NPASS Compound

Structure

CID282003 OpenBabel06191716092D 44 47 0 0 1 0 0 0 0 0999 V2000 3.8815 -3.7855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7295 -2.3167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3032 -2.6193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0730 1.3119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7305 -4.8979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1855 -3.7855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3944 2.7256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0136 -1.5891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7964 -3.1089 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8652 -3.4115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0335 -2.3167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3376 -2.3167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9792 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8815 -2.8063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3720 -2.3167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8652 0.7363 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7567 -4.7956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3376 -4.2751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1811 1.9334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9339 -3.1089 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4896 -2.8063 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3376 -1.3376 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0335 -1.3376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3720 -1.3376 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3584 -1.3376 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7964 -0.5454 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9339 -0.5454 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7964 1.0389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3584 -2.3167 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4896 -0.8480 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8652 -0.2428 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3032 -1.0350 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -0.1811 -5.5877 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3376 -5.2542 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1549 2.0358 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8815 -0.8480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0990 1.9702 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8652 -1.2220 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 -0.3584 -3.9011 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4896 -3.7855 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2171 1.0389 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1855 -0.8480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3720 0.2468 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 2 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 18 1 0 0 0 0 7 19 1 0 0 0 0 9 10 2 0 0 0 0 9 15 1 0 0 0 0 10 20 1 0 0 0 0 11 14 1 0 0 0 0 11 23 1 0 0 0 0 12 21 1 0 0 0 0 12 22 1 0 0 0 0 13 39 1 0 0 0 0 15 24 1 0 0 0 0 16 28 1 0 0 0 0 16 31 1 6 0 0 0 17 33 2 0 0 0 0 17 40 1 0 0 0 0 18 34 2 0 0 0 0 18 41 1 0 0 0 0 19 35 2 0 0 0 0 19 42 1 0 0 0 0 20 29 1 1 0 0 0 20 40 1 0 0 0 0 21 29 1 6 0 0 0 21 41 1 0 0 0 0 22 30 1 6 0 0 0 22 43 1 0 0 0 0 23 36 2 0 0 0 0 23 43 1 0 0 0 0 24 26 1 0 0 0 0 24 32 1 6 0 0 0 25 27 1 0 0 0 0 25 29 1 1 0 0 0 25 30 1 0 0 0 0 26 31 1 6 0 0 0 26 44 1 0 0 0 0 27 31 1 1 0 0 0 27 42 1 0 0 0 0 28 37 2 0 0 0 0 28 44 1 0 0 0 0 29 8 1 1 0 0 0 30 13 1 1 0 0 0 30 39 1 0 0 0 0 31 38 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	640.23
Volume:	612.745
LogP:	3.221
LogD:	1.215
LogS:	-4.627
# Rotatable Bonds:	10
TPSA:	164.26
# H-Bond Aceptor:	12
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.196
Synthetic Accessibility Score:	6.396
Fsp3:	0.71
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:	-5.045
MDCK Permeability:	0.00013139833754394203
Pgp-inhibitor:	1.0
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.044
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.262
Plasma Protein Binding (PPB):	68.33199310302734%
Volume Distribution (VD):	1.549
Pgp-substrate:	39.827232360839844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.013
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.017
CYP2D6-inhibitor:	0.099
CYP2D6-substrate:	0.065
CYP3A4-inhibitor:	0.404
CYP3A4-substrate:	0.221

ADMET: Excretion

Clearance (CL):	2.722
Half-life (T1/2):	0.281

ADMET: Toxicity

hERG Blockers:	0.081
Human Hepatotoxicity (H-HT):	0.955
Drug-inuced Liver Injury (DILI):	0.966
AMES Toxicity:	0.115
Rat Oral Acute Toxicity:	0.759
Maximum Recommended Daily Dose:	0.774
Skin Sensitization:	0.527
Carcinogencity:	0.043
Eye Corrosion:	0.004
Eye Irritation:	0.016
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC282003

Natural Product ID:	NPC282003
*Common Name:**	Gemmacolide I
IUPAC Name:	n.a.
Synonyms:	Gemmacolide I
Standard InCHIKey:	WFEBCPFMBDVKOY-FJMVWVHASA-N
Standard InCHI:	InChI=1S/C31H41ClO12/c1-14(2)11-23(36)43-22-12-21(41-18(6)34)29(8)20(40-17(5)33)10-9-15(3)24(32)26-31(38,16(4)28(37)44-26)27(42-19(7)35)25(29)30(22)13-39-30/h9-10,14,16,20-22,24-27,38H,3,11-13H2,1-2,4-8H3/b10-9+/t16-,20-,21-,22+,24-,25+,26-,27-,29-,30+,31-/m0/s1
SMILES:	CC(C)CC(=O)O[C@@H]1C[C@@H]([C@]2(C)[C@H](/C=C/C(=C)[C@@H]([C@H]3[C@@]([C@@H](C)C(=O)O3)([C@H]([C@H]2[C@]21CO2)OC(=O)C)O)Cl)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1812329
PubChem CID:	53468496
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

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	20600.0	nM	PMID[489624]
NPT2351	Cell Line	MG-63	Homo sapiens	IC50	=	25000.0	nM	PMID[489624]

☑ 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 NPC282003 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	241
0.1-0.2	1359
0.2-0.3	4375
0.3-0.4	7674
0.4-0.5	15419
0.5-0.6	9058
0.6-0.7	3993
0.7-0.8	522
0.8-0.85	30
0.85-0.9	17
0.9-0.95	3
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC310035
1.0	High Similarity	NPC188222
0.9912	High Similarity	NPC303006
0.9333	High Similarity	NPC470185
0.9204	High Similarity	NPC73314
0.9115	High Similarity	NPC89018
0.9035	High Similarity	NPC226608
0.9035	High Similarity	NPC88867
0.8957	High Similarity	NPC470466
0.8889	High Similarity	NPC470186
0.885	High Similarity	NPC140409
0.885	High Similarity	NPC11491
0.885	High Similarity	NPC156248
0.8839	High Similarity	NPC94377
0.8772	High Similarity	NPC170294
0.8673	High Similarity	NPC128210
0.8559	High Similarity	NPC296822
0.8534	High Similarity	NPC473877
0.8522	High Similarity	NPC281624
0.85	High Similarity	NPC475003
0.8475	Intermediate Similarity	NPC474333
0.8448	Intermediate Similarity	NPC470467
0.8435	Intermediate Similarity	NPC42662
0.8376	Intermediate Similarity	NPC470468
0.8333	Intermediate Similarity	NPC476714
0.8291	Intermediate Similarity	NPC194619
0.8276	Intermediate Similarity	NPC475191
0.8261	Intermediate Similarity	NPC475587
0.8261	Intermediate Similarity	NPC475510
0.823	Intermediate Similarity	NPC183571
0.8205	Intermediate Similarity	NPC473975
0.8205	Intermediate Similarity	NPC474586
0.8205	Intermediate Similarity	NPC473594
0.8205	Intermediate Similarity	NPC473843
0.819	Intermediate Similarity	NPC473939
0.819	Intermediate Similarity	NPC473595
0.8158	Intermediate Similarity	NPC69171
0.8158	Intermediate Similarity	NPC474165
0.8142	Intermediate Similarity	NPC98225
0.812	Intermediate Similarity	NPC475922
0.8051	Intermediate Similarity	NPC161816
0.8051	Intermediate Similarity	NPC115257
0.8033	Intermediate Similarity	NPC284707
0.8017	Intermediate Similarity	NPC329869
0.8017	Intermediate Similarity	NPC16313
0.8017	Intermediate Similarity	NPC9303
0.8016	Intermediate Similarity	NPC470973
0.8	Intermediate Similarity	NPC477126
0.7965	Intermediate Similarity	NPC152480
0.7953	Intermediate Similarity	NPC478207
0.7951	Intermediate Similarity	NPC476713
0.7951	Intermediate Similarity	NPC476712
0.7951	Intermediate Similarity	NPC53396
0.7951	Intermediate Similarity	NPC98249
0.7949	Intermediate Similarity	NPC324327
0.7949	Intermediate Similarity	NPC72813
0.7949	Intermediate Similarity	NPC326994
0.7949	Intermediate Similarity	NPC194620
0.7949	Intermediate Similarity	NPC474421
0.7881	Intermediate Similarity	NPC474664
0.7881	Intermediate Similarity	NPC169888
0.7881	Intermediate Similarity	NPC327286
0.7881	Intermediate Similarity	NPC55972
0.7881	Intermediate Similarity	NPC14862
0.7881	Intermediate Similarity	NPC233379
0.7869	Intermediate Similarity	NPC476710
0.7869	Intermediate Similarity	NPC476711
0.7869	Intermediate Similarity	NPC477509
0.7863	Intermediate Similarity	NPC475802
0.7845	Intermediate Similarity	NPC474166
0.7845	Intermediate Similarity	NPC19239
0.7845	Intermediate Similarity	NPC4620
0.7815	Intermediate Similarity	NPC15218
0.7805	Intermediate Similarity	NPC469684
0.7805	Intermediate Similarity	NPC478204
0.7797	Intermediate Similarity	NPC216636
0.7778	Intermediate Similarity	NPC220964
0.7778	Intermediate Similarity	NPC475676
0.776	Intermediate Similarity	NPC475885
0.7759	Intermediate Similarity	NPC474709
0.775	Intermediate Similarity	NPC472215
0.775	Intermediate Similarity	NPC472214
0.7742	Intermediate Similarity	NPC478205
0.7742	Intermediate Similarity	NPC108581
0.7742	Intermediate Similarity	NPC478206
0.7734	Intermediate Similarity	NPC181999
0.7734	Intermediate Similarity	NPC471939
0.768	Intermediate Similarity	NPC156745
0.768	Intermediate Similarity	NPC236918
0.768	Intermediate Similarity	NPC472667
0.7674	Intermediate Similarity	NPC471940
0.7661	Intermediate Similarity	NPC58662
0.7647	Intermediate Similarity	NPC319438
0.7627	Intermediate Similarity	NPC283850
0.7619	Intermediate Similarity	NPC472759
0.7619	Intermediate Similarity	NPC329080
0.7619	Intermediate Similarity	NPC143755
0.7615	Intermediate Similarity	NPC236999
0.7607	Intermediate Similarity	NPC478156
0.7603	Intermediate Similarity	NPC119550
0.76	Intermediate Similarity	NPC146280
0.76	Intermediate Similarity	NPC124676
0.7597	Intermediate Similarity	NPC473635
0.7581	Intermediate Similarity	NPC270478
0.7578	Intermediate Similarity	NPC473802
0.7561	Intermediate Similarity	NPC478212
0.7561	Intermediate Similarity	NPC471204
0.7542	Intermediate Similarity	NPC23584
0.7542	Intermediate Similarity	NPC61442
0.7542	Intermediate Similarity	NPC99510
0.7541	Intermediate Similarity	NPC469656
0.7541	Intermediate Similarity	NPC469655
0.7541	Intermediate Similarity	NPC474846
0.7521	Intermediate Similarity	NPC469370
0.7521	Intermediate Similarity	NPC308824
0.7521	Intermediate Similarity	NPC316974
0.7521	Intermediate Similarity	NPC322912
0.752	Intermediate Similarity	NPC176513
0.752	Intermediate Similarity	NPC470775
0.752	Intermediate Similarity	NPC473590
0.7519	Intermediate Similarity	NPC473919
0.7519	Intermediate Similarity	NPC473709
0.7519	Intermediate Similarity	NPC145238
0.75	Intermediate Similarity	NPC170538
0.75	Intermediate Similarity	NPC187435
0.75	Intermediate Similarity	NPC162009
0.75	Intermediate Similarity	NPC257017
0.75	Intermediate Similarity	NPC470265
0.75	Intermediate Similarity	NPC67321
0.75	Intermediate Similarity	NPC23786
0.748	Intermediate Similarity	NPC269530
0.748	Intermediate Similarity	NPC317687
0.7479	Intermediate Similarity	NPC239162
0.7479	Intermediate Similarity	NPC146731
0.7463	Intermediate Similarity	NPC100017
0.7463	Intermediate Similarity	NPC473548
0.7463	Intermediate Similarity	NPC182266
0.7463	Intermediate Similarity	NPC471137
0.7463	Intermediate Similarity	NPC475154
0.7463	Intermediate Similarity	NPC223356
0.7463	Intermediate Similarity	NPC475500
0.7463	Intermediate Similarity	NPC471136
0.7462	Intermediate Similarity	NPC293112
0.7458	Intermediate Similarity	NPC472552
0.7458	Intermediate Similarity	NPC475091
0.7458	Intermediate Similarity	NPC11956
0.7442	Intermediate Similarity	NPC472399
0.7442	Intermediate Similarity	NPC67251
0.7442	Intermediate Similarity	NPC11895
0.744	Intermediate Similarity	NPC234858
0.744	Intermediate Similarity	NPC179626
0.744	Intermediate Similarity	NPC154363
0.744	Intermediate Similarity	NPC470793
0.744	Intermediate Similarity	NPC471127
0.7438	Intermediate Similarity	NPC217921
0.7438	Intermediate Similarity	NPC102843
0.7438	Intermediate Similarity	NPC128795
0.7438	Intermediate Similarity	NPC473482
0.7438	Intermediate Similarity	NPC469916
0.7438	Intermediate Similarity	NPC311223
0.7438	Intermediate Similarity	NPC475418
0.7438	Intermediate Similarity	NPC48548
0.7438	Intermediate Similarity	NPC318363
0.7438	Intermediate Similarity	NPC181994
0.7438	Intermediate Similarity	NPC135015
0.7438	Intermediate Similarity	NPC472439
0.7436	Intermediate Similarity	NPC477656
0.7436	Intermediate Similarity	NPC272223
0.7436	Intermediate Similarity	NPC474718
0.7422	Intermediate Similarity	NPC67569
0.7422	Intermediate Similarity	NPC310511
0.7419	Intermediate Similarity	NPC475966
0.7419	Intermediate Similarity	NPC469454
0.7419	Intermediate Similarity	NPC469496
0.7419	Intermediate Similarity	NPC469463
0.7417	Intermediate Similarity	NPC470975
0.7417	Intermediate Similarity	NPC477125
0.7417	Intermediate Similarity	NPC103088
0.7417	Intermediate Similarity	NPC470979
0.7414	Intermediate Similarity	NPC120446
0.7405	Intermediate Similarity	NPC470780
0.7398	Intermediate Similarity	NPC304180
0.7398	Intermediate Similarity	NPC317107
0.7398	Intermediate Similarity	NPC179798
0.7395	Intermediate Similarity	NPC156681
0.7395	Intermediate Similarity	NPC72842
0.7385	Intermediate Similarity	NPC81736
0.7385	Intermediate Similarity	NPC172154
0.7381	Intermediate Similarity	NPC13713
0.7381	Intermediate Similarity	NPC10721
0.7377	Intermediate Similarity	NPC475065
0.7377	Intermediate Similarity	NPC284828
0.7377	Intermediate Similarity	NPC40728
0.7377	Intermediate Similarity	NPC173905
0.7377	Intermediate Similarity	NPC472216
0.7377	Intermediate Similarity	NPC5475
0.7373	Intermediate Similarity	NPC472554
0.7368	Intermediate Similarity	NPC475389
0.7368	Intermediate Similarity	NPC251564
0.7368	Intermediate Similarity	NPC475314

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 NPC282003 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	1517
0.2-0.3	3730
0.3-0.4	2502
0.4-0.5	803
0.5-0.6	340
0.6-0.7	60
0.7-0.8	3
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
0.7317	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD6648	Approved
0.7236	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD5344	Discontinued
0.7154	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD7115	Discovery
0.7073	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4225	Approved
0.6897	Remote Similarity	NPD6698	Approved
0.6897	Remote Similarity	NPD46	Approved
0.6894	Remote Similarity	NPD8516	Approved
0.6894	Remote Similarity	NPD8515	Approved
0.6894	Remote Similarity	NPD8517	Approved
0.6894	Remote Similarity	NPD8513	Phase 3
0.6838	Remote Similarity	NPD7983	Approved
0.68	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6371	Approved
0.6752	Remote Similarity	NPD7838	Discovery
0.6746	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD7319	Approved
0.6642	Remote Similarity	NPD8074	Phase 3
0.6642	Remote Similarity	NPD6921	Approved
0.6639	Remote Similarity	NPD5778	Approved
0.6639	Remote Similarity	NPD5779	Approved
0.6613	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD7637	Suspended
0.6519	Remote Similarity	NPD5983	Phase 2
0.6504	Remote Similarity	NPD7638	Approved
0.6493	Remote Similarity	NPD7516	Approved
0.6489	Remote Similarity	NPD4632	Approved
0.6475	Remote Similarity	NPD6033	Approved
0.6466	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD7640	Approved
0.6452	Remote Similarity	NPD7639	Approved
0.6449	Remote Similarity	NPD7507	Approved
0.6449	Remote Similarity	NPD6336	Discontinued
0.6444	Remote Similarity	NPD6319	Approved
0.6418	Remote Similarity	NPD7327	Approved
0.6418	Remote Similarity	NPD7328	Approved
0.6417	Remote Similarity	NPD6411	Approved
0.637	Remote Similarity	NPD7100	Approved
0.6328	Remote Similarity	NPD6008	Approved
0.6311	Remote Similarity	NPD5282	Discontinued
0.6308	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6335	Approved
0.6277	Remote Similarity	NPD7503	Approved
0.626	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD7492	Approved
0.625	Remote Similarity	NPD7101	Approved
0.625	Remote Similarity	NPD6101	Approved
0.625	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD8133	Approved
0.624	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6399	Phase 3
0.6222	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD6009	Approved
0.6218	Remote Similarity	NPD7524	Approved
0.6214	Remote Similarity	NPD6616	Approved
0.6214	Remote Similarity	NPD8273	Phase 1
0.621	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD6054	Approved
0.6187	Remote Similarity	NPD8328	Phase 3
0.6176	Remote Similarity	NPD6313	Approved
0.6176	Remote Similarity	NPD6314	Approved
0.617	Remote Similarity	NPD7078	Approved
0.6165	Remote Similarity	NPD8297	Approved
0.6159	Remote Similarity	NPD8335	Approved
0.6159	Remote Similarity	NPD8379	Approved
0.6159	Remote Similarity	NPD8380	Approved
0.6159	Remote Similarity	NPD8033	Approved
0.6159	Remote Similarity	NPD8378	Approved
0.6159	Remote Similarity	NPD8296	Approved
0.6154	Remote Similarity	NPD5956	Approved
0.6142	Remote Similarity	NPD1700	Approved
0.6127	Remote Similarity	NPD7736	Approved
0.6116	Remote Similarity	NPD1695	Approved
0.6115	Remote Similarity	NPD6370	Approved
0.6111	Remote Similarity	NPD7260	Phase 2
0.609	Remote Similarity	NPD6650	Approved
0.609	Remote Similarity	NPD6649	Approved
0.6087	Remote Similarity	NPD8294	Approved
0.6087	Remote Similarity	NPD8377	Approved
0.6087	Remote Similarity	NPD6059	Approved
0.608	Remote Similarity	NPD7839	Suspended
0.6066	Remote Similarity	NPD3168	Discontinued
0.6066	Remote Similarity	NPD5785	Approved
0.6061	Remote Similarity	NPD6372	Approved
0.6061	Remote Similarity	NPD6373	Approved
0.6056	Remote Similarity	NPD8293	Discontinued
0.605	Remote Similarity	NPD1694	Approved
0.6043	Remote Similarity	NPD6015	Approved
0.6043	Remote Similarity	NPD6016	Approved
0.6032	Remote Similarity	NPD7902	Approved
0.6029	Remote Similarity	NPD6868	Approved
0.6014	Remote Similarity	NPD4522	Approved
0.6014	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5988	Approved
0.5986	Remote Similarity	NPD8451	Approved
0.5985	Remote Similarity	NPD6899	Approved
0.5985	Remote Similarity	NPD6881	Approved
0.597	Remote Similarity	NPD5215	Approved
0.5969	Remote Similarity	NPD7632	Discontinued
0.5966	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD7829	Approved
0.5957	Remote Similarity	NPD7604	Phase 2
0.5957	Remote Similarity	NPD7830	Approved
0.5954	Remote Similarity	NPD6675	Approved
0.5954	Remote Similarity	NPD5739	Approved
0.5954	Remote Similarity	NPD7128	Approved
0.5954	Remote Similarity	NPD6402	Approved
0.5944	Remote Similarity	NPD8448	Approved
0.5932	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD6882	Approved
0.5926	Remote Similarity	NPD6053	Discontinued
0.592	Remote Similarity	NPD7748	Approved
0.5909	Remote Similarity	NPD6412	Phase 2
0.5909	Remote Similarity	NPD5697	Approved
0.5896	Remote Similarity	NPD7102	Approved
0.5896	Remote Similarity	NPD4634	Approved
0.5896	Remote Similarity	NPD5169	Approved
0.5896	Remote Similarity	NPD7290	Approved
0.5896	Remote Similarity	NPD6883	Approved
0.5887	Remote Similarity	NPD8035	Phase 2
0.5887	Remote Similarity	NPD8034	Phase 2
0.5882	Remote Similarity	NPD6695	Phase 3
0.5877	Remote Similarity	NPD8039	Approved
0.5865	Remote Similarity	NPD7320	Approved
0.5852	Remote Similarity	NPD5127	Approved
0.5852	Remote Similarity	NPD6869	Approved
0.5852	Remote Similarity	NPD8130	Phase 1
0.5852	Remote Similarity	NPD6617	Approved
0.5852	Remote Similarity	NPD5216	Approved
0.5852	Remote Similarity	NPD5217	Approved
0.5852	Remote Similarity	NPD6847	Approved
0.585	Remote Similarity	NPD6845	Suspended
0.5847	Remote Similarity	NPD5369	Approved
0.5845	Remote Similarity	NPD7642	Approved
0.5839	Remote Similarity	NPD5167	Approved
0.5822	Remote Similarity	NPD8390	Approved
0.5822	Remote Similarity	NPD8391	Approved
0.5822	Remote Similarity	NPD8392	Approved
0.5821	Remote Similarity	NPD6013	Approved
0.5821	Remote Similarity	NPD6014	Approved
0.5821	Remote Similarity	NPD6012	Approved
0.582	Remote Similarity	NPD4250	Approved
0.582	Remote Similarity	NPD4251	Approved
0.5816	Remote Similarity	NPD8444	Approved
0.5804	Remote Similarity	NPD8341	Approved
0.5804	Remote Similarity	NPD8340	Approved
0.5804	Remote Similarity	NPD8342	Approved
0.5804	Remote Similarity	NPD8299	Approved
0.5798	Remote Similarity	NPD4269	Approved
0.5798	Remote Similarity	NPD4270	Approved
0.5798	Remote Similarity	NPD5209	Approved
0.5794	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD7900	Approved
0.5789	Remote Similarity	NPD5701	Approved
0.576	Remote Similarity	NPD5284	Approved
0.576	Remote Similarity	NPD7515	Phase 2
0.576	Remote Similarity	NPD5281	Approved
0.5752	Remote Similarity	NPD8384	Approved
0.575	Remote Similarity	NPD7154	Phase 3
0.5748	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5746	Remote Similarity	NPD6011	Approved
0.5738	Remote Similarity	NPD5786	Approved
0.5738	Remote Similarity	NPD4249	Approved
0.5735	Remote Similarity	NPD1719	Phase 1
0.5714	Remote Similarity	NPD5357	Phase 1
0.5691	Remote Similarity	NPD7750	Discontinued
0.5682	Remote Similarity	NPD8407	Phase 2
0.5672	Remote Similarity	NPD6614	Approved
0.5659	Remote Similarity	NPD6083	Phase 2
0.5659	Remote Similarity	NPD5959	Approved
0.5659	Remote Similarity	NPD6084	Phase 2
0.5656	Remote Similarity	NPD5363	Approved
0.5649	Remote Similarity	NPD4159	Approved
0.563	Remote Similarity	NPD4252	Approved
0.563	Remote Similarity	NPD6931	Approved
0.563	Remote Similarity	NPD4822	Approved
0.563	Remote Similarity	NPD4819	Approved
0.563	Remote Similarity	NPD5168	Approved
0.563	Remote Similarity	NPD5128	Approved
0.563	Remote Similarity	NPD4820	Approved
0.563	Remote Similarity	NPD4821	Approved
0.563	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.563	Remote Similarity	NPD7514	Phase 3
0.563	Remote Similarity	NPD7332	Phase 2
0.563	Remote Similarity	NPD6930	Phase 2
0.5625	Remote Similarity	NPD5695	Phase 3
0.5625	Remote Similarity	NPD5654	Approved
0.562	Remote Similarity	NPD5362	Discontinued
0.562	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5618	Remote Similarity	NPD8434	Phase 2
0.5615	Remote Similarity	NPD5696	Approved
0.561	Remote Similarity	NPD3618	Phase 1
0.5606	Remote Similarity	NPD5211	Phase 2
0.56	Remote Similarity	NPD8368	Discontinued

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