NPASS Compound

Structure

NPC472507 OpenBabel07101718282D 38 40 0 0 1 0 0 0 0 0999 V2000 6.4249 -3.3372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2909 -1.8372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7974 0.9464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3606 0.4378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6928 -2.3372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8268 -1.8372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1617 1.3847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5588 -0.8372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8959 -0.4718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2023 -0.9675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5900 -0.3347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6123 -0.6328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4249 -2.3372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8418 0.6517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5588 -1.8372 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8268 -0.8372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6928 -0.3372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1645 1.3100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6012 0.4837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6235 -0.7818 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1911 -0.8185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9665 0.4471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2581 -1.7127 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7307 -1.8617 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3542 -1.0799 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9888 -0.1490 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5788 -0.1857 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.6645 2.1760 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8146 -1.6003 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5565 0.1124 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3318 1.3780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8816 -2.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0960 -2.7926 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3430 -1.2290 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4298 0.8032 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9777 0.2981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6123 0.6328 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 13 2 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 27 1 0 0 0 0 5 6 1 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 7 14 2 0 0 0 0 7 18 1 0 0 0 0 8 15 1 0 0 0 0 8 17 1 0 0 0 0 9 16 1 0 0 0 0 9 19 2 0 0 0 0 10 21 1 0 0 0 0 10 27 1 0 0 0 0 11 22 1 0 0 0 0 11 27 1 0 0 0 0 12 36 1 0 0 0 0 14 17 1 0 0 0 0 15 13 1 6 0 0 0 16 17 2 0 0 0 0 18 19 1 0 0 0 0 18 28 2 0 0 0 0 19 37 1 0 0 0 0 20 12 1 1 0 0 0 20 23 1 0 0 0 0 20 38 1 0 0 0 0 21 29 2 0 0 0 0 21 30 1 0 0 0 0 22 31 2 0 0 0 0 22 36 1 0 0 0 0 23 24 1 0 0 0 0 23 32 1 6 0 0 0 24 25 1 0 0 0 0 24 33 1 1 0 0 0 25 26 1 0 0 0 0 25 34 1 6 0 0 0 26 37 1 1 0 0 0 26 38 1 0 0 0 0 27 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	536.23
Volume:	528.116
LogP:	0.751
LogD:	0.226
LogS:	-3.573
# Rotatable Bonds:	10
TPSA:	180.05
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.217
Synthetic Accessibility Score:	4.622
Fsp3:	0.593
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.949
MDCK Permeability:	2.1064455722807907e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.959
Human Intestinal Absorption (HIA):	0.891
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.08
Plasma Protein Binding (PPB):	72.77723693847656%
Volume Distribution (VD):	0.182
Pgp-substrate:	15.305384635925293%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.077
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.096
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.698
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.148
CYP3A4-inhibitor:	0.021
CYP3A4-substrate:	0.044

ADMET: Excretion

Clearance (CL):	2.447
Half-life (T1/2):	0.868

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.295
Drug-inuced Liver Injury (DILI):	0.092
AMES Toxicity:	0.085
Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.428
Skin Sensitization:	0.041
Carcinogencity:	0.071
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.014

Download Data

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

Natural Product: NPC472507

Natural Product ID:	NPC472507
*Common Name:**	IBKYMZARVDRFQT-PFQWCQPSSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IBKYMZARVDRFQT-PFQWCQPSSA-N
Standard InCHI:	InChI=1S/C27H36O11/c1-13(2)15-5-6-16-9-19(18(28)7-14(3)17(16)8-15)37-26-25(34)24(33)23(32)20(38-26)12-36-22(31)11-27(4,35)10-21(29)30/h7,9,15,20,23-26,32-35H,1,5-6,8,10-12H2,2-4H3,(H,29,30)/t15-,20-,23-,24+,25-,26-,27?/m1/s1
SMILES:	CC1=CC(=O)C(=CC2=C1CC(CC2)C(=C)C)OC3C(C(C(C(O3)COC(=O)CC(C)(CC(=O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3426555
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003918] Saccharolipids

*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
NPO32551	liriosma ovata	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18197604]
NPO32551	liriosma ovata	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[25587934]

☑ 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	1
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	=	34000.0	nM	PMID[488717]
NPT315	Cell Line	CEM-SS	Homo sapiens	IC50	>	50000.0	nM	PMID[488717]

☑ 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 NPC472507 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	338
0.1-0.2	1274
0.2-0.3	2946
0.3-0.4	6265
0.4-0.5	10679
0.5-0.6	7254
0.6-0.7	8172
0.7-0.8	5677
0.8-0.85	89
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9802	High Similarity	NPC472508
0.7745	Intermediate Similarity	NPC471755
0.7745	Intermediate Similarity	NPC471756
0.7736	Intermediate Similarity	NPC256230
0.7624	Intermediate Similarity	NPC477746
0.7624	Intermediate Similarity	NPC477747
0.7619	Intermediate Similarity	NPC61201
0.7611	Intermediate Similarity	NPC23497
0.7596	Intermediate Similarity	NPC6414
0.7596	Intermediate Similarity	NPC473311
0.7596	Intermediate Similarity	NPC303451
0.7583	Intermediate Similarity	NPC216866
0.7544	Intermediate Similarity	NPC89408
0.7541	Intermediate Similarity	NPC198714
0.7524	Intermediate Similarity	NPC472199
0.7524	Intermediate Similarity	NPC477749
0.7523	Intermediate Similarity	NPC324667
0.7522	Intermediate Similarity	NPC327106
0.7521	Intermediate Similarity	NPC1980
0.7521	Intermediate Similarity	NPC141196
0.7521	Intermediate Similarity	NPC238005
0.7521	Intermediate Similarity	NPC31797
0.7479	Intermediate Similarity	NPC319570
0.7477	Intermediate Similarity	NPC469543
0.7477	Intermediate Similarity	NPC170204
0.7456	Intermediate Similarity	NPC133625
0.7453	Intermediate Similarity	NPC478036
0.7453	Intermediate Similarity	NPC320552
0.7453	Intermediate Similarity	NPC478037
0.7429	Intermediate Similarity	NPC117596
0.7429	Intermediate Similarity	NPC202886
0.7429	Intermediate Similarity	NPC327253
0.7419	Intermediate Similarity	NPC295220
0.7419	Intermediate Similarity	NPC475636
0.7417	Intermediate Similarity	NPC472076
0.7417	Intermediate Similarity	NPC472075
0.7407	Intermediate Similarity	NPC173329
0.7407	Intermediate Similarity	NPC288350
0.7395	Intermediate Similarity	NPC297179
0.7395	Intermediate Similarity	NPC13710
0.7383	Intermediate Similarity	NPC472198
0.7377	Intermediate Similarity	NPC472077
0.7377	Intermediate Similarity	NPC472078
0.7364	Intermediate Similarity	NPC469871
0.7364	Intermediate Similarity	NPC469870
0.7364	Intermediate Similarity	NPC596
0.736	Intermediate Similarity	NPC54614
0.736	Intermediate Similarity	NPC309096
0.7355	Intermediate Similarity	NPC473228
0.7355	Intermediate Similarity	NPC470829
0.7355	Intermediate Similarity	NPC42675
0.7355	Intermediate Similarity	NPC275675
0.7345	Intermediate Similarity	NPC469852
0.7333	Intermediate Similarity	NPC477748
0.7333	Intermediate Similarity	NPC127530
0.7321	Intermediate Similarity	NPC469980
0.7321	Intermediate Similarity	NPC104161
0.7321	Intermediate Similarity	NPC118902
0.7317	Intermediate Similarity	NPC30188
0.7317	Intermediate Similarity	NPC6615
0.7317	Intermediate Similarity	NPC7850
0.7317	Intermediate Similarity	NPC177820
0.7315	Intermediate Similarity	NPC101051
0.7315	Intermediate Similarity	NPC108141
0.7311	Intermediate Similarity	NPC309433
0.7302	Intermediate Similarity	NPC213634
0.7295	Intermediate Similarity	NPC471965
0.729	Intermediate Similarity	NPC472196
0.729	Intermediate Similarity	NPC238090
0.729	Intermediate Similarity	NPC472195
0.7287	Intermediate Similarity	NPC141215
0.7287	Intermediate Similarity	NPC471089
0.7287	Intermediate Similarity	NPC190065
0.7281	Intermediate Similarity	NPC266514
0.7281	Intermediate Similarity	NPC474285
0.7281	Intermediate Similarity	NPC469853
0.7281	Intermediate Similarity	NPC254538
0.7273	Intermediate Similarity	NPC70733
0.7273	Intermediate Similarity	NPC56071
0.7265	Intermediate Similarity	NPC66108
0.7258	Intermediate Similarity	NPC222307
0.7258	Intermediate Similarity	NPC87662
0.7258	Intermediate Similarity	NPC93368
0.7257	Intermediate Similarity	NPC86095
0.7257	Intermediate Similarity	NPC264584
0.725	Intermediate Similarity	NPC475309
0.725	Intermediate Similarity	NPC176005
0.7248	Intermediate Similarity	NPC241911
0.7238	Intermediate Similarity	NPC137368
0.7236	Intermediate Similarity	NPC262199
0.7236	Intermediate Similarity	NPC227397
0.7236	Intermediate Similarity	NPC471961
0.7236	Intermediate Similarity	NPC471964
0.7236	Intermediate Similarity	NPC14617
0.7236	Intermediate Similarity	NPC202666
0.7232	Intermediate Similarity	NPC471599
0.7232	Intermediate Similarity	NPC476126
0.7232	Intermediate Similarity	NPC13171
0.7232	Intermediate Similarity	NPC222062
0.7232	Intermediate Similarity	NPC476235
0.7232	Intermediate Similarity	NPC195510
0.7231	Intermediate Similarity	NPC140045
0.7231	Intermediate Similarity	NPC295885
0.7227	Intermediate Similarity	NPC235539
0.7227	Intermediate Similarity	NPC134869
0.7227	Intermediate Similarity	NPC152199
0.7222	Intermediate Similarity	NPC159698
0.7222	Intermediate Similarity	NPC294293
0.7217	Intermediate Similarity	NPC473288
0.7217	Intermediate Similarity	NPC473807
0.7213	Intermediate Similarity	NPC75417
0.7209	Intermediate Similarity	NPC262813
0.7207	Intermediate Similarity	NPC255677
0.7207	Intermediate Similarity	NPC306344
0.7207	Intermediate Similarity	NPC22149
0.7203	Intermediate Similarity	NPC326264
0.72	Intermediate Similarity	NPC152091
0.7196	Intermediate Similarity	NPC472126
0.7196	Intermediate Similarity	NPC472124
0.7196	Intermediate Similarity	NPC472197
0.7196	Intermediate Similarity	NPC472125
0.719	Intermediate Similarity	NPC470777
0.719	Intermediate Similarity	NPC279143
0.7182	Intermediate Similarity	NPC474194
0.7182	Intermediate Similarity	NPC278506
0.7182	Intermediate Similarity	NPC476612
0.7182	Intermediate Similarity	NPC476613
0.7177	Intermediate Similarity	NPC190846
0.7177	Intermediate Similarity	NPC470922
0.7177	Intermediate Similarity	NPC469842
0.7177	Intermediate Similarity	NPC277191
0.7177	Intermediate Similarity	NPC471963
0.7177	Intermediate Similarity	NPC471962
0.7177	Intermediate Similarity	NPC469841
0.7177	Intermediate Similarity	NPC247315
0.7168	Intermediate Similarity	NPC234304
0.7168	Intermediate Similarity	NPC197736
0.7168	Intermediate Similarity	NPC267869
0.7168	Intermediate Similarity	NPC197541
0.7168	Intermediate Similarity	NPC118761
0.7168	Intermediate Similarity	NPC284929
0.7167	Intermediate Similarity	NPC23046
0.7167	Intermediate Similarity	NPC224121
0.7155	Intermediate Similarity	NPC38154
0.7154	Intermediate Similarity	NPC275343
0.7154	Intermediate Similarity	NPC251998
0.7154	Intermediate Similarity	NPC287236
0.7143	Intermediate Similarity	NPC4637
0.7143	Intermediate Similarity	NPC18547
0.7143	Intermediate Similarity	NPC476213
0.7143	Intermediate Similarity	NPC477870
0.7143	Intermediate Similarity	NPC476611
0.7143	Intermediate Similarity	NPC475037
0.7143	Intermediate Similarity	NPC98859
0.7143	Intermediate Similarity	NPC477871
0.7143	Intermediate Similarity	NPC476246
0.7143	Intermediate Similarity	NPC270109
0.7143	Intermediate Similarity	NPC219038
0.7143	Intermediate Similarity	NPC28304
0.7143	Intermediate Similarity	NPC474906
0.7143	Intermediate Similarity	NPC298255
0.7129	Intermediate Similarity	NPC100697
0.712	Intermediate Similarity	NPC181066
0.712	Intermediate Similarity	NPC285091
0.712	Intermediate Similarity	NPC469947
0.7117	Intermediate Similarity	NPC198422
0.7117	Intermediate Similarity	NPC40182
0.7117	Intermediate Similarity	NPC472015
0.7117	Intermediate Similarity	NPC161855
0.7115	Intermediate Similarity	NPC470177
0.7115	Intermediate Similarity	NPC470124
0.7109	Intermediate Similarity	NPC100390
0.7109	Intermediate Similarity	NPC254614
0.7107	Intermediate Similarity	NPC286347
0.7107	Intermediate Similarity	NPC17772
0.7107	Intermediate Similarity	NPC204552
0.7107	Intermediate Similarity	NPC188667
0.7107	Intermediate Similarity	NPC234522
0.7105	Intermediate Similarity	NPC472748
0.7105	Intermediate Similarity	NPC469869
0.7103	Intermediate Similarity	NPC307699
0.7094	Intermediate Similarity	NPC127153
0.7091	Intermediate Similarity	NPC255410
0.7087	Intermediate Similarity	NPC477077
0.7087	Intermediate Similarity	NPC477079
0.7087	Intermediate Similarity	NPC470913
0.7087	Intermediate Similarity	NPC477076
0.708	Intermediate Similarity	NPC261117
0.708	Intermediate Similarity	NPC310804
0.708	Intermediate Similarity	NPC223834
0.708	Intermediate Similarity	NPC201191
0.708	Intermediate Similarity	NPC39996
0.7075	Intermediate Similarity	NPC201046
0.7073	Intermediate Similarity	NPC187950
0.7073	Intermediate Similarity	NPC278163
0.7069	Intermediate Similarity	NPC193765
0.7069	Intermediate Similarity	NPC264819
0.7064	Intermediate Similarity	NPC96736
0.7064	Intermediate Similarity	NPC25701
0.7064	Intermediate Similarity	NPC178949

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 NPC472507 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	284
0.1-0.2	864
0.2-0.3	1758
0.3-0.4	2546
0.4-0.5	2118
0.5-0.6	1072
0.6-0.7	402
0.7-0.8	105
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
0.7236	Intermediate Similarity	NPD8328	Phase 3
0.7117	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD8080	Discontinued
0.6935	Remote Similarity	NPD8517	Approved
0.6935	Remote Similarity	NPD8516	Approved
0.6935	Remote Similarity	NPD8515	Approved
0.6935	Remote Similarity	NPD8513	Phase 3
0.6923	Remote Similarity	NPD6686	Approved
0.6885	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7983	Approved
0.688	Remote Similarity	NPD6370	Approved
0.6875	Remote Similarity	NPD7736	Approved
0.6838	Remote Similarity	NPD6412	Phase 2
0.6829	Remote Similarity	NPD7641	Discontinued
0.68	Remote Similarity	NPD7503	Approved
0.68	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD8293	Discontinued
0.6789	Remote Similarity	NPD6698	Approved
0.6789	Remote Similarity	NPD46	Approved
0.6772	Remote Similarity	NPD7492	Approved
0.6762	Remote Similarity	NPD6110	Phase 1
0.672	Remote Similarity	NPD6319	Approved
0.672	Remote Similarity	NPD6054	Approved
0.6719	Remote Similarity	NPD6616	Approved
0.6693	Remote Similarity	NPD7830	Approved
0.6693	Remote Similarity	NPD7829	Approved
0.6667	Remote Similarity	NPD7078	Approved
0.6636	Remote Similarity	NPD7838	Discovery
0.6587	Remote Similarity	NPD6059	Approved
0.6557	Remote Similarity	NPD6882	Approved
0.6555	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6015	Approved
0.6535	Remote Similarity	NPD8444	Approved
0.6535	Remote Similarity	NPD6016	Approved
0.6491	Remote Similarity	NPD7839	Suspended
0.6484	Remote Similarity	NPD5988	Approved
0.648	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.648	Remote Similarity	NPD6009	Approved
0.6475	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.646	Remote Similarity	NPD5282	Discontinued
0.6446	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD7319	Approved
0.6434	Remote Similarity	NPD7642	Approved
0.6423	Remote Similarity	NPD8297	Approved
0.6412	Remote Similarity	NPD8074	Phase 3
0.6396	Remote Similarity	NPD6101	Approved
0.6396	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD6371	Approved
0.6385	Remote Similarity	NPD8340	Approved
0.6385	Remote Similarity	NPD8342	Approved
0.6385	Remote Similarity	NPD8341	Approved
0.6385	Remote Similarity	NPD8299	Approved
0.6372	Remote Similarity	NPD5778	Approved
0.6372	Remote Similarity	NPD5779	Approved
0.6336	Remote Similarity	NPD8451	Approved
0.6336	Remote Similarity	NPD7507	Approved
0.629	Remote Similarity	NPD6053	Discontinued
0.6288	Remote Similarity	NPD8448	Approved
0.6283	Remote Similarity	NPD6411	Approved
0.6241	Remote Similarity	NPD8337	Approved
0.6241	Remote Similarity	NPD8336	Approved
0.624	Remote Similarity	NPD4632	Approved
0.623	Remote Similarity	NPD6881	Approved
0.623	Remote Similarity	NPD6899	Approved
0.6222	Remote Similarity	NPD7260	Phase 2
0.621	Remote Similarity	NPD6649	Approved
0.621	Remote Similarity	NPD6650	Approved
0.6198	Remote Similarity	NPD6675	Approved
0.6198	Remote Similarity	NPD7128	Approved
0.6198	Remote Similarity	NPD5739	Approved
0.6198	Remote Similarity	NPD6402	Approved
0.619	Remote Similarity	NPD4756	Discovery
0.6179	Remote Similarity	NPD6373	Approved
0.6179	Remote Similarity	NPD6372	Approved
0.6172	Remote Similarity	NPD7328	Approved
0.6172	Remote Similarity	NPD7327	Approved
0.6154	Remote Similarity	NPD8033	Approved
0.6154	Remote Similarity	NPD6083	Phase 2
0.6154	Remote Similarity	NPD6084	Phase 2
0.6148	Remote Similarity	NPD8390	Approved
0.6148	Remote Similarity	NPD8392	Approved
0.6148	Remote Similarity	NPD8391	Approved
0.6148	Remote Similarity	NPD5697	Approved
0.6129	Remote Similarity	NPD6883	Approved
0.6129	Remote Similarity	NPD7102	Approved
0.6129	Remote Similarity	NPD7290	Approved
0.6124	Remote Similarity	NPD7516	Approved
0.6119	Remote Similarity	NPD6033	Approved
0.6098	Remote Similarity	NPD7320	Approved
0.6098	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.608	Remote Similarity	NPD6847	Approved
0.608	Remote Similarity	NPD6869	Approved
0.608	Remote Similarity	NPD8130	Phase 1
0.608	Remote Similarity	NPD6617	Approved
0.6077	Remote Similarity	NPD8294	Approved
0.6077	Remote Similarity	NPD8377	Approved
0.6061	Remote Similarity	NPD7604	Phase 2
0.6048	Remote Similarity	NPD6014	Approved
0.6048	Remote Similarity	NPD6013	Approved
0.6048	Remote Similarity	NPD6012	Approved
0.6031	Remote Similarity	NPD5983	Phase 2
0.6031	Remote Similarity	NPD8378	Approved
0.6031	Remote Similarity	NPD8379	Approved
0.6031	Remote Similarity	NPD8296	Approved
0.6031	Remote Similarity	NPD8380	Approved
0.6031	Remote Similarity	NPD8335	Approved
0.6029	Remote Similarity	NPD5956	Approved
0.6016	Remote Similarity	NPD5701	Approved
0.6	Remote Similarity	NPD4634	Approved
0.6	Remote Similarity	NPD7637	Suspended
0.5984	Remote Similarity	NPD8133	Approved
0.5983	Remote Similarity	NPD5695	Phase 3
0.597	Remote Similarity	NPD6336	Discontinued
0.5969	Remote Similarity	NPD7115	Discovery
0.5968	Remote Similarity	NPD6011	Approved
0.5966	Remote Similarity	NPD4225	Approved
0.5966	Remote Similarity	NPD5696	Approved
0.5946	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5942	Remote Similarity	NPD6845	Suspended
0.5929	Remote Similarity	NPD4250	Approved
0.5929	Remote Similarity	NPD4251	Approved
0.5926	Remote Similarity	NPD7329	Approved
0.5872	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD5344	Discontinued
0.5847	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5846	Remote Similarity	NPD7500	Approved
0.5841	Remote Similarity	NPD4249	Approved
0.5833	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD8338	Approved
0.5826	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD6648	Approved
0.5784	Remote Similarity	NPD897	Approved
0.5784	Remote Similarity	NPD898	Approved
0.5784	Remote Similarity	NPD896	Approved
0.5772	Remote Similarity	NPD1407	Approved
0.5769	Remote Similarity	NPD6274	Approved
0.5758	Remote Similarity	NPD7101	Approved
0.5758	Remote Similarity	NPD7100	Approved
0.5739	Remote Similarity	NPD5737	Approved
0.5739	Remote Similarity	NPD6672	Approved
0.5735	Remote Similarity	NPD8273	Phase 1
0.5726	Remote Similarity	NPD6050	Approved
0.5714	Remote Similarity	NPD7154	Phase 3
0.5704	Remote Similarity	NPD6067	Discontinued
0.5704	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD7638	Approved
0.5691	Remote Similarity	NPD8082	Approved
0.5691	Remote Similarity	NPD8084	Approved
0.5691	Remote Similarity	NPD8083	Approved
0.5691	Remote Similarity	NPD8139	Approved
0.5691	Remote Similarity	NPD8085	Approved
0.5691	Remote Similarity	NPD8138	Approved
0.5691	Remote Similarity	NPD8086	Approved
0.5686	Remote Similarity	NPD3704	Approved
0.5682	Remote Similarity	NPD6335	Approved
0.5678	Remote Similarity	NPD6399	Phase 3
0.5676	Remote Similarity	NPD5369	Approved
0.5672	Remote Similarity	NPD6921	Approved
0.5669	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.566	Remote Similarity	NPD3181	Approved
0.5656	Remote Similarity	NPD7640	Approved
0.5656	Remote Similarity	NPD7639	Approved
0.5656	Remote Similarity	NPD4696	Approved
0.5656	Remote Similarity	NPD5286	Approved
0.5656	Remote Similarity	NPD5285	Approved
0.5645	Remote Similarity	NPD8275	Approved
0.5645	Remote Similarity	NPD8276	Approved
0.5641	Remote Similarity	NPD5692	Phase 3
0.5634	Remote Similarity	NPD8415	Approved
0.563	Remote Similarity	NPD7748	Approved
0.5625	Remote Similarity	NPD5209	Approved
0.5625	Remote Similarity	NPD6435	Approved
0.562	Remote Similarity	NPD4755	Approved
0.562	Remote Similarity	NPD7902	Approved
0.5614	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD5363	Approved
0.5614	Remote Similarity	NPD1696	Phase 3
0.561	Remote Similarity	NPD7799	Discontinued
0.5606	Remote Similarity	NPD6317	Approved
0.56	Remote Similarity	NPD8081	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