NPASS Compound

Structure

NPC470818 OpenBabel07101719142D 32 35 0 0 1 0 0 0 0 0999 V2000 -0.3364 -5.5827 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 0.5296 -2.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3546 1.5897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0540 -0.3783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7258 -0.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7258 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8597 0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8597 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9937 -0.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1277 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1277 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5296 -4.0827 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 -0.3364 -4.5827 0.0000 C 0 0 1 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 3.9937 -1.0827 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 -2.0685 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5296 -3.0827 0.0000 C 0 0 2 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 -1.2024 -3.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3364 -2.5827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9345 -3.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2617 -4.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6637 0.6386 0.0000 O 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 1.3956 -2.5827 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 2 16 2 0 0 0 0 4 29 1 0 0 0 0 5 30 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 2 0 0 0 0 9 17 2 0 0 0 0 10 17 1 0 0 0 0 11 12 2 0 0 0 0 11 17 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 13 20 1 0 0 0 0 14 18 2 0 0 0 0 14 19 1 0 0 0 0 15 1 1 6 0 0 0 15 16 1 0 0 0 0 16 22 1 0 0 0 0 18 23 1 0 0 0 0 18 24 1 0 0 0 0 19 22 1 0 0 0 0 19 27 2 0 0 0 0 20 26 1 6 0 0 0 20 31 1 0 0 0 0 21 28 2 0 0 0 0 21 31 1 0 0 0 0 22 26 1 6 0 0 0 23 25 1 0 0 0 0 23 26 1 6 0 0 0 24 29 1 1 0 0 0 24 32 1 0 0 0 0 25 30 1 1 0 0 0 25 32 1 0 0 0 0 26 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	438.2
Volume:	455.676
LogP:	3.423
LogD:	3.447
LogS:	-5.088
# Rotatable Bonds:	6
TPSA:	71.06
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.501
Synthetic Accessibility Score:	4.726
Fsp3:	0.462
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:	-4.64
MDCK Permeability:	2.1092459064675495e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.415
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.227
30% Bioavailability (F30%):	0.843

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.918
Plasma Protein Binding (PPB):	87.24613189697266%
Volume Distribution (VD):	1.426
Pgp-substrate:	10.52771282196045%

ADMET: Metabolism

CYP1A2-inhibitor:	0.443
CYP1A2-substrate:	0.115
CYP2C19-inhibitor:	0.393
CYP2C19-substrate:	0.545
CYP2C9-inhibitor:	0.848
CYP2C9-substrate:	0.095
CYP2D6-inhibitor:	0.52
CYP2D6-substrate:	0.056
CYP3A4-inhibitor:	0.949
CYP3A4-substrate:	0.568

ADMET: Excretion

Clearance (CL):	9.026
Half-life (T1/2):	0.27

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.177
Drug-inuced Liver Injury (DILI):	0.907
AMES Toxicity:	0.051
Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.141
Skin Sensitization:	0.959
Carcinogencity:	0.092
Eye Corrosion:	0.02
Eye Irritation:	0.225
Respiratory Toxicity:	0.857

Download Data

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

Natural Product: NPC470818

Natural Product ID:	NPC470818
*Common Name:**	(1R,3S,5As,7S,9R,9Ar,9Br)-1,3-Dimethoxy-7,9A-Dimethyl-6-Methylene-5-Oxo-1,3,5,5A,6,7,8,9,9A,9B-Decahydronaphtho[2,1-C]Furan-9-Yl Cinnamate
IUPAC Name:	[(1R,3S,5aS,7S,9R,9aR,9bR)-1,3-dimethoxy-7,9a-dimethyl-6-methylidene-5-oxo-3,5a,7,8,9,9b-hexahydro-1H-benzo[e][2]benzofuran-9-yl] (E)-3-phenylprop-2-enoate
Synonyms:
Standard InCHIKey:	QUIOFBAKMJWQEO-UFQTXSPKSA-N
Standard InCHI:	InChI=1S/C26H30O6/c1-15-13-20(31-21(28)12-11-17-9-7-6-8-10-17)26(3)22(16(15)2)19(27)14-18-23(26)25(30-5)32-24(18)29-4/h6-12,14-15,20,22-25H,2,13H2,1,3-5H3/b12-11+/t15-,20+,22+,23+,24-,25+,26-/m0/s1
SMILES:	CO[C@@H]1O[C@@H](C2=CC(=O)[C@@H]3[C@]([C@@H]12)(C)[C@H](OC(=O)/C=C/c1ccccc1)C[C@@H](C3=C)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2252776
PubChem CID:	11611881
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO12007	Pseudowintera axillaris	Species	Winteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16417306]
NPO12007	Pseudowintera axillaris	Species	Winteraceae	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
Others	5

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Unit	Reference
NPT827	Organism	Mycosphaerella graminicola	Mycosphaerella graminicola	Inhibition	=	%	PMID[566566]
NPT6576	Organism	Puccinia graminis f. tritici	Puccinia graminis f. tritici	Inhibition	=	%	PMID[566566]
NPT1095	Organism	Plasmopara viticola	Plasmopara viticola	Inhibition	=	%	PMID[566566]
NPT825	Organism	Phytophthora infestans	Phytophthora infestans	Inhibition	=	%	PMID[566566]
NPT828	Organism	Phaeosphaeria nodorum	Phaeosphaeria nodorum	Inhibition	=	%	PMID[566566]

☑ 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 NPC470818 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	273
0.1-0.2	1167
0.2-0.3	1969
0.3-0.4	4830
0.4-0.5	8906
0.5-0.6	17776
0.6-0.7	6716
0.7-0.8	1004
0.8-0.85	43
0.85-0.9	7
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9244	High Similarity	NPC470814
0.9032	High Similarity	NPC470816
0.8906	High Similarity	NPC475493
0.8871	High Similarity	NPC470815
0.8846	High Similarity	NPC473399
0.8846	High Similarity	NPC473216
0.8615	High Similarity	NPC471880
0.8607	High Similarity	NPC152812
0.8594	High Similarity	NPC195224
0.8594	High Similarity	NPC230331
0.8571	High Similarity	NPC469742
0.8516	High Similarity	NPC473423
0.8444	Intermediate Similarity	NPC475400
0.8425	Intermediate Similarity	NPC140118
0.8425	Intermediate Similarity	NPC12881
0.8397	Intermediate Similarity	NPC472418
0.8385	Intermediate Similarity	NPC225103
0.8374	Intermediate Similarity	NPC470820
0.8333	Intermediate Similarity	NPC80599
0.8321	Intermediate Similarity	NPC472388
0.8321	Intermediate Similarity	NPC473443
0.8321	Intermediate Similarity	NPC147561
0.8306	Intermediate Similarity	NPC84129
0.8295	Intermediate Similarity	NPC473082
0.8258	Intermediate Similarity	NPC472361
0.8214	Intermediate Similarity	NPC469513
0.8209	Intermediate Similarity	NPC471911
0.8209	Intermediate Similarity	NPC4242
0.8195	Intermediate Similarity	NPC472394
0.8195	Intermediate Similarity	NPC209851
0.8154	Intermediate Similarity	NPC100402
0.8154	Intermediate Similarity	NPC9180
0.8134	Intermediate Similarity	NPC472437
0.8095	Intermediate Similarity	NPC89324
0.8077	Intermediate Similarity	NPC473083
0.8074	Intermediate Similarity	NPC474608
0.8071	Intermediate Similarity	NPC111466
0.8065	Intermediate Similarity	NPC473869
0.8058	Intermediate Similarity	NPC473755
0.8058	Intermediate Similarity	NPC475513
0.8056	Intermediate Similarity	NPC87630
0.8056	Intermediate Similarity	NPC116292
0.8056	Intermediate Similarity	NPC162569
0.8056	Intermediate Similarity	NPC267469
0.8056	Intermediate Similarity	NPC179128
0.8056	Intermediate Similarity	NPC35160
0.8049	Intermediate Similarity	NPC469547
0.8047	Intermediate Similarity	NPC300827
0.8047	Intermediate Similarity	NPC473439
0.8047	Intermediate Similarity	NPC311175
0.8047	Intermediate Similarity	NPC37641
0.8043	Intermediate Similarity	NPC477904
0.8043	Intermediate Similarity	NPC183270
0.8029	Intermediate Similarity	NPC184109
0.8028	Intermediate Similarity	NPC208293
0.8015	Intermediate Similarity	NPC472577
0.8015	Intermediate Similarity	NPC195647
0.8015	Intermediate Similarity	NPC291638
0.8015	Intermediate Similarity	NPC66761
0.8015	Intermediate Similarity	NPC17877
0.8014	Intermediate Similarity	NPC40085
0.8014	Intermediate Similarity	NPC264270
0.8	Intermediate Similarity	NPC133430
0.8	Intermediate Similarity	NPC469477
0.8	Intermediate Similarity	NPC69425
0.7986	Intermediate Similarity	NPC77493
0.7984	Intermediate Similarity	NPC473749
0.7984	Intermediate Similarity	NPC70973
0.7959	Intermediate Similarity	NPC469417
0.7945	Intermediate Similarity	NPC469456
0.7943	Intermediate Similarity	NPC471912
0.7943	Intermediate Similarity	NPC80895
0.7941	Intermediate Similarity	NPC329913
0.7941	Intermediate Similarity	NPC48929
0.7929	Intermediate Similarity	NPC63737
0.7923	Intermediate Similarity	NPC12016
0.7917	Intermediate Similarity	NPC469448
0.7914	Intermediate Similarity	NPC473440
0.7899	Intermediate Similarity	NPC283375
0.7899	Intermediate Similarity	NPC475373
0.7899	Intermediate Similarity	NPC183122
0.7891	Intermediate Similarity	NPC476096
0.7887	Intermediate Similarity	NPC471107
0.7887	Intermediate Similarity	NPC301946
0.7887	Intermediate Similarity	NPC471100
0.7887	Intermediate Similarity	NPC277053
0.7883	Intermediate Similarity	NPC477893
0.7868	Intermediate Similarity	NPC476644
0.7868	Intermediate Similarity	NPC15850
0.7863	Intermediate Similarity	NPC472373
0.7862	Intermediate Similarity	NPC329657
0.7857	Intermediate Similarity	NPC476476
0.7852	Intermediate Similarity	NPC469519
0.7852	Intermediate Similarity	NPC470278
0.7842	Intermediate Similarity	NPC210591
0.7842	Intermediate Similarity	NPC475652
0.7842	Intermediate Similarity	NPC472371
0.7842	Intermediate Similarity	NPC214550
0.7842	Intermediate Similarity	NPC472395
0.7826	Intermediate Similarity	NPC472374
0.7826	Intermediate Similarity	NPC472551
0.7826	Intermediate Similarity	NPC472372
0.7826	Intermediate Similarity	NPC472545
0.7823	Intermediate Similarity	NPC471176
0.7823	Intermediate Similarity	NPC5115
0.782	Intermediate Similarity	NPC169913
0.782	Intermediate Similarity	NPC51292
0.7812	Intermediate Similarity	NPC473860
0.781	Intermediate Similarity	NPC203486
0.781	Intermediate Similarity	NPC126516
0.7803	Intermediate Similarity	NPC471758
0.7803	Intermediate Similarity	NPC114927
0.7801	Intermediate Similarity	NPC140021
0.7801	Intermediate Similarity	NPC475135
0.7794	Intermediate Similarity	NPC238370
0.7793	Intermediate Similarity	NPC303429
0.7793	Intermediate Similarity	NPC475417
0.7793	Intermediate Similarity	NPC472761
0.7793	Intermediate Similarity	NPC222102
0.7793	Intermediate Similarity	NPC475561
0.7786	Intermediate Similarity	NPC275592
0.7786	Intermediate Similarity	NPC43241
0.7786	Intermediate Similarity	NPC473112
0.7786	Intermediate Similarity	NPC147880
0.7786	Intermediate Similarity	NPC473081
0.7786	Intermediate Similarity	NPC171207
0.7786	Intermediate Similarity	NPC473109
0.7786	Intermediate Similarity	NPC472547
0.7786	Intermediate Similarity	NPC48017
0.7786	Intermediate Similarity	NPC211137
0.7786	Intermediate Similarity	NPC184747
0.7786	Intermediate Similarity	NPC100913
0.7786	Intermediate Similarity	NPC473613
0.7786	Intermediate Similarity	NPC97667
0.7786	Intermediate Similarity	NPC473758
0.7786	Intermediate Similarity	NPC200592
0.7786	Intermediate Similarity	NPC473085
0.7786	Intermediate Similarity	NPC90614
0.7786	Intermediate Similarity	NPC473060
0.7786	Intermediate Similarity	NPC476094
0.7786	Intermediate Similarity	NPC4341
0.7785	Intermediate Similarity	NPC469399
0.7778	Intermediate Similarity	NPC27712
0.7778	Intermediate Similarity	NPC320734
0.777	Intermediate Similarity	NPC39549
0.776	Intermediate Similarity	NPC128368
0.7755	Intermediate Similarity	NPC472658
0.7755	Intermediate Similarity	NPC472657
0.7754	Intermediate Similarity	NPC477896
0.7754	Intermediate Similarity	NPC471864
0.7748	Intermediate Similarity	NPC165234
0.7748	Intermediate Similarity	NPC475536
0.7744	Intermediate Similarity	NPC45821
0.7744	Intermediate Similarity	NPC476970
0.7744	Intermediate Similarity	NPC470158
0.7744	Intermediate Similarity	NPC475933
0.7744	Intermediate Similarity	NPC473111
0.7744	Intermediate Similarity	NPC473110
0.7744	Intermediate Similarity	NPC275576
0.774	Intermediate Similarity	NPC469415
0.7737	Intermediate Similarity	NPC472656
0.7734	Intermediate Similarity	NPC61651
0.773	Intermediate Similarity	NPC97947
0.773	Intermediate Similarity	NPC87448
0.773	Intermediate Similarity	NPC118080
0.773	Intermediate Similarity	NPC472576
0.773	Intermediate Similarity	NPC291599
0.773	Intermediate Similarity	NPC16912
0.773	Intermediate Similarity	NPC41481
0.773	Intermediate Similarity	NPC27377
0.7727	Intermediate Similarity	NPC473881
0.7727	Intermediate Similarity	NPC307139
0.7724	Intermediate Similarity	NPC112457
0.7721	Intermediate Similarity	NPC72915
0.7721	Intermediate Similarity	NPC291419
0.7721	Intermediate Similarity	NPC60825
0.7721	Intermediate Similarity	NPC305162
0.7721	Intermediate Similarity	NPC475478
0.7703	Intermediate Similarity	NPC34066
0.7703	Intermediate Similarity	NPC469422
0.7698	Intermediate Similarity	NPC307651
0.7697	Intermediate Similarity	NPC475505
0.7697	Intermediate Similarity	NPC475300
0.7697	Intermediate Similarity	NPC475437
0.7697	Intermediate Similarity	NPC295408
0.7697	Intermediate Similarity	NPC150893
0.7697	Intermediate Similarity	NPC475464
0.7697	Intermediate Similarity	NPC329960
0.7697	Intermediate Similarity	NPC473641
0.7697	Intermediate Similarity	NPC473797
0.7692	Intermediate Similarity	NPC473243
0.7692	Intermediate Similarity	NPC470231
0.7687	Intermediate Similarity	NPC476971
0.7687	Intermediate Similarity	NPC253681
0.7687	Intermediate Similarity	NPC476972
0.7687	Intermediate Similarity	NPC171007
0.7687	Intermediate Similarity	NPC190849
0.7681	Intermediate Similarity	NPC310662
0.7676	Intermediate Similarity	NPC183540
0.7671	Intermediate Similarity	NPC254558

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 NPC470818 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	232
0.1-0.2	759
0.2-0.3	1306
0.3-0.4	3091
0.4-0.5	2310
0.5-0.6	1189
0.6-0.7	250
0.7-0.8	13
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
0.776	Intermediate Similarity	NPD6858	Approved
0.776	Intermediate Similarity	NPD7094	Approved
0.7647	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7799	Discontinued
0.7397	Intermediate Similarity	NPD7236	Approved
0.7244	Intermediate Similarity	NPD2067	Discontinued
0.7165	Intermediate Similarity	NPD2182	Approved
0.7152	Intermediate Similarity	NPD7239	Suspended
0.712	Intermediate Similarity	NPD5909	Discontinued
0.705	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD3317	Approved
0.7042	Intermediate Similarity	NPD7961	Discontinued
0.704	Intermediate Similarity	NPD6647	Phase 2
0.7037	Intermediate Similarity	NPD5125	Phase 3
0.7037	Intermediate Similarity	NPD5126	Approved
0.7023	Intermediate Similarity	NPD6010	Discontinued
0.7007	Intermediate Similarity	NPD6637	Approved
0.6988	Remote Similarity	NPD8407	Phase 2
0.697	Remote Similarity	NPD2629	Approved
0.6942	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD2066	Phase 3
0.6934	Remote Similarity	NPD6287	Discontinued
0.6933	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD8166	Discontinued
0.6909	Remote Similarity	NPD8368	Discontinued
0.6901	Remote Similarity	NPD7008	Discontinued
0.687	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD37	Approved
0.685	Remote Similarity	NPD164	Approved
0.6842	Remote Similarity	NPD5951	Approved
0.6835	Remote Similarity	NPD4965	Approved
0.6835	Remote Similarity	NPD7057	Phase 3
0.6835	Remote Similarity	NPD4967	Phase 2
0.6835	Remote Similarity	NPD4966	Approved
0.6835	Remote Similarity	NPD7058	Phase 2
0.6831	Remote Similarity	NPD7055	Discontinued
0.6829	Remote Similarity	NPD1989	Approved
0.6815	Remote Similarity	NPD6065	Approved
0.6803	Remote Similarity	NPD7305	Phase 1
0.6797	Remote Similarity	NPD5048	Discontinued
0.6794	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD3495	Discontinued
0.6774	Remote Similarity	NPD7458	Discontinued
0.6772	Remote Similarity	NPD1929	Approved
0.6772	Remote Similarity	NPD1930	Approved
0.6772	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6234	Discontinued
0.6744	Remote Similarity	NPD6685	Approved
0.6736	Remote Similarity	NPD3764	Approved
0.6695	Remote Similarity	NPD1694	Approved
0.6694	Remote Similarity	NPD3673	Approved
0.6694	Remote Similarity	NPD3672	Approved
0.6692	Remote Similarity	NPD6686	Approved
0.669	Remote Similarity	NPD8032	Phase 2
0.669	Remote Similarity	NPD6663	Approved
0.6689	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD4628	Phase 3
0.6667	Remote Similarity	NPD1238	Approved
0.6667	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4198	Discontinued
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7798	Approved
0.6667	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD5736	Approved
0.6642	Remote Similarity	NPD7741	Discontinued
0.6624	Remote Similarity	NPD7028	Phase 2
0.6623	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD8434	Phase 2
0.6608	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.66	Remote Similarity	NPD2346	Discontinued
0.66	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD3024	Approved
0.6594	Remote Similarity	NPD3025	Approved
0.6587	Remote Similarity	NPD5926	Approved
0.6581	Remote Similarity	NPD6273	Approved
0.6569	Remote Similarity	NPD7610	Discontinued
0.6566	Remote Similarity	NPD7228	Approved
0.6564	Remote Similarity	NPD8127	Discontinued
0.6562	Remote Similarity	NPD1932	Approved
0.6561	Remote Similarity	NPD3226	Approved
0.6547	Remote Similarity	NPD17	Approved
0.6547	Remote Similarity	NPD2932	Approved
0.6543	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD8361	Approved
0.6532	Remote Similarity	NPD8360	Approved
0.6532	Remote Similarity	NPD8435	Approved
0.6531	Remote Similarity	NPD2979	Phase 3
0.6529	Remote Similarity	NPD8312	Approved
0.6529	Remote Similarity	NPD8313	Approved
0.6522	Remote Similarity	NPD7009	Phase 2
0.6516	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD2329	Discontinued
0.6513	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD5765	Approved
0.6503	Remote Similarity	NPD3266	Approved
0.6503	Remote Similarity	NPD3267	Approved
0.65	Remote Similarity	NPD3026	Approved
0.65	Remote Similarity	NPD3023	Approved
0.6493	Remote Similarity	NPD969	Suspended
0.649	Remote Similarity	NPD7266	Discontinued
0.649	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.649	Remote Similarity	NPD6004	Phase 3
0.649	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.649	Remote Similarity	NPD6005	Phase 3
0.649	Remote Similarity	NPD6002	Phase 3
0.649	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.648	Remote Similarity	NPD1693	Approved
0.6475	Remote Similarity	NPD5585	Approved
0.6471	Remote Similarity	NPD4766	Approved
0.6471	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD3748	Approved
0.6458	Remote Similarity	NPD6085	Phase 2
0.6458	Remote Similarity	NPD2798	Approved
0.6458	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD1088	Approved
0.6452	Remote Similarity	NPD7631	Approved
0.6446	Remote Similarity	NPD1087	Approved
0.6429	Remote Similarity	NPD3019	Approved
0.6414	Remote Similarity	NPD7084	Phase 3
0.6412	Remote Similarity	NPD6559	Discontinued
0.6412	Remote Similarity	NPD6764	Approved
0.6412	Remote Similarity	NPD6765	Approved
0.6412	Remote Similarity	NPD7240	Approved
0.641	Remote Similarity	NPD2533	Approved
0.641	Remote Similarity	NPD2534	Approved
0.641	Remote Similarity	NPD2532	Approved
0.6408	Remote Similarity	NPD3972	Approved
0.6408	Remote Similarity	NPD1608	Approved
0.6402	Remote Similarity	NPD5494	Approved
0.64	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD7819	Suspended
0.6395	Remote Similarity	NPD3268	Approved
0.6395	Remote Similarity	NPD2313	Discontinued
0.6385	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD7609	Phase 3
0.637	Remote Similarity	NPD6912	Phase 3
0.6369	Remote Similarity	NPD3818	Discontinued
0.6364	Remote Similarity	NPD7003	Approved
0.6364	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7199	Phase 2
0.6358	Remote Similarity	NPD2799	Discontinued
0.6357	Remote Similarity	NPD5691	Approved
0.6357	Remote Similarity	NPD7503	Approved
0.6351	Remote Similarity	NPD7713	Phase 3
0.6346	Remote Similarity	NPD3950	Discontinued
0.6343	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD1281	Approved
0.6331	Remote Similarity	NPD2347	Approved
0.6328	Remote Similarity	NPD7638	Approved
0.6323	Remote Similarity	NPD6190	Approved
0.6319	Remote Similarity	NPD7736	Approved
0.6316	Remote Similarity	NPD6100	Approved
0.6316	Remote Similarity	NPD6099	Approved
0.6316	Remote Similarity	NPD2438	Suspended
0.6316	Remote Similarity	NPD2796	Approved
0.6312	Remote Similarity	NPD6370	Approved
0.6312	Remote Similarity	NPD1778	Approved
0.6312	Remote Similarity	NPD6599	Discontinued
0.6311	Remote Similarity	NPD1282	Approved
0.6309	Remote Similarity	NPD4140	Approved
0.6304	Remote Similarity	NPD6009	Approved
0.6303	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5761	Phase 2
0.6296	Remote Similarity	NPD8455	Phase 2
0.6296	Remote Similarity	NPD5760	Phase 2
0.6294	Remote Similarity	NPD7507	Approved
0.629	Remote Similarity	NPD1090	Approved
0.629	Remote Similarity	NPD1089	Approved
0.629	Remote Similarity	NPD1086	Approved
0.6287	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD9545	Approved
0.6284	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.628	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD7639	Approved
0.6279	Remote Similarity	NPD7640	Approved
0.6276	Remote Similarity	NPD2797	Approved
0.6276	Remote Similarity	NPD1470	Approved
0.6275	Remote Similarity	NPD1471	Phase 3
0.627	Remote Similarity	NPD1563	Approved
0.627	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.627	Remote Similarity	NPD7900	Approved
0.627	Remote Similarity	NPD1202	Approved
0.6267	Remote Similarity	NPD6355	Discontinued
0.6264	Remote Similarity	NPD6784	Approved
0.6264	Remote Similarity	NPD6785	Approved
0.6259	Remote Similarity	NPD4574	Approved
0.6259	Remote Similarity	NPD4576	Approved
0.6259	Remote Similarity	NPD2613	Approved
0.6258	Remote Similarity	NPD1878	Clinical (unspecified phase)

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