NPASS Compound

Structure

NPC235333 OpenBabel07101718192D 28 30 0 0 0 0 0 0 0 0999 V2000 0.5878 -4.2731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 -5.1391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 -3.4071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -2.5411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -4.2731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5878 0.9230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5878 -2.5411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 15 1 0 0 0 0 5 8 1 0 0 0 0 5 14 2 0 0 0 0 6 9 1 0 0 0 0 6 15 2 0 0 0 0 7 10 2 0 0 0 0 7 16 1 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 21 1 0 0 0 0 11 16 1 0 0 0 0 11 23 2 0 0 0 0 12 17 2 0 0 0 0 12 20 1 0 0 0 0 13 17 1 0 0 0 0 13 22 2 0 0 0 0 16 24 2 0 0 0 0 17 25 1 0 0 0 0 18 20 2 0 0 0 0 18 22 1 0 0 0 0 19 21 2 0 0 0 0 19 24 1 0 0 0 0 20 23 1 0 0 0 0 21 26 1 0 0 0 0 22 27 1 0 0 0 0 23 28 1 0 0 0 0 24 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.18
Volume:	409.424
LogP:	6.851
LogD:	4.219
LogS:	-2.85
# Rotatable Bonds:	5
TPSA:	73.83
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.46
Synthetic Accessibility Score:	3.068
Fsp3:	0.25
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:	-5.001
MDCK Permeability:	1.659540612308774e-05
Pgp-inhibitor:	0.671
Pgp-substrate:	0.323
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	94.50723266601562%
Volume Distribution (VD):	2.959
Pgp-substrate:	7.274226665496826%

ADMET: Metabolism

CYP1A2-inhibitor:	0.954
CYP1A2-substrate:	0.198
CYP2C19-inhibitor:	0.953
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.728
CYP2C9-substrate:	0.949
CYP2D6-inhibitor:	0.902
CYP2D6-substrate:	0.796
CYP3A4-inhibitor:	0.387
CYP3A4-substrate:	0.096

ADMET: Excretion

Clearance (CL):	12.775
Half-life (T1/2):	0.323

ADMET: Toxicity

hERG Blockers:	0.051
Human Hepatotoxicity (H-HT):	0.957
Drug-inuced Liver Injury (DILI):	0.612
AMES Toxicity:	0.053
Rat Oral Acute Toxicity:	0.253
Maximum Recommended Daily Dose:	0.717
Skin Sensitization:	0.91
Carcinogencity:	0.076
Eye Corrosion:	0.003
Eye Irritation:	0.248
Respiratory Toxicity:	0.894

Download Data

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

Natural Product: NPC235333

Natural Product ID:	NPC235333
*Common Name:**	Cathafuran B
IUPAC Name:	5-[6-hydroxy-7-(3-methylbut-2-enyl)-1-benzofuran-2-yl]-4-(3-methylbut-2-enyl)benzene-1,3-diol
Synonyms:
Standard InCHIKey:	RIKHTPZRKHGXPO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H26O4/c1-14(2)5-8-18-20(12-17(25)13-22(18)27)23-11-16-7-10-21(26)19(24(16)28-23)9-6-15(3)4/h5-7,10-13,25-27H,8-9H2,1-4H3
SMILES:	CC(=CCc1c(O)cc(cc1c1oc2c(c1)ccc(c2CC=C(C)C)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL561161
PubChem CID:	44139000
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO14875	Morus cathayana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19338315]
NPO14875	Morus cathayana	Species	Moraceae	Eukaryota	Fruits	Zhenjiang, Jiangsu Province, China		PMID[23060696]
NPO14875	Morus cathayana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14875	Morus cathayana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14875	Morus cathayana	Species	Moraceae	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
IC50	5

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	6.27	ug.mL-1	PMID[539104]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	=	6.27	ug.mL-1	PMID[539104]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	6.27	ug.mL-1	PMID[539104]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	6.27	ug.mL-1	PMID[539104]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6.27	ug.mL-1	PMID[539104]

☑ 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 NPC235333 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	426
0.1-0.2	1706
0.2-0.3	3956
0.3-0.4	10634
0.4-0.5	7726
0.5-0.6	3655
0.6-0.7	5510
0.7-0.8	5021
0.8-0.85	2578
0.85-0.9	1345
0.9-0.95	113
0.95-1	27

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC148938
0.9932	High Similarity	NPC297531
0.9932	High Similarity	NPC213936
0.9863	High Similarity	NPC23668
0.9863	High Similarity	NPC193976
0.9799	High Similarity	NPC246647
0.9799	High Similarity	NPC96342
0.9799	High Similarity	NPC268360
0.9799	High Similarity	NPC212967
0.9799	High Similarity	NPC164110
0.9796	High Similarity	NPC207624
0.9796	High Similarity	NPC142308
0.9795	High Similarity	NPC230713
0.9795	High Similarity	NPC78335
0.9732	High Similarity	NPC180924
0.9728	High Similarity	NPC58668
0.9728	High Similarity	NPC106372
0.9728	High Similarity	NPC115324
0.9728	High Similarity	NPC170169
0.9726	High Similarity	NPC178202
0.9664	High Similarity	NPC99199
0.9597	High Similarity	NPC472462
0.9592	High Similarity	NPC226644
0.9592	High Similarity	NPC37226
0.9533	High Similarity	NPC198490
0.9527	High Similarity	NPC167576
0.9524	High Similarity	NPC135325
0.9521	High Similarity	NPC210826
0.9467	High Similarity	NPC213608
0.9467	High Similarity	NPC183874
0.9467	High Similarity	NPC1477
0.9456	High Similarity	NPC12148
0.9456	High Similarity	NPC130581
0.9456	High Similarity	NPC17816
0.9452	High Similarity	NPC155144
0.94	High Similarity	NPC5871
0.9396	High Similarity	NPC13282
0.9388	High Similarity	NPC51641
0.9388	High Similarity	NPC300267
0.9384	High Similarity	NPC225884
0.9359	High Similarity	NPC53640
0.9342	High Similarity	NPC247677
0.9342	High Similarity	NPC160015
0.9338	High Similarity	NPC72370
0.9329	High Similarity	NPC296030
0.9329	High Similarity	NPC39929
0.9329	High Similarity	NPC65775
0.9329	High Similarity	NPC10027
0.9329	High Similarity	NPC37208
0.9329	High Similarity	NPC221868
0.932	High Similarity	NPC98926
0.932	High Similarity	NPC230943
0.9281	High Similarity	NPC260902
0.9281	High Similarity	NPC65504
0.9281	High Similarity	NPC296957
0.9267	High Similarity	NPC227122
0.9262	High Similarity	NPC272194
0.9252	High Similarity	NPC302181
0.9221	High Similarity	NPC40583
0.9221	High Similarity	NPC476349
0.9221	High Similarity	NPC476350
0.9221	High Similarity	NPC244750
0.9216	High Similarity	NPC137100
0.9205	High Similarity	NPC258249
0.9184	High Similarity	NPC53192
0.9161	High Similarity	NPC304839
0.9161	High Similarity	NPC220582
0.9161	High Similarity	NPC260296
0.9161	High Similarity	NPC115432
0.9145	High Similarity	NPC253872
0.9145	High Similarity	NPC67654
0.9145	High Similarity	NPC263676
0.9133	High Similarity	NPC186397
0.9133	High Similarity	NPC37135
0.9116	High Similarity	NPC49108
0.9114	High Similarity	NPC277480
0.9108	High Similarity	NPC133065
0.9108	High Similarity	NPC159508
0.9103	High Similarity	NPC45124
0.9103	High Similarity	NPC30655
0.9103	High Similarity	NPC74854
0.9085	High Similarity	NPC122365
0.9085	High Similarity	NPC95842
0.9085	High Similarity	NPC280530
0.9085	High Similarity	NPC178964
0.9079	High Similarity	NPC116604
0.9079	High Similarity	NPC156244
0.9073	High Similarity	NPC223988
0.9073	High Similarity	NPC158338
0.9073	High Similarity	NPC266499
0.9073	High Similarity	NPC65589
0.9073	High Similarity	NPC317492
0.9073	High Similarity	NPC288036
0.9073	High Similarity	NPC97029
0.9073	High Similarity	NPC97028
0.9073	High Similarity	NPC100985
0.9057	High Similarity	NPC253730
0.9057	High Similarity	NPC247973
0.9057	High Similarity	NPC50394
0.9057	High Similarity	NPC286230
0.9054	High Similarity	NPC96791
0.9054	High Similarity	NPC470636
0.9054	High Similarity	NPC226942
0.9051	High Similarity	NPC169471
0.9051	High Similarity	NPC39306
0.9051	High Similarity	NPC474591
0.9051	High Similarity	NPC37183
0.9045	High Similarity	NPC477239
0.9045	High Similarity	NPC312056
0.9045	High Similarity	NPC84515
0.9045	High Similarity	NPC193998
0.9045	High Similarity	NPC3448
0.902	High Similarity	NPC154683
0.902	High Similarity	NPC40356
0.9007	High Similarity	NPC27221
0.9007	High Similarity	NPC7025
0.9007	High Similarity	NPC256672
0.9007	High Similarity	NPC39195
0.9007	High Similarity	NPC168085
0.8993	High Similarity	NPC172182
0.8993	High Similarity	NPC262935
0.8993	High Similarity	NPC251182
0.8987	High Similarity	NPC155640
0.8981	High Similarity	NPC304387
0.8981	High Similarity	NPC188486
0.898	High Similarity	NPC472366
0.8974	High Similarity	NPC472877
0.8973	High Similarity	NPC62735
0.8968	High Similarity	NPC45131
0.8961	High Similarity	NPC169990
0.8961	High Similarity	NPC210942
0.8961	High Similarity	NPC329844
0.8954	High Similarity	NPC474417
0.8954	High Similarity	NPC72958
0.8954	High Similarity	NPC232645
0.8954	High Similarity	NPC149526
0.8944	High Similarity	NPC131866
0.894	High Similarity	NPC308200
0.894	High Similarity	NPC17101
0.894	High Similarity	NPC150215
0.894	High Similarity	NPC22005
0.894	High Similarity	NPC7943
0.894	High Similarity	NPC123202
0.894	High Similarity	NPC77903
0.8933	High Similarity	NPC234629
0.8933	High Similarity	NPC311741
0.8931	High Similarity	NPC136641
0.8926	High Similarity	NPC310340
0.8926	High Similarity	NPC144499
0.8926	High Similarity	NPC84266
0.8924	High Similarity	NPC219861
0.8924	High Similarity	NPC272722
0.8919	High Similarity	NPC275734
0.8919	High Similarity	NPC261227
0.8919	High Similarity	NPC270883
0.8919	High Similarity	NPC28337
0.8919	High Similarity	NPC69769
0.8919	High Similarity	NPC172986
0.8917	High Similarity	NPC470810
0.891	High Similarity	NPC196448
0.8903	High Similarity	NPC66508
0.8903	High Similarity	NPC226656
0.8903	High Similarity	NPC166054
0.8903	High Similarity	NPC254351
0.8903	High Similarity	NPC55662
0.8896	High Similarity	NPC38361
0.8896	High Similarity	NPC227906
0.8896	High Similarity	NPC217447
0.8896	High Similarity	NPC125300
0.8896	High Similarity	NPC41326
0.8896	High Similarity	NPC87708
0.8896	High Similarity	NPC474843
0.8896	High Similarity	NPC130015
0.8889	High Similarity	NPC119929
0.8889	High Similarity	NPC202595
0.8889	High Similarity	NPC295036
0.8889	High Similarity	NPC472421
0.8889	High Similarity	NPC470107
0.8889	High Similarity	NPC120105
0.8889	High Similarity	NPC321896
0.8889	High Similarity	NPC101957
0.8889	High Similarity	NPC476185
0.8889	High Similarity	NPC472406
0.8882	High Similarity	NPC216624
0.8882	High Similarity	NPC145467
0.8882	High Similarity	NPC105415
0.8874	High Similarity	NPC24136
0.8874	High Similarity	NPC290133
0.8874	High Similarity	NPC187282
0.8874	High Similarity	NPC477955
0.8874	High Similarity	NPC299011
0.8868	High Similarity	NPC109180
0.8868	High Similarity	NPC472581
0.8868	High Similarity	NPC38591
0.8867	High Similarity	NPC106985
0.8867	High Similarity	NPC190637
0.8867	High Similarity	NPC11700
0.8867	High Similarity	NPC24821
0.8867	High Similarity	NPC17262
0.8867	High Similarity	NPC212932

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 NPC235333 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	385
0.1-0.2	977
0.2-0.3	1484
0.3-0.4	2658
0.4-0.5	1929
0.5-0.6	1103
0.6-0.7	414
0.7-0.8	137
0.8-0.85	51
0.85-0.9	12
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.891	High Similarity	NPD3749	Approved
0.8808	High Similarity	NPD4378	Clinical (unspecified phase)
0.8718	High Similarity	NPD7819	Suspended
0.8716	High Similarity	NPD2344	Approved
0.8684	High Similarity	NPD7410	Clinical (unspecified phase)
0.8625	High Similarity	NPD6959	Discontinued
0.86	High Similarity	NPD2800	Approved
0.8599	High Similarity	NPD2393	Clinical (unspecified phase)
0.8562	High Similarity	NPD2533	Approved
0.8562	High Similarity	NPD2532	Approved
0.8562	High Similarity	NPD2534	Approved
0.8491	Intermediate Similarity	NPD3882	Suspended
0.8487	Intermediate Similarity	NPD2309	Approved
0.8477	Intermediate Similarity	NPD1243	Approved
0.8457	Intermediate Similarity	NPD6232	Discontinued
0.8452	Intermediate Similarity	NPD920	Approved
0.8435	Intermediate Similarity	NPD1240	Approved
0.8428	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD7473	Discontinued
0.8411	Intermediate Similarity	NPD1549	Phase 2
0.8383	Intermediate Similarity	NPD6559	Discontinued
0.8377	Intermediate Similarity	NPD1511	Approved
0.8365	Intermediate Similarity	NPD2801	Approved
0.8354	Intermediate Similarity	NPD7411	Suspended
0.8344	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD5494	Approved
0.8333	Intermediate Similarity	NPD1510	Phase 2
0.8323	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD1607	Approved
0.8302	Intermediate Similarity	NPD1934	Approved
0.8301	Intermediate Similarity	NPD3750	Approved
0.8293	Intermediate Similarity	NPD3926	Phase 2
0.8291	Intermediate Similarity	NPD4380	Phase 2
0.8289	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD2796	Approved
0.8269	Intermediate Similarity	NPD1512	Approved
0.8261	Intermediate Similarity	NPD7768	Phase 2
0.8242	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD3226	Approved
0.8212	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD7075	Discontinued
0.8194	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD1247	Approved
0.8158	Intermediate Similarity	NPD2935	Discontinued
0.8144	Intermediate Similarity	NPD3818	Discontinued
0.8141	Intermediate Similarity	NPD7390	Discontinued
0.8137	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD2346	Discontinued
0.8095	Intermediate Similarity	NPD5844	Phase 1
0.8092	Intermediate Similarity	NPD2799	Discontinued
0.8049	Intermediate Similarity	NPD919	Approved
0.8025	Intermediate Similarity	NPD6799	Approved
0.8024	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD6166	Phase 2
0.8024	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1471	Phase 3
0.7974	Intermediate Similarity	NPD3748	Approved
0.7963	Intermediate Similarity	NPD6801	Discontinued
0.795	Intermediate Similarity	NPD6599	Discontinued
0.7927	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD1465	Phase 2
0.7904	Intermediate Similarity	NPD7229	Phase 3
0.7904	Intermediate Similarity	NPD5710	Approved
0.7904	Intermediate Similarity	NPD5711	Approved
0.7871	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD2296	Approved
0.7866	Intermediate Similarity	NPD3817	Phase 2
0.7841	Intermediate Similarity	NPD4287	Approved
0.7829	Intermediate Similarity	NPD943	Approved
0.7815	Intermediate Similarity	NPD2313	Discontinued
0.7806	Intermediate Similarity	NPD6100	Approved
0.7806	Intermediate Similarity	NPD1551	Phase 2
0.7806	Intermediate Similarity	NPD6099	Approved
0.7803	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD5953	Discontinued
0.7778	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7286	Phase 2
0.7748	Intermediate Similarity	NPD4625	Phase 3
0.7733	Intermediate Similarity	NPD7074	Phase 3
0.7727	Intermediate Similarity	NPD6651	Approved
0.7697	Intermediate Similarity	NPD3764	Approved
0.7697	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5405	Approved
0.7692	Intermediate Similarity	NPD5408	Approved
0.7692	Intermediate Similarity	NPD5406	Approved
0.7692	Intermediate Similarity	NPD5404	Approved
0.7674	Intermediate Similarity	NPD7054	Approved
0.7651	Intermediate Similarity	NPD5402	Approved
0.763	Intermediate Similarity	NPD7472	Approved
0.7628	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1203	Approved
0.76	Intermediate Similarity	NPD1470	Approved
0.7586	Intermediate Similarity	NPD6797	Phase 2
0.7582	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD7251	Discontinued
0.753	Intermediate Similarity	NPD6280	Approved
0.753	Intermediate Similarity	NPD6279	Approved
0.75	Intermediate Similarity	NPD7808	Phase 3
0.75	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4628	Phase 3
0.7486	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5761	Phase 2
0.7485	Intermediate Similarity	NPD5760	Phase 2
0.7459	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD8312	Approved
0.7458	Intermediate Similarity	NPD8313	Approved
0.7451	Intermediate Similarity	NPD4908	Phase 1
0.745	Intermediate Similarity	NPD1201	Approved
0.7444	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD5403	Approved
0.7436	Intermediate Similarity	NPD447	Suspended
0.7434	Intermediate Similarity	NPD2798	Approved
0.743	Intermediate Similarity	NPD8434	Phase 2
0.7429	Intermediate Similarity	NPD1729	Discontinued
0.7427	Intermediate Similarity	NPD7199	Phase 2
0.7423	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD3751	Discontinued
0.74	Intermediate Similarity	NPD1608	Approved
0.74	Intermediate Similarity	NPD9717	Approved
0.7391	Intermediate Similarity	NPD7003	Approved
0.7384	Intermediate Similarity	NPD6808	Phase 2
0.7355	Intermediate Similarity	NPD3268	Approved
0.7341	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6832	Phase 2
0.7337	Intermediate Similarity	NPD4288	Approved
0.7337	Intermediate Similarity	NPD4361	Phase 2
0.7337	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2654	Approved
0.7325	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD230	Phase 1
0.7321	Intermediate Similarity	NPD37	Approved
0.7317	Intermediate Similarity	NPD5401	Approved
0.7314	Intermediate Similarity	NPD7177	Discontinued
0.731	Intermediate Similarity	NPD6234	Discontinued
0.7294	Intermediate Similarity	NPD4967	Phase 2
0.7294	Intermediate Similarity	NPD4966	Approved
0.7294	Intermediate Similarity	NPD4965	Approved
0.7283	Intermediate Similarity	NPD3787	Discontinued
0.7283	Intermediate Similarity	NPD4363	Phase 3
0.7283	Intermediate Similarity	NPD4360	Phase 2
0.7256	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1164	Approved
0.7255	Intermediate Similarity	NPD2797	Approved
0.7248	Intermediate Similarity	NPD1651	Approved
0.7244	Intermediate Similarity	NPD411	Approved
0.724	Intermediate Similarity	NPD8151	Discontinued
0.7226	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1610	Phase 2
0.7219	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD422	Phase 1
0.7212	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2403	Approved
0.72	Intermediate Similarity	NPD17	Approved
0.719	Intermediate Similarity	NPD1283	Approved
0.719	Intermediate Similarity	NPD1876	Approved
0.7188	Intermediate Similarity	NPD7033	Discontinued
0.7188	Intermediate Similarity	NPD4308	Phase 3
0.7181	Intermediate Similarity	NPD6781	Approved
0.7181	Intermediate Similarity	NPD6776	Approved
0.7181	Intermediate Similarity	NPD6780	Approved
0.7181	Intermediate Similarity	NPD6777	Approved
0.7181	Intermediate Similarity	NPD6778	Approved
0.7181	Intermediate Similarity	NPD6782	Approved
0.7181	Intermediate Similarity	NPD6779	Approved
0.7171	Intermediate Similarity	NPD3972	Approved
0.7169	Intermediate Similarity	NPD6273	Approved
0.7162	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4060	Phase 1
0.7135	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD4749	Approved
0.712	Intermediate Similarity	NPD7871	Phase 2
0.712	Intermediate Similarity	NPD7870	Phase 2
0.7112	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD3269	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6696	Suspended
0.7077	Intermediate Similarity	NPD7783	Phase 2
0.7077	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD7697	Approved
0.7068	Intermediate Similarity	NPD7435	Discontinued
0.7068	Intermediate Similarity	NPD7696	Phase 3
0.7068	Intermediate Similarity	NPD7698	Approved
0.7067	Intermediate Similarity	NPD1548	Phase 1
0.7052	Intermediate Similarity	NPD6971	Discontinued
0.7051	Intermediate Similarity	NPD2861	Phase 2
0.7049	Intermediate Similarity	NPD8150	Discontinued

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