NPASS Compound

Structure

CID174191 OpenBabel06191715542D 27 30 0 0 1 0 0 0 0 0999 V2000 2.6831 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7700 -3.0316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3523 0.7091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6705 -2.0115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3578 -2.2226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3578 0.6045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5659 -1.0169 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7569 -2.4182 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 1 5 2 0 0 0 0 2 13 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 6 1 0 0 0 0 6 15 1 0 0 0 0 7 8 2 0 0 0 0 7 14 1 0 0 0 0 8 17 1 0 0 0 0 9 14 2 0 0 0 0 9 18 1 0 0 0 0 10 15 2 0 0 0 0 10 20 1 0 0 0 0 11 16 1 0 0 0 0 11 21 1 0 0 0 0 12 25 1 0 0 0 0 12 26 1 0 0 0 0 13 19 1 0 0 0 0 13 20 1 6 0 0 0 15 16 1 0 0 0 0 16 22 1 6 0 0 0 17 18 2 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 19 14 1 1 0 0 0 19 27 1 0 0 0 0 20 21 1 1 0 0 0 20 23 1 0 0 0 0 21 24 1 1 0 0 0 21 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.17
Volume:	377.105
LogP:	3.219
LogD:	2.94
LogS:	-4.192
# Rotatable Bonds:	5
TPSA:	66.38
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.799
Synthetic Accessibility Score:	4.81
Fsp3:	0.524
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.54
MDCK Permeability:	2.0095030777156353e-05
Pgp-inhibitor:	0.117
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.024
30% Bioavailability (F30%):	0.39

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.686
Plasma Protein Binding (PPB):	81.99632263183594%
Volume Distribution (VD):	1.032
Pgp-substrate:	15.112236022949219%

ADMET: Metabolism

CYP1A2-inhibitor:	0.434
CYP1A2-substrate:	0.967
CYP2C19-inhibitor:	0.211
CYP2C19-substrate:	0.84
CYP2C9-inhibitor:	0.104
CYP2C9-substrate:	0.119
CYP2D6-inhibitor:	0.838
CYP2D6-substrate:	0.579
CYP3A4-inhibitor:	0.952
CYP3A4-substrate:	0.889

ADMET: Excretion

Clearance (CL):	13.806
Half-life (T1/2):	0.462

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.128
Drug-inuced Liver Injury (DILI):	0.187
AMES Toxicity:	0.8
Rat Oral Acute Toxicity:	0.318
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.155
Carcinogencity:	0.942
Eye Corrosion:	0.003
Eye Irritation:	0.023
Respiratory Toxicity:	0.927

Download Data

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

Natural Product: NPC174191

Natural Product ID:	NPC174191
*Common Name:**	(2S,3R,3As,6S,7Ar)-5-Allyl-2-Benzo[1,3]Dioxol-5-Yl-3A,7A-Dimethoxy-3-Methyl-2,3,3A,6,7,7A-Hexahydro-Benzofuran-6-Ol
IUPAC Name:	(2S,3R,3aS,6S,7aR)-2-(1,3-benzodioxol-5-yl)-3a,7a-dimethoxy-3-methyl-5-prop-2-enyl-2,3,6,7-tetrahydro-1-benzofuran-6-ol
Synonyms:
Standard InCHIKey:	MIFKVSCIPCYASV-JXCXWWAUSA-N
Standard InCHI:	InChI=1S/C21H26O6/c1-5-6-15-10-20(23-3)13(2)19(27-21(20,24-4)11-16(15)22)14-7-8-17-18(9-14)26-12-25-17/h5,7-10,13,16,19,22H,1,6,11-12H2,2-4H3/t13-,16+,19+,20+,21-/m1/s1
SMILES:	C=CCC1=C[C@@]2([C@H](C)[C@@H](c3ccc4c(c3)OCO4)O[C@@]2(C[C@@H]1O)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL41463
PubChem CID:	10022290
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11040054]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16724856]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	leaf	n.a.	PMID[17999353]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	Roots; Tubers	n.a.	n.a.	PMID[19639966]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19900811]
NPO9925	Rhododendron latoucheae	Species	Ericaceae	Eukaryota	Twigs; Leaves	n.a.	n.a.	PMID[30106288]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[8237383]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8237383]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8368081]
NPO9480	Huperzia miyoshiana	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9480	Huperzia miyoshiana	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6475	Gymnosporia trigyna	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7522	Streptomyces amakusaensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO313	Castilleja sulphurea	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9571	Pseudobrickellia brasiliensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9301	Dioscorea sativa	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9925	Rhododendron latoucheae	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19174	Anoplophora chinensis	Species	Cerambycidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9480	Huperzia miyoshiana	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1155	Forsythia japonica	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4682	Lindera aggregata	Species	Lauraceae	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	6

Activity Type	# Activity
Uncleic Acid	6

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT317	Uncleic Acid	Nucleic Acid	Binding	=	91.0	pM 30min-1 (mg of DNA)-1	PMID[547005]
NPT317	Uncleic Acid	Nucleic Acid	Binding	=	47.96	pM 30min-1 (mg of DNA)-1	PMID[547005]
NPT317	Uncleic Acid	Nucleic Acid	Binding	=	24.8	pM 30min-1 (mg of DNA)-1	PMID[547005]
NPT317	Uncleic Acid	Nucleic Acid	Inhibition	=	31.0	%	PMID[547005]
NPT317	Uncleic Acid	Nucleic Acid	Inhibition	=	64.0	%	PMID[547005]
NPT317	Uncleic Acid	Nucleic Acid	Inhibition	=	81.0	%	PMID[547005]

☑ 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 NPC174191 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	352
0.1-0.2	1284
0.2-0.3	3272
0.3-0.4	8258
0.4-0.5	10685
0.5-0.6	5762
0.6-0.7	9504
0.7-0.8	2830
0.8-0.85	512
0.85-0.9	201
0.9-0.95	34
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9462	High Similarity	NPC219671
0.9462	High Similarity	NPC147616
0.9462	High Similarity	NPC259742
0.9462	High Similarity	NPC104077
0.9394	High Similarity	NPC18576
0.9318	High Similarity	NPC47181
0.9248	High Similarity	NPC135777
0.9248	High Similarity	NPC142547
0.9185	High Similarity	NPC193666
0.9185	High Similarity	NPC88640
0.9185	High Similarity	NPC123526
0.9167	High Similarity	NPC7744
0.9154	High Similarity	NPC226862
0.9154	High Similarity	NPC158471
0.9154	High Similarity	NPC165128
0.9154	High Similarity	NPC57119
0.913	High Similarity	NPC84181
0.9111	High Similarity	NPC469981
0.9111	High Similarity	NPC185908
0.9111	High Similarity	NPC101807
0.9104	High Similarity	NPC101624
0.9104	High Similarity	NPC184938
0.9091	High Similarity	NPC82111
0.9091	High Similarity	NPC227160
0.9058	High Similarity	NPC474808
0.9058	High Similarity	NPC477898
0.9058	High Similarity	NPC265154
0.9044	High Similarity	NPC156376
0.903	High Similarity	NPC470881
0.9023	High Similarity	NPC106739
0.9023	High Similarity	NPC207400
0.9023	High Similarity	NPC181049
0.9023	High Similarity	NPC471505
0.9015	High Similarity	NPC233224
0.9015	High Similarity	NPC271208
0.9008	High Similarity	NPC470084
0.9	High Similarity	NPC112861
0.9	High Similarity	NPC206882
0.9	High Similarity	NPC40352
0.9	High Similarity	NPC213711
0.8986	High Similarity	NPC302506
0.8986	High Similarity	NPC246947
0.8978	High Similarity	NPC177868
0.8978	High Similarity	NPC46591
0.8971	High Similarity	NPC166184
0.8971	High Similarity	NPC283949
0.8963	High Similarity	NPC474139
0.8963	High Similarity	NPC150534
0.8955	High Similarity	NPC6836
0.8955	High Similarity	NPC196937
0.8955	High Similarity	NPC25821
0.8955	High Similarity	NPC136750
0.8955	High Similarity	NPC169973
0.8955	High Similarity	NPC266848
0.8947	High Similarity	NPC161557
0.8947	High Similarity	NPC115207
0.8947	High Similarity	NPC277804
0.8947	High Similarity	NPC158079
0.8947	High Similarity	NPC228346
0.8947	High Similarity	NPC27843
0.8947	High Similarity	NPC40432
0.8947	High Similarity	NPC7171
0.8929	High Similarity	NPC22150
0.8929	High Similarity	NPC279298
0.8929	High Similarity	NPC18979
0.8929	High Similarity	NPC180953
0.8929	High Similarity	NPC38041
0.8921	High Similarity	NPC255566
0.8921	High Similarity	NPC298317
0.8913	High Similarity	NPC472711
0.8913	High Similarity	NPC471908
0.8889	High Similarity	NPC170779
0.8889	High Similarity	NPC90083
0.8881	High Similarity	NPC18842
0.8881	High Similarity	NPC171928
0.8881	High Similarity	NPC65183
0.8881	High Similarity	NPC33611
0.8881	High Similarity	NPC16830
0.8881	High Similarity	NPC158526
0.8881	High Similarity	NPC4940
0.8881	High Similarity	NPC129687
0.8881	High Similarity	NPC252833
0.8881	High Similarity	NPC100223
0.8881	High Similarity	NPC261812
0.8881	High Similarity	NPC98624
0.8881	High Similarity	NPC72046
0.8872	High Similarity	NPC171550
0.8872	High Similarity	NPC174495
0.8872	High Similarity	NPC187998
0.8872	High Similarity	NPC77040
0.8872	High Similarity	NPC257582
0.8872	High Similarity	NPC153739
0.8872	High Similarity	NPC134764
0.8872	High Similarity	NPC64201
0.8872	High Similarity	NPC145305
0.8872	High Similarity	NPC242807
0.8872	High Similarity	NPC92164
0.8872	High Similarity	NPC241522
0.8872	High Similarity	NPC42300
0.8857	High Similarity	NPC470235
0.8857	High Similarity	NPC179521
0.8857	High Similarity	NPC172171
0.8857	High Similarity	NPC283995
0.8857	High Similarity	NPC129417
0.8857	High Similarity	NPC239254
0.8849	High Similarity	NPC253878
0.8849	High Similarity	NPC287124
0.8846	High Similarity	NPC18449
0.8846	High Similarity	NPC121783
0.8846	High Similarity	NPC34902
0.8841	High Similarity	NPC56091
0.8841	High Similarity	NPC226547
0.8832	High Similarity	NPC304152
0.8832	High Similarity	NPC474039
0.8824	High Similarity	NPC189474
0.8815	High Similarity	NPC58585
0.8815	High Similarity	NPC26394
0.8806	High Similarity	NPC65942
0.8806	High Similarity	NPC192255
0.8806	High Similarity	NPC248307
0.8797	High Similarity	NPC475875
0.8797	High Similarity	NPC270849
0.8797	High Similarity	NPC26653
0.8794	High Similarity	NPC43508
0.8794	High Similarity	NPC476301
0.8794	High Similarity	NPC475868
0.8794	High Similarity	NPC469586
0.8786	High Similarity	NPC470950
0.8786	High Similarity	NPC185071
0.8786	High Similarity	NPC185307
0.8786	High Similarity	NPC12728
0.8786	High Similarity	NPC46092
0.8777	High Similarity	NPC471414
0.8768	High Similarity	NPC9068
0.8759	High Similarity	NPC121651
0.8759	High Similarity	NPC25695
0.8759	High Similarity	NPC172818
0.875	High Similarity	NPC31530
0.875	High Similarity	NPC475224
0.8741	High Similarity	NPC97316
0.8741	High Similarity	NPC230219
0.8732	High Similarity	NPC241846
0.8732	High Similarity	NPC276753
0.8732	High Similarity	NPC93610
0.8732	High Similarity	NPC3982
0.8732	High Similarity	NPC212890
0.8732	High Similarity	NPC205796
0.8732	High Similarity	NPC162193
0.8731	High Similarity	NPC181079
0.8731	High Similarity	NPC80600
0.8731	High Similarity	NPC173308
0.8731	High Similarity	NPC472024
0.8731	High Similarity	NPC275950
0.8723	High Similarity	NPC166884
0.8723	High Similarity	NPC477701
0.8723	High Similarity	NPC141569
0.8723	High Similarity	NPC471667
0.8723	High Similarity	NPC79429
0.8723	High Similarity	NPC217635
0.8722	High Similarity	NPC128208
0.8722	High Similarity	NPC45774
0.8722	High Similarity	NPC282703
0.8722	High Similarity	NPC129570
0.8722	High Similarity	NPC11258
0.8722	High Similarity	NPC184733
0.8722	High Similarity	NPC21867
0.8714	High Similarity	NPC103637
0.8714	High Similarity	NPC36531
0.8714	High Similarity	NPC230538
0.8714	High Similarity	NPC229172
0.8714	High Similarity	NPC476356
0.8712	High Similarity	NPC473960
0.8705	High Similarity	NPC278076
0.8686	High Similarity	NPC99572
0.8686	High Similarity	NPC148893
0.8686	High Similarity	NPC25333
0.8686	High Similarity	NPC126409
0.8686	High Similarity	NPC236522
0.8686	High Similarity	NPC49235
0.8681	High Similarity	NPC51328
0.8681	High Similarity	NPC55158
0.8681	High Similarity	NPC286235
0.8676	High Similarity	NPC112237
0.8671	High Similarity	NPC193473
0.8671	High Similarity	NPC275284
0.8671	High Similarity	NPC213074
0.8671	High Similarity	NPC15956
0.8671	High Similarity	NPC31325
0.8671	High Similarity	NPC224674
0.8671	High Similarity	NPC114505
0.8667	High Similarity	NPC476345
0.8662	High Similarity	NPC178014
0.8662	High Similarity	NPC11422
0.8662	High Similarity	NPC477702
0.8662	High Similarity	NPC474749
0.8662	High Similarity	NPC42716
0.8657	High Similarity	NPC307110
0.8657	High Similarity	NPC248355
0.8657	High Similarity	NPC166040
0.8652	High Similarity	NPC324962

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 NPC174191 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	281
0.1-0.2	795
0.2-0.3	1833
0.3-0.4	2724
0.4-0.5	1811
0.5-0.6	1095
0.6-0.7	517
0.7-0.8	88
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8615	High Similarity	NPD3705	Approved
0.8385	Intermediate Similarity	NPD1357	Approved
0.8278	Intermediate Similarity	NPD4965	Approved
0.8278	Intermediate Similarity	NPD4967	Phase 2
0.8278	Intermediate Similarity	NPD4966	Approved
0.8248	Intermediate Similarity	NPD3027	Phase 3
0.8079	Intermediate Similarity	NPD37	Approved
0.8052	Intermediate Similarity	NPD6234	Discontinued
0.8	Intermediate Similarity	NPD6674	Discontinued
0.7926	Intermediate Similarity	NPD1091	Approved
0.7923	Intermediate Similarity	NPD5283	Phase 1
0.7905	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD1613	Approved
0.7817	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD7228	Approved
0.774	Intermediate Similarity	NPD1375	Discontinued
0.7722	Intermediate Similarity	NPD7199	Phase 2
0.7714	Intermediate Similarity	NPD2861	Phase 2
0.7634	Intermediate Similarity	NPD228	Approved
0.7619	Intermediate Similarity	NPD7266	Discontinued
0.76	Intermediate Similarity	NPD5058	Phase 3
0.7582	Intermediate Similarity	NPD1653	Approved
0.7569	Intermediate Similarity	NPD3620	Phase 2
0.7569	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD4237	Approved
0.7517	Intermediate Similarity	NPD4236	Phase 3
0.7516	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7240	Approved
0.7484	Intermediate Similarity	NPD7028	Phase 2
0.7465	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD2978	Approved
0.7452	Intermediate Similarity	NPD2977	Approved
0.7448	Intermediate Similarity	NPD2238	Phase 2
0.7431	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD4749	Approved
0.7421	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD4908	Phase 1
0.7407	Intermediate Similarity	NPD7157	Approved
0.7405	Intermediate Similarity	NPD2563	Approved
0.7405	Intermediate Similarity	NPD2684	Approved
0.7405	Intermediate Similarity	NPD2560	Approved
0.7394	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD3818	Discontinued
0.7376	Intermediate Similarity	NPD8651	Approved
0.7351	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD4110	Phase 3
0.7343	Intermediate Similarity	NPD3018	Phase 2
0.7337	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4060	Phase 1
0.7315	Intermediate Similarity	NPD2161	Phase 2
0.7313	Intermediate Similarity	NPD7843	Approved
0.731	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD2983	Phase 2
0.7305	Intermediate Similarity	NPD2982	Phase 2
0.7303	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1610	Phase 2
0.7285	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD5735	Approved
0.7279	Intermediate Similarity	NPD6671	Approved
0.7267	Intermediate Similarity	NPD6005	Phase 3
0.7267	Intermediate Similarity	NPD6002	Phase 3
0.7267	Intermediate Similarity	NPD6004	Phase 3
0.7267	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5762	Approved
0.7267	Intermediate Similarity	NPD5763	Approved
0.7267	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD5126	Approved
0.7266	Intermediate Similarity	NPD5125	Phase 3
0.7244	Intermediate Similarity	NPD4210	Discontinued
0.7234	Intermediate Similarity	NPD2981	Phase 2
0.723	Intermediate Similarity	NPD6653	Approved
0.7218	Intermediate Similarity	NPD3021	Approved
0.7218	Intermediate Similarity	NPD3022	Approved
0.7202	Intermediate Similarity	NPD7685	Pre-registration
0.7197	Intermediate Similarity	NPD290	Approved
0.7186	Intermediate Similarity	NPD7074	Phase 3
0.7183	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD3685	Discontinued
0.7183	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD7097	Phase 1
0.7179	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD5177	Phase 3
0.7171	Intermediate Similarity	NPD3060	Approved
0.7162	Intermediate Similarity	NPD6355	Discontinued
0.7151	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6071	Discontinued
0.7134	Intermediate Similarity	NPD3687	Approved
0.7134	Intermediate Similarity	NPD3686	Approved
0.7133	Intermediate Similarity	NPD4108	Discontinued
0.7133	Intermediate Similarity	NPD5588	Approved
0.7133	Intermediate Similarity	NPD6696	Suspended
0.7126	Intermediate Similarity	NPD7054	Approved
0.7125	Intermediate Similarity	NPD5773	Approved
0.7125	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD5772	Approved
0.7124	Intermediate Similarity	NPD6331	Phase 2
0.7115	Intermediate Similarity	NPD7526	Approved
0.7115	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD52	Approved
0.7113	Intermediate Similarity	NPD2233	Approved
0.7113	Intermediate Similarity	NPD2232	Approved
0.7113	Intermediate Similarity	NPD2230	Approved
0.7095	Intermediate Similarity	NPD4140	Approved
0.7091	Intermediate Similarity	NPD2969	Approved
0.7091	Intermediate Similarity	NPD2970	Approved
0.7083	Intermediate Similarity	NPD7472	Approved
0.7078	Intermediate Similarity	NPD2677	Approved
0.7078	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD8127	Discontinued
0.7067	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD4536	Approved
0.7067	Intermediate Similarity	NPD4538	Approved
0.7063	Intermediate Similarity	NPD1934	Approved
0.705	Intermediate Similarity	NPD5536	Phase 2
0.7047	Intermediate Similarity	NPD3657	Discovery
0.7047	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD5124	Phase 1
0.7032	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4626	Approved
0.702	Intermediate Similarity	NPD7033	Discontinued
0.7019	Intermediate Similarity	NPD8455	Phase 2
0.7013	Intermediate Similarity	NPD4628	Phase 3
0.7007	Intermediate Similarity	NPD7095	Approved
0.7007	Intermediate Similarity	NPD4625	Phase 3
0.7006	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6353	Approved
0.7	Intermediate Similarity	NPD1548	Phase 1
0.6993	Remote Similarity	NPD2424	Discontinued
0.6993	Remote Similarity	NPD2231	Phase 2
0.6993	Remote Similarity	NPD2235	Phase 2
0.6983	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.698	Remote Similarity	NPD1558	Phase 1
0.6975	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD3496	Discontinued
0.6966	Remote Similarity	NPD3094	Phase 2
0.6959	Remote Similarity	NPD5109	Approved
0.6959	Remote Similarity	NPD5110	Phase 2
0.6959	Remote Similarity	NPD5111	Phase 2
0.6959	Remote Similarity	NPD7808	Phase 3
0.695	Remote Similarity	NPD5691	Approved
0.6947	Remote Similarity	NPD291	Approved
0.6946	Remote Similarity	NPD2489	Approved
0.6946	Remote Similarity	NPD27	Approved
0.6944	Remote Similarity	NPD5327	Phase 3
0.6943	Remote Similarity	NPD4123	Phase 3
0.6943	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6797	Phase 2
0.6934	Remote Similarity	NPD1138	Approved
0.6933	Remote Similarity	NPD3882	Suspended
0.6932	Remote Similarity	NPD7296	Approved
0.6928	Remote Similarity	NPD3051	Approved
0.6928	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7680	Approved
0.6923	Remote Similarity	NPD5844	Phase 1
0.6919	Remote Similarity	NPD7310	Approved
0.6919	Remote Similarity	NPD7311	Approved
0.6919	Remote Similarity	NPD7312	Approved
0.6919	Remote Similarity	NPD7313	Approved
0.6918	Remote Similarity	NPD4624	Approved
0.6914	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5494	Approved
0.6908	Remote Similarity	NPD5960	Phase 3
0.6908	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6559	Discontinued
0.6901	Remote Similarity	NPD7251	Discontinued
0.6901	Remote Similarity	NPD2667	Approved
0.6901	Remote Similarity	NPD2668	Approved
0.6899	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.689	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.689	Remote Similarity	NPD5604	Discontinued
0.6887	Remote Similarity	NPD2157	Approved
0.6879	Remote Similarity	NPD1774	Approved
0.6879	Remote Similarity	NPD7309	Approved
0.6875	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1608	Approved
0.6875	Remote Similarity	NPD4005	Discontinued
0.6861	Remote Similarity	NPD1139	Approved
0.6861	Remote Similarity	NPD1137	Approved
0.686	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6190	Approved
0.6859	Remote Similarity	NPD5241	Discontinued
0.6852	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD6798	Discontinued
0.6845	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6166	Phase 2
0.6842	Remote Similarity	NPD6111	Discontinued
0.6839	Remote Similarity	NPD4162	Approved
0.6839	Remote Similarity	NPD1652	Phase 2
0.6838	Remote Similarity	NPD556	Approved
0.6838	Remote Similarity	NPD4750	Phase 3
0.6832	Remote Similarity	NPD4678	Approved
0.6832	Remote Similarity	NPD4675	Approved
0.6829	Remote Similarity	NPD4868	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