NPASS Compound

Structure

CID32197 OpenBabel06191715362D 34 38 0 0 1 0 0 0 0 0999 V2000 -0.7883 -1.5471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2286 1.5765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0724 3.0381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1076 0.2455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3848 2.0637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9163 3.5253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0819 0.2455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9267 -1.2755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9163 1.5765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1076 1.9332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6972 2.0637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0724 2.0637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6204 1.0894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5410 1.5765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7601 3.0381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5691 1.0894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7601 2.0637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0819 1.9332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8533 1.5765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4994 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8533 0.6022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3540 1.0894 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.6972 0.1150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9267 0.3011 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 8.6039 3.5253 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5435 1.0894 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6039 1.5765 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5691 2.7770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4481 -0.4872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6972 -0.8594 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5410 0.6022 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9267 1.8776 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 12 1 0 0 0 0 2 5 2 0 0 0 0 2 13 1 0 0 0 0 3 6 2 0 0 0 0 3 13 1 0 0 0 0 4 7 2 0 0 0 0 4 14 1 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 2 0 0 0 0 8 21 1 0 0 0 0 9 13 2 0 0 0 0 9 18 1 0 0 0 0 10 14 2 0 0 0 0 10 19 1 0 0 0 0 11 15 2 0 0 0 0 11 20 1 0 0 0 0 12 34 1 0 0 0 0 14 23 1 0 0 0 0 15 32 1 0 0 0 0 16 18 2 0 0 0 0 16 26 1 0 0 0 0 17 19 2 0 0 0 0 17 27 1 0 0 0 0 18 28 1 0 0 0 0 19 29 1 0 0 0 0 20 22 2 0 0 0 0 20 33 1 0 0 0 0 21 25 1 0 0 0 0 21 30 2 0 0 0 0 22 24 1 0 0 0 0 22 25 1 0 0 0 0 23 25 1 0 0 0 0 23 33 1 0 0 0 0 24 31 2 0 0 0 0 24 32 1 0 0 0 0 25 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	462.1
Volume:	445.648
LogP:	3.134
LogD:	2.484
LogS:	-3.864
# Rotatable Bonds:	3
TPSA:	146.66
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.43
Synthetic Accessibility Score:	4.573
Fsp3:	0.12
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.18
MDCK Permeability:	1.3345994375413284e-05
Pgp-inhibitor:	0.024
Pgp-substrate:	0.196
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.436
30% Bioavailability (F30%):	0.043

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	97.73529815673828%
Volume Distribution (VD):	0.356
Pgp-substrate:	3.8995916843414307%

ADMET: Metabolism

CYP1A2-inhibitor:	0.064
CYP1A2-substrate:	0.359
CYP2C19-inhibitor:	0.101
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.56
CYP2C9-substrate:	0.814
CYP2D6-inhibitor:	0.082
CYP2D6-substrate:	0.406
CYP3A4-inhibitor:	0.697
CYP3A4-substrate:	0.317

ADMET: Excretion

Clearance (CL):	7.238
Half-life (T1/2):	0.818

ADMET: Toxicity

hERG Blockers:	0.087
Human Hepatotoxicity (H-HT):	0.461
Drug-inuced Liver Injury (DILI):	0.966
AMES Toxicity:	0.24
Rat Oral Acute Toxicity:	0.527
Maximum Recommended Daily Dose:	0.904
Skin Sensitization:	0.962
Carcinogencity:	0.645
Eye Corrosion:	0.003
Eye Irritation:	0.887
Respiratory Toxicity:	0.101

Download Data

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

Natural Product: NPC32197

Natural Product ID:	NPC32197
*Common Name:**	Inoscavin A
IUPAC Name:	2-(3,4-dihydroxyphenyl)-6-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-5'-methylspiro[2H-furo[3,2-c]pyran-3,2'-furan]-3',4-dione
Synonyms:
Standard InCHIKey:	ZGKUEJPXTILOCD-GORDUTHDSA-N
Standard InCHI:	InChI=1S/C25H18O9/c1-12-8-21(30)25(34-12)22-20(33-23(25)14-4-7-17(27)19(29)10-14)11-15(32-24(22)31)5-2-13-3-6-16(26)18(28)9-13/h2-11,23,26-29H,1H3/b5-2+
SMILES:	CC1=CC(=O)C2(c3c(cc(/C=C/c4ccc(c(c4)O)O)oc3=O)OC2c2ccc(c(c2)O)O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL487596
PubChem CID:	10434469
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000135] Catechols

*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
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165144]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844878]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16209522]
NPO33057	Inonotus xeranticus	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16488146]
NPO33057	Inonotus xeranticus	Species	Hymenochaetaceae	Eukaryota	n.a.	chonan-si, Korea	2005-APR	PMID[16499338]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17279797]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20583752]
NPO32484	phellinus baumii	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20708931]
NPO32484	phellinus baumii	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21531558]
NPO32484	phellinus baumii	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26077494]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	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	11
Others	6

Activity Type	# Activity
Cell Line	7
Individual Protein	5
NON-MOLECULAR	1
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	108.0	nM	PMID[460150]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	108.0	nM	PMID[460150]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	108.0	nM	PMID[460150]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	88.0	nM	PMID[460150]
NPT1085	Cell Line	KETR3	Homo sapiens	IC50	>	108.0	nM	PMID[460150]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	108.0	nM	PMID[460150]
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	=	18500.0	nM	PMID[460153]
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	=	20000.0	nM	PMID[460153]
NPT493	Individual Protein	Neuraminidase	Influenza A virus	Kiuc	=	24.5	uM	PMID[460153]
NPT493	Individual Protein	Neuraminidase	Influenza A virus	Ratio IC50	=	2.5	n.a.	PMID[460153]
NPT616	Cell Line	MDCK	Canis lupus familiaris	CC50	=	432600.0	nM	PMID[460153]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	78000.0	nM	PMID[460151]
NPT35	Others	n.a.		Retention_time	=	14.9	min	PMID[460153]
NPT742	Organism	Influenza A virus	Influenza A virus	IC50	=	22600.0	nM	PMID[460153]
NPT27	Others	Unspecified		Ratio CC50/IC50	=	4.4	n.a.	PMID[460153]
NPT742	Organism	Influenza A virus	Influenza A virus	Ratio IC50	=	2.9	n.a.	PMID[460153]

☑ 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 NPC32197 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	396
0.1-0.2	1660
0.2-0.3	3977
0.3-0.4	9029
0.4-0.5	9215
0.5-0.6	4295
0.6-0.7	5815
0.7-0.8	6215
0.8-0.85	1981
0.85-0.9	107
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9726	High Similarity	NPC477299
0.9172	High Similarity	NPC183824
0.9161	High Similarity	NPC156709
0.9161	High Similarity	NPC179505
0.9116	High Similarity	NPC283081
0.9116	High Similarity	NPC221383
0.9116	High Similarity	NPC299090
0.9116	High Similarity	NPC143892
0.9103	High Similarity	NPC285550
0.9021	High Similarity	NPC279676
0.9021	High Similarity	NPC67349
0.8986	High Similarity	NPC229264
0.898	High Similarity	NPC53884
0.898	High Similarity	NPC258671
0.8966	High Similarity	NPC9218
0.894	High Similarity	NPC95498
0.894	High Similarity	NPC246566
0.8926	High Similarity	NPC192568
0.8926	High Similarity	NPC471076
0.8926	High Similarity	NPC1580
0.8912	High Similarity	NPC304956
0.8811	High Similarity	NPC106406
0.8741	High Similarity	NPC155209
0.8741	High Similarity	NPC168799
0.8733	High Similarity	NPC322660
0.8671	High Similarity	NPC18074
0.8671	High Similarity	NPC25581
0.8671	High Similarity	NPC5419
0.8671	High Similarity	NPC61
0.8662	High Similarity	NPC44507
0.8658	High Similarity	NPC474692
0.8654	High Similarity	NPC223335
0.8654	High Similarity	NPC40920
0.8639	High Similarity	NPC289690
0.8639	High Similarity	NPC288452
0.863	High Similarity	NPC308976
0.8627	High Similarity	NPC300329
0.8621	High Similarity	NPC311742
0.8601	High Similarity	NPC108553
0.8601	High Similarity	NPC198388
0.86	High Similarity	NPC223185
0.8599	High Similarity	NPC469654
0.8591	High Similarity	NPC319628
0.8591	High Similarity	NPC472016
0.8591	High Similarity	NPC43158
0.8591	High Similarity	NPC192831
0.8591	High Similarity	NPC258469
0.8591	High Similarity	NPC220664
0.8591	High Similarity	NPC284948
0.8591	High Similarity	NPC303090
0.8591	High Similarity	NPC37331
0.8591	High Similarity	NPC277315
0.8581	High Similarity	NPC477279
0.8562	High Similarity	NPC221091
0.8562	High Similarity	NPC259576
0.8533	High Similarity	NPC470130
0.8531	High Similarity	NPC237506
0.8531	High Similarity	NPC329344
0.8531	High Similarity	NPC32626
0.8531	High Similarity	NPC217052
0.8523	High Similarity	NPC206095
0.8523	High Similarity	NPC253722
0.8523	High Similarity	NPC224389
0.8523	High Similarity	NPC31751
0.8523	High Similarity	NPC35702
0.8523	High Similarity	NPC477335
0.8523	High Similarity	NPC297517
0.8523	High Similarity	NPC477278
0.8523	High Similarity	NPC253481
0.8523	High Similarity	NPC477277
0.8523	High Similarity	NPC471027
0.8523	High Similarity	NPC13818
0.8516	High Similarity	NPC44730
0.8514	High Similarity	NPC476820
0.8514	High Similarity	NPC476819
0.8514	High Similarity	NPC303683
0.8514	High Similarity	NPC295492
0.8514	High Similarity	NPC205751
0.8514	High Similarity	NPC474875
0.8514	High Similarity	NPC274891
0.8514	High Similarity	NPC26241
0.8472	Intermediate Similarity	NPC318799
0.8446	Intermediate Similarity	NPC37250
0.8446	Intermediate Similarity	NPC219428
0.8446	Intermediate Similarity	NPC278068
0.8446	Intermediate Similarity	NPC152942
0.8446	Intermediate Similarity	NPC302857
0.8446	Intermediate Similarity	NPC142703
0.8431	Intermediate Similarity	NPC98009
0.8421	Intermediate Similarity	NPC98356
0.8411	Intermediate Similarity	NPC160378
0.8411	Intermediate Similarity	NPC32
0.8411	Intermediate Similarity	NPC122491
0.8408	Intermediate Similarity	NPC38699
0.8389	Intermediate Similarity	NPC147379
0.8385	Intermediate Similarity	NPC134047
0.8385	Intermediate Similarity	NPC223006
0.8385	Intermediate Similarity	NPC173729
0.8385	Intermediate Similarity	NPC272750
0.8377	Intermediate Similarity	NPC125570
0.8375	Intermediate Similarity	NPC112418
0.8355	Intermediate Similarity	NPC477333
0.8354	Intermediate Similarity	NPC470896
0.8354	Intermediate Similarity	NPC473275
0.8354	Intermediate Similarity	NPC123208
0.8333	Intermediate Similarity	NPC270268
0.8333	Intermediate Similarity	NPC93498
0.8333	Intermediate Similarity	NPC38473
0.8333	Intermediate Similarity	NPC163883
0.8333	Intermediate Similarity	NPC100675
0.8333	Intermediate Similarity	NPC476434
0.8323	Intermediate Similarity	NPC164937
0.8323	Intermediate Similarity	NPC144557
0.8323	Intermediate Similarity	NPC471745
0.8323	Intermediate Similarity	NPC306343
0.8322	Intermediate Similarity	NPC283560
0.8322	Intermediate Similarity	NPC24295
0.8313	Intermediate Similarity	NPC471744
0.8311	Intermediate Similarity	NPC255428
0.8302	Intermediate Similarity	NPC475663
0.8302	Intermediate Similarity	NPC286919
0.8299	Intermediate Similarity	NPC474895
0.8291	Intermediate Similarity	NPC476642
0.828	Intermediate Similarity	NPC146277
0.828	Intermediate Similarity	NPC19380
0.828	Intermediate Similarity	NPC327225
0.828	Intermediate Similarity	NPC473236
0.828	Intermediate Similarity	NPC87403
0.8269	Intermediate Similarity	NPC243891
0.8267	Intermediate Similarity	NPC322021
0.8267	Intermediate Similarity	NPC191280
0.8258	Intermediate Similarity	NPC478242
0.8258	Intermediate Similarity	NPC42464
0.8252	Intermediate Similarity	NPC118584
0.825	Intermediate Similarity	NPC469384
0.825	Intermediate Similarity	NPC76211
0.8243	Intermediate Similarity	NPC70680
0.8243	Intermediate Similarity	NPC182217
0.8243	Intermediate Similarity	NPC233350
0.8239	Intermediate Similarity	NPC163635
0.8239	Intermediate Similarity	NPC478055
0.8221	Intermediate Similarity	NPC180586
0.8221	Intermediate Similarity	NPC88243
0.8217	Intermediate Similarity	NPC267091
0.821	Intermediate Similarity	NPC322982
0.8207	Intermediate Similarity	NPC214246
0.8207	Intermediate Similarity	NPC477300
0.82	Intermediate Similarity	NPC284409
0.8199	Intermediate Similarity	NPC130955
0.8194	Intermediate Similarity	NPC43123
0.8194	Intermediate Similarity	NPC473138
0.8194	Intermediate Similarity	NPC28776
0.8194	Intermediate Similarity	NPC472969
0.8188	Intermediate Similarity	NPC90431
0.8188	Intermediate Similarity	NPC471988
0.8182	Intermediate Similarity	NPC132921
0.8182	Intermediate Similarity	NPC67951
0.8182	Intermediate Similarity	NPC197832
0.8176	Intermediate Similarity	NPC145425
0.8176	Intermediate Similarity	NPC68517
0.8176	Intermediate Similarity	NPC135127
0.8176	Intermediate Similarity	NPC131532
0.8169	Intermediate Similarity	NPC306100
0.8169	Intermediate Similarity	NPC14141
0.8165	Intermediate Similarity	NPC473544
0.8165	Intermediate Similarity	NPC83663
0.8165	Intermediate Similarity	NPC475162
0.8165	Intermediate Similarity	NPC475145
0.8165	Intermediate Similarity	NPC475216
0.8165	Intermediate Similarity	NPC475595
0.8165	Intermediate Similarity	NPC266084
0.816	Intermediate Similarity	NPC89131
0.8158	Intermediate Similarity	NPC67467
0.8153	Intermediate Similarity	NPC477334
0.8146	Intermediate Similarity	NPC474784
0.8146	Intermediate Similarity	NPC59775
0.8146	Intermediate Similarity	NPC256162
0.8141	Intermediate Similarity	NPC476394
0.8141	Intermediate Similarity	NPC98809
0.8133	Intermediate Similarity	NPC281780
0.8125	Intermediate Similarity	NPC251407
0.8125	Intermediate Similarity	NPC475695
0.8125	Intermediate Similarity	NPC168653
0.8125	Intermediate Similarity	NPC471500
0.8121	Intermediate Similarity	NPC283041
0.8121	Intermediate Similarity	NPC103398
0.8121	Intermediate Similarity	NPC477301
0.8121	Intermediate Similarity	NPC158325
0.8121	Intermediate Similarity	NPC470990
0.8121	Intermediate Similarity	NPC113295
0.8121	Intermediate Similarity	NPC180171
0.8117	Intermediate Similarity	NPC228940
0.8113	Intermediate Similarity	NPC125487
0.8113	Intermediate Similarity	NPC281703
0.8113	Intermediate Similarity	NPC136757
0.8112	Intermediate Similarity	NPC288945
0.811	Intermediate Similarity	NPC191930
0.8108	Intermediate Similarity	NPC215484
0.8108	Intermediate Similarity	NPC471749
0.8105	Intermediate Similarity	NPC477697

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 NPC32197 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	346
0.1-0.2	914
0.2-0.3	1850
0.3-0.4	2605
0.4-0.5	1928
0.5-0.6	1005
0.6-0.7	355
0.7-0.8	118
0.8-0.85	29
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8591	High Similarity	NPD6190	Approved
0.8063	Intermediate Similarity	NPD3817	Phase 2
0.7901	Intermediate Similarity	NPD3882	Suspended
0.7885	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD7266	Discontinued
0.7826	Intermediate Similarity	NPD1934	Approved
0.7805	Intermediate Similarity	NPD6234	Discontinued
0.7798	Intermediate Similarity	NPD3818	Discontinued
0.7791	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6166	Phase 2
0.7784	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2801	Approved
0.7778	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD6797	Phase 2
0.7744	Intermediate Similarity	NPD7075	Discontinued
0.773	Intermediate Similarity	NPD5402	Approved
0.7719	Intermediate Similarity	NPD7251	Discontinued
0.7673	Intermediate Similarity	NPD1512	Approved
0.7632	Intermediate Similarity	NPD230	Phase 1
0.7616	Intermediate Similarity	NPD6233	Phase 2
0.7607	Intermediate Similarity	NPD6801	Discontinued
0.7576	Intermediate Similarity	NPD4966	Approved
0.7576	Intermediate Similarity	NPD4965	Approved
0.7576	Intermediate Similarity	NPD4967	Phase 2
0.7572	Intermediate Similarity	NPD7808	Phase 3
0.7561	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD6232	Discontinued
0.7558	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD6798	Discontinued
0.7547	Intermediate Similarity	NPD1511	Approved
0.7544	Intermediate Similarity	NPD7054	Approved
0.7529	Intermediate Similarity	NPD7473	Discontinued
0.7516	Intermediate Similarity	NPD6355	Discontinued
0.7516	Intermediate Similarity	NPD5403	Approved
0.7514	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD37	Approved
0.75	Intermediate Similarity	NPD7472	Approved
0.75	Intermediate Similarity	NPD7074	Phase 3
0.7485	Intermediate Similarity	NPD7228	Approved
0.7485	Intermediate Similarity	NPD4380	Phase 2
0.7483	Intermediate Similarity	NPD3027	Phase 3
0.7468	Intermediate Similarity	NPD8166	Discontinued
0.7438	Intermediate Similarity	NPD6799	Approved
0.7434	Intermediate Similarity	NPD3764	Approved
0.7432	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5401	Approved
0.7372	Intermediate Similarity	NPD7033	Discontinued
0.7368	Intermediate Similarity	NPD7095	Approved
0.7358	Intermediate Similarity	NPD4628	Phase 3
0.7341	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD2935	Discontinued
0.7321	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD8434	Phase 2
0.7301	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD3751	Discontinued
0.7273	Intermediate Similarity	NPD6599	Discontinued
0.7273	Intermediate Similarity	NPD4062	Phase 3
0.7226	Intermediate Similarity	NPD1613	Approved
0.7226	Intermediate Similarity	NPD4060	Phase 1
0.7226	Intermediate Similarity	NPD943	Approved
0.7226	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD6559	Discontinued
0.7212	Intermediate Similarity	NPD3455	Phase 2
0.7207	Intermediate Similarity	NPD8150	Discontinued
0.7193	Intermediate Similarity	NPD7199	Phase 2
0.7179	Intermediate Similarity	NPD4340	Discontinued
0.7176	Intermediate Similarity	NPD919	Approved
0.7152	Intermediate Similarity	NPD1653	Approved
0.7152	Intermediate Similarity	NPD1510	Phase 2
0.7151	Intermediate Similarity	NPD3787	Discontinued
0.7143	Intermediate Similarity	NPD4110	Phase 3
0.7143	Intermediate Similarity	NPD1465	Phase 2
0.7143	Intermediate Similarity	NPD7819	Suspended
0.7143	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5494	Approved
0.7115	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD2067	Discontinued
0.7108	Intermediate Similarity	NPD3226	Approved
0.7103	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD8127	Discontinued
0.7081	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD447	Suspended
0.7063	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD5844	Phase 1
0.7037	Intermediate Similarity	NPD3750	Approved
0.7037	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD9545	Approved
0.7024	Intermediate Similarity	NPD7411	Suspended
0.7022	Intermediate Similarity	NPD7240	Approved
0.7019	Intermediate Similarity	NPD4534	Discontinued
0.7019	Intermediate Similarity	NPD5958	Discontinued
0.7019	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD1549	Phase 2
0.7013	Intermediate Similarity	NPD9494	Approved
0.7013	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD3926	Phase 2
0.7	Intermediate Similarity	NPD2796	Approved
0.6994	Remote Similarity	NPD1247	Approved
0.6993	Remote Similarity	NPD2797	Approved
0.6987	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD3268	Approved
0.6987	Remote Similarity	NPD2313	Discontinued
0.6981	Remote Similarity	NPD7097	Phase 1
0.697	Remote Similarity	NPD2533	Approved
0.697	Remote Similarity	NPD2532	Approved
0.697	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.697	Remote Similarity	NPD2534	Approved
0.6959	Remote Similarity	NPD5536	Phase 2
0.6948	Remote Similarity	NPD5647	Approved
0.6947	Remote Similarity	NPD7435	Discontinued
0.6944	Remote Similarity	NPD8313	Approved
0.6944	Remote Similarity	NPD8312	Approved
0.6943	Remote Similarity	NPD6663	Approved
0.6937	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD2799	Discontinued
0.6923	Remote Similarity	NPD6386	Approved
0.6923	Remote Similarity	NPD6385	Approved
0.6908	Remote Similarity	NPD9269	Phase 2
0.6908	Remote Similarity	NPD1608	Approved
0.6906	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD826	Approved
0.6899	Remote Similarity	NPD825	Approved
0.6899	Remote Similarity	NPD1240	Approved
0.6894	Remote Similarity	NPD9570	Approved
0.6894	Remote Similarity	NPD2438	Suspended
0.689	Remote Similarity	NPD2354	Approved
0.689	Remote Similarity	NPD3887	Approved
0.6875	Remote Similarity	NPD3021	Approved
0.6875	Remote Similarity	NPD3022	Approved
0.6867	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD7296	Approved
0.6864	Remote Similarity	NPD7028	Phase 2
0.686	Remote Similarity	NPD7768	Phase 2
0.6852	Remote Similarity	NPD5762	Approved
0.6852	Remote Similarity	NPD2346	Discontinued
0.6852	Remote Similarity	NPD5763	Approved
0.6842	Remote Similarity	NPD8455	Phase 2
0.6829	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4198	Discontinued
0.6823	Remote Similarity	NPD8320	Phase 1
0.6823	Remote Similarity	NPD8319	Approved
0.6821	Remote Similarity	NPD3749	Approved
0.6813	Remote Similarity	NPD1607	Approved
0.6813	Remote Similarity	NPD6653	Approved
0.681	Remote Similarity	NPD2424	Discontinued
0.6807	Remote Similarity	NPD4357	Discontinued
0.68	Remote Similarity	NPD6959	Discontinued
0.6795	Remote Similarity	NPD5736	Approved
0.6795	Remote Similarity	NPD2861	Phase 2
0.6791	Remote Similarity	NPD6534	Approved
0.6791	Remote Similarity	NPD6535	Approved
0.679	Remote Similarity	NPD1551	Phase 2
0.679	Remote Similarity	NPD6032	Approved
0.6789	Remote Similarity	NPD6780	Approved
0.6789	Remote Similarity	NPD6781	Approved
0.6789	Remote Similarity	NPD6782	Approved
0.6789	Remote Similarity	NPD6776	Approved
0.6789	Remote Similarity	NPD6779	Approved
0.6789	Remote Similarity	NPD6777	Approved
0.6789	Remote Similarity	NPD6778	Approved
0.6781	Remote Similarity	NPD228	Approved
0.678	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD1470	Approved
0.6766	Remote Similarity	NPD3146	Approved
0.6766	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD2629	Approved
0.6752	Remote Similarity	NPD6832	Phase 2
0.675	Remote Similarity	NPD1933	Approved
0.6748	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6002	Phase 3
0.6748	Remote Similarity	NPD2344	Approved
0.6748	Remote Similarity	NPD6004	Phase 3
0.6748	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6005	Phase 3
0.6744	Remote Similarity	NPD7972	Discontinued
0.674	Remote Similarity	NPD7039	Approved
0.674	Remote Similarity	NPD7038	Approved
0.6737	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7874	Approved
0.6735	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD1535	Discovery
0.6731	Remote Similarity	NPD2798	Approved
0.6728	Remote Similarity	NPD4308	Phase 3
0.6728	Remote Similarity	NPD3748	Approved
0.6726	Remote Similarity	NPD6273	Approved
0.6726	Remote Similarity	NPD5049	Phase 3
0.6725	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5242	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