NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	280.13
Volume:	272.449
LogP:	0.895
LogD:	0.102
LogS:	-3.742
# Rotatable Bonds:	2
TPSA:	82.59
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.557
Synthetic Accessibility Score:	5.428
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.237
MDCK Permeability:	1.6886402590898797e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.341
Human Intestinal Absorption (HIA):	0.034
20% Bioavailability (F20%):	0.884
30% Bioavailability (F30%):	0.64

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.951
Plasma Protein Binding (PPB):	40.5981330871582%
Volume Distribution (VD):	0.612
Pgp-substrate:	69.25178527832031%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.971
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.836
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.027
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.109
CYP3A4-inhibitor:	0.051
CYP3A4-substrate:	0.666

ADMET: Excretion

Clearance (CL):	2.543
Half-life (T1/2):	0.915

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.285
Drug-inuced Liver Injury (DILI):	0.748
AMES Toxicity:	0.959
Rat Oral Acute Toxicity:	0.744
Maximum Recommended Daily Dose:	0.356
Skin Sensitization:	0.89
Carcinogencity:	0.333
Eye Corrosion:	0.044
Eye Irritation:	0.831
Respiratory Toxicity:	0.587

Download Data

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

Natural Product: NPC478176

Natural Product ID:	NPC478176
*Common Name:**	(+)-Phaseolinone
IUPAC Name:	(1aR,6R,7R,7aR,7bR)-6-hydroxy-1a-[(2R)-2-(hydroxymethyl)oxiran-2-yl]-7,7a-dimethyl-5,6,7,7b-tetrahydro-4H-naphtho[1,2-b]oxiren-2-one
Synonyms:	(+)-Phaseolinone
Standard InCHIKey:	DDKJQSAECJSUNP-BNVLTIKWSA-N
Standard InCHI:	InChI=1S/C15H20O5/c1-8-10(17)4-3-9-5-11(18)15(14(6-16)7-19-14)12(20-15)13(8,9)2/h5,8,10,12,16-17H,3-4,6-7H2,1-2H3/t8-,10+,12+,13+,14+,15+/m0/s1
SMILES:	C[C@H]1[C@@H](CCC2=CC(=O)[C@@]3([C@@H]([C@]12C)O3)[C@]4(CO4)CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	49799779
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO33525	Xylaria sp. BCC 1067	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]

☑ 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
EC50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	EC50	=	0.5	ug/ml	PMID[19299148]

☑ 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 NPC478176 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	233
0.1-0.2	1452
0.2-0.3	5204
0.3-0.4	9516
0.4-0.5	13650
0.5-0.6	7572
0.6-0.7	4530
0.7-0.8	523
0.8-0.85	8
0.85-0.9	8
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9082	High Similarity	NPC112613
0.902	High Similarity	NPC87335
0.8889	High Similarity	NPC207885
0.8866	High Similarity	NPC94337
0.8776	High Similarity	NPC471916
0.8679	High Similarity	NPC477266
0.8667	High Similarity	NPC317107
0.8585	High Similarity	NPC317687
0.84	Intermediate Similarity	NPC236176
0.8381	Intermediate Similarity	NPC322903
0.835	Intermediate Similarity	NPC131366
0.8318	Intermediate Similarity	NPC476023
0.8252	Intermediate Similarity	NPC39996
0.8174	Intermediate Similarity	NPC225049
0.8148	Intermediate Similarity	NPC207689
0.8137	Intermediate Similarity	NPC264378
0.81	Intermediate Similarity	NPC196227
0.8081	Intermediate Similarity	NPC116726
0.8036	Intermediate Similarity	NPC17772
0.8021	Intermediate Similarity	NPC79573
0.8018	Intermediate Similarity	NPC207217
0.8018	Intermediate Similarity	NPC270478
0.8	Intermediate Similarity	NPC7921
0.8	Intermediate Similarity	NPC208998
0.7982	Intermediate Similarity	NPC477046
0.7982	Intermediate Similarity	NPC146945
0.7982	Intermediate Similarity	NPC474229
0.7982	Intermediate Similarity	NPC102822
0.7982	Intermediate Similarity	NPC171888
0.798	Intermediate Similarity	NPC473099
0.798	Intermediate Similarity	NPC477684
0.7946	Intermediate Similarity	NPC474654
0.7946	Intermediate Similarity	NPC97908
0.7946	Intermediate Similarity	NPC287343
0.7946	Intermediate Similarity	NPC122033
0.7946	Intermediate Similarity	NPC470854
0.7944	Intermediate Similarity	NPC144854
0.7944	Intermediate Similarity	NPC3316
0.7928	Intermediate Similarity	NPC80650
0.7928	Intermediate Similarity	NPC247069
0.79	Intermediate Similarity	NPC475441
0.7885	Intermediate Similarity	NPC472972
0.7881	Intermediate Similarity	NPC477712
0.7881	Intermediate Similarity	NPC477713
0.7879	Intermediate Similarity	NPC473100
0.7876	Intermediate Similarity	NPC251310
0.7876	Intermediate Similarity	NPC297179
0.787	Intermediate Similarity	NPC154608
0.787	Intermediate Similarity	NPC277017
0.787	Intermediate Similarity	NPC293850
0.787	Intermediate Similarity	NPC192813
0.7857	Intermediate Similarity	NPC474333
0.7857	Intermediate Similarity	NPC328374
0.7857	Intermediate Similarity	NPC96312
0.7857	Intermediate Similarity	NPC40632
0.7857	Intermediate Similarity	NPC251236
0.785	Intermediate Similarity	NPC128828
0.785	Intermediate Similarity	NPC471332
0.785	Intermediate Similarity	NPC471333
0.7843	Intermediate Similarity	NPC248574
0.7843	Intermediate Similarity	NPC476245
0.7838	Intermediate Similarity	NPC198539
0.7838	Intermediate Similarity	NPC49451
0.7833	Intermediate Similarity	NPC476193
0.783	Intermediate Similarity	NPC118902
0.783	Intermediate Similarity	NPC473624
0.783	Intermediate Similarity	NPC469980
0.783	Intermediate Similarity	NPC104161
0.7807	Intermediate Similarity	NPC470777
0.7788	Intermediate Similarity	NPC296822
0.7788	Intermediate Similarity	NPC469565
0.7788	Intermediate Similarity	NPC58662
0.7778	Intermediate Similarity	NPC8374
0.7778	Intermediate Similarity	NPC476706
0.7778	Intermediate Similarity	NPC476707
0.7778	Intermediate Similarity	NPC473165
0.7768	Intermediate Similarity	NPC473798
0.7767	Intermediate Similarity	NPC279722
0.7767	Intermediate Similarity	NPC91439
0.7757	Intermediate Similarity	NPC296950
0.7755	Intermediate Similarity	NPC262026
0.7748	Intermediate Similarity	NPC474516
0.7748	Intermediate Similarity	NPC473877
0.7745	Intermediate Similarity	NPC478089
0.7739	Intermediate Similarity	NPC478051
0.7736	Intermediate Similarity	NPC283567
0.7727	Intermediate Similarity	NPC210005
0.7719	Intermediate Similarity	NPC240509
0.7719	Intermediate Similarity	NPC204552
0.7719	Intermediate Similarity	NPC188667
0.7714	Intermediate Similarity	NPC46761
0.7706	Intermediate Similarity	NPC469916
0.7706	Intermediate Similarity	NPC472439
0.7706	Intermediate Similarity	NPC151393
0.7699	Intermediate Similarity	NPC134869
0.7699	Intermediate Similarity	NPC235539
0.7699	Intermediate Similarity	NPC152199
0.7692	Intermediate Similarity	NPC20078
0.7692	Intermediate Similarity	NPC473574
0.7692	Intermediate Similarity	NPC27105
0.7692	Intermediate Similarity	NPC272451
0.7685	Intermediate Similarity	NPC102352
0.7685	Intermediate Similarity	NPC470587
0.7685	Intermediate Similarity	NPC166607
0.7679	Intermediate Similarity	NPC317210
0.7679	Intermediate Similarity	NPC159333
0.7679	Intermediate Similarity	NPC477126
0.7679	Intermediate Similarity	NPC194100
0.7672	Intermediate Similarity	NPC67569
0.767	Intermediate Similarity	NPC477438
0.767	Intermediate Similarity	NPC477437
0.7664	Intermediate Similarity	NPC159533
0.766	Intermediate Similarity	NPC178852
0.7658	Intermediate Similarity	NPC471243
0.7658	Intermediate Similarity	NPC201992
0.7647	Intermediate Similarity	NPC477435
0.7647	Intermediate Similarity	NPC477436
0.7642	Intermediate Similarity	NPC181645
0.7642	Intermediate Similarity	NPC97435
0.7636	Intermediate Similarity	NPC77089
0.7636	Intermediate Similarity	NPC475922
0.7636	Intermediate Similarity	NPC470257
0.7632	Intermediate Similarity	NPC27999
0.7632	Intermediate Similarity	NPC477116
0.7632	Intermediate Similarity	NPC53396
0.7632	Intermediate Similarity	NPC98249
0.7632	Intermediate Similarity	NPC469684
0.7629	Intermediate Similarity	NPC64600
0.7627	Intermediate Similarity	NPC24651
0.7624	Intermediate Similarity	NPC475823
0.7624	Intermediate Similarity	NPC134321
0.7624	Intermediate Similarity	NPC128672
0.7624	Intermediate Similarity	NPC474209
0.7619	Intermediate Similarity	NPC471330
0.7619	Intermediate Similarity	NPC471331
0.7619	Intermediate Similarity	NPC99657
0.7619	Intermediate Similarity	NPC203388
0.7619	Intermediate Similarity	NPC472687
0.7615	Intermediate Similarity	NPC266514
0.7615	Intermediate Similarity	NPC67321
0.7615	Intermediate Similarity	NPC187435
0.7611	Intermediate Similarity	NPC268238
0.7611	Intermediate Similarity	NPC18547
0.7611	Intermediate Similarity	NPC474906
0.7611	Intermediate Similarity	NPC45218
0.7611	Intermediate Similarity	NPC323821
0.7611	Intermediate Similarity	NPC238667
0.7611	Intermediate Similarity	NPC143268
0.7607	Intermediate Similarity	NPC153700
0.7607	Intermediate Similarity	NPC88326
0.7607	Intermediate Similarity	NPC23786
0.7607	Intermediate Similarity	NPC470265
0.7607	Intermediate Similarity	NPC312833
0.7596	Intermediate Similarity	NPC472734
0.7596	Intermediate Similarity	NPC469369
0.7596	Intermediate Similarity	NPC472733
0.7596	Intermediate Similarity	NPC469528
0.7596	Intermediate Similarity	NPC272411
0.7593	Intermediate Similarity	NPC72255
0.7593	Intermediate Similarity	NPC160843
0.7593	Intermediate Similarity	NPC146731
0.7593	Intermediate Similarity	NPC258532
0.7593	Intermediate Similarity	NPC40170
0.7589	Intermediate Similarity	NPC11252
0.7589	Intermediate Similarity	NPC289312
0.7589	Intermediate Similarity	NPC90769
0.7589	Intermediate Similarity	NPC42658
0.7586	Intermediate Similarity	NPC112038
0.7576	Intermediate Similarity	NPC94666
0.7576	Intermediate Similarity	NPC196381
0.7576	Intermediate Similarity	NPC179591
0.7576	Intermediate Similarity	NPC255143
0.7573	Intermediate Similarity	NPC103527
0.7573	Intermediate Similarity	NPC477439
0.7573	Intermediate Similarity	NPC245972
0.7573	Intermediate Similarity	NPC174051
0.7573	Intermediate Similarity	NPC67831
0.7573	Intermediate Similarity	NPC196485
0.757	Intermediate Similarity	NPC476126
0.757	Intermediate Similarity	NPC476235
0.7568	Intermediate Similarity	NPC5103
0.7568	Intermediate Similarity	NPC115257
0.7568	Intermediate Similarity	NPC235077
0.7568	Intermediate Similarity	NPC474567
0.7568	Intermediate Similarity	NPC161816
0.7565	Intermediate Similarity	NPC284707
0.7565	Intermediate Similarity	NPC50774
0.7565	Intermediate Similarity	NPC470776
0.7565	Intermediate Similarity	NPC709
0.7565	Intermediate Similarity	NPC186525
0.7553	Intermediate Similarity	NPC197659
0.7551	Intermediate Similarity	NPC469809
0.7551	Intermediate Similarity	NPC60951
0.7549	Intermediate Similarity	NPC73457
0.7549	Intermediate Similarity	NPC476705
0.7549	Intermediate Similarity	NPC26865
0.7545	Intermediate Similarity	NPC264819
0.7544	Intermediate Similarity	NPC16081
0.7544	Intermediate Similarity	NPC173686
0.7544	Intermediate Similarity	NPC179626

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 NPC478176 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	1936
0.2-0.3	3918
0.3-0.4	2046
0.4-0.5	660
0.5-0.6	231
0.6-0.7	146
0.7-0.8	7
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
0.7586	Intermediate Similarity	NPD6319	Approved
0.7568	Intermediate Similarity	NPD4634	Approved
0.7478	Intermediate Similarity	NPD7115	Discovery
0.7477	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6059	Approved
0.7436	Intermediate Similarity	NPD6054	Approved
0.7404	Intermediate Similarity	NPD5282	Discontinued
0.7395	Intermediate Similarity	NPD8328	Phase 3
0.7373	Intermediate Similarity	NPD6016	Approved
0.7373	Intermediate Similarity	NPD6015	Approved
0.7364	Intermediate Similarity	NPD5739	Approved
0.7364	Intermediate Similarity	NPD6675	Approved
0.7364	Intermediate Similarity	NPD7128	Approved
0.7364	Intermediate Similarity	NPD6402	Approved
0.7358	Intermediate Similarity	NPD4755	Approved
0.7321	Intermediate Similarity	NPD6372	Approved
0.7321	Intermediate Similarity	NPD6373	Approved
0.7311	Intermediate Similarity	NPD5988	Approved
0.7311	Intermediate Similarity	NPD6370	Approved
0.7297	Intermediate Similarity	NPD5701	Approved
0.7297	Intermediate Similarity	NPD5697	Approved
0.7281	Intermediate Similarity	NPD8297	Approved
0.7257	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD7320	Approved
0.7232	Intermediate Similarity	NPD6881	Approved
0.7232	Intermediate Similarity	NPD6899	Approved
0.7228	Intermediate Similarity	NPD3618	Phase 1
0.7222	Intermediate Similarity	NPD5285	Approved
0.7222	Intermediate Similarity	NPD4696	Approved
0.7222	Intermediate Similarity	NPD4700	Approved
0.7222	Intermediate Similarity	NPD5286	Approved
0.7217	Intermediate Similarity	NPD4632	Approved
0.7193	Intermediate Similarity	NPD6650	Approved
0.7193	Intermediate Similarity	NPD6649	Approved
0.719	Intermediate Similarity	NPD7492	Approved
0.7168	Intermediate Similarity	NPD6012	Approved
0.7168	Intermediate Similarity	NPD6013	Approved
0.7168	Intermediate Similarity	NPD6014	Approved
0.7131	Intermediate Similarity	NPD6616	Approved
0.713	Intermediate Similarity	NPD4225	Approved
0.7105	Intermediate Similarity	NPD7290	Approved
0.7105	Intermediate Similarity	NPD6883	Approved
0.7105	Intermediate Similarity	NPD7102	Approved
0.7103	Intermediate Similarity	NPD4697	Phase 3
0.7091	Intermediate Similarity	NPD5225	Approved
0.7091	Intermediate Similarity	NPD4633	Approved
0.7091	Intermediate Similarity	NPD5226	Approved
0.7091	Intermediate Similarity	NPD5224	Approved
0.7091	Intermediate Similarity	NPD5211	Phase 2
0.708	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6011	Approved
0.7073	Intermediate Similarity	NPD8293	Discontinued
0.7073	Intermediate Similarity	NPD7078	Approved
0.7054	Intermediate Similarity	NPD6008	Approved
0.7043	Intermediate Similarity	NPD6847	Approved
0.7043	Intermediate Similarity	NPD6617	Approved
0.7043	Intermediate Similarity	NPD8130	Phase 1
0.7043	Intermediate Similarity	NPD6869	Approved
0.7037	Intermediate Similarity	NPD7902	Approved
0.7037	Intermediate Similarity	NPD6084	Phase 2
0.7037	Intermediate Similarity	NPD6083	Phase 2
0.7034	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6009	Approved
0.7027	Intermediate Similarity	NPD5174	Approved
0.7027	Intermediate Similarity	NPD5175	Approved
0.7019	Intermediate Similarity	NPD4753	Phase 2
0.7016	Intermediate Similarity	NPD7736	Approved
0.7009	Intermediate Similarity	NPD5695	Phase 3
0.7	Intermediate Similarity	NPD5344	Discontinued
0.7	Intermediate Similarity	NPD5223	Approved
0.6991	Remote Similarity	NPD6412	Phase 2
0.6991	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD6882	Approved
0.6981	Remote Similarity	NPD4202	Approved
0.6972	Remote Similarity	NPD5696	Approved
0.6967	Remote Similarity	NPD7604	Phase 2
0.6964	Remote Similarity	NPD5141	Approved
0.6944	Remote Similarity	NPD5221	Approved
0.6944	Remote Similarity	NPD5222	Approved
0.6944	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD5983	Phase 2
0.6916	Remote Similarity	NPD7748	Approved
0.6903	Remote Similarity	NPD4767	Approved
0.6903	Remote Similarity	NPD4768	Approved
0.6897	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7515	Phase 2
0.6881	Remote Similarity	NPD5173	Approved
0.688	Remote Similarity	NPD6033	Approved
0.6875	Remote Similarity	NPD4754	Approved
0.6857	Remote Similarity	NPD5328	Approved
0.6852	Remote Similarity	NPD5210	Approved
0.6852	Remote Similarity	NPD4629	Approved
0.6832	Remote Similarity	NPD3667	Approved
0.6822	Remote Similarity	NPD6399	Phase 3
0.681	Remote Similarity	NPD6371	Approved
0.6807	Remote Similarity	NPD6274	Approved
0.68	Remote Similarity	NPD4695	Discontinued
0.6792	Remote Similarity	NPD6698	Approved
0.6792	Remote Similarity	NPD46	Approved
0.6783	Remote Similarity	NPD5128	Approved
0.6783	Remote Similarity	NPD4730	Approved
0.6783	Remote Similarity	NPD4729	Approved
0.6759	Remote Similarity	NPD7900	Approved
0.6759	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD5279	Phase 3
0.6729	Remote Similarity	NPD6079	Approved
0.6729	Remote Similarity	NPD6411	Approved
0.6724	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6336	Discontinued
0.6699	Remote Similarity	NPD3666	Approved
0.6699	Remote Similarity	NPD3665	Phase 1
0.6699	Remote Similarity	NPD4786	Approved
0.6699	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD5248	Approved
0.6667	Remote Similarity	NPD5251	Approved
0.6667	Remote Similarity	NPD5247	Approved
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD5250	Approved
0.6667	Remote Similarity	NPD5249	Phase 3
0.6667	Remote Similarity	NPD5779	Approved
0.6639	Remote Similarity	NPD7101	Approved
0.6639	Remote Similarity	NPD7100	Approved
0.6639	Remote Similarity	NPD4522	Approved
0.6634	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6317	Approved
0.661	Remote Similarity	NPD5216	Approved
0.661	Remote Similarity	NPD5217	Approved
0.661	Remote Similarity	NPD5215	Approved
0.6607	Remote Similarity	NPD6648	Approved
0.6604	Remote Similarity	NPD6672	Approved
0.6604	Remote Similarity	NPD5737	Approved
0.6557	Remote Similarity	NPD6313	Approved
0.6557	Remote Similarity	NPD6314	Approved
0.6557	Remote Similarity	NPD6335	Approved
0.6552	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD6101	Approved
0.6538	Remote Similarity	NPD4197	Approved
0.6532	Remote Similarity	NPD6909	Approved
0.6532	Remote Similarity	NPD6908	Approved
0.6525	Remote Similarity	NPD5135	Approved
0.6525	Remote Similarity	NPD5169	Approved
0.6525	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD7638	Approved
0.6512	Remote Similarity	NPD5956	Approved
0.6496	Remote Similarity	NPD6686	Approved
0.6481	Remote Similarity	NPD3168	Discontinued
0.6476	Remote Similarity	NPD5329	Approved
0.6476	Remote Similarity	NPD1696	Phase 3
0.6476	Remote Similarity	NPD1694	Approved
0.6471	Remote Similarity	NPD5127	Approved
0.646	Remote Similarity	NPD7640	Approved
0.646	Remote Similarity	NPD7639	Approved
0.6442	Remote Similarity	NPD6110	Phase 1
0.6434	Remote Similarity	NPD7319	Approved
0.6415	Remote Similarity	NPD5280	Approved
0.6415	Remote Similarity	NPD5690	Phase 2
0.6415	Remote Similarity	NPD4694	Approved
0.64	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6921	Approved
0.6396	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD6868	Approved
0.6389	Remote Similarity	NPD6673	Approved
0.6389	Remote Similarity	NPD6904	Approved
0.6389	Remote Similarity	NPD6080	Approved
0.6381	Remote Similarity	NPD3668	Phase 3
0.6356	Remote Similarity	NPD5168	Approved
0.6355	Remote Similarity	NPD7524	Approved
0.6355	Remote Similarity	NPD3573	Approved
0.6346	Remote Similarity	NPD4223	Phase 3
0.6346	Remote Similarity	NPD4221	Approved
0.633	Remote Similarity	NPD5692	Phase 3
0.6328	Remote Similarity	NPD7507	Approved
0.6311	Remote Similarity	NPD5167	Approved
0.6306	Remote Similarity	NPD6001	Approved
0.6299	Remote Similarity	NPD6067	Discontinued
0.6275	Remote Similarity	NPD3617	Approved
0.6273	Remote Similarity	NPD5284	Approved
0.6273	Remote Similarity	NPD7983	Approved
0.6273	Remote Similarity	NPD5281	Approved
0.6273	Remote Similarity	NPD5693	Phase 1
0.6273	Remote Similarity	NPD5694	Approved
0.6273	Remote Similarity	NPD6050	Approved
0.627	Remote Similarity	NPD8516	Approved
0.627	Remote Similarity	NPD8517	Approved
0.627	Remote Similarity	NPD8513	Phase 3
0.627	Remote Similarity	NPD8515	Approved
0.6262	Remote Similarity	NPD7146	Approved
0.6262	Remote Similarity	NPD5330	Approved
0.6262	Remote Similarity	NPD7521	Approved
0.6262	Remote Similarity	NPD7334	Approved
0.6262	Remote Similarity	NPD6684	Approved
0.6262	Remote Similarity	NPD6409	Approved
0.6261	Remote Similarity	NPD1700	Approved
0.6239	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD7645	Phase 2
0.6182	Remote Similarity	NPD7838	Discovery

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