NPASS Compound

Structure

NPC108131 OpenBabel07101719122D 33 37 0 0 1 0 0 0 0 0999 V2000 -4.7090 -0.9425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5034 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0165 -0.6173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1337 2.3500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0281 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -2.9211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4557 1.7614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7566 -0.7401 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4557 0.1860 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6865 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6865 -0.9737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5297 -2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 0.4868 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1051 -1.4637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 1.4605 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8432 -1.4605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8432 0.4868 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 3.3729 -2.9211 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4060 -2.3897 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1527 -1.2612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 6 29 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 22 1 0 0 0 0 10 13 1 0 0 0 0 10 19 1 0 0 0 0 11 15 1 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 27 1 0 0 0 0 14 28 1 0 0 0 0 15 30 1 0 0 0 0 16 17 1 0 0 0 0 16 27 1 0 0 0 0 17 29 1 0 0 0 0 18 1 1 1 0 0 0 18 25 1 0 0 0 0 19 18 1 6 0 0 0 19 24 1 0 0 0 0 20 24 1 0 0 0 0 20 29 1 6 0 0 0 21 26 1 0 0 0 0 21 28 1 1 0 0 0 22 28 1 1 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 27 1 1 0 0 0 25 32 2 0 0 0 0 25 33 1 0 0 0 0 27 4 1 1 0 0 0 28 5 1 1 0 0 0 29 30 1 1 0 0 0 30 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.36
Volume:	505.751
LogP:	5.545
LogD:	5.628
LogS:	-4.521
# Rotatable Bonds:	2
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.471
Synthetic Accessibility Score:	4.773
Fsp3:	0.933
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:	-5.312
MDCK Permeability:	4.58893264294602e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.038
30% Bioavailability (F30%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	94.5372543334961%
Volume Distribution (VD):	1.092
Pgp-substrate:	2.000596046447754%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.787
CYP2C19-inhibitor:	0.063
CYP2C19-substrate:	0.967
CYP2C9-inhibitor:	0.149
CYP2C9-substrate:	0.953
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.803
CYP3A4-inhibitor:	0.129
CYP3A4-substrate:	0.141

ADMET: Excretion

Clearance (CL):	2.846
Half-life (T1/2):	0.397

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.309
Drug-inuced Liver Injury (DILI):	0.025
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.05
Maximum Recommended Daily Dose:	0.19
Skin Sensitization:	0.148
Carcinogencity:	0.007
Eye Corrosion:	0.321
Eye Irritation:	0.718
Respiratory Toxicity:	0.937

Download Data

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

Natural Product: NPC108131

Natural Product ID:	NPC108131
*Common Name:**	(20S)-3-Oxolupan-29-Oic Acid
IUPAC Name:	(2S)-2-[(1R,3aR,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-9-oxo-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysen-1-yl]propanoic acid
Synonyms:
Standard InCHIKey:	GUUIRVFLILUCRL-PLUXSBPDSA-N
Standard InCHI:	InChI=1S/C30H48O3/c1-18(25(32)33)19-10-13-27(4)16-17-29(6)20(24(19)27)8-9-22-28(5)14-12-23(31)26(2,3)21(28)11-15-30(22,29)7/h18-22,24H,8-17H2,1-7H3,(H,32,33)/t18-,19-,20+,21-,22+,24+,27+,28-,29+,30+/m0/s1
SMILES:	OC(=O)[C@H]([C@@H]1CC[C@]2([C@H]1[C@H]1CC[C@H]3[C@@]([C@]1(C)CC2)(C)CC[C@@H]1[C@]3(C)CCC(=O)C1(C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3109385
PubChem CID:	76313951
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
NPO33010	euonymus carnosus	Species	Celastraceae	Eukaryota	Plant	n.a.	n.a.	PMID[24467317]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	6

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[543246]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[543246]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[543246]

☑ 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 NPC108131 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	312
0.1-0.2	3725
0.2-0.3	17112
0.3-0.4	8193
0.4-0.5	5704
0.5-0.6	4946
0.6-0.7	2185
0.7-0.8	394
0.8-0.85	74
0.85-0.9	42
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9394	High Similarity	NPC473225
0.9385	High Similarity	NPC42060
0.9254	High Similarity	NPC474962
0.9104	High Similarity	NPC469724
0.9104	High Similarity	NPC100917
0.9104	High Similarity	NPC31187
0.9104	High Similarity	NPC281203
0.9091	High Similarity	NPC477931
0.9091	High Similarity	NPC268736
0.8971	High Similarity	NPC469941
0.8971	High Similarity	NPC476734
0.8971	High Similarity	NPC252032
0.8971	High Similarity	NPC196197
0.8971	High Similarity	NPC319671
0.8955	High Similarity	NPC130459
0.8955	High Similarity	NPC478180
0.8955	High Similarity	NPC474221
0.8904	High Similarity	NPC192744
0.8889	High Similarity	NPC298168
0.8889	High Similarity	NPC143133
0.8841	High Similarity	NPC477929
0.8732	High Similarity	NPC280026
0.8732	High Similarity	NPC167702
0.8714	High Similarity	NPC472309
0.8714	High Similarity	NPC469940
0.8696	High Similarity	NPC64466
0.863	High Similarity	NPC477918
0.863	High Similarity	NPC68828
0.8611	High Similarity	NPC472311
0.8611	High Similarity	NPC97534
0.8611	High Similarity	NPC212733
0.8611	High Similarity	NPC195155
0.8611	High Similarity	NPC174964
0.8571	High Similarity	NPC477850
0.8553	High Similarity	NPC61107
0.8553	High Similarity	NPC30583
0.8553	High Similarity	NPC289486
0.8533	High Similarity	NPC261616
0.8514	High Similarity	NPC185465
0.8493	Intermediate Similarity	NPC475742
0.8493	Intermediate Similarity	NPC4209
0.8493	Intermediate Similarity	NPC5767
0.8472	Intermediate Similarity	NPC477930
0.8451	Intermediate Similarity	NPC197701
0.8451	Intermediate Similarity	NPC320549
0.8451	Intermediate Similarity	NPC151018
0.8451	Intermediate Similarity	NPC156277
0.8451	Intermediate Similarity	NPC58057
0.8442	Intermediate Similarity	NPC472740
0.84	Intermediate Similarity	NPC320144
0.8378	Intermediate Similarity	NPC23884
0.8378	Intermediate Similarity	NPC317913
0.8378	Intermediate Similarity	NPC180199
0.8378	Intermediate Similarity	NPC221420
0.8378	Intermediate Similarity	NPC207010
0.8378	Intermediate Similarity	NPC66105
0.8378	Intermediate Similarity	NPC477919
0.8356	Intermediate Similarity	NPC477934
0.8333	Intermediate Similarity	NPC232112
0.8333	Intermediate Similarity	NPC310766
0.8289	Intermediate Similarity	NPC472853
0.8286	Intermediate Similarity	NPC260319
0.8286	Intermediate Similarity	NPC103647
0.8286	Intermediate Similarity	NPC470956
0.8286	Intermediate Similarity	NPC2568
0.8286	Intermediate Similarity	NPC180777
0.8267	Intermediate Similarity	NPC324700
0.8267	Intermediate Similarity	NPC476732
0.8267	Intermediate Similarity	NPC34046
0.8267	Intermediate Similarity	NPC63020
0.8267	Intermediate Similarity	NPC199965
0.8267	Intermediate Similarity	NPC224802
0.8267	Intermediate Similarity	NPC80089
0.8267	Intermediate Similarity	NPC329117
0.8267	Intermediate Similarity	NPC171426
0.8243	Intermediate Similarity	NPC477932
0.8243	Intermediate Similarity	NPC246445
0.8243	Intermediate Similarity	NPC477933
0.8228	Intermediate Similarity	NPC201655
0.8219	Intermediate Similarity	NPC472854
0.8219	Intermediate Similarity	NPC254340
0.8194	Intermediate Similarity	NPC473267
0.8169	Intermediate Similarity	NPC324607
0.8169	Intermediate Similarity	NPC6120
0.8169	Intermediate Similarity	NPC131892
0.8169	Intermediate Similarity	NPC213178
0.8169	Intermediate Similarity	NPC321732
0.8169	Intermediate Similarity	NPC327728
0.8158	Intermediate Similarity	NPC201459
0.8158	Intermediate Similarity	NPC201276
0.8158	Intermediate Similarity	NPC80891
0.8133	Intermediate Similarity	NPC474404
0.8133	Intermediate Similarity	NPC471035
0.8133	Intermediate Similarity	NPC212661
0.8133	Intermediate Similarity	NPC112463
0.8116	Intermediate Similarity	NPC230047
0.8116	Intermediate Similarity	NPC19311
0.8116	Intermediate Similarity	NPC469791
0.8108	Intermediate Similarity	NPC21220
0.8108	Intermediate Similarity	NPC125767
0.8108	Intermediate Similarity	NPC273366
0.8082	Intermediate Similarity	NPC330659
0.8082	Intermediate Similarity	NPC244708
0.8082	Intermediate Similarity	NPC36310
0.8082	Intermediate Similarity	NPC161187
0.8056	Intermediate Similarity	NPC476731
0.803	Intermediate Similarity	NPC162685
0.8026	Intermediate Similarity	NPC26029
0.8	Intermediate Similarity	NPC151464
0.8	Intermediate Similarity	NPC294438
0.8	Intermediate Similarity	NPC472487
0.8	Intermediate Similarity	NPC143597
0.8	Intermediate Similarity	NPC264317
0.8	Intermediate Similarity	NPC472486
0.8	Intermediate Similarity	NPC20466
0.7973	Intermediate Similarity	NPC255168
0.7949	Intermediate Similarity	NPC58631
0.7949	Intermediate Similarity	NPC147066
0.7949	Intermediate Similarity	NPC103754
0.7949	Intermediate Similarity	NPC12933
0.7949	Intermediate Similarity	NPC474484
0.7945	Intermediate Similarity	NPC290058
0.7945	Intermediate Similarity	NPC247195
0.7945	Intermediate Similarity	NPC89310
0.7927	Intermediate Similarity	NPC474719
0.7922	Intermediate Similarity	NPC472310
0.7917	Intermediate Similarity	NPC178541
0.7901	Intermediate Similarity	NPC2783
0.7901	Intermediate Similarity	NPC12774
0.7895	Intermediate Similarity	NPC475031
0.7895	Intermediate Similarity	NPC264602
0.7887	Intermediate Similarity	NPC41542
0.7875	Intermediate Similarity	NPC471044
0.7875	Intermediate Similarity	NPC473336
0.7875	Intermediate Similarity	NPC319909
0.7867	Intermediate Similarity	NPC24014
0.7867	Intermediate Similarity	NPC27349
0.7867	Intermediate Similarity	NPC179858
0.7867	Intermediate Similarity	NPC72444
0.7848	Intermediate Similarity	NPC477936
0.7848	Intermediate Similarity	NPC477935
0.7848	Intermediate Similarity	NPC121121
0.7846	Intermediate Similarity	NPC184819
0.7838	Intermediate Similarity	NPC81759
0.7838	Intermediate Similarity	NPC68426
0.7838	Intermediate Similarity	NPC475230
0.7838	Intermediate Similarity	NPC282905
0.7838	Intermediate Similarity	NPC477229
0.7821	Intermediate Similarity	NPC477851
0.7805	Intermediate Similarity	NPC252714
0.7805	Intermediate Similarity	NPC264005
0.7805	Intermediate Similarity	NPC269360
0.7805	Intermediate Similarity	NPC33768
0.7792	Intermediate Similarity	NPC31031
0.7792	Intermediate Similarity	NPC243594
0.7792	Intermediate Similarity	NPC472608
0.7792	Intermediate Similarity	NPC321690
0.7778	Intermediate Similarity	NPC475977
0.7778	Intermediate Similarity	NPC474954
0.7763	Intermediate Similarity	NPC471046
0.775	Intermediate Similarity	NPC245866
0.775	Intermediate Similarity	NPC175410
0.775	Intermediate Similarity	NPC475726
0.775	Intermediate Similarity	NPC472743
0.7733	Intermediate Similarity	NPC130011
0.7733	Intermediate Similarity	NPC133922
0.7733	Intermediate Similarity	NPC159325
0.7733	Intermediate Similarity	NPC168511
0.7722	Intermediate Similarity	NPC48756
0.7722	Intermediate Similarity	NPC201912
0.7722	Intermediate Similarity	NPC280781
0.7722	Intermediate Similarity	NPC267691
0.7722	Intermediate Similarity	NPC271572
0.7722	Intermediate Similarity	NPC274050
0.7722	Intermediate Similarity	NPC162632
0.7722	Intermediate Similarity	NPC263272
0.7722	Intermediate Similarity	NPC38350
0.7722	Intermediate Similarity	NPC474870
0.7714	Intermediate Similarity	NPC128608
0.7711	Intermediate Similarity	NPC4309
0.7711	Intermediate Similarity	NPC16377
0.7711	Intermediate Similarity	NPC471900
0.7703	Intermediate Similarity	NPC478227
0.7692	Intermediate Similarity	NPC53245
0.7692	Intermediate Similarity	NPC288296
0.7692	Intermediate Similarity	NPC477371
0.7692	Intermediate Similarity	NPC215843
0.7692	Intermediate Similarity	NPC52951
0.7692	Intermediate Similarity	NPC245029
0.7692	Intermediate Similarity	NPC31302
0.7683	Intermediate Similarity	NPC70661
0.7683	Intermediate Similarity	NPC92139
0.7654	Intermediate Similarity	NPC474233
0.7654	Intermediate Similarity	NPC474996
0.7654	Intermediate Similarity	NPC475745
0.7654	Intermediate Similarity	NPC474482
0.7632	Intermediate Similarity	NPC267753
0.7632	Intermediate Similarity	NPC159789
0.7625	Intermediate Similarity	NPC251779
0.7625	Intermediate Similarity	NPC320514

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 NPC108131 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	363
0.1-0.2	3712
0.2-0.3	3588
0.3-0.4	867
0.4-0.5	257
0.5-0.6	249
0.6-0.7	85
0.7-0.8	5
0.8-0.85	19
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9385	High Similarity	NPD4224	Phase 2
0.9265	High Similarity	NPD6081	Approved
0.8824	High Similarity	NPD5360	Phase 3
0.8824	High Similarity	NPD5361	Clinical (unspecified phase)
0.8732	High Similarity	NPD6113	Clinical (unspecified phase)
0.8571	High Similarity	NPD4789	Approved
0.8493	Intermediate Similarity	NPD6117	Approved
0.8451	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8451	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD6116	Phase 1
0.831	Intermediate Similarity	NPD4245	Approved
0.831	Intermediate Similarity	NPD4244	Approved
0.8267	Intermediate Similarity	NPD6114	Approved
0.8267	Intermediate Similarity	NPD6118	Approved
0.8267	Intermediate Similarity	NPD6697	Approved
0.8267	Intermediate Similarity	NPD6115	Approved
0.8194	Intermediate Similarity	NPD4758	Discontinued
0.8194	Intermediate Similarity	NPD5777	Approved
0.8169	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.8169	Intermediate Similarity	NPD3698	Phase 2
0.8169	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD3702	Approved
0.8	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD5364	Discontinued
0.7632	Intermediate Similarity	NPD3703	Phase 2
0.7442	Intermediate Similarity	NPD8035	Phase 2
0.7442	Intermediate Similarity	NPD8034	Phase 2
0.7342	Intermediate Similarity	NPD3671	Phase 1
0.7317	Intermediate Similarity	NPD4788	Approved
0.7164	Intermediate Similarity	NPD615	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD3617	Approved
0.7024	Intermediate Similarity	NPD4786	Approved
0.6988	Remote Similarity	NPD4221	Approved
0.6988	Remote Similarity	NPD4223	Phase 3
0.6966	Remote Similarity	NPD6399	Phase 3
0.6941	Remote Similarity	NPD5329	Approved
0.6901	Remote Similarity	NPD3198	Approved
0.6897	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4139	Approved
0.6867	Remote Similarity	NPD4692	Approved
0.686	Remote Similarity	NPD6098	Approved
0.6854	Remote Similarity	NPD7515	Phase 2
0.6824	Remote Similarity	NPD4197	Approved
0.6818	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3667	Approved
0.6753	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5737	Approved
0.6705	Remote Similarity	NPD6672	Approved
0.6703	Remote Similarity	NPD7748	Approved
0.6667	Remote Similarity	NPD4690	Approved
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD7146	Approved
0.6667	Remote Similarity	NPD4787	Phase 1
0.6667	Remote Similarity	NPD4689	Approved
0.6667	Remote Similarity	NPD4138	Approved
0.6667	Remote Similarity	NPD5330	Approved
0.6667	Remote Similarity	NPD4688	Approved
0.6667	Remote Similarity	NPD6684	Approved
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD5281	Approved
0.6667	Remote Similarity	NPD5205	Approved
0.6667	Remote Similarity	NPD7521	Approved
0.6667	Remote Similarity	NPD7334	Approved
0.6667	Remote Similarity	NPD6409	Approved
0.6667	Remote Similarity	NPD4693	Phase 3
0.6667	Remote Similarity	NPD5284	Approved
0.6629	Remote Similarity	NPD5328	Approved
0.6629	Remote Similarity	NPD6673	Approved
0.6629	Remote Similarity	NPD6904	Approved
0.6629	Remote Similarity	NPD6080	Approved
0.6628	Remote Similarity	NPD3665	Phase 1
0.6628	Remote Similarity	NPD3666	Approved
0.6628	Remote Similarity	NPD3133	Approved
0.6526	Remote Similarity	NPD8418	Phase 2
0.6517	Remote Similarity	NPD6903	Approved
0.6517	Remote Similarity	NPD5208	Approved
0.6489	Remote Similarity	NPD7902	Approved
0.6484	Remote Similarity	NPD6079	Approved
0.6477	Remote Similarity	NPD5280	Approved
0.6477	Remote Similarity	NPD3618	Phase 1
0.6477	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD4694	Approved
0.6477	Remote Similarity	NPD5690	Phase 2
0.6462	Remote Similarity	NPD634	Phase 3
0.6452	Remote Similarity	NPD5695	Phase 3
0.6444	Remote Similarity	NPD4753	Phase 2
0.6429	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD5696	Approved
0.6383	Remote Similarity	NPD7614	Phase 1
0.6377	Remote Similarity	NPD3186	Phase 1
0.6364	Remote Similarity	NPD375	Phase 2
0.6353	Remote Similarity	NPD6928	Phase 2
0.6304	Remote Similarity	NPD5693	Phase 1
0.6304	Remote Similarity	NPD6050	Approved
0.6292	Remote Similarity	NPD5279	Phase 3
0.6277	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4747	Approved
0.625	Remote Similarity	NPD3668	Phase 3
0.6237	Remote Similarity	NPD4202	Approved
0.6235	Remote Similarity	NPD4195	Approved
0.6203	Remote Similarity	NPD6705	Phase 1
0.62	Remote Similarity	NPD5739	Approved
0.62	Remote Similarity	NPD6402	Approved
0.62	Remote Similarity	NPD7128	Approved
0.62	Remote Similarity	NPD6675	Approved
0.6196	Remote Similarity	NPD5692	Phase 3
0.6196	Remote Similarity	NPD5207	Approved
0.6173	Remote Similarity	NPD4243	Approved
0.617	Remote Similarity	NPD7900	Approved
0.617	Remote Similarity	NPD6001	Approved
0.617	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD4695	Discontinued
0.6129	Remote Similarity	NPD5694	Approved
0.6125	Remote Similarity	NPD4137	Phase 3
0.6119	Remote Similarity	NPD345	Approved
0.6119	Remote Similarity	NPD344	Approved
0.6119	Remote Similarity	NPD343	Approved
0.6118	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD4238	Approved
0.6118	Remote Similarity	NPD4802	Phase 2
0.6111	Remote Similarity	NPD4623	Approved
0.6111	Remote Similarity	NPD4519	Discontinued
0.6105	Remote Similarity	NPD4629	Approved
0.6105	Remote Similarity	NPD5210	Approved
0.6082	Remote Similarity	NPD7638	Approved
0.6078	Remote Similarity	NPD7320	Approved
0.6078	Remote Similarity	NPD6899	Approved
0.6078	Remote Similarity	NPD6881	Approved
0.6064	Remote Similarity	NPD5133	Approved
0.6049	Remote Similarity	NPD4691	Approved
0.6044	Remote Similarity	NPD3573	Approved
0.6042	Remote Similarity	NPD5221	Approved
0.6042	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD4697	Phase 3
0.6042	Remote Similarity	NPD5222	Approved
0.604	Remote Similarity	NPD6920	Discontinued
0.6024	Remote Similarity	NPD4784	Approved
0.6024	Remote Similarity	NPD4785	Approved
0.6024	Remote Similarity	NPD5733	Approved
0.6022	Remote Similarity	NPD4096	Approved
0.602	Remote Similarity	NPD7639	Approved
0.602	Remote Similarity	NPD6404	Discontinued
0.602	Remote Similarity	NPD7640	Approved
0.6019	Remote Similarity	NPD6372	Approved
0.6019	Remote Similarity	NPD6373	Approved
0.6	Remote Similarity	NPD387	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.598	Remote Similarity	NPD5701	Approved
0.598	Remote Similarity	NPD5697	Approved
0.5979	Remote Similarity	NPD4755	Approved
0.5979	Remote Similarity	NPD5173	Approved
0.5977	Remote Similarity	NPD7525	Registered
0.5962	Remote Similarity	NPD7102	Approved
0.5962	Remote Similarity	NPD7290	Approved
0.5962	Remote Similarity	NPD6883	Approved
0.5952	Remote Similarity	NPD7339	Approved
0.5952	Remote Similarity	NPD6942	Approved
0.5938	Remote Similarity	NPD5654	Approved
0.593	Remote Similarity	NPD4776	Phase 2
0.593	Remote Similarity	NPD4777	Suspended
0.5926	Remote Similarity	NPD3725	Approved
0.5926	Remote Similarity	NPD3726	Approved
0.5922	Remote Similarity	NPD6011	Approved
0.5922	Remote Similarity	NPD6415	Discontinued
0.5905	Remote Similarity	NPD6650	Approved
0.5905	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD6617	Approved
0.5905	Remote Similarity	NPD6847	Approved
0.5905	Remote Similarity	NPD8130	Phase 1
0.5905	Remote Similarity	NPD6649	Approved
0.5905	Remote Similarity	NPD6869	Approved
0.59	Remote Similarity	NPD7632	Discontinued
0.5897	Remote Similarity	NPD7909	Approved
0.5876	Remote Similarity	NPD7732	Phase 3
0.5865	Remote Similarity	NPD6014	Approved
0.5865	Remote Similarity	NPD6012	Approved
0.5865	Remote Similarity	NPD6013	Approved
0.5859	Remote Similarity	NPD5286	Approved
0.5859	Remote Similarity	NPD5285	Approved
0.5859	Remote Similarity	NPD4696	Approved
0.5859	Remote Similarity	NPD4700	Approved
0.5849	Remote Similarity	NPD6882	Approved
0.5849	Remote Similarity	NPD8297	Approved
0.5846	Remote Similarity	NPD2270	Approved
0.5842	Remote Similarity	NPD6052	Approved
0.5833	Remote Similarity	NPD6940	Discontinued
0.5833	Remote Similarity	NPD4687	Approved
0.5833	Remote Similarity	NPD4058	Approved
0.5825	Remote Similarity	NPD6412	Phase 2
0.5816	Remote Similarity	NPD5959	Approved
0.5806	Remote Similarity	NPD4518	Approved
0.58	Remote Similarity	NPD5223	Approved
0.5794	Remote Similarity	NPD8133	Approved
0.5794	Remote Similarity	NPD8298	Phase 2
0.5783	Remote Similarity	NPD5276	Approved
0.578	Remote Similarity	NPD7115	Discovery
0.5765	Remote Similarity	NPD5275	Approved
0.5765	Remote Similarity	NPD4190	Phase 3

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