NPASS Compound

Structure

CID98187 OpenBabel06191715442D 33 37 0 0 1 0 0 0 0 0999 V2000 -2.8181 3.7263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5446 2.4820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7636 3.9302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9403 2.2453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3352 -2.3742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4044 -2.0720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 -1.4689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6957 -0.9796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2391 1.4669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2389 0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6948 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8484 1.4678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 0.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6965 1.9572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0623 -1.7191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8478 -1.4684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9277 -0.4598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3928 2.9348 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2006 -1.1148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9791 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6951 -0.9786 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6960 -0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3925 1.9567 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5441 0.4888 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8481 0.4893 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2698 -0.8127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5444 1.4674 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8585 -0.7619 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5427 -1.4677 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3656 3.0368 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.0661 0.1445 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 32 1 0 0 0 0 5 32 1 0 0 0 0 6 7 2 0 0 0 0 6 16 1 0 0 0 0 7 20 1 0 0 0 0 8 9 1 0 0 0 0 8 21 1 0 0 0 0 10 11 1 0 0 0 0 10 24 1 0 0 0 0 11 25 1 0 0 0 0 12 14 1 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 13 26 1 0 0 0 0 14 28 1 0 0 0 0 15 29 1 0 0 0 0 16 30 2 0 0 0 0 17 21 1 0 0 0 0 17 22 1 0 0 0 0 18 20 2 0 0 0 0 18 30 1 0 0 0 0 19 1 1 1 0 0 0 19 24 1 0 0 0 0 19 32 1 0 0 0 0 20 27 1 0 0 0 0 21 28 1 6 0 0 0 22 31 1 6 0 0 0 23 9 1 1 0 0 0 23 25 1 0 0 0 0 23 26 1 0 0 0 0 24 29 1 6 0 0 0 25 29 1 6 0 0 0 26 28 1 6 0 0 0 27 31 2 3 0 0 0 27 33 1 0 0 0 0 28 2 1 6 0 0 0 29 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	451.36
Volume:	498.592
LogP:	5.626
LogD:	4.56
LogS:	-2.287
# Rotatable Bonds:	5
TPSA:	45.23
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.63
Synthetic Accessibility Score:	4.301
Fsp3:	0.793
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:	-4.837
MDCK Permeability:	1.2496102499426343e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.681
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.028

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.291
Plasma Protein Binding (PPB):	59.00351333618164%
Volume Distribution (VD):	1.862
Pgp-substrate:	31.908008575439453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.451
CYP1A2-substrate:	0.45
CYP2C19-inhibitor:	0.209
CYP2C19-substrate:	0.925
CYP2C9-inhibitor:	0.315
CYP2C9-substrate:	0.052
CYP2D6-inhibitor:	0.597
CYP2D6-substrate:	0.901
CYP3A4-inhibitor:	0.94
CYP3A4-substrate:	0.652

ADMET: Excretion

Clearance (CL):	12.408
Half-life (T1/2):	0.144

ADMET: Toxicity

hERG Blockers:	0.99
Human Hepatotoxicity (H-HT):	0.439
Drug-inuced Liver Injury (DILI):	0.786
AMES Toxicity:	0.087
Rat Oral Acute Toxicity:	0.692
Maximum Recommended Daily Dose:	0.787
Skin Sensitization:	0.964
Carcinogencity:	0.452
Eye Corrosion:	0.017
Eye Irritation:	0.017
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC98187

Natural Product ID:	NPC98187
*Common Name:**	Epipachysamine B
IUPAC Name:	N-[(3S,5S,8R,9S,10S,13S,14S,17S)-17-[(1S)-1-(dimethylamino)ethyl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]pyridine-3-carboxamide
Synonyms:	Epipachysamine B
Standard InCHIKey:	LMILOBNADVQQTH-QECVUFATSA-N
Standard InCHI:	InChI=1S/C29H45N3O/c1-19(32(4)5)24-10-11-25-23-9-8-21-17-22(31-27(33)20-7-6-16-30-18-20)12-14-28(21,2)26(23)13-15-29(24,25)3/h6-7,16,18-19,21-26H,8-15,17H2,1-5H3,(H,31,33)/t19-,21-,22-,23-,24+,25-,26-,28-,29+/m0/s1
SMILES:	CN([C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC[C@@H]2[C@]1(C)CC[C@@H](C2)N=C(c1cccnc1)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2087209
PubChem CID:	70688998
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002340] Azasteroids and derivatives

*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
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12951092]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[12951092]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[15930771]
NPO6711	Streptomyces mirabilis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19818612]
NPO13852	Pachysandra terminalis	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22804108]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13852	Pachysandra terminalis	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12328	Ampelopsis japonica	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12560	Cassia leptophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12328	Ampelopsis japonica	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13852	Pachysandra terminalis	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13852	Pachysandra terminalis	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12328	Ampelopsis japonica	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12560	Cassia leptophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4160	Cephalosporium polyaleurum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11838	Euphorbia regis-jubae	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7351	Uncaria pteropoda	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6711	Streptomyces mirabilis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13852	Pachysandra terminalis	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18213	Strychnos variabilis	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12328	Ampelopsis japonica	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10911	Euphorbia peplis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13128	Crotalaria rosenii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9527	Dendrodoa grossularia	Species	Styelidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2332	Plantago serraria	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	350.0	nM	PMID[546031]

☑ 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 NPC98187 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	504
0.1-0.2	2213
0.2-0.3	10068
0.3-0.4	20656
0.4-0.5	5184
0.5-0.6	2606
0.6-0.7	1405
0.7-0.8	60
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7947	Intermediate Similarity	NPC212125
0.7857	Intermediate Similarity	NPC473057
0.784	Intermediate Similarity	NPC477974
0.7811	Intermediate Similarity	NPC471178
0.7798	Intermediate Similarity	NPC471177
0.7798	Intermediate Similarity	NPC59779
0.7798	Intermediate Similarity	NPC124542
0.7764	Intermediate Similarity	NPC471323
0.7722	Intermediate Similarity	NPC3715
0.7712	Intermediate Similarity	NPC306397
0.7706	Intermediate Similarity	NPC477975
0.7688	Intermediate Similarity	NPC471294
0.7624	Intermediate Similarity	NPC95783
0.7619	Intermediate Similarity	NPC129721
0.76	Intermediate Similarity	NPC150048
0.76	Intermediate Similarity	NPC203754
0.7597	Intermediate Similarity	NPC471313
0.7597	Intermediate Similarity	NPC165370
0.7597	Intermediate Similarity	NPC471311
0.7547	Intermediate Similarity	NPC29702
0.7544	Intermediate Similarity	NPC97367
0.7514	Intermediate Similarity	NPC176199
0.7514	Intermediate Similarity	NPC215795
0.7486	Intermediate Similarity	NPC477976
0.7471	Intermediate Similarity	NPC194411
0.7416	Intermediate Similarity	NPC232340
0.7405	Intermediate Similarity	NPC103230
0.7405	Intermediate Similarity	NPC324611
0.7405	Intermediate Similarity	NPC256893
0.7389	Intermediate Similarity	NPC19679
0.7389	Intermediate Similarity	NPC133306
0.7386	Intermediate Similarity	NPC259545
0.7378	Intermediate Similarity	NPC477977
0.7356	Intermediate Similarity	NPC108469
0.7353	Intermediate Similarity	NPC51054
0.7345	Intermediate Similarity	NPC37423
0.7345	Intermediate Similarity	NPC275305
0.7341	Intermediate Similarity	NPC159319
0.7338	Intermediate Similarity	NPC290094
0.733	Intermediate Similarity	NPC158129
0.7312	Intermediate Similarity	NPC289786
0.7284	Intermediate Similarity	NPC314102
0.7284	Intermediate Similarity	NPC251722
0.7267	Intermediate Similarity	NPC56765
0.7263	Intermediate Similarity	NPC68354
0.7241	Intermediate Similarity	NPC32028
0.7225	Intermediate Similarity	NPC131718
0.7216	Intermediate Similarity	NPC201700
0.7208	Intermediate Similarity	NPC265605
0.7208	Intermediate Similarity	NPC182570
0.7208	Intermediate Similarity	NPC109151
0.7208	Intermediate Similarity	NPC48564
0.7197	Intermediate Similarity	NPC202957
0.7197	Intermediate Similarity	NPC169625
0.7191	Intermediate Similarity	NPC313791
0.7184	Intermediate Similarity	NPC315214
0.7184	Intermediate Similarity	NPC47298
0.7182	Intermediate Similarity	NPC300688
0.7182	Intermediate Similarity	NPC471997
0.7178	Intermediate Similarity	NPC471312
0.7171	Intermediate Similarity	NPC471402
0.7171	Intermediate Similarity	NPC297486
0.7171	Intermediate Similarity	NPC240136
0.717	Intermediate Similarity	NPC475090
0.717	Intermediate Similarity	NPC475105
0.717	Intermediate Similarity	NPC329896
0.7168	Intermediate Similarity	NPC41257
0.7167	Intermediate Similarity	NPC151939
0.7161	Intermediate Similarity	NPC329825
0.7158	Intermediate Similarity	NPC265576
0.7128	Intermediate Similarity	NPC329541
0.7128	Intermediate Similarity	NPC475835
0.7124	Intermediate Similarity	NPC91958
0.7118	Intermediate Similarity	NPC105818
0.7118	Intermediate Similarity	NPC24678
0.7111	Intermediate Similarity	NPC134586
0.711	Intermediate Similarity	NPC193740
0.711	Intermediate Similarity	NPC167635
0.7107	Intermediate Similarity	NPC89490
0.7083	Intermediate Similarity	NPC470279
0.7072	Intermediate Similarity	NPC211997
0.7072	Intermediate Similarity	NPC326575
0.707	Intermediate Similarity	NPC476322
0.7069	Intermediate Similarity	NPC206819
0.7069	Intermediate Similarity	NPC318065
0.7069	Intermediate Similarity	NPC84508
0.7062	Intermediate Similarity	NPC160105
0.7062	Intermediate Similarity	NPC474561
0.7062	Intermediate Similarity	NPC49954
0.7045	Intermediate Similarity	NPC102423
0.7045	Intermediate Similarity	NPC474217
0.7041	Intermediate Similarity	NPC473362
0.7041	Intermediate Similarity	NPC166492
0.7035	Intermediate Similarity	NPC469763
0.7035	Intermediate Similarity	NPC73952
0.7035	Intermediate Similarity	NPC292517
0.7035	Intermediate Similarity	NPC469765
0.7035	Intermediate Similarity	NPC469786
0.7035	Intermediate Similarity	NPC25008
0.7035	Intermediate Similarity	NPC259644
0.7035	Intermediate Similarity	NPC469760
0.7033	Intermediate Similarity	NPC248462
0.703	Intermediate Similarity	NPC169433
0.7026	Intermediate Similarity	NPC289086
0.7022	Intermediate Similarity	NPC63751
0.7019	Intermediate Similarity	NPC69914
0.7019	Intermediate Similarity	NPC282398
0.7018	Intermediate Similarity	NPC33421
0.7016	Intermediate Similarity	NPC229332
0.7013	Intermediate Similarity	NPC143603
0.7011	Intermediate Similarity	NPC286427
0.7011	Intermediate Similarity	NPC138018
0.7005	Intermediate Similarity	NPC183805
0.7	Intermediate Similarity	NPC133366
0.7	Intermediate Similarity	NPC475602
0.7	Intermediate Similarity	NPC314603
0.6994	Remote Similarity	NPC80597
0.6994	Remote Similarity	NPC75540
0.6994	Remote Similarity	NPC212376
0.6994	Remote Similarity	NPC70922
0.6994	Remote Similarity	NPC211572
0.6989	Remote Similarity	NPC71079
0.6988	Remote Similarity	NPC32002
0.6988	Remote Similarity	NPC315348
0.6988	Remote Similarity	NPC316811
0.6983	Remote Similarity	NPC126481
0.698	Remote Similarity	NPC6981
0.6975	Remote Similarity	NPC471322
0.697	Remote Similarity	NPC48042
0.697	Remote Similarity	NPC304179
0.697	Remote Similarity	NPC472550
0.6963	Remote Similarity	NPC473053
0.6961	Remote Similarity	NPC329688
0.6961	Remote Similarity	NPC189812
0.6957	Remote Similarity	NPC476131
0.6949	Remote Similarity	NPC194640
0.6947	Remote Similarity	NPC474177
0.6946	Remote Similarity	NPC144779
0.6946	Remote Similarity	NPC294579
0.6944	Remote Similarity	NPC201634
0.6939	Remote Similarity	NPC475070
0.6935	Remote Similarity	NPC475422
0.6935	Remote Similarity	NPC476319
0.6932	Remote Similarity	NPC255229
0.6932	Remote Similarity	NPC81229
0.6931	Remote Similarity	NPC477907
0.6931	Remote Similarity	NPC477909
0.6931	Remote Similarity	NPC30570
0.6931	Remote Similarity	NPC42678
0.6919	Remote Similarity	NPC48938
0.6919	Remote Similarity	NPC87755
0.6919	Remote Similarity	NPC63041
0.6918	Remote Similarity	NPC151489
0.6918	Remote Similarity	NPC245244
0.6918	Remote Similarity	NPC146373
0.6918	Remote Similarity	NPC166424
0.6915	Remote Similarity	NPC173028
0.6915	Remote Similarity	NPC65215
0.6914	Remote Similarity	NPC315320
0.6912	Remote Similarity	NPC301368
0.6912	Remote Similarity	NPC216428
0.6912	Remote Similarity	NPC84815
0.6909	Remote Similarity	NPC328029
0.6904	Remote Similarity	NPC475288
0.6898	Remote Similarity	NPC171171
0.6897	Remote Similarity	NPC206343
0.6897	Remote Similarity	NPC477908
0.6897	Remote Similarity	NPC162812
0.6893	Remote Similarity	NPC282231
0.6882	Remote Similarity	NPC314372
0.6882	Remote Similarity	NPC159856
0.6882	Remote Similarity	NPC472294
0.6882	Remote Similarity	NPC86288
0.6882	Remote Similarity	NPC167400
0.6875	Remote Similarity	NPC135141
0.6875	Remote Similarity	NPC92796
0.6872	Remote Similarity	NPC127730
0.6872	Remote Similarity	NPC300183
0.6872	Remote Similarity	NPC278366
0.6868	Remote Similarity	NPC469938
0.6867	Remote Similarity	NPC65408
0.6866	Remote Similarity	NPC472553
0.6866	Remote Similarity	NPC251160
0.6864	Remote Similarity	NPC20144
0.6863	Remote Similarity	NPC62367
0.6862	Remote Similarity	NPC204565
0.6857	Remote Similarity	NPC469785
0.6855	Remote Similarity	NPC27740
0.6854	Remote Similarity	NPC472587
0.6854	Remote Similarity	NPC469813
0.6854	Remote Similarity	NPC78375
0.6854	Remote Similarity	NPC90723
0.6854	Remote Similarity	NPC311276
0.6854	Remote Similarity	NPC476446
0.6848	Remote Similarity	NPC133261
0.6848	Remote Similarity	NPC213468
0.6847	Remote Similarity	NPC470306
0.6845	Remote Similarity	NPC280290
0.6837	Remote Similarity	NPC328318
0.6837	Remote Similarity	NPC328596

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 NPC98187 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	252
0.1-0.2	554
0.2-0.3	715
0.3-0.4	1670
0.4-0.5	3070
0.5-0.6	2153
0.6-0.7	679
0.7-0.8	56
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8693	High Similarity	NPD3813	Approved
0.8225	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD6026	Approved
0.8063	Intermediate Similarity	NPD4702	Approved
0.8063	Intermediate Similarity	NPD4703	Approved
0.8056	Intermediate Similarity	NPD7021	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD5100	Phase 3
0.8	Intermediate Similarity	NPD5255	Approved
0.7947	Intermediate Similarity	NPD9284	Approved
0.7925	Intermediate Similarity	NPD3717	Discontinued
0.7911	Intermediate Similarity	NPD1649	Discontinued
0.7898	Intermediate Similarity	NPD6241	Phase 1
0.7888	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD7469	Discontinued
0.7821	Intermediate Similarity	NPD6281	Approved
0.7751	Intermediate Similarity	NPD6635	Approved
0.7712	Intermediate Similarity	NPD9080	Approved
0.7709	Intermediate Similarity	NPD8021	Approved
0.7709	Intermediate Similarity	NPD8020	Approved
0.7657	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD1352	Discontinued
0.7644	Intermediate Similarity	NPD5065	Approved
0.7643	Intermediate Similarity	NPD4030	Approved
0.7643	Intermediate Similarity	NPD4029	Approved
0.7643	Intermediate Similarity	NPD4028	Approved
0.763	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD5541	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD4638	Approved
0.7616	Intermediate Similarity	NPD4640	Approved
0.7616	Intermediate Similarity	NPD4639	Approved
0.759	Intermediate Similarity	NPD6158	Phase 2
0.759	Intermediate Similarity	NPD2882	Phase 1
0.759	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD4044	Discontinued
0.75	Intermediate Similarity	NPD9506	Approved
0.7485	Intermediate Similarity	NPD3262	Approved
0.7484	Intermediate Similarity	NPD2119	Approved
0.7484	Intermediate Similarity	NPD2118	Approved
0.7471	Intermediate Similarity	NPD3433	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7474	Suspended
0.7459	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD3404	Approved
0.7432	Intermediate Similarity	NPD8063	Discontinued
0.743	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD5862	Discovery
0.7412	Intermediate Similarity	NPD2581	Approved
0.7412	Intermediate Similarity	NPD2582	Approved
0.7399	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD4998	Phase 3
0.7366	Intermediate Similarity	NPD4999	Phase 3
0.7342	Intermediate Similarity	NPD3476	Approved
0.7342	Intermediate Similarity	NPD3475	Approved
0.7341	Intermediate Similarity	NPD3323	Discontinued
0.7326	Intermediate Similarity	NPD2511	Approved
0.7318	Intermediate Similarity	NPD4079	Approved
0.7318	Intermediate Similarity	NPD4076	Approved
0.7312	Intermediate Similarity	NPD3942	Approved
0.7312	Intermediate Similarity	NPD3944	Approved
0.7288	Intermediate Similarity	NPD7418	Discontinued
0.7283	Intermediate Similarity	NPD5315	Discontinued
0.7283	Intermediate Similarity	NPD7233	Approved
0.7283	Intermediate Similarity	NPD6363	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD8026	Phase 1
0.7283	Intermediate Similarity	NPD7234	Approved
0.7263	Intermediate Similarity	NPD3505	Approved
0.7263	Intermediate Similarity	NPD3506	Approved
0.7239	Intermediate Similarity	NPD2896	Discontinued
0.7216	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD271	Approved
0.7208	Intermediate Similarity	NPD268	Approved
0.7208	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD926	Approved
0.72	Intermediate Similarity	NPD925	Approved
0.7184	Intermediate Similarity	NPD1684	Approved
0.7184	Intermediate Similarity	NPD1685	Approved
0.7175	Intermediate Similarity	NPD1326	Approved
0.7175	Intermediate Similarity	NPD1325	Approved
0.7167	Intermediate Similarity	NPD4181	Approved
0.7167	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD6665	Discontinued
0.7135	Intermediate Similarity	NPD8431	Approved
0.7128	Intermediate Similarity	NPD4551	Phase 2
0.7127	Intermediate Similarity	NPD6555	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD3082	Discontinued
0.712	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD2781	Approved
0.7102	Intermediate Similarity	NPD2780	Approved
0.7102	Intermediate Similarity	NPD2782	Approved
0.7098	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD8123	Approved
0.7072	Intermediate Similarity	NPD8122	Approved
0.7071	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6492	Phase 2
0.7052	Intermediate Similarity	NPD2580	Discontinued
0.7049	Intermediate Similarity	NPD8408	Discontinued
0.7035	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6227	Discontinued
0.7026	Intermediate Similarity	NPD6323	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7948	Phase 1
0.7011	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD6975	Discontinued
0.7006	Intermediate Similarity	NPD2720	Phase 1
0.7006	Intermediate Similarity	NPD5020	Approved
0.7006	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8094	Discontinued
0.7	Intermediate Similarity	NPD1599	Approved
0.7	Intermediate Similarity	NPD4547	Phase 3
0.6995	Remote Similarity	NPD7168	Phase 3
0.6994	Remote Similarity	NPD2809	Approved
0.6988	Remote Similarity	NPD2071	Approved
0.6988	Remote Similarity	NPD2072	Approved
0.6988	Remote Similarity	NPD2073	Approved
0.6988	Remote Similarity	NPD2070	Approved
0.6988	Remote Similarity	NPD2074	Approved
0.6988	Remote Similarity	NPD2075	Approved
0.6988	Remote Similarity	NPD2069	Approved
0.6988	Remote Similarity	NPD2068	Approved
0.6984	Remote Similarity	NPD6569	Phase 2
0.6979	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD1032	Phase 2
0.6977	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4641	Discontinued
0.6966	Remote Similarity	NPD6446	Discontinued
0.6966	Remote Similarity	NPD424	Approved
0.6966	Remote Similarity	NPD425	Approved
0.6964	Remote Similarity	NPD4510	Discontinued
0.6959	Remote Similarity	NPD3575	Approved
0.6959	Remote Similarity	NPD3576	Approved
0.6954	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.695	Remote Similarity	NPD8093	Discontinued
0.6949	Remote Similarity	NPD3583	Phase 2
0.6947	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3609	Approved
0.6944	Remote Similarity	NPD3610	Approved
0.6943	Remote Similarity	NPD6999	Discontinued
0.6943	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD991	Phase 2
0.6937	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD3014	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD3013	Phase 3
0.6935	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1995	Approved
0.6933	Remote Similarity	NPD1994	Approved
0.6933	Remote Similarity	NPD1993	Approved
0.6923	Remote Similarity	NPD1918	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD9206	Approved
0.6914	Remote Similarity	NPD9207	Approved
0.6907	Remote Similarity	NPD6389	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD2077	Approved
0.6906	Remote Similarity	NPD2076	Approved
0.6906	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD976	Approved
0.6897	Remote Similarity	NPD975	Approved
0.6897	Remote Similarity	NPD977	Approved
0.6897	Remote Similarity	NPD5358	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD6887	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD4886	Phase 2
0.6885	Remote Similarity	NPD6159	Phase 2
0.6882	Remote Similarity	NPD9075	Approved
0.6882	Remote Similarity	NPD9074	Approved
0.6878	Remote Similarity	NPD3321	Discontinued
0.6878	Remote Similarity	NPD5117	Phase 2
0.6875	Remote Similarity	NPD704	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD4128	Approved
0.6868	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD200	Phase 2
0.6867	Remote Similarity	NPD201	Phase 2
0.6864	Remote Similarity	NPD3525	Discontinued
0.6859	Remote Similarity	NPD6361	Phase 2
0.6857	Remote Similarity	NPD2748	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD5088	Discontinued
0.6854	Remote Similarity	NPD5925	Phase 1
0.6842	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4823	Approved
0.6842	Remote Similarity	NPD4824	Approved
0.6842	Remote Similarity	NPD6022	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD748	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD4612	Discontinued
0.6833	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD4075	Phase 2
0.6828	Remote Similarity	NPD2391	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD6522	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD4021	Phase 2
0.6821	Remote Similarity	NPD2462	Phase 3
0.6821	Remote Similarity	NPD2465	Approved
0.6821	Remote Similarity	NPD2466	Phase 3

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