NPASS Compound

Structure

CID307780 OpenBabel06191716112D 42 44 0 0 0 0 0 0 0 0999 V2000 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 6.0000 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 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 5.0000 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 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 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 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -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 -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 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 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 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 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 -0.8660 0.5000 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 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 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 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 5 1 0 0 0 0 3 6 1 0 0 0 0 4 7 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 8 1 0 0 0 0 8 11 1 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 20 2 0 0 0 0 12 21 1 0 0 0 0 13 18 2 0 0 0 0 13 22 1 0 0 0 0 14 19 2 0 0 0 0 14 23 1 0 0 0 0 15 21 2 0 0 0 0 15 24 1 0 0 0 0 16 22 2 0 0 0 0 16 25 1 0 0 0 0 17 23 2 0 0 0 0 17 26 1 0 0 0 0 18 27 1 0 0 0 0 19 28 1 0 0 0 0 20 29 1 0 0 0 0 21 33 1 0 0 0 0 22 41 1 0 0 0 0 23 42 1 0 0 0 0 24 29 2 0 0 0 0 24 34 1 0 0 0 0 25 27 2 0 0 0 0 25 35 1 0 0 0 0 26 28 2 0 0 0 0 26 36 1 0 0 0 0 27 30 1 0 0 0 0 28 31 1 0 0 0 0 29 32 1 0 0 0 0 30 37 2 0 0 0 0 30 38 1 0 0 0 0 31 39 2 0 0 0 0 31 41 1 0 0 0 0 32 40 2 0 0 0 0 32 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	580.23
Volume:	592.623
LogP:	7.723
LogD:	4.682
LogS:	-2.459
# Rotatable Bonds:	15
TPSA:	170.82
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.088
Synthetic Accessibility Score:	3.083
Fsp3:	0.344
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.802
MDCK Permeability:	2.1994290364091285e-05
Pgp-inhibitor:	0.054
Pgp-substrate:	0.04
Human Intestinal Absorption (HIA):	0.758
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	101.19908905029297%
Volume Distribution (VD):	0.349
Pgp-substrate:	0.2724341154098511%

ADMET: Metabolism

CYP1A2-inhibitor:	0.74
CYP1A2-substrate:	0.125
CYP2C19-inhibitor:	0.36
CYP2C19-substrate:	0.042
CYP2C9-inhibitor:	0.562
CYP2C9-substrate:	0.196
CYP2D6-inhibitor:	0.482
CYP2D6-substrate:	0.13
CYP3A4-inhibitor:	0.128
CYP3A4-substrate:	0.009

ADMET: Excretion

Clearance (CL):	4.042
Half-life (T1/2):	0.771

ADMET: Toxicity

hERG Blockers:	0.27
Human Hepatotoxicity (H-HT):	0.203
Drug-inuced Liver Injury (DILI):	0.968
AMES Toxicity:	0.044
Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.905
Carcinogencity:	0.02
Eye Corrosion:	0.003
Eye Irritation:	0.877
Respiratory Toxicity:	0.121

Download Data

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

Natural Product: NPC307780

Natural Product ID:	NPC307780
*Common Name:**	Cytonic Acid A
IUPAC Name:	4-[4-(2,4-dihydroxy-6-pentylbenzoyl)oxy-2-hydroxy-6-propylbenzoyl]oxy-2-hydroxy-6-propylbenzoic acid
Synonyms:
Standard InCHIKey:	SQZYUOYBTIOEEA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C32H36O10/c1-4-7-8-11-20-12-21(33)15-24(34)29(20)32(40)42-23-14-19(10-6-3)28(26(36)17-23)31(39)41-22-13-18(9-5-2)27(30(37)38)25(35)16-22/h12-17,33-36H,4-11H2,1-3H3,(H,37,38)
SMILES:	CCCCCc1cc(cc(c1C(=O)Oc1cc(CCC)c(c(c1)O)C(=O)Oc1cc(CCC)c(c(c1)O)C(=O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL444424
PubChem CID:	491708
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001645] Depsides and depsidones

*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
NPO30188	Cytonaema	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(02)00083-7]
NPO30188	Cytonaema	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10843568]

☑ 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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	43000.0	nM	PMID[516702]

☑ 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 NPC307780 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	373
0.1-0.2	1648
0.2-0.3	3921
0.3-0.4	9513
0.4-0.5	8854
0.5-0.6	3477
0.6-0.7	5407
0.7-0.8	5996
0.8-0.85	2667
0.85-0.9	790
0.9-0.95	41
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC309979
0.979	High Similarity	NPC12305
0.965	High Similarity	NPC29577
0.9583	High Similarity	NPC237208
0.9521	High Similarity	NPC6923
0.9514	High Similarity	NPC134621
0.9456	High Similarity	NPC60413
0.9444	High Similarity	NPC95123
0.9444	High Similarity	NPC66404
0.9441	High Similarity	NPC105648
0.94	High Similarity	NPC146211
0.9379	High Similarity	NPC32470
0.9371	High Similarity	NPC220106
0.9324	High Similarity	NPC475460
0.932	High Similarity	NPC105415
0.9315	High Similarity	NPC267509
0.9262	High Similarity	NPC133856
0.9257	High Similarity	NPC291049
0.9257	High Similarity	NPC233267
0.9195	High Similarity	NPC194379
0.9189	High Similarity	NPC221352
0.9172	High Similarity	NPC250755
0.9133	High Similarity	NPC227166
0.9128	High Similarity	NPC476684
0.911	High Similarity	NPC310340
0.9103	High Similarity	NPC275734
0.9079	High Similarity	NPC149618
0.9079	High Similarity	NPC89625
0.9073	High Similarity	NPC217447
0.9073	High Similarity	NPC273483
0.9026	High Similarity	NPC474373
0.9007	High Similarity	NPC478148
0.9	High Similarity	NPC473978
0.8993	High Similarity	NPC125801
0.8987	High Similarity	NPC76647
0.8986	High Similarity	NPC312789
0.8981	High Similarity	NPC7752
0.8973	High Similarity	NPC67650
0.8973	High Similarity	NPC1704
0.894	High Similarity	NPC473466
0.894	High Similarity	NPC470107
0.894	High Similarity	NPC295036
0.894	High Similarity	NPC150928
0.8933	High Similarity	NPC35150
0.8933	High Similarity	NPC37139
0.8933	High Similarity	NPC106328
0.8926	High Similarity	NPC225173
0.8926	High Similarity	NPC154217
0.8926	High Similarity	NPC163846
0.8926	High Similarity	NPC181388
0.8924	High Similarity	NPC30027
0.8903	High Similarity	NPC55443
0.8903	High Similarity	NPC18699
0.8896	High Similarity	NPC54928
0.8889	High Similarity	NPC472799
0.8882	High Similarity	NPC149526
0.8882	High Similarity	NPC474417
0.8874	High Similarity	NPC100985
0.8874	High Similarity	NPC10027
0.8874	High Similarity	NPC158338
0.8874	High Similarity	NPC97028
0.8874	High Similarity	NPC65589
0.8874	High Similarity	NPC65775
0.8874	High Similarity	NPC288036
0.8874	High Similarity	NPC97029
0.8868	High Similarity	NPC249977
0.8867	High Similarity	NPC259632
0.8859	High Similarity	NPC131766
0.8859	High Similarity	NPC1886
0.8859	High Similarity	NPC178627
0.8859	High Similarity	NPC469935
0.8859	High Similarity	NPC196137
0.8851	High Similarity	NPC469542
0.8851	High Similarity	NPC51106
0.8851	High Similarity	NPC36181
0.8851	High Similarity	NPC472006
0.8846	High Similarity	NPC143050
0.8846	High Similarity	NPC312993
0.8831	High Similarity	NPC20541
0.8831	High Similarity	NPC254351
0.8831	High Similarity	NPC471800
0.8828	High Similarity	NPC135837
0.8824	High Similarity	NPC40356
0.8824	High Similarity	NPC142308
0.8824	High Similarity	NPC154683
0.8819	High Similarity	NPC182496
0.8819	High Similarity	NPC180905
0.8816	High Similarity	NPC158866
0.8816	High Similarity	NPC227122
0.8816	High Similarity	NPC474660
0.8808	High Similarity	NPC2569
0.8808	High Similarity	NPC27221
0.8808	High Similarity	NPC471642
0.8808	High Similarity	NPC256672
0.8808	High Similarity	NPC7025
0.8808	High Similarity	NPC240253
0.8808	High Similarity	NPC172329
0.8808	High Similarity	NPC471641
0.8808	High Similarity	NPC240622
0.88	High Similarity	NPC473927
0.88	High Similarity	NPC470322
0.88	High Similarity	NPC25844
0.88	High Similarity	NPC153758
0.8797	High Similarity	NPC474350
0.8797	High Similarity	NPC284007
0.8792	High Similarity	NPC470296
0.8792	High Similarity	NPC112791
0.8792	High Similarity	NPC188632
0.8792	High Similarity	NPC94794
0.8792	High Similarity	NPC87609
0.8792	High Similarity	NPC196459
0.879	High Similarity	NPC273467
0.879	High Similarity	NPC189552
0.8784	High Similarity	NPC49108
0.8784	High Similarity	NPC469579
0.8784	High Similarity	NPC474385
0.8782	High Similarity	NPC177650
0.8776	High Similarity	NPC254994
0.8774	High Similarity	NPC4547
0.8766	High Similarity	NPC475895
0.8766	High Similarity	NPC329844
0.8766	High Similarity	NPC169990
0.8766	High Similarity	NPC210942
0.8759	High Similarity	NPC242712
0.8758	High Similarity	NPC78835
0.8758	High Similarity	NPC204561
0.8758	High Similarity	NPC317715
0.8758	High Similarity	NPC316960
0.8758	High Similarity	NPC58668
0.8758	High Similarity	NPC193976
0.8758	High Similarity	NPC309512
0.8758	High Similarity	NPC72958
0.8758	High Similarity	NPC23668
0.8758	High Similarity	NPC106372
0.8758	High Similarity	NPC232645
0.8758	High Similarity	NPC148945
0.8758	High Similarity	NPC178484
0.875	High Similarity	NPC469932
0.875	High Similarity	NPC175943
0.8742	High Similarity	NPC7943
0.8742	High Similarity	NPC34802
0.8742	High Similarity	NPC140120
0.8742	High Similarity	NPC22005
0.8742	High Similarity	NPC142863
0.8742	High Similarity	NPC123202
0.8742	High Similarity	NPC267153
0.8734	High Similarity	NPC93739
0.8726	High Similarity	NPC186325
0.8725	High Similarity	NPC73028
0.8718	High Similarity	NPC324358
0.8718	High Similarity	NPC263483
0.8718	High Similarity	NPC323627
0.8718	High Similarity	NPC322459
0.8718	High Similarity	NPC318527
0.8716	High Similarity	NPC475730
0.8716	High Similarity	NPC53649
0.871	High Similarity	NPC297531
0.871	High Similarity	NPC99199
0.871	High Similarity	NPC213936
0.8707	High Similarity	NPC57380
0.8701	High Similarity	NPC474843
0.8701	High Similarity	NPC87708
0.8701	High Similarity	NPC207624
0.8701	High Similarity	NPC175978
0.8699	High Similarity	NPC194579
0.8699	High Similarity	NPC13408
0.8699	High Similarity	NPC70380
0.8696	High Similarity	NPC49487
0.8696	High Similarity	NPC99613
0.8693	High Similarity	NPC151973
0.8693	High Similarity	NPC325983
0.8684	High Similarity	NPC469933
0.8684	High Similarity	NPC208303
0.8684	High Similarity	NPC161864
0.8679	High Similarity	NPC300984
0.8675	High Similarity	NPC24136
0.8675	High Similarity	NPC187282
0.8675	High Similarity	NPC138978
0.8675	High Similarity	NPC290133
0.8675	High Similarity	NPC196114
0.8675	High Similarity	NPC57470
0.8675	High Similarity	NPC107625
0.8671	High Similarity	NPC303565
0.8667	High Similarity	NPC19896
0.8667	High Similarity	NPC11700
0.8667	High Similarity	NPC277426
0.8667	High Similarity	NPC210425
0.8667	High Similarity	NPC280404
0.8667	High Similarity	NPC86373
0.8662	High Similarity	NPC238381
0.8658	High Similarity	NPC96692
0.8658	High Similarity	NPC14871
0.8654	High Similarity	NPC56049
0.8654	High Similarity	NPC54830
0.8654	High Similarity	NPC475799
0.8654	High Similarity	NPC472907
0.8654	High Similarity	NPC13779
0.8649	High Similarity	NPC241975
0.8649	High Similarity	NPC216978
0.8649	High Similarity	NPC303633

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 NPC307780 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	338
0.1-0.2	987
0.2-0.3	1581
0.3-0.4	2609
0.4-0.5	1818
0.5-0.6	1153
0.6-0.7	455
0.7-0.8	150
0.8-0.85	46
0.85-0.9	12
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9139	High Similarity	NPD7819	Suspended
0.8836	High Similarity	NPD970	Clinical (unspecified phase)
0.8718	High Similarity	NPD3749	Approved
0.871	High Similarity	NPD8443	Clinical (unspecified phase)
0.8654	High Similarity	NPD7768	Phase 2
0.8636	High Similarity	NPD7411	Suspended
0.8616	High Similarity	NPD6232	Discontinued
0.8609	High Similarity	NPD7410	Clinical (unspecified phase)
0.8591	High Similarity	NPD3750	Approved
0.8571	High Similarity	NPD7473	Discontinued
0.8553	High Similarity	NPD6959	Discontinued
0.8509	High Similarity	NPD7852	Clinical (unspecified phase)
0.8487	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD7075	Discontinued
0.8418	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD3226	Approved
0.8366	Intermediate Similarity	NPD2533	Approved
0.8366	Intermediate Similarity	NPD2532	Approved
0.8366	Intermediate Similarity	NPD2534	Approved
0.8333	Intermediate Similarity	NPD1549	Phase 2
0.8301	Intermediate Similarity	NPD1511	Approved
0.8291	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD1465	Phase 2
0.8255	Intermediate Similarity	NPD3748	Approved
0.8255	Intermediate Similarity	NPD1510	Phase 2
0.8242	Intermediate Similarity	NPD5844	Phase 1
0.8239	Intermediate Similarity	NPD3817	Phase 2
0.8231	Intermediate Similarity	NPD1240	Approved
0.8228	Intermediate Similarity	NPD1934	Approved
0.8219	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD2796	Approved
0.8194	Intermediate Similarity	NPD1512	Approved
0.8182	Intermediate Similarity	NPD6799	Approved
0.8176	Intermediate Similarity	NPD2801	Approved
0.8171	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD6166	Phase 2
0.8171	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD1607	Approved
0.8113	Intermediate Similarity	NPD6801	Discontinued
0.8105	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD6599	Discontinued
0.8079	Intermediate Similarity	NPD2935	Discontinued
0.8079	Intermediate Similarity	NPD6100	Approved
0.8079	Intermediate Similarity	NPD6099	Approved
0.8079	Intermediate Similarity	NPD1551	Phase 2
0.8065	Intermediate Similarity	NPD7390	Discontinued
0.8039	Intermediate Similarity	NPD1243	Approved
0.8025	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1203	Approved
0.7987	Intermediate Similarity	NPD4380	Phase 2
0.7976	Intermediate Similarity	NPD7074	Phase 3
0.7963	Intermediate Similarity	NPD3882	Suspended
0.7959	Intermediate Similarity	NPD6832	Phase 2
0.7929	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD2800	Approved
0.7917	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7054	Approved
0.7908	Intermediate Similarity	NPD2346	Discontinued
0.7895	Intermediate Similarity	NPD2799	Discontinued
0.7879	Intermediate Similarity	NPD7199	Phase 2
0.7877	Intermediate Similarity	NPD2797	Approved
0.787	Intermediate Similarity	NPD7472	Approved
0.7857	Intermediate Similarity	NPD3818	Discontinued
0.7852	Intermediate Similarity	NPD3764	Approved
0.7852	Intermediate Similarity	NPD3268	Approved
0.7843	Intermediate Similarity	NPD5406	Approved
0.7843	Intermediate Similarity	NPD5404	Approved
0.7843	Intermediate Similarity	NPD5405	Approved
0.7843	Intermediate Similarity	NPD5408	Approved
0.7836	Intermediate Similarity	NPD7808	Phase 3
0.7831	Intermediate Similarity	NPD7229	Phase 3
0.7799	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD5403	Approved
0.7793	Intermediate Similarity	NPD9717	Approved
0.7793	Intermediate Similarity	NPD1608	Approved
0.7792	Intermediate Similarity	NPD2344	Approved
0.7791	Intermediate Similarity	NPD5402	Approved
0.7785	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6559	Discontinued
0.7778	Intermediate Similarity	NPD7251	Discontinued
0.7763	Intermediate Similarity	NPD6651	Approved
0.7756	Intermediate Similarity	NPD4628	Phase 3
0.7733	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD5710	Approved
0.7725	Intermediate Similarity	NPD5711	Approved
0.7724	Intermediate Similarity	NPD422	Phase 1
0.7719	Intermediate Similarity	NPD5953	Discontinued
0.7719	Intermediate Similarity	NPD6797	Phase 2
0.7718	Intermediate Similarity	NPD4908	Phase 1
0.7702	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD920	Approved
0.7688	Intermediate Similarity	NPD8313	Approved
0.7688	Intermediate Similarity	NPD8312	Approved
0.7684	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD4288	Approved
0.7673	Intermediate Similarity	NPD5401	Approved
0.767	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD4287	Approved
0.7662	Intermediate Similarity	NPD4308	Phase 3
0.7658	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD2313	Discontinued
0.7616	Intermediate Similarity	NPD411	Approved
0.761	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD5494	Approved
0.7602	Intermediate Similarity	NPD7286	Phase 2
0.7595	Intermediate Similarity	NPD2309	Approved
0.7586	Intermediate Similarity	NPD17	Approved
0.7582	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD447	Suspended
0.7574	Intermediate Similarity	NPD3926	Phase 2
0.7568	Intermediate Similarity	NPD3225	Approved
0.7562	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD37	Approved
0.755	Intermediate Similarity	NPD4625	Phase 3
0.7548	Intermediate Similarity	NPD7033	Discontinued
0.7545	Intermediate Similarity	NPD6234	Discontinued
0.7545	Intermediate Similarity	NPD919	Approved
0.7532	Intermediate Similarity	NPD7003	Approved
0.753	Intermediate Similarity	NPD4967	Phase 2
0.753	Intermediate Similarity	NPD4966	Approved
0.753	Intermediate Similarity	NPD4965	Approved
0.7517	Intermediate Similarity	NPD3267	Approved
0.7517	Intermediate Similarity	NPD3266	Approved
0.7516	Intermediate Similarity	NPD6273	Approved
0.7516	Intermediate Similarity	NPD943	Approved
0.7514	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1201	Approved
0.7468	Intermediate Similarity	NPD230	Phase 1
0.7467	Intermediate Similarity	NPD2798	Approved
0.746	Intermediate Similarity	NPD7783	Phase 2
0.746	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD8032	Phase 2
0.7447	Intermediate Similarity	NPD8151	Discontinued
0.7442	Intermediate Similarity	NPD7177	Discontinued
0.7429	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD4307	Phase 2
0.74	Intermediate Similarity	NPD1470	Approved
0.7386	Intermediate Similarity	NPD1296	Phase 2
0.7386	Intermediate Similarity	NPD6798	Discontinued
0.7383	Intermediate Similarity	NPD4749	Approved
0.7381	Intermediate Similarity	NPD6971	Discontinued
0.7365	Intermediate Similarity	NPD1610	Phase 2
0.7341	Intermediate Similarity	NPD7228	Approved
0.732	Intermediate Similarity	NPD7095	Approved
0.7305	Intermediate Similarity	NPD8455	Phase 2
0.7303	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD4060	Phase 1
0.7289	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7458	Discontinued
0.7263	Intermediate Similarity	NPD8150	Discontinued
0.7263	Intermediate Similarity	NPD8434	Phase 2
0.7255	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6355	Discontinued
0.7244	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1933	Approved
0.7244	Intermediate Similarity	NPD5124	Phase 1
0.7241	Intermediate Similarity	NPD3751	Discontinued
0.7219	Intermediate Similarity	NPD1283	Approved
0.7215	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD9545	Approved
0.7211	Intermediate Similarity	NPD1548	Phase 1
0.7209	Intermediate Similarity	NPD3787	Discontinued
0.7207	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD9493	Approved
0.7181	Intermediate Similarity	NPD7435	Discontinued
0.7171	Intermediate Similarity	NPD1164	Approved
0.717	Intermediate Similarity	NPD4476	Approved
0.717	Intermediate Similarity	NPD4477	Approved
0.7161	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD5535	Approved
0.7151	Intermediate Similarity	NPD8127	Discontinued
0.7143	Intermediate Similarity	NPD2654	Approved
0.7143	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7870	Phase 2
0.7143	Intermediate Similarity	NPD7871	Phase 2
0.7134	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1471	Phase 3
0.7124	Intermediate Similarity	NPD1019	Discontinued
0.7117	Intermediate Similarity	NPD7440	Discontinued
0.7115	Intermediate Similarity	NPD6233	Phase 2
0.7114	Intermediate Similarity	NPD4626	Approved
0.7093	Intermediate Similarity	NPD6746	Phase 2
0.709	Intermediate Similarity	NPD7696	Phase 3
0.709	Intermediate Similarity	NPD7697	Approved
0.709	Intermediate Similarity	NPD7698	Approved
0.7086	Intermediate Similarity	NPD1481	Phase 2
0.7073	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD1613	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