NPASS Compound

Structure

NPC180834 OpenBabel07101718292D 32 36 0 0 1 0 0 0 0 0999 V2000 3.2159 -4.0934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6289 -3.7777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0414 2.3021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0143 2.3021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3705 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3705 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5279 -0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5279 -0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 -2.9189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3705 -1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 -1.4595 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6852 -1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 0.9730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8426 -0.4865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3705 0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3705 -2.9189 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5279 -3.4054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5279 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5279 -1.4595 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6852 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8426 -0.4865 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 -4.2131 1.4595 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2131 -3.4054 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 7 29 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 22 1 0 0 0 0 11 14 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 23 1 0 0 0 0 13 28 1 0 0 0 0 14 30 1 0 0 0 0 15 16 1 0 0 0 0 15 27 1 0 0 0 0 16 29 1 0 0 0 0 17 20 2 0 0 0 0 17 25 1 0 0 0 0 18 24 1 0 0 0 0 18 27 1 0 0 0 0 19 20 1 0 0 0 0 19 29 1 1 0 0 0 20 27 1 0 0 0 0 21 26 1 0 0 0 0 21 28 1 6 0 0 0 22 28 1 6 0 0 0 22 30 1 0 0 0 0 23 26 1 0 0 0 0 23 31 2 0 0 0 0 24 25 1 0 0 0 0 24 32 1 1 0 0 0 27 5 1 6 0 0 0 28 6 1 6 0 0 0 29 30 1 6 0 0 0 30 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.37
Volume:	496.961
LogP:	5.775
LogD:	4.896
LogS:	-5.736
# Rotatable Bonds:	0
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.4
Synthetic Accessibility Score:	4.887
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.17
MDCK Permeability:	1.1077535418735351e-05
Pgp-inhibitor:	0.439
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.914
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.174
Plasma Protein Binding (PPB):	94.09415435791016%
Volume Distribution (VD):	1.038
Pgp-substrate:	3.500880718231201%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.579
CYP2C19-inhibitor:	0.132
CYP2C19-substrate:	0.962
CYP2C9-inhibitor:	0.21
CYP2C9-substrate:	0.825
CYP2D6-inhibitor:	0.076
CYP2D6-substrate:	0.639
CYP3A4-inhibitor:	0.634
CYP3A4-substrate:	0.67

ADMET: Excretion

Clearance (CL):	5.261
Half-life (T1/2):	0.146

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.284
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.676
Maximum Recommended Daily Dose:	0.979
Skin Sensitization:	0.121
Carcinogencity:	0.035
Eye Corrosion:	0.122
Eye Irritation:	0.353
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC180834

Natural Product ID:	NPC180834
*Common Name:**	21Alpha-Hydroxy-3-Oxo-Olean-18-Ene
IUPAC Name:	(4aR,6aS,6aR,6bR,8aS,10R,14aR,14bR)-10-hydroxy-4,4,6a,6b,8a,11,11,14b-octamethyl-2,4a,5,6,6a,7,8,9,10,13,14,14a-dodecahydro-1H-picen-3-one
Synonyms:
Standard InCHIKey:	GEOCBTODUJBQNE-ZSRYNZGBSA-N
Standard InCHI:	InChI=1S/C30H48O2/c1-25(2)17-20-19-9-10-22-28(6)13-12-23(31)26(3,4)21(28)11-14-30(22,8)29(19,7)16-15-27(20,5)18-24(25)32/h17,19,21-22,24,32H,9-16,18H2,1-8H3/t19-,21+,22-,24-,27+,28+,29-,30-/m1/s1
SMILES:	CC1(C)C=C2[C@H]3CC[C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@@]2(C)C[C@H]1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2023100
PubChem CID:	60145809
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
NPO33201	celastraceae sp.	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22487595]

☑ 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
Others	4

Activity Type	# Activity
Cell Line	2
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT460	Cell Line	MT2	Homo sapiens	Activity	=	74.0	%	PMID[565755]
NPT460	Cell Line	MT2	Homo sapiens	CC50	>	100000.0	nM	PMID[565755]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	=	22.0	%	PMID[565755]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	20000.0	nM	PMID[565755]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	<	50.0	%	PMID[565755]

☑ 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 NPC180834 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	194
0.1-0.2	1282
0.2-0.3	5487
0.3-0.4	15890
0.4-0.5	7920
0.5-0.6	5515
0.6-0.7	4516
0.7-0.8	1412
0.8-0.85	252
0.85-0.9	171
0.9-0.95	52
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9744	High Similarity	NPC310989
0.963	High Similarity	NPC73064
0.9625	High Similarity	NPC133954
0.9615	High Similarity	NPC3915
0.9506	High Similarity	NPC213412
0.9506	High Similarity	NPC475862
0.9506	High Similarity	NPC74363
0.9383	High Similarity	NPC274724
0.9277	High Similarity	NPC474512
0.9277	High Similarity	NPC17733
0.9277	High Similarity	NPC470629
0.9277	High Similarity	NPC290690
0.9277	High Similarity	NPC473242
0.9277	High Similarity	NPC181225
0.9268	High Similarity	NPC235341
0.9268	High Similarity	NPC95594
0.9268	High Similarity	NPC477579
0.9167	High Similarity	NPC198664
0.9167	High Similarity	NPC69627
0.9167	High Similarity	NPC274330
0.9167	High Similarity	NPC143232
0.9167	High Similarity	NPC470588
0.9157	High Similarity	NPC18064
0.9157	High Similarity	NPC171203
0.9157	High Similarity	NPC98442
0.9157	High Similarity	NPC68160
0.9157	High Similarity	NPC307426
0.9157	High Similarity	NPC142415
0.9157	High Similarity	NPC293564
0.9157	High Similarity	NPC88716
0.9157	High Similarity	NPC102683
0.9157	High Similarity	NPC71507
0.9157	High Similarity	NPC51700
0.9157	High Similarity	NPC242468
0.9157	High Similarity	NPC130577
0.9059	High Similarity	NPC46441
0.9059	High Similarity	NPC470589
0.9059	High Similarity	NPC126369
0.9059	High Similarity	NPC291028
0.9059	High Similarity	NPC111110
0.9048	High Similarity	NPC474511
0.9048	High Similarity	NPC246708
0.9048	High Similarity	NPC1753
0.9048	High Similarity	NPC40552
0.9048	High Similarity	NPC52169
0.9048	High Similarity	NPC182797
0.9036	High Similarity	NPC72638
0.9024	High Similarity	NPC59453
0.9024	High Similarity	NPC221758
0.9012	High Similarity	NPC69101
0.9012	High Similarity	NPC151519
0.9012	High Similarity	NPC163236
0.9012	High Similarity	NPC251779
0.9	High Similarity	NPC2482
0.8953	High Similarity	NPC158030
0.8953	High Similarity	NPC187722
0.8953	High Similarity	NPC38754
0.8953	High Similarity	NPC233455
0.8953	High Similarity	NPC474525
0.8953	High Similarity	NPC105189
0.8953	High Similarity	NPC65120
0.8953	High Similarity	NPC4036
0.8953	High Similarity	NPC145067
0.8941	High Similarity	NPC225585
0.8941	High Similarity	NPC25906
0.8941	High Similarity	NPC474972
0.8941	High Similarity	NPC474686
0.8941	High Similarity	NPC95246
0.8941	High Similarity	NPC161751
0.8941	High Similarity	NPC130520
0.8941	High Similarity	NPC234346
0.8941	High Similarity	NPC290972
0.8941	High Similarity	NPC263393
0.8941	High Similarity	NPC127689
0.8941	High Similarity	NPC281524
0.8941	High Similarity	NPC61543
0.8941	High Similarity	NPC270768
0.8941	High Similarity	NPC64872
0.8941	High Similarity	NPC121798
0.8941	High Similarity	NPC59263
0.8941	High Similarity	NPC293048
0.8929	High Similarity	NPC173089
0.8929	High Similarity	NPC158141
0.8889	High Similarity	NPC274050
0.8889	High Similarity	NPC14151
0.8889	High Similarity	NPC263272
0.8889	High Similarity	NPC162632
0.8889	High Similarity	NPC267691
0.8851	High Similarity	NPC214756
0.8851	High Similarity	NPC295643
0.8851	High Similarity	NPC158059
0.8851	High Similarity	NPC229281
0.8851	High Similarity	NPC118519
0.8851	High Similarity	NPC202728
0.8851	High Similarity	NPC272075
0.8837	High Similarity	NPC172361
0.8837	High Similarity	NPC210037
0.8837	High Similarity	NPC18872
0.8837	High Similarity	NPC130278
0.8837	High Similarity	NPC290614
0.8837	High Similarity	NPC120968
0.8837	High Similarity	NPC273621
0.8837	High Similarity	NPC193750
0.8837	High Similarity	NPC227467
0.8837	High Similarity	NPC474728
0.8837	High Similarity	NPC477872
0.8837	High Similarity	NPC86372
0.8837	High Similarity	NPC7260
0.8824	High Similarity	NPC474474
0.8824	High Similarity	NPC230387
0.8824	High Similarity	NPC206060
0.8824	High Similarity	NPC472802
0.881	High Similarity	NPC474778
0.881	High Similarity	NPC158393
0.881	High Similarity	NPC56588
0.881	High Similarity	NPC145879
0.881	High Similarity	NPC51014
0.881	High Similarity	NPC474732
0.881	High Similarity	NPC31564
0.881	High Similarity	NPC474733
0.878	High Similarity	NPC48362
0.878	High Similarity	NPC212083
0.8764	High Similarity	NPC62516
0.8764	High Similarity	NPC157113
0.875	High Similarity	NPC191412
0.875	High Similarity	NPC470396
0.875	High Similarity	NPC114159
0.875	High Similarity	NPC23170
0.875	High Similarity	NPC159365
0.875	High Similarity	NPC474989
0.875	High Similarity	NPC99168
0.875	High Similarity	NPC6818
0.875	High Similarity	NPC474529
0.875	High Similarity	NPC209868
0.875	High Similarity	NPC87095
0.875	High Similarity	NPC22955
0.8736	High Similarity	NPC301244
0.8736	High Similarity	NPC52021
0.8736	High Similarity	NPC470590
0.8736	High Similarity	NPC472149
0.8736	High Similarity	NPC324341
0.8736	High Similarity	NPC306541
0.8736	High Similarity	NPC60755
0.8736	High Similarity	NPC966
0.8736	High Similarity	NPC288833
0.8736	High Similarity	NPC471588
0.8736	High Similarity	NPC84319
0.8736	High Similarity	NPC25299
0.8736	High Similarity	NPC235884
0.8736	High Similarity	NPC71074
0.8736	High Similarity	NPC155120
0.8736	High Similarity	NPC282616
0.8736	High Similarity	NPC285184
0.8736	High Similarity	NPC6255
0.8736	High Similarity	NPC300351
0.8736	High Similarity	NPC228784
0.8736	High Similarity	NPC77099
0.8734	High Similarity	NPC106364
0.8721	High Similarity	NPC474700
0.8706	High Similarity	NPC58063
0.8706	High Similarity	NPC475740
0.8675	High Similarity	NPC70834
0.8659	High Similarity	NPC121984
0.8659	High Similarity	NPC328264
0.8652	High Similarity	NPC96916
0.8652	High Similarity	NPC148523
0.8652	High Similarity	NPC473240
0.8652	High Similarity	NPC139570
0.8642	High Similarity	NPC16394
0.8642	High Similarity	NPC291379
0.8642	High Similarity	NPC53744
0.8636	High Similarity	NPC86368
0.8636	High Similarity	NPC63118
0.8636	High Similarity	NPC474806
0.8636	High Similarity	NPC49776
0.8636	High Similarity	NPC275809
0.8636	High Similarity	NPC298554
0.8636	High Similarity	NPC118490
0.8636	High Similarity	NPC136313
0.8636	High Similarity	NPC74855
0.8636	High Similarity	NPC474436
0.8636	High Similarity	NPC307335
0.8636	High Similarity	NPC133579
0.8625	High Similarity	NPC40394
0.8625	High Similarity	NPC101475
0.8625	High Similarity	NPC34177
0.8625	High Similarity	NPC157996
0.8621	High Similarity	NPC49320
0.8621	High Similarity	NPC198818
0.8621	High Similarity	NPC85173
0.8621	High Similarity	NPC120840
0.8621	High Similarity	NPC113989
0.8605	High Similarity	NPC328313
0.8588	High Similarity	NPC470955
0.8588	High Similarity	NPC155011
0.8588	High Similarity	NPC94666
0.8588	High Similarity	NPC20688
0.8571	High Similarity	NPC214043
0.8571	High Similarity	NPC227132
0.8571	High Similarity	NPC312660

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 NPC180834 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	175
0.1-0.2	1648
0.2-0.3	3988
0.3-0.4	2323
0.4-0.5	594
0.5-0.6	172
0.6-0.7	186
0.7-0.8	55
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9024	High Similarity	NPD4786	Approved
0.9012	High Similarity	NPD3667	Approved
0.8953	High Similarity	NPD7515	Phase 2
0.8539	High Similarity	NPD7748	Approved
0.8415	Intermediate Similarity	NPD7645	Phase 2
0.8372	Intermediate Similarity	NPD3618	Phase 1
0.8353	Intermediate Similarity	NPD3666	Approved
0.8353	Intermediate Similarity	NPD3133	Approved
0.8353	Intermediate Similarity	NPD3665	Phase 1
0.8295	Intermediate Similarity	NPD5328	Approved
0.8261	Intermediate Similarity	NPD7902	Approved
0.814	Intermediate Similarity	NPD3668	Phase 3
0.8111	Intermediate Similarity	NPD6079	Approved
0.8046	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8022	Intermediate Similarity	NPD6399	Phase 3
0.7935	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD7900	Approved
0.7927	Intermediate Similarity	NPD6942	Approved
0.7927	Intermediate Similarity	NPD7339	Approved
0.7889	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD4695	Discontinued
0.7831	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD4202	Approved
0.7778	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD5279	Phase 3
0.7701	Intermediate Similarity	NPD4221	Approved
0.7701	Intermediate Similarity	NPD4223	Phase 3
0.7692	Intermediate Similarity	NPD4753	Phase 2
0.764	Intermediate Similarity	NPD5329	Approved
0.7614	Intermediate Similarity	NPD4788	Approved
0.7579	Intermediate Similarity	NPD5221	Approved
0.7579	Intermediate Similarity	NPD5222	Approved
0.7579	Intermediate Similarity	NPD4697	Phase 3
0.7579	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD7521	Approved
0.7556	Intermediate Similarity	NPD6409	Approved
0.7556	Intermediate Similarity	NPD6684	Approved
0.7556	Intermediate Similarity	NPD7146	Approved
0.7556	Intermediate Similarity	NPD7334	Approved
0.7556	Intermediate Similarity	NPD5330	Approved
0.7528	Intermediate Similarity	NPD4197	Approved
0.75	Intermediate Similarity	NPD5173	Approved
0.75	Intermediate Similarity	NPD4755	Approved
0.7471	Intermediate Similarity	NPD7525	Registered
0.7442	Intermediate Similarity	NPD3617	Approved
0.7391	Intermediate Similarity	NPD6903	Approved
0.7363	Intermediate Similarity	NPD4690	Approved
0.7363	Intermediate Similarity	NPD4623	Approved
0.7363	Intermediate Similarity	NPD5205	Approved
0.7363	Intermediate Similarity	NPD4519	Discontinued
0.7363	Intermediate Similarity	NPD4693	Phase 3
0.7363	Intermediate Similarity	NPD4689	Approved
0.7363	Intermediate Similarity	NPD4138	Approved
0.7363	Intermediate Similarity	NPD4688	Approved
0.7349	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5286	Approved
0.7347	Intermediate Similarity	NPD4700	Approved
0.7347	Intermediate Similarity	NPD4696	Approved
0.7347	Intermediate Similarity	NPD5285	Approved
0.734	Intermediate Similarity	NPD8035	Phase 2
0.734	Intermediate Similarity	NPD8034	Phase 2
0.732	Intermediate Similarity	NPD6084	Phase 2
0.732	Intermediate Similarity	NPD6083	Phase 2
0.7317	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4629	Approved
0.7292	Intermediate Similarity	NPD5210	Approved
0.7273	Intermediate Similarity	NPD5223	Approved
0.7229	Intermediate Similarity	NPD4244	Approved
0.7229	Intermediate Similarity	NPD4245	Approved
0.7216	Intermediate Similarity	NPD7614	Phase 1
0.7204	Intermediate Similarity	NPD5737	Approved
0.7204	Intermediate Similarity	NPD6672	Approved
0.72	Intermediate Similarity	NPD5225	Approved
0.72	Intermediate Similarity	NPD5211	Phase 2
0.72	Intermediate Similarity	NPD4633	Approved
0.72	Intermediate Similarity	NPD5226	Approved
0.72	Intermediate Similarity	NPD5224	Approved
0.7176	Intermediate Similarity	NPD6926	Approved
0.7176	Intermediate Similarity	NPD6924	Approved
0.7174	Intermediate Similarity	NPD5690	Phase 2
0.7174	Intermediate Similarity	NPD4694	Approved
0.7174	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD5280	Approved
0.7158	Intermediate Similarity	NPD6411	Approved
0.7157	Intermediate Similarity	NPD7128	Approved
0.7157	Intermediate Similarity	NPD5739	Approved
0.7157	Intermediate Similarity	NPD6675	Approved
0.7157	Intermediate Similarity	NPD6402	Approved
0.7129	Intermediate Similarity	NPD4754	Approved
0.7129	Intermediate Similarity	NPD5175	Approved
0.7129	Intermediate Similarity	NPD5174	Approved
0.7108	Intermediate Similarity	NPD3698	Phase 2
0.7108	Intermediate Similarity	NPD4137	Phase 3
0.7097	Intermediate Similarity	NPD3573	Approved
0.7087	Intermediate Similarity	NPD6412	Phase 2
0.7079	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7638	Approved
0.7059	Intermediate Similarity	NPD5141	Approved
0.7024	Intermediate Similarity	NPD4691	Approved
0.7024	Intermediate Similarity	NPD4747	Approved
0.7024	Intermediate Similarity	NPD4789	Approved
0.7019	Intermediate Similarity	NPD6899	Approved
0.7019	Intermediate Similarity	NPD6881	Approved
0.7019	Intermediate Similarity	NPD7320	Approved
0.7011	Intermediate Similarity	NPD6933	Approved
0.7	Intermediate Similarity	NPD4692	Approved
0.7	Intermediate Similarity	NPD4139	Approved
0.7	Intermediate Similarity	NPD7639	Approved
0.7	Intermediate Similarity	NPD7640	Approved
0.699	Remote Similarity	NPD4768	Approved
0.699	Remote Similarity	NPD4767	Approved
0.6989	Remote Similarity	NPD6098	Approved
0.6988	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4785	Approved
0.6977	Remote Similarity	NPD4784	Approved
0.6977	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4195	Approved
0.6952	Remote Similarity	NPD6372	Approved
0.6952	Remote Similarity	NPD6373	Approved
0.6947	Remote Similarity	NPD6101	Approved
0.6947	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD4243	Approved
0.6941	Remote Similarity	NPD7150	Approved
0.6941	Remote Similarity	NPD7152	Approved
0.6941	Remote Similarity	NPD7151	Approved
0.6939	Remote Similarity	NPD5695	Phase 3
0.6923	Remote Similarity	NPD5701	Approved
0.6923	Remote Similarity	NPD5697	Approved
0.6915	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6922	Approved
0.6905	Remote Similarity	NPD6923	Approved
0.69	Remote Similarity	NPD5696	Approved
0.6897	Remote Similarity	NPD3703	Phase 2
0.6897	Remote Similarity	NPD8264	Approved
0.6887	Remote Similarity	NPD7102	Approved
0.6887	Remote Similarity	NPD7290	Approved
0.6887	Remote Similarity	NPD6883	Approved
0.6869	Remote Similarity	NPD7732	Phase 3
0.6857	Remote Similarity	NPD4730	Approved
0.6857	Remote Similarity	NPD5128	Approved
0.6857	Remote Similarity	NPD6011	Approved
0.6857	Remote Similarity	NPD5168	Approved
0.6857	Remote Similarity	NPD4729	Approved
0.6829	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7144	Approved
0.6824	Remote Similarity	NPD7143	Approved
0.6822	Remote Similarity	NPD8130	Phase 1
0.6822	Remote Similarity	NPD6617	Approved
0.6822	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6869	Approved
0.6822	Remote Similarity	NPD6650	Approved
0.6822	Remote Similarity	NPD6649	Approved
0.6822	Remote Similarity	NPD6847	Approved
0.6818	Remote Similarity	NPD6117	Approved
0.6818	Remote Similarity	NPD7115	Discovery
0.6813	Remote Similarity	NPD8028	Phase 2
0.6804	Remote Similarity	NPD5284	Approved
0.6804	Remote Similarity	NPD5281	Approved
0.6792	Remote Similarity	NPD6014	Approved
0.6792	Remote Similarity	NPD6013	Approved
0.6792	Remote Similarity	NPD6012	Approved
0.6792	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5360	Phase 3
0.6786	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD5733	Approved
0.6782	Remote Similarity	NPD4058	Approved
0.6778	Remote Similarity	NPD6929	Approved
0.6771	Remote Similarity	NPD6080	Approved
0.6771	Remote Similarity	NPD6904	Approved
0.6771	Remote Similarity	NPD6673	Approved
0.6759	Remote Similarity	NPD6882	Approved
0.6759	Remote Similarity	NPD8297	Approved
0.6754	Remote Similarity	NPD8328	Phase 3
0.6747	Remote Similarity	NPD7331	Phase 2
0.6742	Remote Similarity	NPD6116	Phase 1
0.6729	Remote Similarity	NPD5249	Phase 3
0.6729	Remote Similarity	NPD5251	Approved
0.6729	Remote Similarity	NPD5247	Approved
0.6729	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD5135	Approved
0.6729	Remote Similarity	NPD5250	Approved
0.6729	Remote Similarity	NPD5169	Approved
0.6729	Remote Similarity	NPD5248	Approved
0.6729	Remote Similarity	NPD4634	Approved
0.6703	Remote Similarity	NPD7509	Discontinued
0.6703	Remote Similarity	NPD6930	Phase 2
0.6703	Remote Similarity	NPD6931	Approved
0.6703	Remote Similarity	NPD4748	Discontinued
0.6701	Remote Similarity	NPD4096	Approved
0.6667	Remote Similarity	NPD5215	Approved
0.6667	Remote Similarity	NPD3671	Phase 1
0.6667	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD6115	Approved
0.6667	Remote Similarity	NPD5208	Approved
0.6667	Remote Similarity	NPD6697	Approved
0.6667	Remote Similarity	NPD5216	Approved
0.6667	Remote Similarity	NPD6118	Approved
0.6667	Remote Similarity	NPD6114	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