NPASS Compound

Structure

NPC89018 OpenBabel07101718302D 45 48 0 0 1 0 0 0 0 0999 V2000 -4.3051 2.6204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0735 -1.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7461 2.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7312 4.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1865 3.7871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0349 2.3177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3946 -2.7268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0140 1.5898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 3.4130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3381 2.3177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9796 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3734 2.3177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 -0.7367 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3477 3.8004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7570 4.7977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3381 4.2769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0349 1.3381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1812 -1.9343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7976 3.1102 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9343 3.1102 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4898 2.8075 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3381 1.3381 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3734 1.3381 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3586 1.3381 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7976 0.5456 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9343 0.5456 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7976 -1.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3586 2.3177 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4898 0.8484 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8660 0.2429 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3051 1.0354 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -4.9234 4.5929 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1812 5.5902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3381 5.2565 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8832 0.8484 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1554 -2.0367 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1004 -1.9710 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 1.2225 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 -3.3734 3.9028 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3586 3.9028 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4898 3.7871 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1865 0.8484 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2172 -1.0394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3734 -0.2469 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 2 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 6 17 1 0 0 0 0 7 18 1 0 0 0 0 9 19 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 10 22 1 0 0 0 0 11 39 1 0 0 0 0 12 19 1 0 0 0 0 12 23 1 0 0 0 0 13 27 1 0 0 0 0 13 30 1 1 0 0 0 14 32 2 0 0 0 0 14 40 1 0 0 0 0 15 33 2 0 0 0 0 15 41 1 0 0 0 0 16 34 2 0 0 0 0 16 42 1 0 0 0 0 17 35 2 0 0 0 0 17 43 1 0 0 0 0 18 36 2 0 0 0 0 18 44 1 0 0 0 0 19 40 1 6 0 0 0 20 28 1 6 0 0 0 20 41 1 0 0 0 0 21 28 1 1 0 0 0 21 42 1 0 0 0 0 22 29 1 1 0 0 0 22 43 1 0 0 0 0 23 25 1 0 0 0 0 23 31 1 1 0 0 0 24 26 1 0 0 0 0 24 28 1 6 0 0 0 24 29 1 0 0 0 0 25 30 1 1 0 0 0 25 45 1 0 0 0 0 26 30 1 6 0 0 0 26 44 1 0 0 0 0 27 37 2 0 0 0 0 27 45 1 0 0 0 0 28 8 1 6 0 0 0 29 11 1 6 0 0 0 29 39 1 0 0 0 0 30 38 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	658.2
Volume:	613.029
LogP:	2.077
LogD:	0.494
LogS:	-3.96
# Rotatable Bonds:	10
TPSA:	190.56
# H-Bond Aceptor:	14
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.146
Synthetic Accessibility Score:	6.396
Fsp3:	0.733
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.243
MDCK Permeability:	0.00031940528424456716
Pgp-inhibitor:	0.999
Pgp-substrate:	0.168
Human Intestinal Absorption (HIA):	0.333
20% Bioavailability (F20%):	0.04
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.071
Plasma Protein Binding (PPB):	51.63289260864258%
Volume Distribution (VD):	1.535
Pgp-substrate:	39.847415924072266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.012
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.006
CYP2D6-inhibitor:	0.085
CYP2D6-substrate:	0.056
CYP3A4-inhibitor:	0.223
CYP3A4-substrate:	0.165

ADMET: Excretion

Clearance (CL):	2.584
Half-life (T1/2):	0.195

ADMET: Toxicity

hERG Blockers:	0.152
Human Hepatotoxicity (H-HT):	0.992
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.073
Rat Oral Acute Toxicity:	0.694
Maximum Recommended Daily Dose:	0.69
Skin Sensitization:	0.386
Carcinogencity:	0.041
Eye Corrosion:	0.004
Eye Irritation:	0.017
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC89018

Natural Product ID:	NPC89018
*Common Name:**	DLPMIBNBRFELNO-CZIIIUHOSA-N
IUPAC Name:	n.a.
Synonyms:	Rel-Gemmacolide V
Standard InCHIKey:	DLPMIBNBRFELNO-CZIIIUHOSA-N
Standard InCHI:	InChI=1S/C30H39ClO14/c1-12-19(40-14(3)32)9-20(41-15(4)33)28(8)21(42-16(5)34)10-22(43-17(6)35)29(11-39-29)24(28)26(44-18(7)36)30(38)13(2)27(37)45-25(30)23(12)31/h13,19-26,38H,1,9-11H2,2-8H3/t13-,19+,20-,21-,22+,23-,24+,25-,26-,28-,29+,30-/m0/s1
SMILES:	CC(=O)O[C@@H]1C[C@H](OC(=O)C)[C@@]2(C)[C@@H](OC(=O)C)C[C@H]([C@]3([C@@H]2[C@@H]([C@]2([C@H]([C@H](C1=C)Cl)OC(=O)[C@@H]2C)O)OC(=O)C)OC3)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2043336
PubChem CID:	66575026
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO15994	Dichotella gemmacea	Species	Ellisellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21721519]
NPO15994	Dichotella gemmacea	Species	Ellisellidae	Eukaryota	n.a.	South China Sea	n.a.	PMID[21721519]
NPO15994	Dichotella gemmacea	Species	Ellisellidae	Eukaryota	n.a.	South China Sea	n.a.	PMID[22647719]
NPO15994	Dichotella gemmacea	Species	Ellisellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23477504]
NPO15994	Dichotella gemmacea	Species	Ellisellidae	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
Others	3

Activity Type	# Activity
Cell Line	2
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	<	1500.0	nM	PMID[510604]
NPT2351	Cell Line	MG-63	Homo sapiens	IC50	=	20500.0	nM	PMID[510604]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	20.0	mm	PMID[510604]
NPT1231	Organism	Microbotryum violaceum	Microbotryum violaceum	IZ	=	11.0	mm	PMID[510604]
NPT3534	Organism	Xanthomonas campestris	Xanthomonas campestris	IZ	=	13.0	mm	PMID[510604]

☑ 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 NPC89018 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	270
0.1-0.2	2102
0.2-0.3	6173
0.3-0.4	12606
0.4-0.5	10726
0.5-0.6	7866
0.6-0.7	2714
0.7-0.8	209
0.8-0.85	13
0.85-0.9	9
0.9-0.95	0
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9905	High Similarity	NPC88867
0.9905	High Similarity	NPC226608
0.9811	High Similarity	NPC470466
0.9712	High Similarity	NPC11491
0.9712	High Similarity	NPC156248
0.9712	High Similarity	NPC140409
0.9619	High Similarity	NPC170294
0.9519	High Similarity	NPC128210
0.9115	High Similarity	NPC282003
0.9115	High Similarity	NPC188222
0.9115	High Similarity	NPC310035
0.9074	High Similarity	NPC470467
0.9035	High Similarity	NPC303006
0.8991	High Similarity	NPC470468
0.8942	High Similarity	NPC98225
0.8929	High Similarity	NPC476714
0.8889	High Similarity	NPC475191
0.8512	High Similarity	NPC470185
0.8455	Intermediate Similarity	NPC94377
0.8333	Intermediate Similarity	NPC73314
0.819	Intermediate Similarity	NPC296822
0.8182	Intermediate Similarity	NPC283850
0.8158	Intermediate Similarity	NPC473877
0.8103	Intermediate Similarity	NPC474333
0.8091	Intermediate Similarity	NPC99510
0.8091	Intermediate Similarity	NPC61442
0.8087	Intermediate Similarity	NPC477126
0.8053	Intermediate Similarity	NPC42662
0.8051	Intermediate Similarity	NPC470186
0.7949	Intermediate Similarity	NPC329869
0.7928	Intermediate Similarity	NPC72842
0.7913	Intermediate Similarity	NPC194619
0.789	Intermediate Similarity	NPC152480
0.7876	Intermediate Similarity	NPC475510
0.7876	Intermediate Similarity	NPC475587
0.7838	Intermediate Similarity	NPC183571
0.7833	Intermediate Similarity	NPC475003
0.7826	Intermediate Similarity	NPC473975
0.7826	Intermediate Similarity	NPC473594
0.7826	Intermediate Similarity	NPC474586
0.7826	Intermediate Similarity	NPC473843
0.7807	Intermediate Similarity	NPC473939
0.7807	Intermediate Similarity	NPC473595
0.7805	Intermediate Similarity	NPC470973
0.7798	Intermediate Similarity	NPC474395
0.7768	Intermediate Similarity	NPC474165
0.7768	Intermediate Similarity	NPC69171
0.7748	Intermediate Similarity	NPC308824
0.7739	Intermediate Similarity	NPC475922
0.7731	Intermediate Similarity	NPC476712
0.7731	Intermediate Similarity	NPC476713
0.7706	Intermediate Similarity	NPC473964
0.7672	Intermediate Similarity	NPC281624
0.7672	Intermediate Similarity	NPC161816
0.7672	Intermediate Similarity	NPC115257
0.7664	Intermediate Similarity	NPC122057
0.7658	Intermediate Similarity	NPC477656
0.7652	Intermediate Similarity	NPC37628
0.7647	Intermediate Similarity	NPC476710
0.7647	Intermediate Similarity	NPC476711
0.7636	Intermediate Similarity	NPC136781
0.7636	Intermediate Similarity	NPC473963
0.7611	Intermediate Similarity	NPC156681
0.7607	Intermediate Similarity	NPC157476
0.7589	Intermediate Similarity	NPC475958
0.7565	Intermediate Similarity	NPC78966
0.7565	Intermediate Similarity	NPC216636
0.7565	Intermediate Similarity	NPC284732
0.7545	Intermediate Similarity	NPC93245
0.7541	Intermediate Similarity	NPC317635
0.7541	Intermediate Similarity	NPC329008
0.7522	Intermediate Similarity	NPC474709
0.75	Intermediate Similarity	NPC477655
0.7478	Intermediate Similarity	NPC9303
0.7478	Intermediate Similarity	NPC16313
0.7477	Intermediate Similarity	NPC253618
0.7477	Intermediate Similarity	NPC77001
0.7477	Intermediate Similarity	NPC474921
0.746	Intermediate Similarity	NPC478207
0.7458	Intermediate Similarity	NPC94650
0.7456	Intermediate Similarity	NPC474166
0.7456	Intermediate Similarity	NPC19239
0.7455	Intermediate Similarity	NPC259042
0.7455	Intermediate Similarity	NPC157686
0.7438	Intermediate Similarity	NPC53396
0.7438	Intermediate Similarity	NPC58662
0.7438	Intermediate Similarity	NPC469684
0.7438	Intermediate Similarity	NPC98249
0.7436	Intermediate Similarity	NPC154906
0.7414	Intermediate Similarity	NPC319438
0.7414	Intermediate Similarity	NPC324327
0.7414	Intermediate Similarity	NPC72813
0.7414	Intermediate Similarity	NPC474421
0.7414	Intermediate Similarity	NPC194620
0.7414	Intermediate Similarity	NPC326994
0.7407	Intermediate Similarity	NPC471378
0.7407	Intermediate Similarity	NPC312471
0.7387	Intermediate Similarity	NPC284518
0.7377	Intermediate Similarity	NPC284707
0.7373	Intermediate Similarity	NPC472214
0.7373	Intermediate Similarity	NPC472215
0.7368	Intermediate Similarity	NPC164551
0.7364	Intermediate Similarity	NPC469596
0.7364	Intermediate Similarity	NPC225474
0.7364	Intermediate Similarity	NPC148000
0.7355	Intermediate Similarity	NPC270478
0.7355	Intermediate Similarity	NPC477509
0.735	Intermediate Similarity	NPC469916
0.735	Intermediate Similarity	NPC472439
0.735	Intermediate Similarity	NPC169888
0.735	Intermediate Similarity	NPC55972
0.735	Intermediate Similarity	NPC233379
0.735	Intermediate Similarity	NPC14862
0.735	Intermediate Similarity	NPC208461
0.735	Intermediate Similarity	NPC474664
0.735	Intermediate Similarity	NPC289702
0.735	Intermediate Similarity	NPC327286
0.735	Intermediate Similarity	NPC273155
0.7339	Intermediate Similarity	NPC91251
0.7328	Intermediate Similarity	NPC475802
0.7321	Intermediate Similarity	NPC472998
0.7317	Intermediate Similarity	NPC472667
0.7311	Intermediate Similarity	NPC469655
0.7311	Intermediate Similarity	NPC469656
0.7311	Intermediate Similarity	NPC474846
0.7304	Intermediate Similarity	NPC4620
0.7297	Intermediate Similarity	NPC56369
0.7295	Intermediate Similarity	NPC478204
0.7295	Intermediate Similarity	NPC470775
0.7295	Intermediate Similarity	NPC473590
0.7295	Intermediate Similarity	NPC176513
0.7288	Intermediate Similarity	NPC322912
0.7288	Intermediate Similarity	NPC15218
0.7281	Intermediate Similarity	NPC111292
0.7281	Intermediate Similarity	NPC242666
0.7265	Intermediate Similarity	NPC67321
0.7265	Intermediate Similarity	NPC166993
0.7265	Intermediate Similarity	NPC187435
0.7258	Intermediate Similarity	NPC143755
0.7258	Intermediate Similarity	NPC251226
0.7258	Intermediate Similarity	NPC142882
0.725	Intermediate Similarity	NPC269530
0.725	Intermediate Similarity	NPC317687
0.725	Intermediate Similarity	NPC42658
0.7248	Intermediate Similarity	NPC153853
0.7248	Intermediate Similarity	NPC475776
0.7244	Intermediate Similarity	NPC473635
0.7241	Intermediate Similarity	NPC475676
0.7241	Intermediate Similarity	NPC146731
0.7241	Intermediate Similarity	NPC220964
0.7241	Intermediate Similarity	NPC477127
0.7236	Intermediate Similarity	NPC478205
0.7236	Intermediate Similarity	NPC478206
0.7236	Intermediate Similarity	NPC124676
0.7236	Intermediate Similarity	NPC108581
0.7236	Intermediate Similarity	NPC146280
0.7232	Intermediate Similarity	NPC158416
0.7232	Intermediate Similarity	NPC256227
0.7232	Intermediate Similarity	NPC39859
0.7232	Intermediate Similarity	NPC76862
0.7232	Intermediate Similarity	NPC470883
0.7222	Intermediate Similarity	NPC473802
0.7222	Intermediate Similarity	NPC67251
0.7222	Intermediate Similarity	NPC472399
0.7217	Intermediate Similarity	NPC472552
0.7213	Intermediate Similarity	NPC154363
0.7213	Intermediate Similarity	NPC234858
0.7213	Intermediate Similarity	NPC471127
0.7207	Intermediate Similarity	NPC66581
0.7207	Intermediate Similarity	NPC24861
0.7203	Intermediate Similarity	NPC181994
0.7203	Intermediate Similarity	NPC218123
0.7203	Intermediate Similarity	NPC151393
0.7203	Intermediate Similarity	NPC112895
0.7203	Intermediate Similarity	NPC231278
0.72	Intermediate Similarity	NPC477046
0.72	Intermediate Similarity	NPC159456
0.72	Intermediate Similarity	NPC4021
0.72	Intermediate Similarity	NPC102822
0.72	Intermediate Similarity	NPC310511
0.7196	Intermediate Similarity	NPC246347
0.7193	Intermediate Similarity	NPC188968
0.7193	Intermediate Similarity	NPC79303
0.7193	Intermediate Similarity	NPC272223
0.7193	Intermediate Similarity	NPC271295
0.7193	Intermediate Similarity	NPC474718
0.7193	Intermediate Similarity	NPC47024
0.719	Intermediate Similarity	NPC94509
0.7188	Intermediate Similarity	NPC470780
0.7182	Intermediate Similarity	NPC312805
0.7179	Intermediate Similarity	NPC200957
0.7179	Intermediate Similarity	NPC474101
0.7179	Intermediate Similarity	NPC295366
0.7179	Intermediate Similarity	NPC470979
0.7179	Intermediate Similarity	NPC138908
0.7179	Intermediate Similarity	NPC470975
0.7179	Intermediate Similarity	NPC103088
0.7168	Intermediate Similarity	NPC111348
0.7167	Intermediate Similarity	NPC317107
0.7165	Intermediate Similarity	NPC473919

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 NPC89018 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	242
0.1-0.2	2572
0.2-0.3	3841
0.3-0.4	1730
0.4-0.5	500
0.5-0.6	241
0.6-0.7	24
0.7-0.8	0
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
0.735	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD5344	Discontinued
0.681	Remote Similarity	NPD4225	Approved
0.6797	Remote Similarity	NPD6921	Approved
0.6746	Remote Similarity	NPD7115	Discovery
0.664	Remote Similarity	NPD8133	Approved
0.6637	Remote Similarity	NPD46	Approved
0.6637	Remote Similarity	NPD6698	Approved
0.661	Remote Similarity	NPD6648	Approved
0.6557	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD1700	Approved
0.6532	Remote Similarity	NPD6371	Approved
0.6504	Remote Similarity	NPD6686	Approved
0.65	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD7319	Approved
0.637	Remote Similarity	NPD6033	Approved
0.632	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD8035	Phase 2
0.6293	Remote Similarity	NPD8034	Phase 2
0.6288	Remote Similarity	NPD5983	Phase 2
0.6288	Remote Similarity	NPD8517	Approved
0.6288	Remote Similarity	NPD8513	Phase 3
0.6288	Remote Similarity	NPD8516	Approved
0.6288	Remote Similarity	NPD8515	Approved
0.626	Remote Similarity	NPD7516	Approved
0.625	Remote Similarity	NPD7638	Approved
0.625	Remote Similarity	NPD4632	Approved
0.6231	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD7507	Approved
0.6222	Remote Similarity	NPD6336	Discontinued
0.6212	Remote Similarity	NPD6319	Approved
0.621	Remote Similarity	NPD6008	Approved
0.6198	Remote Similarity	NPD7639	Approved
0.6198	Remote Similarity	NPD7640	Approved
0.6195	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD7327	Approved
0.6183	Remote Similarity	NPD7328	Approved
0.6154	Remote Similarity	NPD7983	Approved
0.6136	Remote Similarity	NPD7100	Approved
0.6102	Remote Similarity	NPD6399	Phase 3
0.6094	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6074	Remote Similarity	NPD8328	Phase 3
0.6068	Remote Similarity	NPD7838	Discovery
0.6061	Remote Similarity	NPD6335	Approved
0.6058	Remote Similarity	NPD8074	Phase 3
0.605	Remote Similarity	NPD5282	Discontinued
0.6029	Remote Similarity	NPD7492	Approved
0.6015	Remote Similarity	NPD7101	Approved
0.6	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5985	Remote Similarity	NPD6616	Approved
0.5985	Remote Similarity	NPD6009	Approved
0.5983	Remote Similarity	NPD1695	Approved
0.597	Remote Similarity	NPD6054	Approved
0.597	Remote Similarity	NPD6059	Approved
0.5966	Remote Similarity	NPD5778	Approved
0.5966	Remote Similarity	NPD5779	Approved
0.5942	Remote Similarity	NPD8293	Discontinued
0.5942	Remote Similarity	NPD7078	Approved
0.594	Remote Similarity	NPD6313	Approved
0.594	Remote Similarity	NPD6314	Approved
0.5938	Remote Similarity	NPD6372	Approved
0.5938	Remote Similarity	NPD6373	Approved
0.5932	Remote Similarity	NPD3168	Discontinued
0.5929	Remote Similarity	NPD5956	Approved
0.5926	Remote Similarity	NPD8378	Approved
0.5926	Remote Similarity	NPD8379	Approved
0.5926	Remote Similarity	NPD8296	Approved
0.5926	Remote Similarity	NPD8033	Approved
0.5926	Remote Similarity	NPD8335	Approved
0.5926	Remote Similarity	NPD8380	Approved
0.5923	Remote Similarity	NPD8297	Approved
0.5913	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD7902	Approved
0.5899	Remote Similarity	NPD7736	Approved
0.5882	Remote Similarity	NPD6370	Approved
0.5882	Remote Similarity	NPD7637	Suspended
0.5882	Remote Similarity	NPD6411	Approved
0.5852	Remote Similarity	NPD8377	Approved
0.5852	Remote Similarity	NPD8294	Approved
0.5846	Remote Similarity	NPD6649	Approved
0.5846	Remote Similarity	NPD6650	Approved
0.584	Remote Similarity	NPD7632	Discontinued
0.5827	Remote Similarity	NPD5739	Approved
0.5827	Remote Similarity	NPD7128	Approved
0.5827	Remote Similarity	NPD6402	Approved
0.5827	Remote Similarity	NPD6675	Approved
0.582	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD7524	Approved
0.5809	Remote Similarity	NPD6015	Approved
0.5809	Remote Similarity	NPD6016	Approved
0.5789	Remote Similarity	NPD6868	Approved
0.5785	Remote Similarity	NPD7748	Approved
0.5781	Remote Similarity	NPD6412	Phase 2
0.5778	Remote Similarity	NPD4522	Approved
0.5766	Remote Similarity	NPD5988	Approved
0.5736	Remote Similarity	NPD6899	Approved
0.5736	Remote Similarity	NPD6881	Approved
0.5736	Remote Similarity	NPD7320	Approved
0.5725	Remote Similarity	NPD5215	Approved
0.5725	Remote Similarity	NPD7604	Phase 2
0.5714	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6101	Approved
0.5693	Remote Similarity	NPD7503	Approved
0.5682	Remote Similarity	NPD6882	Approved
0.5682	Remote Similarity	NPD6053	Discontinued
0.5667	Remote Similarity	NPD5785	Approved
0.5659	Remote Similarity	NPD5697	Approved
0.5659	Remote Similarity	NPD5701	Approved
0.5656	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD7900	Approved
0.5652	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5649	Remote Similarity	NPD5169	Approved
0.5649	Remote Similarity	NPD7290	Approved
0.5649	Remote Similarity	NPD6883	Approved
0.5649	Remote Similarity	NPD7102	Approved
0.5649	Remote Similarity	NPD4634	Approved
0.5648	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5643	Remote Similarity	NPD8273	Phase 1
0.5641	Remote Similarity	NPD1694	Approved
0.562	Remote Similarity	NPD7515	Phase 2
0.561	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5606	Remote Similarity	NPD6869	Approved
0.5606	Remote Similarity	NPD5216	Approved
0.5606	Remote Similarity	NPD8130	Phase 1
0.5606	Remote Similarity	NPD5127	Approved
0.5606	Remote Similarity	NPD6617	Approved
0.5606	Remote Similarity	NPD6847	Approved
0.5606	Remote Similarity	NPD5217	Approved
0.56	Remote Similarity	NPD8029	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