NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	266.708
LogP:	2.75
LogD:	1.846
LogS:	-2.783
# Rotatable Bonds:	1
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.725
Synthetic Accessibility Score:	4.88
Fsp3:	0.533
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:	-4.518
MDCK Permeability:	1.7275668142247014e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.588
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.982
Plasma Protein Binding (PPB):	62.26622772216797%
Volume Distribution (VD):	2.037
Pgp-substrate:	33.2911376953125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.244
CYP1A2-substrate:	0.355
CYP2C19-inhibitor:	0.358
CYP2C19-substrate:	0.812
CYP2C9-inhibitor:	0.192
CYP2C9-substrate:	0.089
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.133
CYP3A4-inhibitor:	0.334
CYP3A4-substrate:	0.442

ADMET: Excretion

Clearance (CL):	6.41
Half-life (T1/2):	0.582

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.91
Drug-inuced Liver Injury (DILI):	0.931
AMES Toxicity:	0.09
Rat Oral Acute Toxicity:	0.959
Maximum Recommended Daily Dose:	0.471
Skin Sensitization:	0.771
Carcinogencity:	0.478
Eye Corrosion:	0.796
Eye Irritation:	0.319
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC23622

Natural Product ID:	NPC23622
*Common Name:**	Bisabolangelone
IUPAC Name:	(2Z,3S,3aS,7aR)-3-hydroxy-3,6-dimethyl-2-(3-methylbut-2-enylidene)-7,7a-dihydro-3aH-1-benzofuran-4-one
Synonyms:	Bisabolangelone
Standard InCHIKey:	GNWNPLBSEQDDQV-FRPWFYLFSA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-9(2)5-6-13-15(4,17)14-11(16)7-10(3)8-12(14)18-13/h5-7,12,14,17H,8H2,1-4H3/b13-6-/t12-,14+,15-/m1/s1
SMILES:	CC(=C/C=C/1O[C@H]2[C@@H]([C@]1(C)O)C(=O)C=C(C2)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2016934
PubChem CID:	12300142
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans

*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
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	leaf	n.a.	PMID[14727919]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	root	n.a.	PMID[14727919]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	xylem	n.a.	PMID[14727919]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	bark	n.a.	PMID[14727919]
NPO11147	Spongia hispida	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1479380]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[17238120]
NPO22063	Solanum lycocarpum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17249729]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[18405608]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[18496782]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[18661821]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21417376]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21627108]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25466114]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28737396]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[7700984]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	leaf	n.a.	Database[Article]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Stem Bark	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Testa	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Embryo	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12730	Heracleum maximum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15022	Baccharis flabellata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3127	Aralia continentalis	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22063	Solanum lycocarpum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18926	Tephrosia lupinifolia	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16778	Leptospermum liversidgei	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14231	Senecio barba-johannis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11147	Spongia hispida	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19012	Gasteria bicolor	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15022	Baccharis flabellata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3127	Aralia continentalis	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12730	Heracleum maximum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15484	Adlumia fungosa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18674	Juglans regia	Species	Juglandaceae	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	2
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT319	Cell Line	B16	Mus musculus	IC50	=	5.3	ug.mL-1	PMID[496095]
NPT2739	Individual Protein	Tyrosinase	Mus musculus	Inhibition	=	99.0	%	PMID[496096]
NPT2739	Individual Protein	Tyrosinase	Mus musculus	IC50	=	9000.0	nM	PMID[496096]

☑ 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 NPC23622 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	160
0.1-0.2	968
0.2-0.3	4355
0.3-0.4	9484
0.4-0.5	17178
0.5-0.6	7384
0.6-0.7	2834
0.7-0.8	325
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8193	Intermediate Similarity	NPC474197
0.8182	Intermediate Similarity	NPC187529
0.8085	Intermediate Similarity	NPC135576
0.8085	Intermediate Similarity	NPC93271
0.8065	Intermediate Similarity	NPC477241
0.8	Intermediate Similarity	NPC472007
0.7912	Intermediate Similarity	NPC228415
0.7912	Intermediate Similarity	NPC87189
0.7889	Intermediate Similarity	NPC472009
0.7812	Intermediate Similarity	NPC239895
0.7742	Intermediate Similarity	NPC477684
0.7732	Intermediate Similarity	NPC278008
0.7732	Intermediate Similarity	NPC35717
0.7727	Intermediate Similarity	NPC275766
0.7717	Intermediate Similarity	NPC472008
0.7692	Intermediate Similarity	NPC196381
0.766	Intermediate Similarity	NPC476705
0.7624	Intermediate Similarity	NPC469852
0.7586	Intermediate Similarity	NPC478122
0.7579	Intermediate Similarity	NPC29798
0.7579	Intermediate Similarity	NPC282644
0.7553	Intermediate Similarity	NPC469464
0.7553	Intermediate Similarity	NPC166554
0.7553	Intermediate Similarity	NPC15059
0.7549	Intermediate Similarity	NPC469853
0.7526	Intermediate Similarity	NPC472733
0.7526	Intermediate Similarity	NPC472734
0.75	Intermediate Similarity	NPC291260
0.7474	Intermediate Similarity	NPC230623
0.7449	Intermediate Similarity	NPC472731
0.7449	Intermediate Similarity	NPC472732
0.7449	Intermediate Similarity	NPC27105
0.7426	Intermediate Similarity	NPC473624
0.74	Intermediate Similarity	NPC469851
0.7396	Intermediate Similarity	NPC469692
0.7396	Intermediate Similarity	NPC469645
0.7391	Intermediate Similarity	NPC15807
0.7374	Intermediate Similarity	NPC472687
0.7374	Intermediate Similarity	NPC471330
0.7374	Intermediate Similarity	NPC177680
0.7374	Intermediate Similarity	NPC99657
0.7374	Intermediate Similarity	NPC472730
0.7374	Intermediate Similarity	NPC472729
0.7374	Intermediate Similarity	NPC203388
0.7374	Intermediate Similarity	NPC153776
0.7374	Intermediate Similarity	NPC471331
0.7374	Intermediate Similarity	NPC306908
0.7368	Intermediate Similarity	NPC265856
0.7363	Intermediate Similarity	NPC477784
0.7363	Intermediate Similarity	NPC477786
0.7363	Intermediate Similarity	NPC477785
0.734	Intermediate Similarity	NPC476803
0.734	Intermediate Similarity	NPC476706
0.734	Intermediate Similarity	NPC476707
0.734	Intermediate Similarity	NPC476708
0.7333	Intermediate Similarity	NPC470298
0.732	Intermediate Similarity	NPC121825
0.732	Intermediate Similarity	NPC114162
0.732	Intermediate Similarity	NPC469819
0.7312	Intermediate Similarity	NPC476043
0.7303	Intermediate Similarity	NPC258231
0.7303	Intermediate Similarity	NPC473981
0.7303	Intermediate Similarity	NPC473980
0.73	Intermediate Similarity	NPC472727
0.73	Intermediate Similarity	NPC472728
0.7292	Intermediate Similarity	NPC475441
0.7292	Intermediate Similarity	NPC261607
0.7292	Intermediate Similarity	NPC142838
0.7292	Intermediate Similarity	NPC300312
0.7292	Intermediate Similarity	NPC111114
0.7283	Intermediate Similarity	NPC295799
0.7282	Intermediate Similarity	NPC477125
0.7282	Intermediate Similarity	NPC471332
0.7282	Intermediate Similarity	NPC471333
0.7273	Intermediate Similarity	NPC471694
0.7273	Intermediate Similarity	NPC97173
0.7263	Intermediate Similarity	NPC295448
0.7255	Intermediate Similarity	NPC469980
0.7255	Intermediate Similarity	NPC104161
0.7255	Intermediate Similarity	NPC118902
0.7234	Intermediate Similarity	NPC113370
0.7234	Intermediate Similarity	NPC476079
0.7234	Intermediate Similarity	NPC103743
0.7234	Intermediate Similarity	NPC300779
0.7228	Intermediate Similarity	NPC224172
0.7228	Intermediate Similarity	NPC469657
0.7228	Intermediate Similarity	NPC9878
0.7228	Intermediate Similarity	NPC244456
0.7222	Intermediate Similarity	NPC162741
0.7222	Intermediate Similarity	NPC472948
0.7222	Intermediate Similarity	NPC91332
0.7212	Intermediate Similarity	NPC473284
0.7204	Intermediate Similarity	NPC307126
0.7204	Intermediate Similarity	NPC179006
0.7204	Intermediate Similarity	NPC307112
0.7204	Intermediate Similarity	NPC474853
0.7204	Intermediate Similarity	NPC125290
0.7204	Intermediate Similarity	NPC68303
0.72	Intermediate Similarity	NPC300584
0.7196	Intermediate Similarity	NPC66108
0.7195	Intermediate Similarity	NPC101670
0.7191	Intermediate Similarity	NPC475699
0.7188	Intermediate Similarity	NPC474232
0.7188	Intermediate Similarity	NPC131864
0.7184	Intermediate Similarity	NPC296950
0.7184	Intermediate Similarity	NPC146731
0.7174	Intermediate Similarity	NPC475083
0.7172	Intermediate Similarity	NPC8803
0.717	Intermediate Similarity	NPC99760
0.7158	Intermediate Similarity	NPC119740
0.7158	Intermediate Similarity	NPC150063
0.7158	Intermediate Similarity	NPC473658
0.7158	Intermediate Similarity	NPC476805
0.7157	Intermediate Similarity	NPC70369
0.7157	Intermediate Similarity	NPC39996
0.7143	Intermediate Similarity	NPC475418
0.7143	Intermediate Similarity	NPC473482
0.7143	Intermediate Similarity	NPC318363
0.7143	Intermediate Similarity	NPC167219
0.7128	Intermediate Similarity	NPC203795
0.7128	Intermediate Similarity	NPC278283
0.7128	Intermediate Similarity	NPC469910
0.7113	Intermediate Similarity	NPC6099
0.7113	Intermediate Similarity	NPC116726
0.7113	Intermediate Similarity	NPC252433
0.7113	Intermediate Similarity	NPC146852
0.7113	Intermediate Similarity	NPC303230
0.7113	Intermediate Similarity	NPC327760
0.7113	Intermediate Similarity	NPC114345
0.7111	Intermediate Similarity	NPC475210
0.71	Intermediate Similarity	NPC53844
0.71	Intermediate Similarity	NPC20066
0.71	Intermediate Similarity	NPC474938
0.71	Intermediate Similarity	NPC474785
0.7097	Intermediate Similarity	NPC32676
0.7087	Intermediate Similarity	NPC475050
0.7083	Intermediate Similarity	NPC307092
0.7079	Intermediate Similarity	NPC82666
0.7079	Intermediate Similarity	NPC471061
0.7079	Intermediate Similarity	NPC34110
0.7079	Intermediate Similarity	NPC272267
0.7075	Intermediate Similarity	NPC38154
0.7075	Intermediate Similarity	NPC471400
0.7075	Intermediate Similarity	NPC87335
0.7075	Intermediate Similarity	NPC475065
0.7071	Intermediate Similarity	NPC316215
0.7071	Intermediate Similarity	NPC91408
0.7065	Intermediate Similarity	NPC475690
0.7059	Intermediate Similarity	NPC185141
0.7059	Intermediate Similarity	NPC110443
0.7059	Intermediate Similarity	NPC474742
0.7059	Intermediate Similarity	NPC46998
0.7059	Intermediate Similarity	NPC133907
0.7059	Intermediate Similarity	NPC128733
0.7059	Intermediate Similarity	NPC181645
0.7059	Intermediate Similarity	NPC207885
0.7059	Intermediate Similarity	NPC471401
0.7054	Intermediate Similarity	NPC478051
0.7048	Intermediate Similarity	NPC329048
0.7048	Intermediate Similarity	NPC330011
0.7048	Intermediate Similarity	NPC266514
0.7041	Intermediate Similarity	NPC61275
0.7033	Intermediate Similarity	NPC233352
0.7033	Intermediate Similarity	NPC824
0.7033	Intermediate Similarity	NPC172013
0.7033	Intermediate Similarity	NPC138492
0.703	Intermediate Similarity	NPC159763
0.703	Intermediate Similarity	NPC475284
0.703	Intermediate Similarity	NPC281608
0.703	Intermediate Similarity	NPC124512
0.703	Intermediate Similarity	NPC278386
0.7021	Intermediate Similarity	NPC470755
0.7011	Intermediate Similarity	NPC186042
0.7011	Intermediate Similarity	NPC275098
0.701	Intermediate Similarity	NPC473099
0.701	Intermediate Similarity	NPC230332
0.701	Intermediate Similarity	NPC471399
0.7009	Intermediate Similarity	NPC286880
0.7	Intermediate Similarity	NPC93763
0.7	Intermediate Similarity	NPC21681
0.7	Intermediate Similarity	NPC248624
0.7	Intermediate Similarity	NPC231739
0.7	Intermediate Similarity	NPC108816
0.7	Intermediate Similarity	NPC218817
0.7	Intermediate Similarity	NPC11796
0.7	Intermediate Similarity	NPC475994
0.7	Intermediate Similarity	NPC472675
0.7	Intermediate Similarity	NPC267231
0.699	Remote Similarity	NPC478176
0.6989	Remote Similarity	NPC66764
0.6989	Remote Similarity	NPC110150
0.6981	Remote Similarity	NPC264819
0.6979	Remote Similarity	NPC260343
0.6979	Remote Similarity	NPC475819
0.6979	Remote Similarity	NPC26078
0.6979	Remote Similarity	NPC136879
0.697	Remote Similarity	NPC217624
0.697	Remote Similarity	NPC14322
0.697	Remote Similarity	NPC181393
0.697	Remote Similarity	NPC53685

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 NPC23622 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	150
0.1-0.2	1334
0.2-0.3	3813
0.3-0.4	2636
0.4-0.5	822
0.5-0.6	334
0.6-0.7	58
0.7-0.8	3
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
0.7143	Intermediate Similarity	NPD5282	Discontinued
0.703	Intermediate Similarity	NPD4225	Approved
0.6989	Remote Similarity	NPD6110	Phase 1
0.6869	Remote Similarity	NPD5778	Approved
0.6869	Remote Similarity	NPD5779	Approved
0.6842	Remote Similarity	NPD1696	Phase 3
0.6786	Remote Similarity	NPD7115	Discovery
0.6768	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD5363	Approved
0.6632	Remote Similarity	NPD7154	Phase 3
0.6574	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD6101	Approved
0.6566	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD8517	Approved
0.6552	Remote Similarity	NPD8515	Approved
0.6552	Remote Similarity	NPD8513	Phase 3
0.6552	Remote Similarity	NPD8516	Approved
0.6545	Remote Similarity	NPD6371	Approved
0.6526	Remote Similarity	NPD4270	Approved
0.6526	Remote Similarity	NPD4269	Approved
0.6522	Remote Similarity	NPD4756	Discovery
0.65	Remote Similarity	NPD6698	Approved
0.65	Remote Similarity	NPD5785	Approved
0.65	Remote Similarity	NPD46	Approved
0.6436	Remote Similarity	NPD6411	Approved
0.6429	Remote Similarity	NPD3618	Phase 1
0.6429	Remote Similarity	NPD368	Approved
0.6429	Remote Similarity	NPD5786	Approved
0.6421	Remote Similarity	NPD5369	Approved
0.6354	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD7331	Phase 2
0.6316	Remote Similarity	NPD4252	Approved
0.6281	Remote Similarity	NPD8074	Phase 3
0.6275	Remote Similarity	NPD7637	Suspended
0.6263	Remote Similarity	NPD5279	Phase 3
0.6263	Remote Similarity	NPD4249	Approved
0.6263	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD4519	Discontinued
0.6263	Remote Similarity	NPD4623	Approved
0.6226	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD3665	Phase 1
0.6224	Remote Similarity	NPD3666	Approved
0.6224	Remote Similarity	NPD3133	Approved
0.62	Remote Similarity	NPD4251	Approved
0.62	Remote Similarity	NPD4250	Approved
0.62	Remote Similarity	NPD7524	Approved
0.6195	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7839	Suspended
0.6186	Remote Similarity	NPD5209	Approved
0.6186	Remote Similarity	NPD3667	Approved
0.6176	Remote Similarity	NPD7838	Discovery
0.6146	Remote Similarity	NPD4821	Approved
0.6146	Remote Similarity	NPD4820	Approved
0.6146	Remote Similarity	NPD4819	Approved
0.6146	Remote Similarity	NPD4822	Approved
0.6146	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD5362	Discontinued
0.61	Remote Similarity	NPD5280	Approved
0.61	Remote Similarity	NPD4694	Approved
0.6095	Remote Similarity	NPD5695	Phase 3
0.6078	Remote Similarity	NPD4753	Phase 2
0.6078	Remote Similarity	NPD5328	Approved
0.6075	Remote Similarity	NPD5696	Approved
0.6061	Remote Similarity	NPD4786	Approved
0.6058	Remote Similarity	NPD4202	Approved
0.6058	Remote Similarity	NPD6399	Phase 3
0.6055	Remote Similarity	NPD5211	Phase 2
0.6023	Remote Similarity	NPD7341	Phase 2
0.602	Remote Similarity	NPD4223	Phase 3
0.602	Remote Similarity	NPD4221	Approved
0.6019	Remote Similarity	NPD5207	Approved
0.6019	Remote Similarity	NPD6648	Approved
0.6	Remote Similarity	NPD7748	Approved
0.6	Remote Similarity	NPD6053	Discontinued
0.5982	Remote Similarity	NPD6412	Phase 2
0.5981	Remote Similarity	NPD7902	Approved
0.5981	Remote Similarity	NPD6084	Phase 2
0.5981	Remote Similarity	NPD4755	Approved
0.5981	Remote Similarity	NPD6083	Phase 2
0.598	Remote Similarity	NPD4518	Approved
0.5979	Remote Similarity	NPD4695	Discontinued
0.5965	Remote Similarity	NPD4634	Approved
0.5963	Remote Similarity	NPD5344	Discontinued
0.5962	Remote Similarity	NPD6079	Approved
0.5962	Remote Similarity	NPD5281	Approved
0.5962	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD5284	Approved
0.596	Remote Similarity	NPD6695	Phase 3
0.5957	Remote Similarity	NPD8264	Approved
0.5955	Remote Similarity	NPD3704	Approved
0.5946	Remote Similarity	NPD5141	Approved
0.5943	Remote Similarity	NPD4629	Approved
0.5943	Remote Similarity	NPD5210	Approved
0.5941	Remote Similarity	NPD7334	Approved
0.5941	Remote Similarity	NPD5330	Approved
0.5941	Remote Similarity	NPD6684	Approved
0.5941	Remote Similarity	NPD7521	Approved
0.5941	Remote Similarity	NPD7146	Approved
0.5941	Remote Similarity	NPD6409	Approved
0.5938	Remote Similarity	NPD4268	Approved
0.5938	Remote Similarity	NPD4271	Approved
0.5938	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD5370	Suspended
0.5922	Remote Similarity	NPD1695	Approved
0.5917	Remote Similarity	NPD6319	Approved
0.5917	Remote Similarity	NPD6054	Approved
0.5917	Remote Similarity	NPD6059	Approved
0.5913	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD342	Phase 1
0.59	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.59	Remote Similarity	NPD4197	Approved
0.5895	Remote Similarity	NPD6933	Approved
0.5893	Remote Similarity	NPD7128	Approved
0.5893	Remote Similarity	NPD6675	Approved
0.5893	Remote Similarity	NPD5739	Approved
0.5893	Remote Similarity	NPD6402	Approved
0.5888	Remote Similarity	NPD4697	Phase 3
0.5877	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD6372	Approved
0.5877	Remote Similarity	NPD6373	Approved
0.5872	Remote Similarity	NPD4700	Approved
0.5872	Remote Similarity	NPD7639	Approved
0.5872	Remote Similarity	NPD5285	Approved
0.5872	Remote Similarity	NPD5286	Approved
0.5872	Remote Similarity	NPD4696	Approved
0.5872	Remote Similarity	NPD7640	Approved
0.5868	Remote Similarity	NPD6015	Approved
0.5868	Remote Similarity	NPD6016	Approved
0.5862	Remote Similarity	NPD8297	Approved
0.5859	Remote Similarity	NPD6435	Approved
0.5842	Remote Similarity	NPD5329	Approved
0.5841	Remote Similarity	NPD5701	Approved
0.5841	Remote Similarity	NPD5697	Approved
0.5826	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD6903	Approved
0.582	Remote Similarity	NPD6370	Approved
0.582	Remote Similarity	NPD5988	Approved
0.5816	Remote Similarity	NPD7514	Phase 3
0.5816	Remote Similarity	NPD6931	Approved
0.5816	Remote Similarity	NPD6930	Phase 2
0.5816	Remote Similarity	NPD7332	Phase 2
0.581	Remote Similarity	NPD7515	Phase 2
0.58	Remote Similarity	NPD5331	Approved
0.58	Remote Similarity	NPD5332	Approved
0.5798	Remote Similarity	NPD7500	Approved
0.5795	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD7320	Approved
0.5789	Remote Similarity	NPD6881	Approved
0.5789	Remote Similarity	NPD6686	Approved
0.5789	Remote Similarity	NPD6899	Approved
0.5789	Remote Similarity	NPD8039	Approved
0.5784	Remote Similarity	NPD4689	Approved
0.5784	Remote Similarity	NPD4693	Phase 3
0.5784	Remote Similarity	NPD5690	Phase 2
0.5784	Remote Similarity	NPD4690	Approved
0.5784	Remote Similarity	NPD4688	Approved
0.5784	Remote Similarity	NPD4138	Approved
0.5784	Remote Similarity	NPD5205	Approved
0.578	Remote Similarity	NPD7638	Approved
0.5778	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD6650	Approved
0.5776	Remote Similarity	NPD6649	Approved
0.5773	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD3617	Approved
0.5769	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD5225	Approved
0.5766	Remote Similarity	NPD5226	Approved
0.5766	Remote Similarity	NPD4633	Approved
0.5766	Remote Similarity	NPD5224	Approved
0.5758	Remote Similarity	NPD4790	Discontinued
0.5752	Remote Similarity	NPD6008	Approved
0.5743	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD3668	Phase 3
0.5741	Remote Similarity	NPD5222	Approved
0.5741	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD5221	Approved
0.5739	Remote Similarity	NPD6012	Approved
0.5739	Remote Similarity	NPD6013	Approved
0.5739	Remote Similarity	NPD6014	Approved
0.5738	Remote Similarity	NPD7503	Approved
0.5728	Remote Similarity	NPD7750	Discontinued
0.5726	Remote Similarity	NPD7492	Approved
0.5714	Remote Similarity	NPD6647	Phase 2
0.5714	Remote Similarity	NPD5692	Phase 3
0.5714	Remote Similarity	NPD5175	Approved
0.5714	Remote Similarity	NPD4096	Approved
0.5714	Remote Similarity	NPD6929	Approved
0.5714	Remote Similarity	NPD5174	Approved
0.5701	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD7900	Approved
0.5701	Remote Similarity	NPD6001	Approved
0.57	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.569	Remote Similarity	NPD7290	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