NPASS Compound

Structure

CID93181 OpenBabel06191715432D 22 24 0 0 1 0 0 0 0 0999 V2000 -2.4879 -1.4364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6586 -2.8728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3172 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5830 1.4467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9494 0.5620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1728 1.1728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6586 0.6870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4879 -1.4364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6586 -1.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4858 1.1728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6586 -1.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4879 -0.4788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8293 -1.4364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6586 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8293 -1.4364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8293 -0.4788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8293 -0.4788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.6870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6586 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 19 1 0 0 0 0 5 19 1 0 0 0 0 6 7 1 0 0 0 0 6 10 1 0 0 0 0 7 15 1 0 0 0 0 8 9 2 0 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 10 19 1 0 0 0 0 11 14 1 0 0 0 0 11 16 2 0 0 0 0 12 16 1 0 0 0 0 13 15 2 0 0 0 0 14 17 2 0 0 0 0 15 17 1 0 0 0 0 16 18 1 0 0 0 0 17 20 1 0 0 0 0 18 20 1 0 0 0 0 18 21 2 0 0 0 0 19 20 1 0 0 0 0 20 22 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.19
Volume:	333.205
LogP:	4.9
LogD:	3.976
LogS:	-5.251
# Rotatable Bonds:	1
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.845
Synthetic Accessibility Score:	3.561
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.906
MDCK Permeability:	2.152380875486415e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.64
30% Bioavailability (F30%):	0.564

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.263
Plasma Protein Binding (PPB):	96.27061462402344%
Volume Distribution (VD):	1.969
Pgp-substrate:	2.417584180831909%

ADMET: Metabolism

CYP1A2-inhibitor:	0.432
CYP1A2-substrate:	0.81
CYP2C19-inhibitor:	0.863
CYP2C19-substrate:	0.914
CYP2C9-inhibitor:	0.78
CYP2C9-substrate:	0.163
CYP2D6-inhibitor:	0.284
CYP2D6-substrate:	0.658
CYP3A4-inhibitor:	0.526
CYP3A4-substrate:	0.76

ADMET: Excretion

Clearance (CL):	1.257
Half-life (T1/2):	0.043

ADMET: Toxicity

hERG Blockers:	0.082
Human Hepatotoxicity (H-HT):	0.362
Drug-inuced Liver Injury (DILI):	0.164
AMES Toxicity:	0.284
Rat Oral Acute Toxicity:	0.119
Maximum Recommended Daily Dose:	0.91
Skin Sensitization:	0.164
Carcinogencity:	0.47
Eye Corrosion:	0.003
Eye Irritation:	0.037
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC93181

Natural Product ID:	NPC93181
*Common Name:**	KIXMQGXACFNMEM-FQEVSTJZSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KIXMQGXACFNMEM-FQEVSTJZSA-N
Standard InCHI:	InChI=1S/C20H26O2/c1-12(2)16-11-14-9-8-13(3)15-7-6-10-19(4,5)20(22,17(14)15)18(16)21/h8-9,11-12,22H,6-7,10H2,1-5H3/t20-/m0/s1
SMILES:	CC(C1=Cc2ccc(c3c2[C@@](C1=O)(O)C(C)(C)CCC3)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3814422
PubChem CID:	403772
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes

*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
NPO16570	Didemnum obscurum	Species	Didemnidae	Eukaryota	n.a.	Tiruchandur coast in the Gulf of Mannar, Tamilnadu, India	2002-FEB	PMID[15270574]
NPO19278	Taxodium distichum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17869103]
NPO13852	Pachysandra terminalis	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22804108]
NPO19278	Taxodium distichum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26905523]
NPO5795	Koelpinia linearis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2052	Hedyotis acutangula	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13852	Pachysandra terminalis	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21045	Salvia staminea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19278	Taxodium distichum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19278	Taxodium distichum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21045	Salvia staminea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2052	Hedyotis acutangula	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5795	Koelpinia linearis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15519	Lysimachia candida	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13852	Pachysandra terminalis	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13852	Pachysandra terminalis	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12898	Rhaphiolepis umbellata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15519	Lysimachia candida	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11191	Campylospermum flavum	Species	Ochnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19247	Viburnum jucundum	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19278	Taxodium distichum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13852	Pachysandra terminalis	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21044	Sphaerellopsis filum	Species	Leptosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14820	Petasites spurius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10233	Nicotiana trigonophylla	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19835	Melodorum oldhamii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22284	Acacia myrtifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2052	Hedyotis acutangula	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16334	Polystictus versicolor	Species	Tyrannidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27607	Saussurea candicans	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18607	Eria macrophylla	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16570	Didemnum obscurum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22377	Lechevalieria flava	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO18270	Betula divaricata	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21045	Salvia staminea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19313	Herniaria fontanesii	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5795	Koelpinia linearis	Species	Asteraceae	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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	>	10.0	ug.mL-1	PMID[513279]
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	IC50	>	10.0	ug.mL-1	PMID[513279]

☑ 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 NPC93181 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	245
0.1-0.2	1293
0.2-0.3	2659
0.3-0.4	8673
0.4-0.5	13506
0.5-0.6	11925
0.6-0.7	3784
0.7-0.8	563
0.8-0.85	37
0.85-0.9	9
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8909	High Similarity	NPC474057
0.8545	High Similarity	NPC100767
0.8496	Intermediate Similarity	NPC292834
0.844	Intermediate Similarity	NPC247976
0.8435	Intermediate Similarity	NPC186933
0.8421	Intermediate Similarity	NPC143768
0.8407	Intermediate Similarity	NPC95126
0.8407	Intermediate Similarity	NPC475002
0.8403	Intermediate Similarity	NPC472981
0.8333	Intermediate Similarity	NPC471188
0.8333	Intermediate Similarity	NPC269923
0.8333	Intermediate Similarity	NPC167323
0.8288	Intermediate Similarity	NPC172483
0.8197	Intermediate Similarity	NPC85511
0.8174	Intermediate Similarity	NPC66208
0.8136	Intermediate Similarity	NPC469843
0.812	Intermediate Similarity	NPC274839
0.8108	Intermediate Similarity	NPC274443
0.8095	Intermediate Similarity	NPC171460
0.8067	Intermediate Similarity	NPC323440
0.8067	Intermediate Similarity	NPC222968
0.8067	Intermediate Similarity	NPC80605
0.8065	Intermediate Similarity	NPC123506
0.8049	Intermediate Similarity	NPC273683
0.8036	Intermediate Similarity	NPC472222
0.8036	Intermediate Similarity	NPC472221
0.8034	Intermediate Similarity	NPC326664
0.8034	Intermediate Similarity	NPC471721
0.8033	Intermediate Similarity	NPC154696
0.8018	Intermediate Similarity	NPC244427
0.8018	Intermediate Similarity	NPC222390
0.8017	Intermediate Similarity	NPC471189
0.8	Intermediate Similarity	NPC474106
0.7983	Intermediate Similarity	NPC212891
0.7966	Intermediate Similarity	NPC221275
0.7966	Intermediate Similarity	NPC474095
0.7965	Intermediate Similarity	NPC471186
0.7951	Intermediate Similarity	NPC32322
0.7951	Intermediate Similarity	NPC259703
0.7949	Intermediate Similarity	NPC470253
0.7937	Intermediate Similarity	NPC72667
0.7937	Intermediate Similarity	NPC115797
0.7937	Intermediate Similarity	NPC51448
0.7934	Intermediate Similarity	NPC204784
0.7934	Intermediate Similarity	NPC476645
0.7931	Intermediate Similarity	NPC133308
0.7931	Intermediate Similarity	NPC265513
0.7928	Intermediate Similarity	NPC225079
0.7913	Intermediate Similarity	NPC318327
0.7881	Intermediate Similarity	NPC196673
0.7876	Intermediate Similarity	NPC329282
0.7863	Intermediate Similarity	NPC186128
0.7857	Intermediate Similarity	NPC304873
0.7857	Intermediate Similarity	NPC254492
0.7857	Intermediate Similarity	NPC25458
0.7851	Intermediate Similarity	NPC318173
0.784	Intermediate Similarity	NPC295664
0.7826	Intermediate Similarity	NPC472980
0.7826	Intermediate Similarity	NPC249811
0.7823	Intermediate Similarity	NPC282577
0.7818	Intermediate Similarity	NPC239185
0.7815	Intermediate Similarity	NPC476357
0.7807	Intermediate Similarity	NPC134120
0.7797	Intermediate Similarity	NPC93287
0.7795	Intermediate Similarity	NPC176130
0.7795	Intermediate Similarity	NPC69424
0.7795	Intermediate Similarity	NPC78364
0.7795	Intermediate Similarity	NPC84672
0.7788	Intermediate Similarity	NPC19856
0.7786	Intermediate Similarity	NPC212207
0.7786	Intermediate Similarity	NPC23894
0.7786	Intermediate Similarity	NPC474659
0.7778	Intermediate Similarity	NPC153885
0.7769	Intermediate Similarity	NPC45794
0.776	Intermediate Similarity	NPC328107
0.7752	Intermediate Similarity	NPC108129
0.7752	Intermediate Similarity	NPC253488
0.7748	Intermediate Similarity	NPC229242
0.7748	Intermediate Similarity	NPC134882
0.7748	Intermediate Similarity	NPC75724
0.7742	Intermediate Similarity	NPC293831
0.7742	Intermediate Similarity	NPC369
0.7734	Intermediate Similarity	NPC96024
0.7724	Intermediate Similarity	NPC232958
0.7724	Intermediate Similarity	NPC133389
0.7724	Intermediate Similarity	NPC183339
0.7724	Intermediate Similarity	NPC234337
0.7719	Intermediate Similarity	NPC249067
0.7717	Intermediate Similarity	NPC15837
0.7717	Intermediate Similarity	NPC71610
0.771	Intermediate Similarity	NPC78307
0.7706	Intermediate Similarity	NPC238219
0.7698	Intermediate Similarity	NPC474766
0.7698	Intermediate Similarity	NPC199273
0.7698	Intermediate Similarity	NPC164014
0.7686	Intermediate Similarity	NPC158157
0.7685	Intermediate Similarity	NPC133461
0.768	Intermediate Similarity	NPC176208
0.768	Intermediate Similarity	NPC164947
0.768	Intermediate Similarity	NPC307174
0.7679	Intermediate Similarity	NPC217621
0.7674	Intermediate Similarity	NPC276238
0.7674	Intermediate Similarity	NPC303910
0.7672	Intermediate Similarity	NPC112903
0.7672	Intermediate Similarity	NPC27252
0.7672	Intermediate Similarity	NPC211439
0.7672	Intermediate Similarity	NPC472979
0.7667	Intermediate Similarity	NPC228936
0.7667	Intermediate Similarity	NPC215419
0.7661	Intermediate Similarity	NPC241001
0.7658	Intermediate Similarity	NPC156021
0.7658	Intermediate Similarity	NPC265220
0.7652	Intermediate Similarity	NPC105899
0.7642	Intermediate Similarity	NPC472708
0.7636	Intermediate Similarity	NPC260233
0.7634	Intermediate Similarity	NPC312560
0.7632	Intermediate Similarity	NPC255676
0.7632	Intermediate Similarity	NPC329556
0.7619	Intermediate Similarity	NPC275145
0.7619	Intermediate Similarity	NPC135062
0.7615	Intermediate Similarity	NPC323420
0.7615	Intermediate Similarity	NPC155232
0.7611	Intermediate Similarity	NPC469481
0.7611	Intermediate Similarity	NPC476993
0.7611	Intermediate Similarity	NPC136810
0.7611	Intermediate Similarity	NPC128248
0.7611	Intermediate Similarity	NPC133809
0.7611	Intermediate Similarity	NPC109514
0.7597	Intermediate Similarity	NPC3009
0.7594	Intermediate Similarity	NPC309056
0.7589	Intermediate Similarity	NPC329387
0.7589	Intermediate Similarity	NPC317280
0.7586	Intermediate Similarity	NPC142326
0.7586	Intermediate Similarity	NPC83409
0.7586	Intermediate Similarity	NPC94751
0.7586	Intermediate Similarity	NPC37914
0.7586	Intermediate Similarity	NPC185763
0.7581	Intermediate Similarity	NPC318552
0.7581	Intermediate Similarity	NPC190501
0.7581	Intermediate Similarity	NPC238861
0.7581	Intermediate Similarity	NPC77000
0.7576	Intermediate Similarity	NPC138472
0.7568	Intermediate Similarity	NPC185208
0.7568	Intermediate Similarity	NPC219573
0.7563	Intermediate Similarity	NPC218855
0.7557	Intermediate Similarity	NPC471851
0.7557	Intermediate Similarity	NPC476847
0.7556	Intermediate Similarity	NPC230811
0.7541	Intermediate Similarity	NPC242764
0.7541	Intermediate Similarity	NPC105141
0.7541	Intermediate Similarity	NPC325646
0.7541	Intermediate Similarity	NPC28951
0.754	Intermediate Similarity	NPC121168
0.7538	Intermediate Similarity	NPC131684
0.7538	Intermediate Similarity	NPC25736
0.7538	Intermediate Similarity	NPC49272
0.7538	Intermediate Similarity	NPC471832
0.7537	Intermediate Similarity	NPC471670
0.7537	Intermediate Similarity	NPC474311
0.7519	Intermediate Similarity	NPC478162
0.7519	Intermediate Similarity	NPC478165
0.7519	Intermediate Similarity	NPC202225
0.75	Intermediate Similarity	NPC258366
0.75	Intermediate Similarity	NPC471481
0.75	Intermediate Similarity	NPC58685
0.75	Intermediate Similarity	NPC473974
0.75	Intermediate Similarity	NPC470765
0.75	Intermediate Similarity	NPC243601
0.75	Intermediate Similarity	NPC42657
0.75	Intermediate Similarity	NPC13784
0.75	Intermediate Similarity	NPC79933
0.75	Intermediate Similarity	NPC253423
0.75	Intermediate Similarity	NPC289201
0.75	Intermediate Similarity	NPC31296
0.7481	Intermediate Similarity	NPC475957
0.7481	Intermediate Similarity	NPC27659
0.748	Intermediate Similarity	NPC318067
0.748	Intermediate Similarity	NPC471187
0.7479	Intermediate Similarity	NPC291799
0.7479	Intermediate Similarity	NPC137315
0.7479	Intermediate Similarity	NPC222905
0.7477	Intermediate Similarity	NPC194326
0.7462	Intermediate Similarity	NPC48248
0.7462	Intermediate Similarity	NPC193203
0.746	Intermediate Similarity	NPC162935
0.746	Intermediate Similarity	NPC249340
0.7459	Intermediate Similarity	NPC135730
0.7458	Intermediate Similarity	NPC192577
0.7458	Intermediate Similarity	NPC64642
0.7458	Intermediate Similarity	NPC472982
0.7458	Intermediate Similarity	NPC149455
0.7455	Intermediate Similarity	NPC1682
0.7455	Intermediate Similarity	NPC188844
0.7455	Intermediate Similarity	NPC59677
0.7444	Intermediate Similarity	NPC477139
0.7444	Intermediate Similarity	NPC111845
0.7444	Intermediate Similarity	NPC310662
0.7442	Intermediate Similarity	NPC470753
0.7442	Intermediate Similarity	NPC253681
0.7442	Intermediate Similarity	NPC473220

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 NPC93181 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	251
0.1-0.2	940
0.2-0.3	1244
0.3-0.4	2743
0.4-0.5	2442
0.5-0.6	1187
0.6-0.7	293
0.7-0.8	46
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8276	Intermediate Similarity	NPD5951	Approved
0.823	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.8017	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2066	Phase 3
0.7931	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD3495	Discontinued
0.7724	Intermediate Similarity	NPD2932	Approved
0.7719	Intermediate Similarity	NPD1237	Approved
0.7667	Intermediate Similarity	NPD2629	Approved
0.7632	Intermediate Similarity	NPD1930	Approved
0.7632	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD1929	Approved
0.7615	Intermediate Similarity	NPD1088	Approved
0.7581	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD3019	Approved
0.7545	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD7610	Discontinued
0.7477	Intermediate Similarity	NPD1693	Approved
0.7455	Intermediate Similarity	NPD7631	Approved
0.7431	Intermediate Similarity	NPD1090	Approved
0.7431	Intermediate Similarity	NPD1086	Approved
0.7431	Intermediate Similarity	NPD1089	Approved
0.7419	Intermediate Similarity	NPD7009	Phase 2
0.7417	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7008	Discontinued
0.7405	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD4878	Approved
0.7364	Intermediate Similarity	NPD7609	Phase 3
0.736	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD800	Approved
0.7244	Intermediate Similarity	NPD4879	Approved
0.7236	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6049	Phase 2
0.7168	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD1087	Approved
0.7156	Intermediate Similarity	NPD650	Approved
0.713	Intermediate Similarity	NPD9495	Approved
0.712	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD9258	Approved
0.7117	Intermediate Similarity	NPD9256	Approved
0.7109	Intermediate Similarity	NPD3026	Approved
0.7109	Intermediate Similarity	NPD3023	Approved
0.7109	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD1932	Approved
0.7087	Intermediate Similarity	NPD3024	Approved
0.7087	Intermediate Similarity	NPD3025	Approved
0.7054	Intermediate Similarity	NPD1201	Approved
0.7054	Intermediate Similarity	NPD1239	Approved
0.7049	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD1565	Approved
0.7043	Intermediate Similarity	NPD1564	Approved
0.7043	Intermediate Similarity	NPD1566	Phase 3
0.7042	Intermediate Similarity	NPD7236	Approved
0.7031	Intermediate Similarity	NPD5306	Approved
0.7031	Intermediate Similarity	NPD5305	Approved
0.7029	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2329	Discontinued
0.6975	Remote Similarity	NPD5909	Discontinued
0.697	Remote Similarity	NPD1470	Approved
0.6953	Remote Similarity	NPD4102	Approved
0.6953	Remote Similarity	NPD4105	Approved
0.6947	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7635	Approved
0.6923	Remote Similarity	NPD4806	Approved
0.6923	Remote Similarity	NPD4807	Approved
0.6918	Remote Similarity	NPD7239	Suspended
0.6917	Remote Similarity	NPD4980	Approved
0.6912	Remote Similarity	NPD7961	Discontinued
0.6905	Remote Similarity	NPD3317	Approved
0.6905	Remote Similarity	NPD4198	Discontinued
0.6901	Remote Similarity	NPD7003	Approved
0.6894	Remote Similarity	NPD1283	Approved
0.6891	Remote Similarity	NPD6647	Phase 2
0.6885	Remote Similarity	NPD2182	Approved
0.687	Remote Similarity	NPD3972	Approved
0.6846	Remote Similarity	NPD4106	Approved
0.6846	Remote Similarity	NPD4136	Approved
0.6846	Remote Similarity	NPD4135	Approved
0.6833	Remote Similarity	NPD164	Approved
0.6822	Remote Similarity	NPD1651	Approved
0.6818	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.681	Remote Similarity	NPD1989	Approved
0.6806	Remote Similarity	NPD3300	Phase 2
0.68	Remote Similarity	NPD6858	Approved
0.68	Remote Similarity	NPD7094	Approved
0.6794	Remote Similarity	NPD6287	Discontinued
0.6791	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD9491	Approved
0.6788	Remote Similarity	NPD6663	Approved
0.6783	Remote Similarity	NPD8166	Discontinued
0.6783	Remote Similarity	NPD845	Approved
0.6783	Remote Similarity	NPD1563	Approved
0.6783	Remote Similarity	NPD1202	Approved
0.6769	Remote Similarity	NPD2345	Approved
0.6757	Remote Similarity	NPD9257	Approved
0.6757	Remote Similarity	NPD9259	Approved
0.6746	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD5736	Approved
0.6738	Remote Similarity	NPD5405	Approved
0.6738	Remote Similarity	NPD5406	Approved
0.6738	Remote Similarity	NPD5408	Approved
0.6738	Remote Similarity	NPD5404	Approved
0.6726	Remote Similarity	NPD5347	Phase 2
0.6726	Remote Similarity	NPD5346	Phase 2
0.6694	Remote Similarity	NPD1317	Discontinued
0.6692	Remote Similarity	NPD5157	Phase 1
0.6692	Remote Similarity	NPD5159	Phase 2
0.6692	Remote Similarity	NPD1755	Approved
0.6692	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.669	Remote Similarity	NPD2346	Discontinued
0.6667	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1281	Approved
0.6667	Remote Similarity	NPD2342	Discontinued
0.6667	Remote Similarity	NPD7714	Approved
0.6667	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5277	Phase 2
0.6667	Remote Similarity	NPD7715	Approved
0.6667	Remote Similarity	NPD1809	Phase 2
0.6642	Remote Similarity	NPD6966	Discovery
0.6641	Remote Similarity	NPD4059	Approved
0.6641	Remote Similarity	NPD4626	Approved
0.6639	Remote Similarity	NPD3020	Approved
0.6636	Remote Similarity	NPD3971	Phase 1
0.6615	Remote Similarity	NPD3091	Approved
0.6614	Remote Similarity	NPD6010	Discontinued
0.661	Remote Similarity	NPD288	Approved
0.6587	Remote Similarity	NPD9508	Approved
0.6581	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.656	Remote Similarity	NPD4750	Phase 3
0.6552	Remote Similarity	NPD1508	Approved
0.6549	Remote Similarity	NPD2799	Discontinued
0.6549	Remote Similarity	NPD4793	Discontinued
0.6544	Remote Similarity	NPD2798	Approved
0.6529	Remote Similarity	NPD4818	Approved
0.6529	Remote Similarity	NPD4817	Approved
0.6525	Remote Similarity	NPD844	Approved
0.6525	Remote Similarity	NPD2860	Approved
0.6525	Remote Similarity	NPD2859	Approved
0.6522	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD1876	Approved
0.6503	Remote Similarity	NPD6100	Approved
0.6503	Remote Similarity	NPD6099	Approved
0.65	Remote Similarity	NPD1238	Approved
0.6496	Remote Similarity	NPD5204	Approved
0.6496	Remote Similarity	NPD3662	Phase 3
0.6496	Remote Similarity	NPD3664	Approved
0.6496	Remote Similarity	NPD3663	Approved
0.6496	Remote Similarity	NPD3661	Approved
0.6494	Remote Similarity	NPD7057	Phase 3
0.6494	Remote Similarity	NPD7058	Phase 2
0.6489	Remote Similarity	NPD7741	Discontinued
0.6484	Remote Similarity	NPD1241	Discontinued
0.6475	Remote Similarity	NPD3764	Approved
0.6471	Remote Similarity	NPD1164	Approved
0.6471	Remote Similarity	NPD2797	Approved
0.6462	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD942	Approved
0.6455	Remote Similarity	NPD226	Approved
0.6449	Remote Similarity	NPD4617	Approved
0.6449	Remote Similarity	NPD4620	Approved
0.6449	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD5201	Approved
0.6449	Remote Similarity	NPD5203	Approved
0.6446	Remote Similarity	NPD1616	Discontinued
0.6446	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD6273	Approved
0.6441	Remote Similarity	NPD2933	Approved
0.6441	Remote Similarity	NPD2934	Approved
0.6439	Remote Similarity	NPD1245	Approved
0.6434	Remote Similarity	NPD7305	Phase 1
0.6429	Remote Similarity	NPD2067	Discontinued
0.6429	Remote Similarity	NPD8032	Phase 2
0.6429	Remote Similarity	NPD7713	Phase 3
0.6424	Remote Similarity	NPD7458	Discontinued
0.6423	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD6085	Phase 2
0.6422	Remote Similarity	NPD9490	Approved
0.6419	Remote Similarity	NPD7390	Discontinued
0.6418	Remote Similarity	NPD3092	Approved
0.64	Remote Similarity	NPD9267	Approved
0.64	Remote Similarity	NPD9264	Approved
0.64	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.64	Remote Similarity	NPD9263	Approved
0.6397	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD3095	Discontinued
0.6391	Remote Similarity	NPD4199	Phase 3
0.6391	Remote Similarity	NPD1751	Approved
0.6391	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD1843	Approved
0.6383	Remote Similarity	NPD2979	Phase 3
0.6383	Remote Similarity	NPD5119	Approved
0.6383	Remote Similarity	NPD5121	Approved
0.6383	Remote Similarity	NPD5120	Approved
0.6383	Remote Similarity	NPD4445	Approved
0.6383	Remote Similarity	NPD4452	Approved
0.6383	Remote Similarity	NPD4453	Approved
0.6379	Remote Similarity	NPD3673	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