NPASS Compound

Structure

NPC474408 OpenBabel07101719152D 24 27 0 0 0 0 0 0 0 0999 V2000 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 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 -4.5000 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 3.4641 -1.0000 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 -1.7321 -4.0000 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 2.5981 -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 -1.7321 -3.0000 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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 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 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 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 23 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 7 1 0 0 0 0 4 8 2 0 0 0 0 5 6 2 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 12 2 0 0 0 0 8 12 1 0 0 0 0 9 13 2 0 0 0 0 10 14 2 0 0 0 0 11 13 1 0 0 0 0 11 24 1 0 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 15 19 2 0 0 0 0 16 18 1 0 0 0 0 16 20 2 0 0 0 0 17 20 1 0 0 0 0 17 21 2 0 0 0 0 18 19 1 0 0 0 0 18 22 2 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.09
Volume:	329.047
LogP:	3.053
LogD:	2.943
LogS:	-5.022
# Rotatable Bonds:	2
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.798
Synthetic Accessibility Score:	2.551
Fsp3:	0.1
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.779
MDCK Permeability:	2.2238134988583624e-05
Pgp-inhibitor:	0.868
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.115

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	99.96593475341797%
Volume Distribution (VD):	0.596
Pgp-substrate:	0.9157013297080994%

ADMET: Metabolism

CYP1A2-inhibitor:	0.975
CYP1A2-substrate:	0.542
CYP2C19-inhibitor:	0.971
CYP2C19-substrate:	0.087
CYP2C9-inhibitor:	0.908
CYP2C9-substrate:	0.688
CYP2D6-inhibitor:	0.942
CYP2D6-substrate:	0.016
CYP3A4-inhibitor:	0.768
CYP3A4-substrate:	0.097

ADMET: Excretion

Clearance (CL):	2.914
Half-life (T1/2):	0.036

ADMET: Toxicity

hERG Blockers:	0.101
Human Hepatotoxicity (H-HT):	0.368
Drug-inuced Liver Injury (DILI):	0.986
AMES Toxicity:	0.659
Rat Oral Acute Toxicity:	0.363
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.058
Carcinogencity:	0.726
Eye Corrosion:	0.003
Eye Irritation:	0.054
Respiratory Toxicity:	0.034

Download Data

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

Natural Product: NPC474408

Natural Product ID:	NPC474408
*Common Name:**	Betulinan B
IUPAC Name:	2-methoxy-3-phenyl-6H-benzo[c]chromene-1,4-dione
Synonyms:
Standard InCHIKey:	IIJJGBPPKPHWQB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H14O4/c1-23-19-15(12-7-3-2-4-8-12)17(21)20-16(18(19)22)14-10-6-5-9-13(14)11-24-20/h2-10H,11H2,1H3
SMILES:	COC1=C(c2ccccc2)C(=O)C2=C(c3ccccc3CO2)C1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL467204
PubChem CID:	3050396
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003411] 2-benzopyrans

*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
NPO41065	Floricola striata	Species	Teichosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27557136]
NPO41065	Floricola striata	Species	Teichosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30137985]
NPO32499	lenzites betulina	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8946751]

☑ 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
Others	1

Activity Type	# Activity
NON-MOLECULAR	1
Others	1
Subcellular	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1084	Subcellular	Liver microsomes	Rattus norvegicus	IC50	=	2.88	ug.mL-1	PMID[533853]
NPT2	Others	Unspecified		IC50	=	2.88	ug.mL-1	PMID[533854]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC80	>	128.0	ug.mL-1	PMID[533855]

☑ 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 NPC474408 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	284
0.1-0.2	1325
0.2-0.3	3013
0.3-0.4	8166
0.4-0.5	11600
0.5-0.6	10106
0.6-0.7	7742
0.7-0.8	430
0.8-0.85	28
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.8636	High Similarity	NPC470391
0.8509	High Similarity	NPC196075
0.8475	Intermediate Similarity	NPC988
0.8475	Intermediate Similarity	NPC289432
0.8435	Intermediate Similarity	NPC228936
0.8421	Intermediate Similarity	NPC13784
0.8407	Intermediate Similarity	NPC291799
0.8403	Intermediate Similarity	NPC144547
0.8362	Intermediate Similarity	NPC135730
0.8333	Intermediate Similarity	NPC212415
0.8318	Intermediate Similarity	NPC103048
0.8279	Intermediate Similarity	NPC295664
0.8224	Intermediate Similarity	NPC12695
0.819	Intermediate Similarity	NPC477411
0.8167	Intermediate Similarity	NPC238861
0.8167	Intermediate Similarity	NPC77000
0.8167	Intermediate Similarity	NPC232958
0.8142	Intermediate Similarity	NPC203732
0.8131	Intermediate Similarity	NPC5472
0.8125	Intermediate Similarity	NPC209632
0.812	Intermediate Similarity	NPC470764
0.812	Intermediate Similarity	NPC210092
0.8091	Intermediate Similarity	NPC112552
0.8087	Intermediate Similarity	NPC137315
0.8087	Intermediate Similarity	NPC474157
0.8051	Intermediate Similarity	NPC471616
0.8051	Intermediate Similarity	NPC226093
0.8049	Intermediate Similarity	NPC51079
0.8036	Intermediate Similarity	NPC114594
0.8034	Intermediate Similarity	NPC67377
0.8017	Intermediate Similarity	NPC473243
0.7983	Intermediate Similarity	NPC190298
0.7966	Intermediate Similarity	NPC474095
0.7949	Intermediate Similarity	NPC272524
0.7949	Intermediate Similarity	NPC161611
0.7946	Intermediate Similarity	NPC60679
0.7931	Intermediate Similarity	NPC210089
0.7913	Intermediate Similarity	NPC99846
0.7913	Intermediate Similarity	NPC269023
0.7913	Intermediate Similarity	NPC192577
0.7909	Intermediate Similarity	NPC145052
0.7881	Intermediate Similarity	NPC308744
0.7863	Intermediate Similarity	NPC309056
0.7863	Intermediate Similarity	NPC79496
0.785	Intermediate Similarity	NPC476484
0.7845	Intermediate Similarity	NPC273837
0.7823	Intermediate Similarity	NPC65627
0.7815	Intermediate Similarity	NPC474685
0.7812	Intermediate Similarity	NPC471832
0.7788	Intermediate Similarity	NPC474365
0.7788	Intermediate Similarity	NPC301943
0.7787	Intermediate Similarity	NPC204784
0.7769	Intermediate Similarity	NPC476644
0.7768	Intermediate Similarity	NPC42211
0.7759	Intermediate Similarity	NPC10251
0.7759	Intermediate Similarity	NPC17417
0.775	Intermediate Similarity	NPC149691
0.7739	Intermediate Similarity	NPC30594
0.7739	Intermediate Similarity	NPC119271
0.7739	Intermediate Similarity	NPC37622
0.7731	Intermediate Similarity	NPC241851
0.7731	Intermediate Similarity	NPC326664
0.7731	Intermediate Similarity	NPC307651
0.7706	Intermediate Similarity	NPC34243
0.7692	Intermediate Similarity	NPC93084
0.7692	Intermediate Similarity	NPC251854
0.7692	Intermediate Similarity	NPC196246
0.7692	Intermediate Similarity	NPC214067
0.7679	Intermediate Similarity	NPC118343
0.7679	Intermediate Similarity	NPC476042
0.7672	Intermediate Similarity	NPC56493
0.7658	Intermediate Similarity	NPC270654
0.7656	Intermediate Similarity	NPC428300
0.7652	Intermediate Similarity	NPC269457
0.7652	Intermediate Similarity	NPC212207
0.7647	Intermediate Similarity	NPC128368
0.7638	Intermediate Similarity	NPC476599
0.7638	Intermediate Similarity	NPC236405
0.7627	Intermediate Similarity	NPC305912
0.7627	Intermediate Similarity	NPC1082
0.7623	Intermediate Similarity	NPC228318
0.7612	Intermediate Similarity	NPC284184
0.7612	Intermediate Similarity	NPC186647
0.7612	Intermediate Similarity	NPC301341
0.7607	Intermediate Similarity	NPC83628
0.7607	Intermediate Similarity	NPC281604
0.7607	Intermediate Similarity	NPC265407
0.7607	Intermediate Similarity	NPC474364
0.7607	Intermediate Similarity	NPC40178
0.7581	Intermediate Similarity	NPC476225
0.7565	Intermediate Similarity	NPC31786
0.7565	Intermediate Similarity	NPC269644
0.7563	Intermediate Similarity	NPC82899
0.7563	Intermediate Similarity	NPC270699
0.7561	Intermediate Similarity	NPC318173
0.7561	Intermediate Similarity	NPC152159
0.7559	Intermediate Similarity	NPC474766
0.7542	Intermediate Similarity	NPC174099
0.7541	Intermediate Similarity	NPC325646
0.7541	Intermediate Similarity	NPC28951
0.754	Intermediate Similarity	NPC164947
0.7537	Intermediate Similarity	NPC232996
0.7537	Intermediate Similarity	NPC475549
0.7536	Intermediate Similarity	NPC472840
0.7521	Intermediate Similarity	NPC470007
0.7521	Intermediate Similarity	NPC47536
0.7519	Intermediate Similarity	NPC23894
0.75	Intermediate Similarity	NPC134120
0.75	Intermediate Similarity	NPC92754
0.75	Intermediate Similarity	NPC201284
0.75	Intermediate Similarity	NPC249912
0.75	Intermediate Similarity	NPC276775
0.7482	Intermediate Similarity	NPC245522
0.7482	Intermediate Similarity	NPC114513
0.7481	Intermediate Similarity	NPC290601
0.7481	Intermediate Similarity	NPC27659
0.748	Intermediate Similarity	NPC469954
0.748	Intermediate Similarity	NPC318067
0.748	Intermediate Similarity	NPC135062
0.748	Intermediate Similarity	NPC473942
0.7479	Intermediate Similarity	NPC243355
0.7479	Intermediate Similarity	NPC260818
0.7479	Intermediate Similarity	NPC167504
0.7479	Intermediate Similarity	NPC21162
0.7478	Intermediate Similarity	NPC89886
0.7458	Intermediate Similarity	NPC469636
0.7456	Intermediate Similarity	NPC70624
0.7444	Intermediate Similarity	NPC310662
0.7442	Intermediate Similarity	NPC177925
0.744	Intermediate Similarity	NPC280827
0.744	Intermediate Similarity	NPC105709
0.744	Intermediate Similarity	NPC243059
0.7438	Intermediate Similarity	NPC153053
0.7438	Intermediate Similarity	NPC196673
0.7434	Intermediate Similarity	NPC35448
0.7434	Intermediate Similarity	NPC225060
0.7434	Intermediate Similarity	NPC78701
0.7431	Intermediate Similarity	NPC110420
0.7431	Intermediate Similarity	NPC303967
0.7431	Intermediate Similarity	NPC67585
0.7426	Intermediate Similarity	NPC475104
0.7426	Intermediate Similarity	NPC476643
0.7424	Intermediate Similarity	NPC477412
0.7424	Intermediate Similarity	NPC475569
0.7422	Intermediate Similarity	NPC246166
0.7419	Intermediate Similarity	NPC64340
0.7417	Intermediate Similarity	NPC186128
0.7417	Intermediate Similarity	NPC321852
0.7417	Intermediate Similarity	NPC474689
0.7414	Intermediate Similarity	NPC249067
0.7405	Intermediate Similarity	NPC473247
0.7394	Intermediate Similarity	NPC474556
0.7391	Intermediate Similarity	NPC222390
0.7391	Intermediate Similarity	NPC244427
0.7388	Intermediate Similarity	NPC474659
0.7385	Intermediate Similarity	NPC478162
0.7385	Intermediate Similarity	NPC478165
0.7381	Intermediate Similarity	NPC50872
0.7373	Intermediate Similarity	NPC211439
0.7373	Intermediate Similarity	NPC156648
0.7368	Intermediate Similarity	NPC325497
0.7368	Intermediate Similarity	NPC203925
0.7368	Intermediate Similarity	NPC146351
0.7368	Intermediate Similarity	NPC183103
0.7364	Intermediate Similarity	NPC119631
0.736	Intermediate Similarity	NPC54243
0.7357	Intermediate Similarity	NPC472836
0.7355	Intermediate Similarity	NPC469547
0.7348	Intermediate Similarity	NPC291419
0.7348	Intermediate Similarity	NPC469519
0.7348	Intermediate Similarity	NPC475478
0.7348	Intermediate Similarity	NPC60825
0.7345	Intermediate Similarity	NPC156021
0.7344	Intermediate Similarity	NPC471466
0.7344	Intermediate Similarity	NPC328107
0.7339	Intermediate Similarity	NPC469574
0.7339	Intermediate Similarity	NPC45794
0.7339	Intermediate Similarity	NPC323440
0.7339	Intermediate Similarity	NPC80605
0.7339	Intermediate Similarity	NPC222968
0.7333	Intermediate Similarity	NPC217914
0.7333	Intermediate Similarity	NPC22644
0.7328	Intermediate Similarity	NPC274443
0.7328	Intermediate Similarity	NPC469930
0.7324	Intermediate Similarity	NPC478163
0.7321	Intermediate Similarity	NPC130398
0.7317	Intermediate Similarity	NPC62138
0.7317	Intermediate Similarity	NPC216387
0.7317	Intermediate Similarity	NPC100353
0.7313	Intermediate Similarity	NPC470406
0.7311	Intermediate Similarity	NPC85493
0.7308	Intermediate Similarity	NPC81135
0.7308	Intermediate Similarity	NPC51292
0.7308	Intermediate Similarity	NPC474264
0.7308	Intermediate Similarity	NPC51037
0.7305	Intermediate Similarity	NPC478166
0.7302	Intermediate Similarity	NPC474223
0.7302	Intermediate Similarity	NPC475827
0.7293	Intermediate Similarity	NPC205360
0.7292	Intermediate Similarity	NPC475718

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 NPC474408 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	244
0.1-0.2	947
0.2-0.3	1050
0.3-0.4	2666
0.4-0.5	2415
0.5-0.6	1390
0.6-0.7	411
0.7-0.8	25
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
0.8333	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.8167	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD2182	Approved
0.7679	Intermediate Similarity	NPD1238	Approved
0.7667	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD1241	Discontinued
0.7565	Intermediate Similarity	NPD164	Approved
0.7565	Intermediate Similarity	NPD5909	Discontinued
0.7542	Intermediate Similarity	NPD2067	Discontinued
0.7422	Intermediate Similarity	NPD1876	Approved
0.7414	Intermediate Similarity	NPD1237	Approved
0.7364	Intermediate Similarity	NPD3266	Approved
0.7364	Intermediate Similarity	NPD3267	Approved
0.7308	Intermediate Similarity	NPD2788	Approved
0.7279	Intermediate Similarity	NPD3748	Approved
0.7273	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD3972	Approved
0.7222	Intermediate Similarity	NPD1651	Approved
0.7188	Intermediate Similarity	NPD6287	Discontinued
0.7188	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD4198	Discontinued
0.7176	Intermediate Similarity	NPD2798	Approved
0.7174	Intermediate Similarity	NPD1471	Phase 3
0.7163	Intermediate Similarity	NPD7236	Approved
0.7154	Intermediate Similarity	NPD5667	Approved
0.7143	Intermediate Similarity	NPD7008	Discontinued
0.7109	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1989	Approved
0.709	Intermediate Similarity	NPD3268	Approved
0.708	Intermediate Similarity	NPD1202	Approved
0.7054	Intermediate Similarity	NPD1281	Approved
0.7031	Intermediate Similarity	NPD17	Approved
0.7021	Intermediate Similarity	NPD3750	Approved
0.7	Intermediate Similarity	NPD4878	Approved
0.7	Intermediate Similarity	NPD2897	Discontinued
0.6985	Remote Similarity	NPD2979	Phase 3
0.6978	Remote Similarity	NPD2796	Approved
0.697	Remote Similarity	NPD2797	Approved
0.6963	Remote Similarity	NPD3764	Approved
0.6963	Remote Similarity	NPD6798	Discontinued
0.6963	Remote Similarity	NPD2313	Discontinued
0.696	Remote Similarity	NPD2629	Approved
0.696	Remote Similarity	NPD5951	Approved
0.694	Remote Similarity	NPD6832	Phase 2
0.6935	Remote Similarity	NPD6858	Approved
0.6935	Remote Similarity	NPD7094	Approved
0.6934	Remote Similarity	NPD6355	Discontinued
0.6929	Remote Similarity	NPD2346	Discontinued
0.6918	Remote Similarity	NPD7239	Suspended
0.6912	Remote Similarity	NPD7713	Phase 3
0.6912	Remote Similarity	NPD6233	Phase 2
0.6899	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD1283	Approved
0.6891	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD1930	Approved
0.6891	Remote Similarity	NPD1929	Approved
0.6875	Remote Similarity	NPD1894	Discontinued
0.687	Remote Similarity	NPD1608	Approved
0.6861	Remote Similarity	NPD4307	Phase 2
0.6853	Remote Similarity	NPD3887	Approved
0.6847	Remote Similarity	NPD1282	Approved
0.6846	Remote Similarity	NPD4879	Approved
0.6838	Remote Similarity	NPD9495	Approved
0.6833	Remote Similarity	NPD3048	Approved
0.6833	Remote Similarity	NPD3046	Approved
0.6833	Remote Similarity	NPD3047	Approved
0.6828	Remote Similarity	NPD5401	Approved
0.6828	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5585	Approved
0.6809	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD2353	Approved
0.6797	Remote Similarity	NPD2347	Approved
0.6797	Remote Similarity	NPD5536	Phase 2
0.6788	Remote Similarity	NPD4062	Phase 3
0.6786	Remote Similarity	NPD1510	Phase 2
0.6783	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7798	Approved
0.678	Remote Similarity	NPD2066	Phase 3
0.6774	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD3225	Approved
0.6765	Remote Similarity	NPD6039	Approved
0.6759	Remote Similarity	NPD6799	Approved
0.6748	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD9545	Approved
0.6742	Remote Similarity	NPD6637	Approved
0.6738	Remote Similarity	NPD2531	Phase 2
0.6738	Remote Similarity	NPD2438	Suspended
0.6735	Remote Similarity	NPD5403	Approved
0.6724	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD4106	Approved
0.6718	Remote Similarity	NPD4136	Approved
0.6718	Remote Similarity	NPD4135	Approved
0.6713	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD650	Approved
0.6692	Remote Similarity	NPD3025	Approved
0.6692	Remote Similarity	NPD3024	Approved
0.6692	Remote Similarity	NPD5691	Approved
0.6691	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.669	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.669	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6273	Approved
0.6667	Remote Similarity	NPD8032	Phase 2
0.6667	Remote Similarity	NPD7003	Approved
0.6667	Remote Similarity	NPD2799	Discontinued
0.6667	Remote Similarity	NPD4628	Phase 3
0.6667	Remote Similarity	NPD8166	Discontinued
0.6667	Remote Similarity	NPD4308	Phase 3
0.6667	Remote Similarity	NPD1201	Approved
0.6667	Remote Similarity	NPD5535	Approved
0.6645	Remote Similarity	NPD3817	Phase 2
0.6644	Remote Similarity	NPD3950	Discontinued
0.6642	Remote Similarity	NPD7095	Approved
0.6641	Remote Similarity	NPD2932	Approved
0.6641	Remote Similarity	NPD5306	Approved
0.6641	Remote Similarity	NPD5305	Approved
0.6621	Remote Similarity	NPD2354	Approved
0.6621	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.662	Remote Similarity	NPD4477	Approved
0.662	Remote Similarity	NPD4476	Approved
0.6619	Remote Similarity	NPD4060	Phase 1
0.6619	Remote Similarity	NPD3142	Approved
0.6619	Remote Similarity	NPD3140	Approved
0.6612	Remote Similarity	NPD6647	Phase 2
0.661	Remote Similarity	NPD3495	Discontinued
0.6609	Remote Similarity	NPD7609	Phase 3
0.6607	Remote Similarity	NPD9257	Approved
0.6607	Remote Similarity	NPD9259	Approved
0.6601	Remote Similarity	NPD7058	Phase 2
0.6601	Remote Similarity	NPD7057	Phase 3
0.66	Remote Similarity	NPD6599	Discontinued
0.6594	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD1470	Approved
0.6591	Remote Similarity	NPD3026	Approved
0.6591	Remote Similarity	NPD3023	Approved
0.6589	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD3134	Approved
0.6583	Remote Similarity	NPD2549	Approved
0.6583	Remote Similarity	NPD2552	Approved
0.6583	Remote Similarity	NPD2558	Approved
0.6583	Remote Similarity	NPD2555	Approved
0.6583	Remote Similarity	NPD2550	Approved
0.6583	Remote Similarity	NPD2553	Approved
0.6579	Remote Similarity	NPD7819	Suspended
0.6579	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD2344	Approved
0.6573	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4622	Approved
0.6571	Remote Similarity	NPD4618	Approved
0.6571	Remote Similarity	NPD1933	Approved
0.6569	Remote Similarity	NPD7055	Discontinued
0.6567	Remote Similarity	NPD4359	Approved
0.6565	Remote Similarity	NPD4105	Approved
0.6565	Remote Similarity	NPD4102	Approved
0.656	Remote Similarity	NPD5240	Approved
0.656	Remote Similarity	NPD5236	Approved
0.656	Remote Similarity	NPD5235	Approved
0.656	Remote Similarity	NPD5237	Approved
0.656	Remote Similarity	NPD5239	Approved
0.6555	Remote Similarity	NPD5926	Approved
0.6552	Remote Similarity	NPD7631	Approved
0.6544	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD4806	Approved
0.6541	Remote Similarity	NPD4807	Approved
0.6536	Remote Similarity	NPD5402	Approved
0.6533	Remote Similarity	NPD3226	Approved
0.6533	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD7458	Discontinued
0.6532	Remote Similarity	NPD1358	Approved
0.6529	Remote Similarity	NPD1932	Approved
0.6529	Remote Similarity	NPD4189	Approved
0.6529	Remote Similarity	NPD4188	Approved
0.6528	Remote Similarity	NPD1549	Phase 2
0.6528	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD4534	Discontinued
0.6522	Remote Similarity	NPD3673	Approved
0.6522	Remote Similarity	NPD3672	Approved
0.6519	Remote Similarity	NPD2199	Approved
0.6519	Remote Similarity	NPD2198	Approved
0.6515	Remote Similarity	NPD5126	Approved
0.6515	Remote Similarity	NPD3019	Approved
0.6515	Remote Similarity	NPD5125	Phase 3
0.6514	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD6801	Discontinued
0.6512	Remote Similarity	NPD3317	Approved
0.65	Remote Similarity	NPD1240	Approved
0.6496	Remote Similarity	NPD1563	Approved
0.6493	Remote Similarity	NPD1481	Phase 2
0.649	Remote Similarity	NPD4380	Phase 2
0.6486	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5283	Phase 1
0.6479	Remote Similarity	NPD5688	Approved
0.6479	Remote Similarity	NPD5689	Approved
0.6471	Remote Similarity	NPD1203	Approved
0.6466	Remote Similarity	NPD3847	Discontinued
0.6466	Remote Similarity	NPD1239	Approved
0.6462	Remote Similarity	NPD9493	Approved
0.6457	Remote Similarity	NPD969	Suspended
0.6455	Remote Similarity	NPD942	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