NPASS Compound

Structure

NPC471365 OpenBabel07101718272D 34 36 0 0 1 0 0 0 0 0999 V2000 3.3006 -1.0780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7471 1.0534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7741 2.7387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6978 -0.4060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6201 -2.9928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3417 1.8960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5153 0.0804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3489 -1.2803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7741 1.0534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6978 -0.5573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3146 1.8960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8281 1.0534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0126 -0.4060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3273 2.5129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0126 2.5129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2876 1.8960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8552 0.0804 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9691 -2.2698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1699 2.9994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3273 1.5399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0126 1.5399 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1699 0.0804 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9985 0.3681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3957 0.8889 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9676 0.1017 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8552 1.0534 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1699 1.0534 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0174 -2.4721 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1699 3.9723 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9502 0.5704 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3273 -0.4060 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2697 -1.3444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3475 1.0911 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 8 1 0 0 0 0 2 9 2 0 0 0 0 3 16 2 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 7 31 1 0 0 0 0 8 10 1 0 0 0 0 9 16 1 0 0 0 0 10 23 1 0 0 0 0 11 12 1 0 0 0 0 11 16 1 0 0 0 0 12 26 1 0 0 0 0 13 17 1 0 0 0 0 13 22 1 0 0 0 0 14 19 1 0 0 0 0 14 20 2 0 0 0 0 15 19 1 0 0 0 0 15 21 1 0 0 0 0 17 26 1 6 0 0 0 18 28 2 0 0 0 0 18 32 1 0 0 0 0 19 29 2 0 0 0 0 20 24 1 0 0 0 0 21 26 1 1 0 0 0 21 27 1 0 0 0 0 22 27 1 6 0 0 0 22 31 1 0 0 0 0 23 30 2 0 0 0 0 23 33 1 0 0 0 0 24 33 1 6 0 0 0 24 34 1 0 0 0 0 25 27 1 6 0 0 0 25 32 1 0 0 0 0 25 34 1 0 0 0 0 26 6 1 1 0 0 0 27 20 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.26
Volume:	495.592
LogP:	3.533
LogD:	3.171
LogS:	-4.403
# Rotatable Bonds:	11
TPSA:	88.13
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.343
Synthetic Accessibility Score:	5.698
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.544
MDCK Permeability:	2.3489379600505345e-05
Pgp-inhibitor:	0.855
Pgp-substrate:	0.127
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.885

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.961
Plasma Protein Binding (PPB):	63.4541015625%
Volume Distribution (VD):	1.117
Pgp-substrate:	50.95884323120117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.06
CYP2C19-inhibitor:	0.044
CYP2C19-substrate:	0.597
CYP2C9-inhibitor:	0.165
CYP2C9-substrate:	0.078
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.085
CYP3A4-inhibitor:	0.773
CYP3A4-substrate:	0.454

ADMET: Excretion

Clearance (CL):	3.011
Half-life (T1/2):	0.875

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.829
Drug-inuced Liver Injury (DILI):	0.785
AMES Toxicity:	0.633
Rat Oral Acute Toxicity:	0.252
Maximum Recommended Daily Dose:	0.82
Skin Sensitization:	0.956
Carcinogencity:	0.686
Eye Corrosion:	0.372
Eye Irritation:	0.197
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC471365

Natural Product ID:	NPC471365
*Common Name:**	Rel-(5R,6R,8S,9S,10R,18S,19R)-19-Acetoxy-18-Butanoyloxy-18,19-Epoxy-6-Methoxycleroda-3,13(16),14-Trien-2-One
IUPAC Name:	[(1R,3S,6aR,7S,8S,10R,10aR)-1-acetyloxy-10-methoxy-7,8-dimethyl-7-(3-methylidenepent-4-enyl)-5-oxo-3,6,6a,8,9,10-hexahydro-1H-benzo[d][2]benzofuran-3-yl] butanoate
Synonyms:
Standard InCHIKey:	IBCAWXJQHQPFKN-IIQDEMOSSA-N
Standard InCHI:	InChI=1S/C27H38O7/c1-8-10-23(30)33-24-20-14-19(29)15-21-26(6,12-11-16(3)9-2)17(4)13-22(31-7)27(20,21)25(34-24)32-18(5)28/h9,14,17,21-22,24-25H,2-3,8,10-13,15H2,1,4-7H3/t17-,21+,22+,24+,25-,26-,27-/m0/s1
SMILES:	CCCC(=O)OC1C2=CC(=O)CC3C2(C(CC(C3(C)CCC(=C)C=C)C)OC)C(O1)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2419872
PubChem CID:	73349185
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane 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
NPO32459	casearia balansae	Species	Salicaceae	Eukaryota	leaves and twigs	n.a.	n.a.	PMID[24033131]
NPO32459	casearia balansae	Species	Salicaceae	Eukaryota	twigs	n.a.	n.a.	PMID[25286284]
NPO32459	casearia balansae	Species	Salicaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[26699618]

☑ 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

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1374	Cell Line	WI-38	Homo sapiens	IC50	=	14800.0	nM	PMID[497196]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	11300.0	nM	PMID[497196]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	7200.0	nM	PMID[497196]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	7200.0	nM	PMID[497196]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	4600.0	nM	PMID[497196]

☑ 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 NPC471365 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	234
0.1-0.2	1170
0.2-0.3	4040
0.3-0.4	7906
0.4-0.5	13666
0.5-0.6	7465
0.6-0.7	6405
0.7-0.8	1654
0.8-0.85	108
0.85-0.9	44
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC132395
1.0	High Similarity	NPC471364
0.8878	High Similarity	NPC472188
0.8788	High Similarity	NPC471366
0.8788	High Similarity	NPC318917
0.8788	High Similarity	NPC472186
0.8788	High Similarity	NPC476800
0.875	High Similarity	NPC112457
0.87	High Similarity	NPC473204
0.87	High Similarity	NPC472187
0.87	High Similarity	NPC473545
0.8673	High Similarity	NPC471372
0.8673	High Similarity	NPC472189
0.8673	High Similarity	NPC473369
0.8673	High Similarity	NPC471362
0.8641	High Similarity	NPC252296
0.8614	High Similarity	NPC473384
0.8586	High Similarity	NPC112654
0.8586	High Similarity	NPC311166
0.8586	High Similarity	NPC171598
0.8571	High Similarity	NPC477129
0.8571	High Similarity	NPC477130
0.8558	High Similarity	NPC184512
0.8557	High Similarity	NPC65513
0.8542	High Similarity	NPC284561
0.8529	High Similarity	NPC471363
0.8529	High Similarity	NPC238397
0.85	High Similarity	NPC38530
0.85	High Similarity	NPC84335
0.85	High Similarity	NPC110937
0.8469	Intermediate Similarity	NPC471571
0.8454	Intermediate Similarity	NPC152467
0.8447	Intermediate Similarity	NPC475889
0.8447	Intermediate Similarity	NPC134270
0.8447	Intermediate Similarity	NPC127933
0.8447	Intermediate Similarity	NPC7644
0.8447	Intermediate Similarity	NPC7613
0.8438	Intermediate Similarity	NPC477128
0.8426	Intermediate Similarity	NPC157441
0.8421	Intermediate Similarity	NPC220478
0.8393	Intermediate Similarity	NPC204731
0.8384	Intermediate Similarity	NPC38830
0.8384	Intermediate Similarity	NPC88507
0.8365	Intermediate Similarity	NPC201880
0.8365	Intermediate Similarity	NPC470321
0.8365	Intermediate Similarity	NPC264867
0.8365	Intermediate Similarity	NPC473207
0.8365	Intermediate Similarity	NPC81567
0.8351	Intermediate Similarity	NPC73995
0.8333	Intermediate Similarity	NPC194951
0.8333	Intermediate Similarity	NPC12046
0.8318	Intermediate Similarity	NPC119550
0.8317	Intermediate Similarity	NPC257726
0.8317	Intermediate Similarity	NPC204054
0.8316	Intermediate Similarity	NPC300985
0.8269	Intermediate Similarity	NPC254202
0.8252	Intermediate Similarity	NPC472643
0.8247	Intermediate Similarity	NPC196407
0.8247	Intermediate Similarity	NPC215831
0.8235	Intermediate Similarity	NPC473154
0.8235	Intermediate Similarity	NPC176845
0.8208	Intermediate Similarity	NPC88013
0.8208	Intermediate Similarity	NPC125423
0.8208	Intermediate Similarity	NPC109376
0.82	Intermediate Similarity	NPC470697
0.8198	Intermediate Similarity	NPC23046
0.819	Intermediate Similarity	NPC189616
0.8182	Intermediate Similarity	NPC474631
0.8173	Intermediate Similarity	NPC32577
0.8173	Intermediate Similarity	NPC114540
0.8173	Intermediate Similarity	NPC155332
0.8165	Intermediate Similarity	NPC222834
0.8163	Intermediate Similarity	NPC174765
0.8155	Intermediate Similarity	NPC470761
0.8155	Intermediate Similarity	NPC472644
0.8155	Intermediate Similarity	NPC473219
0.8137	Intermediate Similarity	NPC2049
0.8137	Intermediate Similarity	NPC476768
0.8131	Intermediate Similarity	NPC128795
0.8131	Intermediate Similarity	NPC224660
0.8131	Intermediate Similarity	NPC135015
0.8131	Intermediate Similarity	NPC469844
0.8131	Intermediate Similarity	NPC217921
0.8131	Intermediate Similarity	NPC48548
0.8131	Intermediate Similarity	NPC311223
0.8131	Intermediate Similarity	NPC470024
0.8125	Intermediate Similarity	NPC473617
0.8125	Intermediate Similarity	NPC473828
0.8113	Intermediate Similarity	NPC469607
0.8113	Intermediate Similarity	NPC127790
0.8113	Intermediate Similarity	NPC172867
0.8113	Intermediate Similarity	NPC218158
0.8113	Intermediate Similarity	NPC472645
0.81	Intermediate Similarity	NPC79117
0.8081	Intermediate Similarity	NPC220454
0.8081	Intermediate Similarity	NPC469595
0.8081	Intermediate Similarity	NPC212679
0.8058	Intermediate Similarity	NPC474440
0.8056	Intermediate Similarity	NPC316974
0.8056	Intermediate Similarity	NPC40728
0.8056	Intermediate Similarity	NPC469370
0.8039	Intermediate Similarity	NPC8954
0.8039	Intermediate Similarity	NPC94905
0.8021	Intermediate Similarity	NPC71626
0.802	Intermediate Similarity	NPC474554
0.8019	Intermediate Similarity	NPC222161
0.8019	Intermediate Similarity	NPC474898
0.8019	Intermediate Similarity	NPC476764
0.8019	Intermediate Similarity	NPC118911
0.8019	Intermediate Similarity	NPC470297
0.8019	Intermediate Similarity	NPC476763
0.8018	Intermediate Similarity	NPC475163
0.8	Intermediate Similarity	NPC473944
0.8	Intermediate Similarity	NPC179517
0.8	Intermediate Similarity	NPC134077
0.8	Intermediate Similarity	NPC165904
0.7982	Intermediate Similarity	NPC151616
0.7982	Intermediate Similarity	NPC316708
0.7982	Intermediate Similarity	NPC83005
0.7982	Intermediate Similarity	NPC253906
0.7982	Intermediate Similarity	NPC48692
0.798	Intermediate Similarity	NPC293044
0.7963	Intermediate Similarity	NPC275539
0.7963	Intermediate Similarity	NPC189075
0.7961	Intermediate Similarity	NPC285513
0.7961	Intermediate Similarity	NPC254496
0.7961	Intermediate Similarity	NPC474343
0.7961	Intermediate Similarity	NPC292133
0.7946	Intermediate Similarity	NPC471816
0.7946	Intermediate Similarity	NPC243981
0.7944	Intermediate Similarity	NPC476762
0.7944	Intermediate Similarity	NPC476761
0.7944	Intermediate Similarity	NPC476760
0.7944	Intermediate Similarity	NPC477125
0.7941	Intermediate Similarity	NPC316215
0.7941	Intermediate Similarity	NPC183012
0.7938	Intermediate Similarity	NPC177932
0.7938	Intermediate Similarity	NPC472442
0.7938	Intermediate Similarity	NPC110405
0.7938	Intermediate Similarity	NPC189311
0.7928	Intermediate Similarity	NPC75167
0.7928	Intermediate Similarity	NPC25909
0.7928	Intermediate Similarity	NPC311592
0.7925	Intermediate Similarity	NPC475526
0.7925	Intermediate Similarity	NPC120009
0.7925	Intermediate Similarity	NPC329345
0.7925	Intermediate Similarity	NPC473283
0.7925	Intermediate Similarity	NPC476770
0.7921	Intermediate Similarity	NPC166346
0.7917	Intermediate Similarity	NPC193198
0.7917	Intermediate Similarity	NPC472440
0.7909	Intermediate Similarity	NPC470026
0.7909	Intermediate Similarity	NPC17791
0.7905	Intermediate Similarity	NPC63249
0.7905	Intermediate Similarity	NPC476240
0.7905	Intermediate Similarity	NPC476223
0.7905	Intermediate Similarity	NPC224720
0.7905	Intermediate Similarity	NPC310981
0.7905	Intermediate Similarity	NPC194028
0.7905	Intermediate Similarity	NPC115899
0.7905	Intermediate Similarity	NPC168319
0.79	Intermediate Similarity	NPC474842
0.79	Intermediate Similarity	NPC161638
0.79	Intermediate Similarity	NPC475965
0.79	Intermediate Similarity	NPC469372
0.7895	Intermediate Similarity	NPC122971
0.7895	Intermediate Similarity	NPC476529
0.7895	Intermediate Similarity	NPC475775
0.7885	Intermediate Similarity	NPC108368
0.7885	Intermediate Similarity	NPC252295
0.7885	Intermediate Similarity	NPC57079
0.7881	Intermediate Similarity	NPC42399
0.7879	Intermediate Similarity	NPC226863
0.7876	Intermediate Similarity	NPC473968
0.787	Intermediate Similarity	NPC110496
0.787	Intermediate Similarity	NPC133422
0.7864	Intermediate Similarity	NPC240673
0.7864	Intermediate Similarity	NPC17578
0.7864	Intermediate Similarity	NPC73858
0.7857	Intermediate Similarity	NPC181145
0.785	Intermediate Similarity	NPC476001
0.785	Intermediate Similarity	NPC119493
0.7843	Intermediate Similarity	NPC473435
0.7843	Intermediate Similarity	NPC473431
0.7843	Intermediate Similarity	NPC473434
0.7843	Intermediate Similarity	NPC471446
0.7843	Intermediate Similarity	NPC474841
0.7843	Intermediate Similarity	NPC473280
0.7843	Intermediate Similarity	NPC471078
0.7838	Intermediate Similarity	NPC328074
0.7838	Intermediate Similarity	NPC321272
0.7838	Intermediate Similarity	NPC317460
0.7838	Intermediate Similarity	NPC470025
0.7835	Intermediate Similarity	NPC159635
0.7835	Intermediate Similarity	NPC30486
0.783	Intermediate Similarity	NPC476081
0.783	Intermediate Similarity	NPC162973
0.783	Intermediate Similarity	NPC469606
0.783	Intermediate Similarity	NPC476769
0.783	Intermediate Similarity	NPC136289

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 NPC471365 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	1433
0.2-0.3	3605
0.3-0.4	2502
0.4-0.5	909
0.5-0.6	254
0.6-0.7	189
0.7-0.8	63
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
0.7938	Intermediate Similarity	NPD1694	Approved
0.7679	Intermediate Similarity	NPD6882	Approved
0.75	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7900	Approved
0.7477	Intermediate Similarity	NPD6881	Approved
0.7477	Intermediate Similarity	NPD6899	Approved
0.7477	Intermediate Similarity	NPD6686	Approved
0.7455	Intermediate Similarity	NPD6675	Approved
0.7455	Intermediate Similarity	NPD7128	Approved
0.7455	Intermediate Similarity	NPD6402	Approved
0.7455	Intermediate Similarity	NPD6008	Approved
0.7455	Intermediate Similarity	NPD5739	Approved
0.7449	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD3573	Approved
0.7387	Intermediate Similarity	NPD5697	Approved
0.7355	Intermediate Similarity	NPD7507	Approved
0.7345	Intermediate Similarity	NPD7290	Approved
0.7345	Intermediate Similarity	NPD6883	Approved
0.7345	Intermediate Similarity	NPD7102	Approved
0.7333	Intermediate Similarity	NPD7748	Approved
0.7327	Intermediate Similarity	NPD6409	Approved
0.7327	Intermediate Similarity	NPD6684	Approved
0.7327	Intermediate Similarity	NPD7146	Approved
0.7327	Intermediate Similarity	NPD7521	Approved
0.7327	Intermediate Similarity	NPD7334	Approved
0.7327	Intermediate Similarity	NPD5330	Approved
0.7321	Intermediate Similarity	NPD7320	Approved
0.729	Intermediate Similarity	NPD7902	Approved
0.7281	Intermediate Similarity	NPD6869	Approved
0.7281	Intermediate Similarity	NPD6649	Approved
0.7281	Intermediate Similarity	NPD6617	Approved
0.7281	Intermediate Similarity	NPD6650	Approved
0.7281	Intermediate Similarity	NPD6847	Approved
0.7281	Intermediate Similarity	NPD8130	Phase 1
0.7265	Intermediate Similarity	NPD7115	Discovery
0.7257	Intermediate Similarity	NPD6372	Approved
0.7257	Intermediate Similarity	NPD6012	Approved
0.7257	Intermediate Similarity	NPD6013	Approved
0.7257	Intermediate Similarity	NPD6014	Approved
0.7257	Intermediate Similarity	NPD6373	Approved
0.725	Intermediate Similarity	NPD6370	Approved
0.7238	Intermediate Similarity	NPD6399	Phase 3
0.7236	Intermediate Similarity	NPD7736	Approved
0.7232	Intermediate Similarity	NPD5701	Approved
0.7222	Intermediate Similarity	NPD4225	Approved
0.7222	Intermediate Similarity	NPD7638	Approved
0.7217	Intermediate Similarity	NPD8297	Approved
0.7184	Intermediate Similarity	NPD6903	Approved
0.7184	Intermediate Similarity	NPD5737	Approved
0.7184	Intermediate Similarity	NPD6672	Approved
0.7184	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD7319	Approved
0.7168	Intermediate Similarity	NPD6011	Approved
0.7167	Intermediate Similarity	NPD8515	Approved
0.7167	Intermediate Similarity	NPD8517	Approved
0.7167	Intermediate Similarity	NPD8513	Phase 3
0.7167	Intermediate Similarity	NPD8516	Approved
0.7156	Intermediate Similarity	NPD7640	Approved
0.7156	Intermediate Similarity	NPD7639	Approved
0.7154	Intermediate Similarity	NPD8293	Discontinued
0.7143	Intermediate Similarity	NPD6411	Approved
0.7143	Intermediate Similarity	NPD6079	Approved
0.7143	Intermediate Similarity	NPD7515	Phase 2
0.7131	Intermediate Similarity	NPD7492	Approved
0.7115	Intermediate Similarity	NPD5328	Approved
0.7103	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6054	Approved
0.708	Intermediate Similarity	NPD6412	Phase 2
0.7075	Intermediate Similarity	NPD5778	Approved
0.7075	Intermediate Similarity	NPD5779	Approved
0.7073	Intermediate Similarity	NPD6616	Approved
0.7049	Intermediate Similarity	NPD8328	Phase 3
0.7027	Intermediate Similarity	NPD5211	Phase 2
0.7016	Intermediate Similarity	NPD7078	Approved
0.7	Intermediate Similarity	NPD5286	Approved
0.7	Intermediate Similarity	NPD4696	Approved
0.7	Intermediate Similarity	NPD5285	Approved
0.6983	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5693	Phase 1
0.6975	Remote Similarity	NPD6009	Approved
0.6972	Remote Similarity	NPD4755	Approved
0.6961	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6101	Approved
0.6952	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD6059	Approved
0.693	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD8039	Approved
0.6903	Remote Similarity	NPD5141	Approved
0.6887	Remote Similarity	NPD5207	Approved
0.6885	Remote Similarity	NPD7503	Approved
0.6885	Remote Similarity	NPD6016	Approved
0.6885	Remote Similarity	NPD6015	Approved
0.6881	Remote Similarity	NPD5222	Approved
0.6881	Remote Similarity	NPD5221	Approved
0.6881	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5225	Approved
0.6875	Remote Similarity	NPD5226	Approved
0.6875	Remote Similarity	NPD5224	Approved
0.6875	Remote Similarity	NPD4633	Approved
0.686	Remote Similarity	NPD7101	Approved
0.686	Remote Similarity	NPD7100	Approved
0.6847	Remote Similarity	NPD4700	Approved
0.6829	Remote Similarity	NPD5988	Approved
0.6827	Remote Similarity	NPD3618	Phase 1
0.6822	Remote Similarity	NPD6050	Approved
0.6822	Remote Similarity	NPD5694	Approved
0.6818	Remote Similarity	NPD6084	Phase 2
0.6818	Remote Similarity	NPD6083	Phase 2
0.6818	Remote Similarity	NPD5173	Approved
0.6814	Remote Similarity	NPD5175	Approved
0.6814	Remote Similarity	NPD5174	Approved
0.681	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.681	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6080	Approved
0.6792	Remote Similarity	NPD6673	Approved
0.6792	Remote Similarity	NPD6904	Approved
0.6789	Remote Similarity	NPD5695	Phase 3
0.6786	Remote Similarity	NPD5223	Approved
0.678	Remote Similarity	NPD6053	Discontinued
0.6777	Remote Similarity	NPD6335	Approved
0.6777	Remote Similarity	NPD7327	Approved
0.6777	Remote Similarity	NPD7328	Approved
0.6752	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6868	Approved
0.675	Remote Similarity	NPD6274	Approved
0.6748	Remote Similarity	NPD8033	Approved
0.6729	Remote Similarity	NPD5692	Phase 3
0.6727	Remote Similarity	NPD4697	Phase 3
0.6723	Remote Similarity	NPD4632	Approved
0.6721	Remote Similarity	NPD7516	Approved
0.6697	Remote Similarity	NPD6001	Approved
0.6694	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6317	Approved
0.6667	Remote Similarity	NPD6319	Approved
0.6667	Remote Similarity	NPD5284	Approved
0.6667	Remote Similarity	NPD8377	Approved
0.6667	Remote Similarity	NPD8294	Approved
0.6667	Remote Similarity	NPD5281	Approved
0.664	Remote Similarity	NPD6067	Discontinued
0.6639	Remote Similarity	NPD6314	Approved
0.6639	Remote Similarity	NPD6313	Approved
0.6636	Remote Similarity	NPD6051	Approved
0.6635	Remote Similarity	NPD4786	Approved
0.6635	Remote Similarity	NPD3668	Phase 3
0.6614	Remote Similarity	NPD8074	Phase 3
0.6613	Remote Similarity	NPD8379	Approved
0.6613	Remote Similarity	NPD6909	Approved
0.6613	Remote Similarity	NPD8378	Approved
0.6613	Remote Similarity	NPD8296	Approved
0.6613	Remote Similarity	NPD6908	Approved
0.6613	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD8380	Approved
0.6613	Remote Similarity	NPD8335	Approved
0.6607	Remote Similarity	NPD5696	Approved
0.6606	Remote Similarity	NPD4202	Approved
0.6602	Remote Similarity	NPD5209	Approved
0.6602	Remote Similarity	NPD3667	Approved
0.6583	Remote Similarity	NPD8133	Approved
0.6581	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD4729	Approved
0.6581	Remote Similarity	NPD4730	Approved
0.6579	Remote Similarity	NPD7632	Discontinued
0.6574	Remote Similarity	NPD5785	Approved
0.6552	Remote Similarity	NPD4767	Approved
0.6552	Remote Similarity	NPD4768	Approved
0.6549	Remote Similarity	NPD6648	Approved
0.6542	Remote Similarity	NPD5208	Approved
0.6538	Remote Similarity	NPD7260	Phase 2
0.6522	Remote Similarity	NPD4754	Approved
0.6514	Remote Similarity	NPD8035	Phase 2
0.6514	Remote Similarity	NPD8034	Phase 2
0.6509	Remote Similarity	NPD6098	Approved
0.6508	Remote Similarity	NPD7604	Phase 2
0.6481	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.648	Remote Similarity	NPD5983	Phase 2
0.6476	Remote Similarity	NPD3133	Approved
0.6476	Remote Similarity	NPD3666	Approved
0.6476	Remote Similarity	NPD3665	Phase 1
0.6471	Remote Similarity	NPD5250	Approved
0.6471	Remote Similarity	NPD5248	Approved
0.6471	Remote Similarity	NPD5251	Approved
0.6471	Remote Similarity	NPD4634	Approved
0.6471	Remote Similarity	NPD5249	Phase 3
0.6471	Remote Similarity	NPD5247	Approved
0.6442	Remote Similarity	NPD6435	Approved
0.6441	Remote Similarity	NPD5128	Approved
0.6434	Remote Similarity	NPD6033	Approved
0.6422	Remote Similarity	NPD6698	Approved
0.6422	Remote Similarity	NPD46	Approved
0.6417	Remote Similarity	NPD5216	Approved
0.6417	Remote Similarity	NPD5217	Approved
0.6417	Remote Similarity	NPD5215	Approved
0.6406	Remote Similarity	NPD6336	Discontinued
0.6364	Remote Similarity	NPD7637	Suspended
0.6355	Remote Similarity	NPD4623	Approved
0.6355	Remote Similarity	NPD5279	Phase 3
0.6355	Remote Similarity	NPD4519	Discontinued
0.6348	Remote Similarity	NPD5344	Discontinued
0.6339	Remote Similarity	NPD5654	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