NPASS Compound

Structure

NPC475380 OpenBabel07101718322D 42 45 0 0 1 0 0 0 0 0999 V2000 6.7617 1.4362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1033 2.3936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2741 -1.9149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3592 -0.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3173 -3.7954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7866 -3.3511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9237 0.3504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9325 0.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7866 1.4362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9574 0.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6158 -1.9149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8801 -1.3625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4024 -0.4787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8801 -2.9117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4787 -0.8292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1283 -1.4362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1033 1.4362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4450 -1.4362 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5301 -1.4362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3599 -3.7954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9574 -2.8723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3173 -2.1371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6158 0.9574 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3599 -2.1371 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7866 -1.4362 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7907 -1.6583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6158 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2741 0.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4450 -0.4787 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9574 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7866 -0.4787 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5301 -2.3936 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8811 -4.6246 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1283 -3.3511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5653 -1.0956 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2741 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7907 -2.6158 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7009 -0.9574 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8811 -2.9662 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9574 -1.9149 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4450 1.4362 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 5 20 1 0 0 0 0 6 21 1 0 0 0 0 8 17 2 0 0 0 0 9 10 1 0 0 0 0 9 23 1 0 0 0 0 10 30 1 0 0 0 0 11 18 1 0 0 0 0 11 25 1 0 0 0 0 12 22 2 0 0 0 0 12 26 1 0 0 0 0 13 29 1 0 0 0 0 14 22 1 0 0 0 0 14 37 1 0 0 0 0 15 30 1 0 0 0 0 15 39 1 0 0 0 0 16 38 1 0 0 0 0 17 28 1 0 0 0 0 18 29 1 6 0 0 0 19 32 2 0 0 0 0 19 38 1 0 0 0 0 20 33 2 0 0 0 0 20 40 1 0 0 0 0 21 34 2 0 0 0 0 21 41 1 0 0 0 0 22 24 1 0 0 0 0 23 27 1 0 0 0 0 23 42 1 1 0 0 0 24 13 1 1 0 0 0 24 40 1 0 0 0 0 25 31 1 6 0 0 0 25 41 1 0 0 0 0 26 35 2 0 0 0 0 26 37 1 0 0 0 0 27 29 1 6 0 0 0 27 31 1 0 0 0 0 28 36 2 0 0 0 0 28 42 1 0 0 0 0 29 7 1 6 0 0 0 30 31 1 6 0 0 0 30 39 1 0 0 0 0 31 16 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	590.27
Volume:	588.743
LogP:	3.245
LogD:	2.212
LogS:	-3.986
# Rotatable Bonds:	13
TPSA:	151.1
# H-Bond Aceptor:	11
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.186
Synthetic Accessibility Score:	5.837
Fsp3:	0.677
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.325
MDCK Permeability:	6.711651803925633e-05
Pgp-inhibitor:	0.943
Pgp-substrate:	0.929
Human Intestinal Absorption (HIA):	0.21
20% Bioavailability (F20%):	0.906
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.217
Plasma Protein Binding (PPB):	86.57568359375%
Volume Distribution (VD):	1.305
Pgp-substrate:	10.689403533935547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.092
CYP2C19-inhibitor:	0.129
CYP2C19-substrate:	0.143
CYP2C9-inhibitor:	0.761
CYP2C9-substrate:	0.068
CYP2D6-inhibitor:	0.173
CYP2D6-substrate:	0.089
CYP3A4-inhibitor:	0.629
CYP3A4-substrate:	0.523

ADMET: Excretion

Clearance (CL):	4.385
Half-life (T1/2):	0.786

ADMET: Toxicity

hERG Blockers:	0.053
Human Hepatotoxicity (H-HT):	0.797
Drug-inuced Liver Injury (DILI):	0.84
AMES Toxicity:	0.058
Rat Oral Acute Toxicity:	0.66
Maximum Recommended Daily Dose:	0.906
Skin Sensitization:	0.149
Carcinogencity:	0.068
Eye Corrosion:	0.003
Eye Irritation:	0.041
Respiratory Toxicity:	0.672

Download Data

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

Natural Product: NPC475380

Natural Product ID:	NPC475380
*Common Name:**	((1R,4R,4Ar,5S,6R,8S,8Ar)-8-Acetoxy-5-((S)-2-Acetoxy-2-(5-Oxo-2,5-Dihydrofuran-3-Yl)Ethyl)-8A-(Acetoxymethyl)-5,6-Dimethyloctahydro-2H-Spiro[Naphthalene-1,2'-Oxirane]-4-Yl) 2-Methylbut-2-Enoate
IUPAC Name:	[(1R,4R,4aR,5S,7R,8S,8aR)-5-acetyloxy-4a-(acetyloxymethyl)-8-[(2S)-2-acetyloxy-2-(5-oxo-2H-furan-3-yl)ethyl]-7,8-dimethylspiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxirane]-1-yl] (Z)-2-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	IAAHUGSOWYSQSN-BVGCTOFVSA-N
Standard InCHI:	InChI=1S/C31H42O11/c1-8-17(2)28(36)42-23-9-10-30(15-39-30)31(16-38-19(4)32)25(41-21(6)34)11-18(3)29(7,27(23)31)13-24(40-20(5)33)22-12-26(35)37-14-22/h8,12,18,23-25,27H,9-11,13-16H2,1-7H3/b17-8-/t18-,23-,24+,25+,27-,29+,30+,31-/m1/s1
SMILES:	C/C=C(C(=O)O[C@@H]1CC[C@@]2([C@]3([C@H]1[C@@](C)(C[C@@H](C1=CC(=O)OC1)OC(=O)C)[C@H](C)C[C@@H]3OC(=O)C)COC(=O)C)CO2)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL504528
PubChem CID:	44566350
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic acids 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
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	flowering whole plant	n.a.	n.a.	PMID[10425119]
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9748375]
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17539	Ajuga decumbens	Species	Lamiaceae	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
Others	8

Activity Type	# Activity
Cell Line	4
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[507806]
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[507806]
NPT2	Others	Unspecified		Activity	=	42.6	%	PMID[507806]
NPT2	Others	Unspecified		Activity	=	73.5	%	PMID[507806]
NPT2	Others	Unspecified		Activity	=	0.0	%	PMID[507806]
NPT2	Others	Unspecified		Activity	=	100.0	%	PMID[507806]

☑ 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 NPC475380 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	232
0.1-0.2	1496
0.2-0.3	5005
0.3-0.4	10157
0.4-0.5	12052
0.5-0.6	7232
0.6-0.7	5228
0.7-0.8	1206
0.8-0.85	59
0.85-0.9	16
0.9-0.95	6
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC209297
0.9889	High Similarity	NPC475446
0.9889	High Similarity	NPC311241
0.978	High Similarity	NPC72647
0.978	High Similarity	NPC107806
0.9775	High Similarity	NPC140277
0.967	High Similarity	NPC100912
0.956	High Similarity	NPC194132
0.9468	High Similarity	NPC109195
0.9468	High Similarity	NPC475038
0.9213	High Similarity	NPC93411
0.913	High Similarity	NPC161998
0.9022	High Similarity	NPC7349
0.8925	High Similarity	NPC105490
0.8854	High Similarity	NPC16601
0.8763	High Similarity	NPC11974
0.87	High Similarity	NPC319438
0.8673	High Similarity	NPC162973
0.8632	High Similarity	NPC276110
0.8614	High Similarity	NPC181994
0.8587	High Similarity	NPC106332
0.8586	High Similarity	NPC471938
0.8529	High Similarity	NPC322912
0.8515	High Similarity	NPC216636
0.85	High Similarity	NPC471937
0.8485	Intermediate Similarity	NPC472552
0.8485	Intermediate Similarity	NPC471914
0.8469	Intermediate Similarity	NPC324841
0.8469	Intermediate Similarity	NPC471413
0.8462	Intermediate Similarity	NPC474013
0.8438	Intermediate Similarity	NPC476519
0.8416	Intermediate Similarity	NPC51719
0.8384	Intermediate Similarity	NPC471412
0.8384	Intermediate Similarity	NPC472554
0.8367	Intermediate Similarity	NPC278673
0.8351	Intermediate Similarity	NPC260796
0.8333	Intermediate Similarity	NPC471205
0.8315	Intermediate Similarity	NPC469802
0.83	Intermediate Similarity	NPC476081
0.8283	Intermediate Similarity	NPC38855
0.828	Intermediate Similarity	NPC475087
0.828	Intermediate Similarity	NPC102640
0.8265	Intermediate Similarity	NPC51499
0.8247	Intermediate Similarity	NPC471915
0.8247	Intermediate Similarity	NPC111273
0.8235	Intermediate Similarity	NPC218158
0.8235	Intermediate Similarity	NPC471206
0.8218	Intermediate Similarity	NPC160583
0.8218	Intermediate Similarity	NPC165608
0.8218	Intermediate Similarity	NPC120009
0.8211	Intermediate Similarity	NPC78973
0.8191	Intermediate Similarity	NPC69713
0.8182	Intermediate Similarity	NPC275086
0.8182	Intermediate Similarity	NPC325229
0.8172	Intermediate Similarity	NPC102996
0.8172	Intermediate Similarity	NPC131813
0.8163	Intermediate Similarity	NPC234993
0.8163	Intermediate Similarity	NPC29952
0.8163	Intermediate Similarity	NPC134072
0.8155	Intermediate Similarity	NPC122816
0.8152	Intermediate Similarity	NPC32223
0.8152	Intermediate Similarity	NPC96055
0.8152	Intermediate Similarity	NPC306951
0.8132	Intermediate Similarity	NPC471218
0.8125	Intermediate Similarity	NPC78594
0.8125	Intermediate Similarity	NPC473944
0.8105	Intermediate Similarity	NPC170633
0.8095	Intermediate Similarity	NPC253906
0.8085	Intermediate Similarity	NPC264546
0.8085	Intermediate Similarity	NPC166857
0.8081	Intermediate Similarity	NPC474921
0.8061	Intermediate Similarity	NPC472441
0.8058	Intermediate Similarity	NPC220217
0.8058	Intermediate Similarity	NPC119855
0.8058	Intermediate Similarity	NPC477090
0.8058	Intermediate Similarity	NPC34768
0.8056	Intermediate Similarity	NPC470793
0.8041	Intermediate Similarity	NPC162615
0.8041	Intermediate Similarity	NPC205034
0.8041	Intermediate Similarity	NPC152778
0.8041	Intermediate Similarity	NPC139692
0.8041	Intermediate Similarity	NPC472641
0.8041	Intermediate Similarity	NPC110022
0.8041	Intermediate Similarity	NPC472640
0.8039	Intermediate Similarity	NPC10232
0.8039	Intermediate Similarity	NPC187302
0.8039	Intermediate Similarity	NPC23584
0.8039	Intermediate Similarity	NPC474822
0.8039	Intermediate Similarity	NPC189588
0.8039	Intermediate Similarity	NPC196471
0.8039	Intermediate Similarity	NPC97487
0.8039	Intermediate Similarity	NPC281378
0.8039	Intermediate Similarity	NPC120321
0.8039	Intermediate Similarity	NPC45897
0.8039	Intermediate Similarity	NPC254202
0.8021	Intermediate Similarity	NPC302280
0.802	Intermediate Similarity	NPC295110
0.802	Intermediate Similarity	NPC25177
0.802	Intermediate Similarity	NPC268829
0.802	Intermediate Similarity	NPC222875
0.802	Intermediate Similarity	NPC247701
0.8019	Intermediate Similarity	NPC470076
0.8	Intermediate Similarity	NPC471366
0.8	Intermediate Similarity	NPC318917
0.8	Intermediate Similarity	NPC476800
0.8	Intermediate Similarity	NPC218107
0.8	Intermediate Similarity	NPC472186
0.8	Intermediate Similarity	NPC475586
0.7981	Intermediate Similarity	NPC187435
0.7981	Intermediate Similarity	NPC180744
0.7981	Intermediate Similarity	NPC475074
0.7981	Intermediate Similarity	NPC67321
0.7981	Intermediate Similarity	NPC302788
0.798	Intermediate Similarity	NPC165632
0.798	Intermediate Similarity	NPC171598
0.798	Intermediate Similarity	NPC16967
0.7979	Intermediate Similarity	NPC471219
0.7978	Intermediate Similarity	NPC189206
0.7961	Intermediate Similarity	NPC477127
0.7959	Intermediate Similarity	NPC57117
0.7959	Intermediate Similarity	NPC477722
0.7941	Intermediate Similarity	NPC11956
0.7938	Intermediate Similarity	NPC473675
0.7938	Intermediate Similarity	NPC329842
0.7938	Intermediate Similarity	NPC72845
0.7925	Intermediate Similarity	NPC177047
0.7921	Intermediate Similarity	NPC472187
0.7921	Intermediate Similarity	NPC473545
0.7921	Intermediate Similarity	NPC251680
0.7921	Intermediate Similarity	NPC473204
0.7921	Intermediate Similarity	NPC47024
0.7909	Intermediate Similarity	NPC470420
0.7905	Intermediate Similarity	NPC38948
0.7905	Intermediate Similarity	NPC475263
0.7905	Intermediate Similarity	NPC50124
0.79	Intermediate Similarity	NPC199099
0.79	Intermediate Similarity	NPC472998
0.79	Intermediate Similarity	NPC472188
0.79	Intermediate Similarity	NPC205143
0.79	Intermediate Similarity	NPC84335
0.79	Intermediate Similarity	NPC38530
0.7895	Intermediate Similarity	NPC476600
0.789	Intermediate Similarity	NPC471816
0.789	Intermediate Similarity	NPC470075
0.7885	Intermediate Similarity	NPC81630
0.7879	Intermediate Similarity	NPC471372
0.7879	Intermediate Similarity	NPC281134
0.7879	Intermediate Similarity	NPC471362
0.7879	Intermediate Similarity	NPC56369
0.7879	Intermediate Similarity	NPC472189
0.7879	Intermediate Similarity	NPC469583
0.787	Intermediate Similarity	NPC477126
0.787	Intermediate Similarity	NPC171126
0.787	Intermediate Similarity	NPC159333
0.7864	Intermediate Similarity	NPC112009
0.7864	Intermediate Similarity	NPC297617
0.7864	Intermediate Similarity	NPC472821
0.7864	Intermediate Similarity	NPC473523
0.7864	Intermediate Similarity	NPC180204
0.7857	Intermediate Similarity	NPC475657
0.7857	Intermediate Similarity	NPC53555
0.7849	Intermediate Similarity	NPC476927
0.7849	Intermediate Similarity	NPC12283
0.7849	Intermediate Similarity	NPC474193
0.7835	Intermediate Similarity	NPC472642
0.7835	Intermediate Similarity	NPC475776
0.7835	Intermediate Similarity	NPC310479
0.783	Intermediate Similarity	NPC206618
0.783	Intermediate Similarity	NPC299590
0.783	Intermediate Similarity	NPC469370
0.7826	Intermediate Similarity	NPC170303
0.7822	Intermediate Similarity	NPC264378
0.7812	Intermediate Similarity	NPC291665
0.781	Intermediate Similarity	NPC473586
0.781	Intermediate Similarity	NPC179380
0.781	Intermediate Similarity	NPC109376
0.78	Intermediate Similarity	NPC94905
0.78	Intermediate Similarity	NPC472997
0.78	Intermediate Similarity	NPC472995
0.78	Intermediate Similarity	NPC472996
0.78	Intermediate Similarity	NPC242848
0.78	Intermediate Similarity	NPC473964
0.78	Intermediate Similarity	NPC8954
0.7798	Intermediate Similarity	NPC216665
0.7798	Intermediate Similarity	NPC90472
0.7798	Intermediate Similarity	NPC43213
0.7788	Intermediate Similarity	NPC473543
0.7778	Intermediate Similarity	NPC119562
0.7778	Intermediate Similarity	NPC279410
0.7778	Intermediate Similarity	NPC38830
0.7778	Intermediate Similarity	NPC191521
0.7778	Intermediate Similarity	NPC475391
0.7778	Intermediate Similarity	NPC470063
0.7768	Intermediate Similarity	NPC4548
0.7767	Intermediate Similarity	NPC475344
0.7767	Intermediate Similarity	NPC472815
0.7767	Intermediate Similarity	NPC121423
0.7767	Intermediate Similarity	NPC165250
0.7767	Intermediate Similarity	NPC476471
0.7767	Intermediate Similarity	NPC470972

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 NPC475380 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	202
0.1-0.2	1713
0.2-0.3	4054
0.3-0.4	2150
0.4-0.5	654
0.5-0.6	225
0.6-0.7	136
0.7-0.8	15
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8155	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7638	Approved
0.7925	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD7639	Approved
0.7921	Intermediate Similarity	NPD7640	Approved
0.783	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7745	Intermediate Similarity	NPD6648	Approved
0.7742	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD5344	Discontinued
0.7589	Intermediate Similarity	NPD7328	Approved
0.7589	Intermediate Similarity	NPD7327	Approved
0.757	Intermediate Similarity	NPD6686	Approved
0.7522	Intermediate Similarity	NPD7516	Approved
0.7476	Intermediate Similarity	NPD4225	Approved
0.7383	Intermediate Similarity	NPD6008	Approved
0.7304	Intermediate Similarity	NPD8294	Approved
0.7304	Intermediate Similarity	NPD8377	Approved
0.7264	Intermediate Similarity	NPD7632	Discontinued
0.7241	Intermediate Similarity	NPD8296	Approved
0.7241	Intermediate Similarity	NPD8380	Approved
0.7241	Intermediate Similarity	NPD8335	Approved
0.7241	Intermediate Similarity	NPD8379	Approved
0.7241	Intermediate Similarity	NPD8033	Approved
0.7241	Intermediate Similarity	NPD8378	Approved
0.72	Intermediate Similarity	NPD6051	Approved
0.7193	Intermediate Similarity	NPD7115	Discovery
0.7143	Intermediate Similarity	NPD1694	Approved
0.7143	Intermediate Similarity	NPD7507	Approved
0.7129	Intermediate Similarity	NPD7838	Discovery
0.7094	Intermediate Similarity	NPD7503	Approved
0.7087	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7900	Approved
0.6967	Remote Similarity	NPD7319	Approved
0.6961	Remote Similarity	NPD6698	Approved
0.6961	Remote Similarity	NPD46	Approved
0.6937	Remote Similarity	NPD6899	Approved
0.6937	Remote Similarity	NPD6881	Approved
0.6923	Remote Similarity	NPD7748	Approved
0.6909	Remote Similarity	NPD6675	Approved
0.6909	Remote Similarity	NPD7128	Approved
0.6909	Remote Similarity	NPD5739	Approved
0.6909	Remote Similarity	NPD6402	Approved
0.6903	Remote Similarity	NPD6650	Approved
0.6903	Remote Similarity	NPD6649	Approved
0.69	Remote Similarity	NPD7146	Approved
0.69	Remote Similarity	NPD6409	Approved
0.69	Remote Similarity	NPD7334	Approved
0.69	Remote Similarity	NPD7521	Approved
0.69	Remote Similarity	NPD5330	Approved
0.69	Remote Similarity	NPD6684	Approved
0.6887	Remote Similarity	NPD7902	Approved
0.6875	Remote Similarity	NPD6372	Approved
0.6875	Remote Similarity	NPD6373	Approved
0.6857	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD5697	Approved
0.6842	Remote Similarity	NPD6882	Approved
0.6842	Remote Similarity	NPD8297	Approved
0.6832	Remote Similarity	NPD3573	Approved
0.6814	Remote Similarity	NPD7102	Approved
0.6814	Remote Similarity	NPD6883	Approved
0.6814	Remote Similarity	NPD7290	Approved
0.6786	Remote Similarity	NPD7320	Approved
0.6765	Remote Similarity	NPD6672	Approved
0.6765	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5737	Approved
0.6765	Remote Similarity	NPD6903	Approved
0.6754	Remote Similarity	NPD6847	Approved
0.6754	Remote Similarity	NPD6617	Approved
0.6754	Remote Similarity	NPD8130	Phase 1
0.6754	Remote Similarity	NPD6869	Approved
0.6742	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7515	Phase 2
0.6731	Remote Similarity	NPD5693	Phase 1
0.6726	Remote Similarity	NPD6014	Approved
0.6726	Remote Similarity	NPD6012	Approved
0.6726	Remote Similarity	NPD6013	Approved
0.6723	Remote Similarity	NPD6319	Approved
0.6699	Remote Similarity	NPD1695	Approved
0.6696	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD6399	Phase 3
0.6638	Remote Similarity	NPD4632	Approved
0.6637	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD6011	Approved
0.6633	Remote Similarity	NPD7525	Registered
0.6574	Remote Similarity	NPD6083	Phase 2
0.6574	Remote Similarity	NPD6084	Phase 2
0.6571	Remote Similarity	NPD7637	Suspended
0.6557	Remote Similarity	NPD7604	Phase 2
0.6552	Remote Similarity	NPD6053	Discontinued
0.6538	Remote Similarity	NPD6904	Approved
0.6538	Remote Similarity	NPD6080	Approved
0.6538	Remote Similarity	NPD6673	Approved
0.6535	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6371	Approved
0.6514	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD7492	Approved
0.65	Remote Similarity	NPD5209	Approved
0.6496	Remote Similarity	NPD8133	Approved
0.6486	Remote Similarity	NPD5211	Phase 2
0.6471	Remote Similarity	NPD6009	Approved
0.6471	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD4696	Approved
0.6455	Remote Similarity	NPD5286	Approved
0.6455	Remote Similarity	NPD5285	Approved
0.6452	Remote Similarity	NPD6616	Approved
0.6449	Remote Similarity	NPD6001	Approved
0.6446	Remote Similarity	NPD6054	Approved
0.6436	Remote Similarity	NPD6695	Phase 3
0.6422	Remote Similarity	NPD4755	Approved
0.6415	Remote Similarity	NPD8034	Phase 2
0.6415	Remote Similarity	NPD6079	Approved
0.6415	Remote Similarity	NPD8035	Phase 2
0.6408	Remote Similarity	NPD3618	Phase 1
0.6404	Remote Similarity	NPD6412	Phase 2
0.6404	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7078	Approved
0.6393	Remote Similarity	NPD5983	Phase 2
0.6389	Remote Similarity	NPD5695	Phase 3
0.6387	Remote Similarity	NPD6274	Approved
0.6381	Remote Similarity	NPD5328	Approved
0.6372	Remote Similarity	NPD5141	Approved
0.6364	Remote Similarity	NPD5696	Approved
0.6364	Remote Similarity	NPD7101	Approved
0.6364	Remote Similarity	NPD7645	Phase 2
0.6364	Remote Similarity	NPD7100	Approved
0.6355	Remote Similarity	NPD4202	Approved
0.6349	Remote Similarity	NPD7736	Approved
0.6341	Remote Similarity	NPD6370	Approved
0.6339	Remote Similarity	NPD5224	Approved
0.6339	Remote Similarity	NPD5226	Approved
0.6339	Remote Similarity	NPD4633	Approved
0.6339	Remote Similarity	NPD5225	Approved
0.6321	Remote Similarity	NPD3168	Discontinued
0.632	Remote Similarity	NPD6336	Discontinued
0.6311	Remote Similarity	NPD6059	Approved
0.6306	Remote Similarity	NPD4700	Approved
0.6293	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.629	Remote Similarity	NPD8328	Phase 3
0.6286	Remote Similarity	NPD5208	Approved
0.6283	Remote Similarity	NPD5174	Approved
0.6283	Remote Similarity	NPD5175	Approved
0.6281	Remote Similarity	NPD6335	Approved
0.627	Remote Similarity	NPD8293	Discontinued
0.6262	Remote Similarity	NPD6050	Approved
0.626	Remote Similarity	NPD6016	Approved
0.626	Remote Similarity	NPD6015	Approved
0.625	Remote Similarity	NPD6098	Approved
0.625	Remote Similarity	NPD5223	Approved
0.6239	Remote Similarity	NPD4634	Approved
0.621	Remote Similarity	NPD5988	Approved
0.6207	Remote Similarity	NPD4730	Approved
0.6207	Remote Similarity	NPD4729	Approved
0.6204	Remote Similarity	NPD5779	Approved
0.6204	Remote Similarity	NPD5778	Approved
0.6198	Remote Similarity	NPD6317	Approved
0.619	Remote Similarity	NPD7524	Approved
0.619	Remote Similarity	NPD7750	Discontinued
0.6182	Remote Similarity	NPD5222	Approved
0.6182	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD5221	Approved
0.6174	Remote Similarity	NPD4768	Approved
0.6174	Remote Similarity	NPD4767	Approved
0.6168	Remote Similarity	NPD5692	Phase 3
0.6154	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD6313	Approved
0.6148	Remote Similarity	NPD6314	Approved
0.6139	Remote Similarity	NPD6931	Approved
0.6139	Remote Similarity	NPD6930	Phase 2
0.6129	Remote Similarity	NPD6921	Approved
0.6129	Remote Similarity	NPD6909	Approved
0.6129	Remote Similarity	NPD6908	Approved
0.6126	Remote Similarity	NPD5173	Approved
0.6122	Remote Similarity	NPD8039	Approved
0.6116	Remote Similarity	NPD6868	Approved
0.6111	Remote Similarity	NPD5694	Approved
0.6102	Remote Similarity	NPD5247	Approved
0.6102	Remote Similarity	NPD5248	Approved
0.6102	Remote Similarity	NPD5250	Approved
0.6102	Remote Similarity	NPD5251	Approved
0.6102	Remote Similarity	NPD5249	Phase 3
0.6095	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD7260	Phase 2
0.6075	Remote Similarity	NPD4753	Phase 2
0.6068	Remote Similarity	NPD5128	Approved
0.6058	Remote Similarity	NPD3665	Phase 1
0.6058	Remote Similarity	NPD3666	Approved
0.6058	Remote Similarity	NPD4786	Approved
0.6058	Remote Similarity	NPD3133	Approved
0.6058	Remote Similarity	NPD3668	Phase 3
0.6053	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.604	Remote Similarity	NPD4195	Approved
0.604	Remote Similarity	NPD6929	Approved
0.6038	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD4697	Phase 3
0.6019	Remote Similarity	NPD5207	Approved
0.6019	Remote Similarity	NPD5785	Approved
0.6019	Remote Similarity	NPD3667	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