NPASS Compound

Structure

NPC475006 OpenBabel07101718232D 26 28 0 0 1 0 0 0 0 0999 V2000 -4.3301 4.5000 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 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 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 -2.5981 3.5000 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 -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 -0.0000 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 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 -1.7321 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 -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 -1.7321 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 2 0 0 0 0 0 0 0 0 0 3.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 C 0 0 0 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 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 5 10 1 0 0 0 0 5 11 1 0 0 0 0 6 8 2 0 0 0 0 6 15 1 0 0 0 0 7 9 1 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 15 2 0 0 0 0 12 16 1 0 0 0 0 13 19 1 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 16 17 2 0 0 0 0 17 21 1 0 0 0 0 18 21 1 6 0 0 0 18 22 1 0 0 0 0 19 23 2 0 0 0 0 19 24 1 0 0 0 0 20 25 2 0 0 0 0 20 26 1 0 0 0 0 21 3 1 6 0 0 0 22 4 1 6 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.21
Volume:	385.377
LogP:	4.506
LogD:	2.997
LogS:	-4.558
# Rotatable Bonds:	5
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.631
Synthetic Accessibility Score:	3.745
Fsp3:	0.636
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.122
MDCK Permeability:	3.855227623716928e-05
Pgp-inhibitor:	0.078
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.13
30% Bioavailability (F30%):	0.906

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.095
Plasma Protein Binding (PPB):	95.35338592529297%
Volume Distribution (VD):	0.239
Pgp-substrate:	3.4368112087249756%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.425
CYP2C19-inhibitor:	0.082
CYP2C19-substrate:	0.895
CYP2C9-inhibitor:	0.223
CYP2C9-substrate:	0.889
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.279
CYP3A4-inhibitor:	0.213
CYP3A4-substrate:	0.424

ADMET: Excretion

Clearance (CL):	3.204
Half-life (T1/2):	0.631

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.515
Drug-inuced Liver Injury (DILI):	0.499
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.162
Maximum Recommended Daily Dose:	0.093
Skin Sensitization:	0.907
Carcinogencity:	0.2
Eye Corrosion:	0.036
Eye Irritation:	0.398
Respiratory Toxicity:	0.701

Download Data

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

Natural Product: NPC475006

Natural Product ID:	NPC475006
*Common Name:**	3-[[(1R,4As,10Ar)-1,4A-Dimethyl-7-Propan-2-Yl-2,3,4,9,10,10A-Hexahydrophenanthren-1-Yl]Oxy]-3-Oxopropanoic Acid
IUPAC Name:	3-[[(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]oxy]-3-oxopropanoic acid
Synonyms:
Standard InCHIKey:	OKHGAAQNADNSGY-STZQEDGTSA-N
Standard InCHI:	InChI=1S/C22H30O4/c1-14(2)15-6-8-17-16(12-15)7-9-18-21(17,3)10-5-11-22(18,4)26-20(25)13-19(23)24/h6,8,12,14,18H,5,7,9-11,13H2,1-4H3,(H,23,24)/t18-,21-,22-/m1/s1
SMILES:	OC(=O)CC(=O)O[C@]1(C)CCC[C@]2([C@H]1CCc1c2ccc(c1)C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491703
PubChem CID:	44566216
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
NPO33152	calceolaria pinifolia	Species	Calceolariaceae	Eukaryota	aerial part	46 km west of Puesto de Gendarmeria in the province of San Juan, Argentina (3021 S; 6940 W)	1997-Jan	PMID[12608857]

☑ 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
MIC	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	128.0	ug.mL-1	PMID[526092]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[526092]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128.0	ug.mL-1	PMID[526092]

☑ 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 NPC475006 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	209
0.1-0.2	1006
0.2-0.3	2114
0.3-0.4	7020
0.4-0.5	14429
0.5-0.6	15654
0.6-0.7	2033
0.7-0.8	207
0.8-0.85	22
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8598	High Similarity	NPC21929
0.8558	High Similarity	NPC133809
0.8558	High Similarity	NPC225079
0.8558	High Similarity	NPC136810
0.8558	High Similarity	NPC128248
0.8286	Intermediate Similarity	NPC221825
0.8246	Intermediate Similarity	NPC242764
0.8246	Intermediate Similarity	NPC105141
0.8198	Intermediate Similarity	NPC475002
0.8198	Intermediate Similarity	NPC95126
0.8165	Intermediate Similarity	NPC94751
0.8165	Intermediate Similarity	NPC142326
0.8103	Intermediate Similarity	NPC254233
0.8095	Intermediate Similarity	NPC324602
0.8095	Intermediate Similarity	NPC226041
0.807	Intermediate Similarity	NPC221275
0.8017	Intermediate Similarity	NPC45794
0.8	Intermediate Similarity	NPC77691
0.7982	Intermediate Similarity	NPC472222
0.7982	Intermediate Similarity	NPC472221
0.7961	Intermediate Similarity	NPC220596
0.7931	Intermediate Similarity	NPC212891
0.7917	Intermediate Similarity	NPC273336
0.7917	Intermediate Similarity	NPC182333
0.7909	Intermediate Similarity	NPC471186
0.7895	Intermediate Similarity	NPC93287
0.7881	Intermediate Similarity	NPC202015
0.7851	Intermediate Similarity	NPC307139
0.7833	Intermediate Similarity	NPC293831
0.7833	Intermediate Similarity	NPC369
0.7826	Intermediate Similarity	NPC294458
0.7807	Intermediate Similarity	NPC471189
0.7805	Intermediate Similarity	NPC5486
0.7768	Intermediate Similarity	NPC27252
0.7768	Intermediate Similarity	NPC472979
0.7759	Intermediate Similarity	NPC473869
0.7739	Intermediate Similarity	NPC477475
0.7739	Intermediate Similarity	NPC477476
0.7727	Intermediate Similarity	NPC19856
0.7719	Intermediate Similarity	NPC133308
0.7686	Intermediate Similarity	NPC473889
0.7685	Intermediate Similarity	NPC271475
0.7672	Intermediate Similarity	NPC471721
0.7667	Intermediate Similarity	NPC234337
0.7667	Intermediate Similarity	NPC183339
0.7667	Intermediate Similarity	NPC133389
0.7661	Intermediate Similarity	NPC253681
0.7652	Intermediate Similarity	NPC280789
0.7627	Intermediate Similarity	NPC470820
0.7624	Intermediate Similarity	NPC267704
0.7623	Intermediate Similarity	NPC473870
0.7623	Intermediate Similarity	NPC473871
0.7611	Intermediate Similarity	NPC472980
0.7607	Intermediate Similarity	NPC215419
0.7593	Intermediate Similarity	NPC477767
0.7589	Intermediate Similarity	NPC243601
0.7565	Intermediate Similarity	NPC265513
0.7563	Intermediate Similarity	NPC84129
0.7561	Intermediate Similarity	NPC85511
0.7545	Intermediate Similarity	NPC264728
0.7544	Intermediate Similarity	NPC64642
0.7544	Intermediate Similarity	NPC472982
0.7544	Intermediate Similarity	NPC149455
0.7542	Intermediate Similarity	NPC9274
0.7541	Intermediate Similarity	NPC269923
0.7541	Intermediate Similarity	NPC167323
0.7523	Intermediate Similarity	NPC120393
0.75	Intermediate Similarity	NPC473860
0.75	Intermediate Similarity	NPC469893
0.75	Intermediate Similarity	NPC471188
0.75	Intermediate Similarity	NPC56168
0.75	Intermediate Similarity	NPC218855
0.746	Intermediate Similarity	NPC51448
0.746	Intermediate Similarity	NPC115797
0.7458	Intermediate Similarity	NPC186933
0.744	Intermediate Similarity	NPC475933
0.744	Intermediate Similarity	NPC476970
0.744	Intermediate Similarity	NPC470158
0.7431	Intermediate Similarity	NPC469892
0.7431	Intermediate Similarity	NPC469890
0.7431	Intermediate Similarity	NPC469891
0.7429	Intermediate Similarity	NPC298115
0.7419	Intermediate Similarity	NPC328107
0.7411	Intermediate Similarity	NPC247976
0.7398	Intermediate Similarity	NPC162935
0.7398	Intermediate Similarity	NPC249340
0.7387	Intermediate Similarity	NPC469481
0.7381	Intermediate Similarity	NPC476972
0.7381	Intermediate Similarity	NPC476971
0.7373	Intermediate Similarity	NPC234637
0.7373	Intermediate Similarity	NPC130591
0.7368	Intermediate Similarity	NPC244933
0.7368	Intermediate Similarity	NPC85560
0.7368	Intermediate Similarity	NPC100767
0.736	Intermediate Similarity	NPC10154
0.736	Intermediate Similarity	NPC265413
0.7358	Intermediate Similarity	NPC26224
0.7353	Intermediate Similarity	NPC473592
0.7345	Intermediate Similarity	NPC329282
0.7339	Intermediate Similarity	NPC478058
0.7339	Intermediate Similarity	NPC121168
0.7333	Intermediate Similarity	NPC472862
0.7321	Intermediate Similarity	NPC474820
0.7321	Intermediate Similarity	NPC475978
0.7317	Intermediate Similarity	NPC241001
0.7317	Intermediate Similarity	NPC311175
0.7317	Intermediate Similarity	NPC37641
0.7302	Intermediate Similarity	NPC470765
0.7295	Intermediate Similarity	NPC42657
0.7295	Intermediate Similarity	NPC476645
0.729	Intermediate Similarity	NPC86987
0.7288	Intermediate Similarity	NPC470253
0.7288	Intermediate Similarity	NPC471481
0.7287	Intermediate Similarity	NPC476977
0.728	Intermediate Similarity	NPC140118
0.728	Intermediate Similarity	NPC12881
0.7273	Intermediate Similarity	NPC152812
0.7258	Intermediate Similarity	NPC70973
0.725	Intermediate Similarity	NPC469719
0.725	Intermediate Similarity	NPC260886
0.7248	Intermediate Similarity	NPC172925
0.7244	Intermediate Similarity	NPC473220
0.7244	Intermediate Similarity	NPC470753
0.7244	Intermediate Similarity	NPC190849
0.7244	Intermediate Similarity	NPC171007
0.7239	Intermediate Similarity	NPC474250
0.7236	Intermediate Similarity	NPC475827
0.7236	Intermediate Similarity	NPC474223
0.7232	Intermediate Similarity	NPC94487
0.7231	Intermediate Similarity	NPC476976
0.7222	Intermediate Similarity	NPC473083
0.7222	Intermediate Similarity	NPC471758
0.7212	Intermediate Similarity	NPC475710
0.7209	Intermediate Similarity	NPC131684
0.72	Intermediate Similarity	NPC12016
0.7196	Intermediate Similarity	NPC274455
0.7196	Intermediate Similarity	NPC86670
0.7196	Intermediate Similarity	NPC70940
0.7188	Intermediate Similarity	NPC472678
0.7179	Intermediate Similarity	NPC273837
0.7177	Intermediate Similarity	NPC164852
0.7167	Intermediate Similarity	NPC217111
0.7165	Intermediate Similarity	NPC473082
0.7165	Intermediate Similarity	NPC275576
0.7165	Intermediate Similarity	NPC45821
0.7165	Intermediate Similarity	NPC470816
0.7154	Intermediate Similarity	NPC472692
0.7154	Intermediate Similarity	NPC472682
0.7154	Intermediate Similarity	NPC471334
0.7143	Intermediate Similarity	NPC470815
0.7143	Intermediate Similarity	NPC143768
0.7143	Intermediate Similarity	NPC318067
0.7143	Intermediate Similarity	NPC472373
0.7143	Intermediate Similarity	NPC54647
0.7143	Intermediate Similarity	NPC472804
0.7132	Intermediate Similarity	NPC93632
0.7131	Intermediate Similarity	NPC268930
0.713	Intermediate Similarity	NPC125226
0.7109	Intermediate Similarity	NPC474106
0.7109	Intermediate Similarity	NPC169913
0.7109	Intermediate Similarity	NPC470648
0.7105	Intermediate Similarity	NPC329556
0.71	Intermediate Similarity	NPC249018
0.71	Intermediate Similarity	NPC3190
0.7099	Intermediate Similarity	NPC209851
0.7097	Intermediate Similarity	NPC472680
0.7097	Intermediate Similarity	NPC472679
0.7097	Intermediate Similarity	NPC478121
0.7094	Intermediate Similarity	NPC469511
0.7087	Intermediate Similarity	NPC474979
0.7087	Intermediate Similarity	NPC114927
0.7077	Intermediate Similarity	NPC471832
0.7077	Intermediate Similarity	NPC475138
0.7073	Intermediate Similarity	NPC472697
0.7073	Intermediate Similarity	NPC89324
0.7073	Intermediate Similarity	NPC472698
0.7069	Intermediate Similarity	NPC37914
0.7069	Intermediate Similarity	NPC474111
0.7069	Intermediate Similarity	NPC329705
0.7063	Intermediate Similarity	NPC474254
0.7063	Intermediate Similarity	NPC474159
0.7059	Intermediate Similarity	NPC260323
0.7059	Intermediate Similarity	NPC66208
0.7059	Intermediate Similarity	NPC292834
0.7059	Intermediate Similarity	NPC176279
0.7054	Intermediate Similarity	NPC230331
0.7054	Intermediate Similarity	NPC478165
0.7054	Intermediate Similarity	NPC478162
0.7049	Intermediate Similarity	NPC471668
0.7049	Intermediate Similarity	NPC92
0.7049	Intermediate Similarity	NPC469663
0.7045	Intermediate Similarity	NPC159811
0.7043	Intermediate Similarity	NPC19136
0.704	Intermediate Similarity	NPC300827
0.704	Intermediate Similarity	NPC32322
0.704	Intermediate Similarity	NPC259703
0.704	Intermediate Similarity	NPC473439
0.7037	Intermediate Similarity	NPC84288
0.7031	Intermediate Similarity	NPC478107
0.7031	Intermediate Similarity	NPC100402

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 NPC475006 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	190
0.1-0.2	769
0.2-0.3	1356
0.3-0.4	3090
0.4-0.5	2367
0.5-0.6	1175
0.6-0.7	192
0.7-0.8	11
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7542	Intermediate Similarity	NPD4198	Discontinued
0.7458	Intermediate Similarity	NPD5951	Approved
0.7407	Intermediate Similarity	NPD6049	Phase 2
0.7407	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1088	Approved
0.7373	Intermediate Similarity	NPD6010	Discontinued
0.7315	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD2066	Phase 3
0.7288	Intermediate Similarity	NPD7094	Approved
0.7288	Intermediate Similarity	NPD6858	Approved
0.7248	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD4199	Phase 3
0.7196	Intermediate Similarity	NPD1090	Approved
0.7196	Intermediate Similarity	NPD1089	Approved
0.7196	Intermediate Similarity	NPD1086	Approved
0.7131	Intermediate Similarity	NPD7610	Discontinued
0.7119	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD3317	Approved
0.7105	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1929	Approved
0.7105	Intermediate Similarity	NPD1930	Approved
0.7103	Intermediate Similarity	NPD800	Approved
0.7099	Intermediate Similarity	NPD7961	Discontinued
0.7097	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD1693	Approved
0.7077	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6685	Approved
0.7054	Intermediate Similarity	NPD5736	Approved
0.7043	Intermediate Similarity	NPD5909	Discontinued
0.7027	Intermediate Similarity	NPD1989	Approved
0.7025	Intermediate Similarity	NPD2629	Approved
0.6991	Remote Similarity	NPD7798	Approved
0.6983	Remote Similarity	NPD5048	Discontinued
0.6972	Remote Similarity	NPD1239	Approved
0.6964	Remote Similarity	NPD3495	Discontinued
0.6964	Remote Similarity	NPD1564	Approved
0.6964	Remote Similarity	NPD1565	Approved
0.6964	Remote Similarity	NPD1566	Phase 3
0.6944	Remote Similarity	NPD5346	Phase 2
0.6944	Remote Similarity	NPD5347	Phase 2
0.6935	Remote Similarity	NPD7741	Discontinued
0.6916	Remote Similarity	NPD1087	Approved
0.6887	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD3672	Approved
0.6881	Remote Similarity	NPD3673	Approved
0.687	Remote Similarity	NPD1932	Approved
0.6857	Remote Similarity	NPD3971	Phase 1
0.685	Remote Similarity	NPD5618	Discontinued
0.6842	Remote Similarity	NPD6663	Approved
0.6827	Remote Similarity	NPD226	Approved
0.6825	Remote Similarity	NPD3019	Approved
0.6818	Remote Similarity	NPD7008	Discontinued
0.681	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6647	Phase 2
0.681	Remote Similarity	NPD5765	Approved
0.6807	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD2329	Discontinued
0.6803	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD2650	Approved
0.6803	Remote Similarity	NPD2652	Approved
0.68	Remote Similarity	NPD7009	Phase 2
0.6759	Remote Similarity	NPD4793	Discontinued
0.6723	Remote Similarity	NPD2342	Discontinued
0.6721	Remote Similarity	NPD7635	Approved
0.6696	Remote Similarity	NPD1563	Approved
0.6693	Remote Similarity	NPD5126	Approved
0.6693	Remote Similarity	NPD5125	Phase 3
0.6693	Remote Similarity	NPD2932	Approved
0.6667	Remote Similarity	NPD5408	Approved
0.6667	Remote Similarity	NPD4140	Approved
0.6667	Remote Similarity	NPD5404	Approved
0.6667	Remote Similarity	NPD5405	Approved
0.6667	Remote Similarity	NPD5406	Approved
0.6641	Remote Similarity	NPD3023	Approved
0.6641	Remote Similarity	NPD3026	Approved
0.6639	Remote Similarity	NPD6912	Phase 3
0.662	Remote Similarity	NPD7236	Approved
0.6619	Remote Similarity	NPD2346	Discontinued
0.6614	Remote Similarity	NPD3025	Approved
0.6614	Remote Similarity	NPD3024	Approved
0.6587	Remote Similarity	NPD6065	Approved
0.6567	Remote Similarity	NPD7095	Approved
0.6565	Remote Similarity	NPD1283	Approved
0.6562	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4626	Approved
0.6562	Remote Similarity	NPD4059	Approved
0.6562	Remote Similarity	NPD3095	Discontinued
0.6557	Remote Similarity	NPD3642	Approved
0.6557	Remote Similarity	NPD3643	Approved
0.6557	Remote Similarity	NPD3644	Approved
0.6542	Remote Similarity	NPD9491	Approved
0.6538	Remote Similarity	NPD227	Approved
0.6538	Remote Similarity	NPD225	Approved
0.6538	Remote Similarity	NPD3880	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD3091	Approved
0.6535	Remote Similarity	NPD4479	Discontinued
0.6525	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD7239	Suspended
0.65	Remote Similarity	NPD5704	Approved
0.65	Remote Similarity	NPD5705	Approved
0.65	Remote Similarity	NPD5706	Approved
0.6484	Remote Similarity	NPD5691	Approved
0.6484	Remote Similarity	NPD5981	Approved
0.6479	Remote Similarity	NPD7003	Approved
0.6475	Remote Similarity	NPD5240	Approved
0.6475	Remote Similarity	NPD5235	Approved
0.6475	Remote Similarity	NPD5237	Approved
0.6475	Remote Similarity	NPD5236	Approved
0.6475	Remote Similarity	NPD5239	Approved
0.6475	Remote Similarity	NPD1317	Discontinued
0.6471	Remote Similarity	NPD7715	Approved
0.6471	Remote Similarity	NPD7714	Approved
0.6471	Remote Similarity	NPD8032	Phase 2
0.6466	Remote Similarity	NPD5926	Approved
0.6462	Remote Similarity	NPD1611	Approved
0.6435	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD4060	Phase 1
0.6396	Remote Similarity	NPD1101	Approved
0.6391	Remote Similarity	NPD3094	Phase 2
0.6385	Remote Similarity	NPD3881	Discontinued
0.6385	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD1875	Phase 1
0.6364	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8166	Discontinued
0.6357	Remote Similarity	NPD4209	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD4766	Approved
0.6343	Remote Similarity	NPD4624	Approved
0.6341	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD2611	Approved
0.6336	Remote Similarity	NPD3131	Approved
0.6336	Remote Similarity	NPD2610	Approved
0.6336	Remote Similarity	NPD3132	Approved
0.6336	Remote Similarity	NPD3092	Approved
0.6336	Remote Similarity	NPD1201	Approved
0.6336	Remote Similarity	NPD4218	Approved
0.6336	Remote Similarity	NPD4215	Approved
0.6336	Remote Similarity	NPD4216	Approved
0.6336	Remote Similarity	NPD2609	Approved
0.6336	Remote Similarity	NPD2612	Approved
0.6336	Remote Similarity	NPD2608	Approved
0.6336	Remote Similarity	NPD1281	Approved
0.6336	Remote Similarity	NPD4217	Approved
0.6331	Remote Similarity	NPD4097	Suspended
0.6324	Remote Similarity	NPD4625	Phase 3
0.6316	Remote Similarity	NPD7631	Approved
0.6308	Remote Similarity	NPD5305	Approved
0.6308	Remote Similarity	NPD5306	Approved
0.6304	Remote Similarity	NPD2979	Phase 3
0.6296	Remote Similarity	NPD7084	Phase 3
0.629	Remote Similarity	NPD2201	Approved
0.629	Remote Similarity	NPD5927	Discontinued
0.6271	Remote Similarity	NPD3020	Approved
0.6269	Remote Similarity	NPD2797	Approved
0.6269	Remote Similarity	NPD1470	Approved
0.6261	Remote Similarity	NPD845	Approved
0.6261	Remote Similarity	NPD1066	Discontinued
0.6261	Remote Similarity	NPD719	Approved
0.6261	Remote Similarity	NPD720	Approved
0.6261	Remote Similarity	NPD3719	Approved
0.6261	Remote Similarity	NPD3718	Approved
0.625	Remote Similarity	NPD531	Approved
0.6242	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD3226	Approved
0.6241	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD7305	Phase 1
0.6241	Remote Similarity	NPD2799	Discontinued
0.6239	Remote Similarity	NPD288	Approved
0.6231	Remote Similarity	NPD4105	Approved
0.6231	Remote Similarity	NPD4102	Approved
0.6228	Remote Similarity	NPD7609	Phase 3
0.6222	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD6085	Phase 2
0.6222	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD6287	Discontinued
0.6212	Remote Similarity	NPD4807	Approved
0.6212	Remote Similarity	NPD3529	Phase 2
0.6212	Remote Similarity	NPD4806	Approved
0.621	Remote Similarity	NPD4750	Phase 3
0.6207	Remote Similarity	NPD4814	Discontinued
0.6207	Remote Similarity	NPD3772	Phase 3
0.6202	Remote Similarity	NPD7644	Approved
0.6197	Remote Similarity	NPD6100	Approved
0.6197	Remote Similarity	NPD6099	Approved
0.6197	Remote Similarity	NPD2438	Suspended
0.619	Remote Similarity	NPD5535	Approved
0.619	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6187	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD253	Approved
0.6183	Remote Similarity	NPD7725	Approved
0.6183	Remote Similarity	NPD1778	Approved
0.6183	Remote Similarity	NPD2345	Approved
0.6182	Remote Similarity	NPD4544	Approved
0.6174	Remote Similarity	NPD752	Approved
0.6168	Remote Similarity	NPD9490	Approved
0.6165	Remote Similarity	NPD6637	Approved
0.616	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD3268	Approved
0.6159	Remote Similarity	NPD3764	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