NPASS Compound

Structure

NPC284865 OpenBabel07101718332D 36 40 0 0 1 0 0 0 0 0999 V2000 -5.0694 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5103 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0225 -0.6185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8674 -0.8449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2245 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3796 1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2245 0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6898 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 -0.9756 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9756 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6898 -2.9268 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5347 0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5347 -2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 -2.4390 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5347 2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 0.4878 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 0.8449 -1.4634 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3796 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5347 1.4634 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6898 -3.9024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3796 -2.9268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.9268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 2.9268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3796 2.9268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8918 -0.8449 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 8 9 1 0 0 0 0 8 17 2 0 0 0 0 9 19 1 0 0 0 0 10 13 1 0 0 0 0 10 16 1 0 0 0 0 11 12 1 0 0 0 0 11 18 1 0 0 0 0 12 27 1 0 0 0 0 13 30 1 0 0 0 0 14 15 1 0 0 0 0 14 26 1 0 0 0 0 15 30 1 0 0 0 0 16 29 1 6 0 0 0 17 21 1 0 0 0 0 17 26 1 0 0 0 0 18 25 1 0 0 0 0 18 28 1 1 0 0 0 19 27 1 1 0 0 0 19 28 1 0 0 0 0 20 22 1 0 0 0 0 20 23 1 0 0 0 0 20 31 1 6 0 0 0 21 29 1 6 0 0 0 21 30 1 0 0 0 0 22 25 1 0 0 0 0 22 32 2 0 0 0 0 23 28 1 1 0 0 0 23 33 1 0 0 0 0 24 34 2 0 0 0 0 24 35 1 0 0 0 0 26 27 1 1 0 0 0 27 5 1 1 0 0 0 28 6 1 1 0 0 0 29 7 1 1 0 0 0 29 36 1 0 0 0 0 30 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	502.33
Volume:	529.486
LogP:	3.833
LogD:	3.315
LogS:	-3.785
# Rotatable Bonds:	1
TPSA:	115.06
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.396
Synthetic Accessibility Score:	5.274
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
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:	-5.702
MDCK Permeability:	1.4396834558283444e-05
Pgp-inhibitor:	0.064
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.064
20% Bioavailability (F20%):	0.064
30% Bioavailability (F30%):	0.45

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.913
Plasma Protein Binding (PPB):	80.19274139404297%
Volume Distribution (VD):	0.424
Pgp-substrate:	21.726924896240234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.396
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.656
CYP2C9-inhibitor:	0.024
CYP2C9-substrate:	0.19
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.095
CYP3A4-inhibitor:	0.199
CYP3A4-substrate:	0.162

ADMET: Excretion

Clearance (CL):	2.642
Half-life (T1/2):	0.169

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.2
Drug-inuced Liver Injury (DILI):	0.062
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.893
Maximum Recommended Daily Dose:	0.875
Skin Sensitization:	0.074
Carcinogencity:	0.44
Eye Corrosion:	0.026
Eye Irritation:	0.035
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: NPC284865

Natural Product ID:	NPC284865
*Common Name:**	1Beta,2Alpha,19Alpha-Trihydroxy-3-Oxo-12-Ursen-28-Oic Acid
IUPAC Name:	(1R,2R,4aS,6aS,6aS,6bR,8aR,11R,12S,12aR,14bS)-1,11,12-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-2H-picene-4a-carboxylic acid
Synonyms:
Standard InCHIKey:	DOADEZLVINXRRP-KZJJSQHKSA-N
Standard InCHI:	InChI=1S/C30H46O6/c1-16-10-13-30(24(34)35)15-14-26(4)17(21(30)29(16,7)36)8-9-19-27(26,5)12-11-18-25(2,3)22(32)20(31)23(33)28(18,19)6/h8,16,18-21,23,31,33,36H,9-15H2,1-7H3,(H,34,35)/t16-,18+,19+,20+,21-,23-,26-,27-,28+,29-,30+/m1/s1
SMILES:	O[C@@H]1[C@@H](O)[C@@]2(C)[C@H](C(C1=O)(C)C)CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2[C@](C)(O)[C@H](C)CC1)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518162
PubChem CID:	11730824
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
NPO3613	Eriobotrya deflexa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473413]
NPO3613	Eriobotrya deflexa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3613	Eriobotrya deflexa	Species	Rosaceae	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
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	26900.0	nM	PMID[529424]

☑ 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 NPC284865 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	240
0.1-0.2	1541
0.2-0.3	4939
0.3-0.4	10779
0.4-0.5	11549
0.5-0.6	6330
0.6-0.7	4766
0.7-0.8	2058
0.8-0.85	288
0.85-0.9	172
0.9-0.95	34
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9381	High Similarity	NPC35239
0.9278	High Similarity	NPC29765
0.9278	High Similarity	NPC271614
0.9278	High Similarity	NPC111214
0.9271	High Similarity	NPC259733
0.9271	High Similarity	NPC62516
0.9271	High Similarity	NPC158371
0.9271	High Similarity	NPC157113
0.9271	High Similarity	NPC207922
0.9175	High Similarity	NPC259788
0.9175	High Similarity	NPC106112
0.9175	High Similarity	NPC9613
0.9175	High Similarity	NPC247139
0.9175	High Similarity	NPC261935
0.9175	High Similarity	NPC255589
0.9167	High Similarity	NPC96916
0.9072	High Similarity	NPC73004
0.9072	High Similarity	NPC173744
0.9072	High Similarity	NPC201657
0.9072	High Similarity	NPC132824
0.9072	High Similarity	NPC204961
0.9062	High Similarity	NPC148964
0.9062	High Similarity	NPC474529
0.898	High Similarity	NPC43686
0.898	High Similarity	NPC187933
0.8958	High Similarity	NPC158059
0.8958	High Similarity	NPC275809
0.8958	High Similarity	NPC202728
0.8958	High Similarity	NPC118519
0.89	High Similarity	NPC118964
0.89	High Similarity	NPC256247
0.89	High Similarity	NPC54909
0.89	High Similarity	NPC233012
0.8889	High Similarity	NPC188833
0.8889	High Similarity	NPC174663
0.8866	High Similarity	NPC145667
0.8866	High Similarity	NPC88116
0.8866	High Similarity	NPC191412
0.8866	High Similarity	NPC32407
0.8866	High Similarity	NPC263548
0.8866	High Similarity	NPC114159
0.8866	High Similarity	NPC20235
0.8866	High Similarity	NPC231063
0.8866	High Similarity	NPC299996
0.8866	High Similarity	NPC282395
0.8866	High Similarity	NPC6818
0.8854	High Similarity	NPC38754
0.8854	High Similarity	NPC71074
0.8854	High Similarity	NPC25299
0.8854	High Similarity	NPC306541
0.8854	High Similarity	NPC84319
0.8854	High Similarity	NPC472149
0.8854	High Similarity	NPC474525
0.8854	High Similarity	NPC187722
0.8854	High Similarity	NPC300351
0.8854	High Similarity	NPC52021
0.8854	High Similarity	NPC235884
0.8854	High Similarity	NPC105189
0.8824	High Similarity	NPC475036
0.8788	High Similarity	NPC203343
0.8788	High Similarity	NPC312075
0.8776	High Similarity	NPC473240
0.8776	High Similarity	NPC139570
0.8776	High Similarity	NPC32118
0.8763	High Similarity	NPC307335
0.8763	High Similarity	NPC74855
0.8763	High Similarity	NPC133579
0.8763	High Similarity	NPC136313
0.8763	High Similarity	NPC118490
0.8763	High Similarity	NPC229281
0.8763	High Similarity	NPC474806
0.875	High Similarity	NPC46441
0.875	High Similarity	NPC273621
0.875	High Similarity	NPC193750
0.875	High Similarity	NPC7260
0.875	High Similarity	NPC210037
0.875	High Similarity	NPC49320
0.875	High Similarity	NPC290614
0.875	High Similarity	NPC477872
0.875	High Similarity	NPC291028
0.875	High Similarity	NPC227467
0.875	High Similarity	NPC120968
0.875	High Similarity	NPC18872
0.8687	High Similarity	NPC305464
0.8687	High Similarity	NPC327179
0.8687	High Similarity	NPC476318
0.8687	High Similarity	NPC476327
0.8687	High Similarity	NPC19376
0.8687	High Similarity	NPC116457
0.8687	High Similarity	NPC307282
0.8687	High Similarity	NPC25848
0.8673	High Similarity	NPC209868
0.8673	High Similarity	NPC87095
0.866	High Similarity	NPC324341
0.866	High Similarity	NPC228784
0.866	High Similarity	NPC288833
0.866	High Similarity	NPC282616
0.866	High Similarity	NPC6255
0.866	High Similarity	NPC471588
0.866	High Similarity	NPC966
0.866	High Similarity	NPC155120
0.8646	High Similarity	NPC69627
0.8646	High Similarity	NPC290972
0.8646	High Similarity	NPC274330
0.8646	High Similarity	NPC25906
0.8646	High Similarity	NPC64872
0.8646	High Similarity	NPC143232
0.8646	High Similarity	NPC198664
0.86	High Similarity	NPC189880
0.8586	High Similarity	NPC148523
0.8586	High Similarity	NPC198245
0.8586	High Similarity	NPC53565
0.8571	High Similarity	NPC298554
0.8557	High Similarity	NPC470589
0.8557	High Similarity	NPC130278
0.8557	High Similarity	NPC126369
0.8557	High Similarity	NPC86372
0.8557	High Similarity	NPC111110
0.8557	High Similarity	NPC172361
0.8544	High Similarity	NPC90177
0.8542	High Similarity	NPC1753
0.8542	High Similarity	NPC470629
0.8542	High Similarity	NPC290690
0.8542	High Similarity	NPC473242
0.8542	High Similarity	NPC182797
0.8542	High Similarity	NPC474511
0.8542	High Similarity	NPC17733
0.8542	High Similarity	NPC474512
0.8542	High Similarity	NPC52169
0.8542	High Similarity	NPC181225
0.8515	High Similarity	NPC260149
0.8515	High Similarity	NPC164349
0.8515	High Similarity	NPC58942
0.8505	High Similarity	NPC146945
0.8505	High Similarity	NPC171888
0.85	High Similarity	NPC230151
0.85	High Similarity	NPC88847
0.85	High Similarity	NPC223169
0.85	High Similarity	NPC98874
0.8485	Intermediate Similarity	NPC188102
0.8485	Intermediate Similarity	NPC60692
0.8485	Intermediate Similarity	NPC222047
0.8469	Intermediate Similarity	NPC145067
0.8469	Intermediate Similarity	NPC233455
0.8469	Intermediate Similarity	NPC4036
0.8469	Intermediate Similarity	NPC65120
0.8469	Intermediate Similarity	NPC158030
0.8469	Intermediate Similarity	NPC235704
0.8462	Intermediate Similarity	NPC213366
0.8454	Intermediate Similarity	NPC121798
0.8454	Intermediate Similarity	NPC263393
0.8454	Intermediate Similarity	NPC127689
0.8454	Intermediate Similarity	NPC130520
0.8454	Intermediate Similarity	NPC470588
0.8454	Intermediate Similarity	NPC61543
0.8454	Intermediate Similarity	NPC293048
0.8454	Intermediate Similarity	NPC225585
0.8454	Intermediate Similarity	NPC234346
0.8454	Intermediate Similarity	NPC59263
0.8454	Intermediate Similarity	NPC270768
0.8438	Intermediate Similarity	NPC242468
0.8438	Intermediate Similarity	NPC293564
0.8438	Intermediate Similarity	NPC73064
0.8438	Intermediate Similarity	NPC477926
0.8438	Intermediate Similarity	NPC158141
0.8438	Intermediate Similarity	NPC68160
0.8438	Intermediate Similarity	NPC173089
0.8438	Intermediate Similarity	NPC102683
0.8438	Intermediate Similarity	NPC171203
0.8438	Intermediate Similarity	NPC142415
0.8438	Intermediate Similarity	NPC51700
0.8438	Intermediate Similarity	NPC88716
0.8438	Intermediate Similarity	NPC307426
0.8438	Intermediate Similarity	NPC18064
0.8438	Intermediate Similarity	NPC130577
0.8438	Intermediate Similarity	NPC98442
0.84	Intermediate Similarity	NPC290481
0.84	Intermediate Similarity	NPC195715
0.84	Intermediate Similarity	NPC83693
0.8384	Intermediate Similarity	NPC214756
0.8384	Intermediate Similarity	NPC295643
0.8384	Intermediate Similarity	NPC272075
0.8381	Intermediate Similarity	NPC80566
0.8367	Intermediate Similarity	NPC474728
0.8351	Intermediate Similarity	NPC40552
0.8351	Intermediate Similarity	NPC246708
0.8349	Intermediate Similarity	NPC7921
0.8349	Intermediate Similarity	NPC208998
0.8333	Intermediate Similarity	NPC72638
0.8333	Intermediate Similarity	NPC475862
0.8333	Intermediate Similarity	NPC74363
0.8319	Intermediate Similarity	NPC75417
0.8318	Intermediate Similarity	NPC310546
0.8317	Intermediate Similarity	NPC167193
0.8317	Intermediate Similarity	NPC472806
0.8302	Intermediate Similarity	NPC144854
0.8302	Intermediate Similarity	NPC3316
0.8302	Intermediate Similarity	NPC301666
0.83	Intermediate Similarity	NPC296164
0.83	Intermediate Similarity	NPC184006

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 NPC284865 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	217
0.1-0.2	1917
0.2-0.3	3818
0.3-0.4	2050
0.4-0.5	686
0.5-0.6	237
0.6-0.7	153
0.7-0.8	67
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8469	Intermediate Similarity	NPD7515	Phase 2
0.8235	Intermediate Similarity	NPD7902	Approved
0.8119	Intermediate Similarity	NPD7748	Approved
0.8017	Intermediate Similarity	NPD8328	Phase 3
0.7965	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD7900	Approved
0.7941	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD5739	Approved
0.787	Intermediate Similarity	NPD6675	Approved
0.787	Intermediate Similarity	NPD7128	Approved
0.787	Intermediate Similarity	NPD6402	Approved
0.7818	Intermediate Similarity	NPD6372	Approved
0.7818	Intermediate Similarity	NPD6373	Approved
0.7727	Intermediate Similarity	NPD6881	Approved
0.7727	Intermediate Similarity	NPD6899	Approved
0.7727	Intermediate Similarity	NPD7320	Approved
0.7727	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD4755	Approved
0.7679	Intermediate Similarity	NPD6650	Approved
0.7679	Intermediate Similarity	NPD6649	Approved
0.767	Intermediate Similarity	NPD6399	Phase 3
0.7636	Intermediate Similarity	NPD5701	Approved
0.7636	Intermediate Similarity	NPD5697	Approved
0.7619	Intermediate Similarity	NPD4697	Phase 3
0.7611	Intermediate Similarity	NPD8297	Approved
0.7589	Intermediate Similarity	NPD4634	Approved
0.7589	Intermediate Similarity	NPD6883	Approved
0.7589	Intermediate Similarity	NPD7290	Approved
0.7589	Intermediate Similarity	NPD7102	Approved
0.757	Intermediate Similarity	NPD5286	Approved
0.757	Intermediate Similarity	NPD4696	Approved
0.757	Intermediate Similarity	NPD4700	Approved
0.757	Intermediate Similarity	NPD5285	Approved
0.7568	Intermediate Similarity	NPD6011	Approved
0.7549	Intermediate Similarity	NPD5328	Approved
0.7549	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD4632	Approved
0.7522	Intermediate Similarity	NPD8130	Phase 1
0.7522	Intermediate Similarity	NPD6617	Approved
0.7522	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD6869	Approved
0.7522	Intermediate Similarity	NPD6847	Approved
0.75	Intermediate Similarity	NPD5223	Approved
0.75	Intermediate Similarity	NPD6013	Approved
0.75	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6012	Approved
0.75	Intermediate Similarity	NPD6014	Approved
0.75	Intermediate Similarity	NPD7115	Discovery
0.7458	Intermediate Similarity	NPD6319	Approved
0.7456	Intermediate Similarity	NPD6882	Approved
0.7453	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD5222	Approved
0.7453	Intermediate Similarity	NPD5221	Approved
0.7431	Intermediate Similarity	NPD5224	Approved
0.7431	Intermediate Similarity	NPD5226	Approved
0.7431	Intermediate Similarity	NPD5211	Phase 2
0.7431	Intermediate Similarity	NPD5225	Approved
0.7431	Intermediate Similarity	NPD4633	Approved
0.7426	Intermediate Similarity	NPD3618	Phase 1
0.7404	Intermediate Similarity	NPD8034	Phase 2
0.7404	Intermediate Similarity	NPD6411	Approved
0.7404	Intermediate Similarity	NPD8035	Phase 2
0.7404	Intermediate Similarity	NPD6079	Approved
0.74	Intermediate Similarity	NPD4786	Approved
0.7383	Intermediate Similarity	NPD5173	Approved
0.7374	Intermediate Similarity	NPD3667	Approved
0.7364	Intermediate Similarity	NPD5175	Approved
0.7364	Intermediate Similarity	NPD4754	Approved
0.7364	Intermediate Similarity	NPD5174	Approved
0.7345	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7736	Approved
0.7297	Intermediate Similarity	NPD5141	Approved
0.7245	Intermediate Similarity	NPD7645	Phase 2
0.7232	Intermediate Similarity	NPD4767	Approved
0.7232	Intermediate Similarity	NPD4768	Approved
0.7222	Intermediate Similarity	NPD6083	Phase 2
0.7222	Intermediate Similarity	NPD6084	Phase 2
0.7213	Intermediate Similarity	NPD7492	Approved
0.7212	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6101	Approved
0.7203	Intermediate Similarity	NPD6009	Approved
0.7184	Intermediate Similarity	NPD3573	Approved
0.717	Intermediate Similarity	NPD4202	Approved
0.7167	Intermediate Similarity	NPD6059	Approved
0.7167	Intermediate Similarity	NPD6054	Approved
0.7154	Intermediate Similarity	NPD6616	Approved
0.7143	Intermediate Similarity	NPD6335	Approved
0.7119	Intermediate Similarity	NPD6274	Approved
0.7105	Intermediate Similarity	NPD4730	Approved
0.7105	Intermediate Similarity	NPD5128	Approved
0.7105	Intermediate Similarity	NPD4729	Approved
0.7097	Intermediate Similarity	NPD7078	Approved
0.7097	Intermediate Similarity	NPD8293	Discontinued
0.7087	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7100	Approved
0.7083	Intermediate Similarity	NPD7101	Approved
0.708	Intermediate Similarity	NPD6008	Approved
0.7059	Intermediate Similarity	NPD6317	Approved
0.7049	Intermediate Similarity	NPD6370	Approved
0.7048	Intermediate Similarity	NPD4753	Phase 2
0.7	Intermediate Similarity	NPD6314	Approved
0.7	Intermediate Similarity	NPD6313	Approved
0.7	Intermediate Similarity	NPD4695	Discontinued
0.7	Intermediate Similarity	NPD5696	Approved
0.7	Intermediate Similarity	NPD7525	Registered
0.7	Intermediate Similarity	NPD4225	Approved
0.6992	Remote Similarity	NPD7604	Phase 2
0.6983	Remote Similarity	NPD5169	Approved
0.6983	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD5248	Approved
0.6983	Remote Similarity	NPD5250	Approved
0.6983	Remote Similarity	NPD5247	Approved
0.6983	Remote Similarity	NPD5135	Approved
0.6983	Remote Similarity	NPD5251	Approved
0.6983	Remote Similarity	NPD5249	Phase 3
0.6975	Remote Similarity	NPD6868	Approved
0.6967	Remote Similarity	NPD5983	Phase 2
0.6967	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD6016	Approved
0.6967	Remote Similarity	NPD6908	Approved
0.6967	Remote Similarity	NPD6015	Approved
0.6967	Remote Similarity	NPD6921	Approved
0.6967	Remote Similarity	NPD6909	Approved
0.6952	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD5737	Approved
0.6952	Remote Similarity	NPD6672	Approved
0.6923	Remote Similarity	NPD5127	Approved
0.6923	Remote Similarity	NPD5215	Approved
0.6923	Remote Similarity	NPD5217	Approved
0.6923	Remote Similarity	NPD5216	Approved
0.6911	Remote Similarity	NPD5988	Approved
0.6893	Remote Similarity	NPD3665	Phase 1
0.6893	Remote Similarity	NPD3133	Approved
0.6893	Remote Similarity	NPD3666	Approved
0.6893	Remote Similarity	NPD3668	Phase 3
0.6881	Remote Similarity	NPD5695	Phase 3
0.6881	Remote Similarity	NPD4629	Approved
0.6881	Remote Similarity	NPD5210	Approved
0.688	Remote Similarity	NPD6336	Discontinued
0.6852	Remote Similarity	NPD5779	Approved
0.6852	Remote Similarity	NPD5778	Approved
0.685	Remote Similarity	NPD7319	Approved
0.6847	Remote Similarity	NPD7638	Approved
0.6827	Remote Similarity	NPD5329	Approved
0.6818	Remote Similarity	NPD7614	Phase 1
0.681	Remote Similarity	NPD5168	Approved
0.6786	Remote Similarity	NPD7640	Approved
0.6786	Remote Similarity	NPD7639	Approved
0.6772	Remote Similarity	NPD6033	Approved
0.6762	Remote Similarity	NPD5279	Phase 3
0.6762	Remote Similarity	NPD6684	Approved
0.6762	Remote Similarity	NPD7334	Approved
0.6762	Remote Similarity	NPD7146	Approved
0.6762	Remote Similarity	NPD6409	Approved
0.6762	Remote Similarity	NPD5330	Approved
0.6762	Remote Similarity	NPD7521	Approved
0.6762	Remote Similarity	NPD6098	Approved
0.6759	Remote Similarity	NPD5281	Approved
0.6759	Remote Similarity	NPD5284	Approved
0.6752	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5167	Approved
0.6746	Remote Similarity	NPD7507	Approved
0.6731	Remote Similarity	NPD4197	Approved
0.6729	Remote Similarity	NPD6080	Approved
0.6729	Remote Similarity	NPD6904	Approved
0.6729	Remote Similarity	NPD6673	Approved
0.6727	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6412	Phase 2
0.67	Remote Similarity	NPD6116	Phase 1
0.6694	Remote Similarity	NPD8515	Approved
0.6694	Remote Similarity	NPD8513	Phase 3
0.6694	Remote Similarity	NPD8517	Approved
0.6694	Remote Similarity	NPD8516	Approved
0.6636	Remote Similarity	NPD6903	Approved
0.6602	Remote Similarity	NPD5369	Approved
0.66	Remote Similarity	NPD6117	Approved
0.6555	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4221	Approved
0.6538	Remote Similarity	NPD4223	Phase 3
0.6529	Remote Similarity	NPD8133	Approved
0.6518	Remote Similarity	NPD7732	Phase 3
0.6505	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6942	Approved
0.65	Remote Similarity	NPD7339	Approved
0.6476	Remote Similarity	NPD4788	Approved
0.6471	Remote Similarity	NPD6115	Approved
0.6471	Remote Similarity	NPD6118	Approved
0.6471	Remote Similarity	NPD6697	Approved
0.6471	Remote Similarity	NPD6114	Approved
0.6471	Remote Similarity	NPD3617	Approved
0.6455	Remote Similarity	NPD6050	Approved
0.6455	Remote Similarity	NPD5693	Phase 1
0.6449	Remote Similarity	NPD5690	Phase 2
0.6449	Remote Similarity	NPD5786	Approved
0.6449	Remote Similarity	NPD5280	Approved
0.6449	Remote Similarity	NPD4694	Approved
0.6436	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4522	Approved
0.64	Remote Similarity	NPD6113	Clinical (unspecified phase)

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