NPASS Compound

Structure

CID106739 OpenBabel06191715452D 25 27 0 0 1 0 0 0 0 0999 V2000 -4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7453 0.1910 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 -6.1472 2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0132 3.1910 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 -3.5491 0.1910 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 -7.0132 1.1910 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 -4.4152 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2812 0.1910 0.0000 C 0 0 2 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 -6.1472 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8793 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 -7.8793 1.6910 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 -5.2812 1.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.7453 3.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 1.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7453 1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 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 3 23 1 0 0 0 0 4 7 2 0 0 0 0 4 14 1 0 0 0 0 5 6 2 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 7 17 1 0 0 0 0 8 12 1 0 0 0 0 8 14 1 0 0 0 0 9 14 2 0 0 0 0 9 19 1 0 0 0 0 10 15 2 0 0 0 0 10 18 1 0 0 0 0 11 24 1 0 0 0 0 11 25 1 0 0 0 0 12 1 1 1 0 0 0 12 13 1 0 0 0 0 13 2 1 1 0 0 0 13 20 1 0 0 0 0 15 20 1 0 0 0 0 16 18 2 0 0 0 0 16 21 1 0 0 0 0 17 19 2 0 0 0 0 17 24 1 0 0 0 0 18 23 1 0 0 0 0 19 25 1 0 0 0 0 20 22 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.16
Volume:	356.939
LogP:	3.866
LogD:	4.015
LogS:	-4.451
# Rotatable Bonds:	6
TPSA:	68.15
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.837
Synthetic Accessibility Score:	3.303
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.803
MDCK Permeability:	2.1768650185549632e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.024
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.029

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.136
Plasma Protein Binding (PPB):	98.85904693603516%
Volume Distribution (VD):	0.953
Pgp-substrate:	3.0733296871185303%

ADMET: Metabolism

CYP1A2-inhibitor:	0.926
CYP1A2-substrate:	0.867
CYP2C19-inhibitor:	0.957
CYP2C19-substrate:	0.632
CYP2C9-inhibitor:	0.886
CYP2C9-substrate:	0.914
CYP2D6-inhibitor:	0.978
CYP2D6-substrate:	0.919
CYP3A4-inhibitor:	0.954
CYP3A4-substrate:	0.81

ADMET: Excretion

Clearance (CL):	17.265
Half-life (T1/2):	0.441

ADMET: Toxicity

hERG Blockers:	0.089
Human Hepatotoxicity (H-HT):	0.107
Drug-inuced Liver Injury (DILI):	0.336
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.075
Skin Sensitization:	0.627
Carcinogencity:	0.727
Eye Corrosion:	0.004
Eye Irritation:	0.241
Respiratory Toxicity:	0.107

Download Data

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

Natural Product: NPC106739

Natural Product ID:	NPC106739
*Common Name:**	4-[(1S,2R,3R)-4-(1,3-Benzodioxol-5-Yl)-1-Hydroxy-2,3-Dimethylbutyl]-2-Methoxyphenol
IUPAC Name:	4-[(1S,2R,3R)-4-(1,3-benzodioxol-5-yl)-1-hydroxy-2,3-dimethylbutyl]-2-methoxyphenol
Synonyms:
Standard InCHIKey:	GSIZVLCQLAZSSP-IZDJOXEWSA-N
Standard InCHI:	InChI=1S/C20H24O5/c1-12(8-14-4-7-17-19(9-14)25-11-24-17)13(2)20(22)15-5-6-16(21)18(10-15)23-3/h4-7,9-10,12-13,20-22H,8,11H2,1-3H3/t12-,13-,20+/m1/s1
SMILES:	COc1cc(ccc1O)[C@H]([C@@H]([C@@H](Cc1ccc2c(c1)OCO2)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL253433
PubChem CID:	44447179
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001969] Dibenzylbutane 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
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	seeds	n.a.	n.a.	PMID[17998162]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1955885]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	fruit	n.a.	PMID[20879744]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27419473]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Aril	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8303	Catalpa bignonioides	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1382	Hyptis tomentosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO1382	Hyptis tomentosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8303	Catalpa bignonioides	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1382	Hyptis tomentosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17811	Cephalonoplos segetum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5746	Pancratium trianthum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7393	Esenbeckia nesiotica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5334	Rhodotypos scandens	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19928	Lachnoanaerobaculum saburreum	Species	Lachnospiraceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2665	Andinobates fulguritus	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7237	Xanthostemon oppositifolius	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8303	Catalpa bignonioides	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28409	Lens phaseoloides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8532	Helipterum tenellum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1382	Hyptis tomentosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6113	Piper pedicellosum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5162	Comaster multifida	Species	Comatulidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4539	Ipomoea cristulata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO490	Lophozonia menziesii	Species	0thofagaceae	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	1
Others	1

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	45.7	%	PMID[504293]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6300.0	nM	PMID[504293]

☑ 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 NPC106739 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	351
0.1-0.2	1378
0.2-0.3	3610
0.3-0.4	10245
0.4-0.5	8645
0.5-0.6	5167
0.6-0.7	8634
0.7-0.8	3352
0.8-0.85	858
0.85-0.9	352
0.9-0.95	96
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9841	High Similarity	NPC471505
0.9766	High Similarity	NPC101624
0.9766	High Similarity	NPC184938
0.9612	High Similarity	NPC135777
0.9612	High Similarity	NPC142547
0.9531	High Similarity	NPC104077
0.9531	High Similarity	NPC219671
0.9531	High Similarity	NPC147616
0.9531	High Similarity	NPC259742
0.9528	High Similarity	NPC173308
0.9528	High Similarity	NPC275950
0.9528	High Similarity	NPC181079
0.952	High Similarity	NPC274356
0.9466	High Similarity	NPC474039
0.9457	High Similarity	NPC169973
0.9453	High Similarity	NPC476345
0.9449	High Similarity	NPC475875
0.9398	High Similarity	NPC472711
0.9394	High Similarity	NPC193666
0.9394	High Similarity	NPC123526
0.9394	High Similarity	NPC88640
0.9375	High Similarity	NPC77040
0.9375	High Similarity	NPC145305
0.9375	High Similarity	NPC92164
0.9375	High Similarity	NPC42300
0.9375	High Similarity	NPC257582
0.9375	High Similarity	NPC174495
0.9375	High Similarity	NPC153739
0.9375	High Similarity	NPC187998
0.9375	High Similarity	NPC241522
0.9375	High Similarity	NPC64201
0.9375	High Similarity	NPC242807
0.937	High Similarity	NPC128208
0.937	High Similarity	NPC11258
0.937	High Similarity	NPC282703
0.937	High Similarity	NPC45774
0.937	High Similarity	NPC184733
0.937	High Similarity	NPC21867
0.937	High Similarity	NPC129570
0.9302	High Similarity	NPC277804
0.9291	High Similarity	NPC118533
0.9291	High Similarity	NPC165045
0.9286	High Similarity	NPC148627
0.928	High Similarity	NPC249788
0.9259	High Similarity	NPC477898
0.9259	High Similarity	NPC470950
0.9259	High Similarity	NPC185307
0.9219	High Similarity	NPC470084
0.9213	High Similarity	NPC40352
0.9213	High Similarity	NPC213711
0.92	High Similarity	NPC85488
0.9191	High Similarity	NPC84181
0.9191	High Similarity	NPC283995
0.9191	High Similarity	NPC470235
0.9191	High Similarity	NPC129417
0.9185	High Similarity	NPC253878
0.9185	High Similarity	NPC476356
0.9179	High Similarity	NPC177868
0.9167	High Similarity	NPC18576
0.916	High Similarity	NPC196937
0.9154	High Similarity	NPC40432
0.9154	High Similarity	NPC158079
0.9154	High Similarity	NPC7171
0.9154	High Similarity	NPC27843
0.9154	High Similarity	NPC161557
0.9154	High Similarity	NPC228346
0.9154	High Similarity	NPC115207
0.9141	High Similarity	NPC5428
0.9127	High Similarity	NPC31344
0.9127	High Similarity	NPC317769
0.9127	High Similarity	NPC280704
0.9127	High Similarity	NPC471693
0.9124	High Similarity	NPC279298
0.9124	High Similarity	NPC22150
0.9124	High Similarity	NPC38041
0.9118	High Similarity	NPC298317
0.9118	High Similarity	NPC265154
0.9118	High Similarity	NPC255566
0.9118	High Similarity	NPC46092
0.9111	High Similarity	NPC471414
0.9098	High Similarity	NPC177035
0.9098	High Similarity	NPC199459
0.9098	High Similarity	NPC52277
0.9091	High Similarity	NPC47181
0.9091	High Similarity	NPC67247
0.9091	High Similarity	NPC470881
0.9091	High Similarity	NPC287745
0.9084	High Similarity	NPC181049
0.9084	High Similarity	NPC207400
0.9084	High Similarity	NPC97316
0.9084	High Similarity	NPC227002
0.907	High Similarity	NPC158471
0.907	High Similarity	NPC57119
0.907	High Similarity	NPC226862
0.907	High Similarity	NPC165128
0.9062	High Similarity	NPC206882
0.9058	High Similarity	NPC112861
0.9051	High Similarity	NPC118385
0.9051	High Similarity	NPC187774
0.9051	High Similarity	NPC472713
0.9051	High Similarity	NPC473046
0.9051	High Similarity	NPC472712
0.9044	High Similarity	NPC302506
0.904	High Similarity	NPC207613
0.9037	High Similarity	NPC284464
0.9023	High Similarity	NPC174191
0.9015	High Similarity	NPC112237
0.9015	High Similarity	NPC6836
0.9015	High Similarity	NPC158331
0.9008	High Similarity	NPC65942
0.9008	High Similarity	NPC474017
0.9008	High Similarity	NPC248307
0.8993	High Similarity	NPC39657
0.8993	High Similarity	NPC275284
0.8993	High Similarity	NPC15956
0.8993	High Similarity	NPC114505
0.8993	High Similarity	NPC193473
0.8993	High Similarity	NPC213074
0.8993	High Similarity	NPC31325
0.8993	High Similarity	NPC224674
0.8986	High Similarity	NPC166506
0.8986	High Similarity	NPC189239
0.8986	High Similarity	NPC110763
0.8986	High Similarity	NPC18979
0.8986	High Similarity	NPC197352
0.8978	High Similarity	NPC474808
0.8978	High Similarity	NPC185071
0.8978	High Similarity	NPC278961
0.8978	High Similarity	NPC12728
0.8978	High Similarity	NPC113680
0.8968	High Similarity	NPC470212
0.8968	High Similarity	NPC312675
0.8968	High Similarity	NPC324571
0.8968	High Similarity	NPC262156
0.8968	High Similarity	NPC343720
0.8968	High Similarity	NPC113865
0.8968	High Similarity	NPC476343
0.8968	High Similarity	NPC473853
0.8968	High Similarity	NPC184651
0.8968	High Similarity	NPC54872
0.8963	High Similarity	NPC30951
0.8963	High Similarity	NPC6369
0.8963	High Similarity	NPC156376
0.896	High Similarity	NPC117780
0.896	High Similarity	NPC344161
0.896	High Similarity	NPC242885
0.896	High Similarity	NPC232316
0.896	High Similarity	NPC56214
0.896	High Similarity	NPC227217
0.896	High Similarity	NPC165133
0.896	High Similarity	NPC95614
0.8955	High Similarity	NPC263367
0.8955	High Similarity	NPC10737
0.8955	High Similarity	NPC156502
0.8955	High Similarity	NPC25695
0.8955	High Similarity	NPC77861
0.8955	High Similarity	NPC172818
0.8955	High Similarity	NPC29799
0.8955	High Similarity	NPC209985
0.8955	High Similarity	NPC477939
0.8955	High Similarity	NPC471988
0.8955	High Similarity	NPC54743
0.8955	High Similarity	NPC177160
0.8947	High Similarity	NPC326095
0.8947	High Similarity	NPC187616
0.8947	High Similarity	NPC471942
0.8947	High Similarity	NPC244983
0.8947	High Similarity	NPC193026
0.8947	High Similarity	NPC49603
0.8939	High Similarity	NPC4940
0.8939	High Similarity	NPC252833
0.8939	High Similarity	NPC175067
0.8939	High Similarity	NPC204215
0.8931	High Similarity	NPC143483
0.8931	High Similarity	NPC134764
0.8931	High Similarity	NPC63574
0.8931	High Similarity	NPC233224
0.8931	High Similarity	NPC271208
0.8931	High Similarity	NPC171550
0.8929	High Similarity	NPC304048
0.8929	High Similarity	NPC226153
0.8923	High Similarity	NPC245826
0.8923	High Similarity	NPC252307
0.8923	High Similarity	NPC474178
0.8921	High Similarity	NPC212890
0.8915	High Similarity	NPC191037
0.8915	High Similarity	NPC178284
0.8915	High Similarity	NPC58607
0.8913	High Similarity	NPC121661
0.8913	High Similarity	NPC179521
0.8913	High Similarity	NPC73467
0.8905	High Similarity	NPC52664
0.8905	High Similarity	NPC5262
0.8905	High Similarity	NPC48309
0.8905	High Similarity	NPC472714
0.8905	High Similarity	NPC41782
0.8905	High Similarity	NPC246947
0.8889	High Similarity	NPC304152
0.8889	High Similarity	NPC469981
0.8889	High Similarity	NPC185908

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 NPC106739 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	284
0.1-0.2	847
0.2-0.3	1713
0.3-0.4	2722
0.4-0.5	1781
0.5-0.6	1027
0.6-0.7	635
0.7-0.8	128
0.8-0.85	11
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8855	High Similarity	NPD3027	Phase 3
0.8583	High Similarity	NPD1357	Approved
0.8527	High Similarity	NPD3705	Approved
0.84	Intermediate Similarity	NPD5283	Phase 1
0.8248	Intermediate Similarity	NPD3620	Phase 2
0.8248	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.824	Intermediate Similarity	NPD228	Approved
0.8188	Intermediate Similarity	NPD2978	Approved
0.8188	Intermediate Similarity	NPD2977	Approved
0.8121	Intermediate Similarity	NPD37	Approved
0.8116	Intermediate Similarity	NPD1613	Approved
0.8116	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD6234	Discontinued
0.808	Intermediate Similarity	NPD3022	Approved
0.808	Intermediate Similarity	NPD3021	Approved
0.8028	Intermediate Similarity	NPD7266	Discontinued
0.7985	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD4966	Approved
0.7961	Intermediate Similarity	NPD4965	Approved
0.7961	Intermediate Similarity	NPD4967	Phase 2
0.7945	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD6674	Discontinued
0.7883	Intermediate Similarity	NPD2861	Phase 2
0.7848	Intermediate Similarity	NPD7228	Approved
0.7826	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD4060	Phase 1
0.7704	Intermediate Similarity	NPD1091	Approved
0.7671	Intermediate Similarity	NPD3060	Approved
0.7643	Intermediate Similarity	NPD7199	Phase 2
0.7635	Intermediate Similarity	NPD5058	Phase 3
0.7625	Intermediate Similarity	NPD3818	Discontinued
0.7616	Intermediate Similarity	NPD1653	Approved
0.7591	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD2684	Approved
0.7576	Intermediate Similarity	NPD7157	Approved
0.7551	Intermediate Similarity	NPD4236	Phase 3
0.7551	Intermediate Similarity	NPD4237	Approved
0.7534	Intermediate Similarity	NPD1375	Discontinued
0.75	Intermediate Similarity	NPD4110	Phase 3
0.75	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1558	Phase 1
0.7481	Intermediate Similarity	NPD7843	Approved
0.7464	Intermediate Similarity	NPD2983	Phase 2
0.7464	Intermediate Similarity	NPD2982	Phase 2
0.7463	Intermediate Similarity	NPD5536	Phase 2
0.7447	Intermediate Similarity	NPD4908	Phase 1
0.7439	Intermediate Similarity	NPD7685	Pre-registration
0.7438	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD5735	Approved
0.7431	Intermediate Similarity	NPD6355	Discontinued
0.7426	Intermediate Similarity	NPD5126	Approved
0.7426	Intermediate Similarity	NPD5125	Phase 3
0.7423	Intermediate Similarity	NPD7074	Phase 3
0.7415	Intermediate Similarity	NPD5763	Approved
0.7415	Intermediate Similarity	NPD5762	Approved
0.7403	Intermediate Similarity	NPD7028	Phase 2
0.7397	Intermediate Similarity	NPD5588	Approved
0.7391	Intermediate Similarity	NPD2981	Phase 2
0.7383	Intermediate Similarity	NPD6331	Phase 2
0.7376	Intermediate Similarity	NPD3018	Phase 2
0.7372	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD7054	Approved
0.7361	Intermediate Similarity	NPD2238	Phase 2
0.736	Intermediate Similarity	NPD3020	Approved
0.7357	Intermediate Similarity	NPD3094	Phase 2
0.7343	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD5110	Phase 2
0.7343	Intermediate Similarity	NPD5109	Approved
0.7343	Intermediate Similarity	NPD5111	Phase 2
0.7342	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7240	Approved
0.7333	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4536	Approved
0.7329	Intermediate Similarity	NPD4538	Approved
0.732	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD3092	Approved
0.7319	Intermediate Similarity	NPD1610	Phase 2
0.7317	Intermediate Similarity	NPD7472	Approved
0.7315	Intermediate Similarity	NPD5177	Phase 3
0.7315	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD3657	Discovery
0.7308	Intermediate Similarity	NPD1934	Approved
0.7297	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD2674	Phase 3
0.7285	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4108	Discontinued
0.7273	Intermediate Similarity	NPD7095	Approved
0.7267	Intermediate Similarity	NPD4628	Phase 3
0.726	Intermediate Similarity	NPD6653	Approved
0.7241	Intermediate Similarity	NPD4140	Approved
0.723	Intermediate Similarity	NPD2161	Phase 2
0.7222	Intermediate Similarity	NPD3144	Approved
0.7222	Intermediate Similarity	NPD3145	Approved
0.7219	Intermediate Similarity	NPD5241	Discontinued
0.7214	Intermediate Similarity	NPD3685	Discontinued
0.7202	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4162	Approved
0.7185	Intermediate Similarity	NPD6671	Approved
0.7183	Intermediate Similarity	NPD6584	Phase 3
0.7178	Intermediate Similarity	NPD2489	Approved
0.7178	Intermediate Similarity	NPD27	Approved
0.7174	Intermediate Similarity	NPD6516	Phase 2
0.7174	Intermediate Similarity	NPD5846	Approved
0.7172	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD3882	Suspended
0.7169	Intermediate Similarity	NPD6797	Phase 2
0.7163	Intermediate Similarity	NPD8651	Approved
0.7162	Intermediate Similarity	NPD5960	Phase 3
0.7154	Intermediate Similarity	NPD968	Approved
0.7153	Intermediate Similarity	NPD3091	Approved
0.7152	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2232	Approved
0.7143	Intermediate Similarity	NPD2235	Phase 2
0.7143	Intermediate Similarity	NPD2230	Approved
0.7143	Intermediate Similarity	NPD2231	Phase 2
0.7143	Intermediate Similarity	NPD2233	Approved
0.7133	Intermediate Similarity	NPD9494	Approved
0.7126	Intermediate Similarity	NPD7251	Discontinued
0.7125	Intermediate Similarity	NPD5604	Discontinued
0.7123	Intermediate Similarity	NPD3062	Approved
0.7123	Intermediate Similarity	NPD3059	Approved
0.7123	Intermediate Similarity	NPD3061	Approved
0.712	Intermediate Similarity	NPD2859	Approved
0.712	Intermediate Similarity	NPD2860	Approved
0.7105	Intermediate Similarity	NPD2677	Approved
0.7105	Intermediate Similarity	NPD6190	Approved
0.7105	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6798	Discontinued
0.7099	Intermediate Similarity	NPD290	Approved
0.7099	Intermediate Similarity	NPD8127	Discontinued
0.7095	Intermediate Similarity	NPD7097	Phase 1
0.7095	Intermediate Similarity	NPD6896	Approved
0.7095	Intermediate Similarity	NPD6895	Approved
0.7092	Intermediate Similarity	NPD5327	Phase 3
0.7089	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7808	Phase 3
0.7083	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD4123	Phase 3
0.7073	Intermediate Similarity	NPD6166	Phase 2
0.7073	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4624	Approved
0.7059	Intermediate Similarity	NPD709	Approved
0.7055	Intermediate Similarity	NPD6233	Phase 2
0.7055	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3686	Approved
0.7051	Intermediate Similarity	NPD3687	Approved
0.705	Intermediate Similarity	NPD2668	Approved
0.705	Intermediate Similarity	NPD2667	Approved
0.705	Intermediate Similarity	NPD9381	Approved
0.705	Intermediate Similarity	NPD4626	Approved
0.705	Intermediate Similarity	NPD9384	Approved
0.7047	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD5773	Approved
0.7044	Intermediate Similarity	NPD8455	Phase 2
0.7044	Intermediate Similarity	NPD2801	Approved
0.7044	Intermediate Similarity	NPD5772	Approved
0.7044	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD1283	Approved
0.704	Intermediate Similarity	NPD2934	Approved
0.704	Intermediate Similarity	NPD2933	Approved
0.704	Intermediate Similarity	NPD9296	Approved
0.7032	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD7526	Approved
0.7032	Intermediate Similarity	NPD52	Approved
0.7032	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD1548	Phase 1
0.7027	Intermediate Similarity	NPD5314	Approved
0.7024	Intermediate Similarity	NPD6559	Discontinued
0.7021	Intermediate Similarity	NPD1608	Approved
0.7019	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD2970	Approved
0.7012	Intermediate Similarity	NPD2969	Approved
0.7007	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4005	Discontinued
0.7	Intermediate Similarity	NPD2563	Approved
0.7	Intermediate Similarity	NPD2560	Approved
0.7	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3847	Discontinued
0.6992	Remote Similarity	NPD5451	Approved
0.6986	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD5585	Approved
0.6977	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD291	Approved
0.6972	Remote Similarity	NPD9622	Approved
0.6972	Remote Similarity	NPD6582	Phase 2
0.6972	Remote Similarity	NPD4749	Approved
0.6972	Remote Similarity	NPD6583	Phase 3
0.6968	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD1138	Approved
0.6963	Remote Similarity	NPD5535	Approved
0.6951	Remote Similarity	NPD3051	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