NPASS Compound

Structure

CID328682 OpenBabel06191716202D 32 35 0 0 1 0 0 0 0 0999 V2000 -1.9323 -4.4207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0638 -1.0751 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 -0.7615 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4639 -3.6519 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 -1.7232 -2.4317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4277 -0.8494 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9040 0.8613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9040 -0.8613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6187 -1.4371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4973 -0.0523 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.4973 0.0523 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.6368 -2.8384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3413 -1.2561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7052 -1.0304 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.7052 1.0304 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.4458 -2.2506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7413 -3.8329 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1503 -0.6683 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3594 -2.6574 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1609 -1.5304 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1609 1.5304 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 29 1 0 0 0 0 6 30 1 0 0 0 0 7 13 2 0 0 0 0 7 17 1 0 0 0 0 8 13 1 0 0 0 0 8 18 2 0 0 0 0 9 14 2 0 0 0 0 9 19 1 0 0 0 0 10 14 1 0 0 0 0 10 20 2 0 0 0 0 11 15 1 0 0 0 0 11 32 1 0 0 0 0 12 16 1 0 0 0 0 12 31 1 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 23 2 0 0 0 0 17 25 1 0 0 0 0 18 23 1 0 0 0 0 18 26 1 0 0 0 0 19 24 2 0 0 0 0 19 27 1 0 0 0 0 20 24 1 0 0 0 0 20 28 1 0 0 0 0 21 31 1 0 0 0 0 22 32 1 0 0 0 0 23 29 1 0 0 0 0 24 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	446.19
Volume:	443.937
LogP:	2.383
LogD:	3.072
LogS:	-4.133
# Rotatable Bonds:	8
TPSA:	73.84
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.606
Synthetic Accessibility Score:	3.578
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.861
MDCK Permeability:	4.244664523866959e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.197

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.102
Plasma Protein Binding (PPB):	56.73590087890625%
Volume Distribution (VD):	0.632
Pgp-substrate:	21.278644561767578%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.977
CYP2C19-inhibitor:	0.056
CYP2C19-substrate:	0.949
CYP2C9-inhibitor:	0.06
CYP2C9-substrate:	0.711
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.904
CYP3A4-inhibitor:	0.57
CYP3A4-substrate:	0.92

ADMET: Excretion

Clearance (CL):	5.352
Half-life (T1/2):	0.25

ADMET: Toxicity

hERG Blockers:	0.287
Human Hepatotoxicity (H-HT):	0.085
Drug-inuced Liver Injury (DILI):	0.681
AMES Toxicity:	0.112
Rat Oral Acute Toxicity:	0.115
Maximum Recommended Daily Dose:	0.266
Skin Sensitization:	0.752
Carcinogencity:	0.037
Eye Corrosion:	0.003
Eye Irritation:	0.019
Respiratory Toxicity:	0.052

Download Data

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

Natural Product: NPC328682

Natural Product ID:	NPC328682
*Common Name:**	3,6-Bis(3,4,5-Trimethoxyphenyl)-1,3,3A,4,6,6A-Hexahydrofuro[3,4-C]Furan
IUPAC Name:	3,6-bis(3,4,5-trimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan
Synonyms:
Standard InCHIKey:	HRLFUIXSXUASEX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H30O8/c1-25-17-7-13(8-18(26-2)23(17)29-5)21-15-11-32-22(16(15)12-31-21)14-9-19(27-3)24(30-6)20(10-14)28-4/h7-10,15-16,21-22H,11-12H2,1-6H3
SMILES:	COc1cc(cc(c1OC)OC)C1OCC2C1COC2c1cc(OC)c(c(c1)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1412125
PubChem CID:	99091
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans

*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
NPO18811	Magnolia biondii	Species	Magnoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[17628872]
NPO18811	Magnolia biondii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19370929]
NPO18811	Magnolia biondii	Species	Magnoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[7779269]
NPO18811	Magnolia biondii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO542	Artemisia absinthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18811	Magnolia biondii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO542	Artemisia absinthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO542	Artemisia absinthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18811	Magnolia biondii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18811	Magnolia biondii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO542	Artemisia absinthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18811	Magnolia biondii	Species	Magnoliaceae	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
Potency	8

Activity Type	# Activity
Individual Protein	6
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3	Individual Protein	Thioredoxin glutathione reductase	Schistosoma mansoni	Potency	=	35481.3	nM	PMID[507599]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	29081.0	nM	PMID[507599]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[507599]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[507599]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	4.6	nM	PMID[507599]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	23109.3	nM	PMID[507599]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	10417.9	nM	PMID[507599]
NPT2	Others	Unspecified		Potency	n.a.	8912.5	nM	PMID[507599]

☑ 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 NPC328682 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	504
0.1-0.2	1472
0.2-0.3	4311
0.3-0.4	12245
0.4-0.5	6747
0.5-0.6	5983
0.6-0.7	8781
0.7-0.8	2026
0.8-0.85	482
0.85-0.9	98
0.9-0.95	37
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC54321
1.0	High Similarity	NPC281864
0.9917	High Similarity	NPC473092
0.9917	High Similarity	NPC8050
0.9917	High Similarity	NPC473093
0.9836	High Similarity	NPC82862
0.9836	High Similarity	NPC222127
0.9672	High Similarity	NPC285725
0.9672	High Similarity	NPC112571
0.9672	High Similarity	NPC88297
0.9672	High Similarity	NPC186845
0.9672	High Similarity	NPC50683
0.9672	High Similarity	NPC9891
0.9524	High Similarity	NPC72046
0.9524	High Similarity	NPC261812
0.9524	High Similarity	NPC65183
0.9508	High Similarity	NPC18449
0.9508	High Similarity	NPC34902
0.9508	High Similarity	NPC121783
0.9453	High Similarity	NPC141765
0.9453	High Similarity	NPC25333
0.9453	High Similarity	NPC165155
0.9453	High Similarity	NPC49235
0.9453	High Similarity	NPC148893
0.9453	High Similarity	NPC24490
0.9453	High Similarity	NPC34103
0.9449	High Similarity	NPC266848
0.9449	High Similarity	NPC136750
0.938	High Similarity	NPC121651
0.9375	High Similarity	NPC31530
0.9365	High Similarity	NPC470624
0.9365	High Similarity	NPC237169
0.9302	High Similarity	NPC126409
0.9302	High Similarity	NPC189474
0.9302	High Similarity	NPC99572
0.9297	High Similarity	NPC1474
0.9291	High Similarity	NPC192255
0.9262	High Similarity	NPC126935
0.9262	High Similarity	NPC57268
0.9262	High Similarity	NPC172676
0.9262	High Similarity	NPC216929
0.9262	High Similarity	NPC65933
0.9262	High Similarity	NPC312713
0.9237	High Similarity	NPC113550
0.9231	High Similarity	NPC11453
0.9231	High Similarity	NPC78047
0.9225	High Similarity	NPC326095
0.9225	High Similarity	NPC244983
0.9219	High Similarity	NPC204215
0.9219	High Similarity	NPC475856
0.9219	High Similarity	NPC175067
0.9167	High Similarity	NPC46591
0.916	High Similarity	NPC283949
0.9154	High Similarity	NPC150534
0.9147	High Similarity	NPC158331
0.9106	High Similarity	NPC477886
0.9098	High Similarity	NPC312199
0.9077	High Similarity	NPC287745
0.9077	High Similarity	NPC474478
0.907	High Similarity	NPC7744
0.9055	High Similarity	NPC57119
0.9055	High Similarity	NPC158471
0.9055	High Similarity	NPC165128
0.9055	High Similarity	NPC226862
0.9048	High Similarity	NPC206882
0.9032	High Similarity	NPC261661
0.903	High Similarity	NPC287124
0.9023	High Similarity	NPC103448
0.9023	High Similarity	NPC226547
0.9023	High Similarity	NPC177868
0.9023	High Similarity	NPC56091
0.9023	High Similarity	NPC216434
0.9016	High Similarity	NPC254625
0.9016	High Similarity	NPC475961
0.9015	High Similarity	NPC185908
0.9008	High Similarity	NPC236522
0.8992	High Similarity	NPC27843
0.8992	High Similarity	NPC40432
0.8992	High Similarity	NPC161557
0.8992	High Similarity	NPC115207
0.8992	High Similarity	NPC184928
0.8992	High Similarity	NPC227160
0.8992	High Similarity	NPC141493
0.8992	High Similarity	NPC82111
0.8992	High Similarity	NPC7171
0.8992	High Similarity	NPC228346
0.8992	High Similarity	NPC158079
0.8963	High Similarity	NPC12728
0.8963	High Similarity	NPC185071
0.8939	High Similarity	NPC143895
0.8923	High Similarity	NPC181049
0.8923	High Similarity	NPC4940
0.8923	High Similarity	NPC207400
0.8915	High Similarity	NPC233224
0.8915	High Similarity	NPC271208
0.8906	High Similarity	NPC31707
0.8906	High Similarity	NPC470084
0.8897	High Similarity	NPC477701
0.8897	High Similarity	NPC470097
0.8897	High Similarity	NPC141569
0.8897	High Similarity	NPC471415
0.8897	High Similarity	NPC166884
0.8897	High Similarity	NPC114119
0.8889	High Similarity	NPC472562
0.8889	High Similarity	NPC80326
0.8889	High Similarity	NPC474295
0.8872	High Similarity	NPC477938
0.8871	High Similarity	NPC472596
0.8864	High Similarity	NPC72796
0.8864	High Similarity	NPC44245
0.8862	High Similarity	NPC15805
0.8855	High Similarity	NPC196937
0.8846	High Similarity	NPC474017
0.8832	High Similarity	NPC477702
0.8828	High Similarity	NPC202904
0.8828	High Similarity	NPC242032
0.8828	High Similarity	NPC98745
0.8828	High Similarity	NPC189248
0.8824	High Similarity	NPC255566
0.8824	High Similarity	NPC298317
0.8815	High Similarity	NPC311530
0.8815	High Similarity	NPC300798
0.8815	High Similarity	NPC58137
0.8797	High Similarity	NPC32189
0.8788	High Similarity	NPC145769
0.8779	High Similarity	NPC33611
0.8779	High Similarity	NPC171928
0.8779	High Similarity	NPC100223
0.8779	High Similarity	NPC158526
0.8779	High Similarity	NPC129687
0.8779	High Similarity	NPC16830
0.877	High Similarity	NPC123948
0.8769	High Similarity	NPC77040
0.8769	High Similarity	NPC469612
0.8769	High Similarity	NPC92164
0.8769	High Similarity	NPC257582
0.8769	High Similarity	NPC307042
0.8769	High Similarity	NPC64201
0.8769	High Similarity	NPC153739
0.8769	High Similarity	NPC174495
0.8769	High Similarity	NPC145305
0.8769	High Similarity	NPC469614
0.8769	High Similarity	NPC79184
0.8769	High Similarity	NPC187998
0.8769	High Similarity	NPC242807
0.8769	High Similarity	NPC241522
0.8769	High Similarity	NPC42300
0.8768	High Similarity	NPC317053
0.8768	High Similarity	NPC212890
0.8768	High Similarity	NPC324492
0.876	High Similarity	NPC207702
0.876	High Similarity	NPC128208
0.876	High Similarity	NPC283114
0.876	High Similarity	NPC149008
0.876	High Similarity	NPC11258
0.876	High Similarity	NPC21867
0.876	High Similarity	NPC282703
0.876	High Similarity	NPC184733
0.876	High Similarity	NPC210674
0.876	High Similarity	NPC45774
0.876	High Similarity	NPC129570
0.875	High Similarity	NPC151423
0.875	High Similarity	NPC311057
0.875	High Similarity	NPC174522
0.875	High Similarity	NPC76451
0.875	High Similarity	NPC40237
0.8741	High Similarity	NPC309124
0.8741	High Similarity	NPC254759
0.8741	High Similarity	NPC27495
0.8741	High Similarity	NPC184797
0.8741	High Similarity	NPC160283
0.8731	High Similarity	NPC865
0.8731	High Similarity	NPC474039
0.8722	High Similarity	NPC474139
0.8722	High Similarity	NPC211386
0.8705	High Similarity	NPC320671
0.8705	High Similarity	NPC327412
0.8705	High Similarity	NPC320970
0.8705	High Similarity	NPC328567
0.8702	High Similarity	NPC277804
0.8702	High Similarity	NPC30043
0.8702	High Similarity	NPC470095
0.8702	High Similarity	NPC469613
0.8702	High Similarity	NPC470096
0.8702	High Similarity	NPC469625
0.8696	High Similarity	NPC205316
0.8696	High Similarity	NPC180953
0.8696	High Similarity	NPC475868
0.8692	High Similarity	NPC476968
0.8692	High Similarity	NPC3439
0.8692	High Similarity	NPC202582
0.8692	High Similarity	NPC273295
0.8692	High Similarity	NPC222004
0.8692	High Similarity	NPC475875
0.8692	High Similarity	NPC226788
0.8692	High Similarity	NPC285339
0.8692	High Similarity	NPC190629
0.8692	High Similarity	NPC210623
0.8692	High Similarity	NPC218856
0.8692	High Similarity	NPC470258

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 NPC328682 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	386
0.1-0.2	866
0.2-0.3	1842
0.3-0.4	2904
0.4-0.5	1690
0.5-0.6	987
0.6-0.7	416
0.7-0.8	54
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8692	High Similarity	NPD3027	Phase 3
0.8525	High Similarity	NPD5283	Phase 1
0.8438	Intermediate Similarity	NPD2981	Phase 2
0.8372	Intermediate Similarity	NPD2982	Phase 2
0.8372	Intermediate Similarity	NPD2983	Phase 2
0.8359	Intermediate Similarity	NPD3705	Approved
0.8258	Intermediate Similarity	NPD3018	Phase 2
0.8176	Intermediate Similarity	NPD4966	Approved
0.8176	Intermediate Similarity	NPD4967	Phase 2
0.8176	Intermediate Similarity	NPD4965	Approved
0.8088	Intermediate Similarity	NPD1613	Approved
0.8088	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD6234	Discontinued
0.8028	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7985	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD37	Approved
0.7926	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD4908	Phase 1
0.7748	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD7124	Phase 2
0.7707	Intermediate Similarity	NPD7228	Approved
0.7681	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD3539	Phase 1
0.7669	Intermediate Similarity	NPD1610	Phase 2
0.7662	Intermediate Similarity	NPD5494	Approved
0.766	Intermediate Similarity	NPD6111	Discontinued
0.7635	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD3540	Phase 1
0.7613	Intermediate Similarity	NPD7199	Phase 2
0.7591	Intermediate Similarity	NPD2861	Phase 2
0.7557	Intermediate Similarity	NPD5536	Phase 2
0.7518	Intermediate Similarity	NPD3657	Discovery
0.7516	Intermediate Similarity	NPD7240	Approved
0.7516	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD3620	Phase 2
0.7429	Intermediate Similarity	NPD5109	Approved
0.7429	Intermediate Similarity	NPD5110	Phase 2
0.7429	Intermediate Similarity	NPD5111	Phase 2
0.7426	Intermediate Similarity	NPD4749	Approved
0.7419	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD4005	Discontinued
0.7405	Intermediate Similarity	NPD7157	Approved
0.7397	Intermediate Similarity	NPD4236	Phase 3
0.7397	Intermediate Similarity	NPD4237	Approved
0.7391	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1934	Approved
0.7368	Intermediate Similarity	NPD1548	Phase 1
0.7364	Intermediate Similarity	NPD228	Approved
0.7333	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD1357	Approved
0.7308	Intermediate Similarity	NPD7843	Approved
0.7305	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD5327	Phase 3
0.729	Intermediate Similarity	NPD3817	Phase 2
0.7286	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD6674	Discontinued
0.7266	Intermediate Similarity	NPD2684	Approved
0.726	Intermediate Similarity	NPD1375	Discontinued
0.7255	Intermediate Similarity	NPD4678	Approved
0.7255	Intermediate Similarity	NPD4675	Approved
0.7244	Intermediate Similarity	NPD3882	Suspended
0.7244	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD4210	Discontinued
0.7234	Intermediate Similarity	NPD4625	Phase 3
0.723	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD6331	Phase 2
0.723	Intermediate Similarity	NPD4110	Phase 3
0.723	Intermediate Similarity	NPD7466	Approved
0.7226	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD3022	Approved
0.7209	Intermediate Similarity	NPD3021	Approved
0.72	Intermediate Similarity	NPD4357	Discontinued
0.7192	Intermediate Similarity	NPD2438	Suspended
0.7192	Intermediate Similarity	NPD2161	Phase 2
0.719	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD3926	Phase 2
0.7183	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6895	Approved
0.7172	Intermediate Similarity	NPD6896	Approved
0.7162	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD3818	Discontinued
0.7153	Intermediate Similarity	NPD5735	Approved
0.7143	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6166	Phase 2
0.7143	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1653	Approved
0.7123	Intermediate Similarity	NPD5588	Approved
0.7115	Intermediate Similarity	NPD2801	Approved
0.7114	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD3892	Phase 2
0.7105	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4055	Discovery
0.7086	Intermediate Similarity	NPD5297	Approved
0.7083	Intermediate Similarity	NPD2238	Phase 2
0.7083	Intermediate Similarity	NPD4060	Phase 1
0.7081	Intermediate Similarity	NPD5242	Approved
0.7077	Intermediate Similarity	NPD5451	Approved
0.7075	Intermediate Similarity	NPD2796	Approved
0.707	Intermediate Similarity	NPD5353	Approved
0.7067	Intermediate Similarity	NPD2219	Phase 1
0.7067	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5585	Approved
0.7055	Intermediate Similarity	NPD4538	Approved
0.7055	Intermediate Similarity	NPD4536	Approved
0.7055	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3384	Approved
0.7051	Intermediate Similarity	NPD3382	Approved
0.7051	Intermediate Similarity	NPD3383	Approved
0.705	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD3060	Approved
0.7047	Intermediate Similarity	NPD5177	Phase 3
0.7045	Intermediate Similarity	NPD5535	Approved
0.7034	Intermediate Similarity	NPD6355	Discontinued
0.7027	Intermediate Similarity	NPD7266	Discontinued
0.702	Intermediate Similarity	NPD5058	Phase 3
0.7019	Intermediate Similarity	NPD6232	Discontinued
0.7014	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD5844	Phase 1
0.7007	Intermediate Similarity	NPD17	Approved
0.7	Intermediate Similarity	NPD2922	Phase 1
0.7	Intermediate Similarity	NPD8651	Approved
0.6994	Remote Similarity	NPD7473	Discontinued
0.6993	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD1182	Approved
0.6978	Remote Similarity	NPD1840	Phase 2
0.697	Remote Similarity	NPD7074	Phase 3
0.6966	Remote Similarity	NPD1558	Phase 1
0.6966	Remote Similarity	NPD2979	Phase 3
0.6957	Remote Similarity	NPD1247	Approved
0.6948	Remote Similarity	NPD5976	Discontinued
0.6947	Remote Similarity	NPD4750	Phase 3
0.6944	Remote Similarity	NPD5718	Phase 2
0.6937	Remote Similarity	NPD919	Approved
0.6934	Remote Similarity	NPD5691	Approved
0.6934	Remote Similarity	NPD1651	Approved
0.6933	Remote Similarity	NPD4162	Approved
0.6928	Remote Similarity	NPD4123	Phase 3
0.6923	Remote Similarity	NPD1358	Approved
0.6923	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4380	Phase 2
0.6913	Remote Similarity	NPD5762	Approved
0.6913	Remote Similarity	NPD5763	Approved
0.6909	Remote Similarity	NPD7054	Approved
0.6908	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD1091	Approved
0.6892	Remote Similarity	NPD5960	Phase 3
0.6884	Remote Similarity	NPD5846	Approved
0.6884	Remote Similarity	NPD6516	Phase 2
0.6883	Remote Similarity	NPD7526	Approved
0.6883	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD52	Approved
0.6879	Remote Similarity	NPD5090	Approved
0.6879	Remote Similarity	NPD5089	Approved
0.6875	Remote Similarity	NPD7095	Approved
0.6875	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6353	Approved
0.6867	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7472	Approved
0.6863	Remote Similarity	NPD1511	Approved
0.6857	Remote Similarity	NPD1608	Approved
0.6855	Remote Similarity	NPD2563	Approved
0.6855	Remote Similarity	NPD2560	Approved
0.6852	Remote Similarity	NPD8127	Discontinued
0.685	Remote Similarity	NPD1242	Phase 1
0.6849	Remote Similarity	NPD4140	Approved
0.6846	Remote Similarity	NPD6099	Approved
0.6846	Remote Similarity	NPD3134	Approved
0.6846	Remote Similarity	NPD6100	Approved
0.6845	Remote Similarity	NPD7549	Discontinued
0.6842	Remote Similarity	NPD2677	Approved
0.6838	Remote Similarity	NPD3596	Phase 2
0.6821	Remote Similarity	NPD1652	Phase 2
0.6813	Remote Similarity	NPD6788	Approved
0.681	Remote Similarity	NPD7229	Phase 3
0.6809	Remote Similarity	NPD4359	Approved
0.6807	Remote Similarity	NPD8156	Discontinued
0.6806	Remote Similarity	NPD3537	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD230	Phase 1
0.6803	Remote Similarity	NPD5124	Phase 1
0.68	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD290	Approved
0.6792	Remote Similarity	NPD5773	Approved
0.6792	Remote Similarity	NPD2978	Approved
0.6792	Remote Similarity	NPD5772	Approved
0.6792	Remote Similarity	NPD7819	Suspended
0.6792	Remote Similarity	NPD4585	Approved
0.6792	Remote Similarity	NPD2977	Approved
0.6792	Remote Similarity	NPD1465	Phase 2
0.6788	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD422	Phase 1

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