NPASS Compound

Structure

NPC470906 OpenBabel07101718282D 36 40 0 0 1 0 0 0 0 0999 V2000 -7.5628 0.3864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9885 2.7044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1261 -0.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1859 0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7375 2.1045 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 -5.6065 0.8023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2757 1.5454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6284 1.0102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 3.0827 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 -1.9400 2.9781 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 -2.5981 0.5000 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 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9229 2.0806 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 -7.2538 1.3375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3194 1.9612 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3412 2.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 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 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4049 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 -1.7321 2.0000 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 1 0 0 0 0 0 0 0 0 0 -8.9011 1.8727 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4049 1.0000 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 1.8171 1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 3 21 2 0 0 0 0 4 28 1 0 0 0 0 6 35 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 19 2 0 0 0 0 9 20 1 0 0 0 0 10 12 1 0 0 0 0 10 22 1 0 0 0 0 11 13 1 0 0 0 0 11 25 1 0 0 0 0 12 29 1 0 0 0 0 14 15 1 0 0 0 0 14 28 1 0 0 0 0 15 30 1 0 0 0 0 16 24 1 0 0 0 0 17 19 1 0 0 0 0 17 32 2 0 0 0 0 18 30 1 0 0 0 0 18 31 1 0 0 0 0 20 2 1 6 0 0 0 20 22 1 0 0 0 0 21 26 1 0 0 0 0 21 27 1 0 0 0 0 22 28 1 6 0 0 0 23 16 1 6 0 0 0 23 26 1 0 0 0 0 23 36 1 0 0 0 0 24 29 1 6 0 0 0 24 30 1 0 0 0 0 25 33 2 0 0 0 0 25 35 1 0 0 0 0 26 31 1 6 0 0 0 27 34 2 0 0 0 0 27 36 1 0 0 0 0 28 29 1 1 0 0 0 29 5 1 6 0 0 0 30 31 1 1 0 0 0 31 13 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	496.32
Volume:	532.719
LogP:	4.373
LogD:	4.052
LogS:	-5.235
# Rotatable Bonds:	9
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.227
Synthetic Accessibility Score:	5.677
Fsp3:	0.774
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	3
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.862
MDCK Permeability:	3.759854007512331e-05
Pgp-inhibitor:	0.913
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.894

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.077
Plasma Protein Binding (PPB):	95.27483367919922%
Volume Distribution (VD):	0.762
Pgp-substrate:	3.55717134475708%

ADMET: Metabolism

CYP1A2-inhibitor:	0.07
CYP1A2-substrate:	0.408
CYP2C19-inhibitor:	0.626
CYP2C19-substrate:	0.832
CYP2C9-inhibitor:	0.833
CYP2C9-substrate:	0.12
CYP2D6-inhibitor:	0.232
CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.967
CYP3A4-substrate:	0.508

ADMET: Excretion

Clearance (CL):	7.98
Half-life (T1/2):	0.345

ADMET: Toxicity

hERG Blockers:	0.588
Human Hepatotoxicity (H-HT):	0.204
Drug-inuced Liver Injury (DILI):	0.738
AMES Toxicity:	0.167
Rat Oral Acute Toxicity:	0.263
Maximum Recommended Daily Dose:	0.891
Skin Sensitization:	0.975
Carcinogencity:	0.642
Eye Corrosion:	0.906
Eye Irritation:	0.112
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC470906

Natural Product ID:	NPC470906
*Common Name:**	Coronalolide Methyl Ester
IUPAC Name:	n.a.
Synonyms:	Coronalolide Methyl Ester
Standard InCHIKey:	FPFAZZFTBDKRJL-AWZAQAKTSA-N
Standard InCHI:	InChI=1S/C31H44O5/c1-19(17-32)8-7-9-20(2)22-10-12-29(5)24-16-23-26(21(3)27(34)36-23)31(13-11-25(33)35-6)18-30(24,31)15-14-28(22,29)4/h8,17,20,22-24,26H,3,7,9-16,18H2,1-2,4-6H3/b19-8+/t20-,22-,23-,24-,26-,28+,29-,30+,31+/m0/s1
SMILES:	CC(CCC=C(C)C=O)C1CCC2(C1(CCC34C2CC5C(C3(C4)CCC(=O)OC)C(=C)C(=O)O5)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2308377
PubChem CID:	71720331
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
NPO11647	Gardenia sootepensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19456120]
NPO33315	gardenia spp.	Species	Rubiaceae	Eukaryota	n.a.	Thai	n.a.	PMID[22142538]
NPO11647	Gardenia sootepensis	Species	Rubiaceae	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	5
Others	1

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	2
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT323	Cell Line	SW-620	Homo sapiens	IC50	=	6.19	ug.mL-1	PMID[543403]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	6.8	ug.mL-1	PMID[543403]
NPT845	Cell Line	BT-474	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[543403]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	8.64	ug.mL-1	PMID[543403]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10.0	ug.mL-1	PMID[543403]
NPT177	Tissue	Aorta	Rattus norvegicus	Inhibition	=	10.0	%	PMID[543404]

☑ 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 NPC470906 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	248
0.1-0.2	1422
0.2-0.3	5243
0.3-0.4	13402
0.4-0.5	8626
0.5-0.6	7147
0.6-0.7	5422
0.7-0.8	1129
0.8-0.85	44
0.85-0.9	7
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9684	High Similarity	NPC176883
0.9677	High Similarity	NPC252295
0.9674	High Similarity	NPC307164
0.9368	High Similarity	NPC476303
0.9082	High Similarity	NPC476237
0.8817	High Similarity	NPC288699
0.875	High Similarity	NPC33473
0.8737	High Similarity	NPC474185
0.8673	High Similarity	NPC473155
0.8598	High Similarity	NPC470275
0.8519	High Similarity	NPC470276
0.8485	Intermediate Similarity	NPC98868
0.8478	Intermediate Similarity	NPC470011
0.8431	Intermediate Similarity	NPC189616
0.8421	Intermediate Similarity	NPC73995
0.84	Intermediate Similarity	NPC201406
0.8384	Intermediate Similarity	NPC292133
0.8384	Intermediate Similarity	NPC110937
0.8333	Intermediate Similarity	NPC112009
0.8333	Intermediate Similarity	NPC152467
0.8333	Intermediate Similarity	NPC474842
0.8333	Intermediate Similarity	NPC475965
0.8333	Intermediate Similarity	NPC180204
0.8317	Intermediate Similarity	NPC310981
0.8316	Intermediate Similarity	NPC226863
0.8316	Intermediate Similarity	NPC215831
0.83	Intermediate Similarity	NPC176845
0.8288	Intermediate Similarity	NPC470277
0.8283	Intermediate Similarity	NPC106425
0.8283	Intermediate Similarity	NPC122324
0.8283	Intermediate Similarity	NPC151725
0.828	Intermediate Similarity	NPC100391
0.828	Intermediate Similarity	NPC219011
0.8265	Intermediate Similarity	NPC477130
0.8265	Intermediate Similarity	NPC477129
0.8265	Intermediate Similarity	NPC294266
0.8261	Intermediate Similarity	NPC226988
0.8247	Intermediate Similarity	NPC49420
0.8247	Intermediate Similarity	NPC476187
0.8224	Intermediate Similarity	NPC69291
0.8211	Intermediate Similarity	NPC175293
0.82	Intermediate Similarity	NPC2049
0.8182	Intermediate Similarity	NPC183012
0.8182	Intermediate Similarity	NPC293052
0.8172	Intermediate Similarity	NPC194637
0.8163	Intermediate Similarity	NPC475657
0.8163	Intermediate Similarity	NPC470224
0.8155	Intermediate Similarity	NPC120321
0.8155	Intermediate Similarity	NPC254202
0.8155	Intermediate Similarity	NPC36688
0.8144	Intermediate Similarity	NPC161638
0.8137	Intermediate Similarity	NPC168319
0.8137	Intermediate Similarity	NPC194028
0.8137	Intermediate Similarity	NPC303559
0.8137	Intermediate Similarity	NPC118174
0.8131	Intermediate Similarity	NPC470960
0.8125	Intermediate Similarity	NPC80335
0.8125	Intermediate Similarity	NPC477128
0.8119	Intermediate Similarity	NPC108368
0.8119	Intermediate Similarity	NPC57079
0.8085	Intermediate Similarity	NPC96055
0.8081	Intermediate Similarity	NPC269729
0.8081	Intermediate Similarity	NPC470697
0.8065	Intermediate Similarity	NPC178676
0.8061	Intermediate Similarity	NPC72845
0.8061	Intermediate Similarity	NPC233345
0.8061	Intermediate Similarity	NPC186363
0.8061	Intermediate Similarity	NPC470113
0.8058	Intermediate Similarity	NPC155332
0.8058	Intermediate Similarity	NPC32577
0.8058	Intermediate Similarity	NPC114540
0.8041	Intermediate Similarity	NPC128496
0.8041	Intermediate Similarity	NPC177141
0.8039	Intermediate Similarity	NPC35751
0.8021	Intermediate Similarity	NPC470012
0.8021	Intermediate Similarity	NPC167877
0.802	Intermediate Similarity	NPC474343
0.802	Intermediate Similarity	NPC23680
0.802	Intermediate Similarity	NPC253826
0.802	Intermediate Similarity	NPC226986
0.8	Intermediate Similarity	NPC274417
0.8	Intermediate Similarity	NPC127790
0.8	Intermediate Similarity	NPC280877
0.8	Intermediate Similarity	NPC470223
0.7982	Intermediate Similarity	NPC122056
0.7981	Intermediate Similarity	NPC297617
0.7981	Intermediate Similarity	NPC36321
0.798	Intermediate Similarity	NPC472871
0.798	Intermediate Similarity	NPC475700
0.798	Intermediate Similarity	NPC139692
0.798	Intermediate Similarity	NPC79117
0.798	Intermediate Similarity	NPC229976
0.7979	Intermediate Similarity	NPC22611
0.7959	Intermediate Similarity	NPC475776
0.7959	Intermediate Similarity	NPC328141
0.7959	Intermediate Similarity	NPC302280
0.7959	Intermediate Similarity	NPC159748
0.7959	Intermediate Similarity	NPC101651
0.7959	Intermediate Similarity	NPC471896
0.7959	Intermediate Similarity	NPC212679
0.7959	Intermediate Similarity	NPC220454
0.7959	Intermediate Similarity	NPC469595
0.7957	Intermediate Similarity	NPC38642
0.7946	Intermediate Similarity	NPC475520
0.7941	Intermediate Similarity	NPC194196
0.7938	Intermediate Similarity	NPC28227
0.7938	Intermediate Similarity	NPC473229
0.7925	Intermediate Similarity	NPC131665
0.7925	Intermediate Similarity	NPC255387
0.7921	Intermediate Similarity	NPC327788
0.7921	Intermediate Similarity	NPC471039
0.7917	Intermediate Similarity	NPC264127
0.7917	Intermediate Similarity	NPC470051
0.7917	Intermediate Similarity	NPC477920
0.7917	Intermediate Similarity	NPC470050
0.7905	Intermediate Similarity	NPC470297
0.7905	Intermediate Similarity	NPC472868
0.79	Intermediate Similarity	NPC471720
0.79	Intermediate Similarity	NPC38830
0.79	Intermediate Similarity	NPC476186
0.79	Intermediate Similarity	NPC473431
0.79	Intermediate Similarity	NPC57117
0.79	Intermediate Similarity	NPC473280
0.79	Intermediate Similarity	NPC471078
0.79	Intermediate Similarity	NPC471040
0.79	Intermediate Similarity	NPC473435
0.7895	Intermediate Similarity	NPC139566
0.7885	Intermediate Similarity	NPC136289
0.7885	Intermediate Similarity	NPC476081
0.7879	Intermediate Similarity	NPC190442
0.7879	Intermediate Similarity	NPC472953
0.7879	Intermediate Similarity	NPC26888
0.7872	Intermediate Similarity	NPC200513
0.787	Intermediate Similarity	NPC470496
0.787	Intermediate Similarity	NPC179642
0.7864	Intermediate Similarity	NPC471413
0.7864	Intermediate Similarity	NPC47024
0.7864	Intermediate Similarity	NPC476274
0.7864	Intermediate Similarity	NPC470761
0.7864	Intermediate Similarity	NPC473219
0.7864	Intermediate Similarity	NPC470074
0.7864	Intermediate Similarity	NPC266955
0.7857	Intermediate Similarity	NPC473720
0.7857	Intermediate Similarity	NPC474396
0.7857	Intermediate Similarity	NPC50488
0.7857	Intermediate Similarity	NPC66344
0.7857	Intermediate Similarity	NPC474679
0.785	Intermediate Similarity	NPC61411
0.785	Intermediate Similarity	NPC306265
0.785	Intermediate Similarity	NPC189075
0.785	Intermediate Similarity	NPC275539
0.7849	Intermediate Similarity	NPC170038
0.7843	Intermediate Similarity	NPC10057
0.7843	Intermediate Similarity	NPC73911
0.7843	Intermediate Similarity	NPC84335
0.7843	Intermediate Similarity	NPC151488
0.7843	Intermediate Similarity	NPC476768
0.7843	Intermediate Similarity	NPC108078
0.7843	Intermediate Similarity	NPC291634
0.7843	Intermediate Similarity	NPC126815
0.7843	Intermediate Similarity	NPC38530
0.7838	Intermediate Similarity	NPC196931
0.7835	Intermediate Similarity	NPC181103
0.7835	Intermediate Similarity	NPC305029
0.783	Intermediate Similarity	NPC475414
0.783	Intermediate Similarity	NPC173172
0.783	Intermediate Similarity	NPC470267
0.783	Intermediate Similarity	NPC266570
0.7822	Intermediate Similarity	NPC476519
0.7822	Intermediate Similarity	NPC476174
0.7822	Intermediate Similarity	NPC84383
0.7818	Intermediate Similarity	NPC473535
0.7812	Intermediate Similarity	NPC110405
0.7812	Intermediate Similarity	NPC177932
0.7812	Intermediate Similarity	NPC474013
0.7812	Intermediate Similarity	NPC189311
0.781	Intermediate Similarity	NPC473283
0.781	Intermediate Similarity	NPC475526
0.781	Intermediate Similarity	NPC329345
0.78	Intermediate Similarity	NPC476304
0.78	Intermediate Similarity	NPC38232
0.7798	Intermediate Similarity	NPC474315
0.7789	Intermediate Similarity	NPC139206
0.7788	Intermediate Similarity	NPC224720
0.7788	Intermediate Similarity	NPC81530
0.7788	Intermediate Similarity	NPC115899
0.7788	Intermediate Similarity	NPC471412
0.7788	Intermediate Similarity	NPC476223
0.7788	Intermediate Similarity	NPC476240
0.7778	Intermediate Similarity	NPC148414
0.7778	Intermediate Similarity	NPC474901
0.7778	Intermediate Similarity	NPC175628
0.7778	Intermediate Similarity	NPC475941
0.7778	Intermediate Similarity	NPC273199
0.7778	Intermediate Similarity	NPC112457
0.7778	Intermediate Similarity	NPC8062
0.7778	Intermediate Similarity	NPC111585
0.7768	Intermediate Similarity	NPC167606
0.7768	Intermediate Similarity	NPC286528
0.7768	Intermediate Similarity	NPC140055

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 NPC470906 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	208
0.1-0.2	1649
0.2-0.3	4023
0.3-0.4	2259
0.4-0.5	589
0.5-0.6	189
0.6-0.7	182
0.7-0.8	49
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8367	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6008	Approved
0.79	Intermediate Similarity	NPD6001	Approved
0.7872	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD1694	Approved
0.78	Intermediate Similarity	NPD6399	Phase 3
0.7768	Intermediate Similarity	NPD7115	Discovery
0.7767	Intermediate Similarity	NPD7638	Approved
0.7755	Intermediate Similarity	NPD6672	Approved
0.7755	Intermediate Similarity	NPD5737	Approved
0.7755	Intermediate Similarity	NPD6903	Approved
0.7732	Intermediate Similarity	NPD6409	Approved
0.7732	Intermediate Similarity	NPD6684	Approved
0.7732	Intermediate Similarity	NPD5330	Approved
0.7732	Intermediate Similarity	NPD7521	Approved
0.7732	Intermediate Similarity	NPD7334	Approved
0.7732	Intermediate Similarity	NPD7146	Approved
0.7692	Intermediate Similarity	NPD7639	Approved
0.7692	Intermediate Similarity	NPD7640	Approved
0.7596	Intermediate Similarity	NPD4225	Approved
0.7576	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD7900	Approved
0.7525	Intermediate Similarity	NPD5693	Phase 1
0.7404	Intermediate Similarity	NPD4697	Phase 3
0.7379	Intermediate Similarity	NPD7748	Approved
0.7374	Intermediate Similarity	NPD3618	Phase 1
0.7364	Intermediate Similarity	NPD7320	Approved
0.7364	Intermediate Similarity	NPD6899	Approved
0.7364	Intermediate Similarity	NPD6881	Approved
0.7353	Intermediate Similarity	NPD8035	Phase 2
0.7353	Intermediate Similarity	NPD8034	Phase 2
0.7353	Intermediate Similarity	NPD6079	Approved
0.7339	Intermediate Similarity	NPD7128	Approved
0.7339	Intermediate Similarity	NPD5739	Approved
0.7339	Intermediate Similarity	NPD6675	Approved
0.7339	Intermediate Similarity	NPD6402	Approved
0.7333	Intermediate Similarity	NPD7902	Approved
0.7327	Intermediate Similarity	NPD6904	Approved
0.7327	Intermediate Similarity	NPD6673	Approved
0.7327	Intermediate Similarity	NPD5328	Approved
0.7327	Intermediate Similarity	NPD6080	Approved
0.7321	Intermediate Similarity	NPD6650	Approved
0.7321	Intermediate Similarity	NPD6649	Approved
0.7297	Intermediate Similarity	NPD6372	Approved
0.7297	Intermediate Similarity	NPD6373	Approved
0.7273	Intermediate Similarity	NPD5697	Approved
0.7255	Intermediate Similarity	NPD5207	Approved
0.7232	Intermediate Similarity	NPD7102	Approved
0.7232	Intermediate Similarity	NPD6883	Approved
0.7232	Intermediate Similarity	NPD7290	Approved
0.7207	Intermediate Similarity	NPD6011	Approved
0.7184	Intermediate Similarity	NPD7515	Phase 2
0.7172	Intermediate Similarity	NPD4786	Approved
0.717	Intermediate Similarity	NPD6083	Phase 2
0.717	Intermediate Similarity	NPD6084	Phase 2
0.7168	Intermediate Similarity	NPD6847	Approved
0.7168	Intermediate Similarity	NPD8130	Phase 1
0.7168	Intermediate Similarity	NPD6869	Approved
0.7168	Intermediate Similarity	NPD6617	Approved
0.7157	Intermediate Similarity	NPD6051	Approved
0.7143	Intermediate Similarity	NPD6014	Approved
0.7143	Intermediate Similarity	NPD6013	Approved
0.7143	Intermediate Similarity	NPD6012	Approved
0.7129	Intermediate Similarity	NPD3573	Approved
0.7117	Intermediate Similarity	NPD5701	Approved
0.7107	Intermediate Similarity	NPD7507	Approved
0.7105	Intermediate Similarity	NPD8297	Approved
0.7105	Intermediate Similarity	NPD6882	Approved
0.7103	Intermediate Similarity	NPD5696	Approved
0.71	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5221	Approved
0.7075	Intermediate Similarity	NPD5222	Approved
0.7064	Intermediate Similarity	NPD7632	Discontinued
0.7059	Intermediate Similarity	NPD5208	Approved
0.703	Intermediate Similarity	NPD6098	Approved
0.7019	Intermediate Similarity	NPD6050	Approved
0.7018	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5173	Approved
0.7	Intermediate Similarity	NPD3668	Phase 3
0.7	Intermediate Similarity	NPD6052	Approved
0.699	Remote Similarity	NPD1695	Approved
0.6981	Remote Similarity	NPD5695	Phase 3
0.697	Remote Similarity	NPD3667	Approved
0.6964	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD4202	Approved
0.6935	Remote Similarity	NPD7319	Approved
0.6923	Remote Similarity	NPD6868	Approved
0.6923	Remote Similarity	NPD5692	Phase 3
0.6923	Remote Similarity	NPD5785	Approved
0.6917	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5211	Phase 2
0.6881	Remote Similarity	NPD4696	Approved
0.6881	Remote Similarity	NPD5286	Approved
0.6881	Remote Similarity	NPD5285	Approved
0.6863	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5694	Approved
0.6852	Remote Similarity	NPD4755	Approved
0.6832	Remote Similarity	NPD3666	Approved
0.6832	Remote Similarity	NPD3133	Approved
0.6832	Remote Similarity	NPD3665	Phase 1
0.6822	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5223	Approved
0.6807	Remote Similarity	NPD6335	Approved
0.6803	Remote Similarity	NPD7604	Phase 2
0.6786	Remote Similarity	NPD5141	Approved
0.6783	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6274	Approved
0.6757	Remote Similarity	NPD5224	Approved
0.6757	Remote Similarity	NPD5226	Approved
0.6757	Remote Similarity	NPD5225	Approved
0.6757	Remote Similarity	NPD4633	Approved
0.6754	Remote Similarity	NPD6686	Approved
0.6752	Remote Similarity	NPD4632	Approved
0.675	Remote Similarity	NPD7101	Approved
0.675	Remote Similarity	NPD7100	Approved
0.6748	Remote Similarity	NPD7492	Approved
0.6727	Remote Similarity	NPD4700	Approved
0.6723	Remote Similarity	NPD6317	Approved
0.6698	Remote Similarity	NPD5281	Approved
0.6698	Remote Similarity	NPD5284	Approved
0.6697	Remote Similarity	NPD5959	Approved
0.6696	Remote Similarity	NPD5174	Approved
0.6696	Remote Similarity	NPD5175	Approved
0.6696	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6616	Approved
0.6694	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD6053	Discontinued
0.6667	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD6313	Approved
0.6667	Remote Similarity	NPD6614	Approved
0.6667	Remote Similarity	NPD5210	Approved
0.664	Remote Similarity	NPD7078	Approved
0.6634	Remote Similarity	NPD5209	Approved
0.6634	Remote Similarity	NPD4221	Approved
0.6634	Remote Similarity	NPD4223	Phase 3
0.6602	Remote Similarity	NPD5329	Approved
0.66	Remote Similarity	NPD7525	Registered
0.6587	Remote Similarity	NPD7736	Approved
0.6585	Remote Similarity	NPD6370	Approved
0.6583	Remote Similarity	NPD6009	Approved
0.6569	Remote Similarity	NPD5362	Discontinued
0.6557	Remote Similarity	NPD6059	Approved
0.6557	Remote Similarity	NPD6319	Approved
0.6549	Remote Similarity	NPD4754	Approved
0.6542	Remote Similarity	NPD7637	Suspended
0.6538	Remote Similarity	NPD5279	Phase 3
0.6531	Remote Similarity	NPD6117	Approved
0.6529	Remote Similarity	NPD7327	Approved
0.6529	Remote Similarity	NPD7328	Approved
0.6526	Remote Similarity	NPD4747	Approved
0.6526	Remote Similarity	NPD4691	Approved
0.6514	Remote Similarity	NPD5654	Approved
0.6508	Remote Similarity	NPD8293	Discontinued
0.6505	Remote Similarity	NPD4197	Approved
0.6504	Remote Similarity	NPD6015	Approved
0.6504	Remote Similarity	NPD6908	Approved
0.6504	Remote Similarity	NPD6909	Approved
0.6504	Remote Similarity	NPD5983	Phase 2
0.6504	Remote Similarity	NPD8033	Approved
0.6504	Remote Similarity	NPD6016	Approved
0.6496	Remote Similarity	NPD6371	Approved
0.6475	Remote Similarity	NPD7516	Approved
0.6466	Remote Similarity	NPD5128	Approved
0.6466	Remote Similarity	NPD5168	Approved
0.6466	Remote Similarity	NPD4729	Approved
0.6466	Remote Similarity	NPD4730	Approved
0.6465	Remote Similarity	NPD6116	Phase 1
0.6452	Remote Similarity	NPD5988	Approved
0.6442	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD5363	Approved
0.6436	Remote Similarity	NPD4695	Discontinued
0.6435	Remote Similarity	NPD4767	Approved
0.6435	Remote Similarity	NPD4768	Approved
0.6429	Remote Similarity	NPD8039	Approved
0.6429	Remote Similarity	NPD6942	Approved
0.6429	Remote Similarity	NPD7339	Approved
0.6429	Remote Similarity	NPD6336	Discontinued
0.6423	Remote Similarity	NPD8294	Approved
0.6423	Remote Similarity	NPD8377	Approved
0.6421	Remote Similarity	NPD4137	Phase 3
0.6408	Remote Similarity	NPD4788	Approved
0.64	Remote Similarity	NPD6114	Approved
0.64	Remote Similarity	NPD6115	Approved
0.64	Remote Similarity	NPD6118	Approved
0.64	Remote Similarity	NPD6697	Approved
0.64	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6411	Approved
0.6381	Remote Similarity	NPD4138	Approved
0.6381	Remote Similarity	NPD4688	Approved
0.6381	Remote Similarity	NPD4693	Phase 3
0.6381	Remote Similarity	NPD4690	Approved
0.6381	Remote Similarity	NPD5205	Approved
0.6381	Remote Similarity	NPD4689	Approved
0.6381	Remote Similarity	NPD5690	Phase 2
0.6379	Remote Similarity	NPD6412	Phase 2

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