NPASS Compound

Structure

CID144739 OpenBabel06191715502D 25 28 0 0 1 0 0 0 0 0999 V2000 1.9883 0.9851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5879 -0.5398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0011 -1.2555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4705 -1.1726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6544 -1.3590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4498 -2.5111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1747 -2.0926 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4498 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7066 -2.0820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4705 0.3357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8338 -0.4185 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.8370 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4498 -0.8370 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7249 -2.0926 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7249 0.4185 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6544 0.5219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8458 -0.5206 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1747 -1.2555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7249 -1.2555 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7066 -2.9085 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0092 -2.5058 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7249 1.2450 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4695 1.3316 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7526 -0.9287 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 2 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 4 5 1 0 0 0 0 5 12 1 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 18 1 0 0 0 0 8 13 1 0 0 0 0 8 15 1 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 16 1 0 0 0 0 11 4 1 6 0 0 0 11 17 1 0 0 0 0 12 19 1 1 0 0 0 12 20 1 0 0 0 0 13 18 1 0 0 0 0 13 19 1 1 0 0 0 14 19 1 1 0 0 0 14 22 1 0 0 0 0 15 20 1 1 0 0 0 15 23 1 0 0 0 0 16 24 2 0 0 0 0 17 20 1 1 0 0 0 17 25 1 0 0 0 0 19 9 1 1 0 0 0 20 16 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	350.21
Volume:	358.929
LogP:	1.082
LogD:	0.595
LogS:	-3.257
# Rotatable Bonds:	1
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.53
Synthetic Accessibility Score:	6.138
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.979
MDCK Permeability:	7.990107405930758e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.118
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.366
30% Bioavailability (F30%):	0.484

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.445
Plasma Protein Binding (PPB):	45.979103088378906%
Volume Distribution (VD):	0.723
Pgp-substrate:	60.755123138427734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.068
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.528
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.113
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.256
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.169

ADMET: Excretion

Clearance (CL):	3.174
Half-life (T1/2):	0.59

ADMET: Toxicity

hERG Blockers:	0.216
Human Hepatotoxicity (H-HT):	0.105
Drug-inuced Liver Injury (DILI):	0.055
AMES Toxicity:	0.239
Rat Oral Acute Toxicity:	0.967
Maximum Recommended Daily Dose:	0.992
Skin Sensitization:	0.752
Carcinogencity:	0.075
Eye Corrosion:	0.008
Eye Irritation:	0.074
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC144739

Natural Product ID:	NPC144739
*Common Name:**	Kamebakaurin
IUPAC Name:	n.a.
Synonyms:	Kamebakaurin
Standard InCHIKey:	WHSUEVLJUHPROF-BIGDWJEQSA-N
Standard InCHI:	InChI=1S/C20H30O5/c1-10-11-4-5-12-19(9-21)13(18(2,3)7-6-14(19)22)8-15(23)20(12,16(10)24)17(11)25/h11-15,17,21-23,25H,1,4-9H2,2-3H3/t11-,12-,13+,14-,15+,17+,19-,20-/m0/s1
SMILES:	OC[C@]12[C@@H](O)CCC([C@H]2C[C@H]([C@]23[C@H]1CC[C@H]([C@H]2O)C(=C)C3=O)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL472436
PubChem CID:	13945489
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO17628	Rabdosia excisa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043413]
NPO8282	Physalis viscosa	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730264]
NPO1680	Physalis angulata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17580910]
NPO6895	Elateriospermum tapos	Species	Euphorbiaceae	Eukaryota	leaves and stem	Nakorn Si Thammarat Province, Thailand	2004-MAR	PMID[18179177]
NPO1680	Physalis angulata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21954931]
NPO1680	Physalis angulata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23270478]
NPO1680	Physalis angulata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25396337]
NPO1680	Physalis angulata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27295506]
NPO26123	Isodon serra	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32993289]
NPO458	Ophiarachna incrassata	Species	Ophiodermatidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7853009]
NPO74	Artemisia indica	Species	Asteraceae	Eukaryota	n.a.	stem	n.a.	PMID[9748386]
NPO17628	Rabdosia excisa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6996	Rubus hirsutus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16019	Isodon japonica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25359	Isodon kameba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13628	Rabdosia longituba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4014	Erigeron breviscapus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15475.1	Isodon umbrosa var. latifolia	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15475.1	Isodon umbrosa var. latifolia	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17628	Rabdosia excisa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26123	Isodon serra	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4014	Erigeron breviscapus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2248	Aiphanes horrida	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16019	Isodon japonica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13628	Rabdosia longituba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6996	Rubus hirsutus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25359	Isodon kameba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4014	Erigeron breviscapus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4530	Erysimum marschallianum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1361	Chenopodium vulvaria	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17628	Rabdosia excisa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO458	Ophiarachna incrassata	Species	Ophiodermatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO74	Artemisia indica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4014	Erigeron breviscapus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6895	Elateriospermum tapos	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26123	Isodon serra	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10263	Alternaria tagetica	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8282	Physalis viscosa	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27832	Pyrobaculum neutrophilum	Species	Thermoproteaceae	Archaea	n.a.	n.a.	n.a.	Database[UNPD]
NPO13628	Rabdosia longituba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14622	Micromonospora lacustris	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2248	Aiphanes horrida	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25359	Isodon kameba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2313	Jungia spectabilis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1680	Physalis angulata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4989	Tricholoma orirubens	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19924	Trachycladiella aurea	Species	Meteoriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6318	Caulerpa flexilis	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3591	Halleria lucida	Species	Stilbaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6996	Rubus hirsutus	Species	Rosaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.82	ug.mL-1	PMID[500856]

☑ 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 NPC144739 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	212
0.1-0.2	1694
0.2-0.3	5971
0.3-0.4	11434
0.4-0.5	10035
0.5-0.6	5962
0.6-0.7	5239
0.7-0.8	1832
0.8-0.85	167
0.85-0.9	70
0.9-0.95	50
0.95-1	31

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC181594
0.9885	High Similarity	NPC111524
0.9885	High Similarity	NPC129004
0.9885	High Similarity	NPC289539
0.9885	High Similarity	NPC292374
0.9885	High Similarity	NPC153775
0.9885	High Similarity	NPC215271
0.9885	High Similarity	NPC104371
0.9885	High Similarity	NPC29247
0.9885	High Similarity	NPC261333
0.9885	High Similarity	NPC91772
0.9885	High Similarity	NPC101233
0.9884	High Similarity	NPC476168
0.9884	High Similarity	NPC299185
0.9773	High Similarity	NPC84018
0.9773	High Similarity	NPC231060
0.9773	High Similarity	NPC138245
0.9767	High Similarity	NPC470378
0.9767	High Similarity	NPC261994
0.9767	High Similarity	NPC180849
0.9767	High Similarity	NPC80401
0.9767	High Similarity	NPC149761
0.9663	High Similarity	NPC264979
0.9663	High Similarity	NPC140242
0.9663	High Similarity	NPC135548
0.9659	High Similarity	NPC302008
0.9659	High Similarity	NPC191094
0.9545	High Similarity	NPC59170
0.9545	High Similarity	NPC59350
0.9438	High Similarity	NPC64006
0.9419	High Similarity	NPC153604
0.9419	High Similarity	NPC165895
0.9419	High Similarity	NPC259009
0.9419	High Similarity	NPC174619
0.9348	High Similarity	NPC156324
0.9348	High Similarity	NPC127408
0.9348	High Similarity	NPC55503
0.9348	High Similarity	NPC291785
0.9333	High Similarity	NPC29112
0.9247	High Similarity	NPC471790
0.9247	High Similarity	NPC289148
0.9247	High Similarity	NPC163963
0.9247	High Similarity	NPC52899
0.9231	High Similarity	NPC13949
0.9213	High Similarity	NPC211403
0.9213	High Similarity	NPC198242
0.9213	High Similarity	NPC278106
0.9186	High Similarity	NPC471034
0.9186	High Similarity	NPC190704
0.9186	High Similarity	NPC102292
0.9149	High Similarity	NPC88203
0.9149	High Similarity	NPC76866
0.9149	High Similarity	NPC304832
0.9149	High Similarity	NPC148628
0.9149	High Similarity	NPC214946
0.9149	High Similarity	NPC246736
0.9149	High Similarity	NPC286519
0.9149	High Similarity	NPC309388
0.9149	High Similarity	NPC475803
0.914	High Similarity	NPC287676
0.9111	High Similarity	NPC82138
0.907	High Similarity	NPC146683
0.9053	High Similarity	NPC216114
0.9053	High Similarity	NPC87927
0.9032	High Similarity	NPC16911
0.9032	High Similarity	NPC78427
0.9011	High Similarity	NPC470386
0.9011	High Similarity	NPC280804
0.9011	High Similarity	NPC470385
0.8958	High Similarity	NPC98603
0.8958	High Similarity	NPC84928
0.8958	High Similarity	NPC13149
0.8953	High Similarity	NPC471036
0.8953	High Similarity	NPC118800
0.8953	High Similarity	NPC291320
0.8947	High Similarity	NPC272472
0.8913	High Similarity	NPC210214
0.8913	High Similarity	NPC41070
0.8913	High Similarity	NPC470232
0.8889	High Similarity	NPC100313
0.8866	High Similarity	NPC4115
0.8866	High Similarity	NPC12823
0.8842	High Similarity	NPC46848
0.8842	High Similarity	NPC60947
0.8837	High Similarity	NPC110780
0.883	High Similarity	NPC471038
0.8817	High Similarity	NPC470387
0.8817	High Similarity	NPC329910
0.8804	High Similarity	NPC475118
0.8791	High Similarity	NPC250753
0.8764	High Similarity	NPC472497
0.8763	High Similarity	NPC202793
0.8763	High Similarity	NPC474558
0.875	High Similarity	NPC275990
0.8737	High Similarity	NPC470388
0.8723	High Similarity	NPC170978
0.8723	High Similarity	NPC10864
0.871	High Similarity	NPC470229
0.871	High Similarity	NPC98639
0.8696	High Similarity	NPC294263
0.8687	High Similarity	NPC231278
0.8687	High Similarity	NPC469733
0.8687	High Similarity	NPC112895
0.8687	High Similarity	NPC55973
0.8687	High Similarity	NPC469729
0.8687	High Similarity	NPC218123
0.866	High Similarity	NPC470310
0.866	High Similarity	NPC139347
0.8646	High Similarity	NPC14634
0.8646	High Similarity	NPC71706
0.8632	High Similarity	NPC38296
0.8632	High Similarity	NPC38471
0.8632	High Similarity	NPC98837
0.8632	High Similarity	NPC20479
0.8632	High Similarity	NPC28864
0.8632	High Similarity	NPC89099
0.8632	High Similarity	NPC162459
0.8632	High Similarity	NPC474793
0.8617	High Similarity	NPC200054
0.8617	High Similarity	NPC29410
0.8617	High Similarity	NPC234564
0.8602	High Similarity	NPC47853
0.8586	High Similarity	NPC469746
0.8586	High Similarity	NPC471461
0.8586	High Similarity	NPC67745
0.8556	High Similarity	NPC57469
0.8556	High Similarity	NPC472495
0.8542	High Similarity	NPC293866
0.8515	High Similarity	NPC473324
0.8515	High Similarity	NPC471093
0.8511	High Similarity	NPC288906
0.8511	High Similarity	NPC142352
0.8511	High Similarity	NPC263135
0.85	High Similarity	NPC189663
0.85	High Similarity	NPC273155
0.85	High Similarity	NPC89860
0.85	High Similarity	NPC211224
0.8495	Intermediate Similarity	NPC224060
0.8495	Intermediate Similarity	NPC472496
0.8495	Intermediate Similarity	NPC244356
0.8485	Intermediate Similarity	NPC37600
0.8485	Intermediate Similarity	NPC138908
0.8485	Intermediate Similarity	NPC200957
0.8478	Intermediate Similarity	NPC46758
0.8469	Intermediate Similarity	NPC122811
0.8469	Intermediate Similarity	NPC96217
0.8469	Intermediate Similarity	NPC159442
0.8469	Intermediate Similarity	NPC277074
0.8469	Intermediate Similarity	NPC209298
0.8454	Intermediate Similarity	NPC148279
0.8454	Intermediate Similarity	NPC236585
0.8438	Intermediate Similarity	NPC288
0.8438	Intermediate Similarity	NPC109059
0.8431	Intermediate Similarity	NPC29505
0.8431	Intermediate Similarity	NPC329953
0.8431	Intermediate Similarity	NPC122339
0.8421	Intermediate Similarity	NPC104568
0.8416	Intermediate Similarity	NPC252679
0.8416	Intermediate Similarity	NPC118721
0.8416	Intermediate Similarity	NPC469744
0.84	Intermediate Similarity	NPC176949
0.84	Intermediate Similarity	NPC201908
0.84	Intermediate Similarity	NPC166993
0.8387	Intermediate Similarity	NPC470230
0.8384	Intermediate Similarity	NPC96268
0.8351	Intermediate Similarity	NPC267921
0.835	Intermediate Similarity	NPC473303
0.835	Intermediate Similarity	NPC471245
0.8333	Intermediate Similarity	NPC76518
0.8333	Intermediate Similarity	NPC190080
0.8333	Intermediate Similarity	NPC471476
0.8333	Intermediate Similarity	NPC111187
0.8333	Intermediate Similarity	NPC190554
0.8317	Intermediate Similarity	NPC63841
0.8317	Intermediate Similarity	NPC9013
0.8316	Intermediate Similarity	NPC266431
0.8316	Intermediate Similarity	NPC472485
0.8315	Intermediate Similarity	NPC472498
0.83	Intermediate Similarity	NPC295366
0.83	Intermediate Similarity	NPC307660
0.83	Intermediate Similarity	NPC265127
0.83	Intermediate Similarity	NPC130511
0.8283	Intermediate Similarity	NPC312900
0.8283	Intermediate Similarity	NPC266
0.8269	Intermediate Similarity	NPC471248
0.8269	Intermediate Similarity	NPC471252
0.8265	Intermediate Similarity	NPC295276
0.8265	Intermediate Similarity	NPC121218
0.8265	Intermediate Similarity	NPC253886
0.8265	Intermediate Similarity	NPC252614
0.8261	Intermediate Similarity	NPC472739
0.8256	Intermediate Similarity	NPC106078
0.8252	Intermediate Similarity	NPC470281
0.8252	Intermediate Similarity	NPC63244
0.8252	Intermediate Similarity	NPC213320
0.8247	Intermediate Similarity	NPC26270
0.8247	Intermediate Similarity	NPC114274
0.8242	Intermediate Similarity	NPC34190
0.8235	Intermediate Similarity	NPC102741
0.8222	Intermediate Similarity	NPC474482

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 NPC144739 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	2089
0.2-0.3	4128
0.3-0.4	1820
0.4-0.5	482
0.5-0.6	164
0.6-0.7	155
0.7-0.8	117
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
0.8	Intermediate Similarity	NPD6079	Approved
0.7981	Intermediate Similarity	NPD4634	Approved
0.798	Intermediate Similarity	NPD4696	Approved
0.798	Intermediate Similarity	NPD5286	Approved
0.798	Intermediate Similarity	NPD5285	Approved
0.7979	Intermediate Similarity	NPD5328	Approved
0.7959	Intermediate Similarity	NPD4755	Approved
0.7912	Intermediate Similarity	NPD4788	Approved
0.7857	Intermediate Similarity	NPD5221	Approved
0.7857	Intermediate Similarity	NPD4697	Phase 3
0.7857	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD5222	Approved
0.7849	Intermediate Similarity	NPD3618	Phase 1
0.7822	Intermediate Similarity	NPD5224	Approved
0.7822	Intermediate Similarity	NPD4633	Approved
0.7822	Intermediate Similarity	NPD5226	Approved
0.7822	Intermediate Similarity	NPD5211	Phase 2
0.7822	Intermediate Similarity	NPD5225	Approved
0.7816	Intermediate Similarity	NPD3703	Phase 2
0.78	Intermediate Similarity	NPD4700	Approved
0.7778	Intermediate Similarity	NPD5173	Approved
0.7745	Intermediate Similarity	NPD5174	Approved
0.7745	Intermediate Similarity	NPD5175	Approved
0.7742	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7723	Intermediate Similarity	NPD5223	Approved
0.767	Intermediate Similarity	NPD5141	Approved
0.766	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD4786	Approved
0.7609	Intermediate Similarity	NPD3667	Approved
0.7551	Intermediate Similarity	NPD4202	Approved
0.7524	Intermediate Similarity	NPD5697	Approved
0.7453	Intermediate Similarity	NPD5128	Approved
0.7453	Intermediate Similarity	NPD4730	Approved
0.7453	Intermediate Similarity	NPD6899	Approved
0.7453	Intermediate Similarity	NPD6881	Approved
0.7453	Intermediate Similarity	NPD4729	Approved
0.7449	Intermediate Similarity	NPD8034	Phase 2
0.7449	Intermediate Similarity	NPD8035	Phase 2
0.7447	Intermediate Similarity	NPD3665	Phase 1
0.7447	Intermediate Similarity	NPD3666	Approved
0.7447	Intermediate Similarity	NPD3133	Approved
0.7429	Intermediate Similarity	NPD4768	Approved
0.7429	Intermediate Similarity	NPD6675	Approved
0.7429	Intermediate Similarity	NPD7128	Approved
0.7429	Intermediate Similarity	NPD4767	Approved
0.7429	Intermediate Similarity	NPD6402	Approved
0.7429	Intermediate Similarity	NPD5739	Approved
0.7423	Intermediate Similarity	NPD4753	Phase 2
0.7407	Intermediate Similarity	NPD6649	Approved
0.7407	Intermediate Similarity	NPD6650	Approved
0.7404	Intermediate Similarity	NPD4754	Approved
0.74	Intermediate Similarity	NPD4629	Approved
0.74	Intermediate Similarity	NPD5210	Approved
0.7383	Intermediate Similarity	NPD6373	Approved
0.7383	Intermediate Similarity	NPD6013	Approved
0.7383	Intermediate Similarity	NPD6012	Approved
0.7383	Intermediate Similarity	NPD6014	Approved
0.7383	Intermediate Similarity	NPD6372	Approved
0.7363	Intermediate Similarity	NPD6115	Approved
0.7363	Intermediate Similarity	NPD6697	Approved
0.7363	Intermediate Similarity	NPD6118	Approved
0.7363	Intermediate Similarity	NPD6114	Approved
0.7358	Intermediate Similarity	NPD5701	Approved
0.7345	Intermediate Similarity	NPD6054	Approved
0.7345	Intermediate Similarity	NPD6319	Approved
0.7315	Intermediate Similarity	NPD6883	Approved
0.7315	Intermediate Similarity	NPD7102	Approved
0.7315	Intermediate Similarity	NPD5247	Approved
0.7315	Intermediate Similarity	NPD5248	Approved
0.7315	Intermediate Similarity	NPD5249	Phase 3
0.7315	Intermediate Similarity	NPD7290	Approved
0.7315	Intermediate Similarity	NPD5251	Approved
0.7315	Intermediate Similarity	NPD5250	Approved
0.729	Intermediate Similarity	NPD7320	Approved
0.729	Intermediate Similarity	NPD6011	Approved
0.7281	Intermediate Similarity	NPD6016	Approved
0.7281	Intermediate Similarity	NPD6015	Approved
0.7273	Intermediate Similarity	NPD4632	Approved
0.7273	Intermediate Similarity	NPD7515	Phase 2
0.7273	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD6008	Approved
0.7248	Intermediate Similarity	NPD5216	Approved
0.7248	Intermediate Similarity	NPD8130	Phase 1
0.7248	Intermediate Similarity	NPD6847	Approved
0.7248	Intermediate Similarity	NPD6617	Approved
0.7248	Intermediate Similarity	NPD5215	Approved
0.7248	Intermediate Similarity	NPD6869	Approved
0.7248	Intermediate Similarity	NPD5217	Approved
0.7241	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD6370	Approved
0.7217	Intermediate Similarity	NPD5988	Approved
0.72	Intermediate Similarity	NPD6399	Phase 3
0.7193	Intermediate Similarity	NPD6059	Approved
0.7182	Intermediate Similarity	NPD8297	Approved
0.7182	Intermediate Similarity	NPD6882	Approved
0.7156	Intermediate Similarity	NPD5135	Approved
0.7156	Intermediate Similarity	NPD5169	Approved
0.7156	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6117	Approved
0.713	Intermediate Similarity	NPD5168	Approved
0.7094	Intermediate Similarity	NPD7492	Approved
0.7091	Intermediate Similarity	NPD5127	Approved
0.7083	Intermediate Similarity	NPD3668	Phase 3
0.708	Intermediate Similarity	NPD7115	Discovery
0.708	Intermediate Similarity	NPD6009	Approved
0.7065	Intermediate Similarity	NPD6116	Phase 1
0.7059	Intermediate Similarity	NPD7736	Approved
0.7053	Intermediate Similarity	NPD4221	Approved
0.7053	Intermediate Similarity	NPD4223	Phase 3
0.7045	Intermediate Similarity	NPD3698	Phase 2
0.7034	Intermediate Similarity	NPD6616	Approved
0.7021	Intermediate Similarity	NPD7525	Registered
0.7019	Intermediate Similarity	NPD7638	Approved
0.6991	Remote Similarity	NPD6274	Approved
0.6975	Remote Similarity	NPD7078	Approved
0.6972	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4245	Approved
0.6966	Remote Similarity	NPD4244	Approved
0.6961	Remote Similarity	NPD7748	Approved
0.6952	Remote Similarity	NPD7639	Approved
0.6952	Remote Similarity	NPD7640	Approved
0.6939	Remote Similarity	NPD5279	Phase 3
0.6937	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6083	Phase 2
0.6923	Remote Similarity	NPD6084	Phase 2
0.6923	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7902	Approved
0.6907	Remote Similarity	NPD4197	Approved
0.6903	Remote Similarity	NPD5167	Approved
0.6857	Remote Similarity	NPD4225	Approved
0.6857	Remote Similarity	NPD5696	Approved
0.6842	Remote Similarity	NPD4695	Discontinued
0.6838	Remote Similarity	NPD5983	Phase 2
0.6837	Remote Similarity	NPD5329	Approved
0.6833	Remote Similarity	NPD8293	Discontinued
0.681	Remote Similarity	NPD7101	Approved
0.681	Remote Similarity	NPD7100	Approved
0.6783	Remote Similarity	NPD6317	Approved
0.6782	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD4789	Approved
0.6774	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD4690	Approved
0.6768	Remote Similarity	NPD4689	Approved
0.6768	Remote Similarity	NPD5205	Approved
0.6768	Remote Similarity	NPD4693	Phase 3
0.6768	Remote Similarity	NPD4138	Approved
0.6768	Remote Similarity	NPD5690	Phase 2
0.6768	Remote Similarity	NPD4688	Approved
0.6765	Remote Similarity	NPD6411	Approved
0.6742	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5360	Phase 3
0.6731	Remote Similarity	NPD5695	Phase 3
0.6727	Remote Similarity	NPD6412	Phase 2
0.6724	Remote Similarity	NPD6335	Approved
0.6724	Remote Similarity	NPD6313	Approved
0.6724	Remote Similarity	NPD6314	Approved
0.6723	Remote Similarity	NPD7604	Phase 2
0.6723	Remote Similarity	NPD8328	Phase 3
0.6721	Remote Similarity	NPD7319	Approved
0.6696	Remote Similarity	NPD6868	Approved
0.6695	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6942	Approved
0.6667	Remote Similarity	NPD7339	Approved
0.6667	Remote Similarity	NPD4522	Approved
0.6639	Remote Similarity	NPD6033	Approved
0.6638	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD7900	Approved
0.6635	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD3671	Phase 1
0.6632	Remote Similarity	NPD3617	Approved
0.6612	Remote Similarity	NPD7507	Approved
0.6612	Remote Similarity	NPD6336	Discontinued
0.6602	Remote Similarity	NPD5281	Approved
0.6602	Remote Similarity	NPD5284	Approved
0.66	Remote Similarity	NPD7334	Approved
0.66	Remote Similarity	NPD7521	Approved
0.66	Remote Similarity	NPD6409	Approved
0.66	Remote Similarity	NPD5280	Approved
0.66	Remote Similarity	NPD4694	Approved
0.66	Remote Similarity	NPD6684	Approved
0.66	Remote Similarity	NPD5330	Approved
0.66	Remote Similarity	NPD7146	Approved
0.6571	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6101	Approved
0.6569	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7645	Phase 2
0.6562	Remote Similarity	NPD4195	Approved
0.6555	Remote Similarity	NPD6908	Approved
0.6555	Remote Similarity	NPD6909	Approved
0.6538	Remote Similarity	NPD5778	Approved
0.6538	Remote Similarity	NPD5779	Approved
0.6535	Remote Similarity	NPD3573	Approved
0.6535	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4758	Discontinued
0.6522	Remote Similarity	NPD8133	Approved
0.6517	Remote Similarity	NPD4224	Phase 2
0.6514	Remote Similarity	NPD7632	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