NPASS Compound

Structure

CID137104 OpenBabel06191715492D 32 36 0 0 1 0 0 0 0 0999 V2000 2.9111 -1.9534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2313 2.5213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7884 -3.0823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1779 0.4209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7928 -3.2038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0001 -2.7461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9115 -1.6630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9486 -0.9274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5855 -1.8307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0327 0.1800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7927 -0.4577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0432 -1.9534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4501 1.6606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9911 -3.4735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5855 -2.7461 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.8307 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3133 -2.0926 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6713 -0.5674 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7081 -1.3730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0343 -0.1600 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3966 -0.4399 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7927 -1.3731 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7928 -1.3730 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7927 -0.4577 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3049 1.4196 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9313 -4.3597 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1420 -0.6214 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0321 0.7256 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6762 -0.3665 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8140 1.0407 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 -1.2535 -2.9787 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 2 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 5 6 1 0 0 0 0 6 16 1 0 0 0 0 7 8 1 0 0 0 0 7 17 1 0 0 0 0 8 21 1 0 0 0 0 9 15 1 0 0 0 0 9 23 1 0 0 0 0 10 21 1 0 0 0 0 10 30 1 0 0 0 0 11 31 1 0 0 0 0 12 15 1 0 0 0 0 12 19 1 0 0 0 0 13 25 2 0 0 0 0 13 30 1 0 0 0 0 14 26 2 0 0 0 0 14 32 1 0 0 0 0 15 5 1 6 0 0 0 16 22 1 1 0 0 0 16 23 1 0 0 0 0 17 22 1 1 0 0 0 17 32 1 0 0 0 0 18 20 1 0 0 0 0 18 21 1 1 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 19 27 2 0 0 0 0 20 24 1 6 0 0 0 20 28 1 0 0 0 0 21 4 1 6 0 0 0 22 11 1 1 0 0 0 23 24 1 1 0 0 0 24 29 1 6 0 0 0 24 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.21
Volume:	440.654
LogP:	1.53
LogD:	1.281
LogS:	-3.871
# Rotatable Bonds:	5
TPSA:	119.36
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.493
Synthetic Accessibility Score:	6.824
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:	-5.265
MDCK Permeability:	4.07910774811171e-05
Pgp-inhibitor:	0.418
Pgp-substrate:	0.023
Human Intestinal Absorption (HIA):	0.048
20% Bioavailability (F20%):	0.833
30% Bioavailability (F30%):	0.947

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.732
Plasma Protein Binding (PPB):	65.64087677001953%
Volume Distribution (VD):	1.312
Pgp-substrate:	48.19905471801758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.128
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.428
CYP2C9-inhibitor:	0.019
CYP2C9-substrate:	0.015
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.121
CYP3A4-inhibitor:	0.487
CYP3A4-substrate:	0.237

ADMET: Excretion

Clearance (CL):	2.1
Half-life (T1/2):	0.671

ADMET: Toxicity

hERG Blockers:	0.085
Human Hepatotoxicity (H-HT):	0.205
Drug-inuced Liver Injury (DILI):	0.463
AMES Toxicity:	0.167
Rat Oral Acute Toxicity:	0.298
Maximum Recommended Daily Dose:	0.788
Skin Sensitization:	0.37
Carcinogencity:	0.549
Eye Corrosion:	0.004
Eye Irritation:	0.021
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC137104

Natural Product ID:	NPC137104
*Common Name:**	Effusanin D
IUPAC Name:	n.a.
Synonyms:	Effusanin D
Standard InCHIKey:	IYWHJYKWKCMAGI-LTDHTRFUSA-N
Standard InCHI:	InChI=1S/C24H32O8/c1-12-15-5-6-16-22-11-31-24(29,23(16,9-15)19(12)27)20(28)18(22)21(4,10-30-13(2)25)8-7-17(22)32-14(3)26/h15-18,20,28-29H,1,5-11H2,2-4H3/t15-,16+,17+,18-,20+,21+,22-,23+,24-/m1/s1
SMILES:	C=C1[C@@H]2CC[C@H]3[C@]45CO[C@]([C@H]([C@@H]5[C@@](C)(CC[C@@H]4OC(=O)C)COC(=O)C)O)([C@]3(C2)C1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL521396
PubChem CID:	44585547
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]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17020288]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18491868]
NPO3361	Plocamium cartilagineum	Species	Plocamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2089127]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[20949916]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[20949916]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22624550]
NPO10640	Euchresta formosana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3071	Rabdosia effusa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10640	Euchresta formosana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11346	Acetobacter pasteurianus	Species	Acetobacteraceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO3361	Plocamium cartilagineum	Species	Plocamiaceae	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	3300.0	nM	PMID[477627]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	5900.0	nM	PMID[477628]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[477628]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	9100.0	nM	PMID[477628]

☑ 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 NPC137104 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	290
0.1-0.2	1992
0.2-0.3	6071
0.3-0.4	10478
0.4-0.5	10261
0.5-0.6	6106
0.6-0.7	4347
0.7-0.8	2132
0.8-0.85	832
0.85-0.9	113
0.9-0.95	35
0.95-1	40

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474786
1.0	High Similarity	NPC320383
0.9901	High Similarity	NPC131903
0.9901	High Similarity	NPC274827
0.9806	High Similarity	NPC474927
0.9804	High Similarity	NPC85391
0.9802	High Similarity	NPC469984
0.9802	High Similarity	NPC471094
0.9802	High Similarity	NPC473410
0.9709	High Similarity	NPC213320
0.9703	High Similarity	NPC471474
0.9615	High Similarity	NPC473397
0.9608	High Similarity	NPC63841
0.9604	High Similarity	NPC56656
0.9604	High Similarity	NPC307660
0.9604	High Similarity	NPC130511
0.9528	High Similarity	NPC88945
0.9524	High Similarity	NPC132668
0.9524	High Similarity	NPC471252
0.9515	High Similarity	NPC102741
0.951	High Similarity	NPC186054
0.9429	High Similarity	NPC473352
0.9423	High Similarity	NPC471093
0.9417	High Similarity	NPC89860
0.9417	High Similarity	NPC189663
0.9333	High Similarity	NPC29505
0.9327	High Similarity	NPC118721
0.9327	High Similarity	NPC252679
0.932	High Similarity	NPC166993
0.9259	High Similarity	NPC473304
0.9245	High Similarity	NPC471244
0.9238	High Similarity	NPC471476
0.9231	High Similarity	NPC273155
0.9231	High Similarity	NPC232133
0.9231	High Similarity	NPC55973
0.9223	High Similarity	NPC138908
0.9223	High Similarity	NPC200957
0.9216	High Similarity	NPC139347
0.9216	High Similarity	NPC277074
0.9216	High Similarity	NPC209298
0.9216	High Similarity	NPC122811
0.9208	High Similarity	NPC14634
0.9167	High Similarity	NPC229752
0.9159	High Similarity	NPC320118
0.9159	High Similarity	NPC471248
0.9159	High Similarity	NPC194273
0.9151	High Similarity	NPC63244
0.9143	High Similarity	NPC469983
0.9135	High Similarity	NPC67745
0.9135	High Similarity	NPC471461
0.9126	High Similarity	NPC202793
0.9126	High Similarity	NPC301787
0.9083	High Similarity	NPC78836
0.9074	High Similarity	NPC243354
0.9065	High Similarity	NPC471245
0.9057	High Similarity	NPC473324
0.9038	High Similarity	NPC222833
0.902	High Similarity	NPC236585
0.902	High Similarity	NPC252614
0.901	High Similarity	NPC474793
0.8981	High Similarity	NPC94141
0.8972	High Similarity	NPC471243
0.8972	High Similarity	NPC56025
0.8972	High Similarity	NPC122339
0.8932	High Similarity	NPC275990
0.8922	High Similarity	NPC470388
0.8899	High Similarity	NPC17165
0.8889	High Similarity	NPC157929
0.8889	High Similarity	NPC145625
0.8889	High Similarity	NPC473303
0.8868	High Similarity	NPC112895
0.8868	High Similarity	NPC231278
0.8868	High Similarity	NPC218123
0.8846	High Similarity	NPC96217
0.8835	High Similarity	NPC46848
0.8824	High Similarity	NPC471038
0.8807	High Similarity	NPC73986
0.8796	High Similarity	NPC329953
0.8785	High Similarity	NPC469744
0.8774	High Similarity	NPC469746
0.8774	High Similarity	NPC88833
0.8774	High Similarity	NPC96333
0.8762	High Similarity	NPC474558
0.875	High Similarity	NPC475803
0.875	High Similarity	NPC309388
0.875	High Similarity	NPC470172
0.8716	High Similarity	NPC207845
0.8716	High Similarity	NPC472719
0.8679	High Similarity	NPC4115
0.8667	High Similarity	NPC87927
0.8667	High Similarity	NPC473406
0.8654	High Similarity	NPC163963
0.8654	High Similarity	NPC289148
0.8654	High Similarity	NPC52899
0.8654	High Similarity	NPC148279
0.8641	High Similarity	NPC38471
0.8641	High Similarity	NPC98837
0.8641	High Similarity	NPC20479
0.8641	High Similarity	NPC162459
0.8641	High Similarity	NPC28864
0.8641	High Similarity	NPC38296
0.8627	High Similarity	NPC329910
0.8627	High Similarity	NPC200054
0.8627	High Similarity	NPC29410
0.8624	High Similarity	NPC274833
0.8624	High Similarity	NPC11035
0.8611	High Similarity	NPC8431
0.8598	High Similarity	NPC61071
0.8598	High Similarity	NPC201908
0.8598	High Similarity	NPC176949
0.8585	High Similarity	NPC101842
0.8571	High Similarity	NPC76866
0.8571	High Similarity	NPC214946
0.8571	High Similarity	NPC218970
0.8571	High Similarity	NPC148628
0.8571	High Similarity	NPC304832
0.8571	High Similarity	NPC246736
0.8571	High Similarity	NPC286519
0.8571	High Similarity	NPC471254
0.8571	High Similarity	NPC88203
0.8571	High Similarity	NPC470171
0.8558	High Similarity	NPC287676
0.8558	High Similarity	NPC293866
0.8558	High Similarity	NPC267921
0.8545	High Similarity	NPC205534
0.8545	High Similarity	NPC470543
0.8532	High Similarity	NPC100908
0.8532	High Similarity	NPC49730
0.8532	High Similarity	NPC98069
0.8529	High Similarity	NPC470232
0.8529	High Similarity	NPC470229
0.8529	High Similarity	NPC98639
0.8519	High Similarity	NPC469733
0.8519	High Similarity	NPC469729
0.8505	High Similarity	NPC12823
0.8505	High Similarity	NPC103172
0.8505	High Similarity	NPC164600
0.8496	Intermediate Similarity	NPC297179
0.8491	Intermediate Similarity	NPC471253
0.8482	Intermediate Similarity	NPC472718
0.8476	Intermediate Similarity	NPC471790
0.8468	Intermediate Similarity	NPC146563
0.8462	Intermediate Similarity	NPC16911
0.8462	Intermediate Similarity	NPC89099
0.8462	Intermediate Similarity	NPC78427
0.8462	Intermediate Similarity	NPC26270
0.8455	Intermediate Similarity	NPC272242
0.844	Intermediate Similarity	NPC91583
0.844	Intermediate Similarity	NPC473844
0.844	Intermediate Similarity	NPC51947
0.844	Intermediate Similarity	NPC240125
0.8435	Intermediate Similarity	NPC470478
0.8431	Intermediate Similarity	NPC47853
0.8431	Intermediate Similarity	NPC470385
0.8431	Intermediate Similarity	NPC470386
0.8431	Intermediate Similarity	NPC475118
0.8411	Intermediate Similarity	NPC98603
0.8411	Intermediate Similarity	NPC13149
0.8393	Intermediate Similarity	NPC18547
0.8393	Intermediate Similarity	NPC474906
0.8393	Intermediate Similarity	NPC54395
0.8378	Intermediate Similarity	NPC289312
0.8378	Intermediate Similarity	NPC11252
0.8378	Intermediate Similarity	NPC243572
0.8378	Intermediate Similarity	NPC476964
0.8376	Intermediate Similarity	NPC469841
0.8376	Intermediate Similarity	NPC469842
0.8365	Intermediate Similarity	NPC10864
0.8365	Intermediate Similarity	NPC96839
0.8349	Intermediate Similarity	NPC88744
0.8348	Intermediate Similarity	NPC476961
0.8333	Intermediate Similarity	NPC239293
0.8333	Intermediate Similarity	NPC294263
0.8333	Intermediate Similarity	NPC188667
0.8333	Intermediate Similarity	NPC295366
0.8333	Intermediate Similarity	NPC204552
0.8319	Intermediate Similarity	NPC469820
0.8319	Intermediate Similarity	NPC152199
0.8319	Intermediate Similarity	NPC235539
0.8319	Intermediate Similarity	NPC469823
0.8319	Intermediate Similarity	NPC134869
0.8319	Intermediate Similarity	NPC137414
0.8318	Intermediate Similarity	NPC216114
0.8305	Intermediate Similarity	NPC47113
0.8305	Intermediate Similarity	NPC174367
0.8304	Intermediate Similarity	NPC102619
0.8288	Intermediate Similarity	NPC240734
0.8288	Intermediate Similarity	NPC94650
0.8288	Intermediate Similarity	NPC201992
0.8288	Intermediate Similarity	NPC263827
0.8288	Intermediate Similarity	NPC250481
0.8288	Intermediate Similarity	NPC275668
0.8288	Intermediate Similarity	NPC204392
0.8288	Intermediate Similarity	NPC91838
0.8288	Intermediate Similarity	NPC471251
0.8288	Intermediate Similarity	NPC1876
0.8288	Intermediate Similarity	NPC285410
0.8286	Intermediate Similarity	NPC469725
0.8276	Intermediate Similarity	NPC102822
0.8276	Intermediate Similarity	NPC477046

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 NPC137104 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	287
0.1-0.2	2375
0.2-0.3	3938
0.3-0.4	1640
0.4-0.5	466
0.5-0.6	250
0.6-0.7	145
0.7-0.8	46
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8136	Intermediate Similarity	NPD8328	Phase 3
0.8018	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7982	Intermediate Similarity	NPD8133	Approved
0.7946	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD6319	Approved
0.7805	Intermediate Similarity	NPD7319	Approved
0.7769	Intermediate Similarity	NPD7492	Approved
0.7731	Intermediate Similarity	NPD6054	Approved
0.7724	Intermediate Similarity	NPD7736	Approved
0.7705	Intermediate Similarity	NPD6616	Approved
0.7705	Intermediate Similarity	NPD7507	Approved
0.7642	Intermediate Similarity	NPD7078	Approved
0.7611	Intermediate Similarity	NPD6412	Phase 2
0.7603	Intermediate Similarity	NPD6370	Approved
0.7586	Intermediate Similarity	NPD8297	Approved
0.7586	Intermediate Similarity	NPD6882	Approved
0.7583	Intermediate Similarity	NPD6059	Approved
0.7547	Intermediate Similarity	NPD8035	Phase 2
0.7547	Intermediate Similarity	NPD8034	Phase 2
0.7544	Intermediate Similarity	NPD6686	Approved
0.7521	Intermediate Similarity	NPD6016	Approved
0.7521	Intermediate Similarity	NPD6015	Approved
0.7521	Intermediate Similarity	NPD4632	Approved
0.75	Intermediate Similarity	NPD6649	Approved
0.75	Intermediate Similarity	NPD6650	Approved
0.75	Intermediate Similarity	NPD8293	Discontinued
0.7479	Intermediate Similarity	NPD7115	Discovery
0.7479	Intermediate Similarity	NPD6009	Approved
0.7478	Intermediate Similarity	NPD6373	Approved
0.7478	Intermediate Similarity	NPD6372	Approved
0.7459	Intermediate Similarity	NPD5988	Approved
0.7434	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6899	Approved
0.7391	Intermediate Similarity	NPD6881	Approved
0.7377	Intermediate Similarity	NPD6921	Approved
0.7368	Intermediate Similarity	NPD6402	Approved
0.7368	Intermediate Similarity	NPD7128	Approved
0.7368	Intermediate Similarity	NPD5739	Approved
0.7368	Intermediate Similarity	NPD6675	Approved
0.7308	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD5697	Approved
0.7265	Intermediate Similarity	NPD6883	Approved
0.7265	Intermediate Similarity	NPD7290	Approved
0.7265	Intermediate Similarity	NPD7102	Approved
0.7265	Intermediate Similarity	NPD4634	Approved
0.7241	Intermediate Similarity	NPD7320	Approved
0.7213	Intermediate Similarity	NPD7516	Approved
0.7203	Intermediate Similarity	NPD8130	Phase 1
0.7203	Intermediate Similarity	NPD6847	Approved
0.7203	Intermediate Similarity	NPD6617	Approved
0.7203	Intermediate Similarity	NPD6869	Approved
0.7179	Intermediate Similarity	NPD6014	Approved
0.7179	Intermediate Similarity	NPD6012	Approved
0.7179	Intermediate Similarity	NPD6013	Approved
0.7156	Intermediate Similarity	NPD6399	Phase 3
0.7155	Intermediate Similarity	NPD5701	Approved
0.7154	Intermediate Similarity	NPD8294	Approved
0.7154	Intermediate Similarity	NPD8377	Approved
0.7131	Intermediate Similarity	NPD7327	Approved
0.7131	Intermediate Similarity	NPD7328	Approved
0.712	Intermediate Similarity	NPD7604	Phase 2
0.7097	Intermediate Similarity	NPD8033	Approved
0.7097	Intermediate Similarity	NPD8380	Approved
0.7097	Intermediate Similarity	NPD8296	Approved
0.7097	Intermediate Similarity	NPD8378	Approved
0.7097	Intermediate Similarity	NPD8379	Approved
0.7097	Intermediate Similarity	NPD8515	Approved
0.7097	Intermediate Similarity	NPD8513	Phase 3
0.7097	Intermediate Similarity	NPD8516	Approved
0.7097	Intermediate Similarity	NPD5983	Phase 2
0.7097	Intermediate Similarity	NPD8517	Approved
0.7097	Intermediate Similarity	NPD8335	Approved
0.7094	Intermediate Similarity	NPD6011	Approved
0.7069	Intermediate Similarity	NPD6008	Approved
0.7064	Intermediate Similarity	NPD6079	Approved
0.7054	Intermediate Similarity	NPD7902	Approved
0.7037	Intermediate Similarity	NPD5328	Approved
0.7034	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6033	Approved
0.7008	Intermediate Similarity	NPD6336	Discontinued
0.6991	Remote Similarity	NPD7638	Approved
0.6991	Remote Similarity	NPD4225	Approved
0.6975	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.696	Remote Similarity	NPD7503	Approved
0.6937	Remote Similarity	NPD7748	Approved
0.693	Remote Similarity	NPD5286	Approved
0.693	Remote Similarity	NPD7639	Approved
0.693	Remote Similarity	NPD5285	Approved
0.693	Remote Similarity	NPD7640	Approved
0.693	Remote Similarity	NPD4696	Approved
0.6917	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7515	Phase 2
0.6903	Remote Similarity	NPD4755	Approved
0.6829	Remote Similarity	NPD6274	Approved
0.6814	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD4697	Phase 3
0.6814	Remote Similarity	NPD5221	Approved
0.6814	Remote Similarity	NPD5222	Approved
0.681	Remote Similarity	NPD5225	Approved
0.681	Remote Similarity	NPD4633	Approved
0.681	Remote Similarity	NPD5226	Approved
0.681	Remote Similarity	NPD5224	Approved
0.681	Remote Similarity	NPD5211	Phase 2
0.68	Remote Similarity	NPD7101	Approved
0.68	Remote Similarity	NPD7100	Approved
0.6796	Remote Similarity	NPD6114	Approved
0.6796	Remote Similarity	NPD6115	Approved
0.6796	Remote Similarity	NPD6118	Approved
0.6796	Remote Similarity	NPD6697	Approved
0.6786	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7900	Approved
0.6783	Remote Similarity	NPD4700	Approved
0.6759	Remote Similarity	NPD3618	Phase 1
0.6757	Remote Similarity	NPD6411	Approved
0.6754	Remote Similarity	NPD6084	Phase 2
0.6754	Remote Similarity	NPD5173	Approved
0.6754	Remote Similarity	NPD6083	Phase 2
0.6752	Remote Similarity	NPD5174	Approved
0.6752	Remote Similarity	NPD5175	Approved
0.6724	Remote Similarity	NPD5223	Approved
0.6723	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6335	Approved
0.6699	Remote Similarity	NPD6116	Phase 1
0.6697	Remote Similarity	NPD3573	Approved
0.6695	Remote Similarity	NPD5141	Approved
0.6694	Remote Similarity	NPD6868	Approved
0.6692	Remote Similarity	NPD8074	Phase 3
0.6667	Remote Similarity	NPD4729	Approved
0.6667	Remote Similarity	NPD4730	Approved
0.664	Remote Similarity	NPD6317	Approved
0.6639	Remote Similarity	NPD4768	Approved
0.6639	Remote Similarity	NPD4767	Approved
0.6636	Remote Similarity	NPD4788	Approved
0.6602	Remote Similarity	NPD6117	Approved
0.6589	Remote Similarity	NPD6067	Discontinued
0.6587	Remote Similarity	NPD6313	Approved
0.6587	Remote Similarity	NPD6314	Approved
0.6581	Remote Similarity	NPD1700	Approved
0.6577	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6101	Approved
0.6574	Remote Similarity	NPD4786	Approved
0.6562	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6908	Approved
0.6562	Remote Similarity	NPD6909	Approved
0.6557	Remote Similarity	NPD5249	Phase 3
0.6557	Remote Similarity	NPD5250	Approved
0.6557	Remote Similarity	NPD5248	Approved
0.6557	Remote Similarity	NPD6371	Approved
0.6557	Remote Similarity	NPD5251	Approved
0.6557	Remote Similarity	NPD5247	Approved
0.6552	Remote Similarity	NPD5696	Approved
0.6549	Remote Similarity	NPD8171	Discontinued
0.6549	Remote Similarity	NPD4202	Approved
0.6529	Remote Similarity	NPD5128	Approved
0.6525	Remote Similarity	NPD7632	Discontinued
0.6505	Remote Similarity	NPD3703	Phase 2
0.6504	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6672	Approved
0.6486	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD5737	Approved
0.6471	Remote Similarity	NPD4754	Approved
0.646	Remote Similarity	NPD7983	Approved
0.6455	Remote Similarity	NPD7521	Approved
0.6455	Remote Similarity	NPD5330	Approved
0.6455	Remote Similarity	NPD6684	Approved
0.6455	Remote Similarity	NPD7146	Approved
0.6455	Remote Similarity	NPD7334	Approved
0.6455	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6409	Approved
0.6435	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD5695	Phase 3
0.6429	Remote Similarity	NPD6940	Discontinued
0.6418	Remote Similarity	NPD5956	Approved
0.6408	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5778	Approved
0.6404	Remote Similarity	NPD5779	Approved
0.6391	Remote Similarity	NPD8337	Approved
0.6391	Remote Similarity	NPD8336	Approved
0.6389	Remote Similarity	NPD3667	Approved
0.6372	Remote Similarity	NPD46	Approved
0.6372	Remote Similarity	NPD6698	Approved
0.6371	Remote Similarity	NPD5217	Approved
0.6371	Remote Similarity	NPD5215	Approved
0.6371	Remote Similarity	NPD5216	Approved
0.637	Remote Similarity	NPD7260	Phase 2
0.6339	Remote Similarity	NPD6903	Approved
0.6331	Remote Similarity	NPD6334	Approved
0.6331	Remote Similarity	NPD6333	Approved
0.633	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.633	Remote Similarity	NPD3669	Approved
0.6324	Remote Similarity	NPD8338	Approved
0.632	Remote Similarity	NPD6053	Discontinued
0.6316	Remote Similarity	NPD7637	Suspended
0.6296	Remote Similarity	NPD1779	Approved
0.6296	Remote Similarity	NPD1780	Approved
0.6293	Remote Similarity	NPD5210	Approved
0.6293	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD4629	Approved
0.629	Remote Similarity	NPD5169	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