NPASS Compound

Structure

NPC220094 OpenBabel07101718312D 23 26 0 0 1 0 0 0 0 0999 V2000 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 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 2.5981 -2.5000 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9487 -2.7024 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 -1.7796 -1.0933 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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 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 -2.4487 -1.8364 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 3 4 1 0 0 0 0 3 5 2 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 6 8 1 0 0 0 0 6 13 2 0 0 0 0 7 9 2 0 0 0 0 7 12 1 0 0 0 0 8 18 1 0 0 0 0 9 22 1 0 0 0 0 10 14 1 0 0 0 0 10 19 1 0 0 0 0 11 12 2 0 0 0 0 11 22 1 0 0 0 0 13 17 1 0 0 0 0 13 19 1 0 0 0 0 14 12 1 6 0 0 0 14 23 1 0 0 0 0 15 18 1 1 0 0 0 15 19 1 0 0 0 0 16 18 1 0 0 0 0 16 20 2 0 0 0 0 17 21 2 0 0 0 0 17 23 1 0 0 0 0 18 1 1 6 0 0 0 19 2 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	312.14
Volume:	322.296
LogP:	2.993
LogD:	2.181
LogS:	-4.168
# Rotatable Bonds:	1
TPSA:	56.51
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.741
Synthetic Accessibility Score:	4.678
Fsp3:	0.474
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:	-4.677
MDCK Permeability:	2.585824768175371e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.959
30% Bioavailability (F30%):	0.024

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.04
Plasma Protein Binding (PPB):	96.21968841552734%
Volume Distribution (VD):	2.276
Pgp-substrate:	5.588924884796143%

ADMET: Metabolism

CYP1A2-inhibitor:	0.403
CYP1A2-substrate:	0.721
CYP2C19-inhibitor:	0.867
CYP2C19-substrate:	0.671
CYP2C9-inhibitor:	0.647
CYP2C9-substrate:	0.109
CYP2D6-inhibitor:	0.266
CYP2D6-substrate:	0.144
CYP3A4-inhibitor:	0.891
CYP3A4-substrate:	0.311

ADMET: Excretion

Clearance (CL):	10.176
Half-life (T1/2):	0.351

ADMET: Toxicity

hERG Blockers:	0.084
Human Hepatotoxicity (H-HT):	0.533
Drug-inuced Liver Injury (DILI):	0.103
AMES Toxicity:	0.222
Rat Oral Acute Toxicity:	0.962
Maximum Recommended Daily Dose:	0.949
Skin Sensitization:	0.609
Carcinogencity:	0.931
Eye Corrosion:	0.074
Eye Irritation:	0.23
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC220094

Natural Product ID:	NPC220094
*Common Name:**	Fibaruretin D
IUPAC Name:	(2R,6aR,10aS,10bS)-2-(furan-3-yl)-6a,10b-dimethyl-2,6,10,10a-tetrahydro-1H-benzo[f]isochromene-4,7-dione
Synonyms:	Fibaruretin D
Standard InCHIKey:	LAXIYINGQJWPCG-OHDICMOHSA-N
Standard InCHI:	InChI=1S/C19H20O4/c1-18-8-6-13-17(21)23-14(12-7-9-22-11-12)10-19(13,2)15(18)4-3-5-16(18)20/h3,5-7,9,11,14-15H,4,8,10H2,1-2H3/t14-,15-,18-,19-/m1/s1
SMILES:	C[C@@]12CC=C3C(=O)O[C@H](C[C@@]3(C)[C@@H]1CC=CC2=O)c1ccoc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL485038
PubChem CID:	44588977
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans [CHEMONTID:0001641] Naphthopyranones

*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
NPO10715	Fibraurea tinctoria	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17994701]
NPO10715	Fibraurea tinctoria	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18829331]
NPO10715	Fibraurea tinctoria	Species	Menispermaceae	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
Others	12

Activity Type	# Activity
Organism	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	23.41	%	PMID[495500]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	23.67	%	PMID[495500]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	21.47	%	PMID[495500]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	22.79	%	PMID[495500]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	20.91	%	PMID[495500]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	17.0	%	PMID[495500]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	20.5	%	PMID[495500]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	20.67	%	PMID[495500]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	21.55	%	PMID[495500]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	25.18	%	PMID[495500]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	24.17	%	PMID[495500]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	19.44	%	PMID[495500]

☑ 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 NPC220094 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	309
0.1-0.2	1344
0.2-0.3	3369
0.3-0.4	6921
0.4-0.5	12369
0.5-0.6	8328
0.6-0.7	8484
0.7-0.8	1383
0.8-0.85	142
0.85-0.9	42
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9771	High Similarity	NPC310830
0.9697	High Similarity	NPC476943
0.947	High Similarity	NPC92941
0.9416	High Similarity	NPC142113
0.9328	High Similarity	NPC470742
0.9203	High Similarity	NPC470741
0.9143	High Similarity	NPC262198
0.9143	High Similarity	NPC346
0.9137	High Similarity	NPC476944
0.9091	High Similarity	NPC21460
0.9078	High Similarity	NPC250228
0.903	High Similarity	NPC470740
0.9021	High Similarity	NPC469335
0.9021	High Similarity	NPC46551
0.9021	High Similarity	NPC159927
0.8978	High Similarity	NPC236532
0.8971	High Similarity	NPC146872
0.8944	High Similarity	NPC470941
0.8929	High Similarity	NPC223415
0.8929	High Similarity	NPC267632
0.8905	High Similarity	NPC42400
0.8897	High Similarity	NPC44577
0.8889	High Similarity	NPC196864
0.8889	High Similarity	NPC477404
0.8881	High Similarity	NPC298190
0.8864	High Similarity	NPC319140
0.8864	High Similarity	NPC95567
0.8836	High Similarity	NPC178932
0.8811	High Similarity	NPC10088
0.8788	High Similarity	NPC74612
0.8776	High Similarity	NPC469336
0.8776	High Similarity	NPC469850
0.8776	High Similarity	NPC281258
0.8776	High Similarity	NPC264943
0.8767	High Similarity	NPC469503
0.8759	High Similarity	NPC476122
0.875	High Similarity	NPC476941
0.875	High Similarity	NPC476942
0.8732	High Similarity	NPC86935
0.8722	High Similarity	NPC83178
0.8716	High Similarity	NPC209364
0.8716	High Similarity	NPC60973
0.8714	High Similarity	NPC56197
0.8712	High Similarity	NPC179354
0.8707	High Similarity	NPC30222
0.8707	High Similarity	NPC57998
0.869	High Similarity	NPC329180
0.8681	High Similarity	NPC221809
0.8681	High Similarity	NPC476938
0.8681	High Similarity	NPC476937
0.8658	High Similarity	NPC472283
0.8658	High Similarity	NPC286722
0.8652	High Similarity	NPC20500
0.8649	High Similarity	NPC214541
0.8649	High Similarity	NPC44675
0.8649	High Similarity	NPC35000
0.8643	High Similarity	NPC474722
0.8639	High Similarity	NPC476201
0.8613	High Similarity	NPC471006
0.8611	High Similarity	NPC276676
0.8611	High Similarity	NPC471292
0.8601	High Similarity	NPC238843
0.8601	High Similarity	NPC199044
0.86	High Similarity	NPC473473
0.86	High Similarity	NPC477403
0.86	High Similarity	NPC475295
0.86	High Similarity	NPC262872
0.8592	High Similarity	NPC473152
0.8591	High Similarity	NPC263265
0.8591	High Similarity	NPC107646
0.8581	High Similarity	NPC282445
0.8562	High Similarity	NPC195325
0.8561	High Similarity	NPC16922
0.855	High Similarity	NPC1848
0.8543	High Similarity	NPC477402
0.854	High Similarity	NPC471817
0.8533	High Similarity	NPC167142
0.8533	High Similarity	NPC261597
0.8533	High Similarity	NPC472772
0.8533	High Similarity	NPC249021
0.8523	High Similarity	NPC476262
0.8521	High Similarity	NPC205765
0.8519	High Similarity	NPC207294
0.8519	High Similarity	NPC112706
0.8514	High Similarity	NPC75906
0.8511	High Similarity	NPC90953
0.8503	High Similarity	NPC156189
0.8503	High Similarity	NPC476936
0.8503	High Similarity	NPC470997
0.8489	Intermediate Similarity	NPC158525
0.8487	Intermediate Similarity	NPC5079
0.8487	Intermediate Similarity	NPC69028
0.8483	Intermediate Similarity	NPC62799
0.8477	Intermediate Similarity	NPC307383
0.8477	Intermediate Similarity	NPC474932
0.8477	Intermediate Similarity	NPC237155
0.8472	Intermediate Similarity	NPC137295
0.8467	Intermediate Similarity	NPC126723
0.8467	Intermediate Similarity	NPC469485
0.8446	Intermediate Similarity	NPC18135
0.8435	Intermediate Similarity	NPC472654
0.8431	Intermediate Similarity	NPC51568
0.8431	Intermediate Similarity	NPC165218
0.8431	Intermediate Similarity	NPC469338
0.8431	Intermediate Similarity	NPC292389
0.8431	Intermediate Similarity	NPC234660
0.8421	Intermediate Similarity	NPC475381
0.8421	Intermediate Similarity	NPC25255
0.8421	Intermediate Similarity	NPC305016
0.8411	Intermediate Similarity	NPC173544
0.8411	Intermediate Similarity	NPC299038
0.8411	Intermediate Similarity	NPC187149
0.8411	Intermediate Similarity	NPC36655
0.8411	Intermediate Similarity	NPC45101
0.8389	Intermediate Similarity	NPC476939
0.8389	Intermediate Similarity	NPC476940
0.8389	Intermediate Similarity	NPC33938
0.8382	Intermediate Similarity	NPC477039
0.8377	Intermediate Similarity	NPC469849
0.8377	Intermediate Similarity	NPC276551
0.8377	Intermediate Similarity	NPC146991
0.8377	Intermediate Similarity	NPC470940
0.837	Intermediate Similarity	NPC138139
0.837	Intermediate Similarity	NPC46536
0.8369	Intermediate Similarity	NPC186626
0.8367	Intermediate Similarity	NPC19747
0.8366	Intermediate Similarity	NPC263432
0.8366	Intermediate Similarity	NPC193798
0.8366	Intermediate Similarity	NPC472771
0.8366	Intermediate Similarity	NPC207978
0.8366	Intermediate Similarity	NPC470939
0.8366	Intermediate Similarity	NPC82851
0.8366	Intermediate Similarity	NPC149896
0.8366	Intermediate Similarity	NPC211777
0.8356	Intermediate Similarity	NPC233763
0.8355	Intermediate Similarity	NPC475967
0.8355	Intermediate Similarity	NPC474611
0.8345	Intermediate Similarity	NPC84479
0.8345	Intermediate Similarity	NPC251865
0.8344	Intermediate Similarity	NPC204663
0.8333	Intermediate Similarity	NPC471863
0.8333	Intermediate Similarity	NPC61788
0.8333	Intermediate Similarity	NPC121158
0.8323	Intermediate Similarity	NPC478178
0.8323	Intermediate Similarity	NPC470875
0.8321	Intermediate Similarity	NPC198904
0.8321	Intermediate Similarity	NPC243704
0.8321	Intermediate Similarity	NPC208389
0.8312	Intermediate Similarity	NPC224394
0.8312	Intermediate Similarity	NPC472773
0.8312	Intermediate Similarity	NPC476197
0.8312	Intermediate Similarity	NPC477405
0.8312	Intermediate Similarity	NPC198047
0.8312	Intermediate Similarity	NPC663
0.8312	Intermediate Similarity	NPC419
0.8311	Intermediate Similarity	NPC470791
0.8311	Intermediate Similarity	NPC234494
0.8311	Intermediate Similarity	NPC211625
0.8311	Intermediate Similarity	NPC470790
0.8311	Intermediate Similarity	NPC471001
0.831	Intermediate Similarity	NPC472376
0.8301	Intermediate Similarity	NPC335761
0.8301	Intermediate Similarity	NPC472653
0.8299	Intermediate Similarity	NPC471174
0.8298	Intermediate Similarity	NPC46896
0.8289	Intermediate Similarity	NPC195131
0.8289	Intermediate Similarity	NPC472776
0.8289	Intermediate Similarity	NPC472778
0.8289	Intermediate Similarity	NPC472777
0.8288	Intermediate Similarity	NPC41182
0.8286	Intermediate Similarity	NPC471998
0.8276	Intermediate Similarity	NPC476946
0.8269	Intermediate Similarity	NPC173516
0.8269	Intermediate Similarity	NPC473766
0.8269	Intermediate Similarity	NPC473753
0.8258	Intermediate Similarity	NPC476857
0.8258	Intermediate Similarity	NPC476856
0.8258	Intermediate Similarity	NPC123088
0.8258	Intermediate Similarity	NPC476858
0.8258	Intermediate Similarity	NPC470182
0.8258	Intermediate Similarity	NPC476860
0.8248	Intermediate Similarity	NPC477123
0.8248	Intermediate Similarity	NPC476917
0.8248	Intermediate Similarity	NPC477966
0.8248	Intermediate Similarity	NPC327527
0.8247	Intermediate Similarity	NPC329938
0.8247	Intermediate Similarity	NPC197596
0.8247	Intermediate Similarity	NPC200782
0.8247	Intermediate Similarity	NPC18347
0.8239	Intermediate Similarity	NPC307401
0.8239	Intermediate Similarity	NPC310043
0.8235	Intermediate Similarity	NPC23086
0.8235	Intermediate Similarity	NPC473368
0.8217	Intermediate Similarity	NPC471397
0.8209	Intermediate Similarity	NPC36255
0.8209	Intermediate Similarity	NPC317217
0.8205	Intermediate Similarity	NPC23387
0.8201	Intermediate Similarity	NPC89133
0.82	Intermediate Similarity	NPC116717
0.82	Intermediate Similarity	NPC272590

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 NPC220094 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	268
0.1-0.2	962
0.2-0.3	1901
0.3-0.4	2685
0.4-0.5	2072
0.5-0.6	975
0.6-0.7	253
0.7-0.8	34
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8065	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD5760	Phase 2
0.8039	Intermediate Similarity	NPD5761	Phase 2
0.7532	Intermediate Similarity	NPD920	Approved
0.7517	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD8434	Phase 2
0.7403	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1471	Phase 3
0.7285	Intermediate Similarity	NPD2346	Discontinued
0.7273	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6764	Approved
0.7219	Intermediate Similarity	NPD6765	Approved
0.7192	Intermediate Similarity	NPD6832	Phase 2
0.7152	Intermediate Similarity	NPD2799	Discontinued
0.7143	Intermediate Similarity	NPD7819	Suspended
0.7143	Intermediate Similarity	NPD4628	Phase 3
0.7134	Intermediate Similarity	NPD6273	Approved
0.7134	Intermediate Similarity	NPD5494	Approved
0.7105	Intermediate Similarity	NPD2796	Approved
0.7095	Intermediate Similarity	NPD2313	Discontinued
0.7078	Intermediate Similarity	NPD1243	Approved
0.7063	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6599	Discontinued
0.7052	Intermediate Similarity	NPD6784	Approved
0.7052	Intermediate Similarity	NPD6785	Approved
0.7042	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD3972	Approved
0.7012	Intermediate Similarity	NPD3749	Approved
0.7	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD3266	Approved
0.6986	Remote Similarity	NPD3267	Approved
0.697	Remote Similarity	NPD919	Approved
0.6962	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD2344	Approved
0.6946	Remote Similarity	NPD6808	Phase 2
0.6939	Remote Similarity	NPD1019	Discontinued
0.6933	Remote Similarity	NPD8032	Phase 2
0.6928	Remote Similarity	NPD3748	Approved
0.6923	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6559	Discontinued
0.6914	Remote Similarity	NPD7411	Suspended
0.6909	Remote Similarity	NPD7075	Discontinued
0.6894	Remote Similarity	NPD3226	Approved
0.6887	Remote Similarity	NPD4307	Phase 2
0.6882	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD3268	Approved
0.6859	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD2800	Approved
0.6855	Remote Similarity	NPD2533	Approved
0.6855	Remote Similarity	NPD2534	Approved
0.6855	Remote Similarity	NPD2532	Approved
0.6842	Remote Similarity	NPD1933	Approved
0.6824	Remote Similarity	NPD2798	Approved
0.6812	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD1549	Phase 2
0.6792	Remote Similarity	NPD6799	Approved
0.679	Remote Similarity	NPD7458	Discontinued
0.6788	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD1241	Discontinued
0.6786	Remote Similarity	NPD1247	Approved
0.6781	Remote Similarity	NPD9717	Approved
0.6774	Remote Similarity	NPD1551	Phase 2
0.6774	Remote Similarity	NPD2935	Discontinued
0.6772	Remote Similarity	NPD2309	Approved
0.6768	Remote Similarity	NPD6801	Discontinued
0.6757	Remote Similarity	NPD2797	Approved
0.675	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD5585	Approved
0.6731	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.673	Remote Similarity	NPD7236	Approved
0.6727	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.671	Remote Similarity	NPD4308	Phase 3
0.6709	Remote Similarity	NPD7003	Approved
0.6709	Remote Similarity	NPD3750	Approved
0.6707	Remote Similarity	NPD5890	Approved
0.6707	Remote Similarity	NPD5889	Approved
0.669	Remote Similarity	NPD17	Approved
0.6689	Remote Similarity	NPD1876	Approved
0.6667	Remote Similarity	NPD6280	Approved
0.6667	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6279	Approved
0.6667	Remote Similarity	NPD3887	Approved
0.6667	Remote Similarity	NPD2979	Phase 3
0.6647	Remote Similarity	NPD5844	Phase 1
0.6646	Remote Similarity	NPD4380	Phase 2
0.6644	Remote Similarity	NPD1203	Approved
0.6643	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD4618	Approved
0.6623	Remote Similarity	NPD4622	Approved
0.6623	Remote Similarity	NPD447	Suspended
0.6607	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD7033	Discontinued
0.66	Remote Similarity	NPD5647	Approved
0.6595	Remote Similarity	NPD4107	Approved
0.6588	Remote Similarity	NPD6959	Discontinued
0.6587	Remote Similarity	NPD5402	Approved
0.6587	Remote Similarity	NPD3817	Phase 2
0.6582	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD1934	Approved
0.6564	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD5403	Approved
0.6561	Remote Similarity	NPD6099	Approved
0.6561	Remote Similarity	NPD2438	Suspended
0.6561	Remote Similarity	NPD6100	Approved
0.6559	Remote Similarity	NPD4482	Phase 3
0.6558	Remote Similarity	NPD4140	Approved
0.6558	Remote Similarity	NPD3142	Approved
0.6558	Remote Similarity	NPD3140	Approved
0.6554	Remote Similarity	NPD8312	Approved
0.6554	Remote Similarity	NPD8313	Approved
0.6554	Remote Similarity	NPD1608	Approved
0.6548	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD7768	Phase 2
0.6547	Remote Similarity	NPD2182	Approved
0.6545	Remote Similarity	NPD6585	Discontinued
0.6543	Remote Similarity	NPD5401	Approved
0.6538	Remote Similarity	NPD5689	Approved
0.6538	Remote Similarity	NPD5688	Approved
0.6536	Remote Similarity	NPD411	Approved
0.6532	Remote Similarity	NPD7473	Discontinued
0.6524	Remote Similarity	NPD7239	Suspended
0.6519	Remote Similarity	NPD6004	Phase 3
0.6519	Remote Similarity	NPD6002	Phase 3
0.6519	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD6005	Phase 3
0.6516	Remote Similarity	NPD6355	Discontinued
0.6513	Remote Similarity	NPD8404	Phase 2
0.6512	Remote Similarity	NPD3926	Phase 2
0.651	Remote Similarity	NPD4359	Approved
0.65	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4110	Phase 3
0.65	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD1510	Phase 2
0.6494	Remote Similarity	NPD3818	Discontinued
0.6491	Remote Similarity	NPD8127	Discontinued
0.6486	Remote Similarity	NPD1281	Approved
0.6453	Remote Similarity	NPD5710	Approved
0.6453	Remote Similarity	NPD6232	Discontinued
0.6453	Remote Similarity	NPD5711	Approved
0.645	Remote Similarity	NPD3882	Suspended
0.6444	Remote Similarity	NPD8150	Discontinued
0.6442	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3764	Approved
0.6429	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD2353	Approved
0.6415	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5327	Phase 3
0.6398	Remote Similarity	NPD8166	Discontinued
0.6395	Remote Similarity	NPD5691	Approved
0.6393	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD4870	Approved
0.6387	Remote Similarity	NPD6233	Phase 2
0.6375	Remote Similarity	NPD2897	Discontinued
0.6375	Remote Similarity	NPD2424	Discontinued
0.6369	Remote Similarity	NPD6844	Discontinued
0.6369	Remote Similarity	NPD1607	Approved
0.6364	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD7229	Phase 3
0.6358	Remote Similarity	NPD1283	Approved
0.6352	Remote Similarity	NPD2531	Phase 2
0.6351	Remote Similarity	NPD1778	Approved
0.6347	Remote Similarity	NPD7028	Phase 2
0.6346	Remote Similarity	NPD1240	Approved
0.6343	Remote Similarity	NPD3446	Phase 1
0.6331	Remote Similarity	NPD2801	Approved
0.6329	Remote Similarity	NPD7097	Phase 1
0.6323	Remote Similarity	NPD6798	Discontinued
0.6318	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6362	Approved
0.6309	Remote Similarity	NPD3496	Discontinued
0.6301	Remote Similarity	NPD9493	Approved
0.6294	Remote Similarity	NPD5353	Approved
0.6294	Remote Similarity	NPD2296	Approved
0.6292	Remote Similarity	NPD5953	Discontinued
0.6286	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6166	Phase 2
0.6286	Remote Similarity	NPD3134	Approved
0.6286	Remote Similarity	NPD2403	Approved
0.6284	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD1651	Approved
0.6277	Remote Similarity	NPD8285	Discontinued
0.6275	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD37	Approved
0.6271	Remote Similarity	NPD7286	Phase 2
0.6271	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD6287	Discontinued
0.6266	Remote Similarity	NPD6651	Approved
0.6266	Remote Similarity	NPD6653	Approved
0.6265	Remote Similarity	NPD3869	Phase 3

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