NPASS Compound

Structure

NPC474460 OpenBabel07101719522D 23 22 0 0 1 0 0 0 0 0999 V2000 2.9641 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4282 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6962 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8301 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5622 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6962 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6962 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5622 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.5622 4.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6962 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 6 13 2 0 0 0 0 7 11 1 0 0 0 0 7 14 1 0 0 0 0 8 17 2 0 0 0 0 9 18 1 0 0 0 0 10 17 1 0 0 0 0 11 19 2 0 0 0 0 12 15 1 0 0 0 0 12 18 2 0 0 0 0 13 20 1 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 16 19 1 0 0 0 0 16 22 1 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	322.25
Volume:	370.301
LogP:	2.405
LogD:	2.755
LogS:	-4.167
# Rotatable Bonds:	11
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	0
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.503
Synthetic Accessibility Score:	3.935
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.556
MDCK Permeability:	3.2924304832704365e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.026
Human Intestinal Absorption (HIA):	0.472
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.092
Plasma Protein Binding (PPB):	82.46198272705078%
Volume Distribution (VD):	0.648
Pgp-substrate:	5.038461685180664%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.107
CYP2C19-inhibitor:	0.063
CYP2C19-substrate:	0.319
CYP2C9-inhibitor:	0.043
CYP2C9-substrate:	0.291
CYP2D6-inhibitor:	0.239
CYP2D6-substrate:	0.057
CYP3A4-inhibitor:	0.55
CYP3A4-substrate:	0.187

ADMET: Excretion

Clearance (CL):	5.093
Half-life (T1/2):	0.844

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.103
Drug-inuced Liver Injury (DILI):	0.01
AMES Toxicity:	0.0
Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.934
Skin Sensitization:	0.977
Carcinogencity:	0.01
Eye Corrosion:	0.011
Eye Irritation:	0.875
Respiratory Toxicity:	0.005

Download Data

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

Natural Product: NPC474460

Natural Product ID:	NPC474460
*Common Name:**	Boletinin A
IUPAC Name:	(2E,7E,10E,14E)-2,6,10,14-tetramethylhexadeca-2,7,10,14-tetraene-1,6,16-triol
Synonyms:
Standard InCHIKey:	QVPAFHFVRMUTMO-AOMRLLSLSA-N
Standard InCHI:	InChI=1S/C20H34O3/c1-17(8-5-9-18(2)12-15-21)10-6-13-20(4,23)14-7-11-19(3)16-22/h6,8,11-13,21-23H,5,7,9-10,14-16H2,1-4H3/b13-6+,17-8+,18-12+,19-11+
SMILES:	CC(=CCO)CCC=C(C)CC=CC(C)(CCC=C(C)CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469296
PubChem CID:	11198071
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001357] Acyclic 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
NPO28298	Boletinus cavipes	Species	Gyrodontaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15217273]
NPO28298	Boletinus cavipes	Species	Gyrodontaceae	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
Others	6

Activity Type	# Activity
Individual Protein	2
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	=	12.0	%	PMID[521355]
NPT2	Others	Unspecified		Inhibition	=	18.0	%	PMID[521355]
NPT27	Others	Unspecified		Activity	=	98.0	%	PMID[521355]
NPT967	Individual Protein	Xanthine dehydrogenase	Homo sapiens	Inhibition	=	5.0	%	PMID[521355]
NPT967	Individual Protein	Xanthine dehydrogenase	Homo sapiens	Inhibition	=	7.0	%	PMID[521355]
NPT27	Others	Unspecified		Activity	=	86.0	%	PMID[521355]

☑ 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 NPC474460 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	116
0.1-0.2	4040
0.2-0.3	19419
0.3-0.4	11791
0.4-0.5	5314
0.5-0.6	1540
0.6-0.7	360
0.7-0.8	94
0.8-0.85	10
0.85-0.9	12
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8723	High Similarity	NPC140501
0.8696	High Similarity	NPC116934
0.8519	High Similarity	NPC181872
0.8478	Intermediate Similarity	NPC67761
0.8478	Intermediate Similarity	NPC108494
0.8478	Intermediate Similarity	NPC51758
0.8478	Intermediate Similarity	NPC68889
0.8478	Intermediate Similarity	NPC88079
0.8478	Intermediate Similarity	NPC209279
0.8478	Intermediate Similarity	NPC194586
0.8478	Intermediate Similarity	NPC180871
0.8431	Intermediate Similarity	NPC35756
0.8333	Intermediate Similarity	NPC160628
0.8261	Intermediate Similarity	NPC269823
0.8235	Intermediate Similarity	NPC473672
0.8235	Intermediate Similarity	NPC474495
0.8125	Intermediate Similarity	NPC138935
0.8085	Intermediate Similarity	NPC256766
0.8085	Intermediate Similarity	NPC213538
0.8036	Intermediate Similarity	NPC475931
0.7963	Intermediate Similarity	NPC227135
0.7963	Intermediate Similarity	NPC329686
0.7925	Intermediate Similarity	NPC474496
0.7857	Intermediate Similarity	NPC226848
0.7843	Intermediate Similarity	NPC267110
0.7826	Intermediate Similarity	NPC29091
0.7826	Intermediate Similarity	NPC255042
0.7826	Intermediate Similarity	NPC182840
0.7826	Intermediate Similarity	NPC103213
0.7759	Intermediate Similarity	NPC55376
0.7719	Intermediate Similarity	NPC122239
0.7692	Intermediate Similarity	NPC328784
0.7692	Intermediate Similarity	NPC182102
0.7692	Intermediate Similarity	NPC291437
0.7692	Intermediate Similarity	NPC26960
0.7667	Intermediate Similarity	NPC308844
0.766	Intermediate Similarity	NPC56917
0.7636	Intermediate Similarity	NPC281590
0.7547	Intermediate Similarity	NPC71053
0.7547	Intermediate Similarity	NPC151782
0.7547	Intermediate Similarity	NPC59408
0.75	Intermediate Similarity	NPC153538
0.75	Intermediate Similarity	NPC188596
0.7455	Intermediate Similarity	NPC474127
0.7447	Intermediate Similarity	NPC15934
0.7419	Intermediate Similarity	NPC73603
0.7407	Intermediate Similarity	NPC68014
0.7407	Intermediate Similarity	NPC208638
0.7368	Intermediate Similarity	NPC268185
0.7368	Intermediate Similarity	NPC52012
0.7368	Intermediate Similarity	NPC71755
0.7358	Intermediate Similarity	NPC72699
0.7321	Intermediate Similarity	NPC474644
0.7321	Intermediate Similarity	NPC251666
0.7321	Intermediate Similarity	NPC232247
0.7288	Intermediate Similarity	NPC66020
0.7288	Intermediate Similarity	NPC258788
0.7288	Intermediate Similarity	NPC471081
0.7288	Intermediate Similarity	NPC240506
0.7273	Intermediate Similarity	NPC217188
0.7255	Intermediate Similarity	NPC24824
0.7255	Intermediate Similarity	NPC210560
0.7255	Intermediate Similarity	NPC165651
0.7241	Intermediate Similarity	NPC155025
0.7234	Intermediate Similarity	NPC34873
0.7234	Intermediate Similarity	NPC40434
0.7222	Intermediate Similarity	NPC93639
0.7222	Intermediate Similarity	NPC244038
0.7213	Intermediate Similarity	NPC300593
0.7193	Intermediate Similarity	NPC473865
0.7193	Intermediate Similarity	NPC48891
0.7193	Intermediate Similarity	NPC474643
0.717	Intermediate Similarity	NPC248884
0.717	Intermediate Similarity	NPC85079
0.717	Intermediate Similarity	NPC31194
0.7167	Intermediate Similarity	NPC321867
0.7167	Intermediate Similarity	NPC207007
0.7167	Intermediate Similarity	NPC68679
0.7143	Intermediate Similarity	NPC256209
0.7143	Intermediate Similarity	NPC473532
0.7143	Intermediate Similarity	NPC259299
0.7143	Intermediate Similarity	NPC110732
0.7143	Intermediate Similarity	NPC49059
0.7119	Intermediate Similarity	NPC278202
0.7115	Intermediate Similarity	NPC124183
0.7115	Intermediate Similarity	NPC35141
0.7037	Intermediate Similarity	NPC20934
0.7037	Intermediate Similarity	NPC471281
0.7037	Intermediate Similarity	NPC199286
0.7037	Intermediate Similarity	NPC249670
0.7037	Intermediate Similarity	NPC474642
0.7037	Intermediate Similarity	NPC288381
0.7037	Intermediate Similarity	NPC477727
0.7037	Intermediate Similarity	NPC329773
0.7037	Intermediate Similarity	NPC225974
0.7037	Intermediate Similarity	NPC473913
0.7031	Intermediate Similarity	NPC224532
0.7031	Intermediate Similarity	NPC305698
0.7018	Intermediate Similarity	NPC473910
0.7018	Intermediate Similarity	NPC473896
0.7018	Intermediate Similarity	NPC477725
0.7018	Intermediate Similarity	NPC475353
0.7018	Intermediate Similarity	NPC473735
0.7018	Intermediate Similarity	NPC477726
0.7018	Intermediate Similarity	NPC130209
0.7018	Intermediate Similarity	NPC473725
0.7018	Intermediate Similarity	NPC148163
0.7018	Intermediate Similarity	NPC298299
0.7018	Intermediate Similarity	NPC148216
0.7018	Intermediate Similarity	NPC473721
0.7	Intermediate Similarity	NPC206906
0.7	Intermediate Similarity	NPC99487
0.7	Intermediate Similarity	NPC304151
0.6984	Remote Similarity	NPC267027
0.6957	Remote Similarity	NPC58957
0.6949	Remote Similarity	NPC223679
0.6923	Remote Similarity	NPC472947
0.6923	Remote Similarity	NPC76976
0.6923	Remote Similarity	NPC269074
0.6923	Remote Similarity	NPC329989
0.6923	Remote Similarity	NPC239373
0.6909	Remote Similarity	NPC256656
0.6909	Remote Similarity	NPC165447
0.6909	Remote Similarity	NPC76198
0.6909	Remote Similarity	NPC9273
0.6909	Remote Similarity	NPC170776
0.6909	Remote Similarity	NPC475477
0.6909	Remote Similarity	NPC129263
0.6909	Remote Similarity	NPC224148
0.6909	Remote Similarity	NPC471959
0.6909	Remote Similarity	NPC477723
0.6909	Remote Similarity	NPC89824
0.6909	Remote Similarity	NPC329608
0.6909	Remote Similarity	NPC197272
0.6909	Remote Similarity	NPC55383
0.6909	Remote Similarity	NPC294278
0.6897	Remote Similarity	NPC55412
0.6897	Remote Similarity	NPC470967
0.6897	Remote Similarity	NPC249645
0.6897	Remote Similarity	NPC477661
0.6897	Remote Similarity	NPC161838
0.6897	Remote Similarity	NPC470969
0.6897	Remote Similarity	NPC473847
0.6897	Remote Similarity	NPC470968
0.6897	Remote Similarity	NPC470966
0.6897	Remote Similarity	NPC475384
0.6897	Remote Similarity	NPC471960
0.6885	Remote Similarity	NPC475251
0.6885	Remote Similarity	NPC64971
0.6875	Remote Similarity	NPC106613
0.6852	Remote Similarity	NPC302310
0.6852	Remote Similarity	NPC125122
0.6852	Remote Similarity	NPC471275
0.6852	Remote Similarity	NPC471280
0.6852	Remote Similarity	NPC91765
0.6852	Remote Similarity	NPC62755
0.6852	Remote Similarity	NPC471276
0.6842	Remote Similarity	NPC189677
0.6833	Remote Similarity	NPC322186
0.6833	Remote Similarity	NPC322002
0.6825	Remote Similarity	NPC19569
0.6809	Remote Similarity	NPC79544
0.6792	Remote Similarity	NPC19834
0.6792	Remote Similarity	NPC308331
0.6792	Remote Similarity	NPC55063
0.6792	Remote Similarity	NPC180575
0.6786	Remote Similarity	NPC294358
0.6786	Remote Similarity	NPC142092
0.6786	Remote Similarity	NPC40417
0.678	Remote Similarity	NPC11130
0.678	Remote Similarity	NPC470970
0.678	Remote Similarity	NPC129150
0.678	Remote Similarity	NPC472445
0.6774	Remote Similarity	NPC473508
0.6774	Remote Similarity	NPC471023
0.6739	Remote Similarity	NPC250734
0.6731	Remote Similarity	NPC101616
0.6731	Remote Similarity	NPC108195
0.6724	Remote Similarity	NPC317899
0.6721	Remote Similarity	NPC130807
0.6721	Remote Similarity	NPC327112
0.6721	Remote Similarity	NPC469694
0.6719	Remote Similarity	NPC250977
0.6716	Remote Similarity	NPC316185
0.6667	Remote Similarity	NPC254095
0.6667	Remote Similarity	NPC249801
0.6667	Remote Similarity	NPC309300
0.6667	Remote Similarity	NPC471560
0.6667	Remote Similarity	NPC61177
0.6667	Remote Similarity	NPC318549
0.6667	Remote Similarity	NPC74722
0.6667	Remote Similarity	NPC46248
0.6667	Remote Similarity	NPC110241
0.6667	Remote Similarity	NPC304690
0.6667	Remote Similarity	NPC34577
0.6618	Remote Similarity	NPC329763
0.6618	Remote Similarity	NPC130665
0.6615	Remote Similarity	NPC82337
0.6615	Remote Similarity	NPC68703
0.6615	Remote Similarity	NPC136813

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 NPC474460 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	115
0.1-0.2	3617
0.2-0.3	4096
0.3-0.4	1080
0.4-0.5	155
0.5-0.6	75
0.6-0.7	9
0.7-0.8	2
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8723	High Similarity	NPD4265	Approved
0.7167	Intermediate Similarity	NPD368	Approved
0.7018	Intermediate Similarity	NPD342	Phase 1
0.6897	Remote Similarity	NPD4219	Approved
0.6721	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD4732	Discontinued
0.6545	Remote Similarity	NPD4220	Pre-registration
0.6508	Remote Similarity	NPD3210	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8264	Approved
0.6393	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6927	Phase 3
0.6296	Remote Similarity	NPD39	Approved
0.6226	Remote Similarity	NPD5326	Phase 3
0.6216	Remote Similarity	NPD7332	Phase 2
0.6216	Remote Similarity	NPD7514	Phase 3
0.614	Remote Similarity	NPD2268	Discontinued
0.6119	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD5783	Phase 3
0.6	Remote Similarity	NPD4222	Approved
0.6	Remote Similarity	NPD4821	Approved
0.6	Remote Similarity	NPD4820	Approved
0.6	Remote Similarity	NPD4822	Approved
0.6	Remote Similarity	NPD4819	Approved
0.5946	Remote Similarity	NPD7145	Approved
0.5946	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD4268	Approved
0.5946	Remote Similarity	NPD4271	Approved
0.5921	Remote Similarity	NPD6902	Approved
0.5873	Remote Similarity	NPD6109	Phase 1
0.5857	Remote Similarity	NPD3212	Clinical (unspecified phase)
0.5857	Remote Similarity	NPD7143	Approved
0.5857	Remote Similarity	NPD7144	Approved
0.5846	Remote Similarity	NPD4194	Approved
0.5846	Remote Similarity	NPD4191	Approved
0.5846	Remote Similarity	NPD4192	Approved
0.5846	Remote Similarity	NPD4193	Approved
0.5833	Remote Similarity	NPD6926	Approved
0.5833	Remote Similarity	NPD6924	Approved
0.5821	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD6097	Approved
0.5818	Remote Similarity	NPD6096	Approved
0.5811	Remote Similarity	NPD6932	Approved
0.5811	Remote Similarity	NPD5776	Phase 2
0.5811	Remote Similarity	NPD6925	Approved
0.5789	Remote Similarity	NPD6931	Approved
0.5789	Remote Similarity	NPD6930	Phase 2
0.5789	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD5343	Approved
0.5789	Remote Similarity	NPD4252	Approved
0.5775	Remote Similarity	NPD7151	Approved
0.5775	Remote Similarity	NPD7150	Approved
0.5775	Remote Similarity	NPD7152	Approved
0.5769	Remote Similarity	NPD7154	Phase 3
0.5769	Remote Similarity	NPD5332	Approved
0.5769	Remote Similarity	NPD5331	Approved
0.5769	Remote Similarity	NPD5362	Discontinued
0.5735	Remote Similarity	NPD7331	Phase 2
0.5714	Remote Similarity	NPD6922	Approved
0.5714	Remote Similarity	NPD6923	Approved
0.5714	Remote Similarity	NPD4790	Discontinued
0.5714	Remote Similarity	NPD6898	Phase 1
0.569	Remote Similarity	NPD3173	Approved
0.5676	Remote Similarity	NPD6933	Approved
0.5672	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5672	Remote Similarity	NPD3197	Phase 1
0.5658	Remote Similarity	NPD6929	Approved
0.5641	Remote Similarity	NPD4270	Approved
0.5641	Remote Similarity	NPD4269	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