NPASS Compound

Structure

NPC472744 OpenBabel07101718302D 34 39 0 0 1 0 0 0 0 0999 V2000 3.0981 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3388 -1.1465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5957 -1.8156 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3198 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1285 -1.6045 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 -2.5827 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 -1.0739 -2.4781 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 -1.7321 -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 -3.7624 -0.5102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1225 -2.2044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4533 -1.4612 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4752 -1.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7405 -0.3023 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4096 -1.0454 0.0000 C 0 0 1 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 -6.3878 -0.8375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 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 -5.0495 0.6488 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6968 0.1136 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1006 -1.9965 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 7 8 1 0 0 0 0 7 21 1 0 0 0 0 8 22 1 0 0 0 0 9 11 1 0 0 0 0 9 19 1 0 0 0 0 10 12 1 0 0 0 0 10 23 1 0 0 0 0 11 28 1 0 0 0 0 12 29 1 0 0 0 0 13 14 1 0 0 0 0 13 27 1 0 0 0 0 15 20 1 0 0 0 0 16 18 1 0 0 0 0 16 34 1 0 0 0 0 17 29 1 0 0 0 0 17 30 1 0 0 0 0 18 15 1 6 0 0 0 18 19 1 0 0 0 0 19 27 1 6 0 0 0 20 24 1 0 0 0 0 20 31 1 1 0 0 0 21 25 1 0 0 0 0 21 29 1 6 0 0 0 22 28 1 1 0 0 0 22 30 1 0 0 0 0 23 25 1 0 0 0 0 23 32 2 0 0 0 0 24 26 1 6 0 0 0 24 34 1 0 0 0 0 26 33 1 0 0 0 0 27 28 1 6 0 0 0 28 6 1 1 0 0 0 29 30 1 1 0 0 0 30 14 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.36
Volume:	508.622
LogP:	3.91
LogD:	3.922
LogS:	-4.585
# Rotatable Bonds:	2
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.554
Synthetic Accessibility Score:	5.801
Fsp3:	0.967
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.127
MDCK Permeability:	1.979676198970992e-05
Pgp-inhibitor:	0.352
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.36
30% Bioavailability (F30%):	0.959

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.813
Plasma Protein Binding (PPB):	95.54113006591797%
Volume Distribution (VD):	1.238
Pgp-substrate:	3.7134125232696533%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.599
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.943
CYP2C9-inhibitor:	0.081
CYP2C9-substrate:	0.166
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.625
CYP3A4-inhibitor:	0.259
CYP3A4-substrate:	0.392

ADMET: Excretion

Clearance (CL):	8.17
Half-life (T1/2):	0.069

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.371
Drug-inuced Liver Injury (DILI):	0.02
AMES Toxicity:	0.047
Rat Oral Acute Toxicity:	0.297
Maximum Recommended Daily Dose:	0.74
Skin Sensitization:	0.068
Carcinogencity:	0.069
Eye Corrosion:	0.003
Eye Irritation:	0.03
Respiratory Toxicity:	0.95

Download Data

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

Natural Product: NPC472744

Natural Product ID:	NPC472744
*Common Name:**	YEENJEQGAWLURT-CEFGYFKCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YEENJEQGAWLURT-CEFGYFKCSA-N
Standard InCHI:	InChI=1S/C30H48O4/c1-25(2)21-7-8-22-28(6)11-9-19(18-15-20(31)24(34-16-18)26(3,4)33)27(28,5)13-14-30(22)17-29(21,30)12-10-23(25)32/h18-22,24,31,33H,7-17H2,1-6H3/t18-,19+,20-,21-,22-,24-,27+,28-,29+,30-/m0/s1
SMILES:	CC1(C2CCC3C4(CCC(C4(CCC35C2(C5)CCC1=O)C)C6CC(C(OC6)C(C)(C)O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581989
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols 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
NPO32573	dysoxylum gotadhora	Species	Meliaceae	Eukaryota	Leaves and Twigs	n.a.	n.a.	PMID[25945867]

☑ 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
Others	5

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	23.2	%	PMID[549025]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	49.0	%	PMID[549025]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	76.2	%	PMID[549025]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	25500.0	nM	PMID[549025]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	18.5	%	PMID[549025]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	12.5	%	PMID[549025]

☑ 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 NPC472744 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	388
0.1-0.2	3390
0.2-0.3	12040
0.3-0.4	11675
0.4-0.5	5899
0.5-0.6	5148
0.6-0.7	3452
0.7-0.8	637
0.8-0.85	55
0.85-0.9	9
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9221	High Similarity	NPC264602
0.9146	High Similarity	NPC472745
0.8916	High Similarity	NPC474448
0.881	High Similarity	NPC202937
0.8765	High Similarity	NPC77311
0.8554	High Similarity	NPC217559
0.8554	High Similarity	NPC268578
0.8554	High Similarity	NPC292458
0.8554	High Similarity	NPC259173
0.8519	High Similarity	NPC31302
0.8519	High Similarity	NPC245029
0.85	High Similarity	NPC475031
0.8471	Intermediate Similarity	NPC92139
0.8415	Intermediate Similarity	NPC472853
0.8354	Intermediate Similarity	NPC472854
0.8313	Intermediate Similarity	NPC12933
0.8256	Intermediate Similarity	NPC80700
0.825	Intermediate Similarity	NPC273366
0.8235	Intermediate Similarity	NPC474996
0.8228	Intermediate Similarity	NPC474123
0.8222	Intermediate Similarity	NPC206878
0.8222	Intermediate Similarity	NPC470423
0.8214	Intermediate Similarity	NPC477936
0.8214	Intermediate Similarity	NPC477935
0.8214	Intermediate Similarity	NPC317066
0.8172	Intermediate Similarity	NPC41843
0.8171	Intermediate Similarity	NPC476732
0.8171	Intermediate Similarity	NPC199965
0.8132	Intermediate Similarity	NPC215570
0.8125	Intermediate Similarity	NPC472945
0.8125	Intermediate Similarity	NPC472944
0.8118	Intermediate Similarity	NPC269684
0.8101	Intermediate Similarity	NPC58057
0.8101	Intermediate Similarity	NPC151018
0.8101	Intermediate Similarity	NPC473267
0.8101	Intermediate Similarity	NPC320549
0.8101	Intermediate Similarity	NPC156277
0.8095	Intermediate Similarity	NPC469745
0.8072	Intermediate Similarity	NPC52951
0.8068	Intermediate Similarity	NPC255176
0.8049	Intermediate Similarity	NPC23884
0.8049	Intermediate Similarity	NPC477918
0.8049	Intermediate Similarity	NPC477919
0.8049	Intermediate Similarity	NPC180199
0.8025	Intermediate Similarity	NPC195155
0.8025	Intermediate Similarity	NPC174964
0.8025	Intermediate Similarity	NPC24014
0.8025	Intermediate Similarity	NPC27349
0.8025	Intermediate Similarity	NPC97534
0.8023	Intermediate Similarity	NPC319909
0.8022	Intermediate Similarity	NPC174051
0.8022	Intermediate Similarity	NPC67831
0.8	Intermediate Similarity	NPC289486
0.8	Intermediate Similarity	NPC100366
0.8	Intermediate Similarity	NPC311642
0.8	Intermediate Similarity	NPC164289
0.8	Intermediate Similarity	NPC61107
0.8	Intermediate Similarity	NPC242771
0.8	Intermediate Similarity	NPC310766
0.8	Intermediate Similarity	NPC232112
0.7976	Intermediate Similarity	NPC470609
0.7955	Intermediate Similarity	NPC469322
0.7955	Intermediate Similarity	NPC263802
0.7949	Intermediate Similarity	NPC473225
0.7935	Intermediate Similarity	NPC17336
0.7935	Intermediate Similarity	NPC470031
0.7927	Intermediate Similarity	NPC475742
0.7927	Intermediate Similarity	NPC477932
0.7927	Intermediate Similarity	NPC5767
0.7927	Intermediate Similarity	NPC477933
0.7917	Intermediate Similarity	NPC34562
0.7907	Intermediate Similarity	NPC327451
0.7901	Intermediate Similarity	NPC254340
0.7895	Intermediate Similarity	NPC477172
0.7889	Intermediate Similarity	NPC77756
0.7889	Intermediate Similarity	NPC475056
0.7875	Intermediate Similarity	NPC131506
0.7875	Intermediate Similarity	NPC157422
0.7875	Intermediate Similarity	NPC100586
0.7875	Intermediate Similarity	NPC109457
0.7875	Intermediate Similarity	NPC473279
0.7875	Intermediate Similarity	NPC469940
0.7875	Intermediate Similarity	NPC157777
0.7848	Intermediate Similarity	NPC213178
0.7848	Intermediate Similarity	NPC131892
0.7848	Intermediate Similarity	NPC321732
0.7848	Intermediate Similarity	NPC327728
0.7848	Intermediate Similarity	NPC324607
0.7848	Intermediate Similarity	NPC6120
0.7848	Intermediate Similarity	NPC99264
0.7841	Intermediate Similarity	NPC476727
0.7841	Intermediate Similarity	NPC476726
0.7831	Intermediate Similarity	NPC317913
0.7831	Intermediate Similarity	NPC474404
0.7831	Intermediate Similarity	NPC221420
0.7831	Intermediate Similarity	NPC207010
0.7816	Intermediate Similarity	NPC50438
0.7816	Intermediate Similarity	NPC34984
0.7816	Intermediate Similarity	NPC25037
0.7805	Intermediate Similarity	NPC21220
0.7805	Intermediate Similarity	NPC179858
0.7805	Intermediate Similarity	NPC477934
0.7805	Intermediate Similarity	NPC125767
0.7802	Intermediate Similarity	NPC262870
0.7792	Intermediate Similarity	NPC472946
0.7791	Intermediate Similarity	NPC102156
0.7791	Intermediate Similarity	NPC121121
0.7791	Intermediate Similarity	NPC148740
0.7791	Intermediate Similarity	NPC475388
0.7791	Intermediate Similarity	NPC328007
0.7789	Intermediate Similarity	NPC20028
0.7778	Intermediate Similarity	NPC473238
0.7778	Intermediate Similarity	NPC24705
0.7778	Intermediate Similarity	NPC81759
0.7778	Intermediate Similarity	NPC56962
0.7778	Intermediate Similarity	NPC472341
0.7766	Intermediate Similarity	NPC472273
0.7765	Intermediate Similarity	NPC261616
0.7753	Intermediate Similarity	NPC474174
0.7753	Intermediate Similarity	NPC251808
0.775	Intermediate Similarity	NPC477929
0.775	Intermediate Similarity	NPC282454
0.775	Intermediate Similarity	NPC477850
0.7738	Intermediate Similarity	NPC185465
0.7722	Intermediate Similarity	NPC474954
0.7717	Intermediate Similarity	NPC274046
0.7717	Intermediate Similarity	NPC198074
0.7711	Intermediate Similarity	NPC470145
0.7711	Intermediate Similarity	NPC472487
0.7711	Intermediate Similarity	NPC4209
0.7711	Intermediate Similarity	NPC472486
0.7708	Intermediate Similarity	NPC178853
0.7701	Intermediate Similarity	NPC86370
0.77	Intermediate Similarity	NPC208333
0.77	Intermediate Similarity	NPC227879
0.7683	Intermediate Similarity	NPC167702
0.7683	Intermediate Similarity	NPC280026
0.7683	Intermediate Similarity	NPC477930
0.7674	Intermediate Similarity	NPC58631
0.7667	Intermediate Similarity	NPC226491
0.7667	Intermediate Similarity	NPC476379
0.7667	Intermediate Similarity	NPC470417
0.7667	Intermediate Similarity	NPC477614
0.766	Intermediate Similarity	NPC116683
0.7654	Intermediate Similarity	NPC89310
0.7654	Intermediate Similarity	NPC127283
0.7654	Intermediate Similarity	NPC8004
0.7647	Intermediate Similarity	NPC477282
0.7647	Intermediate Similarity	NPC80891
0.7647	Intermediate Similarity	NPC320144
0.7647	Intermediate Similarity	NPC201276
0.7647	Intermediate Similarity	NPC81074
0.764	Intermediate Similarity	NPC472272
0.7634	Intermediate Similarity	NPC309127
0.7634	Intermediate Similarity	NPC191915
0.7634	Intermediate Similarity	NPC318332
0.7634	Intermediate Similarity	NPC151214
0.7634	Intermediate Similarity	NPC247877
0.7629	Intermediate Similarity	NPC80191
0.7629	Intermediate Similarity	NPC310031
0.7625	Intermediate Similarity	NPC319671
0.7625	Intermediate Similarity	NPC241085
0.7625	Intermediate Similarity	NPC470830
0.7625	Intermediate Similarity	NPC476734
0.7625	Intermediate Similarity	NPC107919
0.7625	Intermediate Similarity	NPC252032
0.7625	Intermediate Similarity	NPC299948
0.7625	Intermediate Similarity	NPC469941
0.7625	Intermediate Similarity	NPC474962
0.7619	Intermediate Similarity	NPC474574
0.7619	Intermediate Similarity	NPC143133
0.7619	Intermediate Similarity	NPC133596
0.7619	Intermediate Similarity	NPC171658
0.7619	Intermediate Similarity	NPC64081
0.7619	Intermediate Similarity	NPC298168
0.7619	Intermediate Similarity	NPC11907
0.7614	Intermediate Similarity	NPC471044
0.7614	Intermediate Similarity	NPC105895
0.7614	Intermediate Similarity	NPC473336
0.7609	Intermediate Similarity	NPC473166
0.7609	Intermediate Similarity	NPC52756
0.76	Intermediate Similarity	NPC472079
0.759	Intermediate Similarity	NPC472311
0.759	Intermediate Similarity	NPC212733
0.7586	Intermediate Similarity	NPC30583
0.7586	Intermediate Similarity	NPC202688
0.7586	Intermediate Similarity	NPC60018
0.7586	Intermediate Similarity	NPC145143
0.7586	Intermediate Similarity	NPC154043
0.7586	Intermediate Similarity	NPC268040
0.7586	Intermediate Similarity	NPC477858
0.7582	Intermediate Similarity	NPC61688
0.7579	Intermediate Similarity	NPC471241
0.7558	Intermediate Similarity	NPC16449
0.7556	Intermediate Similarity	NPC90652
0.7549	Intermediate Similarity	NPC473062
0.7531	Intermediate Similarity	NPC108131
0.7531	Intermediate Similarity	NPC476731
0.7529	Intermediate Similarity	NPC478128
0.7529	Intermediate Similarity	NPC324700

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 NPC472744 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	409
0.1-0.2	3526
0.2-0.3	3621
0.3-0.4	945
0.4-0.5	271
0.5-0.6	262
0.6-0.7	87
0.7-0.8	29
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
0.8101	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD4789	Approved
0.7975	Intermediate Similarity	NPD4244	Approved
0.7975	Intermediate Similarity	NPD4245	Approved
0.7848	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD3698	Phase 2
0.7848	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD6116	Phase 1
0.7792	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD5360	Phase 3
0.7711	Intermediate Similarity	NPD6117	Approved
0.7683	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD3702	Approved
0.7529	Intermediate Similarity	NPD6697	Approved
0.7529	Intermediate Similarity	NPD6115	Approved
0.7529	Intermediate Similarity	NPD6118	Approved
0.7529	Intermediate Similarity	NPD6114	Approved
0.7475	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6081	Approved
0.7439	Intermediate Similarity	NPD5777	Approved
0.7381	Intermediate Similarity	NPD3703	Phase 2
0.725	Intermediate Similarity	NPD4224	Phase 2
0.7229	Intermediate Similarity	NPD4758	Discontinued
0.7126	Intermediate Similarity	NPD5364	Discontinued
0.7126	Intermediate Similarity	NPD3671	Phase 1
0.7111	Intermediate Similarity	NPD4788	Approved
0.7053	Intermediate Similarity	NPD8035	Phase 2
0.7053	Intermediate Similarity	NPD8034	Phase 2
0.699	Remote Similarity	NPD6412	Phase 2
0.6957	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4786	Approved
0.6804	Remote Similarity	NPD6399	Phase 3
0.6804	Remote Similarity	NPD8171	Discontinued
0.6778	Remote Similarity	NPD6928	Phase 2
0.6759	Remote Similarity	NPD8133	Approved
0.6731	Remote Similarity	NPD6920	Discontinued
0.6706	Remote Similarity	NPD4787	Phase 1
0.67	Remote Similarity	NPD6083	Phase 2
0.67	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD4753	Phase 2
0.6636	Remote Similarity	NPD6940	Discontinued
0.663	Remote Similarity	NPD3667	Approved
0.6577	Remote Similarity	NPD7115	Discovery
0.6571	Remote Similarity	NPD5739	Approved
0.6571	Remote Similarity	NPD7128	Approved
0.6571	Remote Similarity	NPD6675	Approved
0.6571	Remote Similarity	NPD6402	Approved
0.6535	Remote Similarity	NPD4755	Approved
0.6514	Remote Similarity	NPD8297	Approved
0.6495	Remote Similarity	NPD5328	Approved
0.6489	Remote Similarity	NPD3133	Approved
0.6489	Remote Similarity	NPD3666	Approved
0.6489	Remote Similarity	NPD3665	Phase 1
0.6465	Remote Similarity	NPD4202	Approved
0.6449	Remote Similarity	NPD6881	Approved
0.6449	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD7320	Approved
0.6449	Remote Similarity	NPD6899	Approved
0.6413	Remote Similarity	NPD7525	Registered
0.6408	Remote Similarity	NPD4700	Approved
0.6408	Remote Similarity	NPD4696	Approved
0.6408	Remote Similarity	NPD5285	Approved
0.6408	Remote Similarity	NPD5286	Approved
0.6392	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6373	Approved
0.6389	Remote Similarity	NPD6372	Approved
0.6364	Remote Similarity	NPD6079	Approved
0.6355	Remote Similarity	NPD5697	Approved
0.6355	Remote Similarity	NPD5701	Approved
0.6354	Remote Similarity	NPD3618	Phase 1
0.6337	Remote Similarity	NPD5695	Phase 3
0.6337	Remote Similarity	NPD5210	Approved
0.6337	Remote Similarity	NPD4629	Approved
0.633	Remote Similarity	NPD7290	Approved
0.633	Remote Similarity	NPD6883	Approved
0.633	Remote Similarity	NPD7102	Approved
0.6311	Remote Similarity	NPD5696	Approved
0.6296	Remote Similarity	NPD6415	Discontinued
0.6286	Remote Similarity	NPD5211	Phase 2
0.6286	Remote Similarity	NPD5225	Approved
0.6286	Remote Similarity	NPD5226	Approved
0.6286	Remote Similarity	NPD4633	Approved
0.6286	Remote Similarity	NPD5224	Approved
0.6277	Remote Similarity	NPD4221	Approved
0.6277	Remote Similarity	NPD4223	Phase 3
0.6273	Remote Similarity	NPD6650	Approved
0.6273	Remote Similarity	NPD6847	Approved
0.6273	Remote Similarity	NPD6617	Approved
0.6273	Remote Similarity	NPD6649	Approved
0.6273	Remote Similarity	NPD6869	Approved
0.6273	Remote Similarity	NPD8130	Phase 1
0.6271	Remote Similarity	NPD7507	Approved
0.625	Remote Similarity	NPD5329	Approved
0.6239	Remote Similarity	NPD6012	Approved
0.6239	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6014	Approved
0.6239	Remote Similarity	NPD6013	Approved
0.6238	Remote Similarity	NPD7748	Approved
0.6226	Remote Similarity	NPD5174	Approved
0.6226	Remote Similarity	NPD5175	Approved
0.6224	Remote Similarity	NPD5737	Approved
0.6224	Remote Similarity	NPD6672	Approved
0.6216	Remote Similarity	NPD6882	Approved
0.6214	Remote Similarity	NPD7902	Approved
0.62	Remote Similarity	NPD7515	Phase 2
0.6196	Remote Similarity	NPD3617	Approved
0.619	Remote Similarity	NPD5223	Approved
0.619	Remote Similarity	NPD1700	Approved
0.619	Remote Similarity	NPD371	Approved
0.6186	Remote Similarity	NPD5279	Phase 3
0.6186	Remote Similarity	NPD7334	Approved
0.6186	Remote Similarity	NPD7146	Approved
0.6186	Remote Similarity	NPD6409	Approved
0.6186	Remote Similarity	NPD5330	Approved
0.6186	Remote Similarity	NPD6684	Approved
0.6186	Remote Similarity	NPD7521	Approved
0.6182	Remote Similarity	NPD4634	Approved
0.6176	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.617	Remote Similarity	NPD4139	Approved
0.617	Remote Similarity	NPD4692	Approved
0.6168	Remote Similarity	NPD5141	Approved
0.6161	Remote Similarity	NPD4632	Approved
0.6147	Remote Similarity	NPD6686	Approved
0.6147	Remote Similarity	NPD6011	Approved
0.6146	Remote Similarity	NPD4197	Approved
0.6146	Remote Similarity	NPD3668	Phase 3
0.6126	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD7524	Approved
0.6121	Remote Similarity	NPD6054	Approved
0.6121	Remote Similarity	NPD6319	Approved
0.6121	Remote Similarity	NPD6059	Approved
0.6117	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD4697	Phase 3
0.6117	Remote Similarity	NPD5222	Approved
0.6117	Remote Similarity	NPD5221	Approved
0.6116	Remote Similarity	NPD7319	Approved
0.6111	Remote Similarity	NPD4768	Approved
0.6111	Remote Similarity	NPD4767	Approved
0.6102	Remote Similarity	NPD7604	Phase 2
0.6098	Remote Similarity	NPD3198	Approved
0.6095	Remote Similarity	NPD8418	Phase 2
0.6075	Remote Similarity	NPD4754	Approved
0.6061	Remote Similarity	NPD6903	Approved
0.6058	Remote Similarity	NPD5173	Approved
0.6033	Remote Similarity	NPD7736	Approved
0.6022	Remote Similarity	NPD4238	Approved
0.6022	Remote Similarity	NPD4802	Phase 2
0.602	Remote Similarity	NPD4690	Approved
0.602	Remote Similarity	NPD6098	Approved
0.602	Remote Similarity	NPD4693	Phase 3
0.602	Remote Similarity	NPD5205	Approved
0.602	Remote Similarity	NPD4688	Approved
0.602	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.602	Remote Similarity	NPD4138	Approved
0.602	Remote Similarity	NPD4689	Approved
0.6017	Remote Similarity	NPD6370	Approved
0.6	Remote Similarity	NPD6080	Approved
0.6	Remote Similarity	NPD6904	Approved
0.6	Remote Similarity	NPD6673	Approved
0.6	Remote Similarity	NPD7638	Approved
0.6	Remote Similarity	NPD5128	Approved
0.6	Remote Similarity	NPD4729	Approved
0.6	Remote Similarity	NPD4730	Approved
0.6	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD6933	Approved
0.5948	Remote Similarity	NPD7328	Approved
0.5948	Remote Similarity	NPD7327	Approved
0.5943	Remote Similarity	NPD7639	Approved
0.5943	Remote Similarity	NPD7640	Approved
0.5932	Remote Similarity	NPD6015	Approved
0.5932	Remote Similarity	NPD6016	Approved
0.5922	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD7900	Approved
0.5917	Remote Similarity	NPD7492	Approved
0.5913	Remote Similarity	NPD6274	Approved
0.5909	Remote Similarity	NPD6705	Phase 1
0.5897	Remote Similarity	NPD7101	Approved
0.5897	Remote Similarity	NPD7100	Approved
0.5897	Remote Similarity	NPD7516	Approved
0.5893	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD5250	Approved
0.5893	Remote Similarity	NPD5249	Phase 3
0.5893	Remote Similarity	NPD5248	Approved
0.5893	Remote Similarity	NPD5251	Approved
0.5893	Remote Similarity	NPD5247	Approved
0.5882	Remote Similarity	NPD5988	Approved
0.5882	Remote Similarity	NPD5281	Approved
0.5882	Remote Similarity	NPD5284	Approved
0.5876	Remote Similarity	NPD3669	Approved
0.5876	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD6695	Phase 3
0.5875	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD3730	Approved
0.5875	Remote Similarity	NPD3728	Approved
0.587	Remote Similarity	NPD7339	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