NPASS Compound

Structure

NPC473837 OpenBabel07101718312D 39 45 0 0 1 0 0 0 0 0999 V2000 2.7481 -1.3904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9817 0.9145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3637 -2.8855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5088 0.9331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8391 -1.8073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9818 -2.7435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4541 -1.8620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9823 -2.7752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9268 -1.0123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2844 -1.5086 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0712 -1.3855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6359 -1.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4115 0.0102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2148 0.4559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5216 -1.4589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4551 -1.9255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3890 -0.8299 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0751 0.0599 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9273 -1.0440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6115 -0.1450 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1227 -0.5894 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2225 -0.9749 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4976 -1.3855 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0751 -0.6787 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9960 0.0896 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4556 -1.9573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0712 -1.1393 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4976 0.5205 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4976 -1.1393 0.0000 C 0 0 2 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 -2.4001 -0.1943 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.0236 -1.2286 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.9833 -2.8387 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1086 1.3157 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9612 0.2759 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6025 -0.0108 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3637 -1.8855 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5089 0.9481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9283 -1.1075 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 36 1 0 0 0 0 3 37 1 0 0 0 0 4 38 1 0 0 0 0 5 32 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 16 2 0 0 0 0 9 19 2 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 27 1 0 0 0 0 12 22 1 0 0 0 0 13 18 1 0 0 0 0 13 21 1 0 0 0 0 14 20 1 0 0 0 0 14 28 1 0 0 0 0 15 27 1 0 0 0 0 15 32 1 0 0 0 0 16 19 1 0 0 0 0 16 26 1 0 0 0 0 17 12 1 1 0 0 0 17 20 1 0 0 0 0 17 25 1 0 0 0 0 18 24 1 0 0 0 0 18 28 1 1 0 0 0 19 31 1 0 0 0 0 20 36 1 6 0 0 0 21 27 1 1 0 0 0 21 29 1 0 0 0 0 22 29 1 1 0 0 0 22 30 1 0 0 0 0 23 29 1 1 0 0 0 23 37 1 0 0 0 0 24 29 1 6 0 0 0 24 32 1 0 0 0 0 25 30 1 1 0 0 0 25 38 1 0 0 0 0 26 33 2 0 0 0 0 26 39 1 0 0 0 0 27 39 1 1 0 0 0 28 30 1 6 0 0 0 28 34 1 0 0 0 0 30 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	542.3
Volume:	540.52
LogP:	2.754
LogD:	2.426
LogS:	-3.961
# Rotatable Bonds:	7
TPSA:	123.71
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	7
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.365
Synthetic Accessibility Score:	7.124
Fsp3:	0.767
Lipinski Rule-of-5:	Accepted
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:	-5.322
MDCK Permeability:	6.330316682578996e-05
Pgp-inhibitor:	0.112
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.036
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.935

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.147
Plasma Protein Binding (PPB):	22.710474014282227%
Volume Distribution (VD):	0.78
Pgp-substrate:	52.69989776611328%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.693
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.617
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.01
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.357
CYP3A4-inhibitor:	0.198
CYP3A4-substrate:	0.442

ADMET: Excretion

Clearance (CL):	8.202
Half-life (T1/2):	0.175

ADMET: Toxicity

hERG Blockers:	0.286
Human Hepatotoxicity (H-HT):	0.399
Drug-inuced Liver Injury (DILI):	0.134
AMES Toxicity:	0.108
Rat Oral Acute Toxicity:	0.224
Maximum Recommended Daily Dose:	0.142
Skin Sensitization:	0.611
Carcinogencity:	0.466
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.988

Download Data

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

Natural Product: NPC473837

Natural Product ID:	NPC473837
*Common Name:**	VSUODASNSRJNCP-VHALVFBVSA-N
IUPAC Name:	n.a.
Synonyms:	N-Deacetyl-Lappaconitine
Standard InCHIKey:	VSUODASNSRJNCP-VHALVFBVSA-N
Standard InCHI:	InChI=1S/C30H42N2O7/c1-5-32-15-27(39-26(33)16-8-6-7-9-19(16)31)11-10-23(37-3)29-21(27)13-18(24(29)32)28(34)14-20(36-2)17-12-22(29)30(28,35)25(17)38-4/h6-9,17-18,20-25,34-35H,5,10-15,31H2,1-4H3/t17-,18-,20+,21-,22+,23+,24-,25+,27-,28+,29+,30+/m1/s1
SMILES:	CCN1C[C@@]2(CC[C@@H]([C@]34[C@H]1[C@@H](C[C@H]23)[C@@]1(O)C[C@@H]([C@H]2C[C@@H]4[C@]1(O)[C@H]2OC)OC)OC)OC(=O)c1ccccc1N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453139
PubChem CID:	44566467
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003789] Lappaconitine-type diterpenoid alkaloids

*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
NPO33014	delphinium cashmirianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[541686]

☑ 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
Others	9

Activity Type	# Activity
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Activity	=	8.0	bpm	PMID[533169]
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Activity	=	5.0	bpm	PMID[533169]
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Activity	=	0.0	bpm	PMID[533169]
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Activity	=	1.0	mg kg-1	PMID[533169]
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Activity	=	52.0	s	PMID[533169]
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Activity	=	85.0	s	PMID[533169]

☑ 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 NPC473837 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	344
0.1-0.2	1469
0.2-0.3	3225
0.3-0.4	9921
0.4-0.5	20310
0.5-0.6	5916
0.6-0.7	1376
0.7-0.8	89
0.8-0.85	10
0.85-0.9	31
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9594	High Similarity	NPC223590
0.9545	High Similarity	NPC140311
0.9307	High Similarity	NPC473667
0.9163	High Similarity	NPC106593
0.8857	High Similarity	NPC470631
0.8857	High Similarity	NPC473781
0.8857	High Similarity	NPC35390
0.8815	High Similarity	NPC473486
0.8815	High Similarity	NPC475316
0.852	High Similarity	NPC281470
0.852	High Similarity	NPC172769
0.852	High Similarity	NPC184195
0.852	High Similarity	NPC124690
0.852	High Similarity	NPC205
0.852	High Similarity	NPC166521
0.8418	Intermediate Similarity	NPC40539
0.8376	Intermediate Similarity	NPC108276
0.8376	Intermediate Similarity	NPC163578
0.7952	Intermediate Similarity	NPC476496
0.7923	Intermediate Similarity	NPC475223
0.7885	Intermediate Similarity	NPC475448
0.7885	Intermediate Similarity	NPC246983
0.7857	Intermediate Similarity	NPC326895
0.782	Intermediate Similarity	NPC106840
0.782	Intermediate Similarity	NPC94687
0.782	Intermediate Similarity	NPC476495
0.7756	Intermediate Similarity	NPC198205
0.7756	Intermediate Similarity	NPC21483
0.7681	Intermediate Similarity	NPC198390
0.7644	Intermediate Similarity	NPC112752
0.7644	Intermediate Similarity	NPC311054
0.7608	Intermediate Similarity	NPC90358
0.7608	Intermediate Similarity	NPC107828
0.7536	Intermediate Similarity	NPC136573
0.7536	Intermediate Similarity	NPC176371
0.7235	Intermediate Similarity	NPC476500
0.7209	Intermediate Similarity	NPC471512
0.7163	Intermediate Similarity	NPC475489
0.7162	Intermediate Similarity	NPC473458
0.7143	Intermediate Similarity	NPC316841
0.7143	Intermediate Similarity	NPC475596
0.7143	Intermediate Similarity	NPC475303
0.7137	Intermediate Similarity	NPC127720
0.7137	Intermediate Similarity	NPC127026
0.7124	Intermediate Similarity	NPC475406
0.7118	Intermediate Similarity	NPC476436
0.7112	Intermediate Similarity	NPC30456
0.7109	Intermediate Similarity	NPC25401
0.7105	Intermediate Similarity	NPC471980
0.7094	Intermediate Similarity	NPC327904
0.7094	Intermediate Similarity	NPC154922
0.7094	Intermediate Similarity	NPC38959
0.7089	Intermediate Similarity	NPC476206
0.7089	Intermediate Similarity	NPC259791
0.7089	Intermediate Similarity	NPC476256
0.7089	Intermediate Similarity	NPC476207
0.7089	Intermediate Similarity	NPC476257
0.7089	Intermediate Similarity	NPC476212
0.7089	Intermediate Similarity	NPC476129
0.7089	Intermediate Similarity	NPC221687
0.7089	Intermediate Similarity	NPC476205
0.7087	Intermediate Similarity	NPC475631
0.7087	Intermediate Similarity	NPC328186
0.7087	Intermediate Similarity	NPC476110
0.7087	Intermediate Similarity	NPC475600
0.7087	Intermediate Similarity	NPC122968
0.7087	Intermediate Similarity	NPC87152
0.7087	Intermediate Similarity	NPC228377
0.7087	Intermediate Similarity	NPC471513
0.7087	Intermediate Similarity	NPC477787
0.708	Intermediate Similarity	NPC84815
0.708	Intermediate Similarity	NPC288110
0.708	Intermediate Similarity	NPC301368
0.7079	Intermediate Similarity	NPC30171
0.7069	Intermediate Similarity	NPC473689
0.7069	Intermediate Similarity	NPC292416
0.7056	Intermediate Similarity	NPC476218
0.7056	Intermediate Similarity	NPC475644
0.7056	Intermediate Similarity	NPC471977
0.7056	Intermediate Similarity	NPC471190
0.7056	Intermediate Similarity	NPC470486
0.7056	Intermediate Similarity	NPC108804
0.7051	Intermediate Similarity	NPC327769
0.7039	Intermediate Similarity	NPC319880
0.7039	Intermediate Similarity	NPC244839
0.7039	Intermediate Similarity	NPC320324
0.7039	Intermediate Similarity	NPC476429
0.7031	Intermediate Similarity	NPC76565
0.7031	Intermediate Similarity	NPC57797
0.7031	Intermediate Similarity	NPC250807
0.7023	Intermediate Similarity	NPC36607
0.7021	Intermediate Similarity	NPC17160
0.7021	Intermediate Similarity	NPC313720
0.7017	Intermediate Similarity	NPC113455
0.7015	Intermediate Similarity	NPC253738
0.7014	Intermediate Similarity	NPC327699
0.7013	Intermediate Similarity	NPC146824
0.7009	Intermediate Similarity	NPC237702
0.7	Intermediate Similarity	NPC120239
0.7	Intermediate Similarity	NPC475137
0.7	Intermediate Similarity	NPC473850
0.7	Intermediate Similarity	NPC475498
0.6991	Remote Similarity	NPC471016
0.6991	Remote Similarity	NPC6981
0.6983	Remote Similarity	NPC475362
0.6979	Remote Similarity	NPC170751
0.6979	Remote Similarity	NPC160113
0.6979	Remote Similarity	NPC476220
0.6977	Remote Similarity	NPC473375
0.6977	Remote Similarity	NPC97100
0.697	Remote Similarity	NPC473506
0.696	Remote Similarity	NPC212768
0.696	Remote Similarity	NPC144779
0.696	Remote Similarity	NPC473115
0.696	Remote Similarity	NPC473089
0.696	Remote Similarity	NPC294579
0.696	Remote Similarity	NPC6576
0.696	Remote Similarity	NPC158020
0.696	Remote Similarity	NPC75600
0.696	Remote Similarity	NPC62367
0.6953	Remote Similarity	NPC477397
0.695	Remote Similarity	NPC73644
0.6947	Remote Similarity	NPC477907
0.6947	Remote Similarity	NPC42678
0.6947	Remote Similarity	NPC477909
0.6947	Remote Similarity	NPC470306
0.6946	Remote Similarity	NPC469452
0.6942	Remote Similarity	NPC475427
0.6934	Remote Similarity	NPC477998
0.6933	Remote Similarity	NPC476258
0.6933	Remote Similarity	NPC304837
0.6933	Remote Similarity	NPC469450
0.693	Remote Similarity	NPC216428
0.6926	Remote Similarity	NPC328154
0.6917	Remote Similarity	NPC475648
0.6916	Remote Similarity	NPC471014
0.6916	Remote Similarity	NPC475408
0.6913	Remote Similarity	NPC477788
0.6903	Remote Similarity	NPC4421
0.6889	Remote Similarity	NPC127996
0.6888	Remote Similarity	NPC329932
0.6887	Remote Similarity	NPC14994
0.6875	Remote Similarity	NPC469451
0.6875	Remote Similarity	NPC203005
0.6872	Remote Similarity	NPC478263
0.6872	Remote Similarity	NPC52262
0.687	Remote Similarity	NPC477912
0.6867	Remote Similarity	NPC211920
0.6866	Remote Similarity	NPC90967
0.6862	Remote Similarity	NPC471782
0.6862	Remote Similarity	NPC471583
0.6862	Remote Similarity	NPC253482
0.6857	Remote Similarity	NPC159963
0.6856	Remote Similarity	NPC222046
0.6853	Remote Similarity	NPC477902
0.6853	Remote Similarity	NPC19175
0.6853	Remote Similarity	NPC477394
0.6835	Remote Similarity	NPC473558
0.6835	Remote Similarity	NPC473490
0.6832	Remote Similarity	NPC476750
0.683	Remote Similarity	NPC48042
0.683	Remote Similarity	NPC304179
0.683	Remote Similarity	NPC472550
0.6829	Remote Similarity	NPC476749
0.6829	Remote Similarity	NPC131273
0.6829	Remote Similarity	NPC473441
0.6824	Remote Similarity	NPC148860
0.6822	Remote Similarity	NPC22689
0.6822	Remote Similarity	NPC105055
0.6822	Remote Similarity	NPC471623
0.6821	Remote Similarity	NPC478264
0.682	Remote Similarity	NPC191193
0.682	Remote Similarity	NPC242662
0.682	Remote Similarity	NPC321072
0.682	Remote Similarity	NPC215892
0.682	Remote Similarity	NPC278540
0.6818	Remote Similarity	NPC472329
0.6818	Remote Similarity	NPC472330
0.6814	Remote Similarity	NPC472553
0.6798	Remote Similarity	NPC234772
0.6795	Remote Similarity	NPC124029
0.6794	Remote Similarity	NPC218594
0.6794	Remote Similarity	NPC99043
0.6791	Remote Similarity	NPC324251
0.6791	Remote Similarity	NPC275170
0.6791	Remote Similarity	NPC206211
0.6791	Remote Similarity	NPC473300
0.6791	Remote Similarity	NPC471754
0.6791	Remote Similarity	NPC306001
0.6791	Remote Similarity	NPC475336
0.6791	Remote Similarity	NPC317882
0.6791	Remote Similarity	NPC453583
0.6791	Remote Similarity	NPC471629
0.6791	Remote Similarity	NPC473400
0.6789	Remote Similarity	NPC471606
0.6789	Remote Similarity	NPC208553
0.6789	Remote Similarity	NPC181964
0.6783	Remote Similarity	NPC472555
0.6781	Remote Similarity	NPC231924
0.678	Remote Similarity	NPC150698

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 NPC473837 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	592
0.2-0.3	834
0.3-0.4	2220
0.4-0.5	3703
0.5-0.6	1495
0.6-0.7	112
0.7-0.8	1
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
0.8058	Intermediate Similarity	NPD7497	Discontinued
0.7184	Intermediate Similarity	NPD8658	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD6997	Phase 2
0.6864	Remote Similarity	NPD6625	Approved
0.6822	Remote Similarity	NPD8435	Approved
0.6822	Remote Similarity	NPD8360	Approved
0.6822	Remote Similarity	NPD8361	Approved
0.6789	Remote Similarity	NPD8485	Approved
0.6746	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5928	Phase 1
0.6729	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD7047	Phase 3
0.6697	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.662	Remote Similarity	NPD7962	Phase 2
0.6585	Remote Similarity	NPD8468	Phase 2
0.6561	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD8407	Phase 2
0.6471	Remote Similarity	NPD2672	Discontinued
0.6468	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD3170	Approved
0.6462	Remote Similarity	NPD1109	Approved
0.6462	Remote Similarity	NPD1110	Approved
0.6453	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD6723	Discontinued
0.6445	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD7036	Phase 3
0.6442	Remote Similarity	NPD7035	Approved
0.6429	Remote Similarity	NPD6874	Approved
0.6426	Remote Similarity	NPD2899	Discontinued
0.6419	Remote Similarity	NPD8368	Discontinued
0.6413	Remote Similarity	NPD2973	Approved
0.6413	Remote Similarity	NPD2975	Approved
0.6413	Remote Similarity	NPD2974	Approved
0.6411	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.6411	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4580	Approved
0.6398	Remote Similarity	NPD3437	Discontinued
0.6393	Remote Similarity	NPD7906	Approved
0.639	Remote Similarity	NPD2836	Approved
0.6388	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD4668	Phase 2
0.6382	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.638	Remote Similarity	NPD7569	Approved
0.638	Remote Similarity	NPD7570	Approved
0.638	Remote Similarity	NPD8146	Phase 2
0.6379	Remote Similarity	NPD7922	Phase 1
0.6372	Remote Similarity	NPD2494	Approved
0.6372	Remote Similarity	NPD3452	Approved
0.6372	Remote Similarity	NPD7476	Discontinued
0.6372	Remote Similarity	NPD2493	Approved
0.6372	Remote Similarity	NPD3450	Approved
0.6371	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD5997	Discontinued
0.6368	Remote Similarity	NPD1802	Approved
0.6368	Remote Similarity	NPD1801	Approved
0.6367	Remote Similarity	NPD7048	Phase 3
0.6364	Remote Similarity	NPD5430	Discontinued
0.636	Remote Similarity	NPD4583	Approved
0.636	Remote Similarity	NPD4582	Approved
0.6356	Remote Similarity	NPD5609	Approved
0.6356	Remote Similarity	NPD5608	Approved
0.6355	Remote Similarity	NPD7606	Phase 3
0.6351	Remote Similarity	NPD7795	Phase 2
0.6348	Remote Similarity	NPD7302	Phase 3
0.6348	Remote Similarity	NPD7300	Phase 3
0.6344	Remote Similarity	NPD5005	Approved
0.6344	Remote Similarity	NPD5006	Approved
0.6338	Remote Similarity	NPD7940	Phase 3
0.6337	Remote Similarity	NPD7528	Approved
0.6336	Remote Similarity	NPD1945	Phase 1
0.6333	Remote Similarity	NPD7186	Phase 3
0.6323	Remote Similarity	NPD7256	Discontinued
0.6318	Remote Similarity	NPD3912	Discontinued
0.6316	Remote Similarity	NPD8008	Approved
0.6316	Remote Similarity	NPD4004	Approved
0.6316	Remote Similarity	NPD4002	Approved
0.6316	Remote Similarity	NPD8007	Approved
0.6313	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4420	Approved
0.6309	Remote Similarity	NPD8462	Phase 1
0.6305	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7907	Approved
0.6298	Remote Similarity	NPD8149	Discontinued
0.6295	Remote Similarity	NPD5411	Discontinued
0.6295	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD8319	Approved
0.6288	Remote Similarity	NPD8320	Phase 1
0.6278	Remote Similarity	NPD5610	Approved
0.6277	Remote Similarity	NPD4082	Approved
0.6273	Remote Similarity	NPD4663	Approved
0.6271	Remote Similarity	NPD8404	Phase 2
0.6269	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD7295	Approved
0.6269	Remote Similarity	NPD7803	Approved
0.6266	Remote Similarity	NPD5676	Approved
0.6262	Remote Similarity	NPD5741	Approved
0.6262	Remote Similarity	NPD5743	Approved
0.6262	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5742	Approved
0.6262	Remote Similarity	NPD5466	Approved
0.6261	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.626	Remote Similarity	NPD8363	Approved
0.626	Remote Similarity	NPD5891	Approved
0.626	Remote Similarity	NPD8364	Approved
0.6256	Remote Similarity	NPD5184	Approved
0.6256	Remote Similarity	NPD5182	Approved
0.6256	Remote Similarity	NPD4888	Discontinued
0.6256	Remote Similarity	NPD5185	Approved
0.6241	Remote Similarity	NPD8466	Approved
0.6241	Remote Similarity	NPD8467	Approved
0.6241	Remote Similarity	NPD8465	Approved
0.624	Remote Similarity	NPD7708	Approved
0.6239	Remote Similarity	NPD7827	Phase 1
0.6239	Remote Similarity	NPD7301	Phase 3
0.6239	Remote Similarity	NPD5197	Approved
0.6239	Remote Similarity	NPD5194	Approved
0.6239	Remote Similarity	NPD8281	Discontinued
0.6239	Remote Similarity	NPD5196	Approved
0.6238	Remote Similarity	NPD7236	Approved
0.6234	Remote Similarity	NPD6296	Discontinued
0.6233	Remote Similarity	NPD7799	Discontinued
0.6222	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.622	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6219	Remote Similarity	NPD7487	Discontinued
0.6218	Remote Similarity	NPD4111	Phase 1
0.6218	Remote Similarity	NPD6770	Approved
0.6218	Remote Similarity	NPD4665	Approved
0.6215	Remote Similarity	NPD7854	Phase 2
0.6214	Remote Similarity	NPD4121	Phase 3
0.6214	Remote Similarity	NPD4120	Approved
0.6214	Remote Similarity	NPD5086	Approved
0.6212	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.621	Remote Similarity	NPD4578	Approved
0.621	Remote Similarity	NPD7546	Discontinued
0.621	Remote Similarity	NPD4577	Approved
0.6207	Remote Similarity	NPD7701	Phase 2
0.6207	Remote Similarity	NPD7478	Approved
0.6204	Remote Similarity	NPD8006	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD7956	Approved
0.6202	Remote Similarity	NPD7955	Approved
0.619	Remote Similarity	NPD8161	Suspended
0.619	Remote Similarity	NPD7999	Approved
0.6188	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD5042	Phase 1
0.6184	Remote Similarity	NPD4107	Approved
0.6182	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD7775	Approved
0.6174	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.6165	Remote Similarity	NPD7239	Suspended
0.6164	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD4596	Phase 1
0.6164	Remote Similarity	NPD7583	Approved
0.6163	Remote Similarity	NPD7688	Phase 1
0.6162	Remote Similarity	NPD2569	Approved
0.6162	Remote Similarity	NPD2567	Approved
0.616	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6570	Approved
0.6154	Remote Similarity	NPD3154	Approved
0.6154	Remote Similarity	NPD3153	Approved
0.6154	Remote Similarity	NPD6571	Approved
0.6154	Remote Similarity	NPD5036	Approved
0.615	Remote Similarity	NPD2247	Approved
0.615	Remote Similarity	NPD2681	Approved
0.615	Remote Similarity	NPD2680	Approved
0.615	Remote Similarity	NPD2249	Approved
0.6148	Remote Similarity	NPD8492	Approved
0.6148	Remote Similarity	NPD8460	Approved
0.6148	Remote Similarity	NPD8426	Approved
0.6148	Remote Similarity	NPD8459	Approved
0.6148	Remote Similarity	NPD8425	Approved
0.6147	Remote Similarity	NPD7891	Discontinued
0.6147	Remote Similarity	NPD4040	Phase 1
0.6147	Remote Similarity	NPD6250	Discontinued
0.6147	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD1294	Discontinued
0.614	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.614	Remote Similarity	NPD2248	Approved
0.614	Remote Similarity	NPD2246	Approved
0.614	Remote Similarity	NPD4481	Phase 3
0.6139	Remote Similarity	NPD2575	Approved
0.6137	Remote Similarity	NPD7585	Approved
0.6136	Remote Similarity	NPD7312	Approved
0.6136	Remote Similarity	NPD7311	Approved
0.6136	Remote Similarity	NPD7313	Approved
0.6136	Remote Similarity	NPD7310	Approved
0.6134	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD6212	Phase 3
0.6133	Remote Similarity	NPD7262	Phase 1
0.6133	Remote Similarity	NPD6213	Phase 3
0.6133	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.613	Remote Similarity	NPD3057	Approved
0.613	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6128	Remote Similarity	NPD4493	Discontinued
0.6126	Remote Similarity	NPD5037	Approved
0.6126	Remote Similarity	NPD4951	Discontinued
0.6126	Remote Similarity	NPD5038	Approved
0.6123	Remote Similarity	NPD6621	Clinical (unspecified phase)

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