NPASS Compound

Structure

CID255026 OpenBabel06191716062D 44 49 0 0 1 0 0 0 0 0999 V2000 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 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 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 -5.1962 1.0000 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 -4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 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 -1.7321 -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 1.5000 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 -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 -3.4641 -3.0000 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 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 -2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 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 -3.4641 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 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 10 2 0 0 0 0 1 25 1 0 0 0 0 2 13 1 0 0 0 0 2 25 2 0 0 0 0 3 14 2 0 0 0 0 3 25 1 0 0 0 0 4 15 1 0 0 0 0 4 26 2 0 0 0 0 5 16 2 0 0 0 0 5 26 1 0 0 0 0 6 17 1 0 0 0 0 6 27 2 0 0 0 0 7 18 2 0 0 0 0 7 27 1 0 0 0 0 8 21 1 0 0 0 0 8 26 1 0 0 0 0 9 22 1 0 0 0 0 9 27 1 0 0 0 0 11 19 1 0 0 0 0 11 28 2 0 0 0 0 12 20 2 0 0 0 0 12 28 1 0 0 0 0 13 30 2 0 0 0 0 14 30 1 0 0 0 0 15 31 2 0 0 0 0 16 31 1 0 0 0 0 17 32 2 0 0 0 0 18 32 1 0 0 0 0 19 33 2 0 0 0 0 20 33 1 0 0 0 0 23 29 1 0 0 0 0 23 34 1 0 0 0 0 24 35 1 0 0 0 0 28 38 1 0 0 0 0 29 10 1 6 0 0 0 29 37 1 0 0 0 0 30 39 1 0 0 0 0 31 40 1 0 0 0 0 32 41 1 0 0 0 0 33 42 1 0 0 0 0 34 21 1 6 0 0 0 34 43 1 0 0 0 0 35 22 1 6 0 0 0 35 44 1 0 0 0 0 36 24 1 6 0 0 0 36 37 1 0 0 0 0 36 43 1 0 0 0 0 37 38 1 0 0 0 0 38 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	592.28
Volume:	632.933
LogP:	6.734
LogD:	4.687
LogS:	-3.041
# Rotatable Bonds:	9
TPSA:	99.38
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.159
Synthetic Accessibility Score:	4.393
Fsp3:	0.316
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.035
MDCK Permeability:	1.2225884347571991e-05
Pgp-inhibitor:	0.807
Pgp-substrate:	0.471
Human Intestinal Absorption (HIA):	0.123
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.059
Plasma Protein Binding (PPB):	99.9129409790039%
Volume Distribution (VD):	0.445
Pgp-substrate:	1.1229839324951172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.508
CYP1A2-substrate:	0.076
CYP2C19-inhibitor:	0.901
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.67
CYP2C9-substrate:	0.988
CYP2D6-inhibitor:	0.94
CYP2D6-substrate:	0.916
CYP3A4-inhibitor:	0.828
CYP3A4-substrate:	0.678

ADMET: Excretion

Clearance (CL):	16.373
Half-life (T1/2):	0.629

ADMET: Toxicity

hERG Blockers:	0.927
Human Hepatotoxicity (H-HT):	0.345
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.141
Rat Oral Acute Toxicity:	0.48
Maximum Recommended Daily Dose:	0.942
Skin Sensitization:	0.982
Carcinogencity:	0.381
Eye Corrosion:	0.003
Eye Irritation:	0.373
Respiratory Toxicity:	0.733

Download Data

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

Natural Product: NPC255026

Natural Product ID:	NPC255026
*Common Name:**	Blepharocalyxin D
IUPAC Name:	4-[2-[(2S,4S,4aS,5S,7S,8aR)-5-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-7-[2-(4-hydroxyphenyl)ethyl]-2,3,4,4a,5,7,8,8a-octahydropyrano[3,2-c]pyran-2-yl]ethyl]phenol
Synonyms:	Blepharocalyxin D
Standard InCHIKey:	NEVDYTIAHUSATO-LEGNDWSYSA-N
Standard InCHI:	InChI=1S/C38H40O6/c39-30-13-2-25(3-14-30)1-10-29-23-34(21-8-26-4-15-31(40)16-5-26)43-36-24-35(22-9-27-6-17-32(41)18-7-27)44-38(37(29)36)28-11-19-33(42)20-12-28/h1-7,10-20,29,34-42H,8-9,21-24H2/b10-1+/t29-,34+,35+,36-,37+,38-/m1/s1
SMILES:	C(=C[C@@H]1C[C@H](CCc2ccc(cc2)O)O[C@@H]2C[C@H](CCc3ccc(cc3)O)O[C@H](c3ccc(cc3)O)[C@@H]12)/c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446847
PubChem CID:	9985898
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
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	Mengha, Yunnan Province, China	1991-Aug	PMID[11277741]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11325233]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11430002]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461664]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	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
ED50	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	=	25.7	uM	PMID[450562]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	3.61	uM	PMID[450562]

☑ 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 NPC255026 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	366
0.1-0.2	1375
0.2-0.3	2882
0.3-0.4	9071
0.4-0.5	10712
0.5-0.6	6945
0.6-0.7	9256
0.7-0.8	2013
0.8-0.85	65
0.85-0.9	9
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9828	High Similarity	NPC174977
0.9032	High Similarity	NPC471064
0.8906	High Similarity	NPC476616
0.8906	High Similarity	NPC476617
0.8906	High Similarity	NPC476615
0.8879	High Similarity	NPC153795
0.8879	High Similarity	NPC290353
0.8879	High Similarity	NPC42911
0.8769	High Similarity	NPC471522
0.8702	High Similarity	NPC470308
0.8702	High Similarity	NPC470307
0.8667	High Similarity	NPC476266
0.8644	High Similarity	NPC123175
0.8644	High Similarity	NPC176730
0.8621	High Similarity	NPC265211
0.8621	High Similarity	NPC306045
0.8583	High Similarity	NPC301651
0.8583	High Similarity	NPC473556
0.8385	Intermediate Similarity	NPC238168
0.8385	Intermediate Similarity	NPC237424
0.8385	Intermediate Similarity	NPC473309
0.8385	Intermediate Similarity	NPC471517
0.837	Intermediate Similarity	NPC100482
0.837	Intermediate Similarity	NPC277331
0.8321	Intermediate Similarity	NPC475492
0.8271	Intermediate Similarity	NPC15109
0.8271	Intermediate Similarity	NPC125579
0.8271	Intermediate Similarity	NPC11727
0.8231	Intermediate Similarity	NPC471519
0.8231	Intermediate Similarity	NPC471518
0.8209	Intermediate Similarity	NPC141717
0.8205	Intermediate Similarity	NPC135464
0.8205	Intermediate Similarity	NPC92623
0.8195	Intermediate Similarity	NPC184269
0.8189	Intermediate Similarity	NPC473451
0.814	Intermediate Similarity	NPC50315
0.814	Intermediate Similarity	NPC283049
0.814	Intermediate Similarity	NPC230479
0.814	Intermediate Similarity	NPC26879
0.8134	Intermediate Similarity	NPC472370
0.8129	Intermediate Similarity	NPC149633
0.8125	Intermediate Similarity	NPC131747
0.8125	Intermediate Similarity	NPC146355
0.8125	Intermediate Similarity	NPC257682
0.812	Intermediate Similarity	NPC233396
0.812	Intermediate Similarity	NPC154899
0.8102	Intermediate Similarity	NPC470372
0.8095	Intermediate Similarity	NPC470414
0.8092	Intermediate Similarity	NPC93962
0.8088	Intermediate Similarity	NPC260842
0.8071	Intermediate Similarity	NPC155564
0.8071	Intermediate Similarity	NPC248053
0.8071	Intermediate Similarity	NPC14468
0.8071	Intermediate Similarity	NPC102280
0.806	Intermediate Similarity	NPC473107
0.8047	Intermediate Similarity	NPC76465
0.8047	Intermediate Similarity	NPC38761
0.8045	Intermediate Similarity	NPC254275
0.8042	Intermediate Similarity	NPC259707
0.8042	Intermediate Similarity	NPC471403
0.8031	Intermediate Similarity	NPC193364
0.8031	Intermediate Similarity	NPC469686
0.8031	Intermediate Similarity	NPC54972
0.803	Intermediate Similarity	NPC254000
0.8029	Intermediate Similarity	NPC213607
0.8029	Intermediate Similarity	NPC164743
0.8029	Intermediate Similarity	NPC262189
0.8029	Intermediate Similarity	NPC182509
0.8029	Intermediate Similarity	NPC174787
0.8017	Intermediate Similarity	NPC91461
0.8017	Intermediate Similarity	NPC7686
0.8017	Intermediate Similarity	NPC40258
0.8016	Intermediate Similarity	NPC69006
0.8015	Intermediate Similarity	NPC39064
0.8015	Intermediate Similarity	NPC148366
0.8015	Intermediate Similarity	NPC53986
0.8015	Intermediate Similarity	NPC38664
0.8015	Intermediate Similarity	NPC311293
0.8015	Intermediate Similarity	NPC47283
0.8014	Intermediate Similarity	NPC70409
0.8014	Intermediate Similarity	NPC58190
0.8014	Intermediate Similarity	NPC153182
0.8014	Intermediate Similarity	NPC262911
0.8014	Intermediate Similarity	NPC6702
0.8014	Intermediate Similarity	NPC294558
0.8014	Intermediate Similarity	NPC82917
0.8014	Intermediate Similarity	NPC108811
0.8014	Intermediate Similarity	NPC133209
0.8014	Intermediate Similarity	NPC111134
0.8014	Intermediate Similarity	NPC202742
0.8014	Intermediate Similarity	NPC224921
0.8014	Intermediate Similarity	NPC18185
0.8014	Intermediate Similarity	NPC112819
0.8014	Intermediate Similarity	NPC174251
0.8014	Intermediate Similarity	NPC236202
0.8014	Intermediate Similarity	NPC263940
0.8014	Intermediate Similarity	NPC237546
0.8014	Intermediate Similarity	NPC204770
0.8014	Intermediate Similarity	NPC231712
0.8014	Intermediate Similarity	NPC242774
0.8014	Intermediate Similarity	NPC170103
0.8	Intermediate Similarity	NPC471215
0.8	Intermediate Similarity	NPC262573
0.7986	Intermediate Similarity	NPC226809
0.7986	Intermediate Similarity	NPC279406
0.7985	Intermediate Similarity	NPC77196
0.7972	Intermediate Similarity	NPC477612
0.797	Intermediate Similarity	NPC300875
0.797	Intermediate Similarity	NPC268917
0.797	Intermediate Similarity	NPC12875
0.797	Intermediate Similarity	NPC129106
0.797	Intermediate Similarity	NPC280653
0.797	Intermediate Similarity	NPC118114
0.797	Intermediate Similarity	NPC181497
0.797	Intermediate Similarity	NPC196765
0.797	Intermediate Similarity	NPC150011
0.797	Intermediate Similarity	NPC244888
0.797	Intermediate Similarity	NPC293203
0.797	Intermediate Similarity	NPC118683
0.797	Intermediate Similarity	NPC164804
0.797	Intermediate Similarity	NPC207892
0.797	Intermediate Similarity	NPC236014
0.797	Intermediate Similarity	NPC129784
0.797	Intermediate Similarity	NPC206224
0.797	Intermediate Similarity	NPC211413
0.797	Intermediate Similarity	NPC271945
0.797	Intermediate Similarity	NPC164574
0.797	Intermediate Similarity	NPC476166
0.797	Intermediate Similarity	NPC17343
0.797	Intermediate Similarity	NPC228369
0.797	Intermediate Similarity	NPC68205
0.7969	Intermediate Similarity	NPC100099
0.7969	Intermediate Similarity	NPC36016
0.7969	Intermediate Similarity	NPC150026
0.7958	Intermediate Similarity	NPC281549
0.7953	Intermediate Similarity	NPC469703
0.7953	Intermediate Similarity	NPC201402
0.7953	Intermediate Similarity	NPC469704
0.7953	Intermediate Similarity	NPC160854
0.7943	Intermediate Similarity	NPC274454
0.7943	Intermediate Similarity	NPC176804
0.7943	Intermediate Similarity	NPC215678
0.7943	Intermediate Similarity	NPC71686
0.7943	Intermediate Similarity	NPC96576
0.7937	Intermediate Similarity	NPC121866
0.7931	Intermediate Similarity	NPC213730
0.7931	Intermediate Similarity	NPC224161
0.7929	Intermediate Similarity	NPC28440
0.7929	Intermediate Similarity	NPC171932
0.7926	Intermediate Similarity	NPC97834
0.7926	Intermediate Similarity	NPC223008
0.7926	Intermediate Similarity	NPC296915
0.7926	Intermediate Similarity	NPC115335
0.7926	Intermediate Similarity	NPC198154
0.7926	Intermediate Similarity	NPC225696
0.7923	Intermediate Similarity	NPC188022
0.7923	Intermediate Similarity	NPC113495
0.7923	Intermediate Similarity	NPC103420
0.7923	Intermediate Similarity	NPC81641
0.7923	Intermediate Similarity	NPC102540
0.7923	Intermediate Similarity	NPC285040
0.7923	Intermediate Similarity	NPC17809
0.7917	Intermediate Similarity	NPC201959
0.7914	Intermediate Similarity	NPC186033
0.791	Intermediate Similarity	NPC13005
0.791	Intermediate Similarity	NPC321086
0.7902	Intermediate Similarity	NPC148516
0.7902	Intermediate Similarity	NPC122980
0.7902	Intermediate Similarity	NPC107862
0.7902	Intermediate Similarity	NPC211561
0.7902	Intermediate Similarity	NPC321657
0.7902	Intermediate Similarity	NPC180605
0.7902	Intermediate Similarity	NPC318373
0.7902	Intermediate Similarity	NPC177172
0.7899	Intermediate Similarity	NPC55793
0.7899	Intermediate Similarity	NPC273623
0.7895	Intermediate Similarity	NPC27187
0.7895	Intermediate Similarity	NPC470225
0.7883	Intermediate Similarity	NPC71465
0.7883	Intermediate Similarity	NPC472646
0.7883	Intermediate Similarity	NPC474390
0.7879	Intermediate Similarity	NPC274717
0.7879	Intermediate Similarity	NPC245826
0.7879	Intermediate Similarity	NPC474178
0.7879	Intermediate Similarity	NPC252307
0.7877	Intermediate Similarity	NPC46335
0.7874	Intermediate Similarity	NPC93398
0.7874	Intermediate Similarity	NPC258979
0.7874	Intermediate Similarity	NPC8283
0.7868	Intermediate Similarity	NPC37410
0.7868	Intermediate Similarity	NPC93783
0.7868	Intermediate Similarity	NPC258780
0.7863	Intermediate Similarity	NPC276212
0.7862	Intermediate Similarity	NPC59692
0.7862	Intermediate Similarity	NPC233467
0.7857	Intermediate Similarity	NPC113680
0.7857	Intermediate Similarity	NPC173203
0.7857	Intermediate Similarity	NPC163508
0.7857	Intermediate Similarity	NPC278961
0.7852	Intermediate Similarity	NPC469610

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 NPC255026 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	310
0.1-0.2	804
0.2-0.3	1301
0.3-0.4	2799
0.4-0.5	2079
0.5-0.6	1282
0.6-0.7	521
0.7-0.8	52
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8438	Intermediate Similarity	NPD4908	Phase 1
0.8308	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8031	Intermediate Similarity	NPD1610	Phase 2
0.7939	Intermediate Similarity	NPD2861	Phase 2
0.7845	Intermediate Similarity	NPD3020	Approved
0.7586	Intermediate Similarity	NPD2859	Approved
0.7586	Intermediate Similarity	NPD2860	Approved
0.7578	Intermediate Similarity	NPD7741	Discontinued
0.7578	Intermediate Similarity	NPD1548	Phase 1
0.7517	Intermediate Similarity	NPD8455	Phase 2
0.75	Intermediate Similarity	NPD2934	Approved
0.75	Intermediate Similarity	NPD2933	Approved
0.7448	Intermediate Similarity	NPD7447	Phase 1
0.7447	Intermediate Similarity	NPD7266	Discontinued
0.7426	Intermediate Similarity	NPD3027	Phase 3
0.7419	Intermediate Similarity	NPD3022	Approved
0.7419	Intermediate Similarity	NPD3021	Approved
0.7391	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1613	Approved
0.7379	Intermediate Similarity	NPD7213	Phase 3
0.7379	Intermediate Similarity	NPD7212	Phase 2
0.7372	Intermediate Similarity	NPD3764	Approved
0.7368	Intermediate Similarity	NPD6583	Phase 3
0.7368	Intermediate Similarity	NPD6582	Phase 2
0.7351	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6584	Phase 3
0.7329	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD3091	Approved
0.728	Intermediate Similarity	NPD5451	Approved
0.726	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD7041	Phase 2
0.7259	Intermediate Similarity	NPD3094	Phase 2
0.7246	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD7843	Approved
0.7239	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD4749	Approved
0.7234	Intermediate Similarity	NPD7097	Phase 1
0.7234	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD3092	Approved
0.7211	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7157	Approved
0.7203	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6516	Phase 2
0.7197	Intermediate Similarity	NPD5846	Approved
0.719	Intermediate Similarity	NPD7768	Phase 2
0.719	Intermediate Similarity	NPD1242	Phase 1
0.7188	Intermediate Similarity	NPD5283	Phase 1
0.7185	Intermediate Similarity	NPD8651	Approved
0.7177	Intermediate Similarity	NPD968	Approved
0.7174	Intermediate Similarity	NPD4625	Phase 3
0.7172	Intermediate Similarity	NPD8166	Discontinued
0.7153	Intermediate Similarity	NPD5736	Approved
0.7153	Intermediate Similarity	NPD7037	Approved
0.7153	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD846	Approved
0.7131	Intermediate Similarity	NPD940	Approved
0.7113	Intermediate Similarity	NPD4538	Approved
0.7113	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4536	Approved
0.7111	Intermediate Similarity	NPD5327	Phase 3
0.7111	Intermediate Similarity	NPD4659	Approved
0.7111	Intermediate Similarity	NPD7876	Discontinued
0.7109	Intermediate Similarity	NPD5535	Approved
0.7103	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD5735	Approved
0.7077	Intermediate Similarity	NPD6671	Approved
0.7071	Intermediate Similarity	NPD6407	Approved
0.7071	Intermediate Similarity	NPD6405	Approved
0.7068	Intermediate Similarity	NPD5126	Approved
0.7068	Intermediate Similarity	NPD3095	Discontinued
0.7068	Intermediate Similarity	NPD5125	Phase 3
0.7063	Intermediate Similarity	NPD5960	Phase 3
0.7063	Intermediate Similarity	NPD5588	Approved
0.7063	Intermediate Similarity	NPD2684	Approved
0.7055	Intermediate Similarity	NPD7466	Approved
0.7054	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4060	Phase 1
0.7008	Intermediate Similarity	NPD4750	Phase 3
0.7007	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD4103	Phase 2
0.7006	Intermediate Similarity	NPD6959	Discontinued
0.7	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6798	Discontinued
0.6993	Remote Similarity	NPD7119	Phase 2
0.6992	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD2342	Discontinued
0.6981	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD5124	Phase 1
0.6972	Remote Similarity	NPD6355	Discontinued
0.6968	Remote Similarity	NPD7773	Phase 2
0.6966	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD1091	Approved
0.6959	Remote Similarity	NPD6815	Approved
0.6957	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.695	Remote Similarity	NPD7265	Discontinued
0.695	Remote Similarity	NPD6233	Phase 2
0.695	Remote Similarity	NPD6663	Approved
0.694	Remote Similarity	NPD2668	Approved
0.694	Remote Similarity	NPD2667	Approved
0.6929	Remote Similarity	NPD7095	Approved
0.6923	Remote Similarity	NPD2228	Approved
0.6923	Remote Similarity	NPD2229	Approved
0.6923	Remote Similarity	NPD2234	Approved
0.6923	Remote Similarity	NPD6353	Approved
0.6918	Remote Similarity	NPD1549	Phase 2
0.6917	Remote Similarity	NPD6581	Approved
0.6917	Remote Similarity	NPD6580	Approved
0.6912	Remote Similarity	NPD7250	Approved
0.6912	Remote Similarity	NPD7249	Approved
0.6901	Remote Similarity	NPD2238	Phase 2
0.6901	Remote Similarity	NPD4140	Approved
0.6901	Remote Similarity	NPD3620	Phase 2
0.6901	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6674	Discontinued
0.6866	Remote Similarity	NPD4093	Discontinued
0.6863	Remote Similarity	NPD4380	Phase 2
0.6848	Remote Similarity	NPD8313	Approved
0.6848	Remote Similarity	NPD8312	Approved
0.6846	Remote Similarity	NPD7635	Approved
0.6846	Remote Similarity	NPD5058	Phase 3
0.6835	Remote Similarity	NPD4624	Approved
0.6833	Remote Similarity	NPD845	Approved
0.6828	Remote Similarity	NPD1510	Phase 2
0.6828	Remote Similarity	NPD7033	Discontinued
0.6828	Remote Similarity	NPD4108	Discontinued
0.6824	Remote Similarity	NPD3750	Approved
0.6824	Remote Similarity	NPD7003	Approved
0.6824	Remote Similarity	NPD4628	Phase 3
0.6815	Remote Similarity	NPD4059	Approved
0.6815	Remote Similarity	NPD3019	Approved
0.6815	Remote Similarity	NPD2286	Discontinued
0.6803	Remote Similarity	NPD288	Approved
0.6797	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD9545	Approved
0.679	Remote Similarity	NPD7228	Approved
0.6788	Remote Similarity	NPD1608	Approved
0.6788	Remote Similarity	NPD2235	Phase 2
0.6788	Remote Similarity	NPD2231	Phase 2
0.6781	Remote Similarity	NPD5406	Approved
0.6781	Remote Similarity	NPD5404	Approved
0.6781	Remote Similarity	NPD5408	Approved
0.6781	Remote Similarity	NPD5405	Approved
0.6781	Remote Similarity	NPD6099	Approved
0.6781	Remote Similarity	NPD6100	Approved
0.6779	Remote Similarity	NPD6190	Approved
0.6774	Remote Similarity	NPD3028	Approved
0.677	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6166	Phase 2
0.677	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD228	Approved
0.6768	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD3847	Discontinued
0.6763	Remote Similarity	NPD2797	Approved
0.6752	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD3685	Discontinued
0.6736	Remote Similarity	NPD4340	Discontinued
0.6733	Remote Similarity	NPD6667	Approved
0.6733	Remote Similarity	NPD6666	Approved
0.6724	Remote Similarity	NPD111	Approved
0.6721	Remote Similarity	NPD1809	Phase 2
0.6721	Remote Similarity	NPD844	Approved
0.6719	Remote Similarity	NPD290	Approved
0.6718	Remote Similarity	NPD821	Approved
0.6715	Remote Similarity	NPD422	Phase 1
0.671	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.671	Remote Similarity	NPD7411	Suspended
0.6707	Remote Similarity	NPD8053	Approved
0.6707	Remote Similarity	NPD8054	Approved
0.6692	Remote Similarity	NPD4198	Discontinued
0.6691	Remote Similarity	NPD2932	Approved
0.6691	Remote Similarity	NPD3225	Approved
0.6691	Remote Similarity	NPD7725	Approved
0.669	Remote Similarity	NPD4097	Suspended
0.669	Remote Similarity	NPD3054	Approved
0.669	Remote Similarity	NPD6179	Discontinued
0.669	Remote Similarity	NPD3052	Approved
0.6689	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD7458	Discontinued
0.6667	Remote Similarity	NPD2561	Approved
0.6667	Remote Similarity	NPD2230	Approved
0.6667	Remote Similarity	NPD1894	Discontinued
0.6667	Remote Similarity	NPD2232	Approved
0.6667	Remote Similarity	NPD2562	Approved
0.6667	Remote Similarity	NPD2233	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