NPASS Compound

Structure

CID96024 OpenBabel06191715432D 22 24 0 0 0 0 0 0 0 0999 V2000 1.7321 -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 -4.3301 -0.5000 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 -1.7321 -2.0000 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 0.0000 -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 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 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 -0.8660 -1.5000 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 0.8660 -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 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 0.8660 -0.5000 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 -2.5981 2.5000 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 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 4 11 1 0 0 0 0 5 6 2 0 0 0 0 5 12 1 0 0 0 0 6 13 1 0 0 0 0 7 12 1 0 0 0 0 7 14 2 0 0 0 0 8 15 2 0 0 0 0 8 16 1 0 0 0 0 9 14 1 0 0 0 0 10 11 1 0 0 0 0 10 13 2 0 0 0 0 11 16 2 0 0 0 0 12 17 2 0 0 0 0 13 15 1 0 0 0 0 14 18 1 0 0 0 0 15 17 1 0 0 0 0 16 20 1 0 0 0 0 17 19 1 0 0 0 0 18 19 1 0 0 0 0 18 21 2 0 0 0 0 19 22 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	294.13
Volume:	316.79
LogP:	4.571
LogD:	3.682
LogS:	-6.27
# Rotatable Bonds:	1
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.81
Synthetic Accessibility Score:	2.824
Fsp3:	0.263
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.954
MDCK Permeability:	1.797528784663882e-05
Pgp-inhibitor:	0.133
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.399
30% Bioavailability (F30%):	0.964

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.048
Plasma Protein Binding (PPB):	100.176025390625%
Volume Distribution (VD):	0.303
Pgp-substrate:	0.7430053949356079%

ADMET: Metabolism

CYP1A2-inhibitor:	0.932
CYP1A2-substrate:	0.925
CYP2C19-inhibitor:	0.699
CYP2C19-substrate:	0.154
CYP2C9-inhibitor:	0.808
CYP2C9-substrate:	0.784
CYP2D6-inhibitor:	0.755
CYP2D6-substrate:	0.283
CYP3A4-inhibitor:	0.504
CYP3A4-substrate:	0.162

ADMET: Excretion

Clearance (CL):	4.331
Half-life (T1/2):	0.084

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.272
Drug-inuced Liver Injury (DILI):	0.915
AMES Toxicity:	0.837
Rat Oral Acute Toxicity:	0.556
Maximum Recommended Daily Dose:	0.928
Skin Sensitization:	0.862
Carcinogencity:	0.917
Eye Corrosion:	0.025
Eye Irritation:	0.983
Respiratory Toxicity:	0.653

Download Data

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

Natural Product: NPC96024

Natural Product ID:	NPC96024
*Common Name:**	Demethylmultiorthoquinone
IUPAC Name:	6-hydroxy-7,8-dimethyl-2-propan-2-ylphenanthrene-3,4-dione
Synonyms:	Demethylmultiorthoquinone
Standard InCHIKey:	OVYJWDSHGYTZSE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H18O3/c1-9(2)14-7-12-5-6-13-10(3)11(4)16(20)8-15(13)17(12)19(22)18(14)21/h5-9,20H,1-4H3
SMILES:	CC(C)C1=Cc2ccc3c(C)c(C)c(cc3c2C(=O)C1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449749
PubChem CID:	467785
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002548] Tanshinones, isotanshinones, and derivatives

*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	2
Others	1

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	1.2	ug.mL-1	PMID[491705]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	4.6	ug.mL-1	PMID[491705]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	>	7.0	mm	PMID[491705]

☑ 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 NPC96024 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	328
0.1-0.2	1582
0.2-0.3	3292
0.3-0.4	9817
0.4-0.5	9239
0.5-0.6	5668
0.6-0.7	8548
0.7-0.8	3641
0.8-0.85	430
0.85-0.9	121
0.9-0.95	27
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9669	High Similarity	NPC199273
0.9597	High Similarity	NPC276238
0.9593	High Similarity	NPC72667
0.9512	High Similarity	NPC254492
0.9504	High Similarity	NPC282577
0.944	High Similarity	NPC171460
0.9435	High Similarity	NPC84672
0.9435	High Similarity	NPC69424
0.9435	High Similarity	NPC176130
0.9435	High Similarity	NPC78364
0.9274	High Similarity	NPC123506
0.9225	High Similarity	NPC50924
0.9213	High Similarity	NPC108129
0.9141	High Similarity	NPC471851
0.9134	High Similarity	NPC303910
0.9106	High Similarity	NPC154696
0.9055	High Similarity	NPC3009
0.9055	High Similarity	NPC48248
0.9032	High Similarity	NPC176208
0.9024	High Similarity	NPC32322
0.9024	High Similarity	NPC259703
0.9008	High Similarity	NPC283088
0.9008	High Similarity	NPC153088
0.9	High Similarity	NPC477139
0.9	High Similarity	NPC78307
0.9	High Similarity	NPC138472
0.8992	High Similarity	NPC244699
0.896	High Similarity	NPC273683
0.8952	High Similarity	NPC120545
0.8931	High Similarity	NPC202225
0.8923	High Similarity	NPC183103
0.8915	High Similarity	NPC27659
0.8898	High Similarity	NPC160499
0.8889	High Similarity	NPC164014
0.888	High Similarity	NPC91478
0.8872	High Similarity	NPC36868
0.8872	High Similarity	NPC53001
0.8855	High Similarity	NPC53896
0.8855	High Similarity	NPC111845
0.8855	High Similarity	NPC225051
0.8846	High Similarity	NPC93015
0.8846	High Similarity	NPC474517
0.8846	High Similarity	NPC41847
0.8846	High Similarity	NPC72669
0.8843	High Similarity	NPC322197
0.8837	High Similarity	NPC117899
0.8837	High Similarity	NPC146647
0.8837	High Similarity	NPC34414
0.8815	High Similarity	NPC181560
0.8815	High Similarity	NPC169452
0.881	High Similarity	NPC275145
0.8806	High Similarity	NPC87723
0.8788	High Similarity	NPC12070
0.8779	High Similarity	NPC58685
0.8769	High Similarity	NPC55949
0.876	High Similarity	NPC193203
0.875	High Similarity	NPC71610
0.875	High Similarity	NPC15837
0.8741	High Similarity	NPC242994
0.8741	High Similarity	NPC138099
0.874	High Similarity	NPC142956
0.874	High Similarity	NPC173978
0.8731	High Similarity	NPC475957
0.873	High Similarity	NPC307174
0.8722	High Similarity	NPC249272
0.8722	High Similarity	NPC80035
0.872	High Similarity	NPC190971
0.872	High Similarity	NPC216216
0.8712	High Similarity	NPC52407
0.8712	High Similarity	NPC115458
0.8712	High Similarity	NPC114183
0.8702	High Similarity	NPC18798
0.8692	High Similarity	NPC99731
0.8686	High Similarity	NPC239136
0.8686	High Similarity	NPC193555
0.8686	High Similarity	NPC19631
0.8678	High Similarity	NPC242136
0.8672	High Similarity	NPC137750
0.8667	High Similarity	NPC230811
0.8667	High Similarity	NPC4214
0.8667	High Similarity	NPC13715
0.8657	High Similarity	NPC155211
0.8657	High Similarity	NPC471670
0.8657	High Similarity	NPC191976
0.8651	High Similarity	NPC295034
0.8647	High Similarity	NPC282780
0.8647	High Similarity	NPC270899
0.8647	High Similarity	NPC166480
0.8636	High Similarity	NPC175738
0.8633	High Similarity	NPC478160
0.8629	High Similarity	NPC328694
0.8626	High Similarity	NPC253488
0.8615	High Similarity	NPC229894
0.8615	High Similarity	NPC282923
0.8605	High Similarity	NPC3224
0.8603	High Similarity	NPC470407
0.8595	High Similarity	NPC231717
0.8593	High Similarity	NPC264022
0.8593	High Similarity	NPC53414
0.8593	High Similarity	NPC471905
0.8593	High Similarity	NPC53206
0.8583	High Similarity	NPC300274
0.8582	High Similarity	NPC258502
0.8571	High Similarity	NPC267205
0.8571	High Similarity	NPC59459
0.8571	High Similarity	NPC241001
0.8561	High Similarity	NPC239134
0.8561	High Similarity	NPC85342
0.855	High Similarity	NPC92624
0.8529	High Similarity	NPC416
0.8529	High Similarity	NPC61398
0.8519	High Similarity	NPC272268
0.8519	High Similarity	NPC254847
0.8519	High Similarity	NPC118919
0.8516	High Similarity	NPC471187
0.8516	High Similarity	NPC375356
0.8507	High Similarity	NPC472262
0.8507	High Similarity	NPC161964
0.8507	High Similarity	NPC287604
0.8504	High Similarity	NPC249340
0.8504	High Similarity	NPC162935
0.8492	Intermediate Similarity	NPC478121
0.8492	Intermediate Similarity	NPC285829
0.8492	Intermediate Similarity	NPC206778
0.8489	Intermediate Similarity	NPC296752
0.8489	Intermediate Similarity	NPC451542
0.8489	Intermediate Similarity	NPC313047
0.8489	Intermediate Similarity	NPC478164
0.8489	Intermediate Similarity	NPC474203
0.8489	Intermediate Similarity	NPC295712
0.8485	Intermediate Similarity	NPC259942
0.8485	Intermediate Similarity	NPC199253
0.8485	Intermediate Similarity	NPC136588
0.8478	Intermediate Similarity	NPC246638
0.8473	Intermediate Similarity	NPC234175
0.8468	Intermediate Similarity	NPC477453
0.8462	Intermediate Similarity	NPC474737
0.8462	Intermediate Similarity	NPC306765
0.8456	Intermediate Similarity	NPC186647
0.8456	Intermediate Similarity	NPC245923
0.8456	Intermediate Similarity	NPC277559
0.845	Intermediate Similarity	NPC181334
0.845	Intermediate Similarity	NPC236189
0.8444	Intermediate Similarity	NPC290803
0.8444	Intermediate Similarity	NPC477596
0.8444	Intermediate Similarity	NPC22644
0.8443	Intermediate Similarity	NPC286222
0.8443	Intermediate Similarity	NPC46940
0.8438	Intermediate Similarity	NPC121168
0.8438	Intermediate Similarity	NPC11250
0.8433	Intermediate Similarity	NPC314048
0.8433	Intermediate Similarity	NPC294226
0.843	Intermediate Similarity	NPC116842
0.8421	Intermediate Similarity	NPC205992
0.8421	Intermediate Similarity	NPC476847
0.8421	Intermediate Similarity	NPC164295
0.8417	Intermediate Similarity	NPC135524
0.8417	Intermediate Similarity	NPC469520
0.8417	Intermediate Similarity	NPC201297
0.8417	Intermediate Similarity	NPC477209
0.8413	Intermediate Similarity	NPC473767
0.8409	Intermediate Similarity	NPC109123
0.8409	Intermediate Similarity	NPC25736
0.8406	Intermediate Similarity	NPC471853
0.8406	Intermediate Similarity	NPC315578
0.8406	Intermediate Similarity	NPC168471
0.8397	Intermediate Similarity	NPC471530
0.8385	Intermediate Similarity	NPC103540
0.8382	Intermediate Similarity	NPC7464
0.8382	Intermediate Similarity	NPC474311
0.8382	Intermediate Similarity	NPC475549
0.8382	Intermediate Similarity	NPC474813
0.8374	Intermediate Similarity	NPC715
0.8372	Intermediate Similarity	NPC198014
0.8372	Intermediate Similarity	NPC174991
0.837	Intermediate Similarity	NPC477594
0.837	Intermediate Similarity	NPC44437
0.8361	Intermediate Similarity	NPC95716
0.8359	Intermediate Similarity	NPC253627
0.8358	Intermediate Similarity	NPC312560
0.8358	Intermediate Similarity	NPC165612
0.8358	Intermediate Similarity	NPC70622
0.8357	Intermediate Similarity	NPC174905
0.8357	Intermediate Similarity	NPC293545
0.8357	Intermediate Similarity	NPC100242
0.8357	Intermediate Similarity	NPC66593
0.8347	Intermediate Similarity	NPC95172
0.8347	Intermediate Similarity	NPC58865
0.8346	Intermediate Similarity	NPC318552
0.8346	Intermediate Similarity	NPC31799
0.8346	Intermediate Similarity	NPC117609
0.8346	Intermediate Similarity	NPC190501
0.8346	Intermediate Similarity	NPC245395
0.8345	Intermediate Similarity	NPC477275
0.8345	Intermediate Similarity	NPC305845
0.8345	Intermediate Similarity	NPC204045
0.8345	Intermediate Similarity	NPC110810
0.8333	Intermediate Similarity	NPC162939
0.8333	Intermediate Similarity	NPC474890
0.8333	Intermediate Similarity	NPC161943

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 NPC96024 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	336
0.1-0.2	977
0.2-0.3	1153
0.3-0.4	2521
0.4-0.5	2320
0.5-0.6	1213
0.6-0.7	508
0.7-0.8	112
0.8-0.85	8
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8519	High Similarity	NPD1509	Clinical (unspecified phase)
0.8504	High Similarity	NPD1201	Approved
0.8492	Intermediate Similarity	NPD2932	Approved
0.8385	Intermediate Similarity	NPD1470	Approved
0.8346	Intermediate Similarity	NPD3019	Approved
0.8321	Intermediate Similarity	NPD5408	Approved
0.8321	Intermediate Similarity	NPD5406	Approved
0.8321	Intermediate Similarity	NPD5405	Approved
0.8321	Intermediate Similarity	NPD5404	Approved
0.8298	Intermediate Similarity	NPD7390	Discontinued
0.8268	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.8175	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD7003	Approved
0.8	Intermediate Similarity	NPD7635	Approved
0.797	Intermediate Similarity	NPD1164	Approved
0.7895	Intermediate Similarity	NPD1283	Approved
0.7886	Intermediate Similarity	NPD2342	Discontinued
0.7874	Intermediate Similarity	NPD5951	Approved
0.7862	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7846	Intermediate Similarity	NPD1651	Approved
0.7746	Intermediate Similarity	NPD2346	Discontinued
0.7744	Intermediate Similarity	NPD3972	Approved
0.773	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD3023	Approved
0.7727	Intermediate Similarity	NPD3026	Approved
0.7724	Intermediate Similarity	NPD3300	Phase 2
0.771	Intermediate Similarity	NPD3025	Approved
0.771	Intermediate Similarity	NPD3024	Approved
0.7698	Intermediate Similarity	NPD943	Approved
0.7676	Intermediate Similarity	NPD2935	Discontinued
0.7669	Intermediate Similarity	NPD1281	Approved
0.7652	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD7458	Discontinued
0.7647	Intermediate Similarity	NPD2798	Approved
0.7622	Intermediate Similarity	NPD2344	Approved
0.7606	Intermediate Similarity	NPD2799	Discontinued
0.7603	Intermediate Similarity	NPD3020	Approved
0.7589	Intermediate Similarity	NPD1607	Approved
0.7554	Intermediate Similarity	NPD3764	Approved
0.7533	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD3226	Approved
0.7532	Intermediate Similarity	NPD7473	Discontinued
0.7519	Intermediate Similarity	NPD4626	Approved
0.7517	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6663	Approved
0.75	Intermediate Similarity	NPD1876	Approved
0.7481	Intermediate Similarity	NPD4878	Approved
0.7466	Intermediate Similarity	NPD3750	Approved
0.7466	Intermediate Similarity	NPD8166	Discontinued
0.7464	Intermediate Similarity	NPD5736	Approved
0.746	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6232	Discontinued
0.7451	Intermediate Similarity	NPD7819	Suspended
0.7447	Intermediate Similarity	NPD1240	Approved
0.7438	Intermediate Similarity	NPD288	Approved
0.7419	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD1930	Approved
0.7419	Intermediate Similarity	NPD1929	Approved
0.7415	Intermediate Similarity	NPD2309	Approved
0.7389	Intermediate Similarity	NPD6959	Discontinued
0.7388	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD2286	Discontinued
0.7383	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3091	Approved
0.7361	Intermediate Similarity	NPD1510	Phase 2
0.7361	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2860	Approved
0.7355	Intermediate Similarity	NPD844	Approved
0.7355	Intermediate Similarity	NPD2859	Approved
0.7344	Intermediate Similarity	NPD3021	Approved
0.7344	Intermediate Similarity	NPD3022	Approved
0.7344	Intermediate Similarity	NPD4750	Phase 3
0.7333	Intermediate Similarity	NPD6273	Approved
0.7324	Intermediate Similarity	NPD2979	Phase 3
0.731	Intermediate Similarity	NPD6099	Approved
0.731	Intermediate Similarity	NPD6100	Approved
0.7299	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2933	Approved
0.7273	Intermediate Similarity	NPD2934	Approved
0.7267	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD4059	Approved
0.7239	Intermediate Similarity	NPD9545	Approved
0.7234	Intermediate Similarity	NPD7008	Discontinued
0.7231	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD4628	Phase 3
0.7226	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5844	Phase 1
0.7211	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD2797	Approved
0.719	Intermediate Similarity	NPD845	Approved
0.7185	Intermediate Similarity	NPD5691	Approved
0.7185	Intermediate Similarity	NPD4093	Discontinued
0.7183	Intermediate Similarity	NPD2313	Discontinued
0.7183	Intermediate Similarity	NPD3268	Approved
0.7179	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD2066	Phase 3
0.7174	Intermediate Similarity	NPD1755	Approved
0.7154	Intermediate Similarity	NPD3495	Discontinued
0.7153	Intermediate Similarity	NPD3092	Approved
0.7152	Intermediate Similarity	NPD2534	Approved
0.7152	Intermediate Similarity	NPD2532	Approved
0.7152	Intermediate Similarity	NPD2533	Approved
0.7143	Intermediate Similarity	NPD4380	Phase 2
0.7143	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD74	Approved
0.7132	Intermediate Similarity	NPD9266	Approved
0.7123	Intermediate Similarity	NPD3748	Approved
0.7123	Intermediate Similarity	NPD4308	Phase 3
0.7117	Intermediate Similarity	NPD6020	Phase 2
0.7114	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4625	Phase 3
0.7101	Intermediate Similarity	NPD1608	Approved
0.7095	Intermediate Similarity	NPD1549	Phase 2
0.709	Intermediate Similarity	NPD9493	Approved
0.709	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD1237	Approved
0.7083	Intermediate Similarity	NPD4060	Phase 1
0.708	Intermediate Similarity	NPD4879	Approved
0.7075	Intermediate Similarity	NPD2531	Phase 2
0.7075	Intermediate Similarity	NPD2438	Suspended
0.7075	Intermediate Similarity	NPD2796	Approved
0.7073	Intermediate Similarity	NPD1809	Phase 2
0.7068	Intermediate Similarity	NPD497	Approved
0.7063	Intermediate Similarity	NPD1932	Approved
0.7055	Intermediate Similarity	NPD7177	Discontinued
0.7054	Intermediate Similarity	NPD9267	Approved
0.7054	Intermediate Similarity	NPD9264	Approved
0.7054	Intermediate Similarity	NPD9263	Approved
0.7037	Intermediate Similarity	NPD7610	Discontinued
0.7027	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1471	Phase 3
0.7027	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6884	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD8032	Phase 2
0.7007	Intermediate Similarity	NPD3095	Discontinued
0.7	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2329	Discontinued
0.6992	Remote Similarity	NPD496	Approved
0.6992	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD498	Approved
0.6992	Remote Similarity	NPD495	Approved
0.6987	Remote Similarity	NPD7411	Suspended
0.6984	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD8150	Discontinued
0.6981	Remote Similarity	NPD3749	Approved
0.6981	Remote Similarity	NPD7075	Discontinued
0.6974	Remote Similarity	NPD1511	Approved
0.6972	Remote Similarity	NPD9494	Approved
0.6962	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4476	Approved
0.6959	Remote Similarity	NPD4477	Approved
0.6954	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.695	Remote Similarity	NPD3094	Phase 2
0.6943	Remote Similarity	NPD1934	Approved
0.6933	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7768	Phase 2
0.6906	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD2801	Approved
0.6899	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD17	Approved
0.6884	Remote Similarity	NPD1751	Approved
0.6883	Remote Similarity	NPD1512	Approved
0.6875	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4097	Suspended
0.6871	Remote Similarity	NPD6651	Approved
0.6866	Remote Similarity	NPD1241	Discontinued
0.6866	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD7009	Phase 2
0.6861	Remote Similarity	NPD5304	Approved
0.6861	Remote Similarity	NPD5303	Approved
0.6857	Remote Similarity	NPD9269	Phase 2
0.6855	Remote Similarity	NPD2296	Approved
0.6855	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD4307	Phase 2
0.6831	Remote Similarity	NPD1203	Approved
0.6831	Remote Similarity	NPD3266	Approved
0.6831	Remote Similarity	NPD3267	Approved
0.6829	Remote Similarity	NPD7631	Approved
0.6821	Remote Similarity	NPD2800	Approved
0.6818	Remote Similarity	NPD1792	Phase 2
0.6815	Remote Similarity	NPD6599	Discontinued
0.6813	Remote Similarity	NPD3882	Suspended
0.6812	Remote Similarity	NPD9268	Approved
0.6797	Remote Similarity	NPD7236	Approved
0.6797	Remote Similarity	NPD846	Approved
0.6797	Remote Similarity	NPD940	Approved
0.6792	Remote Similarity	NPD1465	Phase 2
0.679	Remote Similarity	NPD5494	Approved
0.6786	Remote Similarity	NPD6559	Discontinued
0.6786	Remote Similarity	NPD1611	Approved
0.6765	Remote Similarity	NPD3317	Approved
0.6763	Remote Similarity	NPD4589	Approved
0.6759	Remote Similarity	NPD5156	Approved
0.6759	Remote Similarity	NPD5155	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