NPASS Compound

Structure

CID241085 OpenBabel06191716042D 33 37 0 0 1 0 0 0 0 0999 V2000 -1.8862 3.1656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6925 -2.9627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5662 -2.4581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7777 5.3545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9803 4.3998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6928 1.9851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6920 -1.0097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4938 2.6428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 -1.9540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8457 -1.4657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7956 3.5709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3836 0.9754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5373 -0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3833 -0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6917 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8465 1.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8460 0.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5391 2.4401 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5388 1.4642 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8465 -1.4652 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8460 -0.4887 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5376 -1.4647 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7504 3.7736 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6922 -1.9535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0522 4.7017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6925 0.9759 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6922 -0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8463 -0.4882 0.0000 C 0 0 1 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 3.4038 -1.9644 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4032 3.0481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3994 5.4272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 8 11 1 0 0 0 0 8 19 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 24 1 0 0 0 0 12 14 1 0 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 13 23 1 0 0 0 0 14 28 1 0 0 0 0 15 29 1 0 0 0 0 16 17 1 0 0 0 0 16 27 1 0 0 0 0 18 29 1 0 0 0 0 18 30 1 0 0 0 0 19 1 1 1 0 0 0 19 20 1 0 0 0 0 20 27 1 6 0 0 0 21 25 1 0 0 0 0 21 29 1 6 0 0 0 22 28 1 1 0 0 0 22 30 1 0 0 0 0 23 25 1 0 0 0 0 23 31 1 6 0 0 0 24 26 1 0 0 0 0 24 32 1 1 0 0 0 26 33 1 0 0 0 0 27 28 1 6 0 0 0 28 7 1 1 0 0 0 29 30 1 1 0 0 0 30 17 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.39
Volume:	511.024
LogP:	5.89
LogD:	4.826
LogS:	-4.24
# Rotatable Bonds:	5
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.449
Synthetic Accessibility Score:	5.536
Fsp3:	1.0
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:	-5.014
MDCK Permeability:	1.4411369193112478e-05
Pgp-inhibitor:	0.125
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.836
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.096
Plasma Protein Binding (PPB):	95.40259552001953%
Volume Distribution (VD):	1.143
Pgp-substrate:	1.8555673360824585%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.224
CYP2C19-inhibitor:	0.037
CYP2C19-substrate:	0.921
CYP2C9-inhibitor:	0.162
CYP2C9-substrate:	0.293
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.283
CYP3A4-inhibitor:	0.651
CYP3A4-substrate:	0.462

ADMET: Excretion

Clearance (CL):	5.699
Half-life (T1/2):	0.105

ADMET: Toxicity

hERG Blockers:	0.082
Human Hepatotoxicity (H-HT):	0.326
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.951
Maximum Recommended Daily Dose:	0.954
Skin Sensitization:	0.934
Carcinogencity:	0.053
Eye Corrosion:	0.147
Eye Irritation:	0.128
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC241085

Natural Product ID:	NPC241085
*Common Name:**	BKRIPHYESIGPJC-LEDYUWLESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BKRIPHYESIGPJC-LEDYUWLESA-N
Standard InCHI:	InChI=1S/C30H52O3/c1-19(8-11-24(32)26(4,5)33)20-12-14-28(7)22-10-9-21-25(2,3)23(31)13-15-29(21)18-30(22,29)17-16-27(20,28)6/h19-24,31-33H,8-18H2,1-7H3/t19-,20-,21+,22+,23+,24-,27-,28+,29-,30+/m1/s1
SMILES:	C[C@H](CC[C@H](C(C)(C)O)O)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4C(C)(C)[C@H](CC[C@]54C[C@@]35CC[C@]12C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL225922
PubChem CID:	5270670
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols 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
NPO6329	Abies chensiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19435338]
NPO6329	Abies chensiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31557016]
NPO819	Heliotropium olgae	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO819	Heliotropium olgae	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2633	Baccharis minutiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9750	Dysoxylum malabaricum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO819	Heliotropium olgae	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6329	Abies chensiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4668	Sideritis flavovirens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4372	Halimium halimifolium	Species	Cistaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7674	Tragopogon orientalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7856	Streptomyces halstedii	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2480	Amoora rohituka	n.a.	n.a.	n.a.	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
MIC	4
Others	6

Activity Type	# Activity
Cell Line	1
Organism	9
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[453235]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	0.0	%	PMID[453235]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	20.4	%	PMID[453235]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	68.3	%	PMID[453235]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	87.0	%	PMID[453235]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	IC50	=	7.3	nM	PMID[453235]
NPT2	Others	Unspecified		Activity	=	2.1	n.a.	PMID[453235]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	40.0	ug.mL-1	PMID[453236]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	40.0	ug.mL-1	PMID[453236]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	40.0	ug.mL-1	PMID[453236]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	40.0	ug.mL-1	PMID[453236]

☑ 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 NPC241085 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	388
0.1-0.2	4852
0.2-0.3	17456
0.3-0.4	8367
0.4-0.5	4797
0.5-0.6	4424
0.6-0.7	1816
0.7-0.8	442
0.8-0.85	85
0.85-0.9	52
0.9-0.95	12
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC299948
1.0	High Similarity	NPC470830
0.9552	High Similarity	NPC473238
0.9552	High Similarity	NPC472341
0.9394	High Similarity	NPC107919
0.9385	High Similarity	NPC475884
0.9385	High Similarity	NPC473230
0.9375	High Similarity	NPC474380
0.9375	High Similarity	NPC41577
0.9375	High Similarity	NPC473276
0.9254	High Similarity	NPC231945
0.9219	High Similarity	NPC69149
0.9118	High Similarity	NPC195530
0.9118	High Similarity	NPC473279
0.9091	High Similarity	NPC48079
0.9091	High Similarity	NPC63190
0.9062	High Similarity	NPC114891
0.8986	High Similarity	NPC153719
0.8955	High Similarity	NPC472741
0.8939	High Similarity	NPC142712
0.8906	High Similarity	NPC71460
0.8906	High Similarity	NPC148174
0.8906	High Similarity	NPC218585
0.8889	High Similarity	NPC147993
0.8873	High Similarity	NPC470145
0.8857	High Similarity	NPC10476
0.8857	High Similarity	NPC192501
0.8857	High Similarity	NPC228994
0.8841	High Similarity	NPC8004
0.8841	High Similarity	NPC131506
0.8841	High Similarity	NPC157777
0.8841	High Similarity	NPC127283
0.8824	High Similarity	NPC129829
0.8824	High Similarity	NPC66407
0.8824	High Similarity	NPC254037
0.8788	High Similarity	NPC243469
0.8788	High Similarity	NPC475943
0.8788	High Similarity	NPC260116
0.8788	High Similarity	NPC190827
0.8767	High Similarity	NPC287452
0.8732	High Similarity	NPC270306
0.8732	High Similarity	NPC158208
0.8732	High Similarity	NPC243027
0.8732	High Similarity	NPC231680
0.8732	High Similarity	NPC317242
0.8732	High Similarity	NPC196136
0.8732	High Similarity	NPC91387
0.8714	High Similarity	NPC470610
0.8696	High Similarity	NPC192192
0.8696	High Similarity	NPC282454
0.8657	High Similarity	NPC44122
0.8636	High Similarity	NPC167995
0.8636	High Similarity	NPC159654
0.8636	High Similarity	NPC118937
0.8636	High Similarity	NPC281540
0.8615	High Similarity	NPC185547
0.8615	High Similarity	NPC95804
0.8611	High Similarity	NPC91573
0.8611	High Similarity	NPC163597
0.8594	High Similarity	NPC95958
0.8592	High Similarity	NPC478130
0.8592	High Similarity	NPC48795
0.8571	High Similarity	NPC109457
0.8571	High Similarity	NPC127094
0.8571	High Similarity	NPC100586
0.8571	High Similarity	NPC252182
0.8571	High Similarity	NPC1340
0.8571	High Similarity	NPC187471
0.8571	High Similarity	NPC157422
0.8571	High Similarity	NPC470071
0.8551	High Similarity	NPC477820
0.8533	High Similarity	NPC12933
0.8507	High Similarity	NPC472946
0.8493	Intermediate Similarity	NPC302578
0.8493	Intermediate Similarity	NPC64081
0.8493	Intermediate Similarity	NPC11907
0.8493	Intermediate Similarity	NPC474574
0.8493	Intermediate Similarity	NPC128951
0.8493	Intermediate Similarity	NPC133596
0.8493	Intermediate Similarity	NPC192046
0.8493	Intermediate Similarity	NPC185915
0.8493	Intermediate Similarity	NPC475031
0.8493	Intermediate Similarity	NPC477227
0.8493	Intermediate Similarity	NPC105208
0.8472	Intermediate Similarity	NPC230704
0.8472	Intermediate Similarity	NPC70982
0.8472	Intermediate Similarity	NPC273366
0.8438	Intermediate Similarity	NPC476735
0.8429	Intermediate Similarity	NPC63588
0.8429	Intermediate Similarity	NPC232925
0.8429	Intermediate Similarity	NPC251201
0.8421	Intermediate Similarity	NPC475388
0.8406	Intermediate Similarity	NPC475893
0.84	Intermediate Similarity	NPC16449
0.8378	Intermediate Similarity	NPC471769
0.8378	Intermediate Similarity	NPC472342
0.8378	Intermediate Similarity	NPC67657
0.8378	Intermediate Similarity	NPC18857
0.8356	Intermediate Similarity	NPC477601
0.8356	Intermediate Similarity	NPC473916
0.8356	Intermediate Similarity	NPC477602
0.8333	Intermediate Similarity	NPC49168
0.8333	Intermediate Similarity	NPC477508
0.8333	Intermediate Similarity	NPC304499
0.8333	Intermediate Similarity	NPC196358
0.8333	Intermediate Similarity	NPC145552
0.8333	Intermediate Similarity	NPC254509
0.8333	Intermediate Similarity	NPC5046
0.831	Intermediate Similarity	NPC478103
0.8286	Intermediate Similarity	NPC99264
0.8286	Intermediate Similarity	NPC470833
0.8281	Intermediate Similarity	NPC135438
0.8267	Intermediate Similarity	NPC81074
0.8267	Intermediate Similarity	NPC477282
0.8267	Intermediate Similarity	NPC269333
0.8261	Intermediate Similarity	NPC204233
0.8243	Intermediate Similarity	NPC331618
0.8243	Intermediate Similarity	NPC476233
0.8243	Intermediate Similarity	NPC264602
0.8243	Intermediate Similarity	NPC257191
0.8235	Intermediate Similarity	NPC80463
0.8219	Intermediate Similarity	NPC200243
0.8219	Intermediate Similarity	NPC3403
0.8194	Intermediate Similarity	NPC195489
0.8194	Intermediate Similarity	NPC232112
0.8158	Intermediate Similarity	NPC13554
0.8143	Intermediate Similarity	NPC474756
0.8133	Intermediate Similarity	NPC102708
0.8056	Intermediate Similarity	NPC111234
0.8056	Intermediate Similarity	NPC320549
0.8056	Intermediate Similarity	NPC151018
0.8056	Intermediate Similarity	NPC156277
0.8056	Intermediate Similarity	NPC58057
0.8	Intermediate Similarity	NPC236588
0.8	Intermediate Similarity	NPC23884
0.8	Intermediate Similarity	NPC171658
0.7973	Intermediate Similarity	NPC195155
0.7973	Intermediate Similarity	NPC185536
0.7973	Intermediate Similarity	NPC104387
0.7973	Intermediate Similarity	NPC212879
0.7973	Intermediate Similarity	NPC231256
0.7973	Intermediate Similarity	NPC174964
0.7973	Intermediate Similarity	NPC97534
0.7973	Intermediate Similarity	NPC240235
0.7973	Intermediate Similarity	NPC178383
0.7973	Intermediate Similarity	NPC212733
0.7973	Intermediate Similarity	NPC186851
0.7949	Intermediate Similarity	NPC202688
0.7949	Intermediate Similarity	NPC60018
0.7949	Intermediate Similarity	NPC154043
0.7941	Intermediate Similarity	NPC209686
0.7941	Intermediate Similarity	NPC292419
0.7941	Intermediate Similarity	NPC249078
0.7941	Intermediate Similarity	NPC290791
0.7941	Intermediate Similarity	NPC236099
0.7917	Intermediate Similarity	NPC45296
0.7901	Intermediate Similarity	NPC202937
0.7895	Intermediate Similarity	NPC302041
0.7895	Intermediate Similarity	NPC65897
0.7895	Intermediate Similarity	NPC31828
0.7895	Intermediate Similarity	NPC42853
0.7895	Intermediate Similarity	NPC301707
0.7895	Intermediate Similarity	NPC85346
0.7895	Intermediate Similarity	NPC285761
0.7879	Intermediate Similarity	NPC47663
0.7879	Intermediate Similarity	NPC162685
0.7867	Intermediate Similarity	NPC472486
0.7867	Intermediate Similarity	NPC93662
0.7867	Intermediate Similarity	NPC278091
0.7867	Intermediate Similarity	NPC472487
0.7867	Intermediate Similarity	NPC5767
0.7867	Intermediate Similarity	NPC78067
0.7867	Intermediate Similarity	NPC4209
0.7867	Intermediate Similarity	NPC86305
0.7867	Intermediate Similarity	NPC14112
0.7867	Intermediate Similarity	NPC475742
0.7848	Intermediate Similarity	NPC470070
0.7848	Intermediate Similarity	NPC134481
0.7848	Intermediate Similarity	NPC111582
0.7848	Intermediate Similarity	NPC211135
0.7848	Intermediate Similarity	NPC82623
0.7848	Intermediate Similarity	NPC216420
0.7848	Intermediate Similarity	NPC85095
0.7848	Intermediate Similarity	NPC207013
0.7848	Intermediate Similarity	NPC478054
0.7848	Intermediate Similarity	NPC477285
0.7838	Intermediate Similarity	NPC280026
0.7838	Intermediate Similarity	NPC25511
0.7838	Intermediate Similarity	NPC192638
0.7838	Intermediate Similarity	NPC472854
0.7838	Intermediate Similarity	NPC272359
0.7838	Intermediate Similarity	NPC62657
0.7838	Intermediate Similarity	NPC167702
0.7838	Intermediate Similarity	NPC472503
0.7838	Intermediate Similarity	NPC254340
0.7838	Intermediate Similarity	NPC308440
0.7821	Intermediate Similarity	NPC109533
0.7821	Intermediate Similarity	NPC190940
0.7821	Intermediate Similarity	NPC469745
0.7808	Intermediate Similarity	NPC89310

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 NPC241085 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	403
0.1-0.2	4510
0.2-0.3	3052
0.3-0.4	708
0.4-0.5	192
0.5-0.6	212
0.6-0.7	49
0.7-0.8	22
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9394	High Similarity	NPD4267	Clinical (unspecified phase)
0.8429	Intermediate Similarity	NPD4787	Phase 1
0.8056	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD6117	Approved
0.7838	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD6116	Phase 1
0.7692	Intermediate Similarity	NPD7525	Registered
0.7662	Intermediate Similarity	NPD6114	Approved
0.7662	Intermediate Similarity	NPD6115	Approved
0.7662	Intermediate Similarity	NPD6697	Approved
0.7662	Intermediate Similarity	NPD6118	Approved
0.7639	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD5360	Phase 3
0.75	Intermediate Similarity	NPD3703	Phase 2
0.7432	Intermediate Similarity	NPD4244	Approved
0.7432	Intermediate Similarity	NPD4245	Approved
0.7432	Intermediate Similarity	NPD4789	Approved
0.7297	Intermediate Similarity	NPD3698	Phase 2
0.725	Intermediate Similarity	NPD6928	Phase 2
0.7222	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4758	Discontinued
0.7051	Intermediate Similarity	NPD7339	Approved
0.7051	Intermediate Similarity	NPD6942	Approved
0.7024	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3671	Phase 1
0.6962	Remote Similarity	NPD6933	Approved
0.6933	Remote Similarity	NPD6705	Phase 1
0.6829	Remote Similarity	NPD4748	Discontinued
0.679	Remote Similarity	NPD5364	Discontinued
0.675	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD385	Approved
0.6719	Remote Similarity	NPD384	Approved
0.6709	Remote Similarity	NPD6924	Approved
0.6709	Remote Similarity	NPD6926	Approved
0.6707	Remote Similarity	NPD7645	Phase 2
0.6667	Remote Similarity	NPD6081	Approved
0.6667	Remote Similarity	NPD4224	Phase 2
0.6667	Remote Similarity	NPD8171	Discontinued
0.6629	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6700	Approved
0.6625	Remote Similarity	NPD3702	Approved
0.6622	Remote Similarity	NPD371	Approved
0.6588	Remote Similarity	NPD4788	Approved
0.6556	Remote Similarity	NPD6702	Approved
0.6556	Remote Similarity	NPD6703	Approved
0.6517	Remote Similarity	NPD5328	Approved
0.6512	Remote Similarity	NPD4786	Approved
0.6456	Remote Similarity	NPD4243	Approved
0.6456	Remote Similarity	NPD5777	Approved
0.6374	Remote Similarity	NPD8034	Phase 2
0.6374	Remote Similarity	NPD8035	Phase 2
0.6374	Remote Similarity	NPD6079	Approved
0.6364	Remote Similarity	NPD3618	Phase 1
0.6304	Remote Similarity	NPD4202	Approved
0.6296	Remote Similarity	NPD4785	Approved
0.6296	Remote Similarity	NPD4784	Approved
0.6292	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD3667	Approved
0.625	Remote Similarity	NPD7151	Approved
0.625	Remote Similarity	NPD7150	Approved
0.625	Remote Similarity	NPD7152	Approved
0.6235	Remote Similarity	NPD7509	Discontinued
0.6235	Remote Similarity	NPD6931	Approved
0.6235	Remote Similarity	NPD6930	Phase 2
0.6211	Remote Similarity	NPD7920	Phase 3
0.6211	Remote Similarity	NPD7919	Phase 3
0.6203	Remote Similarity	NPD6922	Approved
0.6203	Remote Similarity	NPD6923	Approved
0.6186	Remote Similarity	NPD4159	Approved
0.618	Remote Similarity	NPD8308	Discontinued
0.6146	Remote Similarity	NPD8088	Phase 1
0.6125	Remote Similarity	NPD7144	Approved
0.6125	Remote Similarity	NPD7143	Approved
0.6118	Remote Similarity	NPD6929	Approved
0.6111	Remote Similarity	NPD7524	Approved
0.6082	Remote Similarity	NPD8418	Phase 2
0.6071	Remote Similarity	NPD6932	Approved
0.6061	Remote Similarity	NPD388	Approved
0.6061	Remote Similarity	NPD386	Approved
0.6042	Remote Similarity	NPD4755	Approved
0.6024	Remote Similarity	NPD5275	Approved
0.6024	Remote Similarity	NPD4190	Phase 3
0.6023	Remote Similarity	NPD6695	Phase 3
0.6	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7991	Discontinued
0.5979	Remote Similarity	NPD7638	Approved
0.5977	Remote Similarity	NPD6902	Approved
0.5955	Remote Similarity	NPD3666	Approved
0.5955	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD3133	Approved
0.5955	Remote Similarity	NPD3665	Phase 1
0.5938	Remote Similarity	NPD4697	Phase 3
0.5938	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD5222	Approved
0.5938	Remote Similarity	NPD5221	Approved
0.593	Remote Similarity	NPD4195	Approved
0.593	Remote Similarity	NPD6683	Phase 2
0.5918	Remote Similarity	NPD4696	Approved
0.5918	Remote Similarity	NPD5286	Approved
0.5918	Remote Similarity	NPD7639	Approved
0.5918	Remote Similarity	NPD7640	Approved
0.5918	Remote Similarity	NPD5285	Approved
0.5918	Remote Similarity	NPD4700	Approved
0.5904	Remote Similarity	NPD1811	Approved
0.5904	Remote Similarity	NPD1810	Approved
0.5889	Remote Similarity	NPD6893	Approved
0.5882	Remote Similarity	NPD5776	Phase 2
0.5882	Remote Similarity	NPD6925	Approved
0.5876	Remote Similarity	NPD5173	Approved
0.5862	Remote Similarity	NPD7514	Phase 3
0.5859	Remote Similarity	NPD5223	Approved
0.5851	Remote Similarity	NPD7515	Phase 2
0.5814	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD7145	Approved
0.5806	Remote Similarity	NPD4753	Phase 2
0.58	Remote Similarity	NPD5224	Approved
0.58	Remote Similarity	NPD5211	Phase 2
0.58	Remote Similarity	NPD7632	Discontinued
0.58	Remote Similarity	NPD5226	Approved
0.58	Remote Similarity	NPD4633	Approved
0.58	Remote Similarity	NPD5225	Approved
0.5789	Remote Similarity	NPD6399	Phase 3
0.5784	Remote Similarity	NPD6402	Approved
0.5784	Remote Similarity	NPD6675	Approved
0.5784	Remote Similarity	NPD7128	Approved
0.5784	Remote Similarity	NPD6920	Discontinued
0.5784	Remote Similarity	NPD5739	Approved
0.5761	Remote Similarity	NPD7750	Discontinued
0.5743	Remote Similarity	NPD5174	Approved
0.5743	Remote Similarity	NPD5175	Approved
0.5743	Remote Similarity	NPD4754	Approved
0.573	Remote Similarity	NPD4221	Approved
0.573	Remote Similarity	NPD4223	Phase 3
0.5714	Remote Similarity	NPD5329	Approved
0.5714	Remote Similarity	NPD4634	Approved
0.5688	Remote Similarity	NPD7115	Discovery
0.5686	Remote Similarity	NPD5141	Approved
0.5682	Remote Similarity	NPD7332	Phase 2
0.5673	Remote Similarity	NPD6881	Approved
0.5673	Remote Similarity	NPD7320	Approved
0.5673	Remote Similarity	NPD6899	Approved
0.5658	Remote Similarity	NPD3198	Approved
0.5657	Remote Similarity	NPD5290	Discontinued
0.5652	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD5279	Phase 3
0.5636	Remote Similarity	NPD7327	Approved
0.5636	Remote Similarity	NPD7328	Approved
0.5632	Remote Similarity	NPD3617	Approved
0.5631	Remote Similarity	NPD4768	Approved
0.5631	Remote Similarity	NPD4767	Approved
0.5619	Remote Similarity	NPD6373	Approved
0.5619	Remote Similarity	NPD6372	Approved
0.5618	Remote Similarity	NPD4692	Approved
0.5618	Remote Similarity	NPD4139	Approved
0.5618	Remote Similarity	NPD6898	Phase 1
0.5607	Remote Similarity	NPD8297	Approved
0.5604	Remote Similarity	NPD3668	Phase 3
0.5604	Remote Similarity	NPD4197	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