NPASS Compound

Structure

NPC84121 OpenBabel07101718242D 35 39 0 0 1 0 0 0 0 0999 V2000 -5.0662 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0206 4.2569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0456 4.2569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0206 -2.3069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0456 -2.3069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3775 0.9750 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 0.8444 -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 -3.3775 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 0 0 0 0 0 0 0 0 0 0 3.3775 2.9250 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 2.5331 0.4875 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 -0.0000 -0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0662 -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 2 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 2 0 0 0 0 0 0 0 0 0 -0.8444 0.4875 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3775 -0.9750 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 2.5331 3.4125 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 -1.6887 0.0000 0.0000 C 0 0 1 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 -5.9106 -1.4625 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 -2.4375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2219 -1.4625 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 27 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 8 31 1 0 0 0 0 10 11 1 0 0 0 0 10 21 1 0 0 0 0 11 24 1 0 0 0 0 12 13 1 0 0 0 0 12 25 1 0 0 0 0 13 30 1 0 0 0 0 14 15 1 0 0 0 0 14 27 1 0 0 0 0 15 29 1 0 0 0 0 16 17 1 0 0 0 0 16 29 1 0 0 0 0 17 31 1 0 0 0 0 18 22 2 0 0 0 0 18 27 1 0 0 0 0 19 23 1 0 0 0 0 19 32 1 0 0 0 0 20 33 2 0 0 0 0 20 35 1 0 0 0 0 21 22 1 0 0 0 0 21 31 1 6 0 0 0 22 29 1 0 0 0 0 23 26 1 0 0 0 0 23 34 1 1 0 0 0 24 30 1 1 0 0 0 24 32 1 0 0 0 0 25 28 1 0 0 0 0 25 35 1 1 0 0 0 26 28 1 0 0 0 0 26 30 1 1 0 0 0 29 6 1 1 0 0 0 30 7 1 1 0 0 0 31 32 1 1 0 0 0 32 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	484.39
Volume:	540.343
LogP:	6.747
LogD:	5.189
LogS:	-6.991
# Rotatable Bonds:	2
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.306
Synthetic Accessibility Score:	4.945
Fsp3:	0.906
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:	-5.013
MDCK Permeability:	1.694174534350168e-05
Pgp-inhibitor:	0.642
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.632
30% Bioavailability (F30%):	0.847

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.063
Plasma Protein Binding (PPB):	96.09632873535156%
Volume Distribution (VD):	1.344
Pgp-substrate:	2.3615458011627197%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.219
CYP2C19-inhibitor:	0.071
CYP2C19-substrate:	0.942
CYP2C9-inhibitor:	0.148
CYP2C9-substrate:	0.68
CYP2D6-inhibitor:	0.05
CYP2D6-substrate:	0.689
CYP3A4-inhibitor:	0.369
CYP3A4-substrate:	0.565

ADMET: Excretion

Clearance (CL):	3.247
Half-life (T1/2):	0.059

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.132
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.074
Maximum Recommended Daily Dose:	0.789
Skin Sensitization:	0.506
Carcinogencity:	0.006
Eye Corrosion:	0.772
Eye Irritation:	0.416
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: NPC84121

Natural Product ID:	NPC84121
*Common Name:**	3Beta-Acetoxy-6Beta-Hydroxy-Olean-18-Ene
IUPAC Name:	[(3S,4aR,5R,6aS,6aR,6bR,8aR,14aR,14bR)-5-hydroxy-4,4,6a,6b,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,6a,7,8,9,10,13,14,14a-tetradecahydropicen-3-yl] acetate
Synonyms:
Standard InCHIKey:	AREVFNRRRYVDPO-WKLSDETGSA-N
Standard InCHI:	InChI=1S/C32H52O3/c1-20(33)35-25-12-13-30(7)24-11-10-21-22-18-27(2,3)14-15-29(22,6)16-17-31(21,8)32(24,9)19-23(34)26(30)28(25,4)5/h18,21,23-26,34H,10-17,19H2,1-9H3/t21-,23-,24-,25+,26+,29-,30-,31-,32-/m1/s1
SMILES:	CC(=O)O[C@H]1CC[C@]2([C@H](C1(C)C)[C@H](O)C[C@@]1([C@@H]2CC[C@H]2[C@@]1(C)CC[C@@]1(C2=CC(C)(C)CC1)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2023108
PubChem CID:	60143459
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
Others	2

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT460	Cell Line	MT2	Homo sapiens	Activity	=	124.0	%	PMID[545846]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	=	102.0	%	PMID[545846]

☑ 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 NPC84121 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	202
0.1-0.2	1455
0.2-0.3	5453
0.3-0.4	15960
0.4-0.5	7800
0.5-0.6	4992
0.6-0.7	4590
0.7-0.8	1792
0.8-0.85	197
0.85-0.9	224
0.9-0.95	27
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC137306
0.9875	High Similarity	NPC191965
0.9375	High Similarity	NPC290495
0.9375	High Similarity	NPC195334
0.9259	High Similarity	NPC286786
0.9146	High Similarity	NPC132386
0.9136	High Similarity	NPC108476
0.908	High Similarity	NPC86368
0.907	High Similarity	NPC113989
0.907	High Similarity	NPC120840
0.9059	High Similarity	NPC40552
0.9059	High Similarity	NPC246708
0.9	High Similarity	NPC300499
0.8989	High Similarity	NPC327179
0.8977	High Similarity	NPC215700
0.8966	High Similarity	NPC60755
0.8966	High Similarity	NPC77099
0.8966	High Similarity	NPC470590
0.8966	High Similarity	NPC285184
0.8953	High Similarity	NPC290972
0.8953	High Similarity	NPC64872
0.8953	High Similarity	NPC470588
0.8953	High Similarity	NPC25906
0.8953	High Similarity	NPC30522
0.8941	High Similarity	NPC307426
0.8941	High Similarity	NPC242468
0.8941	High Similarity	NPC293564
0.8941	High Similarity	NPC102683
0.8941	High Similarity	NPC171203
0.8941	High Similarity	NPC68160
0.8941	High Similarity	NPC130577
0.8941	High Similarity	NPC142415
0.8941	High Similarity	NPC18064
0.8941	High Similarity	NPC51700
0.8941	High Similarity	NPC88716
0.8941	High Similarity	NPC98442
0.8916	High Similarity	NPC52108
0.8916	High Similarity	NPC474789
0.8902	High Similarity	NPC142163
0.8876	High Similarity	NPC474727
0.8875	High Similarity	NPC40394
0.8875	High Similarity	NPC101475
0.8875	High Similarity	NPC157996
0.8875	High Similarity	NPC34177
0.8864	High Similarity	NPC63118
0.8864	High Similarity	NPC49776
0.8864	High Similarity	NPC474436
0.8851	High Similarity	NPC474728
0.8851	High Similarity	NPC18872
0.8851	High Similarity	NPC130278
0.8851	High Similarity	NPC210037
0.8851	High Similarity	NPC290614
0.8851	High Similarity	NPC120968
0.8851	High Similarity	NPC273621
0.8851	High Similarity	NPC227467
0.8851	High Similarity	NPC477872
0.8851	High Similarity	NPC7260
0.8837	High Similarity	NPC181225
0.8837	High Similarity	NPC290690
0.8837	High Similarity	NPC17733
0.8837	High Similarity	NPC470629
0.8837	High Similarity	NPC182797
0.8837	High Similarity	NPC473242
0.8837	High Similarity	NPC474512
0.8837	High Similarity	NPC52169
0.8824	High Similarity	NPC10005
0.8824	High Similarity	NPC91525
0.8824	High Similarity	NPC9892
0.8824	High Similarity	NPC329943
0.8824	High Similarity	NPC72638
0.8824	High Similarity	NPC325594
0.8791	High Similarity	NPC58942
0.8791	High Similarity	NPC477876
0.8791	High Similarity	NPC260149
0.8791	High Similarity	NPC477875
0.8778	High Similarity	NPC230151
0.8765	High Similarity	NPC230295
0.8765	High Similarity	NPC474989
0.8765	High Similarity	NPC158662
0.8765	High Similarity	NPC470396
0.8765	High Similarity	NPC196753
0.8765	High Similarity	NPC22955
0.8765	High Similarity	NPC99168
0.8765	High Similarity	NPC98386
0.8765	High Similarity	NPC253807
0.8764	High Similarity	NPC74751
0.8764	High Similarity	NPC296164
0.8764	High Similarity	NPC78580
0.8764	High Similarity	NPC23621
0.8764	High Similarity	NPC184006
0.875	High Similarity	NPC105189
0.875	High Similarity	NPC265328
0.875	High Similarity	NPC187722
0.875	High Similarity	NPC120098
0.875	High Similarity	NPC290598
0.875	High Similarity	NPC27765
0.875	High Similarity	NPC122418
0.875	High Similarity	NPC30590
0.8736	High Similarity	NPC234346
0.8736	High Similarity	NPC293048
0.8736	High Similarity	NPC225585
0.8736	High Similarity	NPC270768
0.8736	High Similarity	NPC127689
0.8736	High Similarity	NPC198664
0.8736	High Similarity	NPC474972
0.8736	High Similarity	NPC95246
0.8736	High Similarity	NPC130520
0.8736	High Similarity	NPC274330
0.8736	High Similarity	NPC59263
0.8736	High Similarity	NPC161751
0.8736	High Similarity	NPC143232
0.8736	High Similarity	NPC121798
0.8736	High Similarity	NPC263393
0.8736	High Similarity	NPC61543
0.8721	High Similarity	NPC46912
0.8721	High Similarity	NPC162107
0.8696	High Similarity	NPC474190
0.8696	High Similarity	NPC476195
0.869	High Similarity	NPC5280
0.8681	High Similarity	NPC476878
0.8681	High Similarity	NPC476879
0.8675	High Similarity	NPC116202
0.8667	High Similarity	NPC23241
0.8667	High Similarity	NPC195715
0.8659	High Similarity	NPC291379
0.8659	High Similarity	NPC53744
0.8659	High Similarity	NPC100906
0.8652	High Similarity	NPC295643
0.8652	High Similarity	NPC118519
0.8652	High Similarity	NPC229281
0.8652	High Similarity	NPC158059
0.8652	High Similarity	NPC202728
0.8652	High Similarity	NPC74855
0.8652	High Similarity	NPC307335
0.8652	High Similarity	NPC136313
0.8652	High Similarity	NPC214756
0.8652	High Similarity	NPC272075
0.8642	High Similarity	NPC84868
0.8636	High Similarity	NPC86372
0.8636	High Similarity	NPC470589
0.8636	High Similarity	NPC172361
0.8636	High Similarity	NPC126369
0.8636	High Similarity	NPC193750
0.8636	High Similarity	NPC111110
0.8636	High Similarity	NPC291028
0.8625	High Similarity	NPC138374
0.8625	High Similarity	NPC34700
0.8621	High Similarity	NPC224145
0.8605	High Similarity	NPC474970
0.8602	High Similarity	NPC233012
0.8602	High Similarity	NPC476132
0.8602	High Similarity	NPC96784
0.8602	High Similarity	NPC235920
0.8602	High Similarity	NPC54909
0.8602	High Similarity	NPC473160
0.8587	High Similarity	NPC164349
0.8587	High Similarity	NPC471966
0.8571	High Similarity	NPC304899
0.8571	High Similarity	NPC253115
0.8571	High Similarity	NPC304285
0.8556	High Similarity	NPC91010
0.8556	High Similarity	NPC282395
0.8556	High Similarity	NPC263548
0.8556	High Similarity	NPC231063
0.8556	High Similarity	NPC145667
0.8556	High Similarity	NPC114159
0.8556	High Similarity	NPC299996
0.8556	High Similarity	NPC20235
0.8556	High Similarity	NPC88116
0.8556	High Similarity	NPC6818
0.8556	High Similarity	NPC32407
0.8556	High Similarity	NPC191412
0.8554	High Similarity	NPC295131
0.8539	High Similarity	NPC84319
0.8539	High Similarity	NPC235884
0.8539	High Similarity	NPC145067
0.8539	High Similarity	NPC472149
0.8539	High Similarity	NPC25299
0.8539	High Similarity	NPC155120
0.8539	High Similarity	NPC306541
0.8539	High Similarity	NPC4036
0.8539	High Similarity	NPC38754
0.8539	High Similarity	NPC233455
0.8539	High Similarity	NPC228784
0.8539	High Similarity	NPC474525
0.8539	High Similarity	NPC288833
0.8539	High Similarity	NPC324341
0.8539	High Similarity	NPC158030
0.8539	High Similarity	NPC52021
0.8539	High Similarity	NPC282616
0.8539	High Similarity	NPC966
0.8539	High Similarity	NPC71074
0.8539	High Similarity	NPC300351
0.8539	High Similarity	NPC65120
0.8523	High Similarity	NPC474686
0.8523	High Similarity	NPC475049
0.8519	High Similarity	NPC106364
0.8511	High Similarity	NPC283343
0.8511	High Similarity	NPC273668
0.8511	High Similarity	NPC258547

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 NPC84121 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	1737
0.2-0.3	4100
0.3-0.4	2198
0.4-0.5	524
0.5-0.6	211
0.6-0.7	177
0.7-0.8	18
0.8-0.85	2
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8889	High Similarity	NPD7645	Phase 2
0.8764	High Similarity	NPD7748	Approved
0.8681	High Similarity	NPD7902	Approved
0.8539	High Similarity	NPD7515	Phase 2
0.8352	Intermediate Similarity	NPD7900	Approved
0.8352	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD8035	Phase 2
0.7935	Intermediate Similarity	NPD8034	Phase 2
0.7907	Intermediate Similarity	NPD7525	Registered
0.7865	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD6399	Phase 3
0.7629	Intermediate Similarity	NPD7638	Approved
0.7551	Intermediate Similarity	NPD7639	Approved
0.7551	Intermediate Similarity	NPD7640	Approved
0.7529	Intermediate Similarity	NPD7339	Approved
0.7529	Intermediate Similarity	NPD6942	Approved
0.7442	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD3618	Phase 1
0.7363	Intermediate Similarity	NPD4786	Approved
0.7353	Intermediate Similarity	NPD6675	Approved
0.7353	Intermediate Similarity	NPD6402	Approved
0.7353	Intermediate Similarity	NPD7128	Approved
0.7353	Intermediate Similarity	NPD5739	Approved
0.734	Intermediate Similarity	NPD5328	Approved
0.7333	Intermediate Similarity	NPD3667	Approved
0.7212	Intermediate Similarity	NPD7320	Approved
0.7212	Intermediate Similarity	NPD6899	Approved
0.7212	Intermediate Similarity	NPD6881	Approved
0.7204	Intermediate Similarity	NPD7334	Approved
0.7204	Intermediate Similarity	NPD7521	Approved
0.7204	Intermediate Similarity	NPD6684	Approved
0.7204	Intermediate Similarity	NPD7146	Approved
0.7204	Intermediate Similarity	NPD6409	Approved
0.7204	Intermediate Similarity	NPD5330	Approved
0.7188	Intermediate Similarity	NPD6079	Approved
0.717	Intermediate Similarity	NPD8130	Phase 1
0.7143	Intermediate Similarity	NPD6373	Approved
0.7143	Intermediate Similarity	NPD6372	Approved
0.7143	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD3573	Approved
0.7115	Intermediate Similarity	NPD5701	Approved
0.7115	Intermediate Similarity	NPD5697	Approved
0.7113	Intermediate Similarity	NPD4202	Approved
0.7103	Intermediate Similarity	NPD8297	Approved
0.708	Intermediate Similarity	NPD8328	Phase 3
0.7075	Intermediate Similarity	NPD6883	Approved
0.7075	Intermediate Similarity	NPD7102	Approved
0.7075	Intermediate Similarity	NPD7290	Approved
0.7053	Intermediate Similarity	NPD6903	Approved
0.7048	Intermediate Similarity	NPD6011	Approved
0.701	Intermediate Similarity	NPD6411	Approved
0.7009	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6869	Approved
0.7009	Intermediate Similarity	NPD6649	Approved
0.7009	Intermediate Similarity	NPD6650	Approved
0.7009	Intermediate Similarity	NPD6847	Approved
0.7009	Intermediate Similarity	NPD6617	Approved
0.7	Intermediate Similarity	NPD6083	Phase 2
0.7	Intermediate Similarity	NPD6084	Phase 2
0.7	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD3133	Approved
0.6989	Remote Similarity	NPD3665	Phase 1
0.6989	Remote Similarity	NPD3666	Approved
0.6981	Remote Similarity	NPD6012	Approved
0.6981	Remote Similarity	NPD6013	Approved
0.6981	Remote Similarity	NPD6014	Approved
0.6979	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6051	Approved
0.6964	Remote Similarity	NPD8377	Approved
0.6964	Remote Similarity	NPD8294	Approved
0.6944	Remote Similarity	NPD6882	Approved
0.6932	Remote Similarity	NPD8264	Approved
0.6931	Remote Similarity	NPD4225	Approved
0.6903	Remote Similarity	NPD8033	Approved
0.6903	Remote Similarity	NPD8378	Approved
0.6903	Remote Similarity	NPD8380	Approved
0.6903	Remote Similarity	NPD8379	Approved
0.6903	Remote Similarity	NPD8296	Approved
0.6903	Remote Similarity	NPD8335	Approved
0.6893	Remote Similarity	NPD7632	Discontinued
0.6875	Remote Similarity	NPD6672	Approved
0.6875	Remote Similarity	NPD5737	Approved
0.6832	Remote Similarity	NPD4755	Approved
0.6818	Remote Similarity	NPD6926	Approved
0.6818	Remote Similarity	NPD6924	Approved
0.6804	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD6101	Approved
0.6786	Remote Similarity	NPD7328	Approved
0.6786	Remote Similarity	NPD7327	Approved
0.6782	Remote Similarity	NPD4243	Approved
0.6778	Remote Similarity	NPD6116	Phase 1
0.6739	Remote Similarity	NPD7509	Discontinued
0.6733	Remote Similarity	NPD4697	Phase 3
0.6733	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD5222	Approved
0.6733	Remote Similarity	NPD5221	Approved
0.6726	Remote Similarity	NPD7516	Approved
0.6699	Remote Similarity	NPD5286	Approved
0.6699	Remote Similarity	NPD5285	Approved
0.6699	Remote Similarity	NPD4700	Approved
0.6699	Remote Similarity	NPD4696	Approved
0.6696	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD6117	Approved
0.6667	Remote Similarity	NPD6933	Approved
0.6667	Remote Similarity	NPD6098	Approved
0.6637	Remote Similarity	NPD6335	Approved
0.6636	Remote Similarity	NPD6412	Phase 2
0.6635	Remote Similarity	NPD5223	Approved
0.6634	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD5695	Phase 3
0.6632	Remote Similarity	NPD3668	Phase 3
0.6632	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4195	Approved
0.6629	Remote Similarity	NPD4784	Approved
0.6629	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD4785	Approved
0.6609	Remote Similarity	NPD7503	Approved
0.6607	Remote Similarity	NPD6274	Approved
0.6607	Remote Similarity	NPD6868	Approved
0.6602	Remote Similarity	NPD5290	Discontinued
0.6602	Remote Similarity	NPD5696	Approved
0.6598	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD7152	Approved
0.6591	Remote Similarity	NPD7150	Approved
0.6591	Remote Similarity	NPD7151	Approved
0.6579	Remote Similarity	NPD7100	Approved
0.6579	Remote Similarity	NPD7101	Approved
0.6577	Remote Similarity	NPD4632	Approved
0.6577	Remote Similarity	NPD8133	Approved
0.6571	Remote Similarity	NPD5225	Approved
0.6571	Remote Similarity	NPD4633	Approved
0.6571	Remote Similarity	NPD5226	Approved
0.6571	Remote Similarity	NPD5224	Approved
0.6571	Remote Similarity	NPD5211	Phase 2
0.6569	Remote Similarity	NPD7614	Phase 1
0.6569	Remote Similarity	NPD7732	Phase 3
0.6559	Remote Similarity	NPD4748	Discontinued
0.6555	Remote Similarity	NPD7736	Approved
0.6552	Remote Similarity	NPD6922	Approved
0.6552	Remote Similarity	NPD6923	Approved
0.6549	Remote Similarity	NPD6317	Approved
0.6542	Remote Similarity	NPD6008	Approved
0.6526	Remote Similarity	NPD6695	Phase 3
0.6522	Remote Similarity	NPD6114	Approved
0.6522	Remote Similarity	NPD6115	Approved
0.6522	Remote Similarity	NPD6697	Approved
0.6522	Remote Similarity	NPD6118	Approved
0.6514	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5175	Approved
0.6509	Remote Similarity	NPD4754	Approved
0.6509	Remote Similarity	NPD5174	Approved
0.65	Remote Similarity	NPD7637	Suspended
0.6495	Remote Similarity	NPD5279	Phase 3
0.6491	Remote Similarity	NPD6313	Approved
0.6491	Remote Similarity	NPD6314	Approved
0.6477	Remote Similarity	NPD7144	Approved
0.6477	Remote Similarity	NPD7143	Approved
0.6466	Remote Similarity	NPD6908	Approved
0.6466	Remote Similarity	NPD6909	Approved
0.6465	Remote Similarity	NPD4753	Phase 2
0.6465	Remote Similarity	NPD6904	Approved
0.6465	Remote Similarity	NPD6673	Approved
0.6465	Remote Similarity	NPD6080	Approved
0.6452	Remote Similarity	NPD6929	Approved
0.6449	Remote Similarity	NPD5141	Approved
0.6436	Remote Similarity	NPD5779	Approved
0.6436	Remote Similarity	NPD5778	Approved
0.6429	Remote Similarity	NPD7750	Discontinued
0.6422	Remote Similarity	NPD6686	Approved
0.6421	Remote Similarity	NPD4221	Approved
0.6421	Remote Similarity	NPD4223	Phase 3
0.6421	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6009	Approved
0.6392	Remote Similarity	NPD5329	Approved
0.6392	Remote Similarity	NPD1694	Approved
0.6389	Remote Similarity	NPD4767	Approved
0.6389	Remote Similarity	NPD4768	Approved
0.6387	Remote Similarity	NPD7507	Approved
0.6383	Remote Similarity	NPD4695	Discontinued
0.6383	Remote Similarity	NPD6930	Phase 2
0.6383	Remote Similarity	NPD6931	Approved
0.6379	Remote Similarity	NPD6319	Approved
0.6374	Remote Similarity	NPD5275	Approved
0.6374	Remote Similarity	NPD4190	Phase 3
0.6373	Remote Similarity	NPD6001	Approved
0.6364	Remote Similarity	NPD5208	Approved
0.6356	Remote Similarity	NPD7604	Phase 2
0.6354	Remote Similarity	NPD4788	Approved
0.6337	Remote Similarity	NPD5284	Approved
0.6337	Remote Similarity	NPD5281	Approved
0.6333	Remote Similarity	NPD8293	Discontinued
0.6327	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD5983	Phase 2
0.6325	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD5344	Discontinued
0.631	Remote Similarity	NPD368	Approved
0.6306	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7492	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