NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	280.06
Volume:	262.004
LogP:	1.948
LogD:	2.072
LogS:	-3.192
# Rotatable Bonds:	3
TPSA:	102.29
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.796
Synthetic Accessibility Score:	2.628
Fsp3:	0.231
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:	-4.804
MDCK Permeability:	2.1964269762975164e-05
Pgp-inhibitor:	0.164
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.09
20% Bioavailability (F20%):	0.027
30% Bioavailability (F30%):	0.561

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.054
Plasma Protein Binding (PPB):	90.70465850830078%
Volume Distribution (VD):	0.479
Pgp-substrate:	7.056981086730957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.98
CYP1A2-substrate:	0.879
CYP2C19-inhibitor:	0.735
CYP2C19-substrate:	0.125
CYP2C9-inhibitor:	0.642
CYP2C9-substrate:	0.731
CYP2D6-inhibitor:	0.896
CYP2D6-substrate:	0.153
CYP3A4-inhibitor:	0.787
CYP3A4-substrate:	0.15

ADMET: Excretion

Clearance (CL):	11.81
Half-life (T1/2):	0.609

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.134
Drug-inuced Liver Injury (DILI):	0.934
AMES Toxicity:	0.765
Rat Oral Acute Toxicity:	0.172
Maximum Recommended Daily Dose:	0.229
Skin Sensitization:	0.227
Carcinogencity:	0.036
Eye Corrosion:	0.01
Eye Irritation:	0.788
Respiratory Toxicity:	0.234

Download Data

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

Natural Product: NPC103509

Natural Product ID:	NPC103509
*Common Name:**	Tricrozarin B
IUPAC Name:	n.a.
Synonyms:	2,3,6-Trimethoxynaphthazarin
Standard InCHIKey:	BMXJCHIEWJGGAA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H12O7/c1-18-6-4-5(14)7-8(9(6)15)11(17)13(20-3)12(19-2)10(7)16/h4,14-15H,1-3H3
SMILES:	COc1cc(c2c(c1O)C(=O)C(=C(C2=O)OC)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL477533
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0000153] Naphthoquinones

*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
NPO20626	Tritonia crocosmaeflora	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3437287]
NPO20626	Tritonia crocosmaeflora	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3668558]
NPO20626	Tritonia crocosmaeflora	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20626	Tritonia crocosmaeflora	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	1
Others	1

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1317	Cell Line	CCRF S-180	Mus musculus	T/C	=	146.0	%	PMID[484999]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.007	ug.mL-1	PMID[484999]

☑ 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 NPC103509 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	427
0.1-0.2	1971
0.2-0.3	5459
0.3-0.4	11538
0.4-0.5	5717
0.5-0.6	4222
0.6-0.7	5109
0.7-0.8	6149
0.8-0.85	1502
0.85-0.9	569
0.9-0.95	30
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9205	High Similarity	NPC472048
0.9205	High Similarity	NPC234485
0.9184	High Similarity	NPC143903
0.9184	High Similarity	NPC226987
0.915	High Similarity	NPC477410
0.9139	High Similarity	NPC127172
0.9128	High Similarity	NPC134293
0.9122	High Similarity	NPC55557
0.9122	High Similarity	NPC30647
0.9122	High Similarity	NPC61871
0.9073	High Similarity	NPC20337
0.906	High Similarity	NPC287395
0.906	High Similarity	NPC183655
0.9038	High Similarity	NPC476822
0.9034	High Similarity	NPC50823
0.9032	High Similarity	NPC201560
0.902	High Similarity	NPC266960
0.902	High Similarity	NPC43243
0.902	High Similarity	NPC268161
0.902	High Similarity	NPC245546
0.9013	High Similarity	NPC477048
0.9013	High Similarity	NPC477047
0.9	High Similarity	NPC102003
0.9	High Similarity	NPC92722
0.8986	High Similarity	NPC472917
0.8974	High Similarity	NPC48860
0.8974	High Similarity	NPC191360
0.8968	High Similarity	NPC84571
0.8961	High Similarity	NPC179732
0.8961	High Similarity	NPC300727
0.8961	High Similarity	NPC78302
0.8961	High Similarity	NPC241904
0.8961	High Similarity	NPC7973
0.8961	High Similarity	NPC287979
0.8961	High Similarity	NPC163524
0.8961	High Similarity	NPC29841
0.8961	High Similarity	NPC110070
0.8961	High Similarity	NPC472438
0.8961	High Similarity	NPC176665
0.8961	High Similarity	NPC203891
0.8961	High Similarity	NPC235215
0.8961	High Similarity	NPC305663
0.8961	High Similarity	NPC101830
0.8954	High Similarity	NPC44079
0.8954	High Similarity	NPC26227
0.8954	High Similarity	NPC201451
0.8951	High Similarity	NPC129752
0.8933	High Similarity	NPC131451
0.8933	High Similarity	NPC15329
0.891	High Similarity	NPC311740
0.8903	High Similarity	NPC191459
0.8903	High Similarity	NPC130894
0.8903	High Similarity	NPC193842
0.8903	High Similarity	NPC152166
0.8903	High Similarity	NPC261004
0.8903	High Similarity	NPC288669
0.8903	High Similarity	NPC195832
0.8903	High Similarity	NPC204854
0.8903	High Similarity	NPC18607
0.8903	High Similarity	NPC22472
0.8903	High Similarity	NPC115798
0.8903	High Similarity	NPC9609
0.8903	High Similarity	NPC18772
0.8903	High Similarity	NPC300943
0.8903	High Similarity	NPC19687
0.8903	High Similarity	NPC176300
0.8903	High Similarity	NPC253634
0.8903	High Similarity	NPC143828
0.8903	High Similarity	NPC476242
0.8903	High Similarity	NPC7846
0.8903	High Similarity	NPC105242
0.8903	High Similarity	NPC4481
0.8903	High Similarity	NPC25495
0.8896	High Similarity	NPC274730
0.8896	High Similarity	NPC292107
0.8896	High Similarity	NPC247017
0.8896	High Similarity	NPC100916
0.8896	High Similarity	NPC200388
0.8896	High Similarity	NPC49824
0.8896	High Similarity	NPC55619
0.8896	High Similarity	NPC474520
0.8896	High Similarity	NPC98661
0.8882	High Similarity	NPC19980
0.8882	High Similarity	NPC171010
0.8882	High Similarity	NPC225731
0.8882	High Similarity	NPC30550
0.8882	High Similarity	NPC202157
0.8882	High Similarity	NPC45291
0.8867	High Similarity	NPC119660
0.8867	High Similarity	NPC93034
0.8859	High Similarity	NPC28632
0.8854	High Similarity	NPC238995
0.8846	High Similarity	NPC161947
0.8846	High Similarity	NPC14353
0.8846	High Similarity	NPC56085
0.8846	High Similarity	NPC155302
0.8846	High Similarity	NPC246478
0.8846	High Similarity	NPC228785
0.8839	High Similarity	NPC189179
0.8839	High Similarity	NPC75215
0.8839	High Similarity	NPC93376
0.8839	High Similarity	NPC227192
0.8839	High Similarity	NPC224137
0.8831	High Similarity	NPC56786
0.8831	High Similarity	NPC214138
0.8831	High Similarity	NPC80534
0.8831	High Similarity	NPC32557
0.8831	High Similarity	NPC189960
0.8827	High Similarity	NPC245975
0.8824	High Similarity	NPC301123
0.8824	High Similarity	NPC131266
0.8824	High Similarity	NPC161277
0.8824	High Similarity	NPC181209
0.8824	High Similarity	NPC256283
0.8824	High Similarity	NPC35763
0.8824	High Similarity	NPC312338
0.8824	High Similarity	NPC100971
0.8824	High Similarity	NPC187498
0.8824	High Similarity	NPC71334
0.8824	High Similarity	NPC245382
0.8824	High Similarity	NPC123886
0.8824	High Similarity	NPC291802
0.8824	High Similarity	NPC39007
0.8824	High Similarity	NPC222830
0.8824	High Similarity	NPC188203
0.8824	High Similarity	NPC149889
0.8824	High Similarity	NPC241498
0.8824	High Similarity	NPC275836
0.8824	High Similarity	NPC101996
0.8824	High Similarity	NPC27208
0.8824	High Similarity	NPC120163
0.8824	High Similarity	NPC156222
0.8824	High Similarity	NPC121522
0.8824	High Similarity	NPC142540
0.8824	High Similarity	NPC216769
0.8824	High Similarity	NPC209487
0.8824	High Similarity	NPC83508
0.8824	High Similarity	NPC100263
0.8824	High Similarity	NPC269451
0.8824	High Similarity	NPC275722
0.8824	High Similarity	NPC100887
0.8824	High Similarity	NPC57030
0.8824	High Similarity	NPC131624
0.8824	High Similarity	NPC198826
0.8824	High Similarity	NPC301323
0.8824	High Similarity	NPC212678
0.8824	High Similarity	NPC180234
0.8824	High Similarity	NPC199100
0.8824	High Similarity	NPC293183
0.8824	High Similarity	NPC120537
0.8824	High Similarity	NPC162313
0.8824	High Similarity	NPC239128
0.8824	High Similarity	NPC279989
0.8824	High Similarity	NPC82325
0.8824	High Similarity	NPC25270
0.8819	High Similarity	NPC143649
0.8816	High Similarity	NPC96501
0.8816	High Similarity	NPC151473
0.8812	High Similarity	NPC247136
0.8805	High Similarity	NPC20237
0.88	High Similarity	NPC165389
0.8797	High Similarity	NPC1755
0.8797	High Similarity	NPC1706
0.8797	High Similarity	NPC249181
0.8797	High Similarity	NPC263092
0.8797	High Similarity	NPC59295
0.8797	High Similarity	NPC39305
0.8792	High Similarity	NPC142165
0.879	High Similarity	NPC61010
0.879	High Similarity	NPC87431
0.879	High Similarity	NPC278052
0.879	High Similarity	NPC40491
0.8782	High Similarity	NPC245891
0.8782	High Similarity	NPC104876
0.8782	High Similarity	NPC45846
0.8782	High Similarity	NPC100123
0.8774	High Similarity	NPC77807
0.8774	High Similarity	NPC5379
0.8774	High Similarity	NPC265511
0.8774	High Similarity	NPC470762
0.8774	High Similarity	NPC474167
0.8774	High Similarity	NPC178854
0.8774	High Similarity	NPC14561
0.8766	High Similarity	NPC274327
0.8766	High Similarity	NPC89474
0.8766	High Similarity	NPC145379
0.8766	High Similarity	NPC250557
0.8766	High Similarity	NPC58382
0.8766	High Similarity	NPC176775
0.8766	High Similarity	NPC183878
0.8766	High Similarity	NPC276409
0.8766	High Similarity	NPC271779
0.8766	High Similarity	NPC86485
0.8766	High Similarity	NPC88645
0.8766	High Similarity	NPC179126
0.8766	High Similarity	NPC78326
0.8766	High Similarity	NPC236223
0.8766	High Similarity	NPC162351
0.8766	High Similarity	NPC206238
0.8766	High Similarity	NPC250822

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 NPC103509 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	402
0.1-0.2	1077
0.2-0.3	2149
0.3-0.4	2706
0.4-0.5	1511
0.5-0.6	861
0.6-0.7	325
0.7-0.8	101
0.8-0.85	15
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8766	High Similarity	NPD2801	Approved
0.8654	High Similarity	NPD3882	Suspended
0.8553	High Similarity	NPD1512	Approved
0.8462	Intermediate Similarity	NPD1934	Approved
0.8421	Intermediate Similarity	NPD1511	Approved
0.8378	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD6232	Discontinued
0.8239	Intermediate Similarity	NPD3817	Phase 2
0.8232	Intermediate Similarity	NPD7473	Discontinued
0.8176	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD6166	Phase 2
0.8155	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD1465	Phase 2
0.7988	Intermediate Similarity	NPD1247	Approved
0.7987	Intermediate Similarity	NPD1240	Approved
0.7987	Intermediate Similarity	NPD943	Approved
0.7933	Intermediate Similarity	NPD230	Phase 1
0.7929	Intermediate Similarity	NPD6797	Phase 2
0.7898	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1510	Phase 2
0.7882	Intermediate Similarity	NPD7251	Discontinued
0.7881	Intermediate Similarity	NPD1607	Approved
0.7857	Intermediate Similarity	NPD3818	Discontinued
0.7836	Intermediate Similarity	NPD7808	Phase 3
0.7834	Intermediate Similarity	NPD6799	Approved
0.7818	Intermediate Similarity	NPD5494	Approved
0.7811	Intermediate Similarity	NPD7054	Approved
0.7806	Intermediate Similarity	NPD2800	Approved
0.7785	Intermediate Similarity	NPD2532	Approved
0.7785	Intermediate Similarity	NPD2534	Approved
0.7785	Intermediate Similarity	NPD2533	Approved
0.7765	Intermediate Similarity	NPD7472	Approved
0.7765	Intermediate Similarity	NPD7074	Phase 3
0.7744	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7075	Discontinued
0.7683	Intermediate Similarity	NPD5402	Approved
0.7679	Intermediate Similarity	NPD3926	Phase 2
0.7677	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD4380	Phase 2
0.7654	Intermediate Similarity	NPD6599	Discontinued
0.7651	Intermediate Similarity	NPD9494	Approved
0.7651	Intermediate Similarity	NPD919	Approved
0.7647	Intermediate Similarity	NPD3751	Discontinued
0.7628	Intermediate Similarity	NPD1549	Phase 2
0.7622	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD5844	Phase 1
0.7582	Intermediate Similarity	NPD447	Suspended
0.7561	Intermediate Similarity	NPD6801	Discontinued
0.756	Intermediate Similarity	NPD6959	Discontinued
0.7532	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6651	Approved
0.7515	Intermediate Similarity	NPD7819	Suspended
0.7514	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2935	Discontinued
0.7486	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD9269	Phase 2
0.7421	Intermediate Similarity	NPD3750	Approved
0.7399	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD6234	Discontinued
0.7326	Intermediate Similarity	NPD2403	Approved
0.732	Intermediate Similarity	NPD3027	Phase 3
0.731	Intermediate Similarity	NPD3787	Discontinued
0.7303	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2796	Approved
0.7278	Intermediate Similarity	NPD3749	Approved
0.7267	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6190	Approved
0.7262	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD5403	Approved
0.7256	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD37	Approved
0.7239	Intermediate Similarity	NPD5401	Approved
0.7239	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5711	Approved
0.7209	Intermediate Similarity	NPD5710	Approved
0.7207	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1613	Approved
0.7178	Intermediate Similarity	NPD7390	Discontinued
0.717	Intermediate Similarity	NPD1551	Phase 2
0.7169	Intermediate Similarity	NPD3226	Approved
0.7162	Intermediate Similarity	NPD9268	Approved
0.7152	Intermediate Similarity	NPD920	Approved
0.7152	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD2344	Approved
0.7118	Intermediate Similarity	NPD4965	Approved
0.7118	Intermediate Similarity	NPD4967	Phase 2
0.7118	Intermediate Similarity	NPD4966	Approved
0.7112	Intermediate Similarity	NPD6781	Approved
0.7112	Intermediate Similarity	NPD6782	Approved
0.7112	Intermediate Similarity	NPD6780	Approved
0.7112	Intermediate Similarity	NPD6777	Approved
0.7112	Intermediate Similarity	NPD6776	Approved
0.7112	Intermediate Similarity	NPD6779	Approved
0.7112	Intermediate Similarity	NPD6778	Approved
0.7108	Intermediate Similarity	NPD1653	Approved
0.7107	Intermediate Similarity	NPD3748	Approved
0.709	Intermediate Similarity	NPD7435	Discontinued
0.7083	Intermediate Similarity	NPD7411	Suspended
0.7063	Intermediate Similarity	NPD6100	Approved
0.7063	Intermediate Similarity	NPD6099	Approved
0.7059	Intermediate Similarity	NPD1470	Approved
0.7052	Intermediate Similarity	NPD7199	Phase 2
0.7045	Intermediate Similarity	NPD7228	Approved
0.7037	Intermediate Similarity	NPD1243	Approved
0.7037	Intermediate Similarity	NPD2654	Approved
0.703	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD1471	Phase 3
0.6983	Remote Similarity	NPD6559	Discontinued
0.6982	Remote Similarity	NPD5090	Approved
0.6982	Remote Similarity	NPD5089	Approved
0.6978	Remote Similarity	NPD8434	Phase 2
0.6978	Remote Similarity	NPD8150	Discontinued
0.697	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD228	Approved
0.6959	Remote Similarity	NPD5353	Approved
0.6951	Remote Similarity	NPD2309	Approved
0.6943	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7768	Phase 2
0.6914	Remote Similarity	NPD2346	Discontinued
0.6911	Remote Similarity	NPD7696	Phase 3
0.6911	Remote Similarity	NPD7698	Approved
0.6911	Remote Similarity	NPD7697	Approved
0.6909	Remote Similarity	NPD3300	Phase 2
0.6908	Remote Similarity	NPD1201	Approved
0.689	Remote Similarity	NPD4628	Phase 3
0.689	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5242	Approved
0.6875	Remote Similarity	NPD7871	Phase 2
0.6875	Remote Similarity	NPD7870	Phase 2
0.6872	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7874	Approved
0.6863	Remote Similarity	NPD9717	Approved
0.6856	Remote Similarity	NPD7701	Phase 2
0.6846	Remote Similarity	NPD9493	Approved
0.6845	Remote Similarity	NPD6535	Approved
0.6845	Remote Similarity	NPD6534	Approved
0.6839	Remote Similarity	NPD1203	Approved
0.6833	Remote Similarity	NPD5953	Discontinued
0.6821	Remote Similarity	NPD8151	Discontinued
0.6816	Remote Similarity	NPD7286	Phase 2
0.6813	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD1933	Approved
0.6807	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD422	Phase 1
0.6796	Remote Similarity	NPD7685	Pre-registration
0.679	Remote Similarity	NPD2799	Discontinued
0.6782	Remote Similarity	NPD7907	Approved
0.6766	Remote Similarity	NPD4357	Discontinued
0.6755	Remote Similarity	NPD9545	Approved
0.6752	Remote Similarity	NPD3018	Phase 2
0.6751	Remote Similarity	NPD7801	Approved
0.675	Remote Similarity	NPD4060	Phase 1
0.6737	Remote Similarity	NPD7699	Phase 2
0.6737	Remote Similarity	NPD7700	Phase 2
0.673	Remote Similarity	NPD411	Approved
0.6727	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4585	Approved
0.6689	Remote Similarity	NPD5536	Phase 2
0.6688	Remote Similarity	NPD2798	Approved
0.6687	Remote Similarity	NPD6233	Phase 2
0.6686	Remote Similarity	NPD6386	Approved
0.6686	Remote Similarity	NPD6385	Approved
0.6686	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD4665	Approved
0.6683	Remote Similarity	NPD4111	Phase 1
0.6683	Remote Similarity	NPD2899	Discontinued
0.6667	Remote Similarity	NPD824	Approved
0.6667	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1876	Approved
0.6648	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD1608	Approved
0.6632	Remote Similarity	NPD2493	Approved
0.6632	Remote Similarity	NPD2494	Approved
0.663	Remote Similarity	NPD8312	Approved
0.663	Remote Similarity	NPD8313	Approved
0.6625	Remote Similarity	NPD3764	Approved
0.6625	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD2313	Discontinued
0.6612	Remote Similarity	NPD7240	Approved
0.6605	Remote Similarity	NPD6355	Discontinued
0.6605	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD2982	Phase 2
0.6603	Remote Similarity	NPD4749	Approved
0.6603	Remote Similarity	NPD2983	Phase 2
0.6598	Remote Similarity	NPD6823	Phase 2
0.6597	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD7090	Clinical (unspecified phase)

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