NPASS Compound

Structure

NPC200957 OpenBabel07101718182D 35 38 0 0 1 0 0 0 0 0999 V2000 -1.4160 2.0771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6106 4.6379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2117 -1.9430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0768 -1.3213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3033 0.2080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7890 1.0493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2355 1.5351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2290 0.9801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2117 2.0987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8933 -0.3818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0342 1.1838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8267 3.6908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0530 -1.4572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2355 -1.8070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5325 0.3498 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5469 1.1357 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8175 1.7489 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6058 1.7489 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2117 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 0.6996 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2117 0.6996 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0871 0.9676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6058 -0.3498 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8175 1.0493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6058 1.0493 0.0000 C 0 0 2 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 -1.7551 3.4044 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8944 -1.9430 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2355 -2.7785 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6589 2.2347 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2355 2.2347 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6445 1.6068 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1146 3.0300 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0530 -0.4857 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6058 -1.3213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 2 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 24 1 0 0 0 0 6 24 1 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 9 18 1 0 0 0 0 10 15 1 0 0 0 0 11 15 1 0 0 0 0 11 22 1 0 0 0 0 12 27 2 0 0 0 0 12 33 1 0 0 0 0 13 28 2 0 0 0 0 13 34 1 0 0 0 0 14 29 2 0 0 0 0 14 35 1 0 0 0 0 15 8 1 1 0 0 0 16 20 1 0 0 0 0 16 33 1 6 0 0 0 17 24 1 0 0 0 0 17 30 1 6 0 0 0 18 25 1 1 0 0 0 18 31 1 0 0 0 0 19 21 1 0 0 0 0 19 23 1 0 0 0 0 19 34 1 1 0 0 0 20 25 1 1 0 0 0 20 26 1 0 0 0 0 21 24 1 0 0 0 0 21 25 1 1 0 0 0 22 26 1 0 0 0 0 22 32 2 0 0 0 0 23 26 1 6 0 0 0 23 35 1 0 0 0 0 25 7 1 1 0 0 0 26 10 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	492.24
Volume:	489.956
LogP:	1.336
LogD:	1.48
LogS:	-3.413
# Rotatable Bonds:	6
TPSA:	136.43
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.343
Synthetic Accessibility Score:	6.266
Fsp3:	0.769
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.248
MDCK Permeability:	8.852186874719337e-05
Pgp-inhibitor:	0.938
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.319
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.177
Plasma Protein Binding (PPB):	30.668296813964844%
Volume Distribution (VD):	0.98
Pgp-substrate:	52.25297164916992%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.029
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.113
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.038
CYP2D6-inhibitor:	0.357
CYP2D6-substrate:	0.083
CYP3A4-inhibitor:	0.168
CYP3A4-substrate:	0.288

ADMET: Excretion

Clearance (CL):	2.913
Half-life (T1/2):	0.767

ADMET: Toxicity

hERG Blockers:	0.737
Human Hepatotoxicity (H-HT):	0.737
Drug-inuced Liver Injury (DILI):	0.224
AMES Toxicity:	0.042
Rat Oral Acute Toxicity:	0.654
Maximum Recommended Daily Dose:	0.959
Skin Sensitization:	0.464
Carcinogencity:	0.077
Eye Corrosion:	0.005
Eye Irritation:	0.01
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC200957

Natural Product ID:	NPC200957
*Common Name:**	Nervonin B
IUPAC Name:	n.a.
Synonyms:	nervonin B
Standard InCHIKey:	NOZXMJPFKFLMJK-LYVLPCRDSA-N
Standard InCHI:	InChI=1S/C26H36O9/c1-11-15-8-16(33-12(2)27)20-25(7)18(31)9-17(30)24(5,6)21(25)19(34-13(3)28)23(35-14(4)29)26(20,10-15)22(11)32/h15-21,23,30-31H,1,8-10H2,2-7H3/t15-,16+,17+,18+,19-,20+,21-,23+,25+,26+/m1/s1
SMILES:	CC(=O)O[C@H]1C[C@@H]2C[C@]3([C@@H]1[C@]1(C)[C@@H](O)C[C@@H](C([C@H]1[C@H]([C@@H]3OC(=O)C)OC(=O)C)(C)C)O)C(=O)C2=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL468383
PubChem CID:	24862639
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
NPO8269	Isodon nervosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18345641]
NPO8269	Isodon nervosus	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	1180.0	nM	PMID[525637]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	1530.0	nM	PMID[525637]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	1160.0	nM	PMID[525637]

☑ 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 NPC200957 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	243
0.1-0.2	1705
0.2-0.3	5427
0.3-0.4	8701
0.4-0.5	11776
0.5-0.6	6048
0.6-0.7	5367
0.7-0.8	2897
0.8-0.85	318
0.85-0.9	150
0.9-0.95	53
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC138908
0.9898	High Similarity	NPC166993
0.9798	High Similarity	NPC273155
0.9794	High Similarity	NPC122811
0.9694	High Similarity	NPC301787
0.9691	High Similarity	NPC275990
0.9596	High Similarity	NPC222833
0.9592	High Similarity	NPC209298
0.9592	High Similarity	NPC277074
0.9588	High Similarity	NPC46848
0.9588	High Similarity	NPC252614
0.9406	High Similarity	NPC231278
0.9406	High Similarity	NPC112895
0.9406	High Similarity	NPC218123
0.9381	High Similarity	NPC162459
0.9381	High Similarity	NPC20479
0.9381	High Similarity	NPC38296
0.9381	High Similarity	NPC38471
0.9381	High Similarity	NPC28864
0.9381	High Similarity	NPC471038
0.9381	High Similarity	NPC98837
0.9307	High Similarity	NPC201908
0.9307	High Similarity	NPC176949
0.9293	High Similarity	NPC88203
0.9293	High Similarity	NPC246736
0.9293	High Similarity	NPC214946
0.9293	High Similarity	NPC148628
0.9293	High Similarity	NPC304832
0.9293	High Similarity	NPC286519
0.9293	High Similarity	NPC76866
0.9286	High Similarity	NPC470388
0.9286	High Similarity	NPC293866
0.9223	High Similarity	NPC85391
0.9223	High Similarity	NPC320383
0.9223	High Similarity	NPC137104
0.9223	High Similarity	NPC474786
0.9216	High Similarity	NPC63841
0.92	High Similarity	NPC87927
0.9192	High Similarity	NPC289148
0.9192	High Similarity	NPC52899
0.9192	High Similarity	NPC236585
0.9192	High Similarity	NPC163963
0.9184	High Similarity	NPC89099
0.9184	High Similarity	NPC474793
0.9175	High Similarity	NPC29410
0.9175	High Similarity	NPC200054
0.9175	High Similarity	NPC329910
0.9143	High Similarity	NPC471252
0.9126	High Similarity	NPC274827
0.9126	High Similarity	NPC131903
0.9118	High Similarity	NPC186054
0.9091	High Similarity	NPC287676
0.9082	High Similarity	NPC10864
0.9072	High Similarity	NPC98639
0.9072	High Similarity	NPC470229
0.9072	High Similarity	NPC470232
0.9048	High Similarity	NPC474927
0.9038	High Similarity	NPC471093
0.9038	High Similarity	NPC100908
0.9029	High Similarity	NPC471094
0.9029	High Similarity	NPC469984
0.9029	High Similarity	NPC473410
0.902	High Similarity	NPC295366
0.901	High Similarity	NPC139347
0.901	High Similarity	NPC96217
0.899	High Similarity	NPC16911
0.899	High Similarity	NPC78427
0.8969	High Similarity	NPC475118
0.8969	High Similarity	NPC470386
0.8969	High Similarity	NPC470385
0.8969	High Similarity	NPC47853
0.8952	High Similarity	NPC29505
0.8952	High Similarity	NPC213320
0.8932	High Similarity	NPC471474
0.8922	High Similarity	NPC84928
0.8922	High Similarity	NPC98603
0.8889	High Similarity	NPC473304
0.8868	High Similarity	NPC473397
0.8866	High Similarity	NPC294263
0.8846	High Similarity	NPC55973
0.8835	High Similarity	NPC130511
0.8835	High Similarity	NPC37600
0.8835	High Similarity	NPC56656
0.8835	High Similarity	NPC307660
0.8824	High Similarity	NPC216114
0.8812	High Similarity	NPC253886
0.8812	High Similarity	NPC121218
0.8812	High Similarity	NPC148279
0.8812	High Similarity	NPC471790
0.8796	High Similarity	NPC88945
0.8788	High Similarity	NPC470387
0.8788	High Similarity	NPC13949
0.8785	High Similarity	NPC132668
0.8774	High Similarity	NPC94650
0.8763	High Similarity	NPC211403
0.8763	High Similarity	NPC470230
0.8763	High Similarity	NPC198242
0.8763	High Similarity	NPC250753
0.8762	High Similarity	NPC469983
0.8762	High Similarity	NPC102741
0.875	High Similarity	NPC471461
0.875	High Similarity	NPC67745
0.8738	High Similarity	NPC47281
0.8725	High Similarity	NPC170615
0.8713	High Similarity	NPC291785
0.8713	High Similarity	NPC94906
0.8713	High Similarity	NPC127408
0.8713	High Similarity	NPC267921
0.8713	High Similarity	NPC293890
0.8692	High Similarity	NPC471245
0.8692	High Similarity	NPC473352
0.8687	High Similarity	NPC210214
0.8679	High Similarity	NPC473324
0.8667	High Similarity	NPC189663
0.8667	High Similarity	NPC232133
0.8667	High Similarity	NPC89860
0.8654	High Similarity	NPC28791
0.8654	High Similarity	NPC50535
0.8654	High Similarity	NPC4115
0.8627	High Similarity	NPC14634
0.8627	High Similarity	NPC71706
0.8614	High Similarity	NPC26270
0.8614	High Similarity	NPC472028
0.8611	High Similarity	NPC471248
0.86	High Similarity	NPC256227
0.86	High Similarity	NPC104568
0.8598	High Similarity	NPC122339
0.8598	High Similarity	NPC470281
0.8598	High Similarity	NPC329953
0.8586	High Similarity	NPC153775
0.8586	High Similarity	NPC292374
0.8586	High Similarity	NPC91772
0.8586	High Similarity	NPC289539
0.8586	High Similarity	NPC261333
0.8586	High Similarity	NPC129004
0.8586	High Similarity	NPC111524
0.8586	High Similarity	NPC29247
0.8586	High Similarity	NPC215271
0.8586	High Similarity	NPC104371
0.8586	High Similarity	NPC101233
0.8585	High Similarity	NPC118721
0.8585	High Similarity	NPC252679
0.8571	High Similarity	NPC251824
0.8571	High Similarity	NPC96333
0.8571	High Similarity	NPC86852
0.8571	High Similarity	NPC61071
0.8571	High Similarity	NPC88833
0.8558	High Similarity	NPC474558
0.8558	High Similarity	NPC96268
0.8558	High Similarity	NPC13149
0.8558	High Similarity	NPC202793
0.8557	High Similarity	NPC471043
0.8544	High Similarity	NPC124544
0.8544	High Similarity	NPC309388
0.8544	High Similarity	NPC475803
0.8532	High Similarity	NPC243354
0.8529	High Similarity	NPC180733
0.8529	High Similarity	NPC37047
0.8529	High Similarity	NPC477656
0.8529	High Similarity	NPC41971
0.8529	High Similarity	NPC477655
0.8519	High Similarity	NPC471244
0.8519	High Similarity	NPC473303
0.8519	High Similarity	NPC476964
0.8515	High Similarity	NPC190080
0.8515	High Similarity	NPC96839
0.8515	High Similarity	NPC170978
0.8515	High Similarity	NPC253586
0.8515	High Similarity	NPC111187
0.8505	High Similarity	NPC471476
0.85	High Similarity	NPC84018
0.85	High Similarity	NPC263135
0.85	High Similarity	NPC138245
0.85	High Similarity	NPC288906
0.85	High Similarity	NPC231060
0.8491	Intermediate Similarity	NPC37628
0.8491	Intermediate Similarity	NPC211224
0.8485	Intermediate Similarity	NPC181594
0.8485	Intermediate Similarity	NPC144739
0.8469	Intermediate Similarity	NPC80401
0.8462	Intermediate Similarity	NPC469985
0.8462	Intermediate Similarity	NPC159442
0.8462	Intermediate Similarity	NPC470310
0.8455	Intermediate Similarity	NPC229752
0.8447	Intermediate Similarity	NPC75941
0.8447	Intermediate Similarity	NPC295276
0.844	Intermediate Similarity	NPC73986
0.844	Intermediate Similarity	NPC194273
0.844	Intermediate Similarity	NPC320118
0.8426	Intermediate Similarity	NPC157476
0.8426	Intermediate Similarity	NPC471243
0.8426	Intermediate Similarity	NPC63244
0.8416	Intermediate Similarity	NPC135548
0.8416	Intermediate Similarity	NPC264979
0.8416	Intermediate Similarity	NPC219353
0.84	Intermediate Similarity	NPC191094
0.84	Intermediate Similarity	NPC302008
0.8396	Intermediate Similarity	NPC78966
0.8396	Intermediate Similarity	NPC284732
0.8384	Intermediate Similarity	NPC476168

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 NPC200957 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	2140
0.2-0.3	3948
0.3-0.4	1783
0.4-0.5	555
0.5-0.6	242
0.6-0.7	154
0.7-0.8	95
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8148	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6319	Approved
0.7857	Intermediate Similarity	NPD8297	Approved
0.7843	Intermediate Similarity	NPD8034	Phase 2
0.7843	Intermediate Similarity	NPD8035	Phase 2
0.7768	Intermediate Similarity	NPD6649	Approved
0.7768	Intermediate Similarity	NPD6650	Approved
0.7748	Intermediate Similarity	NPD6372	Approved
0.7748	Intermediate Similarity	NPD6373	Approved
0.7731	Intermediate Similarity	NPD7492	Approved
0.7692	Intermediate Similarity	NPD6054	Approved
0.7686	Intermediate Similarity	NPD7736	Approved
0.7667	Intermediate Similarity	NPD6616	Approved
0.7658	Intermediate Similarity	NPD6881	Approved
0.7658	Intermediate Similarity	NPD6899	Approved
0.7647	Intermediate Similarity	NPD8328	Phase 3
0.7636	Intermediate Similarity	NPD6402	Approved
0.7636	Intermediate Similarity	NPD5739	Approved
0.7636	Intermediate Similarity	NPD7128	Approved
0.7636	Intermediate Similarity	NPD6675	Approved
0.7632	Intermediate Similarity	NPD4632	Approved
0.7623	Intermediate Similarity	NPD7319	Approved
0.7603	Intermediate Similarity	NPD7078	Approved
0.76	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD5697	Approved
0.7563	Intermediate Similarity	NPD6370	Approved
0.7544	Intermediate Similarity	NPD6882	Approved
0.7542	Intermediate Similarity	NPD6059	Approved
0.7522	Intermediate Similarity	NPD7102	Approved
0.7522	Intermediate Similarity	NPD7290	Approved
0.7522	Intermediate Similarity	NPD6883	Approved
0.75	Intermediate Similarity	NPD7320	Approved
0.7479	Intermediate Similarity	NPD6016	Approved
0.7479	Intermediate Similarity	NPD6921	Approved
0.7479	Intermediate Similarity	NPD6015	Approved
0.7478	Intermediate Similarity	NPD8133	Approved
0.7459	Intermediate Similarity	NPD8293	Discontinued
0.7456	Intermediate Similarity	NPD8130	Phase 1
0.7456	Intermediate Similarity	NPD6847	Approved
0.7456	Intermediate Similarity	NPD6617	Approved
0.7456	Intermediate Similarity	NPD6869	Approved
0.7436	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7115	Discovery
0.7436	Intermediate Similarity	NPD6009	Approved
0.7434	Intermediate Similarity	NPD6013	Approved
0.7434	Intermediate Similarity	NPD6012	Approved
0.7434	Intermediate Similarity	NPD6014	Approved
0.7434	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6399	Phase 3
0.7417	Intermediate Similarity	NPD5988	Approved
0.7411	Intermediate Similarity	NPD5701	Approved
0.7407	Intermediate Similarity	NPD7638	Approved
0.7377	Intermediate Similarity	NPD7507	Approved
0.7368	Intermediate Similarity	NPD4634	Approved
0.7368	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD7604	Phase 2
0.7345	Intermediate Similarity	NPD6011	Approved
0.7339	Intermediate Similarity	NPD7640	Approved
0.7339	Intermediate Similarity	NPD7639	Approved
0.7333	Intermediate Similarity	NPD5983	Phase 2
0.7333	Intermediate Similarity	NPD6079	Approved
0.7321	Intermediate Similarity	NPD6008	Approved
0.7315	Intermediate Similarity	NPD7902	Approved
0.7308	Intermediate Similarity	NPD5328	Approved
0.7281	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD6115	Approved
0.7245	Intermediate Similarity	NPD6114	Approved
0.7245	Intermediate Similarity	NPD6697	Approved
0.7245	Intermediate Similarity	NPD6118	Approved
0.7236	Intermediate Similarity	NPD6336	Discontinued
0.7196	Intermediate Similarity	NPD7748	Approved
0.7193	Intermediate Similarity	NPD6686	Approved
0.7182	Intermediate Similarity	NPD5285	Approved
0.7182	Intermediate Similarity	NPD5286	Approved
0.7182	Intermediate Similarity	NPD4696	Approved
0.717	Intermediate Similarity	NPD7515	Phase 2
0.7156	Intermediate Similarity	NPD4755	Approved
0.7155	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6116	Phase 1
0.7105	Intermediate Similarity	NPD6412	Phase 2
0.7105	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4225	Approved
0.7064	Intermediate Similarity	NPD5222	Approved
0.7064	Intermediate Similarity	NPD4697	Phase 3
0.7064	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD5221	Approved
0.7059	Intermediate Similarity	NPD6274	Approved
0.7059	Intermediate Similarity	NPD4788	Approved
0.7054	Intermediate Similarity	NPD5225	Approved
0.7054	Intermediate Similarity	NPD5226	Approved
0.7054	Intermediate Similarity	NPD4633	Approved
0.7054	Intermediate Similarity	NPD5224	Approved
0.7054	Intermediate Similarity	NPD5211	Phase 2
0.7041	Intermediate Similarity	NPD6117	Approved
0.7037	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7900	Approved
0.7027	Intermediate Similarity	NPD4700	Approved
0.7025	Intermediate Similarity	NPD7100	Approved
0.7025	Intermediate Similarity	NPD7516	Approved
0.7025	Intermediate Similarity	NPD7101	Approved
0.7019	Intermediate Similarity	NPD3618	Phase 1
0.7	Intermediate Similarity	NPD5173	Approved
0.7	Intermediate Similarity	NPD6083	Phase 2
0.7	Intermediate Similarity	NPD6084	Phase 2
0.6991	Remote Similarity	NPD5174	Approved
0.6991	Remote Similarity	NPD5175	Approved
0.6984	Remote Similarity	NPD6033	Approved
0.6964	Remote Similarity	NPD5223	Approved
0.6964	Remote Similarity	NPD1700	Approved
0.6942	Remote Similarity	NPD7328	Approved
0.6942	Remote Similarity	NPD6335	Approved
0.6942	Remote Similarity	NPD7327	Approved
0.6939	Remote Similarity	NPD3703	Phase 2
0.693	Remote Similarity	NPD5141	Approved
0.693	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD6868	Approved
0.6903	Remote Similarity	NPD7632	Discontinued
0.6897	Remote Similarity	NPD4730	Approved
0.6897	Remote Similarity	NPD4729	Approved
0.687	Remote Similarity	NPD4768	Approved
0.687	Remote Similarity	NPD4767	Approved
0.686	Remote Similarity	NPD6317	Approved
0.6852	Remote Similarity	NPD6411	Approved
0.6837	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD4786	Approved
0.6803	Remote Similarity	NPD6313	Approved
0.6803	Remote Similarity	NPD6314	Approved
0.6789	Remote Similarity	NPD4202	Approved
0.6786	Remote Similarity	NPD5696	Approved
0.678	Remote Similarity	NPD5248	Approved
0.678	Remote Similarity	NPD5247	Approved
0.678	Remote Similarity	NPD5251	Approved
0.678	Remote Similarity	NPD5249	Phase 3
0.678	Remote Similarity	NPD5250	Approved
0.6774	Remote Similarity	NPD6908	Approved
0.6774	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD8380	Approved
0.6774	Remote Similarity	NPD8379	Approved
0.6774	Remote Similarity	NPD6909	Approved
0.6774	Remote Similarity	NPD8378	Approved
0.6774	Remote Similarity	NPD8296	Approved
0.6774	Remote Similarity	NPD8335	Approved
0.6752	Remote Similarity	NPD5128	Approved
0.6729	Remote Similarity	NPD6672	Approved
0.6729	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD5737	Approved
0.6698	Remote Similarity	NPD7334	Approved
0.6698	Remote Similarity	NPD6684	Approved
0.6698	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD6409	Approved
0.6698	Remote Similarity	NPD7146	Approved
0.6698	Remote Similarity	NPD7521	Approved
0.6698	Remote Similarity	NPD5330	Approved
0.6697	Remote Similarity	NPD7637	Suspended
0.6696	Remote Similarity	NPD4754	Approved
0.6694	Remote Similarity	NPD8377	Approved
0.6694	Remote Similarity	NPD8294	Approved
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6101	Approved
0.664	Remote Similarity	NPD8033	Approved
0.6639	Remote Similarity	NPD6371	Approved
0.6636	Remote Similarity	NPD5779	Approved
0.6636	Remote Similarity	NPD3573	Approved
0.6636	Remote Similarity	NPD5778	Approved
0.6635	Remote Similarity	NPD3667	Approved
0.6633	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD7525	Registered
0.6583	Remote Similarity	NPD5217	Approved
0.6583	Remote Similarity	NPD5216	Approved
0.6583	Remote Similarity	NPD5215	Approved
0.6574	Remote Similarity	NPD6903	Approved
0.6545	Remote Similarity	NPD7983	Approved
0.6535	Remote Similarity	NPD6067	Discontinued
0.6529	Remote Similarity	NPD6053	Discontinued
0.6519	Remote Similarity	NPD6334	Approved
0.6519	Remote Similarity	NPD6333	Approved
0.6518	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD5210	Approved
0.6518	Remote Similarity	NPD4629	Approved
0.6514	Remote Similarity	NPD4753	Phase 2
0.6509	Remote Similarity	NPD3665	Phase 1
0.6509	Remote Similarity	NPD3133	Approved
0.6509	Remote Similarity	NPD3666	Approved
0.6508	Remote Similarity	NPD8513	Phase 3
0.6508	Remote Similarity	NPD8515	Approved
0.6508	Remote Similarity	NPD8517	Approved
0.6508	Remote Similarity	NPD8516	Approved
0.6508	Remote Similarity	NPD7503	Approved
0.65	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5169	Approved
0.65	Remote Similarity	NPD5135	Approved
0.6471	Remote Similarity	NPD5168	Approved
0.6446	Remote Similarity	NPD5127	Approved
0.6439	Remote Similarity	NPD7260	Phase 2
0.6429	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD5281	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