NPASS Compound

Structure

NPC474991 OpenBabel07101719512D 25 28 0 0 1 0 0 0 0 0999 V2000 3.5016 -0.0039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4867 0.3397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0294 1.1356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7306 2.3039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1636 1.8372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0956 2.2564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0056 -0.5206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5038 -0.0740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6876 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6741 -0.4973 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.8331 -0.0273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1646 -0.0506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6629 -0.5440 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5173 0.8893 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1511 0.9126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8196 0.9360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9786 1.4060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0120 0.8574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0687 1.2076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6898 1.3826 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5285 -1.9305 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6471 1.4293 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9651 2.3693 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7121 1.7176 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 10 1 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 19 1 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 14 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 11 16 1 0 0 0 0 12 13 1 0 0 0 0 12 15 2 0 0 0 0 13 8 1 6 0 0 0 13 25 1 0 0 0 0 14 19 1 0 0 0 0 14 20 1 1 0 0 0 15 17 1 0 0 0 0 15 20 1 0 0 0 0 16 17 2 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 18 20 1 0 0 0 0 18 24 2 0 0 0 0 18 25 1 0 0 0 0 20 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.18
Volume:	353.656
LogP:	3.181
LogD:	2.256
LogS:	-3.543
# Rotatable Bonds:	2
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.565
Synthetic Accessibility Score:	5.525
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.739
MDCK Permeability:	2.2968095436226577e-05
Pgp-inhibitor:	0.097
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.789
Plasma Protein Binding (PPB):	94.78756713867188%
Volume Distribution (VD):	1.332
Pgp-substrate:	10.4318265914917%

ADMET: Metabolism

CYP1A2-inhibitor:	0.051
CYP1A2-substrate:	0.776
CYP2C19-inhibitor:	0.047
CYP2C19-substrate:	0.809
CYP2C9-inhibitor:	0.252
CYP2C9-substrate:	0.948
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.419
CYP3A4-inhibitor:	0.302
CYP3A4-substrate:	0.454

ADMET: Excretion

Clearance (CL):	11.47
Half-life (T1/2):	0.275

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.259
Drug-inuced Liver Injury (DILI):	0.196
AMES Toxicity:	0.077
Rat Oral Acute Toxicity:	0.952
Maximum Recommended Daily Dose:	0.974
Skin Sensitization:	0.906
Carcinogencity:	0.572
Eye Corrosion:	0.003
Eye Irritation:	0.816
Respiratory Toxicity:	0.945

Download Data

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

Natural Product: NPC474991

Natural Product ID:	NPC474991
*Common Name:**	MWLHJCBZAWPKEY-NUDIBWDTSA-N
IUPAC Name:	n.a.
Synonyms:	16-Hydroxycarnosol
Standard InCHIKey:	MWLHJCBZAWPKEY-NUDIBWDTSA-N
Standard InCHI:	InChI=1S/C20H26O5/c1-10(9-21)11-7-12-13-8-14-19(2,3)5-4-6-20(14,18(24)25-13)15(12)17(23)16(11)22/h7,10,13-14,21-23H,4-6,8-9H2,1-3H3/t10?,13-,14-,20+/m0/s1
SMILES:	OCC(c1cc2[C@H]3OC(=O)[C@@]4(c2c(c1O)O)[C@@H](C3)C(C)(C)CCC4)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491307
PubChem CID:	44566424
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO20067	Salvia pachyphylla	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190465]
NPO2794	Salvia clevelandii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190465]
NPO2794	Salvia clevelandii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
GI50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	GI50	=	3600.0	nM	PMID[553372]
NPT1577	Cell Line	SW1573	Homo sapiens	GI50	=	9000.0	nM	PMID[553372]
NPT1183	Cell Line	WiDr	Homo sapiens	GI50	=	28000.0	nM	PMID[553372]
NPT396	Cell Line	T47D	Homo sapiens	GI50	=	35000.0	nM	PMID[553372]
NPT1723	Cell Line	HBL-100	Homo sapiens	GI50	=	3600.0	nM	PMID[553372]

☑ 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 NPC474991 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	331
0.1-0.2	1284
0.2-0.3	2809
0.3-0.4	5597
0.4-0.5	9725
0.5-0.6	8262
0.6-0.7	9592
0.7-0.8	4919
0.8-0.85	136
0.85-0.9	31
0.9-0.95	6
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9787	High Similarity	NPC127046
0.9786	High Similarity	NPC84786
0.9577	High Similarity	NPC191899
0.9577	High Similarity	NPC246229
0.9437	High Similarity	NPC126707
0.9172	High Similarity	NPC58752
0.9137	High Similarity	NPC293454
0.911	High Similarity	NPC470757
0.9091	High Similarity	NPC272907
0.9091	High Similarity	NPC2681
0.9021	High Similarity	NPC3218
0.8973	High Similarity	NPC75295
0.8929	High Similarity	NPC49742
0.8859	High Similarity	NPC303989
0.8857	High Similarity	NPC59239
0.8844	High Similarity	NPC258856
0.8759	High Similarity	NPC471853
0.8759	High Similarity	NPC475907
0.875	High Similarity	NPC62051
0.8733	High Similarity	NPC142654
0.8714	High Similarity	NPC99795
0.8667	High Similarity	NPC471852
0.8652	High Similarity	NPC312341
0.8652	High Similarity	NPC291001
0.8639	High Similarity	NPC248068
0.8618	High Similarity	NPC124842
0.8571	High Similarity	NPC472835
0.8544	High Similarity	NPC25889
0.8535	High Similarity	NPC266365
0.8521	High Similarity	NPC78575
0.8483	Intermediate Similarity	NPC475111
0.8472	Intermediate Similarity	NPC213122
0.8462	Intermediate Similarity	NPC167098
0.8462	Intermediate Similarity	NPC296044
0.8438	Intermediate Similarity	NPC263212
0.8418	Intermediate Similarity	NPC177100
0.8418	Intermediate Similarity	NPC139540
0.8415	Intermediate Similarity	NPC475054
0.8403	Intermediate Similarity	NPC476282
0.8397	Intermediate Similarity	NPC165483
0.8389	Intermediate Similarity	NPC184935
0.8377	Intermediate Similarity	NPC221249
0.8366	Intermediate Similarity	NPC247219
0.8356	Intermediate Similarity	NPC68292
0.8333	Intermediate Similarity	NPC165612
0.8323	Intermediate Similarity	NPC65591
0.8323	Intermediate Similarity	NPC200726
0.8323	Intermediate Similarity	NPC178574
0.8299	Intermediate Similarity	NPC471152
0.8298	Intermediate Similarity	NPC253681
0.8291	Intermediate Similarity	NPC471750
0.8278	Intermediate Similarity	NPC309169
0.8278	Intermediate Similarity	NPC260152
0.8278	Intermediate Similarity	NPC196941
0.8276	Intermediate Similarity	NPC239855
0.8276	Intermediate Similarity	NPC111845
0.8272	Intermediate Similarity	NPC177362
0.8272	Intermediate Similarity	NPC107009
0.8269	Intermediate Similarity	NPC125487
0.8269	Intermediate Similarity	NPC281703
0.8267	Intermediate Similarity	NPC469447
0.8267	Intermediate Similarity	NPC314271
0.8267	Intermediate Similarity	NPC477873
0.8264	Intermediate Similarity	NPC243305
0.8258	Intermediate Similarity	NPC270268
0.8255	Intermediate Similarity	NPC327187
0.8243	Intermediate Similarity	NPC230811
0.8239	Intermediate Similarity	NPC21046
0.8239	Intermediate Similarity	NPC24627
0.8239	Intermediate Similarity	NPC471077
0.8235	Intermediate Similarity	NPC81835
0.8235	Intermediate Similarity	NPC52692
0.8235	Intermediate Similarity	NPC5568
0.8231	Intermediate Similarity	NPC326847
0.8228	Intermediate Similarity	NPC143328
0.8224	Intermediate Similarity	NPC470038
0.8221	Intermediate Similarity	NPC266545
0.8221	Intermediate Similarity	NPC202428
0.8217	Intermediate Similarity	NPC82190
0.8217	Intermediate Similarity	NPC192219
0.8217	Intermediate Similarity	NPC174599
0.8212	Intermediate Similarity	NPC100242
0.8212	Intermediate Similarity	NPC470130
0.8207	Intermediate Similarity	NPC476389
0.8205	Intermediate Similarity	NPC180388
0.8188	Intermediate Similarity	NPC191280
0.8187	Intermediate Similarity	NPC124747
0.8187	Intermediate Similarity	NPC109061
0.8187	Intermediate Similarity	NPC155754
0.8182	Intermediate Similarity	NPC473719
0.8182	Intermediate Similarity	NPC220006
0.8182	Intermediate Similarity	NPC181452
0.8176	Intermediate Similarity	NPC470339
0.8176	Intermediate Similarity	NPC98083
0.8176	Intermediate Similarity	NPC7543
0.8176	Intermediate Similarity	NPC94220
0.8176	Intermediate Similarity	NPC24339
0.8176	Intermediate Similarity	NPC166456
0.8176	Intermediate Similarity	NPC4950
0.8171	Intermediate Similarity	NPC472803
0.817	Intermediate Similarity	NPC268366
0.8165	Intermediate Similarity	NPC478027
0.8165	Intermediate Similarity	NPC283480
0.8165	Intermediate Similarity	NPC148323
0.8165	Intermediate Similarity	NPC471968
0.8163	Intermediate Similarity	NPC153088
0.8163	Intermediate Similarity	NPC103082
0.8163	Intermediate Similarity	NPC279463
0.816	Intermediate Similarity	NPC217781
0.8158	Intermediate Similarity	NPC53520
0.8156	Intermediate Similarity	NPC181334
0.8151	Intermediate Similarity	NPC138472
0.8151	Intermediate Similarity	NPC227719
0.8148	Intermediate Similarity	NPC162169
0.8148	Intermediate Similarity	NPC166851
0.8141	Intermediate Similarity	NPC48671
0.8137	Intermediate Similarity	NPC291957
0.8137	Intermediate Similarity	NPC14030
0.8133	Intermediate Similarity	NPC29599
0.8133	Intermediate Similarity	NPC470035
0.8129	Intermediate Similarity	NPC183380
0.8129	Intermediate Similarity	NPC474305
0.8129	Intermediate Similarity	NPC327962
0.8125	Intermediate Similarity	NPC472055
0.8117	Intermediate Similarity	NPC117788
0.8117	Intermediate Similarity	NPC474940
0.8117	Intermediate Similarity	NPC476463
0.8117	Intermediate Similarity	NPC325032
0.8117	Intermediate Similarity	NPC474856
0.8117	Intermediate Similarity	NPC290902
0.8117	Intermediate Similarity	NPC474834
0.8117	Intermediate Similarity	NPC477483
0.8117	Intermediate Similarity	NPC159697
0.8117	Intermediate Similarity	NPC474795
0.8117	Intermediate Similarity	NPC130959
0.8117	Intermediate Similarity	NPC291326
0.8117	Intermediate Similarity	NPC119767
0.8117	Intermediate Similarity	NPC303013
0.8113	Intermediate Similarity	NPC206641
0.8113	Intermediate Similarity	NPC208651
0.8113	Intermediate Similarity	NPC302258
0.8105	Intermediate Similarity	NPC170055
0.8105	Intermediate Similarity	NPC8102
0.8105	Intermediate Similarity	NPC66894
0.8105	Intermediate Similarity	NPC471608
0.8101	Intermediate Similarity	NPC472807
0.8101	Intermediate Similarity	NPC16082
0.8101	Intermediate Similarity	NPC82592
0.8101	Intermediate Similarity	NPC203757
0.8099	Intermediate Similarity	NPC87985
0.8099	Intermediate Similarity	NPC137750
0.8098	Intermediate Similarity	NPC317671
0.8098	Intermediate Similarity	NPC142707
0.8098	Intermediate Similarity	NPC49983
0.8098	Intermediate Similarity	NPC472621
0.8098	Intermediate Similarity	NPC26536
0.8095	Intermediate Similarity	NPC477893
0.8095	Intermediate Similarity	NPC204582
0.8095	Intermediate Similarity	NPC477896
0.8095	Intermediate Similarity	NPC202225
0.8092	Intermediate Similarity	NPC159721
0.8092	Intermediate Similarity	NPC477207
0.8092	Intermediate Similarity	NPC471731
0.8092	Intermediate Similarity	NPC25491
0.8089	Intermediate Similarity	NPC474534
0.8089	Intermediate Similarity	NPC295646
0.8089	Intermediate Similarity	NPC474533
0.8086	Intermediate Similarity	NPC116759
0.8086	Intermediate Similarity	NPC470898
0.8086	Intermediate Similarity	NPC14294
0.8086	Intermediate Similarity	NPC476295
0.8085	Intermediate Similarity	NPC471187
0.8077	Intermediate Similarity	NPC470037
0.8077	Intermediate Similarity	NPC225854
0.8077	Intermediate Similarity	NPC118033
0.8077	Intermediate Similarity	NPC31132
0.8072	Intermediate Similarity	NPC471871
0.8071	Intermediate Similarity	NPC249340
0.8071	Intermediate Similarity	NPC162935
0.8065	Intermediate Similarity	NPC475940
0.8065	Intermediate Similarity	NPC279442
0.8065	Intermediate Similarity	NPC477206
0.8065	Intermediate Similarity	NPC475848
0.8065	Intermediate Similarity	NPC474306
0.8065	Intermediate Similarity	NPC474893
0.8063	Intermediate Similarity	NPC239118
0.8063	Intermediate Similarity	NPC85121
0.8054	Intermediate Similarity	NPC277559
0.8054	Intermediate Similarity	NPC49911
0.8054	Intermediate Similarity	NPC308976
0.8052	Intermediate Similarity	NPC285122
0.8052	Intermediate Similarity	NPC473023
0.8052	Intermediate Similarity	NPC147250
0.8052	Intermediate Similarity	NPC63918
0.8049	Intermediate Similarity	NPC472622
0.8042	Intermediate Similarity	NPC5486
0.8042	Intermediate Similarity	NPC476022
0.8042	Intermediate Similarity	NPC474945
0.8039	Intermediate Similarity	NPC48130
0.8039	Intermediate Similarity	NPC469683

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 NPC474991 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	277
0.1-0.2	838
0.2-0.3	1626
0.3-0.4	2638
0.4-0.5	2062
0.5-0.6	1134
0.6-0.7	489
0.7-0.8	86
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
0.8079	Intermediate Similarity	NPD8166	Discontinued
0.8	Intermediate Similarity	NPD5844	Phase 1
0.7987	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD6234	Discontinued
0.7939	Intermediate Similarity	NPD7228	Approved
0.7937	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD37	Approved
0.7826	Intermediate Similarity	NPD4966	Approved
0.7826	Intermediate Similarity	NPD4965	Approved
0.7826	Intermediate Similarity	NPD4967	Phase 2
0.7805	Intermediate Similarity	NPD6232	Discontinued
0.7792	Intermediate Similarity	NPD6190	Approved
0.7771	Intermediate Similarity	NPD7473	Discontinued
0.7727	Intermediate Similarity	NPD4628	Phase 3
0.7702	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD230	Phase 1
0.7662	Intermediate Similarity	NPD6674	Discontinued
0.7651	Intermediate Similarity	NPD6663	Approved
0.7644	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD2534	Approved
0.7643	Intermediate Similarity	NPD2533	Approved
0.7643	Intermediate Similarity	NPD2532	Approved
0.763	Intermediate Similarity	NPD8150	Discontinued
0.7619	Intermediate Similarity	NPD5736	Approved
0.7532	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD8127	Discontinued
0.75	Intermediate Similarity	NPD7003	Approved
0.7485	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1465	Phase 2
0.7483	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD3620	Phase 2
0.7468	Intermediate Similarity	NPD6099	Approved
0.7468	Intermediate Similarity	NPD6100	Approved
0.7453	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD7458	Discontinued
0.7442	Intermediate Similarity	NPD7240	Approved
0.7425	Intermediate Similarity	NPD7199	Phase 2
0.7425	Intermediate Similarity	NPD6959	Discontinued
0.7423	Intermediate Similarity	NPD1934	Approved
0.7419	Intermediate Similarity	NPD7266	Discontinued
0.7415	Intermediate Similarity	NPD1283	Approved
0.7396	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6166	Phase 2
0.7396	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD6273	Approved
0.7368	Intermediate Similarity	NPD2979	Phase 3
0.7368	Intermediate Similarity	NPD4060	Phase 1
0.736	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD8312	Approved
0.7356	Intermediate Similarity	NPD8313	Approved
0.7355	Intermediate Similarity	NPD5408	Approved
0.7355	Intermediate Similarity	NPD5404	Approved
0.7355	Intermediate Similarity	NPD5406	Approved
0.7355	Intermediate Similarity	NPD5405	Approved
0.7351	Intermediate Similarity	NPD3764	Approved
0.7346	Intermediate Similarity	NPD3226	Approved
0.7325	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD3019	Approved
0.7308	Intermediate Similarity	NPD2346	Discontinued
0.7301	Intermediate Similarity	NPD4380	Phase 2
0.7278	Intermediate Similarity	NPD4110	Phase 3
0.7278	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7819	Suspended
0.7273	Intermediate Similarity	NPD8455	Phase 2
0.7261	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD4140	Approved
0.7248	Intermediate Similarity	NPD3094	Phase 2
0.7244	Intermediate Similarity	NPD2438	Suspended
0.7241	Intermediate Similarity	NPD7685	Pre-registration
0.7235	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7074	Phase 3
0.7215	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD3092	Approved
0.7211	Intermediate Similarity	NPD1281	Approved
0.72	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD2932	Approved
0.7179	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD5711	Approved
0.7176	Intermediate Similarity	NPD7229	Phase 3
0.7176	Intermediate Similarity	NPD5710	Approved
0.7171	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2801	Approved
0.7168	Intermediate Similarity	NPD7054	Approved
0.7162	Intermediate Similarity	NPD1608	Approved
0.716	Intermediate Similarity	NPD5494	Approved
0.7143	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1613	Approved
0.7143	Intermediate Similarity	NPD7390	Discontinued
0.7143	Intermediate Similarity	NPD7075	Discontinued
0.7133	Intermediate Similarity	NPD2629	Approved
0.7126	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7472	Approved
0.7124	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD6798	Discontinued
0.7124	Intermediate Similarity	NPD7985	Registered
0.712	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD2488	Approved
0.7111	Intermediate Similarity	NPD2490	Approved
0.711	Intermediate Similarity	NPD3818	Discontinued
0.7097	Intermediate Similarity	NPD6355	Discontinued
0.7089	Intermediate Similarity	NPD5762	Approved
0.7089	Intermediate Similarity	NPD6005	Phase 3
0.7089	Intermediate Similarity	NPD6002	Phase 3
0.7089	Intermediate Similarity	NPD6004	Phase 3
0.7089	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5763	Approved
0.7088	Intermediate Similarity	NPD6535	Approved
0.7088	Intermediate Similarity	NPD6534	Approved
0.7086	Intermediate Similarity	NPD6797	Phase 2
0.7081	Intermediate Similarity	NPD7236	Approved
0.7078	Intermediate Similarity	NPD8032	Phase 2
0.7076	Intermediate Similarity	NPD3787	Discontinued
0.7075	Intermediate Similarity	NPD4626	Approved
0.7075	Intermediate Similarity	NPD1778	Approved
0.7066	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7008	Discontinued
0.7059	Intermediate Similarity	NPD3027	Phase 3
0.7055	Intermediate Similarity	NPD3091	Approved
0.7055	Intermediate Similarity	NPD9545	Approved
0.7048	Intermediate Similarity	NPD7411	Suspended
0.7045	Intermediate Similarity	NPD7251	Discontinued
0.7043	Intermediate Similarity	NPD2494	Approved
0.7043	Intermediate Similarity	NPD2493	Approved
0.7037	Intermediate Similarity	NPD1511	Approved
0.7025	Intermediate Similarity	NPD2935	Discontinued
0.7025	Intermediate Similarity	NPD2531	Phase 2
0.7024	Intermediate Similarity	NPD3817	Phase 2
0.7022	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4582	Approved
0.7021	Intermediate Similarity	NPD8319	Approved
0.7021	Intermediate Similarity	NPD8320	Phase 1
0.7021	Intermediate Similarity	NPD4583	Approved
0.7013	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7177	Discontinued
0.7007	Intermediate Similarity	NPD5691	Approved
0.7006	Intermediate Similarity	NPD7097	Phase 1
0.6988	Remote Similarity	NPD6599	Discontinued
0.6987	Remote Similarity	NPD5735	Approved
0.6982	Remote Similarity	NPD3882	Suspended
0.6973	Remote Similarity	NPD7700	Phase 2
0.6973	Remote Similarity	NPD7699	Phase 2
0.697	Remote Similarity	NPD7239	Suspended
0.6968	Remote Similarity	NPD4002	Approved
0.6968	Remote Similarity	NPD7680	Approved
0.6968	Remote Similarity	NPD4004	Approved
0.6968	Remote Similarity	NPD7435	Discontinued
0.6966	Remote Similarity	NPD4198	Discontinued
0.6963	Remote Similarity	NPD8151	Discontinued
0.6962	Remote Similarity	NPD7033	Discontinued
0.6959	Remote Similarity	NPD5126	Approved
0.6959	Remote Similarity	NPD5125	Phase 3
0.6959	Remote Similarity	NPD17	Approved
0.6957	Remote Similarity	NPD3750	Approved
0.6952	Remote Similarity	NPD3450	Approved
0.6952	Remote Similarity	NPD3452	Approved
0.6951	Remote Similarity	NPD1512	Approved
0.6949	Remote Similarity	NPD6559	Discontinued
0.6948	Remote Similarity	NPD7095	Approved
0.6946	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD8434	Phase 2
0.6941	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.694	Remote Similarity	NPD6213	Phase 3
0.694	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.694	Remote Similarity	NPD6212	Phase 3
0.6933	Remote Similarity	NPD9269	Phase 2
0.6928	Remote Similarity	NPD2861	Phase 2
0.6928	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD943	Approved
0.6918	Remote Similarity	NPD4477	Approved
0.6918	Remote Similarity	NPD4476	Approved
0.6914	Remote Similarity	NPD3751	Discontinued
0.6913	Remote Similarity	NPD3026	Approved
0.6913	Remote Similarity	NPD3023	Approved
0.691	Remote Similarity	NPD7808	Phase 3
0.6909	Remote Similarity	NPD7427	Discontinued
0.6908	Remote Similarity	NPD1470	Approved
0.6905	Remote Similarity	NPD6801	Discontinued
0.6901	Remote Similarity	NPD3022	Approved
0.6901	Remote Similarity	NPD3021	Approved
0.6898	Remote Similarity	NPD6781	Approved
0.6898	Remote Similarity	NPD6782	Approved
0.6898	Remote Similarity	NPD6779	Approved
0.6898	Remote Similarity	NPD6780	Approved
0.6898	Remote Similarity	NPD6778	Approved
0.6898	Remote Similarity	NPD6776	Approved
0.6898	Remote Similarity	NPD6777	Approved
0.6897	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD1651	Approved
0.6892	Remote Similarity	NPD3024	Approved
0.6892	Remote Similarity	NPD3025	Approved
0.689	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD4908	Phase 1

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