NPASS Compound

Structure

NPC476196 OpenBabel07101719252D 42 47 0 0 1 0 0 0 0 0999 V2000 0.4432 -2.9108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1237 -2.9108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7705 -2.9175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0782 0.1279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5931 -0.7123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7406 -0.0738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4407 0.8490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9308 -0.0111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2834 -1.4554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4432 -0.9703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0925 -2.8250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8863 0.5117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1079 0.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4680 -1.7636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0218 0.4629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3107 0.7609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2834 -2.4257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9583 -2.3868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1722 0.2559 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6648 0.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4432 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2216 0.3838 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.0065 0.6982 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2216 0.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4432 0.5117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.5117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6648 0.1279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2216 0.1279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0784 -0.4365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0117 -1.4180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1079 0.1279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7915 0.1279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5214 -0.7948 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2216 0.1279 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4432 1.4820 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.4820 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8881 -0.9710 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1994 -0.8874 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8774 -0.9799 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8863 -0.0000 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 -1.4917 -0.7948 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 31 1 0 0 0 0 5 31 1 0 0 0 0 6 32 1 0 0 0 0 7 32 1 0 0 0 0 8 39 1 0 0 0 0 9 10 1 0 0 0 0 9 17 2 0 0 0 0 10 21 1 0 0 0 0 11 14 1 0 0 0 0 11 18 2 0 0 0 0 12 13 2 0 0 0 0 12 20 1 0 0 0 0 13 31 1 0 0 0 0 14 33 1 0 0 0 0 15 22 1 0 0 0 0 16 19 1 0 0 0 0 16 23 1 0 0 0 0 18 30 1 0 0 0 0 19 15 1 1 0 0 0 19 29 1 0 0 0 0 20 25 2 0 0 0 0 20 27 1 0 0 0 0 21 27 2 0 0 0 0 21 28 1 0 0 0 0 22 26 1 0 0 0 0 22 34 1 0 0 0 0 23 32 1 0 0 0 0 23 34 1 1 0 0 0 24 25 1 0 0 0 0 24 26 1 0 0 0 0 24 28 2 0 0 0 0 25 35 1 0 0 0 0 26 36 2 0 0 0 0 27 40 1 0 0 0 0 28 41 1 0 0 0 0 29 33 1 0 0 0 0 29 37 2 0 0 0 0 30 38 2 0 0 0 0 30 39 1 0 0 0 0 31 40 1 0 0 0 0 32 42 1 0 0 0 0 33 34 1 1 0 0 0 33 42 1 0 0 0 0 34 41 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	576.27
Volume:	591.875
LogP:	7.069
LogD:	4.418
LogS:	-3.692
# Rotatable Bonds:	6
TPSA:	108.36
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.271
Synthetic Accessibility Score:	6.61
Fsp3:	0.559
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.728
MDCK Permeability:	1.8425953385303728e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.261
20% Bioavailability (F20%):	0.894
30% Bioavailability (F30%):	0.933

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.352
Plasma Protein Binding (PPB):	95.30217742919922%
Volume Distribution (VD):	1.795
Pgp-substrate:	5.710737228393555%

ADMET: Metabolism

CYP1A2-inhibitor:	0.119
CYP1A2-substrate:	0.533
CYP2C19-inhibitor:	0.699
CYP2C19-substrate:	0.8
CYP2C9-inhibitor:	0.894
CYP2C9-substrate:	0.384
CYP2D6-inhibitor:	0.632
CYP2D6-substrate:	0.117
CYP3A4-inhibitor:	0.93
CYP3A4-substrate:	0.763

ADMET: Excretion

Clearance (CL):	6.407
Half-life (T1/2):	0.02

ADMET: Toxicity

hERG Blockers:	0.181
Human Hepatotoxicity (H-HT):	0.964
Drug-inuced Liver Injury (DILI):	0.684
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.97
Maximum Recommended Daily Dose:	0.925
Skin Sensitization:	0.189
Carcinogencity:	0.903
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC476196

Natural Product ID:	NPC476196
*Common Name:**	JTEQWNATEJGXHW-VCNFGNKZSA-N
IUPAC Name:	n.a.
Synonyms:	Methyl 8,8A-Dihydromorellate
Standard InCHIKey:	JTEQWNATEJGXHW-VCNFGNKZSA-N
Standard InCHI:	InChI=1S/C34H40O8/c1-17(2)9-10-21-27-20(12-13-31(4,5)40-27)25(35)24-26(36)22-15-19-16-23-32(6,7)42-33(29(19)37,34(22,23)41-28(21)24)14-11-18(3)30(38)39-8/h9,11-13,19,22-23,35H,10,14-16H2,1-8H3/b18-11-/t19-,22?,23+,33+,34-/m1/s1
SMILES:	COC(=O)/C(=CC[C@]12OC([C@H]3[C@]42Oc2c(CC=C(C)C)c5OC(C)(C)C=Cc5c(c2C(=O)C4C[C@@H](C1=O)C3)O)(C)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL552883
PubChem CID:	45268013
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones [CHEMONTID:0003521] Pyranoxanthones

*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
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	latex	n.a.	PMID[17117343]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[17117343]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	resin	n.a.	n.a.	PMID[19072548]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21486005]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	111000.0	nM	PMID[493011]

☑ 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 NPC476196 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	403
0.1-0.2	1573
0.2-0.3	3214
0.3-0.4	6626
0.4-0.5	10526
0.5-0.6	6933
0.6-0.7	5784
0.7-0.8	7356
0.8-0.85	215
0.85-0.9	29
0.9-0.95	31
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9812	High Similarity	NPC476146
0.9812	High Similarity	NPC158329
0.9812	High Similarity	NPC40089
0.9753	High Similarity	NPC476152
0.9695	High Similarity	NPC476210
0.9695	High Similarity	NPC476199
0.9689	High Similarity	NPC75141
0.9689	High Similarity	NPC47634
0.9689	High Similarity	NPC55422
0.9689	High Similarity	NPC41598
0.9632	High Similarity	NPC476229
0.9568	High Similarity	NPC476216
0.9568	High Similarity	NPC63514
0.9512	High Similarity	NPC476311
0.9512	High Similarity	NPC476139
0.9503	High Similarity	NPC189689
0.9448	High Similarity	NPC102810
0.9441	High Similarity	NPC131578
0.9387	High Similarity	NPC223413
0.9337	High Similarity	NPC162248
0.9333	High Similarity	NPC476159
0.9286	High Similarity	NPC473729
0.9255	High Similarity	NPC286422
0.9172	High Similarity	NPC473607
0.9167	High Similarity	NPC227275
0.9112	High Similarity	NPC233978
0.9091	High Similarity	NPC476255
0.9036	High Similarity	NPC193222
0.9024	High Similarity	NPC94796
0.8988	High Similarity	NPC118128
0.8976	High Similarity	NPC476056
0.8976	High Similarity	NPC62444
0.8902	High Similarity	NPC475107
0.8902	High Similarity	NPC43490
0.8896	High Similarity	NPC476930
0.8882	High Similarity	NPC475398
0.8876	High Similarity	NPC169018
0.8855	High Similarity	NPC476931
0.883	High Similarity	NPC98943
0.882	High Similarity	NPC476162
0.8765	High Similarity	NPC477529
0.8735	High Similarity	NPC476929
0.8713	High Similarity	NPC17105
0.8713	High Similarity	NPC474276
0.8713	High Similarity	NPC147363
0.8713	High Similarity	NPC475080
0.8713	High Similarity	NPC73899
0.8706	High Similarity	NPC193698
0.869	High Similarity	NPC473908
0.8683	High Similarity	NPC475106
0.8623	High Similarity	NPC61382
0.8623	High Similarity	NPC103816
0.8614	High Similarity	NPC125969
0.8605	High Similarity	NPC469393
0.8588	High Similarity	NPC292233
0.858	High Similarity	NPC106700
0.8571	High Similarity	NPC208069
0.8563	High Similarity	NPC172687
0.8563	High Similarity	NPC243701
0.8555	High Similarity	NPC294149
0.8545	High Similarity	NPC469934
0.8538	High Similarity	NPC286074
0.8538	High Similarity	NPC54903
0.8529	High Similarity	NPC85047
0.8529	High Similarity	NPC17274
0.8529	High Similarity	NPC120857
0.8529	High Similarity	NPC323137
0.8523	High Similarity	NPC475656
0.8523	High Similarity	NPC475148
0.8512	High Similarity	NPC92589
0.8506	High Similarity	NPC469345
0.8503	High Similarity	NPC264932
0.8503	High Similarity	NPC311574
0.8492	Intermediate Similarity	NPC295436
0.8483	Intermediate Similarity	NPC294863
0.8483	Intermediate Similarity	NPC174486
0.8483	Intermediate Similarity	NPC282636
0.848	Intermediate Similarity	NPC472622
0.848	Intermediate Similarity	NPC76647
0.8452	Intermediate Similarity	NPC121647
0.8448	Intermediate Similarity	NPC232412
0.8448	Intermediate Similarity	NPC86809
0.8448	Intermediate Similarity	NPC98667
0.8443	Intermediate Similarity	NPC323627
0.8443	Intermediate Similarity	NPC318527
0.8443	Intermediate Similarity	NPC322459
0.8443	Intermediate Similarity	NPC161650
0.8443	Intermediate Similarity	NPC210048
0.8443	Intermediate Similarity	NPC324358
0.8439	Intermediate Similarity	NPC472620
0.8434	Intermediate Similarity	NPC476169
0.843	Intermediate Similarity	NPC217378
0.843	Intermediate Similarity	NPC472619
0.843	Intermediate Similarity	NPC20734
0.843	Intermediate Similarity	NPC291795
0.843	Intermediate Similarity	NPC207574
0.843	Intermediate Similarity	NPC297195
0.8421	Intermediate Similarity	NPC469394
0.8421	Intermediate Similarity	NPC475109
0.8421	Intermediate Similarity	NPC82330
0.8421	Intermediate Similarity	NPC472621
0.8415	Intermediate Similarity	NPC476509
0.8415	Intermediate Similarity	NPC321387
0.8415	Intermediate Similarity	NPC327059
0.8412	Intermediate Similarity	NPC469395
0.8412	Intermediate Similarity	NPC473009
0.8409	Intermediate Similarity	NPC244903
0.8407	Intermediate Similarity	NPC470194
0.8407	Intermediate Similarity	NPC470200
0.8407	Intermediate Similarity	NPC470193
0.8407	Intermediate Similarity	NPC316274
0.8407	Intermediate Similarity	NPC470196
0.8407	Intermediate Similarity	NPC470195
0.8407	Intermediate Similarity	NPC470197
0.8407	Intermediate Similarity	NPC282474
0.8407	Intermediate Similarity	NPC470198
0.8405	Intermediate Similarity	NPC211811
0.8402	Intermediate Similarity	NPC472346
0.8402	Intermediate Similarity	NPC97812
0.84	Intermediate Similarity	NPC312630
0.84	Intermediate Similarity	NPC324220
0.8393	Intermediate Similarity	NPC474373
0.8383	Intermediate Similarity	NPC56049
0.8383	Intermediate Similarity	NPC192587
0.8383	Intermediate Similarity	NPC469936
0.8383	Intermediate Similarity	NPC474738
0.8383	Intermediate Similarity	NPC78554
0.8383	Intermediate Similarity	NPC54830
0.8383	Intermediate Similarity	NPC321372
0.8383	Intermediate Similarity	NPC475797
0.8383	Intermediate Similarity	NPC474609
0.8383	Intermediate Similarity	NPC129053
0.8383	Intermediate Similarity	NPC109967
0.8382	Intermediate Similarity	NPC251144
0.8382	Intermediate Similarity	NPC241387
0.8373	Intermediate Similarity	NPC311579
0.8373	Intermediate Similarity	NPC477669
0.8373	Intermediate Similarity	NPC236756
0.8373	Intermediate Similarity	NPC100134
0.8373	Intermediate Similarity	NPC209760
0.8372	Intermediate Similarity	NPC150131
0.8364	Intermediate Similarity	NPC305965
0.8363	Intermediate Similarity	NPC204088
0.8363	Intermediate Similarity	NPC329215
0.8363	Intermediate Similarity	NPC473010
0.8363	Intermediate Similarity	NPC259007
0.8354	Intermediate Similarity	NPC104236
0.8354	Intermediate Similarity	NPC469932
0.8354	Intermediate Similarity	NPC164205
0.8353	Intermediate Similarity	NPC473012
0.8353	Intermediate Similarity	NPC473022
0.8353	Intermediate Similarity	NPC219861
0.8352	Intermediate Similarity	NPC207467
0.8344	Intermediate Similarity	NPC474108
0.8344	Intermediate Similarity	NPC177995
0.8344	Intermediate Similarity	NPC140120
0.8343	Intermediate Similarity	NPC472055
0.8343	Intermediate Similarity	NPC195136
0.8333	Intermediate Similarity	NPC206212
0.8333	Intermediate Similarity	NPC201127
0.8333	Intermediate Similarity	NPC469953
0.8333	Intermediate Similarity	NPC473113
0.8333	Intermediate Similarity	NPC263483
0.8333	Intermediate Similarity	NPC71184
0.8323	Intermediate Similarity	NPC275575
0.8323	Intermediate Similarity	NPC108937
0.8323	Intermediate Similarity	NPC279218
0.8315	Intermediate Similarity	NPC313452
0.8315	Intermediate Similarity	NPC182693
0.8314	Intermediate Similarity	NPC13481
0.8314	Intermediate Similarity	NPC207575
0.8314	Intermediate Similarity	NPC125465
0.8313	Intermediate Similarity	NPC210597
0.8313	Intermediate Similarity	NPC469818
0.8313	Intermediate Similarity	NPC477957
0.8313	Intermediate Similarity	NPC142527
0.8313	Intermediate Similarity	NPC288534
0.8305	Intermediate Similarity	NPC473785
0.8305	Intermediate Similarity	NPC121888
0.8304	Intermediate Similarity	NPC12461
0.8304	Intermediate Similarity	NPC472581
0.8303	Intermediate Similarity	NPC29777
0.8303	Intermediate Similarity	NPC151973
0.8303	Intermediate Similarity	NPC158866
0.8303	Intermediate Similarity	NPC470908
0.8303	Intermediate Similarity	NPC180351
0.8303	Intermediate Similarity	NPC471115
0.8297	Intermediate Similarity	NPC470199
0.8297	Intermediate Similarity	NPC314459
0.8295	Intermediate Similarity	NPC156955
0.8294	Intermediate Similarity	NPC301256
0.8294	Intermediate Similarity	NPC312273
0.8294	Intermediate Similarity	NPC175513
0.8293	Intermediate Similarity	NPC469933
0.8293	Intermediate Similarity	NPC208303
0.8293	Intermediate Similarity	NPC472345
0.8293	Intermediate Similarity	NPC296869
0.8293	Intermediate Similarity	NPC161864
0.8287	Intermediate Similarity	NPC314672
0.8284	Intermediate Similarity	NPC15815

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 NPC476196 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	356
0.1-0.2	939
0.2-0.3	1849
0.3-0.4	2674
0.4-0.5	1998
0.5-0.6	914
0.6-0.7	280
0.7-0.8	139
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
0.8554	High Similarity	NPD7075	Discontinued
0.8434	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD7819	Suspended
0.8364	Intermediate Similarity	NPD7411	Suspended
0.8363	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8218	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8208	Intermediate Similarity	NPD7473	Discontinued
0.8204	Intermediate Similarity	NPD6801	Discontinued
0.8118	Intermediate Similarity	NPD3749	Approved
0.811	Intermediate Similarity	NPD2534	Approved
0.811	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD2532	Approved
0.811	Intermediate Similarity	NPD2533	Approved
0.8077	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD3882	Suspended
0.8035	Intermediate Similarity	NPD6232	Discontinued
0.8	Intermediate Similarity	NPD3817	Phase 2
0.7976	Intermediate Similarity	NPD4380	Phase 2
0.7976	Intermediate Similarity	NPD6599	Discontinued
0.7953	Intermediate Similarity	NPD7768	Phase 2
0.7943	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD6166	Phase 2
0.7943	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD6799	Approved
0.7933	Intermediate Similarity	NPD7808	Phase 3
0.7919	Intermediate Similarity	NPD5494	Approved
0.7877	Intermediate Similarity	NPD7251	Discontinued
0.7874	Intermediate Similarity	NPD6959	Discontinued
0.7857	Intermediate Similarity	NPD8434	Phase 2
0.7849	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD6797	Phase 2
0.7821	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD3226	Approved
0.7809	Intermediate Similarity	NPD5844	Phase 1
0.7805	Intermediate Similarity	NPD2800	Approved
0.7803	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD5403	Approved
0.7791	Intermediate Similarity	NPD5402	Approved
0.776	Intermediate Similarity	NPD8150	Discontinued
0.7759	Intermediate Similarity	NPD919	Approved
0.7758	Intermediate Similarity	NPD3750	Approved
0.7753	Intermediate Similarity	NPD3818	Discontinued
0.7744	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD2801	Approved
0.7709	Intermediate Similarity	NPD7054	Approved
0.7697	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD8312	Approved
0.7692	Intermediate Similarity	NPD8313	Approved
0.768	Intermediate Similarity	NPD6559	Discontinued
0.7679	Intermediate Similarity	NPD5401	Approved
0.7674	Intermediate Similarity	NPD1934	Approved
0.767	Intermediate Similarity	NPD1247	Approved
0.7667	Intermediate Similarity	NPD7472	Approved
0.7667	Intermediate Similarity	NPD7074	Phase 3
0.7636	Intermediate Similarity	NPD1549	Phase 2
0.7633	Intermediate Similarity	NPD1512	Approved
0.7627	Intermediate Similarity	NPD5710	Approved
0.7627	Intermediate Similarity	NPD5711	Approved
0.7619	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD7435	Discontinued
0.7561	Intermediate Similarity	NPD1510	Phase 2
0.7557	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD6651	Approved
0.7545	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD1465	Phase 2
0.7515	Intermediate Similarity	NPD1511	Approved
0.7515	Intermediate Similarity	NPD2796	Approved
0.7487	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD3926	Phase 2
0.7486	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1243	Approved
0.7485	Intermediate Similarity	NPD920	Approved
0.747	Intermediate Similarity	NPD2346	Discontinued
0.7459	Intermediate Similarity	NPD3751	Discontinued
0.7455	Intermediate Similarity	NPD3748	Approved
0.7455	Intermediate Similarity	NPD2799	Discontinued
0.7439	Intermediate Similarity	NPD1607	Approved
0.7424	Intermediate Similarity	NPD7874	Approved
0.7424	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD1240	Approved
0.741	Intermediate Similarity	NPD6100	Approved
0.741	Intermediate Similarity	NPD6099	Approved
0.7399	Intermediate Similarity	NPD7458	Discontinued
0.7385	Intermediate Similarity	NPD7698	Approved
0.7385	Intermediate Similarity	NPD7697	Approved
0.7385	Intermediate Similarity	NPD7696	Phase 3
0.7384	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD5124	Phase 1
0.7378	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD8151	Discontinued
0.7368	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD7228	Approved
0.7358	Intermediate Similarity	NPD8285	Discontinued
0.7353	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD2403	Approved
0.7347	Intermediate Similarity	NPD8319	Approved
0.7347	Intermediate Similarity	NPD7871	Phase 2
0.7347	Intermediate Similarity	NPD7870	Phase 2
0.7347	Intermediate Similarity	NPD8320	Phase 1
0.7337	Intermediate Similarity	NPD5953	Discontinued
0.7333	Intermediate Similarity	NPD3787	Discontinued
0.732	Intermediate Similarity	NPD6776	Approved
0.732	Intermediate Similarity	NPD6779	Approved
0.732	Intermediate Similarity	NPD6781	Approved
0.732	Intermediate Similarity	NPD6780	Approved
0.732	Intermediate Similarity	NPD6778	Approved
0.732	Intermediate Similarity	NPD6782	Approved
0.732	Intermediate Similarity	NPD6777	Approved
0.732	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD2935	Discontinued
0.7305	Intermediate Similarity	NPD1551	Phase 2
0.7302	Intermediate Similarity	NPD4287	Approved
0.7301	Intermediate Similarity	NPD2313	Discontinued
0.7278	Intermediate Similarity	NPD7199	Phase 2
0.7273	Intermediate Similarity	NPD37	Approved
0.7263	Intermediate Similarity	NPD6234	Discontinued
0.7262	Intermediate Similarity	NPD1471	Phase 3
0.7258	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD4967	Phase 2
0.7247	Intermediate Similarity	NPD4966	Approved
0.7247	Intermediate Similarity	NPD4965	Approved
0.7246	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7229	Phase 3
0.7236	Intermediate Similarity	NPD7701	Phase 2
0.7235	Intermediate Similarity	NPD4628	Phase 3
0.7235	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7286	Phase 2
0.7216	Intermediate Similarity	NPD7699	Phase 2
0.7216	Intermediate Similarity	NPD7700	Phase 2
0.7214	Intermediate Similarity	NPD7783	Phase 2
0.7214	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD7801	Approved
0.7209	Intermediate Similarity	NPD7390	Discontinued
0.72	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD3268	Approved
0.7195	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2344	Approved
0.7158	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD6535	Approved
0.715	Intermediate Similarity	NPD8366	Approved
0.715	Intermediate Similarity	NPD6534	Approved
0.7135	Intermediate Similarity	NPD7003	Approved
0.7112	Intermediate Similarity	NPD7685	Pre-registration
0.7101	Intermediate Similarity	NPD5408	Approved
0.7101	Intermediate Similarity	NPD5405	Approved
0.7101	Intermediate Similarity	NPD5404	Approved
0.7101	Intermediate Similarity	NPD5406	Approved
0.7091	Intermediate Similarity	NPD3764	Approved
0.7091	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD8127	Discontinued
0.7067	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6355	Discontinued
0.7039	Intermediate Similarity	NPD8455	Phase 2
0.7039	Intermediate Similarity	NPD5760	Phase 2
0.7039	Intermediate Similarity	NPD5761	Phase 2
0.7021	Intermediate Similarity	NPD7240	Approved
0.7014	Intermediate Similarity	NPD8491	Approved
0.7011	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4060	Phase 1
0.6994	Remote Similarity	NPD6190	Approved
0.6994	Remote Similarity	NPD2309	Approved
0.6989	Remote Similarity	NPD7799	Discontinued
0.6985	Remote Similarity	NPD6823	Phase 2
0.6981	Remote Similarity	NPD8469	Approved
0.697	Remote Similarity	NPD4908	Phase 1
0.697	Remote Similarity	NPD6832	Phase 2
0.6966	Remote Similarity	NPD6585	Discontinued
0.6964	Remote Similarity	NPD447	Suspended
0.6959	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD7033	Discontinued
0.6941	Remote Similarity	NPD4308	Phase 3
0.6936	Remote Similarity	NPD8166	Discontinued
0.6932	Remote Similarity	NPD5049	Phase 3
0.6932	Remote Similarity	NPD6273	Approved
0.6931	Remote Similarity	NPD6765	Approved
0.6931	Remote Similarity	NPD6764	Approved
0.6931	Remote Similarity	NPD7584	Approved
0.6927	Remote Similarity	NPD5889	Approved
0.6927	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5890	Approved
0.6906	Remote Similarity	NPD4288	Approved
0.6905	Remote Similarity	NPD943	Approved
0.689	Remote Similarity	NPD3267	Approved
0.689	Remote Similarity	NPD3266	Approved
0.689	Remote Similarity	NPD2797	Approved
0.689	Remote Similarity	NPD1203	Approved
0.6888	Remote Similarity	NPD4360	Phase 2
0.6888	Remote Similarity	NPD4363	Phase 3
0.6886	Remote Similarity	NPD6798	Discontinued
0.6882	Remote Similarity	NPD7097	Phase 1
0.6864	Remote Similarity	NPD1933	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