NPASS Compound

Structure

NPC474224 OpenBabel07101718242D 35 37 0 0 1 0 0 0 0 0999 V2000 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6962 2.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 7 9 1 0 0 0 0 7 16 1 0 0 0 0 8 10 1 0 0 0 0 8 20 1 0 0 0 0 9 27 1 0 0 0 0 10 28 1 0 0 0 0 11 15 1 0 0 0 0 11 17 1 0 0 0 0 12 16 1 0 0 0 0 12 21 1 0 0 0 0 13 18 1 0 0 0 0 13 29 2 0 0 0 0 14 19 1 0 0 0 0 14 30 2 0 0 0 0 16 26 1 6 0 0 0 17 20 1 0 0 0 0 17 22 1 0 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 19 23 1 0 0 0 0 19 25 2 0 0 0 0 20 27 1 6 0 0 0 21 27 1 6 0 0 0 21 28 1 0 0 0 0 22 24 2 0 0 0 0 22 25 1 0 0 0 0 23 31 1 0 0 0 0 24 32 1 0 0 0 0 25 33 1 0 0 0 0 26 34 1 0 0 0 0 27 5 1 6 0 0 0 28 6 1 6 0 0 0 28 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	490.29
Volume:	515.524
LogP:	5.832
LogD:	3.348
LogS:	-4.04
# Rotatable Bonds:	7
TPSA:	135.29
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.343
Synthetic Accessibility Score:	4.953
Fsp3:	0.714
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.896
MDCK Permeability:	7.493567409255775e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.083
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.234
Plasma Protein Binding (PPB):	100.32774353027344%
Volume Distribution (VD):	1.243
Pgp-substrate:	1.9641008377075195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.055
CYP1A2-substrate:	0.222
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.354
CYP2C9-inhibitor:	0.437
CYP2C9-substrate:	0.883
CYP2D6-inhibitor:	0.026
CYP2D6-substrate:	0.131
CYP3A4-inhibitor:	0.127
CYP3A4-substrate:	0.162

ADMET: Excretion

Clearance (CL):	2.053
Half-life (T1/2):	0.16

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.018
Drug-inuced Liver Injury (DILI):	0.034
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.057
Maximum Recommended Daily Dose:	0.516
Skin Sensitization:	0.686
Carcinogencity:	0.115
Eye Corrosion:	0.005
Eye Irritation:	0.738
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC474224

Natural Product ID:	NPC474224
*Common Name:**	Macrocarpal J
IUPAC Name:	5-[1-[(1S,4R,4aR,6R,8aS)-4-hydroxy-6-(2-hydroxypropan-2-yl)-4,8a-dimethyl-1,2,3,4a,5,6,7,8-octahydronaphthalen-1-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde
Synonyms:	Macrocarpal J
Standard InCHIKey:	PXQFFMATXFLUPK-FBWULOCESA-N
Standard InCHI:	InChI=1S/C28H42O7/c1-15(2)11-17(22-24(32)18(13-29)23(31)19(14-30)25(22)33)20-8-10-28(6,35)21-12-16(26(3,4)34)7-9-27(20,21)5/h13-17,20-21,31-35H,7-12H2,1-6H3/t16-,17?,20+,21-,27+,28-/m1/s1
SMILES:	CC(C)CC(C1CCC(C2C1(CCC(C2)C(C)(C)O)C)(C)O)C3=C(C(=C(C(=C3O)C=O)O)C=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463716
PubChem CID:	177346
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0000101] Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids

*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
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	fruit	n.a.	PMID[18020353]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22934600]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[23678820]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[30543429]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[30848923]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[8864235]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	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
MIC	10
Others	3

Activity Type	# Activity
Organism	10
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4829	Organism	Prevotella melaninogenica	Prevotella melaninogenica	MIC	=	12.5	ug.mL-1	PMID[490120]
NPT1128	Organism	Prevotella intermedia	Prevotella intermedia	MIC	=	12.5	ug.mL-1	PMID[490120]
NPT5408	Organism	Capnocytophaga ochracea	Capnocytophaga ochracea	MIC	=	12.5	ug.mL-1	PMID[490120]
NPT1484	Organism	Fusobacterium nucleatum	Fusobacterium nucleatum	MIC	=	25.0	ug.mL-1	PMID[490120]
NPT2	Others	Unspecified		Inhibition	=	77.1	%	PMID[490120]
NPT2	Others	Unspecified		Inhibition	=	29.7	%	PMID[490120]
NPT2	Others	Unspecified		Inhibition	=	6.9	%	PMID[490120]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MIC	=	50.0	ug.mL-1	PMID[490120]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MIC	=	25.0	ug.mL-1	PMID[490120]
NPT1483	Organism	Streptococcus sobrinus	Streptococcus sobrinus	MIC	=	100.0	ug.mL-1	PMID[490120]
NPT1129	Organism	Actinomyces viscosus	Actinomyces viscosus	MIC	=	12.5	ug.mL-1	PMID[490120]
NPT1127	Organism	Porphyromonas gingivalis	Porphyromonas gingivalis	MIC	=	6.25	ug.mL-1	PMID[490120]

☑ 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 NPC474224 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	334
0.1-0.2	1515
0.2-0.3	3250
0.3-0.4	7796
0.4-0.5	11874
0.5-0.6	7285
0.6-0.7	7909
0.7-0.8	2612
0.8-0.85	100
0.85-0.9	7
0.9-0.95	9
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474117
0.9767	High Similarity	NPC475917
0.8947	High Similarity	NPC474109
0.8889	High Similarity	NPC474076
0.8889	High Similarity	NPC244640
0.8889	High Similarity	NPC279291
0.8837	High Similarity	NPC306288
0.8803	High Similarity	NPC304351
0.8803	High Similarity	NPC245757
0.876	High Similarity	NPC218333
0.8759	High Similarity	NPC147691
0.8722	High Similarity	NPC73203
0.8686	High Similarity	NPC299734
0.8551	High Similarity	NPC191976
0.854	High Similarity	NPC475088
0.8511	High Similarity	NPC92079
0.8507	High Similarity	NPC475553
0.8507	High Similarity	NPC164894
0.85	High Similarity	NPC162939
0.8473	Intermediate Similarity	NPC232708
0.8473	Intermediate Similarity	NPC66252
0.8472	Intermediate Similarity	NPC476535
0.8462	Intermediate Similarity	NPC229649
0.8456	Intermediate Similarity	NPC275504
0.8451	Intermediate Similarity	NPC474961
0.8429	Intermediate Similarity	NPC473622
0.8421	Intermediate Similarity	NPC290466
0.8406	Intermediate Similarity	NPC474519
0.8394	Intermediate Similarity	NPC175738
0.8382	Intermediate Similarity	NPC62219
0.8358	Intermediate Similarity	NPC328983
0.8357	Intermediate Similarity	NPC53001
0.8345	Intermediate Similarity	NPC278375
0.8333	Intermediate Similarity	NPC267205
0.8322	Intermediate Similarity	NPC285659
0.8322	Intermediate Similarity	NPC81337
0.8322	Intermediate Similarity	NPC135524
0.8322	Intermediate Similarity	NPC193555
0.8322	Intermediate Similarity	NPC73061
0.8322	Intermediate Similarity	NPC157497
0.831	Intermediate Similarity	NPC181560
0.831	Intermediate Similarity	NPC169452
0.8309	Intermediate Similarity	NPC476119
0.8298	Intermediate Similarity	NPC87723
0.8296	Intermediate Similarity	NPC316625
0.8296	Intermediate Similarity	NPC329205
0.8284	Intermediate Similarity	NPC475733
0.8278	Intermediate Similarity	NPC272196
0.8276	Intermediate Similarity	NPC12402
0.8273	Intermediate Similarity	NPC270899
0.8252	Intermediate Similarity	NPC469818
0.8252	Intermediate Similarity	NPC305845
0.8252	Intermediate Similarity	NPC204045
0.8243	Intermediate Similarity	NPC476532
0.8239	Intermediate Similarity	NPC242994
0.8239	Intermediate Similarity	NPC138099
0.8227	Intermediate Similarity	NPC245058
0.8227	Intermediate Similarity	NPC471905
0.8219	Intermediate Similarity	NPC143685
0.8214	Intermediate Similarity	NPC249272
0.8214	Intermediate Similarity	NPC290803
0.8207	Intermediate Similarity	NPC5990
0.8201	Intermediate Similarity	NPC477139
0.8201	Intermediate Similarity	NPC37299
0.8201	Intermediate Similarity	NPC114183
0.8201	Intermediate Similarity	NPC180261
0.8188	Intermediate Similarity	NPC41847
0.8175	Intermediate Similarity	NPC303910
0.8175	Intermediate Similarity	NPC474998
0.8169	Intermediate Similarity	NPC477593
0.8162	Intermediate Similarity	NPC116513
0.8156	Intermediate Similarity	NPC156967
0.8156	Intermediate Similarity	NPC472599
0.8156	Intermediate Similarity	NPC254847
0.8156	Intermediate Similarity	NPC118919
0.8151	Intermediate Similarity	NPC470674
0.8151	Intermediate Similarity	NPC34482
0.8151	Intermediate Similarity	NPC117716
0.8151	Intermediate Similarity	NPC470673
0.8143	Intermediate Similarity	NPC12070
0.8143	Intermediate Similarity	NPC282780
0.8143	Intermediate Similarity	NPC166480
0.8138	Intermediate Similarity	NPC451542
0.8138	Intermediate Similarity	NPC313047
0.8138	Intermediate Similarity	NPC174905
0.8138	Intermediate Similarity	NPC295712
0.8138	Intermediate Similarity	NPC474203
0.8138	Intermediate Similarity	NPC293545
0.8134	Intermediate Similarity	NPC472029
0.8134	Intermediate Similarity	NPC65761
0.8133	Intermediate Similarity	NPC476533
0.8125	Intermediate Similarity	NPC187843
0.8121	Intermediate Similarity	NPC474191
0.8116	Intermediate Similarity	NPC296158
0.8116	Intermediate Similarity	NPC259942
0.8112	Intermediate Similarity	NPC190457
0.8105	Intermediate Similarity	NPC472617
0.8102	Intermediate Similarity	NPC21305
0.8102	Intermediate Similarity	NPC473017
0.8102	Intermediate Similarity	NPC3009
0.8099	Intermediate Similarity	NPC53206
0.8099	Intermediate Similarity	NPC53414
0.8095	Intermediate Similarity	NPC470570
0.8095	Intermediate Similarity	NPC63918
0.8095	Intermediate Similarity	NPC82534
0.8088	Intermediate Similarity	NPC267846
0.8088	Intermediate Similarity	NPC473691
0.8082	Intermediate Similarity	NPC21599
0.8082	Intermediate Similarity	NPC193703
0.8082	Intermediate Similarity	NPC244691
0.8082	Intermediate Similarity	NPC471906
0.8082	Intermediate Similarity	NPC48762
0.8079	Intermediate Similarity	NPC472211
0.8071	Intermediate Similarity	NPC139074
0.8071	Intermediate Similarity	NPC213485
0.8071	Intermediate Similarity	NPC40524
0.8067	Intermediate Similarity	NPC470675
0.8067	Intermediate Similarity	NPC477672
0.8067	Intermediate Similarity	NPC478148
0.8067	Intermediate Similarity	NPC473131
0.8067	Intermediate Similarity	NPC477673
0.806	Intermediate Similarity	NPC91105
0.8058	Intermediate Similarity	NPC475042
0.8058	Intermediate Similarity	NPC279566
0.8056	Intermediate Similarity	NPC99441
0.8054	Intermediate Similarity	NPC329933
0.8054	Intermediate Similarity	NPC477221
0.8043	Intermediate Similarity	NPC92624
0.8042	Intermediate Similarity	NPC255801
0.8042	Intermediate Similarity	NPC322301
0.8041	Intermediate Similarity	NPC34802
0.8041	Intermediate Similarity	NPC290194
0.8029	Intermediate Similarity	NPC100067
0.8029	Intermediate Similarity	NPC23126
0.8029	Intermediate Similarity	NPC169250
0.8029	Intermediate Similarity	NPC162612
0.8029	Intermediate Similarity	NPC105157
0.8029	Intermediate Similarity	NPC98254
0.8029	Intermediate Similarity	NPC83572
0.8029	Intermediate Similarity	NPC190043
0.8029	Intermediate Similarity	NPC103356
0.8029	Intermediate Similarity	NPC30501
0.8029	Intermediate Similarity	NPC266689
0.8029	Intermediate Similarity	NPC72158
0.8028	Intermediate Similarity	NPC471690
0.8025	Intermediate Similarity	NPC125465
0.8015	Intermediate Similarity	NPC477454
0.8015	Intermediate Similarity	NPC137750
0.8014	Intermediate Similarity	NPC202225
0.8014	Intermediate Similarity	NPC474394
0.8014	Intermediate Similarity	NPC44437
0.8014	Intermediate Similarity	NPC470984
0.8014	Intermediate Similarity	NPC297600
0.8013	Intermediate Similarity	NPC161778
0.8013	Intermediate Similarity	NPC100849
0.8	Intermediate Similarity	NPC246638
0.8	Intermediate Similarity	NPC37530
0.8	Intermediate Similarity	NPC48949
0.7986	Intermediate Similarity	NPC143438
0.7986	Intermediate Similarity	NPC17840
0.7986	Intermediate Similarity	NPC247477
0.7986	Intermediate Similarity	NPC186628
0.7985	Intermediate Similarity	NPC226275
0.7985	Intermediate Similarity	NPC215392
0.7974	Intermediate Similarity	NPC280497
0.7973	Intermediate Similarity	NPC110882
0.7973	Intermediate Similarity	NPC473132
0.7973	Intermediate Similarity	NPC271944
0.7973	Intermediate Similarity	NPC473135
0.7973	Intermediate Similarity	NPC470676
0.7973	Intermediate Similarity	NPC85393
0.7972	Intermediate Similarity	NPC477592
0.7972	Intermediate Similarity	NPC194579
0.7971	Intermediate Similarity	NPC221777
0.7971	Intermediate Similarity	NPC229894
0.7971	Intermediate Similarity	NPC470981
0.7961	Intermediate Similarity	NPC273248
0.7961	Intermediate Similarity	NPC208806
0.7961	Intermediate Similarity	NPC477669
0.7959	Intermediate Similarity	NPC227841
0.7958	Intermediate Similarity	NPC283590
0.7958	Intermediate Similarity	NPC70859
0.7958	Intermediate Similarity	NPC130899
0.7958	Intermediate Similarity	NPC61153
0.7956	Intermediate Similarity	NPC472047
0.7956	Intermediate Similarity	NPC62952
0.7947	Intermediate Similarity	NPC474417
0.7947	Intermediate Similarity	NPC149526
0.7947	Intermediate Similarity	NPC305965
0.7945	Intermediate Similarity	NPC232021
0.7945	Intermediate Similarity	NPC137649
0.7945	Intermediate Similarity	NPC126534
0.7945	Intermediate Similarity	NPC85310
0.7945	Intermediate Similarity	NPC40118
0.7945	Intermediate Similarity	NPC476508
0.7943	Intermediate Similarity	NPC470988
0.7943	Intermediate Similarity	NPC48036
0.7943	Intermediate Similarity	NPC285054
0.7943	Intermediate Similarity	NPC103105
0.7935	Intermediate Similarity	NPC472618

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 NPC474224 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	308
0.1-0.2	998
0.2-0.3	1883
0.3-0.4	2952
0.4-0.5	2003
0.5-0.6	756
0.6-0.7	221
0.7-0.8	29
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
0.8156	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD6651	Approved
0.7959	Intermediate Similarity	NPD7390	Discontinued
0.7677	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD2533	Approved
0.7667	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD2534	Approved
0.7667	Intermediate Similarity	NPD2532	Approved
0.7603	Intermediate Similarity	NPD5405	Approved
0.7603	Intermediate Similarity	NPD5406	Approved
0.7603	Intermediate Similarity	NPD5404	Approved
0.7603	Intermediate Similarity	NPD5408	Approved
0.7568	Intermediate Similarity	NPD2800	Approved
0.7464	Intermediate Similarity	NPD1201	Approved
0.7438	Intermediate Similarity	NPD6959	Discontinued
0.7434	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1510	Phase 2
0.7389	Intermediate Similarity	NPD7819	Suspended
0.7383	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD943	Approved
0.7376	Intermediate Similarity	NPD1470	Approved
0.7362	Intermediate Similarity	NPD7473	Discontinued
0.7284	Intermediate Similarity	NPD6232	Discontinued
0.7279	Intermediate Similarity	NPD1607	Approved
0.7278	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD7411	Suspended
0.726	Intermediate Similarity	NPD1240	Approved
0.7248	Intermediate Similarity	NPD6099	Approved
0.7248	Intermediate Similarity	NPD6100	Approved
0.7246	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4380	Phase 2
0.7188	Intermediate Similarity	NPD7768	Phase 2
0.7152	Intermediate Similarity	NPD1549	Phase 2
0.7143	Intermediate Similarity	NPD7075	Discontinued
0.7091	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5711	Approved
0.7073	Intermediate Similarity	NPD5710	Approved
0.7071	Intermediate Similarity	NPD3019	Approved
0.7067	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD2796	Approved
0.702	Intermediate Similarity	NPD2935	Discontinued
0.7014	Intermediate Similarity	NPD1164	Approved
0.7	Intermediate Similarity	NPD1934	Approved
0.6981	Remote Similarity	NPD6599	Discontinued
0.695	Remote Similarity	NPD2932	Approved
0.6918	Remote Similarity	NPD7458	Discontinued
0.6914	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1551	Phase 2
0.6894	Remote Similarity	NPD6801	Discontinued
0.6883	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD3300	Phase 2
0.6852	Remote Similarity	NPD5761	Phase 2
0.6852	Remote Similarity	NPD2801	Approved
0.6852	Remote Similarity	NPD5760	Phase 2
0.6846	Remote Similarity	NPD6663	Approved
0.6842	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7003	Approved
0.6829	Remote Similarity	NPD3749	Approved
0.6815	Remote Similarity	NPD1511	Approved
0.6803	Remote Similarity	NPD5736	Approved
0.6786	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6166	Phase 2
0.6786	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD3882	Suspended
0.6765	Remote Similarity	NPD6020	Phase 2
0.6765	Remote Similarity	NPD4750	Phase 3
0.6765	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5844	Phase 1
0.6747	Remote Similarity	NPD5494	Approved
0.6744	Remote Similarity	NPD6559	Discontinued
0.6731	Remote Similarity	NPD8166	Discontinued
0.6731	Remote Similarity	NPD3750	Approved
0.673	Remote Similarity	NPD1512	Approved
0.6727	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD6799	Approved
0.6708	Remote Similarity	NPD3226	Approved
0.6705	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD920	Approved
0.6667	Remote Similarity	NPD3764	Approved
0.6667	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3026	Approved
0.6667	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3023	Approved
0.6667	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD8150	Discontinued
0.6648	Remote Similarity	NPD8434	Phase 2
0.6645	Remote Similarity	NPD230	Phase 1
0.6643	Remote Similarity	NPD3024	Approved
0.6643	Remote Similarity	NPD3025	Approved
0.6643	Remote Similarity	NPD5951	Approved
0.6628	Remote Similarity	NPD7074	Phase 3
0.6624	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD4628	Phase 3
0.6623	Remote Similarity	NPD2799	Discontinued
0.6622	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD3817	Phase 2
0.6592	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD9269	Phase 2
0.6573	Remote Similarity	NPD3091	Approved
0.657	Remote Similarity	NPD7286	Phase 2
0.657	Remote Similarity	NPD7054	Approved
0.6562	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD3094	Phase 2
0.6549	Remote Similarity	NPD9493	Approved
0.6541	Remote Similarity	NPD7236	Approved
0.6541	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD2346	Discontinued
0.6536	Remote Similarity	NPD5124	Phase 1
0.6536	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD4908	Phase 1
0.6532	Remote Similarity	NPD7472	Approved
0.6528	Remote Similarity	NPD9268	Approved
0.6512	Remote Similarity	NPD3818	Discontinued
0.651	Remote Similarity	NPD2798	Approved
0.6507	Remote Similarity	NPD3092	Approved
0.6503	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD5953	Discontinued
0.6493	Remote Similarity	NPD846	Approved
0.6493	Remote Similarity	NPD940	Approved
0.6488	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD37	Approved
0.6483	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7229	Phase 3
0.6463	Remote Similarity	NPD3972	Approved
0.646	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD9545	Approved
0.6457	Remote Similarity	NPD7251	Discontinued
0.6456	Remote Similarity	NPD1243	Approved
0.6449	Remote Similarity	NPD74	Approved
0.6449	Remote Similarity	NPD9266	Approved
0.6449	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD2344	Approved
0.6432	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6535	Approved
0.6429	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6534	Approved
0.642	Remote Similarity	NPD7808	Phase 3
0.642	Remote Similarity	NPD6273	Approved
0.6413	Remote Similarity	NPD7699	Phase 2
0.6413	Remote Similarity	NPD7700	Phase 2
0.6412	Remote Similarity	NPD1247	Approved
0.641	Remote Similarity	NPD3748	Approved
0.64	Remote Similarity	NPD6797	Phase 2
0.6391	Remote Similarity	NPD919	Approved
0.6391	Remote Similarity	NPD6234	Discontinued
0.6383	Remote Similarity	NPD7635	Approved
0.6382	Remote Similarity	NPD4625	Phase 3
0.6382	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD9263	Approved
0.6377	Remote Similarity	NPD9267	Approved
0.6377	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD9264	Approved
0.6375	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.637	Remote Similarity	NPD3095	Discontinued
0.637	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.637	Remote Similarity	NPD4059	Approved
0.6369	Remote Similarity	NPD4967	Phase 2
0.6369	Remote Similarity	NPD4965	Approved
0.6369	Remote Similarity	NPD4966	Approved
0.6364	Remote Similarity	NPD1809	Phase 2
0.6352	Remote Similarity	NPD2654	Approved
0.6347	Remote Similarity	NPD1465	Phase 2
0.6341	Remote Similarity	NPD7239	Suspended
0.634	Remote Similarity	NPD3268	Approved
0.634	Remote Similarity	NPD2313	Discontinued
0.6339	Remote Similarity	NPD4360	Phase 2
0.6339	Remote Similarity	NPD4363	Phase 3
0.6338	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6832	Phase 2
0.6312	Remote Similarity	NPD3400	Discontinued
0.6309	Remote Similarity	NPD4749	Approved
0.6304	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD4361	Phase 2
0.6298	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD8320	Phase 1
0.6296	Remote Similarity	NPD8319	Approved
0.6292	Remote Similarity	NPD5035	Approved
0.6292	Remote Similarity	NPD8312	Approved
0.6292	Remote Similarity	NPD8313	Approved
0.6284	Remote Similarity	NPD1610	Phase 2
0.628	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.628	Remote Similarity	NPD5403	Approved
0.6276	Remote Similarity	NPD7610	Discontinued
0.6275	Remote Similarity	NPD7008	Discontinued
0.6273	Remote Similarity	NPD2309	Approved
0.6273	Remote Similarity	NPD6190	Approved
0.6267	Remote Similarity	NPD1283	Approved
0.6259	Remote Similarity	NPD2342	Discontinued
0.6257	Remote Similarity	NPD6779	Approved
0.6257	Remote Similarity	NPD6777	Approved
0.6257	Remote Similarity	NPD6778	Approved
0.6257	Remote Similarity	NPD6781	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