NPASS Compound

Structure

NPC136649 OpenBabel07101718332D 27 29 0 0 1 0 0 0 0 0999 V2000 6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 8 1 0 0 0 0 4 13 2 0 0 0 0 5 9 2 0 0 0 0 5 13 1 0 0 0 0 6 10 1 0 0 0 0 6 14 2 0 0 0 0 7 11 2 0 0 0 0 7 14 1 0 0 0 0 8 15 2 0 0 0 0 9 15 1 0 0 0 0 10 16 2 0 0 0 0 11 16 1 0 0 0 0 12 17 1 0 0 0 0 12 21 1 0 0 0 0 13 18 1 0 0 0 0 14 21 1 0 0 0 0 15 25 1 0 0 0 0 16 26 1 0 0 0 0 17 18 2 0 0 0 0 17 27 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 19 22 2 0 0 0 0 20 21 1 6 0 0 0 20 23 1 0 0 0 0 21 24 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	370.14
Volume:	377.752
LogP:	2.294
LogD:	2.428
LogS:	-4.402
# Rotatable Bonds:	5
TPSA:	82.06
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.813
Synthetic Accessibility Score:	3.503
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.633
MDCK Permeability:	3.0850660550640896e-05
Pgp-inhibitor:	0.507
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.531

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.646
Plasma Protein Binding (PPB):	91.65184783935547%
Volume Distribution (VD):	0.857
Pgp-substrate:	3.999434471130371%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.83
CYP2C19-inhibitor:	0.575
CYP2C19-substrate:	0.899
CYP2C9-inhibitor:	0.215
CYP2C9-substrate:	0.423
CYP2D6-inhibitor:	0.054
CYP2D6-substrate:	0.745
CYP3A4-inhibitor:	0.918
CYP3A4-substrate:	0.894

ADMET: Excretion

Clearance (CL):	6.585
Half-life (T1/2):	0.047

ADMET: Toxicity

hERG Blockers:	0.137
Human Hepatotoxicity (H-HT):	0.293
Drug-inuced Liver Injury (DILI):	0.631
AMES Toxicity:	0.725
Rat Oral Acute Toxicity:	0.742
Maximum Recommended Daily Dose:	0.912
Skin Sensitization:	0.065
Carcinogencity:	0.341
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.037

Download Data

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

Natural Product: NPC136649

Natural Product ID:	NPC136649
*Common Name:**	Gliocladinin A
IUPAC Name:	(5S,6R)-5,6-dihydroxy-3-methoxy-2,5-bis(4-methoxyphenyl)cyclohex-2-en-1-one
Synonyms:
Standard InCHIKey:	GZSCQNISHIIIPB-SFTDATJTSA-N
Standard InCHI:	InChI=1S/C21H22O6/c1-25-15-8-4-13(5-9-15)18-17(27-3)12-21(24,20(23)19(18)22)14-6-10-16(26-2)11-7-14/h4-11,20,23-24H,12H2,1-3H3/t20-,21-/m0/s1
SMILES:	COc1ccc(cc1)C1=C(C[C@](c2ccc(cc2)OC)([C@H](C1=O)O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL400085
PubChem CID:	23642504
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers [CHEMONTID:0000138] Anisoles

*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
NPO32544	gliocladium sp.	Species	n.a.	Eukaryota	n.a.	New Zealand	n.a.	PMID[16643039]
NPO32544	gliocladium sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[17854154]

☑ 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
MIC	1
Others	1

Activity Type	# Activity
Cell Line	2
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	54000.0	nM	PMID[454419]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	270000.0	nM	PMID[454419]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	15.0	mm	PMID[454419]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	270000.0	nM	PMID[454419]

☑ 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 NPC136649 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	316
0.1-0.2	1180
0.2-0.3	2868
0.3-0.4	6534
0.4-0.5	11432
0.5-0.6	4595
0.6-0.7	7082
0.7-0.8	8009
0.8-0.85	634
0.85-0.9	46
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8723	High Similarity	NPC475104
0.8571	High Similarity	NPC222298
0.8571	High Similarity	NPC51070
0.8533	High Similarity	NPC327225
0.8533	High Similarity	NPC470340
0.8503	High Similarity	NPC316769
0.8493	Intermediate Similarity	NPC95751
0.8493	Intermediate Similarity	NPC301751
0.8493	Intermediate Similarity	NPC245482
0.8467	Intermediate Similarity	NPC319910
0.8467	Intermediate Similarity	NPC471229
0.8467	Intermediate Similarity	NPC262039
0.8467	Intermediate Similarity	NPC254412
0.8467	Intermediate Similarity	NPC262038
0.8467	Intermediate Similarity	NPC278476
0.8456	Intermediate Similarity	NPC277032
0.8451	Intermediate Similarity	NPC475549
0.8446	Intermediate Similarity	NPC122828
0.8446	Intermediate Similarity	NPC472918
0.8446	Intermediate Similarity	NPC44721
0.8446	Intermediate Similarity	NPC211466
0.8446	Intermediate Similarity	NPC40086
0.8446	Intermediate Similarity	NPC3779
0.8446	Intermediate Similarity	NPC176869
0.8446	Intermediate Similarity	NPC476182
0.8442	Intermediate Similarity	NPC470183
0.8425	Intermediate Similarity	NPC148545
0.8421	Intermediate Similarity	NPC48579
0.8421	Intermediate Similarity	NPC68727
0.8421	Intermediate Similarity	NPC326910
0.8421	Intermediate Similarity	NPC259710
0.8421	Intermediate Similarity	NPC304207
0.8421	Intermediate Similarity	NPC207809
0.8421	Intermediate Similarity	NPC217706
0.8414	Intermediate Similarity	NPC265178
0.8411	Intermediate Similarity	NPC210597
0.8411	Intermediate Similarity	NPC268992
0.8411	Intermediate Similarity	NPC113608
0.8411	Intermediate Similarity	NPC470337
0.8411	Intermediate Similarity	NPC470338
0.8411	Intermediate Similarity	NPC35567
0.8411	Intermediate Similarity	NPC217149
0.8411	Intermediate Similarity	NPC51824
0.8411	Intermediate Similarity	NPC138288
0.8411	Intermediate Similarity	NPC216035
0.8411	Intermediate Similarity	NPC180944
0.8411	Intermediate Similarity	NPC171651
0.8411	Intermediate Similarity	NPC243171
0.8403	Intermediate Similarity	NPC474784
0.84	Intermediate Similarity	NPC61258
0.84	Intermediate Similarity	NPC267117
0.84	Intermediate Similarity	NPC105136
0.8392	Intermediate Similarity	NPC470722
0.8392	Intermediate Similarity	NPC156888
0.8392	Intermediate Similarity	NPC470721
0.8392	Intermediate Similarity	NPC6100
0.8389	Intermediate Similarity	NPC218569
0.8367	Intermediate Similarity	NPC475705
0.8367	Intermediate Similarity	NPC117836
0.8367	Intermediate Similarity	NPC477409
0.8367	Intermediate Similarity	NPC476178
0.8367	Intermediate Similarity	NPC51887
0.8366	Intermediate Similarity	NPC215917
0.8366	Intermediate Similarity	NPC10754
0.8366	Intermediate Similarity	NPC164427
0.8366	Intermediate Similarity	NPC20530
0.8356	Intermediate Similarity	NPC232021
0.8356	Intermediate Similarity	NPC321980
0.8356	Intermediate Similarity	NPC40118
0.8356	Intermediate Similarity	NPC470087
0.8356	Intermediate Similarity	NPC126534
0.8355	Intermediate Similarity	NPC248793
0.8355	Intermediate Similarity	NPC203080
0.8355	Intermediate Similarity	NPC155686
0.8355	Intermediate Similarity	NPC209760
0.8355	Intermediate Similarity	NPC100134
0.8355	Intermediate Similarity	NPC180301
0.8355	Intermediate Similarity	NPC193200
0.8355	Intermediate Similarity	NPC293286
0.8354	Intermediate Similarity	NPC473094
0.8345	Intermediate Similarity	NPC201541
0.8344	Intermediate Similarity	NPC472420
0.8344	Intermediate Similarity	NPC471677
0.8344	Intermediate Similarity	NPC471676
0.8344	Intermediate Similarity	NPC263384
0.8344	Intermediate Similarity	NPC472422
0.8344	Intermediate Similarity	NPC46882
0.8344	Intermediate Similarity	NPC244577
0.8344	Intermediate Similarity	NPC132990
0.8333	Intermediate Similarity	NPC89442
0.8323	Intermediate Similarity	NPC284495
0.8322	Intermediate Similarity	NPC21835
0.8322	Intermediate Similarity	NPC472627
0.8312	Intermediate Similarity	NPC282390
0.8312	Intermediate Similarity	NPC246466
0.8312	Intermediate Similarity	NPC281137
0.8311	Intermediate Similarity	NPC62290
0.8311	Intermediate Similarity	NPC4152
0.8311	Intermediate Similarity	NPC306607
0.8311	Intermediate Similarity	NPC30890
0.8311	Intermediate Similarity	NPC49130
0.8311	Intermediate Similarity	NPC326506
0.8311	Intermediate Similarity	NPC124780
0.8311	Intermediate Similarity	NPC208176
0.8311	Intermediate Similarity	NPC142731
0.8311	Intermediate Similarity	NPC87486
0.8311	Intermediate Similarity	NPC279417
0.8302	Intermediate Similarity	NPC473096
0.8302	Intermediate Similarity	NPC473095
0.8301	Intermediate Similarity	NPC111341
0.8301	Intermediate Similarity	NPC304745
0.8301	Intermediate Similarity	NPC476169
0.8301	Intermediate Similarity	NPC471116
0.8299	Intermediate Similarity	NPC297600
0.8299	Intermediate Similarity	NPC239608
0.8299	Intermediate Similarity	NPC46161
0.8289	Intermediate Similarity	NPC321363
0.8289	Intermediate Similarity	NPC474843
0.8289	Intermediate Similarity	NPC475790
0.8289	Intermediate Similarity	NPC253904
0.8289	Intermediate Similarity	NPC324233
0.8289	Intermediate Similarity	NPC323626
0.8278	Intermediate Similarity	NPC37348
0.8278	Intermediate Similarity	NPC231668
0.8278	Intermediate Similarity	NPC225854
0.8276	Intermediate Similarity	NPC322021
0.8269	Intermediate Similarity	NPC316457
0.8269	Intermediate Similarity	NPC478222
0.8267	Intermediate Similarity	NPC474903
0.8267	Intermediate Similarity	NPC191634
0.8258	Intermediate Similarity	NPC152904
0.8258	Intermediate Similarity	NPC22192
0.8255	Intermediate Similarity	NPC472629
0.8255	Intermediate Similarity	NPC148011
0.8255	Intermediate Similarity	NPC124729
0.8255	Intermediate Similarity	NPC1940
0.8255	Intermediate Similarity	NPC229190
0.8247	Intermediate Similarity	NPC471500
0.8247	Intermediate Similarity	NPC320825
0.8247	Intermediate Similarity	NPC303255
0.8247	Intermediate Similarity	NPC326037
0.8247	Intermediate Similarity	NPC24640
0.8247	Intermediate Similarity	NPC13858
0.8247	Intermediate Similarity	NPC478223
0.8235	Intermediate Similarity	NPC223701
0.8235	Intermediate Similarity	NPC236756
0.8235	Intermediate Similarity	NPC25127
0.8235	Intermediate Similarity	NPC88983
0.8235	Intermediate Similarity	NPC268193
0.8235	Intermediate Similarity	NPC7989
0.8235	Intermediate Similarity	NPC244250
0.8235	Intermediate Similarity	NPC472583
0.8235	Intermediate Similarity	NPC20907
0.8235	Intermediate Similarity	NPC311579
0.8231	Intermediate Similarity	NPC469404
0.8231	Intermediate Similarity	NPC470089
0.8228	Intermediate Similarity	NPC234052
0.8228	Intermediate Similarity	NPC472049
0.8228	Intermediate Similarity	NPC224280
0.8224	Intermediate Similarity	NPC474023
0.8224	Intermediate Similarity	NPC474772
0.8224	Intermediate Similarity	NPC472423
0.8224	Intermediate Similarity	NPC207346
0.8224	Intermediate Similarity	NPC472636
0.8224	Intermediate Similarity	NPC46564
0.8224	Intermediate Similarity	NPC474744
0.8224	Intermediate Similarity	NPC471675
0.8224	Intermediate Similarity	NPC474021
0.8224	Intermediate Similarity	NPC151425
0.8219	Intermediate Similarity	NPC470211
0.8219	Intermediate Similarity	NPC469523
0.8217	Intermediate Similarity	NPC478229
0.8217	Intermediate Similarity	NPC473961
0.8212	Intermediate Similarity	NPC472628
0.8212	Intermediate Similarity	NPC5173
0.8212	Intermediate Similarity	NPC270160
0.8212	Intermediate Similarity	NPC237440
0.8212	Intermediate Similarity	NPC470461
0.8207	Intermediate Similarity	NPC7013
0.8207	Intermediate Similarity	NPC209560
0.8207	Intermediate Similarity	NPC162680
0.8207	Intermediate Similarity	NPC303644
0.8207	Intermediate Similarity	NPC294409
0.8207	Intermediate Similarity	NPC116632
0.8207	Intermediate Similarity	NPC181124
0.8205	Intermediate Similarity	NPC287328
0.8205	Intermediate Similarity	NPC282009
0.8205	Intermediate Similarity	NPC263449
0.8205	Intermediate Similarity	NPC471976
0.82	Intermediate Similarity	NPC210320
0.82	Intermediate Similarity	NPC192568
0.82	Intermediate Similarity	NPC471076
0.8194	Intermediate Similarity	NPC471515
0.8194	Intermediate Similarity	NPC67876
0.8194	Intermediate Similarity	NPC471479
0.8194	Intermediate Similarity	NPC52530
0.8188	Intermediate Similarity	NPC224714
0.8188	Intermediate Similarity	NPC98356
0.8188	Intermediate Similarity	NPC212697
0.8188	Intermediate Similarity	NPC474799

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 NPC136649 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	270
0.1-0.2	800
0.2-0.3	1439
0.3-0.4	2411
0.4-0.5	2174
0.5-0.6	1206
0.6-0.7	680
0.7-0.8	162
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8188	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD4628	Phase 3
0.8158	Intermediate Similarity	NPD4380	Phase 2
0.8117	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD1510	Phase 2
0.8052	Intermediate Similarity	NPD1934	Approved
0.8	Intermediate Similarity	NPD6166	Phase 2
0.8	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD7075	Discontinued
0.7959	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD6801	Discontinued
0.7931	Intermediate Similarity	NPD1607	Approved
0.7922	Intermediate Similarity	NPD6599	Discontinued
0.7917	Intermediate Similarity	NPD1240	Approved
0.7905	Intermediate Similarity	NPD1549	Phase 2
0.7895	Intermediate Similarity	NPD1512	Approved
0.7891	Intermediate Similarity	NPD2796	Approved
0.7885	Intermediate Similarity	NPD2801	Approved
0.7881	Intermediate Similarity	NPD6799	Approved
0.7867	Intermediate Similarity	NPD6190	Approved
0.7848	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD6233	Phase 2
0.7834	Intermediate Similarity	NPD5402	Approved
0.7834	Intermediate Similarity	NPD3817	Phase 2
0.7798	Intermediate Similarity	NPD8434	Phase 2
0.7791	Intermediate Similarity	NPD3751	Discontinued
0.7785	Intermediate Similarity	NPD3882	Suspended
0.777	Intermediate Similarity	NPD2935	Discontinued
0.7763	Intermediate Similarity	NPD1511	Approved
0.7744	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD5403	Approved
0.7722	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD3027	Phase 3
0.7703	Intermediate Similarity	NPD7033	Discontinued
0.7658	Intermediate Similarity	NPD7819	Suspended
0.7655	Intermediate Similarity	NPD6798	Discontinued
0.7654	Intermediate Similarity	NPD3787	Discontinued
0.7651	Intermediate Similarity	NPD6797	Phase 2
0.7633	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6355	Discontinued
0.7616	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD7251	Discontinued
0.7597	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD5401	Approved
0.7593	Intermediate Similarity	NPD6959	Discontinued
0.759	Intermediate Similarity	NPD7074	Phase 3
0.7589	Intermediate Similarity	NPD3972	Approved
0.7576	Intermediate Similarity	NPD3818	Discontinued
0.7566	Intermediate Similarity	NPD3750	Approved
0.756	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD7808	Phase 3
0.7546	Intermediate Similarity	NPD6232	Discontinued
0.7534	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7411	Suspended
0.7531	Intermediate Similarity	NPD5494	Approved
0.753	Intermediate Similarity	NPD5844	Phase 1
0.753	Intermediate Similarity	NPD7054	Approved
0.7515	Intermediate Similarity	NPD7473	Discontinued
0.75	Intermediate Similarity	NPD6559	Discontinued
0.75	Intermediate Similarity	NPD2798	Approved
0.7485	Intermediate Similarity	NPD7472	Approved
0.7484	Intermediate Similarity	NPD37	Approved
0.7484	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD7095	Approved
0.7465	Intermediate Similarity	NPD1608	Approved
0.7453	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD1651	Approved
0.7417	Intermediate Similarity	NPD6099	Approved
0.7417	Intermediate Similarity	NPD6100	Approved
0.7415	Intermediate Similarity	NPD3268	Approved
0.7413	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD3226	Approved
0.7372	Intermediate Similarity	NPD2533	Approved
0.7372	Intermediate Similarity	NPD2532	Approved
0.7372	Intermediate Similarity	NPD1241	Discontinued
0.7372	Intermediate Similarity	NPD2534	Approved
0.7365	Intermediate Similarity	NPD4062	Phase 3
0.7361	Intermediate Similarity	NPD1283	Approved
0.7351	Intermediate Similarity	NPD2799	Discontinued
0.7351	Intermediate Similarity	NPD3748	Approved
0.7346	Intermediate Similarity	NPD4967	Phase 2
0.7346	Intermediate Similarity	NPD4965	Approved
0.7346	Intermediate Similarity	NPD7768	Phase 2
0.7346	Intermediate Similarity	NPD4966	Approved
0.7338	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2861	Phase 2
0.7318	Intermediate Similarity	NPD6776	Approved
0.7318	Intermediate Similarity	NPD6781	Approved
0.7318	Intermediate Similarity	NPD6782	Approved
0.7318	Intermediate Similarity	NPD6780	Approved
0.7318	Intermediate Similarity	NPD6778	Approved
0.7318	Intermediate Similarity	NPD6777	Approved
0.7318	Intermediate Similarity	NPD6779	Approved
0.7315	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1613	Approved
0.731	Intermediate Similarity	NPD2797	Approved
0.7303	Intermediate Similarity	NPD1551	Phase 2
0.7299	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD3764	Approved
0.7296	Intermediate Similarity	NPD7458	Discontinued
0.7283	Intermediate Similarity	NPD8150	Discontinued
0.7279	Intermediate Similarity	NPD4908	Phase 1
0.7278	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2800	Approved
0.7273	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6234	Discontinued
0.7255	Intermediate Similarity	NPD2344	Approved
0.7255	Intermediate Similarity	NPD2346	Discontinued
0.7254	Intermediate Similarity	NPD17	Approved
0.7246	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD3300	Phase 2
0.7241	Intermediate Similarity	NPD1876	Approved
0.7222	Intermediate Similarity	NPD8455	Phase 2
0.7219	Intermediate Similarity	NPD6651	Approved
0.7215	Intermediate Similarity	NPD6273	Approved
0.7208	Intermediate Similarity	NPD2424	Discontinued
0.7208	Intermediate Similarity	NPD4534	Discontinued
0.72	Intermediate Similarity	NPD943	Approved
0.72	Intermediate Similarity	NPD4060	Phase 1
0.72	Intermediate Similarity	NPD2979	Phase 3
0.7198	Intermediate Similarity	NPD7435	Discontinued
0.7195	Intermediate Similarity	NPD3749	Approved
0.719	Intermediate Similarity	NPD2438	Suspended
0.7181	Intermediate Similarity	NPD2313	Discontinued
0.7181	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2354	Approved
0.7179	Intermediate Similarity	NPD3887	Approved
0.7163	Intermediate Similarity	NPD5536	Phase 2
0.7153	Intermediate Similarity	NPD1201	Approved
0.7153	Intermediate Similarity	NPD1281	Approved
0.7153	Intermediate Similarity	NPD1610	Phase 2
0.7152	Intermediate Similarity	NPD4340	Discontinued
0.7152	Intermediate Similarity	NPD230	Phase 1
0.7143	Intermediate Similarity	NPD5647	Approved
0.7124	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD4308	Phase 3
0.7117	Intermediate Similarity	NPD5761	Phase 2
0.7117	Intermediate Similarity	NPD5760	Phase 2
0.7115	Intermediate Similarity	NPD8166	Discontinued
0.7115	Intermediate Similarity	NPD7003	Approved
0.7113	Intermediate Similarity	NPD9545	Approved
0.711	Intermediate Similarity	NPD8313	Approved
0.711	Intermediate Similarity	NPD8312	Approved
0.7104	Intermediate Similarity	NPD7696	Phase 3
0.7104	Intermediate Similarity	NPD7698	Approved
0.7104	Intermediate Similarity	NPD7697	Approved
0.7103	Intermediate Similarity	NPD1481	Phase 2
0.7097	Intermediate Similarity	NPD5958	Discontinued
0.7095	Intermediate Similarity	NPD9494	Approved
0.7093	Intermediate Similarity	NPD7685	Pre-registration
0.7089	Intermediate Similarity	NPD7390	Discontinued
0.7086	Intermediate Similarity	NPD2238	Phase 2
0.7083	Intermediate Similarity	NPD3847	Discontinued
0.7083	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3926	Phase 2
0.7081	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD3267	Approved
0.7075	Intermediate Similarity	NPD1470	Approved
0.7075	Intermediate Similarity	NPD3266	Approved
0.707	Intermediate Similarity	NPD2309	Approved
0.7067	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD7199	Phase 2
0.7066	Intermediate Similarity	NPD1247	Approved
0.7065	Intermediate Similarity	NPD7871	Phase 2
0.7065	Intermediate Similarity	NPD7870	Phase 2
0.7059	Intermediate Similarity	NPD7228	Approved
0.7059	Intermediate Similarity	NPD4536	Approved
0.7059	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4538	Approved
0.7055	Intermediate Similarity	NPD4749	Approved
0.7055	Intermediate Similarity	NPD6844	Discontinued
0.7052	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6832	Phase 2
0.7047	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD7701	Phase 2
0.7039	Intermediate Similarity	NPD6535	Approved
0.7039	Intermediate Similarity	NPD6534	Approved
0.7039	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5124	Phase 1
0.7037	Intermediate Similarity	NPD7028	Phase 2
0.7034	Intermediate Similarity	NPD1535	Discovery
0.7032	Intermediate Similarity	NPD5763	Approved
0.7032	Intermediate Similarity	NPD7266	Discontinued
0.7032	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6002	Phase 3
0.7032	Intermediate Similarity	NPD6004	Phase 3
0.7032	Intermediate Similarity	NPD1471	Phase 3
0.7032	Intermediate Similarity	NPD5762	Approved
0.7032	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6005	Phase 3
0.7027	Intermediate Similarity	NPD6917	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