NPASS Compound

Structure

CID45449 OpenBabel06191715382D 22 24 0 0 0 0 0 0 0 0999 V2000 2.4609 -3.4750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7154 1.0695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0027 -0.7186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6243 1.1702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5163 -1.4536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5165 -0.4847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6779 -1.9369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8388 -1.4529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5164 -1.4526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6777 -1.9376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6780 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8387 -1.4532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8386 -0.4840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5162 -0.4837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8389 -0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6775 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3962 -1.9603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6776 -2.9059 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6784 0.9679 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3545 0.0007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6772 0.9686 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 18 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 6 2 0 0 0 0 5 10 1 0 0 0 0 6 11 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 12 1 0 0 0 0 8 13 1 0 0 0 0 9 14 2 0 0 0 0 9 17 1 0 0 0 0 10 12 2 0 0 0 0 10 18 1 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 13 16 2 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 14 20 1 0 0 0 0 15 22 1 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.09
Volume:	296.545
LogP:	2.816
LogD:	3.053
LogS:	-4.293
# Rotatable Bonds:	4
TPSA:	70.29
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.797
Synthetic Accessibility Score:	2.488
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.753
MDCK Permeability:	4.0005081245908514e-05
Pgp-inhibitor:	0.555
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.04
Plasma Protein Binding (PPB):	75.8475112915039%
Volume Distribution (VD):	0.963
Pgp-substrate:	29.015016555786133%

ADMET: Metabolism

CYP1A2-inhibitor:	0.929
CYP1A2-substrate:	0.979
CYP2C19-inhibitor:	0.468
CYP2C19-substrate:	0.866
CYP2C9-inhibitor:	0.39
CYP2C9-substrate:	0.914
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.904
CYP3A4-inhibitor:	0.457
CYP3A4-substrate:	0.612

ADMET: Excretion

Clearance (CL):	11.759
Half-life (T1/2):	0.705

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.246
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.64
Rat Oral Acute Toxicity:	0.7
Maximum Recommended Daily Dose:	0.051
Skin Sensitization:	0.468
Carcinogencity:	0.268
Eye Corrosion:	0.005
Eye Irritation:	0.144
Respiratory Toxicity:	0.661

Download Data

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

Natural Product: NPC45449

Natural Product ID:	NPC45449
*Common Name:**	3,4,6,9-Tetramethoxydibenzofuran-2-Ol
IUPAC Name:	3,4,6,9-tetramethoxydibenzofuran-2-ol
Synonyms:
Standard InCHIKey:	UKLAPCYGHOYTBR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H16O6/c1-18-10-5-6-11(19-2)15-12(10)8-7-9(17)14(20-3)16(21-4)13(8)22-15/h5-7,17H,1-4H3
SMILES:	COc1ccc(c2c1c1cc(c(c(c1o2)OC)OC)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1270045
PubChem CID:	49831388
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans [CHEMONTID:0000015] Dibenzofurans

*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
NPO5061.1	Rhaphiolepis indica var. tashiroi	Varieties	Rosaceae	Eukaryota	n.a.	root	n.a.	DOI[10.1021/np100200s]
NPO5061.1	Rhaphiolepis indica var. tashiroi	Varieties	Rosaceae	Eukaryota	Roots	Wutai, Pingtung County, Taiwan	2007-SEP	PMID[20839880]

☑ 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

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7610.0	nM	PMID[514586]

☑ 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 NPC45449 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	440
0.1-0.2	1934
0.2-0.3	4854
0.3-0.4	11265
0.4-0.5	6331
0.5-0.6	3878
0.6-0.7	5214
0.7-0.8	5341
0.8-0.85	1805
0.85-0.9	1119
0.9-0.95	476
0.95-1	40

Similarity Score	Similarity Level	Natural Product ID
0.9872	High Similarity	NPC36320
0.9871	High Similarity	NPC238995
0.9808	High Similarity	NPC39305
0.9808	High Similarity	NPC1706
0.9808	High Similarity	NPC59295
0.9808	High Similarity	NPC263092
0.9808	High Similarity	NPC1755
0.9744	High Similarity	NPC272722
0.9744	High Similarity	NPC84515
0.9744	High Similarity	NPC312056
0.9679	High Similarity	NPC188486
0.9627	High Similarity	NPC82217
0.9627	High Similarity	NPC216842
0.9627	High Similarity	NPC476640
0.9568	High Similarity	NPC287243
0.9565	High Similarity	NPC230619
0.9565	High Similarity	NPC54098
0.9563	High Similarity	NPC247136
0.9557	High Similarity	NPC133065
0.9551	High Similarity	NPC196879
0.9551	High Similarity	NPC195832
0.9551	High Similarity	NPC16935
0.9509	High Similarity	NPC8127
0.9509	High Similarity	NPC49667
0.9503	High Similarity	NPC476641
0.95	High Similarity	NPC247973
0.9497	High Similarity	NPC39306
0.9423	High Similarity	NPC45131
0.9423	High Similarity	NPC472461
0.9387	High Similarity	NPC65885
0.9379	High Similarity	NPC470704
0.9325	High Similarity	NPC174700
0.9317	High Similarity	NPC277480
0.9304	High Similarity	NPC193842
0.9268	High Similarity	NPC473834
0.9268	High Similarity	NPC310794
0.9259	High Similarity	NPC50394
0.9255	High Similarity	NPC37183
0.9255	High Similarity	NPC291110
0.9241	High Similarity	NPC203891
0.9241	High Similarity	NPC110070
0.9241	High Similarity	NPC101830
0.9231	High Similarity	NPC125300
0.9231	High Similarity	NPC304954
0.9217	High Similarity	NPC297807
0.9217	High Similarity	NPC98546
0.9212	High Similarity	NPC289244
0.9202	High Similarity	NPC202470
0.9182	High Similarity	NPC7846
0.9182	High Similarity	NPC261004
0.9182	High Similarity	NPC18607
0.9182	High Similarity	NPC4481
0.9182	High Similarity	NPC288669
0.9182	High Similarity	NPC130894
0.9182	High Similarity	NPC152166
0.9182	High Similarity	NPC25495
0.9182	High Similarity	NPC300943
0.9182	High Similarity	NPC176300
0.9182	High Similarity	NPC253634
0.9182	High Similarity	NPC204854
0.9182	High Similarity	NPC9609
0.9182	High Similarity	NPC18772
0.9182	High Similarity	NPC191459
0.9182	High Similarity	NPC115798
0.9182	High Similarity	NPC19687
0.9182	High Similarity	NPC22472
0.9182	High Similarity	NPC143828
0.9182	High Similarity	NPC105242
0.9177	High Similarity	NPC43243
0.9177	High Similarity	NPC292107
0.9177	High Similarity	NPC268161
0.9177	High Similarity	NPC266960
0.9177	High Similarity	NPC245546
0.9177	High Similarity	NPC265511
0.9177	High Similarity	NPC49824
0.9157	High Similarity	NPC24258
0.9152	High Similarity	NPC30550
0.9152	High Similarity	NPC149846
0.9146	High Similarity	NPC28042
0.9146	High Similarity	NPC131866
0.9125	High Similarity	NPC246478
0.9119	High Similarity	NPC75215
0.9119	High Similarity	NPC163524
0.9119	High Similarity	NPC227192
0.9119	High Similarity	NPC176665
0.9119	High Similarity	NPC305663
0.9119	High Similarity	NPC93376
0.9119	High Similarity	NPC78302
0.9119	High Similarity	NPC224137
0.9119	High Similarity	NPC287979
0.9119	High Similarity	NPC29841
0.9119	High Similarity	NPC189179
0.9119	High Similarity	NPC472438
0.9119	High Similarity	NPC235215
0.9119	High Similarity	NPC7973
0.9114	High Similarity	NPC189960
0.9114	High Similarity	NPC32557
0.9114	High Similarity	NPC201451
0.9114	High Similarity	NPC268008
0.9114	High Similarity	NPC44079
0.9114	High Similarity	NPC20830
0.9114	High Similarity	NPC256612
0.9114	High Similarity	NPC26227
0.9108	High Similarity	NPC161277
0.9108	High Similarity	NPC39007
0.9107	High Similarity	NPC47883
0.9103	High Similarity	NPC260582
0.9068	High Similarity	NPC308992
0.9062	High Similarity	NPC55738
0.9062	High Similarity	NPC152904
0.9057	High Similarity	NPC98661
0.9057	High Similarity	NPC178854
0.9057	High Similarity	NPC247017
0.9057	High Similarity	NPC55619
0.9057	High Similarity	NPC200388
0.9057	High Similarity	NPC100916
0.9057	High Similarity	NPC474520
0.9057	High Similarity	NPC472916
0.9051	High Similarity	NPC176775
0.9051	High Similarity	NPC206238
0.9051	High Similarity	NPC231018
0.9051	High Similarity	NPC183878
0.9051	High Similarity	NPC88645
0.9051	High Similarity	NPC167091
0.9051	High Similarity	NPC145379
0.9051	High Similarity	NPC255350
0.9051	High Similarity	NPC274327
0.9051	High Similarity	NPC160951
0.9051	High Similarity	NPC78326
0.9051	High Similarity	NPC292214
0.9051	High Similarity	NPC236223
0.9051	High Similarity	NPC271779
0.9051	High Similarity	NPC179126
0.9051	High Similarity	NPC47781
0.9051	High Similarity	NPC189130
0.9051	High Similarity	NPC22519
0.9051	High Similarity	NPC270620
0.9051	High Similarity	NPC69394
0.9051	High Similarity	NPC86485
0.9048	High Similarity	NPC476273
0.9045	High Similarity	NPC171010
0.9042	High Similarity	NPC471841
0.9038	High Similarity	NPC102003
0.9038	High Similarity	NPC92722
0.9036	High Similarity	NPC277510
0.9036	High Similarity	NPC261471
0.9036	High Similarity	NPC233956
0.903	High Similarity	NPC281835
0.9024	High Similarity	NPC86477
0.9024	High Similarity	NPC76482
0.9024	High Similarity	NPC186392
0.9018	High Similarity	NPC234052
0.9018	High Similarity	NPC224280
0.9018	High Similarity	NPC29411
0.9018	High Similarity	NPC187923
0.9012	High Similarity	NPC81679
0.9006	High Similarity	NPC263449
0.9006	High Similarity	NPC476980
0.9	High Similarity	NPC36852
0.9	High Similarity	NPC476170
0.9	High Similarity	NPC475267
0.9	High Similarity	NPC210084
0.9	High Similarity	NPC299520
0.9	High Similarity	NPC472911
0.9	High Similarity	NPC99597
0.9	High Similarity	NPC262286
0.9	High Similarity	NPC245758
0.9	High Similarity	NPC78225
0.9	High Similarity	NPC472910
0.9	High Similarity	NPC48208
0.9	High Similarity	NPC156057
0.9	High Similarity	NPC474208
0.9	High Similarity	NPC241904
0.9	High Similarity	NPC471515
0.9	High Similarity	NPC222814
0.9	High Similarity	NPC472913
0.9	High Similarity	NPC96167
0.9	High Similarity	NPC469584
0.9	High Similarity	NPC300727
0.9	High Similarity	NPC471479
0.9	High Similarity	NPC474836
0.9	High Similarity	NPC162869
0.9	High Similarity	NPC472914
0.9	High Similarity	NPC129684
0.9	High Similarity	NPC181960
0.9	High Similarity	NPC67876
0.8994	High Similarity	NPC183597
0.8994	High Similarity	NPC163780
0.8994	High Similarity	NPC214138
0.8994	High Similarity	NPC208197
0.8994	High Similarity	NPC201136
0.8994	High Similarity	NPC128863
0.8994	High Similarity	NPC213622
0.8994	High Similarity	NPC227325
0.8994	High Similarity	NPC92659
0.8994	High Similarity	NPC167815
0.8994	High Similarity	NPC4455
0.8994	High Similarity	NPC2476
0.8994	High Similarity	NPC146165
0.8994	High Similarity	NPC138360

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 NPC45449 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	399
0.1-0.2	992
0.2-0.3	1904
0.3-0.4	2701
0.4-0.5	1696
0.5-0.6	959
0.6-0.7	344
0.7-0.8	114
0.8-0.85	22
0.85-0.9	14
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9299	High Similarity	NPD3882	Suspended
0.9051	High Similarity	NPD2801	Approved
0.875	High Similarity	NPD1934	Approved
0.8727	High Similarity	NPD3926	Phase 2
0.872	High Similarity	NPD1247	Approved
0.8675	High Similarity	NPD6167	Clinical (unspecified phase)
0.8675	High Similarity	NPD6168	Clinical (unspecified phase)
0.8675	High Similarity	NPD6166	Phase 2
0.8608	High Similarity	NPD1512	Approved
0.858	High Similarity	NPD2393	Clinical (unspecified phase)
0.8571	High Similarity	NPD3818	Discontinued
0.8545	High Similarity	NPD5494	Approved
0.8528	High Similarity	NPD3817	Phase 2
0.8481	Intermediate Similarity	NPD1511	Approved
0.843	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD919	Approved
0.8313	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD6799	Approved
0.8225	Intermediate Similarity	NPD6232	Discontinued
0.8208	Intermediate Similarity	NPD6797	Phase 2
0.8204	Intermediate Similarity	NPD7075	Discontinued
0.8187	Intermediate Similarity	NPD7473	Discontinued
0.8171	Intermediate Similarity	NPD6599	Discontinued
0.8161	Intermediate Similarity	NPD7251	Discontinued
0.815	Intermediate Similarity	NPD7074	Phase 3
0.8133	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD1465	Phase 2
0.8114	Intermediate Similarity	NPD7808	Phase 3
0.8101	Intermediate Similarity	NPD2344	Approved
0.8095	Intermediate Similarity	NPD3749	Approved
0.8092	Intermediate Similarity	NPD7054	Approved
0.8092	Intermediate Similarity	NPD5844	Phase 1
0.8084	Intermediate Similarity	NPD5402	Approved
0.8072	Intermediate Similarity	NPD6801	Discontinued
0.8057	Intermediate Similarity	NPD6559	Discontinued
0.8046	Intermediate Similarity	NPD7472	Approved
0.8	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD4380	Phase 2
0.7949	Intermediate Similarity	NPD1240	Approved
0.7949	Intermediate Similarity	NPD943	Approved
0.7937	Intermediate Similarity	NPD1549	Phase 2
0.7901	Intermediate Similarity	NPD2309	Approved
0.7888	Intermediate Similarity	NPD2800	Approved
0.7882	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD920	Approved
0.7875	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD1510	Phase 2
0.7849	Intermediate Similarity	NPD6959	Discontinued
0.7848	Intermediate Similarity	NPD1607	Approved
0.7812	Intermediate Similarity	NPD2796	Approved
0.7811	Intermediate Similarity	NPD7819	Suspended
0.7784	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD2935	Discontinued
0.7692	Intermediate Similarity	NPD7411	Suspended
0.7669	Intermediate Similarity	NPD1243	Approved
0.7665	Intermediate Similarity	NPD5403	Approved
0.7651	Intermediate Similarity	NPD2534	Approved
0.7651	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD2532	Approved
0.7651	Intermediate Similarity	NPD2533	Approved
0.765	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD3751	Discontinued
0.7616	Intermediate Similarity	NPD7768	Phase 2
0.7614	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD447	Suspended
0.7562	Intermediate Similarity	NPD230	Phase 1
0.7545	Intermediate Similarity	NPD5401	Approved
0.7543	Intermediate Similarity	NPD7199	Phase 2
0.7541	Intermediate Similarity	NPD8434	Phase 2
0.753	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD3750	Approved
0.7514	Intermediate Similarity	NPD2403	Approved
0.75	Intermediate Similarity	NPD3787	Discontinued
0.7485	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD6190	Approved
0.7468	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD1471	Phase 3
0.7429	Intermediate Similarity	NPD6234	Discontinued
0.7421	Intermediate Similarity	NPD3027	Phase 3
0.741	Intermediate Similarity	NPD4628	Phase 3
0.7405	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1613	Approved
0.7378	Intermediate Similarity	NPD1551	Phase 2
0.7356	Intermediate Similarity	NPD2296	Approved
0.7349	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2163	Approved
0.7317	Intermediate Similarity	NPD2799	Discontinued
0.7296	Intermediate Similarity	NPD9494	Approved
0.7293	Intermediate Similarity	NPD7286	Phase 2
0.7292	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3226	Approved
0.7261	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD37	Approved
0.7229	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD4966	Approved
0.7216	Intermediate Similarity	NPD4967	Phase 2
0.7216	Intermediate Similarity	NPD4965	Approved
0.7213	Intermediate Similarity	NPD5953	Discontinued
0.7212	Intermediate Similarity	NPD3748	Approved
0.7212	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD1653	Approved
0.7202	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6651	Approved
0.7181	Intermediate Similarity	NPD4287	Approved
0.7176	Intermediate Similarity	NPD7390	Discontinued
0.7169	Intermediate Similarity	NPD6099	Approved
0.7169	Intermediate Similarity	NPD6100	Approved
0.7167	Intermediate Similarity	NPD5242	Approved
0.7143	Intermediate Similarity	NPD6280	Approved
0.7143	Intermediate Similarity	NPD7228	Approved
0.7143	Intermediate Similarity	NPD6279	Approved
0.7135	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6355	Discontinued
0.7134	Intermediate Similarity	NPD1933	Approved
0.7126	Intermediate Similarity	NPD2346	Discontinued
0.7122	Intermediate Similarity	NPD7907	Approved
0.7117	Intermediate Similarity	NPD6233	Phase 2
0.7113	Intermediate Similarity	NPD6782	Approved
0.7113	Intermediate Similarity	NPD6781	Approved
0.7113	Intermediate Similarity	NPD6778	Approved
0.7113	Intermediate Similarity	NPD6780	Approved
0.7113	Intermediate Similarity	NPD6776	Approved
0.7113	Intermediate Similarity	NPD6777	Approved
0.7113	Intermediate Similarity	NPD6779	Approved
0.7111	Intermediate Similarity	NPD5710	Approved
0.7111	Intermediate Similarity	NPD5711	Approved
0.7111	Intermediate Similarity	NPD7229	Phase 3
0.7092	Intermediate Similarity	NPD7435	Discontinued
0.7081	Intermediate Similarity	NPD7685	Pre-registration
0.7063	Intermediate Similarity	NPD1203	Approved
0.7055	Intermediate Similarity	NPD6798	Discontinued
0.7055	Intermediate Similarity	NPD2313	Discontinued
0.7049	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4908	Phase 1
0.7035	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD4111	Phase 1
0.7024	Intermediate Similarity	NPD4665	Approved
0.7017	Intermediate Similarity	NPD6808	Phase 2
0.7005	Intermediate Similarity	NPD8312	Approved
0.7005	Intermediate Similarity	NPD8313	Approved
0.7	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD8150	Discontinued
0.6981	Remote Similarity	NPD9269	Phase 2
0.6977	Remote Similarity	NPD4357	Discontinued
0.6973	Remote Similarity	NPD1729	Discontinued
0.697	Remote Similarity	NPD7870	Phase 2
0.697	Remote Similarity	NPD4060	Phase 1
0.697	Remote Similarity	NPD7871	Phase 2
0.6959	Remote Similarity	NPD2354	Approved
0.6951	Remote Similarity	NPD3764	Approved
0.6951	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD2654	Approved
0.6933	Remote Similarity	NPD6832	Phase 2
0.6928	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7696	Phase 3
0.6919	Remote Similarity	NPD7698	Approved
0.6919	Remote Similarity	NPD7697	Approved
0.6915	Remote Similarity	NPD8151	Discontinued
0.6914	Remote Similarity	NPD2798	Approved
0.691	Remote Similarity	NPD5760	Phase 2
0.691	Remote Similarity	NPD5761	Phase 2
0.6904	Remote Similarity	NPD2493	Approved
0.6904	Remote Similarity	NPD2494	Approved
0.6898	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6385	Approved
0.6893	Remote Similarity	NPD6386	Approved
0.6881	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7874	Approved
0.6875	Remote Similarity	NPD9717	Approved
0.6875	Remote Similarity	NPD1608	Approved
0.6872	Remote Similarity	NPD5353	Approved
0.6871	Remote Similarity	NPD2861	Phase 2
0.6866	Remote Similarity	NPD7701	Phase 2
0.6862	Remote Similarity	NPD7549	Discontinued
0.686	Remote Similarity	NPD2899	Discontinued
0.6856	Remote Similarity	NPD6534	Approved
0.6856	Remote Similarity	NPD6535	Approved
0.6854	Remote Similarity	NPD6844	Discontinued
0.6848	Remote Similarity	NPD3268	Approved
0.6847	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD7783	Phase 2
0.6821	Remote Similarity	NPD4361	Phase 2
0.6821	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3452	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