NPASS Compound

Structure

CID153007 OpenBabel06191715522D 34 38 0 0 1 0 0 0 0 0999 V2000 -3.6659 5.1947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3925 3.9505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8481 2.4831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6115 5.3987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7881 3.7137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2145 -0.2507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4874 -0.9057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0107 0.7065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5566 -0.6036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0799 1.0087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5435 0.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6954 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0869 2.9353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0867 1.9568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6962 2.9363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8470 1.4689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5443 3.4256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2406 4.4032 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3528 0.3536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5438 1.4680 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2403 3.4251 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3919 1.9573 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6959 1.9578 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8475 0.4893 0.0000 C 0 0 1 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 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4220 0.6558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3922 2.9358 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8478 1.4684 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6949 0.0007 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.2134 4.5052 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2183 1.6130 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 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 2 0 0 0 0 9 20 2 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 12 25 1 0 0 0 0 13 14 1 0 0 0 0 13 22 1 0 0 0 0 14 23 1 0 0 0 0 15 17 1 0 0 0 0 15 24 1 0 0 0 0 16 18 1 0 0 0 0 16 26 2 0 0 0 0 17 29 1 0 0 0 0 18 30 1 0 0 0 0 19 1 1 1 0 0 0 19 22 1 0 0 0 0 19 32 1 0 0 0 0 20 28 1 0 0 0 0 21 11 1 1 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 22 29 1 6 0 0 0 23 29 1 6 0 0 0 24 30 1 6 0 0 0 25 27 1 0 0 0 0 25 30 1 6 0 0 0 26 27 1 0 0 0 0 26 31 1 0 0 0 0 27 33 2 0 0 0 0 28 31 2 3 0 0 0 28 34 1 0 0 0 0 29 2 1 6 0 0 0 30 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	462.32
Volume:	508.409
LogP:	4.979
LogD:	4.448
LogS:	-5.038
# Rotatable Bonds:	4
TPSA:	49.74
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.549
Synthetic Accessibility Score:	4.499
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.788
MDCK Permeability:	1.8748616639641114e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.16
Plasma Protein Binding (PPB):	92.9706802368164%
Volume Distribution (VD):	0.758
Pgp-substrate:	3.6821165084838867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.297
CYP1A2-substrate:	0.368
CYP2C19-inhibitor:	0.132
CYP2C19-substrate:	0.958
CYP2C9-inhibitor:	0.409
CYP2C9-substrate:	0.108
CYP2D6-inhibitor:	0.912
CYP2D6-substrate:	0.906
CYP3A4-inhibitor:	0.711
CYP3A4-substrate:	0.667

ADMET: Excretion

Clearance (CL):	6.187
Half-life (T1/2):	0.06

ADMET: Toxicity

hERG Blockers:	0.982
Human Hepatotoxicity (H-HT):	0.362
Drug-inuced Liver Injury (DILI):	0.841
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.814
Maximum Recommended Daily Dose:	0.48
Skin Sensitization:	0.943
Carcinogencity:	0.423
Eye Corrosion:	0.004
Eye Irritation:	0.016
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC153007

Natural Product ID:	NPC153007
*Common Name:**	(+)-Axillaridine A
IUPAC Name:	N-[(5R,8S,9S,10R,13S,14S,17S)-17-[(1S)-1-(dimethylamino)ethyl]-10,13-dimethyl-4-oxo-1,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-yl]benzamide
Synonyms:	(+)-Axillaridine A
Standard InCHIKey:	ZMAOKPMWBVUQPK-IWDJEAQTSA-N
Standard InCHI:	InChI=1S/C30H42N2O2/c1-19(32(4)5)22-13-14-23-21-11-12-25-27(33)26(31-28(34)20-9-7-6-8-10-20)16-18-30(25,3)24(21)15-17-29(22,23)2/h6-10,16,19,21-25H,11-15,17-18H2,1-5H3,(H,31,34)/t19-,21-,22+,23-,24-,25-,29+,30+/m0/s1
SMILES:	C[C@@H]([C@H]1CC[C@H]2[C@@H]3CC[C@H]4C(=O)C(=CC[C@]4(C)[C@H]3CC[C@]12C)N=C(c1ccccc1)O)N(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL335133
PubChem CID:	3004425
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001194] Oxosteroids

*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
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14584959]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14643329]
NPO26156	Mahurea palustris	Species	Calophyllaceae	Eukaryota	leaves	French Guiana	1996-OCT	PMID[16038535]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9548847]
NPO4994	Pachysandra procumbens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9784163]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26204	Arisaema curvatum	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26204	Arisaema curvatum	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26556	Pterocephalus pinardi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4994	Pachysandra procumbens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26673	Casearia ilicifolia	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26156	Mahurea palustris	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26204	Arisaema curvatum	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26471	Lenormandia smithiae	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26423	Scaevola racemigera	Species	Goodeniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26372	Sarcandra hainanensis	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26446	Lecanora frustulosa	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25707	Euchaeta russelli	Species	Euchaetidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23047	Streptomyces griseoviridis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO18582	Cosmospora butyri	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23214	Drosera congolana	Species	Droseraceae	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	4
Ki	2

Activity Type	# Activity
Individual Protein	5
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2668	Individual Protein	Acetylcholinesterase	Torpedo californica	IC50	=	5200.0	nM	PMID[488145]
NPT2668	Individual Protein	Acetylcholinesterase	Torpedo californica	Ki	=	3030.0	nM	PMID[488145]
NPT439	Individual Protein	Butyrylcholinesterase	Homo sapiens	IC50	=	2490.0	nM	PMID[488145]
NPT439	Individual Protein	Butyrylcholinesterase	Homo sapiens	Ki	=	2150.0	nM	PMID[488145]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	=	5248.07	nM	PMID[488146]
NPT3844	Protein Complex	Anti-estrogen binding site (AEBS)	Homo sapiens	IC50	=	8000.0	nM	PMID[488147]

☑ 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 NPC153007 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	210
0.1-0.2	902
0.2-0.3	2241
0.3-0.4	7182
0.4-0.5	22103
0.5-0.6	9011
0.6-0.7	1017
0.7-0.8	28
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8409	Intermediate Similarity	NPC109151
0.8322	Intermediate Similarity	NPC473922
0.8014	Intermediate Similarity	NPC132847
0.7943	Intermediate Similarity	NPC3202
0.7756	Intermediate Similarity	NPC476750
0.7736	Intermediate Similarity	NPC476749
0.766	Intermediate Similarity	NPC116057
0.7613	Intermediate Similarity	NPC93343
0.76	Intermediate Similarity	NPC475578
0.7535	Intermediate Similarity	NPC472413
0.75	Intermediate Similarity	NPC2672
0.7483	Intermediate Similarity	NPC328824
0.7442	Intermediate Similarity	NPC469958
0.7419	Intermediate Similarity	NPC275839
0.7415	Intermediate Similarity	NPC208725
0.7394	Intermediate Similarity	NPC119326
0.7386	Intermediate Similarity	NPC476757
0.7255	Intermediate Similarity	NPC44649
0.7254	Intermediate Similarity	NPC285394
0.7203	Intermediate Similarity	NPC472414
0.7203	Intermediate Similarity	NPC4974
0.7192	Intermediate Similarity	NPC183722
0.719	Intermediate Similarity	NPC473804
0.7183	Intermediate Similarity	NPC472415
0.7179	Intermediate Similarity	NPC470274
0.717	Intermediate Similarity	NPC217801
0.7154	Intermediate Similarity	NPC152718
0.7152	Intermediate Similarity	NPC150712
0.7143	Intermediate Similarity	NPC119569
0.7143	Intermediate Similarity	NPC246913
0.7133	Intermediate Similarity	NPC473938
0.7103	Intermediate Similarity	NPC210950
0.7103	Intermediate Similarity	NPC199738
0.7101	Intermediate Similarity	NPC473573
0.7095	Intermediate Similarity	NPC313663
0.7081	Intermediate Similarity	NPC235460
0.7055	Intermediate Similarity	NPC71271
0.7034	Intermediate Similarity	NPC478107
0.7034	Intermediate Similarity	NPC470649
0.7023	Intermediate Similarity	NPC226509
0.7012	Intermediate Similarity	NPC71205
0.7007	Intermediate Similarity	NPC478147
0.698	Remote Similarity	NPC328070
0.6966	Remote Similarity	NPC79698
0.6963	Remote Similarity	NPC175585
0.6943	Remote Similarity	NPC254798
0.694	Remote Similarity	NPC191215
0.694	Remote Similarity	NPC274089
0.6934	Remote Similarity	NPC471188
0.6913	Remote Similarity	NPC42423
0.6906	Remote Similarity	NPC246904
0.6906	Remote Similarity	NPC93181
0.6887	Remote Similarity	NPC203486
0.6867	Remote Similarity	NPC244866
0.6863	Remote Similarity	NPC322526
0.6861	Remote Similarity	NPC95126
0.6861	Remote Similarity	NPC475002
0.6853	Remote Similarity	NPC190663
0.6853	Remote Similarity	NPC470585
0.6853	Remote Similarity	NPC190501
0.6853	Remote Similarity	NPC318552
0.6835	Remote Similarity	NPC476444
0.6831	Remote Similarity	NPC220698
0.6797	Remote Similarity	NPC316906
0.6797	Remote Similarity	NPC473055
0.6797	Remote Similarity	NPC473052
0.6783	Remote Similarity	NPC473974
0.6783	Remote Similarity	NPC79933
0.6783	Remote Similarity	NPC31296
0.6783	Remote Similarity	NPC258366
0.6766	Remote Similarity	NPC278887
0.6759	Remote Similarity	NPC269923
0.6759	Remote Similarity	NPC160493
0.6759	Remote Similarity	NPC167323
0.6757	Remote Similarity	NPC305717
0.6757	Remote Similarity	NPC474106
0.6753	Remote Similarity	NPC471201
0.675	Remote Similarity	NPC233702
0.6741	Remote Similarity	NPC211551
0.6739	Remote Similarity	NPC474057
0.6733	Remote Similarity	NPC126458
0.6718	Remote Similarity	NPC33168
0.6713	Remote Similarity	NPC472698
0.6713	Remote Similarity	NPC472697
0.6711	Remote Similarity	NPC296712
0.6711	Remote Similarity	NPC474473
0.6711	Remote Similarity	NPC473322
0.6709	Remote Similarity	NPC16188
0.6691	Remote Similarity	NPC85560
0.6691	Remote Similarity	NPC244933
0.669	Remote Similarity	NPC473050
0.669	Remote Similarity	NPC472981
0.669	Remote Similarity	NPC473051
0.6689	Remote Similarity	NPC473962
0.6688	Remote Similarity	NPC477596
0.6687	Remote Similarity	NPC476231
0.6687	Remote Similarity	NPC114808
0.6667	Remote Similarity	NPC85511
0.6667	Remote Similarity	NPC279045
0.6667	Remote Similarity	NPC113325
0.6667	Remote Similarity	NPC292758
0.6667	Remote Similarity	NPC65855
0.6667	Remote Similarity	NPC274839
0.6667	Remote Similarity	NPC329913
0.6667	Remote Similarity	NPC33742
0.6667	Remote Similarity	NPC126516
0.6647	Remote Similarity	NPC126676
0.6647	Remote Similarity	NPC469671
0.6645	Remote Similarity	NPC249899
0.6643	Remote Similarity	NPC306977
0.6643	Remote Similarity	NPC287055
0.6643	Remote Similarity	NPC242957
0.6643	Remote Similarity	NPC206414
0.6643	Remote Similarity	NPC470545
0.6642	Remote Similarity	NPC318154
0.6642	Remote Similarity	NPC249811
0.6627	Remote Similarity	NPC73644
0.6623	Remote Similarity	NPC89769
0.6623	Remote Similarity	NPC477594
0.6623	Remote Similarity	NPC126859
0.6623	Remote Similarity	NPC259665
0.6623	Remote Similarity	NPC255447
0.6621	Remote Similarity	NPC80150
0.6618	Remote Similarity	NPC230677
0.6618	Remote Similarity	NPC471186
0.6606	Remote Similarity	NPC104345
0.6603	Remote Similarity	NPC472243
0.6603	Remote Similarity	NPC239770
0.6601	Remote Similarity	NPC228511
0.66	Remote Similarity	NPC51448
0.66	Remote Similarity	NPC115797
0.66	Remote Similarity	NPC40488
0.6597	Remote Similarity	NPC470546
0.6596	Remote Similarity	NPC276949
0.6596	Remote Similarity	NPC471721
0.6596	Remote Similarity	NPC35850
0.6593	Remote Similarity	NPC471317
0.6593	Remote Similarity	NPC202613
0.6591	Remote Similarity	NPC184033
0.6591	Remote Similarity	NPC251579
0.6591	Remote Similarity	NPC133135
0.6587	Remote Similarity	NPC289776
0.6587	Remote Similarity	NPC133470
0.6587	Remote Similarity	NPC191863
0.6587	Remote Similarity	NPC67080
0.6579	Remote Similarity	NPC72915
0.6579	Remote Similarity	NPC257390
0.6579	Remote Similarity	NPC326966
0.6577	Remote Similarity	NPC470765
0.6575	Remote Similarity	NPC273830
0.6573	Remote Similarity	NPC212891
0.6573	Remote Similarity	NPC470544
0.6571	Remote Similarity	NPC218855
0.6569	Remote Similarity	NPC45033
0.6568	Remote Similarity	NPC98187
0.6567	Remote Similarity	NPC264728
0.6567	Remote Similarity	NPC474582
0.6567	Remote Similarity	NPC469457
0.6562	Remote Similarity	NPC9373
0.6561	Remote Similarity	NPC234548
0.6561	Remote Similarity	NPC248287
0.6561	Remote Similarity	NPC33011
0.6558	Remote Similarity	NPC293377
0.6558	Remote Similarity	NPC260045
0.6558	Remote Similarity	NPC476102
0.6558	Remote Similarity	NPC9687
0.6558	Remote Similarity	NPC474787
0.6558	Remote Similarity	NPC475346
0.6558	Remote Similarity	NPC475627
0.6558	Remote Similarity	NPC273907
0.6558	Remote Similarity	NPC76785
0.6558	Remote Similarity	NPC18982
0.6558	Remote Similarity	NPC90194
0.6558	Remote Similarity	NPC474811
0.6558	Remote Similarity	NPC48929
0.6558	Remote Similarity	NPC118099
0.6558	Remote Similarity	NPC475598
0.6558	Remote Similarity	NPC474855
0.6558	Remote Similarity	NPC475457
0.6558	Remote Similarity	NPC475318
0.6558	Remote Similarity	NPC79465
0.6558	Remote Similarity	NPC49577
0.6558	Remote Similarity	NPC151706
0.6556	Remote Similarity	NPC124802
0.6556	Remote Similarity	NPC325651
0.6552	Remote Similarity	NPC203005
0.6549	Remote Similarity	NPC221275
0.6549	Remote Similarity	NPC476357
0.6548	Remote Similarity	NPC189116
0.6543	Remote Similarity	NPC470019
0.6541	Remote Similarity	NPC297322
0.6538	Remote Similarity	NPC193358
0.6536	Remote Similarity	NPC18798
0.6533	Remote Similarity	NPC470753
0.6533	Remote Similarity	NPC473220
0.6532	Remote Similarity	NPC471743
0.6531	Remote Similarity	NPC154696
0.6528	Remote Similarity	NPC45794
0.6525	Remote Similarity	NPC143768
0.6525	Remote Similarity	NPC474584

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 NPC153007 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	144
0.1-0.2	470
0.2-0.3	718
0.3-0.4	1193
0.4-0.5	3697
0.5-0.6	2532
0.6-0.7	385
0.7-0.8	11
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7826	Intermediate Similarity	NPD6330	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD8148	Approved
0.7365	Intermediate Similarity	NPD8147	Approved
0.7299	Intermediate Similarity	NPD3123	Discovery
0.7267	Intermediate Similarity	NPD6897	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD5158	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD5157	Phase 1
0.7254	Intermediate Similarity	NPD5159	Phase 2
0.7237	Intermediate Similarity	NPD7082	Approved
0.719	Intermediate Similarity	NPD7259	Approved
0.7172	Intermediate Similarity	NPD7084	Phase 3
0.7143	Intermediate Similarity	NPD7740	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7295	Approved
0.7095	Intermediate Similarity	NPD7715	Approved
0.7095	Intermediate Similarity	NPD7714	Approved
0.7067	Intermediate Similarity	NPD6817	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2173	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD4980	Approved
0.6985	Remote Similarity	NPD3644	Approved
0.6985	Remote Similarity	NPD3642	Approved
0.6985	Remote Similarity	NPD3643	Approved
0.698	Remote Similarity	NPD7713	Phase 3
0.6928	Remote Similarity	NPD6522	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7602	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7011	Discontinued
0.6894	Remote Similarity	NPD4818	Approved
0.6894	Remote Similarity	NPD4817	Approved
0.6889	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD6789	Approved
0.6883	Remote Similarity	NPD7720	Phase 2
0.6879	Remote Similarity	NPD7610	Discontinued
0.6867	Remote Similarity	NPD7086	Phase 2
0.6866	Remote Similarity	NPD5717	Approved
0.6859	Remote Similarity	NPD7487	Discontinued
0.6853	Remote Similarity	NPD7725	Approved
0.6853	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD2932	Approved
0.6853	Remote Similarity	NPD3019	Approved
0.6846	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6624	Discontinued
0.6821	Remote Similarity	NPD6346	Approved
0.6805	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6565	Approved
0.6803	Remote Similarity	NPD6564	Approved
0.6803	Remote Similarity	NPD6563	Approved
0.6797	Remote Similarity	NPD7230	Approved
0.6797	Remote Similarity	NPD7231	Approved
0.6786	Remote Similarity	NPD5951	Approved
0.6768	Remote Similarity	NPD4335	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5618	Discontinued
0.6739	Remote Similarity	NPD4253	Approved
0.6739	Remote Similarity	NPD4254	Approved
0.6738	Remote Similarity	NPD4031	Approved
0.6738	Remote Similarity	NPD4032	Approved
0.6736	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6325	Discontinued
0.6735	Remote Similarity	NPD3125	Approved
0.673	Remote Similarity	NPD7478	Approved
0.6716	Remote Similarity	NPD3682	Approved
0.6716	Remote Similarity	NPD4229	Approved
0.6716	Remote Similarity	NPD3680	Approved
0.6716	Remote Similarity	NPD3681	Approved
0.6716	Remote Similarity	NPD4231	Approved
0.6716	Remote Similarity	NPD3683	Approved
0.6715	Remote Similarity	NPD4720	Approved
0.6715	Remote Similarity	NPD4717	Approved
0.6715	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD4718	Approved
0.6713	Remote Similarity	NPD4479	Discontinued
0.6713	Remote Similarity	NPD7009	Phase 2
0.6709	Remote Similarity	NPD8131	Suspended
0.6689	Remote Similarity	NPD8011	Discontinued
0.6687	Remote Similarity	NPD7463	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6994	Approved
0.6667	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2605	Approved
0.6667	Remote Similarity	NPD6993	Approved
0.6667	Remote Similarity	NPD2606	Approved
0.6667	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1755	Approved
0.6647	Remote Similarity	NPD5190	Phase 2
0.6646	Remote Similarity	NPD7253	Phase 3
0.6646	Remote Similarity	NPD6676	Phase 2
0.6643	Remote Similarity	NPD6858	Approved
0.6643	Remote Similarity	NPD7094	Approved
0.6643	Remote Similarity	NPD7522	Discontinued
0.6642	Remote Similarity	NPD5716	Approved
0.6642	Remote Similarity	NPD4119	Approved
0.6623	Remote Similarity	NPD5156	Approved
0.6623	Remote Similarity	NPD6039	Approved
0.6623	Remote Similarity	NPD5155	Approved
0.6623	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD5578	Approved
0.6622	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD3589	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD7606	Phase 3
0.6603	Remote Similarity	NPD7450	Phase 2
0.6601	Remote Similarity	NPD4445	Approved
0.6601	Remote Similarity	NPD4453	Approved
0.6601	Remote Similarity	NPD4452	Approved
0.6593	Remote Similarity	NPD4656	Approved
0.6593	Remote Similarity	NPD4658	Approved
0.6591	Remote Similarity	NPD4655	Approved
0.6591	Remote Similarity	NPD4657	Approved
0.659	Remote Similarity	NPD4603	Phase 2
0.6579	Remote Similarity	NPD4621	Approved
0.6579	Remote Similarity	NPD4619	Approved
0.6575	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD6775	Clinical (unspecified phase)
0.657	Remote Similarity	NPD5033	Approved
0.6562	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD6086	Phase 2
0.6558	Remote Similarity	NPD8643	Discontinued
0.6556	Remote Similarity	NPD3595	Approved
0.6556	Remote Similarity	NPD3594	Approved
0.6554	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4105	Approved
0.6552	Remote Similarity	NPD4102	Approved
0.6549	Remote Similarity	NPD4766	Approved
0.6534	Remote Similarity	NPD5032	Approved
0.6531	Remote Similarity	NPD4806	Approved
0.6531	Remote Similarity	NPD6287	Discontinued
0.6531	Remote Similarity	NPD4807	Approved
0.6528	Remote Similarity	NPD1758	Phase 1
0.6525	Remote Similarity	NPD2607	Approved
0.6522	Remote Similarity	NPD8165	Discontinued
0.6519	Remote Similarity	NPD4719	Phase 2
0.6519	Remote Similarity	NPD6024	Approved
0.6519	Remote Similarity	NPD8146	Phase 2
0.6519	Remote Similarity	NPD6027	Approved
0.6516	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6894	Phase 1
0.6507	Remote Similarity	NPD5306	Approved
0.6507	Remote Similarity	NPD5305	Approved
0.6506	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD7131	Phase 3
0.65	Remote Similarity	NPD6836	Approved
0.6497	Remote Similarity	NPD5035	Approved
0.6494	Remote Similarity	NPD5119	Approved
0.6494	Remote Similarity	NPD5120	Approved
0.6494	Remote Similarity	NPD6309	Approved
0.6494	Remote Similarity	NPD6310	Approved
0.6494	Remote Similarity	NPD6311	Approved
0.6494	Remote Similarity	NPD5121	Approved
0.6493	Remote Similarity	NPD2066	Phase 3
0.6491	Remote Similarity	NPD7795	Phase 2
0.649	Remote Similarity	NPD3636	Approved
0.649	Remote Similarity	NPD3635	Approved
0.649	Remote Similarity	NPD3637	Approved
0.6486	Remote Similarity	NPD4878	Approved
0.6483	Remote Similarity	NPD998	Approved
0.6483	Remote Similarity	NPD1759	Phase 1
0.6478	Remote Similarity	NPD7179	Phase 2
0.6478	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD5031	Approved
0.6477	Remote Similarity	NPD5030	Phase 2
0.6477	Remote Similarity	NPD5029	Approved
0.6477	Remote Similarity	NPD5027	Approved
0.6467	Remote Similarity	NPD2628	Approved
0.6467	Remote Similarity	NPD2627	Approved
0.6467	Remote Similarity	NPD2159	Approved
0.6467	Remote Similarity	NPD2626	Approved
0.6467	Remote Similarity	NPD2625	Approved
0.6467	Remote Similarity	NPD2160	Approved
0.6463	Remote Similarity	NPD3023	Approved
0.6463	Remote Similarity	NPD3026	Approved
0.646	Remote Similarity	NPD7236	Approved
0.6457	Remote Similarity	NPD4956	Approved
0.6456	Remote Similarity	NPD2174	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD4617	Approved
0.6447	Remote Similarity	NPD4620	Approved
0.6447	Remote Similarity	NPD5201	Approved
0.6447	Remote Similarity	NPD5203	Approved
0.6446	Remote Similarity	NPD7193	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD6025	Phase 1
0.6441	Remote Similarity	NPD4954	Approved
0.6441	Remote Similarity	NPD36	Approved
0.6441	Remote Similarity	NPD5026	Approved
0.6441	Remote Similarity	NPD4955	Approved
0.6441	Remote Similarity	NPD5028	Approved
0.6441	Remote Similarity	NPD5034	Approved
0.6439	Remote Similarity	NPD4094	Approved
0.6438	Remote Similarity	NPD3024	Approved
0.6438	Remote Similarity	NPD5981	Approved
0.6438	Remote Similarity	NPD4093	Discontinued
0.6438	Remote Similarity	NPD3025	Approved
0.6438	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5236	Approved
0.6429	Remote Similarity	NPD5239	Approved
0.6429	Remote Similarity	NPD5235	Approved
0.6429	Remote Similarity	NPD1792	Phase 2
0.6429	Remote Similarity	NPD5240	Approved
0.6429	Remote Similarity	NPD5237	Approved
0.6424	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD5086	Approved
0.6419	Remote Similarity	NPD4218	Approved
0.6419	Remote Similarity	NPD4216	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