NPASS Compound

Structure

CID181464 OpenBabel06191715552D 26 31 0 0 0 0 0 0 0 0999 V2000 -0.5296 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3956 -4.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3956 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9345 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8005 -3.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -5.6654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5296 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2617 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2617 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9345 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -4.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3849 -1.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2127 -4.3917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2127 -2.7737 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6776 -4.7518 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2764 -5.5608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 10 1 0 0 0 0 2 14 1 0 0 0 0 3 11 2 0 0 0 0 3 12 1 0 0 0 0 4 10 2 0 0 0 0 4 15 1 0 0 0 0 5 11 1 0 0 0 0 5 16 2 0 0 0 0 6 13 1 0 0 0 0 6 17 2 0 0 0 0 7 12 1 0 0 0 0 7 22 1 0 0 0 0 8 23 1 0 0 0 0 8 24 1 0 0 0 0 9 25 1 0 0 0 0 9 26 1 0 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 12 19 2 0 0 0 0 13 18 2 0 0 0 0 14 15 2 0 0 0 0 14 23 1 0 0 0 0 15 24 1 0 0 0 0 16 17 1 0 0 0 0 16 25 1 0 0 0 0 17 26 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 21 2 0 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.06
Volume:	332.151
LogP:	4.306
LogD:	3.207
LogS:	-7.015
# Rotatable Bonds:	1
TPSA:	63.22
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.626
Synthetic Accessibility Score:	2.644
Fsp3:	0.15
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.227
MDCK Permeability:	5.502131534740329e-05
Pgp-inhibitor:	0.039
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.023

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.053
Plasma Protein Binding (PPB):	96.67000579833984%
Volume Distribution (VD):	0.993
Pgp-substrate:	0.7599031925201416%

ADMET: Metabolism

CYP1A2-inhibitor:	0.989
CYP1A2-substrate:	0.149
CYP2C19-inhibitor:	0.982
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.773
CYP2C9-substrate:	0.917
CYP2D6-inhibitor:	0.969
CYP2D6-substrate:	0.935
CYP3A4-inhibitor:	0.935
CYP3A4-substrate:	0.095

ADMET: Excretion

Clearance (CL):	16.249
Half-life (T1/2):	0.099

ADMET: Toxicity

hERG Blockers:	0.12
Human Hepatotoxicity (H-HT):	0.103
Drug-inuced Liver Injury (DILI):	0.922
AMES Toxicity:	0.875
Rat Oral Acute Toxicity:	0.048
Maximum Recommended Daily Dose:	0.874
Skin Sensitization:	0.418
Carcinogencity:	0.943
Eye Corrosion:	0.003
Eye Irritation:	0.407
Respiratory Toxicity:	0.359

Download Data

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

Natural Product: NPC181464

Natural Product ID:	NPC181464
*Common Name:**	Taiwanin C
IUPAC Name:	5-(1,3-benzodioxol-5-yl)-8H-[2]benzofuro[5,6-f][1,3]benzodioxol-6-one
Synonyms:	Taiwanin C
Standard InCHIKey:	YMGOOHXUOWZQOE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H12O6/c21-20-19-12(7-22-20)3-11-5-16-17(26-9-25-16)6-13(11)18(19)10-1-2-14-15(4-10)24-8-23-14/h1-6H,7-9H2
SMILES:	c1cc2c(cc1c1c3cc4c(cc3cc3COC(=O)c13)OCO4)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL65755
PubChem CID:	363127
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001610] Arylnaphthalene lignans

*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
NPO33358	phyllanthus acutissima	Species	n.a.	Eukaryota	aerial parts	n.a.	n.a.	PMID[18271551]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	twig	n.a.	PMID[22474975]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31347365]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9014350]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	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	6
IC50	2
Others	1

Activity Type	# Activity
Cell Line	5
Individual Protein	2
NON-MOLECULAR	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	IC50	=	250.0	nM	PMID[494888]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	Inhibition	=	88.2	%	PMID[494889]
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[494889]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[494889]
NPT1851	Cell Line	Col2	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[494889]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[494889]
NPT168	Cell Line	P388	Mus musculus	ED50	>	5.0	ug ml-1	PMID[494889]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	>	125.0	ug.mL-1	PMID[494889]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	>	125.0	ug.mL-1	PMID[494889]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	5.0	ug ml-1	PMID[494889]

☑ 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 NPC181464 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	438
0.1-0.2	1854
0.2-0.3	4252
0.3-0.4	11407
0.4-0.5	6876
0.5-0.6	4629
0.6-0.7	11374
0.7-0.8	1761
0.8-0.85	70
0.85-0.9	24
0.9-0.95	8
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9929	High Similarity	NPC24193
0.965	High Similarity	NPC127827
0.9589	High Similarity	NPC54179
0.9583	High Similarity	NPC475722
0.9396	High Similarity	NPC19600
0.9329	High Similarity	NPC473900
0.9225	High Similarity	NPC218092
0.9225	High Similarity	NPC246474
0.9225	High Similarity	NPC162851
0.9211	High Similarity	NPC15212
0.92	High Similarity	NPC115123
0.92	High Similarity	NPC239113
0.915	High Similarity	NPC198796
0.9133	High Similarity	NPC234730
0.902	High Similarity	NPC78944
0.8954	High Similarity	NPC474043
0.8933	High Similarity	NPC118332
0.8903	High Similarity	NPC22130
0.8903	High Similarity	NPC116838
0.8811	High Similarity	NPC230968
0.8811	High Similarity	NPC102260
0.8803	High Similarity	NPC19890
0.8803	High Similarity	NPC110958
0.88	High Similarity	NPC261322
0.8734	High Similarity	NPC471923
0.8707	High Similarity	NPC125134
0.8707	High Similarity	NPC137920
0.8707	High Similarity	NPC86455
0.8701	High Similarity	NPC109765
0.8696	High Similarity	NPC184624
0.8679	High Similarity	NPC473531
0.8679	High Similarity	NPC475453
0.8654	High Similarity	NPC65784
0.8645	High Similarity	NPC202495
0.8616	High Similarity	NPC474042
0.8616	High Similarity	NPC174734
0.8609	High Similarity	NPC177476
0.8609	High Similarity	NPC262455
0.8601	High Similarity	NPC205915
0.859	High Similarity	NPC125713
0.8537	High Similarity	NPC35266
0.8519	High Similarity	NPC129930
0.8519	High Similarity	NPC471920
0.8519	High Similarity	NPC471922
0.8519	High Similarity	NPC292712
0.8519	High Similarity	NPC20114
0.8519	High Similarity	NPC474075
0.8519	High Similarity	NPC312006
0.8519	High Similarity	NPC471921
0.8519	High Similarity	NPC114550
0.8519	High Similarity	NPC473697
0.8509	High Similarity	NPC117911
0.8477	Intermediate Similarity	NPC104024
0.8477	Intermediate Similarity	NPC80230
0.8477	Intermediate Similarity	NPC65574
0.8477	Intermediate Similarity	NPC101755
0.8477	Intermediate Similarity	NPC304687
0.8467	Intermediate Similarity	NPC229787
0.8431	Intermediate Similarity	NPC300983
0.8415	Intermediate Similarity	NPC193377
0.8408	Intermediate Similarity	NPC143328
0.8365	Intermediate Similarity	NPC239890
0.8365	Intermediate Similarity	NPC191352
0.8365	Intermediate Similarity	NPC209411
0.8365	Intermediate Similarity	NPC258322
0.8364	Intermediate Similarity	NPC196771
0.8344	Intermediate Similarity	NPC261484
0.8333	Intermediate Similarity	NPC167045
0.8333	Intermediate Similarity	NPC114120
0.8313	Intermediate Similarity	NPC19948
0.8312	Intermediate Similarity	NPC149505
0.831	Intermediate Similarity	NPC100129
0.8301	Intermediate Similarity	NPC40654
0.8301	Intermediate Similarity	NPC262804
0.8291	Intermediate Similarity	NPC76458
0.8291	Intermediate Similarity	NPC82733
0.828	Intermediate Similarity	NPC254163
0.8278	Intermediate Similarity	NPC177644
0.8278	Intermediate Similarity	NPC191158
0.8263	Intermediate Similarity	NPC275690
0.8263	Intermediate Similarity	NPC161609
0.8258	Intermediate Similarity	NPC210642
0.8258	Intermediate Similarity	NPC13985
0.8239	Intermediate Similarity	NPC68619
0.8239	Intermediate Similarity	NPC15764
0.8235	Intermediate Similarity	NPC313063
0.8235	Intermediate Similarity	NPC286301
0.8231	Intermediate Similarity	NPC88065
0.8231	Intermediate Similarity	NPC89504
0.8231	Intermediate Similarity	NPC95485
0.8224	Intermediate Similarity	NPC91694
0.8224	Intermediate Similarity	NPC300603
0.82	Intermediate Similarity	NPC166137
0.82	Intermediate Similarity	NPC282291
0.82	Intermediate Similarity	NPC29599
0.8194	Intermediate Similarity	NPC37220
0.8187	Intermediate Similarity	NPC96593
0.8187	Intermediate Similarity	NPC470637
0.8187	Intermediate Similarity	NPC139876
0.8182	Intermediate Similarity	NPC223807
0.8182	Intermediate Similarity	NPC177167
0.817	Intermediate Similarity	NPC3982
0.817	Intermediate Similarity	NPC193779
0.8158	Intermediate Similarity	NPC218841
0.8158	Intermediate Similarity	NPC92693
0.8153	Intermediate Similarity	NPC308555
0.8146	Intermediate Similarity	NPC210354
0.8146	Intermediate Similarity	NPC176586
0.8137	Intermediate Similarity	NPC319749
0.8137	Intermediate Similarity	NPC309335
0.8137	Intermediate Similarity	NPC288149
0.8137	Intermediate Similarity	NPC296540
0.8121	Intermediate Similarity	NPC14022
0.8117	Intermediate Similarity	NPC153620
0.8117	Intermediate Similarity	NPC24257
0.8117	Intermediate Similarity	NPC39361
0.8113	Intermediate Similarity	NPC301897
0.8113	Intermediate Similarity	NPC261090
0.811	Intermediate Similarity	NPC79322
0.8105	Intermediate Similarity	NPC472836
0.8105	Intermediate Similarity	NPC327052
0.8105	Intermediate Similarity	NPC308006
0.8101	Intermediate Similarity	NPC103197
0.8101	Intermediate Similarity	NPC30009
0.8101	Intermediate Similarity	NPC273578
0.8089	Intermediate Similarity	NPC104353
0.8086	Intermediate Similarity	NPC280778
0.8075	Intermediate Similarity	NPC239818
0.8075	Intermediate Similarity	NPC218471
0.8069	Intermediate Similarity	NPC476748
0.8063	Intermediate Similarity	NPC167098
0.8063	Intermediate Similarity	NPC296044
0.805	Intermediate Similarity	NPC3273
0.8042	Intermediate Similarity	NPC17348
0.8039	Intermediate Similarity	NPC475000
0.8026	Intermediate Similarity	NPC151423
0.8026	Intermediate Similarity	NPC40237
0.8025	Intermediate Similarity	NPC109238
0.8013	Intermediate Similarity	NPC472839
0.8013	Intermediate Similarity	NPC223336
0.8012	Intermediate Similarity	NPC52598
0.8	Intermediate Similarity	NPC237946
0.8	Intermediate Similarity	NPC32373
0.7988	Intermediate Similarity	NPC474301
0.7988	Intermediate Similarity	NPC477884
0.7987	Intermediate Similarity	NPC178195
0.7987	Intermediate Similarity	NPC471305
0.7987	Intermediate Similarity	NPC348849
0.7975	Intermediate Similarity	NPC61141
0.7963	Intermediate Similarity	NPC474770
0.7961	Intermediate Similarity	NPC323601
0.7961	Intermediate Similarity	NPC28398
0.795	Intermediate Similarity	NPC115281
0.795	Intermediate Similarity	NPC207584
0.795	Intermediate Similarity	NPC181168
0.795	Intermediate Similarity	NPC163527
0.795	Intermediate Similarity	NPC19947
0.7939	Intermediate Similarity	NPC83049
0.7939	Intermediate Similarity	NPC320471
0.7939	Intermediate Similarity	NPC118162
0.7937	Intermediate Similarity	NPC472835
0.7935	Intermediate Similarity	NPC189054
0.7931	Intermediate Similarity	NPC286683
0.7931	Intermediate Similarity	NPC158737
0.7931	Intermediate Similarity	NPC428300
0.7922	Intermediate Similarity	NPC46880
0.7922	Intermediate Similarity	NPC474036
0.7914	Intermediate Similarity	NPC99968
0.7911	Intermediate Similarity	NPC303519
0.7901	Intermediate Similarity	NPC325122
0.7898	Intermediate Similarity	NPC95526
0.7892	Intermediate Similarity	NPC311912
0.7888	Intermediate Similarity	NPC213401
0.7871	Intermediate Similarity	NPC474158
0.7871	Intermediate Similarity	NPC290038
0.7862	Intermediate Similarity	NPC70320
0.7857	Intermediate Similarity	NPC474288
0.7857	Intermediate Similarity	NPC141817
0.7857	Intermediate Similarity	NPC229218
0.7857	Intermediate Similarity	NPC192597
0.7857	Intermediate Similarity	NPC176030
0.7857	Intermediate Similarity	NPC169214
0.7853	Intermediate Similarity	NPC268718
0.7853	Intermediate Similarity	NPC119910
0.7853	Intermediate Similarity	NPC150943
0.7853	Intermediate Similarity	NPC91634
0.7848	Intermediate Similarity	NPC474305
0.7844	Intermediate Similarity	NPC88557
0.7829	Intermediate Similarity	NPC233780
0.7829	Intermediate Similarity	NPC178290
0.7826	Intermediate Similarity	NPC186316
0.7818	Intermediate Similarity	NPC100420
0.7815	Intermediate Similarity	NPC90431
0.7812	Intermediate Similarity	NPC3744
0.7812	Intermediate Similarity	NPC137125
0.7812	Intermediate Similarity	NPC245948
0.7811	Intermediate Similarity	NPC72455
0.7806	Intermediate Similarity	NPC15743
0.7805	Intermediate Similarity	NPC152424
0.7805	Intermediate Similarity	NPC115624

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 NPC181464 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	382
0.1-0.2	1013
0.2-0.3	1450
0.3-0.4	2740
0.4-0.5	1946
0.5-0.6	1102
0.6-0.7	457
0.7-0.8	59
0.8-0.85	1
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	NPD6143	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4967	Phase 2
0.8	Intermediate Similarity	NPD4966	Approved
0.8	Intermediate Similarity	NPD4965	Approved
0.7901	Intermediate Similarity	NPD6234	Discontinued
0.7887	Intermediate Similarity	NPD1281	Approved
0.7812	Intermediate Similarity	NPD37	Approved
0.7785	Intermediate Similarity	NPD2979	Phase 3
0.7763	Intermediate Similarity	NPD2438	Suspended
0.7758	Intermediate Similarity	NPD6232	Discontinued
0.7724	Intermediate Similarity	NPD1283	Approved
0.7633	Intermediate Similarity	NPD5844	Phase 1
0.7625	Intermediate Similarity	NPD7458	Discontinued
0.7619	Intermediate Similarity	NPD7473	Discontinued
0.76	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7199	Phase 2
0.7584	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD7028	Phase 2
0.7574	Intermediate Similarity	NPD7228	Approved
0.7564	Intermediate Similarity	NPD7003	Approved
0.7552	Intermediate Similarity	NPD1651	Approved
0.7533	Intermediate Similarity	NPD3764	Approved
0.7532	Intermediate Similarity	NPD2531	Phase 2
0.7516	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1933	Approved
0.7484	Intermediate Similarity	NPD2346	Discontinued
0.7438	Intermediate Similarity	NPD6273	Approved
0.7431	Intermediate Similarity	NPD5691	Approved
0.7399	Intermediate Similarity	NPD7240	Approved
0.7397	Intermediate Similarity	NPD3705	Approved
0.733	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD8032	Phase 2
0.7248	Intermediate Similarity	NPD1876	Approved
0.7233	Intermediate Similarity	NPD4110	Phase 3
0.7233	Intermediate Similarity	NPD4628	Phase 3
0.7233	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5494	Approved
0.7216	Intermediate Similarity	NPD8312	Approved
0.7216	Intermediate Similarity	NPD8313	Approved
0.7212	Intermediate Similarity	NPD6873	Phase 2
0.72	Intermediate Similarity	NPD6559	Discontinued
0.7195	Intermediate Similarity	NPD3226	Approved
0.7188	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5536	Phase 2
0.717	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD3818	Discontinued
0.716	Intermediate Similarity	NPD919	Approved
0.7143	Intermediate Similarity	NPD4626	Approved
0.7143	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2799	Discontinued
0.7134	Intermediate Similarity	NPD3748	Approved
0.7133	Intermediate Similarity	NPD5283	Phase 1
0.7126	Intermediate Similarity	NPD8455	Phase 2
0.712	Intermediate Similarity	NPD4420	Approved
0.7114	Intermediate Similarity	NPD3972	Approved
0.7108	Intermediate Similarity	NPD6386	Approved
0.7108	Intermediate Similarity	NPD6385	Approved
0.7089	Intermediate Similarity	NPD2935	Discontinued
0.7078	Intermediate Similarity	NPD6798	Discontinued
0.7078	Intermediate Similarity	NPD2313	Discontinued
0.7076	Intermediate Similarity	NPD8127	Discontinued
0.7055	Intermediate Similarity	NPD2532	Approved
0.7055	Intermediate Similarity	NPD2534	Approved
0.7055	Intermediate Similarity	NPD2533	Approved
0.7047	Intermediate Similarity	NPD1611	Approved
0.7024	Intermediate Similarity	NPD7819	Suspended
0.7024	Intermediate Similarity	NPD1465	Phase 2
0.7021	Intermediate Similarity	NPD7680	Approved
0.7019	Intermediate Similarity	NPD8166	Discontinued
0.7006	Intermediate Similarity	NPD7685	Pre-registration
0.6993	Remote Similarity	NPD9494	Approved
0.6987	Remote Similarity	NPD4307	Phase 2
0.6987	Remote Similarity	NPD4060	Phase 1
0.6982	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD5977	Approved
0.6982	Remote Similarity	NPD5978	Approved
0.6982	Remote Similarity	NPD3817	Phase 2
0.6981	Remote Similarity	NPD5404	Approved
0.6981	Remote Similarity	NPD5406	Approved
0.6981	Remote Similarity	NPD5405	Approved
0.6981	Remote Similarity	NPD5408	Approved
0.6968	Remote Similarity	NPD5005	Approved
0.6968	Remote Similarity	NPD5006	Approved
0.6957	Remote Similarity	NPD6674	Discontinued
0.6951	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD447	Suspended
0.6943	Remote Similarity	NPD6355	Discontinued
0.694	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD1471	Phase 3
0.6928	Remote Similarity	NPD2798	Approved
0.6923	Remote Similarity	NPD6233	Phase 2
0.6914	Remote Similarity	NPD3750	Approved
0.6913	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD17	Approved
0.6903	Remote Similarity	NPD7095	Approved
0.6901	Remote Similarity	NPD3749	Approved
0.6897	Remote Similarity	NPD5242	Approved
0.6897	Remote Similarity	NPD3926	Phase 2
0.6879	Remote Similarity	NPD4140	Approved
0.6879	Remote Similarity	NPD1247	Approved
0.6875	Remote Similarity	NPD4477	Approved
0.6875	Remote Similarity	NPD7177	Discontinued
0.6875	Remote Similarity	NPD4476	Approved
0.6872	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD1934	Approved
0.6842	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3882	Suspended
0.6842	Remote Similarity	NPD7768	Phase 2
0.6839	Remote Similarity	NPD7229	Phase 3
0.6839	Remote Similarity	NPD6832	Phase 2
0.6835	Remote Similarity	NPD3657	Discovery
0.6835	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD2344	Approved
0.6829	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD5535	Approved
0.6824	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7038	Approved
0.6816	Remote Similarity	NPD7039	Approved
0.6815	Remote Similarity	NPD6663	Approved
0.6813	Remote Similarity	NPD4108	Discontinued
0.6813	Remote Similarity	NPD4308	Phase 3
0.6809	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD7074	Phase 3
0.6795	Remote Similarity	NPD7008	Discontinued
0.679	Remote Similarity	NPD2897	Discontinued
0.6782	Remote Similarity	NPD6959	Discontinued
0.6781	Remote Similarity	NPD1241	Discontinued
0.678	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD1894	Discontinued
0.6776	Remote Similarity	NPD1608	Approved
0.6772	Remote Similarity	NPD3620	Phase 2
0.6772	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD7999	Approved
0.6768	Remote Similarity	NPD3887	Approved
0.6766	Remote Similarity	NPD7427	Discontinued
0.6766	Remote Similarity	NPD920	Approved
0.6753	Remote Similarity	NPD3266	Approved
0.6753	Remote Similarity	NPD3267	Approved
0.675	Remote Similarity	NPD7097	Phase 1
0.6747	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6599	Discontinued
0.6742	Remote Similarity	NPD7054	Approved
0.6733	Remote Similarity	NPD5585	Approved
0.6733	Remote Similarity	NPD1357	Approved
0.6732	Remote Similarity	NPD5327	Phase 3
0.6728	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD2353	Approved
0.6727	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7440	Discontinued
0.6725	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD2801	Approved
0.6713	Remote Similarity	NPD1358	Approved
0.6706	Remote Similarity	NPD7411	Suspended
0.6704	Remote Similarity	NPD7472	Approved
0.6687	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7693	Approved
0.6667	Remote Similarity	NPD2309	Approved
0.6667	Remote Similarity	NPD5736	Approved
0.6667	Remote Similarity	NPD6166	Phase 2
0.6667	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8151	Discontinued
0.6667	Remote Similarity	NPD6190	Approved
0.6667	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1243	Approved
0.6645	Remote Similarity	NPD2797	Approved
0.6645	Remote Similarity	NPD1470	Approved
0.6626	Remote Similarity	NPD7266	Discontinued
0.6625	Remote Similarity	NPD230	Phase 1
0.6623	Remote Similarity	NPD3024	Approved
0.6623	Remote Similarity	NPD3025	Approved
0.6609	Remote Similarity	NPD7075	Discontinued
0.6609	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD4062	Phase 3
0.6601	Remote Similarity	NPD1201	Approved
0.6599	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD7783	Phase 2
0.6596	Remote Similarity	NPD2745	Approved
0.6596	Remote Similarity	NPD2746	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7808	Phase 3
0.6592	Remote Similarity	NPD3751	Discontinued
0.659	Remote Similarity	NPD5353	Approved
0.6588	Remote Similarity	NPD3455	Phase 2
0.6587	Remote Similarity	NPD1511	Approved
0.6587	Remote Similarity	NPD6799	Approved
0.6585	Remote Similarity	NPD5958	Discontinued
0.6584	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD2492	Phase 1
0.658	Remote Similarity	NPD7435	Discontinued
0.6575	Remote Similarity	NPD6797	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