NPASS Compound

Structure

CID272268 OpenBabel06191716082D 27 29 0 0 0 0 0 0 0 0999 V2000 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -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 1.7321 -2.0000 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 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -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 0.8660 -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 -3.4641 -0.0000 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 -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 -0.8660 -0.5000 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 -0.0000 -2.0000 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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 5 2 0 0 0 0 4 6 1 0 0 0 0 5 11 1 0 0 0 0 6 12 2 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 13 1 0 0 0 0 10 14 1 0 0 0 0 10 18 2 0 0 0 0 11 15 2 0 0 0 0 11 19 1 0 0 0 0 12 15 1 0 0 0 0 12 22 1 0 0 0 0 13 14 1 0 0 0 0 13 23 2 0 0 0 0 14 20 2 0 0 0 0 15 21 1 0 0 0 0 16 17 2 0 0 0 0 16 18 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 17 21 1 0 0 0 0 18 24 1 0 0 0 0 19 25 2 0 0 0 0 20 26 1 0 0 0 0 21 27 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	368.13
Volume:	375.116
LogP:	5.686
LogD:	2.725
LogS:	-3.453
# Rotatable Bonds:	3
TPSA:	118.22
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.203
Synthetic Accessibility Score:	3.139
Fsp3:	0.19
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.142
MDCK Permeability:	6.749925432814052e-06
Pgp-inhibitor:	0.078
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.349
20% Bioavailability (F20%):	0.326
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	94.02872467041016%
Volume Distribution (VD):	0.559
Pgp-substrate:	8.177470207214355%

ADMET: Metabolism

CYP1A2-inhibitor:	0.801
CYP1A2-substrate:	0.191
CYP2C19-inhibitor:	0.19
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.76
CYP2C9-substrate:	0.59
CYP2D6-inhibitor:	0.288
CYP2D6-substrate:	0.164
CYP3A4-inhibitor:	0.067
CYP3A4-substrate:	0.055

ADMET: Excretion

Clearance (CL):	9.439
Half-life (T1/2):	0.593

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.326
Drug-inuced Liver Injury (DILI):	0.961
AMES Toxicity:	0.714
Rat Oral Acute Toxicity:	0.104
Maximum Recommended Daily Dose:	0.451
Skin Sensitization:	0.928
Carcinogencity:	0.483
Eye Corrosion:	0.004
Eye Irritation:	0.918
Respiratory Toxicity:	0.279

Download Data

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

Natural Product: NPC272268

Natural Product ID:	NPC272268
*Common Name:**	Galvaquinone B
IUPAC Name:	1,4,5-trihydroxy-2-methyl-3-(4-methylpentanoyl)anthracene-9,10-dione
Synonyms:	Galvaquinone B
Standard InCHIKey:	PKWTYZNHEWSFNN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H20O6/c1-9(2)7-8-13(23)14-10(3)18(24)16-17(20(14)26)21(27)15-11(19(16)25)5-4-6-12(15)22/h4-6,9,22,24,26H,7-8H2,1-3H3
SMILES:	CC(C)CCC(=O)c1c(C)c(c2c(c1O)C(=O)c1c(cccc1O)C2=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2152648
PubChem CID:	71456588
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones

*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
NPO12925	Streptomyces spinoverrucosus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23057874]
NPO12925	Streptomyces spinoverrucosus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26489038]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2311	Cell Line	Calu-3	Homo sapiens	IC50	=	12200.0	nM	PMID[521235]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5000.0	nM	PMID[521235]

☑ 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 NPC272268 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	370
0.1-0.2	1559
0.2-0.3	3378
0.3-0.4	9769
0.4-0.5	9835
0.5-0.6	5568
0.6-0.7	8289
0.7-0.8	3491
0.8-0.85	283
0.85-0.9	118
0.9-0.95	34
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9767	High Similarity	NPC115458
0.9612	High Similarity	NPC205992
0.9474	High Similarity	NPC245923
0.9398	High Similarity	NPC474813
0.938	High Similarity	NPC282923
0.9248	High Similarity	NPC288089
0.9242	High Similarity	NPC58685
0.9231	High Similarity	NPC48248
0.9225	High Similarity	NPC96915
0.9179	High Similarity	NPC283088
0.916	High Similarity	NPC99731
0.9147	High Similarity	NPC103540
0.913	High Similarity	NPC193555
0.9124	High Similarity	NPC315578
0.9118	High Similarity	NPC13715
0.9111	High Similarity	NPC155211
0.9111	High Similarity	NPC472308
0.9098	High Similarity	NPC70622
0.9077	High Similarity	NPC3224
0.9077	High Similarity	NPC306765
0.907	High Similarity	NPC173978
0.907	High Similarity	NPC142956
0.9058	High Similarity	NPC124365
0.9051	High Similarity	NPC26924
0.9044	High Similarity	NPC305060
0.9037	High Similarity	NPC80035
0.903	High Similarity	NPC53896
0.9021	High Similarity	NPC315520
0.9015	High Similarity	NPC34414
0.9015	High Similarity	NPC146647
0.8992	High Similarity	NPC375356
0.8986	High Similarity	NPC181560
0.8986	High Similarity	NPC169452
0.8963	High Similarity	NPC287604
0.8963	High Similarity	NPC472262
0.8963	High Similarity	NPC161964
0.8955	High Similarity	NPC246693
0.8955	High Similarity	NPC242358
0.8955	High Similarity	NPC110609
0.8947	High Similarity	NPC199253
0.8947	High Similarity	NPC55949
0.8947	High Similarity	NPC136588
0.8936	High Similarity	NPC471683
0.8915	High Similarity	NPC300274
0.8913	High Similarity	NPC143438
0.8913	High Similarity	NPC242994
0.8913	High Similarity	NPC138099
0.8889	High Similarity	NPC225051
0.8881	High Similarity	NPC17083
0.8872	High Similarity	NPC278928
0.8864	High Similarity	NPC471530
0.8849	High Similarity	NPC96421
0.8849	High Similarity	NPC225243
0.8841	High Similarity	NPC4214
0.8832	High Similarity	NPC193358
0.8794	High Similarity	NPC471682
0.8786	High Similarity	NPC187843
0.8777	High Similarity	NPC1268
0.8769	High Similarity	NPC307174
0.8768	High Similarity	NPC53414
0.8768	High Similarity	NPC471905
0.8768	High Similarity	NPC53206
0.8759	High Similarity	NPC161632
0.875	High Similarity	NPC52407
0.875	High Similarity	NPC314048
0.8741	High Similarity	NPC72669
0.8741	High Similarity	NPC244699
0.8741	High Similarity	NPC300540
0.8741	High Similarity	NPC85342
0.8741	High Similarity	NPC474517
0.8732	High Similarity	NPC10764
0.8723	High Similarity	NPC239136
0.8723	High Similarity	NPC257644
0.8723	High Similarity	NPC19631
0.8723	High Similarity	NPC474300
0.8716	High Similarity	NPC474861
0.8705	High Similarity	NPC61398
0.8705	High Similarity	NPC416
0.8696	High Similarity	NPC254847
0.8686	High Similarity	NPC50924
0.8667	High Similarity	NPC31539
0.8667	High Similarity	NPC31799
0.8662	High Similarity	NPC476473
0.8652	High Similarity	NPC290550
0.8647	High Similarity	NPC136342
0.8647	High Similarity	NPC295202
0.8647	High Similarity	NPC231774
0.8647	High Similarity	NPC227741
0.8647	High Similarity	NPC1991
0.8647	High Similarity	NPC49647
0.8633	High Similarity	NPC147418
0.8592	High Similarity	NPC73061
0.8592	High Similarity	NPC135524
0.8582	High Similarity	NPC42262
0.8582	High Similarity	NPC241349
0.8582	High Similarity	NPC220496
0.8582	High Similarity	NPC147542
0.8582	High Similarity	NPC32749
0.8582	High Similarity	NPC37992
0.8582	High Similarity	NPC327916
0.8581	High Similarity	NPC474824
0.8581	High Similarity	NPC470408
0.8581	High Similarity	NPC182921
0.8581	High Similarity	NPC218870
0.8571	High Similarity	NPC131799
0.8561	High Similarity	NPC141934
0.8561	High Similarity	NPC275145
0.8561	High Similarity	NPC474311
0.8561	High Similarity	NPC191976
0.8561	High Similarity	NPC477153
0.8551	High Similarity	NPC166480
0.8551	High Similarity	NPC44437
0.8551	High Similarity	NPC12070
0.8551	High Similarity	NPC282780
0.8538	High Similarity	NPC285829
0.8538	High Similarity	NPC206778
0.8531	High Similarity	NPC66593
0.8529	High Similarity	NPC108129
0.8521	High Similarity	NPC204045
0.8521	High Similarity	NPC246638
0.8521	High Similarity	NPC477275
0.8521	High Similarity	NPC305845
0.8519	High Similarity	NPC96024
0.8511	High Similarity	NPC476477
0.8511	High Similarity	NPC216312
0.8511	High Similarity	NPC256463
0.8511	High Similarity	NPC299405
0.8511	High Similarity	NPC111422
0.8511	High Similarity	NPC306835
0.8511	High Similarity	NPC29771
0.8511	High Similarity	NPC190457
0.8511	High Similarity	NPC471602
0.8496	Intermediate Similarity	NPC152525
0.8496	Intermediate Similarity	NPC74507
0.8496	Intermediate Similarity	NPC310540
0.8496	Intermediate Similarity	NPC234890
0.8496	Intermediate Similarity	NPC68756
0.8489	Intermediate Similarity	NPC22222
0.8489	Intermediate Similarity	NPC258502
0.8489	Intermediate Similarity	NPC281513
0.8489	Intermediate Similarity	NPC249272
0.8483	Intermediate Similarity	NPC147250
0.8478	Intermediate Similarity	NPC254603
0.8478	Intermediate Similarity	NPC114183
0.8478	Intermediate Similarity	NPC267205
0.8478	Intermediate Similarity	NPC193169
0.8473	Intermediate Similarity	NPC472046
0.8472	Intermediate Similarity	NPC244691
0.8472	Intermediate Similarity	NPC193703
0.8472	Intermediate Similarity	NPC79627
0.8472	Intermediate Similarity	NPC471906
0.8472	Intermediate Similarity	NPC21599
0.8462	Intermediate Similarity	NPC232178
0.8462	Intermediate Similarity	NPC474961
0.8456	Intermediate Similarity	NPC25736
0.8456	Intermediate Similarity	NPC276238
0.8456	Intermediate Similarity	NPC109123
0.8451	Intermediate Similarity	NPC183345
0.845	Intermediate Similarity	NPC269414
0.8444	Intermediate Similarity	NPC84672
0.8444	Intermediate Similarity	NPC176130
0.8444	Intermediate Similarity	NPC78364
0.8444	Intermediate Similarity	NPC69424
0.844	Intermediate Similarity	NPC206207
0.8429	Intermediate Similarity	NPC86524
0.8425	Intermediate Similarity	NPC37709
0.8417	Intermediate Similarity	NPC202225
0.8417	Intermediate Similarity	NPC1249
0.8417	Intermediate Similarity	NPC270899
0.8414	Intermediate Similarity	NPC170055
0.8414	Intermediate Similarity	NPC34482
0.8406	Intermediate Similarity	NPC309430
0.8403	Intermediate Similarity	NPC295712
0.8403	Intermediate Similarity	NPC238629
0.8403	Intermediate Similarity	NPC313047
0.8403	Intermediate Similarity	NPC53016
0.8403	Intermediate Similarity	NPC451542
0.8403	Intermediate Similarity	NPC474203
0.84	Intermediate Similarity	NPC66029
0.8394	Intermediate Similarity	NPC198305
0.8394	Intermediate Similarity	NPC475741
0.8392	Intermediate Similarity	NPC257003
0.8392	Intermediate Similarity	NPC471444
0.838	Intermediate Similarity	NPC162939
0.8378	Intermediate Similarity	NPC294646
0.8372	Intermediate Similarity	NPC477453
0.837	Intermediate Similarity	NPC160499
0.8369	Intermediate Similarity	NPC53001
0.8369	Intermediate Similarity	NPC62272
0.8369	Intermediate Similarity	NPC471452
0.8369	Intermediate Similarity	NPC475957
0.8358	Intermediate Similarity	NPC199273
0.8356	Intermediate Similarity	NPC314437
0.8356	Intermediate Similarity	NPC470570
0.8356	Intermediate Similarity	NPC285122
0.8346	Intermediate Similarity	NPC91478
0.8345	Intermediate Similarity	NPC48762
0.8345	Intermediate Similarity	NPC477139
0.8345	Intermediate Similarity	NPC294226
0.8345	Intermediate Similarity	NPC84568

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 NPC272268 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	331
0.1-0.2	953
0.2-0.3	1376
0.3-0.4	2711
0.4-0.5	2184
0.5-0.6	1117
0.6-0.7	413
0.7-0.8	58
0.8-0.85	4
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9147	High Similarity	NPD1470	Approved
0.8837	High Similarity	NPD1201	Approved
0.8696	High Similarity	NPD1509	Clinical (unspecified phase)
0.8435	Intermediate Similarity	NPD3226	Approved
0.8369	Intermediate Similarity	NPD5404	Approved
0.8369	Intermediate Similarity	NPD5405	Approved
0.8369	Intermediate Similarity	NPD5406	Approved
0.8369	Intermediate Similarity	NPD5408	Approved
0.8231	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD7390	Discontinued
0.8163	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD2346	Discontinued
0.7905	Intermediate Similarity	NPD3300	Phase 2
0.7862	Intermediate Similarity	NPD2935	Discontinued
0.7786	Intermediate Similarity	NPD7635	Approved
0.7721	Intermediate Similarity	NPD3019	Approved
0.7702	Intermediate Similarity	NPD7473	Discontinued
0.7671	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD943	Approved
0.7625	Intermediate Similarity	NPD6232	Discontinued
0.7591	Intermediate Similarity	NPD2932	Approved
0.7589	Intermediate Similarity	NPD2798	Approved
0.7551	Intermediate Similarity	NPD2799	Discontinued
0.7537	Intermediate Similarity	NPD5951	Approved
0.7518	Intermediate Similarity	NPD1164	Approved
0.75	Intermediate Similarity	NPD3764	Approved
0.75	Intermediate Similarity	NPD2313	Discontinued
0.7432	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD7003	Approved
0.7405	Intermediate Similarity	NPD2342	Discontinued
0.7358	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD8150	Discontinued
0.7351	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6959	Discontinued
0.7338	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1607	Approved
0.7296	Intermediate Similarity	NPD7819	Suspended
0.7286	Intermediate Similarity	NPD3023	Approved
0.7286	Intermediate Similarity	NPD3026	Approved
0.7283	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD8313	Approved
0.7278	Intermediate Similarity	NPD8312	Approved
0.7267	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD3024	Approved
0.7266	Intermediate Similarity	NPD3025	Approved
0.7266	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2533	Approved
0.7226	Intermediate Similarity	NPD2534	Approved
0.7226	Intermediate Similarity	NPD2532	Approved
0.7226	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1471	Phase 3
0.7219	Intermediate Similarity	NPD2344	Approved
0.7214	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1510	Phase 2
0.7188	Intermediate Similarity	NPD2801	Approved
0.7188	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7411	Suspended
0.7162	Intermediate Similarity	NPD1240	Approved
0.7107	Intermediate Similarity	NPD4380	Phase 2
0.7102	Intermediate Similarity	NPD6534	Approved
0.7102	Intermediate Similarity	NPD6535	Approved
0.709	Intermediate Similarity	NPD9266	Approved
0.709	Intermediate Similarity	NPD74	Approved
0.7083	Intermediate Similarity	NPD5844	Phase 1
0.7083	Intermediate Similarity	NPD1283	Approved
0.7078	Intermediate Similarity	NPD3750	Approved
0.7073	Intermediate Similarity	NPD5494	Approved
0.7063	Intermediate Similarity	NPD4878	Approved
0.7059	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5027	Approved
0.7059	Intermediate Similarity	NPD5031	Approved
0.7059	Intermediate Similarity	NPD5029	Approved
0.705	Intermediate Similarity	NPD9493	Approved
0.7045	Intermediate Similarity	NPD6213	Phase 3
0.7045	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6212	Phase 3
0.7044	Intermediate Similarity	NPD7458	Discontinued
0.7037	Intermediate Similarity	NPD4750	Phase 3
0.7032	Intermediate Similarity	NPD2309	Approved
0.7029	Intermediate Similarity	NPD497	Approved
0.7027	Intermediate Similarity	NPD3268	Approved
0.7021	Intermediate Similarity	NPD1651	Approved
0.7015	Intermediate Similarity	NPD9263	Approved
0.7015	Intermediate Similarity	NPD9264	Approved
0.7015	Intermediate Similarity	NPD9267	Approved
0.7006	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6780	Approved
0.7	Intermediate Similarity	NPD6779	Approved
0.7	Intermediate Similarity	NPD6778	Approved
0.7	Intermediate Similarity	NPD6777	Approved
0.7	Intermediate Similarity	NPD6782	Approved
0.7	Intermediate Similarity	NPD6776	Approved
0.7	Intermediate Similarity	NPD6781	Approved
0.6994	Remote Similarity	NPD7768	Phase 2
0.6993	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7699	Phase 2
0.6983	Remote Similarity	NPD7700	Phase 2
0.698	Remote Similarity	NPD6663	Approved
0.6977	Remote Similarity	NPD288	Approved
0.697	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1930	Approved
0.697	Remote Similarity	NPD1929	Approved
0.6968	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD8166	Discontinued
0.6968	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD1876	Approved
0.6964	Remote Similarity	NPD5033	Approved
0.6959	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD498	Approved
0.6957	Remote Similarity	NPD495	Approved
0.6957	Remote Similarity	NPD496	Approved
0.6951	Remote Similarity	NPD3749	Approved
0.6948	Remote Similarity	NPD1549	Phase 2
0.6947	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1511	Approved
0.6939	Remote Similarity	NPD5736	Approved
0.6933	Remote Similarity	NPD5402	Approved
0.6928	Remote Similarity	NPD6100	Approved
0.6928	Remote Similarity	NPD1551	Phase 2
0.6928	Remote Similarity	NPD6099	Approved
0.6919	Remote Similarity	NPD5028	Approved
0.6919	Remote Similarity	NPD4954	Approved
0.6919	Remote Similarity	NPD5026	Approved
0.6919	Remote Similarity	NPD5034	Approved
0.6919	Remote Similarity	NPD4955	Approved
0.6919	Remote Similarity	NPD36	Approved
0.6918	Remote Similarity	NPD1203	Approved
0.6914	Remote Similarity	NPD1934	Approved
0.6914	Remote Similarity	NPD6844	Discontinued
0.6899	Remote Similarity	NPD844	Approved
0.6885	Remote Similarity	NPD7696	Phase 3
0.6885	Remote Similarity	NPD7435	Discontinued
0.6885	Remote Similarity	NPD7698	Approved
0.6885	Remote Similarity	NPD7697	Approved
0.6883	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6020	Phase 2
0.6875	Remote Similarity	NPD1281	Approved
0.6875	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.687	Remote Similarity	NPD3020	Approved
0.6863	Remote Similarity	NPD4308	Phase 3
0.6861	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6559	Discontinued
0.686	Remote Similarity	NPD5030	Phase 2
0.6857	Remote Similarity	NPD5037	Approved
0.6857	Remote Similarity	NPD5038	Approved
0.6855	Remote Similarity	NPD1512	Approved
0.6855	Remote Similarity	NPD6273	Approved
0.6853	Remote Similarity	NPD4626	Approved
0.6853	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7075	Discontinued
0.6848	Remote Similarity	NPD7870	Phase 2
0.6848	Remote Similarity	NPD7871	Phase 2
0.6846	Remote Similarity	NPD4625	Phase 3
0.6846	Remote Similarity	NPD7008	Discontinued
0.6838	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD3091	Approved
0.6831	Remote Similarity	NPD6823	Phase 2
0.6829	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD3972	Approved
0.6824	Remote Similarity	NPD7177	Discontinued
0.6821	Remote Similarity	NPD2979	Phase 3
0.6821	Remote Similarity	NPD5032	Approved
0.6818	Remote Similarity	NPD2796	Approved
0.6809	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD3094	Phase 2
0.6803	Remote Similarity	NPD2797	Approved
0.68	Remote Similarity	NPD5036	Approved
0.68	Remote Similarity	NPD411	Approved
0.6795	Remote Similarity	NPD2800	Approved
0.6788	Remote Similarity	NPD3021	Approved
0.6788	Remote Similarity	NPD3882	Suspended
0.6788	Remote Similarity	NPD3022	Approved
0.6786	Remote Similarity	NPD9281	Approved
0.6781	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6836	Approved
0.6776	Remote Similarity	NPD447	Suspended
0.6768	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD1932	Approved
0.6765	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD5039	Approved
0.6759	Remote Similarity	NPD1611	Approved
0.6759	Remote Similarity	NPD3092	Approved
0.6757	Remote Similarity	NPD8320	Phase 1
0.6757	Remote Similarity	NPD8319	Approved
0.6753	Remote Similarity	NPD3748	Approved
0.6752	Remote Similarity	NPD4628	Phase 3
0.6744	Remote Similarity	NPD845	Approved
0.6742	Remote Similarity	NPD2066	Phase 3
0.6738	Remote Similarity	NPD7701	Phase 2
0.6736	Remote Similarity	NPD4059	Approved
0.6736	Remote Similarity	NPD2286	Discontinued
0.6735	Remote Similarity	NPD6696	Suspended
0.672	Remote Similarity	NPD7801	Approved
0.672	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD9261	Approved
0.6715	Remote Similarity	NPD2329	Discontinued
0.6712	Remote Similarity	NPD9717	Approved
0.6712	Remote Similarity	NPD1608	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