NPASS Compound

Structure

NPC476064 OpenBabel07101719512D 35 39 0 0 1 0 0 0 0 0999 V2000 2.7855 -0.5207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3066 -2.0560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5331 2.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1969 0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0662 -2.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 -0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 -2.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 -2.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3775 1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2219 1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3775 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5331 0.4875 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6887 -0.9750 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9750 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5331 -2.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7094 -0.3569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5331 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5331 1.4625 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2219 0.4875 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8444 -1.4625 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8444 0.4875 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3775 -2.9250 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.6844 -0.3569 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2219 -1.2012 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 -2.4375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 26 1 0 0 0 0 6 30 1 0 0 0 0 8 35 1 0 0 0 0 9 10 1 0 0 0 0 9 20 2 0 0 0 0 10 23 1 0 0 0 0 11 14 1 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 12 24 1 0 0 0 0 13 29 1 0 0 0 0 14 31 1 0 0 0 0 15 16 1 0 0 0 0 15 27 1 0 0 0 0 16 28 1 0 0 0 0 17 18 1 0 0 0 0 17 27 1 0 0 0 0 18 30 1 0 0 0 0 19 21 1 0 0 0 0 19 28 1 0 0 0 0 20 21 1 0 0 0 0 20 30 1 0 0 0 0 21 27 1 6 0 0 0 22 26 1 0 0 0 0 22 29 1 1 0 0 0 23 29 1 1 0 0 0 23 31 1 0 0 0 0 24 26 1 0 0 0 0 24 32 2 0 0 0 0 25 28 1 0 0 0 0 25 33 2 0 0 0 0 25 34 1 0 0 0 0 27 3 1 1 0 0 0 28 4 1 1 0 0 0 29 5 1 1 0 0 0 30 31 1 1 0 0 0 31 7 1 1 0 0 0 32 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	483.37
Volume:	531.408
LogP:	7.062
LogD:	5.143
LogS:	-5.405
# Rotatable Bonds:	2
TPSA:	58.89
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.321
Synthetic Accessibility Score:	4.905
Fsp3:	0.871
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.325
MDCK Permeability:	1.5765877833473496e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.165
30% Bioavailability (F30%):	0.917

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	97.15404510498047%
Volume Distribution (VD):	1.05
Pgp-substrate:	2.12412166595459%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.656
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.942
CYP2C9-inhibitor:	0.119
CYP2C9-substrate:	0.647
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.139
CYP3A4-inhibitor:	0.34
CYP3A4-substrate:	0.432

ADMET: Excretion

Clearance (CL):	0.85
Half-life (T1/2):	0.087

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.663
Drug-inuced Liver Injury (DILI):	0.018
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.096
Maximum Recommended Daily Dose:	0.842
Skin Sensitization:	0.068
Carcinogencity:	0.11
Eye Corrosion:	0.029
Eye Irritation:	0.221
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC476064

Natural Product ID:	NPC476064
*Common Name:**	3-Methyloximo-Olean-12-En-29-Oic Acid
IUPAC Name:	(2R,4aS,6aR,6aS,6bR,8aR,10Z,12aR,14bR)-10-methoxyimino-2,4a,6a,6b,9,9,12a-heptamethyl-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1H-picene-2-carboxylic acid
Synonyms:
Standard InCHIKey:	SAJCKHUHILYREB-VMJQRFLMSA-N
Standard InCHI:	InChI=1S/C31H49NO3/c1-26(2)22-11-14-31(7)23(29(22,5)13-12-24(26)32-35-8)10-9-20-21-19-28(4,25(33)34)16-15-27(21,3)17-18-30(20,31)6/h9,21-23H,10-19H2,1-8H3,(H,33,34)/b32-24-/t21-,22-,23+,27+,28+,29-,30+,31+/m0/s1
SMILES:	CO/N=C1/CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2C[C@@](C)(CC1)C(=O)O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL524160
PubChem CID:	44566379
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO15299	Sandoricum koetjape	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479314]
NPO15299	Sandoricum koetjape	Species	Meliaceae	Eukaryota	stems	n.a.	n.a.	PMID[1517737]
NPO15299	Sandoricum koetjape	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22672802]
NPO15299	Sandoricum koetjape	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15299	Sandoricum koetjape	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	1
Others	4

Activity Type	# Activity
Individual Protein	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2216	Individual Protein	DNA polymerase beta	Rattus norvegicus	IC50	=	36000.0	nM	PMID[492290]
NPT2216	Individual Protein	DNA polymerase beta	Rattus norvegicus	Kii	=	35.0	uM	PMID[492290]
NPT2216	Individual Protein	DNA polymerase beta	Rattus norvegicus	Kis	=	9.1	uM	PMID[492290]
NPT2216	Individual Protein	DNA polymerase beta	Rattus norvegicus	Kis	=	73.0	uM	PMID[492290]

☑ 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 NPC476064 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	99
0.1-0.2	913
0.2-0.3	6966
0.3-0.4	18122
0.4-0.5	8118
0.5-0.6	6042
0.6-0.7	1959
0.7-0.8	417
0.8-0.85	57
0.85-0.9	1
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9882	High Similarity	NPC477288
0.9882	High Similarity	NPC474964
0.8588	High Similarity	NPC16394
0.8495	Intermediate Similarity	NPC477290
0.8409	Intermediate Similarity	NPC200752
0.8391	Intermediate Similarity	NPC267691
0.8391	Intermediate Similarity	NPC274050
0.8391	Intermediate Similarity	NPC263272
0.8391	Intermediate Similarity	NPC162632
0.8353	Intermediate Similarity	NPC107039
0.8353	Intermediate Similarity	NPC471899
0.8353	Intermediate Similarity	NPC471897
0.8315	Intermediate Similarity	NPC477289
0.8295	Intermediate Similarity	NPC251779
0.8295	Intermediate Similarity	NPC69101
0.8276	Intermediate Similarity	NPC104545
0.8256	Intermediate Similarity	NPC280654
0.8256	Intermediate Similarity	NPC260385
0.8256	Intermediate Similarity	NPC110094
0.8235	Intermediate Similarity	NPC89294
0.8202	Intermediate Similarity	NPC70834
0.8161	Intermediate Similarity	NPC231431
0.8161	Intermediate Similarity	NPC199595
0.8111	Intermediate Similarity	NPC96095
0.8068	Intermediate Similarity	NPC267517
0.8068	Intermediate Similarity	NPC477057
0.8068	Intermediate Similarity	NPC37038
0.8043	Intermediate Similarity	NPC98442
0.8043	Intermediate Similarity	NPC158141
0.8043	Intermediate Similarity	NPC130577
0.8043	Intermediate Similarity	NPC173089
0.8043	Intermediate Similarity	NPC307426
0.8043	Intermediate Similarity	NPC242468
0.8043	Intermediate Similarity	NPC142415
0.8043	Intermediate Similarity	NPC68160
0.8043	Intermediate Similarity	NPC88716
0.8043	Intermediate Similarity	NPC102683
0.8043	Intermediate Similarity	NPC18064
0.8043	Intermediate Similarity	NPC171203
0.8043	Intermediate Similarity	NPC293564
0.8043	Intermediate Similarity	NPC51700
0.7978	Intermediate Similarity	NPC471898
0.7978	Intermediate Similarity	NPC221647
0.7978	Intermediate Similarity	NPC142244
0.7978	Intermediate Similarity	NPC3915
0.7957	Intermediate Similarity	NPC470629
0.7957	Intermediate Similarity	NPC473242
0.7957	Intermediate Similarity	NPC52169
0.7957	Intermediate Similarity	NPC474511
0.7957	Intermediate Similarity	NPC246708
0.7957	Intermediate Similarity	NPC182797
0.7957	Intermediate Similarity	NPC290690
0.7957	Intermediate Similarity	NPC181225
0.7957	Intermediate Similarity	NPC40552
0.7957	Intermediate Similarity	NPC474512
0.7957	Intermediate Similarity	NPC474474
0.7957	Intermediate Similarity	NPC1753
0.7957	Intermediate Similarity	NPC17733
0.7935	Intermediate Similarity	NPC72638
0.7907	Intermediate Similarity	NPC192540
0.7907	Intermediate Similarity	NPC279666
0.7889	Intermediate Similarity	NPC310989
0.7882	Intermediate Similarity	NPC36310
0.7872	Intermediate Similarity	NPC474700
0.7872	Intermediate Similarity	NPC130520
0.7872	Intermediate Similarity	NPC293048
0.7872	Intermediate Similarity	NPC59263
0.7872	Intermediate Similarity	NPC64872
0.7872	Intermediate Similarity	NPC143232
0.7872	Intermediate Similarity	NPC121798
0.7872	Intermediate Similarity	NPC470588
0.7872	Intermediate Similarity	NPC290972
0.7872	Intermediate Similarity	NPC198664
0.7872	Intermediate Similarity	NPC61543
0.7872	Intermediate Similarity	NPC127689
0.7872	Intermediate Similarity	NPC95246
0.7872	Intermediate Similarity	NPC225585
0.7872	Intermediate Similarity	NPC274330
0.7872	Intermediate Similarity	NPC25906
0.7872	Intermediate Similarity	NPC474972
0.7872	Intermediate Similarity	NPC281524
0.7872	Intermediate Similarity	NPC234346
0.7872	Intermediate Similarity	NPC263393
0.7872	Intermediate Similarity	NPC270768
0.7872	Intermediate Similarity	NPC161751
0.7849	Intermediate Similarity	NPC71507
0.7826	Intermediate Similarity	NPC474537
0.7816	Intermediate Similarity	NPC69143
0.7791	Intermediate Similarity	NPC255168
0.7791	Intermediate Similarity	NPC241854
0.7791	Intermediate Similarity	NPC161923
0.7791	Intermediate Similarity	NPC103958
0.7791	Intermediate Similarity	NPC251970
0.7791	Intermediate Similarity	NPC183503
0.7791	Intermediate Similarity	NPC283908
0.7791	Intermediate Similarity	NPC476046
0.7789	Intermediate Similarity	NPC120968
0.7789	Intermediate Similarity	NPC18872
0.7789	Intermediate Similarity	NPC273621
0.7789	Intermediate Similarity	NPC474728
0.7789	Intermediate Similarity	NPC46441
0.7789	Intermediate Similarity	NPC126369
0.7789	Intermediate Similarity	NPC113989
0.7789	Intermediate Similarity	NPC193750
0.7789	Intermediate Similarity	NPC477872
0.7789	Intermediate Similarity	NPC130278
0.7789	Intermediate Similarity	NPC290614
0.7789	Intermediate Similarity	NPC291028
0.7789	Intermediate Similarity	NPC172361
0.7789	Intermediate Similarity	NPC120840
0.7789	Intermediate Similarity	NPC470589
0.7789	Intermediate Similarity	NPC210037
0.7789	Intermediate Similarity	NPC111110
0.7789	Intermediate Similarity	NPC7260
0.7789	Intermediate Similarity	NPC86372
0.7789	Intermediate Similarity	NPC227467
0.7789	Intermediate Similarity	NPC198818
0.7765	Intermediate Similarity	NPC160817
0.7742	Intermediate Similarity	NPC324063
0.7717	Intermediate Similarity	NPC180834
0.7717	Intermediate Similarity	NPC156981
0.7717	Intermediate Similarity	NPC312660
0.7708	Intermediate Similarity	NPC474525
0.7708	Intermediate Similarity	NPC84319
0.7708	Intermediate Similarity	NPC228784
0.7708	Intermediate Similarity	NPC235884
0.7708	Intermediate Similarity	NPC966
0.7708	Intermediate Similarity	NPC145067
0.7708	Intermediate Similarity	NPC288833
0.7708	Intermediate Similarity	NPC285184
0.7708	Intermediate Similarity	NPC52021
0.7708	Intermediate Similarity	NPC470590
0.7708	Intermediate Similarity	NPC105189
0.7708	Intermediate Similarity	NPC25299
0.7708	Intermediate Similarity	NPC472149
0.7708	Intermediate Similarity	NPC4036
0.7708	Intermediate Similarity	NPC324341
0.7708	Intermediate Similarity	NPC158030
0.7708	Intermediate Similarity	NPC6255
0.7708	Intermediate Similarity	NPC233455
0.7708	Intermediate Similarity	NPC155120
0.7708	Intermediate Similarity	NPC187722
0.7708	Intermediate Similarity	NPC282616
0.7708	Intermediate Similarity	NPC38754
0.7708	Intermediate Similarity	NPC71074
0.7708	Intermediate Similarity	NPC60755
0.7708	Intermediate Similarity	NPC306541
0.7708	Intermediate Similarity	NPC471588
0.7708	Intermediate Similarity	NPC65120
0.7708	Intermediate Similarity	NPC300351
0.7708	Intermediate Similarity	NPC77099
0.7684	Intermediate Similarity	NPC474686
0.7684	Intermediate Similarity	NPC30522
0.764	Intermediate Similarity	NPC321514
0.7634	Intermediate Similarity	NPC274724
0.7634	Intermediate Similarity	NPC133954
0.7629	Intermediate Similarity	NPC298554
0.7629	Intermediate Similarity	NPC86368
0.7629	Intermediate Similarity	NPC275809
0.7629	Intermediate Similarity	NPC158059
0.7629	Intermediate Similarity	NPC118519
0.7629	Intermediate Similarity	NPC118490
0.7629	Intermediate Similarity	NPC202728
0.7629	Intermediate Similarity	NPC74855
0.7629	Intermediate Similarity	NPC136313
0.7629	Intermediate Similarity	NPC214756
0.7629	Intermediate Similarity	NPC295643
0.7629	Intermediate Similarity	NPC169343
0.7629	Intermediate Similarity	NPC63118
0.7629	Intermediate Similarity	NPC49776
0.7629	Intermediate Similarity	NPC272075
0.7629	Intermediate Similarity	NPC229281
0.7629	Intermediate Similarity	NPC307335
0.7629	Intermediate Similarity	NPC474436
0.7614	Intermediate Similarity	NPC309399
0.7604	Intermediate Similarity	NPC49320
0.7586	Intermediate Similarity	NPC166797
0.7582	Intermediate Similarity	NPC147066
0.7582	Intermediate Similarity	NPC278459
0.7556	Intermediate Similarity	NPC327674
0.7553	Intermediate Similarity	NPC235341
0.7553	Intermediate Similarity	NPC329943
0.7553	Intermediate Similarity	NPC477579
0.7553	Intermediate Similarity	NPC74363
0.7553	Intermediate Similarity	NPC9892
0.7553	Intermediate Similarity	NPC91525
0.7553	Intermediate Similarity	NPC475862
0.7553	Intermediate Similarity	NPC95594
0.7553	Intermediate Similarity	NPC10005
0.7553	Intermediate Similarity	NPC213412
0.7551	Intermediate Similarity	NPC88116
0.7551	Intermediate Similarity	NPC263548
0.7551	Intermediate Similarity	NPC78580
0.7551	Intermediate Similarity	NPC87095
0.7551	Intermediate Similarity	NPC159365
0.7551	Intermediate Similarity	NPC282395
0.7551	Intermediate Similarity	NPC145667
0.7551	Intermediate Similarity	NPC191412
0.7551	Intermediate Similarity	NPC23621
0.7551	Intermediate Similarity	NPC74751

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 NPC476064 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	105
0.1-0.2	917
0.2-0.3	3902
0.3-0.4	3095
0.4-0.5	765
0.5-0.6	288
0.6-0.7	70
0.7-0.8	8
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
0.7708	Intermediate Similarity	NPD7515	Phase 2
0.7551	Intermediate Similarity	NPD7748	Approved
0.7525	Intermediate Similarity	NPD6404	Discontinued
0.74	Intermediate Similarity	NPD7614	Phase 1
0.7327	Intermediate Similarity	NPD7902	Approved
0.732	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5707	Approved
0.7083	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7732	Phase 3
0.7041	Intermediate Similarity	NPD4723	Approved
0.7041	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4722	Approved
0.703	Intermediate Similarity	NPD7900	Approved
0.703	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD4786	Approved
0.6947	Remote Similarity	NPD3667	Approved
0.6931	Remote Similarity	NPD6399	Phase 3
0.6837	Remote Similarity	NPD7146	Approved
0.6837	Remote Similarity	NPD7521	Approved
0.6837	Remote Similarity	NPD6684	Approved
0.6837	Remote Similarity	NPD6409	Approved
0.6837	Remote Similarity	NPD7334	Approved
0.6837	Remote Similarity	NPD5330	Approved
0.6809	Remote Similarity	NPD7645	Phase 2
0.6804	Remote Similarity	NPD3665	Phase 1
0.6804	Remote Similarity	NPD3666	Approved
0.6804	Remote Similarity	NPD3133	Approved
0.6771	Remote Similarity	NPD4221	Approved
0.6771	Remote Similarity	NPD4223	Phase 3
0.6737	Remote Similarity	NPD4695	Discontinued
0.6735	Remote Similarity	NPD5329	Approved
0.67	Remote Similarity	NPD5737	Approved
0.67	Remote Similarity	NPD6903	Approved
0.67	Remote Similarity	NPD6672	Approved
0.6667	Remote Similarity	NPD3618	Phase 1
0.6667	Remote Similarity	NPD8034	Phase 2
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD8035	Phase 2
0.6667	Remote Similarity	NPD6939	Phase 2
0.6667	Remote Similarity	NPD6098	Approved
0.6634	Remote Similarity	NPD5328	Approved
0.6633	Remote Similarity	NPD4197	Approved
0.66	Remote Similarity	NPD3573	Approved
0.6526	Remote Similarity	NPD3617	Approved
0.6505	Remote Similarity	NPD5281	Approved
0.6505	Remote Similarity	NPD5284	Approved
0.6505	Remote Similarity	NPD6079	Approved
0.65	Remote Similarity	NPD4688	Approved
0.65	Remote Similarity	NPD4138	Approved
0.65	Remote Similarity	NPD5205	Approved
0.65	Remote Similarity	NPD4689	Approved
0.65	Remote Similarity	NPD4519	Discontinued
0.65	Remote Similarity	NPD4623	Approved
0.65	Remote Similarity	NPD4690	Approved
0.65	Remote Similarity	NPD4693	Phase 3
0.6495	Remote Similarity	NPD8028	Phase 2
0.6476	Remote Similarity	NPD5695	Phase 3
0.6471	Remote Similarity	NPD6904	Approved
0.6471	Remote Similarity	NPD6080	Approved
0.6471	Remote Similarity	NPD4753	Phase 2
0.6471	Remote Similarity	NPD6673	Approved
0.6465	Remote Similarity	NPD3668	Phase 3
0.6449	Remote Similarity	NPD5696	Approved
0.6429	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4096	Approved
0.6373	Remote Similarity	NPD5208	Approved
0.6364	Remote Similarity	NPD4788	Approved
0.6346	Remote Similarity	NPD6411	Approved
0.6337	Remote Similarity	NPD4694	Approved
0.6337	Remote Similarity	NPD5690	Phase 2
0.6337	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD5279	Phase 3
0.6337	Remote Similarity	NPD5280	Approved
0.6321	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD7812	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD7638	Approved
0.6286	Remote Similarity	NPD4202	Approved
0.6264	Remote Similarity	NPD6705	Phase 1
0.6262	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6675	Approved
0.625	Remote Similarity	NPD6402	Approved
0.625	Remote Similarity	NPD5739	Approved
0.625	Remote Similarity	NPD7128	Approved
0.6239	Remote Similarity	NPD7640	Approved
0.6239	Remote Similarity	NPD7639	Approved
0.6237	Remote Similarity	NPD4243	Approved
0.6222	Remote Similarity	NPD4224	Phase 2
0.6211	Remote Similarity	NPD7339	Approved
0.6211	Remote Similarity	NPD6942	Approved
0.6196	Remote Similarity	NPD4137	Phase 3
0.619	Remote Similarity	NPD5693	Phase 1
0.619	Remote Similarity	NPD6050	Approved
0.6168	Remote Similarity	NPD4629	Approved
0.6168	Remote Similarity	NPD5210	Approved
0.6162	Remote Similarity	NPD857	Phase 3
0.6162	Remote Similarity	NPD4139	Approved
0.6162	Remote Similarity	NPD4692	Approved
0.6154	Remote Similarity	NPD6101	Approved
0.6154	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.614	Remote Similarity	NPD6881	Approved
0.614	Remote Similarity	NPD7320	Approved
0.614	Remote Similarity	NPD6899	Approved
0.6129	Remote Similarity	NPD4691	Approved
0.6129	Remote Similarity	NPD4747	Approved
0.6122	Remote Similarity	NPD4195	Approved
0.6111	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD4697	Phase 3
0.6111	Remote Similarity	NPD5222	Approved
0.6111	Remote Similarity	NPD5221	Approved
0.6105	Remote Similarity	NPD4784	Approved
0.6105	Remote Similarity	NPD4785	Approved
0.6105	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD5207	Approved
0.6095	Remote Similarity	NPD5692	Phase 3
0.6087	Remote Similarity	NPD6373	Approved
0.6087	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6372	Approved
0.6075	Remote Similarity	NPD6001	Approved
0.6064	Remote Similarity	NPD6081	Approved
0.6061	Remote Similarity	NPD7525	Registered
0.6055	Remote Similarity	NPD5173	Approved
0.6055	Remote Similarity	NPD4755	Approved
0.6053	Remote Similarity	NPD6412	Phase 2
0.6053	Remote Similarity	NPD5697	Approved
0.6053	Remote Similarity	NPD5701	Approved
0.6042	Remote Similarity	NPD8039	Approved
0.6038	Remote Similarity	NPD5694	Approved
0.6034	Remote Similarity	NPD7102	Approved
0.6034	Remote Similarity	NPD7290	Approved
0.6034	Remote Similarity	NPD6883	Approved
0.6034	Remote Similarity	NPD6420	Discontinued
0.6	Remote Similarity	NPD6011	Approved
0.5983	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD8130	Phase 1
0.5983	Remote Similarity	NPD6650	Approved
0.5983	Remote Similarity	NPD3644	Approved
0.5983	Remote Similarity	NPD6617	Approved
0.5983	Remote Similarity	NPD6847	Approved
0.5983	Remote Similarity	NPD3642	Approved
0.5983	Remote Similarity	NPD6649	Approved
0.5983	Remote Similarity	NPD6869	Approved
0.5983	Remote Similarity	NPD3643	Approved
0.5979	Remote Similarity	NPD1346	Approved
0.5979	Remote Similarity	NPD6117	Approved
0.5968	Remote Similarity	NPD8328	Phase 3
0.5948	Remote Similarity	NPD6012	Approved
0.5948	Remote Similarity	NPD6013	Approved
0.5948	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD6014	Approved
0.5946	Remote Similarity	NPD5285	Approved
0.5946	Remote Similarity	NPD5286	Approved
0.5946	Remote Similarity	NPD4696	Approved
0.5946	Remote Similarity	NPD8418	Phase 2
0.5946	Remote Similarity	NPD4700	Approved
0.5938	Remote Similarity	NPD4058	Approved
0.5938	Remote Similarity	NPD5733	Approved
0.5935	Remote Similarity	NPD6909	Approved
0.5935	Remote Similarity	NPD6908	Approved
0.5932	Remote Similarity	NPD8297	Approved
0.5932	Remote Similarity	NPD6882	Approved
0.5926	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5771	Approved
0.5918	Remote Similarity	NPD6116	Phase 1
0.5893	Remote Similarity	NPD5223	Approved
0.5882	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD4190	Phase 3
0.5876	Remote Similarity	NPD5275	Approved
0.587	Remote Similarity	NPD7331	Phase 2
0.5868	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD7115	Discovery
0.5862	Remote Similarity	NPD6686	Approved
0.5859	Remote Similarity	NPD3732	Approved
0.5859	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD4776	Phase 2
0.5859	Remote Similarity	NPD6118	Approved
0.5859	Remote Similarity	NPD6697	Approved
0.5859	Remote Similarity	NPD6114	Approved
0.5859	Remote Similarity	NPD4777	Suspended
0.5859	Remote Similarity	NPD6115	Approved
0.5851	Remote Similarity	NPD15	Approved
0.5851	Remote Similarity	NPD791	Approved
0.5849	Remote Similarity	NPD6051	Approved
0.5841	Remote Similarity	NPD5226	Approved
0.5841	Remote Similarity	NPD4633	Approved
0.5841	Remote Similarity	NPD5225	Approved
0.5841	Remote Similarity	NPD5211	Phase 2
0.5841	Remote Similarity	NPD5224	Approved
0.584	Remote Similarity	NPD7604	Phase 2
0.5833	Remote Similarity	NPD5133	Approved
0.5833	Remote Similarity	NPD5779	Approved
0.5833	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5778	Approved
0.5827	Remote Similarity	NPD8074	Phase 3
0.5789	Remote Similarity	NPD5175	Approved
0.5789	Remote Similarity	NPD4754	Approved
0.5789	Remote Similarity	NPD4789	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