NPASS Compound

Structure

NPC244191 OpenBabel07101718312D 48 55 0 0 1 0 0 0 0 0999 V2000 1.0818 2.3541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7517 -4.7160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1887 3.7396 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 1.5336 -1.8854 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 2.9585 0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2971 -2.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0575 0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2395 -3.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.7708 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 2.2847 1.9185 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 4.5362 2.6130 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 4.6857 0.6186 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 2.3996 1.1563 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 1.7321 -0.0000 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 3.7100 2.0497 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8090 2.4835 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5119 1.1819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4372 2.1791 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 3.0672 0.7708 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 3.0672 -0.0000 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 2.3996 -0.3854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7847 1.0525 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9828 1.9202 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6026 -3.7272 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.4129 0.7480 0.0000 O 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 3.9332 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2634 2.7424 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3996 -1.3854 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 39 1 0 0 0 0 2 40 1 0 0 0 0 3 45 1 0 0 0 0 4 46 1 0 0 0 0 5 47 1 0 0 0 0 6 48 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 39 1 0 0 0 0 10 40 1 0 0 0 0 11 19 2 0 0 0 0 11 21 1 0 0 0 0 12 20 2 0 0 0 0 12 22 1 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 15 23 1 0 0 0 0 15 29 2 0 0 0 0 16 24 1 0 0 0 0 16 30 2 0 0 0 0 17 27 1 0 0 0 0 17 37 1 0 0 0 0 18 28 1 0 0 0 0 18 38 1 0 0 0 0 19 31 1 0 0 0 0 20 32 1 0 0 0 0 21 22 1 0 0 0 0 21 35 2 0 0 0 0 22 36 2 0 0 0 0 23 25 1 0 0 0 0 23 37 1 1 0 0 0 24 26 1 0 0 0 0 24 38 1 1 0 0 0 25 13 1 1 0 0 0 25 39 1 0 0 0 0 26 14 1 6 0 0 0 26 40 1 0 0 0 0 27 29 1 0 0 0 0 27 41 2 0 0 0 0 28 30 1 0 0 0 0 28 42 2 0 0 0 0 29 45 1 0 0 0 0 30 46 1 0 0 0 0 31 33 2 0 0 0 0 31 37 1 0 0 0 0 32 34 2 0 0 0 0 32 38 1 0 0 0 0 33 35 1 0 0 0 0 33 43 1 0 0 0 0 34 36 1 0 0 0 0 34 44 1 0 0 0 0 35 47 1 0 0 0 0 36 48 1 0 0 0 0 37 7 1 6 0 0 0 38 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	656.31
Volume:	663.303
LogP:	1.933
LogD:	1.684
LogS:	-2.969
# Rotatable Bonds:	5
TPSA:	118.0
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	8
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.46
Synthetic Accessibility Score:	6.377
Fsp3:	0.526
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.184
MDCK Permeability:	1.4498102245852351e-05
Pgp-inhibitor:	0.882
Pgp-substrate:	0.84
Human Intestinal Absorption (HIA):	0.082
20% Bioavailability (F20%):	0.15
30% Bioavailability (F30%):	0.963

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.908
Plasma Protein Binding (PPB):	71.10718536376953%
Volume Distribution (VD):	1.699
Pgp-substrate:	24.831459045410156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.702
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.955
CYP2C9-inhibitor:	0.041
CYP2C9-substrate:	0.395
CYP2D6-inhibitor:	0.053
CYP2D6-substrate:	0.873
CYP3A4-inhibitor:	0.348
CYP3A4-substrate:	0.939

ADMET: Excretion

Clearance (CL):	6.058
Half-life (T1/2):	0.426

ADMET: Toxicity

hERG Blockers:	0.308
Human Hepatotoxicity (H-HT):	0.346
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.313
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.138
Carcinogencity:	0.069
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC244191

Natural Product ID:	NPC244191
*Common Name:**	HPPAEVBARLOWJB-QULPKBGFSA-N
IUPAC Name:	n.a.
Synonyms:	2,2'-Disinomenine
Standard InCHIKey:	HPPAEVBARLOWJB-QULPKBGFSA-N
Standard InCHI:	InChI=1S/C38H44N2O8/c1-39-9-7-37-17-27(41)29(45-3)15-23(37)25(39)13-19-11-21(35(47-5)33(43)31(19)37)22-12-20-14-26-24-16-30(46-4)28(42)18-38(24,8-10-40(26)2)32(20)34(44)36(22)48-6/h11-12,15-16,23-26,43-44H,7-10,13-14,17-18H2,1-6H3/t23-,24-,25+,26+,37-,38-/m1/s1
SMILES:	COC1=C[C@@H]2[C@@H]3Cc4c([C@@]2(CC1=O)CCN3C)c(O)c(c(c4)c1cc2C[C@@H]3N(C)CC[C@]4(c2c(c1OC)O)[C@@H]3C=C(C(=O)C4)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL256341
PubChem CID:	24770039
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000058] Morphinans

*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
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.3987/COM-96-7609.]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038566]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	stem	n.a.	PMID[16964757]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18081254]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23059629]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1315	Sinomenium acutum	Species	Menispermaceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	65500.0	nM	PMID[566107]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	71700.0	nM	PMID[566107]

☑ 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 NPC244191 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	339
0.1-0.2	1539
0.2-0.3	3819
0.3-0.4	10024
0.4-0.5	8951
0.5-0.6	9919
0.6-0.7	7744
0.7-0.8	346
0.8-0.85	13
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9611	High Similarity	NPC279665
0.8895	High Similarity	NPC298339
0.8254	Intermediate Similarity	NPC214629
0.8187	Intermediate Similarity	NPC255607
0.8187	Intermediate Similarity	NPC3375
0.8177	Intermediate Similarity	NPC196231
0.8173	Intermediate Similarity	NPC67346
0.8173	Intermediate Similarity	NPC97086
0.8122	Intermediate Similarity	NPC64576
0.8122	Intermediate Similarity	NPC226428
0.8122	Intermediate Similarity	NPC151470
0.8122	Intermediate Similarity	NPC201055
0.8122	Intermediate Similarity	NPC254045
0.8095	Intermediate Similarity	NPC115906
0.8081	Intermediate Similarity	NPC232533
0.8081	Intermediate Similarity	NPC43069
0.8081	Intermediate Similarity	NPC140577
0.801	Intermediate Similarity	NPC66909
0.799	Intermediate Similarity	NPC243483
0.7923	Intermediate Similarity	NPC475780
0.7903	Intermediate Similarity	NPC474931
0.7903	Intermediate Similarity	NPC306555
0.7903	Intermediate Similarity	NPC81218
0.7903	Intermediate Similarity	NPC205421
0.7903	Intermediate Similarity	NPC117188
0.7903	Intermediate Similarity	NPC12053
0.7903	Intermediate Similarity	NPC158376
0.7903	Intermediate Similarity	NPC145832
0.7892	Intermediate Similarity	NPC212794
0.7892	Intermediate Similarity	NPC253043
0.7892	Intermediate Similarity	NPC136508
0.7892	Intermediate Similarity	NPC13504
0.7892	Intermediate Similarity	NPC477563
0.7892	Intermediate Similarity	NPC196447
0.7892	Intermediate Similarity	NPC78222
0.7892	Intermediate Similarity	NPC306843
0.7892	Intermediate Similarity	NPC96603
0.7885	Intermediate Similarity	NPC82056
0.7879	Intermediate Similarity	NPC293624
0.7868	Intermediate Similarity	NPC174783
0.7838	Intermediate Similarity	NPC324144
0.7833	Intermediate Similarity	NPC157958
0.7817	Intermediate Similarity	NPC30182
0.7817	Intermediate Similarity	NPC473589
0.7817	Intermediate Similarity	NPC478092
0.7817	Intermediate Similarity	NPC478091
0.7783	Intermediate Similarity	NPC126211
0.7766	Intermediate Similarity	NPC478093
0.7761	Intermediate Similarity	NPC471489
0.7761	Intermediate Similarity	NPC311781
0.7744	Intermediate Similarity	NPC162694
0.7742	Intermediate Similarity	NPC1229
0.7735	Intermediate Similarity	NPC85747
0.7735	Intermediate Similarity	NPC8337
0.772	Intermediate Similarity	NPC305847
0.7703	Intermediate Similarity	NPC38964
0.7684	Intermediate Similarity	NPC239775
0.768	Intermediate Similarity	NPC302449
0.7673	Intermediate Similarity	NPC316164
0.7668	Intermediate Similarity	NPC32154
0.7644	Intermediate Similarity	NPC477020
0.7644	Intermediate Similarity	NPC192135
0.7644	Intermediate Similarity	NPC66341
0.7634	Intermediate Similarity	NPC166014
0.7634	Intermediate Similarity	NPC27410
0.7632	Intermediate Similarity	NPC26240
0.7632	Intermediate Similarity	NPC118274
0.7632	Intermediate Similarity	NPC69712
0.7632	Intermediate Similarity	NPC168753
0.7632	Intermediate Similarity	NPC477562
0.7617	Intermediate Similarity	NPC114364
0.7617	Intermediate Similarity	NPC320223
0.7614	Intermediate Similarity	NPC22115
0.7614	Intermediate Similarity	NPC275680
0.7612	Intermediate Similarity	NPC17677
0.7606	Intermediate Similarity	NPC44040
0.7604	Intermediate Similarity	NPC229166
0.7604	Intermediate Similarity	NPC128560
0.7604	Intermediate Similarity	NPC199465
0.7565	Intermediate Similarity	NPC472639
0.7565	Intermediate Similarity	NPC241704
0.7565	Intermediate Similarity	NPC472638
0.7527	Intermediate Similarity	NPC476572
0.7524	Intermediate Similarity	NPC476500
0.7524	Intermediate Similarity	NPC314946
0.7514	Intermediate Similarity	NPC325871
0.7514	Intermediate Similarity	NPC99659
0.7513	Intermediate Similarity	NPC16357
0.7513	Intermediate Similarity	NPC329969
0.7513	Intermediate Similarity	NPC95426
0.7513	Intermediate Similarity	NPC302245
0.75	Intermediate Similarity	NPC30779
0.75	Intermediate Similarity	NPC116284
0.75	Intermediate Similarity	NPC60186
0.75	Intermediate Similarity	NPC227683
0.7489	Intermediate Similarity	NPC211215
0.7488	Intermediate Similarity	NPC267414
0.7488	Intermediate Similarity	NPC314596
0.7475	Intermediate Similarity	NPC14507
0.7475	Intermediate Similarity	NPC47077
0.7475	Intermediate Similarity	NPC65312
0.7475	Intermediate Similarity	NPC139783
0.7474	Intermediate Similarity	NPC124657
0.7462	Intermediate Similarity	NPC302275
0.7459	Intermediate Similarity	NPC306011
0.7459	Intermediate Similarity	NPC472838
0.7449	Intermediate Similarity	NPC286119
0.7421	Intermediate Similarity	NPC318081
0.7411	Intermediate Similarity	NPC290582
0.7411	Intermediate Similarity	NPC185639
0.7411	Intermediate Similarity	NPC7715
0.7411	Intermediate Similarity	NPC258657
0.7411	Intermediate Similarity	NPC217748
0.7411	Intermediate Similarity	NPC54654
0.7411	Intermediate Similarity	NPC181796
0.7411	Intermediate Similarity	NPC311973
0.7411	Intermediate Similarity	NPC42663
0.7411	Intermediate Similarity	NPC239824
0.7411	Intermediate Similarity	NPC251735
0.7411	Intermediate Similarity	NPC104196
0.7411	Intermediate Similarity	NPC290005
0.7411	Intermediate Similarity	NPC182052
0.7411	Intermediate Similarity	NPC8836
0.7411	Intermediate Similarity	NPC90998
0.7411	Intermediate Similarity	NPC222661
0.7411	Intermediate Similarity	NPC49075
0.7411	Intermediate Similarity	NPC229373
0.7411	Intermediate Similarity	NPC223690
0.7411	Intermediate Similarity	NPC279228
0.7411	Intermediate Similarity	NPC15414
0.7411	Intermediate Similarity	NPC285931
0.7411	Intermediate Similarity	NPC328155
0.7411	Intermediate Similarity	NPC271013
0.74	Intermediate Similarity	NPC206900
0.7398	Intermediate Similarity	NPC474507
0.7396	Intermediate Similarity	NPC470324
0.7394	Intermediate Similarity	NPC288353
0.7387	Intermediate Similarity	NPC116465
0.7387	Intermediate Similarity	NPC212237
0.7385	Intermediate Similarity	NPC173416
0.7385	Intermediate Similarity	NPC35680
0.7385	Intermediate Similarity	NPC148709
0.7385	Intermediate Similarity	NPC476577
0.7382	Intermediate Similarity	NPC240841
0.7382	Intermediate Similarity	NPC35627
0.7382	Intermediate Similarity	NPC256012
0.7382	Intermediate Similarity	NPC250846
0.7382	Intermediate Similarity	NPC317272
0.7382	Intermediate Similarity	NPC268503
0.7382	Intermediate Similarity	NPC42549
0.7382	Intermediate Similarity	NPC81247
0.7382	Intermediate Similarity	NPC476573
0.7374	Intermediate Similarity	NPC135772
0.7374	Intermediate Similarity	NPC167116
0.7374	Intermediate Similarity	NPC274716
0.7374	Intermediate Similarity	NPC254441
0.7368	Intermediate Similarity	NPC476569
0.7366	Intermediate Similarity	NPC471031
0.7366	Intermediate Similarity	NPC469689
0.736	Intermediate Similarity	NPC477561
0.736	Intermediate Similarity	NPC312918
0.736	Intermediate Similarity	NPC155442
0.736	Intermediate Similarity	NPC476574
0.7358	Intermediate Similarity	NPC109925
0.7348	Intermediate Similarity	NPC201297
0.734	Intermediate Similarity	NPC33256
0.7337	Intermediate Similarity	NPC470757
0.7333	Intermediate Similarity	NPC304125
0.7333	Intermediate Similarity	NPC265563
0.7333	Intermediate Similarity	NPC476496
0.733	Intermediate Similarity	NPC24465
0.7326	Intermediate Similarity	NPC249797
0.7326	Intermediate Similarity	NPC184026
0.7326	Intermediate Similarity	NPC2413
0.7326	Intermediate Similarity	NPC278799
0.7326	Intermediate Similarity	NPC207757
0.7326	Intermediate Similarity	NPC110416
0.7326	Intermediate Similarity	NPC189266
0.7326	Intermediate Similarity	NPC5238
0.7326	Intermediate Similarity	NPC127674
0.7326	Intermediate Similarity	NPC276588
0.7326	Intermediate Similarity	NPC54379
0.7326	Intermediate Similarity	NPC193949
0.7326	Intermediate Similarity	NPC204828
0.7326	Intermediate Similarity	NPC39701
0.7326	Intermediate Similarity	NPC469817
0.7326	Intermediate Similarity	NPC295691
0.7326	Intermediate Similarity	NPC172765
0.7324	Intermediate Similarity	NPC473746
0.7323	Intermediate Similarity	NPC47191
0.7321	Intermediate Similarity	NPC326895
0.7313	Intermediate Similarity	NPC82763
0.7312	Intermediate Similarity	NPC295977
0.7312	Intermediate Similarity	NPC58310
0.731	Intermediate Similarity	NPC149285
0.7304	Intermediate Similarity	NPC281629
0.73	Intermediate Similarity	NPC124626
0.7297	Intermediate Similarity	NPC220858
0.7297	Intermediate Similarity	NPC192768
0.7297	Intermediate Similarity	NPC88249

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 NPC244191 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	216
0.1-0.2	744
0.2-0.3	1162
0.3-0.4	2451
0.4-0.5	2691
0.5-0.6	1378
0.6-0.7	438
0.7-0.8	53
0.8-0.85	15
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8895	High Similarity	NPD3534	Clinical (unspecified phase)
0.8413	Intermediate Similarity	NPD2490	Approved
0.8413	Intermediate Similarity	NPD2488	Approved
0.8214	Intermediate Similarity	NPD2493	Approved
0.8214	Intermediate Similarity	NPD2494	Approved
0.8209	Intermediate Similarity	NPD5676	Approved
0.8182	Intermediate Similarity	NPD4582	Approved
0.8182	Intermediate Similarity	NPD4583	Approved
0.8173	Intermediate Similarity	NPD3057	Approved
0.8131	Intermediate Similarity	NPD4004	Approved
0.8131	Intermediate Similarity	NPD4002	Approved
0.8122	Intermediate Similarity	NPD3450	Approved
0.8122	Intermediate Similarity	NPD3452	Approved
0.8095	Intermediate Similarity	NPD2968	Approved
0.8095	Intermediate Similarity	NPD2971	Approved
0.8081	Intermediate Similarity	NPD2491	Approved
0.8081	Intermediate Similarity	NPD3533	Approved
0.8081	Intermediate Similarity	NPD2972	Approved
0.8029	Intermediate Similarity	NPD7907	Approved
0.801	Intermediate Similarity	NPD2973	Approved
0.801	Intermediate Similarity	NPD2974	Approved
0.801	Intermediate Similarity	NPD2975	Approved
0.799	Intermediate Similarity	NPD3448	Approved
0.798	Intermediate Similarity	NPD4580	Approved
0.7952	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD4040	Phase 1
0.7889	Intermediate Similarity	NPD4107	Approved
0.7762	Intermediate Similarity	NPD4111	Phase 1
0.7762	Intermediate Similarity	NPD4665	Approved
0.7761	Intermediate Similarity	NPD4482	Phase 3
0.772	Intermediate Similarity	NPD7312	Approved
0.772	Intermediate Similarity	NPD7310	Approved
0.772	Intermediate Similarity	NPD7313	Approved
0.772	Intermediate Similarity	NPD7311	Approved
0.768	Intermediate Similarity	NPD7309	Approved
0.7579	Intermediate Similarity	NPD2489	Approved
0.7579	Intermediate Similarity	NPD27	Approved
0.7563	Intermediate Similarity	NPD7906	Approved
0.7526	Intermediate Similarity	NPD2969	Approved
0.7526	Intermediate Similarity	NPD2970	Approved
0.75	Intermediate Similarity	NPD7922	Phase 1
0.7477	Intermediate Similarity	NPD7048	Phase 3
0.7474	Intermediate Similarity	NPD3051	Approved
0.7411	Intermediate Similarity	NPD8053	Approved
0.7411	Intermediate Similarity	NPD8054	Approved
0.7407	Intermediate Similarity	NPD6997	Phase 2
0.7396	Intermediate Similarity	NPD2898	Approved
0.7371	Intermediate Similarity	NPD7047	Phase 3
0.7368	Intermediate Similarity	NPD7701	Phase 2
0.736	Intermediate Similarity	NPD4577	Approved
0.736	Intermediate Similarity	NPD4578	Approved
0.7343	Intermediate Similarity	NPD7497	Discontinued
0.7337	Intermediate Similarity	NPD4663	Approved
0.7336	Intermediate Similarity	NPD5980	Discovery
0.7306	Intermediate Similarity	NPD4481	Phase 3
0.7282	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD5190	Phase 2
0.7151	Intermediate Similarity	NPD3640	Phase 3
0.7151	Intermediate Similarity	NPD3639	Approved
0.7151	Intermediate Similarity	NPD3641	Approved
0.7143	Intermediate Similarity	NPD8319	Approved
0.7143	Intermediate Similarity	NPD8320	Phase 1
0.7107	Intermediate Similarity	NPD4603	Phase 2
0.7094	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD2420	Approved
0.7081	Intermediate Similarity	NPD2421	Approved
0.7065	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD8252	Approved
0.7056	Intermediate Similarity	NPD8251	Approved
0.7056	Intermediate Similarity	NPD7177	Discontinued
0.7056	Intermediate Similarity	NPD8099	Discontinued
0.702	Intermediate Similarity	NPD8156	Discontinued
0.702	Intermediate Similarity	NPD42	Phase 2
0.702	Intermediate Similarity	NPD6042	Phase 2
0.7	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7110	Phase 1
0.6968	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD4584	Approved
0.6944	Remote Similarity	NPD7801	Approved
0.6934	Remote Similarity	NPD7697	Approved
0.6934	Remote Similarity	NPD7698	Approved
0.6934	Remote Similarity	NPD7696	Phase 3
0.693	Remote Similarity	NPD8151	Discontinued
0.6919	Remote Similarity	NPD7473	Discontinued
0.6911	Remote Similarity	NPD6386	Approved
0.6911	Remote Similarity	NPD6385	Approved
0.6911	Remote Similarity	NPD6873	Phase 2
0.6907	Remote Similarity	NPD7833	Phase 2
0.6907	Remote Similarity	NPD7831	Phase 2
0.6907	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD7874	Approved
0.6891	Remote Similarity	NPD5978	Approved
0.6891	Remote Similarity	NPD5977	Approved
0.6882	Remote Similarity	NPD5241	Discontinued
0.6881	Remote Similarity	NPD5032	Approved
0.6875	Remote Similarity	NPD7298	Approved
0.6872	Remote Similarity	NPD6778	Approved
0.6872	Remote Similarity	NPD6781	Approved
0.6872	Remote Similarity	NPD6779	Approved
0.6872	Remote Similarity	NPD6776	Approved
0.6872	Remote Similarity	NPD6780	Approved
0.6872	Remote Similarity	NPD6782	Approved
0.6872	Remote Similarity	NPD6777	Approved
0.6863	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6876	Approved
0.6859	Remote Similarity	NPD6875	Approved
0.6857	Remote Similarity	NPD7700	Phase 2
0.6857	Remote Similarity	NPD7699	Phase 2
0.685	Remote Similarity	NPD5312	Approved
0.685	Remote Similarity	NPD5313	Approved
0.6839	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7827	Phase 1
0.6834	Remote Similarity	NPD5033	Approved
0.6829	Remote Similarity	NPD8150	Discontinued
0.6822	Remote Similarity	NPD7870	Phase 2
0.6822	Remote Similarity	NPD7871	Phase 2
0.6818	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD4859	Phase 1
0.6796	Remote Similarity	NPD7291	Discontinued
0.6796	Remote Similarity	NPD3110	Approved
0.6796	Remote Similarity	NPD3109	Approved
0.6789	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6166	Phase 2
0.6784	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD5968	Phase 3
0.6772	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6232	Discontinued
0.6751	Remote Similarity	NPD4666	Phase 3
0.6749	Remote Similarity	NPD7038	Approved
0.6749	Remote Similarity	NPD5039	Approved
0.6749	Remote Similarity	NPD5031	Approved
0.6749	Remote Similarity	NPD5027	Approved
0.6749	Remote Similarity	NPD5029	Approved
0.6749	Remote Similarity	NPD7039	Approved
0.6745	Remote Similarity	NPD8285	Discontinued
0.6738	Remote Similarity	NPD8166	Discontinued
0.6733	Remote Similarity	NPD4956	Approved
0.6732	Remote Similarity	NPD6618	Phase 2
0.6723	Remote Similarity	NPD8152	Approved
0.6723	Remote Similarity	NPD8153	Approved
0.672	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD6959	Discontinued
0.6716	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD6535	Approved
0.6714	Remote Similarity	NPD6534	Approved
0.6713	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5709	Phase 3
0.67	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD4420	Approved
0.6698	Remote Similarity	NPD7435	Discontinued
0.6684	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD6071	Discontinued
0.6683	Remote Similarity	NPD6836	Approved
0.6683	Remote Similarity	NPD5844	Phase 1
0.6683	Remote Similarity	NPD5035	Approved
0.6667	Remote Similarity	NPD6212	Phase 3
0.6667	Remote Similarity	NPD6213	Phase 3
0.6667	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4585	Approved
0.6667	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5038	Approved
0.6667	Remote Similarity	NPD8059	Phase 3
0.6667	Remote Similarity	NPD5037	Approved
0.6651	Remote Similarity	NPD6823	Phase 2
0.6649	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD4772	Phase 2
0.6649	Remote Similarity	NPD4773	Phase 2
0.6649	Remote Similarity	NPD5089	Approved
0.6649	Remote Similarity	NPD5090	Approved
0.6649	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7783	Phase 2
0.6636	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD6835	Approved
0.6634	Remote Similarity	NPD7228	Approved
0.6634	Remote Similarity	NPD7549	Discontinued
0.6633	Remote Similarity	NPD8127	Discontinued
0.6633	Remote Similarity	NPD6107	Approved
0.6632	Remote Similarity	NPD7458	Discontinued
0.663	Remote Similarity	NPD5156	Approved
0.663	Remote Similarity	NPD5155	Approved
0.6618	Remote Similarity	NPD6297	Approved
0.6618	Remote Similarity	NPD5036	Approved
0.6603	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.66	Remote Similarity	NPD4010	Discontinued
0.6597	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD6895	Approved
0.6595	Remote Similarity	NPD6896	Approved
0.6582	Remote Similarity	NPD1465	Phase 2
0.6579	Remote Similarity	NPD6666	Approved
0.6579	Remote Similarity	NPD7124	Phase 2
0.6579	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6667	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