NPASS Compound

Structure

NPC472618 OpenBabel07101718242D 30 34 0 0 1 0 0 0 0 0999 V2000 3.7229 -1.0341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2575 -2.6088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 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 23 1 0 0 0 0 2 23 1 0 0 0 0 5 8 1 0 0 0 0 5 19 1 0 0 0 0 6 7 2 0 0 0 0 6 21 1 0 0 0 0 7 24 1 0 0 0 0 8 25 1 0 0 0 0 9 13 1 0 0 0 0 9 15 1 0 0 0 0 10 13 1 0 0 0 0 10 16 1 0 0 0 0 11 14 1 0 0 0 0 11 20 1 0 0 0 0 12 17 1 0 0 0 0 12 18 2 0 0 0 0 13 26 1 1 0 0 0 14 15 2 0 0 0 0 14 18 1 0 0 0 0 15 22 1 0 0 0 0 16 22 1 0 0 0 0 16 27 2 0 0 0 0 17 22 2 0 0 0 0 17 28 1 0 0 0 0 18 30 1 0 0 0 0 19 23 1 0 0 0 0 19 24 1 1 0 0 0 20 24 1 6 0 0 0 20 25 1 0 0 0 0 21 23 1 0 0 0 0 21 29 2 0 0 0 0 24 3 1 1 0 0 0 25 4 1 6 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	410.21
Volume:	426.306
LogP:	4.901
LogD:	3.103
LogS:	-6.417
# Rotatable Bonds:	0
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.68
Synthetic Accessibility Score:	4.735
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.15
MDCK Permeability:	1.774729389580898e-05
Pgp-inhibitor:	0.066
Pgp-substrate:	0.62
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.089
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.303
Plasma Protein Binding (PPB):	91.10089874267578%
Volume Distribution (VD):	0.572
Pgp-substrate:	7.130544662475586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.218
CYP1A2-substrate:	0.842
CYP2C19-inhibitor:	0.1
CYP2C19-substrate:	0.664
CYP2C9-inhibitor:	0.325
CYP2C9-substrate:	0.361
CYP2D6-inhibitor:	0.493
CYP2D6-substrate:	0.091
CYP3A4-inhibitor:	0.822
CYP3A4-substrate:	0.785

ADMET: Excretion

Clearance (CL):	13.084
Half-life (T1/2):	0.145

ADMET: Toxicity

hERG Blockers:	0.248
Human Hepatotoxicity (H-HT):	0.249
Drug-inuced Liver Injury (DILI):	0.071
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.478
Maximum Recommended Daily Dose:	0.962
Skin Sensitization:	0.37
Carcinogencity:	0.922
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC472618

Natural Product ID:	NPC472618
*Common Name:**	LLZGCNVJOFHLTD-TWJITQDPSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LLZGCNVJOFHLTD-TWJITQDPSA-N
Standard InCHI:	InChI=1S/C25H30O5/c1-23(2)19-5-8-25(4)20(24(19,3)7-6-21(23)29)11-14-15-9-13(26)10-16(27)22(15)17(28)12-18(14)30-25/h6-7,12-13,19-20,26,28H,5,8-11H2,1-4H3/t13-,19+,20+,24+,25+/m1/s1
SMILES:	O[C@H]1CC(=O)c2c(C1)c1C[C@@H]3[C@](Oc1cc2O)(C)CC[C@@H]1[C@]3(C)C=CC(=O)C1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581313
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] 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
NPO32870	penicillium funiculosum gwt2-24	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26046820]

☑ 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	5
MIC	2

Activity Type	# Activity
Cell Line	4
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	50000.0	nM	PMID[493847]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	50000.0	nM	PMID[493847]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	50000.0	nM	PMID[493847]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[493847]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	600.0	ug.mL-1	PMID[493847]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	600.0	ug.mL-1	PMID[493847]
NPT1453	Organism	Influenza A virus (A/PR/8/34(H1N1))	Influenza A virus (A/Puerto Rico/8/1934(H1N1))	IC50	>	200000.0	nM	PMID[493847]

☑ 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 NPC472618 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	402
0.1-0.2	1544
0.2-0.3	3062
0.3-0.4	7238
0.4-0.5	10835
0.5-0.6	4736
0.6-0.7	5564
0.7-0.8	6646
0.8-0.85	2131
0.85-0.9	503
0.9-0.95	33
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9673	High Similarity	NPC472617
0.9613	High Similarity	NPC473022
0.9434	High Similarity	NPC472619
0.9355	High Similarity	NPC272196
0.9317	High Similarity	NPC472620
0.9281	High Similarity	NPC305965
0.9281	High Similarity	NPC470675
0.9281	High Similarity	NPC473131
0.925	High Similarity	NPC472622
0.9202	High Similarity	NPC294149
0.9187	High Similarity	NPC472621
0.9182	High Similarity	NPC469395
0.9177	High Similarity	NPC18380
0.9177	High Similarity	NPC137232
0.9172	High Similarity	NPC195167
0.9139	High Similarity	NPC117716
0.9139	High Similarity	NPC470673
0.9139	High Similarity	NPC470674
0.9114	High Similarity	NPC292863
0.9114	High Similarity	NPC184326
0.9097	High Similarity	NPC87708
0.9079	High Similarity	NPC473132
0.9079	High Similarity	NPC473135
0.9079	High Similarity	NPC470676
0.9068	High Similarity	NPC125465
0.9062	High Similarity	NPC290160
0.9062	High Similarity	NPC100849
0.9051	High Similarity	NPC105584
0.9038	High Similarity	NPC329844
0.9032	High Similarity	NPC72958
0.9032	High Similarity	NPC474417
0.9032	High Similarity	NPC149526
0.9032	High Similarity	NPC478148
0.9032	High Similarity	NPC232645
0.9026	High Similarity	NPC473016
0.902	High Similarity	NPC10990
0.902	High Similarity	NPC300988
0.9	High Similarity	NPC475106
0.9	High Similarity	NPC15374
0.8994	High Similarity	NPC195136
0.8974	High Similarity	NPC470340
0.8974	High Similarity	NPC154683
0.8974	High Similarity	NPC40356
0.8968	High Similarity	NPC472633
0.8961	High Similarity	NPC106328
0.8961	High Similarity	NPC35150
0.8957	High Similarity	NPC286074
0.8957	High Similarity	NPC54903
0.8954	High Similarity	NPC477955
0.8951	High Similarity	NPC251336
0.8951	High Similarity	NPC85047
0.8951	High Similarity	NPC17274
0.8951	High Similarity	NPC120857
0.8944	High Similarity	NPC12461
0.8944	High Similarity	NPC476295
0.8931	High Similarity	NPC186113
0.8931	High Similarity	NPC4950
0.8931	High Similarity	NPC15815
0.8924	High Similarity	NPC78492
0.8924	High Similarity	NPC4547
0.8924	High Similarity	NPC208152
0.8917	High Similarity	NPC472799
0.8917	High Similarity	NPC210942
0.8917	High Similarity	NPC169990
0.891	High Similarity	NPC178484
0.891	High Similarity	NPC470569
0.8903	High Similarity	NPC329933
0.8903	High Similarity	NPC10027
0.8903	High Similarity	NPC471114
0.8903	High Similarity	NPC65775
0.8896	High Similarity	NPC473077
0.8896	High Similarity	NPC296998
0.8896	High Similarity	NPC110303
0.8896	High Similarity	NPC23728
0.8896	High Similarity	NPC225419
0.8889	High Similarity	NPC316262
0.8889	High Similarity	NPC131568
0.8889	High Similarity	NPC131579
0.8889	High Similarity	NPC473013
0.8889	High Similarity	NPC209040
0.8889	High Similarity	NPC271288
0.8889	High Similarity	NPC314653
0.8889	High Similarity	NPC473015
0.8882	High Similarity	NPC473961
0.8882	High Similarity	NPC206605
0.8868	High Similarity	NPC475184
0.8868	High Similarity	NPC196448
0.8868	High Similarity	NPC281137
0.8868	High Similarity	NPC282390
0.8868	High Similarity	NPC257166
0.8868	High Similarity	NPC158542
0.8861	High Similarity	NPC55662
0.8861	High Similarity	NPC166054
0.8854	High Similarity	NPC180944
0.8854	High Similarity	NPC113608
0.8854	High Similarity	NPC474843
0.8854	High Similarity	NPC470338
0.8854	High Similarity	NPC268992
0.8854	High Similarity	NPC470337
0.8854	High Similarity	NPC51824
0.8846	High Similarity	NPC255641
0.8846	High Similarity	NPC470568
0.8846	High Similarity	NPC202595
0.8846	High Similarity	NPC150928
0.8846	High Similarity	NPC188403
0.8846	High Similarity	NPC290954
0.8846	High Similarity	NPC471115
0.8846	High Similarity	NPC29777
0.8841	High Similarity	NPC300307
0.8841	High Similarity	NPC20734
0.8839	High Similarity	NPC39195
0.8839	High Similarity	NPC6511
0.8839	High Similarity	NPC160821
0.8839	High Similarity	NPC132592
0.8839	High Similarity	NPC161191
0.8834	High Similarity	NPC178173
0.8834	High Similarity	NPC469394
0.8834	High Similarity	NPC272502
0.8831	High Similarity	NPC127059
0.8831	High Similarity	NPC301276
0.8831	High Similarity	NPC470131
0.8831	High Similarity	NPC20488
0.8831	High Similarity	NPC312973
0.8831	High Similarity	NPC67805
0.8831	High Similarity	NPC142405
0.8831	High Similarity	NPC176229
0.8831	High Similarity	NPC290133
0.8831	High Similarity	NPC88964
0.8831	High Similarity	NPC24136
0.8831	High Similarity	NPC470134
0.8831	High Similarity	NPC111786
0.8831	High Similarity	NPC187282
0.8831	High Similarity	NPC246948
0.8831	High Similarity	NPC285630
0.8831	High Similarity	NPC83357
0.8831	High Similarity	NPC470133
0.8831	High Similarity	NPC109183
0.8831	High Similarity	NPC54577
0.8831	High Similarity	NPC195621
0.8831	High Similarity	NPC472629
0.8831	High Similarity	NPC470647
0.8831	High Similarity	NPC196114
0.8831	High Similarity	NPC267375
0.8831	High Similarity	NPC475052
0.8831	High Similarity	NPC214774
0.8831	High Similarity	NPC470132
0.8831	High Similarity	NPC473078
0.8827	High Similarity	NPC473009
0.8824	High Similarity	NPC221432
0.8824	High Similarity	NPC107177
0.8824	High Similarity	NPC257097
0.8824	High Similarity	NPC143896
0.8824	High Similarity	NPC106985
0.8824	High Similarity	NPC75049
0.8824	High Similarity	NPC278249
0.8824	High Similarity	NPC316816
0.8824	High Similarity	NPC175504
0.8824	High Similarity	NPC77794
0.8824	High Similarity	NPC223812
0.8824	High Similarity	NPC68104
0.8824	High Similarity	NPC310130
0.8824	High Similarity	NPC166138
0.8824	High Similarity	NPC149026
0.8824	High Similarity	NPC18585
0.8824	High Similarity	NPC81697
0.8824	High Similarity	NPC214166
0.8824	High Similarity	NPC150408
0.8824	High Similarity	NPC169591
0.8824	High Similarity	NPC91560
0.8824	High Similarity	NPC478086
0.8824	High Similarity	NPC39329
0.8824	High Similarity	NPC164980
0.8824	High Similarity	NPC85162
0.8824	High Similarity	NPC125894
0.882	High Similarity	NPC312273
0.882	High Similarity	NPC301256
0.882	High Similarity	NPC472906
0.8816	High Similarity	NPC96692
0.8812	High Similarity	NPC51247
0.8812	High Similarity	NPC239118
0.8812	High Similarity	NPC474373
0.8805	High Similarity	NPC164427
0.8797	High Similarity	NPC95842
0.8797	High Similarity	NPC280530
0.8797	High Similarity	NPC7989
0.8797	High Similarity	NPC178964
0.8797	High Similarity	NPC472583
0.8797	High Similarity	NPC121568
0.8797	High Similarity	NPC223701
0.8797	High Similarity	NPC135522
0.8795	High Similarity	NPC469393
0.879	High Similarity	NPC316960
0.879	High Similarity	NPC204561
0.879	High Similarity	NPC132990
0.879	High Similarity	NPC263384
0.879	High Similarity	NPC471676
0.879	High Similarity	NPC472422
0.879	High Similarity	NPC309512
0.879	High Similarity	NPC317715
0.879	High Similarity	NPC46882

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 NPC472618 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	353
0.1-0.2	952
0.2-0.3	1669
0.3-0.4	2562
0.4-0.5	2006
0.5-0.6	991
0.6-0.7	437
0.7-0.8	150
0.8-0.85	27
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8938	High Similarity	NPD6959	Discontinued
0.8742	High Similarity	NPD8443	Clinical (unspecified phase)
0.8679	High Similarity	NPD7819	Suspended
0.8562	High Similarity	NPD2393	Clinical (unspecified phase)
0.8526	High Similarity	NPD7410	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD1549	Phase 2
0.8491	Intermediate Similarity	NPD4380	Phase 2
0.8438	Intermediate Similarity	NPD7411	Suspended
0.8431	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8431	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8408	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6166	Phase 2
0.8323	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD7075	Discontinued
0.8284	Intermediate Similarity	NPD5844	Phase 1
0.8272	Intermediate Similarity	NPD1934	Approved
0.8247	Intermediate Similarity	NPD2796	Approved
0.8247	Intermediate Similarity	NPD6100	Approved
0.8247	Intermediate Similarity	NPD6099	Approved
0.8221	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD2800	Approved
0.8193	Intermediate Similarity	NPD5494	Approved
0.8182	Intermediate Similarity	NPD1510	Phase 2
0.8182	Intermediate Similarity	NPD3749	Approved
0.8182	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD6801	Discontinued
0.8153	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD3750	Approved
0.8141	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD7768	Phase 2
0.807	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD2532	Approved
0.8063	Intermediate Similarity	NPD2534	Approved
0.8063	Intermediate Similarity	NPD2533	Approved
0.8059	Intermediate Similarity	NPD7473	Discontinued
0.8052	Intermediate Similarity	NPD6651	Approved
0.8052	Intermediate Similarity	NPD1607	Approved
0.8039	Intermediate Similarity	NPD1240	Approved
0.8037	Intermediate Similarity	NPD6599	Discontinued
0.8023	Intermediate Similarity	NPD7074	Phase 3
0.7988	Intermediate Similarity	NPD6232	Discontinued
0.7975	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD7054	Approved
0.795	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD6559	Discontinued
0.7919	Intermediate Similarity	NPD7472	Approved
0.7904	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD3882	Suspended
0.7892	Intermediate Similarity	NPD2801	Approved
0.7888	Intermediate Similarity	NPD1511	Approved
0.7888	Intermediate Similarity	NPD7390	Discontinued
0.7874	Intermediate Similarity	NPD6797	Phase 2
0.7866	Intermediate Similarity	NPD3226	Approved
0.7862	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD8313	Approved
0.7841	Intermediate Similarity	NPD8312	Approved
0.7834	Intermediate Similarity	NPD3748	Approved
0.7829	Intermediate Similarity	NPD7251	Discontinued
0.7812	Intermediate Similarity	NPD4628	Phase 3
0.7803	Intermediate Similarity	NPD3751	Discontinued
0.7803	Intermediate Similarity	NPD3818	Discontinued
0.7792	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6273	Approved
0.7791	Intermediate Similarity	NPD1512	Approved
0.7784	Intermediate Similarity	NPD7808	Phase 3
0.7778	Intermediate Similarity	NPD6799	Approved
0.7736	Intermediate Similarity	NPD2346	Discontinued
0.7709	Intermediate Similarity	NPD8150	Discontinued
0.7702	Intermediate Similarity	NPD7003	Approved
0.7684	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD5761	Phase 2
0.7679	Intermediate Similarity	NPD5760	Phase 2
0.7673	Intermediate Similarity	NPD1551	Phase 2
0.7673	Intermediate Similarity	NPD2935	Discontinued
0.767	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD4908	Phase 1
0.7651	Intermediate Similarity	NPD7458	Discontinued
0.7636	Intermediate Similarity	NPD5403	Approved
0.7634	Intermediate Similarity	NPD6782	Approved
0.7634	Intermediate Similarity	NPD6778	Approved
0.7634	Intermediate Similarity	NPD6777	Approved
0.7634	Intermediate Similarity	NPD6776	Approved
0.7634	Intermediate Similarity	NPD6781	Approved
0.7634	Intermediate Similarity	NPD6779	Approved
0.7634	Intermediate Similarity	NPD6780	Approved
0.7633	Intermediate Similarity	NPD5402	Approved
0.7633	Intermediate Similarity	NPD3817	Phase 2
0.7613	Intermediate Similarity	NPD4625	Phase 3
0.761	Intermediate Similarity	NPD2799	Discontinued
0.7584	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD1465	Phase 2
0.7572	Intermediate Similarity	NPD3787	Discontinued
0.7572	Intermediate Similarity	NPD5710	Approved
0.7572	Intermediate Similarity	NPD5711	Approved
0.7554	Intermediate Similarity	NPD4363	Phase 3
0.7554	Intermediate Similarity	NPD4360	Phase 2
0.7532	Intermediate Similarity	NPD5124	Phase 1
0.7532	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD920	Approved
0.7527	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD5401	Approved
0.7514	Intermediate Similarity	NPD8434	Phase 2
0.7513	Intermediate Similarity	NPD7697	Approved
0.7513	Intermediate Similarity	NPD7698	Approved
0.7513	Intermediate Similarity	NPD7696	Phase 3
0.7513	Intermediate Similarity	NPD7435	Discontinued
0.7485	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7871	Phase 2
0.7474	Intermediate Similarity	NPD7870	Phase 2
0.7472	Intermediate Similarity	NPD5953	Discontinued
0.7458	Intermediate Similarity	NPD7286	Phase 2
0.7453	Intermediate Similarity	NPD5408	Approved
0.7453	Intermediate Similarity	NPD5406	Approved
0.7453	Intermediate Similarity	NPD5404	Approved
0.7453	Intermediate Similarity	NPD5405	Approved
0.7452	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD4749	Approved
0.7423	Intermediate Similarity	NPD1243	Approved
0.7409	Intermediate Similarity	NPD8151	Discontinued
0.7407	Intermediate Similarity	NPD2344	Approved
0.7394	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7229	Phase 3
0.7368	Intermediate Similarity	NPD6823	Phase 2
0.7366	Intermediate Similarity	NPD6535	Approved
0.7366	Intermediate Similarity	NPD6534	Approved
0.7358	Intermediate Similarity	NPD7701	Phase 2
0.7355	Intermediate Similarity	NPD1470	Approved
0.7354	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7801	Approved
0.7333	Intermediate Similarity	NPD7783	Phase 2
0.732	Intermediate Similarity	NPD1610	Phase 2
0.732	Intermediate Similarity	NPD1201	Approved
0.732	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD7199	Phase 2
0.731	Intermediate Similarity	NPD37	Approved
0.7308	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD7228	Approved
0.7303	Intermediate Similarity	NPD7177	Discontinued
0.7299	Intermediate Similarity	NPD919	Approved
0.7287	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7033	Discontinued
0.7283	Intermediate Similarity	NPD4966	Approved
0.7283	Intermediate Similarity	NPD4965	Approved
0.7283	Intermediate Similarity	NPD4967	Phase 2
0.7282	Intermediate Similarity	NPD7874	Approved
0.7282	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8166	Discontinued
0.7268	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD943	Approved
0.7249	Intermediate Similarity	NPD7700	Phase 2
0.7249	Intermediate Similarity	NPD7699	Phase 2
0.7243	Intermediate Similarity	NPD4287	Approved
0.7234	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD4361	Phase 2
0.7233	Intermediate Similarity	NPD2313	Discontinued
0.7232	Intermediate Similarity	NPD3926	Phase 2
0.7229	Intermediate Similarity	NPD2309	Approved
0.7225	Intermediate Similarity	NPD4288	Approved
0.7216	Intermediate Similarity	NPD8127	Discontinued
0.7216	Intermediate Similarity	NPD1247	Approved
0.7202	Intermediate Similarity	NPD8320	Phase 1
0.7202	Intermediate Similarity	NPD8319	Approved
0.72	Intermediate Similarity	NPD6234	Discontinued
0.7197	Intermediate Similarity	NPD2798	Approved
0.7161	Intermediate Similarity	NPD3972	Approved
0.7151	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1613	Approved
0.7143	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4140	Approved
0.7143	Intermediate Similarity	NPD6104	Discontinued
0.7135	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1203	Approved
0.7128	Intermediate Similarity	NPD7584	Approved
0.7125	Intermediate Similarity	NPD3268	Approved
0.7125	Intermediate Similarity	NPD3764	Approved
0.7118	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD6844	Discontinued
0.7108	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6832	Phase 2
0.7102	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD1471	Phase 3
0.7083	Intermediate Similarity	NPD7236	Approved
0.7081	Intermediate Similarity	NPD8032	Phase 2
0.7073	Intermediate Similarity	NPD4308	Phase 3
0.7073	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD8455	Phase 2
0.7051	Intermediate Similarity	NPD9717	Approved
0.7051	Intermediate Similarity	NPD1608	Approved
0.7049	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD2861	Phase 2
0.7037	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6213	Phase 3

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