NPASS Compound

Structure

CID148628 OpenBabel06191715522D 28 31 0 0 1 0 0 0 0 0999 V2000 -2.0894 1.0345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0699 -3.4428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1530 -1.3191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7188 -0.5672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0097 -1.7532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5232 -2.6382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2847 -2.1985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6874 -1.4279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5232 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5451 0.3523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6418 -2.6747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5448 -1.2323 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5232 -0.8794 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.8794 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7616 -2.1985 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7616 0.4397 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9264 -0.4401 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6878 0.5481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8886 -0.5472 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2847 -1.3191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7616 -1.3191 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7626 -2.6614 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0097 -2.6326 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7616 1.3079 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4936 1.3999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7907 -0.9759 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0929 -1.9199 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 2 0 0 0 0 2 11 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 6 7 1 0 0 0 0 6 15 1 0 0 0 0 7 20 1 0 0 0 0 8 12 1 0 0 0 0 8 14 1 0 0 0 0 9 13 1 0 0 0 0 9 16 1 0 0 0 0 10 18 1 0 0 0 0 11 23 2 0 0 0 0 11 28 1 0 0 0 0 12 17 1 0 0 0 0 12 28 1 6 0 0 0 13 20 1 0 0 0 0 13 21 1 6 0 0 0 14 21 1 6 0 0 0 14 22 1 0 0 0 0 15 21 1 6 0 0 0 15 24 1 0 0 0 0 16 22 1 6 0 0 0 16 25 1 0 0 0 0 17 10 1 1 0 0 0 17 19 1 0 0 0 0 18 26 2 0 0 0 0 19 22 1 6 0 0 0 19 27 1 0 0 0 0 21 5 1 6 0 0 0 22 18 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.22
Volume:	399.674
LogP:	1.52
LogD:	1.283
LogS:	-3.222
# Rotatable Bonds:	2
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.463
Synthetic Accessibility Score:	6.157
Fsp3:	0.818
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.876
MDCK Permeability:	4.598354280460626e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.795
Human Intestinal Absorption (HIA):	0.041
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.375

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.206
Plasma Protein Binding (PPB):	39.23394012451172%
Volume Distribution (VD):	0.641
Pgp-substrate:	63.63785171508789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.042
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.424
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.097
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.141
CYP3A4-inhibitor:	0.029
CYP3A4-substrate:	0.239

ADMET: Excretion

Clearance (CL):	2.807
Half-life (T1/2):	0.657

ADMET: Toxicity

hERG Blockers:	0.265
Human Hepatotoxicity (H-HT):	0.121
Drug-inuced Liver Injury (DILI):	0.086
AMES Toxicity:	0.094
Rat Oral Acute Toxicity:	0.964
Maximum Recommended Daily Dose:	0.989
Skin Sensitization:	0.529
Carcinogencity:	0.041
Eye Corrosion:	0.013
Eye Irritation:	0.056
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC148628

Natural Product ID:	NPC148628
*Common Name:**	Excisanin B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VAAUVQKKXHANPM-DQHXIWAQSA-N
Standard InCHI:	InChI=1S/C22H32O6/c1-10-17-12(28-11(2)23)8-14-21(5)13(20(3,4)7-6-15(21)24)9-16(25)22(14,18(10)26)19(17)27/h12-17,19,24-25,27H,1,6-9H2,2-5H3/t12-,13+,14-,15-,16+,17+,19+,21+,22-/m0/s1
SMILES:	CC(=O)O[C@H]1C[C@@H]2[C@]3([C@@H]([C@@H]1C(=C)C3=O)O)[C@H](O)C[C@H]1[C@@]2(C)[C@@H](O)CCC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL470766
PubChem CID:	13193213
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/C39730000707]
NPO17628	Rabdosia excisa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043413]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18491868]
NPO17628	Rabdosia excisa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17628	Rabdosia excisa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17628	Rabdosia excisa	Species	Lamiaceae	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

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.63	ug.mL-1	PMID[466281]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	3300.0	nM	PMID[466282]

☑ 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 NPC148628 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	230
0.1-0.2	1668
0.2-0.3	5408
0.3-0.4	9081
0.4-0.5	11592
0.5-0.6	6107
0.6-0.7	5689
0.7-0.8	2438
0.8-0.85	282
0.85-0.9	90
0.9-0.95	86
0.95-1	26

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC304832
1.0	High Similarity	NPC214946
1.0	High Similarity	NPC88203
1.0	High Similarity	NPC286519
1.0	High Similarity	NPC76866
1.0	High Similarity	NPC246736
0.9894	High Similarity	NPC289148
0.9894	High Similarity	NPC52899
0.9894	High Similarity	NPC163963
0.9787	High Similarity	NPC287676
0.9688	High Similarity	NPC87927
0.9684	High Similarity	NPC46848
0.9681	High Similarity	NPC78427
0.9681	High Similarity	NPC16911
0.9588	High Similarity	NPC98603
0.9588	High Similarity	NPC84928
0.9583	High Similarity	NPC275990
0.9495	High Similarity	NPC231278
0.9495	High Similarity	NPC112895
0.9495	High Similarity	NPC218123
0.9485	High Similarity	NPC216114
0.9479	High Similarity	NPC471790
0.9474	High Similarity	NPC38471
0.9474	High Similarity	NPC20479
0.9474	High Similarity	NPC98837
0.9474	High Similarity	NPC28864
0.9474	High Similarity	NPC162459
0.9474	High Similarity	NPC38296
0.9474	High Similarity	NPC471038
0.9468	High Similarity	NPC13949
0.9468	High Similarity	NPC329910
0.9375	High Similarity	NPC293866
0.9362	High Similarity	NPC470232
0.9362	High Similarity	NPC210214
0.9362	High Similarity	NPC470229
0.93	High Similarity	NPC273155
0.9293	High Similarity	NPC200957
0.9293	High Similarity	NPC4115
0.9293	High Similarity	NPC138908
0.9293	High Similarity	NPC37600
0.9271	High Similarity	NPC474793
0.9271	High Similarity	NPC89099
0.9263	High Similarity	NPC29410
0.9263	High Similarity	NPC200054
0.9255	High Similarity	NPC91772
0.9255	High Similarity	NPC153775
0.9255	High Similarity	NPC29247
0.9255	High Similarity	NPC111524
0.9255	High Similarity	NPC292374
0.9255	High Similarity	NPC289539
0.9255	High Similarity	NPC470386
0.9255	High Similarity	NPC215271
0.9255	High Similarity	NPC261333
0.9255	High Similarity	NPC129004
0.9255	High Similarity	NPC104371
0.9255	High Similarity	NPC475118
0.9255	High Similarity	NPC470385
0.9255	High Similarity	NPC47853
0.9255	High Similarity	NPC101233
0.92	High Similarity	NPC166993
0.92	High Similarity	NPC176949
0.92	High Similarity	NPC201908
0.9192	High Similarity	NPC474558
0.9192	High Similarity	NPC202793
0.9184	High Similarity	NPC475803
0.9184	High Similarity	NPC309388
0.9167	High Similarity	NPC10864
0.9158	High Similarity	NPC98639
0.9149	High Similarity	NPC144739
0.9149	High Similarity	NPC294263
0.9149	High Similarity	NPC181594
0.91	High Similarity	NPC295366
0.9091	High Similarity	NPC277074
0.9091	High Similarity	NPC470310
0.9091	High Similarity	NPC122811
0.9091	High Similarity	NPC139347
0.9091	High Similarity	NPC209298
0.9082	High Similarity	NPC236585
0.9082	High Similarity	NPC121218
0.9082	High Similarity	NPC253886
0.9062	High Similarity	NPC135548
0.9062	High Similarity	NPC264979
0.9062	High Similarity	NPC470387
0.9043	High Similarity	NPC470230
0.9043	High Similarity	NPC198242
0.9043	High Similarity	NPC299185
0.9043	High Similarity	NPC476168
0.9043	High Similarity	NPC250753
0.9043	High Similarity	NPC211403
0.9029	High Similarity	NPC329953
0.9	High Similarity	NPC13149
0.9	High Similarity	NPC301787
0.9	High Similarity	NPC96268
0.899	High Similarity	NPC170615
0.898	High Similarity	NPC94906
0.898	High Similarity	NPC470388
0.8958	High Similarity	NPC231060
0.8958	High Similarity	NPC84018
0.8958	High Similarity	NPC138245
0.8936	High Similarity	NPC80401
0.8936	High Similarity	NPC261994
0.8936	High Similarity	NPC180849
0.8936	High Similarity	NPC470378
0.8936	High Similarity	NPC149761
0.8932	High Similarity	NPC471093
0.8922	High Similarity	NPC211224
0.8911	High Similarity	NPC12823
0.8911	High Similarity	NPC222833
0.89	High Similarity	NPC159442
0.89	High Similarity	NPC96217
0.8889	High Similarity	NPC71706
0.8889	High Similarity	NPC148279
0.8889	High Similarity	NPC252614
0.8889	High Similarity	NPC295276
0.8878	High Similarity	NPC472028
0.8866	High Similarity	NPC140242
0.8857	High Similarity	NPC471252
0.8854	High Similarity	NPC191094
0.8854	High Similarity	NPC302008
0.8846	High Similarity	NPC29505
0.8846	High Similarity	NPC94650
0.8846	High Similarity	NPC470281
0.883	High Similarity	NPC471043
0.8812	High Similarity	NPC47281
0.88	High Similarity	NPC124544
0.8788	High Similarity	NPC156324
0.8788	High Similarity	NPC180733
0.8788	High Similarity	NPC267921
0.8788	High Similarity	NPC41971
0.8788	High Similarity	NPC37047
0.8788	High Similarity	NPC291785
0.8788	High Similarity	NPC127408
0.8788	High Similarity	NPC55503
0.8763	High Similarity	NPC288906
0.8763	High Similarity	NPC263135
0.8762	High Similarity	NPC474927
0.875	High Similarity	NPC59350
0.875	High Similarity	NPC59170
0.8738	High Similarity	NPC469729
0.8738	High Similarity	NPC63841
0.8738	High Similarity	NPC55973
0.8738	High Similarity	NPC469733
0.8725	High Similarity	NPC265127
0.8725	High Similarity	NPC50535
0.8725	High Similarity	NPC28791
0.8713	High Similarity	NPC469985
0.87	High Similarity	NPC14634
0.87	High Similarity	NPC75941
0.8687	High Similarity	NPC26270
0.8673	High Similarity	NPC234564
0.8673	High Similarity	NPC104568
0.8667	High Similarity	NPC213320
0.866	High Similarity	NPC64006
0.8654	High Similarity	NPC469744
0.8654	High Similarity	NPC102741
0.8654	High Similarity	NPC469983
0.8641	High Similarity	NPC186054
0.8641	High Similarity	NPC88833
0.8641	High Similarity	NPC67745
0.8641	High Similarity	NPC61071
0.8641	High Similarity	NPC96333
0.8641	High Similarity	NPC251824
0.8641	High Similarity	NPC86852
0.8641	High Similarity	NPC471461
0.8641	High Similarity	NPC469746
0.8617	High Similarity	NPC259009
0.8617	High Similarity	NPC153604
0.8617	High Similarity	NPC165895
0.8617	High Similarity	NPC174619
0.8611	High Similarity	NPC473304
0.86	High Similarity	NPC293890
0.86	High Similarity	NPC108371
0.8586	High Similarity	NPC190080
0.8586	High Similarity	NPC253586
0.8586	High Similarity	NPC111187
0.8586	High Similarity	NPC96839
0.8585	High Similarity	NPC473397
0.8585	High Similarity	NPC476964
0.8585	High Similarity	NPC471245
0.8585	High Similarity	NPC473352
0.8571	High Similarity	NPC473324
0.8571	High Similarity	NPC320383
0.8571	High Similarity	NPC85391
0.8571	High Similarity	NPC137104
0.8571	High Similarity	NPC474786
0.8571	High Similarity	NPC29112
0.8558	High Similarity	NPC232133
0.8558	High Similarity	NPC473410
0.8558	High Similarity	NPC189663
0.8558	High Similarity	NPC471094
0.8558	High Similarity	NPC469984
0.8558	High Similarity	NPC89860
0.8557	High Similarity	NPC244356
0.8557	High Similarity	NPC224060
0.8529	High Similarity	NPC312900
0.8519	High Similarity	NPC88945
0.8515	High Similarity	NPC39683
0.8511	High Similarity	NPC471042
0.8505	High Similarity	NPC471248
0.8505	High Similarity	NPC132668

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 NPC148628 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	220
0.1-0.2	2066
0.2-0.3	3920
0.3-0.4	1894
0.4-0.5	565
0.5-0.6	210
0.6-0.7	164
0.7-0.8	111
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
0.79	Intermediate Similarity	NPD8035	Phase 2
0.79	Intermediate Similarity	NPD8034	Phase 2
0.787	Intermediate Similarity	NPD6881	Approved
0.787	Intermediate Similarity	NPD6899	Approved
0.785	Intermediate Similarity	NPD5739	Approved
0.785	Intermediate Similarity	NPD6675	Approved
0.785	Intermediate Similarity	NPD7128	Approved
0.785	Intermediate Similarity	NPD6402	Approved
0.7835	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD6649	Approved
0.7818	Intermediate Similarity	NPD6650	Approved
0.7798	Intermediate Similarity	NPD6373	Approved
0.7798	Intermediate Similarity	NPD6372	Approved
0.7778	Intermediate Similarity	NPD5697	Approved
0.7739	Intermediate Similarity	NPD6319	Approved
0.7727	Intermediate Similarity	NPD7290	Approved
0.7727	Intermediate Similarity	NPD6883	Approved
0.7727	Intermediate Similarity	NPD7102	Approved
0.7706	Intermediate Similarity	NPD7320	Approved
0.7706	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD6008	Approved
0.7658	Intermediate Similarity	NPD6869	Approved
0.7658	Intermediate Similarity	NPD6847	Approved
0.7658	Intermediate Similarity	NPD8130	Phase 1
0.7658	Intermediate Similarity	NPD6617	Approved
0.7647	Intermediate Similarity	NPD6399	Phase 3
0.7636	Intermediate Similarity	NPD6012	Approved
0.7636	Intermediate Similarity	NPD6014	Approved
0.7636	Intermediate Similarity	NPD6013	Approved
0.7627	Intermediate Similarity	NPD7492	Approved
0.7619	Intermediate Similarity	NPD7638	Approved
0.7615	Intermediate Similarity	NPD5701	Approved
0.7589	Intermediate Similarity	NPD8297	Approved
0.7589	Intermediate Similarity	NPD6882	Approved
0.7586	Intermediate Similarity	NPD6054	Approved
0.7583	Intermediate Similarity	NPD7736	Approved
0.7563	Intermediate Similarity	NPD6616	Approved
0.7549	Intermediate Similarity	NPD6079	Approved
0.7547	Intermediate Similarity	NPD7639	Approved
0.7547	Intermediate Similarity	NPD7640	Approved
0.7545	Intermediate Similarity	NPD6011	Approved
0.7525	Intermediate Similarity	NPD5328	Approved
0.7522	Intermediate Similarity	NPD4632	Approved
0.75	Intermediate Similarity	NPD7078	Approved
0.7478	Intermediate Similarity	NPD7115	Discovery
0.7474	Intermediate Similarity	NPD6697	Approved
0.7474	Intermediate Similarity	NPD6115	Approved
0.7474	Intermediate Similarity	NPD6118	Approved
0.7474	Intermediate Similarity	NPD6114	Approved
0.7458	Intermediate Similarity	NPD6370	Approved
0.7449	Intermediate Similarity	NPD4788	Approved
0.7436	Intermediate Similarity	NPD6059	Approved
0.7411	Intermediate Similarity	NPD4634	Approved
0.7404	Intermediate Similarity	NPD7748	Approved
0.7383	Intermediate Similarity	NPD5286	Approved
0.7383	Intermediate Similarity	NPD5285	Approved
0.7383	Intermediate Similarity	NPD4696	Approved
0.7379	Intermediate Similarity	NPD7515	Phase 2
0.7377	Intermediate Similarity	NPD7319	Approved
0.7373	Intermediate Similarity	NPD6015	Approved
0.7373	Intermediate Similarity	NPD6016	Approved
0.7358	Intermediate Similarity	NPD6083	Phase 2
0.7358	Intermediate Similarity	NPD4755	Approved
0.7358	Intermediate Similarity	NPD6084	Phase 2
0.7358	Intermediate Similarity	NPD7902	Approved
0.7355	Intermediate Similarity	NPD8293	Discontinued
0.7345	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD6009	Approved
0.7311	Intermediate Similarity	NPD5988	Approved
0.7264	Intermediate Similarity	NPD5222	Approved
0.7264	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD4697	Phase 3
0.7264	Intermediate Similarity	NPD5221	Approved
0.7263	Intermediate Similarity	NPD6117	Approved
0.725	Intermediate Similarity	NPD8328	Phase 3
0.725	Intermediate Similarity	NPD7604	Phase 2
0.7248	Intermediate Similarity	NPD5226	Approved
0.7248	Intermediate Similarity	NPD5224	Approved
0.7248	Intermediate Similarity	NPD5211	Phase 2
0.7248	Intermediate Similarity	NPD5225	Approved
0.7248	Intermediate Similarity	NPD4633	Approved
0.7241	Intermediate Similarity	NPD6274	Approved
0.7228	Intermediate Similarity	NPD3618	Phase 1
0.7227	Intermediate Similarity	NPD5983	Phase 2
0.7222	Intermediate Similarity	NPD4700	Approved
0.7212	Intermediate Similarity	NPD6411	Approved
0.7203	Intermediate Similarity	NPD7101	Approved
0.7203	Intermediate Similarity	NPD7100	Approved
0.72	Intermediate Similarity	NPD4786	Approved
0.7196	Intermediate Similarity	NPD5173	Approved
0.7188	Intermediate Similarity	NPD6116	Phase 1
0.7182	Intermediate Similarity	NPD5174	Approved
0.7182	Intermediate Similarity	NPD5175	Approved
0.7179	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD3703	Phase 2
0.7156	Intermediate Similarity	NPD5223	Approved
0.7131	Intermediate Similarity	NPD7507	Approved
0.7131	Intermediate Similarity	NPD6336	Discontinued
0.713	Intermediate Similarity	NPD4225	Approved
0.713	Intermediate Similarity	NPD5696	Approved
0.7119	Intermediate Similarity	NPD6335	Approved
0.7117	Intermediate Similarity	NPD5141	Approved
0.7094	Intermediate Similarity	NPD6868	Approved
0.7091	Intermediate Similarity	NPD7632	Discontinued
0.7087	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD7900	Approved
0.7069	Intermediate Similarity	NPD8133	Approved
0.7059	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7521	Approved
0.7059	Intermediate Similarity	NPD7334	Approved
0.7059	Intermediate Similarity	NPD6684	Approved
0.7059	Intermediate Similarity	NPD5330	Approved
0.7059	Intermediate Similarity	NPD6409	Approved
0.7059	Intermediate Similarity	NPD7146	Approved
0.7053	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7637	Suspended
0.7034	Intermediate Similarity	NPD6317	Approved
0.7019	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6101	Approved
0.7009	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5695	Phase 3
0.7	Intermediate Similarity	NPD3667	Approved
0.6991	Remote Similarity	NPD6412	Phase 2
0.6981	Remote Similarity	NPD5778	Approved
0.6981	Remote Similarity	NPD4202	Approved
0.6981	Remote Similarity	NPD5779	Approved
0.6975	Remote Similarity	NPD6314	Approved
0.6975	Remote Similarity	NPD6313	Approved
0.6942	Remote Similarity	NPD6908	Approved
0.6942	Remote Similarity	NPD6909	Approved
0.6942	Remote Similarity	NPD6921	Approved
0.6942	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.693	Remote Similarity	NPD4729	Approved
0.693	Remote Similarity	NPD5128	Approved
0.693	Remote Similarity	NPD4730	Approved
0.6923	Remote Similarity	NPD6672	Approved
0.6923	Remote Similarity	NPD6903	Approved
0.6923	Remote Similarity	NPD5737	Approved
0.6903	Remote Similarity	NPD4767	Approved
0.6903	Remote Similarity	NPD4768	Approved
0.688	Remote Similarity	NPD6033	Approved
0.6875	Remote Similarity	NPD4754	Approved
0.687	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.687	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD3665	Phase 1
0.6863	Remote Similarity	NPD3133	Approved
0.6863	Remote Similarity	NPD3666	Approved
0.6857	Remote Similarity	NPD4753	Phase 2
0.6852	Remote Similarity	NPD5210	Approved
0.6852	Remote Similarity	NPD4629	Approved
0.6842	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6053	Discontinued
0.6827	Remote Similarity	NPD3573	Approved
0.681	Remote Similarity	NPD5250	Approved
0.681	Remote Similarity	NPD5251	Approved
0.681	Remote Similarity	NPD5248	Approved
0.681	Remote Similarity	NPD5249	Phase 3
0.681	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5247	Approved
0.6783	Remote Similarity	NPD6686	Approved
0.6752	Remote Similarity	NPD5217	Approved
0.6752	Remote Similarity	NPD5216	Approved
0.6752	Remote Similarity	NPD5215	Approved
0.6698	Remote Similarity	NPD6080	Approved
0.6698	Remote Similarity	NPD6673	Approved
0.6698	Remote Similarity	NPD6904	Approved
0.6697	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD1700	Approved
0.6694	Remote Similarity	NPD7327	Approved
0.6694	Remote Similarity	NPD7328	Approved
0.6667	Remote Similarity	NPD5169	Approved
0.6667	Remote Similarity	NPD6334	Approved
0.6667	Remote Similarity	NPD5135	Approved
0.6667	Remote Similarity	NPD5777	Approved
0.6667	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6333	Approved
0.6667	Remote Similarity	NPD6371	Approved
0.6639	Remote Similarity	NPD7516	Approved
0.6638	Remote Similarity	NPD5168	Approved
0.6636	Remote Similarity	NPD5785	Approved
0.6634	Remote Similarity	NPD7525	Registered
0.6633	Remote Similarity	NPD3702	Approved
0.6632	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.661	Remote Similarity	NPD5127	Approved
0.6606	Remote Similarity	NPD6001	Approved
0.6574	Remote Similarity	NPD5281	Approved
0.6574	Remote Similarity	NPD5284	Approved
0.6571	Remote Similarity	NPD6098	Approved
0.6571	Remote Similarity	NPD5786	Approved
0.6569	Remote Similarity	NPD5369	Approved
0.6562	Remote Similarity	NPD4245	Approved
0.6562	Remote Similarity	NPD4244	Approved
0.6552	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD3668	Phase 3
0.6532	Remote Similarity	NPD8379	Approved
0.6532	Remote Similarity	NPD8378	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