NPASS Compound

Structure

NPC187435 OpenBabel07101718202D 33 35 0 0 1 0 0 0 0 0999 V2000 5.0518 0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6680 0.8603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5259 0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9722 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0120 -2.3003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9722 -3.3679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8420 1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2098 -0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3679 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6839 0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8938 -0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1164 -0.8132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6839 -1.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0518 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4659 -0.0907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7358 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8420 -1.4583 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5259 -0.4861 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.6303 -1.6551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5777 -0.4861 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8420 -0.4861 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9722 -1.6839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6839 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5259 -1.4583 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7358 0.9722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0258 -2.5433 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9444 -1.6839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4981 -1.4583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4861 -2.5259 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6793 -1.4530 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 16 1 0 0 0 0 6 32 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 9 1 0 0 0 0 8 15 1 0 0 0 0 9 19 1 0 0 0 0 10 24 1 0 0 0 0 11 25 1 0 0 0 0 12 15 2 0 0 0 0 12 17 1 0 0 0 0 13 16 2 0 0 0 0 13 20 1 0 0 0 0 14 18 1 0 0 0 0 14 26 1 0 0 0 0 16 21 1 0 0 0 0 17 27 1 6 0 0 0 18 22 1 0 0 0 0 18 28 1 6 0 0 0 19 24 1 1 0 0 0 19 26 1 0 0 0 0 20 29 2 0 0 0 0 20 33 1 0 0 0 0 21 17 1 6 0 0 0 21 33 1 0 0 0 0 22 24 1 1 0 0 0 22 25 1 0 0 0 0 23 25 1 0 0 0 0 23 30 2 0 0 0 0 23 32 1 0 0 0 0 24 3 1 1 0 0 0 25 4 1 1 0 0 0 26 5 1 1 0 0 0 26 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	464.28
Volume:	483.568
LogP:	2.986
LogD:	2.968
LogS:	-4.032
# Rotatable Bonds:	7
TPSA:	120.36
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.368
Synthetic Accessibility Score:	5.193
Fsp3:	0.731
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.131
MDCK Permeability:	1.3170556485420093e-05
Pgp-inhibitor:	0.036
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.716
20% Bioavailability (F20%):	0.167
30% Bioavailability (F30%):	0.892

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.66
Plasma Protein Binding (PPB):	90.98091888427734%
Volume Distribution (VD):	0.821
Pgp-substrate:	10.135001182556152%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.855
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.814
CYP2C9-inhibitor:	0.132
CYP2C9-substrate:	0.494
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.16
CYP3A4-inhibitor:	0.777
CYP3A4-substrate:	0.333

ADMET: Excretion

Clearance (CL):	7.613
Half-life (T1/2):	0.76

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.459
Drug-inuced Liver Injury (DILI):	0.245
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.123
Maximum Recommended Daily Dose:	0.751
Skin Sensitization:	0.233
Carcinogencity:	0.044
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.886

Download Data

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

Natural Product: NPC187435

Natural Product ID:	NPC187435
*Common Name:**	6Alpha,8Alpha,15(S)-Trihydroxy-23-Carbossimethyllabd-13(14),17-Dien-16(S),19-Olide
IUPAC Name:	methyl (1R,4aS,5R,6R,8S,8aR)-6,8-dihydroxy-5-[(E,5S)-5-hydroxy-3-methyl-5-[(2S)-3-methyl-5-oxo-2H-furan-2-yl]pent-3-enyl]-1,4a,6-trimethyl-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylate
Synonyms:
Standard InCHIKey:	XTBDCOLQKPTUSD-LJEPAFQVSA-N
Standard InCHI:	InChI=1S/C26H40O7/c1-15(12-17(27)21-16(2)13-20(29)33-21)8-9-19-24(3)10-7-11-25(4,23(30)32-6)22(24)18(28)14-26(19,5)31/h12-13,17-19,21-22,27-28,31H,7-11,14H2,1-6H3/b15-12+/t17-,18-,19+,21-,22+,24+,25+,26+/m0/s1
SMILES:	COC(=O)[C@]1(C)CCC[C@]2([C@H]1[C@@H](O)C[C@@]([C@@H]2CC/C(=C/[C@@H]([C@H]1OC(=O)C=C1C)O)/C)(C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL497636
PubChem CID:	44157608
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids

*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
NPO33075	salvia dominica	Species	Lamiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[19459643]
NPO40338	Salvia tingitana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32182064]

☑ 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
Kd	1
MIC	22

Activity Type	# Activity
Individual Protein	1
Organism	22

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6478	Individual Protein	Tubulin--tyrosine ligase	Homo sapiens	Kd	=	6200.0	nM	PMID[526025]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	276000.0	nM	PMID[526026]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[526026]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	276000.0	nM	PMID[526026]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	128.0	ug.mL-1	PMID[526026]
NPT1863	Organism	Staphylococcus saprophyticus	Staphylococcus saprophyticus	MIC	>	128.0	ug.mL-1	PMID[526026]
NPT3599	Organism	Staphylococcus capitis	Staphylococcus capitis	MIC	=	276000.0	nM	PMID[526026]
NPT5312	Organism	Staphylococcus warneri	Staphylococcus warneri	MIC	=	138000.0	nM	PMID[526026]
NPT4427	Organism	Staphylococcus simulans	Staphylococcus simulans	MIC	>	128.0	ug.mL-1	PMID[526026]
NPT4840	Organism	Staphylococcus lugdunensis	Staphylococcus lugdunensis	MIC	>	128.0	ug.mL-1	PMID[526026]
NPT1477	Organism	Staphylococcus haemolyticus	Staphylococcus haemolyticus	MIC	=	276000.0	nM	PMID[526026]
NPT4025	Organism	Staphylococcus hominis	Staphylococcus hominis	MIC	=	138000.0	nM	PMID[526026]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	138000.0	nM	PMID[526026]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	276000.0	nM	PMID[526026]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	276000.0	nM	PMID[526026]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	138000.0	nM	PMID[526026]
NPT4075	Organism	Enterococcus avium	Enterococcus avium	MIC	=	138000.0	nM	PMID[526026]
NPT23872	ORGANISM	Enterococcus casseliflavus	Enterococcus casseliflavus	MIC	=	276000.0	nM	PMID[526026]
NPT3730	Organism	Enterococcus durans	Enterococcus durans	MIC	=	138000.0	nM	PMID[526026]
NPT4844	Organism	Enterococcus gallinarum	Enterococcus gallinarum	MIC	=	276000.0	nM	PMID[526026]

☑ 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 NPC187435 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	205
0.1-0.2	1185
0.2-0.3	3593
0.3-0.4	6173
0.4-0.5	12747
0.5-0.6	8231
0.6-0.7	6462
0.7-0.8	3617
0.8-0.85	423
0.85-0.9	50
0.9-0.95	6
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC67321
0.97	High Similarity	NPC306265
0.9592	High Similarity	NPC476081
0.9388	High Similarity	NPC38855
0.93	High Similarity	NPC120321
0.9118	High Similarity	NPC34768
0.91	High Similarity	NPC303559
0.898	High Similarity	NPC276110
0.8922	High Similarity	NPC159533
0.8889	High Similarity	NPC134072
0.8889	High Similarity	NPC234993
0.8857	High Similarity	NPC173905
0.8857	High Similarity	NPC472216
0.8857	High Similarity	NPC284828
0.8857	High Similarity	NPC5475
0.8846	High Similarity	NPC179380
0.8846	High Similarity	NPC143609
0.8824	High Similarity	NPC472552
0.8824	High Similarity	NPC295791
0.8812	High Similarity	NPC47024
0.8785	High Similarity	NPC269530
0.8785	High Similarity	NPC470063
0.8776	High Similarity	NPC53555
0.8762	High Similarity	NPC38948
0.875	High Similarity	NPC111952
0.8738	High Similarity	NPC99266
0.8725	High Similarity	NPC471412
0.8725	High Similarity	NPC472554
0.8716	High Similarity	NPC471816
0.8692	High Similarity	NPC469655
0.8692	High Similarity	NPC469656
0.8692	High Similarity	NPC474846
0.8679	High Similarity	NPC206618
0.8667	High Similarity	NPC302788
0.8654	High Similarity	NPC146731
0.8654	High Similarity	NPC296950
0.8641	High Similarity	NPC137430
0.8641	High Similarity	NPC162973
0.8641	High Similarity	NPC165250
0.8627	High Similarity	NPC471413
0.8611	High Similarity	NPC472002
0.8598	High Similarity	NPC5103
0.8586	High Similarity	NPC139692
0.8585	High Similarity	NPC472218
0.8585	High Similarity	NPC151393
0.8585	High Similarity	NPC472217
0.8585	High Similarity	NPC472219
0.8571	High Similarity	NPC78973
0.8558	High Similarity	NPC8196
0.8558	High Similarity	NPC61442
0.8558	High Similarity	NPC471208
0.8558	High Similarity	NPC23584
0.8545	High Similarity	NPC471127
0.8545	High Similarity	NPC154363
0.8545	High Similarity	NPC234858
0.8544	High Similarity	NPC11974
0.8544	High Similarity	NPC97435
0.8532	High Similarity	NPC469454
0.8532	High Similarity	NPC469463
0.8532	High Similarity	NPC477126
0.8532	High Similarity	NPC471204
0.8532	High Similarity	NPC469496
0.8529	High Similarity	NPC124512
0.8529	High Similarity	NPC216478
0.8529	High Similarity	NPC222303
0.8529	High Similarity	NPC159763
0.8529	High Similarity	NPC278386
0.8529	High Similarity	NPC278673
0.8519	High Similarity	NPC473921
0.8519	High Similarity	NPC475668
0.8519	High Similarity	NPC317107
0.8519	High Similarity	NPC475480
0.8515	High Similarity	NPC242848
0.8509	High Similarity	NPC67251
0.8505	High Similarity	NPC299590
0.8505	High Similarity	NPC273433
0.8505	High Similarity	NPC42662
0.8505	High Similarity	NPC475065
0.85	High Similarity	NPC57117
0.85	High Similarity	NPC105490
0.85	High Similarity	NPC24861
0.8496	Intermediate Similarity	NPC67569
0.8491	Intermediate Similarity	NPC329048
0.8491	Intermediate Similarity	NPC330011
0.8491	Intermediate Similarity	NPC471205
0.8491	Intermediate Similarity	NPC475176
0.8482	Intermediate Similarity	NPC475041
0.8476	Intermediate Similarity	NPC258532
0.8468	Intermediate Similarity	NPC473590
0.8468	Intermediate Similarity	NPC473968
0.8468	Intermediate Similarity	NPC58662
0.8468	Intermediate Similarity	NPC13713
0.8468	Intermediate Similarity	NPC469684
0.8468	Intermediate Similarity	NPC10721
0.8462	Intermediate Similarity	NPC109195
0.8462	Intermediate Similarity	NPC11956
0.8462	Intermediate Similarity	NPC472815
0.8462	Intermediate Similarity	NPC475038
0.8455	Intermediate Similarity	NPC472400
0.844	Intermediate Similarity	NPC42658
0.844	Intermediate Similarity	NPC317687
0.8431	Intermediate Similarity	NPC121402
0.8431	Intermediate Similarity	NPC151681
0.8431	Intermediate Similarity	NPC473963
0.8431	Intermediate Similarity	NPC132753
0.8431	Intermediate Similarity	NPC73911
0.8431	Intermediate Similarity	NPC175351
0.8431	Intermediate Similarity	NPC224356
0.8426	Intermediate Similarity	NPC475563
0.8426	Intermediate Similarity	NPC478211
0.8426	Intermediate Similarity	NPC472214
0.8426	Intermediate Similarity	NPC235014
0.8426	Intermediate Similarity	NPC475134
0.8426	Intermediate Similarity	NPC472215
0.8426	Intermediate Similarity	NPC177047
0.8421	Intermediate Similarity	NPC470265
0.8421	Intermediate Similarity	NPC23786
0.8416	Intermediate Similarity	NPC259042
0.8416	Intermediate Similarity	NPC157686
0.8416	Intermediate Similarity	NPC53565
0.8411	Intermediate Similarity	NPC275539
0.8411	Intermediate Similarity	NPC475418
0.8411	Intermediate Similarity	NPC50124
0.8411	Intermediate Similarity	NPC318363
0.8411	Intermediate Similarity	NPC189075
0.8411	Intermediate Similarity	NPC88701
0.8411	Intermediate Similarity	NPC469916
0.8411	Intermediate Similarity	NPC325054
0.8411	Intermediate Similarity	NPC181994
0.8411	Intermediate Similarity	NPC473482
0.8411	Intermediate Similarity	NPC472439
0.8407	Intermediate Similarity	NPC475885
0.84	Intermediate Similarity	NPC110022
0.84	Intermediate Similarity	NPC7349
0.8396	Intermediate Similarity	NPC475414
0.8396	Intermediate Similarity	NPC477125
0.8396	Intermediate Similarity	NPC173172
0.8393	Intermediate Similarity	NPC124676
0.8393	Intermediate Similarity	NPC146280
0.8393	Intermediate Similarity	NPC709
0.8393	Intermediate Similarity	NPC50774
0.8381	Intermediate Similarity	NPC72842
0.8381	Intermediate Similarity	NPC474822
0.8381	Intermediate Similarity	NPC112009
0.8381	Intermediate Similarity	NPC99510
0.8381	Intermediate Similarity	NPC478057
0.8378	Intermediate Similarity	NPC474734
0.8365	Intermediate Similarity	NPC308824
0.8364	Intermediate Similarity	NPC25909
0.8364	Intermediate Similarity	NPC250109
0.8364	Intermediate Similarity	NPC472757
0.8362	Intermediate Similarity	NPC293112
0.835	Intermediate Similarity	NPC275086
0.835	Intermediate Similarity	NPC325229
0.835	Intermediate Similarity	NPC316598
0.8349	Intermediate Similarity	NPC100329
0.8349	Intermediate Similarity	NPC247031
0.8349	Intermediate Similarity	NPC179798
0.8349	Intermediate Similarity	NPC132790
0.8349	Intermediate Similarity	NPC97939
0.8349	Intermediate Similarity	NPC304180
0.8349	Intermediate Similarity	NPC324683
0.8348	Intermediate Similarity	NPC473979
0.8348	Intermediate Similarity	NPC469789
0.8333	Intermediate Similarity	NPC93245
0.8333	Intermediate Similarity	NPC284518
0.8333	Intermediate Similarity	NPC472362
0.8333	Intermediate Similarity	NPC87335
0.8333	Intermediate Similarity	NPC29952
0.8333	Intermediate Similarity	NPC202833
0.8333	Intermediate Similarity	NPC474243
0.8333	Intermediate Similarity	NPC154526
0.8333	Intermediate Similarity	NPC165632
0.8333	Intermediate Similarity	NPC473964
0.8333	Intermediate Similarity	NPC472363
0.8319	Intermediate Similarity	NPC469380
0.8319	Intermediate Similarity	NPC156745
0.8319	Intermediate Similarity	NPC236918
0.8318	Intermediate Similarity	NPC301666
0.8318	Intermediate Similarity	NPC473284
0.8318	Intermediate Similarity	NPC180744
0.8318	Intermediate Similarity	NPC110496
0.8318	Intermediate Similarity	NPC230541
0.8318	Intermediate Similarity	NPC255387
0.8318	Intermediate Similarity	NPC131665
0.8318	Intermediate Similarity	NPC122816
0.8317	Intermediate Similarity	NPC225474
0.8317	Intermediate Similarity	NPC469596
0.8317	Intermediate Similarity	NPC148000
0.8304	Intermediate Similarity	NPC98249
0.8304	Intermediate Similarity	NPC470493
0.8304	Intermediate Similarity	NPC470492
0.8304	Intermediate Similarity	NPC167606
0.8304	Intermediate Similarity	NPC286528
0.8304	Intermediate Similarity	NPC312824
0.8304	Intermediate Similarity	NPC183580
0.8304	Intermediate Similarity	NPC284068
0.8304	Intermediate Similarity	NPC55296
0.8304	Intermediate Similarity	NPC474483
0.8304	Intermediate Similarity	NPC475323

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 NPC187435 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	1462
0.2-0.3	3393
0.3-0.4	2513
0.4-0.5	1019
0.5-0.6	296
0.6-0.7	212
0.7-0.8	70
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8529	High Similarity	NPD4225	Approved
0.8505	High Similarity	NPD4061	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD7115	Discovery
0.8269	Intermediate Similarity	NPD7640	Approved
0.8269	Intermediate Similarity	NPD7639	Approved
0.8257	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.8241	Intermediate Similarity	NPD6686	Approved
0.8173	Intermediate Similarity	NPD7638	Approved
0.7982	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD7507	Approved
0.7851	Intermediate Similarity	NPD7319	Approved
0.785	Intermediate Similarity	NPD5344	Discontinued
0.7759	Intermediate Similarity	NPD7327	Approved
0.7759	Intermediate Similarity	NPD7328	Approved
0.7748	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7516	Approved
0.767	Intermediate Similarity	NPD46	Approved
0.767	Intermediate Similarity	NPD6698	Approved
0.7615	Intermediate Similarity	NPD7632	Discontinued
0.7611	Intermediate Similarity	NPD6371	Approved
0.7576	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD7902	Approved
0.7568	Intermediate Similarity	NPD6402	Approved
0.7568	Intermediate Similarity	NPD7128	Approved
0.7568	Intermediate Similarity	NPD5739	Approved
0.7568	Intermediate Similarity	NPD6675	Approved
0.7563	Intermediate Similarity	NPD8380	Approved
0.7563	Intermediate Similarity	NPD8335	Approved
0.7563	Intermediate Similarity	NPD8379	Approved
0.7563	Intermediate Similarity	NPD8378	Approved
0.7563	Intermediate Similarity	NPD8296	Approved
0.7563	Intermediate Similarity	NPD8033	Approved
0.7524	Intermediate Similarity	NPD6399	Phase 3
0.7522	Intermediate Similarity	NPD6372	Approved
0.7522	Intermediate Similarity	NPD6373	Approved
0.7479	Intermediate Similarity	NPD8294	Approved
0.7479	Intermediate Similarity	NPD8377	Approved
0.7478	Intermediate Similarity	NPD8297	Approved
0.7453	Intermediate Similarity	NPD7748	Approved
0.7434	Intermediate Similarity	NPD6881	Approved
0.7434	Intermediate Similarity	NPD6899	Approved
0.7434	Intermediate Similarity	NPD7320	Approved
0.7431	Intermediate Similarity	NPD6648	Approved
0.7429	Intermediate Similarity	NPD7515	Phase 2
0.7414	Intermediate Similarity	NPD4632	Approved
0.7391	Intermediate Similarity	NPD6649	Approved
0.7391	Intermediate Similarity	NPD6650	Approved
0.7345	Intermediate Similarity	NPD6412	Phase 2
0.7345	Intermediate Similarity	NPD5701	Approved
0.7345	Intermediate Similarity	NPD5697	Approved
0.7333	Intermediate Similarity	NPD6319	Approved
0.7304	Intermediate Similarity	NPD7102	Approved
0.7304	Intermediate Similarity	NPD7290	Approved
0.7304	Intermediate Similarity	NPD6883	Approved
0.729	Intermediate Similarity	NPD7900	Approved
0.729	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD3618	Phase 1
0.7265	Intermediate Similarity	NPD8133	Approved
0.7264	Intermediate Similarity	NPD7637	Suspended
0.7257	Intermediate Similarity	NPD6008	Approved
0.7248	Intermediate Similarity	NPD6084	Phase 2
0.7248	Intermediate Similarity	NPD6083	Phase 2
0.7241	Intermediate Similarity	NPD8130	Phase 1
0.7241	Intermediate Similarity	NPD6847	Approved
0.7241	Intermediate Similarity	NPD6617	Approved
0.7241	Intermediate Similarity	NPD6869	Approved
0.7217	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD6012	Approved
0.7217	Intermediate Similarity	NPD6013	Approved
0.7217	Intermediate Similarity	NPD6014	Approved
0.7212	Intermediate Similarity	NPD7524	Approved
0.7196	Intermediate Similarity	NPD5778	Approved
0.7196	Intermediate Similarity	NPD5779	Approved
0.7193	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD1694	Approved
0.7179	Intermediate Similarity	NPD6053	Discontinued
0.7179	Intermediate Similarity	NPD6882	Approved
0.7154	Intermediate Similarity	NPD8328	Phase 3
0.7143	Intermediate Similarity	NPD5211	Phase 2
0.7131	Intermediate Similarity	NPD8513	Phase 3
0.7131	Intermediate Similarity	NPD8516	Approved
0.7131	Intermediate Similarity	NPD7503	Approved
0.7131	Intermediate Similarity	NPD8515	Approved
0.7131	Intermediate Similarity	NPD8517	Approved
0.713	Intermediate Similarity	NPD6011	Approved
0.7103	Intermediate Similarity	NPD8034	Phase 2
0.7103	Intermediate Similarity	NPD8035	Phase 2
0.7097	Intermediate Similarity	NPD7492	Approved
0.7094	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4755	Approved
0.7087	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6009	Approved
0.7075	Intermediate Similarity	NPD5328	Approved
0.7049	Intermediate Similarity	NPD6054	Approved
0.7049	Intermediate Similarity	NPD6059	Approved
0.704	Intermediate Similarity	NPD6616	Approved
0.7037	Intermediate Similarity	NPD4202	Approved
0.7027	Intermediate Similarity	NPD5696	Approved
0.7027	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5141	Approved
0.7016	Intermediate Similarity	NPD7604	Phase 2
0.7009	Intermediate Similarity	NPD4634	Approved
0.7009	Intermediate Similarity	NPD7838	Discovery
0.7009	Intermediate Similarity	NPD5785	Approved
0.6992	Remote Similarity	NPD5983	Phase 2
0.6992	Remote Similarity	NPD6921	Approved
0.699	Remote Similarity	NPD6695	Phase 3
0.6984	Remote Similarity	NPD7078	Approved
0.6984	Remote Similarity	NPD8293	Discontinued
0.6964	Remote Similarity	NPD5286	Approved
0.6964	Remote Similarity	NPD4700	Approved
0.6964	Remote Similarity	NPD4696	Approved
0.6964	Remote Similarity	NPD5285	Approved
0.6952	Remote Similarity	NPD6409	Approved
0.6952	Remote Similarity	NPD7146	Approved
0.6952	Remote Similarity	NPD7521	Approved
0.6952	Remote Similarity	NPD5330	Approved
0.6952	Remote Similarity	NPD6684	Approved
0.6952	Remote Similarity	NPD7334	Approved
0.6944	Remote Similarity	NPD7983	Approved
0.6944	Remote Similarity	NPD6079	Approved
0.6942	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6370	Approved
0.6929	Remote Similarity	NPD7736	Approved
0.6923	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4786	Approved
0.6909	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5695	Phase 3
0.6905	Remote Similarity	NPD6336	Discontinued
0.6893	Remote Similarity	NPD3667	Approved
0.686	Remote Similarity	NPD6274	Approved
0.6857	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6016	Approved
0.6855	Remote Similarity	NPD6015	Approved
0.685	Remote Similarity	NPD8074	Phase 3
0.6847	Remote Similarity	NPD4697	Phase 3
0.6842	Remote Similarity	NPD4633	Approved
0.6842	Remote Similarity	NPD5226	Approved
0.6842	Remote Similarity	NPD5224	Approved
0.6842	Remote Similarity	NPD5225	Approved
0.6829	Remote Similarity	NPD7100	Approved
0.6829	Remote Similarity	NPD7101	Approved
0.6822	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5737	Approved
0.6822	Remote Similarity	NPD6903	Approved
0.6822	Remote Similarity	NPD6672	Approved
0.68	Remote Similarity	NPD5988	Approved
0.6789	Remote Similarity	NPD6411	Approved
0.6789	Remote Similarity	NPD5693	Phase 1
0.6783	Remote Similarity	NPD5174	Approved
0.6783	Remote Similarity	NPD5175	Approved
0.6762	Remote Similarity	NPD3666	Approved
0.6762	Remote Similarity	NPD3665	Phase 1
0.6762	Remote Similarity	NPD3133	Approved
0.6759	Remote Similarity	NPD4753	Phase 2
0.6754	Remote Similarity	NPD5223	Approved
0.6748	Remote Similarity	NPD6335	Approved
0.6729	Remote Similarity	NPD3573	Approved
0.6729	Remote Similarity	NPD7750	Discontinued
0.672	Remote Similarity	NPD6909	Approved
0.672	Remote Similarity	NPD6908	Approved
0.6699	Remote Similarity	NPD6931	Approved
0.6699	Remote Similarity	NPD7525	Registered
0.6699	Remote Similarity	NPD6930	Phase 2
0.6696	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5222	Approved
0.6696	Remote Similarity	NPD5221	Approved
0.6667	Remote Similarity	NPD4767	Approved
0.6667	Remote Similarity	NPD4768	Approved
0.6667	Remote Similarity	NPD5282	Discontinued
0.6667	Remote Similarity	NPD6317	Approved
0.6667	Remote Similarity	NPD7154	Phase 3
0.6641	Remote Similarity	NPD7260	Phase 2
0.6638	Remote Similarity	NPD4754	Approved
0.6637	Remote Similarity	NPD5173	Approved
0.6636	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5284	Approved
0.6636	Remote Similarity	NPD4623	Approved
0.6636	Remote Similarity	NPD5281	Approved
0.6636	Remote Similarity	NPD4519	Discontinued
0.6614	Remote Similarity	NPD6067	Discontinued
0.6613	Remote Similarity	NPD6313	Approved
0.6613	Remote Similarity	NPD6314	Approved
0.6607	Remote Similarity	NPD5210	Approved
0.6607	Remote Similarity	NPD4629	Approved
0.6606	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6101	Approved
0.6606	Remote Similarity	NPD6904	Approved
0.6606	Remote Similarity	NPD6673	Approved
0.6606	Remote Similarity	NPD6080	Approved
0.6606	Remote Similarity	NPD6051	Approved
0.6602	Remote Similarity	NPD6929	Approved
0.6587	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6868	Approved
0.6555	Remote Similarity	NPD4729	Approved
0.6555	Remote Similarity	NPD5128	Approved
0.6555	Remote Similarity	NPD4730	Approved
0.6542	Remote Similarity	NPD1733	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