NPASS Compound

Structure

CID20479 OpenBabel06191715342D 31 34 0 0 1 0 0 0 0 0999 V2000 2.1120 -0.5705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0402 -3.2822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1173 2.6460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9014 2.1059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7745 2.1059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5586 -0.8731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0001 -1.7998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1172 -0.0001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7793 -0.4499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.8999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2293 -0.5705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3715 -2.6800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8734 2.2094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7794 -1.3498 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7793 1.3498 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7793 -1.3498 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3379 -0.4500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1172 0.8998 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5586 0.8998 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7793 -0.4499 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8999 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3379 1.3497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5586 -0.0000 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 -0.5156 -2.9581 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6295 2.6460 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7793 2.2229 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3379 -1.3231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3422 0.7663 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5586 -1.7998 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8734 1.3363 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 22 1 0 0 0 0 5 22 1 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 8 18 1 0 0 0 0 9 14 1 0 0 0 0 10 15 1 0 0 0 0 10 24 1 0 0 0 0 11 14 1 0 0 0 0 11 21 1 0 0 0 0 12 25 2 0 0 0 0 12 30 1 0 0 0 0 13 26 2 0 0 0 0 13 31 1 0 0 0 0 14 7 1 6 0 0 0 15 19 1 0 0 0 0 15 27 1 1 0 0 0 16 20 1 0 0 0 0 16 30 1 6 0 0 0 17 23 1 1 0 0 0 17 28 1 0 0 0 0 18 22 1 0 0 0 0 18 31 1 6 0 0 0 19 22 1 0 0 0 0 19 23 1 1 0 0 0 20 23 1 1 0 0 0 20 24 1 0 0 0 0 21 24 1 0 0 0 0 21 29 2 0 0 0 0 23 6 1 1 0 0 0 24 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.23
Volume:	440.42
LogP:	2.169
LogD:	2.242
LogS:	-3.534
# Rotatable Bonds:	4
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.506
Synthetic Accessibility Score:	6.153
Fsp3:	0.792
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:	-5.297
MDCK Permeability:	8.180364238796756e-05
Pgp-inhibitor:	0.442
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.969

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.213
Plasma Protein Binding (PPB):	33.57122039794922%
Volume Distribution (VD):	0.563
Pgp-substrate:	56.72523498535156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.054
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.327
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.065
CYP3A4-inhibitor:	0.323
CYP3A4-substrate:	0.269

ADMET: Excretion

Clearance (CL):	3.584
Half-life (T1/2):	0.278

ADMET: Toxicity

hERG Blockers:	0.575
Human Hepatotoxicity (H-HT):	0.069
Drug-inuced Liver Injury (DILI):	0.163
AMES Toxicity:	0.181
Rat Oral Acute Toxicity:	0.903
Maximum Recommended Daily Dose:	0.976
Skin Sensitization:	0.734
Carcinogencity:	0.299
Eye Corrosion:	0.063
Eye Irritation:	0.017
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: NPC20479

Natural Product ID:	NPC20479
*Common Name:**	Inflexinol
IUPAC Name:	n.a.
Synonyms:	Inflexinol
Standard InCHIKey:	ZMYDEPIDSFWDLQ-AZPRSEESSA-N
Standard InCHI:	InChI=1S/C24H34O7/c1-11-14-7-16(30-12(2)25)20-23(6)17(28)8-18(31-13(3)26)22(4,5)19(23)15(27)10-24(20,9-14)21(11)29/h14-20,27-28H,1,7-10H2,2-6H3/t14-,15+,16+,17+,18+,19-,20+,23-,24+/m1/s1
SMILES:	C=C1[C@@H]2C[C@@H]([C@H]3[C@]4(C)[C@H](C[C@@H](C(C)(C)[C@H]4[C@H](C[C@]3(C2)C1=O)O)OC(=O)C)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL225258
PubChem CID:	44421641
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
NPO26913	Isodon excisus	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[10896056]
NPO26913	Isodon excisus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374970]
NPO26913	Isodon excisus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17338565]
NPO26913	Isodon excisus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21273070]
NPO26913	Isodon excisus	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[22066578]
NPO20759	Isodon inflexa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20759	Isodon inflexa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26913	Isodon excisus	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
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	440.0	nM	PMID[570929]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	940.0	nM	PMID[570929]

☑ 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 NPC20479 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	221
0.1-0.2	1617
0.2-0.3	5464
0.3-0.4	9710
0.4-0.5	11050
0.5-0.6	5575
0.6-0.7	5647
0.7-0.8	2889
0.8-0.85	321
0.85-0.9	118
0.9-0.95	68
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC38296
1.0	High Similarity	NPC28864
1.0	High Similarity	NPC38471
1.0	High Similarity	NPC162459
1.0	High Similarity	NPC98837
0.9891	High Similarity	NPC293866
0.9785	High Similarity	NPC46848
0.9783	High Similarity	NPC89099
0.978	High Similarity	NPC29410
0.978	High Similarity	NPC200054
0.9681	High Similarity	NPC275990
0.9674	High Similarity	NPC10864
0.967	High Similarity	NPC98639
0.957	High Similarity	NPC471038
0.9479	High Similarity	NPC301787
0.9474	High Similarity	NPC76866
0.9474	High Similarity	NPC246736
0.9474	High Similarity	NPC214946
0.9474	High Similarity	NPC148628
0.9474	High Similarity	NPC304832
0.9474	High Similarity	NPC88203
0.9474	High Similarity	NPC286519
0.9451	High Similarity	NPC294263
0.9381	High Similarity	NPC222833
0.9381	High Similarity	NPC200957
0.9381	High Similarity	NPC138908
0.9375	High Similarity	NPC87927
0.9368	High Similarity	NPC52899
0.9368	High Similarity	NPC163963
0.9368	High Similarity	NPC289148
0.9368	High Similarity	NPC253886
0.9368	High Similarity	NPC121218
0.9368	High Similarity	NPC252614
0.9362	High Similarity	NPC474793
0.9355	High Similarity	NPC329910
0.9286	High Similarity	NPC201908
0.9286	High Similarity	NPC176949
0.9286	High Similarity	NPC166993
0.9271	High Similarity	NPC170615
0.9263	High Similarity	NPC287676
0.9247	High Similarity	NPC470229
0.9247	High Similarity	NPC470232
0.9192	High Similarity	NPC218123
0.9192	High Similarity	NPC273155
0.9192	High Similarity	NPC231278
0.9192	High Similarity	NPC112895
0.9175	High Similarity	NPC139347
0.9175	High Similarity	NPC209298
0.9175	High Similarity	NPC122811
0.9175	High Similarity	NPC277074
0.9167	High Similarity	NPC236585
0.9158	High Similarity	NPC16911
0.9158	High Similarity	NPC78427
0.914	High Similarity	NPC475118
0.914	High Similarity	NPC47853
0.914	High Similarity	NPC470385
0.914	High Similarity	NPC470386
0.9082	High Similarity	NPC98603
0.9082	High Similarity	NPC47281
0.9082	High Similarity	NPC84928
0.9062	High Similarity	NPC293890
0.9062	High Similarity	NPC470388
0.899	High Similarity	NPC28791
0.899	High Similarity	NPC50535
0.899	High Similarity	NPC295366
0.899	High Similarity	NPC37600
0.898	High Similarity	NPC96217
0.898	High Similarity	NPC216114
0.8969	High Similarity	NPC148279
0.8969	High Similarity	NPC471790
0.8969	High Similarity	NPC295276
0.8947	High Similarity	NPC13949
0.8947	High Similarity	NPC219353
0.8947	High Similarity	NPC470387
0.8925	High Similarity	NPC198242
0.8925	High Similarity	NPC470230
0.8925	High Similarity	NPC250753
0.8925	High Similarity	NPC211403
0.8901	High Similarity	NPC153604
0.89	High Similarity	NPC86852
0.89	High Similarity	NPC251824
0.8866	High Similarity	NPC94906
0.8866	High Similarity	NPC267921
0.8842	High Similarity	NPC210214
0.883	High Similarity	NPC224060
0.883	High Similarity	NPC244356
0.8812	High Similarity	NPC63841
0.88	High Similarity	NPC4115
0.8791	High Similarity	NPC471042
0.8776	High Similarity	NPC14634
0.8776	High Similarity	NPC71706
0.8763	High Similarity	NPC26270
0.8763	High Similarity	NPC472028
0.875	High Similarity	NPC104568
0.8738	High Similarity	NPC329953
0.8737	High Similarity	NPC261333
0.8737	High Similarity	NPC215271
0.8737	High Similarity	NPC272635
0.8737	High Similarity	NPC169751
0.8737	High Similarity	NPC289539
0.8737	High Similarity	NPC129004
0.8737	High Similarity	NPC91772
0.8737	High Similarity	NPC292374
0.8737	High Similarity	NPC111524
0.8737	High Similarity	NPC104371
0.8737	High Similarity	NPC101233
0.8737	High Similarity	NPC153775
0.8737	High Similarity	NPC29247
0.8725	High Similarity	NPC469983
0.8713	High Similarity	NPC61071
0.8713	High Similarity	NPC186054
0.8713	High Similarity	NPC88833
0.8713	High Similarity	NPC96333
0.871	High Similarity	NPC471043
0.87	High Similarity	NPC474558
0.87	High Similarity	NPC202793
0.87	High Similarity	NPC13149
0.87	High Similarity	NPC96268
0.8696	High Similarity	NPC174619
0.8687	High Similarity	NPC124544
0.8687	High Similarity	NPC475803
0.8687	High Similarity	NPC309388
0.8673	High Similarity	NPC37047
0.8673	High Similarity	NPC41971
0.8673	High Similarity	NPC180733
0.866	High Similarity	NPC253586
0.866	High Similarity	NPC190080
0.866	High Similarity	NPC111187
0.8654	High Similarity	NPC476964
0.8646	High Similarity	NPC157686
0.8646	High Similarity	NPC231060
0.8646	High Similarity	NPC84018
0.8646	High Similarity	NPC138245
0.8646	High Similarity	NPC259042
0.8646	High Similarity	NPC263135
0.8646	High Similarity	NPC288906
0.8641	High Similarity	NPC471093
0.8641	High Similarity	NPC320383
0.8641	High Similarity	NPC137104
0.8641	High Similarity	NPC474786
0.8641	High Similarity	NPC85391
0.8632	High Similarity	NPC144739
0.8632	High Similarity	NPC181594
0.8627	High Similarity	NPC473410
0.8627	High Similarity	NPC471094
0.8627	High Similarity	NPC232133
0.8627	High Similarity	NPC469984
0.8627	High Similarity	NPC211224
0.8617	High Similarity	NPC80401
0.86	High Similarity	NPC159442
0.86	High Similarity	NPC470310
0.86	High Similarity	NPC469985
0.8586	High Similarity	NPC75941
0.8571	High Similarity	NPC146683
0.8571	High Similarity	NPC471252
0.8571	High Similarity	NPC299963
0.8571	High Similarity	NPC476807
0.8571	High Similarity	NPC476806
0.8571	High Similarity	NPC119036
0.8558	High Similarity	NPC470281
0.8558	High Similarity	NPC94650
0.8558	High Similarity	NPC29505
0.8557	High Similarity	NPC256227
0.8557	High Similarity	NPC264979
0.8557	High Similarity	NPC135548
0.8544	High Similarity	NPC131903
0.8544	High Similarity	NPC274827
0.8542	High Similarity	NPC148000
0.8542	High Similarity	NPC302008
0.8542	High Similarity	NPC303863
0.8542	High Similarity	NPC469596
0.8542	High Similarity	NPC191094
0.8542	High Similarity	NPC225474
0.8529	High Similarity	NPC471474
0.8526	High Similarity	NPC198054
0.8526	High Similarity	NPC299185
0.8526	High Similarity	NPC476168
0.8515	High Similarity	NPC101842
0.8515	High Similarity	NPC310586
0.8515	High Similarity	NPC29705
0.85	High Similarity	NPC15396
0.85	High Similarity	NPC136289
0.8495	Intermediate Similarity	NPC259009
0.8485	Intermediate Similarity	NPC291785
0.8485	Intermediate Similarity	NPC108371
0.8485	Intermediate Similarity	NPC127408
0.8476	Intermediate Similarity	NPC474927
0.8469	Intermediate Similarity	NPC96839
0.8469	Intermediate Similarity	NPC473963
0.8469	Intermediate Similarity	NPC111348
0.8462	Intermediate Similarity	NPC118800
0.8462	Intermediate Similarity	NPC49730
0.8462	Intermediate Similarity	NPC100908
0.8462	Intermediate Similarity	NPC98069
0.8462	Intermediate Similarity	NPC471037
0.8447	Intermediate Similarity	NPC55973
0.8447	Intermediate Similarity	NPC469729
0.8447	Intermediate Similarity	NPC469733
0.8438	Intermediate Similarity	NPC59170
0.8438	Intermediate Similarity	NPC199543

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 NPC20479 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	204
0.1-0.2	2042
0.2-0.3	3972
0.3-0.4	1891
0.4-0.5	555
0.5-0.6	210
0.6-0.7	136
0.7-0.8	138
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD8034	Phase 2
0.8333	Intermediate Similarity	NPD8035	Phase 2
0.8095	Intermediate Similarity	NPD6899	Approved
0.8095	Intermediate Similarity	NPD6881	Approved
0.8085	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD7128	Approved
0.8077	Intermediate Similarity	NPD6675	Approved
0.8077	Intermediate Similarity	NPD6402	Approved
0.8077	Intermediate Similarity	NPD5739	Approved
0.8037	Intermediate Similarity	NPD6649	Approved
0.8037	Intermediate Similarity	NPD6650	Approved
0.8019	Intermediate Similarity	NPD6373	Approved
0.8019	Intermediate Similarity	NPD6372	Approved
0.8	Intermediate Similarity	NPD5697	Approved
0.7944	Intermediate Similarity	NPD7290	Approved
0.7944	Intermediate Similarity	NPD7102	Approved
0.7944	Intermediate Similarity	NPD6883	Approved
0.7925	Intermediate Similarity	NPD7320	Approved
0.7879	Intermediate Similarity	NPD6399	Phase 3
0.787	Intermediate Similarity	NPD6617	Approved
0.787	Intermediate Similarity	NPD6869	Approved
0.787	Intermediate Similarity	NPD8130	Phase 1
0.787	Intermediate Similarity	NPD6847	Approved
0.785	Intermediate Similarity	NPD6013	Approved
0.785	Intermediate Similarity	NPD6012	Approved
0.785	Intermediate Similarity	NPD6014	Approved
0.7843	Intermediate Similarity	NPD7638	Approved
0.783	Intermediate Similarity	NPD5701	Approved
0.7798	Intermediate Similarity	NPD8297	Approved
0.7798	Intermediate Similarity	NPD6882	Approved
0.7778	Intermediate Similarity	NPD6079	Approved
0.7767	Intermediate Similarity	NPD7640	Approved
0.7767	Intermediate Similarity	NPD7639	Approved
0.7757	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7757	Intermediate Similarity	NPD6011	Approved
0.7755	Intermediate Similarity	NPD5328	Approved
0.7745	Intermediate Similarity	NPD7902	Approved
0.7736	Intermediate Similarity	NPD6008	Approved
0.7727	Intermediate Similarity	NPD4632	Approved
0.7717	Intermediate Similarity	NPD6697	Approved
0.7717	Intermediate Similarity	NPD6118	Approved
0.7717	Intermediate Similarity	NPD6115	Approved
0.7717	Intermediate Similarity	NPD6114	Approved
0.7632	Intermediate Similarity	NPD6319	Approved
0.7624	Intermediate Similarity	NPD7748	Approved
0.7609	Intermediate Similarity	NPD6116	Phase 1
0.76	Intermediate Similarity	NPD7515	Phase 2
0.7596	Intermediate Similarity	NPD5285	Approved
0.7596	Intermediate Similarity	NPD5286	Approved
0.7596	Intermediate Similarity	NPD4696	Approved
0.7573	Intermediate Similarity	NPD4755	Approved
0.7545	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD6009	Approved
0.7521	Intermediate Similarity	NPD7492	Approved
0.75	Intermediate Similarity	NPD6117	Approved
0.75	Intermediate Similarity	NPD4788	Approved
0.7479	Intermediate Similarity	NPD7736	Approved
0.7478	Intermediate Similarity	NPD6054	Approved
0.7476	Intermediate Similarity	NPD5221	Approved
0.7476	Intermediate Similarity	NPD5222	Approved
0.7476	Intermediate Similarity	NPD4697	Phase 3
0.7476	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD6616	Approved
0.7453	Intermediate Similarity	NPD5224	Approved
0.7453	Intermediate Similarity	NPD5211	Phase 2
0.7453	Intermediate Similarity	NPD5225	Approved
0.7453	Intermediate Similarity	NPD5226	Approved
0.7453	Intermediate Similarity	NPD4633	Approved
0.7451	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD7900	Approved
0.7449	Intermediate Similarity	NPD3618	Phase 1
0.7436	Intermediate Similarity	NPD7604	Phase 2
0.7434	Intermediate Similarity	NPD6274	Approved
0.7429	Intermediate Similarity	NPD4700	Approved
0.7414	Intermediate Similarity	NPD5983	Phase 2
0.7411	Intermediate Similarity	NPD8133	Approved
0.7404	Intermediate Similarity	NPD6084	Phase 2
0.7404	Intermediate Similarity	NPD5173	Approved
0.7404	Intermediate Similarity	NPD6083	Phase 2
0.7395	Intermediate Similarity	NPD7078	Approved
0.7391	Intermediate Similarity	NPD3703	Phase 2
0.7391	Intermediate Similarity	NPD7101	Approved
0.7391	Intermediate Similarity	NPD7100	Approved
0.7383	Intermediate Similarity	NPD5174	Approved
0.7383	Intermediate Similarity	NPD5175	Approved
0.7358	Intermediate Similarity	NPD5223	Approved
0.735	Intermediate Similarity	NPD6370	Approved
0.7328	Intermediate Similarity	NPD6059	Approved
0.7315	Intermediate Similarity	NPD5141	Approved
0.7311	Intermediate Similarity	NPD7507	Approved
0.7311	Intermediate Similarity	NPD6336	Discontinued
0.7304	Intermediate Similarity	NPD6335	Approved
0.7297	Intermediate Similarity	NPD4634	Approved
0.729	Intermediate Similarity	NPD7632	Discontinued
0.7288	Intermediate Similarity	NPD8328	Phase 3
0.7283	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD6868	Approved
0.7273	Intermediate Similarity	NPD7319	Approved
0.7265	Intermediate Similarity	NPD6015	Approved
0.7265	Intermediate Similarity	NPD6016	Approved
0.725	Intermediate Similarity	NPD8293	Discontinued
0.7245	Intermediate Similarity	NPD4786	Approved
0.7217	Intermediate Similarity	NPD7115	Discovery
0.7217	Intermediate Similarity	NPD6317	Approved
0.7207	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD5988	Approved
0.7184	Intermediate Similarity	NPD4202	Approved
0.7182	Intermediate Similarity	NPD6412	Phase 2
0.717	Intermediate Similarity	NPD5696	Approved
0.7155	Intermediate Similarity	NPD6313	Approved
0.7155	Intermediate Similarity	NPD6314	Approved
0.7143	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD5737	Approved
0.7129	Intermediate Similarity	NPD6672	Approved
0.7129	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6908	Approved
0.7119	Intermediate Similarity	NPD6909	Approved
0.7119	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD4729	Approved
0.7117	Intermediate Similarity	NPD4730	Approved
0.7117	Intermediate Similarity	NPD6686	Approved
0.7117	Intermediate Similarity	NPD5128	Approved
0.71	Intermediate Similarity	NPD6684	Approved
0.71	Intermediate Similarity	NPD7334	Approved
0.71	Intermediate Similarity	NPD7146	Approved
0.71	Intermediate Similarity	NPD6409	Approved
0.71	Intermediate Similarity	NPD7521	Approved
0.71	Intermediate Similarity	NPD5330	Approved
0.7091	Intermediate Similarity	NPD4767	Approved
0.7091	Intermediate Similarity	NPD4768	Approved
0.7069	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD4754	Approved
0.7048	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5695	Phase 3
0.7041	Intermediate Similarity	NPD3667	Approved
0.703	Intermediate Similarity	NPD3573	Approved
0.701	Intermediate Similarity	NPD7525	Registered
0.6991	Remote Similarity	NPD5248	Approved
0.6991	Remote Similarity	NPD5251	Approved
0.6991	Remote Similarity	NPD5249	Phase 3
0.6991	Remote Similarity	NPD5250	Approved
0.6991	Remote Similarity	NPD5247	Approved
0.6975	Remote Similarity	NPD6921	Approved
0.6961	Remote Similarity	NPD6903	Approved
0.693	Remote Similarity	NPD5216	Approved
0.693	Remote Similarity	NPD5217	Approved
0.693	Remote Similarity	NPD5215	Approved
0.6923	Remote Similarity	NPD6411	Approved
0.69	Remote Similarity	NPD3666	Approved
0.69	Remote Similarity	NPD3665	Phase 1
0.69	Remote Similarity	NPD3133	Approved
0.6893	Remote Similarity	NPD4753	Phase 2
0.6887	Remote Similarity	NPD5210	Approved
0.6887	Remote Similarity	NPD4629	Approved
0.6875	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6053	Discontinued
0.6864	Remote Similarity	NPD7328	Approved
0.6864	Remote Similarity	NPD7327	Approved
0.6852	Remote Similarity	NPD4225	Approved
0.6848	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5135	Approved
0.6842	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5169	Approved
0.6814	Remote Similarity	NPD5168	Approved
0.6807	Remote Similarity	NPD7516	Approved
0.6783	Remote Similarity	NPD5127	Approved
0.6774	Remote Similarity	NPD6033	Approved
0.6765	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD5284	Approved
0.6762	Remote Similarity	NPD5281	Approved
0.6762	Remote Similarity	NPD7637	Suspended
0.6731	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6904	Approved
0.6731	Remote Similarity	NPD6101	Approved
0.6731	Remote Similarity	NPD6673	Approved
0.6731	Remote Similarity	NPD6080	Approved
0.6703	Remote Similarity	NPD4224	Phase 2
0.6702	Remote Similarity	NPD6081	Approved
0.6702	Remote Similarity	NPD5777	Approved
0.67	Remote Similarity	NPD6435	Approved
0.6698	Remote Similarity	NPD5779	Approved
0.6698	Remote Similarity	NPD5778	Approved
0.6694	Remote Similarity	NPD8335	Approved
0.6694	Remote Similarity	NPD8296	Approved
0.6694	Remote Similarity	NPD8378	Approved
0.6694	Remote Similarity	NPD8380	Approved
0.6694	Remote Similarity	NPD8379	Approved
0.6667	Remote Similarity	NPD3702	Approved
0.6636	Remote Similarity	NPD6001	Approved
0.6612	Remote Similarity	NPD8377	Approved
0.6612	Remote Similarity	NPD8294	Approved
0.661	Remote Similarity	NPD5167	Approved
0.6602	Remote Similarity	NPD6098	Approved
0.6602	Remote Similarity	NPD5279	Phase 3
0.6596	Remote Similarity	NPD4244	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