NPASS Compound

Structure

NPC473038 OpenBabel07101718222D 31 34 0 0 1 0 0 0 0 0999 V2000 -0.5909 3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 2.2601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2382 2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 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 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 3.4190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9074 1.7248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 22 1 0 0 0 0 3 22 1 0 0 0 0 5 24 1 0 0 0 0 7 8 1 0 0 0 0 7 17 1 0 0 0 0 8 23 1 0 0 0 0 9 13 1 0 0 0 0 9 18 1 0 0 0 0 10 14 1 0 0 0 0 10 16 1 0 0 0 0 11 15 1 0 0 0 0 11 24 1 0 0 0 0 12 1 1 1 0 0 0 12 13 1 0 0 0 0 12 21 1 0 0 0 0 13 24 1 6 0 0 0 14 20 1 0 0 0 0 14 26 2 0 0 0 0 15 19 1 0 0 0 0 15 27 2 0 0 0 0 16 22 1 0 0 0 0 16 23 1 6 0 0 0 17 22 1 0 0 0 0 17 28 2 0 0 0 0 18 25 1 0 0 0 0 18 29 2 0 0 0 0 19 20 2 0 0 0 0 19 23 1 0 0 0 0 20 25 1 0 0 0 0 21 30 2 0 0 0 0 21 31 1 0 0 0 0 23 4 1 6 0 0 0 24 25 1 6 0 0 0 25 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	428.22
Volume:	443.653
LogP:	2.16
LogD:	1.434
LogS:	-4.296
# Rotatable Bonds:	2
TPSA:	105.58
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.721
Synthetic Accessibility Score:	4.824
Fsp3:	0.72
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.418
MDCK Permeability:	1.9965649698860943e-05
Pgp-inhibitor:	0.532
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.922

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.8
Plasma Protein Binding (PPB):	79.03852844238281%
Volume Distribution (VD):	0.351
Pgp-substrate:	12.735245704650879%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.886
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.849
CYP2C9-inhibitor:	0.064
CYP2C9-substrate:	0.385
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.076
CYP3A4-inhibitor:	0.052
CYP3A4-substrate:	0.671

ADMET: Excretion

Clearance (CL):	5.758
Half-life (T1/2):	0.858

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.125
Drug-inuced Liver Injury (DILI):	0.404
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.128
Maximum Recommended Daily Dose:	0.075
Skin Sensitization:	0.111
Carcinogencity:	0.247
Eye Corrosion:	0.009
Eye Irritation:	0.03
Respiratory Toxicity:	0.792

Download Data

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

Natural Product: NPC473038

Natural Product ID:	NPC473038
*Common Name:**	UAFWFNZQRZDPMO-FXJQOORKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UAFWFNZQRZDPMO-FXJQOORKSA-N
Standard InCHI:	InChI=1S/C25H32O6/c1-12(21(30)31)13-9-18(29)25(6)20-14(26)10-16-22(2,3)17(28)7-8-23(16,4)19(20)15(27)11-24(13,25)5/h12-13,16H,7-11H2,1-6H3,(H,30,31)/t12-,13+,16-,23-,24+,25-/m0/s1
SMILES:	OC(=O)[C@H]([C@H]1CC(=O)[C@@]2([C@]1(C)CC(=O)C1=C2C(=O)C[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3601515
PubChem CID:	n.a.
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
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.phytochem.2005.10.025]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[11520245]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12045343]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14695801]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791484]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	spore	n.a.	PMID[18827358]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	Nagano, Japan	2008-MAY	PMID[20039640]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20384295]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[20702092]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[21924611]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22014750]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[22044278]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[22047696]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26222905]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[9635497]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1648	Individual Protein	Oligo-1,6-glucosidase	Saccharomyces cerevisiae S288c	IC50	=	144500.0	nM	PMID[477157]

☑ 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 NPC473038 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	168
0.1-0.2	1440
0.2-0.3	7734
0.3-0.4	14831
0.4-0.5	7427
0.5-0.6	6719
0.6-0.7	3477
0.7-0.8	738
0.8-0.85	111
0.85-0.9	41
0.9-0.95	9
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9625	High Similarity	NPC209882
0.9268	High Similarity	NPC311702
0.9268	High Similarity	NPC123319
0.9268	High Similarity	NPC94531
0.9259	High Similarity	NPC271784
0.9036	High Similarity	NPC11711
0.9024	High Similarity	NPC469561
0.9024	High Similarity	NPC168188
0.9024	High Similarity	NPC470015
0.8977	High Similarity	NPC241156
0.8977	High Similarity	NPC255809
0.8876	High Similarity	NPC243525
0.8876	High Similarity	NPC125622
0.8876	High Similarity	NPC40765
0.8837	High Similarity	NPC473039
0.878	High Similarity	NPC38350
0.878	High Similarity	NPC201912
0.878	High Similarity	NPC477372
0.8778	High Similarity	NPC106557
0.8764	High Similarity	NPC37646
0.875	High Similarity	NPC25750
0.869	High Similarity	NPC320801
0.8675	High Similarity	NPC133391
0.8675	High Similarity	NPC320514
0.8675	High Similarity	NPC260956
0.8667	High Similarity	NPC3772
0.8659	High Similarity	NPC26139
0.8605	High Similarity	NPC99909
0.8605	High Similarity	NPC136948
0.8588	High Similarity	NPC29447
0.8588	High Similarity	NPC142649
0.8587	High Similarity	NPC88198
0.8587	High Similarity	NPC157787
0.8587	High Similarity	NPC51370
0.8571	High Similarity	NPC69279
0.8571	High Similarity	NPC43747
0.8571	High Similarity	NPC83569
0.8571	High Similarity	NPC121339
0.8554	High Similarity	NPC147066
0.8537	High Similarity	NPC477371
0.8495	Intermediate Similarity	NPC124211
0.8478	Intermediate Similarity	NPC16021
0.8462	Intermediate Similarity	NPC95565
0.8462	Intermediate Similarity	NPC472941
0.8462	Intermediate Similarity	NPC456
0.8452	Intermediate Similarity	NPC327969
0.8452	Intermediate Similarity	NPC321289
0.8444	Intermediate Similarity	NPC166906
0.8444	Intermediate Similarity	NPC184870
0.8427	Intermediate Similarity	NPC204341
0.8427	Intermediate Similarity	NPC107690
0.8409	Intermediate Similarity	NPC262043
0.8404	Intermediate Similarity	NPC53222
0.8387	Intermediate Similarity	NPC299971
0.8387	Intermediate Similarity	NPC287833
0.8387	Intermediate Similarity	NPC144660
0.8372	Intermediate Similarity	NPC8571
0.837	Intermediate Similarity	NPC122294
0.8354	Intermediate Similarity	NPC223187
0.8353	Intermediate Similarity	NPC477373
0.8352	Intermediate Similarity	NPC318282
0.8352	Intermediate Similarity	NPC317586
0.8352	Intermediate Similarity	NPC173875
0.8352	Intermediate Similarity	NPC469995
0.8352	Intermediate Similarity	NPC470016
0.8352	Intermediate Similarity	NPC174948
0.8333	Intermediate Similarity	NPC278459
0.8333	Intermediate Similarity	NPC470254
0.8316	Intermediate Similarity	NPC33973
0.8316	Intermediate Similarity	NPC70967
0.8315	Intermediate Similarity	NPC289213
0.8313	Intermediate Similarity	NPC192329
0.828	Intermediate Similarity	NPC10364
0.8276	Intermediate Similarity	NPC229717
0.8276	Intermediate Similarity	NPC6247
0.8261	Intermediate Similarity	NPC328371
0.8261	Intermediate Similarity	NPC305483
0.8261	Intermediate Similarity	NPC96859
0.8261	Intermediate Similarity	NPC328162
0.8256	Intermediate Similarity	NPC473246
0.8256	Intermediate Similarity	NPC164577
0.8235	Intermediate Similarity	NPC469325
0.8235	Intermediate Similarity	NPC302661
0.8235	Intermediate Similarity	NPC238991
0.8229	Intermediate Similarity	NPC2436
0.8229	Intermediate Similarity	NPC216245
0.8229	Intermediate Similarity	NPC135854
0.8229	Intermediate Similarity	NPC470251
0.8222	Intermediate Similarity	NPC230064
0.8211	Intermediate Similarity	NPC281702
0.8211	Intermediate Similarity	NPC234892
0.8202	Intermediate Similarity	NPC54689
0.8202	Intermediate Similarity	NPC214387
0.8193	Intermediate Similarity	NPC74410
0.8191	Intermediate Similarity	NPC307954
0.8191	Intermediate Similarity	NPC205899
0.8182	Intermediate Similarity	NPC476409
0.8182	Intermediate Similarity	NPC96496
0.8172	Intermediate Similarity	NPC18319
0.8172	Intermediate Similarity	NPC216904
0.8171	Intermediate Similarity	NPC180886
0.8161	Intermediate Similarity	NPC469948
0.8152	Intermediate Similarity	NPC297199
0.8152	Intermediate Similarity	NPC171395
0.8144	Intermediate Similarity	NPC51452
0.814	Intermediate Similarity	NPC102197
0.814	Intermediate Similarity	NPC97913
0.8132	Intermediate Similarity	NPC206810
0.8125	Intermediate Similarity	NPC251017
0.8118	Intermediate Similarity	NPC471898
0.8111	Intermediate Similarity	NPC129913
0.8111	Intermediate Similarity	NPC477149
0.8111	Intermediate Similarity	NPC477147
0.8095	Intermediate Similarity	NPC196827
0.8095	Intermediate Similarity	NPC274996
0.809	Intermediate Similarity	NPC143767
0.809	Intermediate Similarity	NPC131470
0.809	Intermediate Similarity	NPC242864
0.8085	Intermediate Similarity	NPC112753
0.8085	Intermediate Similarity	NPC275439
0.8085	Intermediate Similarity	NPC197386
0.8072	Intermediate Similarity	NPC74685
0.8072	Intermediate Similarity	NPC165711
0.8068	Intermediate Similarity	NPC28252
0.8068	Intermediate Similarity	NPC72133
0.8068	Intermediate Similarity	NPC55309
0.8065	Intermediate Similarity	NPC7124
0.8061	Intermediate Similarity	NPC473037
0.8046	Intermediate Similarity	NPC109512
0.8046	Intermediate Similarity	NPC214043
0.8046	Intermediate Similarity	NPC85774
0.8046	Intermediate Similarity	NPC96095
0.8046	Intermediate Similarity	NPC472865
0.8043	Intermediate Similarity	NPC318332
0.8023	Intermediate Similarity	NPC193347
0.8023	Intermediate Similarity	NPC100297
0.8023	Intermediate Similarity	NPC142253
0.8023	Intermediate Similarity	NPC3511
0.8023	Intermediate Similarity	NPC240302
0.8022	Intermediate Similarity	NPC297265
0.8022	Intermediate Similarity	NPC150383
0.8021	Intermediate Similarity	NPC293753
0.8021	Intermediate Similarity	NPC204450
0.8021	Intermediate Similarity	NPC56498
0.8021	Intermediate Similarity	NPC195290
0.8	Intermediate Similarity	NPC86319
0.8	Intermediate Similarity	NPC474889
0.8	Intermediate Similarity	NPC477943
0.8	Intermediate Similarity	NPC275740
0.8	Intermediate Similarity	NPC279667
0.8	Intermediate Similarity	NPC474570
0.8	Intermediate Similarity	NPC316964
0.798	Intermediate Similarity	NPC295244
0.7979	Intermediate Similarity	NPC320306
0.7979	Intermediate Similarity	NPC23680
0.7978	Intermediate Similarity	NPC233836
0.7978	Intermediate Similarity	NPC159046
0.7978	Intermediate Similarity	NPC187376
0.7976	Intermediate Similarity	NPC469996
0.7976	Intermediate Similarity	NPC30321
0.7959	Intermediate Similarity	NPC472935
0.7957	Intermediate Similarity	NPC473648
0.7955	Intermediate Similarity	NPC474537
0.7952	Intermediate Similarity	NPC246445
0.7952	Intermediate Similarity	NPC92080
0.7938	Intermediate Similarity	NPC236390
0.7938	Intermediate Similarity	NPC55872
0.7935	Intermediate Similarity	NPC152897
0.7935	Intermediate Similarity	NPC472930
0.7935	Intermediate Similarity	NPC66429
0.7935	Intermediate Similarity	NPC243866
0.7931	Intermediate Similarity	NPC310470
0.7931	Intermediate Similarity	NPC105803
0.7931	Intermediate Similarity	NPC49019
0.7931	Intermediate Similarity	NPC167103
0.7917	Intermediate Similarity	NPC472924
0.7917	Intermediate Similarity	NPC302537
0.7917	Intermediate Similarity	NPC163372
0.7912	Intermediate Similarity	NPC183283
0.7912	Intermediate Similarity	NPC469400
0.7912	Intermediate Similarity	NPC476437
0.7912	Intermediate Similarity	NPC111585
0.7912	Intermediate Similarity	NPC252737
0.7912	Intermediate Similarity	NPC148414
0.7912	Intermediate Similarity	NPC175628
0.7912	Intermediate Similarity	NPC20388
0.7912	Intermediate Similarity	NPC476369
0.7907	Intermediate Similarity	NPC221647
0.7907	Intermediate Similarity	NPC150506
0.7907	Intermediate Similarity	NPC189237
0.7901	Intermediate Similarity	NPC472309
0.7895	Intermediate Similarity	NPC147954
0.7895	Intermediate Similarity	NPC471717
0.7895	Intermediate Similarity	NPC235464
0.7895	Intermediate Similarity	NPC166745
0.7889	Intermediate Similarity	NPC471722
0.7889	Intermediate Similarity	NPC117122
0.7882	Intermediate Similarity	NPC192744
0.7882	Intermediate Similarity	NPC472490
0.7882	Intermediate Similarity	NPC215843

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 NPC473038 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	2033
0.2-0.3	4223
0.3-0.4	1851
0.4-0.5	464
0.5-0.6	172
0.6-0.7	160
0.7-0.8	87
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8222	Intermediate Similarity	NPD5281	Approved
0.8222	Intermediate Similarity	NPD5284	Approved
0.8193	Intermediate Similarity	NPD3617	Approved
0.8023	Intermediate Similarity	NPD4221	Approved
0.8023	Intermediate Similarity	NPD4223	Phase 3
0.7957	Intermediate Similarity	NPD5695	Phase 3
0.7955	Intermediate Similarity	NPD5329	Approved
0.7935	Intermediate Similarity	NPD6399	Phase 3
0.7907	Intermediate Similarity	NPD4139	Approved
0.7907	Intermediate Similarity	NPD4692	Approved
0.7901	Intermediate Similarity	NPD6081	Approved
0.7895	Intermediate Similarity	NPD5696	Approved
0.7889	Intermediate Similarity	NPD6672	Approved
0.7889	Intermediate Similarity	NPD5737	Approved
0.7872	Intermediate Similarity	NPD7614	Phase 1
0.7865	Intermediate Similarity	NPD5690	Phase 2
0.7865	Intermediate Similarity	NPD5280	Approved
0.7865	Intermediate Similarity	NPD4694	Approved
0.7841	Intermediate Similarity	NPD4197	Approved
0.7826	Intermediate Similarity	NPD6050	Approved
0.7802	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD6080	Approved
0.7802	Intermediate Similarity	NPD6904	Approved
0.7802	Intermediate Similarity	NPD5328	Approved
0.7802	Intermediate Similarity	NPD6673	Approved
0.7789	Intermediate Similarity	NPD6084	Phase 2
0.7789	Intermediate Similarity	NPD6083	Phase 2
0.7717	Intermediate Similarity	NPD5692	Phase 3
0.7667	Intermediate Similarity	NPD6409	Approved
0.7667	Intermediate Similarity	NPD4689	Approved
0.7667	Intermediate Similarity	NPD5205	Approved
0.7667	Intermediate Similarity	NPD4688	Approved
0.7667	Intermediate Similarity	NPD4693	Phase 3
0.7667	Intermediate Similarity	NPD4690	Approved
0.7667	Intermediate Similarity	NPD7521	Approved
0.7667	Intermediate Similarity	NPD6684	Approved
0.7667	Intermediate Similarity	NPD5279	Phase 3
0.7667	Intermediate Similarity	NPD7146	Approved
0.7667	Intermediate Similarity	NPD7334	Approved
0.7667	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD5330	Approved
0.7667	Intermediate Similarity	NPD4138	Approved
0.764	Intermediate Similarity	NPD3133	Approved
0.764	Intermediate Similarity	NPD3665	Phase 1
0.764	Intermediate Similarity	NPD4786	Approved
0.764	Intermediate Similarity	NPD3666	Approved
0.7634	Intermediate Similarity	NPD6079	Approved
0.7634	Intermediate Similarity	NPD5694	Approved
0.7609	Intermediate Similarity	NPD4753	Phase 2
0.7579	Intermediate Similarity	NPD5210	Approved
0.7579	Intermediate Similarity	NPD4629	Approved
0.7527	Intermediate Similarity	NPD5207	Approved
0.75	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6903	Approved
0.75	Intermediate Similarity	NPD5208	Approved
0.75	Intermediate Similarity	NPD4697	Phase 3
0.75	Intermediate Similarity	NPD5733	Approved
0.7473	Intermediate Similarity	NPD3618	Phase 1
0.7473	Intermediate Similarity	NPD6098	Approved
0.7447	Intermediate Similarity	NPD5693	Phase 1
0.7447	Intermediate Similarity	NPD7515	Phase 2
0.7426	Intermediate Similarity	NPD5739	Approved
0.7426	Intermediate Similarity	NPD6675	Approved
0.7426	Intermediate Similarity	NPD7128	Approved
0.7426	Intermediate Similarity	NPD6402	Approved
0.7416	Intermediate Similarity	NPD3667	Approved
0.7396	Intermediate Similarity	NPD5654	Approved
0.7396	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4695	Discontinued
0.7379	Intermediate Similarity	NPD6373	Approved
0.7379	Intermediate Similarity	NPD6372	Approved
0.7368	Intermediate Similarity	NPD5133	Approved
0.7349	Intermediate Similarity	NPD4747	Approved
0.734	Intermediate Similarity	NPD4096	Approved
0.732	Intermediate Similarity	NPD5221	Approved
0.732	Intermediate Similarity	NPD5222	Approved
0.732	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7732	Phase 3
0.7294	Intermediate Similarity	NPD4687	Approved
0.7292	Intermediate Similarity	NPD7748	Approved
0.7284	Intermediate Similarity	NPD4224	Phase 2
0.7282	Intermediate Similarity	NPD6881	Approved
0.7282	Intermediate Similarity	NPD7320	Approved
0.7282	Intermediate Similarity	NPD6899	Approved
0.7273	Intermediate Similarity	NPD4195	Approved
0.7273	Intermediate Similarity	NPD6404	Discontinued
0.7262	Intermediate Similarity	NPD5276	Approved
0.7245	Intermediate Similarity	NPD7902	Approved
0.7245	Intermediate Similarity	NPD5959	Approved
0.7245	Intermediate Similarity	NPD4755	Approved
0.7245	Intermediate Similarity	NPD5173	Approved
0.7238	Intermediate Similarity	NPD6649	Approved
0.7238	Intermediate Similarity	NPD6650	Approved
0.7229	Intermediate Similarity	NPD4137	Phase 3
0.7188	Intermediate Similarity	NPD4202	Approved
0.7184	Intermediate Similarity	NPD5701	Approved
0.7184	Intermediate Similarity	NPD5697	Approved
0.7174	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7341	Phase 2
0.7143	Intermediate Similarity	NPD7102	Approved
0.7143	Intermediate Similarity	NPD4691	Approved
0.7143	Intermediate Similarity	NPD4788	Approved
0.7143	Intermediate Similarity	NPD7290	Approved
0.7143	Intermediate Similarity	NPD6883	Approved
0.7129	Intermediate Similarity	NPD5091	Approved
0.7128	Intermediate Similarity	NPD4518	Approved
0.7115	Intermediate Similarity	NPD6011	Approved
0.7113	Intermediate Similarity	NPD6001	Approved
0.71	Intermediate Similarity	NPD5285	Approved
0.71	Intermediate Similarity	NPD5286	Approved
0.71	Intermediate Similarity	NPD4700	Approved
0.71	Intermediate Similarity	NPD4696	Approved
0.7097	Intermediate Similarity	NPD4519	Discontinued
0.7097	Intermediate Similarity	NPD4623	Approved
0.7083	Intermediate Similarity	NPD8035	Phase 2
0.7083	Intermediate Similarity	NPD8034	Phase 2
0.7075	Intermediate Similarity	NPD6869	Approved
0.7075	Intermediate Similarity	NPD6617	Approved
0.7075	Intermediate Similarity	NPD6847	Approved
0.7075	Intermediate Similarity	NPD8130	Phase 1
0.7075	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD3668	Phase 3
0.7048	Intermediate Similarity	NPD6013	Approved
0.7048	Intermediate Similarity	NPD6014	Approved
0.7048	Intermediate Similarity	NPD6012	Approved
0.703	Intermediate Similarity	NPD5223	Approved
0.7021	Intermediate Similarity	NPD3573	Approved
0.7019	Intermediate Similarity	NPD6614	Approved
0.7009	Intermediate Similarity	NPD8297	Approved
0.7009	Intermediate Similarity	NPD6882	Approved
0.6961	Remote Similarity	NPD4633	Approved
0.6961	Remote Similarity	NPD5226	Approved
0.6961	Remote Similarity	NPD5211	Phase 2
0.6961	Remote Similarity	NPD5225	Approved
0.6961	Remote Similarity	NPD5224	Approved
0.6939	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7900	Approved
0.6932	Remote Similarity	NPD6117	Approved
0.6905	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5360	Phase 3
0.6897	Remote Similarity	NPD4058	Approved
0.6897	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD5174	Approved
0.6893	Remote Similarity	NPD6052	Approved
0.6893	Remote Similarity	NPD5175	Approved
0.6893	Remote Similarity	NPD4754	Approved
0.686	Remote Similarity	NPD4243	Approved
0.6854	Remote Similarity	NPD6116	Phase 1
0.6832	Remote Similarity	NPD7638	Approved
0.6827	Remote Similarity	NPD5141	Approved
0.6818	Remote Similarity	NPD3702	Approved
0.6818	Remote Similarity	NPD6868	Approved
0.6789	Remote Similarity	NPD4632	Approved
0.6778	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD6114	Approved
0.6778	Remote Similarity	NPD6115	Approved
0.6778	Remote Similarity	NPD6118	Approved
0.6778	Remote Similarity	NPD6697	Approved
0.6765	Remote Similarity	NPD7640	Approved
0.6765	Remote Similarity	NPD7639	Approved
0.6762	Remote Similarity	NPD4767	Approved
0.6762	Remote Similarity	NPD4768	Approved
0.6762	Remote Similarity	NPD6008	Approved
0.6747	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4789	Approved
0.6735	Remote Similarity	NPD6411	Approved
0.6706	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4785	Approved
0.6705	Remote Similarity	NPD4784	Approved
0.6698	Remote Similarity	NPD6412	Phase 2
0.6696	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD7331	Phase 2
0.6667	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD7101	Approved
0.6637	Remote Similarity	NPD7100	Approved
0.6636	Remote Similarity	NPD4730	Approved
0.6636	Remote Similarity	NPD5128	Approved
0.6636	Remote Similarity	NPD4729	Approved
0.6636	Remote Similarity	NPD5168	Approved
0.6635	Remote Similarity	NPD7632	Discontinued
0.6629	Remote Similarity	NPD7339	Approved
0.6629	Remote Similarity	NPD6942	Approved
0.6607	Remote Similarity	NPD7115	Discovery
0.6607	Remote Similarity	NPD6317	Approved
0.6607	Remote Similarity	NPD6009	Approved
0.6552	Remote Similarity	NPD4245	Approved
0.6552	Remote Similarity	NPD4244	Approved
0.6549	Remote Similarity	NPD6314	Approved
0.6549	Remote Similarity	NPD6313	Approved
0.6531	Remote Similarity	NPD6101	Approved
0.6531	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6909	Approved
0.6522	Remote Similarity	NPD6908	Approved
0.6514	Remote Similarity	NPD5248	Approved
0.6514	Remote Similarity	NPD5135	Approved
0.6514	Remote Similarity	NPD5249	Phase 3
0.6514	Remote Similarity	NPD5247	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