NPASS Compound

Structure

NPC252714 OpenBabel07101718232D 39 43 0 0 1 0 0 0 0 0999 V2000 -4.7264 -0.9460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8463 1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5163 -1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3745 -2.6017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5067 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6927 -0.9773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8463 -1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0429 0.9773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6927 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6927 -2.9318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8463 -2.4432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8463 0.4886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4685 1.7679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8463 1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6927 1.9545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7705 -0.7428 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4685 0.1866 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6927 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.9773 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6927 -0.9773 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5390 -2.4432 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5390 0.4886 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1165 -1.4691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0277 -0.6196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1415 2.3587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8463 -1.4659 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8463 0.4886 0.0000 C 0 0 1 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 2.5390 -1.4659 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5390 1.4659 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3854 -2.9318 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0049 -0.6196 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5390 0.2268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1696 2.4608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7160 3.1493 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4185 -2.3985 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1606 -1.2659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 29 1 0 0 0 0 6 38 1 0 0 0 0 7 39 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 15 1 0 0 0 0 10 19 1 0 0 0 0 11 14 1 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 12 23 1 0 0 0 0 13 28 1 0 0 0 0 14 30 1 0 0 0 0 15 32 1 0 0 0 0 16 17 1 0 0 0 0 16 29 1 0 0 0 0 17 32 1 0 0 0 0 18 1 1 6 0 0 0 18 25 1 0 0 0 0 19 18 1 6 0 0 0 19 24 1 0 0 0 0 20 24 1 0 0 0 0 20 29 1 6 0 0 0 21 28 1 1 0 0 0 21 30 1 0 0 0 0 22 28 1 1 0 0 0 22 31 1 0 0 0 0 23 31 1 6 0 0 0 23 33 1 0 0 0 0 24 32 1 1 0 0 0 25 38 1 0 0 0 0 25 39 1 0 0 0 0 26 31 1 0 0 0 0 26 34 2 0 0 0 0 26 35 1 0 0 0 0 27 36 2 0 0 0 0 27 37 1 0 0 0 0 28 2 1 1 0 0 0 29 30 1 1 0 0 0 30 4 1 1 0 0 0 31 5 1 1 0 0 0 32 27 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	548.37
Volume:	575.504
LogP:	3.358
LogD:	3.951
LogS:	-3.423
# Rotatable Bonds:	6
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.358
Synthetic Accessibility Score:	5.202
Fsp3:	0.938
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.615
MDCK Permeability:	6.0805810790043324e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.039
30% Bioavailability (F30%):	0.826

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	87.71110534667969%
Volume Distribution (VD):	0.548
Pgp-substrate:	3.935427665710449%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.916
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.874
CYP2C9-inhibitor:	0.067
CYP2C9-substrate:	0.224
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.106
CYP3A4-inhibitor:	0.062
CYP3A4-substrate:	0.129

ADMET: Excretion

Clearance (CL):	1.843
Half-life (T1/2):	0.396

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.376
Drug-inuced Liver Injury (DILI):	0.003
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.051
Maximum Recommended Daily Dose:	0.011
Skin Sensitization:	0.051
Carcinogencity:	0.006
Eye Corrosion:	0.02
Eye Irritation:	0.138
Respiratory Toxicity:	0.715

Download Data

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

Natural Product: NPC252714

Natural Product ID:	NPC252714
*Common Name:**	(20R)-3Alpha-Hydroxy-29-Dimethoxylupan-23,28-Dioic Acid
IUPAC Name:	(1R,3aS,5aR,5bR,7aR,8S,9R,11aR,11bR,13aR,13bR)-1-[(2R)-1,1-dimethoxypropan-2-yl]-9-hydroxy-5a,5b,8,11a-tetramethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a,8-dicarboxylic acid
Synonyms:
Standard InCHIKey:	LPZQKKIWBGFZFF-DBXFEVPDSA-N
Standard InCHI:	InChI=1S/C32H52O7/c1-18(25(38-6)39-7)19-10-15-32(27(36)37)17-16-29(3)20(24(19)32)8-9-21-28(2)13-12-23(33)31(5,26(34)35)22(28)11-14-30(21,29)4/h18-25,33H,8-17H2,1-7H3,(H,34,35)(H,36,37)/t18-,19+,20-,21-,22-,23-,24-,28-,29-,30-,31+,32+/m1/s1
SMILES:	COC([C@@H]([C@@H]1CC[C@]2([C@H]1[C@H]1CC[C@H]3[C@@]([C@]1(C)CC2)(C)CC[C@@H]1[C@]3(C)CC[C@H]([C@@]1(C)C(=O)O)O)C(=O)O)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1269322
PubChem CID:	52944262
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO29834	Acanthopanax koreanum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20621475]
NPO29834	Acanthopanax koreanum	n.a.	n.a.	n.a.	steamed leaves	n.a.	n.a.	PMID[20932756]
NPO29834	Acanthopanax koreanum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	4

Activity Type	# Activity
Individual Protein	1
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	<	100.0	%	PMID[485647]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	94.2	%	PMID[485646]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	64.7	%	PMID[485646]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	63.6	%	PMID[485646]

☑ 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 NPC252714 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	398
0.1-0.2	3308
0.2-0.3	11023
0.3-0.4	12743
0.4-0.5	6000
0.5-0.6	3989
0.6-0.7	3926
0.7-0.8	1185
0.8-0.85	108
0.85-0.9	16
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8902	High Similarity	NPC261616
0.8765	High Similarity	NPC298168
0.8765	High Similarity	NPC143133
0.8706	High Similarity	NPC319909
0.869	High Similarity	NPC61107
0.869	High Similarity	NPC289486
0.8642	High Similarity	NPC4209
0.8556	High Similarity	NPC471902
0.8556	High Similarity	NPC473690
0.8556	High Similarity	NPC287118
0.8554	High Similarity	NPC201276
0.8554	High Similarity	NPC80891
0.8537	High Similarity	NPC207010
0.8537	High Similarity	NPC317913
0.8519	High Similarity	NPC212733
0.8488	Intermediate Similarity	NPC473336
0.8488	Intermediate Similarity	NPC471044
0.8471	Intermediate Similarity	NPC30583
0.8444	Intermediate Similarity	NPC471901
0.8444	Intermediate Similarity	NPC475416
0.8438	Intermediate Similarity	NPC469827
0.8434	Intermediate Similarity	NPC224802
0.8434	Intermediate Similarity	NPC324700
0.8434	Intermediate Similarity	NPC80089
0.8434	Intermediate Similarity	NPC171426
0.8434	Intermediate Similarity	NPC34046
0.8427	Intermediate Similarity	NPC213832
0.8427	Intermediate Similarity	NPC57954
0.8415	Intermediate Similarity	NPC477932
0.8415	Intermediate Similarity	NPC477933
0.8395	Intermediate Similarity	NPC280026
0.8395	Intermediate Similarity	NPC167702
0.8395	Intermediate Similarity	NPC477930
0.8333	Intermediate Similarity	NPC320144
0.8315	Intermediate Similarity	NPC471900
0.8313	Intermediate Similarity	NPC477918
0.8313	Intermediate Similarity	NPC471151
0.8295	Intermediate Similarity	NPC302111
0.8293	Intermediate Similarity	NPC97534
0.8293	Intermediate Similarity	NPC174964
0.8293	Intermediate Similarity	NPC195155
0.8293	Intermediate Similarity	NPC477934
0.8214	Intermediate Similarity	NPC243594
0.8214	Intermediate Similarity	NPC185465
0.8214	Intermediate Similarity	NPC31031
0.8202	Intermediate Similarity	NPC33768
0.8202	Intermediate Similarity	NPC269360
0.8202	Intermediate Similarity	NPC264005
0.8193	Intermediate Similarity	NPC5767
0.8193	Intermediate Similarity	NPC475742
0.8191	Intermediate Similarity	NPC472273
0.8182	Intermediate Similarity	NPC469826
0.814	Intermediate Similarity	NPC58631
0.814	Intermediate Similarity	NPC12933
0.8132	Intermediate Similarity	NPC169933
0.8118	Intermediate Similarity	NPC220379
0.8111	Intermediate Similarity	NPC4309
0.81	Intermediate Similarity	NPC469825
0.8095	Intermediate Similarity	NPC221420
0.8095	Intermediate Similarity	NPC23884
0.809	Intermediate Similarity	NPC2783
0.809	Intermediate Similarity	NPC12774
0.809	Intermediate Similarity	NPC83242
0.8068	Intermediate Similarity	NPC219535
0.8068	Intermediate Similarity	NPC473299
0.8068	Intermediate Similarity	NPC237938
0.8049	Intermediate Similarity	NPC232112
0.8046	Intermediate Similarity	NPC121121
0.8046	Intermediate Similarity	NPC13494
0.8046	Intermediate Similarity	NPC477935
0.8025	Intermediate Similarity	NPC477929
0.8022	Intermediate Similarity	NPC24705
0.8022	Intermediate Similarity	NPC56962
0.8	Intermediate Similarity	NPC329117
0.8	Intermediate Similarity	NPC472608
0.7978	Intermediate Similarity	NPC264317
0.7978	Intermediate Similarity	NPC131350
0.7978	Intermediate Similarity	NPC294438
0.7957	Intermediate Similarity	NPC476189
0.7955	Intermediate Similarity	NPC213737
0.7955	Intermediate Similarity	NPC475820
0.7955	Intermediate Similarity	NPC474284
0.7955	Intermediate Similarity	NPC474346
0.7955	Intermediate Similarity	NPC474253
0.7941	Intermediate Similarity	NPC469824
0.7941	Intermediate Similarity	NPC11035
0.7938	Intermediate Similarity	NPC477172
0.7935	Intermediate Similarity	NPC88337
0.7935	Intermediate Similarity	NPC475211
0.7931	Intermediate Similarity	NPC73515
0.7931	Intermediate Similarity	NPC271572
0.7931	Intermediate Similarity	NPC280781
0.7931	Intermediate Similarity	NPC474870
0.7931	Intermediate Similarity	NPC48756
0.7927	Intermediate Similarity	NPC156277
0.7927	Intermediate Similarity	NPC469940
0.7927	Intermediate Similarity	NPC320549
0.7927	Intermediate Similarity	NPC151018
0.7927	Intermediate Similarity	NPC58057
0.7917	Intermediate Similarity	NPC474092
0.7912	Intermediate Similarity	NPC146937
0.7912	Intermediate Similarity	NPC16377
0.7912	Intermediate Similarity	NPC474719
0.7901	Intermediate Similarity	NPC252032
0.7901	Intermediate Similarity	NPC319671
0.7901	Intermediate Similarity	NPC476734
0.7901	Intermediate Similarity	NPC469941
0.7895	Intermediate Similarity	NPC193785
0.7865	Intermediate Similarity	NPC34984
0.7865	Intermediate Similarity	NPC50438
0.7865	Intermediate Similarity	NPC25037
0.7857	Intermediate Similarity	NPC273366
0.7849	Intermediate Similarity	NPC160506
0.7849	Intermediate Similarity	NPC475878
0.7841	Intermediate Similarity	NPC477936
0.7841	Intermediate Similarity	NPC2096
0.7841	Intermediate Similarity	NPC268040
0.7841	Intermediate Similarity	NPC208912
0.7835	Intermediate Similarity	NPC80417
0.7835	Intermediate Similarity	NPC41843
0.7826	Intermediate Similarity	NPC67653
0.7826	Intermediate Similarity	NPC220498
0.7826	Intermediate Similarity	NPC471459
0.7822	Intermediate Similarity	NPC88744
0.7816	Intermediate Similarity	NPC477851
0.7805	Intermediate Similarity	NPC108131
0.7802	Intermediate Similarity	NPC134197
0.7791	Intermediate Similarity	NPC26029
0.7791	Intermediate Similarity	NPC476732
0.7791	Intermediate Similarity	NPC199965
0.7789	Intermediate Similarity	NPC215570
0.7789	Intermediate Similarity	NPC62407
0.7789	Intermediate Similarity	NPC205173
0.7789	Intermediate Similarity	NPC287354
0.7788	Intermediate Similarity	NPC146563
0.7778	Intermediate Similarity	NPC62572
0.7778	Intermediate Similarity	NPC473350
0.7778	Intermediate Similarity	NPC98270
0.7778	Intermediate Similarity	NPC201655
0.7767	Intermediate Similarity	NPC272242
0.7767	Intermediate Similarity	NPC270586
0.7766	Intermediate Similarity	NPC472232
0.7766	Intermediate Similarity	NPC472231
0.7765	Intermediate Similarity	NPC472486
0.7765	Intermediate Similarity	NPC472487
0.7745	Intermediate Similarity	NPC473844
0.7745	Intermediate Similarity	NPC240125
0.7745	Intermediate Similarity	NPC91583
0.7745	Intermediate Similarity	NPC51947
0.7742	Intermediate Similarity	NPC77756
0.7738	Intermediate Similarity	NPC254340
0.7727	Intermediate Similarity	NPC476071
0.7727	Intermediate Similarity	NPC50658
0.7723	Intermediate Similarity	NPC203974
0.7717	Intermediate Similarity	NPC131104
0.7717	Intermediate Similarity	NPC3032
0.7717	Intermediate Similarity	NPC473319
0.7711	Intermediate Similarity	NPC89310
0.7708	Intermediate Similarity	NPC116683
0.7708	Intermediate Similarity	NPC327788
0.7701	Intermediate Similarity	NPC73013
0.7692	Intermediate Similarity	NPC472272
0.7692	Intermediate Similarity	NPC114378
0.7692	Intermediate Similarity	NPC103782
0.7692	Intermediate Similarity	NPC470543
0.7692	Intermediate Similarity	NPC243572
0.7684	Intermediate Similarity	NPC151214
0.7684	Intermediate Similarity	NPC191915
0.7684	Intermediate Similarity	NPC277399
0.7684	Intermediate Similarity	NPC206878
0.7683	Intermediate Similarity	NPC131892
0.7683	Intermediate Similarity	NPC196197
0.7683	Intermediate Similarity	NPC213178
0.7683	Intermediate Similarity	NPC327728
0.7683	Intermediate Similarity	NPC6120
0.7677	Intermediate Similarity	NPC80640
0.7674	Intermediate Similarity	NPC212453
0.7674	Intermediate Similarity	NPC477919
0.7674	Intermediate Similarity	NPC180199
0.7674	Intermediate Similarity	NPC475031
0.7667	Intermediate Similarity	NPC474996
0.7667	Intermediate Similarity	NPC477434
0.7667	Intermediate Similarity	NPC475509
0.7653	Intermediate Similarity	NPC94906
0.7653	Intermediate Similarity	NPC20028
0.7647	Intermediate Similarity	NPC21220
0.7647	Intermediate Similarity	NPC472311
0.7647	Intermediate Similarity	NPC125767
0.7647	Intermediate Similarity	NPC472079
0.7647	Intermediate Similarity	NPC207693
0.7642	Intermediate Similarity	NPC137414
0.7642	Intermediate Similarity	NPC469820
0.7642	Intermediate Similarity	NPC469823
0.7634	Intermediate Similarity	NPC61688
0.7634	Intermediate Similarity	NPC247312
0.7634	Intermediate Similarity	NPC271974
0.7629	Intermediate Similarity	NPC253586
0.7619	Intermediate Similarity	NPC68426
0.7619	Intermediate Similarity	NPC477229
0.7619	Intermediate Similarity	NPC282905

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 NPC252714 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	418
0.1-0.2	3491
0.2-0.3	3539
0.3-0.4	1034
0.4-0.5	284
0.5-0.6	240
0.6-0.7	112
0.7-0.8	24
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8642	High Similarity	NPD6117	Approved
0.8537	High Similarity	NPD6116	Phase 1
0.8434	Intermediate Similarity	NPD6697	Approved
0.8434	Intermediate Similarity	NPD6115	Approved
0.8434	Intermediate Similarity	NPD6118	Approved
0.8434	Intermediate Similarity	NPD6114	Approved
0.8395	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD8035	Phase 2
0.7849	Intermediate Similarity	NPD8034	Phase 2
0.7683	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6081	Approved
0.7442	Intermediate Similarity	NPD3703	Phase 2
0.7381	Intermediate Similarity	NPD4789	Approved
0.7381	Intermediate Similarity	NPD4244	Approved
0.7381	Intermediate Similarity	NPD4245	Approved
0.7353	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD5360	Phase 3
0.7349	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD4224	Phase 2
0.7294	Intermediate Similarity	NPD5777	Approved
0.7262	Intermediate Similarity	NPD3698	Phase 2
0.7262	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3702	Approved
0.7195	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3671	Phase 1
0.6972	Remote Similarity	NPD8133	Approved
0.697	Remote Similarity	NPD7748	Approved
0.6961	Remote Similarity	NPD8418	Phase 2
0.6939	Remote Similarity	NPD7515	Phase 2
0.6937	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4758	Discontinued
0.6869	Remote Similarity	NPD8171	Discontinued
0.6848	Remote Similarity	NPD6928	Phase 2
0.6847	Remote Similarity	NPD6940	Discontinued
0.6813	Remote Similarity	NPD5364	Discontinued
0.678	Remote Similarity	NPD7736	Approved
0.6765	Remote Similarity	NPD7902	Approved
0.6759	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.67	Remote Similarity	NPD6399	Phase 3
0.6636	Remote Similarity	NPD6402	Approved
0.6636	Remote Similarity	NPD7128	Approved
0.6636	Remote Similarity	NPD5739	Approved
0.6636	Remote Similarity	NPD6675	Approved
0.6591	Remote Similarity	NPD4787	Phase 1
0.6583	Remote Similarity	NPD7319	Approved
0.6581	Remote Similarity	NPD8328	Phase 3
0.6577	Remote Similarity	NPD6882	Approved
0.6566	Remote Similarity	NPD5328	Approved
0.6562	Remote Similarity	NPD4786	Approved
0.6555	Remote Similarity	NPD8293	Discontinued
0.6538	Remote Similarity	NPD7638	Approved
0.6514	Remote Similarity	NPD7320	Approved
0.6514	Remote Similarity	NPD6881	Approved
0.6514	Remote Similarity	NPD6899	Approved
0.6491	Remote Similarity	NPD7115	Discovery
0.6486	Remote Similarity	NPD8130	Phase 1
0.6476	Remote Similarity	NPD7639	Approved
0.6476	Remote Similarity	NPD7640	Approved
0.6471	Remote Similarity	NPD7900	Approved
0.6471	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7507	Approved
0.6458	Remote Similarity	NPD4788	Approved
0.6455	Remote Similarity	NPD6372	Approved
0.6455	Remote Similarity	NPD6373	Approved
0.6442	Remote Similarity	NPD6084	Phase 2
0.6442	Remote Similarity	NPD6083	Phase 2
0.6436	Remote Similarity	NPD6079	Approved
0.6429	Remote Similarity	NPD3618	Phase 1
0.6429	Remote Similarity	NPD8297	Approved
0.6422	Remote Similarity	NPD6412	Phase 2
0.6422	Remote Similarity	NPD5701	Approved
0.6422	Remote Similarity	NPD5697	Approved
0.6396	Remote Similarity	NPD7290	Approved
0.6396	Remote Similarity	NPD7102	Approved
0.6396	Remote Similarity	NPD6883	Approved
0.6386	Remote Similarity	NPD3198	Approved
0.6356	Remote Similarity	NPD6370	Approved
0.6355	Remote Similarity	NPD7632	Discontinued
0.6354	Remote Similarity	NPD3667	Approved
0.6339	Remote Similarity	NPD6650	Approved
0.6339	Remote Similarity	NPD6617	Approved
0.6339	Remote Similarity	NPD6847	Approved
0.6339	Remote Similarity	NPD6649	Approved
0.6339	Remote Similarity	NPD6869	Approved
0.6316	Remote Similarity	NPD7525	Registered
0.6306	Remote Similarity	NPD6012	Approved
0.6306	Remote Similarity	NPD6013	Approved
0.6306	Remote Similarity	NPD6014	Approved
0.63	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD4755	Approved
0.6277	Remote Similarity	NPD4802	Phase 2
0.6277	Remote Similarity	NPD4238	Approved
0.6262	Remote Similarity	NPD1700	Approved
0.625	Remote Similarity	NPD7492	Approved
0.6228	Remote Similarity	NPD8298	Phase 2
0.6216	Remote Similarity	NPD6011	Approved
0.6216	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD4202	Approved
0.6211	Remote Similarity	NPD7645	Phase 2
0.6198	Remote Similarity	NPD6616	Approved
0.6195	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4697	Phase 3
0.619	Remote Similarity	NPD5221	Approved
0.619	Remote Similarity	NPD5222	Approved
0.6186	Remote Similarity	NPD6059	Approved
0.6186	Remote Similarity	NPD8377	Approved
0.6186	Remote Similarity	NPD6054	Approved
0.6186	Remote Similarity	NPD8294	Approved
0.6182	Remote Similarity	NPD6920	Discontinued
0.6173	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5285	Approved
0.6168	Remote Similarity	NPD5286	Approved
0.6168	Remote Similarity	NPD4700	Approved
0.6168	Remote Similarity	NPD4696	Approved
0.6154	Remote Similarity	NPD7327	Approved
0.6154	Remote Similarity	NPD7328	Approved
0.6148	Remote Similarity	NPD7078	Approved
0.6139	Remote Similarity	NPD5737	Approved
0.6139	Remote Similarity	NPD6672	Approved
0.6134	Remote Similarity	NPD8296	Approved
0.6134	Remote Similarity	NPD8380	Approved
0.6134	Remote Similarity	NPD8335	Approved
0.6134	Remote Similarity	NPD8379	Approved
0.6134	Remote Similarity	NPD8033	Approved
0.6134	Remote Similarity	NPD8378	Approved
0.6132	Remote Similarity	NPD5173	Approved
0.6122	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD3669	Approved
0.6117	Remote Similarity	NPD6411	Approved
0.6102	Remote Similarity	NPD7516	Approved
0.61	Remote Similarity	NPD7146	Approved
0.61	Remote Similarity	NPD6409	Approved
0.61	Remote Similarity	NPD7334	Approved
0.61	Remote Similarity	NPD7521	Approved
0.61	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.61	Remote Similarity	NPD5330	Approved
0.61	Remote Similarity	NPD6684	Approved
0.6095	Remote Similarity	NPD7991	Discontinued
0.6095	Remote Similarity	NPD5695	Phase 3
0.6082	Remote Similarity	NPD1780	Approved
0.6082	Remote Similarity	NPD1779	Approved
0.6078	Remote Similarity	NPD4753	Phase 2
0.6075	Remote Similarity	NPD5696	Approved
0.6071	Remote Similarity	NPD6686	Approved
0.6068	Remote Similarity	NPD6009	Approved
0.6061	Remote Similarity	NPD3666	Approved
0.6061	Remote Similarity	NPD3133	Approved
0.6061	Remote Similarity	NPD3665	Phase 1
0.6055	Remote Similarity	NPD5211	Phase 2
0.6055	Remote Similarity	NPD5225	Approved
0.6055	Remote Similarity	NPD5226	Approved
0.6055	Remote Similarity	NPD4633	Approved
0.6055	Remote Similarity	NPD5224	Approved
0.605	Remote Similarity	NPD6319	Approved
0.6	Remote Similarity	NPD6015	Approved
0.6	Remote Similarity	NPD6016	Approved
0.6	Remote Similarity	NPD5174	Approved
0.6	Remote Similarity	NPD5175	Approved
0.6	Remote Similarity	NPD229	Approved
0.5983	Remote Similarity	NPD6868	Approved
0.5983	Remote Similarity	NPD6274	Approved
0.598	Remote Similarity	NPD6903	Approved
0.5966	Remote Similarity	NPD7101	Approved
0.5966	Remote Similarity	NPD7100	Approved
0.5965	Remote Similarity	NPD4634	Approved
0.5963	Remote Similarity	NPD5223	Approved
0.5962	Remote Similarity	NPD7637	Suspended
0.595	Remote Similarity	NPD5988	Approved
0.5948	Remote Similarity	NPD4632	Approved
0.5946	Remote Similarity	NPD5141	Approved
0.5943	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD6415	Discontinued
0.5926	Remote Similarity	NPD4225	Approved
0.5922	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD6101	Approved
0.5909	Remote Similarity	NPD7909	Approved
0.59	Remote Similarity	NPD3668	Phase 3
0.5893	Remote Similarity	NPD4767	Approved
0.5893	Remote Similarity	NPD4768	Approved
0.5882	Remote Similarity	NPD6335	Approved
0.5877	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD6908	Approved
0.5868	Remote Similarity	NPD6909	Approved
0.5856	Remote Similarity	NPD4754	Approved
0.5804	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD6317	Approved
0.5794	Remote Similarity	NPD4629	Approved
0.5794	Remote Similarity	NPD5210	Approved
0.5789	Remote Similarity	NPD7339	Approved
0.5789	Remote Similarity	NPD4730	Approved
0.5789	Remote Similarity	NPD6942	Approved
0.5789	Remote Similarity	NPD4729	Approved
0.5789	Remote Similarity	NPD2257	Approved
0.5789	Remote Similarity	NPD5128	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