NPASS Compound

Structure

NPC64340 OpenBabel07101719252D 36 40 0 0 1 0 0 0 0 0999 V2000 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 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 -5.1962 3.0000 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 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 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 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 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 -2.5981 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 1 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 -0.8660 1.5000 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 -4.3301 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 -2.5981 1.5000 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 4 2 0 0 0 0 1 5 1 0 0 0 0 2 6 2 0 0 0 0 2 7 1 0 0 0 0 3 8 2 0 0 0 0 3 9 1 0 0 0 0 4 10 1 0 0 0 0 5 11 2 0 0 0 0 6 12 1 0 0 0 0 7 13 2 0 0 0 0 8 14 1 0 0 0 0 9 15 2 0 0 0 0 10 23 2 0 0 0 0 11 23 1 0 0 0 0 12 24 2 0 0 0 0 13 24 1 0 0 0 0 14 25 2 0 0 0 0 15 25 1 0 0 0 0 16 18 1 0 0 0 0 16 23 1 0 0 0 0 17 19 2 0 0 0 0 17 24 1 0 0 0 0 18 26 1 0 0 0 0 19 27 1 0 0 0 0 20 26 1 0 0 0 0 21 28 1 0 0 0 0 21 29 1 0 0 0 0 22 27 2 0 0 0 0 22 30 1 0 0 0 0 26 33 2 0 0 0 0 27 36 1 0 0 0 0 28 20 1 6 0 0 0 28 35 1 0 0 0 0 29 25 1 1 0 0 0 29 31 1 0 0 0 0 30 31 2 0 0 0 0 30 35 1 0 0 0 0 31 32 1 0 0 0 0 32 34 2 0 0 0 0 32 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	476.2
Volume:	517.496
LogP:	5.783
LogD:	4.54
LogS:	-5.965
# Rotatable Bonds:	8
TPSA:	56.51
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.284
Synthetic Accessibility Score:	3.424
Fsp3:	0.188
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:	-4.978
MDCK Permeability:	1.0754529284895398e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.948
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.973
30% Bioavailability (F30%):	0.643

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.122
Plasma Protein Binding (PPB):	100.67521667480469%
Volume Distribution (VD):	0.217
Pgp-substrate:	0.36175036430358887%

ADMET: Metabolism

CYP1A2-inhibitor:	0.508
CYP1A2-substrate:	0.262
CYP2C19-inhibitor:	0.945
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.976
CYP2C9-substrate:	0.983
CYP2D6-inhibitor:	0.244
CYP2D6-substrate:	0.73
CYP3A4-inhibitor:	0.84
CYP3A4-substrate:	0.773

ADMET: Excretion

Clearance (CL):	4.299
Half-life (T1/2):	0.064

ADMET: Toxicity

hERG Blockers:	0.421
Human Hepatotoxicity (H-HT):	0.979
Drug-inuced Liver Injury (DILI):	0.972
AMES Toxicity:	0.353
Rat Oral Acute Toxicity:	0.895
Maximum Recommended Daily Dose:	0.995
Skin Sensitization:	0.231
Carcinogencity:	0.711
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC64340

Natural Product ID:	NPC64340
*Common Name:**	Katsumadain A
IUPAC Name:	(2S,4S)-2-(2-oxo-4-phenylbutyl)-4-phenyl-7-[(E)-2-phenylethenyl]-3,4-dihydro-2H-pyrano[3,2-c]pyran-5-one
Synonyms:
Standard InCHIKey:	IAIGBNIWSBFKNA-FIACUDKOSA-N
Standard InCHI:	InChI=1S/C32H28O4/c33-26(18-16-23-10-4-1-5-11-23)20-28-21-29(25-14-8-3-9-15-25)31-30(35-28)22-27(36-32(31)34)19-17-24-12-6-2-7-13-24/h1-15,17,19,22,28-29H,16,18,20-21H2/b19-17+/t28-,29+/m1/s1
SMILES:	O=C(C[C@H]1Oc2cc(/C=C/c3ccccc3)oc(=O)c2[C@@H](C1)c1ccccc1)CCc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL480470
PubChem CID:	9982435
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10654416]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	seed	n.a.	PMID[14577694]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20014777]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	seed	n.a.	PMID[21942765]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	seeds	n.a.	n.a.	PMID[21942765]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22459211]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	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	6
Others	5

Activity Type	# Activity
Cell Line	1
Individual Protein	6
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1602	Individual Protein	Neuraminidase	Influenza A virus (A/Puerto Rico/8/1934(H1N1))	IC50	=	1050.0	nM	PMID[484897]
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	=	0.73	nM	PMID[484897]
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	=	0.59	nM	PMID[484897]
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	=	1.11	nM	PMID[484897]
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	=	1.64	nM	PMID[484897]
NPT493	Individual Protein	Neuraminidase	Influenza A virus	Inhibition	=	45.9	%	PMID[484897]
NPT616	Cell Line	MDCK	Canis lupus familiaris	CC50	=	66900.0	nM	PMID[484897]
NPT673	Organism	Gallus gallus	Gallus gallus	Inhibition	=	8.8	%	PMID[484896]
NPT673	Organism	Gallus gallus	Gallus gallus	Inhibition	=	14.5	%	PMID[484896]
NPT673	Organism	Gallus gallus	Gallus gallus	Inhibition	=	50.2	%	PMID[484896]
NPT1453	Organism	Influenza A virus (A/PR/8/34(H1N1))	Influenza A virus (A/Puerto Rico/8/1934(H1N1))	IC50	=	11750.0	nM	PMID[484897]

☑ 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 NPC64340 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	438
0.1-0.2	1592
0.2-0.3	3908
0.3-0.4	9556
0.4-0.5	9462
0.5-0.6	4551
0.6-0.7	6752
0.7-0.8	5814
0.8-0.85	566
0.85-0.9	55
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8584	High Similarity	NPC40178
0.8522	High Similarity	NPC474689
0.8496	Intermediate Similarity	NPC47536
0.7903	Intermediate Similarity	NPC475804
0.7903	Intermediate Similarity	NPC474222
0.7903	Intermediate Similarity	NPC474223
0.7903	Intermediate Similarity	NPC280827
0.7903	Intermediate Similarity	NPC475827
0.7903	Intermediate Similarity	NPC243059
0.7869	Intermediate Similarity	NPC190298
0.7863	Intermediate Similarity	NPC20485
0.7857	Intermediate Similarity	NPC474254
0.7857	Intermediate Similarity	NPC474159
0.7786	Intermediate Similarity	NPC472361
0.7752	Intermediate Similarity	NPC473423
0.7669	Intermediate Similarity	NPC472437
0.7652	Intermediate Similarity	NPC60825
0.7652	Intermediate Similarity	NPC291419
0.7642	Intermediate Similarity	NPC471616
0.7563	Intermediate Similarity	NPC470007
0.7537	Intermediate Similarity	NPC15850
0.752	Intermediate Similarity	NPC152812
0.7519	Intermediate Similarity	NPC289415
0.7519	Intermediate Similarity	NPC319995
0.7519	Intermediate Similarity	NPC469742
0.7519	Intermediate Similarity	NPC475478
0.75	Intermediate Similarity	NPC77273
0.748	Intermediate Similarity	NPC87069
0.748	Intermediate Similarity	NPC476225
0.7479	Intermediate Similarity	NPC477251
0.7463	Intermediate Similarity	NPC475493
0.7445	Intermediate Similarity	NPC184109
0.7434	Intermediate Similarity	NPC23453
0.7429	Intermediate Similarity	NPC284957
0.7419	Intermediate Similarity	NPC474408
0.741	Intermediate Similarity	NPC213567
0.7405	Intermediate Similarity	NPC79608
0.7405	Intermediate Similarity	NPC470818
0.7405	Intermediate Similarity	NPC476033
0.7394	Intermediate Similarity	NPC169942
0.7391	Intermediate Similarity	NPC472395
0.7391	Intermediate Similarity	NPC270654
0.7391	Intermediate Similarity	NPC472371
0.7388	Intermediate Similarity	NPC305162
0.7388	Intermediate Similarity	NPC17567
0.7387	Intermediate Similarity	NPC231591
0.7381	Intermediate Similarity	NPC469574
0.7361	Intermediate Similarity	NPC282335
0.7361	Intermediate Similarity	NPC218300
0.736	Intermediate Similarity	NPC473507
0.7353	Intermediate Similarity	NPC4242
0.7353	Intermediate Similarity	NPC471911
0.7353	Intermediate Similarity	NPC136994
0.7353	Intermediate Similarity	NPC88255
0.7333	Intermediate Similarity	NPC209851
0.7328	Intermediate Similarity	NPC472694
0.7328	Intermediate Similarity	NPC472693
0.7311	Intermediate Similarity	NPC269644
0.7308	Intermediate Similarity	NPC223351
0.7293	Intermediate Similarity	NPC195224
0.7288	Intermediate Similarity	NPC474112
0.728	Intermediate Similarity	NPC210092
0.7279	Intermediate Similarity	NPC270268
0.7273	Intermediate Similarity	NPC473082
0.7266	Intermediate Similarity	NPC476096
0.7265	Intermediate Similarity	NPC476042
0.7258	Intermediate Similarity	NPC128368
0.7258	Intermediate Similarity	NPC477475
0.7258	Intermediate Similarity	NPC477476
0.7254	Intermediate Similarity	NPC285550
0.7252	Intermediate Similarity	NPC473881
0.7252	Intermediate Similarity	NPC325740
0.7244	Intermediate Similarity	NPC61651
0.7239	Intermediate Similarity	NPC225103
0.7239	Intermediate Similarity	NPC471024
0.7236	Intermediate Similarity	NPC474157
0.7231	Intermediate Similarity	NPC473749
0.7226	Intermediate Similarity	NPC153617
0.7226	Intermediate Similarity	NPC470143
0.7226	Intermediate Similarity	NPC322503
0.7222	Intermediate Similarity	NPC260886
0.7218	Intermediate Similarity	NPC190849
0.7218	Intermediate Similarity	NPC171007
0.7217	Intermediate Similarity	NPC206764
0.7213	Intermediate Similarity	NPC281604
0.7207	Intermediate Similarity	NPC96625
0.7206	Intermediate Similarity	NPC475569
0.7203	Intermediate Similarity	NPC470130
0.7203	Intermediate Similarity	NPC183824
0.72	Intermediate Similarity	NPC294458
0.719	Intermediate Similarity	NPC51174
0.7185	Intermediate Similarity	NPC472388
0.7185	Intermediate Similarity	NPC473443
0.7185	Intermediate Similarity	NPC11025
0.7168	Intermediate Similarity	NPC240108
0.7168	Intermediate Similarity	NPC213156
0.7164	Intermediate Similarity	NPC471025
0.7162	Intermediate Similarity	NPC204561
0.7162	Intermediate Similarity	NPC317715
0.7162	Intermediate Similarity	NPC309512
0.7162	Intermediate Similarity	NPC148945
0.7162	Intermediate Similarity	NPC78835
0.7162	Intermediate Similarity	NPC316960
0.7154	Intermediate Similarity	NPC273837
0.7153	Intermediate Similarity	NPC472656
0.7152	Intermediate Similarity	NPC322459
0.7152	Intermediate Similarity	NPC323627
0.7152	Intermediate Similarity	NPC324358
0.7152	Intermediate Similarity	NPC318527
0.7133	Intermediate Similarity	NPC52576
0.7133	Intermediate Similarity	NPC473677
0.7133	Intermediate Similarity	NPC80895
0.7133	Intermediate Similarity	NPC471912
0.7133	Intermediate Similarity	NPC475404
0.7132	Intermediate Similarity	NPC472418
0.7131	Intermediate Similarity	NPC156648
0.7124	Intermediate Similarity	NPC175513
0.7123	Intermediate Similarity	NPC254558
0.7121	Intermediate Similarity	NPC138798
0.7121	Intermediate Similarity	NPC140118
0.7121	Intermediate Similarity	NPC12881
0.7113	Intermediate Similarity	NPC470986
0.7113	Intermediate Similarity	NPC172311
0.7109	Intermediate Similarity	NPC268930
0.7109	Intermediate Similarity	NPC84129
0.7107	Intermediate Similarity	NPC269457
0.7105	Intermediate Similarity	NPC187725
0.7105	Intermediate Similarity	NPC141607
0.7095	Intermediate Similarity	NPC304876
0.7095	Intermediate Similarity	NPC472005
0.7095	Intermediate Similarity	NPC77719
0.7095	Intermediate Similarity	NPC472022
0.7095	Intermediate Similarity	NPC242262
0.7095	Intermediate Similarity	NPC265395
0.7095	Intermediate Similarity	NPC237549
0.7095	Intermediate Similarity	NPC472030
0.7095	Intermediate Similarity	NPC473414
0.7095	Intermediate Similarity	NPC249471
0.7095	Intermediate Similarity	NPC256142
0.7095	Intermediate Similarity	NPC158333
0.7095	Intermediate Similarity	NPC257213
0.7095	Intermediate Similarity	NPC1173
0.7094	Intermediate Similarity	NPC103048
0.7092	Intermediate Similarity	NPC475400
0.7092	Intermediate Similarity	NPC473440
0.709	Intermediate Similarity	NPC204214
0.709	Intermediate Similarity	NPC124878
0.709	Intermediate Similarity	NPC92283
0.709	Intermediate Similarity	NPC253681
0.709	Intermediate Similarity	NPC198918
0.709	Intermediate Similarity	NPC290276
0.709	Intermediate Similarity	NPC63404
0.709	Intermediate Similarity	NPC35338
0.709	Intermediate Similarity	NPC231888
0.709	Intermediate Similarity	NPC146239
0.709	Intermediate Similarity	NPC10121
0.709	Intermediate Similarity	NPC10883
0.7087	Intermediate Similarity	NPC476476
0.7083	Intermediate Similarity	NPC301946
0.7083	Intermediate Similarity	NPC277053
0.7083	Intermediate Similarity	NPC301943
0.7083	Intermediate Similarity	NPC474365
0.708	Intermediate Similarity	NPC9822
0.708	Intermediate Similarity	NPC471880
0.708	Intermediate Similarity	NPC472394
0.7077	Intermediate Similarity	NPC473243
0.7075	Intermediate Similarity	NPC101043
0.7075	Intermediate Similarity	NPC306799
0.7073	Intermediate Similarity	NPC475282
0.7073	Intermediate Similarity	NPC469636
0.7068	Intermediate Similarity	NPC114927
0.7068	Intermediate Similarity	NPC295664
0.7068	Intermediate Similarity	NPC87153
0.7068	Intermediate Similarity	NPC162925
0.7068	Intermediate Similarity	NPC473083
0.7068	Intermediate Similarity	NPC477369
0.7063	Intermediate Similarity	NPC191082
0.7063	Intermediate Similarity	NPC270498
0.7063	Intermediate Similarity	NPC246480
0.7063	Intermediate Similarity	NPC82467
0.7063	Intermediate Similarity	NPC473673
0.7063	Intermediate Similarity	NPC475429
0.7063	Intermediate Similarity	NPC172525
0.7063	Intermediate Similarity	NPC147217
0.7063	Intermediate Similarity	NPC177340
0.7063	Intermediate Similarity	NPC139067
0.7059	Intermediate Similarity	NPC471832
0.7059	Intermediate Similarity	NPC42211
0.7059	Intermediate Similarity	NPC214246
0.7059	Intermediate Similarity	NPC475138
0.7059	Intermediate Similarity	NPC475671
0.7059	Intermediate Similarity	NPC147561
0.7059	Intermediate Similarity	NPC475452
0.7054	Intermediate Similarity	NPC89324
0.705	Intermediate Similarity	NPC477893
0.7047	Intermediate Similarity	NPC228204
0.7047	Intermediate Similarity	NPC26033
0.7047	Intermediate Similarity	NPC114410
0.7047	Intermediate Similarity	NPC112523
0.7045	Intermediate Similarity	NPC141970

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 NPC64340 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	387
0.1-0.2	926
0.2-0.3	1503
0.3-0.4	2626
0.4-0.5	2018
0.5-0.6	1174
0.6-0.7	377
0.7-0.8	112
0.8-0.85	20
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.807	Intermediate Similarity	NPD5909	Discontinued
0.7692	Intermediate Similarity	NPD5048	Discontinued
0.7565	Intermediate Similarity	NPD7798	Approved
0.7295	Intermediate Similarity	NPD2067	Discontinued
0.7258	Intermediate Similarity	NPD7094	Approved
0.7258	Intermediate Similarity	NPD6858	Approved
0.7153	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6647	Phase 2
0.7045	Intermediate Similarity	NPD6637	Approved
0.7034	Intermediate Similarity	NPD5926	Approved
0.7018	Intermediate Similarity	NPD3673	Approved
0.7018	Intermediate Similarity	NPD3672	Approved
0.7015	Intermediate Similarity	NPD3266	Approved
0.7015	Intermediate Similarity	NPD3267	Approved
0.7009	Intermediate Similarity	NPD1989	Approved
0.6993	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1238	Approved
0.6963	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.696	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.695	Remote Similarity	NPD7033	Discontinued
0.6947	Remote Similarity	NPD17	Approved
0.6929	Remote Similarity	NPD6010	Discontinued
0.6905	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD1282	Approved
0.6901	Remote Similarity	NPD2796	Approved
0.6884	Remote Similarity	NPD3268	Approved
0.6871	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD2066	Phase 3
0.6821	Remote Similarity	NPD7411	Suspended
0.6818	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2182	Approved
0.6797	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD1608	Approved
0.6779	Remote Similarity	NPD5403	Approved
0.6765	Remote Similarity	NPD2797	Approved
0.6763	Remote Similarity	NPD3764	Approved
0.6757	Remote Similarity	NPD5401	Approved
0.6736	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD2798	Approved
0.6713	Remote Similarity	NPD3748	Approved
0.6712	Remote Similarity	NPD4628	Phase 3
0.6692	Remote Similarity	NPD3317	Approved
0.6691	Remote Similarity	NPD3225	Approved
0.6691	Remote Similarity	NPD7008	Discontinued
0.6667	Remote Similarity	NPD1930	Approved
0.6667	Remote Similarity	NPD1929	Approved
0.6667	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD6798	Discontinued
0.6643	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD2313	Discontinued
0.664	Remote Similarity	NPD6685	Approved
0.6623	Remote Similarity	NPD7819	Suspended
0.6621	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD6832	Phase 2
0.6615	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD8166	Discontinued
0.6597	Remote Similarity	NPD1510	Phase 2
0.6596	Remote Similarity	NPD7713	Phase 3
0.6593	Remote Similarity	NPD6287	Discontinued
0.6585	Remote Similarity	NPD1932	Approved
0.6577	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6799	Approved
0.6575	Remote Similarity	NPD1549	Phase 2
0.6571	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD6801	Discontinued
0.6555	Remote Similarity	NPD1202	Approved
0.6544	Remote Similarity	NPD3972	Approved
0.6541	Remote Similarity	NPD9545	Approved
0.6538	Remote Similarity	NPD7768	Phase 2
0.6536	Remote Similarity	NPD4380	Phase 2
0.6536	Remote Similarity	NPD6599	Discontinued
0.6532	Remote Similarity	NPD5765	Approved
0.6519	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD4576	Approved
0.6515	Remote Similarity	NPD4574	Approved
0.651	Remote Similarity	NPD7236	Approved
0.651	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD2629	Approved
0.6486	Remote Similarity	NPD3750	Approved
0.6483	Remote Similarity	NPD2799	Discontinued
0.648	Remote Similarity	NPD164	Approved
0.648	Remote Similarity	NPD1237	Approved
0.6479	Remote Similarity	NPD6233	Phase 2
0.6474	Remote Similarity	NPD5402	Approved
0.6471	Remote Similarity	NPD7458	Discontinued
0.6466	Remote Similarity	NPD1087	Approved
0.6466	Remote Similarity	NPD2347	Approved
0.6462	Remote Similarity	NPD5535	Approved
0.6449	Remote Similarity	NPD5667	Approved
0.6447	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD6190	Approved
0.6439	Remote Similarity	NPD4198	Discontinued
0.6424	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD1894	Discontinued
0.6417	Remote Similarity	NPD1563	Approved
0.641	Remote Similarity	NPD8455	Phase 2
0.6406	Remote Similarity	NPD2329	Discontinued
0.64	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD225	Approved
0.6396	Remote Similarity	NPD227	Approved
0.6392	Remote Similarity	NPD7075	Discontinued
0.6392	Remote Similarity	NPD3749	Approved
0.6392	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6355	Discontinued
0.6389	Remote Similarity	NPD4068	Approved
0.6389	Remote Similarity	NPD4069	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD4067	Approved
0.6389	Remote Similarity	NPD2863	Approved
0.6389	Remote Similarity	NPD4065	Approved
0.6389	Remote Similarity	NPD4066	Approved
0.6387	Remote Similarity	NPD1239	Approved
0.6385	Remote Similarity	NPD6912	Phase 3
0.6376	Remote Similarity	NPD7003	Approved
0.637	Remote Similarity	NPD5585	Approved
0.6369	Remote Similarity	NPD3817	Phase 2
0.6364	Remote Similarity	NPD8032	Phase 2
0.6364	Remote Similarity	NPD1693	Approved
0.6364	Remote Similarity	NPD3226	Approved
0.6364	Remote Similarity	NPD7714	Approved
0.6364	Remote Similarity	NPD5951	Approved
0.6364	Remote Similarity	NPD7961	Discontinued
0.6364	Remote Similarity	NPD7715	Approved
0.6364	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD6085	Phase 2
0.6357	Remote Similarity	NPD5239	Approved
0.6357	Remote Similarity	NPD5235	Approved
0.6357	Remote Similarity	NPD5236	Approved
0.6357	Remote Similarity	NPD5240	Approved
0.6357	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD5237	Approved
0.6356	Remote Similarity	NPD5347	Phase 2
0.6356	Remote Similarity	NPD5346	Phase 2
0.6351	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD8312	Approved
0.6347	Remote Similarity	NPD8313	Approved
0.6343	Remote Similarity	NPD6065	Approved
0.634	Remote Similarity	NPD7670	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6185	Discontinued
0.6333	Remote Similarity	NPD3887	Approved
0.6329	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5408	Approved
0.6327	Remote Similarity	NPD5405	Approved
0.6327	Remote Similarity	NPD5406	Approved
0.6327	Remote Similarity	NPD5404	Approved
0.6325	Remote Similarity	NPD4793	Discontinued
0.6324	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD2979	Phase 3
0.6319	Remote Similarity	NPD1240	Approved
0.6316	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD5494	Approved
0.6308	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD4878	Approved
0.6303	Remote Similarity	NPD1086	Approved
0.6303	Remote Similarity	NPD1089	Approved
0.6303	Remote Similarity	NPD1090	Approved
0.6299	Remote Similarity	NPD7239	Suspended
0.6296	Remote Similarity	NPD7741	Discontinued
0.6291	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD1241	Discontinued
0.6288	Remote Similarity	NPD2652	Approved
0.6288	Remote Similarity	NPD2650	Approved
0.6284	Remote Similarity	NPD2346	Discontinued
0.6284	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD5890	Approved
0.6282	Remote Similarity	NPD5889	Approved
0.628	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.628	Remote Similarity	NPD7799	Discontinued
0.6276	Remote Similarity	NPD5124	Phase 1
0.6276	Remote Similarity	NPD4618	Approved
0.6276	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD4622	Approved
0.6275	Remote Similarity	NPD6273	Approved
0.6273	Remote Similarity	NPD6959	Discontinued
0.6268	Remote Similarity	NPD7055	Discontinued
0.6268	Remote Similarity	NPD2613	Approved
0.626	Remote Similarity	NPD1566	Phase 3
0.626	Remote Similarity	NPD1565	Approved
0.626	Remote Similarity	NPD1564	Approved
0.6258	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD6166	Phase 2
0.625	Remote Similarity	NPD3134	Approved
0.625	Remote Similarity	NPD6758	Approved
0.6242	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD5647	Approved
0.6235	Remote Similarity	NPD8150	Discontinued
0.6234	Remote Similarity	NPD920	Approved
0.6233	Remote Similarity	NPD1607	Approved
0.6232	Remote Similarity	NPD1201	Approved
0.6232	Remote Similarity	NPD7437	Approved
0.6232	Remote Similarity	NPD1281	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