NPASS Compound

Structure

NPC476330 OpenBabel07101719132D 31 30 0 0 1 0 0 0 0 0999 V2000 2.0981 1.6340 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 -2.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -0.8660 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 -5.6962 -2.8660 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 3.8301 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 0.1340 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 2.9641 0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8301 0.6340 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 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 2.0981 0.6340 0.0000 C 0 0 3 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 -3.0981 -2.3660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0981 -1.3660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6962 0.1340 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 4.6962 -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 1 0 0 0 0 0 0 0 0 0 5.5622 -1.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5622 0.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -3.8660 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 -4.8301 -2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 19 1 0 0 0 0 4 24 1 0 0 0 0 5 24 1 0 0 0 0 7 31 1 0 0 0 0 8 10 1 0 0 0 0 8 16 1 0 0 0 0 9 11 1 0 0 0 0 9 15 1 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 12 18 1 0 0 0 0 13 22 1 0 0 0 0 14 17 1 0 0 0 0 14 21 1 0 0 0 0 15 24 1 0 0 0 0 16 25 1 0 0 0 0 17 25 1 0 0 0 0 19 26 2 0 0 0 0 20 3 1 1 0 0 0 20 21 1 0 0 0 0 20 23 1 0 0 0 0 21 27 1 6 0 0 0 22 24 1 0 0 0 0 22 28 2 0 0 0 0 23 29 2 0 0 0 0 23 31 1 0 0 0 0 25 6 1 1 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	442.33
Volume:	485.788
LogP:	2.92
LogD:	2.853
LogS:	-4.106
# Rotatable Bonds:	18
TPSA:	100.9
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	0
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.319
Synthetic Accessibility Score:	4.158
Fsp3:	0.88
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.684
MDCK Permeability:	1.88705471373396e-05
Pgp-inhibitor:	0.983
Pgp-substrate:	0.037
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.947
30% Bioavailability (F30%):	0.953

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.422
Plasma Protein Binding (PPB):	76.47573852539062%
Volume Distribution (VD):	1.045
Pgp-substrate:	15.768294334411621%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.81
CYP2C19-inhibitor:	0.135
CYP2C19-substrate:	0.929
CYP2C9-inhibitor:	0.207
CYP2C9-substrate:	0.952
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.294
CYP3A4-inhibitor:	0.511
CYP3A4-substrate:	0.117

ADMET: Excretion

Clearance (CL):	7.087
Half-life (T1/2):	0.816

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.229
Drug-inuced Liver Injury (DILI):	0.182
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.051
Carcinogencity:	0.007
Eye Corrosion:	0.006
Eye Irritation:	0.029
Respiratory Toxicity:	0.024

Download Data

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

Natural Product: NPC476330

Natural Product ID:	NPC476330
*Common Name:**	(+)-Muqubilone B Diol
IUPAC Name:	methyl (2R,3R,6R)-3,6-dihydroxy-2,6,10,14,14-pentamethyl-13,18-dioxononadecanoate
Synonyms:	(+)-Muqubilone B Diol
Standard InCHIKey:	XKGRANJMUQHPIW-ZQYADJKOSA-N
Standard InCHI:	InChI=1S/C25H46O6/c1-18(12-13-22(28)24(4,5)15-9-11-19(2)26)10-8-16-25(6,30)17-14-21(27)20(3)23(29)31-7/h18,20-21,27,30H,8-17H2,1-7H3/t18?,20-,21-,25-/m1/s1
SMILES:	COC(=O)[C@@H]([C@@H](CC[C@@](CCCC(CCC(=O)C(CCCC(=O)C)(C)C)C)(O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL565210
PubChem CID:	25243602
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
NPO4185	Diacarnus bismarckensis	Species	Podospongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19159277]

☑ 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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	>	25.0	ug.mL-1	PMID[573984]

☑ 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 NPC476330 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	547
0.1-0.2	4030
0.2-0.3	12673
0.3-0.4	11484
0.4-0.5	8065
0.5-0.6	5417
0.6-0.7	416
0.7-0.8	56
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.875	High Similarity	NPC306805
0.875	High Similarity	NPC215987
0.873	High Similarity	NPC474552
0.8413	Intermediate Similarity	NPC472021
0.8308	Intermediate Similarity	NPC314103
0.8254	Intermediate Similarity	NPC472020
0.8254	Intermediate Similarity	NPC475821
0.8254	Intermediate Similarity	NPC226602
0.8254	Intermediate Similarity	NPC472019
0.8209	Intermediate Similarity	NPC469925
0.8194	Intermediate Similarity	NPC469867
0.8	Intermediate Similarity	NPC469923
0.7969	Intermediate Similarity	NPC470363
0.7917	Intermediate Similarity	NPC179922
0.7826	Intermediate Similarity	NPC319007
0.7733	Intermediate Similarity	NPC308545
0.7733	Intermediate Similarity	NPC82488
0.7703	Intermediate Similarity	NPC122847
0.7703	Intermediate Similarity	NPC474003
0.7692	Intermediate Similarity	NPC469924
0.7667	Intermediate Similarity	NPC90904
0.76	Intermediate Similarity	NPC476986
0.76	Intermediate Similarity	NPC470905
0.75	Intermediate Similarity	NPC470243
0.7468	Intermediate Similarity	NPC477434
0.7467	Intermediate Similarity	NPC476264
0.7467	Intermediate Similarity	NPC476325
0.7467	Intermediate Similarity	NPC477918
0.7436	Intermediate Similarity	NPC476984
0.7436	Intermediate Similarity	NPC475395
0.7429	Intermediate Similarity	NPC286842
0.7391	Intermediate Similarity	NPC469926
0.7353	Intermediate Similarity	NPC235788
0.7342	Intermediate Similarity	NPC476983
0.7333	Intermediate Similarity	NPC200618
0.7333	Intermediate Similarity	NPC474316
0.7333	Intermediate Similarity	NPC59602
0.7333	Intermediate Similarity	NPC131770
0.7333	Intermediate Similarity	NPC474020
0.7333	Intermediate Similarity	NPC469514
0.7333	Intermediate Similarity	NPC477933
0.7333	Intermediate Similarity	NPC477932
0.7333	Intermediate Similarity	NPC475744
0.7333	Intermediate Similarity	NPC476985
0.7333	Intermediate Similarity	NPC106872
0.7333	Intermediate Similarity	NPC324793
0.7333	Intermediate Similarity	NPC152754
0.7333	Intermediate Similarity	NPC476987
0.7333	Intermediate Similarity	NPC477878
0.7313	Intermediate Similarity	NPC469921
0.7308	Intermediate Similarity	NPC117960
0.7308	Intermediate Similarity	NPC172309
0.7308	Intermediate Similarity	NPC14044
0.7302	Intermediate Similarity	NPC72722
0.7297	Intermediate Similarity	NPC477930
0.7297	Intermediate Similarity	NPC317212
0.7286	Intermediate Similarity	NPC241949
0.7273	Intermediate Similarity	NPC268502
0.7273	Intermediate Similarity	NPC254996
0.725	Intermediate Similarity	NPC471343
0.7237	Intermediate Similarity	NPC307865
0.7229	Intermediate Similarity	NPC477440
0.7229	Intermediate Similarity	NPC477443
0.7215	Intermediate Similarity	NPC476292
0.7215	Intermediate Similarity	NPC474605
0.7215	Intermediate Similarity	NPC477935
0.7206	Intermediate Similarity	NPC469922
0.72	Intermediate Similarity	NPC179858
0.72	Intermediate Similarity	NPC477934
0.72	Intermediate Similarity	NPC228411
0.7188	Intermediate Similarity	NPC320588
0.7188	Intermediate Similarity	NPC469937
0.7188	Intermediate Similarity	NPC23155
0.7188	Intermediate Similarity	NPC53463
0.7183	Intermediate Similarity	NPC41542
0.7167	Intermediate Similarity	NPC328497
0.7167	Intermediate Similarity	NPC21844
0.7167	Intermediate Similarity	NPC324004
0.7164	Intermediate Similarity	NPC17935
0.7162	Intermediate Similarity	NPC474755
0.716	Intermediate Similarity	NPC477205
0.7143	Intermediate Similarity	NPC477444
0.7143	Intermediate Similarity	NPC477442
0.7143	Intermediate Similarity	NPC477433
0.7125	Intermediate Similarity	NPC476100
0.7123	Intermediate Similarity	NPC470268
0.7108	Intermediate Similarity	NPC471221
0.7083	Intermediate Similarity	NPC82315
0.7073	Intermediate Similarity	NPC475181
0.7073	Intermediate Similarity	NPC83242
0.7073	Intermediate Similarity	NPC476104
0.7067	Intermediate Similarity	NPC330016
0.7067	Intermediate Similarity	NPC477867
0.7042	Intermediate Similarity	NPC473899
0.7042	Intermediate Similarity	NPC135043
0.7042	Intermediate Similarity	NPC315525
0.7037	Intermediate Similarity	NPC34984
0.7037	Intermediate Similarity	NPC219535
0.7037	Intermediate Similarity	NPC319909
0.7037	Intermediate Similarity	NPC471044
0.7037	Intermediate Similarity	NPC237938
0.7037	Intermediate Similarity	NPC25037
0.7037	Intermediate Similarity	NPC473336
0.7027	Intermediate Similarity	NPC478227
0.7027	Intermediate Similarity	NPC474590
0.7013	Intermediate Similarity	NPC207010
0.7013	Intermediate Similarity	NPC317913
0.7013	Intermediate Similarity	NPC471151
0.7013	Intermediate Similarity	NPC281296
0.7013	Intermediate Similarity	NPC169389
0.7	Intermediate Similarity	NPC12438
0.7	Intermediate Similarity	NPC314679
0.7	Intermediate Similarity	NPC477936
0.7	Intermediate Similarity	NPC30195
0.6984	Remote Similarity	NPC314084
0.6974	Remote Similarity	NPC132064
0.6962	Remote Similarity	NPC476265
0.6962	Remote Similarity	NPC274522
0.6951	Remote Similarity	NPC471344
0.6951	Remote Similarity	NPC131350
0.6951	Remote Similarity	NPC477445
0.6951	Remote Similarity	NPC473350
0.6944	Remote Similarity	NPC476928
0.6944	Remote Similarity	NPC472984
0.6933	Remote Similarity	NPC474100
0.6933	Remote Similarity	NPC51249
0.6933	Remote Similarity	NPC475260
0.6933	Remote Similarity	NPC475232
0.6933	Remote Similarity	NPC473775
0.6933	Remote Similarity	NPC473699
0.6933	Remote Similarity	NPC167145
0.6923	Remote Similarity	NPC476732
0.6923	Remote Similarity	NPC199965
0.6923	Remote Similarity	NPC121200
0.6923	Remote Similarity	NPC185465
0.6923	Remote Similarity	NPC472608
0.6923	Remote Similarity	NPC26029
0.6914	Remote Similarity	NPC472847
0.6914	Remote Similarity	NPC157328
0.6901	Remote Similarity	NPC469791
0.6901	Remote Similarity	NPC19311
0.6901	Remote Similarity	NPC230047
0.6897	Remote Similarity	NPC206878
0.6892	Remote Similarity	NPC477929
0.6885	Remote Similarity	NPC249754
0.6883	Remote Similarity	NPC4209
0.6875	Remote Similarity	NPC476988
0.6867	Remote Similarity	NPC92139
0.6867	Remote Similarity	NPC120395
0.6867	Remote Similarity	NPC476717
0.6867	Remote Similarity	NPC262085
0.6867	Remote Similarity	NPC476982
0.6849	Remote Similarity	NPC119838
0.6842	Remote Similarity	NPC125164
0.6842	Remote Similarity	NPC472945
0.6842	Remote Similarity	NPC280026
0.6842	Remote Similarity	NPC167702
0.6842	Remote Similarity	NPC472944
0.6842	Remote Similarity	NPC215030
0.6835	Remote Similarity	NPC19841
0.6835	Remote Similarity	NPC201276
0.6835	Remote Similarity	NPC113363
0.6835	Remote Similarity	NPC80891
0.6835	Remote Similarity	NPC275243
0.6835	Remote Similarity	NPC320144
0.6833	Remote Similarity	NPC469781
0.6833	Remote Similarity	NPC55023
0.6829	Remote Similarity	NPC120158
0.6829	Remote Similarity	NPC473299
0.6829	Remote Similarity	NPC475193
0.6829	Remote Similarity	NPC50438
0.6824	Remote Similarity	NPC253618
0.6824	Remote Similarity	NPC471342
0.6824	Remote Similarity	NPC469866
0.6824	Remote Similarity	NPC67653
0.6824	Remote Similarity	NPC77001
0.6824	Remote Similarity	NPC471459
0.68	Remote Similarity	NPC469940
0.6795	Remote Similarity	NPC474433
0.6795	Remote Similarity	NPC214030
0.6795	Remote Similarity	NPC180199
0.6795	Remote Similarity	NPC83108
0.6795	Remote Similarity	NPC264602
0.6795	Remote Similarity	NPC477919
0.679	Remote Similarity	NPC164289
0.679	Remote Similarity	NPC289486
0.679	Remote Similarity	NPC242771
0.679	Remote Similarity	NPC61107
0.679	Remote Similarity	NPC311642
0.679	Remote Similarity	NPC100366
0.6786	Remote Similarity	NPC252714
0.6786	Remote Similarity	NPC51662
0.6786	Remote Similarity	NPC314364
0.6786	Remote Similarity	NPC197333
0.6786	Remote Similarity	NPC134197
0.6782	Remote Similarity	NPC472237
0.6782	Remote Similarity	NPC476189
0.6782	Remote Similarity	NPC472238
0.6774	Remote Similarity	NPC13105
0.6757	Remote Similarity	NPC28526

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 NPC476330 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	791
0.1-0.2	3889
0.2-0.3	2823
0.3-0.4	943
0.4-0.5	462
0.5-0.6	203
0.6-0.7	33
0.7-0.8	5
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD3729	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7909	Approved
0.7424	Intermediate Similarity	NPD3198	Approved
0.7188	Intermediate Similarity	NPD3728	Approved
0.7188	Intermediate Similarity	NPD3730	Approved
0.7049	Intermediate Similarity	NPD2266	Phase 2
0.7013	Intermediate Similarity	NPD6116	Phase 1
0.7	Intermediate Similarity	NPD634	Phase 3
0.6984	Remote Similarity	NPD9638	Phase 2
0.6923	Remote Similarity	NPD4802	Phase 2
0.6923	Remote Similarity	NPD4238	Approved
0.6923	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD6117	Approved
0.6875	Remote Similarity	NPD5369	Approved
0.6875	Remote Similarity	NPD3186	Phase 1
0.6849	Remote Similarity	NPD229	Approved
0.6842	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD6114	Approved
0.6709	Remote Similarity	NPD6115	Approved
0.6709	Remote Similarity	NPD6118	Approved
0.6709	Remote Similarity	NPD6697	Approved
0.6667	Remote Similarity	NPD4244	Approved
0.6667	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4245	Approved
0.6585	Remote Similarity	NPD6435	Approved
0.6579	Remote Similarity	NPD6081	Approved
0.6579	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5777	Approved
0.6579	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD4224	Phase 2
0.6557	Remote Similarity	NPD2699	Approved
0.6543	Remote Similarity	NPD5368	Approved
0.6538	Remote Similarity	NPD3702	Approved
0.6533	Remote Similarity	NPD3698	Phase 2
0.6533	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.65	Remote Similarity	NPD387	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD6411	Approved
0.6447	Remote Similarity	NPD4789	Approved
0.6438	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD4269	Approved
0.6386	Remote Similarity	NPD7345	Approved
0.6386	Remote Similarity	NPD4270	Approved
0.6364	Remote Similarity	NPD5785	Approved
0.6333	Remote Similarity	NPD2270	Approved
0.6296	Remote Similarity	NPD7917	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD7918	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD5786	Approved
0.6264	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6101	Approved
0.625	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD5360	Phase 3
0.6163	Remote Similarity	NPD5363	Approved
0.6145	Remote Similarity	NPD4821	Approved
0.6145	Remote Similarity	NPD4820	Approved
0.6145	Remote Similarity	NPD4819	Approved
0.6145	Remote Similarity	NPD4822	Approved
0.6145	Remote Similarity	NPD4252	Approved
0.6125	Remote Similarity	NPD2257	Approved
0.6125	Remote Similarity	NPD3703	Phase 2
0.6118	Remote Similarity	NPD7154	Phase 3
0.6111	Remote Similarity	NPD7983	Approved
0.6061	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD5778	Approved
0.6044	Remote Similarity	NPD5779	Approved
0.6044	Remote Similarity	NPD6399	Phase 3
0.6042	Remote Similarity	NPD8138	Approved
0.6042	Remote Similarity	NPD8085	Approved
0.6042	Remote Similarity	NPD8084	Approved
0.6042	Remote Similarity	NPD8083	Approved
0.6042	Remote Similarity	NPD8082	Approved
0.6042	Remote Similarity	NPD8086	Approved
0.6042	Remote Similarity	NPD8139	Approved
0.6032	Remote Similarity	NPD3199	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7341	Phase 2
0.6	Remote Similarity	NPD9448	Phase 2
0.6	Remote Similarity	NPD633	Phase 3
0.6	Remote Similarity	NPD73	Approved
0.6	Remote Similarity	NPD9450	Approved
0.6	Remote Similarity	NPD77	Approved
0.6	Remote Similarity	NPD9655	Approved
0.5979	Remote Similarity	NPD8275	Approved
0.5979	Remote Similarity	NPD8276	Approved
0.5978	Remote Similarity	NPD5282	Discontinued
0.5977	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD6084	Phase 2
0.5957	Remote Similarity	NPD6083	Phase 2
0.5955	Remote Similarity	NPD4264	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD6371	Approved
0.5934	Remote Similarity	NPD8034	Phase 2
0.5934	Remote Similarity	NPD8035	Phase 2
0.5934	Remote Similarity	NPD7515	Phase 2
0.593	Remote Similarity	NPD5362	Discontinued
0.5918	Remote Similarity	NPD8081	Approved
0.5918	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD3671	Phase 1
0.5904	Remote Similarity	NPD4271	Approved
0.5904	Remote Similarity	NPD4268	Approved
0.5897	Remote Similarity	NPD3726	Approved
0.5897	Remote Similarity	NPD3725	Approved
0.5859	Remote Similarity	NPD8393	Approved
0.5859	Remote Similarity	NPD5739	Approved
0.5859	Remote Similarity	NPD6402	Approved
0.5859	Remote Similarity	NPD7128	Approved
0.5859	Remote Similarity	NPD6675	Approved
0.5833	Remote Similarity	NPD3206	Approved
0.5824	Remote Similarity	NPD46	Approved
0.5824	Remote Similarity	NPD6698	Approved
0.5823	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD7748	Approved
0.5789	Remote Similarity	NPD7902	Approved
0.5773	Remote Similarity	NPD1700	Approved
0.575	Remote Similarity	NPD4758	Discontinued
0.5747	Remote Similarity	NPD4788	Approved
0.5745	Remote Similarity	NPD5695	Phase 3
0.5743	Remote Similarity	NPD7320	Approved
0.5743	Remote Similarity	NPD6881	Approved
0.5743	Remote Similarity	NPD6899	Approved
0.5714	Remote Similarity	NPD5364	Discontinued
0.5714	Remote Similarity	NPD3732	Approved
0.5714	Remote Similarity	NPD375	Phase 2
0.5714	Remote Similarity	NPD5370	Suspended
0.5696	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD6373	Approved
0.5686	Remote Similarity	NPD6372	Approved
0.5684	Remote Similarity	NPD7839	Suspended
0.5682	Remote Similarity	NPD4786	Approved
0.5676	Remote Similarity	NPD9656	Approved
0.5667	Remote Similarity	NPD9449	Clinical (unspecified phase)
0.5658	Remote Similarity	NPD3197	Phase 1
0.5652	Remote Similarity	NPD66	Approved
0.5652	Remote Similarity	NPD8960	Approved
0.5652	Remote Similarity	NPD64	Approved
0.5652	Remote Similarity	NPD72	Approved
0.5652	Remote Similarity	NPD9009	Approved
0.5652	Remote Similarity	NPD9010	Approved
0.5652	Remote Similarity	NPD9008	Approved
0.5652	Remote Similarity	NPD65	Approved
0.5652	Remote Similarity	NPD9007	Approved
0.5652	Remote Similarity	NPD9011	Approved
0.5644	Remote Similarity	NPD8307	Discontinued
0.5644	Remote Similarity	NPD5697	Approved
0.5644	Remote Similarity	NPD5701	Approved
0.5644	Remote Similarity	NPD8140	Approved
0.5632	Remote Similarity	NPD3667	Approved
0.5631	Remote Similarity	NPD7102	Approved
0.5631	Remote Similarity	NPD6883	Approved
0.5631	Remote Similarity	NPD7290	Approved
0.5606	Remote Similarity	NPD384	Approved
0.5606	Remote Similarity	NPD385	Approved
0.56	Remote Similarity	NPD9676	Phase 3

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