NPASS Compound

Structure

NPC470417 OpenBabel07101718322D 35 38 0 0 1 0 0 0 0 0999 V2000 -2.2382 -2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 -3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9792 -6.0914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2361 -5.4223 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 0.4067 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 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 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 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 -1.2601 -2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8781 -4.1622 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 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 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5909 -3.0032 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9000 -3.9543 0.0000 C 0 0 2 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 -2.1871 -5.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 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 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3872 -2.7953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2308 -4.6974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1653 -5.3212 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 5 28 1 0 0 0 0 6 28 1 0 0 0 0 8 30 1 0 0 0 0 10 11 1 0 0 0 0 10 22 2 0 0 0 0 11 23 1 0 0 0 0 12 16 1 0 0 0 0 12 20 1 0 0 0 0 13 17 1 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 14 24 1 0 0 0 0 15 29 1 0 0 0 0 16 31 1 0 0 0 0 17 30 1 0 0 0 0 18 1 1 6 0 0 0 18 20 1 0 0 0 0 18 25 1 0 0 0 0 19 2 1 1 0 0 0 19 26 1 0 0 0 0 19 28 1 0 0 0 0 20 30 1 6 0 0 0 21 22 1 0 0 0 0 21 29 1 1 0 0 0 22 31 1 0 0 0 0 23 27 1 0 0 0 0 23 29 1 1 0 0 0 24 27 1 0 0 0 0 24 32 2 0 0 0 0 25 26 1 0 0 0 0 25 33 1 1 0 0 0 26 34 1 6 0 0 0 28 35 1 0 0 0 0 29 7 1 1 0 0 0 30 31 1 6 0 0 0 31 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	488.39
Volume:	540.394
LogP:	5.54
LogD:	4.758
LogS:	-4.831
# Rotatable Bonds:	5
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.419
Synthetic Accessibility Score:	5.067
Fsp3:	0.903
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:	-4.802
MDCK Permeability:	1.1775751772802323e-05
Pgp-inhibitor:	0.967
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.619
30% Bioavailability (F30%):	0.823

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.098
Plasma Protein Binding (PPB):	93.24683380126953%
Volume Distribution (VD):	0.949
Pgp-substrate:	2.2710511684417725%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.486
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.938
CYP2C9-inhibitor:	0.106
CYP2C9-substrate:	0.4
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.055
CYP3A4-inhibitor:	0.716
CYP3A4-substrate:	0.648

ADMET: Excretion

Clearance (CL):	5.892
Half-life (T1/2):	0.243

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.277
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.569
Maximum Recommended Daily Dose:	0.634
Skin Sensitization:	0.071
Carcinogencity:	0.105
Eye Corrosion:	0.005
Eye Irritation:	0.019
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC470417

Natural Product ID:	NPC470417
*Common Name:**	Toonaciliatavarin E
IUPAC Name:	(5R,9R,10R,13S,14S,17S)-4,4,10,13,14-pentamethyl-17-[(2R,3R,4R,5S)-3,4,6-trihydroxy-5,6-dimethylheptan-2-yl]-1,2,5,6,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
Synonyms:	Toonaciliatavarin E
Standard InCHIKey:	JPEPAMACPMHGCE-ZKEHMZMFSA-N
Standard InCHI:	InChI=1S/C31H52O4/c1-18(25(33)26(34)19(2)28(5,6)35)20-12-16-31(9)22-10-11-23-27(3,4)24(32)14-15-29(23,7)21(22)13-17-30(20,31)8/h10,18-21,23,25-26,33-35H,11-17H2,1-9H3/t18-,19+,20+,21+,23+,25-,26-,29-,30+,31-/m1/s1
SMILES:	O[C@H]([C@@H]([C@@H]1CC[C@]2([C@@]1(C)CC[C@H]1C2=CC[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C)C)[C@@H]([C@@H](C(O)(C)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2035085
PubChem CID:	70696412
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0001104] Trihydroxy bile acids, alcohols 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
NPO13083	Toona ciliata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19275174]
NPO13083	Toona ciliata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537362]
NPO13083	Toona ciliata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31503490]
NPO13083	Toona ciliata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13083	Toona ciliata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13083	Toona ciliata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13083	Toona ciliata	Species	Meliaceae	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	6

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	17100.0	nM	PMID[558895]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	10200.0	nM	PMID[558895]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	19400.0	nM	PMID[558895]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	11200.0	nM	PMID[558895]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	32100.0	nM	PMID[558895]
NPT2	Others	Unspecified		IC50	=	22600	nM	PMID[20086162]

☑ 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 NPC470417 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	164
0.1-0.2	1046
0.2-0.3	4945
0.3-0.4	14522
0.4-0.5	7640
0.5-0.6	5620
0.6-0.7	5799
0.7-0.8	2593
0.8-0.85	251
0.85-0.9	97
0.9-0.95	16
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9878	High Similarity	NPC90652
0.9425	High Similarity	NPC174051
0.9425	High Similarity	NPC67831
0.9412	High Similarity	NPC32830
0.9302	High Similarity	NPC171441
0.9294	High Similarity	NPC44181
0.9286	High Similarity	NPC473168
0.9195	High Similarity	NPC262870
0.9059	High Similarity	NPC89077
0.9048	High Similarity	NPC59453
0.9048	High Similarity	NPC82902
0.9048	High Similarity	NPC85774
0.9048	High Similarity	NPC214043
0.9048	High Similarity	NPC221758
0.8966	High Similarity	NPC474245
0.8966	High Similarity	NPC1015
0.8966	High Similarity	NPC31985
0.8953	High Similarity	NPC317590
0.8941	High Similarity	NPC474218
0.8941	High Similarity	NPC471224
0.8929	High Similarity	NPC86370
0.8913	High Similarity	NPC167974
0.8864	High Similarity	NPC320026
0.8837	High Similarity	NPC474733
0.8837	High Similarity	NPC31564
0.8837	High Similarity	NPC474778
0.8837	High Similarity	NPC145879
0.8837	High Similarity	NPC474732
0.8837	High Similarity	NPC469994
0.8837	High Similarity	NPC51014
0.8824	High Similarity	NPC473246
0.881	High Similarity	NPC151519
0.881	High Similarity	NPC212083
0.8778	High Similarity	NPC473172
0.8764	High Similarity	NPC155304
0.8764	High Similarity	NPC154101
0.8764	High Similarity	NPC189520
0.875	High Similarity	NPC474704
0.875	High Similarity	NPC477943
0.875	High Similarity	NPC310010
0.875	High Similarity	NPC2983
0.875	High Similarity	NPC215029
0.875	High Similarity	NPC476733
0.875	High Similarity	NPC475921
0.875	High Similarity	NPC76879
0.875	High Similarity	NPC326627
0.8736	High Similarity	NPC58063
0.8736	High Similarity	NPC96496
0.8736	High Similarity	NPC475740
0.8736	High Similarity	NPC99909
0.8736	High Similarity	NPC138756
0.8723	High Similarity	NPC473928
0.8721	High Similarity	NPC474083
0.8721	High Similarity	NPC469948
0.8681	High Similarity	NPC473170
0.8675	High Similarity	NPC215843
0.8667	High Similarity	NPC475255
0.8667	High Similarity	NPC474736
0.8667	High Similarity	NPC474807
0.8659	High Similarity	NPC325946
0.8636	High Similarity	NPC328313
0.8636	High Similarity	NPC193360
0.8632	High Similarity	NPC117185
0.8621	High Similarity	NPC155011
0.8605	High Similarity	NPC329043
0.8605	High Similarity	NPC58841
0.8605	High Similarity	NPC237712
0.8605	High Similarity	NPC321187
0.8605	High Similarity	NPC161423
0.8605	High Similarity	NPC227064
0.8588	High Similarity	NPC145143
0.8588	High Similarity	NPC30166
0.8587	High Similarity	NPC473164
0.8587	High Similarity	NPC49371
0.8571	High Similarity	NPC472478
0.8571	High Similarity	NPC8993
0.8571	High Similarity	NPC111015
0.8556	High Similarity	NPC19114
0.8556	High Similarity	NPC473998
0.8556	High Similarity	NPC475806
0.8554	High Similarity	NPC82635
0.8542	High Similarity	NPC75531
0.8542	High Similarity	NPC100955
0.8542	High Similarity	NPC149124
0.8542	High Similarity	NPC121566
0.8539	High Similarity	NPC26959
0.8539	High Similarity	NPC309603
0.8539	High Similarity	NPC268406
0.8539	High Similarity	NPC473999
0.8539	High Similarity	NPC250592
0.8539	High Similarity	NPC186688
0.8539	High Similarity	NPC77263
0.8539	High Similarity	NPC54689
0.8523	High Similarity	NPC241875
0.8523	High Similarity	NPC469314
0.8523	High Similarity	NPC469317
0.8523	High Similarity	NPC93778
0.8523	High Similarity	NPC474684
0.8523	High Similarity	NPC142361
0.8506	High Similarity	NPC470574
0.8495	Intermediate Similarity	NPC107243
0.8495	Intermediate Similarity	NPC18509
0.8495	Intermediate Similarity	NPC57416
0.8488	Intermediate Similarity	NPC278648
0.8488	Intermediate Similarity	NPC476082
0.8471	Intermediate Similarity	NPC147066
0.8462	Intermediate Similarity	NPC66429
0.8462	Intermediate Similarity	NPC472930
0.8462	Intermediate Similarity	NPC470376
0.8462	Intermediate Similarity	NPC152897
0.8462	Intermediate Similarity	NPC472942
0.8462	Intermediate Similarity	NPC470375
0.8462	Intermediate Similarity	NPC233118
0.8462	Intermediate Similarity	NPC243866
0.8454	Intermediate Similarity	NPC95243
0.8454	Intermediate Similarity	NPC63023
0.8452	Intermediate Similarity	NPC328714
0.8444	Intermediate Similarity	NPC48010
0.8444	Intermediate Similarity	NPC289213
0.8444	Intermediate Similarity	NPC136801
0.8438	Intermediate Similarity	NPC191892
0.8427	Intermediate Similarity	NPC471722
0.8427	Intermediate Similarity	NPC255176
0.8427	Intermediate Similarity	NPC53911
0.8427	Intermediate Similarity	NPC328539
0.8421	Intermediate Similarity	NPC476897
0.8409	Intermediate Similarity	NPC72133
0.8409	Intermediate Similarity	NPC20688
0.8409	Intermediate Similarity	NPC475022
0.8409	Intermediate Similarity	NPC222613
0.8409	Intermediate Similarity	NPC94755
0.8409	Intermediate Similarity	NPC327115
0.8409	Intermediate Similarity	NPC324063
0.8409	Intermediate Similarity	NPC118648
0.8391	Intermediate Similarity	NPC165064
0.8391	Intermediate Similarity	NPC473157
0.8391	Intermediate Similarity	NPC472265
0.8387	Intermediate Similarity	NPC471463
0.8387	Intermediate Similarity	NPC155676
0.8372	Intermediate Similarity	NPC193347
0.837	Intermediate Similarity	NPC196485
0.837	Intermediate Similarity	NPC318332
0.837	Intermediate Similarity	NPC245972
0.837	Intermediate Similarity	NPC292793
0.8367	Intermediate Similarity	NPC83744
0.8367	Intermediate Similarity	NPC144459
0.8353	Intermediate Similarity	NPC2482
0.8352	Intermediate Similarity	NPC185936
0.8352	Intermediate Similarity	NPC272746
0.8352	Intermediate Similarity	NPC212301
0.8352	Intermediate Similarity	NPC86266
0.8352	Intermediate Similarity	NPC110657
0.8352	Intermediate Similarity	NPC473167
0.8352	Intermediate Similarity	NPC168027
0.8333	Intermediate Similarity	NPC275740
0.8333	Intermediate Similarity	NPC86319
0.8333	Intermediate Similarity	NPC474570
0.8333	Intermediate Similarity	NPC469319
0.8333	Intermediate Similarity	NPC229871
0.8333	Intermediate Similarity	NPC477915
0.8316	Intermediate Similarity	NPC83709
0.8316	Intermediate Similarity	NPC110149
0.8316	Intermediate Similarity	NPC154072
0.8316	Intermediate Similarity	NPC144956
0.8315	Intermediate Similarity	NPC187376
0.8315	Intermediate Similarity	NPC312215
0.8315	Intermediate Similarity	NPC477926
0.8315	Intermediate Similarity	NPC472481
0.8315	Intermediate Similarity	NPC233836
0.8315	Intermediate Similarity	NPC159046
0.8315	Intermediate Similarity	NPC469322
0.8315	Intermediate Similarity	NPC474174
0.8315	Intermediate Similarity	NPC472482
0.8315	Intermediate Similarity	NPC251808
0.8315	Intermediate Similarity	NPC136548
0.8315	Intermediate Similarity	NPC472484
0.8315	Intermediate Similarity	NPC136948
0.8298	Intermediate Similarity	NPC474938
0.8298	Intermediate Similarity	NPC474785
0.8298	Intermediate Similarity	NPC473161
0.8298	Intermediate Similarity	NPC190554
0.8295	Intermediate Similarity	NPC197823
0.8295	Intermediate Similarity	NPC202868
0.8283	Intermediate Similarity	NPC329417
0.828	Intermediate Similarity	NPC271195
0.828	Intermediate Similarity	NPC472932
0.828	Intermediate Similarity	NPC472824
0.828	Intermediate Similarity	NPC469599
0.828	Intermediate Similarity	NPC263347
0.828	Intermediate Similarity	NPC472485
0.8276	Intermediate Similarity	NPC207013
0.8276	Intermediate Similarity	NPC470046
0.8276	Intermediate Similarity	NPC477373
0.8276	Intermediate Similarity	NPC470047
0.8276	Intermediate Similarity	NPC474634
0.8265	Intermediate Similarity	NPC50692
0.8265	Intermediate Similarity	NPC152695
0.8265	Intermediate Similarity	NPC260268
0.8265	Intermediate Similarity	NPC476027
0.8265	Intermediate Similarity	NPC85829

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 NPC470417 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	1367
0.2-0.3	4100
0.3-0.4	2423
0.4-0.5	617
0.5-0.6	161
0.6-0.7	128
0.7-0.8	153
0.8-0.85	44
0.85-0.9	11
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9048	High Similarity	NPD4786	Approved
0.881	High Similarity	NPD3667	Approved
0.875	High Similarity	NPD4753	Phase 2
0.8605	High Similarity	NPD3665	Phase 1
0.8605	High Similarity	NPD3133	Approved
0.8605	High Similarity	NPD3666	Approved
0.8539	High Similarity	NPD5328	Approved
0.8495	Intermediate Similarity	NPD4755	Approved
0.8462	Intermediate Similarity	NPD6399	Phase 3
0.8462	Intermediate Similarity	NPD4202	Approved
0.8409	Intermediate Similarity	NPD3618	Phase 1
0.8372	Intermediate Similarity	NPD4221	Approved
0.8372	Intermediate Similarity	NPD4223	Phase 3
0.8352	Intermediate Similarity	NPD6079	Approved
0.8316	Intermediate Similarity	NPD5285	Approved
0.8316	Intermediate Similarity	NPD4700	Approved
0.8316	Intermediate Similarity	NPD4696	Approved
0.8316	Intermediate Similarity	NPD5286	Approved
0.8298	Intermediate Similarity	NPD6083	Phase 2
0.8298	Intermediate Similarity	NPD6084	Phase 2
0.8295	Intermediate Similarity	NPD5329	Approved
0.828	Intermediate Similarity	NPD5210	Approved
0.828	Intermediate Similarity	NPD4629	Approved
0.8202	Intermediate Similarity	NPD5279	Phase 3
0.8182	Intermediate Similarity	NPD3668	Phase 3
0.8182	Intermediate Similarity	NPD4197	Approved
0.8144	Intermediate Similarity	NPD5224	Approved
0.8144	Intermediate Similarity	NPD5226	Approved
0.8144	Intermediate Similarity	NPD4633	Approved
0.8144	Intermediate Similarity	NPD5225	Approved
0.8144	Intermediate Similarity	NPD5211	Phase 2
0.814	Intermediate Similarity	NPD7525	Registered
0.8081	Intermediate Similarity	NPD7128	Approved
0.8081	Intermediate Similarity	NPD6675	Approved
0.8081	Intermediate Similarity	NPD6402	Approved
0.8081	Intermediate Similarity	NPD5739	Approved
0.8068	Intermediate Similarity	NPD4788	Approved
0.8061	Intermediate Similarity	NPD5174	Approved
0.8061	Intermediate Similarity	NPD5175	Approved
0.8041	Intermediate Similarity	NPD5223	Approved
0.8	Intermediate Similarity	NPD5222	Approved
0.8	Intermediate Similarity	NPD4688	Approved
0.8	Intermediate Similarity	NPD5205	Approved
0.8	Intermediate Similarity	NPD4689	Approved
0.8	Intermediate Similarity	NPD5221	Approved
0.8	Intermediate Similarity	NPD4138	Approved
0.8	Intermediate Similarity	NPD4697	Phase 3
0.8	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4693	Phase 3
0.8	Intermediate Similarity	NPD4690	Approved
0.8	Intermediate Similarity	NPD6412	Phase 2
0.798	Intermediate Similarity	NPD5141	Approved
0.7976	Intermediate Similarity	NPD7339	Approved
0.7976	Intermediate Similarity	NPD6942	Approved
0.7941	Intermediate Similarity	NPD4634	Approved
0.7921	Intermediate Similarity	NPD7320	Approved
0.7921	Intermediate Similarity	NPD6899	Approved
0.7921	Intermediate Similarity	NPD6881	Approved
0.7917	Intermediate Similarity	NPD5173	Approved
0.79	Intermediate Similarity	NPD4768	Approved
0.79	Intermediate Similarity	NPD4767	Approved
0.7895	Intermediate Similarity	NPD5695	Phase 3
0.7882	Intermediate Similarity	NPD6933	Approved
0.7879	Intermediate Similarity	NPD4754	Approved
0.7843	Intermediate Similarity	NPD6373	Approved
0.7843	Intermediate Similarity	NPD6372	Approved
0.7835	Intermediate Similarity	NPD5696	Approved
0.7826	Intermediate Similarity	NPD6672	Approved
0.7826	Intermediate Similarity	NPD5737	Approved
0.7822	Intermediate Similarity	NPD5701	Approved
0.7822	Intermediate Similarity	NPD5697	Approved
0.7802	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD5280	Approved
0.7802	Intermediate Similarity	NPD7521	Approved
0.7802	Intermediate Similarity	NPD7334	Approved
0.7802	Intermediate Similarity	NPD7146	Approved
0.7802	Intermediate Similarity	NPD6684	Approved
0.7802	Intermediate Similarity	NPD6409	Approved
0.7802	Intermediate Similarity	NPD5690	Phase 2
0.7802	Intermediate Similarity	NPD5330	Approved
0.7802	Intermediate Similarity	NPD4694	Approved
0.7788	Intermediate Similarity	NPD8297	Approved
0.7767	Intermediate Similarity	NPD7290	Approved
0.7767	Intermediate Similarity	NPD6883	Approved
0.7767	Intermediate Similarity	NPD7102	Approved
0.7766	Intermediate Similarity	NPD5284	Approved
0.7766	Intermediate Similarity	NPD5281	Approved
0.7766	Intermediate Similarity	NPD7515	Phase 2
0.7745	Intermediate Similarity	NPD4730	Approved
0.7745	Intermediate Similarity	NPD4729	Approved
0.7745	Intermediate Similarity	NPD5128	Approved
0.7701	Intermediate Similarity	NPD3617	Approved
0.7692	Intermediate Similarity	NPD6869	Approved
0.7692	Intermediate Similarity	NPD6617	Approved
0.7692	Intermediate Similarity	NPD8130	Phase 1
0.7692	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6650	Approved
0.7692	Intermediate Similarity	NPD6847	Approved
0.7692	Intermediate Similarity	NPD6649	Approved
0.7674	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD6014	Approved
0.767	Intermediate Similarity	NPD6013	Approved
0.767	Intermediate Similarity	NPD6012	Approved
0.7647	Intermediate Similarity	NPD6926	Approved
0.7647	Intermediate Similarity	NPD6924	Approved
0.764	Intermediate Similarity	NPD4692	Approved
0.764	Intermediate Similarity	NPD4139	Approved
0.7634	Intermediate Similarity	NPD6903	Approved
0.7634	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6882	Approved
0.7619	Intermediate Similarity	NPD4243	Approved
0.7614	Intermediate Similarity	NPD4195	Approved
0.7609	Intermediate Similarity	NPD6098	Approved
0.7596	Intermediate Similarity	NPD5247	Approved
0.7596	Intermediate Similarity	NPD5250	Approved
0.7596	Intermediate Similarity	NPD5249	Phase 3
0.7596	Intermediate Similarity	NPD5251	Approved
0.7596	Intermediate Similarity	NPD5248	Approved
0.7573	Intermediate Similarity	NPD6011	Approved
0.7553	Intermediate Similarity	NPD6904	Approved
0.7553	Intermediate Similarity	NPD6673	Approved
0.7553	Intermediate Similarity	NPD6080	Approved
0.7547	Intermediate Similarity	NPD4632	Approved
0.7528	Intermediate Similarity	NPD4695	Discontinued
0.7524	Intermediate Similarity	NPD5217	Approved
0.7524	Intermediate Similarity	NPD5215	Approved
0.7524	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD5216	Approved
0.75	Intermediate Similarity	NPD4747	Approved
0.75	Intermediate Similarity	NPD7115	Discovery
0.7442	Intermediate Similarity	NPD4784	Approved
0.7442	Intermediate Similarity	NPD4785	Approved
0.7429	Intermediate Similarity	NPD5169	Approved
0.7429	Intermediate Similarity	NPD5135	Approved
0.7429	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7748	Approved
0.7419	Intermediate Similarity	NPD4519	Discontinued
0.7419	Intermediate Similarity	NPD4623	Approved
0.7412	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD8035	Phase 2
0.7396	Intermediate Similarity	NPD8034	Phase 2
0.7391	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4137	Phase 3
0.7374	Intermediate Similarity	NPD7902	Approved
0.7364	Intermediate Similarity	NPD4522	Approved
0.7358	Intermediate Similarity	NPD5127	Approved
0.7347	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD7524	Approved
0.7333	Intermediate Similarity	NPD6931	Approved
0.7333	Intermediate Similarity	NPD6930	Phase 2
0.7317	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6054	Approved
0.7297	Intermediate Similarity	NPD6059	Approved
0.7297	Intermediate Similarity	NPD6319	Approved
0.7294	Intermediate Similarity	NPD4245	Approved
0.7294	Intermediate Similarity	NPD4789	Approved
0.7294	Intermediate Similarity	NPD4244	Approved
0.7294	Intermediate Similarity	NPD4691	Approved
0.7292	Intermediate Similarity	NPD4096	Approved
0.7283	Intermediate Similarity	NPD6695	Phase 3
0.7263	Intermediate Similarity	NPD5208	Approved
0.7262	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6274	Approved
0.7241	Intermediate Similarity	NPD5733	Approved
0.7238	Intermediate Similarity	NPD5168	Approved
0.7222	Intermediate Similarity	NPD7645	Phase 2
0.7222	Intermediate Similarity	NPD6929	Approved
0.7216	Intermediate Similarity	NPD5693	Phase 1
0.7216	Intermediate Similarity	NPD6050	Approved
0.7207	Intermediate Similarity	NPD7100	Approved
0.7207	Intermediate Similarity	NPD7101	Approved
0.7191	Intermediate Similarity	NPD6116	Phase 1
0.7191	Intermediate Similarity	NPD6932	Approved
0.7182	Intermediate Similarity	NPD6009	Approved
0.7176	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD3698	Phase 2
0.7176	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6922	Approved
0.7176	Intermediate Similarity	NPD6923	Approved
0.7168	Intermediate Similarity	NPD6370	Approved
0.7159	Intermediate Similarity	NPD5275	Approved
0.7159	Intermediate Similarity	NPD4190	Phase 3
0.7158	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5167	Approved
0.7143	Intermediate Similarity	NPD5133	Approved
0.7143	Intermediate Similarity	NPD7509	Discontinued
0.7143	Intermediate Similarity	NPD5368	Approved
0.7129	Intermediate Similarity	NPD7638	Approved
0.7117	Intermediate Similarity	NPD6335	Approved
0.7113	Intermediate Similarity	NPD5692	Phase 3
0.7093	Intermediate Similarity	NPD7143	Approved
0.7093	Intermediate Similarity	NPD7144	Approved
0.7087	Intermediate Similarity	NPD5091	Approved
0.7083	Intermediate Similarity	NPD4518	Approved
0.708	Intermediate Similarity	NPD6909	Approved
0.708	Intermediate Similarity	NPD6015	Approved
0.708	Intermediate Similarity	NPD6016	Approved
0.708	Intermediate Similarity	NPD6908	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