NPASS Compound

Structure

NPC90953 OpenBabel07101719522D 24 27 0 0 1 0 0 0 0 0999 V2000 3.8005 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7278 0.4739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1592 2.3074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8540 1.7567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1933 2.0486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 0.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3080 0.8657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7099 0.6126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9345 0.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8663 1.6003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 3.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3364 1.5827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0685 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9345 1.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2024 1.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2024 4.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3849 1.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6009 0.1586 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 3 7 1 0 0 0 0 3 13 1 0 0 0 0 4 6 1 0 0 0 0 4 14 1 0 0 0 0 5 8 2 0 0 0 0 5 14 1 0 0 0 0 6 19 1 0 0 0 0 8 23 1 0 0 0 0 9 15 1 0 0 0 0 9 16 1 0 0 0 0 10 15 1 0 0 0 0 10 17 2 0 0 0 0 11 14 2 0 0 0 0 11 23 1 0 0 0 0 12 20 1 0 0 0 0 12 24 1 0 0 0 0 13 19 1 6 0 0 0 15 21 1 1 0 0 0 16 18 1 0 0 0 0 16 20 1 1 0 0 0 17 19 1 0 0 0 0 17 20 1 0 0 0 0 18 22 2 0 0 0 0 18 24 1 0 0 0 0 19 2 1 6 0 0 0 20 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.18
Volume:	344.865
LogP:	2.711
LogD:	2.136
LogS:	-4.374
# Rotatable Bonds:	3
TPSA:	59.67
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.681
Synthetic Accessibility Score:	5.26
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.779
MDCK Permeability:	2.31924896070268e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.602
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.163
30% Bioavailability (F30%):	0.34

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.363
Plasma Protein Binding (PPB):	91.81147003173828%
Volume Distribution (VD):	1.793
Pgp-substrate:	9.029093742370605%

ADMET: Metabolism

CYP1A2-inhibitor:	0.221
CYP1A2-substrate:	0.44
CYP2C19-inhibitor:	0.907
CYP2C19-substrate:	0.756
CYP2C9-inhibitor:	0.615
CYP2C9-substrate:	0.114
CYP2D6-inhibitor:	0.13
CYP2D6-substrate:	0.169
CYP3A4-inhibitor:	0.838
CYP3A4-substrate:	0.385

ADMET: Excretion

Clearance (CL):	4.445
Half-life (T1/2):	0.402

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.17
Drug-inuced Liver Injury (DILI):	0.069
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.835
Maximum Recommended Daily Dose:	0.843
Skin Sensitization:	0.082
Carcinogencity:	0.308
Eye Corrosion:	0.003
Eye Irritation:	0.298
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC90953

Natural Product ID:	NPC90953
*Common Name:**	Guadichaudone
IUPAC Name:	(3aS,5R,7S,8R,10aR)-7-[2-(furan-3-yl)ethyl]-5-hydroxy-7,8-dimethyl-3a,4,5,8,9,10-hexahydro-1H-benzo[d][2]benzofuran-3-one
Synonyms:	guadichaudone
Standard InCHIKey:	MSUGIEBLKPBYGA-RFXCRVDXSA-N
Standard InCHI:	InChI=1S/C20H26O4/c1-13-3-7-20-12-24-18(22)16(20)9-15(21)10-17(20)19(13,2)6-4-14-5-8-23-11-14/h5,8,10-11,13,15-16,21H,3-4,6-7,9,12H2,1-2H3/t13-,15-,16-,19+,20-/m1/s1
SMILES:	O[C@@H]1C[C@@H]2C(=O)OC[C@]32C(=C1)[C@@](C)(CCc1cocc1)[C@@H](CC3)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512696
PubChem CID:	10042282
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO258	Baccharis gaudichaudiana	Species	Asteraceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[16499330]
NPO258	Baccharis gaudichaudiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7931367]
NPO258	Baccharis gaudichaudiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO258	Baccharis gaudichaudiana	Species	Asteraceae	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
ED50	8

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1851	Cell Line	Col2	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[487946]
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[487946]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[487946]
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[487946]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[487946]
NPT168	Cell Line	P388	Mus musculus	ED50	=	11.7	ug ml-1	PMID[487946]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	20.0	ug ml-1	PMID[487946]

☑ 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 NPC90953 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	273
0.1-0.2	1091
0.2-0.3	2464
0.3-0.4	5252
0.4-0.5	10885
0.5-0.6	11859
0.6-0.7	9600
0.7-0.8	962
0.8-0.85	216
0.85-0.9	90
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9424	High Similarity	NPC250228
0.9209	High Similarity	NPC251865
0.916	High Similarity	NPC112706
0.916	High Similarity	NPC207294
0.9118	High Similarity	NPC186626
0.9098	High Similarity	NPC89133
0.9085	High Similarity	NPC476941
0.9085	High Similarity	NPC476942
0.9021	High Similarity	NPC195325
0.9014	High Similarity	NPC476937
0.9014	High Similarity	NPC476938
0.9008	High Similarity	NPC23086
0.8971	High Similarity	NPC92941
0.8955	High Similarity	NPC298190
0.8955	High Similarity	NPC61788
0.8944	High Similarity	NPC346
0.8939	High Similarity	NPC83178
0.8929	High Similarity	NPC121158
0.8905	High Similarity	NPC146872
0.8904	High Similarity	NPC57998
0.8889	High Similarity	NPC472654
0.8881	High Similarity	NPC471174
0.8865	High Similarity	NPC470741
0.8865	High Similarity	NPC223415
0.8865	High Similarity	NPC267632
0.8864	High Similarity	NPC138139
0.8864	High Similarity	NPC46536
0.8841	High Similarity	NPC470742
0.8836	High Similarity	NPC75906
0.8836	High Similarity	NPC476940
0.8836	High Similarity	NPC476939
0.8803	High Similarity	NPC476944
0.8786	High Similarity	NPC67003
0.875	High Similarity	NPC216755
0.8725	High Similarity	NPC470118
0.8725	High Similarity	NPC197137
0.8725	High Similarity	NPC261597
0.8716	High Similarity	NPC92979
0.8716	High Similarity	NPC155939
0.8716	High Similarity	NPC141538
0.8716	High Similarity	NPC296807
0.8716	High Similarity	NPC44675
0.8716	High Similarity	NPC214541
0.8716	High Similarity	NPC35000
0.8707	High Similarity	NPC469503
0.8707	High Similarity	NPC268905
0.8705	High Similarity	NPC310830
0.8696	High Similarity	NPC158525
0.8686	High Similarity	NPC218838
0.8667	High Similarity	NPC223063
0.8667	High Similarity	NPC120836
0.8662	High Similarity	NPC473152
0.8652	High Similarity	NPC148374
0.8649	High Similarity	NPC34421
0.8649	High Similarity	NPC98206
0.8649	High Similarity	NPC178932
0.8649	High Similarity	NPC237259
0.8649	High Similarity	NPC30222
0.8647	High Similarity	NPC179354
0.8643	High Similarity	NPC236532
0.8636	High Similarity	NPC16922
0.863	High Similarity	NPC125182
0.863	High Similarity	NPC69647
0.8623	High Similarity	NPC471998
0.8621	High Similarity	NPC221809
0.8621	High Similarity	NPC255414
0.8621	High Similarity	NPC10088
0.8613	High Similarity	NPC45358
0.8613	High Similarity	NPC471995
0.8601	High Similarity	NPC243577
0.86	High Similarity	NPC472778
0.86	High Similarity	NPC472777
0.86	High Similarity	NPC472776
0.86	High Similarity	NPC304692
0.86	High Similarity	NPC36655
0.8592	High Similarity	NPC205765
0.8592	High Similarity	NPC20500
0.8591	High Similarity	NPC469336
0.8581	High Similarity	NPC246164
0.8581	High Similarity	NPC472672
0.8581	High Similarity	NPC44577
0.8581	High Similarity	NPC33938
0.8571	High Similarity	NPC470997
0.8562	High Similarity	NPC7388
0.8562	High Similarity	NPC471007
0.8561	High Similarity	NPC477967
0.8553	High Similarity	NPC470792
0.8543	High Similarity	NPC475967
0.8543	High Similarity	NPC475226
0.8542	High Similarity	NPC137295
0.8533	High Similarity	NPC104736
0.8523	High Similarity	NPC253201
0.8523	High Similarity	NPC302054
0.8523	High Similarity	NPC282445
0.8519	High Similarity	NPC290955
0.8519	High Similarity	NPC319140
0.8519	High Similarity	NPC95567
0.8514	High Similarity	NPC272590
0.8514	High Similarity	NPC116717
0.8511	High Similarity	NPC476943
0.8511	High Similarity	NPC471996
0.8511	High Similarity	NPC220094
0.8503	High Similarity	NPC234494
0.8503	High Similarity	NPC471001
0.85	High Similarity	NPC46896
0.8487	Intermediate Similarity	NPC477402
0.8483	Intermediate Similarity	NPC5676
0.8478	Intermediate Similarity	NPC97740
0.8477	Intermediate Similarity	NPC299038
0.8477	Intermediate Similarity	NPC214495
0.8477	Intermediate Similarity	NPC187149
0.8477	Intermediate Similarity	NPC475066
0.8477	Intermediate Similarity	NPC470119
0.8472	Intermediate Similarity	NPC476946
0.8467	Intermediate Similarity	NPC264943
0.8456	Intermediate Similarity	NPC477123
0.8456	Intermediate Similarity	NPC477966
0.8446	Intermediate Similarity	NPC5180
0.8446	Intermediate Similarity	NPC196846
0.8444	Intermediate Similarity	NPC74612
0.8433	Intermediate Similarity	NPC130275
0.8433	Intermediate Similarity	NPC243269
0.8429	Intermediate Similarity	NPC476947
0.8425	Intermediate Similarity	NPC276676
0.8421	Intermediate Similarity	NPC477403
0.8421	Intermediate Similarity	NPC472671
0.8421	Intermediate Similarity	NPC262872
0.8417	Intermediate Similarity	NPC470740
0.8417	Intermediate Similarity	NPC471006
0.8411	Intermediate Similarity	NPC469485
0.8406	Intermediate Similarity	NPC17681
0.8392	Intermediate Similarity	NPC56197
0.8392	Intermediate Similarity	NPC90296
0.8389	Intermediate Similarity	NPC291150
0.8389	Intermediate Similarity	NPC18135
0.8378	Intermediate Similarity	NPC470998
0.8377	Intermediate Similarity	NPC224394
0.8377	Intermediate Similarity	NPC283209
0.8377	Intermediate Similarity	NPC198047
0.8377	Intermediate Similarity	NPC663
0.837	Intermediate Similarity	NPC230979
0.8367	Intermediate Similarity	NPC470941
0.8358	Intermediate Similarity	NPC272899
0.8356	Intermediate Similarity	NPC41182
0.8356	Intermediate Similarity	NPC185456
0.8355	Intermediate Similarity	NPC472772
0.8355	Intermediate Similarity	NPC249021
0.8355	Intermediate Similarity	NPC45101
0.8355	Intermediate Similarity	NPC173544
0.8345	Intermediate Similarity	NPC80635
0.8345	Intermediate Similarity	NPC471817
0.8333	Intermediate Similarity	NPC294511
0.8333	Intermediate Similarity	NPC470996
0.8333	Intermediate Similarity	NPC21460
0.8333	Intermediate Similarity	NPC471002
0.8333	Intermediate Similarity	NPC121615
0.8333	Intermediate Similarity	NPC100333
0.8323	Intermediate Similarity	NPC261184
0.8323	Intermediate Similarity	NPC123088
0.8322	Intermediate Similarity	NPC156189
0.8322	Intermediate Similarity	NPC476936
0.8322	Intermediate Similarity	NPC212257
0.8322	Intermediate Similarity	NPC159927
0.8322	Intermediate Similarity	NPC202260
0.8322	Intermediate Similarity	NPC469335
0.8321	Intermediate Similarity	NPC477040
0.8321	Intermediate Similarity	NPC26532
0.8321	Intermediate Similarity	NPC279877
0.8321	Intermediate Similarity	NPC329707
0.8321	Intermediate Similarity	NPC477039
0.8312	Intermediate Similarity	NPC200782
0.8312	Intermediate Similarity	NPC211777
0.8312	Intermediate Similarity	NPC69028
0.8312	Intermediate Similarity	NPC5079
0.8311	Intermediate Similarity	NPC93666
0.831	Intermediate Similarity	NPC4764
0.831	Intermediate Similarity	NPC310043
0.8301	Intermediate Similarity	NPC307383
0.8301	Intermediate Similarity	NPC474611
0.8299	Intermediate Similarity	NPC470999
0.8299	Intermediate Similarity	NPC471292
0.8296	Intermediate Similarity	NPC65735
0.8296	Intermediate Similarity	NPC188377
0.8289	Intermediate Similarity	NPC41880
0.8288	Intermediate Similarity	NPC238843
0.8288	Intermediate Similarity	NPC199044
0.8288	Intermediate Similarity	NPC142113
0.8278	Intermediate Similarity	NPC114880
0.8276	Intermediate Similarity	NPC52412
0.8269	Intermediate Similarity	NPC214600
0.8261	Intermediate Similarity	NPC208389
0.8258	Intermediate Similarity	NPC419
0.8258	Intermediate Similarity	NPC165218
0.8258	Intermediate Similarity	NPC243704
0.8258	Intermediate Similarity	NPC234660
0.8258	Intermediate Similarity	NPC51568
0.8258	Intermediate Similarity	NPC285567
0.8255	Intermediate Similarity	NPC470791
0.8255	Intermediate Similarity	NPC211625
0.8255	Intermediate Similarity	NPC470790

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 NPC90953 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	240
0.1-0.2	812
0.2-0.3	1859
0.3-0.4	2640
0.4-0.5	2147
0.5-0.6	1153
0.6-0.7	275
0.7-0.8	22
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8344	Intermediate Similarity	NPD5761	Phase 2
0.8344	Intermediate Similarity	NPD5760	Phase 2
0.7905	Intermediate Similarity	NPD4628	Phase 3
0.7823	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD8434	Phase 2
0.759	Intermediate Similarity	NPD6765	Approved
0.759	Intermediate Similarity	NPD6764	Approved
0.7532	Intermediate Similarity	NPD6273	Approved
0.7467	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD6002	Phase 3
0.7467	Intermediate Similarity	NPD6004	Phase 3
0.7467	Intermediate Similarity	NPD6005	Phase 3
0.7467	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD6784	Approved
0.7412	Intermediate Similarity	NPD6785	Approved
0.7346	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2799	Discontinued
0.7171	Intermediate Similarity	NPD1551	Phase 2
0.717	Intermediate Similarity	NPD3226	Approved
0.717	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD3764	Approved
0.7152	Intermediate Similarity	NPD920	Approved
0.7124	Intermediate Similarity	NPD2346	Discontinued
0.7097	Intermediate Similarity	NPD7003	Approved
0.7097	Intermediate Similarity	NPD3750	Approved
0.7083	Intermediate Similarity	NPD1608	Approved
0.7076	Intermediate Similarity	NPD6559	Discontinued
0.7048	Intermediate Similarity	NPD8127	Discontinued
0.7047	Intermediate Similarity	NPD2313	Discontinued
0.7025	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2532	Approved
0.7025	Intermediate Similarity	NPD2533	Approved
0.7025	Intermediate Similarity	NPD2534	Approved
0.7012	Intermediate Similarity	NPD4965	Approved
0.7012	Intermediate Similarity	NPD4966	Approved
0.7012	Intermediate Similarity	NPD4967	Phase 2
0.698	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4140	Approved
0.6939	Remote Similarity	NPD2797	Approved
0.6923	Remote Similarity	NPD2800	Approved
0.6914	Remote Similarity	NPD6599	Discontinued
0.6908	Remote Similarity	NPD6355	Discontinued
0.6903	Remote Similarity	NPD2344	Approved
0.6901	Remote Similarity	NPD5844	Phase 1
0.6899	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD5647	Approved
0.689	Remote Similarity	NPD7819	Suspended
0.6884	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD3748	Approved
0.6883	Remote Similarity	NPD4308	Phase 3
0.6883	Remote Similarity	NPD7033	Discontinued
0.6879	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4110	Phase 3
0.6875	Remote Similarity	NPD1778	Approved
0.6875	Remote Similarity	NPD17	Approved
0.6867	Remote Similarity	NPD3749	Approved
0.6853	Remote Similarity	NPD9545	Approved
0.6852	Remote Similarity	NPD7458	Discontinued
0.6849	Remote Similarity	NPD9717	Approved
0.6839	Remote Similarity	NPD2935	Discontinued
0.6829	Remote Similarity	NPD37	Approved
0.6826	Remote Similarity	NPD6234	Discontinued
0.6821	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD3268	Approved
0.6807	Remote Similarity	NPD7768	Phase 2
0.6806	Remote Similarity	NPD5585	Approved
0.68	Remote Similarity	NPD8313	Approved
0.68	Remote Similarity	NPD6832	Phase 2
0.68	Remote Similarity	NPD8312	Approved
0.6795	Remote Similarity	NPD5763	Approved
0.6795	Remote Similarity	NPD5762	Approved
0.6795	Remote Similarity	NPD1471	Phase 3
0.6788	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD8032	Phase 2
0.6768	Remote Similarity	NPD7411	Suspended
0.6766	Remote Similarity	NPD7075	Discontinued
0.6759	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1283	Approved
0.6753	Remote Similarity	NPD6653	Approved
0.6752	Remote Similarity	NPD970	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD5402	Approved
0.6744	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD1241	Discontinued
0.6735	Remote Similarity	NPD3972	Approved
0.6732	Remote Similarity	NPD2979	Phase 3
0.673	Remote Similarity	NPD2309	Approved
0.6728	Remote Similarity	NPD5403	Approved
0.6727	Remote Similarity	NPD6801	Discontinued
0.6712	Remote Similarity	NPD3496	Discontinued
0.6711	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD6362	Approved
0.6711	Remote Similarity	NPD1203	Approved
0.6709	Remote Similarity	NPD1243	Approved
0.6708	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD447	Suspended
0.6687	Remote Similarity	NPD7236	Approved
0.6667	Remote Similarity	NPD2798	Approved
0.6667	Remote Similarity	NPD6663	Approved
0.6667	Remote Similarity	NPD8166	Discontinued
0.6649	Remote Similarity	NPD8404	Phase 2
0.6647	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7228	Approved
0.6647	Remote Similarity	NPD7177	Discontinued
0.6646	Remote Similarity	NPD6799	Approved
0.6646	Remote Similarity	NPD1549	Phase 2
0.6645	Remote Similarity	NPD7008	Discontinued
0.6644	Remote Similarity	NPD1876	Approved
0.6629	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD919	Approved
0.6624	Remote Similarity	NPD6100	Approved
0.6624	Remote Similarity	NPD6099	Approved
0.6624	Remote Similarity	NPD4476	Approved
0.6624	Remote Similarity	NPD4477	Approved
0.6624	Remote Similarity	NPD2796	Approved
0.6623	Remote Similarity	NPD4307	Phase 2
0.6619	Remote Similarity	NPD2182	Approved
0.6619	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD4380	Phase 2
0.6605	Remote Similarity	NPD5401	Approved
0.6601	Remote Similarity	NPD6798	Discontinued
0.6601	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD411	Approved
0.66	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD5494	Approved
0.6587	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD7440	Discontinued
0.6582	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD5735	Approved
0.6581	Remote Similarity	NPD5124	Phase 1
0.6577	Remote Similarity	NPD4359	Approved
0.6568	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD6233	Phase 2
0.6556	Remote Similarity	NPD1019	Discontinued
0.6556	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD1281	Approved
0.6554	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD3818	Discontinued
0.6541	Remote Similarity	NPD4534	Discontinued
0.6533	Remote Similarity	NPD6696	Suspended
0.6532	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4626	Approved
0.6519	Remote Similarity	NPD2438	Suspended
0.6516	Remote Similarity	NPD4060	Phase 1
0.6513	Remote Similarity	NPD5736	Approved
0.6512	Remote Similarity	NPD5710	Approved
0.6512	Remote Similarity	NPD5711	Approved
0.6512	Remote Similarity	NPD7229	Phase 3
0.6512	Remote Similarity	NPD6232	Discontinued
0.651	Remote Similarity	NPD1481	Phase 2
0.6509	Remote Similarity	NPD3882	Suspended
0.6507	Remote Similarity	NPD1894	Discontinued
0.6506	Remote Similarity	NPD7028	Phase 2
0.6497	Remote Similarity	NPD7097	Phase 1
0.6494	Remote Similarity	NPD7473	Discontinued
0.649	Remote Similarity	NPD3267	Approved
0.649	Remote Similarity	NPD3266	Approved
0.6488	Remote Similarity	NPD8455	Phase 2
0.6485	Remote Similarity	NPD7239	Suspended
0.6474	Remote Similarity	NPD4622	Approved
0.6474	Remote Similarity	NPD4618	Approved
0.6474	Remote Similarity	NPD230	Phase 1
0.6471	Remote Similarity	NPD2614	Approved
0.6463	Remote Similarity	NPD5691	Approved
0.6458	Remote Similarity	NPD2629	Approved
0.6458	Remote Similarity	NPD5951	Approved
0.6456	Remote Similarity	NPD1510	Phase 2
0.6453	Remote Similarity	NPD1247	Approved
0.6453	Remote Similarity	NPD6959	Discontinued
0.6453	Remote Similarity	NPD7199	Phase 2
0.6452	Remote Similarity	NPD4870	Approved
0.6452	Remote Similarity	NPD4062	Phase 3
0.645	Remote Similarity	NPD4288	Approved
0.6443	Remote Similarity	NPD1535	Discovery
0.6438	Remote Similarity	NPD5958	Discontinued
0.6438	Remote Similarity	NPD2424	Discontinued
0.6433	Remote Similarity	NPD1607	Approved
0.6429	Remote Similarity	NPD7095	Approved
0.6429	Remote Similarity	NPD1934	Approved
0.6429	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD8651	Approved
0.6424	Remote Similarity	NPD3225	Approved
0.642	Remote Similarity	NPD3887	Approved
0.6416	Remote Similarity	NPD6808	Phase 2
0.6415	Remote Similarity	NPD2531	Phase 2
0.6414	Remote Similarity	NPD7157	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