NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	272.1
Volume:	284.885
LogP:	2.089
LogD:	1.125
LogS:	-3.792
# Rotatable Bonds:	5
TPSA:	60.44
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.357
Synthetic Accessibility Score:	3.543
Fsp3:	0.312
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:	-4.642
MDCK Permeability:	5.492775744642131e-05
Pgp-inhibitor:	0.118
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.966
Plasma Protein Binding (PPB):	53.17061996459961%
Volume Distribution (VD):	0.481
Pgp-substrate:	61.16796112060547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.208
CYP1A2-substrate:	0.361
CYP2C19-inhibitor:	0.401
CYP2C19-substrate:	0.403
CYP2C9-inhibitor:	0.186
CYP2C9-substrate:	0.163
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.137
CYP3A4-inhibitor:	0.773
CYP3A4-substrate:	0.334

ADMET: Excretion

Clearance (CL):	4.512
Half-life (T1/2):	0.698

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.052
Drug-inuced Liver Injury (DILI):	0.658
AMES Toxicity:	0.092
Rat Oral Acute Toxicity:	0.52
Maximum Recommended Daily Dose:	0.015
Skin Sensitization:	0.478
Carcinogencity:	0.196
Eye Corrosion:	0.861
Eye Irritation:	0.947
Respiratory Toxicity:	0.937

Download Data

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

Natural Product: NPC469511

Natural Product ID:	NPC469511
*Common Name:**	Hyperlactone D
IUPAC Name:	(4R)-4-ethenyl-3-[(Z)-3-hydroxy-3-phenylprop-2-enoyl]-4-methyloxolan-2-one
Synonyms:	Hyperlactone D
Standard InCHIKey:	SYWQVHNVGPYUQH-SPMOTUBNSA-N
Standard InCHI:	InChI=1S/C16H16O4/c1-3-16(2)10-20-15(19)14(16)13(18)9-12(17)11-7-5-4-6-8-11/h3-9,14,17H,1,10H2,2H3/b12-9-/t14?,16-/m0/s1
SMILES:	CC1(COC(=O)C1C(=O)C=C(C2=CC=CC=C2)O)C=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1081692
PubChem CID:	46883484
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives

*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
NPO8089	Hypericum chinense	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19606850]
NPO8089	Hypericum chinense	Species	Hypericaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21043475]
NPO8089	Hypericum chinense	Species	Hypericaceae	Eukaryota	n.a.	root	n.a.	PMID[21043475]
NPO8089	Hypericum chinense	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22074257]
NPO8089	Hypericum chinense	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8089	Hypericum chinense	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8089	Hypericum chinense	Species	Hypericaceae	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
IC50	7

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	20.0	ug.mL-1	PMID[455743]
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	=	37.5	ug.mL-1	PMID[455743]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	47.8	ug.mL-1	PMID[455743]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	52.9	ug.mL-1	PMID[455743]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	61.0	ug.mL-1	PMID[455743]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	22.3	ug.mL-1	PMID[455743]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	24.6	ug.mL-1	PMID[455743]

☑ 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 NPC469511 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	173
0.1-0.2	824
0.2-0.3	2459
0.3-0.4	7057
0.4-0.5	13065
0.5-0.6	14989
0.6-0.7	3823
0.7-0.8	304
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9252	High Similarity	NPC469509
0.8319	Intermediate Similarity	NPC216387
0.8019	Intermediate Similarity	NPC476120
0.7925	Intermediate Similarity	NPC278228
0.7909	Intermediate Similarity	NPC321670
0.7838	Intermediate Similarity	NPC51174
0.7826	Intermediate Similarity	NPC474363
0.7826	Intermediate Similarity	NPC153053
0.7815	Intermediate Similarity	NPC475827
0.7815	Intermediate Similarity	NPC474223
0.7778	Intermediate Similarity	NPC105141
0.7778	Intermediate Similarity	NPC242764
0.7767	Intermediate Similarity	NPC220893
0.7742	Intermediate Similarity	NPC268607
0.7727	Intermediate Similarity	NPC91820
0.7727	Intermediate Similarity	NPC474365
0.7727	Intermediate Similarity	NPC82426
0.7727	Intermediate Similarity	NPC301943
0.7712	Intermediate Similarity	NPC325295
0.7712	Intermediate Similarity	NPC76308
0.7705	Intermediate Similarity	NPC472704
0.7692	Intermediate Similarity	NPC471616
0.7685	Intermediate Similarity	NPC179411
0.7679	Intermediate Similarity	NPC477251
0.7672	Intermediate Similarity	NPC87069
0.7652	Intermediate Similarity	NPC321852
0.7627	Intermediate Similarity	NPC190298
0.7623	Intermediate Similarity	NPC472703
0.7623	Intermediate Similarity	NPC474159
0.7623	Intermediate Similarity	NPC474254
0.7596	Intermediate Similarity	NPC173443
0.7573	Intermediate Similarity	NPC89377
0.7565	Intermediate Similarity	NPC260818
0.7565	Intermediate Similarity	NPC476003
0.7545	Intermediate Similarity	NPC469481
0.7544	Intermediate Similarity	NPC31274
0.7544	Intermediate Similarity	NPC469636
0.7525	Intermediate Similarity	NPC270507
0.7522	Intermediate Similarity	NPC136962
0.7521	Intermediate Similarity	NPC474222
0.7521	Intermediate Similarity	NPC307651
0.7521	Intermediate Similarity	NPC475804
0.75	Intermediate Similarity	NPC139946
0.75	Intermediate Similarity	NPC30361
0.75	Intermediate Similarity	NPC254233
0.75	Intermediate Similarity	NPC19136
0.748	Intermediate Similarity	NPC471832
0.748	Intermediate Similarity	NPC469927
0.7478	Intermediate Similarity	NPC214067
0.7478	Intermediate Similarity	NPC196246
0.746	Intermediate Similarity	NPC51448
0.746	Intermediate Similarity	NPC115797
0.7456	Intermediate Similarity	NPC20485
0.7456	Intermediate Similarity	NPC249811
0.7455	Intermediate Similarity	NPC146351
0.744	Intermediate Similarity	NPC137416
0.7438	Intermediate Similarity	NPC472708
0.7438	Intermediate Similarity	NPC204784
0.7436	Intermediate Similarity	NPC17693
0.7436	Intermediate Similarity	NPC474176
0.7426	Intermediate Similarity	NPC103387
0.7426	Intermediate Similarity	NPC323103
0.7419	Intermediate Similarity	NPC236981
0.7417	Intermediate Similarity	NPC122117
0.7414	Intermediate Similarity	NPC305912
0.7414	Intermediate Similarity	NPC133308
0.7414	Intermediate Similarity	NPC1082
0.7414	Intermediate Similarity	NPC183700
0.7414	Intermediate Similarity	NPC477247
0.7411	Intermediate Similarity	NPC160382
0.7411	Intermediate Similarity	NPC304638
0.7405	Intermediate Similarity	NPC217673
0.7405	Intermediate Similarity	NPC52523
0.7395	Intermediate Similarity	NPC210531
0.7395	Intermediate Similarity	NPC149691
0.7395	Intermediate Similarity	NPC23402
0.7391	Intermediate Similarity	NPC17417
0.7391	Intermediate Similarity	NPC474364
0.7391	Intermediate Similarity	NPC281604
0.7391	Intermediate Similarity	NPC10251
0.7391	Intermediate Similarity	NPC265407
0.7391	Intermediate Similarity	NPC85493
0.7391	Intermediate Similarity	NPC83628
0.7391	Intermediate Similarity	NPC470039
0.7381	Intermediate Similarity	NPC472706
0.7381	Intermediate Similarity	NPC169913
0.7379	Intermediate Similarity	NPC58616
0.7377	Intermediate Similarity	NPC72977
0.7368	Intermediate Similarity	NPC472315
0.7368	Intermediate Similarity	NPC475203
0.7368	Intermediate Similarity	NPC37622
0.7368	Intermediate Similarity	NPC474376
0.7368	Intermediate Similarity	NPC472316
0.7368	Intermediate Similarity	NPC30594
0.7364	Intermediate Similarity	NPC78701
0.7364	Intermediate Similarity	NPC229242
0.7364	Intermediate Similarity	NPC35448
0.7364	Intermediate Similarity	NPC225060
0.736	Intermediate Similarity	NPC295664
0.736	Intermediate Similarity	NPC246166
0.735	Intermediate Similarity	NPC474314
0.735	Intermediate Similarity	NPC270699
0.735	Intermediate Similarity	NPC82899
0.7345	Intermediate Similarity	NPC171831
0.7345	Intermediate Similarity	NPC242913
0.7345	Intermediate Similarity	NPC280616
0.7344	Intermediate Similarity	NPC272946
0.7339	Intermediate Similarity	NPC182333
0.7339	Intermediate Similarity	NPC273336
0.7333	Intermediate Similarity	NPC128249
0.7333	Intermediate Similarity	NPC304760
0.7333	Intermediate Similarity	NPC212891
0.7328	Intermediate Similarity	NPC251854
0.7328	Intermediate Similarity	NPC93084
0.7323	Intermediate Similarity	NPC472707
0.7321	Intermediate Similarity	NPC304873
0.7321	Intermediate Similarity	NPC25458
0.7321	Intermediate Similarity	NPC472585
0.7311	Intermediate Similarity	NPC210092
0.7311	Intermediate Similarity	NPC197513
0.7304	Intermediate Similarity	NPC56493
0.7304	Intermediate Similarity	NPC277788
0.7304	Intermediate Similarity	NPC156648
0.7304	Intermediate Similarity	NPC260952
0.7302	Intermediate Similarity	NPC79608
0.7302	Intermediate Similarity	NPC275576
0.7297	Intermediate Similarity	NPC474308
0.7297	Intermediate Similarity	NPC54647
0.7297	Intermediate Similarity	NPC171843
0.7297	Intermediate Similarity	NPC325497
0.7295	Intermediate Similarity	NPC90522
0.7295	Intermediate Similarity	NPC328459
0.729	Intermediate Similarity	NPC119631
0.7288	Intermediate Similarity	NPC477476
0.7288	Intermediate Similarity	NPC161611
0.7288	Intermediate Similarity	NPC477245
0.7288	Intermediate Similarity	NPC477246
0.7288	Intermediate Similarity	NPC477475
0.7288	Intermediate Similarity	NPC272524
0.7282	Intermediate Similarity	NPC44546
0.7281	Intermediate Similarity	NPC127676
0.728	Intermediate Similarity	NPC77691
0.728	Intermediate Similarity	NPC477362
0.728	Intermediate Similarity	NPC85511
0.7273	Intermediate Similarity	NPC253423
0.7273	Intermediate Similarity	NPC289201
0.7273	Intermediate Similarity	NPC45794
0.7273	Intermediate Similarity	NPC249912
0.7273	Intermediate Similarity	NPC94425
0.7273	Intermediate Similarity	NPC276775
0.7273	Intermediate Similarity	NPC92754
0.7265	Intermediate Similarity	NPC63345
0.7265	Intermediate Similarity	NPC95126
0.7265	Intermediate Similarity	NPC222905
0.7265	Intermediate Similarity	NPC475002
0.7257	Intermediate Similarity	NPC234305
0.7257	Intermediate Similarity	NPC68269
0.7257	Intermediate Similarity	NPC89886
0.725	Intermediate Similarity	NPC235421
0.7248	Intermediate Similarity	NPC5472
0.7244	Intermediate Similarity	NPC477365
0.7241	Intermediate Similarity	NPC317305
0.7241	Intermediate Similarity	NPC40178
0.7241	Intermediate Similarity	NPC206341
0.7241	Intermediate Similarity	NPC475282
0.7236	Intermediate Similarity	NPC473243
0.7236	Intermediate Similarity	NPC31314
0.7236	Intermediate Similarity	NPC193193
0.7232	Intermediate Similarity	NPC253746
0.7232	Intermediate Similarity	NPC282895
0.7231	Intermediate Similarity	NPC7012
0.7228	Intermediate Similarity	NPC121800
0.7227	Intermediate Similarity	NPC190212
0.7227	Intermediate Similarity	NPC294458
0.7227	Intermediate Similarity	NPC237366
0.7222	Intermediate Similarity	NPC265413
0.7222	Intermediate Similarity	NPC10154
0.7222	Intermediate Similarity	NPC474532
0.7218	Intermediate Similarity	NPC475955
0.7218	Intermediate Similarity	NPC474726
0.7217	Intermediate Similarity	NPC37115
0.7217	Intermediate Similarity	NPC119271
0.7213	Intermediate Similarity	NPC94637
0.7209	Intermediate Similarity	NPC214246
0.7209	Intermediate Similarity	NPC131684
0.7207	Intermediate Similarity	NPC210529
0.7207	Intermediate Similarity	NPC329387
0.7207	Intermediate Similarity	NPC160548
0.7207	Intermediate Similarity	NPC317280
0.7207	Intermediate Similarity	NPC175852
0.7203	Intermediate Similarity	NPC234376
0.7203	Intermediate Similarity	NPC471188
0.7203	Intermediate Similarity	NPC228609
0.72	Intermediate Similarity	NPC223351
0.72	Intermediate Similarity	NPC132518
0.72	Intermediate Similarity	NPC477151
0.7197	Intermediate Similarity	NPC232888
0.7197	Intermediate Similarity	NPC477367
0.7196	Intermediate Similarity	NPC62765
0.7196	Intermediate Similarity	NPC240108

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 NPC469511 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	646
0.2-0.3	1382
0.3-0.4	2862
0.4-0.5	2542
0.5-0.6	1238
0.6-0.7	307
0.7-0.8	19
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
0.8224	Intermediate Similarity	NPD6647	Phase 2
0.7565	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD2629	Approved
0.7411	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2182	Approved
0.7391	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD5909	Discontinued
0.7328	Intermediate Similarity	NPD2067	Discontinued
0.7311	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD2066	Phase 3
0.725	Intermediate Similarity	NPD4198	Discontinued
0.7248	Intermediate Similarity	NPD1693	Approved
0.7244	Intermediate Similarity	NPD6085	Phase 2
0.7244	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1088	Approved
0.7209	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD9495	Approved
0.7203	Intermediate Similarity	NPD969	Suspended
0.7196	Intermediate Similarity	NPD9256	Approved
0.7196	Intermediate Similarity	NPD9258	Approved
0.713	Intermediate Similarity	NPD5048	Discontinued
0.7109	Intermediate Similarity	NPD5647	Approved
0.7083	Intermediate Similarity	NPD2652	Approved
0.7083	Intermediate Similarity	NPD2650	Approved
0.7069	Intermediate Similarity	NPD3134	Approved
0.7069	Intermediate Similarity	NPD6685	Approved
0.7054	Intermediate Similarity	NPD5736	Approved
0.7049	Intermediate Similarity	NPD9493	Approved
0.7049	Intermediate Similarity	NPD694	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD164	Approved
0.7037	Intermediate Similarity	NPD1086	Approved
0.7037	Intermediate Similarity	NPD3672	Approved
0.7037	Intermediate Similarity	NPD1089	Approved
0.7037	Intermediate Similarity	NPD3673	Approved
0.7037	Intermediate Similarity	NPD1090	Approved
0.7025	Intermediate Similarity	NPD5951	Approved
0.6991	Remote Similarity	NPD1238	Approved
0.696	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.696	Remote Similarity	NPD5305	Approved
0.696	Remote Similarity	NPD5306	Approved
0.6957	Remote Similarity	NPD1930	Approved
0.6957	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1929	Approved
0.6944	Remote Similarity	NPD800	Approved
0.6944	Remote Similarity	NPD689	Discontinued
0.6935	Remote Similarity	NPD9545	Approved
0.6931	Remote Similarity	NPD9294	Approved
0.6916	Remote Similarity	NPD1282	Approved
0.6905	Remote Similarity	NPD3496	Discontinued
0.6897	Remote Similarity	NPD1237	Approved
0.688	Remote Similarity	NPD5585	Approved
0.6875	Remote Similarity	NPD1989	Approved
0.6864	Remote Similarity	NPD1358	Approved
0.6864	Remote Similarity	NPD9263	Approved
0.6864	Remote Similarity	NPD9267	Approved
0.6864	Remote Similarity	NPD9264	Approved
0.686	Remote Similarity	NPD6858	Approved
0.686	Remote Similarity	NPD7094	Approved
0.6857	Remote Similarity	NPD9491	Approved
0.6857	Remote Similarity	NPD3971	Phase 1
0.685	Remote Similarity	NPD4807	Approved
0.685	Remote Similarity	NPD4806	Approved
0.6847	Remote Similarity	NPD1202	Approved
0.6842	Remote Similarity	NPD6663	Approved
0.6838	Remote Similarity	NPD7305	Phase 1
0.6825	Remote Similarity	NPD1778	Approved
0.6822	Remote Similarity	NPD9257	Approved
0.6822	Remote Similarity	NPD9259	Approved
0.681	Remote Similarity	NPD5765	Approved
0.6807	Remote Similarity	NPD74	Approved
0.6807	Remote Similarity	NPD9266	Approved
0.6803	Remote Similarity	NPD6010	Discontinued
0.6797	Remote Similarity	NPD9717	Approved
0.6794	Remote Similarity	NPD3663	Approved
0.6794	Remote Similarity	NPD3662	Phase 3
0.6794	Remote Similarity	NPD3664	Approved
0.6794	Remote Similarity	NPD3661	Approved
0.6789	Remote Similarity	NPD5347	Phase 2
0.6789	Remote Similarity	NPD5346	Phase 2
0.6786	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5291	Approved
0.6774	Remote Similarity	NPD5292	Approved
0.6772	Remote Similarity	NPD4106	Approved
0.6772	Remote Similarity	NPD4136	Approved
0.6772	Remote Similarity	NPD4135	Approved
0.6769	Remote Similarity	NPD2797	Approved
0.6767	Remote Similarity	NPD3268	Approved
0.6759	Remote Similarity	NPD1087	Approved
0.6754	Remote Similarity	NPD5926	Approved
0.6733	Remote Similarity	NPD9716	Approved
0.6721	Remote Similarity	NPD5277	Phase 2
0.6719	Remote Similarity	NPD4215	Approved
0.6719	Remote Similarity	NPD2608	Approved
0.6719	Remote Similarity	NPD2611	Approved
0.6719	Remote Similarity	NPD4216	Approved
0.6719	Remote Similarity	NPD3132	Approved
0.6719	Remote Similarity	NPD2610	Approved
0.6719	Remote Similarity	NPD4217	Approved
0.6719	Remote Similarity	NPD4218	Approved
0.6719	Remote Similarity	NPD6287	Discontinued
0.6719	Remote Similarity	NPD3131	Approved
0.6719	Remote Similarity	NPD2612	Approved
0.6719	Remote Similarity	NPD2609	Approved
0.6715	Remote Similarity	NPD2799	Discontinued
0.6714	Remote Similarity	NPD8166	Discontinued
0.6696	Remote Similarity	NPD845	Approved
0.6696	Remote Similarity	NPD3020	Approved
0.6693	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD2932	Approved
0.6693	Remote Similarity	NPD3019	Approved
0.6692	Remote Similarity	NPD7008	Discontinued
0.6667	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5204	Approved
0.6667	Remote Similarity	NPD226	Approved
0.6667	Remote Similarity	NPD7741	Discontinued
0.6642	Remote Similarity	NPD3764	Approved
0.6641	Remote Similarity	NPD6362	Approved
0.6641	Remote Similarity	NPD2628	Approved
0.6641	Remote Similarity	NPD2160	Approved
0.6641	Remote Similarity	NPD2627	Approved
0.6641	Remote Similarity	NPD2159	Approved
0.6641	Remote Similarity	NPD2626	Approved
0.6641	Remote Similarity	NPD2625	Approved
0.6639	Remote Similarity	NPD6912	Phase 3
0.6637	Remote Similarity	NPD6049	Phase 2
0.6637	Remote Similarity	NPD2934	Approved
0.6637	Remote Similarity	NPD2933	Approved
0.6637	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD4359	Approved
0.6614	Remote Similarity	NPD4102	Approved
0.6614	Remote Similarity	NPD4105	Approved
0.6614	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD9281	Approved
0.6612	Remote Similarity	NPD4234	Approved
0.6612	Remote Similarity	NPD5239	Approved
0.6612	Remote Similarity	NPD5237	Approved
0.6612	Remote Similarity	NPD4233	Approved
0.6612	Remote Similarity	NPD5235	Approved
0.6612	Remote Similarity	NPD5236	Approved
0.6612	Remote Similarity	NPD5240	Approved
0.6606	Remote Similarity	NPD4793	Discontinued
0.6583	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD1932	Approved
0.6579	Remote Similarity	NPD1809	Phase 2
0.6579	Remote Similarity	NPD2859	Approved
0.6579	Remote Similarity	NPD2860	Approved
0.6569	Remote Similarity	NPD6653	Approved
0.6562	Remote Similarity	NPD4626	Approved
0.6557	Remote Similarity	NPD2201	Approved
0.6549	Remote Similarity	NPD1066	Discontinued
0.6538	Remote Similarity	NPD1877	Discontinued
0.6535	Remote Similarity	NPD1894	Discontinued
0.6529	Remote Similarity	NPD2329	Discontinued
0.6525	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD9261	Approved
0.6522	Remote Similarity	NPD1565	Approved
0.6522	Remote Similarity	NPD1564	Approved
0.6522	Remote Similarity	NPD1566	Phase 3
0.6519	Remote Similarity	NPD4621	Approved
0.6519	Remote Similarity	NPD4619	Approved
0.6519	Remote Similarity	NPD2313	Discontinued
0.6518	Remote Similarity	NPD1239	Approved
0.6515	Remote Similarity	NPD1203	Approved
0.6512	Remote Similarity	NPD3847	Discontinued
0.6509	Remote Similarity	NPD9250	Approved
0.6508	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD7236	Approved
0.65	Remote Similarity	NPD6005	Phase 3
0.65	Remote Similarity	NPD6002	Phase 3
0.65	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6004	Phase 3
0.65	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5706	Approved
0.65	Remote Similarity	NPD5705	Approved
0.65	Remote Similarity	NPD5704	Approved
0.6496	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD6355	Discontinued
0.6493	Remote Similarity	NPD6832	Phase 2
0.6493	Remote Similarity	NPD2613	Approved
0.6489	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5691	Approved
0.648	Remote Similarity	NPD4766	Approved
0.6479	Remote Similarity	NPD4628	Phase 3
0.6476	Remote Similarity	NPD9490	Approved
0.6475	Remote Similarity	NPD7033	Discontinued
0.6475	Remote Similarity	NPD1317	Discontinued
0.6471	Remote Similarity	NPD7715	Approved
0.6471	Remote Similarity	NPD7714	Approved
0.6471	Remote Similarity	NPD520	Approved
0.6471	Remote Similarity	NPD7961	Discontinued
0.6466	Remote Similarity	NPD2798	Approved
0.6444	Remote Similarity	NPD7095	Approved
0.6439	Remote Similarity	NPD3225	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