856	Discontinued
0.6634	Remote Similarity	NPD3939	Suspended
0.663	Remote Similarity	NPD5862	Discovery
0.661	Remote Similarity	NPD820	Phase 3
0.6601	Remote Similarity	NPD7069	Discontinued
0.66	Remote Similarity	NPD7452	Approved
0.66	Remote Similarity	NPD7453	Approved
0.6597	Remote Similarity	NPD2544	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD5320	Approved
0.6593	Remote Similarity	NPD5319	Approved
0.659	Remote Similarity	NPD9271	Approved
0.6589	Remote Similarity	NPD7558	Phase 2
0.6588	Remote Similarity	NPD8430	Approved
0.6582	Remote Similarity	NPD1768	Approved
0.658	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.658	Remote Similarity	NPD802	Phase 2
0.6579	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD5863	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD7948	Phase 1
0.6561	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD1503	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD3920	Phase 2
0.6557	Remote Similarity	NPD9548	Phase 2
0.6555	Remote Similarity	NPD4945	Discontinued
0.6552	Remote Similarity	NPD5067	Phase 2
0.6552	Remote Similarity	NPD5936	Approved
0.6552	Remote Similarity	NPD5066	Phase 2
0.6552	Remote Similarity	NPD5939	Approved
0.6548	Remote Similarity	NPD484	Approved
0.6545	Remote Similarity	NPD9714	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD4921	Phase 3
0.6526	Remote Similarity	NPD4920	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD4919	Phase 3
0.6522	Remote Similarity	NPD5948	Phase 2
0.652	Remote Similarity	NPD3815	Phase 1
0.652	Remote Similarity	NPD3816	Phase 1
0.6512	Remote Similarity	NPD6494	Phase 2
0.6508	Remote Similarity	NPD3569	Discontinued
0.65	Remote Similarity	NPD1685	Approved
0.65	Remote Similarity	NPD1684	Approved
0.6497	Remote Similarity	NPD4548	Discontinued
0.6488	Remote Similarity	NPD2616	Phase 3
0.6488	Remote Similarity	NPD2615	Phase 3
0.648	Remote Similarity	NPD704	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