NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	266.13
Volume:	299.26
LogP:	3.063
LogD:	2.907
LogS:	-3.353
# Rotatable Bonds:	5
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.803
Synthetic Accessibility Score:	2.256
Fsp3:	0.111
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.739
MDCK Permeability:	3.0334405892062932e-05
Pgp-inhibitor:	0.898
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.837
30% Bioavailability (F30%):	0.232

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.032
Plasma Protein Binding (PPB):	94.47171783447266%
Volume Distribution (VD):	0.488
Pgp-substrate:	2.431234359741211%

ADMET: Metabolism

CYP1A2-inhibitor:	0.766
CYP1A2-substrate:	0.072
CYP2C19-inhibitor:	0.933
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.805
CYP2C9-substrate:	0.474
CYP2D6-inhibitor:	0.848
CYP2D6-substrate:	0.858
CYP3A4-inhibitor:	0.376
CYP3A4-substrate:	0.272

ADMET: Excretion

Clearance (CL):	16.348
Half-life (T1/2):	0.91

ADMET: Toxicity

hERG Blockers:	0.09
Human Hepatotoxicity (H-HT):	0.071
Drug-inuced Liver Injury (DILI):	0.497
AMES Toxicity:	0.465
Rat Oral Acute Toxicity:	0.079
Maximum Recommended Daily Dose:	0.114
Skin Sensitization:	0.896
Carcinogencity:	0.533
Eye Corrosion:	0.003
Eye Irritation:	0.316
Respiratory Toxicity:	0.131

Download Data

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

Natural Product: NPC151715

Natural Product ID:	NPC151715
*Common Name:**	Anolignan B
IUPAC Name:	4-[3-[(4-hydroxyphenyl)methyl]-2-methylidenebut-3-enyl]phenol
Synonyms:
Standard InCHIKey:	VVKZAZVVUAFFGF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H18O2/c1-13(11-15-3-7-17(19)8-4-15)14(2)12-16-5-9-18(20)10-6-16/h3-10,19-20H,1-2,11-12H2
SMILES:	C=C(C(=C)Cc1ccc(cc1)O)Cc1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL456870
PubChem CID:	72388
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0004646] 1-hydroxy-2-unsubstituted benzenoids

*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
NPO2134	Anogeissus acuminata	Species	Combretaceae	Eukaryota	n.a.	stem	n.a.	PMID[7525878]
NPO33381	terminalia bellerica	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9249982]
NPO28101	Fructus terminaliae billericae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO2134	Anogeissus acuminata	Species	Combretaceae	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
EC50	1
ED50	13
IC50	2
Others	9

Activity Type	# Activity
Cell Line	8
Individual Protein	8
NON-MOLECULAR	5
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	Inhibition	=	32.9	%	PMID[475022]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	Inhibition	=	31.2	%	PMID[475022]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	Inhibition	=	27.4	%	PMID[475022]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	Inhibition	=	20.9	%	PMID[475022]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	Inhibition	=	25.5	%	PMID[475022]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	Inhibition	=	17.7	%	PMID[475022]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	Inhibition	=	10.0	%	PMID[475022]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	=	1072.0	ug.mL-1	PMID[475022]
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[475022]
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[475022]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[475022]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[475022]
NPT168	Cell Line	P388	Mus musculus	ED50	=	1.0	ug ml-1	PMID[475022]
NPT762	Cell Line	A-431	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[475022]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[475022]
NPT133	Cell Line	ZR-75-1	Homo sapiens	ED50	=	9.5	ug ml-1	PMID[475022]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	20500.0	nM	PMID[475021]
NPT3086	Organism	Penicillium expansum	Penicillium expansum	Activity	=	5.0	ug	PMID[475021]
NPT20	Organism	Candida albicans	Candida albicans	Activity	>	200.0	ug	PMID[475021]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	7000.0	nM	PMID[475021]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	5.1	ug ml-1	PMID[475022]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	20.0	ug ml-1	PMID[475022]

☑ 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 NPC151715 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	250
0.1-0.2	1967
0.2-0.3	6245
0.3-0.4	12751
0.4-0.5	5936
0.5-0.6	9339
0.6-0.7	4663
0.7-0.8	1179
0.8-0.85	213
0.85-0.9	107
0.9-0.95	31
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
0.9888	High Similarity	NPC26244
0.9778	High Similarity	NPC473388
0.9773	High Similarity	NPC45040
0.9565	High Similarity	NPC216468
0.9565	High Similarity	NPC132078
0.9565	High Similarity	NPC51333
0.9565	High Similarity	NPC78119
0.956	High Similarity	NPC82664
0.956	High Similarity	NPC292730
0.956	High Similarity	NPC216520
0.956	High Similarity	NPC132271
0.9556	High Similarity	NPC128062
0.9462	High Similarity	NPC213730
0.9451	High Similarity	NPC274678
0.9362	High Similarity	NPC7686
0.9362	High Similarity	NPC91461
0.9362	High Similarity	NPC40258
0.9355	High Similarity	NPC92730
0.9341	High Similarity	NPC76938
0.9326	High Similarity	NPC177420
0.9326	High Similarity	NPC280347
0.9326	High Similarity	NPC318325
0.9326	High Similarity	NPC123273
0.9326	High Similarity	NPC242240
0.9263	High Similarity	NPC168829
0.9247	High Similarity	NPC225464
0.9239	High Similarity	NPC32714
0.9222	High Similarity	NPC55561
0.9213	High Similarity	NPC25493
0.9213	High Similarity	NPC113460
0.9167	High Similarity	NPC120693
0.9167	High Similarity	NPC8931
0.9167	High Similarity	NPC288411
0.9167	High Similarity	NPC261573
0.9111	High Similarity	NPC258219
0.9101	High Similarity	NPC23167
0.9091	High Similarity	NPC175313
0.9072	High Similarity	NPC474839
0.9072	High Similarity	NPC138942
0.9072	High Similarity	NPC154899
0.9072	High Similarity	NPC233396
0.9062	High Similarity	NPC135784
0.9053	High Similarity	NPC294741
0.9043	High Similarity	NPC201967
0.9022	High Similarity	NPC271440
0.9011	High Similarity	NPC300017
0.9011	High Similarity	NPC192
0.8989	High Similarity	NPC197783
0.898	High Similarity	NPC188677
0.898	High Similarity	NPC113457
0.898	High Similarity	NPC135464
0.898	High Similarity	NPC92623
0.8977	High Similarity	NPC265146
0.8969	High Similarity	NPC119860
0.8947	High Similarity	NPC130193
0.8925	High Similarity	NPC27323
0.8925	High Similarity	NPC316301
0.8913	High Similarity	NPC304541
0.8913	High Similarity	NPC270547
0.8901	High Similarity	NPC98772
0.8889	High Similarity	NPC184169
0.8876	High Similarity	NPC248817
0.8842	High Similarity	NPC32674
0.8817	High Similarity	NPC94139
0.8817	High Similarity	NPC147284
0.8817	High Similarity	NPC162314
0.8817	High Similarity	NPC3358
0.8817	High Similarity	NPC325292
0.8817	High Similarity	NPC210497
0.8817	High Similarity	NPC306884
0.8817	High Similarity	NPC138117
0.88	High Similarity	NPC61885
0.88	High Similarity	NPC262365
0.88	High Similarity	NPC63698
0.88	High Similarity	NPC11554
0.8791	High Similarity	NPC104216
0.8788	High Similarity	NPC70843
0.8788	High Similarity	NPC29989
0.8788	High Similarity	NPC271274
0.8788	High Similarity	NPC69332
0.8788	High Similarity	NPC95178
0.8778	High Similarity	NPC155393
0.8776	High Similarity	NPC323810
0.8776	High Similarity	NPC241891
0.8776	High Similarity	NPC30506
0.8776	High Similarity	NPC471511
0.8764	High Similarity	NPC124436
0.875	High Similarity	NPC128723
0.8713	High Similarity	NPC88141
0.8713	High Similarity	NPC254833
0.8713	High Similarity	NPC228343
0.8713	High Similarity	NPC62258
0.8713	High Similarity	NPC55617
0.8713	High Similarity	NPC306045
0.8713	High Similarity	NPC265211
0.871	High Similarity	NPC204210
0.871	High Similarity	NPC155908
0.8687	High Similarity	NPC219286
0.8687	High Similarity	NPC99557
0.8687	High Similarity	NPC239291
0.8687	High Similarity	NPC134829
0.8681	High Similarity	NPC407
0.8681	High Similarity	NPC307235
0.8673	High Similarity	NPC68269
0.866	High Similarity	NPC225506
0.8646	High Similarity	NPC77492
0.8632	High Similarity	NPC313650
0.8632	High Similarity	NPC8392
0.8627	High Similarity	NPC147634
0.8627	High Similarity	NPC296683
0.8627	High Similarity	NPC475018
0.8627	High Similarity	NPC120982
0.8627	High Similarity	NPC174096
0.8627	High Similarity	NPC252544
0.8627	High Similarity	NPC63345
0.8627	High Similarity	NPC44732
0.8627	High Similarity	NPC321252
0.8627	High Similarity	NPC79793
0.8627	High Similarity	NPC226401
0.8614	High Similarity	NPC75440
0.8614	High Similarity	NPC201959
0.8602	High Similarity	NPC300478
0.86	High Similarity	NPC39097
0.86	High Similarity	NPC248904
0.86	High Similarity	NPC39664
0.86	High Similarity	NPC470700
0.86	High Similarity	NPC109691
0.86	High Similarity	NPC54765
0.86	High Similarity	NPC118286
0.86	High Similarity	NPC302681
0.8587	High Similarity	NPC27974
0.8586	High Similarity	NPC327811
0.8586	High Similarity	NPC254965
0.8571	High Similarity	NPC51015
0.8571	High Similarity	NPC100340
0.8571	High Similarity	NPC12221
0.8571	High Similarity	NPC143659
0.8557	High Similarity	NPC275104
0.8557	High Similarity	NPC122005
0.8557	High Similarity	NPC252821
0.8544	High Similarity	NPC308689
0.8544	High Similarity	NPC257430
0.8544	High Similarity	NPC225679
0.8544	High Similarity	NPC476632
0.8544	High Similarity	NPC179002
0.8544	High Similarity	NPC177576
0.8544	High Similarity	NPC95716
0.8544	High Similarity	NPC165770
0.8544	High Similarity	NPC4493
0.8544	High Similarity	NPC187583
0.8526	High Similarity	NPC152415
0.8515	High Similarity	NPC54844
0.8511	High Similarity	NPC306074
0.85	High Similarity	NPC246056
0.8495	Intermediate Similarity	NPC70436
0.8485	Intermediate Similarity	NPC196479
0.8469	Intermediate Similarity	NPC248573
0.8469	Intermediate Similarity	NPC248396
0.8469	Intermediate Similarity	NPC48730
0.8469	Intermediate Similarity	NPC275053
0.8469	Intermediate Similarity	NPC161571
0.8469	Intermediate Similarity	NPC10588
0.8469	Intermediate Similarity	NPC129373
0.8469	Intermediate Similarity	NPC223393
0.8462	Intermediate Similarity	NPC286222
0.8462	Intermediate Similarity	NPC153795
0.8462	Intermediate Similarity	NPC286904
0.8462	Intermediate Similarity	NPC43525
0.8462	Intermediate Similarity	NPC290353
0.8462	Intermediate Similarity	NPC42911
0.8462	Intermediate Similarity	NPC46940
0.8462	Intermediate Similarity	NPC228988
0.8462	Intermediate Similarity	NPC166995
0.8454	Intermediate Similarity	NPC260000
0.8454	Intermediate Similarity	NPC474073
0.8454	Intermediate Similarity	NPC156313
0.8454	Intermediate Similarity	NPC109955
0.8454	Intermediate Similarity	NPC152097
0.8454	Intermediate Similarity	NPC107619
0.8447	Intermediate Similarity	NPC183700
0.8438	Intermediate Similarity	NPC144682
0.8431	Intermediate Similarity	NPC471495
0.8431	Intermediate Similarity	NPC24101
0.8431	Intermediate Similarity	NPC95344
0.8431	Intermediate Similarity	NPC96224
0.8421	Intermediate Similarity	NPC55903
0.8421	Intermediate Similarity	NPC181709
0.8416	Intermediate Similarity	NPC477814
0.84	Intermediate Similarity	NPC102216
0.8384	Intermediate Similarity	NPC72947
0.8384	Intermediate Similarity	NPC284011
0.8384	Intermediate Similarity	NPC471578
0.8384	Intermediate Similarity	NPC101025
0.8384	Intermediate Similarity	NPC472585
0.8381	Intermediate Similarity	NPC141003
0.8381	Intermediate Similarity	NPC176730
0.8381	Intermediate Similarity	NPC35344
0.8381	Intermediate Similarity	NPC117846
0.8381	Intermediate Similarity	NPC123175
0.8367	Intermediate Similarity	NPC280869

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 NPC151715 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	272
0.1-0.2	1079
0.2-0.3	1116
0.3-0.4	2854
0.4-0.5	2041
0.5-0.6	1171
0.6-0.7	501
0.7-0.8	99
0.8-0.85	7
0.85-0.9	5
0.9-0.95	0
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9888	High Similarity	NPD2859	Approved
0.9888	High Similarity	NPD2860	Approved
0.9775	High Similarity	NPD2934	Approved
0.9775	High Similarity	NPD2933	Approved
0.9565	High Similarity	NPD3020	Approved
0.8925	High Similarity	NPD1432	Clinical (unspecified phase)
0.8764	High Similarity	NPD111	Approved
0.8713	High Similarity	NPD3021	Approved
0.8713	High Similarity	NPD3022	Approved
0.8571	High Similarity	NPD846	Approved
0.8571	High Similarity	NPD940	Approved
0.8469	Intermediate Similarity	NPD1242	Phase 1
0.8469	Intermediate Similarity	NPD3028	Approved
0.8438	Intermediate Similarity	NPD1809	Phase 2
0.8438	Intermediate Similarity	NPD844	Approved
0.8421	Intermediate Similarity	NPD845	Approved
0.8208	Intermediate Similarity	NPD2234	Approved
0.8208	Intermediate Similarity	NPD2229	Approved
0.8208	Intermediate Similarity	NPD2228	Approved
0.8163	Intermediate Similarity	NPD288	Approved
0.81	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7981	Intermediate Similarity	NPD2342	Discontinued
0.7944	Intermediate Similarity	NPD7635	Approved
0.7885	Intermediate Similarity	NPD968	Approved
0.7864	Intermediate Similarity	NPD9610	Approved
0.7864	Intermediate Similarity	NPD9608	Approved
0.7857	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD3091	Approved
0.7838	Intermediate Similarity	NPD5304	Approved
0.7838	Intermediate Similarity	NPD5303	Approved
0.783	Intermediate Similarity	NPD4750	Phase 3
0.783	Intermediate Similarity	NPD1792	Phase 2
0.783	Intermediate Similarity	NPD5451	Approved
0.7768	Intermediate Similarity	NPD4093	Discontinued
0.7736	Intermediate Similarity	NPD2684	Approved
0.7727	Intermediate Similarity	NPD9087	Approved
0.7714	Intermediate Similarity	NPD1445	Approved
0.7714	Intermediate Similarity	NPD1444	Approved
0.7699	Intermediate Similarity	NPD2932	Approved
0.7699	Intermediate Similarity	NPD4589	Approved
0.7699	Intermediate Similarity	NPD2286	Discontinued
0.7699	Intermediate Similarity	NPD3019	Approved
0.7699	Intermediate Similarity	NPD4059	Approved
0.7685	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD5535	Approved
0.7586	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6583	Phase 3
0.7586	Intermediate Similarity	NPD6582	Phase 2
0.7586	Intermediate Similarity	NPD4659	Approved
0.7582	Intermediate Similarity	NPD9088	Approved
0.7568	Intermediate Similarity	NPD6671	Approved
0.7565	Intermediate Similarity	NPD3092	Approved
0.7549	Intermediate Similarity	NPD9273	Approved
0.7545	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD5283	Phase 1
0.7523	Intermediate Similarity	NPD228	Approved
0.7522	Intermediate Similarity	NPD1548	Phase 1
0.75	Intermediate Similarity	NPD2561	Approved
0.75	Intermediate Similarity	NPD2562	Approved
0.7478	Intermediate Similarity	NPD3421	Phase 3
0.7478	Intermediate Similarity	NPD3847	Discontinued
0.7473	Intermediate Similarity	NPD9294	Approved
0.7458	Intermediate Similarity	NPD4103	Phase 2
0.7458	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD7843	Approved
0.7455	Intermediate Similarity	NPD9379	Approved
0.7455	Intermediate Similarity	NPD9377	Approved
0.7414	Intermediate Similarity	NPD1610	Phase 2
0.7411	Intermediate Similarity	NPD255	Approved
0.7411	Intermediate Similarity	NPD256	Approved
0.7395	Intermediate Similarity	NPD6584	Phase 3
0.7391	Intermediate Similarity	NPD1751	Approved
0.7391	Intermediate Similarity	NPD2668	Approved
0.7391	Intermediate Similarity	NPD5846	Approved
0.7391	Intermediate Similarity	NPD6516	Phase 2
0.7391	Intermediate Similarity	NPD3095	Discontinued
0.7391	Intermediate Similarity	NPD2667	Approved
0.7373	Intermediate Similarity	NPD5310	Approved
0.7373	Intermediate Similarity	NPD5311	Approved
0.7368	Intermediate Similarity	NPD7330	Discontinued
0.7345	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2861	Phase 2
0.7315	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD3055	Approved
0.7311	Intermediate Similarity	NPD3094	Phase 2
0.7311	Intermediate Similarity	NPD3053	Approved
0.7297	Intermediate Similarity	NPD821	Approved
0.7281	Intermediate Similarity	NPD856	Approved
0.7281	Intermediate Similarity	NPD16	Approved
0.7273	Intermediate Similarity	NPD4908	Phase 1
0.7265	Intermediate Similarity	NPD1535	Discovery
0.7265	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD4658	Approved
0.7264	Intermediate Similarity	NPD9500	Approved
0.7264	Intermediate Similarity	NPD4656	Approved
0.7263	Intermediate Similarity	NPD9089	Approved
0.7257	Intermediate Similarity	NPD7157	Approved
0.725	Intermediate Similarity	NPD7451	Discontinued
0.7217	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD1894	Discontinued
0.7213	Intermediate Similarity	NPD3027	Phase 3
0.7203	Intermediate Similarity	NPD1481	Phase 2
0.7193	Intermediate Similarity	NPD9568	Approved
0.7193	Intermediate Similarity	NPD3596	Phase 2
0.719	Intermediate Similarity	NPD5736	Approved
0.717	Intermediate Similarity	NPD4818	Approved
0.717	Intermediate Similarity	NPD4817	Approved
0.7168	Intermediate Similarity	NPD1791	Approved
0.7168	Intermediate Similarity	NPD475	Phase 2
0.7168	Intermediate Similarity	NPD1793	Approved
0.7167	Intermediate Similarity	NPD1164	Approved
0.7158	Intermediate Similarity	NPD9093	Approved
0.7155	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD317	Approved
0.713	Intermediate Similarity	NPD318	Approved
0.7119	Intermediate Similarity	NPD1201	Approved
0.7117	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2194	Approved
0.7107	Intermediate Similarity	NPD2195	Approved
0.7103	Intermediate Similarity	NPD3682	Approved
0.7103	Intermediate Similarity	NPD3680	Approved
0.7103	Intermediate Similarity	NPD4229	Approved
0.7103	Intermediate Similarity	NPD4231	Approved
0.7097	Intermediate Similarity	NPD6407	Approved
0.7097	Intermediate Similarity	NPD6405	Approved
0.7094	Intermediate Similarity	NPD4626	Approved
0.7075	Intermediate Similarity	NPD1616	Discontinued
0.7073	Intermediate Similarity	NPD5156	Approved
0.7073	Intermediate Similarity	NPD5155	Approved
0.7069	Intermediate Similarity	NPD6581	Approved
0.7069	Intermediate Similarity	NPD6580	Approved
0.7064	Intermediate Similarity	NPD3134	Approved
0.7059	Intermediate Similarity	NPD2233	Approved
0.7059	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2232	Approved
0.7059	Intermediate Similarity	NPD2230	Approved
0.7049	Intermediate Similarity	NPD3636	Approved
0.7049	Intermediate Similarity	NPD3637	Approved
0.7049	Intermediate Similarity	NPD3635	Approved
0.704	Intermediate Similarity	NPD4060	Phase 1
0.7037	Intermediate Similarity	NPD1237	Approved
0.7034	Intermediate Similarity	NPD3143	Discontinued
0.7034	Intermediate Similarity	NPD1983	Approved
0.7034	Intermediate Similarity	NPD3026	Approved
0.7034	Intermediate Similarity	NPD3023	Approved
0.7034	Intermediate Similarity	NPD1980	Approved
0.7034	Intermediate Similarity	NPD1981	Approved
0.7025	Intermediate Similarity	NPD2797	Approved
0.7018	Intermediate Similarity	NPD9614	Approved
0.7018	Intermediate Similarity	NPD9618	Approved
0.7018	Intermediate Similarity	NPD497	Approved
0.7016	Intermediate Similarity	NPD3764	Approved
0.7009	Intermediate Similarity	NPD3025	Approved
0.7009	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD3024	Approved
0.7009	Intermediate Similarity	NPD1651	Approved
0.7	Intermediate Similarity	NPD4095	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1669	Approved
0.7	Intermediate Similarity	NPD290	Approved
0.6992	Remote Similarity	NPD3594	Approved
0.6992	Remote Similarity	NPD3595	Approved
0.6992	Remote Similarity	NPD2606	Approved
0.6992	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD2605	Approved
0.6975	Remote Similarity	NPD422	Phase 1
0.6967	Remote Similarity	NPD4624	Approved
0.696	Remote Similarity	NPD6663	Approved
0.6957	Remote Similarity	NPD709	Approved
0.6957	Remote Similarity	NPD2557	Approved
0.6957	Remote Similarity	NPD6387	Discontinued
0.6949	Remote Similarity	NPD9381	Approved
0.6949	Remote Similarity	NPD9384	Approved
0.6944	Remote Similarity	NPD3681	Approved
0.6944	Remote Similarity	NPD3683	Approved
0.6942	Remote Similarity	NPD1283	Approved
0.6937	Remote Similarity	NPD74	Approved
0.6937	Remote Similarity	NPD9266	Approved
0.6935	Remote Similarity	NPD4625	Phase 3
0.6935	Remote Similarity	NPD2372	Approved
0.6935	Remote Similarity	NPD7095	Approved
0.6931	Remote Similarity	NPD9295	Approved
0.693	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.693	Remote Similarity	NPD495	Approved
0.693	Remote Similarity	NPD496	Approved
0.693	Remote Similarity	NPD498	Approved
0.6923	Remote Similarity	NPD9545	Approved
0.6923	Remote Similarity	NPD1759	Phase 1
0.6917	Remote Similarity	NPD3070	Discontinued
0.6917	Remote Similarity	NPD2235	Phase 2
0.6917	Remote Similarity	NPD3972	Approved
0.6917	Remote Similarity	NPD2231	Phase 2

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