NPASS Compound

Structure

NPC136922 OpenBabel07101719192D 52 56 0 0 1 0 0 0 0 0999 V2000 6.9566 -3.2722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9156 -1.9261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0768 -3.6806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1990 -2.4247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8460 1.0989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2344 -2.7348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6277 1.6526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2645 0.5702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3996 0.8975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5449 -1.9732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5118 -0.4912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0984 -1.1614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9344 0.3036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9099 -0.6534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7058 0.6443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3364 -0.6731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9058 -2.2802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9746 1.2492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8247 -2.2986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2380 -2.2204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9072 0.8093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7044 -2.4452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8607 0.6981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9954 -0.2945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6162 -1.3414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6019 -1.6976 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9344 -1.2861 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7608 -0.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2752 -0.9627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2593 1.4561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3524 -3.0919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2075 0.2947 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8508 -1.4737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7017 -0.9825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5725 -0.7156 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.9825 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.2390 1.5295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3726 -3.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7017 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8508 0.4912 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.4974 -0.3842 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.6847 1.9281 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.8037 0.4226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4938 -1.9206 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7680 2.3069 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8436 -3.9428 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5979 2.4440 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0137 -4.0799 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5525 0.4912 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8508 1.4737 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1505 0.0192 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 6 22 1 0 0 0 0 7 23 1 0 0 0 0 10 12 1 0 0 0 0 10 26 1 0 0 0 0 11 13 1 0 0 0 0 11 27 1 0 0 0 0 12 41 1 0 0 0 0 13 42 1 0 0 0 0 14 24 2 0 0 0 0 14 28 1 0 0 0 0 15 24 1 0 0 0 0 15 30 2 0 0 0 0 16 25 1 0 0 0 0 16 29 2 0 0 0 0 17 25 1 0 0 0 0 17 31 2 0 0 0 0 18 43 2 0 0 0 0 21 28 2 0 0 0 0 21 37 1 0 0 0 0 22 33 2 0 0 0 0 22 38 1 0 0 0 0 23 44 2 0 0 0 0 23 52 1 0 0 0 0 24 29 1 0 0 0 0 25 34 2 0 0 0 0 26 19 1 6 0 0 0 26 35 1 0 0 0 0 27 20 1 1 0 0 0 27 36 1 0 0 0 0 28 35 1 0 0 0 0 29 45 1 0 0 0 0 30 37 1 0 0 0 0 30 46 1 0 0 0 0 31 38 1 0 0 0 0 31 47 1 0 0 0 0 32 18 1 6 0 0 0 32 41 1 0 0 0 0 32 52 1 0 0 0 0 33 34 1 0 0 0 0 33 36 1 0 0 0 0 34 39 1 0 0 0 0 35 41 1 6 0 0 0 36 42 1 1 0 0 0 37 48 2 0 0 0 0 38 49 2 0 0 0 0 39 40 1 0 0 0 0 39 50 1 6 0 0 0 40 42 1 1 0 0 0 40 51 1 0 0 0 0 41 8 1 1 0 0 0 42 9 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	718.37
Volume:	751.107
LogP:	4.316
LogD:	3.057
LogS:	-3.903
# Rotatable Bonds:	10
TPSA:	175.5
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.143
Synthetic Accessibility Score:	5.643
Fsp3:	0.595
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.035
MDCK Permeability:	5.758371571573662e-06
Pgp-inhibitor:	0.064
Pgp-substrate:	0.953
Human Intestinal Absorption (HIA):	0.044
20% Bioavailability (F20%):	0.035
30% Bioavailability (F30%):	0.931

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	85.84852600097656%
Volume Distribution (VD):	0.488
Pgp-substrate:	5.071259021759033%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.275
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.54
CYP2C9-inhibitor:	0.117
CYP2C9-substrate:	0.92
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.104
CYP3A4-inhibitor:	0.21
CYP3A4-substrate:	0.784

ADMET: Excretion

Clearance (CL):	1.641
Half-life (T1/2):	0.228

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.547
Drug-inuced Liver Injury (DILI):	0.854
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.167
Maximum Recommended Daily Dose:	0.867
Skin Sensitization:	0.549
Carcinogencity:	0.002
Eye Corrosion:	0.003
Eye Irritation:	0.131
Respiratory Toxicity:	0.031

Download Data

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

Natural Product: NPC136922

Natural Product ID:	NPC136922
*Common Name:**	Gukulenin F
IUPAC Name:	[(1R)-1-[(1R,2R,3R)-2-[3-[(Z)-2-[(1R,3aR,4R,5R,10bR)-4,5,9-trihydroxy-3a,10-dimethyl-8-oxo-1-propan-2-yl-1,2,3,4,5,10b-hexahydrocyclohepta[e]inden-6-yl]-1-hydroxyethenyl]-6-hydroxy-7-methyl-5-oxocyclohepta-1,3,6-trien-1-yl]-1-methyl-3-propan-2-ylcyclopentyl]-2-oxoethyl] acetate
Synonyms:
Standard InCHIKey:	FLYKZSCSEAHSJD-WUQBFVGZSA-N
Standard InCHI:	InChI=1S/C42H54O10/c1-19(2)26-10-12-41(8,32(18-43)52-23(7)44)35(26)28-14-24(15-30(46)37(48)21(28)5)29(45)16-25-17-31(47)38(49)22(6)33-34(25)39(50)40(51)42(9)13-11-27(20(3)4)36(33)42/h14-20,26-27,32,35-36,39-40,45,50-51H,10-13H2,1-9H3,(H,46,48)(H,47,49)/b29-16-/t26-,27-,32+,35-,36-,39-,40+,41+,42-/m1/s1
SMILES:	O=C[C@@H]([C@]1(C)CC[C@@H]([C@@H]1c1cc(cc(c(=O)c1C)O)/C(=C/c1cc(O)c(=O)c(c2c1[C@@H](O)[C@H](O)[C@]1([C@@H]2[C@H](CC1)C(C)C)C)C)/O)C(C)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2419840
PubChem CID:	73356790
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001565] Iridoids 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
NPO32713	phorbas gukhulensis	Species	Hymedesmiidae	Eukaryota	n.a.	Korean	n.a.	PMID[24025124]

☑ 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	3
Others	3

Activity Type	# Activity
Cell Line	3
Others	2
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	RatioLC50	=	17.0	n.a.	PMID[546119]
NPT81	Cell Line	A549	Homo sapiens	LC50	=	380.0	nM	PMID[546119]
NPT111	Cell Line	K562	Homo sapiens	LC50	=	40.0	nM	PMID[546119]
NPT2890	Protein Complex	Sodium/potassium-transporting ATPase	Homo sapiens	IC50	>	100000.0	nM	PMID[546119]
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[546119]

☑ 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 NPC136922 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	322
0.1-0.2	1199
0.2-0.3	2789
0.3-0.4	6102
0.4-0.5	12281
0.5-0.6	9766
0.6-0.7	9454
0.7-0.8	779
0.8-0.85	2
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9375	High Similarity	NPC290261
0.875	High Similarity	NPC82759
0.7909	Intermediate Similarity	NPC266955
0.7838	Intermediate Similarity	NPC115899
0.7815	Intermediate Similarity	NPC471854
0.7807	Intermediate Similarity	NPC473284
0.7712	Intermediate Similarity	NPC472926
0.768	Intermediate Similarity	NPC262845
0.768	Intermediate Similarity	NPC68293
0.7672	Intermediate Similarity	NPC170221
0.7672	Intermediate Similarity	NPC10064
0.7636	Intermediate Similarity	NPC250757
0.7636	Intermediate Similarity	NPC301534
0.7619	Intermediate Similarity	NPC202394
0.7611	Intermediate Similarity	NPC155332
0.7611	Intermediate Similarity	NPC32577
0.7611	Intermediate Similarity	NPC114540
0.7607	Intermediate Similarity	NPC6206
0.7603	Intermediate Similarity	NPC257457
0.7603	Intermediate Similarity	NPC311554
0.7568	Intermediate Similarity	NPC471815
0.7568	Intermediate Similarity	NPC141401
0.7563	Intermediate Similarity	NPC472929
0.7544	Intermediate Similarity	NPC470839
0.7544	Intermediate Similarity	NPC475050
0.7544	Intermediate Similarity	NPC72151
0.7541	Intermediate Similarity	NPC22628
0.7541	Intermediate Similarity	NPC255081
0.7541	Intermediate Similarity	NPC5991
0.7541	Intermediate Similarity	NPC275696
0.7541	Intermediate Similarity	NPC5989
0.7541	Intermediate Similarity	NPC471108
0.7522	Intermediate Similarity	NPC303559
0.7522	Intermediate Similarity	NPC99411
0.7521	Intermediate Similarity	NPC153651
0.7521	Intermediate Similarity	NPC472927
0.7521	Intermediate Similarity	NPC475065
0.752	Intermediate Similarity	NPC145238
0.75	Intermediate Similarity	NPC108368
0.75	Intermediate Similarity	NPC57079
0.75	Intermediate Similarity	NPC475176
0.748	Intermediate Similarity	NPC19336
0.748	Intermediate Similarity	NPC185876
0.7479	Intermediate Similarity	NPC475970
0.7459	Intermediate Similarity	NPC171905
0.7459	Intermediate Similarity	NPC471125
0.7459	Intermediate Similarity	NPC472397
0.7459	Intermediate Similarity	NPC472758
0.7456	Intermediate Similarity	NPC470840
0.7456	Intermediate Similarity	NPC320447
0.7436	Intermediate Similarity	NPC473482
0.7436	Intermediate Similarity	NPC475418
0.7436	Intermediate Similarity	NPC318363
0.7436	Intermediate Similarity	NPC295244
0.7434	Intermediate Similarity	NPC35751
0.7434	Intermediate Similarity	NPC327431
0.7434	Intermediate Similarity	NPC476274
0.7419	Intermediate Similarity	NPC52839
0.7414	Intermediate Similarity	NPC266570
0.7414	Intermediate Similarity	NPC475414
0.7414	Intermediate Similarity	NPC173172
0.7414	Intermediate Similarity	NPC60315
0.7411	Intermediate Similarity	NPC474785
0.7411	Intermediate Similarity	NPC253826
0.7411	Intermediate Similarity	NPC474938
0.7407	Intermediate Similarity	NPC476388
0.7407	Intermediate Similarity	NPC477215
0.7398	Intermediate Similarity	NPC472933
0.7398	Intermediate Similarity	NPC180640
0.7395	Intermediate Similarity	NPC475480
0.7395	Intermediate Similarity	NPC473921
0.7395	Intermediate Similarity	NPC475668
0.7391	Intermediate Similarity	NPC176883
0.7391	Intermediate Similarity	NPC475623
0.7391	Intermediate Similarity	NPC475334
0.7391	Intermediate Similarity	NPC473694
0.7391	Intermediate Similarity	NPC476237
0.7377	Intermediate Similarity	NPC156252
0.7373	Intermediate Similarity	NPC475941
0.7373	Intermediate Similarity	NPC474901
0.7368	Intermediate Similarity	NPC224720
0.7368	Intermediate Similarity	NPC476223
0.7368	Intermediate Similarity	NPC282524
0.7368	Intermediate Similarity	NPC118174
0.7368	Intermediate Similarity	NPC476240
0.736	Intermediate Similarity	NPC162009
0.736	Intermediate Similarity	NPC257017
0.736	Intermediate Similarity	NPC19464
0.736	Intermediate Similarity	NPC222688
0.7355	Intermediate Similarity	NPC67259
0.7355	Intermediate Similarity	NPC472400
0.7355	Intermediate Similarity	NPC147912
0.735	Intermediate Similarity	NPC330011
0.735	Intermediate Similarity	NPC329048
0.735	Intermediate Similarity	NPC475294
0.735	Intermediate Similarity	NPC472925
0.7345	Intermediate Similarity	NPC235464
0.7345	Intermediate Similarity	NPC166745
0.7339	Intermediate Similarity	NPC109973
0.7339	Intermediate Similarity	NPC145182
0.7339	Intermediate Similarity	NPC471126
0.7339	Intermediate Similarity	NPC475885
0.7339	Intermediate Similarity	NPC472759
0.7339	Intermediate Similarity	NPC157252
0.7339	Intermediate Similarity	NPC329080
0.7339	Intermediate Similarity	NPC471128
0.7333	Intermediate Similarity	NPC264634
0.7333	Intermediate Similarity	NPC69291
0.7328	Intermediate Similarity	NPC80809
0.7328	Intermediate Similarity	NPC181104
0.7328	Intermediate Similarity	NPC288502
0.7328	Intermediate Similarity	NPC103298
0.7328	Intermediate Similarity	NPC201144
0.7328	Intermediate Similarity	NPC475331
0.7328	Intermediate Similarity	NPC470838
0.7328	Intermediate Similarity	NPC475335
0.7328	Intermediate Similarity	NPC472868
0.7328	Intermediate Similarity	NPC121518
0.7321	Intermediate Similarity	NPC473153
0.7317	Intermediate Similarity	NPC472760
0.7311	Intermediate Similarity	NPC475563
0.7311	Intermediate Similarity	NPC129689
0.7311	Intermediate Similarity	NPC475134
0.7311	Intermediate Similarity	NPC239097
0.7304	Intermediate Similarity	NPC308726
0.7304	Intermediate Similarity	NPC136289
0.7304	Intermediate Similarity	NPC119601
0.7297	Intermediate Similarity	NPC299100
0.7297	Intermediate Similarity	NPC469406
0.7297	Intermediate Similarity	NPC474690
0.7295	Intermediate Similarity	NPC266728
0.7295	Intermediate Similarity	NPC49492
0.7288	Intermediate Similarity	NPC220155
0.7281	Intermediate Similarity	NPC201406
0.7281	Intermediate Similarity	NPC477521
0.728	Intermediate Similarity	NPC472401
0.7273	Intermediate Similarity	NPC472757
0.7273	Intermediate Similarity	NPC962
0.7273	Intermediate Similarity	NPC250109
0.7273	Intermediate Similarity	NPC474018
0.7273	Intermediate Similarity	NPC473986
0.7266	Intermediate Similarity	NPC470882
0.7265	Intermediate Similarity	NPC189863
0.7265	Intermediate Similarity	NPC323834
0.7258	Intermediate Similarity	NPC236918
0.7258	Intermediate Similarity	NPC156745
0.7257	Intermediate Similarity	NPC110937
0.7257	Intermediate Similarity	NPC320306
0.7257	Intermediate Similarity	NPC202705
0.7257	Intermediate Similarity	NPC208094
0.725	Intermediate Similarity	NPC43775
0.725	Intermediate Similarity	NPC472928
0.725	Intermediate Similarity	NPC474315
0.725	Intermediate Similarity	NPC115303
0.725	Intermediate Similarity	NPC475937
0.725	Intermediate Similarity	NPC158523
0.7241	Intermediate Similarity	NPC475526
0.7241	Intermediate Similarity	NPC85742
0.7241	Intermediate Similarity	NPC329345
0.7241	Intermediate Similarity	NPC180204
0.7241	Intermediate Similarity	NPC473283
0.7241	Intermediate Similarity	NPC112009
0.7236	Intermediate Similarity	NPC10721
0.7236	Intermediate Similarity	NPC472934
0.7232	Intermediate Similarity	NPC180950
0.7232	Intermediate Similarity	NPC472469
0.7227	Intermediate Similarity	NPC137911
0.7227	Intermediate Similarity	NPC228477
0.7227	Intermediate Similarity	NPC77947
0.7227	Intermediate Similarity	NPC214644
0.7227	Intermediate Similarity	NPC286174
0.7222	Intermediate Similarity	NPC473097
0.7217	Intermediate Similarity	NPC302537
0.7217	Intermediate Similarity	NPC115862
0.7217	Intermediate Similarity	NPC163372
0.7217	Intermediate Similarity	NPC168319
0.7217	Intermediate Similarity	NPC194028
0.7217	Intermediate Similarity	NPC81530
0.7217	Intermediate Similarity	NPC146822
0.7213	Intermediate Similarity	NPC474872
0.7213	Intermediate Similarity	NPC178289
0.7207	Intermediate Similarity	NPC38232
0.7207	Intermediate Similarity	NPC109305
0.7207	Intermediate Similarity	NPC214697
0.7203	Intermediate Similarity	NPC131665
0.7203	Intermediate Similarity	NPC255387
0.7193	Intermediate Similarity	NPC471717
0.7193	Intermediate Similarity	NPC478056
0.7193	Intermediate Similarity	NPC222011
0.719	Intermediate Similarity	NPC100267
0.719	Intermediate Similarity	NPC475524
0.719	Intermediate Similarity	NPC470063
0.719	Intermediate Similarity	NPC147180
0.719	Intermediate Similarity	NPC280782
0.719	Intermediate Similarity	NPC221144
0.7188	Intermediate Similarity	NPC15095
0.7182	Intermediate Similarity	NPC477149
0.7182	Intermediate Similarity	NPC477147
0.7182	Intermediate Similarity	NPC475965
0.7182	Intermediate Similarity	NPC474842

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 NPC136922 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	280
0.1-0.2	828
0.2-0.3	1887
0.3-0.4	2876
0.4-0.5	2103
0.5-0.6	950
0.6-0.7	220
0.7-0.8	6
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
0.7333	Intermediate Similarity	NPD8297	Approved
0.7288	Intermediate Similarity	NPD7320	Approved
0.7143	Intermediate Similarity	NPD6881	Approved
0.7143	Intermediate Similarity	NPD6899	Approved
0.7119	Intermediate Similarity	NPD6675	Approved
0.7119	Intermediate Similarity	NPD7128	Approved
0.7119	Intermediate Similarity	NPD6402	Approved
0.7119	Intermediate Similarity	NPD5739	Approved
0.7107	Intermediate Similarity	NPD6649	Approved
0.7107	Intermediate Similarity	NPD6650	Approved
0.7107	Intermediate Similarity	NPD8130	Phase 1
0.7097	Intermediate Similarity	NPD7115	Discovery
0.7083	Intermediate Similarity	NPD6373	Approved
0.7083	Intermediate Similarity	NPD6372	Approved
0.7059	Intermediate Similarity	NPD5697	Approved
0.7049	Intermediate Similarity	NPD6882	Approved
0.7025	Intermediate Similarity	NPD7102	Approved
0.7025	Intermediate Similarity	NPD6883	Approved
0.7025	Intermediate Similarity	NPD7290	Approved
0.7	Intermediate Similarity	NPD6011	Approved
0.6967	Remote Similarity	NPD6869	Approved
0.6967	Remote Similarity	NPD6847	Approved
0.6967	Remote Similarity	NPD6617	Approved
0.6957	Remote Similarity	NPD6084	Phase 2
0.6957	Remote Similarity	NPD6083	Phase 2
0.6942	Remote Similarity	NPD6012	Approved
0.6942	Remote Similarity	NPD6013	Approved
0.6942	Remote Similarity	NPD6014	Approved
0.6917	Remote Similarity	NPD5701	Approved
0.6897	Remote Similarity	NPD4225	Approved
0.687	Remote Similarity	NPD4697	Phase 3
0.6847	Remote Similarity	NPD5737	Approved
0.6847	Remote Similarity	NPD6672	Approved
0.6838	Remote Similarity	NPD7639	Approved
0.6838	Remote Similarity	NPD7640	Approved
0.6829	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5279	Phase 3
0.6797	Remote Similarity	NPD6319	Approved
0.6783	Remote Similarity	NPD5695	Phase 3
0.6754	Remote Similarity	NPD6399	Phase 3
0.6752	Remote Similarity	NPD7638	Approved
0.6748	Remote Similarity	NPD6371	Approved
0.6746	Remote Similarity	NPD6868	Approved
0.6726	Remote Similarity	NPD5785	Approved
0.6724	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5221	Approved
0.6724	Remote Similarity	NPD5222	Approved
0.6723	Remote Similarity	NPD5211	Phase 2
0.672	Remote Similarity	NPD4632	Approved
0.6698	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD5362	Discontinued
0.6696	Remote Similarity	NPD7748	Approved
0.6667	Remote Similarity	NPD6050	Approved
0.6667	Remote Similarity	NPD7637	Suspended
0.6667	Remote Similarity	NPD7507	Approved
0.6667	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD6079	Approved
0.6641	Remote Similarity	NPD6335	Approved
0.6639	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD5328	Approved
0.6617	Remote Similarity	NPD7078	Approved
0.6614	Remote Similarity	NPD6274	Approved
0.6612	Remote Similarity	NPD5141	Approved
0.661	Remote Similarity	NPD5696	Approved
0.6591	Remote Similarity	NPD7492	Approved
0.6589	Remote Similarity	NPD7100	Approved
0.6589	Remote Similarity	NPD7101	Approved
0.6579	Remote Similarity	NPD5692	Phase 3
0.6577	Remote Similarity	NPD5363	Approved
0.6567	Remote Similarity	NPD7736	Approved
0.6562	Remote Similarity	NPD6009	Approved
0.6562	Remote Similarity	NPD6317	Approved
0.6555	Remote Similarity	NPD4696	Approved
0.6555	Remote Similarity	NPD5285	Approved
0.6555	Remote Similarity	NPD5286	Approved
0.6549	Remote Similarity	NPD6903	Approved
0.6541	Remote Similarity	NPD6616	Approved
0.6538	Remote Similarity	NPD6054	Approved
0.6525	Remote Similarity	NPD7902	Approved
0.6525	Remote Similarity	NPD4755	Approved
0.6522	Remote Similarity	NPD7515	Phase 2
0.6522	Remote Similarity	NPD5694	Approved
0.6519	Remote Similarity	NPD7319	Approved
0.6518	Remote Similarity	NPD3618	Phase 1
0.6515	Remote Similarity	NPD7604	Phase 2
0.6512	Remote Similarity	NPD6314	Approved
0.6512	Remote Similarity	NPD6313	Approved
0.65	Remote Similarity	NPD5223	Approved
0.6493	Remote Similarity	NPD8293	Discontinued
0.6491	Remote Similarity	NPD6904	Approved
0.6491	Remote Similarity	NPD6673	Approved
0.6491	Remote Similarity	NPD6080	Approved
0.6489	Remote Similarity	NPD5983	Phase 2
0.6486	Remote Similarity	NPD4786	Approved
0.6466	Remote Similarity	NPD5778	Approved
0.6466	Remote Similarity	NPD5779	Approved
0.646	Remote Similarity	NPD7524	Approved
0.6452	Remote Similarity	NPD6686	Approved
0.6449	Remote Similarity	NPD4756	Discovery
0.6446	Remote Similarity	NPD5225	Approved
0.6446	Remote Similarity	NPD5226	Approved
0.6446	Remote Similarity	NPD5224	Approved
0.6446	Remote Similarity	NPD4633	Approved
0.6439	Remote Similarity	NPD6370	Approved
0.6422	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD6336	Discontinued
0.6417	Remote Similarity	NPD4700	Approved
0.6412	Remote Similarity	NPD6059	Approved
0.6396	Remote Similarity	NPD5331	Approved
0.6396	Remote Similarity	NPD5332	Approved
0.6396	Remote Similarity	NPD7154	Phase 3
0.6393	Remote Similarity	NPD5175	Approved
0.6393	Remote Similarity	NPD5174	Approved
0.6379	Remote Similarity	NPD8034	Phase 2
0.6379	Remote Similarity	NPD7983	Approved
0.6379	Remote Similarity	NPD5693	Phase 1
0.6379	Remote Similarity	NPD6411	Approved
0.6379	Remote Similarity	NPD8035	Phase 2
0.6378	Remote Similarity	NPD6053	Discontinued
0.6372	Remote Similarity	NPD7146	Approved
0.6372	Remote Similarity	NPD6684	Approved
0.6372	Remote Similarity	NPD5330	Approved
0.6372	Remote Similarity	NPD7521	Approved
0.6372	Remote Similarity	NPD7334	Approved
0.6372	Remote Similarity	NPD6409	Approved
0.6364	Remote Similarity	NPD6015	Approved
0.6364	Remote Similarity	NPD6908	Approved
0.6364	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6016	Approved
0.6364	Remote Similarity	NPD4790	Discontinued
0.6364	Remote Similarity	NPD6909	Approved
0.6364	Remote Similarity	NPD5344	Discontinued
0.6356	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD4634	Approved
0.6348	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD4753	Phase 2
0.6325	Remote Similarity	NPD4202	Approved
0.632	Remote Similarity	NPD4730	Approved
0.632	Remote Similarity	NPD4729	Approved
0.6316	Remote Similarity	NPD5988	Approved
0.6311	Remote Similarity	NPD7632	Discontinued
0.6306	Remote Similarity	NPD3667	Approved
0.6306	Remote Similarity	NPD4269	Approved
0.6306	Remote Similarity	NPD4270	Approved
0.6306	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD7260	Phase 2
0.6293	Remote Similarity	NPD46	Approved
0.6293	Remote Similarity	NPD6698	Approved
0.6293	Remote Similarity	NPD7838	Discovery
0.629	Remote Similarity	NPD4767	Approved
0.629	Remote Similarity	NPD4768	Approved
0.629	Remote Similarity	NPD6008	Approved
0.6283	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD1694	Approved
0.6283	Remote Similarity	NPD1696	Phase 3
0.6281	Remote Similarity	NPD6648	Approved
0.6273	Remote Similarity	NPD4695	Discontinued
0.6271	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD7900	Approved
0.6269	Remote Similarity	NPD8328	Phase 3
0.6261	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.626	Remote Similarity	NPD4754	Approved
0.625	Remote Similarity	NPD6695	Phase 3
0.6241	Remote Similarity	NPD7503	Approved
0.6241	Remote Similarity	NPD8033	Approved
0.6239	Remote Similarity	NPD5284	Approved
0.6239	Remote Similarity	NPD5281	Approved
0.6228	Remote Similarity	NPD4694	Approved
0.6228	Remote Similarity	NPD5280	Approved
0.6228	Remote Similarity	NPD6098	Approved
0.6228	Remote Similarity	NPD5786	Approved
0.622	Remote Similarity	NPD5250	Approved
0.622	Remote Similarity	NPD5248	Approved
0.622	Remote Similarity	NPD5247	Approved
0.622	Remote Similarity	NPD5249	Phase 3
0.622	Remote Similarity	NPD5251	Approved
0.6218	Remote Similarity	NPD5210	Approved
0.6218	Remote Similarity	NPD5654	Approved
0.6218	Remote Similarity	NPD4629	Approved
0.6212	Remote Similarity	NPD7516	Approved
0.6207	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6101	Approved
0.6204	Remote Similarity	NPD6933	Approved
0.6195	Remote Similarity	NPD3666	Approved
0.6195	Remote Similarity	NPD3665	Phase 1
0.6195	Remote Similarity	NPD3133	Approved
0.6195	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5168	Approved
0.619	Remote Similarity	NPD5128	Approved
0.6174	Remote Similarity	NPD7750	Discontinued
0.6165	Remote Similarity	NPD8294	Approved
0.6165	Remote Similarity	NPD8377	Approved
0.6154	Remote Similarity	NPD5207	Approved
0.6148	Remote Similarity	NPD6404	Discontinued
0.6143	Remote Similarity	NPD6845	Suspended
0.6142	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.614	Remote Similarity	NPD5329	Approved
0.614	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD7327	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