NPASS Compound

Structure

CID25648 OpenBabel06191715352D 21 23 0 0 0 0 0 0 0 0999 V2000 -2.5981 0.5000 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 3.5000 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 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 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 0.8660 3.5000 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 0.8660 0.5000 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 3.4641 3.0000 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 2.0000 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 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 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 21 1 0 0 0 0 6 8 2 0 0 0 0 6 13 1 0 0 0 0 7 9 2 0 0 0 0 7 15 1 0 0 0 0 8 17 1 0 0 0 0 9 16 1 0 0 0 0 10 15 2 0 0 0 0 10 18 1 0 0 0 0 11 19 2 0 0 0 0 11 20 1 0 0 0 0 12 18 1 0 0 0 0 13 14 2 0 0 0 0 14 16 1 0 0 0 0 15 19 1 0 0 0 0 16 17 2 0 0 0 0 17 19 1 0 0 0 0 18 20 2 0 0 0 0 20 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	278.17
Volume:	319.142
LogP:	6.277
LogD:	4.958
LogS:	-7.208
# Rotatable Bonds:	2
TPSA:	9.23
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.543
Synthetic Accessibility Score:	2.065
Fsp3:	0.3
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:	-5.005
MDCK Permeability:	1.5030397662485484e-05
Pgp-inhibitor:	0.888
Pgp-substrate:	0.924
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.41
Plasma Protein Binding (PPB):	98.42794036865234%
Volume Distribution (VD):	1.479
Pgp-substrate:	0.9150294661521912%

ADMET: Metabolism

CYP1A2-inhibitor:	0.746
CYP1A2-substrate:	0.965
CYP2C19-inhibitor:	0.737
CYP2C19-substrate:	0.826
CYP2C9-inhibitor:	0.6
CYP2C9-substrate:	0.905
CYP2D6-inhibitor:	0.624
CYP2D6-substrate:	0.945
CYP3A4-inhibitor:	0.468
CYP3A4-substrate:	0.541

ADMET: Excretion

Clearance (CL):	6.908
Half-life (T1/2):	0.061

ADMET: Toxicity

hERG Blockers:	0.074
Human Hepatotoxicity (H-HT):	0.075
Drug-inuced Liver Injury (DILI):	0.93
AMES Toxicity:	0.792
Rat Oral Acute Toxicity:	0.283
Maximum Recommended Daily Dose:	0.941
Skin Sensitization:	0.782
Carcinogencity:	0.876
Eye Corrosion:	0.009
Eye Irritation:	0.979
Respiratory Toxicity:	0.133

Download Data

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

Natural Product: NPC25648

Natural Product ID:	NPC25648
*Common Name:**	Multicaulin
IUPAC Name:	6-methoxy-1,2-dimethyl-7-propan-2-ylphenanthrene
Synonyms:	Multicaulin
Standard InCHIKey:	QSZDTCGHFRXGFB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H22O/c1-12(2)18-10-15-7-9-16-14(4)13(3)6-8-17(16)19(15)11-20(18)21-5/h6-12H,1-5H3
SMILES:	COc1cc2c(cc1C(C)C)ccc1c2ccc(c1C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459187
PubChem CID:	467782
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
NPO21169	Salvia blepharochlaena	Species	Lamiaceae	Eukaryota	roots	n.a.	n.a.	PMID[11325249]
NPO29303	Salvia multicaulis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9428161]
NPO29303	Salvia multicaulis	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[9428161]
NPO29303	Salvia multicaulis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21169	Salvia blepharochlaena	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
MIC	5
Others	4

Activity Type	# Activity
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	5.6	ug.mL-1	PMID[526123]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.2	ug.mL-1	PMID[526123]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	>	7.0	mm	PMID[526123]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	0.7	ug.mL-1	PMID[526123]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	>	7.0	mm	PMID[526123]
NPT172	Organism	Proteus mirabilis	Proteus mirabilis	MIC	=	1.4	ug.mL-1	PMID[526123]
NPT172	Organism	Proteus mirabilis	Proteus mirabilis	IZ	>	7.0	mm	PMID[526123]
NPT174	Organism	Streptococcus	Streptococcus	MIC	=	0.2	ug.mL-1	PMID[526123]
NPT174	Organism	Streptococcus	Streptococcus	IZ	>	7.0	mm	PMID[526123]

☑ 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 NPC25648 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	594
0.1-0.2	2121
0.2-0.3	6005
0.3-0.4	12509
0.4-0.5	4332
0.5-0.6	7783
0.6-0.7	7576
0.7-0.8	1627
0.8-0.85	128
0.85-0.9	16
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9375	High Similarity	NPC312105
0.9273	High Similarity	NPC470723
0.9217	High Similarity	NPC103916
0.9115	High Similarity	NPC283169
0.887	High Similarity	NPC33900
0.8824	High Similarity	NPC152946
0.8814	High Similarity	NPC212559
0.8814	High Similarity	NPC129176
0.8807	High Similarity	NPC241224
0.8772	High Similarity	NPC715
0.8716	High Similarity	NPC12870
0.8716	High Similarity	NPC24327
0.8699	High Similarity	NPC215300
0.8678	High Similarity	NPC75432
0.864	High Similarity	NPC471983
0.864	High Similarity	NPC149337
0.8618	High Similarity	NPC53781
0.8618	High Similarity	NPC100129
0.8609	High Similarity	NPC35344
0.8609	High Similarity	NPC141003
0.8607	High Similarity	NPC4286
0.8607	High Similarity	NPC76119
0.8559	High Similarity	NPC63010
0.8548	High Similarity	NPC38017
0.8537	High Similarity	NPC170485
0.8534	High Similarity	NPC195922
0.8522	High Similarity	NPC46940
0.8492	Intermediate Similarity	NPC282508
0.8468	Intermediate Similarity	NPC186889
0.8455	Intermediate Similarity	NPC232387
0.8455	Intermediate Similarity	NPC105031
0.8455	Intermediate Similarity	NPC300166
0.8435	Intermediate Similarity	NPC95716
0.8425	Intermediate Similarity	NPC228843
0.8425	Intermediate Similarity	NPC183103
0.8421	Intermediate Similarity	NPC58865
0.8421	Intermediate Similarity	NPC314187
0.8374	Intermediate Similarity	NPC228503
0.8374	Intermediate Similarity	NPC61685
0.8374	Intermediate Similarity	NPC138248
0.8372	Intermediate Similarity	NPC37410
0.8361	Intermediate Similarity	NPC30462
0.8347	Intermediate Similarity	NPC100108
0.8347	Intermediate Similarity	NPC277798
0.832	Intermediate Similarity	NPC471986
0.8319	Intermediate Similarity	NPC30416
0.8308	Intermediate Similarity	NPC170328
0.8308	Intermediate Similarity	NPC472647
0.8308	Intermediate Similarity	NPC472649
0.8308	Intermediate Similarity	NPC206525
0.8308	Intermediate Similarity	NPC133463
0.8308	Intermediate Similarity	NPC472648
0.8308	Intermediate Similarity	NPC191462
0.8306	Intermediate Similarity	NPC29008
0.8306	Intermediate Similarity	NPC278955
0.8306	Intermediate Similarity	NPC113495
0.8306	Intermediate Similarity	NPC266705
0.8306	Intermediate Similarity	NPC228771
0.8306	Intermediate Similarity	NPC17348
0.8306	Intermediate Similarity	NPC105718
0.8305	Intermediate Similarity	NPC47194
0.8291	Intermediate Similarity	NPC322239
0.8291	Intermediate Similarity	NPC165106
0.8281	Intermediate Similarity	NPC189482
0.8279	Intermediate Similarity	NPC475839
0.8276	Intermediate Similarity	NPC260323
0.8276	Intermediate Similarity	NPC176279
0.8268	Intermediate Similarity	NPC254000
0.8268	Intermediate Similarity	NPC249425
0.8264	Intermediate Similarity	NPC135467
0.8264	Intermediate Similarity	NPC260832
0.8254	Intermediate Similarity	NPC223912
0.8254	Intermediate Similarity	NPC201069
0.8254	Intermediate Similarity	NPC181675
0.8246	Intermediate Similarity	NPC151477
0.8244	Intermediate Similarity	NPC71465
0.8244	Intermediate Similarity	NPC266006
0.8244	Intermediate Similarity	NPC186647
0.8244	Intermediate Similarity	NPC472646
0.824	Intermediate Similarity	NPC470724
0.8231	Intermediate Similarity	NPC258780
0.8226	Intermediate Similarity	NPC111088
0.8217	Intermediate Similarity	NPC470406
0.8217	Intermediate Similarity	NPC469610
0.8205	Intermediate Similarity	NPC250323
0.8203	Intermediate Similarity	NPC164295
0.8203	Intermediate Similarity	NPC8899
0.819	Intermediate Similarity	NPC141782
0.819	Intermediate Similarity	NPC475852
0.8189	Intermediate Similarity	NPC471518
0.8189	Intermediate Similarity	NPC471519
0.8182	Intermediate Similarity	NPC243996
0.8182	Intermediate Similarity	NPC275061
0.8182	Intermediate Similarity	NPC132804
0.8182	Intermediate Similarity	NPC220344
0.8182	Intermediate Similarity	NPC470161
0.8175	Intermediate Similarity	NPC177167
0.8175	Intermediate Similarity	NPC473221
0.8175	Intermediate Similarity	NPC428300
0.8174	Intermediate Similarity	NPC11554
0.8174	Intermediate Similarity	NPC75440
0.8174	Intermediate Similarity	NPC201959
0.8167	Intermediate Similarity	NPC299180
0.816	Intermediate Similarity	NPC28476
0.816	Intermediate Similarity	NPC9067
0.816	Intermediate Similarity	NPC470726
0.816	Intermediate Similarity	NPC133407
0.8158	Intermediate Similarity	NPC271274
0.8158	Intermediate Similarity	NPC326801
0.8154	Intermediate Similarity	NPC141023
0.8151	Intermediate Similarity	NPC35797
0.8151	Intermediate Similarity	NPC192948
0.8151	Intermediate Similarity	NPC473264
0.8151	Intermediate Similarity	NPC475815
0.814	Intermediate Similarity	NPC303144
0.814	Intermediate Similarity	NPC469611
0.8134	Intermediate Similarity	NPC186033
0.8125	Intermediate Similarity	NPC196193
0.812	Intermediate Similarity	NPC308768
0.812	Intermediate Similarity	NPC12668
0.812	Intermediate Similarity	NPC151537
0.812	Intermediate Similarity	NPC273623
0.811	Intermediate Similarity	NPC23012
0.811	Intermediate Similarity	NPC307050
0.811	Intermediate Similarity	NPC277458
0.8106	Intermediate Similarity	NPC266453
0.8106	Intermediate Similarity	NPC200935
0.8106	Intermediate Similarity	NPC242715
0.8106	Intermediate Similarity	NPC56329
0.8106	Intermediate Similarity	NPC230919
0.8106	Intermediate Similarity	NPC22902
0.8095	Intermediate Similarity	NPC82299
0.8095	Intermediate Similarity	NPC474737
0.8083	Intermediate Similarity	NPC81067
0.8083	Intermediate Similarity	NPC9341
0.8083	Intermediate Similarity	NPC219112
0.8083	Intermediate Similarity	NPC308311
0.8083	Intermediate Similarity	NPC38893
0.8083	Intermediate Similarity	NPC477137
0.807	Intermediate Similarity	NPC117115
0.8067	Intermediate Similarity	NPC268160
0.8062	Intermediate Similarity	NPC160623
0.8062	Intermediate Similarity	NPC473309
0.8062	Intermediate Similarity	NPC239134
0.8062	Intermediate Similarity	NPC471517
0.8049	Intermediate Similarity	NPC102639
0.8049	Intermediate Similarity	NPC131868
0.8047	Intermediate Similarity	NPC206028
0.8047	Intermediate Similarity	NPC16577
0.8045	Intermediate Similarity	NPC105847
0.8045	Intermediate Similarity	NPC243759
0.8045	Intermediate Similarity	NPC218131
0.8034	Intermediate Similarity	NPC13482
0.803	Intermediate Similarity	NPC30632
0.8017	Intermediate Similarity	NPC477136
0.8017	Intermediate Similarity	NPC172219
0.8017	Intermediate Similarity	NPC304510
0.8015	Intermediate Similarity	NPC213122
0.8	Intermediate Similarity	NPC73656
0.8	Intermediate Similarity	NPC147179
0.8	Intermediate Similarity	NPC85595
0.8	Intermediate Similarity	NPC175838
0.8	Intermediate Similarity	NPC183709
0.8	Intermediate Similarity	NPC113457
0.8	Intermediate Similarity	NPC21594
0.7984	Intermediate Similarity	NPC476633
0.7984	Intermediate Similarity	NPC470725
0.7984	Intermediate Similarity	NPC251259
0.7984	Intermediate Similarity	NPC470727
0.7984	Intermediate Similarity	NPC48623
0.7984	Intermediate Similarity	NPC168707
0.7983	Intermediate Similarity	NPC321589
0.7982	Intermediate Similarity	NPC238696
0.797	Intermediate Similarity	NPC151656
0.7955	Intermediate Similarity	NPC313081
0.7955	Intermediate Similarity	NPC158142
0.7955	Intermediate Similarity	NPC108198
0.7955	Intermediate Similarity	NPC69029
0.7955	Intermediate Similarity	NPC294884
0.7955	Intermediate Similarity	NPC241241
0.7955	Intermediate Similarity	NPC10314
0.7955	Intermediate Similarity	NPC200557
0.7951	Intermediate Similarity	NPC471671
0.7951	Intermediate Similarity	NPC190514
0.7951	Intermediate Similarity	NPC474040
0.7939	Intermediate Similarity	NPC227719
0.7939	Intermediate Similarity	NPC472524
0.7937	Intermediate Similarity	NPC248557
0.7934	Intermediate Similarity	NPC471668
0.7934	Intermediate Similarity	NPC469663
0.7934	Intermediate Similarity	NPC92
0.7934	Intermediate Similarity	NPC308828
0.7926	Intermediate Similarity	NPC472523
0.792	Intermediate Similarity	NPC188997
0.792	Intermediate Similarity	NPC473464
0.792	Intermediate Similarity	NPC476332
0.792	Intermediate Similarity	NPC71094
0.792	Intermediate Similarity	NPC150026
0.7917	Intermediate Similarity	NPC249270
0.7907	Intermediate Similarity	NPC96719

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 NPC25648 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	559
0.1-0.2	971
0.2-0.3	1232
0.3-0.4	2808
0.4-0.5	1815
0.5-0.6	1112
0.6-0.7	523
0.7-0.8	118
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8644	High Similarity	NPD1651	Approved
0.8487	Intermediate Similarity	NPD5691	Approved
0.8443	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.843	Intermediate Similarity	NPD1281	Approved
0.8417	Intermediate Similarity	NPD4626	Approved
0.8413	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD5327	Phase 3
0.8291	Intermediate Similarity	NPD5283	Phase 1
0.8261	Intermediate Similarity	NPD5451	Approved
0.8246	Intermediate Similarity	NPD2342	Discontinued
0.8226	Intermediate Similarity	NPD1283	Approved
0.8154	Intermediate Similarity	NPD4097	Suspended
0.813	Intermediate Similarity	NPD1611	Approved
0.8095	Intermediate Similarity	NPD4624	Approved
0.8047	Intermediate Similarity	NPD4625	Phase 3
0.8	Intermediate Similarity	NPD1669	Approved
0.8	Intermediate Similarity	NPD2979	Phase 3
0.7899	Intermediate Similarity	NPD7635	Approved
0.7868	Intermediate Similarity	NPD7003	Approved
0.7863	Intermediate Similarity	NPD4060	Phase 1
0.7851	Intermediate Similarity	NPD709	Approved
0.7846	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD5535	Approved
0.7744	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD3445	Approved
0.7742	Intermediate Similarity	NPD3443	Approved
0.7742	Intermediate Similarity	NPD3444	Approved
0.7727	Intermediate Similarity	NPD4140	Approved
0.7727	Intermediate Similarity	NPD3109	Approved
0.7727	Intermediate Similarity	NPD3110	Approved
0.7705	Intermediate Similarity	NPD6387	Discontinued
0.7704	Intermediate Similarity	NPD2531	Phase 2
0.7704	Intermediate Similarity	NPD2438	Suspended
0.7692	Intermediate Similarity	NPD4908	Phase 1
0.7669	Intermediate Similarity	NPD5735	Approved
0.7664	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD6581	Approved
0.7661	Intermediate Similarity	NPD6580	Approved
0.7652	Intermediate Similarity	NPD4475	Approved
0.7652	Intermediate Similarity	NPD4474	Approved
0.7652	Intermediate Similarity	NPD8032	Phase 2
0.763	Intermediate Similarity	NPD4108	Discontinued
0.7615	Intermediate Similarity	NPD2861	Phase 2
0.7612	Intermediate Similarity	NPD6353	Approved
0.76	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD3620	Phase 2
0.7576	Intermediate Similarity	NPD7294	Phase 1
0.7571	Intermediate Similarity	NPD7041	Phase 2
0.7571	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD496	Approved
0.7541	Intermediate Similarity	NPD498	Approved
0.7541	Intermediate Similarity	NPD495	Approved
0.754	Intermediate Similarity	NPD2286	Discontinued
0.7538	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD6584	Phase 3
0.7537	Intermediate Similarity	NPD3657	Discovery
0.7521	Intermediate Similarity	NPD1137	Approved
0.7521	Intermediate Similarity	NPD1139	Approved
0.752	Intermediate Similarity	NPD3091	Approved
0.75	Intermediate Similarity	NPD7340	Approved
0.75	Intermediate Similarity	NPD2230	Approved
0.75	Intermediate Similarity	NPD2232	Approved
0.75	Intermediate Similarity	NPD2233	Approved
0.748	Intermediate Similarity	NPD497	Approved
0.7478	Intermediate Similarity	NPD3020	Approved
0.7464	Intermediate Similarity	NPD7037	Approved
0.7459	Intermediate Similarity	NPD1138	Approved
0.7456	Intermediate Similarity	NPD288	Approved
0.7444	Intermediate Similarity	NPD5111	Phase 2
0.7444	Intermediate Similarity	NPD5110	Phase 2
0.7444	Intermediate Similarity	NPD5109	Approved
0.7442	Intermediate Similarity	NPD4749	Approved
0.744	Intermediate Similarity	NPD7644	Approved
0.7422	Intermediate Similarity	NPD1610	Phase 2
0.7419	Intermediate Similarity	NPD2557	Approved
0.7419	Intermediate Similarity	NPD6671	Approved
0.7417	Intermediate Similarity	NPD2684	Approved
0.7402	Intermediate Similarity	NPD3095	Discontinued
0.7402	Intermediate Similarity	NPD5846	Approved
0.7402	Intermediate Similarity	NPD2668	Approved
0.7402	Intermediate Similarity	NPD6516	Phase 2
0.7402	Intermediate Similarity	NPD2667	Approved
0.7398	Intermediate Similarity	NPD1398	Phase 1
0.7388	Intermediate Similarity	NPD7265	Discontinued
0.7385	Intermediate Similarity	NPD6696	Suspended
0.7385	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD1876	Approved
0.7368	Intermediate Similarity	NPD844	Approved
0.7364	Intermediate Similarity	NPD3972	Approved
0.736	Intermediate Similarity	NPD3596	Phase 2
0.7353	Intermediate Similarity	NPD2157	Approved
0.7343	Intermediate Similarity	NPD4319	Phase 2
0.7323	Intermediate Similarity	NPD5585	Approved
0.7323	Intermediate Similarity	NPD3024	Approved
0.7323	Intermediate Similarity	NPD3025	Approved
0.7323	Intermediate Similarity	NPD4093	Discontinued
0.7313	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6543	Approved
0.7308	Intermediate Similarity	NPD6582	Phase 2
0.7308	Intermediate Similarity	NPD6542	Approved
0.7308	Intermediate Similarity	NPD6540	Phase 3
0.7308	Intermediate Similarity	NPD6583	Phase 3
0.7308	Intermediate Similarity	NPD6539	Approved
0.7305	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD5536	Phase 2
0.7287	Intermediate Similarity	NPD3092	Approved
0.7286	Intermediate Similarity	NPD6674	Discontinued
0.728	Intermediate Similarity	NPD7157	Approved
0.7273	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD3019	Approved
0.7266	Intermediate Similarity	NPD4059	Approved
0.7252	Intermediate Similarity	NPD8651	Approved
0.7252	Intermediate Similarity	NPD6541	Approved
0.7252	Intermediate Similarity	NPD6538	Approved
0.725	Intermediate Similarity	NPD3134	Approved
0.7246	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7095	Approved
0.7236	Intermediate Similarity	NPD228	Approved
0.7231	Intermediate Similarity	NPD1840	Phase 2
0.7222	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD2859	Approved
0.7217	Intermediate Similarity	NPD2860	Approved
0.7213	Intermediate Similarity	NPD3021	Approved
0.7213	Intermediate Similarity	NPD3022	Approved
0.7209	Intermediate Similarity	NPD3023	Approved
0.7209	Intermediate Similarity	NPD3026	Approved
0.7206	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD4477	Approved
0.7194	Intermediate Similarity	NPD4476	Approved
0.7193	Intermediate Similarity	NPD845	Approved
0.7188	Intermediate Similarity	NPD3049	Approved
0.7185	Intermediate Similarity	NPD6798	Discontinued
0.7177	Intermediate Similarity	NPD7843	Approved
0.7154	Intermediate Similarity	NPD3705	Approved
0.7143	Intermediate Similarity	NPD7018	Phase 2
0.7143	Intermediate Similarity	NPD2798	Approved
0.7143	Intermediate Similarity	NPD5762	Approved
0.7143	Intermediate Similarity	NPD2346	Discontinued
0.7143	Intermediate Similarity	NPD5763	Approved
0.7143	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD17	Approved
0.7132	Intermediate Similarity	NPD2932	Approved
0.713	Intermediate Similarity	NPD2934	Approved
0.713	Intermediate Similarity	NPD2933	Approved
0.712	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD1548	Phase 1
0.7103	Intermediate Similarity	NPD6273	Approved
0.709	Intermediate Similarity	NPD3018	Phase 2
0.709	Intermediate Similarity	NPD1712	Approved
0.709	Intermediate Similarity	NPD5736	Approved
0.709	Intermediate Similarity	NPD2237	Approved
0.7083	Intermediate Similarity	NPD7598	Phase 2
0.708	Intermediate Similarity	NPD2238	Phase 2
0.7077	Intermediate Similarity	NPD3847	Discontinued
0.7073	Intermediate Similarity	NPD4750	Phase 3
0.7071	Intermediate Similarity	NPD2935	Discontinued
0.7069	Intermediate Similarity	NPD1809	Phase 2
0.7068	Intermediate Similarity	NPD2797	Approved
0.7068	Intermediate Similarity	NPD3094	Phase 2
0.7067	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1039	Discontinued
0.7055	Intermediate Similarity	NPD7427	Discontinued
0.7045	Intermediate Similarity	NPD4359	Approved
0.7039	Intermediate Similarity	NPD7400	Phase 3
0.7034	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6355	Discontinued
0.7015	Intermediate Similarity	NPD7905	Discontinued
0.7015	Intermediate Similarity	NPD3691	Phase 2
0.7015	Intermediate Similarity	NPD3690	Phase 2
0.7013	Intermediate Similarity	NPD6232	Discontinued
0.7	Intermediate Similarity	NPD5929	Approved
0.7	Intermediate Similarity	NPD2156	Approved
0.7	Intermediate Similarity	NPD2155	Approved
0.7	Intermediate Similarity	NPD2554	Approved
0.7	Intermediate Similarity	NPD2556	Approved
0.7	Intermediate Similarity	NPD2799	Discontinued
0.7	Intermediate Similarity	NPD1778	Approved
0.7	Intermediate Similarity	NPD2154	Approved
0.6993	Remote Similarity	NPD6331	Phase 2
0.6993	Remote Similarity	NPD5754	Discontinued
0.6993	Remote Similarity	NPD7466	Approved
0.6992	Remote Similarity	NPD2922	Phase 1
0.6987	Remote Similarity	NPD7473	Discontinued
0.6986	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6090	Discontinued
0.6985	Remote Similarity	NPD3027	Phase 3
0.6985	Remote Similarity	NPD1024	Discontinued
0.6984	Remote Similarity	NPD592	Approved
0.6984	Remote Similarity	NPD594	Approved
0.6983	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD2486	Discontinued
0.6977	Remote Similarity	NPD1182	Approved
0.6972	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.697	Remote Similarity	NPD2981	Phase 2
0.697	Remote Similarity	NPD1608	Approved
0.6967	Remote Similarity	NPD968	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