NPASS Compound

Structure

NPC473632 OpenBabel07101718272D 42 47 0 0 1 0 0 0 0 0999 V2000 -4.1397 -1.8796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7292 -2.9545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1816 -2.5292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5209 -2.1636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7770 -1.1286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4900 0.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4900 -5.2712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4900 -4.3128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6600 -5.7504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6600 -3.8336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8300 -5.2712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8300 1.4376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8593 -2.8543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9584 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2022 -2.0789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2500 -3.7845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4296 -1.6034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8300 -4.3128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8124 -2.9545 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6600 0.9584 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.9584 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4900 -1.4376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8300 -0.4792 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8300 -1.4376 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -3.8336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7841 -0.2614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1184 -1.4143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6600 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6600 -1.9168 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4900 -0.4792 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7292 -4.6145 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3554 -1.3554 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4900 1.4376 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8300 -4.3128 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6412 0.6863 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4348 -0.3184 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9584 0.9584 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2916 -3.7845 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9168 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2481 -0.9257 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1737 -0.6776 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 6 28 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 2 0 0 0 0 10 18 2 0 0 0 0 11 18 1 0 0 0 0 12 20 1 0 0 0 0 12 21 1 0 0 0 0 13 19 1 0 0 0 0 14 30 1 0 0 0 0 14 38 1 0 0 0 0 15 19 1 0 0 0 0 15 22 2 0 0 0 0 16 32 2 0 0 0 0 16 39 1 0 0 0 0 17 33 2 0 0 0 0 17 41 1 0 0 0 0 18 25 1 0 0 0 0 19 39 1 6 0 0 0 20 28 1 1 0 0 0 20 34 1 0 0 0 0 21 30 1 1 0 0 0 21 38 1 0 0 0 0 22 29 1 0 0 0 0 22 31 1 0 0 0 0 23 24 1 0 0 0 0 23 28 1 1 0 0 0 23 30 1 0 0 0 0 24 29 1 6 0 0 0 24 40 1 0 0 0 0 25 35 2 0 0 0 0 25 40 1 0 0 0 0 26 31 1 0 0 0 0 26 36 2 0 0 0 0 26 42 1 0 0 0 0 27 29 1 0 0 0 0 27 42 1 0 0 0 0 28 31 1 6 0 0 0 29 13 1 1 0 0 0 30 41 1 6 0 0 0 31 37 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	584.23
Volume:	568.994
LogP:	2.928
LogD:	2.465
LogS:	-4.059
# Rotatable Bonds:	7
TPSA:	154.89
# H-Bond Aceptor:	11
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.303
Synthetic Accessibility Score:	5.777
Fsp3:	0.613
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:	-5.463
MDCK Permeability:	8.76203557709232e-05
Pgp-inhibitor:	0.95
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.323
20% Bioavailability (F20%):	0.989
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.59
Plasma Protein Binding (PPB):	58.255859375%
Volume Distribution (VD):	1.69
Pgp-substrate:	25.944101333618164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.074
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.578
CYP2C9-inhibitor:	0.028
CYP2C9-substrate:	0.014
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.057
CYP3A4-inhibitor:	0.289
CYP3A4-substrate:	0.759

ADMET: Excretion

Clearance (CL):	4.627
Half-life (T1/2):	0.048

ADMET: Toxicity

hERG Blockers:	0.119
Human Hepatotoxicity (H-HT):	0.936
Drug-inuced Liver Injury (DILI):	0.954
AMES Toxicity:	0.788
Rat Oral Acute Toxicity:	0.869
Maximum Recommended Daily Dose:	0.93
Skin Sensitization:	0.494
Carcinogencity:	0.474
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC473632

Natural Product ID:	NPC473632
*Common Name:**	KIAGJENBRDLBMJ-BEZTUGLTSA-N
IUPAC Name:	n.a.
Synonyms:	13-O-Acetyl Wallifoliol
Standard InCHIKey:	KIAGJENBRDLBMJ-BEZTUGLTSA-N
Standard InCHI:	InChI=1S/C31H36O11/c1-15-19(39-16(2)32)13-29-22(15)31(37,26(36)42-27(29,4)5)28(6)20(34)12-21-30(14-38-21,41-17(3)33)23(28)24(29)40-25(35)18-10-8-7-9-11-18/h7-11,19-21,23-24,34,37H,12-14H2,1-6H3/t19-,20-,21+,23-,24-,28+,29-,30-,31+/m0/s1
SMILES:	CC(=O)O[C@H]1C[C@]23C(=C1C)[C@@](O)(C(=O)OC3(C)C)[C@]1([C@H]([C@@H]2OC(=O)c2ccccc2)[C@@]2(CO[C@@H]2C[C@@H]1O)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL447667
PubChem CID:	21603521
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002966] Tetracarboxylic acids and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/j.tet.2004.10.110]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	twig	n.a.	DOI[10.1016/j.tet.2004.10.110]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	leaves and twigs	n.a.	n.a.	PMID[12502326]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	twig	n.a.	PMID[15679325]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15679325]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679325]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18220355]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11554	Taxus sumatrana	Species	Taxaceae	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	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	2.91	ug.mL-1	PMID[520383]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	13.92	ug.mL-1	PMID[520383]

☑ 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 NPC473632 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	347
0.1-0.2	1174
0.2-0.3	2565
0.3-0.4	5004
0.4-0.5	9645
0.5-0.6	11473
0.6-0.7	10338
0.7-0.8	1751
0.8-0.85	174
0.85-0.9	190
0.9-0.95	31
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469730
1.0	High Similarity	NPC132599
0.9862	High Similarity	NPC473611
0.9533	High Similarity	NPC476077
0.9178	High Similarity	NPC92867
0.9178	High Similarity	NPC311825
0.9133	High Similarity	NPC134685
0.9133	High Similarity	NPC248265
0.9133	High Similarity	NPC11588
0.9133	High Similarity	NPC229545
0.9128	High Similarity	NPC471103
0.9122	High Similarity	NPC60509
0.9122	High Similarity	NPC81698
0.9122	High Similarity	NPC250046
0.9116	High Similarity	NPC20255
0.9073	High Similarity	NPC114357
0.9073	High Similarity	NPC155329
0.9073	High Similarity	NPC259144
0.9073	High Similarity	NPC472549
0.906	High Similarity	NPC198455
0.906	High Similarity	NPC165260
0.906	High Similarity	NPC7095
0.906	High Similarity	NPC161239
0.9054	High Similarity	NPC473760
0.9048	High Similarity	NPC125882
0.9048	High Similarity	NPC127857
0.9041	High Similarity	NPC477894
0.9034	High Similarity	NPC97947
0.9034	High Similarity	NPC291599
0.9034	High Similarity	NPC118080
0.9034	High Similarity	NPC27377
0.9034	High Similarity	NPC87448
0.9034	High Similarity	NPC472576
0.9034	High Similarity	NPC41481
0.9013	High Similarity	NPC106895
0.9007	High Similarity	NPC219419
0.9	High Similarity	NPC197037
0.9	High Similarity	NPC51602
0.9	High Similarity	NPC470153
0.8993	High Similarity	NPC476975
0.8986	High Similarity	NPC209592
0.8986	High Similarity	NPC48599
0.898	High Similarity	NPC241951
0.898	High Similarity	NPC34943
0.898	High Similarity	NPC470152
0.898	High Similarity	NPC38696
0.898	High Similarity	NPC475759
0.8974	High Similarity	NPC471134
0.8973	High Similarity	NPC182869
0.8966	High Similarity	NPC90614
0.8966	High Similarity	NPC100913
0.8966	High Similarity	NPC275592
0.8966	High Similarity	NPC97667
0.8966	High Similarity	NPC171207
0.8947	High Similarity	NPC26033
0.8947	High Similarity	NPC282239
0.8947	High Similarity	NPC473670
0.8947	High Similarity	NPC21410
0.8947	High Similarity	NPC228204
0.894	High Similarity	NPC472548
0.894	High Similarity	NPC477905
0.8933	High Similarity	NPC470245
0.8933	High Similarity	NPC91730
0.8933	High Similarity	NPC31829
0.8933	High Similarity	NPC112216
0.8933	High Similarity	NPC473214
0.8919	High Similarity	NPC476973
0.8919	High Similarity	NPC472571
0.8919	High Similarity	NPC177940
0.8919	High Similarity	NPC472572
0.8919	High Similarity	NPC200471
0.8919	High Similarity	NPC472575
0.8919	High Similarity	NPC70403
0.8919	High Similarity	NPC470159
0.8919	High Similarity	NPC174982
0.8919	High Similarity	NPC184817
0.8919	High Similarity	NPC29704
0.8919	High Similarity	NPC472556
0.8919	High Similarity	NPC96903
0.8919	High Similarity	NPC471104
0.8919	High Similarity	NPC472568
0.8919	High Similarity	NPC158663
0.8919	High Similarity	NPC470157
0.8919	High Similarity	NPC469349
0.8919	High Similarity	NPC473088
0.8919	High Similarity	NPC171525
0.8912	High Similarity	NPC163087
0.8904	High Similarity	NPC16912
0.8896	High Similarity	NPC469399
0.8882	High Similarity	NPC473414
0.8882	High Similarity	NPC237549
0.8882	High Similarity	NPC249471
0.8882	High Similarity	NPC256142
0.8882	High Similarity	NPC158333
0.8882	High Similarity	NPC265395
0.8882	High Similarity	NPC472005
0.8882	High Similarity	NPC242262
0.8882	High Similarity	NPC472030
0.8882	High Similarity	NPC472022
0.8882	High Similarity	NPC304876
0.8882	High Similarity	NPC257213
0.8882	High Similarity	NPC1173
0.8874	High Similarity	NPC101043
0.8874	High Similarity	NPC306799
0.8867	High Similarity	NPC473215
0.8859	High Similarity	NPC473602
0.8859	High Similarity	NPC240115
0.8854	High Similarity	NPC471493
0.8851	High Similarity	NPC188865
0.8851	High Similarity	NPC95265
0.8851	High Similarity	NPC475122
0.8851	High Similarity	NPC163719
0.8851	High Similarity	NPC472570
0.8851	High Similarity	NPC95810
0.8851	High Similarity	NPC11685
0.8851	High Similarity	NPC70716
0.8851	High Similarity	NPC125106
0.8851	High Similarity	NPC472573
0.8851	High Similarity	NPC472569
0.8851	High Similarity	NPC57628
0.8851	High Similarity	NPC25768
0.8851	High Similarity	NPC476974
0.8844	High Similarity	NPC192658
0.8836	High Similarity	NPC472547
0.8831	High Similarity	NPC472393
0.8824	High Similarity	NPC114410
0.8824	High Similarity	NPC112523
0.8819	High Similarity	NPC477893
0.8819	High Similarity	NPC477896
0.8816	High Similarity	NPC469647
0.8816	High Similarity	NPC138641
0.8816	High Similarity	NPC283875
0.8816	High Similarity	NPC469648
0.8816	High Similarity	NPC22571
0.88	High Similarity	NPC217918
0.8792	High Similarity	NPC471107
0.8792	High Similarity	NPC471100
0.8784	High Similarity	NPC91703
0.8784	High Similarity	NPC95449
0.8774	High Similarity	NPC471102
0.8767	High Similarity	NPC9905
0.8766	High Similarity	NPC217091
0.8766	High Similarity	NPC11410
0.8758	High Similarity	NPC133430
0.8758	High Similarity	NPC469477
0.8758	High Similarity	NPC77719
0.8742	High Similarity	NPC471101
0.8742	High Similarity	NPC270590
0.8742	High Similarity	NPC266265
0.8742	High Similarity	NPC92293
0.8742	High Similarity	NPC301556
0.8742	High Similarity	NPC161151
0.8733	High Similarity	NPC474935
0.8733	High Similarity	NPC478263
0.8716	High Similarity	NPC472546
0.8716	High Similarity	NPC34012
0.871	High Similarity	NPC469771
0.871	High Similarity	NPC469417
0.8707	High Similarity	NPC87934
0.8707	High Similarity	NPC162613
0.8701	High Similarity	NPC34066
0.8701	High Similarity	NPC251139
0.8699	High Similarity	NPC39549
0.8693	High Similarity	NPC233581
0.8693	High Similarity	NPC145649
0.869	High Similarity	NPC195647
0.869	High Similarity	NPC66761
0.869	High Similarity	NPC17877
0.869	High Similarity	NPC291638
0.869	High Similarity	NPC472577
0.8684	High Similarity	NPC476173
0.8684	High Similarity	NPC469448
0.8684	High Similarity	NPC254558
0.8679	High Similarity	NPC477491
0.8675	High Similarity	NPC327031
0.8675	High Similarity	NPC281717
0.8671	High Similarity	NPC66193
0.8667	High Similarity	NPC478264
0.8649	High Similarity	NPC266374
0.8649	High Similarity	NPC224491
0.8645	High Similarity	NPC70344
0.863	High Similarity	NPC472551
0.863	High Similarity	NPC472545
0.8627	High Similarity	NPC472398
0.8621	High Similarity	NPC474608
0.8618	High Similarity	NPC76103
0.8609	High Similarity	NPC312393
0.86	High Similarity	NPC470231
0.8581	High Similarity	NPC184747
0.8581	High Similarity	NPC476094
0.8581	High Similarity	NPC5115
0.8581	High Similarity	NPC4341
0.8581	High Similarity	NPC473085
0.8581	High Similarity	NPC477904
0.8581	High Similarity	NPC48017
0.8581	High Similarity	NPC473060
0.8581	High Similarity	NPC200592
0.8581	High Similarity	NPC147880
0.8581	High Similarity	NPC43241
0.8581	High Similarity	NPC473613

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 NPC473632 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	289
0.1-0.2	751
0.2-0.3	1643
0.3-0.4	2915
0.4-0.5	2233
0.5-0.6	1014
0.6-0.7	271
0.7-0.8	34
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8421	Intermediate Similarity	NPD7236	Approved
0.8269	Intermediate Similarity	NPD7239	Suspended
0.8084	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD8368	Discontinued
0.8035	Intermediate Similarity	NPD8361	Approved
0.8035	Intermediate Similarity	NPD8360	Approved
0.8024	Intermediate Similarity	NPD7799	Discontinued
0.8023	Intermediate Similarity	NPD8434	Phase 2
0.8012	Intermediate Similarity	NPD8407	Phase 2
0.7931	Intermediate Similarity	NPD8435	Approved
0.7816	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD7058	Phase 2
0.7805	Intermediate Similarity	NPD7057	Phase 3
0.7765	Intermediate Similarity	NPD8485	Approved
0.7759	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD8150	Discontinued
0.7547	Intermediate Similarity	NPD6190	Approved
0.75	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD4628	Phase 3
0.7361	Intermediate Similarity	NPD2629	Approved
0.7356	Intermediate Similarity	NPD5844	Phase 1
0.7303	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD7961	Discontinued
0.7278	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7075	Discontinued
0.7232	Intermediate Similarity	NPD7685	Pre-registration
0.7209	Intermediate Similarity	NPD8127	Discontinued
0.7192	Intermediate Similarity	NPD4198	Discontinued
0.7162	Intermediate Similarity	NPD7741	Discontinued
0.7161	Intermediate Similarity	NPD7008	Discontinued
0.716	Intermediate Similarity	NPD5761	Phase 2
0.716	Intermediate Similarity	NPD5760	Phase 2
0.716	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6273	Approved
0.7143	Intermediate Similarity	NPD7497	Discontinued
0.7091	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4380	Phase 2
0.7081	Intermediate Similarity	NPD6535	Approved
0.7081	Intermediate Similarity	NPD6534	Approved
0.7079	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7700	Phase 2
0.7059	Intermediate Similarity	NPD7699	Phase 2
0.7055	Intermediate Similarity	NPD8166	Discontinued
0.7053	Intermediate Similarity	NPD7435	Discontinued
0.7045	Intermediate Similarity	NPD7473	Discontinued
0.7039	Intermediate Similarity	NPD6764	Approved
0.7039	Intermediate Similarity	NPD6765	Approved
0.7026	Intermediate Similarity	NPD8462	Phase 1
0.7024	Intermediate Similarity	NPD7458	Discontinued
0.7018	Intermediate Similarity	NPD5402	Approved
0.7016	Intermediate Similarity	NPD8320	Phase 1
0.7016	Intermediate Similarity	NPD8319	Approved
0.7006	Intermediate Similarity	NPD3764	Approved
0.7006	Intermediate Similarity	NPD7228	Approved
0.7	Intermediate Similarity	NPD37	Approved
0.7	Intermediate Similarity	NPD6801	Discontinued
0.6989	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6166	Phase 2
0.6982	Remote Similarity	NPD6599	Discontinued
0.6977	Remote Similarity	NPD4965	Approved
0.6977	Remote Similarity	NPD4967	Phase 2
0.6977	Remote Similarity	NPD4966	Approved
0.6971	Remote Similarity	NPD6232	Discontinued
0.697	Remote Similarity	NPD8404	Phase 2
0.6961	Remote Similarity	NPD8312	Approved
0.6961	Remote Similarity	NPD8313	Approved
0.6959	Remote Similarity	NPD7819	Suspended
0.691	Remote Similarity	NPD3751	Discontinued
0.6906	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6234	Discontinued
0.6895	Remote Similarity	NPD6779	Approved
0.6895	Remote Similarity	NPD6781	Approved
0.6895	Remote Similarity	NPD6780	Approved
0.6895	Remote Similarity	NPD6778	Approved
0.6895	Remote Similarity	NPD6782	Approved
0.6895	Remote Similarity	NPD6777	Approved
0.6895	Remote Similarity	NPD6776	Approved
0.6892	Remote Similarity	NPD5951	Approved
0.6885	Remote Similarity	NPD6784	Approved
0.6885	Remote Similarity	NPD6785	Approved
0.6875	Remote Similarity	NPD230	Phase 1
0.6872	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5494	Approved
0.6855	Remote Similarity	NPD6663	Approved
0.6849	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5125	Phase 3
0.6842	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5126	Approved
0.6842	Remote Similarity	NPD7411	Suspended
0.6839	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7874	Approved
0.6824	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD3817	Phase 2
0.6821	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD5736	Approved
0.6807	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD5403	Approved
0.6797	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7696	Phase 3
0.6788	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7698	Approved
0.6788	Remote Similarity	NPD7697	Approved
0.6786	Remote Similarity	NPD2532	Approved
0.6786	Remote Similarity	NPD2534	Approved
0.6786	Remote Similarity	NPD2533	Approved
0.678	Remote Similarity	NPD3787	Discontinued
0.6779	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5762	Approved
0.6768	Remote Similarity	NPD5763	Approved
0.6768	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7266	Discontinued
0.6763	Remote Similarity	NPD1465	Phase 2
0.6763	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD7240	Approved
0.6758	Remote Similarity	NPD7251	Discontinued
0.6757	Remote Similarity	NPD7094	Approved
0.6757	Remote Similarity	NPD6858	Approved
0.6753	Remote Similarity	NPD7871	Phase 2
0.6753	Remote Similarity	NPD7870	Phase 2
0.6748	Remote Similarity	NPD7305	Phase 1
0.6747	Remote Similarity	NPD7003	Approved
0.6742	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.674	Remote Similarity	NPD7074	Phase 3
0.6735	Remote Similarity	NPD7701	Phase 2
0.6732	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6799	Approved
0.6725	Remote Similarity	NPD3226	Approved
0.6723	Remote Similarity	NPD7199	Phase 2
0.6722	Remote Similarity	NPD3818	Discontinued
0.6721	Remote Similarity	NPD7808	Phase 3
0.6717	Remote Similarity	NPD7801	Approved
0.6712	Remote Similarity	NPD2182	Approved
0.6712	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD1934	Approved
0.6703	Remote Similarity	NPD6797	Phase 2
0.6686	Remote Similarity	NPD3882	Suspended
0.6686	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5401	Approved
0.6685	Remote Similarity	NPD7054	Approved
0.6667	Remote Similarity	NPD6355	Discontinued
0.6667	Remote Similarity	NPD8455	Phase 2
0.6667	Remote Similarity	NPD6559	Discontinued
0.6648	Remote Similarity	NPD7472	Approved
0.6648	Remote Similarity	NPD3749	Approved
0.6645	Remote Similarity	NPD7610	Discontinued
0.6629	Remote Similarity	NPD6959	Discontinued
0.6627	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6100	Approved
0.6606	Remote Similarity	NPD6099	Approved
0.6603	Remote Similarity	NPD7507	Approved
0.6601	Remote Similarity	NPD9545	Approved
0.6591	Remote Similarity	NPD7768	Phase 2
0.6588	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7097	Phase 1
0.6582	Remote Similarity	NPD7319	Approved
0.6579	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6212	Phase 3
0.6579	Remote Similarity	NPD6213	Phase 3
0.6571	Remote Similarity	NPD2801	Approved
0.6566	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD6004	Phase 3
0.6566	Remote Similarity	NPD2346	Discontinued
0.6566	Remote Similarity	NPD6002	Phase 3
0.6566	Remote Similarity	NPD6005	Phase 3
0.6566	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD6823	Phase 2
0.6554	Remote Similarity	NPD2067	Discontinued
0.6548	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD3750	Approved
0.6543	Remote Similarity	NPD7714	Approved
0.6543	Remote Similarity	NPD7715	Approved
0.6543	Remote Similarity	NPD6233	Phase 2
0.6541	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD6085	Phase 2
0.6538	Remote Similarity	NPD4807	Approved
0.6538	Remote Similarity	NPD4806	Approved
0.6533	Remote Similarity	NPD8151	Discontinued
0.6531	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7095	Approved
0.6516	Remote Similarity	NPD5306	Approved
0.6516	Remote Similarity	NPD5305	Approved
0.651	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD5406	Approved
0.6506	Remote Similarity	NPD5404	Approved
0.6506	Remote Similarity	NPD2935	Discontinued
0.6506	Remote Similarity	NPD5408	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